JP6923894B2 - 接着性ポリアリールエーテルケトン樹脂材料の製造方法、及びポリアリールエーテルケトン樹脂材料と被着体との接着方法 - Google Patents
接着性ポリアリールエーテルケトン樹脂材料の製造方法、及びポリアリールエーテルケトン樹脂材料と被着体との接着方法 Download PDFInfo
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- JP6923894B2 JP6923894B2 JP2017085653A JP2017085653A JP6923894B2 JP 6923894 B2 JP6923894 B2 JP 6923894B2 JP 2017085653 A JP2017085653 A JP 2017085653A JP 2017085653 A JP2017085653 A JP 2017085653A JP 6923894 B2 JP6923894 B2 JP 6923894B2
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- adhesive
- resin material
- polymerizable monomer
- radically polymerizable
- polyaryletherketone resin
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- 239000000463 material Substances 0.000 title claims description 247
- 229920006260 polyaryletherketone Polymers 0.000 title claims description 243
- 238000000034 method Methods 0.000 title claims description 38
- 238000004519 manufacturing process Methods 0.000 title claims description 25
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- 239000003505 polymerization initiator Substances 0.000 claims description 142
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- 125000000524 functional group Chemical group 0.000 claims description 56
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- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 6
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- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 5
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- 150000003512 tertiary amines Chemical class 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 150000003682 vanadium compounds Chemical class 0.000 description 5
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 4
- VGZZAZYCLRYTNQ-UHFFFAOYSA-N 2-ethoxyethoxycarbonyloxy 2-ethoxyethyl carbonate Chemical compound CCOCCOC(=O)OOC(=O)OCCOCC VGZZAZYCLRYTNQ-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
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- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 3
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- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 3
- BLKRGXCGFRXRNQ-SNAWJCMRSA-N (z)-3-carbonoperoxoyl-4,4-dimethylpent-2-enoic acid Chemical compound OC(=O)/C=C(C(C)(C)C)\C(=O)OO BLKRGXCGFRXRNQ-SNAWJCMRSA-N 0.000 description 3
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- DPGYCJUCJYUHTM-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yloxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)CC(C)(C)C DPGYCJUCJYUHTM-UHFFFAOYSA-N 0.000 description 3
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- 125000001424 substituent group Chemical group 0.000 description 3
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- MYOQALXKVOJACM-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy pentaneperoxoate Chemical compound CCCCC(=O)OOOC(C)(C)C MYOQALXKVOJACM-UHFFFAOYSA-N 0.000 description 2
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- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 description 1
- NBFRQCOZERNGEX-UHFFFAOYSA-N n,n,3,5-tetramethylaniline Chemical group CN(C)C1=CC(C)=CC(C)=C1 NBFRQCOZERNGEX-UHFFFAOYSA-N 0.000 description 1
- CWOMTHDOJCARBY-UHFFFAOYSA-N n,n,3-trimethylaniline Chemical compound CN(C)C1=CC=CC(C)=C1 CWOMTHDOJCARBY-UHFFFAOYSA-N 0.000 description 1
- ISGXOWLMGOPVPB-UHFFFAOYSA-N n,n-dibenzylaniline Chemical compound C=1C=CC=CC=1CN(C=1C=CC=CC=1)CC1=CC=CC=C1 ISGXOWLMGOPVPB-UHFFFAOYSA-N 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
- HKJNHYJTVPWVGV-UHFFFAOYSA-N n,n-diethyl-4-methylaniline Chemical compound CCN(CC)C1=CC=C(C)C=C1 HKJNHYJTVPWVGV-UHFFFAOYSA-N 0.000 description 1
- AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- QMHNQZGXPNCMCO-UHFFFAOYSA-N n,n-dimethylhexan-1-amine Chemical compound CCCCCCN(C)C QMHNQZGXPNCMCO-UHFFFAOYSA-N 0.000 description 1
- IKZPRXHVTFNIEK-UHFFFAOYSA-N n,n-dimethylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C)C)=CC=C21 IKZPRXHVTFNIEK-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- ZKALVNREMFLWAN-UHFFFAOYSA-N n-(4-methylpentan-2-ylidene)hydroxylamine Chemical compound CC(C)CC(C)=NO ZKALVNREMFLWAN-UHFFFAOYSA-N 0.000 description 1
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 1
- UIEKYBOPAVTZKW-UHFFFAOYSA-L naphthalene-2-carboxylate;nickel(2+) Chemical compound [Ni+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 UIEKYBOPAVTZKW-UHFFFAOYSA-L 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000005502 peroxidation Methods 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- SCOAVUHOIJMIBW-UHFFFAOYSA-N phenanthrene-1,2-dione Chemical compound C1=CC=C2C(C=CC(C3=O)=O)=C3C=CC2=C1 SCOAVUHOIJMIBW-UHFFFAOYSA-N 0.000 description 1
- POZPGRADIOPGIR-UHFFFAOYSA-N phenanthrene-1,4-dione Chemical compound C1=CC2=CC=CC=C2C2=C1C(=O)C=CC2=O POZPGRADIOPGIR-UHFFFAOYSA-N 0.000 description 1
- NKGGYWQZHFAHRK-UHFFFAOYSA-N phenanthrene-3,4-dione Chemical compound C1=CC=CC2=C(C(C(=O)C=C3)=O)C3=CC=C21 NKGGYWQZHFAHRK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- XPPWLXNXHSNMKC-UHFFFAOYSA-N phenylboron Chemical compound [B]C1=CC=CC=C1 XPPWLXNXHSNMKC-UHFFFAOYSA-N 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001955 polyphenylene ether Polymers 0.000 description 1
- 229920006375 polyphtalamide Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000019396 potassium bromate Nutrition 0.000 description 1
- 229940094037 potassium bromate Drugs 0.000 description 1
- VKJKEPKFPUWCAS-UHFFFAOYSA-M potassium chlorate Chemical compound [K+].[O-]Cl(=O)=O VKJKEPKFPUWCAS-UHFFFAOYSA-M 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- HPWMVNFJSFHJIW-UHFFFAOYSA-M potassium;2,4,6-tri(propan-2-yl)benzenesulfinate Chemical compound [K+].CC(C)C1=CC(C(C)C)=C(S([O-])=O)C(C(C)C)=C1 HPWMVNFJSFHJIW-UHFFFAOYSA-M 0.000 description 1
- NLZLDWFYQXFPSZ-UHFFFAOYSA-M potassium;2,4,6-triethylbenzenesulfinate Chemical compound [K+].CCC1=CC(CC)=C(S([O-])=O)C(CC)=C1 NLZLDWFYQXFPSZ-UHFFFAOYSA-M 0.000 description 1
- SCRWQCKSJIHKKV-UHFFFAOYSA-M potassium;2,4,6-trimethylbenzenesulfinate Chemical compound [K+].CC1=CC(C)=C(S([O-])=O)C(C)=C1 SCRWQCKSJIHKKV-UHFFFAOYSA-M 0.000 description 1
- YVHWGMMGEAQQRT-UHFFFAOYSA-M potassium;4-methylbenzenesulfinate Chemical compound [K+].CC1=CC=C(S([O-])=O)C=C1 YVHWGMMGEAQQRT-UHFFFAOYSA-M 0.000 description 1
- LZSBNSVOXWMXLL-UHFFFAOYSA-M potassium;benzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=CC=C1 LZSBNSVOXWMXLL-UHFFFAOYSA-M 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 150000003326 scandium compounds Chemical class 0.000 description 1
- HUIHCQPFSRNMNM-UHFFFAOYSA-K scandium(3+);triiodide Chemical compound [Sc+3].[I-].[I-].[I-] HUIHCQPFSRNMNM-UHFFFAOYSA-K 0.000 description 1
- 238000000790 scattering method Methods 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- XKSRVJVOYWLSCI-UHFFFAOYSA-N sodium;1,3,5-trimethylbenzene Chemical compound [Na].CC1=CC(C)=CC(C)=C1 XKSRVJVOYWLSCI-UHFFFAOYSA-N 0.000 description 1
- WWYACYKHLMCNBG-UHFFFAOYSA-M sodium;2,4,6-tri(propan-2-yl)benzenesulfinate Chemical compound [Na+].CC(C)C1=CC(C(C)C)=C(S([O-])=O)C(C(C)C)=C1 WWYACYKHLMCNBG-UHFFFAOYSA-M 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- KGKNBDYZZIBZQL-UHFFFAOYSA-N tert-butyl carboxyoxy carbonate Chemical compound CC(C)(C)OC(=O)OOC(O)=O KGKNBDYZZIBZQL-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Landscapes
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Dental Preparations (AREA)
Description
本発明で使用することが出来るポリアリールエーテルケトン樹脂材料は、高強度であるなどのポリアリールエーテルケトン樹脂を使用する利点が得られる配合量のポリアリールエーテルケトン樹脂を含有しているものであり、好ましくはポリアリールエーテルケトン樹脂を20質量%以上、より好ましくは30質量%以上、さらに好ましくは50質量%以上含むものである。
本発明における接着剤は、化学重合開始剤とラジカル重合性単量体を含有し、光重合開始剤を実質的に含有しないものであり、ポリアリールエーテルケトン樹脂材料と、ラジカル重合性単量体と重合開始剤を含有する硬化性組成物からなる被着体を接着させるために、ポリアリールエーテルケトン樹脂材料の被着面に塗布されるものであり、且つ、ポリアリールエーテルケトン樹脂材料の被着面に塗布された後であり硬化性組成物と接触させる前に光照射されるものである。本発明における化学重合開始剤とラジカル重合性単量体を含有する接着剤は、被着面に塗りひろげられる液体状のものが好ましい。光重合開始剤を実質的に含まない該接着剤は、光照射によって重合硬化しない。化学重合開始剤により徐徐に重合が開始するが、接着剤は変形不能になるほどには重合硬化しない。従って、ラジカル重合性単量体と重合開始剤を含有する硬化性組成物からなる被着体を接触・圧着する際に、接着剤層を薄くする事が容易である。
メチルメタクリレート、エチルメタクリレート、イソプロピルメタクリレート、2−ヒドロキシエチルメタクリレート、テトラヒドロフルフリルメタクリレート、グリシジルメタクリレート、2−メタクリロイルオキシエチルジハイドロジェンホスフェート、2−メタクリロイルオキシエチルフェニルハイドロジェンホスフェート、6−メタクリロイルオキシヘキシルジハイドロジェンホスフェート、10−メタクリロイルオキシヘキシルジハイドロジェンホスフェート、2−メタクリロイルオキシエチル2−ブロモエチルハイドロジェンホスフェート、メタクリル酸、N−メタクリロイルグリシン、N−メタクリロイルアスパラギン酸、N−メタクリロイル−5−アミノサリチル酸、2−メタクリロイルオキシエチルハイドロジェンサクシネート、2−メタクリロイルオキシエチルハイドロジェンフタレート、2−メタクリロイルオキシエチルハイドロジェンマレート、6−メタクリロイルオキシエチルナフタレン−1,2,6−トリカルボン酸、O−メタクリロイルチロシン、N−メタクリロイルチロシン、N−メタクリロイルフェニルアラニン、N−メタクリロイル−p−アミノ安息香酸、N−メタクリロイル−O−アミノ安息香酸、2−メタクリロイルオキシ安息香酸、3−メタクリロイルオキシ安息香酸、4−メタクリロイルオキシ安息香酸、N−メタクリロイル−5−アミノサリチル酸、N−メタクリロイル−4−アミノサリチル酸、11−メタクリロイルオキシウンデカン−1,1−ジカルボン酸、10−メタクリロイルオキシデカン−1,1−ジカルボン酸、12−メタクリロイルオキシドデカン−1,1−ジカルボン酸、6−メタクリロイルオキシヘキサン−1,1−ジカルボン酸、4−(2−メタクリロイルオキシエチル)トリメリテート、4−メタクリロイルオキシエチルトリメリテート、4−メタクリロイルオキシブチルトリメリテート、4−メタクリロイルオキシヘキシルトリメリテート、4−メタクリロイルオキシデシルトリメリテート、6−メタクリロイルオキシエチルナフタレン−1,2,6−トリカルボン酸無水物、6−メタクリロイルオキシエチルナフタレン−2,3,6−トリカルボン酸無水物、4−メタクリロイルオキシエチルカルボニルプロピオノイル−1,8−ナフタル酸無水物、4−メタクリロイルオキシエチルナフタレン−1,8−トリカルボン酸無水物等のメタクリレート、及びこれらのメタクリレートに対応するアクリレート等。
2,2−ビス(メタクリロイルオキシフェニル)プロパン、2,2−ビス[4−(3−メタクリロイルオキシ)−2−ヒドロキシプロポキシフェニル]プロパン、2,2−ビス(4−メタクリロイルオキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシポリエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシジエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシテトラエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシペンタエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシジプロポキシフェニル)プロパン、2(4−メタクリロイルオキシジエトキシフェニル)−2(4−メタクリロイルオキシトリエトキシフェニル)プロパン、2(4−メタクリロイルオキシジプロポキシフェニル)−2−(4−メタクリロイルオキシトリエトキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシプロポキシフェニル)プロパン、2,2−ビス(4−メタクリロイルオキシイソプロポキシフェニル)プロパン、エチレングリコールジメタクリレート、ジエチレングリコールジメタクリレート、トリエチレングリコールジメタクリレート、テトラエチレングリコールジメタクリレート、ネオペンチルグリコールジメタクリレート、1,3−ブタンジオールジメタクリレート、1,4−ブタンジオールジメタクリレート、1,6−ヘキサンジオールジメタクリレート、1,9−ノナンジオールジメタクリレート、グリセリンジメタクリレート、ビス(2−メタクリロイルオキシエチル)ハイドロジェンホスフェート、ビス(6−メタクリロイルオキシヘキシル)ハイドロジェンホスフェート、2−メタクリロイルオキシエチル−3’−メタクリロイルオキシ−2’−(3,4−ジカルボキシベンゾイルオキシ)プロピルサクシネート、N,O−ジメタクリロイルチロシン及びこれらのメタクリレートに対応するアクリレート;2−ヒドロキシエチルメタクリレート、2−ヒドロキシプロピルメタクリレート、3−クロロ−2−ヒドロキシプロピルメタクリレート等のメタクリレートあるいはこれらメタクリレートに対応するアクリレートのような−OH基を有するビニルモノマーと、ジイソシアネートメチルベンゼン、4,4’−ジフェニルメタンジイソシアネート、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、ジイソシアネートメチルシクロヘキサン、イソフォロンジイソシアネート、メチレンビス(4−シクロヘキシルイソシアネート)のようなジイソシアネート化合物との付加体から得られるジアダクト;1,2−ビス(3−メタクリロイルオキシ−2−ヒドロキシプロポキシ)エチル、1,6−ビス(メタクリロイルエチルオキシカルボニルアミノ)2,2,4−トリメチルヘキサン等。
トリメチロールプロパントリメタクリレート、トリメチロールエタントリメタクリレート、ペンタエリスリトールトリメタクリレート、トリメチロールメタントリメタクリレート等のメタクリレート及びこれらのメタクリレートに対応するアクリレート等。
ペンタエリスリトールテトラメタクリレート、ペンタエリスリトールテトラアクリレート及びジイソシアネートメチルベンゼン、ジイソシアネートメチルシクロヘキサン、イソフォロンジイソシアネート、ヘキサメチレンジイソシアネート、トリメチルヘキサメチレンジイソシアネート、メチレンビス(4−シクロヘキシルイソシアネート)、4,4−ジフェニルメタンジイソシアネート、トリレン−2,4−ジイソシアネートのようなジイソシアネート化合物とグリシドールジメタクリレートとの付加体から得られるジアダクト等。
接着剤の粘度は低粘度であることが好ましい。接着剤が低粘度であることによって、ポリアリールエーテルケトン樹脂材料の表面の微細な凹凸に接着剤が侵入しやすくなり、ポリアリールエーテルケトン樹脂材料表面に均一に接着剤を塗布する事が容易となり、より高い接着性が得られやすくなる。また、ラジカル重合性単量体と重合開始剤とを含む硬化性組成物からなる被着体を圧着し、ポリアリールエーテルケトン樹脂材料と被着体とを接着する場合、接着剤層の厚さを薄くすることが容易となる。一方、接着剤の粘度が低すぎる場合には、接着剤が垂れるなどの原因により、複雑な構造を有する場合もあるポリアリールエーテルケトン樹脂材料の被着面に対して均一に接着剤を塗布する事が困難となる場合がある。そのため、接着剤の粘度としては、23℃において、0.3cP〜3000cPの範囲である事が好ましく、0.4cP〜500cPの範囲である事がより好ましく、0.5cP〜30cPの範囲である事が更に好ましく、0.5cP〜10cPの範囲が最も好ましい。粘度の測定は、23℃に保った恒温室内で、コーンプレート型粘度計を用いて行う。化学重合開始剤とラジカル重合性単量体を含有する接着剤の粘度の測定は、化学重合開始剤を含まない組成を調整して測定を行えば良い。
化学重合開始剤とラジカル重合性単量体を含有する接着剤は2つの別個の包装に保存し、使用直前に混和し、使用する。
本発明においては、ポリアリールエーテルケトン樹脂材料の被着面に化学重合開始剤とラジカル重合性単量体を含有する接着剤を塗布した後、光照射を行って接着性ポリアリールエーテルケトン樹脂材料を製造する。光照射を行う際の雰囲気は、特に制限されず空気中で行えばよい。なお、光照射によって発生するラジカルは酸素分子によって補足されるので、酸素のない条件下で光照射を行うと、本願発明の高い接着性が得られるという効果をより効果的に得ることができる。ポリアリールエーテルケトン樹脂材料の表面に光照射を行うことによって、ポリアリールエーテルケトン樹脂材料の、ポリアリールエーテルケトン樹脂に存在する2つの芳香環を置換基として有するケトン基が活性化し、ラジカルが発生する。この発生したラジカルと、接着剤が含有するラジカル重合性単量体のラジカル重合性官能基が反応することによって、ポリアリールエーテルケトン樹脂材料と接着剤の間に結合が形成される。また、接着剤中に含まれる化学重合開始剤により接着剤層自体が徐徐に硬化する。次いで、ラジカル重合性単量体と重合性開始剤とを含む硬化性組成物を接着剤の上から圧着することにより、酸素が遮断され、接着剤の重合阻害が抑制される。さらに、接着剤中の化学重合開始剤により、ここで重合が加速する。その後、この硬化性組成物を重合硬化させることにより、接着剤のラジカル重合性単量体のラジカル重合性官能基と、硬化性組成物のラジカル重合性単量体のラジカル重合性官能基が反応することによって、接着剤と硬化性組成物の間に結合が形成される。このようにして、ポリアリールエーテルケトン樹脂材料とラジカル重合性の硬化性組成物との間で、高い接着性を得ることが可能となると推察される。
本発明の接着性ポリアリールエーテルケトン樹脂は、ポリアリールエーテルケトン樹脂材料の被着面に化学重合開始剤とラジカル重合性単量体を含有する接着剤を塗布した後に、上記したように光照射することで得られる。接着剤の塗布方法は特に限定されないが、歯科用のマイクロブラシや綿球などに染み込ませて塗布すると、均一に塗布しやすい。また、前記接着剤が溶媒を含む場合には、接着剤強度の観点から、溶媒の乾燥を行うことが望ましい。乾燥方法は特に限定されないが、圧縮空気を吹き付ける方法が簡便である。
本発明において、ポリアリールエーテルケトン樹脂材料と接着される被着体は、ラジカル重合性単量体と重合開始剤とを含む硬化性組成物からなる。
本発明の製造方法によって得られた接着性ポリアリールエーテルケトン樹脂材料と、ラジカル重合性単量体と重合開始剤とを含む硬化性組成物からなる被着体との接着方法は特に限定されない。ラジカル重合性単量体と重合開始剤とを含む硬化性組成物を本発明の接着性ポリアリールエーテルケトン樹脂材料の表面に付与する形態は、特に制限されず、たとえば、ラジカル重合性単量体と重合開始剤とを含む硬化性組成物を本発明の接着性ポリアリールエーテルケトン樹脂材料の表面に直接塗布したり、本発明の接着性ポリアリールエーテルケトン樹脂材料以外の他の部材の表面にラジカル重合性単量体と重合開始剤とを含む硬化性組成物を塗布した後、他の部材を本発明の接着性ポリアリールエーテルケトン樹脂材料に接触させることでポリアリールエーテルケトン樹脂材料とラジカル重合性単量体と重合開始剤とを含む硬化性組成物を接触させたりできる。
本発明の製造方法によって得られた接着性ポリアリールエーテルケトン樹脂材料は、如何様な用途にも用いることができるが、歯科分野において用いられることが好ましい。
<分子内に2以上の重合性官能基を有する重合性単量体>
・bisGMA:2,2−ビス[4−(3−メタクリロイルオキシ)−2−ヒドロキシプロポキシフェニル]プロパン
・3G:トリエチレングリコールジメタクリレート
<分子内に1つのみの重合性官能基を有する重合性単量体>
・HEMA:2−ヒドロキシエチルメタクリレート
・BPO:過酸化ベンゾイル
・DMBE:p−ジメチルアミノ安息香酸エチルエステル
[光重合開始剤]
・CQ:カンファーキノン
・DMBE:p−ジメチルアミノ安息香酸エチルエステル
化学重合開始剤とラジカル重合性単量体を含有し、光重合開始剤を実質的に含有しない接着剤としては、表1に組成を示す接着剤を使用した。
表1に記載されるラジカル重合性単量体、揮発性溶媒、化学重合開始剤、光重合開始剤を混合し、全成分が均一になるまで撹拌した。なお、化学重合開始剤を含有する接着剤についてはA包装、B包装の二種類に分けてそれぞれ混合撹拌し、使用直前にA包装とB包装とを同量混合することで最終的な接着剤を調製した。
表1に記載される接着剤の粘度は、23℃に保った恒温室内で、コーンプレート型粘度計を用いて測定した。化学重合開始剤とラジカル重合性単量体を含有する接着剤の粘度の測定は、化学重合開始剤を含まない組成を別途調整し、測定を行った。
ポリアリールエーテルケトン樹脂材料としては、以下に示す2種のポリアリールエーテルケトン樹脂材料C1、C2を使用した。
上記ポリアリールエーテルケトン樹脂材料を射出成形により2mm×13mm×13mmの板状に成形した。13mm×13mmの被着面を#800の耐水研磨紙で磨いた後にサンドブラスト処理(サンドブラスト装置を使用して粒径約50μmのアルミナ粒子を約0.2MPaの圧力で10秒間吹き付けた)にて粗ぞう化を行った。その後、水に浸して超音波に5分間晒し、続いてアセトンに浸して超音波に5分間晒すことで洗浄を行った。次いで、被着面に直径3mmの穴を有する厚さ0.2μmの両面テープを貼り付けた。
上記ポリアリールエーテルケトン樹脂材料を射出成形により2mm×13mm×13mmの板状に成形した。このポリアリールエーテルケトン樹脂材料の被着面を#800の耐水研磨紙で磨いた後にサンドブラスト処理(サンドブラスト装置を使用して粒径約50μmのアルミナ粒子を約0.2MPaの圧力で10秒間吹き付けた)にて粗ぞう化を行った。その後、水に浸して超音波に5分間晒し、続いてアセトンに浸して超音波に5分間晒すことで洗浄を行った。
ラジカル重合性単量体成分として、bisGMAをA包装、B包装にそれぞれ2.5gずつ、3GをA包装、B包装にそれぞれ2.5g、揮発性溶媒成分としてアセトンをA包装、B包装にそれぞれ250g、A包装に化学重合開始剤としてBPOを2g、B包装に化学重合開始剤としてDMBEを2g添加し、それぞれを撹拌混合し、A包装、B包装を得た。得られたA包装とB包装を同量攪拌混合し、接着剤B1を得た。接着剤の組成、粘度は表1に示す。この接着剤をポリアリールエーテルケトン樹脂材料C1の表面に塗布した後、歯科用可視光線照射器L1としてL.E.DemetronII(Kerr社製、LED照射器)をライトガイド先端と光照射面までの距離を調整して光照射面の光強度が800mW/cm2となる条件で使用してポリアリールエーテルケトン樹脂材料の接着剤塗布面に対して10秒間の光照射を行い、本発明の接着性ポリアリールエーテルケトン樹脂材料を得て、本発明の接着性ポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定を行った。歯科用光照射器の光強度、光照射時間、光エネルギーの各値、引っ張り接着強さ、接着剤層の厚みの測定結果を表2に示す。
B1組成から化学重合開始剤の量を変更し、表2に示す組成で調製したB2及びB3を用いた以外は、実施例1に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定の測定を行った。測定結果を表2に示す。
光照射時の光強度、光照射時間、光エネルギーを表2に示すとおり変更した以外は、実施例1に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定の測定を行った。測定結果を表2に示す。
使用する歯科用可視光線照射器を、L2としてOptilux500(Kerr社製、ハロゲン照射器)とした以外は、実施例1に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定の測定を行った。測定結果を表2に示す。
使用するポリアリールエーテルケトン樹脂材料をC2へと変更した以外は、実施例1に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定の測定を行った。測定結果を表3に示す。
使用するポリアリールエーテルケトン樹脂材料をC2へと変更した以外は、実施例4に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定の測定を行った。測定結果を表3に示す。
ポリアリールエーテルケトン樹脂材料C1と、実施例1で作製したB1を使用し、ポリアリールエーテルケトン樹脂材料に塗布したB1に対して光照射を行わずに、本発明の接着性ポリアリールエーテルケトン樹脂材料ではないポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さの測定、接着剤層の厚みの測定を行った。測定結果を表2に示す。
表1に示すように、接着剤に重合開始剤を添加しないB4を調製し、それを用いた以外は、実施例1に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料ではないポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定の測定を行った。測定結果を表2に示す。
表1に示すように、接着剤に重合開始剤を添加しないB4を調製し、それを用いた以外は、実施例4に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料ではないポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定の測定を行った。測定結果を表2に示す。
表1に示すように、接着剤に光重合開始剤を添加したB5を調製し、それを用いた以外は、実施例1に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料ではないポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定の測定を行った。測定結果を表2に示す。
ポリアリールエーテルケトン樹脂材料をC2へと変更した以外は、比較例1に準じて、本発明の接着性ポリアリールエーテルケトン樹脂材料ではないポリアリールエーテルケトン樹脂材料の作製及びそれと硬化性組成物との引っ張り接着強さ測定、接着剤層の厚みの測定を行った。測定結果を表3に示す。
Claims (5)
- 40質量%以上が重合性官能基として分子内に2以上の(メタ)アクリロイル基を有するラジカル重合性単量体であるラジカル重合性単量体及び化学重合開始剤を含有し、光重合開始剤を実質的に含有しない接着剤を、ポリアリールエーテルケトン樹脂材料の表面に塗布した後に、最大ピーク波長が400nm〜500nmである光を前記ポリアリールエーテルケトン樹脂材料の接着剤塗布面に照射することを特徴とする接着性ポリアリールエーテルケトン樹脂材料の製造方法。
- 接着性ポリアリールエーテルケトン樹脂材料が歯科用である請求項1に記載の接着性ポリアリールエーテルケトン樹脂材料の製造方法。
- 40質量%以上が重合性官能基として分子内に2以上の(メタ)アクリロイル基を有するラジカル重合性単量体であるラジカル重合性単量体及び化学重合開始剤を含有し、光重合開始剤を実質的に含有しない接着剤を、ポリアリールエーテルケトン樹脂材料の表面に塗布した後に、最大ピーク波長が400nm〜500nmである光を前記ポリアリールエーテルケトン樹脂材料の接着剤塗布面に照射することを特徴とするポリアリールエーテルケトン樹脂材料の前処理方法。
- ポリアリールエーテルケトン樹脂材料と、ラジカル重合性単量体及び重合開始剤を含む硬化性組成物からなる被着体と、を接着する接着方法であって、
40質量%以上が重合性官能基として分子内に2以上の(メタ)アクリロイル基を有するラジカル重合性単量体であるラジカル重合性単量体及び化学重合開始剤を含有し、光重合開始剤を実質的に含有しない接着剤を、前記ポリアリールエーテルケトン樹脂材料の表面に塗布した後に、最大ピーク波長が400nm〜500nmである光を前記ポリアリールエーテルケトン樹脂材料の接着剤塗布面に照射し、次いで、前記接着剤塗布面上に前記被着体を圧着してから該被着体を重合硬化させることを特徴とする、ポリアリールエーテルケトン樹脂材料と被着体との接着方法。 - 40質量%以上が重合性官能基として分子内に2以上の(メタ)アクリロイル基を有するラジカル重合性単量体であるラジカル重合性単量体及び化学重合開始剤を含有し、光重合開始剤を実質的に含有しない接着剤を、ポリアリールエーテルケトン樹脂材料の表面に塗布した後に、最大ピーク波長が400nm〜500nmである光を前記ポリアリールエーテルケトン樹脂材料の接着剤塗布面に照射し、次いで、前記接着剤塗布面上にラジカル重合性単量体と重合開始剤とを含む硬化性組成物からなる被着体を圧着してから該被着体を重合硬化させることを特徴とする、積層体の製造方法。
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