DETAILED ACTION
Notice of Pre-AIA or AIA Status
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
2. Claims 1-2, 4-7, 9-25 are currently pending. Claims 16-21 have been withdrawn as being drawn to a non elected invention. Claims 1-2, 4-7, 9-15 and 22-25 are currently under examination. This office action is in response to the amendment filed on 11/28/2025.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
3. Claims 4, 25 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Concerning claim 4 the claim recites “the additional component A” which does not have enough antecedent basis to be understood.
Concerning claim 25 the claim recites “component A an itaconimide” which renders the claim indefinite as it is not clear what is present and what is required to be an itaconimide. For the purpose of art examination this is interpreted as “component A comprises an itaconimide”.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
4. Claims 1-2, 4-7, 9-15 and 22-25 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends. Claim 1 recites “an itconamide” as part of “a) a heat curable component A having one or more chemical species selected from the group consisting of” which does not have support in applicants originally filed specification. Applicant does have support for Itaconimide (which has a ring structure) on pg 6 lines 1-10 of applicants specification which is different from the claimed itaconamide (which does not have a ring structure) .
Claims 2, 4-7, 9-15 and 22-25 are rejected as being dependent from a rejected base claim.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
5. Claim(s) 1-2, 5, 9-11, 13-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Evsyukov (WO 2014/154485 A1) in view of Dershem (US 2008/0075965 A1).
Concerning claim 1-2, 5, 9, 11 Evsyukov 485 teaches a resin composition of 30 parts or 29.7 wt% of 4,4’ bismaleimidodiphenyl methane, 18 parts or 17.8 wt% of m-xylylene bismaleimide, 12 parts or 11.9 wt% of 2,2,4-trimethylhexamethylenebismaleimide 1 part or 1 wt% of phenothiazine and 40 parts or 39.6 wt% of 3,3’ diallyl bisphenol A (pg 56 paragraph 4).
This would indicate that the composition comprises 60 parts or approximately 59.4 wt% of bismaleimide compounds which have a structure meeting the claimed formula (I), of which 30 wt% is m-xylene bismaleimide which is a compound of the structure of formula I where n is an integer of 2 and the compound comprises an aromatic residue linked the N-atom of each maleimide ring of Formula I via a methylene group, the methylene group being linked directly to the N-atom, and 20 wt% of which is 2,2,4-trimethylhexamethylenebismaleimide which is a component of Formula I where R2 is an aliphatic residue. The composition comprises 40 parts or 39.6 wt% of a chemical species comprising an allyl group of diallyl bisphenol A. The composition is indicated to include phenothiazine which Evsyukov 485 teaches is a cure inhibitor (pg 41 paragraph 3).
Evsyukov 485 is silent as to the bismaleimide component being heat curable, the allyl component being light curable, and that the composition is for three-dimensional printing or the presence of a photoinitiator suitable for radical polymerization upon light excitation within the wavelength spectrum of 150 nm to 580 nm in the claimed amounts.
However, Component A has the claimed structure and maleimide monomer units are well known to be capable of being heat cured and therefore the component A of Evsyukov 485 would be considered to be a Heat curable component. Also component B of 3,3’ diallyl bisphenol A includes allyl groups which are well known to be able to be able to be polymerized by means of photopolymerization and as such the component B of Evsyukov 485 would be considered to be light curable.
Evsyukov 485 teaches that the definition of “curable” indicated by invention means that the compounds or mixtures of materials can be transformed into a solid substantially non-flowing material by means of chemical reaction, crosslinking, radiation crosslinking or the like (pg 14 paragraph 5), which would indicate to one of ordinary skill in the art that Evsyukov 485 at least recognizes that curing by means of radiation can occur. Evsyukov 485 additionally indicates that the curable mixture can further comprise one or more cure accelerators (pg 40 paragraph 3) which are present in an amount of from 0.05 wt% to 1 wt% based on the total weight of the curable mixture (pg 41 paragraph 1). This amount of cure accelerator corresponds to a range which is within the claimed range of the amount of the photoinitiator. The resin compositions of Evsyukov 485 are indicated to be curable thermosetting resin compositions which can be used as adhesives and electrical composites (pg 1 paragraph 1).
Dershem is drawn to compositions containing maleimide compounds and aromatic diene compounds useful for thermosetting resins (abstract) used as adhesives (paragraph 0001). Dershem teaches that at least one curing initiator is present in the composition from 0.1 wt% to about 5 wt% (paragraph 0038) and teaches that these initiators can include a photo initiator which can be initiated by UV radiation with examples including acylphosphine oxide initiators (paragraph 0039). It should be noted that the acyl phosphine oxides have the same structure that is claimed and the uv spectrum has a range of from 10-400 nm indicating that the initiators of Dershem would be suitable for radical polymerization upon light excitation within the wavelength section of 150 nm to about 400 nm which is within the claimed range.
It would have been obvious to one of ordinary skill in the art at the time of filling to alter the exemplary composition of Evsyukov 485 to use a acrylphosphine oxide photoinitator as the cure accelerator of Evsyukov 485 in the claimed amounts to give the claimed composition because Dershem teaches that it is useful to use acyl phosphine oxide photoinitoatrs in the claimed amount as a free radical initiator for compositions that use bismaleimides and aromatic diene components for adhesives and so would be a useful initiator for the composition of Evsyukov 485.
The indication of “A resin composition for three-dimensional printing” would be considered to be an indication of the intended use of the resin composition.
If the body of a claim fully and intrinsically sets forth all of the limitations of the claimed invention, and the preamble merely states, for example, the purpose or intended use of the invention, rather than any distinct definition of any of the claimed invention’s limitations, then the preamble is not considered a limitation and is of no significance to claim construction. Shoes by Firebug LLC v. Stride Rite Children’s Grp., LLC, 962 F.3d 1362, 2020 USPQ2d 10701 (Fed. Cir. 2020). See MPEP 2111.02.II.
As such since Evsyukov 485 in view of Dershem teaches each of the claimed components in the claimed amounts and the composition would be capable of being used for three dimensional printing the composition would meet the claimed limitations.
Concerning claim 10, 14 Evsyukov 485 teaches that the composition can include one or more cure accelerators and gives that examples of these cure accelerators include peroxides (pg 40 paragraph 4).
Dershem further teaches that in some embodiments both photo initiation and thermal initiation may be desirable in examples such as curing of the photoinitiator containing adhesive can be started by UV irradiation and in a later processing step curing can be completed by the application of heat to accomplish a free radical cure and as such both UV and thermal initiators may be added to the adhesive composition (paragraph 0045). Dershem gives examples of peroxides such as dicumyl peroxided dibenzoyl perioxide, tert butyl perbenzoate, di (tert butyl )peroxide (paragraph 0038) which correspond to the claimed thermal initiators.
It would have been obvious to one of ordinary skill in the art to alter the exemplary composition of Evsyukov 485 to include a combination of the photoinitiator that can be initiated by UV radiation and one of the indicated peroxide thermal initiators because Evsyukov 485 teaches that the composition can include one or more cure accelerators and Dershem teaches that it is useful to have both UV and thermal initiators in the same composition and teaches that the claimed peroxides can be used in the composition.
Concerning claim 13 Evsyukov 485 further teaches that the comonomer component can be selected from at least one comonomer of diallyl bisphenol A, diallyl bisphenol F, diallyl ether bisphenol A, diallyl ether of bisphenyl F , bisphenol A dicyanate ester, diallyl phthalate, triallyl isocyanurate, triallyl cyanurate, styrene, divinyl benzene, diaminodiphenyl methane, diaminobenzene, and bis (4-aminocyclohexyl)methane among others (pg 38 paragraphs 4). Each of these indicated monomers is one of the indicated comonomers. In the even that more than one of these comonomers are used in the composition this would result in the component A further comprising one of the indicated comonomers.
It would have been obvious to one of ordinary skill in the art at the time of filling to alter the composition of Evsyukov 485 in view of Dershem to include an additional monomer having the claimed structure because Esyukov 485 teaches that multiple monomers having the claimed structures can be used as a comonomer in the composition and so it would be obvious to use the monomers in combination with one another.
Concerning claim 15 Evsyukov 485 as stated above teaches a resin composition of 30 parts or 29.7 wt% of 4,4’ bismaleimidodiphenyl methane, 18 parts or 17.8 wt% of m-xylylene bismaleimide, 12 parts or 11.9 wt% of 2,2,4-trimethylhexamethylenebismaleimide 1 part or 1 wt% of phenothiazine and 40 parts or 39.6 wt% of 3,3’ diallyl bisphenol A (pg 56 paragraph 4). The addition of a small amount of photoinitiator as is indicated in the discussion of claim 1 above would not significantly change the viscosity of the composition.
This composition is indicated to have a viscosity at 100°C of 158 mPa*s and a viscosity at 80°C of 710 mPa*s. It should be noted that a drop of 20 °C results in a change in viscosity of a factor of 4.49. It should also be noted that the viscosity at 80°C differs from the claimed viscosity at room temperature by a factor of 2.6 and the difference in temperature is 57 °C. It should also be noted that the greatest increase in viscosity values shown in Evsyukov 485 occurs at lower temperatures (pg 51-53). If the same proportional difference in viscosity per degree C is maintained (approximately 0.2245 times increase in viscosity per 1 °C) this would result in an expected viscosity at room temperature of 9.085 Pa*s, which is almost twice the minimum value of the claimed viscosity. However as is stated above the greatest increase in viscosity values shown in Evsyukov 485 occurs at lower temperatures (pg 51-53) which would indicate that this calculated estimate underestimates the viscosity at room temperature. As such given the viscosity at 80°C of the composition, and the viscosity at 100°C, the viscosity of the composition would have the claimed viscosity at room temperature of greater than 5 Pa*s.
"[T]he discovery of a previously unappreciated property of a prior art composition, or of a scientific explanation for the prior art’s functioning, does not render the old composition patentably new to the discoverer." Atlas Powder Co. v. IRECO Inc., 190 F.3d 1342, 1347, 51 USPQ2d 1943, 1947 (Fed. Cir. 1999). Thus the claiming of a new use, new function or unknown property which is inherently present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). See MPEP 2112.I.
"[T]he PTO can require an applicant to prove that the prior art products do not necessarily or inherently possess the characteristics of his [or her] claimed product. Whether the rejection is based on ‘inherency’ under 35 U.S.C. 102, on ‘prima facie obviousness’ under 35 U.S.C. 103, jointly or alternatively, the burden of proof is the same." In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433-34 (CCPA 1977). See MPEP 2112.V.
As such the composition of Evsyukov 485 in view of Dershem would have the claimed viscosity.
6. Claim 24 is rejected under 35 U.S.C. 103 as being unpatentable over Evsyukov 485 (WO 2014/154485 A1) in view of Dershem (US 2008/0075965 A1)as applied to claim 11 above, and further in view of Kamogawa (Kamogawa, Hiroyoshi Et al “Syntheses of Polymerizable Hydroquinone Derivatives” 1976 Journal of polymer Science Polymer Chemistry Edition Vol 14 1235-1240).
Concerning claim 24 Evsyukov 485 in view of Dershem teaches the composition of claim 11 as is stated above at further teaches that the polymerization inhibitor that can be used in the composition can be a hydroquinone (pg 41 paragraph 0003).
Evsyukov 485 does not specifically teach that the polymerization inhibitor is additionally functionalized with a polymerizable functional group which can undergo copolymerization either with component A or component B.
Kamogawa is drawn to polymerizable hydroquinone derivatives (pg 1235 paragraph 4) that contain vinyl double bonds (pg 1239 paragraph 1). Kamogawa indicates that hydroquinone compounds are well known inhibitors for free radical polymerizations (pg 1235 paragraph 2).
It would have been obvious to one of ordinary skill in the art at the time of filling to alter the composition of Domeier to use the polymerizable hydroquinone derivative as the polymerization inhibitor to give the claimed composition for the purpose of providing polymerization inhibitors that will not leak out of the cured composition because they are polymerized with monomers of the composition thereby avoiding leeching of chemical compounds to unintended areas surfaces and places.
7. Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Evsyukov 485 (WO 2014/154485 A1) in view of Dershem (US 2008/0075965 A1) as applied to claim 1 above, and further in view of Otani (JP H04-096914 A).
Concerning claim 4 Evsyukov 485 in view of Dershem teaches the composition of claim 1 as is stated above.
Evsyukov 485 further teaches that the object of the invention is to provide curable mixture that posses low viscosity at the lowest possible temperature (pg 3 paragraph 2).
Otani is drawn to bismaleimide compositions (pg 1 paragraph 1) which can include reactive diluents such as diallyl substituted bisphenol A (pg 1 paragraph 4). Ontai finds that using 20-95 parts by weight of bismaleimide and 80-5 parts by weight of a monofunctional maleimide helps provide a bismaleimide resin composition which is liquid at room temperature or completely soluble in a low melting point low boiling point solvent at high concentration (pg 1 paragraphs 5-7). Examples of the monofunctional maleimide include phenyl maleimide methyl phenyl maleimide benzylic maleimide lauryl maleimide bromophenylmaleimide and hydroxyphenyl maleimide (pg 1 paragraph 10). This would correspond to an amount of monofunctional maleimide in the maleimide components which ranges from 5 to 80 wt% which is an overlapping range with the claimed range.
It would have been obvious to one of ordinary skill in the art at the time of filling to alter the composition of Evsyukov in view of Dershem to include one of the monofunctional maleimide compounds of Otani which correspond to the claimed additional component A for the purpose of helping to provide low viscosity composition as the lowest possible temperature and to use the component in the claimed amount because Otani teaches an overlapping range with the claimed range of the amount of the monofunctional maleimide.
8. Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over Evsyukov 485 (WO 2014/154485 A1) in view of Dershem (US 2008/0075965 A1) as applied to claim 1 above, and further in view of Turpin (US 4,954,195).
Concerning claim 6 Evsyukov 485 in view of Dershem teaches the composition of claim 1 as is stated above.
Evsyukov 485 further teaches that the curable mixture is applied onto or blended with a fibrous or particular reinforcement (pg 46 paragraph 8-10) and teaches that it is possible to admix the curable mixture with additives such as fillers (pg 46 paragraph 4).
Turpin is drawn to composite materials having a thermoset matrix such as a bismaleimide (column 2 liens 55-65). And teaches that adding a thermoplastic powder or filler of the thermoset matrix can help improve the damage tolerance characteristic of the thermoset (column 2 lines 40-65) and the thermoset composition can be applied to fiber reinforcement (abstract). This thermoplastic resin would be a toughness modifier.
It would have been obvious to one of ordinary skill in the art at the time of filling to alter the exemplary composition of Evsyukov 485 in view of Dershem to include the thermoplastic filler of Turpin for the purpose of improving the toughness and damage resistance characteristics of the composition and Evsyukov 485 teaches that fillers can be used in the composition.
Allowable Subject Matter
9. Claims 7, 12, 22-23, 25 would be allowable if rewritten to overcome the rejection(s) under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), 1st paragraph, set forth in this Office action and to include 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: None of the prior art fairly teach or suggest the claimed method which includes the presence of a multifunctional (meth)Acrylate , one of the particularly indicated (meth)acrylates of claim 22, one f the thermal initiators that comprises a polymerizable functional group of claim 23 or that comprises an itaconimide.
Response to Arguments
10. Applicant's arguments filed 11/28/2025 have been fully considered but they are not persuasive.
Applicant argues that claim 1 has been revised to recite an itaconamide as one the species of the genus of comoante A although applicant respectfully submits that itaconamide is an isomer of the original claim formula (I) when R1 is CH2.
This argument is not found to be persuasive as Itaconamide does not have the structure of formula (1) but is a non cyclic compound that has an additional nitrogen atom compared to the claimed formula(1). Itaconimide is a similarly spelled compound that does have a cyclic structure but does not have the structure of formula (1) as it does not have a double bond in the ring structure but has a double bond which is attached to the ring structure. As such the 112(a) rejection provided above is maintained.
Applicant argues that concerning 102 rejection over Evsyukov 485 that subject matter of non rejected claim 8 has been included in independent claim 1. Concerning the 10 rejections over Evsyukov 485 applicant argues that they have revised claim 1 to include the subject matter of non rejected claims 3 and 8 thereby obviating these rejections. Applicant further argues as noted on pg 12 of the specification when component A further includes a species of formula (I) in which R2 is an aliphatic residue and the species is present in an amount within the range of from 0.5 wt% to 50 wt% these species bring about lower melting temperature or viscosities of the uncured resin and additional light curability which enhances there processability in 3D printing . These present claims therefor would not have been obvious in light of the prior art cited in the office action.
This argument is not found to be persuasive as Evsyukov 485 as is stated above teaches a resin composition of 30 parts or 29.7 wt% of 4,4’ bismaleimidodiphenyl methane, 18 parts or 17.8 wt% of m-xylylene bismaleimide, 12 parts or 11.9 wt% of 2,2,4-trimethylhexamethylenebismaleimide 1 part or 1 wt% of phenothiazine and 40 parts or 39.6 wt% of 3,3’ diallyl bisphenol A (pg 56 paragraph 4). This includes indicated species of formula (I) in which R2 is an aliphatic residue of 2,2,4-trimethylhexamethylenebismaleimide as was recited by former claim 3. While Esyukov 485 does not specifically teach the presence of the photoinitator as is stated in former claim 8 Dershem is drawn to compositions containing maleimide compounds and aromatic diene compounds useful for thermosetting resins (abstract) used as adhesives (paragraph 0001) and teaches that at least one curing initiator is present in the composition from 0.1 wt% to about 5 wt% (paragraph 0038) and teaches that these initiators can include a photo initiator which can be initiated by UV radiation with examples including acylphosphine oxide initiators (paragraph 0039). It should be noted that the acyl phosphine oxides have the same structure that is claimed and the uv spectrum has a range of from 10-400 nm indicating that the initiators of Dershem would be suitable for radical polymerization upon light excitation within the wavelength section of 150 nm to about 400 nm which is within the claimed range. As such Dershem is used in order to teach the use of the claimed photoinitator which can be added to the composition of Esyukov 485 and would render the claimed composition obvious as is stated in the rejection above. As such the rejection provided above is maintained.
Conclusion
11. Claims 1-2 4-6, 9-11, 13-15 and 24 are rejected. Claims 7, 12, 22-23, 25 are allowable over the closest art of record but are rejected under 112(a).
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DAVID L MILLER whose telephone number is (571)270-1297. The examiner can normally be reached M-F 9:30-6:00.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Joseph Del Sole can be reached at 571-272-1130. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DAVID L MILLER/Examiner, Art Unit 1763
/JOSEPH S DEL SOLE/Supervisory Patent Examiner, Art Unit 1763