JP2013520523A - ポリマー光開始剤 - Google Patents
ポリマー光開始剤 Download PDFInfo
- Publication number
- JP2013520523A JP2013520523A JP2012553183A JP2012553183A JP2013520523A JP 2013520523 A JP2013520523 A JP 2013520523A JP 2012553183 A JP2012553183 A JP 2012553183A JP 2012553183 A JP2012553183 A JP 2012553183A JP 2013520523 A JP2013520523 A JP 2013520523A
- Authority
- JP
- Japan
- Prior art keywords
- photoinitiator
- photoinitiators
- ether
- polyalkyl ether
- photoinitiator according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229920000642 polymer Polymers 0.000 title description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- -1 polyethylene Polymers 0.000 claims description 26
- 239000012965 benzophenone Substances 0.000 claims description 23
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- 239000011159 matrix material Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- 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
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 239000003999 initiator Substances 0.000 claims description 10
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
- 150000008366 benzophenones Chemical class 0.000 claims description 8
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 150000003457 sulfones Chemical class 0.000 claims description 8
- 150000003458 sulfonic acid derivatives Chemical class 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 150000004056 anthraquinones Chemical class 0.000 claims description 7
- 150000002170 ethers Chemical class 0.000 claims description 7
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 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 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 5
- 230000005855 radiation Effects 0.000 claims description 5
- 150000007964 xanthones Chemical class 0.000 claims description 5
- 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 claims description 4
- 150000003923 2,5-pyrrolediones Chemical class 0.000 claims description 4
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical class C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 claims description 4
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 4
- 229930006711 bornane-2,3-dione Natural products 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
- 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 claims description 3
- IANQGOCKLOCSFY-UHFFFAOYSA-N 4-phenyl-4H-chromene-2,3-dione Chemical compound O=C1C(=O)OC2=CC=CC=C2C1C1=CC=CC=C1 IANQGOCKLOCSFY-UHFFFAOYSA-N 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
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 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
- 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
- 150000003460 sulfonic acids Chemical class 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 description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 150000002823 nitrates Chemical class 0.000 claims description 2
- 229920000058 polyacrylate Polymers 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 229910000077 silane Inorganic materials 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000006116 polymerization reaction Methods 0.000 description 20
- 238000001723 curing Methods 0.000 description 16
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 14
- 239000005977 Ethylene Substances 0.000 description 11
- 150000002118 epoxides Chemical class 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 150000003254 radicals Chemical class 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
- 238000003786 synthesis reaction Methods 0.000 description 8
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 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 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 244000028419 Styrax benzoin Species 0.000 description 4
- 235000000126 Styrax benzoin Nutrition 0.000 description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 description 4
- 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 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229960002130 benzoin Drugs 0.000 description 4
- 239000008199 coating composition Substances 0.000 description 4
- 235000019382 gum benzoic Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-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
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 238000013508 migration Methods 0.000 description 3
- 230000005012 migration Effects 0.000 description 3
- 239000012038 nucleophile Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical group C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 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
- 238000010546 Norrish type I reaction Methods 0.000 description 2
- 239000002202 Polyethylene glycol Substances 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
- 150000005215 alkyl ethers Chemical group 0.000 description 2
- 229910052786 argon Inorganic materials 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
- 239000012043 crude product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 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
- 150000001993 dienes Chemical class 0.000 description 2
- 230000000694 effects Effects 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
- 239000000835 fiber Substances 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 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 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
- 230000001678 irradiating effect Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- 239000003973 paint Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 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
- 150000005838 radical anions Chemical class 0.000 description 2
- 150000005839 radical cations Chemical class 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- MCULRUJILOGHCJ-UHFFFAOYSA-N triisobutylaluminium Chemical compound CC(C)C[Al](CC(C)C)CC(C)C MCULRUJILOGHCJ-UHFFFAOYSA-N 0.000 description 2
- WIKJQQCCZHVTNR-UHFFFAOYSA-N (4-aminophenyl)-[4-(4-aminosulfanylphenyl)phenyl]methanone Chemical compound C1=CC(SN)=CC=C1C1=CC=C(C(=O)C=2C=CC(N)=CC=2)C=C1 WIKJQQCCZHVTNR-UHFFFAOYSA-N 0.000 description 1
- 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
- NDJCDNQKIINPMP-UHFFFAOYSA-N 2,4-dihydroxy-2,4-dimethyl-1,5-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=CC=C1 NDJCDNQKIINPMP-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
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229910000799 K alloy Inorganic materials 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 238000010547 Norrish type II reaction Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000005011 alkyl ether group Chemical group 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000011021 bench scale process Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000007036 catalytic synthesis reaction Methods 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
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- 229920003020 cross-linked polyethylene Polymers 0.000 description 1
- 239000004703 cross-linked polyethylene Substances 0.000 description 1
- 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000005267 main chain polymer Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 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
- 239000003211 polymerization photoinitiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 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
- 238000009281 ultraviolet germicidal irradiation Methods 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)
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| DKPA201070065 | 2010-02-23 | ||
| DKPA201070065 | 2010-02-23 | ||
| DKPA201170007 | 2011-01-07 | ||
| DKPA201170007 | 2011-01-07 | ||
| PCT/DK2011/050055 WO2011103878A1 (en) | 2010-02-23 | 2011-02-23 | Polymeric photoinitiators |
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| JP (2) | JP2013520523A (https=) |
| CN (1) | CN102762601B (https=) |
| BR (1) | BR112012020628B1 (https=) |
| RU (1) | RU2572839C2 (https=) |
| SG (1) | SG183124A1 (https=) |
| WO (1) | WO2011103878A1 (https=) |
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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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| WO2008071796A1 (en) * | 2006-12-15 | 2008-06-19 | Coloplast A/S | Coatings prepared from poly(ethylene oxide) and photo-initator-containing scaffolds |
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| 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 |
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| 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 |
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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
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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
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008071796A1 (en) * | 2006-12-15 | 2008-06-19 | Coloplast A/S | Coatings prepared from poly(ethylene oxide) and photo-initator-containing scaffolds |
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 |
| BR112012020628B1 (pt) | 2019-12-10 |
| 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 |
| CN102762601A (zh) | 2012-10-31 |
| EP2539374A1 (en) | 2013-01-02 |
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