NO312723B1 - Amino- og hydroksysubstituerte trifenyl-s-triaziner, mellomprodukter, fremgangsmåter for fremstilling, sammensetningerog kosmetiske preparater inneholdende triazinene, fremgangsmåtefor ökning av solbeskyttelse og stabilisering av materialer sa - Google Patents

Info

Publication number

NO312723B1

NO312723B1 NO19984597A NO984597A NO312723B1 NO 312723 B1 NO312723 B1 NO 312723B1 NO 19984597 A NO19984597 A NO 19984597A NO 984597 A NO984597 A NO 984597A NO 312723 B1 NO312723 B1 NO 312723B1

Authority

NO

Norway

Prior art keywords

formula

compound

hydrogen

alkyl

tert

Prior art date

1996-04-02

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• -1 hydroxy-substituted triphenyl-s-triazines Chemical class 0.000 title claims abstract description 129
• 239000000203 mixture Substances 0.000 title claims description 82
• 238000000034 method Methods 0.000 title claims description 52
• 239000000463 material Substances 0.000 title claims description 41
• 238000002360 preparation method Methods 0.000 title claims description 14
• 239000002537 cosmetic Substances 0.000 title claims description 13
• 230000000087 stabilizing effect Effects 0.000 title claims description 8
• 230000037072 sun protection Effects 0.000 title claims description 8
• 150000003918 triazines Chemical class 0.000 title description 5
• 239000000543 intermediate Substances 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 196
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
• 239000001257 hydrogen Substances 0.000 claims abstract description 45
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 31
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 6
• 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims abstract description 5
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 4
• 239000003381 stabilizer Substances 0.000 claims description 36
• 238000000576 coating method Methods 0.000 claims description 25
• 239000002657 fibrous material Substances 0.000 claims description 25
• 125000000217 alkyl group Chemical group 0.000 claims description 21
• 239000004753 textile Substances 0.000 claims description 21
• 239000011230 binding agent Substances 0.000 claims description 19
• 150000001412 amines Chemical class 0.000 claims description 18
• SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims description 15
• 239000004611 light stabiliser Substances 0.000 claims description 15
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
• 230000008569 process Effects 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 229910052760 oxygen Inorganic materials 0.000 claims description 10
• 239000001301 oxygen Substances 0.000 claims description 10
• 229920001169 thermoplastic Polymers 0.000 claims description 10
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 239000000654 additive Substances 0.000 claims description 9
• 230000006378 damage Effects 0.000 claims description 7
• 239000011368 organic material Substances 0.000 claims description 7
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 5
• PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 5
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
• 230000000475 sunscreen effect Effects 0.000 claims description 5
• 239000000516 sunscreening agent Substances 0.000 claims description 5
• FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 4
• 239000007864 aqueous solution Substances 0.000 claims description 4
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 4
• 229920000620 organic polymer Polymers 0.000 claims description 4
• SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 claims description 3
• 238000005984 hydrogenation reaction Methods 0.000 claims description 3
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
• 125000003545 alkoxy group Chemical group 0.000 claims description 2
• 239000002152 aqueous-organic solution Substances 0.000 claims description 2
• 125000006755 (C2-C20) alkyl group Chemical group 0.000 claims 1
• 230000008832 photodamage Effects 0.000 claims 1
• GGUFVZFOCZNPEG-UHFFFAOYSA-N 4,5,6-triphenyltriazine Chemical class C1=CC=CC=C1C1=NN=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 GGUFVZFOCZNPEG-UHFFFAOYSA-N 0.000 abstract description 5
• 229910052736 halogen Inorganic materials 0.000 abstract description 5
• 150000002367 halogens Chemical group 0.000 abstract description 5
• 238000000862 absorption spectrum Methods 0.000 abstract description 4
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 abstract 3
• 229910052799 carbon Inorganic materials 0.000 description 56
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 48
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• 229920000728 polyester Polymers 0.000 description 30
• 238000002844 melting Methods 0.000 description 27
• 230000008018 melting Effects 0.000 description 27
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• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 26
• 238000000921 elemental analysis Methods 0.000 description 26
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• 239000006096 absorbing agent Substances 0.000 description 22
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
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• 239000000835 fiber Substances 0.000 description 17
• 238000012360 testing method Methods 0.000 description 17
• 239000003054 catalyst Substances 0.000 description 16
• 150000002148 esters Chemical class 0.000 description 16
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• 239000002184 metal Substances 0.000 description 16
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 15
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
• 239000004952 Polyamide Substances 0.000 description 14
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• 235000019441 ethanol Nutrition 0.000 description 13
• 239000002253 acid Substances 0.000 description 12
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• 239000006185 dispersion Substances 0.000 description 12
• 238000002211 ultraviolet spectrum Methods 0.000 description 12
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 11
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 11
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
• 239000005977 Ethylene Substances 0.000 description 11
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 11
• 239000004814 polyurethane Substances 0.000 description 11
• 239000004743 Polypropylene Substances 0.000 description 10
• 239000007859 condensation product Substances 0.000 description 10
• 239000000839 emulsion Substances 0.000 description 10
• 239000003921 oil Substances 0.000 description 10
• 239000000843 powder Substances 0.000 description 10
• 229920000877 Melamine resin Polymers 0.000 description 9
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
• 238000004043 dyeing Methods 0.000 description 9
• 239000010408 film Substances 0.000 description 9
• 238000009472 formulation Methods 0.000 description 9
• 239000007788 liquid Substances 0.000 description 9
• 229920001684 low density polyethylene Polymers 0.000 description 9
• 239000004702 low-density polyethylene Substances 0.000 description 9
• 229920002857 polybutadiene Polymers 0.000 description 9
• 229920002635 polyurethane Polymers 0.000 description 9
• 239000000243 solution Substances 0.000 description 9
• 239000000758 substrate Substances 0.000 description 9
• WFSGQBNCVASPMW-UHFFFAOYSA-N 2-ethylhexanoyl chloride Chemical compound CCCCC(CC)C(Cl)=O WFSGQBNCVASPMW-UHFFFAOYSA-N 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 239000003795 chemical substances by application Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 239000004417 polycarbonate Substances 0.000 description 8
• 239000000047 product Substances 0.000 description 8
• 239000004721 Polyphenylene oxide Substances 0.000 description 7
• 125000001931 aliphatic group Chemical group 0.000 description 7
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• 229920000570 polyether Polymers 0.000 description 7
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• 150000003839 salts Chemical class 0.000 description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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• 239000004698 Polyethylene Substances 0.000 description 6
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
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• MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 6
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
• 239000013078 crystal Substances 0.000 description 6
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• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 6
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