TW199179B - - Google Patents
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- TW199179B TW199179B TW081104614A TW81104614A TW199179B TW 199179 B TW199179 B TW 199179B TW 081104614 A TW081104614 A TW 081104614A TW 81104614 A TW81104614 A TW 81104614A TW 199179 B TW199179 B TW 199179B
- Authority
- TW
- Taiwan
- Prior art keywords
- meth
- acrylate
- resin composition
- chemical formula
- patent application
- Prior art date
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 46
- 239000011342 resin composition Substances 0.000 claims description 41
- 239000000126 substance Substances 0.000 claims description 32
- -1 Acrylic ester Chemical class 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 23
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000003822 epoxy resin Substances 0.000 claims description 13
- 229920000647 polyepoxide Polymers 0.000 claims description 13
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 238000011049 filling Methods 0.000 claims description 12
- 230000005540 biological transmission Effects 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 8
- 239000004925 Acrylic resin Substances 0.000 claims description 7
- 239000002699 waste material Substances 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims 2
- 239000003245 coal Substances 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- 150000002148 esters Chemical group 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 230000002079 cooperative effect Effects 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 230000009965 odorless effect Effects 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 231100000241 scar Toxicity 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000001043 yellow dye Substances 0.000 description 3
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 2
- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- BHOQZFDFSMPLOU-UHFFFAOYSA-N C(C)NC(=O)OCC.C(C=C)(=O)O Chemical compound C(C)NC(=O)OCC.C(C=C)(=O)O BHOQZFDFSMPLOU-UHFFFAOYSA-N 0.000 description 2
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000032544 Cicatrix Diseases 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 238000003825 pressing Methods 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 230000037387 scars Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- SLHXYIVFBYHMCZ-UHFFFAOYSA-N (1-cyclohexylcyclohexa-2,4-dien-1-yl)-phenylmethanone Chemical compound C1(CCCCC1)C1(C(=O)C2=CC=CC=C2)CC=CC=C1 SLHXYIVFBYHMCZ-UHFFFAOYSA-N 0.000 description 1
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- MKDZJIHLRSIZOV-UHFFFAOYSA-N 1,2,3-tribromo-4-phenylbenzene Chemical compound BrC1=C(Br)C(Br)=CC=C1C1=CC=CC=C1 MKDZJIHLRSIZOV-UHFFFAOYSA-N 0.000 description 1
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical compound C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- NFPLJTNXOKFJRO-UHFFFAOYSA-N 1-ethenylpyridin-2-one Chemical compound C=CN1C=CC=CC1=O NFPLJTNXOKFJRO-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- GTUIOIQPAWIFIZ-UHFFFAOYSA-N 2-(1-hydroxycyclohexyl)phenol Chemical group OC1=CC=CC=C1C1(O)CCCCC1 GTUIOIQPAWIFIZ-UHFFFAOYSA-N 0.000 description 1
- DVVXXHVHGGWWPE-UHFFFAOYSA-N 2-(dimethylamino)benzoic acid Chemical compound CN(C)C1=CC=CC=C1C(O)=O DVVXXHVHGGWWPE-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
- XXCRXPYEAMCJKH-UHFFFAOYSA-N 3,3,4-trimethyloxepan-2-one Chemical compound CC1CCCOC(=O)C1(C)C XXCRXPYEAMCJKH-UHFFFAOYSA-N 0.000 description 1
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 102000040350 B family Human genes 0.000 description 1
- 108091072128 B family Proteins 0.000 description 1
- QQTGJVBUIOTPGZ-UHFFFAOYSA-N CCC[Zn]CCC Chemical compound CCC[Zn]CCC QQTGJVBUIOTPGZ-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 229910000074 antimony hydride Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 description 1
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical group CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- UQCGQJIWSCHJCO-UHFFFAOYSA-N cyclohexa-2,5-diene-1,4-dione;methanol Chemical compound OC.O=C1C=CC(=O)C=C1 UQCGQJIWSCHJCO-UHFFFAOYSA-N 0.000 description 1
- BMFYCFSWWDXEPB-UHFFFAOYSA-N cyclohexyl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1 BMFYCFSWWDXEPB-UHFFFAOYSA-N 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical group C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- UNOXZZNTIMQKJX-UHFFFAOYSA-N ethyl formate prop-2-enoic acid Chemical compound C(C=C)(=O)O.C(=O)OCC UNOXZZNTIMQKJX-UHFFFAOYSA-N 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 210000004905 finger nail Anatomy 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 238000007373 indentation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 210000000282 nail Anatomy 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- KAZRRCHOBOZQDU-UHFFFAOYSA-N oxiran-2-ylmethyl acetate prop-2-enoic acid Chemical compound C(C=C)(=O)O.C(C)(=O)OCC1CO1 KAZRRCHOBOZQDU-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000010421 standard material Substances 0.000 description 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03175730 | 1991-06-21 | ||
| JP4020726A JPH0558950A (ja) | 1991-06-21 | 1992-01-10 | （メタ）アクリル酸エステル |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW199179B true TW199179B (en, 2012) | 1993-02-01 |
Family
ID=26357701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW081104614A TW199179B (en, 2012) | 1991-06-21 | 1992-06-12 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US5453452A (en, 2012) |
| EP (1) | EP0519410B1 (en, 2012) |
| JP (1) | JPH0558950A (en, 2012) |
| KR (2) | KR100211088B1 (en, 2012) |
| DE (1) | DE69213346T2 (en, 2012) |
| DK (1) | DK0519410T3 (en, 2012) |
| TW (1) | TW199179B (en, 2012) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW312700B (en, 2012) * | 1994-05-17 | 1997-08-11 | Sony Co Ltd | |
| US5874495A (en) * | 1994-10-03 | 1999-02-23 | Rhodia Inc. | Polymers useful as PH responsive thickeners and monomers therefor |
| JP3769075B2 (ja) * | 1996-07-08 | 2006-04-19 | Ｊｓｒ株式会社 | 放射線硬化性樹脂組成物 |
| JPH11240926A (ja) * | 1998-02-26 | 1999-09-07 | Dainippon Printing Co Ltd | フレネルレンズ用電離放射線硬化型樹脂組成物及び透過型スクリーン |
| WO2000003302A1 (en) * | 1998-07-09 | 2000-01-20 | Carl Zeiss Jena Gmbh | Low-cost, simple mass production of light-guiding tips |
| WO2002048220A1 (fr) * | 2000-12-13 | 2002-06-20 | Tokuyama Corporation | Composition photochromique durcissable et articles a base de cette composition |
| US20050256219A1 (en) * | 2002-03-11 | 2005-11-17 | Hideaki Takase | Photocurable resin composition and optical component |
| TW200624510A (en) * | 2004-11-08 | 2006-07-16 | Mitsubishi Chem Corp | Radiative curable composition and cured product thereof, and laminate of the cured product |
| US8012567B2 (en) * | 2006-01-12 | 2011-09-06 | 3M Innovative Properties Company | Light-collimating film |
| JP5328003B2 (ja) * | 2006-06-16 | 2013-10-30 | 日本化薬株式会社 | 樹脂組成物、レンズ用樹脂組成物及びその硬化物 |
| WO2008013217A1 (fr) * | 2006-07-27 | 2008-01-31 | Nippon Kayaku Kabushiki Kaisha | Composition de résine, composition de résine pour lentilles et produits durcis de celles-ci |
| WO2008121465A1 (en) | 2007-02-27 | 2008-10-09 | 3M Innovative Properties Company | Brightness enhancing film comprising nanocomposite structure having improved crack resistance |
| US20080221291A1 (en) * | 2007-03-07 | 2008-09-11 | 3M Innovative Properties Company | Microstructured optical films comprising biphenyl difunctional monomers |
| EP2125914B1 (en) | 2007-03-09 | 2014-01-22 | 3M Innovative Properties Company | Triphenyl monomers suitable for microstructured optical films |
| US8986812B2 (en) | 2007-07-09 | 2015-03-24 | 3M Innovative Properties Company | Thin microstructured optical films |
| US20090105437A1 (en) * | 2007-10-19 | 2009-04-23 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| US8378046B2 (en) | 2007-10-19 | 2013-02-19 | 3M Innovative Properties Company | High refractive index pressure-sensitive adhesives |
| WO2009058513A1 (en) * | 2007-10-30 | 2009-05-07 | 3M Innovative Properties Company | High refractive index adhesives |
| JPWO2010004959A1 (ja) * | 2008-07-11 | 2012-01-05 | 日本化薬株式会社 | 光学レンズシート用エネルギー線硬化型樹脂組成物及びその硬化物 |
| TWI379840B (en) * | 2008-08-01 | 2012-12-21 | Eternal Chemical Co Ltd | Polymerizable composition and its uses |
| EP2346044A4 (en) * | 2008-11-05 | 2013-04-24 | Nippon Kayaku Kk | UV-CURABLE RESIN COMPOSITION FOR OPTICAL PLATES AND HARDENED PRODUCTS THEREOF |
| JP4645925B2 (ja) * | 2009-03-31 | 2011-03-09 | Ｄｉｃ株式会社 | （メタ）アクリル酸エステル誘導体 |
| US8829070B2 (en) * | 2009-08-31 | 2014-09-09 | Kabushiki Kaisha Toshiba | Ultraviolet-curable resin material for pattern transfer and magnetic recording medium manufacturing method using the same |
| WO2013190575A1 (en) * | 2012-06-21 | 2013-12-27 | Council Of Scientific & Industrial Research | High refractive index (meth) acrylates |
| JP6076125B2 (ja) | 2013-02-15 | 2017-02-08 | 三光株式会社 | リン系（メタ）アクリレート化合物及びその製造方法 |
| CN103539667B (zh) * | 2013-09-26 | 2015-06-17 | 上海维凯光电新材料有限公司 | 低色度邻苯基苯氧乙基丙烯酸酯的制备方法 |
| CN103709033A (zh) * | 2013-09-26 | 2014-04-09 | 上海维凯化学品有限公司 | 邻苯基苯氧乙基丙烯酸酯的制备方法 |
| WO2016013341A1 (ja) | 2014-07-23 | 2016-01-28 | Ntn株式会社 | 等速自在継手 |
| CN104788310A (zh) * | 2015-03-11 | 2015-07-22 | 张家港康得新光电材料有限公司 | 一种光学膜用丙烯酸酯类材料的制备方法 |
| JP6753038B2 (ja) * | 2015-04-07 | 2020-09-09 | 三菱ケミカル株式会社 | 光硬化性組成物 |
| TWI743204B (zh) * | 2016-09-26 | 2021-10-21 | 日商三菱瓦斯化學股份有限公司 | (甲基)丙烯酸系共聚物、樹脂組成物及其成形體與成形體之製造方法 |
| JP7081032B1 (ja) * | 2021-09-22 | 2022-06-06 | 東京応化工業株式会社 | 組成物、及び感光性組成物 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4144283A (en) * | 1976-10-07 | 1979-03-13 | Toyo Ink Manufacturing Co., Ltd. | Curable coating compositions |
| EP0126397B1 (en) * | 1983-05-20 | 1989-09-06 | Showa Denko Kabushiki Kaisha | Naphthalene derivative, polymerizable composition containing the same and polymer obtainable by polymerizing this composition |
| EP0226123A3 (en) * | 1985-12-03 | 1988-08-10 | Matsushita Electric Industrial Co., Ltd. | Method for producing transparent plastic article |
| US4745137A (en) * | 1986-06-25 | 1988-05-17 | The Dow Chemical Company | Polyurethanes prepared from solutions or dispersions of polymers of rigid polyaromatic monomers in polyols |
| JP2823016B2 (ja) * | 1986-12-25 | 1998-11-11 | ソニー株式会社 | 透過型スクリーンの製造方法 |
| JPS63199302A (ja) * | 1987-02-16 | 1988-08-17 | Pioneer Electronic Corp | フレネルレンズ |
| US4962163A (en) * | 1989-01-17 | 1990-10-09 | The Dow Chemical Company | Vinyl ester resins containing mesogenic/rigid rodlike moieties |
| US5066750A (en) * | 1989-01-17 | 1991-11-19 | The Dow Chemical Company | Vinyl ester resins containing mesogenic/rigid rodlike moieties |
| US5093386A (en) * | 1989-05-16 | 1992-03-03 | Stamicarbon B.V. | Liquid curable plastic composition |
-
1992
- 1992-01-10 JP JP4020726A patent/JPH0558950A/ja active Pending
- 1992-06-12 TW TW081104614A patent/TW199179B/zh not_active IP Right Cessation
- 1992-06-16 DE DE69213346T patent/DE69213346T2/de not_active Expired - Fee Related
- 1992-06-16 DK DK92110169.7T patent/DK0519410T3/da active
- 1992-06-16 EP EP92110169A patent/EP0519410B1/en not_active Expired - Lifetime
- 1992-06-17 KR KR1019920010469A patent/KR100211088B1/ko not_active Expired - Lifetime
-
1993
- 1993-12-16 US US08/168,674 patent/US5453452A/en not_active Expired - Lifetime
-
1995
- 1995-06-06 US US08/467,941 patent/US5629445A/en not_active Expired - Lifetime
-
1999
- 1999-01-13 KR KR1019990007620A patent/KR100254058B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR100211088B1 (en) | 1999-07-15 |
| EP0519410A3 (en) | 1993-03-31 |
| EP0519410B1 (en) | 1996-09-04 |
| EP0519410A2 (en) | 1992-12-23 |
| US5629445A (en) | 1997-05-13 |
| KR930000458A (ko) | 1993-01-15 |
| DE69213346T2 (de) | 1997-01-02 |
| JPH0558950A (ja) | 1993-03-09 |
| DE69213346D1 (de) | 1996-10-10 |
| US5453452A (en) | 1995-09-26 |
| DK0519410T3 (da) | 1996-09-23 |
| KR100254058B1 (ko) | 2000-04-15 |
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| MM4A | Annulment or lapse of patent due to non-payment of fees |