DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 03/23/2026 has been entered.
In the amendments filed on 03/23/2026, claims 1-15, 22-27, 29, and 32 are canceled. Claims 16-21, 28, 30, 31, and 33-38 are pending. Claims 16, 28, 30, 36, and 38 are amended. Claims 33-35 are withdrawn.
Priority
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claim 30 is objected to because of the following informalities: Claim 30 does not end with a period. Each claim must end with a period (MPEP 608.01(m)). Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claim 38 is rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention. Claim 38 recites the limitation “wherein the oxidizing agent is sodium peroxide” in lines 1-2, which does not have support in the application as filed. The specification of the instant application does not recite “sodium peroxide”, but recites that “oxidizing agents are known in the art, preferred is hydrogen peroxide” (p. 20, l. 9-10).
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 16-21, 28, 31, and 36 are rejected under 35 U.S.C. 103 as being unpatentable over Luterbacher et al. (WO 2017/178513 A1, made of record on 01/31/2025).
Regarding claims 16, Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein the aldehyde is an organic compound which can be generally represented by the following structure:
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(p. 8, l. 35-p. 9, l. 10), wherein R is an aromatic residue or an aliphatic residue (p. 9, l. 12-13) that can be substituted with one or more substituents (p. 9, l. 22-23. 35-36), wherein the aromatic residue is phenyl (p. 9, l. 30), wherein substituents can be selected independently from the substituents halogen or nitro (p. 9, l. 25-26), wherein the aliphatic residue is optionally a linear aliphatic residue with 1 carbon atom (p. 10, l. 5-6), wherein the aldehyde is optionally benzaldehyde (p. 9, l. 30-31) or acetaldehyde (p. 10, l. 9-10), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde optionally selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed.
Luterbacher does not teach a specific embodiment wherein the aldehyde is selected from the claimed group. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method because Luterbacher teaches that a method including the addition of an aldehyde was provided which unexpectedly leads to near theoretical yields of lignin monomers after hydrogenolysis of the extract product (p. 3, l. 39-p. 4, l. 2), that these yields were almost in an order of magnitude higher than those obtained from lignin using the same extraction and upgrading method in the absence of formaldehyde (p. 4, l. 2-4), that the conversion of the fragments of lignin into the monomers from lignin can be carried out by submitting the fragments of lignin to a hydrogenolysis (p. 15, l. 5-7), that an aldehyde is more preferably used than other compounds for heating together with the lignocellulosic-containing composition under acidic conditions (p. 8, l. 26-33), that the aldehyde is an organic compound which can be generally represented by the following structure:
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(p. 8, l. 35-p. 9, l. 10), wherein R is an aromatic residue or an aliphatic residue (p. 9, l. 12-13) that can be substituted with one or more substituents (p. 9, l. 22-23. 35-36), that the aromatic residue is phenyl (p. 9, l. 30), that substituents can be selected independently from the substituents halogen or nitro (p. 9, l. 25-26), that the aliphatic residue is optionally a linear aliphatic residue with 1 carbon atom (p. 10, l. 5-6), and that the aldehyde is optionally benzaldehyde (p. 9, l. 30-31) or acetaldehyde (p. 10, l. 9-10).
Regarding claim 17, Luterbacher teaches that the lignocellulose-containing composition has a lignin content of 10 wt.% to 40 wt.% based on the total weight of the lignocellulose-containing composition (p. 5, l. 22-24), which reads on wherein the lignocellulose-containing composition has a lignin content of 10-40 wt.% as claimed.
Regarding claim 18, Luterbacher teaches that the step (p. 6, l. 11) of providing a lignocellulose-containing composition (p. 4, l. 9) involves suspending the lignocellulose-containing composition in an organic solvent (p. 6, l. 11-12), which reads on wherein step a) involves suspending the lignocellulose-containing composition in an organic solvent as claimed.
Regarding claim 19, Luterbacher teaches that the organic solvent is methanol, ethanol, propanol, isopropanol, butanol, tetrahydrofuran, acetonitrile, formic acid, acetic acid, dimethylformamide, dimethylacetamide, γ-valerolactone, N-methyl-2-pyrrolidone, or dimethyl sulfoxide (p. 7, l. 12-20), and that the organic solvent comprises less than 50 volume percent of water (p. 7, l. 22-23), which reads on wherein the organic solvent is a polar aprotic solvent that contains less than 50% v/v of water as claimed.
Regarding claim 20, Luterbacher teaches that in the step (p. 8, l. 5-6) of heating the composition of the previous step under acidic conditions together with an aldehyde to achieve oligomers from lignin (p. 4, l. 10-13), a temperature, which is considered to be the end temperature of 50 to 120°C or a temperature of 70 to 100°C or a temperature of about 80°C, can be applied (p. 8, l. 5-8), and that the step can be carried out between 0.5 and 12 hours, between 0.75 and 10 hours, between 1 and 8 hours, or between 1.5 and 5.5 hours (p. 13, l. 4-6), which reads on wherein in step b) a temperature of 50 to 120 °C is applied for 0.5 to 12 hours as claimed.
Regarding claim 21, Luterbacher teaches that to achieve the acidic conditions one or more acidic compounds are added to the composition (p. 8, l. 11-12) that is the lignocellulose-containing composition (p. 4, l. 9), and that 1 to 10 mmol of the acidic compound per gram of the lignocellulose-containing composition can be used to achieve the acidic conditions (p. 8, l. 22-24), which reads on wherein the acidic conditions of step b) are generated by adding 1 to 10 mmol of an acidic compound per gram of the lignocellulose-containing composition to the lignocellulose-containing composition as claimed.
Regarding claim 28, Luterbacher teaches that the lignocellulose-containing composition and the aldehyde are present in a weight ratio of 25:1 to 1:1, wherein the weight of aldehyde is based on the weight of formaldehyde (p. 11, l. 31-p. 12, l. 5). As explained above for claim 16, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. Luterbacher therefore renders it obvious wherein the lignocellulose-containing composition and aldehyde selected from 2-chloro acetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde, are present in a weight ratio of 25:1 to 1:1, wherein the aldehyde is based on the weight of formaldehyde as claimed.
Regarding claim 31, Luterbacher teaches that the step c) can comprise the following sub-steps: c1) partitioning the fragments of lignin-containing phase and the residue, c2) neutralizing the fragments of lignin-containing phase and removing the solvent, c3) treating the product of step c3) with a solvent and removing the insoluble parts (p. 13, l. 27-31), which reads on wherein step c) comprises the sub-steps: c1) partitioning the fragments of a lignin-containing phase and a residue, c2) removing solvent from the fragments of lignin-containing phase to generate a residue, c3) treating the residue of step c2) with a second solvent, and c4) separating fragments of lignin from a mixture of step c3) as claimed.
Regarding claim 36, Luterbacher teaches that the method for producing monomers from lignin via depolymerization comprises the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), wherein the conversion, which can be regarded as a kind of depolymerization, can be carried out by oxidation and subsequently submitting the oxidized product to acidic condition (p. 15, l. 1-3), wherein the conversion of the fragments of lignin into the monomers from lignin can be caried out by submitting the fragments of lignin to a hydrogenolysis (p. 15, l. 5-7), wherein the hydrogenolysis is a reaction (p. 15, l. 9), which reads on wherein the one or more functional group(s) of the separated fragments of step c) are reacted thereby generating fragments of lignin as claimed.
Allowable Subject Matter
Claims 30 and 37 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter: Regarding claim 30, Luterbacher et al. (WO 2017/178513 A1, made of record on 01/31/2025) renders obvious the method according to claim 16 as explained above.
Luterbacher does not teach that the lignocellulose-containing composition and the aldehyde are reacted to form an acetal according to one or more of Formulae 2A to 4Z as claimed. Although Luterbacher renders obvious the method according to claim 16, and although Luterbacher teaches that by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), and that further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), Luterbacher’s teachings and the prior art of record do not teach or suggest reacting the lignocellulosic containing composition and the aldehyde to form an acetal according to one or more of Formulae 2A to 4Z. Luterbacher’s method would not inherently result in reaction of the lignocellulosic containing composition and the aldehyde to form an acetal according to one or more of Formulae 2A to 4Z as claimed because Luterbacher teaches that by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), and that further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12).
Regarding claim 37, Luterbacher et al. (WO 2017/178513 A1, made of record on 01/31/2025) renders obvious the method according to claim 16 as explained above.
Luterbacher does not teach that the product obtained from the step c) is brought in contact with a mixture of an oxidizing agent and an alkaline compound in a solvent. Although Luterbacher teaches that the method comprises converting the product of step c) into the monomers (p. 4, l. 6-7, 15), that the conversion, which can be regarded as a kind of depolymerization, can for example be carried out by oxidation and subsequently submitting the oxidized product to acidic condition (p. 15, l. 1-3), that the conversion of the fragments of lignin of step c) into the monomers from lignin can be carried out by submitting the fragments of lignin of step c) to a hydrogenolysis (p. 15, l. 5-7), and that usually hydrogenolysis is conducted in the presence of a catalyst and hydrogen (p. 15, l. 12-13), Luterbacher’s teachings do not read on the product obtained from the step c) is brought in contact with a mixture of an oxidizing agent and an alkaline compound in a solvent. The prior art of record do not teach or suggest bringing the product obtained from step c) in contact with a mixture of an oxidizing agent and an alkaline compound in a solvent.
Response to Arguments
Applicant's arguments filed 03/23/2026 have been fully considered but they are not persuasive. In response to the applicant’s argument that it is believed no new matter is introduced by any of the above amendments (p. 14), the amendment to claim 38 “wherein the oxidizing agent is sodium peroxide” causes the Office to reject claim 38 under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention. Claim 38 recites the limitation “wherein the oxidizing agent is sodium peroxide” in lines 1-2, which does not have support in the application as filed. The specification of the instant application does not recite “sodium peroxide”, but recites that “oxidizing agents are known in the art, preferred is hydrogen peroxide” (p. 20, l. 9-10).
Applicant’s arguments, see p. 14, filed 03/23/2026, with respect to the objection to the specification have been fully considered and are persuasive. The objection to the specification has been withdrawn.
Applicant’s arguments, see p. 15, filed 03/23/2026, with respect to the rejection of claims 16-21, 28, 30, 31, and 36-38 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, have been fully considered and are persuasive. The rejection of claims 16-21, 28, 30, 31, and 36-38 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, has been withdrawn.
Applicant’s arguments, see p. 15-19, filed 03/23/2026, with respect to the rejection of claims 30 under 35 U.S.C. 103 as being unpatentable over Luterbacher et al. (WO 2017/178513 A1, made of record on 01/31/2025) have been fully considered and are persuasive. The rejection of claims 30 under 35 U.S.C. 103 as being unpatentable over Luterbacher et al. (WO 2017/178513 A1, made of record on 01/31/2025) has been withdrawn.
Applicant's arguments filed 03/23/2026 have been fully considered but they are not persuasive. In response to the applicant’s argument that the present invention deliberately selects specific aldehydes in order to introduce defined functional groups into the produced lignin fragments (p. 16), it is noted that aldehydes in order to introduce defined functional groups into the produced lignin fragments is not recited in claim 16. Claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, and claim 16 does not require the one or more functional group(s) to be derived from functional groups of the aldehyde. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
In response to the applicant’s argument that the aldehydes used in Luterbacher are relatively simple aldehydes (p. 16), Luterbacher teaches that the aldehyde is an organic compound which can be generally represented by the following structure:
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(p. 8, l. 35-p. 9, l. 10), wherein R is an aromatic residue or an aliphatic residue (p. 9, l. 12-13) that can be substituted with one or more substituents (p. 9, l. 22-23. 35-36), wherein the aromatic residue is phenyl (p. 9, l. 30), wherein substituents can be selected independently from the substituents halogen or nitro (p. 9, l. 25-26), wherein the aliphatic residue is optionally a linear aliphatic residue with 1 carbon atom (p. 10, l. 5-6), wherein the aldehyde is optionally benzaldehyde (p. 9, l. 30-31) or acetaldehyde (p. 10, l. 9-10), which reads on an aldehyde optionally selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method because Luterbacher teaches that a method including the addition of an aldehyde was provided which unexpectedly leads to near theoretical yields of lignin monomers after hydrogenolysis of the extract product (p. 3, l. 39-p. 4, l. 2), that these yields were almost in an order of magnitude higher than those obtained from lignin using the same extraction and upgrading method in the absence of formaldehyde (p. 4, l. 2-4), that the conversion of the fragments of lignin into the monomers from lignin can be carried out by submitting the fragments of lignin to a hydrogenolysis (p. 15, l. 5-7), that an aldehyde is more preferably used than other compounds for heating together with the lignocellulosic-containing composition under acidic conditions (p. 8, l. 26-33), that the aldehyde is an organic compound which can be generally represented by the following structure:
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(p. 8, l. 35-p. 9, l. 10), wherein R is an aromatic residue or an aliphatic residue (p. 9, l. 12-13) that can be substituted with one or more substituents (p. 9, l. 22-23. 35-36), that the aromatic residue is phenyl (p. 9, l. 30), that substituents can be selected independently from the substituents halogen or nitro (p. 9, l. 25-26), that the aliphatic residue is optionally a linear aliphatic residue with 1 carbon atom (p. 10, l. 5-6), and that the aldehyde is optionally benzaldehyde (p. 9, l. 30-31) or acetaldehyde (p. 10, l. 9-10).
In response to the applicant’s argument that nowhere does Luterbacher teach or suggest that the aldehydes can be selected or used to successfully impart a functional group to the resulting lignin monomer (p. 16), it is noted that the aldehydes can be selected or used to successfully impart a functional group to the resulting lignin monomer is not recited in claim 16. Claim 16 does not require the one or more functional group(s) of the fragments of lignin to be derived from the aldehyde, claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that in the method of the presently claimed invention, the aldehyde is specifically selected as a functionalization tool, so that the resulting lignin fragments contain pre-defined functional groups suitable for subsequent transformations and downstream applications without having to perform additional difficult and costly post-modification steps on the lignin fragment (p. 16), it is noted that the aldehyde being specifically selected as a functionalization tool, so that the resulting lignin fragments contain pre-defined functional groups suitable for subsequent transformations and downstream applications without having to perform additional difficult and costly post-modification steps on the lignin fragment is not recited in claim 16. Claim 16 does not require the one or more functional group(s) of the fragments of lignin to be derived from the aldehyde, and claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993).
In response to the applicant’s argument that one skilled in the art would not have predicted that the method of Luterbacher could have been modified to utilize functionalized aldehydes to successfully insert a functional group into the resulting lignin fragment as required by the presently amended claims and that aldehydes specifically listed in amended claim 16 are able to successfully form a defined group in the resulting lignin fragment (p. 16), it is noted that functionalized aldehydes insert a functional group into the resulting lignin fragment and that aldehydes form a defined group in the resulting lignin fragment are not recited in claim 16. Claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that Luterbacher does not teach or suggest using aldehydes for the purpose of incorporating functional groups into the lignin fragments, nor does Luterbacher recognize the technical concept of directly forming functionalized lignin fragments through selection of such specific aldehydes (p. 17), it is noted that using aldehydes for the purpose of incorporating functional groups into the lignin fragments and directly forming functionalized lignin fragments through selection of such specific aldehydes are not recited in claim 16. Claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that there is no teaching or suggestion that would have motivated one skilled in the art to choose the presently claimed specific aldehydes, include the chloro-substituted aldehydes or hydroxy-substituted aldehydes, for the purpose of forming lignin fragments having specific functional groups (p. 17), it is noted that aldehydes for the purpose of forming lignin fragments having specific functional groups are not recited in claim 16. Claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that there is not teaching or suggestion that would have allowed one skilled in the art to predict that the use of such aldehydes would have successfully imparted the functional group into the lignin fragment (p. 17), it is noted that use of such aldehydes impart the functional group into the lignin fragment are not recited in claim 16. Claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that formation of lignin fragments containing the functional groups is an advantageous property that was not expected in view of Luterbacher (p. 17), claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that the specific aldehydes required in the presently amended method claims produce lignin fragments having different types of useful functionalities, without the need for difficult and costly post-modification (p. 17-18), it is noted that the aldehydes produce lignin fragments having different types of useful functionalities, without the need for difficult and costly post-modification are not recited in claim 16. Claim 16 does not limit the composition of the one or more functional groups(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that none of the potential effects or benefits from the presently recited aldehydes are disclosed or even suggested in Luterbacher, that these functionalities are introduced in the present invention directly through the aldehyde employed in the depolymerization process, rather than by subsequent modification of isolated lignin fragments used in previous methods, and that this direct route is a significant practical and technical advantage over post-modification processes describe in convention prior art approaches (p. 18), it is noted that potential effects or benefits from the presently recited aldehydes are not recited in claim 16. Claim 16 does not require the one or more functional group(s) of the fragments of lignin to be derived from functional groups of the aldehyde, and claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that Luterbacher neither teaches nor suggests selecting such aldehydes for this purpose, that the selection of aldehydes in the present claimed invention is therefore not an arbitrary sampling from a broad genus, but an intentional selection tied to the technical objective of obtaining lignin fragments with useful functional groups already incorporated into the molecule (p. 18), it is noted that lignin fragments with useful functional groups are not recited in claim 16. Claim 16 does not require the one or more functional group(s) of the fragments of lignin to be derived from functional groups of the aldehyde, and claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that the question is whether the prior art Luterbacher would have led one skilled in the art to predictably select these aldehydes as part of a method to produce functionalized lignin fragments having defined functional groups and improved downstream functionality (p. 18), it is noted that functionalized lignin fragments having defined functional groups and improved downstream functionality are not recited in claim 16. Claim 16 does not require the one or more functional group(s) of the fragments of lignin to be derived from functional groups of the aldehyde, and claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Although the claims are interpreted in light of the specification, limitations from the specification are not read into the claims. See In re Van Geuns, 988 F.2d 1181, 26 USPQ2d 1057 (Fed. Cir. 1993). Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that Luterbacher does not even recognize the need for producing lignin fragments having desired functional groups, and that Luterbacher does not suggest any solutions for how to produce such functionalized lignin fragments (p. 18), claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin. Claim 16 recites “a method for producing fragments of lignin having one or more functional group(s)”, “heating the composition of step a) under acidic conditions together with an aldehyde selected from the group”, and “fragments of lignin having one or more functional group(s)”. Luterbacher teaches a method for producing monomers from lignin via depolymerization comprising the steps of a) providing a lignocellulose-containing composition, b) heating the composition of step a) under acidic conditions together with an aldehyde to achieve oligomers from lignin, c) separating the product of step b), and d) converting the product of step c) into the monomers (p. 4, l. 6-15), wherein by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), wherein further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), where in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25), which reads on a method for producing fragments of lignin having one or more functional group(s), wherein the method comprises the steps of: b) heating the composition of step a) under acidic conditions together with an aldehyde, and c) separating fragments of lignin having one or more functional group(s) from the mixture of step b). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select a phenyl substituted with a halogen that is chloride or bromide at the 2, 3, or 4 position with respect to the aldehyde group, a phenyl substituted with a nitro at the 2 or 4 position with respect to the aldehyde group, or a linear aliphatic residue with 1 carbon atom substituted with a halogen that is chloride or bromide as Luterbacher’s R in Luterbacher’s structure
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for Luterbacher’s aldehyde. The proposed modification would read on wherein the aldehyde is selected from 2-chloroacetalaldehyde, 2-bromoacetaldehyde, 2-chlorobenzaldehdye, 2-bromobenzaldehyde, 3-chlorobenzaldehdye, 3-bromobenzaldehyde, 4-chlorobenzaldehyde, 4-bromobenzaldehdye, 2-nitrobenzaldehyde, and 4-nitrobenzaldehyde as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying a yield of lignin monomers produced from Luterbacher’s method, as explained in the rejection of claim 16.
In response to the applicant’s argument that the present obviousness rejections over Luterbacher are based on improper hindsight analysis (p. 18), it must be recognized that any judgment on obviousness is in a sense necessarily a reconstruction based upon hindsight reasoning. But so long as it takes into account only knowledge which was within the level of ordinary skill at the time the claimed invention was made, and does not include knowledge gleaned only from the applicant's disclosure, such a reconstruction is proper. See In re McLaughlin, 443 F.2d 1392, 170 USPQ 209 (CCPA 1971). The Office’s judgment on obviousness takes into account only the teachings of Luterbacher, which is knowledge that was within the level of ordinary skill before the effective filing date of the claimed invention.
In response to the applicant’s argument that based on the lack of teaching in Luterbacher on how to provide functional groups in their resulting lignin monomers, one skilled in the art would not have predicted that the method of Luterbacher could have successfully modified to produce the functionalized lignin fragments as required by the presently amended claims (p. 19), Luterbacher teaches that by applying step b) the bindings in the lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved (p. 13, l. 8-9), that further, bindings within the lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin (p. 13, l. 10-12), and that in step c) of the method the obtained fragments of lignin are separated from the residual mixture of step b) (p. 13, l. 24-25). When the bindings in Luterbacher’s lignocellulose-containing composition between the lignin fraction and the cellulose or hemicellulose fractions are cleaved, and when bindings within Luterbacher’s lignin are also cleaved such that fragments of lignin are obtained which alternatively can be considered as so-called oligomers from lignin, Luterbacher’s fragments of lignin would comprise one or more functional group(s) of some composition. Since claim 16 does not limit the composition of the one or more functional group(s) of the fragments of lignin, Luterbacher’s teachings satisfy the limitation wherein the fragments of lignin have one or more functional group(s) as claimed.
Correspondence
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/DAVID T KARST/Primary Examiner, Art Unit 1767