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 .
Applicant’s amendment dated 26 May 2026 is acknowledged. Claims 1, 5, and 7-17 as amended are pending.
Claim Rejections - 35 USC § 103
Claims 1, 5, 7-9, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over JP 2004-083842 A (“Yoshimune”).
As to claims 1, 7 and 9, Yoshimune teaches a curable composition having a (meth)acrylic ester compound having ethylene oxide and a 3-8C alkylene oxide groups (abstract), preferably the second being oxypropylene (para. 0014). Yoshimune teaches formula (1) which in combination with X being formula (2) (paras. 0021, 0022) provides the compound of formula (1) as recited.
While the weight average molecular weight is not recited, Yoshimune teaches that the integer n in formula (1) ranges from 2 to 3000 (para. 0022) which includes compounds having 100 or more oxyalkylene groups as required by claim 7, and compounds having a weight average molecular eight of 5000 or more. As such, the recited weight average molecular weight and chain length are obvious modifications suggested by Yoshimune.
While the second compound is not exemplified, Yoshimune teaches other water soluble polymerizable monomers may be used, including acryloylmorpholine (para. 0025), which meets recited Formula (2) where R23 is hydrogen, R21 and R22 are monovalent organic groups which are bonded to one another to form a ring as required by claims 1 and 9. As such, given that this is a preferred additional monomer, the use of the recited second monomer is an obvious modification suggested by Yoshimune.
As to claim 5, Yoshimune teaches that the oxyalkylene chain may be a random arrangement of oxyethylene and oxypropylene (para. 0014).
As to claim 7, while the viscosity below the threshold is not recited, Yoshimune teaches the same type of di(meth)acrylate compound with the same recited length of oxyalkylene chain; as such, it is reasonable to presume the use of such an oligomer would have viscosity in the recited range.
As to claim 16, Yoshimune teaches a cured product of the composition (para. 0011).
Claim(s) 1, 7, 9, 11, and 15-17 are rejected under 35 U.S.C. 103 as being unpatentable over JP 2013-018842 A (“Motofuji”) in view of JP 2018-172565 A (“Watanabe”).
As to claims 1 and 9, Motofuji teaches a composition comprising a bifunctional (meth)acrylate having a polyoxyalkylene chain (abstract), which meets the general structure of recited Formula (1)and acryloylmorpholine, which meets Formula 2 where R23 is hydrogen, and R21 and R22 are bonded to each other to form a ring as required by claims 1 and 9 (para. 0198).
While not exemplified, Motofuji teaches that the number average molecular weight ranges from preferably 400 to 10000 (para. 0011), which includes weight average molecular weight in the recited range, since weight average molecular weight is always equal to or greater than number average molecular weight. Further, while Motofuji does not exemplify oxyethylene and oxypropylene groups, it is known that polyoxyalkylene chains in curable acrylates may be combinations of oxyethylene and oxypropylene groups, see Watanabe, para. 0038), and thus the use of at least one oxypropylene unit is obvious as known in the art of curable compositions.
As to claim 7, while the recited number of oxyalkylene groups is not exemplified, Motofuji teaches the bifunctional polyoxyalkylene diacrylate may have number average molecular weight ranging from preferably 400 to 10000 (para. 0011), which range includes compounds having 100 or more oxyethylene, oxypropylene, oxybutylene groups, and as such, bifunctional polyoxyalkylene (meth)acrylates having the recited number of groups is an obvious modification implicitly suggested by Motofuji.
As to claims 11 and 15, while not exemplified, Motofuji teaches the composition may include pigments, including graphite, and alumina (para. 0078), which are thermally conductive as required by claims 11 and 15, and as such, the use of pigment (filler) that is thermally conductive is an obvious modification suggested by Motofuji.
As to claim 16, Motofuji teaches cured product of the composition (para. 0126).
As to claim 17, while not exemplified, Motofuji teaches the cured coating can be applied to flat panel displays for electronics, and electronic components (paras. 0001, 0002), all of which generate heat in operation; as such, an article with a heat source and cured product in contact is an obvious modification suggested by Motofuji.
Claims 12-14 are rejected under 35 U.S.C. 103 as being unpatentable over JP 2013-018842 A (“Motofuji”) in view of JP 2018-172565 A (“Watanabe”) as applied to claim 11, further in view of JP 2004-231913 A (“Terakawa”).
A partial machine translation of JP 2004-231913 A is enclosed.
As to claims 12-14, Motofuji teaches the use of fillers such as alumina, and the use of adhesion (coupling) agents (para. 0091), but does not discuss chemical adsorption of a coupling agent to thermally conductive filler. Terakawa teaches photopolymerizable compositions, including inorganic filler, including heat conductive fillers such as alumina, (para. 0049), and teaches that fillers are preferentially hydrophobized with a surface treatment agent such as methacryloxypropyltrimethoxysilane as required by claims 13 and 14. As such, the surface modification of fillers, including heat conductive fillers, in photocurable compositions is known in the art from Terakawa.
Claim(s) 1, 5, 7, 9, 10, and 16 are rejected under 35 U.S.C. 103 as being unpatentable over JP 2018-172565 A (“Watanabe”) in view of JP 2018-172565 A (“Motofuji”).
As to claims 1 and 7, Watanabe teaches a composition comprising a compound having an alkylene oxide chain and two or more radical polymerizing groups (para. 0010). As one example, Watanabe exemplifies di(meth)acrylate of ethylene oxide adduct of bisphenol A, which meets Chemical Formula 1 with R13 being a divalent group having a polyoxyalkylene chain, specifically oxyethylene as required by claim 2, and R11 and R12 being hydrogen or methyl.
While not exemplified, Watanabe teaches the alkylene oxide chain may include oxypropylene (propylene oxide) units (para. 0038), and thus the same is an obvious modification suggested by Watanabe.
Watanabe teaches greater than 10 (para. 0038), but does not teach the recited weight average molecular weight; however, Motofuji teaches number average (lower than weight average) molecular weight ranges from 400 to 10000 are desirable for heat resistance and adhesion (para. 0011), and as such, the use of polyoxyalkylene di(meth)acrylates of the recited range are an obvious modification suggested by Motofuji; furthermore, average molecular weight in the range of 5000 or greater suggests chains having 100 or more oxyalkylene groups, given the weight of oxyethylene or oxypropylene groups.
Though the recited compound of Chemical Formula 2 is not exemplified, Watanabe teaches the use of a monomer (A), which may include dimethyl (meth)acrylamide, (meth)acryloyl morpholine, isopropyl (meth)acrylamide and others (para. 0024), which meet Chemical Formula 2 where R23 is hydrogen or methyl, and R1 and R22 are hydrogen, monovalent organic group, or bound to form a ring.
As such, the use of a compound of Chemical Formula 2 in the composition of Watanabe is an obvious modification suggested by Watanabe.
As to claim 5, while not exemplified, Watanabe teaches the use of ethylene oxide (oxyethylene) and propylene oxide (oxypropylene) as monomers, and teaches copolymers, including random copolymers (para. 0038), and thus the recited species are an obvious modification suggested by Watanabe.
As to claim 9, Watanabe teaches the composition may include (meth)acryloyl morpholine (para. 0024), which meets Formula (2) where R21 and R22 form a ring.
As to claim 10, Watanabe teaches the composition includes a poly (meth)acrylate with one or more radical polymerizing functional groups (abstract). Specifically, Watanabe prefers polyacrylates with acryloyl groups at both ends of the molecule (para. 0060), which meets Chemical Formula 2 where R21 and R31 are hydrogen, and R33 is a divalent group having a polyacrylate chain.
As to claim 16, Watanabe teaches curing the composition (para. 0055).
Response to Arguments
Applicant’s arguments with respect to claim(s) 1, 5, and7-17 have been considered but are moot because the new ground of rejection does not rely on any combination of references applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
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.
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/KREGG T BROOKS/Primary Examiner, Art Unit 1764
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