DETAILED ACTION
Response to Amendment
This communication responds to the Amendment filed December 22, 2025. Claims 1-34 are currently pending. Claims 1-13, 19-23 and 29-34 were withdrawn. Claims 14-18 and 24-28 are under examination.
In view of the amendment, a new ground of rejections of claims 14-18 and 24-28 under 103 are made.
This office action is made final.
Claim Analysis
Summary of Claim 14:
A modified hydrogenated petroleum resin satisfying the following (A1) to (A4):
(A1)
a bromine value of 0.1 to 10.0
(A2)
containing 0.1 to 5% by mass of silicon element in terms of silicon atom
(A3)
a weight average molecular weight of 500 to 5,000
(A4)
a molecular weight distribution (Mw/Mn) of 1.1 to 3.5.
Summary of Claim 24
A modified hydrogenated petroleum resin, which is a modified hydrogenated petroleum resin (B) obtained by subjecting a modified hydrogenated petroleum resin (A) satisfying the following (A1) to (A4) to a condensation reaction,
wherein the modified hydrogenated petroleum resin (B) satisfies the following (B1) to (B3):
(A1)
a bromine value of 0.1 to 10.0
(A2)
containing 0.1 to 5% by mass of silicon element in terms of silicon atom
(A3)
a weight average molecular weight of 500 to 5,000
(A4)
a molecular weight distribution (Mw/Mn) of 1.1 to 3.5.
(B1)
a viscosity V0.1 measured using a rheometer at 190°C with an angular velocity ω= 0.1 rad/s of 1,000 to 50,000 mPa.s
(B2)
a viscosity V100 measured using a rheometer at 190°C with an angular velocity ω= 100 rad/s of 100 to 1,000 mPa.s
(B3)
a ratio of the viscosity V0.1 to the viscosity V100 [V0. 1/V100] of 10 or more.
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.
Claims 14-18 are rejected under 35 U.S.C. 103 as being unpatentable over Martin et al. (WO 9108240 A1) in view of Son et al. (US 10280266 B2 as listed on the IDS dated 8/29/2025).
Regarding claim 14, Martin et al. teach a silane-modified cross-linkable tackifier resin and its use in adhesive compositions and to materials comprising such as resins cross-linked to each other (p.1:5-10, p.2: 16-26). Martin et al. further teach the tackifier resin which are silane modified are based on hydrogenated hydrocarbon resins, wherein the polymer backbone contain C5, C9 or C10 resins, styrene, dicyclopentadiene, piperylenes, isoprene, among others (p.3:31-37; p.4:1-7). Furthermore, Martin et al. teach the silane modification is performed by reacting the unmodified resin with an unsaturated silane ( i.e. vinyltriethoxysilane, vinyltrimethoxysilane (p.7: 26-28)); in the presence of a catalyst (i.e. peroxide initiator) at a temperature of at least 140°C (p.8:16-19), to produce a silane modified resin according to the formula I (p.5: 36-37; p.6:1-37, p.7: 1-29), thereby reading on the modified hydrogenated petroleum resin .
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wherein R is the residue of the unmodified resin,
n is an integer of at least 2,
A is a bond or a divalent linking group (i.e. alkylene);
Y is a blocking group not displaceable by hydrolysis (i.e. C1-4 alkyl groups);
m is 1,2 or 3 and X is a leaving group displaceable by hydrolysis (i.e. group ZO where Z is a C1-4 alkyl or alkoxyalkyl group).
Additionally, Martin et al. teach in the Example 1, a silane grafting of a tackifier resin is obtained by reacting “ Escorez 5380” with vinyltrimethoxysilane and dicumyl peroxide as the free radical initiator (p.19 and p.20), wherein both Escorez 5380 and Escorez 5300 are used in the Example 2-4 of the instant specification, and both are hydrogenated dicyclopentadiene resins designed to function as a tackifier for a variety of adhesive polymers (See col.4:10-11 of US 61978745 B1 and Datasheet “ Escorez 5380” and “ Escorez 5300”).
Martin et al. teach silane-modified tackifier resin containing at least two silanol or protected silanol groups per resin molecule (example 1), which crosslink by hydrolysis and condensation of silane groups in the presence of a condensation catalyst (p.6: 5-14 and p.12: 4th paragraph). It is noted that Martin et al. do not provide any teaching against using a lower silane or silicon content. Moreover, Martin et al. teach the silane-modified tackifier resins comprises between 5 to 90 % of silane and the ratio of unsaturated silane to resin used in the grafting reaction should be chosen accordingly (p.7:32-35,37 and p.8:1-3) to achieve desired properties including rate of controllability of curing, viscosity, softening point, wetting ability, adhesion (p.19: 2nd paragraph, p.1:31-33 and p.2:1-11). Thus, because the silanol groups provide the reactive sites for condensation crosslinking, the degree of silane modification of the tackifier resin will control crosslinking density and performance adhesion. Therefore, one of ordinary skill I the art before the effective filing date of the claim invention would recognize that Martin et al. teach that the content of silane (silicon atom) is considered a result effective variable that can be adjusted to reach desired properties.
Martin et al. are silent on the bromine value, content of silicon atoms, weight average molecular weight and molecular weight distribution (Mw/Mn) as recited in the instant claim.
Martin et al. uses the same hydrogenated petroleum resins as disclosed by the instant specification (¶0055), similar reaction conditions involving same peroxide initiator and modifying the resin with the same silane compound as the present application. Therefore, one of ordinary skill in the art at the time of invention was made, would have expected that the modified hydrogenated petroleum resin properties of Martin et al. would be the same as the claimed (i.e. bromine value of 0.1-10, weight average molecular weight of 500-5000 and molecular weight distribution of 1.1 to 3.5).
Referring to the limitation of the content of silicon atoms, Son et al. teach a curable petroleum resin containing dicyclopentadiene, C5 fraction or C9 fraction and silanes (col 1: 43-51, title), wherein Son et al. teach a content of elemental silicon in the silane modified petroleum resin as low as 0.3 wt.%, preferably 0.8 wt.% and more preferably 2 wt.% or more would result in modified petroleum resin with excellent curability and adhesive performance (col. 1:58-63 and col.2:10-22). It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to form a silane-modified petroleum resin according to Martin et al. having a content of elemental silicon of 0.3 or more, as Son et al. demonstrates this range as being suitable for similar curable silane modified petroleum resins. This represents the use of a suitable range of elemental silicon in a similar adhesive application. "The combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results." KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 416-21 (2007). See MPEP 2141.
Regarding claim 15, 16 and 17, Martin et al. are silent on the integral ratio of aromatic hydrogen to the total of aromatic hydrogen and aliphatic hydrogen of instant claim 15. Martin et al. are further silent on the softening point as recited by instant claim 16 and the volatile component content of claim 17.
It is noted that the above arguments discussed in the rejection of claim 14 establish a rationale tending to show the modified hydrogenated petroleum resin of Martin et al. properties are expected to be the same as required by the instant claims 15-17.
Regarding claim 18, Martin et al. teach the silane modified resin is obtained by reacting a tackifier resin with an unsaturated silane of formula II in presence of a peroxide catalyst,
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where n,m, X and Y as defined above and A’ is linking group, where the alkoxysilyl group is bonded to the main chain of hydrogenated petroleum resin as taught by the formula below (p.6:35; p.7: 1-11) where R, is the residue of the unmodified resin, as required by the instant claim.
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Regarding claims 24-27, Martin et al. teach a silane modified hydrogenated petroleum resin as discussed in the rejection of claim 14. Martin et al. further teach the silane modified hydrogenated petroleum resin functions as a cross-linking agent, which occurs when the silane groups are hydrolyzed enabling it to engage in a catalyzed silanol condensation (crosslinking reaction) with other silanol groups (p.6:5-10 and p.9 23-30), which implies the alkoxy groups (i.e. methoxy) on the silane is subjected to hydrolysis, converting into free silanol groups (-Si-OH) that can participate in condensation reactions, resulting to cross-linking through Si-O-Si bond formation (see formulas below, p.9-10), thereby reading on the modified hydrogenated petroleum resin B, which is obtained by subjecting a modified hydrogenated petroleum resin (A) to a condensation reaction.
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Martin et al. are silent on the conditions (A1) to (A4) and the conditions (B1) to (B3).
Martin et al. are subjecting similar petroleum resins as disclosed by the instant specification (¶0055), similar reaction conditions involving same peroxide initiator and modifying the resin with the same silane compound as the present application. Furthermore, Martin et al. are subjecting the silane modified resins to a condensation reaction in presence of water as disclosed by the instant specification (¶0118). Therefore, one of ordinary skill in the art at the time of invention was made, would have expected that the properties of the modified hydrogenated petroleum resin A and the modified hydrogenated petroleum resin B of Martin et al. would be the same as the claimed properties (A1)-(A4) and (B1)-(B3). The limitation of the modified hydrogenated petroleum resin (A) has content of silicon element of 0.1 to 5% (A2 is discussed in the rejection of claim 14.
Regarding claims 25-27, Martin et al. are silent on the integral ratio of aromatic hydrogen to the total of aromatic hydrogen and aliphatic hydrogen of instant claim 25. Martin et al. are further silent on the softening point as recited by instant claim 26 and the volatile component content of claim 27.
It is noted that the above arguments discussed in the rejection of claim 24 establish a rationale tending to show the modified hydrogenated petroleum resin of Martin et al. properties are expected to be the same as required by the instant claims 25-27.
Regarding claim 28, The limitation of the modified hydrogenated petroleum resin (A) has an alkoxysilyl group that is bonded to a main chain of a hydrogenated petroleum resin via a bonding portion is discussed in the rejection of claim 18.
Response to Arguments
Applicant' s arguments, see p. 10-13, filed 12/22/2025, with respect to the rejection of instant claims under 103 over Martin et al. have been fully considered but they are not persuasive. However, upon further consideration, and in light of the amendment, a new ground of rejection is made under 103 over Martin et al. in view of Son et al.
Regarding the rejection over Martin et al., Applicant states that “the silicon element concentration of the silane-modified tackifier resin disclosed in Example 1 of Martin is 6.5 mass% and the present claims are distinguished as they recite a respective mass ratio of 0.1-5% by mas of silicon element in terms of silicon atom. Martin is characterized by containing silanol groups in a 1:2 ratio relative to the unmodified resin. A person skilled in the art referring to Example 1 of Martin would be expected to maintain a 1:2 ratio of silanol groups to protected silanol groups relative to the unmodified resin.”. In response, attention is drawn to the rejection as set forth above. Examiner acknowledges that Martin teaches a 1:2 ratio of silanol groups relative to unmodified resin. However, these are just preferred embodiments and Martin et al. do not provide any teaching against using a lower silane or silicon content, nor does it disclose a negative limitation on the content of silicon present in the modified resin would affect the properties of the adhesive. As such, without showing unexpected results, the claimed content of silicon element in terms of silicon atom cannot be considered critical. All the disclosures in a reference must be evaluated for what they fairly teach one of ordinary skill in the art even though the art teachings relied upon are phrased in terms of a non-preferred embodiment or even as being unsatisfactory for the intended purpose, In re Boe, 148 USPQ 507 (CCPA 1966); In re Smith, 65 USPQ 167 (CCPA 1945); In re Nehrenberg, 126 USPQ 383 (CCPA 1960); In re Watanabe, 137 USPQ 350 (CCPA 1963).For these reasons Applicant’s arguments are not persuasive.
Conclusion
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 OLGA L. DONAHUE whose telephone number is (571)270-1152. The examiner can normally be reached M-F 8:00-5:00.
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/OLGA LUCIA DONAHUE/Examiner, Art Unit 1763
/CATHERINE S BRANCH/Primary Examiner, Art Unit 1763