DETAILED ACTION
This office action follows a reply filed on August 10, 2026. Claims 1, 2 and 13 have been amended. Claims 1-13 are currently pending and under examination.
The texts of those sections of Title 35 U.S. Code are not included in this section and can be found in a prior Office action.
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 § 103
Claims 1-13 are rejected under 35 U.S.C. 103 as being unpatentable over Sarbach (US 2,360,896) in view of Reid (US 1,984,284) and further in view of KR 2021014597, as evidenced by Magne (Plasticizers from Aconitic and Tricarballyic Acids, Industrial and Chemical Enginering Chemistry, 45, (7), 1953, pp. 1546-1547).
Sarbach teaches softeners, also known in the art as plasticizers, which are esters of tricarboxylic acids, specifically listed to include tricarballylic acid, where all three carboxyl groups of the acids are esterified with a monohydric alcohol having 2-8 carbon atoms, teaching the monohydric alcohol to include aliphatic or aromatic monohydric alcohols, where hexanol is a known C6 monohydric alcohol. Sarbach teaches that mixed esters are suitable as well (p. 1). Hexyl tricarballyate is a known plasticizer, as evidenced by Magne.
Sarbach broadly suggests a mixed ester of an alkyl/aryl tricarballylate, but does not specifically teach a blend of C6 and benzyl based esters, as claimed.
Reid teaches aryl alkyl polycarboxylic acids as plasticizers, teaching that by esterifying the polycarboxylic acids with an aryl alcohol to neutralize one carboxyl group and an alkyl alcohol to neutralize another carboxyl group of the polycarboxylic acid, compounds are obtained that have greater temperature spans between their melting points and boiling points than when only one alcohol is used, teaching that these mixed esters have low volatility and low freezing range such that they are not easily influenced by temperature variations, preventing the esters from exuding the polymer of which is it plasticizing at high temperatures or crystallization on the surface at low temperatures (p. 1).
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was filed to have used a mixture of an alkyl alcohol, such as a C6 alkyl, and an aryl alcohol, such as benzyl alcohol, when esterifying the tricarboxylic acid of Sarbach, as Reid teaches that the use of a combination of an aliphatic alcohol and aryl alcohol provide plasticizers that can be used over a wider range of temperatures than the alkyl based plasticizers or aryl based plasticizers, alone.
Sarbach nor Reid teach using an isomeric mixture of the aliphatic alcohol, or C6 alcohol used in the esterification, as claimed.
KR ‘597 teaches a tricarboxylic acid based plasticizer derived from an isomer mixture of hexyl alcohol having a branching degree of 2.0 or less, and 0.1 or more, where the isomeric mixture comprises 1-hexanol, 2-methylpentanol and 3-methylpentanol. KR ‘597 shows that the isomeric blend provides a final composition with lower migration loss and lower volatile loss, as well as increased absorption rate, compared to the non-isomeric mixtures, in addition to increased physical properties of the final plasticized composition.
Therefore, it would have been obvious to one of ordinary skill in the art at the time the invention was field to have used a combination of the isomeric hexyl alcohol mixture of KR ‘597 in combination with the benzyl alcohol, as suggested by Reid, to prepare the plasticizers of Sarbach, as Reid teaches that the combination of alkyl and aryl substituents improves the temperature range for which the plasticizers can be used, and KR ‘597 teaches that the isomeric mixture of hexyl alcohol provides reduced migration and volatility and increased absorption by the resin to which it is added.
The combination of the C6 isomeric mixture and the benzyl alcohol during esterification of tricarballylic acid would inherently result in the compounds having the claimed formulae 1-7.
While the examiner recognizes that KR ‘597 is directed to citrates, rather than the tricarballylates of Sarbach, citric acid and tricarballylic acid is structural homologue to citric acid, citrates and tricarballylates are both known types of plasticizers in the polymer art, and one of ordinary skill in the art would expect the improvements obtained from the citrates of KR ‘597 to be similar to the tricarballylates.
Sarbach in view of Reid and KR ‘597 is prima facie obvious over instant claims 1-3.
KR ‘597 teaches and claims the exact same limitations for the hexyl alcohol isomer mixture as claimed for instant claims 4-10.
As to claim, 11, Reid teaches a ratio of aliphatic to aryl such that 1 of the substituents of the triester is aromatic and two are aliphatic and a such that 2 of the substituents of the triester are aromatic and one is aliphatic, suggesting ratios of aliphatic to aromatic alcohols of 33:66 and 66:33 (p. 3).
As to claim 12, Sarbach teaches that the softeners are suitable for use in rubbers in an amount of 10-60 phr (p. 2).
Response to Arguments
Applicant's arguments have been fully considered but they are not persuasive.
Applicants argue that the prior art references, individually, do not teach the claimed combination. The examiner agrees, hence the necessity for the multiple references.
Applicants argue that the advantages reported for the citrate-based plasticizers would not carry over to the tricarballylates of Sarbach.
KR ‘597 shows that using an isomeric mixture of hexanol in place of a non-isomeric alcohol improves plasticization and tensile strength. This improvement is also shown by applicants and is therefore expected.
While the examiner agrees that applicants have shown advantageous results using the mixed plasticizer, applicants have only shown one particular isomeric mixture which requires the presence of at least three isomers, where the claimed invention only requires two isomers. Additionally, applicants have only shown the effects with a ratio of aliphatic to aromatic ratio of 90:10, 70:30 and 50:50, where the claimed invention allows for any ratio of aliphatic to aromatic ratio.
Therefore, applicants’ showing is not commensurate in scope with the claimed invention.
Additionally, US 2,802,802 teaches the following:
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Spew resistance is related to migration of the plasticizer. While the examiner agrees that citrate and tricarballylate are not functional equivalents, one of ordinary skill in the art would expect the tricarballylates to provide increased plasticization over the citrates, as suggested by US ‘802.
Allowable Subject Matter
Amending to claim 1 to include an isomeric mixture of at least 1-hexanol, 2-methylpentanol and 3-methylpentanol, where the weight ratio between the isomer mixture of hexyl alcohol to benzyl alcohol is 90:10 to 50:50 would be sufficient to place the application in condition for allowance, as these limitations are representative of the advantageous results supplied by applicants.
Conclusion
THIS ACTION IS MADE FINAL. 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 BRIEANN R JOHNSTON whose telephone number is (571)270-7344. The examiner can normally be reached Monday-Friday, 8:00 AM - 4:00 PM EST.
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/Brieann R Johnston/Primary Examiner, Art Unit 1766
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