BR112012020628B1 - fotoiniciador de éter polialquílico, uso de um fotoiniciador de éter polialquílico, e, método para curar uma composição de matriz - Google Patents
fotoiniciador de éter polialquílico, uso de um fotoiniciador de éter polialquílico, e, método para curar uma composição de matriz Download PDFInfo
- Publication number
- BR112012020628B1 BR112012020628B1 BR112012020628A BR112012020628A BR112012020628B1 BR 112012020628 B1 BR112012020628 B1 BR 112012020628B1 BR 112012020628 A BR112012020628 A BR 112012020628A BR 112012020628 A BR112012020628 A BR 112012020628A BR 112012020628 B1 BR112012020628 B1 BR 112012020628B1
- Authority
- BR
- Brazil
- Prior art keywords
- polyalkyl ether
- photoinitiator
- ether photoinitiator
- photoinitiator according
- fractions
- Prior art date
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 101
- 239000000203 mixture Substances 0.000 title claims abstract description 21
- 239000011159 matrix material Substances 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 239000012965 benzophenone Substances 0.000 claims description 26
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 21
- -1 polyethylenes Polymers 0.000 claims description 20
- 150000002170 ethers Chemical class 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 150000003457 sulfones Chemical class 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 9
- 150000001540 azides Chemical class 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000004056 anthraquinones Chemical class 0.000 claims description 7
- CHIHQLCVLOXUJW-UHFFFAOYSA-N benzoic anhydride Chemical class C=1C=CC=CC=1C(=O)OC(=O)C1=CC=CC=C1 CHIHQLCVLOXUJW-UHFFFAOYSA-N 0.000 claims description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- 150000008366 benzophenones Chemical class 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000006850 spacer group Chemical group 0.000 claims description 4
- 150000007964 xanthones Chemical class 0.000 claims description 4
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 3
- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims description 3
- IANQGOCKLOCSFY-UHFFFAOYSA-N 4-phenyl-4H-chromene-2,3-dione Chemical class O=C1C(=O)OC2=CC=CC=C2C1C1=CC=CC=C1 IANQGOCKLOCSFY-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 239000004698 Polyethylene Substances 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 150000008376 fluorenones Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 150000002823 nitrates Chemical class 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 229920000573 polyethylene Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 230000005855 radiation Effects 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- 125000001033 ether group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 description 25
- 238000006116 polymerization reaction Methods 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 15
- 238000001723 curing Methods 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 150000002118 epoxides Chemical class 0.000 description 10
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 9
- GJKGAPPUXSSCFI-UHFFFAOYSA-N 2-Hydroxy-4'-(2-hydroxyethoxy)-2-methylpropiophenone Chemical compound CC(C)(O)C(=O)C1=CC=C(OCCO)C=C1 GJKGAPPUXSSCFI-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 239000003999 initiator Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- 238000000576 coating method Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000004132 cross linking Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 5
- LJRIZGQRKVWXSI-UHFFFAOYSA-N [4-(oxiran-2-ylmethoxy)phenyl]-phenylmethanone Chemical compound C=1C=C(OCC2OC2)C=CC=1C(=O)C1=CC=CC=C1 LJRIZGQRKVWXSI-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229920002521 macromolecule Polymers 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000013508 migration Methods 0.000 description 4
- 230000005012 migration Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229930006711 bornane-2,3-dione Natural products 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 3
- VJJZFUUHKVZKLP-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-[4-[2-(oxiran-2-ylmethoxy)ethoxy]phenyl]propan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1OCCOCC1OC1 VJJZFUUHKVZKLP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- 230000035495 ADMET Effects 0.000 description 2
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Chemical group C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 238000010545 Norrish reaction Methods 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010535 acyclic diene metathesis reaction Methods 0.000 description 2
- 150000005215 alkyl ethers Chemical group 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004976 cyclobutylene group Chemical group 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- 125000004979 cyclopentylene group Chemical group 0.000 description 2
- 125000004980 cyclopropylene group Chemical group 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 238000001914 filtration Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
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- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 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 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 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 2
- 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 2
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
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- 229910052700 potassium Inorganic materials 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
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- 125000001544 thienyl group Chemical group 0.000 description 2
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- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- SMNMEQZTPHXYQO-UHFFFAOYSA-N 1-[5-(4-benzoylphenyl)thiophen-3-yl]pyrrole-2,5-dione Chemical compound C=1C=C(C=2SC=C(C=2)N2C(C=CC2=O)=O)C=CC=1C(=O)C1=CC=CC=C1 SMNMEQZTPHXYQO-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- ZWZGXLKXKAPXMZ-UHFFFAOYSA-N 2,2'-dihydroxy-3,3'-dimethoxy-5,5'-dipropyldiphenylmethane Chemical compound COC1=CC(CCC)=CC(CC=2C(=C(OC)C=C(CCC)C=2)O)=C1O ZWZGXLKXKAPXMZ-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical class OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- WCDSVWRUXWCYFN-UHFFFAOYSA-N 4-aminothiophenyl group Chemical group [H]N([H])C1=C([H])C([H])=C(S)C([H])=C1[H] WCDSVWRUXWCYFN-UHFFFAOYSA-N 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 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 1
- KOMDZQSPRDYARS-UHFFFAOYSA-N cyclopenta-1,3-diene titanium Chemical compound [Ti].C1C=CC=C1.C1C=CC=C1 KOMDZQSPRDYARS-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 1
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- 239000003505 polymerization initiator Substances 0.000 description 1
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- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
Classifications
-
- 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyethers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
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|---|---|---|---|
| DKPA201070065 | 2010-02-23 | ||
| DKPA201170007 | 2011-01-07 | ||
| PCT/DK2011/050055 WO2011103878A1 (en) | 2010-02-23 | 2011-02-23 | Polymeric photoinitiators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112012020628A2 BR112012020628A2 (pt) | 2018-03-20 |
| BR112012020628B1 true BR112012020628B1 (pt) | 2019-12-10 |
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| BR112012020628A BR112012020628B1 (pt) | 2010-02-23 | 2011-02-23 | fotoiniciador de éter polialquílico, uso de um fotoiniciador de éter polialquílico, e, método para curar uma composição de matriz |
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| EP (1) | EP2539374B1 (https=) |
| JP (2) | JP2013520523A (https=) |
| CN (1) | CN102762601B (https=) |
| BR (1) | BR112012020628B1 (https=) |
| RU (1) | RU2572839C2 (https=) |
| SG (1) | SG183124A1 (https=) |
| WO (1) | WO2011103878A1 (https=) |
Families Citing this family (19)
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| JP2013520523A (ja) | 2010-02-23 | 2013-06-06 | コロプラスト アクティーゼルスカブ | ポリマー光開始剤 |
| EP2585496A2 (en) * | 2010-06-22 | 2013-05-01 | Coloplast A/S | Hydrophilic gels derived from grafted photoinitiators |
| US9464143B2 (en) * | 2010-06-22 | 2016-10-11 | Coloplast A/S | Grafted photoinitiators |
| US20130096224A1 (en) * | 2010-06-22 | 2013-04-18 | Christian B. Nielsen | Polyurethane based photoinitiators |
| RU2586558C2 (ru) | 2010-06-22 | 2016-06-10 | Колопласт А/С | Гидрофильные гели из фотоинициаторов на основе полиалкиловых эфиров |
| SG186779A1 (en) * | 2010-06-22 | 2013-02-28 | Coloplast As | Skin-friendly adhesives from polyalkylether-based photoinitiators |
| US9114282B2 (en) | 2012-05-30 | 2015-08-25 | Nike, Inc. | Game ball or other article of sports equipment printed with visible light-curable ink and method |
| CN102863323A (zh) * | 2012-08-03 | 2013-01-09 | 北京化工大学常州先进材料研究院 | 可聚合二苯甲酮衍生物光引发剂的制备方法 |
| CN103122041A (zh) * | 2013-01-31 | 2013-05-29 | 北京化工大学常州先进材料研究院 | 一种新型自供氢二苯甲酮大分子光引发剂的制备及其方法 |
| CN104844736B (zh) * | 2015-04-30 | 2016-03-30 | 上海交通大学 | 氟化夺氢型高分子光引发剂、制备方法及其应用 |
| US10414953B2 (en) | 2016-02-19 | 2019-09-17 | Avery Dennison Corporation | Two stage methods for processing adhesives and related compositions |
| EP3301121A1 (en) * | 2016-09-30 | 2018-04-04 | Freie Universität Berlin | A thermoresponsive polymer and its use in a cell culture support |
| EP3665232A4 (en) | 2017-08-10 | 2021-04-07 | Sun Chemical Corporation | UV CURABLE COMPOSITIONS CONTAINING ACYLPHOSPHINE OXIDE PHOTOINITIATORS |
| AU2018392478B2 (en) | 2017-12-19 | 2023-03-16 | Avery Dennison Corporation | Post-polymerization functionalization of pendant functional groups |
| US11760713B2 (en) | 2018-12-17 | 2023-09-19 | Dow Global Technologies Llc | Benzophenone derivative |
| WO2020131339A1 (en) * | 2018-12-17 | 2020-06-25 | Dow Global Technologies Llc | Method for preparing a benzophenone derivative |
| CN109796954B (zh) * | 2019-01-08 | 2021-07-06 | 中国石油化工股份有限公司 | 一种耐温抗盐水溶性多元共聚物及其制备方法与应用 |
| US12595327B2 (en) * | 2020-07-10 | 2026-04-07 | Arkema France | Imide-linked polymeric photoinitiators |
| US11970596B2 (en) | 2020-09-25 | 2024-04-30 | 3M Innovative Properties Company | Photopolymerizable compositions and reaction products thereof |
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| US475018A (en) | 1892-05-17 | Car-wheel | ||
| DE1572060C3 (de) | 1966-01-07 | 1974-10-24 | Kalle Ag, 6202 Wiesbaden-Biebrich | Lichtempfindliche Kopierschicht |
| US4009128A (en) | 1975-01-14 | 1977-02-22 | Hercules Incorporated | Polymerization of epoxides |
| IT1147311B (it) | 1980-02-13 | 1986-11-19 | Stabil Bioterapico Farmachim | Eteri basici di 4-idrossi-benzofenoni con attivita' quali agenti betabloccanti e relativi procedimento di preparazione |
| AU552988B2 (en) | 1982-03-31 | 1986-06-26 | Shell Internationale Research Maatschappij B.V. | Polymerizing epoxides and catalyst suspensions for this |
| US4602097A (en) | 1984-06-11 | 1986-07-22 | Ulano Corporation | Water soluble photoinitiator benzophenone and thioxanthenone ethoxy-ether derivatives |
| SE444950B (sv) | 1984-09-28 | 1986-05-20 | Ytkemiska Inst | Ytbelagd artikel, forfarande och medel for framstellning derav samt anvendning derav |
| DE3512179A1 (de) | 1985-04-03 | 1986-12-04 | Merck Patent Gmbh, 6100 Darmstadt | Fotoinitiatoren fuer die fotopolymerisation in waessrigen systemen |
| US4684558A (en) | 1986-06-30 | 1987-08-04 | Nepera Inc. | Adhesive polyethylene oxide hydrogel sheet and its production |
| US5263992A (en) | 1986-10-17 | 1993-11-23 | Bio-Metric Systems, Inc. | Biocompatible device with covalently bonded biocompatible agent |
| DE3738567A1 (de) | 1987-03-12 | 1988-09-22 | Merck Patent Gmbh | Coreaktive fotoinitiatoren |
| DE4037079A1 (de) | 1990-11-22 | 1992-05-27 | Basf Ag | Ungesaettigte phenonderivate und ihre verwendung als haftklebstoffe |
| GB9507811D0 (en) | 1995-04-18 | 1995-05-31 | Lambson Fine Chemicals Limited | Novel photoinitiators |
| US5722424A (en) | 1995-09-29 | 1998-03-03 | Target Therapeutics, Inc. | Multi-coating stainless steel guidewire |
| GB9613114D0 (en) * | 1996-06-21 | 1996-08-28 | Lambson Fine Chemicals Limited | Photoinitiators |
| US6254802B1 (en) | 1997-05-16 | 2001-07-03 | Cryovac, Inc. | Low migratory photoinitiators for oxygen-scavenging compositions |
| US7547445B2 (en) | 1998-03-19 | 2009-06-16 | Surmodics, Inc. | Crosslinkable macromers |
| US6448301B1 (en) | 2000-09-08 | 2002-09-10 | 3M Innovative Properties Company | Crosslinkable polymeric compositions and use thereof |
| GB0125098D0 (en) | 2001-10-18 | 2001-12-12 | Coates Brothers Plc | Multi-functional thioxanthone photoinitiators |
| US7157535B2 (en) | 2002-06-19 | 2007-01-02 | National Starch And Chemical Investment Holding Corporation | Polymeric photoinitiators |
| DE10238559A1 (de) | 2002-08-22 | 2004-03-04 | Fresenius Medical Care Deutschland Gmbh | Verfahren zur Immobilisierung von Hydrogel-bildenden Polymeren auf Polymersubstratoberflächen |
| EP1549689B1 (en) | 2002-10-02 | 2010-05-26 | Coloplast A/S | A hydrogel |
| JP4585864B2 (ja) | 2002-11-05 | 2010-11-24 | 明成化学工業株式会社 | エチレンオキシド用重合触媒組成物および当該組成物を用いたポリ（エチレンオキシド）の製造方法 |
| WO2004075944A2 (en) | 2003-02-26 | 2004-09-10 | Coloplast A/S | A medical device having a coating comprising hydrogen peroxide and package therefore |
| WO2004099262A1 (en) * | 2003-05-06 | 2004-11-18 | Ciba Specialty Chemicals Holding Inc. | Novel trifunctional photoinitiators |
| US20050070688A1 (en) | 2003-09-26 | 2005-03-31 | 3M Innovative Properties Company | Reactive hydrophilic oligomers |
| US20050186427A1 (en) | 2004-02-19 | 2005-08-25 | The Procter & Gamble Company | Lubricious coated applicator |
| US7074839B2 (en) | 2004-03-01 | 2006-07-11 | 3M Innovative Properties Company | Crosslinkable hydrophilic materials from reactive oligomers having pendent photoinitiator groups |
| CA2589355A1 (en) | 2004-12-06 | 2005-12-06 | Surmodics, Inc. | Multifunctional medical articles |
| US7745505B2 (en) | 2004-12-29 | 2010-06-29 | Henkel Ag & Co. Kgaa | Photoinitiators and UV-crosslinkable acrylic polymers for pressure sensitive adhesives |
| CA2625638C (en) | 2005-11-08 | 2014-03-11 | Surmodics, Inc. | Ultra-thin photo-polymer coatings and uses thereof |
| US8076528B2 (en) | 2006-05-05 | 2011-12-13 | Coloplast A/S | Pressure sensitive adhesive composition comprising cross-linked polyalkylene oxide and water absorbent hydrophilic agents |
| JP2009544381A (ja) | 2006-07-25 | 2009-12-17 | コロプラスト アクティーゼルスカブ | 熱可塑性コーティングの光硬化 |
| WO2008071796A1 (en) * | 2006-12-15 | 2008-06-19 | Coloplast A/S | Coatings prepared from poly(ethylene oxide) and photo-initator-containing scaffolds |
| ES2600178T3 (es) | 2007-07-06 | 2017-02-07 | Coloplast A/S | Un adhesivo de contacto permeable |
| GB0722067D0 (en) | 2007-11-09 | 2007-12-19 | Lambson Fine Chemicals Ltd | Photoinitiators |
| JP2013520523A (ja) | 2010-02-23 | 2013-06-06 | コロプラスト アクティーゼルスカブ | ポリマー光開始剤 |
| EP2576632A1 (en) | 2010-06-01 | 2013-04-10 | Coloplast A/S | Gels from polystyrene-based photoinitiators |
| US9464143B2 (en) | 2010-06-22 | 2016-10-11 | Coloplast A/S | Grafted photoinitiators |
| US20130096224A1 (en) | 2010-06-22 | 2013-04-18 | Christian B. Nielsen | Polyurethane based photoinitiators |
| CN102947349B (zh) | 2010-06-22 | 2015-08-19 | 科洛普拉斯特公司 | 来自基于聚氨酯的光引发剂的亲水性凝胶 |
| EP2585496A2 (en) | 2010-06-22 | 2013-05-01 | Coloplast A/S | Hydrophilic gels derived from grafted photoinitiators |
| RU2586558C2 (ru) * | 2010-06-22 | 2016-06-10 | Колопласт А/С | Гидрофильные гели из фотоинициаторов на основе полиалкиловых эфиров |
-
2011
- 2011-02-23 JP JP2012553183A patent/JP2013520523A/ja not_active Withdrawn
- 2011-02-23 WO PCT/DK2011/050055 patent/WO2011103878A1/en not_active Ceased
- 2011-02-23 SG SG2012056800A patent/SG183124A1/en unknown
- 2011-02-23 RU RU2012139565/04A patent/RU2572839C2/ru active
- 2011-02-23 US US13/575,689 patent/US9175098B2/en active Active
- 2011-02-23 EP EP20110707784 patent/EP2539374B1/en active Active
- 2011-02-23 CN CN201180009912.XA patent/CN102762601B/zh active Active
- 2011-02-23 BR BR112012020628A patent/BR112012020628B1/pt not_active IP Right Cessation
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2015
- 2015-09-15 US US14/854,053 patent/US10040902B2/en active Active
- 2015-12-25 JP JP2015255083A patent/JP6272292B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN102762601B (zh) | 2014-03-26 |
| JP6272292B2 (ja) | 2018-01-31 |
| EP2539374B1 (en) | 2014-10-29 |
| WO2011103878A1 (en) | 2011-09-01 |
| BR112012020628A2 (pt) | 2018-03-20 |
| US10040902B2 (en) | 2018-08-07 |
| US9175098B2 (en) | 2015-11-03 |
| RU2012139565A (ru) | 2014-03-27 |
| US20130059940A1 (en) | 2013-03-07 |
| RU2572839C2 (ru) | 2016-01-20 |
| JP2016047935A (ja) | 2016-04-07 |
| US20160002400A1 (en) | 2016-01-07 |
| SG183124A1 (en) | 2012-09-27 |
| JP2013520523A (ja) | 2013-06-06 |
| CN102762601A (zh) | 2012-10-31 |
| EP2539374A1 (en) | 2013-01-02 |
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