JPS5819323A - 光重合性樹脂およびその製造法 - Google Patents

光重合性樹脂およびその製造法

Info

Publication number: JPS5819323A
Authority: JP; Japan
Prior art keywords: group; carbon atoms; formula; atoms; carbon
Prior art date: 1981-07-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

JP11965682A

Other languages

English (en)

Japanese (ja)

Other versions

JPH029615B2 (da

Inventor

ロ−デリツク・ドナルド・ハサウエイ

エドワ−ド・ア−ビング

ジヨン・シドネイ・ウオ−タ−ハウス

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-07-09

Filing date

1982-07-09

Publication date

1983-02-04

1982-07-09 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1983-02-04 Publication of JPS5819323A publication Critical patent/JPS5819323A/ja

1990-03-02 Publication of JPH029615B2 publication Critical patent/JPH029615B2/ja

Status Granted legal-status Critical Current

Links

239000011347 resin Substances 0.000 title claims description 39
229920005989 resin Polymers 0.000 title claims description 39
238000004519 manufacturing process Methods 0.000 title claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 35
-1 oxyphenyleneoxy group Chemical group 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 17
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 15
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
125000002947 alkylene group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 6
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
125000002723 alicyclic group Chemical group 0.000 claims description 4
125000004450 alkenylene group Chemical group 0.000 claims description 4
125000000732 arylene group Chemical group 0.000 claims description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
150000001721 carbon Chemical group 0.000 claims description 3
125000002993 cycloalkylene group Chemical group 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 2
125000005724 cycloalkenylene group Chemical group 0.000 claims description 2
150000001991 dicarboxylic acids Chemical class 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims 4
239000001301 oxygen Substances 0.000 claims 4
125000004430 oxygen atom Chemical group O* 0.000 claims 4
125000005515 organic divalent group Chemical group 0.000 claims 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
125000003368 amide group Chemical group 0.000 claims 2
ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical class OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 claims 2
125000005462 imide group Chemical group 0.000 claims 2
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
101000893493 Homo sapiens Protein flightless-1 homolog Proteins 0.000 claims 1
102100040923 Protein flightless-1 homolog Human genes 0.000 claims 1
125000002619 bicyclic group Chemical group 0.000 claims 1
239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
125000002843 carboxylic acid group Chemical group 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
150000002118 epoxides Chemical class 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
239000000203 mixture Substances 0.000 description 31
238000006243 chemical reaction Methods 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000000243 solution Substances 0.000 description 12
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
230000005855 radiation Effects 0.000 description 10
239000003054 catalyst Substances 0.000 description 9
230000003247 decreasing effect Effects 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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 6
238000000576 coating method Methods 0.000 description 6
239000000463 material Substances 0.000 description 6
150000002923 oximes Chemical class 0.000 description 6
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 5
125000004429 atom Chemical group 0.000 description 5
239000002585 base Substances 0.000 description 5
239000011248 coating agent Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
238000007142 ring opening reaction Methods 0.000 description 5
230000001235 sensitizing effect Effects 0.000 description 5
238000003756 stirring Methods 0.000 description 5
BVQVLAIMHVDZEL-UHFFFAOYSA-N 1-phenyl-1,2-propanedione Chemical compound CC(=O)C(=O)C1=CC=CC=C1 BVQVLAIMHVDZEL-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
229920000742 Cotton Polymers 0.000 description 4
235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
RPBPCPJJHKASGQ-UHFFFAOYSA-K chromium(3+);octanoate Chemical compound [Cr+3].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O.CCCCCCCC([O-])=O RPBPCPJJHKASGQ-UHFFFAOYSA-K 0.000 description 4
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical group 0.000 description 4
239000002904 solvent Substances 0.000 description 4
RZJKZTPKSRPUFJ-UHFFFAOYSA-N 5,5-dimethyl-1,3-bis(oxiran-2-ylmethyl)imidazolidine-2,4-dione Chemical compound O=C1N(CC2OC2)C(=O)C(C)(C)N1CC1CO1 RZJKZTPKSRPUFJ-UHFFFAOYSA-N 0.000 description 3
150000001252 acrylic acid derivatives Chemical class 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
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
239000010931 gold Substances 0.000 description 3
229910052737 gold Inorganic materials 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
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 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
244000028419 Styrax benzoin Species 0.000 description 2
235000000126 Styrax benzoin Nutrition 0.000 description 2
235000008411 Sumatra benzointree Nutrition 0.000 description 2
239000002253 acid Substances 0.000 description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229960002130 benzoin Drugs 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
235000019382 gum benzoic Nutrition 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
229910052753 mercury Inorganic materials 0.000 description 2
WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920001451 polypropylene glycol Polymers 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
150000003455 sulfinic acids Chemical class 0.000 description 2
239000008096 xylene Substances 0.000 description 2
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
SEULWJSKCVACTH-UHFFFAOYSA-N 1-phenylimidazole Chemical compound C1=NC=CN1C1=CC=CC=C1 SEULWJSKCVACTH-UHFFFAOYSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-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
QWICFSIIRBJAKP-UHFFFAOYSA-N 2,3,5-tributyl-4-methylphenol Chemical compound CCCCC1=CC(O)=C(CCCC)C(CCCC)=C1C QWICFSIIRBJAKP-UHFFFAOYSA-N 0.000 description 1
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FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
SHKUUQIDMUMQQK-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COCCCCOCC1CO1 SHKUUQIDMUMQQK-UHFFFAOYSA-N 0.000 description 1
DZZAHLOABNWIFA-UHFFFAOYSA-N 2-butoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCCCC)C(=O)C1=CC=CC=C1 DZZAHLOABNWIFA-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
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 description 1
UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical group C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
OQAPYXJOOYQXDV-UHFFFAOYSA-N 5,5-dimethyl-3-[2-(oxiran-2-ylmethoxy)propyl]-1-(oxiran-2-ylmethyl)imidazolidine-2,4-dione Chemical compound C1OC1COC(C)CN(C(C1(C)C)=O)C(=O)N1CC1CO1 OQAPYXJOOYQXDV-UHFFFAOYSA-N 0.000 description 1
CUARLQDWYSRQDF-UHFFFAOYSA-N 5-Nitroacenaphthene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] CUARLQDWYSRQDF-UHFFFAOYSA-N 0.000 description 1
RWHRFHQRVDUPIK-UHFFFAOYSA-N 50867-57-7 Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O RWHRFHQRVDUPIK-UHFFFAOYSA-N 0.000 description 1
241000208140 Acer Species 0.000 description 1
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101100136092 Drosophila melanogaster peng gene Proteins 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
108010053823 Rho Guanine Nucleotide Exchange Factors Proteins 0.000 description 1
102100033200 Rho guanine nucleotide exchange factor 7 Human genes 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
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RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical group [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
238000005299 abrasion Methods 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910000272 alkali metal oxide Inorganic materials 0.000 description 1
150000001412 amines Chemical group 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000003287 bathing Methods 0.000 description 1
FWYSSOIRLVHQNC-UHFFFAOYSA-M benzyl(trimethyl)azanium;acetate Chemical compound CC([O-])=O.C[N+](C)(C)CC1=CC=CC=C1 FWYSSOIRLVHQNC-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
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
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239000004020 conductor Substances 0.000 description 1
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239000013078 crystal Substances 0.000 description 1
239000012024 dehydrating agents‎ Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical compound C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 1
QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical compound C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000005611 electricity Effects 0.000 description 1
238000005265 energy consumption Methods 0.000 description 1
230000003628 erosive effect Effects 0.000 description 1
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125000001033 ether group Chemical group 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
239000004744 fabric Substances 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000003651 hexanedioyl group Chemical group C(CCCCC(=O)*)(=O)* 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
210000000088 lip Anatomy 0.000 description 1
229910001507 metal halide Inorganic materials 0.000 description 1
150000005309 metal halides Chemical class 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical group CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 1
CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
229960000907 methylthioninium chloride Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
101150032584 oxy-4 gene Proteins 0.000 description 1
QQBPIHBUCMDKFG-UHFFFAOYSA-N phenazopyridine hydrochloride Chemical group Cl.NC1=NC(N)=CC=C1N=NC1=CC=CC=C1 QQBPIHBUCMDKFG-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
150000003003 phosphines Chemical class 0.000 description 1
238000005424 photoluminescence Methods 0.000 description 1
239000003504 photosensitizing agent Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000000644 propagated effect Effects 0.000 description 1
230000001902 propagating effect Effects 0.000 description 1
239000001294 propane Substances 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
230000007115 recruitment Effects 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000000344 soap Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011775 sodium fluoride Substances 0.000 description 1
235000013024 sodium fluoride Nutrition 0.000 description 1
238000009987 spinning Methods 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940014800 succinic anhydride Drugs 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
238000004018 waxing Methods 0.000 description 1
229910052724 xenon Inorganic materials 0.000 description 1
FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1

Landscapes

Polymerisation Methods In General (AREA)
Epoxy Resins (AREA)
Macromonomer-Based Addition Polymer (AREA)

JP11965682A 1981-07-09 1982-07-09 光重合性樹脂およびその製造法 Granted JPS5819323A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB8121172		1981-07-09
GB8121172		1981-07-09
GB8209955		1982-04-03

Publications (2)

Publication Number	Publication Date
JPS5819323A true JPS5819323A (ja)	1983-02-04
JPH029615B2 JPH029615B2 (da)	1990-03-02

Family

ID=10523118

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP11965682A Granted JPS5819323A (ja)	1981-07-09	1982-07-09	光重合性樹脂およびその製造法

Country Status (1)

Country	Link
JP (1)	JPS5819323A (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60166306A (ja) *	1984-02-09	1985-08-29	Daicel Chem Ind Ltd	光重合開始剤

1982
- 1982-07-09 JP JP11965682A patent/JPS5819323A/ja active Granted

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS60166306A (ja) *	1984-02-09	1985-08-29	Daicel Chem Ind Ltd	光重合開始剤

Also Published As

Publication number	Publication date
JPH029615B2 (da)	1990-03-02

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AU672645B2 (en)	1996-10-10	Novel (cyclo)aliphatic epoxy compounds
DE2153860C2 (de)	1982-06-09	Verwendung von photopolymerisierbaren Gemischen zur Herstellung ätzmittelbeständiger Masken
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HK1005623B (en)	1999-01-15	New(cyclo) aliphatic epoxy compounds
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US5624788A (en)	1997-04-29	Organic silicon compound, resist thermal polymerization composition and photopolymerization composition
US4392930A (en)	1983-07-12	Photopolymerizable resins
JPH0756354A (ja)	1995-03-03	珪素含有高分子化合物及びそれを用いたレジスト材料
KR920013028A (ko)	1992-07-28	광증감제 조성물
JPS61292634A (ja)	1986-12-23	フオトレジスト用ポリマ−組成物
Davies et al.	1996	Imaging of Aliphatic polycarbonates with photogenerated base
JP3460212B2 (ja)	2003-10-27	感放射線性樹脂組成物
DE2352348A1 (de)	1974-05-09	Funktionelles polymeres und damit durchfuehrbares bildwiedergabeverfahren
JPS6361651B2 (da)	1988-11-29

JPS5819323A - 光重合性樹脂およびその製造法 - Google Patents

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Links

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Applications Claiming Priority (3)

Publications (2)

Family

ID=10523118

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Also Published As

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