CA2258523A1 - Polyoxyalkene substituted and bridged triazine, benzotriazole and benzophenone derivatives as uv absorbers - Google Patents

Info

Publication number

CA2258523A1

CA2258523A1 CA002258523A CA2258523A CA2258523A1 CA 2258523 A1 CA2258523 A1 CA 2258523A1 CA 002258523 A CA002258523 A CA 002258523A CA 2258523 A CA2258523 A CA 2258523A CA 2258523 A1 CA2258523 A1 CA 2258523A1

Authority

CA

Canada

Prior art keywords

hydrogen

formula

phenyl

polyoxyalkylene

radical

Prior art date

1996-07-18

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

• Espacenet
• Global Dossier
• CIPO
• Discuss

• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 title abstract description 48
• 150000008366 benzophenones Chemical class 0.000 title abstract description 44
• 239000012964 benzotriazole Substances 0.000 title abstract description 44
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title abstract description 42
• 239000006096 absorbing agent Substances 0.000 title abstract description 17
• 239000000203 mixture Substances 0.000 claims abstract description 104
• 239000000463 material Substances 0.000 claims abstract description 68
• -1 C1-C18alkyl Chemical class 0.000 claims description 152
• 229910052739 hydrogen Inorganic materials 0.000 claims description 145
• 239000001257 hydrogen Substances 0.000 claims description 139
• 150000001875 compounds Chemical class 0.000 claims description 131
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 79
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 64
• 238000000034 method Methods 0.000 claims description 62
• GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 60
• 229920005989 resin Polymers 0.000 claims description 43
• 239000011347 resin Substances 0.000 claims description 43
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
• 239000000460 chlorine Chemical group 0.000 claims description 36
• 239000002904 solvent Substances 0.000 claims description 35
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
• 238000000576 coating method Methods 0.000 claims description 30
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 26
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
• 229910052801 chlorine Chemical group 0.000 claims description 25
• 239000001301 oxygen Substances 0.000 claims description 25
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
• 239000000975 dye Substances 0.000 claims description 22
• 239000011248 coating agent Substances 0.000 claims description 20
• 150000001412 amines Chemical class 0.000 claims description 19
• 229910052751 metal Inorganic materials 0.000 claims description 19
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• 239000003381 stabilizer Substances 0.000 claims description 17
• 239000011230 binding agent Substances 0.000 claims description 16
• 229920000728 polyester Polymers 0.000 claims description 16
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
• 239000004952 Polyamide Substances 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 13
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
• 239000000654 additive Substances 0.000 claims description 12
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• 229920000877 Melamine resin Polymers 0.000 claims description 11
• 229920002647 polyamide Polymers 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
• 229920002635 polyurethane Polymers 0.000 claims description 10
• 239000004925 Acrylic resin Substances 0.000 claims description 9
• 125000003118 aryl group Chemical group 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 9
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• 239000000839 emulsion Substances 0.000 claims description 6
• 239000004611 light stabiliser Substances 0.000 claims description 6
• AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 6
• 230000000087 stabilizing effect Effects 0.000 claims description 6
• 239000003963 antioxidant agent Substances 0.000 claims description 5
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• XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 4
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• 239000013008 thixotropic agent Substances 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
• 229910052709 silver Inorganic materials 0.000 claims description 3
• 239000004332 silver Substances 0.000 claims description 3
• 230000000996 additive effect Effects 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 30
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 2
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical class OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims 1
• YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 claims 1
• HTTGVORJOBRXRJ-UHFFFAOYSA-N 2-(triazin-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=NN=N1 HTTGVORJOBRXRJ-UHFFFAOYSA-N 0.000 claims 1
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• 125000004432 carbon atom Chemical group C* 0.000 description 35
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
• 125000000217 alkyl group Chemical group 0.000 description 31
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• 238000001228 spectrum Methods 0.000 description 27
• 150000002148 esters Chemical class 0.000 description 26
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• 239000003054 catalyst Substances 0.000 description 24
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• 238000005481 NMR spectroscopy Methods 0.000 description 22
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• 238000006243 chemical reaction Methods 0.000 description 20
• 239000007787 solid Substances 0.000 description 20
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• 239000008199 coating composition Substances 0.000 description 19
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 19
• 239000000243 solution Substances 0.000 description 19
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
• 150000004985 diamines Chemical class 0.000 description 17
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 16
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
• 229920001515 polyalkylene glycol Polymers 0.000 description 16
• 150000002118 epoxides Chemical class 0.000 description 15
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
• 150000003918 triazines Chemical class 0.000 description 15
• 101150041968 CDC13 gene Proteins 0.000 description 14
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• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 14
• 238000003756 stirring Methods 0.000 description 14
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• CRQJERFKOCCFPE-UHFFFAOYSA-N 5-methyl-1,3-bis(piperidin-1-ylmethyl)-1,3,5-triazinane-2-thione Chemical class S=C1N(CN2CCCCC2)CN(C)CN1CN1CCCCC1 CRQJERFKOCCFPE-UHFFFAOYSA-N 0.000 description 13
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• RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 12
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• ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 description 8
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