CA1199145A - Melanges photopolymerisables; methode de photopolymerisation de composes polymerisables par l'intermediaires des cations - Google Patents

Melanges photopolymerisables; methode de photopolymerisation de composes polymerisables par l'intermediaires des cations

Info

Publication number: CA1199145A
Authority: CA; Canada
Prior art keywords: alkyl; phenyl; compounds; catalyst; alkoxy
Prior art date: 1981-06-04
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.): Expired

Application number

CA000404348A

Other languages

English (en)

Inventor

Godwin Berner

Rudolf Kirchmayr

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.)

BASF Schweiz AG

Original Assignee

Ciba Geigy Investments Ltd

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.)

1981-06-04

Filing date

1982-06-02

Publication date

1986-01-07

1982-06-02 Application filed by Ciba Geigy Investments Ltd filed Critical Ciba Geigy Investments Ltd

1986-01-07 Application granted granted Critical

1986-01-07 Publication of CA1199145A publication Critical patent/CA1199145A/fr

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 36
239000000203 mixture Substances 0.000 title claims abstract description 28
238000000034 method Methods 0.000 title claims abstract description 17
230000008569 process Effects 0.000 title claims abstract description 15
-1 epoxide compounds Chemical class 0.000 claims abstract description 39
239000003054 catalyst Substances 0.000 claims abstract description 20
239000003426 co-catalyst Substances 0.000 claims abstract description 20
150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 8
229910021630 Antimony pentafluoride Inorganic materials 0.000 claims abstract description 6
229910017048 AsF6 Inorganic materials 0.000 claims abstract description 6
VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 claims abstract description 6
150000001450 anions Chemical class 0.000 claims abstract description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 8
150000003863 ammonium salts Chemical class 0.000 claims description 7
239000000654 additive Substances 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 claims description 3
125000005605 benzo group Chemical group 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
LCYXYLLJXMAEMT-SAXRGWBVSA-N Pyridinoline Chemical group OC(=O)[C@@H](N)CCC1=C[N+](C[C@H](O)CC[C@H](N)C([O-])=O)=CC(O)=C1C[C@H](N)C(O)=O LCYXYLLJXMAEMT-SAXRGWBVSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
JYNZIOFUHBJABQ-UHFFFAOYSA-N allyl-{6-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-hexyl-}-methyl-amin Chemical compound C=1OC2=CC(OCCCCCCN(C)CC=C)=CC=C2C=1C1=CC=C(Br)C=C1 JYNZIOFUHBJABQ-UHFFFAOYSA-N 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 3
125000004846 (C1-C4) allyl group Chemical group 0.000 claims 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 1
NFGODEMQGQNUKK-UHFFFAOYSA-M [6-(diethylamino)-9-(2-octadecoxycarbonylphenyl)xanthen-3-ylidene]-diethylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCOC(=O)C1=CC=CC=C1C1=C2C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C21 NFGODEMQGQNUKK-UHFFFAOYSA-M 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
238000009281 ultraviolet germicidal irradiation Methods 0.000 abstract description 2
229920000647 polyepoxide Polymers 0.000 description 14
238000001723 curing Methods 0.000 description 10
150000003254 radicals Chemical class 0.000 description 6
150000003839 salts Chemical class 0.000 description 5
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
238000007792 addition Methods 0.000 description 4
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
125000002091 cationic group Chemical group 0.000 description 4
238000000576 coating method Methods 0.000 description 4
238000001035 drying Methods 0.000 description 4
150000002118 epoxides Chemical class 0.000 description 4
239000003822 epoxy resin Substances 0.000 description 4
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
239000003999 initiator Substances 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
125000003118 aryl group Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000011248 coating agent Substances 0.000 description 3
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
239000003365 glass fiber Substances 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
229920001451 polypropylene glycol Polymers 0.000 description 3
238000007639 printing Methods 0.000 description 3
239000000126 substance Substances 0.000 description 3
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 2
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 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
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 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
125000001931 aliphatic group Chemical group 0.000 description 2
125000000217 alkyl group Chemical group 0.000 description 2
229920003180 amino resin Polymers 0.000 description 2
239000002585 base Substances 0.000 description 2
229960002130 benzoin Drugs 0.000 description 2
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000000975 dye Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
229940052303 ethers for general anesthesia Drugs 0.000 description 2
239000011521 glass Substances 0.000 description 2
235000019382 gum benzoic Nutrition 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000000463 material Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
238000000465 moulding Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000049 pigment Substances 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
239000000758 substrate Substances 0.000 description 2
ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
239000002023 wood Substances 0.000 description 2
JLLAWIKMLAQZCZ-UHFFFAOYSA-N (2,6-dichlorophenyl)-diphenylphosphorylmethanone Chemical compound ClC1=CC=CC(Cl)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 JLLAWIKMLAQZCZ-UHFFFAOYSA-N 0.000 description 1
SUEDCWGEKSLKOM-UHFFFAOYSA-N (2,6-dimethoxyphenyl)-diphenylphosphorylmethanone Chemical compound COC1=CC=CC(OC)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 SUEDCWGEKSLKOM-UHFFFAOYSA-N 0.000 description 1
NZXFPAIYBJMGPQ-UHFFFAOYSA-N (4-chlorophenyl)-(1-hydroxycyclooctyl)methanone Chemical compound ClC1=CC=C(C(=O)C2(CCCCCCC2)O)C=C1 NZXFPAIYBJMGPQ-UHFFFAOYSA-N 0.000 description 1
MFEWNFVBWPABCX-UHFFFAOYSA-N 1,1,2,2-tetraphenylethane-1,2-diol Chemical compound C=1C=CC=CC=1C(C(O)(C=1C=CC=CC=1)C=1C=CC=CC=1)(O)C1=CC=CC=C1 MFEWNFVBWPABCX-UHFFFAOYSA-N 0.000 description 1
FQERLIOIVXPZKH-UHFFFAOYSA-N 1,2,4-trioxane Chemical compound C1COOCO1 FQERLIOIVXPZKH-UHFFFAOYSA-N 0.000 description 1
UCXPESOPEKJXJR-UHFFFAOYSA-N 1,2-bis(4-chlorophenyl)-2-hydroxyethanone Chemical compound C=1C=C(Cl)C=CC=1C(O)C(=O)C1=CC=C(Cl)C=C1 UCXPESOPEKJXJR-UHFFFAOYSA-N 0.000 description 1
UVACFPCUKHMXQX-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)-2-propan-2-yloxyethanone Chemical compound C(C)(C)OC(C(C1=CC=C(C=C1)OC)=O)C1=CC=C(C=C1)OC UVACFPCUKHMXQX-UHFFFAOYSA-N 0.000 description 1
ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 description 1
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 1
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HAOXTAJLDMZCQJ-UHFFFAOYSA-N 1-ethoxydodecane Chemical compound CCCCCCCCCCCCOCC HAOXTAJLDMZCQJ-UHFFFAOYSA-N 0.000 description 1
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RIAWWRJHTAZJSU-UHFFFAOYSA-N 1-methoxyoctane Chemical compound CCCCCCCCOC RIAWWRJHTAZJSU-UHFFFAOYSA-N 0.000 description 1
DBUJFULDVAZULB-UHFFFAOYSA-N 1-methoxypentane Chemical compound CCCCCOC DBUJFULDVAZULB-UHFFFAOYSA-N 0.000 description 1
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FVNIMHIOIXPIQT-UHFFFAOYSA-N 2-methoxybutane Chemical compound CCC(C)OC FVNIMHIOIXPIQT-UHFFFAOYSA-N 0.000 description 1
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125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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150000008062 acetophenones Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
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230000032683 aging Effects 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
239000004411 aluminium Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001454 anthracenes Chemical class 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000002216 antistatic agent Substances 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical compound C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
230000008859 change Effects 0.000 description 1
WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000010924 continuous production Methods 0.000 description 1
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
KQQHLHAGUIMAPM-UHFFFAOYSA-N diphenylphosphoryl-(1,3,5-trimethylcyclohexa-2,4-dien-1-yl)methanone Chemical compound C1C(C)=CC(C)=CC1(C)C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 KQQHLHAGUIMAPM-UHFFFAOYSA-N 0.000 description 1
238000000295 emission spectrum Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
LDLDYFCCDKENPD-UHFFFAOYSA-N ethenylcyclohexane Chemical compound C=CC1CCCCC1 LDLDYFCCDKENPD-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000006112 glass ceramic composition Substances 0.000 description 1
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical class CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
239000000976 ink Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000004611 light stabiliser Substances 0.000 description 1
230000007246 mechanism Effects 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
150000002739 metals Chemical class 0.000 description 1
229940086559 methyl benzoin Drugs 0.000 description 1
KWKAKUADMBZCLK-UHFFFAOYSA-N methyl heptene Natural products CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
229920003986 novolac Polymers 0.000 description 1
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
150000002921 oxetanes Chemical class 0.000 description 1
150000002924 oxiranes Chemical class 0.000 description 1
239000000123 paper Substances 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229930015698 phenylpropene Natural products 0.000 description 1
239000011941 photocatalyst Substances 0.000 description 1
238000000016 photochemical curing Methods 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920001225 polyester resin Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
150000008442 polyphenolic compounds Chemical class 0.000 description 1
235000013824 polyphenols Nutrition 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
229960000380 propiolactone Drugs 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000003847 radiation curing Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012779 reinforcing material Substances 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
231100000489 sensitizer Toxicity 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000003595 spectral effect Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000007984 tetrahydrofuranes Chemical class 0.000 description 1
238000001029 thermal curing Methods 0.000 description 1
XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 1
150000003552 thietanes Chemical class 0.000 description 1
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
150000003553 thiiranes Chemical class 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
229920001567 vinyl ester resin Polymers 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Epoxy Resins (AREA)
Paints Or Removers (AREA)
Polymerization Catalysts (AREA)
Adhesives Or Adhesive Processes (AREA)
Polyethers (AREA)
Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

CA000404348A 1981-06-04 1982-06-02 Melanges photopolymerisables; methode de photopolymerisation de composes polymerisables par l'intermediaires des cations Expired CA1199145A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
CH3673/81-1		1981-06-04
CH367381		1981-06-04

Publications (1)

Publication Number	Publication Date
CA1199145A true CA1199145A (fr)	1986-01-07

Family

ID=4261051

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000404348A Expired CA1199145A (fr)	1981-06-04	1982-06-02	Melanges photopolymerisables; methode de photopolymerisation de composes polymerisables par l'intermediaires des cations

Country Status (5)

Country	Link
JP (1)	JPS57209931A (fr)
CA (1)	CA1199145A (fr)
DE (1)	DE3220550A1 (fr)
FR (1)	FR2507342A1 (fr)
GB (1)	GB2099825B (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0152377B1 (fr) *	1984-02-10	1987-12-09	Ciba-Geigy Ag	Compositions durcissables et leur emploi
US5503937A (en) *	1984-07-17	1996-04-02	The Dow Chemical Company	Curable composition which comprises adducts of heterocyclic compounds
DE68927300T2 (de) *	1988-02-12	1997-04-30	Dow Chemical Co	Verwendung eines Katalysators für Epoxyharz-Zusammensetzungen
JP3269106B2 (ja) *	1992-02-10	2002-03-25	日本曹達株式会社	ピリジニウム塩化合物を含有する硬化性組成物
JP3285053B2 (ja) *	1993-05-11	2002-05-27	日本曹達株式会社	新規ピラジニウム塩化合物および重合開始剤
IN2012DN03022A (fr)	2009-10-01	2015-07-31	Hitachi Chemical Co Ltd
EP2562839A4 (fr)	2010-04-22	2015-07-22	Hitachi Chemical Co Ltd	Matériau électronique organique, initiateur de polymérisation et initiateur de polymérisation thermique, composition d'encre, couche mince organique et son procédé de production, élément électronique organique, élément électroluminescent organique, dispositif d'éclairage, élément d'affichage, et dispositif d'affichage
KR20150127077A (ko)	2013-03-08	2015-11-16	히타치가세이가부시끼가이샤	이온성 화합물을 함유하는 처리액, 유기 일렉트로닉스 소자, 및 유기 일렉트로닉스 소자의 제조 방법

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4234732A (en) *	1974-05-02	1980-11-18	General Electric Company	Photoinitiators
US4026705A (en) *	1975-05-02	1977-05-31	General Electric Company	Photocurable compositions and methods
GB2034318B (en) *	1978-10-27	1983-05-11	Ici Ltd	Photopolymerisable compositions derived coatings and other polymerised products
NL7904171A (nl) *	1978-11-22	1980-05-27	Gen Electric	Hardbare, hars bevattende materialen en werkwijze voor het opschuimen hiervan.

1982
- 1982-05-27 GB GB8215578A patent/GB2099825B/en not_active Expired
- 1982-06-01 DE DE19823220550 patent/DE3220550A1/de not_active Withdrawn
- 1982-06-02 CA CA000404348A patent/CA1199145A/fr not_active Expired
- 1982-06-03 FR FR8209647A patent/FR2507342A1/fr not_active Withdrawn
- 1982-06-04 JP JP9606082A patent/JPS57209931A/ja active Pending

Also Published As

Publication number	Publication date
FR2507342A1 (fr)	1982-12-10
JPS57209931A (en)	1982-12-23
GB2099825B (en)	1984-12-05
GB2099825A (en)	1982-12-15
DE3220550A1 (de)	1983-03-17

Legal Events

Date	Code	Title	Description
2003-01-07	MKEX	Expiry

Publication	Publication Date	Title
US4069055A (en)	1978-01-17	Photocurable epoxy compositions containing group Va onium salts
US3835003A (en)	1974-09-10	Photopolymerization of oxetanes
US4058401A (en)	1977-11-15	Photocurable compositions containing group via aromatic onium salts
US4150988A (en)	1979-04-24	Method of photopolymerizing polymerizable compositions containing group Va onium salts
US4138255A (en)	1979-02-06	Photo-curing method for epoxy resin using group VIa onium salt
US4175972A (en)	1979-11-27	Curable epoxy compositions containing aromatic onium salts and hydroxy compounds
KR100355313B1 (ko)	2003-03-04	부가적인관능기를갖는비닐에테르화합물
US3794576A (en)	1974-02-26	Epoxide blend radiation sensitive catalyst precursor
CA1293835C (fr)	1991-12-31	Composition durcissable, et son emploi
CA1156793A (fr)	1983-11-08	Melange polymerisable par voie photochimique ou thermique, renfermant un sel d'iodonium aromatique et un photo-initiateur aromatique carbonyle
US4593052A (en)	1986-06-03	Polymerizable compositions containing diphenyliodosyl salts
US3721617A (en)	1973-03-20	Photopolymerizable epoxy systems containing cyclic amide gelation inhibitors
JPH08511569A (ja)	1996-12-03	安定化された硬化性接着剤
CZ5799A3 (cs)	1999-04-14	Způsob vytvrzování kationtově fotovytvrzovatelných formulací
US3711390A (en)	1973-01-16	Photopolymerizable epoxy systems containing substituted cyclic amides or substituted ureas as gelation inhibitors
JPH04980B2 (fr)	1992-01-09
CA2171504A1 (fr)	1996-09-14	Stabilisation de compositions liquides contre une polymerisation prematuree par rayonnement
JPH0413374B2 (fr)	1992-03-09
US4175973A (en)	1979-11-27	Curable compositions
IE42085B1 (en)	1980-06-04	Photopolymerisable compositions
EP0276716A2 (fr)	1988-08-03	Compositions de résine époxyde à durcissement retardé
JPS6047029A (ja)	1985-03-14	光重合性有機組成物に使用するジアリールヨードニウム塩及びその製造方法
US6562410B1 (en)	2003-05-13	Heat curable epoxy compositions
GB2099825A (en)	1982-12-15	Photopolymerisable mixtures, and processes for the photopolymerisation of cationically polymerisable compounds
JP7490345B2 (ja)	2024-05-27	重合体