CA2371607A1 - Stabilized adhesive compositions containing highly soluble, high extinction, photostable hydroxyphenyl-s-triazine uv absorbers and laminated articles derived therefrom - Google Patents
Stabilized adhesive compositions containing highly soluble, high extinction, photostable hydroxyphenyl-s-triazine uv absorbers and laminated articles derived therefrom Download PDFInfo
- Publication number
- CA2371607A1 CA2371607A1 CA002371607A CA2371607A CA2371607A1 CA 2371607 A1 CA2371607 A1 CA 2371607A1 CA 002371607 A CA002371607 A CA 002371607A CA 2371607 A CA2371607 A CA 2371607A CA 2371607 A1 CA2371607 A1 CA 2371607A1
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- triazine
- alkyl
- hydroxy
- phenyl
- 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.)
- Abandoned
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 108
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 84
- 239000000853 adhesive Substances 0.000 title claims abstract description 83
- 239000006096 absorbing agent Substances 0.000 title claims abstract description 74
- 230000008033 biological extinction Effects 0.000 title claims abstract description 15
- NJCDRURWJZAMBM-UHFFFAOYSA-N 6-phenyl-1h-1,3,5-triazin-2-one Chemical compound OC1=NC=NC(C=2C=CC=CC=2)=N1 NJCDRURWJZAMBM-UHFFFAOYSA-N 0.000 title abstract description 4
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims abstract description 96
- 239000010408 film Substances 0.000 claims abstract description 24
- 239000011521 glass Substances 0.000 claims abstract description 22
- 238000000576 coating method Methods 0.000 claims abstract description 17
- 125000006612 decyloxy group Chemical group 0.000 claims abstract description 6
- 125000006611 nonyloxy group Chemical group 0.000 claims abstract description 6
- 125000005447 octyloxy group Chemical group [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])O* 0.000 claims abstract description 6
- 239000012788 optical film Substances 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 188
- -1 2,2,6,6-tetramethylpiperidinyl Chemical group 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 125000002947 alkylene group Chemical group 0.000 claims description 36
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
- 238000002835 absorbance Methods 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 229920000642 polymer Polymers 0.000 claims description 25
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 238000010276 construction Methods 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 19
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 15
- 239000010410 layer Substances 0.000 claims description 15
- 239000003381 stabilizer Substances 0.000 claims description 15
- 239000007983 Tris buffer Substances 0.000 claims description 13
- 229920000058 polyacrylate Polymers 0.000 claims description 13
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 12
- 229920002635 polyurethane Polymers 0.000 claims description 12
- 239000004814 polyurethane Substances 0.000 claims description 12
- 230000005855 radiation Effects 0.000 claims description 12
- DRXGKQPTFWTTJW-UHFFFAOYSA-N 5-butoxy-2-[4-(4-butoxy-2-hydroxyphenyl)-6-(2,4-dibutoxyphenyl)-1,3,5-triazin-2-yl]phenol Chemical compound OC1=CC(OCCCC)=CC=C1C1=NC(C=2C(=CC(OCCCC)=CC=2)O)=NC(C=2C(=CC(OCCCC)=CC=2)OCCCC)=N1 DRXGKQPTFWTTJW-UHFFFAOYSA-N 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 150000001412 amines Chemical class 0.000 claims description 10
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 9
- 239000005977 Ethylene Substances 0.000 claims description 9
- 239000004952 Polyamide Substances 0.000 claims description 9
- 239000012790 adhesive layer Substances 0.000 claims description 9
- 229920002647 polyamide Polymers 0.000 claims description 9
- 229920002721 polycyanoacrylate Polymers 0.000 claims description 9
- 235000013824 polyphenols Nutrition 0.000 claims description 9
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 9
- 230000006641 stabilisation Effects 0.000 claims description 9
- 238000011105 stabilization Methods 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- 229920000647 polyepoxide Polymers 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- 239000001993 wax Substances 0.000 claims description 7
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 6
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 6
- 239000004593 Epoxy Substances 0.000 claims description 6
- 244000043261 Hevea brasiliensis Species 0.000 claims description 6
- 239000004642 Polyimide Substances 0.000 claims description 6
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 6
- 229920003052 natural elastomer Polymers 0.000 claims description 6
- 229920001194 natural rubber Polymers 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- 229920001721 polyimide Polymers 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 229920006132 styrene block copolymer Polymers 0.000 claims description 6
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 6
- SGZWJGRZDJCDIM-UHFFFAOYSA-N 4-[4,6-bis(2,4-dihydroxyphenyl)-1,3,5-triazin-2-yl]benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1=NC(C=2C(=CC(O)=CC=2)O)=NC(C=2C(=CC(O)=CC=2)O)=N1 SGZWJGRZDJCDIM-UHFFFAOYSA-N 0.000 claims description 5
- 239000005062 Polybutadiene Substances 0.000 claims description 5
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 5
- 239000000975 dye Substances 0.000 claims description 5
- 229920001971 elastomer Polymers 0.000 claims description 5
- 239000000839 emulsion Substances 0.000 claims description 5
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
- 229920002857 polybutadiene Polymers 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000004831 Hot glue Substances 0.000 claims description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- 239000000539 dimer Substances 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 4
- 229920000554 ionomer Polymers 0.000 claims description 4
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 229910052724 xenon Inorganic materials 0.000 claims description 4
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 claims description 3
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 claims description 3
- GZQKBPSHUCTQCZ-UHFFFAOYSA-N 2-[4,6-bis[4-(3-butan-2-yloxy-2-hydroxypropoxy)-2-hydroxyphenyl]-1,3,5-triazin-2-yl]-5-(3-butan-2-yloxy-2-hydroxypropoxy)phenol Chemical compound OC1=CC(OCC(O)COC(C)CC)=CC=C1C1=NC(C=2C(=CC(OCC(O)COC(C)CC)=CC=2)O)=NC(C=2C(=CC(OCC(O)COC(C)CC)=CC=2)O)=N1 GZQKBPSHUCTQCZ-UHFFFAOYSA-N 0.000 claims description 3
- JKKPQQAIEAQNPR-UHFFFAOYSA-N 5-(3-butan-2-yloxy-2-hydroxypropoxy)-2-[4-[2-hydroxy-4-(2-hydroxy-3-pentan-2-yloxypropoxy)phenyl]-6-phenyl-1,3,5-triazin-2-yl]phenol Chemical compound CCCC(C)OCC(O)COc1ccc(c(O)c1)-c1nc(nc(n1)-c1ccc(OCC(O)COC(C)CC)cc1O)-c1ccccc1 JKKPQQAIEAQNPR-UHFFFAOYSA-N 0.000 claims description 3
- YAWARMNTAGPPGS-UHFFFAOYSA-N 5-(3-butoxy-2-hydroxypropoxy)-2-[3-[[6-[4-(3-butoxy-2-hydroxypropoxy)-2-hydroxyphenyl]-2,4-bis(2,4-dimethylphenyl)-2H-1,3,5-triazin-1-yl]methyl]-2,6-bis(2,4-dimethylphenyl)-2H-1,3,5-triazin-4-yl]phenol Chemical compound OC1=CC(OCC(O)COCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)N1CN1C(C=2C(=CC(OCC(O)COCCCC)=CC=2)O)=NC(C=2C(=CC(C)=CC=2)C)=NC1C1=CC=C(C)C=C1C YAWARMNTAGPPGS-UHFFFAOYSA-N 0.000 claims description 3
- YPFBPAKTPNIEJE-UHFFFAOYSA-N 5-(3-butoxy-2-hydroxypropoxy)-2-[4-[4-(3-butoxy-2-hydroxypropoxy)-2-hydroxyphenyl]-6-(2,4,6-trimethylphenyl)-1,3,5-triazin-2-yl]phenol Chemical compound OC1=CC(OCC(O)COCCCC)=CC=C1C1=NC(C=2C(=CC(OCC(O)COCCCC)=CC=2)O)=NC(C=2C(=CC(C)=CC=2C)C)=N1 YPFBPAKTPNIEJE-UHFFFAOYSA-N 0.000 claims description 3
- 239000004604 Blowing Agent Substances 0.000 claims description 3
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 claims description 3
- 239000004743 Polypropylene Substances 0.000 claims description 3
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 3
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 239000002216 antistatic agent Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 125000003700 epoxy group Chemical group 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000000314 lubricant Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 229930014626 natural product Natural products 0.000 claims description 3
- 239000003921 oil Substances 0.000 claims description 3
- 230000003287 optical effect Effects 0.000 claims description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 229920001084 poly(chloroprene) Polymers 0.000 claims description 3
- 229920001155 polypropylene Polymers 0.000 claims description 3
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 3
- 239000011118 polyvinyl acetate Substances 0.000 claims description 3
- 239000012744 reinforcing agent Substances 0.000 claims description 3
- 239000005060 rubber Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- 239000004332 silver Substances 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims description 3
- CTQAYJKMGXQVQH-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(2-hydroxy-3-phenylmethoxypropoxy)phenol Chemical compound CC1=CC(C)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(OCC(O)COCC=3C=CC=CC=3)=CC=2)O)=N1 CTQAYJKMGXQVQH-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 2
- 229920002121 Hydroxyl-terminated polybutadiene Polymers 0.000 claims description 2
- 239000004698 Polyethylene Substances 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000002318 adhesion promoter Substances 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000000732 arylene group Chemical group 0.000 claims description 2
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 239000000806 elastomer Substances 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 229920006270 hydrocarbon resin Polymers 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 150000002443 hydroxylamines Chemical class 0.000 claims description 2
- 239000004200 microcrystalline wax Substances 0.000 claims description 2
- 235000019808 microcrystalline wax Nutrition 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 239000012188 paraffin wax Substances 0.000 claims description 2
- 239000012169 petroleum derived wax Substances 0.000 claims description 2
- 235000019381 petroleum wax Nutrition 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 229920000573 polyethylene Polymers 0.000 claims description 2
- 229920003048 styrene butadiene rubber Polymers 0.000 claims description 2
- 150000003505 terpenes Chemical class 0.000 claims description 2
- 235000007586 terpenes Nutrition 0.000 claims description 2
- 229920001187 thermosetting polymer Polymers 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 26
- 238000009472 formulation Methods 0.000 abstract description 13
- 230000015556 catabolic process Effects 0.000 abstract description 8
- 238000006731 degradation reaction Methods 0.000 abstract description 7
- 238000010348 incorporation Methods 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000012360 testing method Methods 0.000 description 16
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 9
- 239000012965 benzophenone Substances 0.000 description 8
- 150000001565 benzotriazoles Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000008366 benzophenones Chemical class 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 7
- 229920000139 polyethylene terephthalate Polymers 0.000 description 7
- 239000005020 polyethylene terephthalate Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- 239000000243 solution Substances 0.000 description 6
- 238000002211 ultraviolet spectrum Methods 0.000 description 6
- VDHIEQOYPSVNIM-UHFFFAOYSA-N 2-hexyldecyl 2-ethylhexanoate Chemical compound CCCCCCCCC(CCCCCC)COC(=O)C(CC)CCCC VDHIEQOYPSVNIM-UHFFFAOYSA-N 0.000 description 5
- GUCMKIKYKIHUTM-UHFFFAOYSA-N 3,3,5,5-tetramethyl-1-[2-(3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]piperazin-2-one Chemical compound O=C1C(C)(C)NC(C)(C)CN1CCN1C(=O)C(C)(C)NC(C)(C)C1 GUCMKIKYKIHUTM-UHFFFAOYSA-N 0.000 description 5
- 229920001651 Cyanoacrylate Polymers 0.000 description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 230000007774 longterm Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- MEZZCSHVIGVWFI-UHFFFAOYSA-N 2,2'-Dihydroxy-4-methoxybenzophenone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1O MEZZCSHVIGVWFI-UHFFFAOYSA-N 0.000 description 4
- YZXTWMQYSSMUFH-UHFFFAOYSA-N 4-[6-(1-amino-2,2,6,6-tetramethylpiperidin-4-yl)hexyl]-2,2,6,6-tetramethylpiperidin-1-amine Chemical compound C1C(C)(C)N(N)C(C)(C)CC1CCCCCCC1CC(C)(C)N(N)C(C)(C)C1 YZXTWMQYSSMUFH-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
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- 230000004224 protection Effects 0.000 description 4
- 150000003902 salicylic acid esters Chemical class 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VNQNXQYZMPJLQX-UHFFFAOYSA-N 1,3,5-tris[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CN2C(N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C(=O)N(CC=3C=C(C(O)=C(C=3)C(C)(C)C)C(C)(C)C)C2=O)=O)=C1 VNQNXQYZMPJLQX-UHFFFAOYSA-N 0.000 description 3
- MMKOHTDGXBBEAH-UHFFFAOYSA-N 2,2,6,6-tetramethyl-1-octoxypiperidin-4-ol Chemical compound CCCCCCCCON1C(C)(C)CC(O)CC1(C)C MMKOHTDGXBBEAH-UHFFFAOYSA-N 0.000 description 3
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical compound CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 3
- HPFWYRKGZUGGPB-UHFFFAOYSA-N 4,6-dichloro-n-(2,4,4-trimethylpentan-2-yl)-1,3,5-triazin-2-amine Chemical compound CC(C)(C)CC(C)(C)NC1=NC(Cl)=NC(Cl)=N1 HPFWYRKGZUGGPB-UHFFFAOYSA-N 0.000 description 3
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- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OHRVKCZTBPSUIK-UHFFFAOYSA-N tridodecyl phosphate Chemical compound CCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCC)OCCCCCCCCCCCC OHRVKCZTBPSUIK-UHFFFAOYSA-N 0.000 description 1
- FDGZUBKNYGBWHI-UHFFFAOYSA-N trioctadecyl phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(=O)(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC FDGZUBKNYGBWHI-UHFFFAOYSA-N 0.000 description 1
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 1
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C AZSKHRTUXHLAHS-UHFFFAOYSA-N 0.000 description 1
- OOZBTDPWFHJVEK-UHFFFAOYSA-N tris(2-nonylphenyl) phosphate Chemical compound CCCCCCCCCC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC OOZBTDPWFHJVEK-UHFFFAOYSA-N 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical group C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10678—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer comprising UV absorbers or stabilizers, e.g. antioxidants
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10743—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing acrylate (co)polymers or salts thereof
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
-
- 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
- C09J201/00—Adhesives based on unspecified macromolecular compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/40—Properties of the layers or laminate having particular optical properties
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/303,581 | 1999-05-03 | ||
| US09/303,581 US6191199B1 (en) | 1999-05-03 | 1999-05-03 | Stabilized adhesive compositions containing highly soluble, high extinction photostable hydroxyphenyl-s-triazine UV absorbers and laminated articles derived therefrom |
| PCT/EP2000/003615 WO2000066675A1 (en) | 1999-05-03 | 2000-04-20 | STABILIZED ADHESIVE COMPOSITIONS CONTAINING HIGHLY SOLUBLE, HIGH EXTINCTION, PHOTOSTABLE HYDROXYPHENYL-s-TRIAZINE UV ABSORBERS AND LAMINATED ARTICLES DERIVED THEREFROM |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2371607A1 true CA2371607A1 (en) | 2000-11-09 |
Family
ID=23172747
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002371607A Abandoned CA2371607A1 (en) | 1999-05-03 | 2000-04-20 | Stabilized adhesive compositions containing highly soluble, high extinction, photostable hydroxyphenyl-s-triazine uv absorbers and laminated articles derived therefrom |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US6191199B1 (enExample) |
| EP (1) | EP1181338B1 (enExample) |
| JP (1) | JP4743971B2 (enExample) |
| KR (1) | KR100583343B1 (enExample) |
| CN (1) | CN1186418C (enExample) |
| AT (1) | ATE317882T1 (enExample) |
| AU (1) | AU759952B2 (enExample) |
| BR (1) | BR0010227A (enExample) |
| CA (1) | CA2371607A1 (enExample) |
| CZ (1) | CZ20013936A3 (enExample) |
| DE (1) | DE60026018T2 (enExample) |
| DK (1) | DK1181338T3 (enExample) |
| ES (1) | ES2257292T3 (enExample) |
| PT (1) | PT1181338E (enExample) |
| RU (1) | RU2245894C9 (enExample) |
| TW (1) | TW513476B (enExample) |
| WO (1) | WO2000066675A1 (enExample) |
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| TWI316513B (en) * | 2001-07-02 | 2009-11-01 | Ciba Sc Holding Ag | Highly compatible hydroxyphenyltriazine uv-absorbers |
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-
1999
- 1999-05-03 US US09/303,581 patent/US6191199B1/en not_active Expired - Lifetime
-
2000
- 2000-04-17 US US09/551,033 patent/US6225384B1/en not_active Expired - Lifetime
- 2000-04-20 DE DE60026018T patent/DE60026018T2/de not_active Expired - Lifetime
- 2000-04-20 PT PT00925232T patent/PT1181338E/pt unknown
- 2000-04-20 KR KR1020017013946A patent/KR100583343B1/ko not_active Expired - Fee Related
- 2000-04-20 AU AU44022/00A patent/AU759952B2/en not_active Ceased
- 2000-04-20 CZ CZ20013936A patent/CZ20013936A3/cs unknown
- 2000-04-20 RU RU2001132584/04A patent/RU2245894C9/ru not_active IP Right Cessation
- 2000-04-20 JP JP2000615701A patent/JP4743971B2/ja not_active Expired - Fee Related
- 2000-04-20 CN CNB008070687A patent/CN1186418C/zh not_active Expired - Fee Related
- 2000-04-20 WO PCT/EP2000/003615 patent/WO2000066675A1/en not_active Ceased
- 2000-04-20 AT AT00925232T patent/ATE317882T1/de not_active IP Right Cessation
- 2000-04-20 CA CA002371607A patent/CA2371607A1/en not_active Abandoned
- 2000-04-20 EP EP00925232A patent/EP1181338B1/en not_active Expired - Lifetime
- 2000-04-20 DK DK00925232T patent/DK1181338T3/da active
- 2000-04-20 BR BR0010227-0A patent/BR0010227A/pt not_active IP Right Cessation
- 2000-04-20 ES ES00925232T patent/ES2257292T3/es not_active Expired - Lifetime
- 2000-05-03 TW TW089108424A patent/TW513476B/zh active
Also Published As
| Publication number | Publication date |
|---|---|
| DE60026018D1 (de) | 2006-04-20 |
| KR20020034077A (ko) | 2002-05-08 |
| RU2245894C9 (ru) | 2005-05-10 |
| BR0010227A (pt) | 2002-02-13 |
| EP1181338A1 (en) | 2002-02-27 |
| KR100583343B1 (ko) | 2006-05-24 |
| PT1181338E (pt) | 2006-05-31 |
| EP1181338B1 (en) | 2006-02-15 |
| US6225384B1 (en) | 2001-05-01 |
| RU2245894C2 (ru) | 2005-02-10 |
| CZ20013936A3 (cs) | 2002-02-13 |
| ES2257292T3 (es) | 2006-08-01 |
| TW513476B (en) | 2002-12-11 |
| ATE317882T1 (de) | 2006-03-15 |
| AU4402200A (en) | 2000-11-17 |
| CN1186418C (zh) | 2005-01-26 |
| WO2000066675A1 (en) | 2000-11-09 |
| CN1349553A (zh) | 2002-05-15 |
| JP4743971B2 (ja) | 2011-08-10 |
| JP2002543265A (ja) | 2002-12-17 |
| AU759952B2 (en) | 2003-05-01 |
| US6191199B1 (en) | 2001-02-20 |
| DE60026018T2 (de) | 2006-08-03 |
| DK1181338T3 (da) | 2006-06-12 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |