DE2602419A1 - Photopolymerisierbare masse - Google Patents
Photopolymerisierbare masseInfo
- Publication number
- DE2602419A1 DE2602419A1 DE19762602419 DE2602419A DE2602419A1 DE 2602419 A1 DE2602419 A1 DE 2602419A1 DE 19762602419 DE19762602419 DE 19762602419 DE 2602419 A DE2602419 A DE 2602419A DE 2602419 A1 DE2602419 A1 DE 2602419A1
- Authority
- DE
- Germany
- Prior art keywords
- benzophenone
- photopolymerizable composition
- methylthio
- composition according
- compounds
- Prior art date
- 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.)
- Withdrawn
Links
- 239000000203 mixture Substances 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000012965 benzophenone Substances 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 8
- 238000000576 coating method Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 6
- 150000003568 thioethers Chemical class 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- ILDSTJYAYOHBEH-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanethione Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=CC=C1 ILDSTJYAYOHBEH-UHFFFAOYSA-N 0.000 claims description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 4
- 238000003848 UV Light-Curing Methods 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003512 tertiary amines Chemical class 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 239000000976 ink Substances 0.000 claims description 3
- 150000003384 small molecules Chemical class 0.000 claims description 3
- 229920006305 unsaturated polyester Polymers 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- -1 aromatic disulfides Chemical class 0.000 description 11
- 239000010410 layer Substances 0.000 description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- 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 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000004383 yellowing Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- YNSNJGRCQCDRDM-UHFFFAOYSA-N 1-chlorothioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2Cl YNSNJGRCQCDRDM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229920003180 amino resin Polymers 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- ZBIAQUSSQDJCSS-UHFFFAOYSA-N bis(4-methylsulfanylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)C1=CC=C(SC)C=C1 ZBIAQUSSQDJCSS-UHFFFAOYSA-N 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 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
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000003678 scratch resistant effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- UCBXWZQSJMIWQZ-UHFFFAOYSA-N (2,4-dimethylphenyl)-(2-methylsulfanylphenyl)methanone Chemical compound CSC1=CC=CC=C1C(=O)C1=CC=C(C)C=C1C UCBXWZQSJMIWQZ-UHFFFAOYSA-N 0.000 description 1
- ODKBLXXTGKPHME-UHFFFAOYSA-N (2-chlorophenyl)-(4-methylphenyl)methanethione Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=CC=C1Cl ODKBLXXTGKPHME-UHFFFAOYSA-N 0.000 description 1
- VMLHMNYOFPEUEY-UHFFFAOYSA-N (2-fluorophenyl)-(4-methylphenyl)methanethione Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=CC=C1F VMLHMNYOFPEUEY-UHFFFAOYSA-N 0.000 description 1
- FZMQHPTVOWAMOL-UHFFFAOYSA-N (2-hydroxy-5-methylphenyl)-(2-methylsulfanylphenyl)methanone Chemical compound CSC1=CC=CC=C1C(=O)C1=CC(C)=CC=C1O FZMQHPTVOWAMOL-UHFFFAOYSA-N 0.000 description 1
- WPIVVNAJOMHAOP-UHFFFAOYSA-N (2-methylphenyl)-(4-methylphenyl)methanethione Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=CC=C1C WPIVVNAJOMHAOP-UHFFFAOYSA-N 0.000 description 1
- GZENQBXBKZHQTL-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanethione Chemical compound CC1=CC=CC=C1C(=S)C1=CC=CC=C1 GZENQBXBKZHQTL-UHFFFAOYSA-N 0.000 description 1
- ZAQYXVABXCUGPA-UHFFFAOYSA-N (2-methylsulfanylphenyl)-(2,4,6-trimethylphenyl)methanone Chemical compound CSC1=CC=CC=C1C(=O)C1=C(C)C=C(C)C=C1C ZAQYXVABXCUGPA-UHFFFAOYSA-N 0.000 description 1
- RYZYDSINUXQRRQ-UHFFFAOYSA-N (4-methylphenyl)-naphthalen-2-ylmethanethione Chemical compound C1=CC(C)=CC=C1C(=S)C1=CC=C(C=CC=C2)C2=C1 RYZYDSINUXQRRQ-UHFFFAOYSA-N 0.000 description 1
- MOYDKAXTOCBGMS-UHFFFAOYSA-N (4-methylsulfanylphenyl)-(2,4,6-trimethylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)C1=C(C)C=C(C)C=C1C MOYDKAXTOCBGMS-UHFFFAOYSA-N 0.000 description 1
- WGNHYOSRJXYRMI-UHFFFAOYSA-N 1,2-diphenylethanethione Chemical compound C=1C=CC=CC=1C(=S)CC1=CC=CC=C1 WGNHYOSRJXYRMI-UHFFFAOYSA-N 0.000 description 1
- XQLXSGCTOLBFAK-UHFFFAOYSA-N 1-prop-2-enoyloxypentyl prop-2-enoate Chemical compound CCCCC(OC(=O)C=C)OC(=O)C=C XQLXSGCTOLBFAK-UHFFFAOYSA-N 0.000 description 1
- PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical class C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical class CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 210000004905 finger nail Anatomy 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical class NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000011087 paperboard Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920002587 poly(1,3-butadiene) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000006120 scratch resistant coating Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/106—Binder containing
- Y10S430/108—Polyolefin or halogen containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
- Y10S430/1053—Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
- Y10S430/1055—Radiation sensitive composition or product or process of making
- Y10S430/114—Initiator containing
- Y10S430/122—Sulfur compound containing
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31525—Next to glass or quartz
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
- Y10T428/31529—Next to metal
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762602419 DE2602419A1 (de) | 1976-01-23 | 1976-01-23 | Photopolymerisierbare masse |
| IT30903/76A IT1067967B (it) | 1976-01-23 | 1976-12-27 | Composizione fotopolimerizzabile |
| US05/757,382 US4054682A (en) | 1976-01-23 | 1977-01-06 | Photopolymerizable composition containing a thioether sensitizer |
| BE174191A BE850519A (fr) | 1976-01-23 | 1977-01-19 | Matiere photopolymerisable |
| NL7700579A NL7700579A (nl) | 1976-01-23 | 1977-01-20 | Fotopolymeriseerbare massa. |
| FR7701579A FR2338952A1 (fr) | 1976-01-23 | 1977-01-20 | Matiere photopolymerisable |
| GB2482/77A GB1566953A (en) | 1976-01-23 | 1977-01-21 | Photopolymerizable composition |
| JP598077A JPS52104592A (en) | 1976-01-23 | 1977-01-24 | Photopolymerizable material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762602419 DE2602419A1 (de) | 1976-01-23 | 1976-01-23 | Photopolymerisierbare masse |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2602419A1 true DE2602419A1 (de) | 1977-07-28 |
Family
ID=5968057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762602419 Withdrawn DE2602419A1 (de) | 1976-01-23 | 1976-01-23 | Photopolymerisierbare masse |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4054682A (enExample) |
| JP (1) | JPS52104592A (enExample) |
| BE (1) | BE850519A (enExample) |
| DE (1) | DE2602419A1 (enExample) |
| FR (1) | FR2338952A1 (enExample) |
| GB (1) | GB1566953A (enExample) |
| IT (1) | IT1067967B (enExample) |
| NL (1) | NL7700579A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005530A1 (de) * | 1978-05-23 | 1979-11-28 | Ciba-Geigy Ag | Neue Mercaptophenylketone und deren Verwendung als Initiatoren für die Photopolymerisation äthylenisch ungesättigter Verbindungen |
| CN113056529A (zh) * | 2018-11-26 | 2021-06-29 | 爱克发-格法特公司 | 用于制造印刷电路板的可辐射固化的喷墨油墨 |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54130633A (en) * | 1978-04-01 | 1979-10-11 | Nippon Synthetic Chem Ind Co Ltd:The | Ultraviolet-curing coating composition |
| US4199420A (en) * | 1978-04-06 | 1980-04-22 | Stauffer Chemical Company | Alkoxymethylbenzophenones as photoinitiators for photopolymerizable compositions and process based thereon |
| DE2923602A1 (de) * | 1978-06-23 | 1980-01-10 | Sandoz Ag | Verwendung von substituierten alkylarylsulfoxiden und phenylarylsulfoxiden als photoinitiatoren |
| DE3167493D1 (en) * | 1980-11-05 | 1985-01-10 | Akzo Nv | Photopolymerizable composition, photoinitiator mixture and curing process |
| JPS6049038A (ja) * | 1983-08-29 | 1985-03-18 | Toyobo Co Ltd | ナイロンレンズ表面硬化剤 |
| DE3331157A1 (de) * | 1983-08-30 | 1985-03-14 | Basf Ag, 6700 Ludwigshafen | Photopolymerisierbare mischungen, enthaltend tertiaere amine als photoaktivatoren |
| DE3505998A1 (de) * | 1985-02-21 | 1986-08-21 | Merck Patent Gmbh, 6100 Darmstadt | Verwendung thiosubstituierter ketone als photoinitiatoren |
| JP2622113B2 (ja) * | 1986-12-02 | 1997-06-18 | キヤノン 株式会社 | 転写記録媒体及び画像記録方法 |
| DE3710281A1 (de) * | 1987-03-28 | 1988-10-06 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| DE3710282A1 (de) * | 1987-03-28 | 1988-10-13 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| US4753965A (en) * | 1987-04-09 | 1988-06-28 | Merrell Dow Pharmaceuticals, Inc. | Method of treating multiple sclerosis with chalcone derivatives |
| US4863968A (en) * | 1987-04-09 | 1989-09-05 | Merrell Dow Pharmaceuticals Inc. | Methods of treating gout with chalcone derivatives |
| US4904697A (en) * | 1987-04-09 | 1990-02-27 | Merrell Dow Pharmaceuticals Inc. | Controlling the growth of certain tumor tissue with chalcone derivatives |
| DE3738864A1 (de) * | 1987-11-16 | 1989-05-24 | Hoechst Ag | Polymerisierbare verbindungen und diese enthaltendes durch strahlung polymerisierbares gemisch |
| DE3743455A1 (de) * | 1987-12-22 | 1989-07-06 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| DE3743454A1 (de) * | 1987-12-22 | 1989-07-06 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| DE3743457A1 (de) * | 1987-12-22 | 1989-07-06 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| DE3824903A1 (de) * | 1988-07-22 | 1990-02-01 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| DE3832032A1 (de) * | 1988-09-21 | 1990-03-22 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| DE4007428A1 (de) * | 1990-03-09 | 1991-09-12 | Hoechst Ag | Photopolymerisierbares gemisch und daraus hergestelltes aufzeichnungsmaterial |
| JPH0497152A (ja) * | 1990-08-09 | 1992-03-30 | Kansai Paint Co Ltd | 光重合性組成物からパターンを形成する方法 |
| CN1305911C (zh) * | 2002-04-26 | 2007-03-21 | 雅宝公司 | 一种光引发聚合中的新型胺共引发剂 |
| US20080103222A1 (en) * | 2002-04-26 | 2008-05-01 | Albemarle Corporation | New Class of Amine Coinitiators in Photoinitiated Polymerizations |
| US7157535B2 (en) * | 2002-06-19 | 2007-01-02 | National Starch And Chemical Investment Holding Corporation | Polymeric photoinitiators |
| US20060293404A1 (en) * | 2003-04-24 | 2006-12-28 | Santobianco John G | New class of amine coinitiators in photoinitiated polymerizations |
| JP6753779B2 (ja) | 2014-08-05 | 2020-09-09 | ミヨシ油脂株式会社 | マトリックスに紫外線吸収能及び／又は高屈折率を付与するための添加剤とそれを用いた樹脂部材 |
| JP7712720B2 (ja) * | 2022-03-29 | 2025-07-24 | 国立研究開発法人産業技術総合研究所 | ポリエーテルエーテルケトン分解方法およびこの分解方法によって得られた分解生成物を原料とした新規物質 |
| WO2025063284A1 (ja) * | 2023-09-22 | 2025-03-27 | ミヨシ油脂株式会社 | 重合開始剤又は光増感剤、重合開始組成物及び樹脂の製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6905795A (enExample) * | 1968-04-16 | 1969-10-20 | ||
| DE2155000A1 (de) * | 1971-11-05 | 1973-05-10 | Bayer Ag | Thiomethylierte benzophenone |
| US3827959A (en) * | 1973-01-12 | 1974-08-06 | Scm Corp | Process for photopolymerization with carbonylated phenyl nuclear sulfonyl chloride sensitizer |
-
1976
- 1976-01-23 DE DE19762602419 patent/DE2602419A1/de not_active Withdrawn
- 1976-12-27 IT IT30903/76A patent/IT1067967B/it active
-
1977
- 1977-01-06 US US05/757,382 patent/US4054682A/en not_active Expired - Lifetime
- 1977-01-19 BE BE174191A patent/BE850519A/xx not_active IP Right Cessation
- 1977-01-20 FR FR7701579A patent/FR2338952A1/fr active Granted
- 1977-01-20 NL NL7700579A patent/NL7700579A/xx not_active Application Discontinuation
- 1977-01-21 GB GB2482/77A patent/GB1566953A/en not_active Expired
- 1977-01-24 JP JP598077A patent/JPS52104592A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0005530A1 (de) * | 1978-05-23 | 1979-11-28 | Ciba-Geigy Ag | Neue Mercaptophenylketone und deren Verwendung als Initiatoren für die Photopolymerisation äthylenisch ungesättigter Verbindungen |
| CN113056529A (zh) * | 2018-11-26 | 2021-06-29 | 爱克发-格法特公司 | 用于制造印刷电路板的可辐射固化的喷墨油墨 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2338952A1 (fr) | 1977-08-19 |
| NL7700579A (nl) | 1977-07-26 |
| FR2338952B3 (enExample) | 1979-09-21 |
| BE850519A (fr) | 1977-07-19 |
| GB1566953A (en) | 1980-05-08 |
| IT1067967B (it) | 1985-03-21 |
| JPS52104592A (en) | 1977-09-02 |
| US4054682A (en) | 1977-10-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |