CN101293910B - Muliti-alicyclic base acrylic ester and acrylic ester composition - Google Patents
Muliti-alicyclic base acrylic ester and acrylic ester composition Download PDFInfo
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- CN101293910B CN101293910B CN 200710102142 CN200710102142A CN101293910B CN 101293910 B CN101293910 B CN 101293910B CN 200710102142 CN200710102142 CN 200710102142 CN 200710102142 A CN200710102142 A CN 200710102142A CN 101293910 B CN101293910 B CN 101293910B
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- Prior art keywords
- acrylic ester
- muliti
- acrylate
- composition
- formula
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 38
- -1 acrylic ester Chemical class 0.000 title claims description 35
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 30
- 239000003999 initiator Substances 0.000 claims abstract description 17
- 238000000576 coating method Methods 0.000 claims abstract description 6
- 238000007639 printing Methods 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 16
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical class C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 7
- 210000000941 bile Anatomy 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 5
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims description 4
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 4
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 claims description 3
- SMEROWZSTRWXGI-UHFFFAOYSA-N Lithocholsaeure Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)CC2 SMEROWZSTRWXGI-UHFFFAOYSA-N 0.000 claims description 3
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 3
- SMEROWZSTRWXGI-HVATVPOCSA-N lithocholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 SMEROWZSTRWXGI-HVATVPOCSA-N 0.000 claims description 3
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 claims description 3
- LSDPWZHWYPCBBB-UHFFFAOYSA-N methyl mercaptane Natural products SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 2
- XTHNOXDNMLKBFF-UHFFFAOYSA-N 4-(1-phenylpropan-2-yl)morpholine Chemical compound C1COCCN1C(C)CC1=CC=CC=C1 XTHNOXDNMLKBFF-UHFFFAOYSA-N 0.000 claims 1
- 230000009477 glass transition Effects 0.000 abstract description 13
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 2
- 230000003287 optical effect Effects 0.000 abstract description 2
- 239000011230 binding agent Substances 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 36
- 239000002585 base Substances 0.000 description 25
- 208000034189 Sclerosis Diseases 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- FTFNFGIOGXKJSP-UHFFFAOYSA-N 1-ethoxy-4-methoxybenzene Chemical compound CCOC1=CC=C(OC)C=C1 FTFNFGIOGXKJSP-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- 239000004411 aluminium Substances 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000008247 solid mixture Substances 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2,2'-azo-bis-isobutyronitrile Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 230000003321 amplification Effects 0.000 description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Chemical class CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 3
- 150000004056 anthraquinones Chemical class 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- 238000003199 nucleic acid amplification method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GZBSIABKXVPBFY-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OC(=O)C=C.OCC(CO)(CO)CO GZBSIABKXVPBFY-UHFFFAOYSA-N 0.000 description 2
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 2
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 2
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 2
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000007046 ethoxylation reaction Methods 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical compound CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- GZAROOOHRGKEPC-UHFFFAOYSA-N n-butyl-2-methylpropanamide Chemical compound CCCCNC(=O)C(C)C GZAROOOHRGKEPC-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
- UICXTANXZJJIBC-UHFFFAOYSA-N 1-(1-hydroperoxycyclohexyl)peroxycyclohexan-1-ol Chemical compound C1CCCCC1(O)OOC1(OO)CCCCC1 UICXTANXZJJIBC-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- CKSAKVMRQYOFBC-UHFFFAOYSA-N 2-cyanopropan-2-yliminourea Chemical compound N#CC(C)(C)N=NC(N)=O CKSAKVMRQYOFBC-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- WNXTZVMMNCCZTP-UHFFFAOYSA-N 2-hydroxyethyl 2-methylprop-2-enoate 5-hydroxy-2-methylpent-2-enoic acid Chemical compound OCCC=C(C(=O)O)C.C(C(=C)C)(=O)OCCO WNXTZVMMNCCZTP-UHFFFAOYSA-N 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- KZPMXWBRKHQGQJ-UHFFFAOYSA-N 2-methyl-4-(oxiran-2-yl)but-2-enoic acid oxiran-2-ylmethyl 2-methylprop-2-enoate Chemical compound O1C(CC=C(C(=O)O)C)C1.C(C(=C)C)(=O)OCC1CO1 KZPMXWBRKHQGQJ-UHFFFAOYSA-N 0.000 description 1
- LNGIIXGLYTUUHJ-UHFFFAOYSA-N 2-methylbut-2-enoic acid methyl 2-methylprop-2-enoate Chemical group COC(=O)C(C)=C.CC=C(C)C(O)=O LNGIIXGLYTUUHJ-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- PELLIXXLXFYBCG-UHFFFAOYSA-N 4-methyl-2-methylidenepentanoic acid 2-methylpropyl prop-2-enoate Chemical compound C(C(C)C)C(C(=O)O)=C.C(C=C)(=O)OCC(C)C PELLIXXLXFYBCG-UHFFFAOYSA-N 0.000 description 1
- HSFSSBXPCKRIMP-UHFFFAOYSA-N 4-tert-butylperoxy-3,6-dimethylcyclohexyne Chemical compound C(C)(C)(C)OOC1C(C#CC(C1)C)C HSFSSBXPCKRIMP-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- BIXNRGRTJGILCH-UHFFFAOYSA-N C(C)(C)C1=CC=2C(C3=CC=CC=C3SC2C=C1)=O.C(C)(C)C1=CC=2C(C3=CC=CC=C3SC2C=C1)=O Chemical compound C(C)(C)C1=CC=2C(C3=CC=CC=C3SC2C=C1)=O.C(C)(C)C1=CC=2C(C3=CC=CC=C3SC2C=C1)=O BIXNRGRTJGILCH-UHFFFAOYSA-N 0.000 description 1
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- YBXSFGKRWPBPJU-UHFFFAOYSA-N C(C1=CC=CC=C1)C(C(=O)C1=CC=C(C=C1)N1CCOCC1)(CC)N(C)C.C(CCC)=O Chemical compound C(C1=CC=CC=C1)C(C(=O)C1=CC=C(C=C1)N1CCOCC1)(CC)N(C)C.C(CCC)=O YBXSFGKRWPBPJU-UHFFFAOYSA-N 0.000 description 1
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- UOIBFTLLLBZSQP-UHFFFAOYSA-N C(C1=CC=CC=C1)C=C(C(=O)OC)C.C1=CC=CC=C1.C(C(=C)C)(=O)O Chemical compound C(C1=CC=CC=C1)C=C(C(=O)OC)C.C1=CC=CC=C1.C(C(=C)C)(=O)O UOIBFTLLLBZSQP-UHFFFAOYSA-N 0.000 description 1
- NSOPTJHDXDYIMB-UHFFFAOYSA-N CC(CC1=CC=C(C=C1)SC)(C)N1CCOCC1.CCC Chemical compound CC(CC1=CC=C(C=C1)SC)(C)N1CCOCC1.CCC NSOPTJHDXDYIMB-UHFFFAOYSA-N 0.000 description 1
- 239000004380 Cholic acid Substances 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- ZDWIRZDSGZSCJW-UHFFFAOYSA-N OCCCC(C(=O)OC(COC(C=C)=O)C)=C Chemical compound OCCCC(C(=O)OC(COC(C=C)=O)C)=C ZDWIRZDSGZSCJW-UHFFFAOYSA-N 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- SSOONFBDIYMPEU-UHFFFAOYSA-N [3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propyl] prop-2-enoate Chemical compound OCC(CO)(CO)COCC(CO)(CO)COC(=O)C=C SSOONFBDIYMPEU-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000003613 bile acid Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
- 229960002471 cholic acid Drugs 0.000 description 1
- 235000019416 cholic acid Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- VBWIZSYFQSOUFQ-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#CC1CCCCC1 VBWIZSYFQSOUFQ-UHFFFAOYSA-N 0.000 description 1
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 1
- 125000004980 cyclopropylene group Chemical group 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- HXDBMSZZSWTGKB-UHFFFAOYSA-N ethyl prop-2-enoate;2-methylidenebutanoic acid Chemical compound CCOC(=O)C=C.CCC(=C)C(O)=O HXDBMSZZSWTGKB-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- WMRNGPYHLQSTDL-UHFFFAOYSA-N n-cyclohexyl-2-[[1-(cyclohexylamino)-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound C1CCCCC1NC(=O)C(C)(C)N=NC(C)(C)C(=O)NC1CCCCC1 WMRNGPYHLQSTDL-UHFFFAOYSA-N 0.000 description 1
- NPFIXJIFUHTLRP-UHFFFAOYSA-N n-cyclohexyl-2-methylpropanamide Chemical compound CC(C)C(=O)NC1CCCCC1 NPFIXJIFUHTLRP-UHFFFAOYSA-N 0.000 description 1
- 230000005622 photoelectricity Effects 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- GSECCTDWEGTEBD-UHFFFAOYSA-N tert-butylperoxycyclohexane Chemical compound CC(C)(C)OOC1CCCCC1 GSECCTDWEGTEBD-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- MHNHYTDAOYJUEZ-UHFFFAOYSA-N triphenylphosphane Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 MHNHYTDAOYJUEZ-UHFFFAOYSA-N 0.000 description 1
Abstract
The invention provides a polyalcyl acrylate, which can be further mixed with a photo and/or a thermal initiator or other acrylates to form an acrylate composition. The inventive acrylate composition has high glass transition temperature and high heat-conducting property after curing. Therefore, the composition can be used as optical devices, photoelectric devices, electronic devices, coatings, printing ink or binders.
Description
Technical field
The present invention relates to a kind of acrylate composition, more particularly relate to the Muliti-alicyclic base acrylic ester that it comprises.
Background technology
The range of application of acrylate (acrylate is commonly called as acryl) is quite extensive, is example with present information society, and electronics/photoelectricity/optics all needs to finish by the acrylate processing treatment.Except above-mentioned application, acrylate also is applied to fields such as printing-ink, coating, tackiness agent, and the modern life is had very important influence.Under the situation that science and technology is maked rapid progress, the product innovation that how to develop high function and high added value is the common objective of each industry.Should there be novel material and the frontier of more application acrylate to obtain continuing exploitation from now on.
At present, photodiode (LED) material as solid state light emitter has following demand: the packaged material of (1) optical property such as high transmission rate, high refractive index; (2) high heat radiation, heat conductivility such as high-power encapsulation or baseplate material; (3) high-photoelectric transformation efficiency is as the chip material of high brightness/power; (4) compact assembly is as high glass transition temp (T
g) acrylate.
Open 2002-49157 and the spy opens among the 2002-365803 the Japanese Patent spy, the shape activator that discloses a kind of eurymeric chemical amplification photo-corrosion-resisting agent composition and comprised, its structure is suc as formula 1.
R wherein
7, R
8, R
9, R
10Independent separately, be selected from H, OH, alkoxyl group (alkoxy) or ethanoyl (acetoxy).R
11For meeting the functional group that acid is decomposed, as the tertiary butyl (t-butyl).
Open among the 2004-12545 the Japanese Patent spy, the shape activator that discloses another kind of eurymeric chemical amplification photo-corrosion-resisting agent composition and comprised, its structure is suc as formula 2.
R wherein
12, R
13, R
14Independent separately, be H or OH, at least one is OH among the three; R
15Be alkyl.
In Japanese patent laid-open 11-279118, a kind of photosensitive composition is disclosed, the Acrylic Acid Monomer of its alkali soluble resins is suc as formula 3.This photosensitive composition can be applicable to unicircuit, liquid crystal panel, printed circuit board (PCB), printing plate and light procedure for processing.
R wherein
16, R
17Be H or OH, R
18Be H or CH
3
At periodical Steroids 2005,70, in 531, respectively with methacrylic acid, methacrylic chloride (methacryloyl chloride), and derivative (suc as formula the 4) reaction of methacryloyl acid anhydrides (methacryloyl anhydride) and bile acide (cholic acid), disclose that the reactivity of OH base is C3 on the bile acid derivative〉C12〉C7.
R wherein
19Be general alkanes.
At periodical Chem.Mater.1998, in 10,4037, carry out heat embrittlement with the bile acid derivative of formula 4 and the composition of other polyfunctional group acrylic acid derivative, the product after the sclerosis can be used as the selective absorber of cholesterol in the Digestive tract.
Above-mentioned patent or periodical are all relevant with the derivative of bile acide.The spy open 2002-49157, spy open 2002-365803, and the special compound of opening 2004-12545 all as the shape activator of eurymeric chemical amplification photo-corrosion-resisting agent composition.Bile acid derivative in above-mentioned three pieces of patents is not all had an Acrylic Acid Monomer.Bile acid derivative among the Te Kaiping 11-279118 only has single acrylic-functional, if make up with other vinylformic acid, will influence rerum natura such as glass transition temp or the thermal conductive property of composition under the situation of crosslinking degree deficiency.In addition, in the bile acid derivative in two pieces of papers, the acrylic-functional molecular chain between the alicyclic ring core at the most is shorter, will be too hard and crisp after the sclerosis, and is not suitable for purposes such as electron device or packaged material.
Summary of the invention
The invention provides a kind of Muliti-alicyclic base acrylic ester, can effectively improve glass transition temp and the thermal conductive property of acrylic acid composition, its structure is suc as formula 5.
R wherein
1Be selected from H or CH
3, and R
2, R
3, R
4Independent separately, at least one is formula 6 among the three, and all the other are H or OH.
R wherein
5Be selected from ethyl, propyl group or cyclohexyl, and R
6Be selected from H or CH
3
The present invention also provides a kind of acrylate composition, comprises the Muliti-alicyclic base acrylic ester that 100 weight parts are above-mentioned; And the reaction initiator of 0.1～40 weight part.
Embodiment
The invention provides a kind of Muliti-alicyclic base acrylic ester, its structure is suc as formula 5.
R wherein
1Be selected from H or CH
3, and R
2, R
3, R
4Independent separately, at least one is formula 6 among the three, and all the other are H or OH.
R wherein
5Be selected from ethyl, propyl group or cyclohexyl, and R
6Be selected from H or CH
3
The center of above-mentioned Muliti-alicyclic base acrylic ester is made up of the greasiness ring, and sturdy construction and be easy to the oneself and arrange is conducive to improve heat conductivility.In addition, then there is plural acrylate-functional groups the molecule periphery, has higher crosslinking temperature after the sclerosis, can have preferable rerum natura such as high glass transition temp.On the other hand, but the R of the greasiness nucleolus heart to the molecular chain length through type 6 of terminal acrylate functional group
5Design adjustment.
In order to improve the rate of crosslinking of above-mentioned Muliti-alicyclic base acrylic ester, the greasiness cyclopropylene acid esters of desirable 100 weight parts adds the reaction initiator of 0.1～40 weight part, mixes and namely forms acrylate composition.Reaction initiator can be light trigger, thermal initiator or above-mentioned combination.Light trigger comprises acetophenones, st-yrax class, phenylbenzene ketone, thioxanthene ketone, anthraquinone class or above-mentioned combination.Thermal initiator comprises azo class, peroxide or above-mentioned combination.
Light trigger has determined the kind of irradiates light, wavelength, and energy intensity, can be that acetophenones such as 2-methyl isophthalic acid-(4-(methyl mercaptan base) phenyl-2-woods is for propane (2-methyl-1-(4-(methylthio) phenyl)-2-morpholino-propane), 1-hydroxycyclohexylphenylketone (1-hydroxycyclohexylphenyl ketone), diethoxy acetophenone (diethoxyacetophenone), 2-hydroxy-2-methyl-1-phenyl-1-propane-1-ketone (2-hydroxy-2-methyl-1-phenyl-propane-1-one), 2-tolyl-2-(dimethylamino)-1-[4-(woods generation) phenyl]-the 1-butanone (2-benzyl-2-(dimethylamino)-1-[4-(morpholinyl) phenyl]-1-butanone), the methyl phenyl ketone that other is suitable; St-yrax class such as st-yrax (benzoin), st-yrax methyl ether (benzoin methyl ether), st-yrax dme (benzyldimethyl ketal), other suitable st-yrax; Phenylbenzene ketone such as diphenylketone (benzophenone), 4-phenyl diphenylketone (4-phenyl benzophenone), hydroxy diphenyl ketone (hydroxylbenzophenone) or other suitable diphenylketone; Thioxanthene ketone such as isopropyl thioxanthone (isopropylthioxanthone), 2-clopenthixal ketone (2-chlorothioxanthone) or other suitable thioxanthone; Anthraquinone class such as 2-ethyl-anthraquinone (2-ethylanthraquinone) or other suitable anthraquinone.Above-mentioned light trigger also can mix use obtaining film speed faster except can using separately, such as isopropyl thioxanthone and 2-tolyl-2-(dimethylamino)-1-[4-(woods generation) phenyl]-the 1-butanone mixes.
The starting temperature of thermal initiator is preferably between 50 ℃～220 ℃, this thermal initiator can be the azo class as 2,2 '-azo two (2,4-dimethyl n valeronitrile) (2,2 '-azobis (2,4-dimethyl valeronitrile)), dimethyl-2, two (2-the methyl propionate) (dimethyl-2 of 2 '-azo, 2 '-azobis (2-methylpropionate), 2,2-azobis isobutyronitrile (2,2-azobisisobutyronitrile, hereinafter to be referred as AIBN), 2, two (the 2-methyl isopropyl cyanides) (2 of 2-azo, 2-azobis (2-methylisobutyronitrile)), 1, two (hexanaphthenes-1-nitrile) (1 of 1 '-azo, 1 '-azobis (cyclohexane-1-carbonitrile)), 2, two [the N-2-propenyl-2-methyl propanamide] (2 of 2 '-azo, 2 '-azobis[N-(2-propenyl)-2-methylpropionamide]), 1-[(cyano group-1-methylethyl)-and azo-group] methane amide (1-[(cyano-1-methylethyl) azo] formamide), 2, two (the N-butyl-2-methyl propanamide) (2 of 2 '-azo, 2 '-azobis (N-butyl-2-methylpropionamide)), 2,2 '-azo two (N-cyclohexyl-2-methyl propanamide) (2,2 '-azobis (N-cyclohexyl-2-methylpropionamide), or other suitable azo-initiator; Peroxide comprises benzoyl peroxide (benzoyl peroxide); 1; 1-bis(t-butylperoxy) cyclohexane (1; 1-bis (tert-butylperoxy) cyclohexane); 2; 5-bis(t-butylperoxy)-2; 5-dimethyl cyclohexane (2; 5-bis (tert-butylperoxy)-2; 5-dimethylcyclohexane); 2; 5-bis(t-butylperoxy)-2; 5-dimethyl-3-cyclohexyne (2; 5-bis (tert-butylperoxy)-2,5-dimethyl-3-cyclohexyne); two (1-(t-butylperoxy)-1-methylethyl) benzene (bis (1-(tert-butylpeorxy)-1-methy-ethyl) benzene); tertbutyl peroxide (tert-butyl hydroperoxide); tert-butyl peroxide (tert-butyl peroxide); t-butylperoxy benzoic ether (tert-butylperoxybenzoate); cumene hydroperoxide (Cumene hydroperoxide); pimelinketone superoxide (cyclohexanone peroxide); two cumenyl superoxide (dicumyl peroxide); lauroyl superoxide (lauroyl peroxide); or other suitable superoxide.Above-mentioned thermal initiator also can mix use except can using separately, end depends on the needs.
Because its glass transition temp is more than or equal to 145 ℃ after sclerosis for above-mentioned composition, therefore heat-conduction coefficient is applicable to purposes such as optics, photoelectric device, electron device, coating, printing ink or tackiness agent more than or equal to 0.20W/mK.Except the reaction initiator of directly Muliti-alicyclic base acrylic ester of the present invention being arranged in pairs or groups, Muliti-alicyclic base vinylformic acid that can also 100 weight parts is made standard, add 0.1～100 parts by weight of acrylic ester, methacrylic ester or aforesaid combination, the rerum natura of the composition after hardening with further adjustment such as hardness, elasticity, fastness to rubbing, density etc.
Suitable methyl acrylic ester can be methyl methacrylate (methyl methacrylate), methacrylic acid benzene methyl (benzyl methacrylate), Jia Jibingxisuanyizhi (ethyl methacrylate), 2-hydroxyethyl methacrylate (2-hydroxyethyl methacrylate), methacrylic acid hydroxyl propyl ester (hydroxypropyl methacrylate), Propenoic acid, 2-methyl, isobutyl ester (isobutyl methacrylate), ethylene glycol dimethacrylate (ethylene glycol dimethacrylate), or other suitable methacrylic ester.Suitable esters of acrylic acid can be diethylene glycol diacrylate (diethylene glycoldiacrylate), 1,4-butylene glycol diacrylate (1,4-butanediol diacrylate), pentaerythritol triacrylate (pentaerythritol triacrylate), ethoxylation pentaerythritol triacrylate (ethoxylated pentaerythritol triacrylate), Dipentaerythritol five acrylate (dipentaetrythritol pentaacrylate), ethoxylation tetramethylol methane tetraacrylate (ethoxylatedpentaerythritol tetraacrylate), tetramethylol methane tetraacrylate ((pentaerythritoltetraacrylate), dipentaerythritol acrylate (dipentaerythritol hexaacrylate), methacrylic ester (methyl acrylate), vinylformic acid benzene methyl (benzyl acrylate), ethyl propenoate (ethyl acrylate), vinylformic acid 2-hydroxy methacrylate (2-hydroxyethyl acrylate), Propylene glycol monoacrylate (hydroxylpropyl acrylate), isobutyl acrylate (isobutyl acrylate), or other suitable acrylate.
For making those skilled in the art more clearly understand feature of the present invention, especially exemplified by following preferred embodiment.
Embodiment 1 (synthesizing of Muliti-alicyclic base tetraacrylate)
Get the 13.63g bile acide, 10.2g succinyl oxide (succinic anhydride) is dissolved in 60g dimethyl sulfoxide (DMSO) (dimethyl sulfoxide, hereinafter to be referred as DMSO) the logical nitrogen in back, be cooled to 80 ℃ in 110-120 ℃ of reaction after three hours, add 0.04g hydroquinone monomethyl ethyl ether (hydroquinonemonomethylethyl ether) as inhibitor to avoid crosslinking reaction, add 0.4g triphenylphosphine (triphenylphosphine) again as catalyzer, add 19.5g glycidyl methacrylate (glycidyl methacrylate) after the dissolving again and reacted three hours, namely get the DMSO solution of the Muliti-alicyclic base tetraacrylate of formula 7.
Embodiment 2 (synthesizing of Muliti-alicyclic base diacrylate)
Get 9.425g lithocholic acid (lithocholic acid), 2.5g succinyl oxide and be dissolved in logical nitrogen after the 60g dimethyl sulfoxide (DMSO), be cooled to 80 ℃ in 110-120 ℃ of reaction after three hours, the hydroquinone monomethyl ethyl ether that adds 0.04g as inhibitor to avoid crosslinking reaction, add the triphenylphosphine of 0.4g again as catalyzer, the glycidyl methacrylate that adds 7.48g after the dissolving was again reacted three hours, namely got the DMSO solution of the Muliti-alicyclic base diacrylate of formula 8.
Embodiment 3 (synthesizing of Muliti-alicyclic base triacrylate)
The Pyroglutaric acid (glutaric anhydride) of getting 13.63g bile acide, 11.3g is dissolved in logical nitrogen after the 60g dimethyl sulfoxide (DMSO), be cooled to 80 ℃ in 110-120 ℃ of reaction after three hours, add 0.04g hydroquinone monomethyl ethyl ether as inhibitor to avoid crosslinking reaction, add the triphenylphosphine of 0.4g again as catalyzer, add the 19.5g glycidyl methacrylate after the dissolving again and reacted three hours, namely get the DMSO solution of the Muliti-alicyclic base tetraacrylate of formula 9.
Embodiment 4 (synthesizing of Muliti-alicyclic base triacrylate)
Get 13.63g bile acide, 15.75g hexahydrophthalic anhydride (hexahydrophthalicanhydride) and be dissolved in logical nitrogen after the 60g dimethyl sulfoxide (DMSO), be cooled to 80 ℃ in 110-120 ℃ of reaction after three hours, the hydroquinone monomethyl ethyl ether that adds 0.04g as inhibitor to avoid crosslinking reaction, add the 0.4g triphenylphosphine again as catalyzer, add the 19.5g glycidyl methacrylate after the dissolving again and reacted three hours, namely get the DMSO solution of the Muliti-alicyclic base tetraacrylate of formula 10.
Embodiment 5 (acrylate composition)
Get the Muliti-alicyclic base tetraacrylate of 10g formula 7 DMSO solution (the solid composition is about 4.2g), 0.5g light trigger Irgacure907 (available from Ciba), and 0.125g light trigger 2-isopropyl thioxanthone (2-isopropylthioxanthone) (available from Lamberti, hereinafter to be referred as ITX), mix the back rotary coating on glass.Then place baking oven to toast 30 minutes to remove solvent, again with UV (intensity 500mJ/cm with 80 ℃
2) after the exposure, with 180 ℃ of bakings 40 minutes, the glass transition temp of the composition after the sclerosis was 161 ℃.
Embodiment 6 (acrylate composition)
Get DMSO solution (the solid composition is about 3g), 0.5g light trigger Irgacure907, and the 0.125g light trigger ITX of the Muliti-alicyclic base diacrylate of 15g formula 8, mix the back rotary coating on glass.Then place baking oven to toast 30 minutes to remove solvent, again with UV (intensity 500mJ/cm with 80 ℃
2) after the exposure, with 180 ℃ of bakings 40 minutes, the glass transition temp of the composition after the sclerosis was 160 ℃.From the above, the glass transition temp of acrylate composition of the present invention is all greater than 145 ℃
Embodiment 7 (acrylate composition)
Get the DMSO solution (the solid composition is about 4.2g) of the Muliti-alicyclic base tetraacrylate of 7.1g formula 7, the CN-966J75 of 1g (available from the urethane acrylate (urethane acrylate) of Sartomer), 0.5g light trigger Irgacure907, and 0.125g light trigger ITX, mixing and being placed on diameter is on 2 o'clock the aluminium dish.Then place baking oven to toast 4 hours to remove solvent, again with UV (intensity 500mJ/cm with 80 ℃
2) after the exposure, with 180 ℃ of bakings 40 minutes, after the sclerosis the dry film of thick about 1mm.The heat-conduction coefficient k of dry film is 0.27W/mK, 20 ℃ C
p(J/g ℃) is 1.413,30 ℃ C
p(J/g ℃) is 1.648.
Comparing embodiment 1 (acrylate composition)
Get 4gCN-966J75,0.5g light trigger Irgacure907,0.125g light trigger ITX, and a little solvent (acetone), mixing and being placed on diameter is on 2 o'clock the aluminium dish.Then place baking oven to toast 4 hours to remove solvent, again with UV (intensity 500mJ/cm with 80 ℃
2) after the exposure, with 180 ℃ of bakings 40 minutes, after the sclerosis the dry film of thick about 1mm.The heat-conduction coefficient k of dry film is 0.182W/mK, 20 ℃ C
p(J/g ℃) is 1.723,30 ℃ C
p(J/g ℃) is 1.747.Can find that with the comparison of comparing embodiment 1 be mixed with the acrylate composition of Muliti-alicyclic base acrylic ester of the present invention, the heat-conduction coefficient (0.182) of the acrylate composition that its heat-conduction coefficient (0.27) is more general exceeds about 50% by embodiment 7.
Embodiment 8 (acrylate composition)
Get DMSO solution (the solid composition is about 4.2g), 1gCN-966J75, and the 0.5g thermal initiator two cumenyl superoxide (dicumyl peroxide) of the Muliti-alicyclic base tetraacrylate of 7.1g formula 7, mixing and being placed on diameter is on 2 o'clock the aluminium dish.Then place baking oven to toast 4 hours to remove solvent, again with UV (intensity 500mJ/cm with 80 ℃
2) after the exposure, with 180 ℃ of bakings 40 minutes, after the sclerosis the dry film of thick about 1mm.The glass transition temp of dry film is 161 ℃.
Comparing embodiment 2 (acrylate composition)
Get 4gCN-966J75,0.5g thermal initiator two cumenyl superoxide, and a little solvent (acetone), mixing and being placed on diameter is on 2 o'clock the aluminium dish.Then place baking oven to toast 4 hours to remove solvent, again with UV (intensity 500mJ/cm with 80 ℃
2) after the exposure, with 180 ℃ of bakings 40 minutes, after the sclerosis the dry film of thick about 1mm.The glass transition temp of dry film is 145 ℃.
By embodiment 8 as can be known the present invention also be fit to use thermal initiator.No matter take thermal initiator or light trigger, be mixed with the acrylate composition of Muliti-alicyclic base acrylic ester of the present invention, glass transition temp (145 ℃) height of the acrylate composition that its glass transition temp (161 ℃) is more general.
Though the present invention discloses as above with a plurality of preferred embodiments; so it is not in order to limit the present invention; any person of ordinary skill in the field; without departing from the spirit and scope of the present invention; Ying Kezuo is change and retouching arbitrarily, so protection scope of the present invention should be as the criterion with the appended claims restricted portion.
Claims (4)
1. Muliti-alicyclic base acrylic ester, it is to be reacted by the glycidyl methacrylate of the bile acid derivative of 1 molar part and 2～4 molar part to form, and wherein this bile acid derivative is to be formed by the bile acide of 1 molar part or succinyl oxide, Pyroglutaric acid or the hexahydrophthalic anhydride reaction of lithocholic acid and 1～3 molar part.
2. acrylate composition comprises:
The described Muliti-alicyclic base acrylic ester of the claim 1 of 100 weight parts; And
0.1 the reaction initiator of～40 weight parts, wherein this reaction initiator is 2-methyl isophthalic acid-4-(methyl mercaptan base) phenyl-2-morpholino propane, isopropyl thioxanthone, two cumenyl superoxide or above-mentioned combination.
3. acrylate composition as claimed in claim 2 further comprises 0.1～100 parts by weight of acrylic ester, methacrylic ester or above-mentioned combination.
4. acrylate composition as claimed in claim 2, it is as optics, photoelectric device, electron device, coating, printing ink or tackiness agent.
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|---|---|---|---|---|
| JP2002049157A (en) * | 2000-08-03 | 2002-02-15 | Nec Corp | Positive type chemical amplification resist and its pattern forming method |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002049157A (en) * | 2000-08-03 | 2002-02-15 | Nec Corp | Positive type chemical amplification resist and its pattern forming method |
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| CN101293910A (en) | 2008-10-29 |
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