CA2215261A1 - Hydroxyphenyltriazines - Google Patents
Hydroxyphenyltriazines Download PDFInfo
- Publication number
- CA2215261A1 CA2215261A1 CA002215261A CA2215261A CA2215261A1 CA 2215261 A1 CA2215261 A1 CA 2215261A1 CA 002215261 A CA002215261 A CA 002215261A CA 2215261 A CA2215261 A CA 2215261A CA 2215261 A1 CA2215261 A1 CA 2215261A1
- Authority
- CA
- Canada
- Prior art keywords
- substituted
- halogen
- c12alkyl
- c12alkoxy
- tert
- 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
- VMRIVYANZGSGRV-UHFFFAOYSA-N 4-phenyl-2h-triazin-5-one Chemical class OC1=CN=NN=C1C1=CC=CC=C1 VMRIVYANZGSGRV-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 150000002367 halogens Chemical class 0.000 claims abstract description 52
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 51
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims abstract description 29
- 125000001424 substituent group Chemical group 0.000 claims abstract description 28
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000011368 organic material Substances 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 11
- 230000006641 stabilisation Effects 0.000 claims abstract description 9
- 229910006069 SO3H Inorganic materials 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 5
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 5
- -1 C4-C12cycloalkyl Chemical group 0.000 claims description 172
- 239000000203 mixture Substances 0.000 claims description 68
- 238000000576 coating method Methods 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 239000003381 stabilizer Substances 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 25
- 239000011347 resin Substances 0.000 claims description 25
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 22
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- 239000011230 binding agent Substances 0.000 claims description 19
- 239000000463 material Substances 0.000 claims description 15
- 239000011248 coating agent Substances 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 14
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 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
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- 230000003019 stabilising effect Effects 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 6
- 229920000180 alkyd Polymers 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 4
- 229920001225 polyester resin Polymers 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 229920000178 Acrylic resin Polymers 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 229920000620 organic polymer Polymers 0.000 claims description 2
- 229920006122 polyamide resin Polymers 0.000 claims description 2
- 229920005749 polyurethane 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
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- POXYEBBFGJFTDI-UHFFFAOYSA-N [3-[4-(4,6-diphenyl-1,3,5-triazin-2-yl)-3-hydroxyphenoxy]-2-hydroxypropyl] benzoate Chemical compound C1(=CC=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=C(C=C(C=C1)OCC(COC(C1=CC=CC=C1)=O)O)O POXYEBBFGJFTDI-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 abstract description 17
- 230000000254 damaging effect Effects 0.000 abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 51
- 229920001577 copolymer Polymers 0.000 description 35
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
- 239000008199 coating composition Substances 0.000 description 26
- 239000007787 solid Substances 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
- 239000004922 lacquer Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 229910052799 carbon Inorganic materials 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 239000006096 absorbing agent Substances 0.000 description 14
- 239000004743 Polypropylene Substances 0.000 description 13
- 229920001155 polypropylene Polymers 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- 239000005977 Ethylene Substances 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 11
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 10
- 239000005062 Polybutadiene Substances 0.000 description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 229920000877 Melamine resin Polymers 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 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
- 239000004611 light stabiliser Substances 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 238000001723 curing Methods 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920002635 polyurethane Polymers 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000007859 condensation product Substances 0.000 description 7
- 229920001684 low density polyethylene Polymers 0.000 description 7
- 239000004702 low-density polyethylene Substances 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 229920000570 polyether Polymers 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 239000004698 Polyethylene Substances 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229920000573 polyethylene Polymers 0.000 description 6
- 239000005056 polyisocyanate Substances 0.000 description 6
- 229920001228 polyisocyanate Polymers 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 229920001169 thermoplastic Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 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 5
- 239000004925 Acrylic resin Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 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 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000000839 emulsion Substances 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
- 239000012948 isocyanate Substances 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 229920000647 polyepoxide 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
- 150000003254 radicals Chemical class 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
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- 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 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-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
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical class OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-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
- 239000004593 Epoxy Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000012964 benzotriazole Substances 0.000 description 4
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 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
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 238000005286 illumination Methods 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 229910052748 manganese Inorganic materials 0.000 description 4
- 239000011572 manganese Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 4
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- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- 239000011732 tocopherol Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical class OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-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
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
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- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(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 JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- XITRBUPOXXBIJN-UHFFFAOYSA-N bis(2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)NC(C)(C)C1 XITRBUPOXXBIJN-UHFFFAOYSA-N 0.000 description 3
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 3
- 235000013539 calcium stearate Nutrition 0.000 description 3
- 239000008116 calcium stearate Substances 0.000 description 3
- 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
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 229920001971 elastomer Polymers 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 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
- 238000001704 evaporation Methods 0.000 description 3
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- 150000004665 fatty acids Chemical class 0.000 description 3
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- 229920000554 ionomer Polymers 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
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- WGCBLWIBXXQTAW-UHFFFAOYSA-N n-hexadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC WGCBLWIBXXQTAW-UHFFFAOYSA-N 0.000 description 1
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- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
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- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
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- 239000003380 propellant Substances 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 239000012744 reinforcing agent Substances 0.000 description 1
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
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- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
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- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
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- 239000011115 styrene butadiene Substances 0.000 description 1
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- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
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- 125000004306 triazinyl group Chemical group 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- SHEXSXZCZQBTFI-UHFFFAOYSA-N tridecyl 3-(3,5-ditert-butyl-4-hydroxyphenyl)-2-sulfanylpropanoate Chemical compound CCCCCCCCCCCCCOC(=O)C(S)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SHEXSXZCZQBTFI-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
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 239000002023 wood Substances 0.000 description 1
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- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000001043 yellow dye Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Hydrogenated Pyridines (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH225496 | 1996-09-13 | ||
| CH2254/96 | 1996-09-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2215261A1 true CA2215261A1 (en) | 1998-03-13 |
Family
ID=4229481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002215261A Abandoned CA2215261A1 (en) | 1996-09-13 | 1997-09-11 | Hydroxyphenyltriazines |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6013704A (enExample) |
| JP (1) | JP4280943B2 (enExample) |
| KR (1) | KR100525173B1 (enExample) |
| BE (1) | BE1011451A5 (enExample) |
| BR (1) | BR9704717A (enExample) |
| CA (1) | CA2215261A1 (enExample) |
| DE (1) | DE19739781A1 (enExample) |
| FR (1) | FR2753447B1 (enExample) |
| GB (1) | GB2317174B (enExample) |
| IT (1) | IT1295009B1 (enExample) |
| NL (1) | NL1007031C2 (enExample) |
| SE (1) | SE522822C2 (enExample) |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20020165298A1 (en) | 1996-04-02 | 2002-11-07 | Dieter Reinehr | Amino- and hydroxysubstituted triphenyl-s-triazines as stabilizers |
| US6191199B1 (en) | 1999-05-03 | 2001-02-20 | Ciba Speciatly Chemicals Corporation | Stabilized adhesive compositions containing highly soluble, high extinction photostable hydroxyphenyl-s-triazine UV absorbers and laminated articles derived therefrom |
| MX229551B (es) | 2000-02-01 | 2005-07-29 | Ciba Sc Holding Ag | Metodo de proteccion de contenido con absorbentes de uv durables. |
| DE10030658C1 (de) * | 2000-06-23 | 2002-01-03 | Trespa Int Bv | Flammwidrige Harzbeschichtung |
| BR0208220A (pt) | 2001-03-22 | 2004-04-13 | Ciba Sc Holding Ag | Uso de compostos aromáticos como diretores de fase e redutores de tamanho de partìcula para pigmentos quinacridona |
| KR100803888B1 (ko) | 2001-04-06 | 2008-02-14 | 가부시키가이샤 아데카 | 합성 수지용 자외선 흡수제 및 이것을 함유하여 된 합성수지 조성물 |
| TWI318208B (en) * | 2001-07-02 | 2009-12-11 | Ciba Sc Holding Ag | Highly compatible hydroxyphenyltriazine uv-absorbers |
| EP1308084A1 (en) * | 2002-10-02 | 2003-05-07 | Ciba SC Holding AG | Synergistic UV absorber combination |
| CA2517334A1 (en) | 2003-02-26 | 2004-09-10 | Ciba Specialty Chemicals Holding Inc. | Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines |
| WO2004077885A2 (en) * | 2003-02-28 | 2004-09-10 | Ciba Specialty Chemicals Holding Inc. | Electroluminescent device |
| US7611829B2 (en) | 2004-01-30 | 2009-11-03 | Fujifilm Corporation | Silver halide color photographic light-sensitive material and color image-forming method |
| US7595011B2 (en) | 2004-07-12 | 2009-09-29 | Ciba Specialty Chemicals Corporation | Stabilized electrochromic media |
| DE102005041952A1 (de) * | 2005-09-03 | 2007-03-08 | Bayer Materialscience Ag | Zusammensetzungen enthaltend Polycarbonat und neuartige UV-Absorber |
| US20090115328A1 (en) | 2006-05-26 | 2009-05-07 | Seiji Yamashita | Surface emitting-type electroluminescent device |
| EP1980409A3 (en) | 2007-03-29 | 2010-09-29 | FUJIFILM Corporation | Heat-sensitive transfer sheet for use in heat-sensitive transfer system and image-forming method using heat-sensitive transfer system |
| US8119562B2 (en) | 2007-03-29 | 2012-02-21 | Fujifilm Corporation | Heat-sensitive transfer sheet and image-forming method using heat-sensitive transfer system |
| EP1974948A3 (en) | 2007-03-29 | 2012-02-08 | FUJIFILM Corporation | Image-forming method using heat-sensitive transfer system |
| WO2008124797A1 (en) * | 2007-04-09 | 2008-10-16 | Designer Molecules, Inc. | Curatives for epoxy compositions |
| US8431655B2 (en) * | 2007-04-09 | 2013-04-30 | Designer Molecules, Inc. | Curatives for epoxy compositions |
| US20100056671A1 (en) * | 2007-04-12 | 2010-03-04 | Designer Molecules, Inc. | Polyfunctional epoxy oligomers |
| DE102007017936A1 (de) | 2007-04-13 | 2008-10-16 | Bayer Materialscience Ag | Erzeugnisse mit verbesserter Flammwidrigkeit |
| JP2008273641A (ja) | 2007-04-25 | 2008-11-13 | Fujifilm Corp | 感熱転写受像シート用紙管、感熱転写受像シートのロール形態加工物、及び画像形成方法 |
| US8399536B2 (en) | 2007-06-29 | 2013-03-19 | Basell Poliolefine Italia, s.r.l. | Irradiated polyolefin composition comprising a non-phenolic stabilizer |
| DE102007050192A1 (de) * | 2007-10-20 | 2009-04-23 | Bayer Materialscience Ag | Zusammensetzung mit UV-Schutz |
| US8349925B2 (en) | 2008-09-05 | 2013-01-08 | Thor Gmbh | Flame-retardant composition comprising a phosphonic acid derivative |
| JP5631331B2 (ja) | 2008-12-22 | 2014-11-26 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 引掻耐性の向上方法及び関連製品及びその使用 |
| CN102292397B (zh) | 2009-01-19 | 2014-12-10 | 巴斯夫欧洲公司 | 有机黑色颜料及其制备 |
| BR112012000425A2 (pt) | 2009-07-07 | 2018-04-10 | Basf Se | particulas de solução sólida de bronze de potássio-césio-tungstênio, processo para a preparação de partículas de solução sólida de bronze de potássio-césio-tungstênio, potássio-césio-tungstênio. |
| DE102009052042A1 (de) | 2009-11-05 | 2011-05-12 | Bayer Materialscience Ag | Polycarbonatzusammensetzung mit verbesserter Flammwidrigkeit für Extrusionsanwendungen |
| KR20120108974A (ko) | 2009-11-05 | 2012-10-05 | 바이엘 머티리얼사이언스 아게 | 압출된 제품에 사용되는 난연성이 개선된 폴리카르보네이트 조성물 |
| RU2012127826A (ru) | 2009-12-05 | 2014-01-10 | Байер Интеллектуэль Проперти Гмбх | Поликарбонатные композиции с фенолзамещенным производным триазина |
| WO2011139111A1 (en) * | 2010-05-07 | 2011-11-10 | Rohm And Haas Electronic Materials Korea Ltd. | Resin composition, insulating film using the same, and electronic component |
| JP5544239B2 (ja) | 2010-07-29 | 2014-07-09 | 富士フイルム株式会社 | 重合性組成物 |
| CN103118657A (zh) | 2010-09-14 | 2013-05-22 | 巴斯夫欧洲公司 | 特殊二(联苯基)三嗪衍生物及其混合物作为uv吸收剂的用途 |
| EP2447236A1 (de) | 2010-10-12 | 2012-05-02 | Bayer MaterialScience AG | Spezielle UV-Absorber für härtbare UV-Schutz Beschichtungen |
| EP2801847A4 (en) | 2012-01-06 | 2015-08-26 | Konica Minolta Inc | FILM MIRRORS, FILM MIRROR PRODUCTION METHODS, FILM MIRRORS FOR PHOTOVOLTAIC POWER GENERATION AND REFLECTION DEVICES FOR PHOTOVOLTAIC ENERGY PRODUCTION |
| CN104736258A (zh) | 2012-08-23 | 2015-06-24 | 拜尔材料科学股份公司 | 有机uv吸收剂在塑料基底上的气相沉积 |
| JP6246223B2 (ja) | 2012-10-23 | 2017-12-13 | ビーエーエスエフ エスイー | ポリマー安定剤基を含有するエチレン性不飽和オリゴマー |
| BR112016006528B1 (pt) | 2013-09-27 | 2021-07-27 | Basf Se | Artigo extrudado compreendendo uma composição de poliolefina |
| WO2015077635A2 (en) | 2013-11-22 | 2015-05-28 | Polnox Corporation | Macromolecular antioxidants based on dual type moiety per molecule: structures methods of making and using the same |
| TWI685524B (zh) | 2013-12-17 | 2020-02-21 | 美商畢克美國股份有限公司 | 預先脫層之層狀材料 |
| US20190010308A1 (en) | 2015-07-20 | 2019-01-10 | Basf Se | Flame Retardant Polyolefin Articles |
| CN110352223B (zh) | 2017-04-25 | 2022-08-02 | 巴斯夫欧洲公司 | 具有共价结合紫外线吸收剂的涂料组合物 |
| EP3841166B2 (en) | 2018-08-22 | 2025-05-07 | Basf Se | Stabilized rotomolded polyolefin |
| WO2020190833A1 (en) | 2019-03-18 | 2020-09-24 | Basf Se | Uv curable compositions for dirt pick-up resistance |
| US20220282064A1 (en) | 2019-07-30 | 2022-09-08 | Basf Se | Stabilizer composition |
| MX2023009501A (es) * | 2021-03-30 | 2023-08-23 | Apeel Tech Inc | Composicion de pelicula de barrera comestible. |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3118887A (en) * | 1961-03-06 | 1964-01-21 | American Cyanamid Co | O-hydroxy substituted tris aryl-s-triazines |
| BE639330A (enExample) * | 1962-10-30 | |||
| NL130993C (enExample) * | 1963-02-07 | |||
| CH469053A (de) * | 1963-07-26 | 1969-02-28 | Ciba Geigy | Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Schutzmittel gegen Ultraviolettstrahlung für nichttextile organische Materialien |
| CH533853A (de) * | 1970-03-23 | 1973-02-15 | Ciba Geigy Ag | Verwendung von 2'-Hydroxyphenyl-1,3,5-triazinen als Stabilisierungsmittel gegen Ultraviolettstrahlung in photographischem Material |
| US4619956A (en) * | 1985-05-03 | 1986-10-28 | American Cyanamid Co. | Stabilization of high solids coatings with synergistic combinations |
| US5073278A (en) * | 1988-07-18 | 1991-12-17 | Ciba-Geigy Corporation | Lubricant composition |
| US5273669A (en) * | 1988-07-18 | 1993-12-28 | Ciba-Geigy Corporation | Lubricant composition |
| SG49847A1 (en) * | 1989-12-05 | 1999-07-20 | Ciba Sc Holding Ag | Stabilized organic material |
| EP0444323B1 (en) * | 1990-02-28 | 1997-03-19 | Cytec Technology Corp. | Stabilization of high solids coating with liquid compositions of triazine UV absorbers |
| EP0453405B1 (de) * | 1990-04-20 | 2000-07-12 | Ciba SC Holding AG | Verbindungen aus o-Hydroxyphenyl-1,3,5-triazinen und sterisch gehinderten Aminen |
| ES2099721T3 (es) * | 1990-10-29 | 1997-06-01 | Cytec Tech Corp | Composiciones sinergicas absorbentes de radiacion ultravioleta que contienen hidroxi aril triazinas y tetraalquil piperidinas. |
| US5489503A (en) * | 1992-12-03 | 1996-02-06 | Ciba-Geigy Corp. | UV absorbers |
| US5354794A (en) * | 1993-02-03 | 1994-10-11 | Ciba-Geigy Corporation | Electro coat/base coat/clear coat finishes stabilized with S-triazine UV absorbers |
| US5556973A (en) * | 1994-07-27 | 1996-09-17 | Ciba-Geigy Corporation | Red-shifted tris-aryl-s-triazines and compositions stabilized therewith |
| EP0815089B1 (en) * | 1995-03-15 | 2002-09-25 | Ciba SC Holding AG | Biphenyl-substituted triazines as light stabilizer |
-
1997
- 1997-09-10 IT IT97MI002059A patent/IT1295009B1/it active IP Right Grant
- 1997-09-10 DE DE19739781A patent/DE19739781A1/de not_active Withdrawn
- 1997-09-10 US US08/929,147 patent/US6013704A/en not_active Expired - Lifetime
- 1997-09-10 GB GB9719145A patent/GB2317174B/en not_active Expired - Fee Related
- 1997-09-11 FR FR9711288A patent/FR2753447B1/fr not_active Expired - Fee Related
- 1997-09-11 CA CA002215261A patent/CA2215261A1/en not_active Abandoned
- 1997-09-11 SE SE9703288A patent/SE522822C2/sv not_active IP Right Cessation
- 1997-09-11 BE BE9700741A patent/BE1011451A5/fr not_active IP Right Cessation
- 1997-09-12 JP JP28900797A patent/JP4280943B2/ja not_active Expired - Fee Related
- 1997-09-12 NL NL1007031A patent/NL1007031C2/nl not_active IP Right Cessation
- 1997-09-13 KR KR1019970047758A patent/KR100525173B1/ko not_active Expired - Fee Related
- 1997-09-15 BR BR9704717A patent/BR9704717A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR100525173B1 (ko) | 2006-05-16 |
| ITMI972059A1 (it) | 1999-03-10 |
| GB9719145D0 (en) | 1997-11-12 |
| SE9703288L (sv) | 1998-03-14 |
| FR2753447B1 (fr) | 2000-07-13 |
| FR2753447A1 (fr) | 1998-03-20 |
| GB2317174B (en) | 2000-05-17 |
| SE9703288D0 (sv) | 1997-09-11 |
| NL1007031A1 (nl) | 1998-03-16 |
| DE19739781A1 (de) | 1998-03-19 |
| US6013704A (en) | 2000-01-11 |
| GB2317174A (en) | 1998-03-18 |
| BE1011451A5 (fr) | 1999-09-07 |
| JP4280943B2 (ja) | 2009-06-17 |
| KR19980024774A (ko) | 1998-07-06 |
| BR9704717A (pt) | 1998-12-22 |
| JPH10147577A (ja) | 1998-06-02 |
| SE522822C2 (sv) | 2004-03-09 |
| IT1295009B1 (it) | 1999-04-27 |
| MX9706949A (es) | 1998-08-30 |
| NL1007031C2 (nl) | 1999-01-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |