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 .
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.
Claims 1-20 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.
Regarding claims 1, 3 and 8, the phrase “divinylarene-like” renders the claim indefinite because it does not clearly define what “like” is intended to convey. Please refer to MPEP 2173.05 (b). Please amend “divinylarene-like” to simply “divinylarene”.
Claims 2, 4-7 and 9-20 are rejected for being dependent upon a previously rejected claim.
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, 14 and 18 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Farrar et al (US 3,652,516).
Regarding claim 1, Farrar teaches a method of manufacturing conjugated diene-based polymers comprising:
Step a) reacting a divinylarene-like compound such as 1,4-diisopropenylbenzene with an organic alkali metal such as S-BuLi to obtain an initiator wherein the molar ratio of the divinylarene-like compound to the organic alkali metal is a ratio of 1.4 (Example 1, Run B).
Step b) polymerizing a diene monomer such a butadiene to obtain the conjugated diene-based polymers (Example 1, Run B).
Regarding claim 14, Farrar teaches a conjugated diene-based polymer obtained by the manufacturing method of claim 1 (Example 1, Run B).
Regarding claim 18, Farrar teaches a rubber made from the conjugated diene-based polymer according to claim 14 (Example 1 and col. 4, lines 70-75).
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) 1-2, 6-7, 9, 11-15 and 17-20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Chen et al (US 2019/0106511) in view of Farrar et al (US 3,652,516).
Regarding claims 1-2, Chen teaches a method of manufacturing conjugated diene-based polymers comprising: reacting sec-butyllithium with diisopropenylbenzene ([0049]) and then polymerizing a conjugated diene monomer to obtain the conjugated diene polymers ([0047]-[0048]).
However, Chen fails to teach that the diisopropenylbenzene is in the 1,3 structure and Chen also fails to teach the ratio between the diisopropenylbenzene and the sec-butyllithium.
Farrar teaches a method for the polymerization of conjugated dienes (Title) which uses a multifunctional polymerization initiator made from 1,3-diisopropenylbenzene (col. 2, lines 30-35) and sec-butyl lithium (col. 2, lines 50-60). The ratio of the diisopropenylbenzene to the sec-butyl lithium ranges from 0.1:1 to 4:1 (col. 2, lines 65-72).
It would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to have the diisopropenylbenzene and sec-butyl lithium of Chen have the ratio and the 1,3 structure as taught by Farrar. One would have been motivated to do so in order to receive the benefit of using a stable, hydrocarbon soluble initiator for polymerization reaction (Farrar, col. 1, lines 45-55).
Regarding claim 6-7, Chen teaches that the polymerization step (b) can comprise a cyclic ether such as tetrahydrofuran and/or a diether compound such as ethylene glycol diethyl ether ([0050])
Regarding claim 9, Chen teaches that there is a third step in which a silicon containing modifier is added with the following structure:
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(Abstract).
Regarding claims 11-13, Chen teaches that the molar ratio of the modifier to the conjugated diene rubber containing alkali metal ions is 0.01, 1.0 and 5.0 ([0059]). Given these amounts, it would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to modify the molar ratio of the modifier to the effective alkali metal ion to range between approximately 0.01 to 5. It would have been obvious to a person having ordinary skill in the art at the time of the invention to have optimized the ratio of the modifier to the alkali metal ion and the motivation to so would have been, as Chen suggests, to adjust the degree of modification of the polymer.
Regarding claims 14-15, 17-18 and 20, Chen teaches a diene-based polymer obtained by the manufacturing method according to claims 1, 10 and 11 respectively ([0073]) and then can be made into a rubber for use in a tire ([0073]).
Regarding claim 19, Chen teaches that the rubber can further contain a vulcanizing accelerator ([0072]), stearic acid ([0069]), silicon dioxide ([0069]) etc.
Claim(s) 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Chen et al (US 2019/0106511) in view of Farrar et al (US 3,652,516) and Willis et al (US 5,002,676).
The discussion regarding Chen and Farrar in paragraph 5 above is incorporated here by reference.
Regarding claim 8, Chen fails to teach that a cyclic ether compound is added to the divinylarene-like compound before adding the organic alkali metal.
Willis teaches a process for making a difunctional lithium initiator in which the diisopropenylbenzene compound is mixed with tetrahydrofuran (a cyclic ether) prior to adding to the lithium compound (Illustrative Embodiment III).
It would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to have the cyclic ether of Willis be added to the divinylarene-like compound prior to adding to the organic alkali metal of Chen. One would have been motivated to do so in order to receive the expected benefit of using a standard solvent system for the formation of a difunctional initiator. KSR v. Teleflex, 550 U.S. _, 82 USPQ2d 1385 (2007).
Claim(s) 9-10 and 16 is/are rejected under 35 U.S.C. 103 as being unpatentable over Chen et al (US 2019/0106511) in view of Farrar et al (US 3,652,516) and Ito (JP 2011 144264, please refer to machine translation for mapping).
The discussion regarding Chen and Farrar in paragraph 5 above is incorporated here by reference.
Regarding claims 9-10 and 16, Chen teaches that additives can be added to the conjugated diene-polymer composition ([0069]).
However, it fails to teach the addition of a silicon-containing modifier such as 3-(trimethoxysilyl)-N,N-dimethylpropan-1-amine.
Ito teaches a rubber composition (Abstract) which incorporate this modifier:
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(Abstract) which is -(trimethoxysilyl)-N,N-dimethylpropan-1-amine when R1, R2 and R3 are methoxy groups (page 3), n is 3 (page 3) and R4 and R5 can be methyl groups (page 2).
It would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to have the method of Chen include the step of adding the silane compound of Ito. One would have been motivated to do so in order to receive the expected benefit of improving rolling resistance, rubber strength and processability (Ito, page 2).
Claim(s) 1 and 3 is/are rejected under 35 U.S.C. 103 as being unpatentable over Strecker (US 3,862,251).
Regarding claim 1, Strecker teaches a method for manufacturing conjugated diene-based polymers (col. 4, lines 1-15) comprising: step a) reaction an organic alkali metal (col. 2, lines 55-65) with m-divinyl benzene (col. 2, lines 20-25). The ratio of the divinylbenzene to the alkali metal compound ranges from 1 to 2 (col. 2, lines 35-40). Following step a), step b) is polymerizing a conjugated diene monomer to obtain the conjugated diene-based polymer (col. 2, lines 60-67).
Strecker fails to specifically exemplify the exact recited method with the recited ratio of the alkali metal component and the divinyl arene compound. However, Strecker discloses each of the components of the method, including the recited ratio, and teaches that they are all suitable for use in the manufacturing of a conjugated diene-based polymer. It is within the ordinary level of skill in the art to make any of the polymers suggested by a reference elucidated by the methods recited in the body of the prior art reference. Therefore, a person of ordinary skill would have been motivated to prepare any of the polymers suggested by Strecker, including the claimed diene-based polymers. In view of this, it would have been obvious to a person of ordinary skill in the art at the time of the present invention to use the teachings of Strecker to arrive at the presently claimed invention. It would have been nothing more using known process in a typical manner to achieve predictable results. KSR v. Teleflex, 550 U.S. _, 82 USPQ2d 1385 (2007).
Regarding claim 3, Strecker teaches that the divinylbenzene is added dropwise to the alkyl lithium metal (one drop every 5 second) (col, 2, lines 30-35) and hence, part of the divinylarene-like compound is reacted with the organic alkali metal for a first period of time and then the remaining part of the divinylarene-like compound is then added and allowed to react for a second period of time.
Claim(s) 4 is/are rejected under 35 U.S.C. 103 as being unpatentable over Strecker (US 3,862,251) with evidence provided by Chevron Phillips (cyclohexane, 2019) and Chemical Book (1,3 Divinylbenzene, 2023)
The discussion regarding Streaker in paragraph 8 above is incorporated here by reference.
Regarding claim 4, Strecker teaches that three mL of m-divinylbenzene is added to 100 mL of cyclohexane (Example 1). According to Chemical Book, the density of m-divinylbenzene is 0.925 g/mL and according to Chevron Phillips, the density of cyclohexane is 0.8 g/mL. Therefore, the weight of the m-divinylbenzene is 2.775 g and the weight of the cyclohexane is 80. Therefore, the concentration of the m-divinylbenzene in the cyclohexane can be calculated to be 2.775/80 = 3.4 % wt.
Claim(s) 5 is/are rejected under 35 U.S.C. 103 as being unpatentable over Strecker (US 3,862,251) in view of Van Der Steen et al (US 5,750,055)
The discussion regarding Streaker in paragraph 8 above is incorporated here by reference.
Regarding claim 5, Strecker teaches that the addition of the divinyl benzene to the alkyl lithium compound is performed at temperatures of -20 to about 20 C (col. 2, lines 25-35).
Strecker teaches that higher temperatures can be utilized (col. 2, lines 30-35), however, fails to teach the temperature of 55-60 C.
Van Der Steen teaches a reaction of an organolithium with a diisopropenylbenzene at temperatures of -20 to 60 C (Abstract).
It would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to have the reaction of Strecker be at the elevated temperature as noted by Van Der Steen. One would have been motivated to do so in order to adjust the kinetics of the reaction within the bounds of appropriate temperatures of the reaction of an organic alkali metal and a divinylarene-like compound.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DORIS L LEE whose telephone number is (571)270-3872. The examiner can normally be reached M-F 8 am - 5 pm.
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DORIS L. LEE
Primary Examiner
Art Unit 1764
/DORIS L LEE/Primary Examiner, Art Unit 1764