SE443794C - Fotopolymeriserbar komposition - Google Patents
Fotopolymeriserbar kompositionInfo
- Publication number
- SE443794C SE443794C SE7900979A SE7900979A SE443794C SE 443794 C SE443794 C SE 443794C SE 7900979 A SE7900979 A SE 7900979A SE 7900979 A SE7900979 A SE 7900979A SE 443794 C SE443794 C SE 443794C
- Authority
- SE
- Sweden
- Prior art keywords
- organic material
- integer
- organic
- hydroxyl
- aromatic
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 42
- 239000000463 material Substances 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 239000011368 organic material Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000003700 epoxy group Chemical group 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052752 metalloid Inorganic materials 0.000 claims description 2
- 150000002738 metalloids Chemical class 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- -1 cyclicidol Chemical compound 0.000 description 18
- 239000004593 Epoxy Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 150000002118 epoxides Chemical class 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 125000006353 oxyethylene group Chemical group 0.000 description 9
- 229920000647 polyepoxide Polymers 0.000 description 8
- 239000003822 epoxy resin Substances 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- ORTVZLZNOYNASJ-UPHRSURJSA-N (z)-but-2-ene-1,4-diol Chemical compound OC\C=C/CO ORTVZLZNOYNASJ-UPHRSURJSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJUPATPRPWEWEG-UHFFFAOYSA-N 4,14,20-triazahexacyclo[13.6.2.02,14.03,11.05,10.016,21]tricosa-2,4,6,8,10,12,17,19-octaene Chemical compound C1CC2C3C=CC=NC3C1c1n2ccc2c1nc1ccccc21 IJUPATPRPWEWEG-UHFFFAOYSA-N 0.000 description 2
- OECTYKWYRCHAKR-UHFFFAOYSA-N 4-vinylcyclohexene dioxide Chemical compound C1OC1C1CC2OC2CC1 OECTYKWYRCHAKR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
- 239000011354 acetal resin Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000001346 alkyl aryl ethers Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- LMMDJMWIHPEQSJ-UHFFFAOYSA-N bis[(3-methyl-7-oxabicyclo[4.1.0]heptan-4-yl)methyl] hexanedioate Chemical compound C1C2OC2CC(C)C1COC(=O)CCCCC(=O)OCC1CC2OC2CC1C LMMDJMWIHPEQSJ-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000000466 oxiranyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920006267 polyester film Polymers 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 125000005409 triarylsulfonium group Chemical group 0.000 description 2
- 150000004072 triols Chemical class 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YFRKDLHKSICTKM-KCXSEMKSSA-N (Z)-4-oxo-4-(3-phenylprop-2-enoxy)but-2-enoic acid Chemical compound OC(=O)\C=C/C(=O)OCC=CC1=CC=CC=C1 YFRKDLHKSICTKM-KCXSEMKSSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-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
- AJKXDPSHWRTFOZ-UHFFFAOYSA-N 2-ethylhexane-1,6-diol Chemical compound CCC(CO)CCCCO AJKXDPSHWRTFOZ-UHFFFAOYSA-N 0.000 description 1
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 description 1
- QBJWYMFTMJFGOL-UHFFFAOYSA-N 2-hexadecyloxirane Chemical compound CCCCCCCCCCCCCCCCC1CO1 QBJWYMFTMJFGOL-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical class OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- UTHHKUBZIBBOIT-UHFFFAOYSA-N 4-methyl-2-[(4-methyl-7-oxabicyclo[4.1.0]heptan-3-yl)methyl]-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylic acid Chemical compound CC1CC2OC2C(CC2CC3OC3CC2C)=C1C(O)=O UTHHKUBZIBBOIT-UHFFFAOYSA-N 0.000 description 1
- XAYDWGMOPRHLEP-UHFFFAOYSA-N 6-ethenyl-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCCC2OC21C=C XAYDWGMOPRHLEP-UHFFFAOYSA-N 0.000 description 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 description 1
- NHJIDZUQMHKGRE-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-yl 2-(7-oxabicyclo[4.1.0]heptan-4-yl)acetate Chemical compound C1CC2OC2CC1OC(=O)CC1CC2OC2CC1 NHJIDZUQMHKGRE-UHFFFAOYSA-N 0.000 description 1
- AOYQDLJWKKUFEG-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]hept-4-ene-4-carboxylate Chemical compound C=1C2OC2CCC=1C(=O)OCC1CC2OC2CC1 AOYQDLJWKKUFEG-UHFFFAOYSA-N 0.000 description 1
- YXALYBMHAYZKAP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptan-4-ylmethyl 7-oxabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1CC2OC2CC1C(=O)OCC1CC2OC2CC1 YXALYBMHAYZKAP-UHFFFAOYSA-N 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 1
- ADAHGVUHKDNLEB-UHFFFAOYSA-N Bis(2,3-epoxycyclopentyl)ether Chemical compound C1CC2OC2C1OC1CCC2OC21 ADAHGVUHKDNLEB-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 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
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- RCTTZBARGUOWRR-UHFFFAOYSA-N CCC.C(CC)OC1=C2C(=C(C=C1)O)O2 Chemical compound CCC.C(CC)OC1=C2C(=C(C=C1)O)O2 RCTTZBARGUOWRR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KBEBGUQPQBELIU-CMDGGOBGSA-N Ethyl cinnamate Chemical compound CCOC(=O)\C=C\C1=CC=CC=C1 KBEBGUQPQBELIU-CMDGGOBGSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910052787 antimony Chemical group 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000005410 aryl sulfonium group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 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 1
- 229910052796 boron Inorganic materials 0.000 description 1
- DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
- 239000001405 butyl (E)-3-phenylprop-2-enoate Substances 0.000 description 1
- OHHIVLJVBNCSHV-KTKRTIGZSA-N butyl cinnamate Chemical compound CCCCOC(=O)\C=C/C1=CC=CC=C1 OHHIVLJVBNCSHV-KTKRTIGZSA-N 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229920006217 cellulose acetate butyrate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000004965 chloroalkyl group Chemical group 0.000 description 1
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- KBEBGUQPQBELIU-UHFFFAOYSA-N cinnamic acid ethyl ester Natural products CCOC(=O)C=CC1=CC=CC=C1 KBEBGUQPQBELIU-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical group C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZTFPVUVWTIJYHK-UHFFFAOYSA-N ethyl prop-2-enoate;methyl 2-methylprop-2-enoate;oxiran-2-ylmethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C=C.COC(=O)C(C)=C.CC(=C)C(=O)OCC1CO1 ZTFPVUVWTIJYHK-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- ACXCWUMCBFSPDP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;oxiran-2-ylmethyl 2-methylprop-2-enoate Chemical compound COC(=O)C(C)=C.CC(=C)C(=O)OCC1CO1 ACXCWUMCBFSPDP-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LOTWRKOXHCMWDB-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)benzamide Chemical compound OCCN(CCO)C(=O)C1=CC=CC=C1 LOTWRKOXHCMWDB-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- LUUFSCNUZAYHAT-UHFFFAOYSA-N octadecane-1,18-diol Chemical compound OCCCCCCCCCCCCCCCCCCO LUUFSCNUZAYHAT-UHFFFAOYSA-N 0.000 description 1
- 125000001741 organic sulfur group Chemical group 0.000 description 1
- YPNZYYWORCABPU-UHFFFAOYSA-N oxiran-2-ylmethyl 2-methylprop-2-enoate;styrene Chemical compound C=CC1=CC=CC=C1.CC(=C)C(=O)OCC1CO1 YPNZYYWORCABPU-UHFFFAOYSA-N 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 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
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920005906 polyester polyol Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
-
- 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
- C08G59/687—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 containing sulfur
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/876,113 US4218531A (en) | 1978-02-08 | 1978-02-08 | Addition of ethylenically unsaturated materials to control odor in photopolymerizable epoxy compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE7900979L SE7900979L (sv) | 1979-08-09 |
| SE443794B SE443794B (sv) | 1986-03-10 |
| SE443794C true SE443794C (sv) | 1991-10-21 |
Family
ID=25367022
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7900979A SE443794C (sv) | 1978-02-08 | 1979-02-05 | Fotopolymeriserbar komposition |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4218531A (de) |
| JP (1) | JPS54117599A (de) |
| AU (1) | AU527513B2 (de) |
| BE (1) | BE874003A (de) |
| BR (1) | BR7900746A (de) |
| CA (1) | CA1134536A (de) |
| CH (1) | CH642387A5 (de) |
| DE (1) | DE2904625A1 (de) |
| FR (1) | FR2416920A1 (de) |
| GB (2) | GB2014151B (de) |
| IN (1) | IN150880B (de) |
| SE (1) | SE443794C (de) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2452731A1 (fr) * | 1979-03-28 | 1980-10-24 | Rhone Poulenc Syst | Compositions photopolymerisables filmogenes developpables a l'eau |
| FR2452729A1 (fr) * | 1979-03-28 | 1980-10-24 | Rhone Poulenc Syst | Article pour la realisation d'auxiliaires visuels tels que films de montage pour l'impression phonographique |
| FR2475753B1 (fr) * | 1980-02-11 | 1987-03-20 | Rhone Poulenc Syst | Plaque lithographique a base de fluoborate de paradiazodiphenylamine et de resine epoxy liquide |
| US4339567A (en) * | 1980-03-07 | 1982-07-13 | Ciba-Geigy Corporation | Photopolymerization by means of sulphoxonium salts |
| US4362263A (en) * | 1980-04-24 | 1982-12-07 | Westinghouse Electric Corp. | Solderable solventless UV curable enamel |
| US4383025A (en) * | 1980-07-10 | 1983-05-10 | Ciba-Geigy Corporation | Photopolymerization by means of sulfoxonium salts |
| US4398014A (en) * | 1980-11-04 | 1983-08-09 | Ciba-Geigy Corporation | Sulfoxonium salts and their use as polymerization catalysts |
| JPS5943015A (ja) * | 1982-09-02 | 1984-03-09 | Toyobo Co Ltd | 硬化型樹脂組成物 |
| US4593051A (en) * | 1983-02-07 | 1986-06-03 | Union Carbide Corporation | Photocopolymerizable compositons based on epoxy and polymer/hydroxyl-containing organic materials |
| US4818776A (en) * | 1983-02-07 | 1989-04-04 | Union Carbide Corporation | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials having primary hydroxyl content |
| US4814361A (en) * | 1983-02-07 | 1989-03-21 | Union Carbide Corporation | Blends of epoxides and monoepoxides |
| US4874798A (en) * | 1983-02-07 | 1989-10-17 | Union Carbide Corporation | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials and substituted cycloaliphatic monoepoxide reactive diluents |
| US4812488A (en) * | 1983-02-07 | 1989-03-14 | Union Carbide Corporation | Photocopolymerizable compositions based on hydroxyl-containing organic materials and substituted cycloaliphatic monoepoxide reactive diluents |
| US4622349A (en) * | 1983-02-07 | 1986-11-11 | Union Carbide Corporation | Blends of epoxides and monoepoxides |
| JPS6014729U (ja) * | 1983-07-08 | 1985-01-31 | 小瀬木 勇 | ナイフケ−ス等の吊下係止具 |
| US4694029A (en) * | 1985-04-09 | 1987-09-15 | Cook Paint And Varnish Company | Hybrid photocure system |
| US4892894A (en) * | 1985-11-07 | 1990-01-09 | Union Carbide Chemical And Plastics Company Inc. | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials |
| US4657779A (en) * | 1986-03-19 | 1987-04-14 | Desoto, Inc. | Shrinkage-resistant ultraviolet-curing coatings |
| US5110711A (en) * | 1989-10-10 | 1992-05-05 | International Business Machines Corporation | Method for forming a pattern |
| US5059512A (en) * | 1989-10-10 | 1991-10-22 | International Business Machines Corporation | Ultraviolet light sensitive photoinitiator compositions, use thereof and radiation sensitive compositions |
| DE4421623A1 (de) * | 1994-06-21 | 1996-01-04 | Thera Ges Fuer Patente | Mehrkomponentige, kationisch härtende Epoxidmassen und deren Verwendung sowie Verfahren zur Herstellung gehärteter Massen |
| US20030108810A1 (en) * | 2001-08-22 | 2003-06-12 | Williamson Sue Ellen | Deodorizing agent for sulfur- or nitrogen-containing salt photoinitiators |
| CA2804049A1 (en) | 2010-06-28 | 2012-01-19 | Dow Global Technologies Llc | Curable resin compositions |
| JP5778768B2 (ja) | 2010-06-28 | 2015-09-16 | ダウ グローバル テクノロジーズ エルエルシー | 硬化性樹脂組成物 |
| WO2013188070A1 (en) | 2012-06-15 | 2013-12-19 | Dow Global Technologies Llc | Curable compositions |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3018262A (en) * | 1957-05-01 | 1962-01-23 | Shell Oil Co | Curing polyepoxides with certain metal salts of inorganic acids |
| NL128404C (de) * | 1959-12-24 | |||
| FR1411267A (fr) * | 1963-08-20 | 1965-09-17 | Denki Kagaku Kogyo Kk | Perfectionnements aux caoutchoucs au polychloroprène |
| US4058401A (en) * | 1974-05-02 | 1977-11-15 | General Electric Company | Photocurable compositions containing group via aromatic onium salts |
| US4058400A (en) * | 1974-05-02 | 1977-11-15 | General Electric Company | Cationically polymerizable compositions containing group VIa onium salts |
| IE42085B1 (en) * | 1974-09-18 | 1980-06-04 | Ici Ltd | Photopolymerisable compositions |
| US4069054A (en) * | 1975-09-02 | 1978-01-17 | Minnesota Mining And Manufacturing Company | Photopolymerizable composition containing a sensitized aromatic sulfonium compound and a cationacally polymerizable monomer |
| US4108747A (en) * | 1976-07-14 | 1978-08-22 | General Electric Company | Curable compositions and method for curing such compositions |
| US4138255A (en) * | 1977-06-27 | 1979-02-06 | General Electric Company | Photo-curing method for epoxy resin using group VIa onium salt |
| US4156035A (en) * | 1978-05-09 | 1979-05-22 | W. R. Grace & Co. | Photocurable epoxy-acrylate compositions |
-
1978
- 1978-02-08 US US05/876,113 patent/US4218531A/en not_active Expired - Lifetime
- 1978-12-28 CA CA000318743A patent/CA1134536A/en not_active Expired
-
1979
- 1979-02-05 SE SE7900979A patent/SE443794C/sv not_active IP Right Cessation
- 1979-02-07 JP JP1318779A patent/JPS54117599A/ja active Granted
- 1979-02-07 AU AU44026/79A patent/AU527513B2/en not_active Ceased
- 1979-02-07 BR BR7900746A patent/BR7900746A/pt unknown
- 1979-02-07 FR FR7903068A patent/FR2416920A1/fr active Granted
- 1979-02-07 CH CH121279A patent/CH642387A5/de not_active IP Right Cessation
- 1979-02-07 BE BE0/193325A patent/BE874003A/xx not_active IP Right Cessation
- 1979-02-07 DE DE19792904625 patent/DE2904625A1/de active Granted
- 1979-02-07 GB GB7904288A patent/GB2014151B/en not_active Expired
- 1979-02-07 IN IN116/CAL/79A patent/IN150880B/en unknown
- 1979-02-07 GB GB8114579A patent/GB2074595B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB2074595B (en) | 1982-12-22 |
| JPS54117599A (en) | 1979-09-12 |
| AU527513B2 (en) | 1983-03-10 |
| IN150880B (de) | 1983-01-08 |
| BE874003A (fr) | 1979-08-07 |
| JPS6357450B2 (de) | 1988-11-11 |
| CH642387A5 (de) | 1984-04-13 |
| AU4402679A (en) | 1979-08-16 |
| BR7900746A (pt) | 1979-08-28 |
| CA1134536A (en) | 1982-10-26 |
| DE2904625A1 (de) | 1979-08-09 |
| DE2904625C2 (de) | 1988-08-11 |
| SE7900979L (sv) | 1979-08-09 |
| US4218531A (en) | 1980-08-19 |
| GB2014151B (en) | 1982-07-07 |
| GB2014151A (en) | 1979-08-22 |
| FR2416920A1 (fr) | 1979-09-07 |
| SE443794B (sv) | 1986-03-10 |
| GB2074595A (en) | 1981-11-04 |
| FR2416920B1 (de) | 1983-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SE443794C (sv) | Fotopolymeriserbar komposition | |
| US4231951A (en) | Complex salt photoinitiator | |
| CA1121092A (en) | Triarylsulfonium complex salt photoinitiator containing a fluoroantimonate anion | |
| US4256828A (en) | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials | |
| US4318766A (en) | Process of using photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials | |
| US4977199A (en) | Photo curable blends of 2-methyoxytetrahydropyran and a cycloaliphatic diepoxide | |
| CA1243147A (en) | Photocopolymerizable compositions based on epoxy and hydroxyl containing organic materials and substituted cycloaliphatic monoepoxide reactive diluents | |
| US4175963A (en) | Method of exposing and curing an epoxy composition containing an aromatic onium salt | |
| US4874798A (en) | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials and substituted cycloaliphatic monoepoxide reactive diluents | |
| US4069055A (en) | Photocurable epoxy compositions containing group Va onium salts | |
| US4977198A (en) | UV curable epoxy functional silicones | |
| US4378277A (en) | Photopolymerizable epoxy-containing compositions | |
| CH618674A5 (de) | ||
| DE2731396A1 (de) | Haertbare zusammensetzungen | |
| US4622349A (en) | Blends of epoxides and monoepoxides | |
| US4115295A (en) | Polymerizable compositions containing highly fluorinated aliphatic sulfonyl protonic acid catalyst | |
| DE3902114A1 (de) | Strahlungsempfindliche, ethylenisch ungesaettigte, copolymerisierbare sulfoniumsalze und verfahren zu deren herstellung | |
| JP2024069387A5 (ja) | ウエットエッチング液に対する保護膜形成組成物及びパターン形成方法 | |
| CA1246786A (en) | Blends of cyclic vinyl ether containing compounds and epoxides | |
| US4818776A (en) | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials having primary hydroxyl content | |
| US4175973A (en) | Curable compositions | |
| US4892894A (en) | Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials | |
| US4812488A (en) | Photocopolymerizable compositions based on hydroxyl-containing organic materials and substituted cycloaliphatic monoepoxide reactive diluents | |
| US4324679A (en) | Controlling odor in photopolymerization | |
| KR20060133482A (ko) | 알칼리 현상성 감광성 수지조성물 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
Ref document number: 7900979-1 Effective date: 19920510 Format of ref document f/p: F |