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 .
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.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1 – 35 in the reply filed on 5/21/26 is acknowledged. Applicant elects kraft softwood lignin for species a and d, formaldehyde for species b and lignin bound aromatic hydroxyl groups for species c. Claims 15 – 18 require higher aldehydes than the elected formaldehyde and therefore are withdrawn. Therefore, claims 1 – 14 and 19 – 35 are under examination.
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.
Claim 23 is 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. Claim 23 addresses a gelation time for the adhesive without specifying any type of curing conditions therefore it is unclear how the gelation time could be within the range of 4 minutes to 30 minutes.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1 – 2, 5, 7 – 10, 13, 19, 21, 24, 26 – 27, 29 - 30 and 33 – 35 are rejected under 35 U.S.C. 102(a) as being anticipated by US 20150159061 A1 to Kouisni et al. hereinafter “Kouisni” and as evidenced by the NPL titled On the structure of softwood kraft lignin, Crestini et al., Green Chemistry, 2017,, 19, 4104.
Kouisni is directed to phenol formaldehyde adhesive polymer and lignin phenol formaldehyde adhesive polymer [0001].
Regarding claims 1 – 2, 5, 7 – 10, 19, 21, 24 and 33 - 35, Kouisni teaches a composition at Example 4 which comprises 500 parts (18.85%) phenol, 272 parts (10.25%) kraft softwood lignin, 430 parts (16.21%) of paraformaldehyde, 140 parts (5.28 %) of a 50% sodium hydroxide solution and 1310 parts (49.40 %) of water [0080]. The process is outlined in paragraph [0056 – 0062] reproduced below.
[0056] The first step of the method described herein is the
mixing of lignin (if applicable), phenol, formaldehyde, a hydroxide and the carbon black (i.e. see EXAMPLES 1, and 2) and allowing the mixture to react at elevated temperatures. The order of addition of the above starting compounds may vary. In a preferred embodiment, phenol is added with water first. Then caustic (the hydroxide, in a preferred embodiment is sodium and/or potassium hydroxide) is loaded to adjust the pH in the range of 7 to 11, preferably less than 10. The form of the hydroxide solution is usually 50% by weight. Subsequently, carbon black is added followed by formaldehyde
which is added slowly over a period of30 min. This prepared medium methylolation is, subsequently, heated to methylolation temperatures ranging between 60-75° C., preferably 70° C., for a period of 1 to 2 hours. At this time, the methylolation
reaction takes place, with formaldehyde typically reacting at the ortho- (and para) position of the phenol and/or with available reaction sites on the lignin, to produce a methylolated medium comprising methylolated phenols.
[0057] The second step of the method described herein is the raising of the temperature to 75-95° C. to promote a condensation reaction(s) of the methylolated phenols, and
preferably 80-85° C. for a certain period of time. At this stage, temperature control is important to obtain a proper viscosity range. [0058] The method further includes a third step, where the temperature is reduced to temperatures ranging between
60-75° C., preferably 70° C. During this step, a second portion of formaldehyde is slowly added over 30 min and the temperature is kept at 70° C. for another 30-60 min.
[0059] It should be noted here that it is possible to combine the first and third steps into a single step to produce a similar phenolic resin. The phenolic resins obtained in a single step process may have different properties compared to the phenolic resins produced in two steps.
[0060] The fourth step is loading a second portion of sodium hydroxide over 10 min and raising the temperature to 80-85° C., while closely monitoring the viscosity. The viscosity is typically varied for different applications and is in the range of approximately 100-200 cps for OSB with a solids content around 45-60%, approximately 250-3000 cps or higher for plywood applications, and approximately 60-200 cps for spray-drying conversion to a powder resin used in OSB manufacturing. At this stage, temperature control is important to obtain the proper viscosity range.
[0061] Once the first and third steps are combined into one step, the second and fourth steps can also be combined into one step in which polymer condensation takes place until the required viscosity is reached at a certain pH.
[0062] The quantities of raw materials added at each step,
the temperature at which the reactions occur and/or the molar
ratios of formaldehyde to phenol, may all vary depending on
the final phenolic resin/adhesive requirements. In practice,
the molar ratio of formaldehyde to phenol is preferably from
1.5:1 to 3.0:1. More preferably, the molar ratio varies from
1.8: 1 to 2.8: 1; the weight ratio of base (sodium hydroxide
and/or potassium hydroxide) to phenol and (lignin if applicable)
varies from 0.03: 1.00 to 0.30: 1.00. More preferably, the weight ratio varies from 0.10: 1.00 to 0.20: 1.00.
Paraformaldehyde when mixed with water and / or heated produces formaldehyde. The molar ratio of phenol (aromatic hydroxyl groups) / aldehyde is 1 / 1.5 to 1 / 3.5 [0062] . Kouisni teaches that the phenol (and lignin if included) is added with water first, then the caustic (sodium hydroxide) solution is added. [0056]. Next the carbon black, if required, and the formaldehyde is added, heated 60 – 75 C and at this time the methylation reaction takes place with the formaldehyde typically reacting at the ortho (and para) position of the phenol and / or with available reaction sites on the lignin to produce a methylolated medium comprising methylolated phenols [0056]. The base solution is added in 2 or 3 aliquots (batchwise) and no solid precipitate is recorded (less than 0.1wt. % solids). The viscosity of Example 4 is 150 – 200 cPs [0080]. Kouisni teaches that the viscosity of the adhesive for plywood applications is 250 – 3000 cPs [0060].
As to claim 13, the NPL to Crestini shows that the structure of the kraft softwood lignin comprises aromatic ether groups and carbons which are ortho to hydroxyl groups which are reactive carbons due to the electron withdrawing ability of the hydroxyl group. See at least figure 4.
Regarding claims 26 – 27 and 29 - 30, a second addition of 70 parts (2.64%) aqueous sodium hydroxide (catalyst in water) was added before reaction at 70 C [0080]. Subsequently, the adhesive of Example 4 is applied to two Aspen strands and cured in a press at 150C [0084].
Claim Rejections - 35 USC § 103
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.
Claim(s) 3 – 4, 6, 25 and 31 are rejected under 35 U.S.C. 103 as being unpatentable over US 20150159061 A1 to Kouisni et al. hereinafter “Kouisni” and as evidenced by the NPL titled On the structure of softwood kraft lignin, Crestini et al., Green Chemistry, 2017,, 19, 4104.
The limitations for the independent claim refer to paragraphs 8 – 11 supra.
Regarding claims 3 – 4, Kouisni is silent as to an adhesive having a pH of at least 12 and the amount of water in the adhesive. Kouisni teaches that the pH can range from 7 – 11 [0056]. It would have been obvious to one of ordinary skill to adjust the pH to achieve the desired reaction rate of the reactants and to optimize the water level in the adhesive to the required application viscosity.
As to claim 6, Kouisni is silent as to the amount of unreacted formaldehyde in the adhesive. It would have been obvious to one of ordinary skill to minimize or eliminate any free formaldehyde in the system because of it toxicity.
Regarding claim 25, Kouisni teaches that the ratio of aromatic hydroxyl groups to aldehyde functionality is 1 / 1.5 to 1 / 3.0 [0062].
In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990) (The prior art taught carbon monoxide concentrations of "about 1-5%" while the claim was limited to "more than 5%." The court held that "about 1-5%" allowed for concentrations slightly above 5% thus the ranges overlapped.); In re Geisler, 116 F.3d 1465, 1469-71, 43 USPQ2d 1362, 1365-66 (Fed. Cir. 1997) (Claim reciting thickness of a protective layer as falling within a range of "50 to 100 Angstroms" considered prima facie obvious in view of prior art reference teaching that "for suitable protection, the thickness of the protective layer should be not less than about 10 nm [i.e., 100 Angstroms]." The court stated that "by stating that ‘suitable protection’ is provided if the protective layer is ‘about’ 100 Angstroms thick, [the prior art reference] directly teaches the use of a thickness within [applicant’s] claimed range."). MPEP 2144.05
As to claim 31, Kouisni teaches that the ratio of the molar ratio of phenol (aromatic hydroxyl groups) / aldehyde is 1 / 1.5 to 1 / 3.0 [0062] . As some embodiments of Kouisni comprise phenol and lignin this ratio was taken as to include all aldehyde reactive sites / aldehyde was 1 / 1.5 to 1 / 3.0. This encompasses both reaction ratios of claim 31. The viscosity of the final product for plywood applications is 250 – 3000 cPs or higher [0060]. The lignin comprises aromatic ether groups and ortho reactive carbon atoms. See paragraph 12 supra. The lignin is derived from kraft softwood lignin [0080]. The pH of Example 4 is 10.2. Kouisni is silent as to the solids content of 20 – 25 wt. %. Kouisni teaches a solids content of approximately 50.6 wt. %.
However, it would have been obvious to one of ordinary skill to dilute the adhesive by the addition of more water to achieve the application viscosity desired.
Allowable Subject Matter
Claims 11 – 12, 14, 20, 22, 28 and 32 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.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to PETER A. SALAMON whose telephone number is 571-270-3018. The examiner can normally be reached M-F: 9AM - 6PM.
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PAS 6/25/26
/PETER A SALAMON/Primary Examiner, Art Unit 1759
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