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 Analysis
Summary of Claim 1:
A process for the synthesis of a 1,4-cis polydiene comprising the steps of:
polymerizing at least a 1,3-butadiene monomer in the presence of a lanthanide catalyst system and a bis-diene additive.
Claim Objections
Claims 2-3 are objected to because of the following informalities:
Claims 2-3 recite “the bis-diene”. Applicants are advised to rephrase to “the bis-diene additive” to be consistent with the bis-diene additive of Claim 1.
Appropriate corrections are required.
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 5 and 15 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 pre-AIA the applicant regards as the invention.
Claim 5, Line 8 recites “the molar ratio of isoprene monomer to neodymium”. There is insufficient antecedent basis for this limitation in the claim. In this case, it is unclear to what the isoprene monomer and neodymium are referring. For example, it is unclear if the neodymium is referring to the neodymium in the neodymium carboxylate, the neodymium-aluminum catalyst component, or the neodymium catalyst system.
Claim 15 recites “bridged by ethylene oxides or propylene oxides group” (emphasis added). However, the pluralized “ethylene oxides” and “propylene oxides” implies there are multiple ethylene oxides or propylene oxides in the bridge which directly contradicts the singular “group”. It is unclear if the bridge comprises more than one ethylene oxide or propylene oxide group. For the purposes of examination, the bis-diene additive will be interpreted to be bridged by at least one ethylene oxide or propylene oxide group.
Accordingly, the scope of Claims 5 and 15 is deemed indefinite.
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.
Claims 1, 3-4, 6-7, 9 and 12 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Steinhauser et al. (US 2002/0035226A1; hereafter as “Steinhauser”).
Regarding Claims 1, 4, and 6, Steinhauser teaches a method of polymerization of cis-1,4 polybutadiene [Claim 1; Examples 2-6; 0004], corresponding to the process for the synthesis of a 1,4-cis polydiene of Claim 1, and 1,4-cis polydiene of Claim 6, comprising:
copolymerization of 1,3-butadiene [Examples 2-6], corresponding to the step of polymerizing at least a 1,3-butadiene monomer of Claim 1;
polymerization of butadiene with catalyst comprising neodymium versatate [Examples 2-6; ¶ 0021-0035], corresponding to polymerizing in the presence of a lanthanide catalyst system of Claim 1, and corresponding to the neodymium catalyst of Claim 4; and
mixing dimethyl-di-2,4-pentadienyl-(E,E)-silane (shown below), corresponding to the bis-diene additive of Claim 1, with the catalyst [Examples 3, 5-6; Claim 4].
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.
Regarding Claim 3, Steinhauser further teaches:
dimethyl-di-2,4-pentadienyl-(E,E)-silane [Examples 3, 5-6], corresponding to the Diene-(CH2)n-X-CH2)m-Diene of Claim 3;
wherein the silane thereby reads on wherein X is a silane of Claim 3;
wherein the di-pentadienyl groups read on the diene groups and m+n = 10, which corresponds with m+n is greater than 2 of Claim 3.
Regarding Claims 7, 9 and 12, Steinhauser further teaches:
a Mooney viscosity (ML 1+4 at 100°C) of 80 MU [Example 6], which is encompassed by a Mooney viscosity (ML1+4 at 100C) from about 40 to about 90 of Claim 7;
a tire tread comprising the polybutadiene [Claims 17-18; ¶ 0071-0072], corresponding to the tire having a tread or carcass compound comprising the at least 1,4-cis polydiene of Claim 9; and
the silane group in the dimethyl-di-2,4-pentadienyl-(E,E)-silane [Examples 3, 5-6], corresponding to the silane of Claim 12.
In light of the above, the cited claims are rendered anticipated by Steinhauser.
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.
Claims 2, 5, and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Steinhauser et al. (US 2002/0035226A1; hereafter as “Steinhauser”).
Steinhauser teaches the 1,4-cis polydiene, 1,3-butadiene, lanthanide catalyst, and bis-diene additive as set forth above and incorporated herein by reference.
Regarding Claim 2, Steinhauser teaches dienes [¶ 0007-0014].
However, Steinhauser does not explicitly mention the claimed particular bis-diene additives of the formula with sufficient specificity to constitute anticipation within the meaning of 35 U.S.C. 102.
Nevertheless, Steinhauser does teach dienes selected from, among other things, including those having the general formula [¶ 0007-0014]
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wherein R in each case independent of one another, and is monounsaturated C1-C20-alkyl group, or -H [¶ 0009], corresponding to the terminal dienes and -CH2 groups, respectively, of Claim 2; and
wherein X is O or S [¶ 0010], thereby reading on Y is an oxygen or sulfur of Claim 2.
Moreover, although Steinhauser exemplifies multiple X groups and R groups other than the claimed bis-diene additives, this indicates that the other structures listed are equally suitable as a bis-diene for the purposes of synthesizing a 1,4-cis polydiene, see MPEP §2123 [R-5]. Thus, it would have been obvious to one of ordinary skill in the art to select the claimed particular bis-diene additives of the formula from those listed in Steinhauser, with a reasonable expectation of successfully using the same for producing the claimed 1,4-cis polydiene and obtaining desirable Mooney viscosity values (ML 1+4 at 100°C) of 40-80 MU [¶ 0078, 0080, 0085, 0095] which are similar to the Mooney viscosity values of the instantly claimed invention [instant Specification; ¶ 0056].
Regarding Claim 5, Steinhauser further teaches preforming of catalysts, such as neodymium versatate, for polymerization of dienes [Examples 4-6; ¶ 0021-0054], corresponding to preparing the lanthanide catalyst system of Claim 5, comprising:
mixing and stirring neodymium versatate and diisobutylaluminum hydride [Examples 4-6; ¶ 0023, 0026], corresponding to reacting the neodymium carboxylate with the organoaluminium compound of Claim 5, and thereby reading on the dialkylaluminum hydride compound of Claim 5;
then further adding ethylaluminum sesquichloride [Examples 4-6], which corresponds to subsequently reacting the neodymium-aluminum catalyst component with an alkyl aluminum chloride of Claim 5;
then mixing 1,3-butadiene [Examples 2-6], which corresponds to the conjugated diolefin monomer of Claim 5;
Stirring the mixture at 50°C and then cooling to 5°C [Example 5], which corresponds to wherein the neodymium catalyst is prepared at a temperature that is within the range of about −60° C. to about 150° C of Claim 5;
Wherein the mixture comprises 12 mmol of isoprene and 3 mmol of neodymium versatate [Example 5], which is equivalent to a ratio of 4/1, which will be interpreted to be encompassed by the molar ratio of isoprene monomer to neodymium from about 5/1 to about 500/1 of Claim 5.
However, Steinhauser does not explicitly teach the addition of the conjugated diolefin monomer in step (1) before the addition of the alkyl aluminum chloride in step (2), and the molar ratio of isoprene monomer to neodymium from about 5/1 to about 500/1 of Claim 5 as claimed .
Nevertheless, Steinhauser teaches the same steps of polymerizing a polydiene in the presence of 1,3-butadiene monomer, lanthanide catalyst, and bis-diene additive, and preparation of the lanthanide catalyst at the same temperature as the instantly claimed invention. Selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results. Therefore, it would have been obvious to one of ordinary skill to select any order for the steps, including those claimed, for the purposes of preparing the 1,4-cis polydiene. See MPEP section 2144.04.IV.C.
Regarding Claim 8, Steinhauser further teaches a molar ratio of 1,4-butadiene to bis-diene of 1:10 to 1:20,000 [¶ 0019], which overlaps the mole ratio of monomer to bis-diene range is from 4200 to 29000 of Claim 8.
However, Steinhauser does not explicitly teach the specific mole ratio of monomer to bis-diene range is from 4200 to 29000 of Claim 8.
Nevertheless, one of ordinary skill in the art at the time the invention was made would have considered the invention to have been obvious because the range taught by Steinhauser for the molar ratio of 1,4-butadiene to bis-diene (1:10 to 1:20,000) overlaps the instantly claimed range (4200-29000) and is therefore considered to establish a prima facie case of obviousness. It would have been obvious to one of ordinary skill in the art to select any portion of the disclosed ranges including the instantly claimed ranges from the ranges disclosed in the prior art reference, MPEP 2144.05.
Claims 10-11, 14 are rejected under 35 U.S.C. 103 as being unpatentable over Steinhauser et al. (US 2002/0035226A1; hereafter as “Steinhauser”) in view of Ono et al. (US 2019/0160870 A1; as cited in the IDS submitted on 12/17/2025; hereafter as “Ono”).
Steinhauser teaches the 1,4-cis polydiene, 1,3-butadiene, lanthanide catalyst, and bis-diene additive as set forth above and incorporated herein by reference.
However, Steinhauser does not explicitly teach wherein the bis-diene additive is bridged by an aliphatic hydrocarbon group, a cycloaliphatic hydrocarbon, aliphatic perfluoro carbon, or an aromatic hydrocarbon or a combination thereof of Claim 10, wherein the bis-diene additive is bridged by sulfur, a chalcogen or a combination thereof of Claim 11, and wherein the bis-diene additive is bridged by epoxide of Claim 14.
Nevertheless, Ono teaches a rubber composition for tire treads, comprising 1,3-butadiene [Claims 1, 5-6¶ 0154] and further comprising farnesene [Claim 4; ¶ 0049, 0158], wherein the fourth carbon atom (–CH2–) reads on the aliphatic hydrocarbon group of Claim 10.
Ono offers the motivation that farnesene can be suitably used as a softening agent for a tire since it is liquid at a normal temperature [¶ 0045].
Thus, it would have been obvious to one of ordinary skill in the art to add the claimed bis-diene additive with the aliphatic hydrocarbon taught by Ono to the cis-1,4 polybutadiene of Steinhauser with a reasonable expectation of successfully obtaining improved tire properties.
Regarding Claims 11 and 14, Ono further teaches a butadiene rubber wherein the main chain is modified with:
oxygen [¶ 0030], thereby reading on the chalogen of Claim 11; and
an epoxy group [¶ 0030-0031, 0037], which corresponds with the epoxide of Claim 14.
The representative examples of bis-diene bridging groups provided in the instant Specification [¶ 0049-0054], show that the bridging groups are a part of the main chain between the butadiene groups. Thus, for the purposes of examination the oxygen taught by Ono [¶ 0030], will be interpreted to read on wherein the bis-diene additive is bridged by chalogen of Claim 11; and the epoxy group taught by Ono [¶ 0030-0031, 0037] will be interpreted to correspond with wherein the bis-diene additive is bridged by epoxide of Claim 14.
Ono offers the motivation that the rubber composition has good on-ice performance [¶ 0021] and the epoxy group modifications on the butadiene rubber are preferred because the effect of enhancing fuel efficiency is high [¶ 0031].
Thus, it would have been obvious to one of ordinary skill in the art to add the claimed oxygen and epoxy groups taught by Ono to the cis-1,4 polybutadiene of Steinhauser with a reasonable expectation of successfully obtaining improved tire properties.
Claim 13 is rejected under 35 U.S.C. 103 as being unpatentable over Steinhauser et al. (US 2002/0035226A1; hereafter as “Steinhauser”) in view of Runzi et al. (EP 3366709 A1; hereafter as “Runzi”).
Steinhauser teaches the 1,4-cis polydiene, 1,3-butadiene, lanthanide catalyst, and bis-diene additive as set forth above and incorporated herein by reference.
However, Steinhauser does not explicitly teach wherein the bis-diene additive is bridged by phosphine or phosphine oxides of Claim 13.
Nevertheless, Runiz teaches a process for forming diene-polymers containing in-chain phosphine for the production of tires, comprising a polymer of formula A2 [Abstract; Claim 15] (shown below), wherein n = 1, R1 and R3 are each H, and X is 1,3-hexadienyl [Claim 15], which corresponds with wherein the bis-diene additive is bridged by phosphine of Claim 13.
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Formula A2
Runiz offers the motivation that in-chain phosphine containing diene-polymers demonstrate improved dynamic performance properties [¶ 0009].
Thus, it would have been obvious to one of ordinary skill in the art to add the claimed phosphine bridge taught by Runiz to the cis-1,4 polybutadiene of Steinhauser with a reasonable expectation of successfully obtaining improved tire properties.
Claim 15 is rejected under 35 U.S.C. 103 as being unpatentable over Steinhauser et al. (US 2002/0035226A1; hereafter as “Steinhauser”) in view of Choe et al. (KR 2019/0111275A; English translation incorporated herein; hereafter as “Choe”).
Steinhauser teaches the 1,4-cis polydiene, 1,3-butadiene, lanthanide catalyst, and bis-diene additive as set forth above and incorporated herein by reference.
However, Steinhauser does not explicitly teach wherein the bis-diene additive is bridged by ethylene oxides or propylene oxides group of Claim 15.
Nevertheless, Choe teaches conjugated diene compounds as a rubber material for tires [¶ 0003, 0011], comprising a diene compound with General Formula 1-1b (shown below):
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[General Formula 1-1b],
which corresponds to the bis-diene additive bridged by an ethylene oxide group of Claim 15.
Choe offers the motivation that conjugated diene-based polymers having low rolling resistance, excellent wear resistance and tensile characteristics, and adjustment stability represented by wet road resistance as a rubber material for tires [¶ 0003].
Thus, it would have been obvious to one of ordinary skill in the art to add the claimed ethylene oxide bridge taught by Choe to the cis-1,4 polybutadiene of Steinhauser with a reasonable expectation of successfully obtaining improved tire properties.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DORIS LING whose telephone number is (571)270-3961. The examiner can normally be reached Monday-Friday, 8:30am-5:00pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, ARRIE LANEE REUTHER can be reached on (571)270-7026. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/DORIS LING/Examiner, Art Unit 1764
/HANNAH J PAK/Primary Examiner, Art Unit 1764
