AU775747B2 - Surface-active photoinitiators - Google Patents

Info

Publication number

AU775747B2

AU775747B2 AU48906/00A AU4890600A AU775747B2 AU 775747 B2 AU775747 B2 AU 775747B2 AU 48906/00 A AU48906/00 A AU 48906/00A AU 4890600 A AU4890600 A AU 4890600A AU 775747 B2 AU775747 B2 AU 775747B2

Authority

AU

Australia

Prior art keywords

formula

alkyl

photoinitiator

mixture

phenyl

Prior art date

1999-07-29

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.)

Ceased

Links

• Espacenet
• Global Dossier
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• 239000000203 mixture Substances 0.000 claims abstract description 160
• 150000001875 compounds Chemical class 0.000 claims abstract description 89
• 238000000034 method Methods 0.000 claims abstract description 64
• 238000000576 coating method Methods 0.000 claims abstract description 58
• 230000003678 scratch resistant effect Effects 0.000 claims abstract description 4
• -1 siloxanes Chemical class 0.000 claims description 90
• 238000009472 formulation Methods 0.000 claims description 45
• 229910008051 Si-OH Inorganic materials 0.000 claims description 36
• 229910006358 Si—OH Inorganic materials 0.000 claims description 36
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
• 230000008569 process Effects 0.000 claims description 29
• KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 26
• 229920005989 resin Polymers 0.000 claims description 26
• 239000011347 resin Substances 0.000 claims description 26
• 239000008199 coating composition Substances 0.000 claims description 24
• 239000000843 powder Substances 0.000 claims description 24
• 239000000758 substrate Substances 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
• 229910014033 C-OH Inorganic materials 0.000 claims description 17
• 229910014570 C—OH Inorganic materials 0.000 claims description 17
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 239000000654 additive Substances 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 239000011230 binding agent Substances 0.000 claims description 14
• 229920005862 polyol Polymers 0.000 claims description 14
• 229920000877 Melamine resin Polymers 0.000 claims description 12
• 229920000058 polyacrylate Polymers 0.000 claims description 12
• 150000003077 polyols Chemical class 0.000 claims description 12
• 239000007858 starting material Substances 0.000 claims description 10
• 239000001257 hydrogen Substances 0.000 claims description 9
• 229920001228 polyisocyanate Polymers 0.000 claims description 9
• 239000005056 polyisocyanate Substances 0.000 claims description 9
• 230000009471 action Effects 0.000 claims description 7
• 230000005670 electromagnetic radiation Effects 0.000 claims description 7
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
• 239000000126 substance Substances 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 150000002367 halogens Chemical class 0.000 claims description 6
• 150000002431 hydrogen Chemical class 0.000 claims description 6
• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
• 239000003365 glass fiber Substances 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
• 125000004450 alkenylene group Chemical group 0.000 claims description 3
• 239000002131 composite material Substances 0.000 claims description 3
• 229920000582 polyisocyanurate Polymers 0.000 claims description 3
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
• 150000007974 melamines Chemical class 0.000 claims description 2
• 239000011495 polyisocyanurate Substances 0.000 claims description 2
• 101800001195 Crustacean hyperglycemic hormone 3 Proteins 0.000 claims 1
• 235000005505 Ziziphus oenoplia Nutrition 0.000 claims 1
• 244000104547 Ziziphus oenoplia Species 0.000 claims 1
• 229920005906 polyester polyol Polymers 0.000 claims 1
• 239000011248 coating agent Substances 0.000 abstract description 23
• 238000010438 heat treatment Methods 0.000 abstract description 4
• 239000005977 Ethylene Substances 0.000 abstract description 3
• ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 abstract description 2
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract description 2
• 230000007246 mechanism Effects 0.000 abstract description 2
• 230000004931 aggregating effect Effects 0.000 abstract 1
• 238000005160 1H NMR spectroscopy Methods 0.000 description 30
• 239000003054 catalyst Substances 0.000 description 28
• 238000006243 chemical reaction Methods 0.000 description 27
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 22
• 238000001723 curing Methods 0.000 description 22
• 229920000642 polymer Polymers 0.000 description 22
• 239000000047 product Substances 0.000 description 22
• 150000003254 radicals Chemical class 0.000 description 22
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• 229920001577 copolymer Polymers 0.000 description 19
• 239000003999 initiator Substances 0.000 description 19
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 18
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 18
• 229910052751 metal Inorganic materials 0.000 description 17
• 239000002184 metal Substances 0.000 description 17
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 17
• 239000002904 solvent Substances 0.000 description 16
• 239000004814 polyurethane Substances 0.000 description 15
• 229920002635 polyurethane Polymers 0.000 description 15
• 239000000243 solution Substances 0.000 description 14
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
• 239000000178 monomer Substances 0.000 description 12
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
• 229920000728 polyester Polymers 0.000 description 12
• YYCUCYKNOQSLPT-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-(4-prop-2-enoxyphenyl)propan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=C(OCC=C)C=C1 YYCUCYKNOQSLPT-UHFFFAOYSA-N 0.000 description 11
• 239000004593 Epoxy Substances 0.000 description 11
• 125000001931 aliphatic group Chemical group 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• 239000000049 pigment Substances 0.000 description 11
• 125000000524 functional group Chemical group 0.000 description 10
• 239000012948 isocyanate Substances 0.000 description 10
• 238000004519 manufacturing process Methods 0.000 description 10
• 229920000647 polyepoxide Polymers 0.000 description 10
• 238000001228 spectrum Methods 0.000 description 10
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000002253 acid Substances 0.000 description 9
• VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 150000001735 carboxylic acids Chemical class 0.000 description 8
• 239000000460 chlorine Substances 0.000 description 8
• 239000007788 liquid Substances 0.000 description 8
• NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 7
• TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 7
• FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 7
• FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 7
• CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
• OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 7
• QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 7
• 125000003277 amino group Chemical group 0.000 description 7
• 125000004432 carbon atom Chemical group C* 0.000 description 7
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
• 239000003795 chemical substances by application Substances 0.000 description 7
• 150000002513 isocyanates Chemical class 0.000 description 7
• VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 7
• 239000011976 maleic acid Substances 0.000 description 7
• 229920000570 polyether Polymers 0.000 description 7
• 239000007787 solid Substances 0.000 description 7
• 239000000600 sorbitol Substances 0.000 description 7
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 6
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
• 150000002148 esters Chemical class 0.000 description 6
• 238000001914 filtration Methods 0.000 description 6
• 239000010410 layer Substances 0.000 description 6
• 150000002739 metals Chemical class 0.000 description 6
• 229940063557 methacrylate Drugs 0.000 description 6
• SWGZAKPJNWCPRY-UHFFFAOYSA-N methyl-bis(trimethylsilyloxy)silicon Chemical compound C[Si](C)(C)O[Si](C)O[Si](C)(C)C SWGZAKPJNWCPRY-UHFFFAOYSA-N 0.000 description 6
• 229910052697 platinum Inorganic materials 0.000 description 6
• LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Inorganic materials [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 6
• 239000000725 suspension Substances 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 239000004721 Polyphenylene oxide Substances 0.000 description 5
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
• 125000003118 aryl group Chemical group 0.000 description 5
• 230000015572 biosynthetic process Effects 0.000 description 5
• 229910052799 carbon Inorganic materials 0.000 description 5
• 239000000470 constituent Substances 0.000 description 5
• 150000002009 diols Chemical class 0.000 description 5
• 238000001035 drying Methods 0.000 description 5
• 239000000975 dye Substances 0.000 description 5
• UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 5
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• ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
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• DJRWYZYGAQGXSC-UHFFFAOYSA-N 2-methyl-2-prop-2-enoxy-1-(4-prop-2-enoxyphenyl)propan-1-one Chemical compound C=CCOC(C)(C)C(=O)C1=CC=C(OCC=C)C=C1 DJRWYZYGAQGXSC-UHFFFAOYSA-N 0.000 description 4
• KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
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• 101000585693 Homo sapiens Mitochondrial 2-oxodicarboxylate carrier Proteins 0.000 description 4
• 101001041245 Homo sapiens Ornithine decarboxylase Proteins 0.000 description 4
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• RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
• 239000012965 benzophenone Substances 0.000 description 4
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• 239000012964 benzotriazole Substances 0.000 description 4
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• 238000006482 condensation reaction Methods 0.000 description 4
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
• 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 4
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• 125000001424 substituent group Chemical group 0.000 description 4
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• HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 4
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• 239000006096 absorbing agent Substances 0.000 description 3
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• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
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