KR100996586B1 - 상승적 ｕｖ 흡수제 배합물 - Google Patents

Info

Publication number

KR100996586B1

KR100996586B1 KR1020057005789A KR20057005789A KR100996586B1 KR 100996586 B1 KR100996586 B1 KR 100996586B1 KR 1020057005789 A KR1020057005789 A KR 1020057005789A KR 20057005789 A KR20057005789 A KR 20057005789A KR 100996586 B1 KR100996586 B1 KR 100996586B1

Authority

KR

South Korea

Prior art keywords

compound

hydroxy

tert

bis

butyl

Prior art date

2002-10-02

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.)

Expired - Lifetime

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• 239000000203 mixture Substances 0.000 title claims abstract description 204
• 238000009472 formulation Methods 0.000 title abstract description 81
• 230000035939 shock Effects 0.000 title description 3
• 230000002745 absorbent Effects 0.000 title 1
• 239000002250 absorbent Substances 0.000 title 1
• 230000002195 synergetic effect Effects 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 218
• -1 light Substances 0.000 claims abstract description 192
• 239000003381 stabilizer Substances 0.000 claims abstract description 83
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 54
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 53
• 239000006096 absorbing agent Substances 0.000 claims abstract description 31
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
• 239000011368 organic material Substances 0.000 claims abstract description 12
• 239000001301 oxygen Substances 0.000 claims abstract description 12
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 239000012964 benzotriazole Substances 0.000 claims abstract description 10
• 230000000087 stabilizing effect Effects 0.000 claims abstract description 10
• QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims abstract description 8
• HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims abstract description 7
• HTTGVORJOBRXRJ-UHFFFAOYSA-N 2-(triazin-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CC=NN=N1 HTTGVORJOBRXRJ-UHFFFAOYSA-N 0.000 claims abstract description 5
• FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 claims abstract description 5
• 229940114081 cinnamate Drugs 0.000 claims abstract description 3
• WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims abstract description 3
• 239000000654 additive Substances 0.000 claims description 53
• 150000001412 amines Chemical class 0.000 claims description 53
• 239000001257 hydrogen Substances 0.000 claims description 51
• 239000000126 substance Substances 0.000 claims description 47
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 239000000049 pigment Substances 0.000 claims description 28
• 238000000034 method Methods 0.000 claims description 26
• 230000000996 additive effect Effects 0.000 claims description 25
• 150000002431 hydrogen Chemical class 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 239000003054 catalyst Substances 0.000 claims description 19
• 239000000047 product Substances 0.000 claims description 14
• 239000004611 light stabiliser Substances 0.000 claims description 13
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
• RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000004423 acyloxy group Chemical group 0.000 claims description 7
• 239000003063 flame retardant Substances 0.000 claims description 7
• 229910052736 halogen Inorganic materials 0.000 claims description 7
• 150000002367 halogens Chemical class 0.000 claims description 7
• ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 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 claims description 5
• 239000007795 chemical reaction product Substances 0.000 claims description 5
• FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 claims description 4
• LHPPDQUVECZQSW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-ditert-butylphenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=CC=CC3=N2)=C1O LHPPDQUVECZQSW-UHFFFAOYSA-N 0.000 claims description 4
• 239000003963 antioxidant agent Substances 0.000 claims description 4
• 239000002216 antistatic agent Substances 0.000 claims description 4
• LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 claims description 3
• VQMHSKWEJGIXGA-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-6-dodecyl-4-methylphenol Chemical compound CCCCCCCCCCCCC1=CC(C)=CC(N2N=C3C=CC=CC3=N2)=C1O VQMHSKWEJGIXGA-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
• YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 claims description 3
• 150000001298 alcohols Chemical class 0.000 claims description 3
• 125000004432 carbon atom Chemical group C* 0.000 claims description 3
• UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 claims description 3
• 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 claims description 3
• DMFXLIFZVRXRRR-UHFFFAOYSA-N octyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O DMFXLIFZVRXRRR-UHFFFAOYSA-N 0.000 claims description 3
• 239000004014 plasticizer Substances 0.000 claims description 3
• 229940068886 polyethylene glycol 300 Drugs 0.000 claims description 3
• 238000005809 transesterification reaction Methods 0.000 claims description 3
• ARVUDIQYNJVQIW-UHFFFAOYSA-N (4-dodecoxy-2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC(OCCCCCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 ARVUDIQYNJVQIW-UHFFFAOYSA-N 0.000 claims description 2
• 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 2
• 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 claims description 2
• ZXDDPOHVAMWLBH-UHFFFAOYSA-N 2,4-Dihydroxybenzophenone Chemical compound OC1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 ZXDDPOHVAMWLBH-UHFFFAOYSA-N 0.000 claims description 2
• NEAHJFGPHPHWND-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)-6-[5-(trifluoromethyl)benzotriazol-2-yl]-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound C=1C(C(C)(C)CC(C)(C)C)=CC(N2N=C3C=C(C=CC3=N2)C(F)(F)F)=C(O)C=1C(C)(C)C1=CC=CC=C1 NEAHJFGPHPHWND-UHFFFAOYSA-N 0.000 claims description 2
• OLFNXLXEGXRUOI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 claims description 2
• IYAZLDLPUNDVAG-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 IYAZLDLPUNDVAG-UHFFFAOYSA-N 0.000 claims description 2
• CHKKZILXOJVMAD-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-(2-hydroxyethyl)phenol Chemical compound OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 CHKKZILXOJVMAD-UHFFFAOYSA-N 0.000 claims description 2
• WXHVQMGINBSVAY-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 WXHVQMGINBSVAY-UHFFFAOYSA-N 0.000 claims description 2
• VCYCUECVHJJFIQ-UHFFFAOYSA-N 2-[3-(benzotriazol-2-yl)-4-hydroxyphenyl]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 VCYCUECVHJJFIQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 239000004604 Blowing Agent Substances 0.000 claims description 2
• HEQXWFXUNCJOSL-UHFFFAOYSA-N C1(=CC=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=C(C=C(C=C1)CCOC(C(=O)CC)CCCC)O Chemical compound C1(=CC=CC=C1)C1=NC(=NC(=N1)C1=CC=CC=C1)C1=C(C=C(C=C1)CCOC(C(=O)CC)CCCC)O HEQXWFXUNCJOSL-UHFFFAOYSA-N 0.000 claims description 2
• 230000003078 antioxidant effect Effects 0.000 claims description 2
• OCWYEMOEOGEQAN-UHFFFAOYSA-N bumetrizole Chemical compound CC(C)(C)C1=CC(C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O OCWYEMOEOGEQAN-UHFFFAOYSA-N 0.000 claims description 2
• MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 claims description 2
• 239000003995 emulsifying agent Substances 0.000 claims description 2
• JLXNKSKTFQDTGM-UHFFFAOYSA-N ethyl 2-[4-[4,6-bis[4-(1-ethoxy-1-oxopropan-2-yl)oxy-2-hydroxyphenyl]-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]propanoate Chemical compound OC1=CC(OC(C)C(=O)OCC)=CC=C1C1=NC(C=2C(=CC(OC(C)C(=O)OCC)=CC=2)O)=NC(C=2C(=CC(OC(C)C(=O)OCC)=CC=2)O)=N1 JLXNKSKTFQDTGM-UHFFFAOYSA-N 0.000 claims description 2
• 239000000314 lubricant Substances 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 claims description 2
• DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 claims description 2
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
• 238000000518 rheometry Methods 0.000 claims description 2
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 2
• KIPGIZCKZDHTJB-UHFFFAOYSA-N 2-(4-phenylphenyl)-1,3,5-triazine Chemical compound C1=CC=CC=C1C1=CC=C(C=2N=CN=CN=2)C=C1 KIPGIZCKZDHTJB-UHFFFAOYSA-N 0.000 claims 1
• CMLFRMDBDNHMRA-UHFFFAOYSA-N 2h-1,2-benzoxazine Chemical compound C1=CC=C2C=CNOC2=C1 CMLFRMDBDNHMRA-UHFFFAOYSA-N 0.000 claims 1
• CNGYZEMWVAWWOB-VAWYXSNFSA-N 5-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-[(e)-2-[4-[[4-anilino-6-[bis(2-hydroxyethyl)amino]-1,3,5-triazin-2-yl]amino]-2-sulfophenyl]ethenyl]benzenesulfonic acid Chemical compound N=1C(NC=2C=C(C(\C=C\C=3C(=CC(NC=4N=C(N=C(NC=5C=CC=CC=5)N=4)N(CCO)CCO)=CC=3)S(O)(=O)=O)=CC=2)S(O)(=O)=O)=NC(N(CCO)CCO)=NC=1NC1=CC=CC=C1 CNGYZEMWVAWWOB-VAWYXSNFSA-N 0.000 claims 1
• 125000005605 benzo group Chemical group 0.000 claims 1
• TWCBCCIODCKPGX-UHFFFAOYSA-N octyl 2-[4-[4,6-bis(4-phenylphenyl)-1,3,5-triazin-2-yl]-3-hydroxyphenoxy]propanoate Chemical compound OC1=CC(OC(C)C(=O)OCCCCCCCC)=CC=C1C1=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=NC(C=2C=CC(=CC=2)C=2C=CC=CC=2)=N1 TWCBCCIODCKPGX-UHFFFAOYSA-N 0.000 claims 1
• 239000003223 protective agent Substances 0.000 claims 1
• 239000000516 sunscreening agent Substances 0.000 claims 1
• 125000003118 aryl group Chemical group 0.000 abstract description 7
• 229910052799 carbon Inorganic materials 0.000 abstract description 6
• 230000003647 oxidation Effects 0.000 abstract description 6
• 238000007254 oxidation reaction Methods 0.000 abstract description 6
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 abstract description 5
• 150000001558 benzoic acid derivatives Chemical class 0.000 abstract description 3
• 150000001565 benzotriazoles Chemical class 0.000 abstract description 3
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 abstract description 2
• 125000003358 C2-C20 alkenyl group Chemical group 0.000 abstract description 2
• 238000000354 decomposition reaction Methods 0.000 abstract description 2
• GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 abstract description 2
• 239000010408 film Substances 0.000 description 80
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• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 50
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• CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 24
• 239000008188 pellet Substances 0.000 description 23
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• 229920000570 polyether Polymers 0.000 description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
• 239000005062 Polybutadiene Substances 0.000 description 9
• 229920000180 alkyd Polymers 0.000 description 9
• 230000008859 change Effects 0.000 description 9
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