CA2786630C - Macro-photoinitiators and curable compositions thereof - Google Patents
Macro-photoinitiators and curable compositions thereof Download PDFInfo
- Publication number
- CA2786630C CA2786630C CA2786630A CA2786630A CA2786630C CA 2786630 C CA2786630 C CA 2786630C CA 2786630 A CA2786630 A CA 2786630A CA 2786630 A CA2786630 A CA 2786630A CA 2786630 C CA2786630 C CA 2786630C
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- Canada
- Prior art keywords
- photoinitiator
- macro
- group
- alkyl
- 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.)
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- 239000000203 mixture Substances 0.000 title claims abstract description 183
- 229920000642 polymer Polymers 0.000 claims abstract description 107
- 238000000034 method Methods 0.000 claims abstract description 39
- 238000010560 atom transfer radical polymerization reaction Methods 0.000 claims abstract description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 33
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 29
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 24
- 230000027756 respiratory electron transport chain Effects 0.000 claims abstract description 9
- -1 C3-C12 cycloalkyl Chemical group 0.000 claims description 104
- 239000000178 monomer Substances 0.000 claims description 92
- 239000003999 initiator Substances 0.000 claims description 80
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 230000005855 radiation Effects 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000000376 reactant Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 229920002554 vinyl polymer Polymers 0.000 claims description 22
- 150000001336 alkenes Chemical class 0.000 claims description 20
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 125000005647 linker group Chemical group 0.000 claims description 16
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 16
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 14
- 150000001735 carboxylic acids Chemical class 0.000 claims description 14
- 150000002148 esters Chemical class 0.000 claims description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 11
- 150000007824 aliphatic compounds Chemical class 0.000 claims description 10
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 10
- 125000000746 allylic group Chemical group 0.000 claims description 9
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 7
- 239000000853 adhesive Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 229920001567 vinyl ester resin Polymers 0.000 claims description 7
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 6
- 230000001070 adhesive effect Effects 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000003505 polymerization initiator Substances 0.000 claims description 6
- 229920001400 block copolymer Polymers 0.000 claims description 5
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
- 229920001519 homopolymer Polymers 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920005604 random copolymer Polymers 0.000 claims description 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052799 carbon Inorganic materials 0.000 claims description 3
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 3
- 229920000587 hyperbranched polymer Polymers 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims 2
- 125000003396 thiol group Chemical class [H]S* 0.000 abstract description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 47
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- 229920001897 terpolymer Polymers 0.000 description 29
- 239000002904 solvent Substances 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 22
- 239000000758 substrate Substances 0.000 description 22
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- 239000003054 catalyst Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 150000003573 thiols Chemical class 0.000 description 18
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 description 17
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 125000001246 bromo group Chemical group Br* 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000000052 comparative effect Effects 0.000 description 15
- 230000000670 limiting effect Effects 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- 125000005843 halogen group Chemical group 0.000 description 14
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 13
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 230000004044 response Effects 0.000 description 12
- 229910052723 transition metal Inorganic materials 0.000 description 12
- 150000003624 transition metals Chemical class 0.000 description 12
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 239000010408 film Substances 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 11
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 229940102838 methylmethacrylate Drugs 0.000 description 10
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001723 curing Methods 0.000 description 9
- 230000000977 initiatory effect Effects 0.000 description 9
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 8
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 8
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000011521 glass Substances 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 8
- 239000004926 polymethyl methacrylate Substances 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 238000003848 UV Light-Curing Methods 0.000 description 7
- 239000010949 copper Substances 0.000 description 7
- 239000003446 ligand Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000001542 size-exclusion chromatography Methods 0.000 description 7
- 150000003623 transition metal compounds Chemical class 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
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- 239000012634 fragment Substances 0.000 description 6
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- 125000005842 heteroatom Chemical group 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 229910052786 argon Inorganic materials 0.000 description 5
- 125000000732 arylene group Chemical group 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
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- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 4
- QLLUAUADIMPKIH-UHFFFAOYSA-N 1,2-bis(ethenyl)naphthalene Chemical compound C1=CC=CC2=C(C=C)C(C=C)=CC=C21 QLLUAUADIMPKIH-UHFFFAOYSA-N 0.000 description 4
- HIACAHMKXQESOV-UHFFFAOYSA-N 1,2-bis(prop-1-en-2-yl)benzene Chemical class CC(=C)C1=CC=CC=C1C(C)=C HIACAHMKXQESOV-UHFFFAOYSA-N 0.000 description 4
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
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- 125000002346 iodo group Chemical group I* 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
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- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 3
- 125000006649 (C2-C20) alkynyl group Chemical group 0.000 description 3
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- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 3
- 125000005865 C2-C10alkynyl group Chemical group 0.000 description 3
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- 125000003342 alkenyl group Chemical group 0.000 description 3
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- VMGSQCIDWAUGLQ-UHFFFAOYSA-N n',n'-bis[2-(dimethylamino)ethyl]-n,n-dimethylethane-1,2-diamine Chemical compound CN(C)CCN(CCN(C)C)CCN(C)C VMGSQCIDWAUGLQ-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
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- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 3
- 238000000016 photochemical curing Methods 0.000 description 3
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Classifications
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- 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
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
-
- 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
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- 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
- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polymerisation Methods In General (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US31619010P | 2010-03-22 | 2010-03-22 | |
| US61/316,190 | 2010-03-22 | ||
| PCT/US2011/025153 WO2011119272A2 (en) | 2010-03-22 | 2011-02-17 | Macro-photoinitiators and curable compositions thereof |
Publications (2)
| Publication Number | Publication Date |
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| CA2786630A1 CA2786630A1 (en) | 2011-09-29 |
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| US9097979B2 (en) | 2013-03-13 | 2015-08-04 | Wisconsin Alumni Research Foundation | Block copolymer-based mask structures for the growth of nanopatterned polymer brushes |
| US10340816B2 (en) * | 2014-08-29 | 2019-07-02 | Mitsubishi Electric Corporation | Semiconductor device and multiphase semiconductor device |
| US9587062B2 (en) * | 2014-12-15 | 2017-03-07 | Henkel IP & Holding GmbH and Henkel AG & Co. KGaA | Photocrosslinkable block copolymers for hot-melt adhesives |
| JP2018501383A (ja) * | 2015-01-08 | 2018-01-18 | ヘンケル アイピー アンド ホールディング ゲゼルシャフト ミット ベシュレンクテル ハフツング | 狭い多分散指数を有する高分子量ポリアクリレートの製造方法、および、それから製造された組成物 |
| US10492888B2 (en) | 2015-07-07 | 2019-12-03 | Align Technology, Inc. | Dental materials using thermoset polymers |
| WO2017180998A2 (en) * | 2016-04-15 | 2017-10-19 | Beckman Coulter, Inc. | Photoactive macromolecules and uses thereof |
| CN109476774B (zh) * | 2016-07-11 | 2021-01-12 | 3M创新有限公司 | 使用可控自由基引发剂的聚合物材料及制备方法 |
| CN111095046B (zh) | 2017-09-15 | 2022-07-22 | 富士胶片株式会社 | 组合物、膜、层叠体、红外线透射滤波器、固体摄像元件及红外线传感器 |
| KR102935711B1 (ko) | 2018-05-04 | 2026-03-09 | 얼라인 테크널러지, 인크. | 고온 석판인쇄-기반 광중합 공정에서 사용하기 위한 경화형 조성물 및 이로부터 가교 중합체를 제조하는 방법 |
| CN116640061A (zh) | 2018-05-04 | 2023-08-25 | 阿莱恩技术有限公司 | 可聚合单体及其聚合方法 |
| EP3854821A4 (en) | 2018-09-20 | 2021-11-17 | FUJIFILM Corporation | CURING COMPOSITION, CURED FILM, INFRARED TRANSMISSION FILTER, LAMINATE, SOLID STATE IMAGING ELEMENT, SENSOR, AND PATTERN FORMING METHOD |
| JP7260847B2 (ja) | 2019-02-26 | 2023-04-19 | 株式会社リコー | 活性エネルギー線重合性開始剤、活性エネルギー線重合性組成物、活性エネルギー線重合性インク、インク収容容器、画像形成方法および画像形成装置 |
| TWI842917B (zh) | 2019-06-27 | 2024-05-21 | 日商富士軟片股份有限公司 | 組成物、膜及光感測器 |
| EP4024097B1 (en) | 2019-08-29 | 2024-05-22 | FUJIFILM Corporation | Composition, film, near-infrared cut-off filter, pattern formation method, laminate, solid-state imaging element, infrared sensor, image display device, camera module and compound |
| EP4024096A4 (en) | 2019-08-30 | 2022-12-14 | FUJIFILM Corporation | COMPOSITION, FILM, OPTICAL FILTER AND METHOD OF MANUFACTURE THEREOF, SOLID STATE IMAGING ELEMENT, INFRARED SENSOR AND SENSOR MODULE |
| US12215223B2 (en) | 2019-10-31 | 2025-02-04 | Align Technology, Inc. | Crystallizable resins |
| CN110981995B (zh) * | 2019-12-27 | 2021-12-07 | 阜阳欣奕华材料科技有限公司 | 一种低迁移型光引发剂及其制备方法和应用 |
| JP7470780B2 (ja) | 2020-03-30 | 2024-04-18 | 富士フイルム株式会社 | 組成物、膜及び光センサ |
| WO2022065006A1 (ja) | 2020-09-28 | 2022-03-31 | 富士フイルム株式会社 | 積層体の製造方法、アンテナインパッケージの製造方法、積層体及び組成物 |
| CN112430279A (zh) * | 2020-11-23 | 2021-03-02 | 濮阳展辰新材料有限公司 | 一种酰化法制备大分子光引发剂的方法及其应用 |
| TW202231641A (zh) | 2020-12-16 | 2022-08-16 | 日商富士軟片股份有限公司 | 組成物、膜、濾光器、固體攝像元件、圖像顯示裝置及紅外線感測器 |
| EP4266093A4 (en) | 2020-12-17 | 2024-08-28 | FUJIFILM Corporation | Composition, film, optical filter, solid-state imaging element, image display device, and infrared sensor |
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| TW202248755A (zh) | 2021-03-22 | 2022-12-16 | 日商富士軟片股份有限公司 | 負型感光性樹脂組成物、硬化物、積層體、硬化物的製造方法以及半導體元件 |
| EP4318057A4 (en) | 2021-03-29 | 2024-11-06 | FUJIFILM Corporation | BLACK PHOTOSENSITIVE COMPOSITION, METHOD FOR MANUFACTURING BLACK PHOTOSENSITIVE COMPOSITION, CURED FILM, COLOR FILTER, LIGHT-SHIELDING FILM, OPTICAL ELEMENT, SOLID-STATE IMAGE PICK-UP ELEMENT, AND HEADLIGHT UNIT |
| JP7259141B1 (ja) | 2021-08-31 | 2023-04-17 | 富士フイルム株式会社 | 硬化物の製造方法、積層体の製造方法、及び、半導体デバイスの製造方法、並びに、処理液 |
| WO2023054142A1 (ja) | 2021-09-29 | 2023-04-06 | 富士フイルム株式会社 | 組成物、樹脂、膜および光センサ |
| WO2023120037A1 (ja) | 2021-12-23 | 2023-06-29 | 富士フイルム株式会社 | 接合体の製造方法、接合体、積層体の製造方法、積層体、デバイスの製造方法、及び、デバイス、並びに、ポリイミド含有前駆体部形成用組成物 |
| WO2023162687A1 (ja) | 2022-02-24 | 2023-08-31 | 富士フイルム株式会社 | 樹脂組成物、硬化物、積層体、硬化物の製造方法、積層体の製造方法、半導体デバイスの製造方法、及び、半導体デバイス |
| JPWO2023190064A1 (enExample) | 2022-03-29 | 2023-10-05 | ||
| EP4579342A4 (en) | 2022-08-22 | 2026-01-14 | Fujifilm Corp | PHOTOSENSITIVE COMPOSITION, FILM AND OPTICAL SENSOR |
| CN117700588A (zh) * | 2022-09-15 | 2024-03-15 | 首尔大学校产学协力团 | 聚合物、制备聚合物的方法和使用聚合物制备的聚氨酯 |
| WO2024070963A1 (ja) | 2022-09-30 | 2024-04-04 | 富士フイルム株式会社 | 膜の製造方法、感光性樹脂組成物、硬化物の製造方法、硬化物、及び積層体 |
| WO2024071237A1 (ja) | 2022-09-30 | 2024-04-04 | 富士フイルム株式会社 | 樹脂組成物、硬化物、積層体、硬化物の製造方法、積層体の製造方法、半導体デバイスの製造方法、及び、半導体デバイス |
| TW202424051A (zh) | 2022-09-30 | 2024-06-16 | 日商富士軟片股份有限公司 | 樹脂組成物、硬化物、積層體、硬化物的製造方法、積層體的製造方法、半導體元件的製造方法及半導體元件 |
| EP4692947A4 (en) | 2023-03-31 | 2026-07-15 | Fujifilm Corp | CHEMICAL SOLUTION AND PATTERN FORMATION PROCESS |
| US20250021006A1 (en) * | 2023-07-11 | 2025-01-16 | Tokyo Electron Limited | Wafer Bow Mitigation |
| GB202416930D0 (en) * | 2024-11-18 | 2025-01-01 | Scott Bader Co | Polymeric photoinitiating compositions |
| CN121271472B (zh) * | 2025-10-21 | 2026-06-19 | 拓迪化学(上海)股份有限公司 | 一种uv延迟固化耐电解液胶带及其制备方法和应用 |
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| IE45111B1 (en) | 1976-07-14 | 1982-06-30 | Loctite Ltd | Cyanoacrylate adhesive paste compositions |
| IE45626B1 (en) | 1976-07-14 | 1982-10-20 | Loctite Ltd | Filled cyanoacrylate adhesive compositions |
| US6458864B1 (en) | 1998-05-29 | 2002-10-01 | Ciba Specialty Chemicals Corporation | Photoinitiators having chain transfer groups polymerized to obtain macrophotoinitiators useful to give block copolymers |
| JP2002544205A (ja) * | 1999-05-10 | 2002-12-24 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | 新規な光開始剤及びその応用 |
| EP1517958B1 (en) * | 2002-07-03 | 2009-03-25 | The Procter & Gamble Company | Radiation curable low stress relaxation elastomeric materials |
| JP2009209275A (ja) * | 2008-03-05 | 2009-09-17 | Fujifilm Corp | 光硬化性コーティング組成物、オーバープリント及びその製造方法 |
| US9243083B2 (en) * | 2008-04-03 | 2016-01-26 | Henkel IP & Holding GmbH | Thiol-ene cured oil-resistant polyacrylate sealants for in-place gasketing applications |
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| EP2550307B1 (en) | 2017-11-22 |
| EP2550307A2 (en) | 2013-01-30 |
| KR20130018702A (ko) | 2013-02-25 |
| KR101437751B1 (ko) | 2014-09-03 |
| CA2786630A1 (en) | 2011-09-29 |
| CN102770465A (zh) | 2012-11-07 |
| JP2013522445A (ja) | 2013-06-13 |
| JP5955832B2 (ja) | 2016-07-20 |
| US20130018122A1 (en) | 2013-01-17 |
| ES2657710T3 (es) | 2018-03-06 |
| US8748503B2 (en) | 2014-06-10 |
| WO2011119272A2 (en) | 2011-09-29 |
| CN102770465B (zh) | 2015-04-22 |
| WO2011119272A3 (en) | 2012-01-05 |
| EP2550307A4 (en) | 2014-03-19 |
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