NL1007031C2 - Hydroxyfenyltriazinen. - Google Patents

Info

Publication number

NL1007031C2

NL1007031C2 NL1007031A NL1007031A NL1007031C2 NL 1007031 C2 NL1007031 C2 NL 1007031C2 NL 1007031 A NL1007031 A NL 1007031A NL 1007031 A NL1007031 A NL 1007031A NL 1007031 C2 NL1007031 C2 NL 1007031C2

Authority

NL

Netherlands

Prior art keywords

alkyl

substituted

alkoxy

halogen

tert

Prior art date

1996-09-13

Links

• Espacenet
• Global Dossier
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• VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 title 1
• -1 acrylamino Chemical group 0.000 claims description 196
• 150000001875 compounds Chemical class 0.000 claims description 72
• 239000000203 mixture Substances 0.000 claims description 70
• 125000000217 alkyl group Chemical group 0.000 claims description 68
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
• 229910052736 halogen Inorganic materials 0.000 claims description 31
• 150000002367 halogens Chemical class 0.000 claims description 30
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
• 239000003381 stabilizer Substances 0.000 claims description 29
• 125000001424 substituent group Chemical group 0.000 claims description 27
• 229920000642 polymer Polymers 0.000 claims description 26
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 23
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 125000003118 aryl group Chemical group 0.000 claims description 21
• 229910052751 metal Inorganic materials 0.000 claims description 19
• 239000011230 binding agent Substances 0.000 claims description 18
• 239000004922 lacquer Substances 0.000 claims description 18
• 239000002184 metal Substances 0.000 claims description 18
• NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 239000002537 cosmetic Substances 0.000 claims description 15
• 239000000463 material Substances 0.000 claims description 15
• 229910052760 oxygen Inorganic materials 0.000 claims description 15
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
• 238000000034 method Methods 0.000 claims description 13
• 239000001301 oxygen Substances 0.000 claims description 13
• 235000010290 biphenyl Nutrition 0.000 claims description 12
• 239000004305 biphenyl Substances 0.000 claims description 12
• 239000001257 hydrogen Substances 0.000 claims description 12
• 239000004814 polyurethane Substances 0.000 claims description 12
• 230000000087 stabilizing effect Effects 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000001624 naphthyl group Chemical group 0.000 claims description 11
• 239000011368 organic material Substances 0.000 claims description 11
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 10
• 125000001188 haloalkyl group Chemical group 0.000 claims description 10
• 229920000178 Acrylic resin Polymers 0.000 claims description 9
• 239000002253 acid Substances 0.000 claims description 9
• 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 claims description 9
• 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 8
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 8
• 239000000654 additive Substances 0.000 claims description 7
• 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
• 229920000098 polyolefin Polymers 0.000 claims description 7
• 150000003839 salts Chemical class 0.000 claims description 7
• 229920000180 alkyd Polymers 0.000 claims description 6
• 229910006069 SO3H Inorganic materials 0.000 claims description 5
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 229910052783 alkali metal Inorganic materials 0.000 claims description 4
• 150000001340 alkali metals Chemical class 0.000 claims description 4
• 229920001225 polyester resin Polymers 0.000 claims description 4
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
• 229920005749 polyurethane resin Polymers 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 150000001616 biphenylenes Chemical class 0.000 claims description 2
• 125000002529 biphenylenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
• 229920000620 organic polymer Polymers 0.000 claims description 2
• 229920006122 polyamide resin Polymers 0.000 claims description 2
• 239000000516 sunscreening agent Substances 0.000 claims description 2
• 229920001059 synthetic polymer Polymers 0.000 claims description 2
• 125000003884 phenylalkyl group Chemical group 0.000 claims 1
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 47
• 229920001577 copolymer Polymers 0.000 description 35
• 238000000576 coating method Methods 0.000 description 21
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 21
• 150000001412 amines Chemical class 0.000 description 19
• 239000003054 catalyst Substances 0.000 description 18
• 239000011248 coating agent Substances 0.000 description 18
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 239000004743 Polypropylene Substances 0.000 description 15
• 150000002148 esters Chemical class 0.000 description 15
• 229920001155 polypropylene Polymers 0.000 description 15
• 229920005989 resin Polymers 0.000 description 15
• 239000011347 resin Substances 0.000 description 15
• 239000006096 absorbing agent Substances 0.000 description 14
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
• MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
• 239000003973 paint Substances 0.000 description 12
• 239000004952 Polyamide Substances 0.000 description 11
• 239000003795 chemical substances by application Substances 0.000 description 11
• 229920002647 polyamide Polymers 0.000 description 11
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
• 239000005977 Ethylene Substances 0.000 description 10
• 239000000047 product Substances 0.000 description 10
• 239000007787 solid Substances 0.000 description 10
• 239000002904 solvent Substances 0.000 description 10
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 9
• 229920000877 Melamine resin Polymers 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
• 229920001684 low density polyethylene Polymers 0.000 description 9
• 239000004702 low-density polyethylene Substances 0.000 description 9
• 239000003921 oil Substances 0.000 description 9
• 229920002857 polybutadiene Polymers 0.000 description 9
• 239000000243 solution Substances 0.000 description 9
• NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
• 239000004925 Acrylic resin Substances 0.000 description 8
• 239000005062 Polybutadiene Substances 0.000 description 8
• 239000004721 Polyphenylene oxide Substances 0.000 description 8
• KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
• 239000000835 fiber Substances 0.000 description 8
• GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
• 229920000728 polyester Polymers 0.000 description 8
• 229920002635 polyurethane Polymers 0.000 description 8
• 239000000843 powder Substances 0.000 description 8
• 238000001228 spectrum Methods 0.000 description 8
• 239000004698 Polyethylene Substances 0.000 description 7
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 7
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
• 239000007983 Tris buffer Substances 0.000 description 7
• 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
• 239000007859 condensation product Substances 0.000 description 7
• 238000005336 cracking Methods 0.000 description 7
• 150000001993 dienes Chemical class 0.000 description 7
• 239000000049 pigment Substances 0.000 description 7
• 229920000647 polyepoxide Polymers 0.000 description 7
• 229920000570 polyether Polymers 0.000 description 7
• 229920000573 polyethylene Polymers 0.000 description 7
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
• 238000005481 NMR spectroscopy Methods 0.000 description 6
• OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 6
• 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
• 125000001931 aliphatic group Chemical group 0.000 description 6
• 239000012964 benzotriazole Substances 0.000 description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
• 150000002739 metals Chemical class 0.000 description 6
• 239000004417 polycarbonate Substances 0.000 description 6
• 239000005056 polyisocyanate Substances 0.000 description 6
• 229920001228 polyisocyanate Polymers 0.000 description 6
• 229920006324 polyoxymethylene Polymers 0.000 description 6
• 229920000915 polyvinyl chloride Polymers 0.000 description 6
• 239000004800 polyvinyl chloride Substances 0.000 description 6
• 238000002360 preparation method Methods 0.000 description 6
• 239000011814 protection agent Substances 0.000 description 6
• 229920001169 thermoplastic Polymers 0.000 description 6
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
• RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 5
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
• GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
• 125000003277 amino group Chemical group 0.000 description 5
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
• 238000006243 chemical reaction Methods 0.000 description 5
• 239000006185 dispersion Substances 0.000 description 5
• 229920001971 elastomer Polymers 0.000 description 5
• 238000009472 formulation Methods 0.000 description 5
• 229920001903 high density polyethylene Polymers 0.000 description 5
• 239000004700 high-density polyethylene Substances 0.000 description 5
• 150000002431 hydrogen Chemical class 0.000 description 5
• 239000012948 isocyanate Substances 0.000 description 5
• WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
• 229920000058 polyacrylate Polymers 0.000 description 5
• 235000013772 propylene glycol Nutrition 0.000 description 5
• 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
• 229910052709 silver Inorganic materials 0.000 description 5
• 239000004332 silver Substances 0.000 description 5
• 239000000758 substrate Substances 0.000 description 5
• 150000005846 sugar alcohols Polymers 0.000 description 5
• 239000004416 thermosoftening plastic Substances 0.000 description 5
• DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 4
• DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
• RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
• CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
• BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
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• 238000009835 boiling Methods 0.000 description 4
• 230000015556 catabolic process Effects 0.000 description 4
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• 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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• 238000006731 degradation reaction Methods 0.000 description 4
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• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
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• NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
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• 229910052748 manganese Inorganic materials 0.000 description 4
• 239000011572 manganese Substances 0.000 description 4
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• 230000001590 oxidative effect Effects 0.000 description 4
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
• YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
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• BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 3
• FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
• RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 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
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• 229910002091 carbon monoxide Inorganic materials 0.000 description 3
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• 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
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• JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 3
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• JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
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