JP2004525185A - 長鎖立体障害アミン及びこれにより安定化された組成物 - Google Patents
長鎖立体障害アミン及びこれにより安定化された組成物 Download PDFInfo
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- JP2004525185A JP2004525185A JP2002582126A JP2002582126A JP2004525185A JP 2004525185 A JP2004525185 A JP 2004525185A JP 2002582126 A JP2002582126 A JP 2002582126A JP 2002582126 A JP2002582126 A JP 2002582126A JP 2004525185 A JP2004525185 A JP 2004525185A
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- carbon atoms
- alkyl
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- hydrogen
- methyl
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- 150000001412 amines Chemical class 0.000 title claims abstract description 30
- 239000000203 mixture Substances 0.000 title claims description 76
- -1 amine compounds Chemical group 0.000 claims abstract description 184
- 239000006096 absorbing agent Substances 0.000 claims abstract description 40
- 125000003118 aryl group Chemical group 0.000 claims abstract description 27
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 223
- 125000000217 alkyl group Chemical group 0.000 claims description 160
- 239000001257 hydrogen Substances 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 52
- 150000002431 hydrogen Chemical class 0.000 claims description 51
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 28
- 150000003254 radicals Chemical class 0.000 claims description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 229920005989 resin Polymers 0.000 claims description 23
- 239000011347 resin Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 21
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 21
- 239000005977 Ethylene Substances 0.000 claims description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 21
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 21
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 18
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
- 230000000087 stabilizing effect Effects 0.000 claims description 17
- 229920000098 polyolefin Polymers 0.000 claims description 16
- 239000004952 Polyamide Substances 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 239000012964 benzotriazole Substances 0.000 claims description 15
- 239000000460 chlorine Substances 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 229920002647 polyamide Polymers 0.000 claims description 15
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 14
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 14
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 14
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 claims description 14
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 14
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 claims description 14
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 14
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 14
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical compound NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 12
- 230000003078 antioxidant effect Effects 0.000 claims description 12
- 229920000728 polyester Polymers 0.000 claims description 12
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 12
- 239000007983 Tris buffer Substances 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 11
- 239000003205 fragrance Substances 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- RLMGYIOTPQVQJR-UHFFFAOYSA-N cyclohexane-1,3-diol Chemical compound OC1CCCC(O)C1 RLMGYIOTPQVQJR-UHFFFAOYSA-N 0.000 claims description 9
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 8
- 229920005992 thermoplastic resin Polymers 0.000 claims description 8
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 7
- NMRPBPVERJPACX-UHFFFAOYSA-N (3S)-octan-3-ol Natural products CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 claims description 7
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 7
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims description 7
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 7
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 7
- 239000005968 1-Decanol Substances 0.000 claims description 7
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 7
- WOFPPJOZXUTRAU-UHFFFAOYSA-N 2-Ethyl-1-hexanol Natural products CCCCC(O)CCC WOFPPJOZXUTRAU-UHFFFAOYSA-N 0.000 claims description 7
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 7
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- BMRWNKZVCUKKSR-UHFFFAOYSA-N butane-1,2-diol Chemical compound CCC(O)CO BMRWNKZVCUKKSR-UHFFFAOYSA-N 0.000 claims description 7
- PMMYEEVYMWASQN-IMJSIDKUSA-N cis-4-Hydroxy-L-proline Chemical compound O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 claims description 7
- FHADSMKORVFYOS-UHFFFAOYSA-N cyclooctanol Chemical compound OC1CCCCCCC1 FHADSMKORVFYOS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 7
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 claims description 7
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 7
- 235000013772 propylene glycol Nutrition 0.000 claims description 7
- 229920001187 thermosetting polymer Polymers 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
- 229920001169 thermoplastic Polymers 0.000 claims description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 5
- 239000012965 benzophenone Substances 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 239000011368 organic material Substances 0.000 claims description 5
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 5
- 239000004416 thermosoftening plastic Substances 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 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 description 4
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 3
- 239000002250 absorbent Substances 0.000 claims description 3
- 230000002745 absorbent Effects 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- FJNSCHNEOHRLNF-UHFFFAOYSA-N 1-(3-amino-2,2,6,6-tetramethylpiperidin-1-yl)oxy-2-methylpropan-2-ol Chemical compound CC(C)(O)CON1C(C)(C)CCC(N)C1(C)C FJNSCHNEOHRLNF-UHFFFAOYSA-N 0.000 claims description 2
- RSWUFKBWHFSVIY-UHFFFAOYSA-N 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine-4-carboxylic acid Chemical compound CC1(C)CC(C(O)=O)CC(C)(C)N1OC1CCCCC1 RSWUFKBWHFSVIY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 229940114081 cinnamate Drugs 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000005724 cycloalkenylene group Chemical group 0.000 claims description 2
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 claims description 2
- 125000003367 polycyclic group Chemical group 0.000 claims description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 claims description 2
- 229960001860 salicylate Drugs 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 4
- ARXKVVRQIIOZGF-UHFFFAOYSA-N 1,2,4-butanetriol Chemical compound OCCC(O)CO ARXKVVRQIIOZGF-UHFFFAOYSA-N 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
- 238000002845 discoloration Methods 0.000 abstract description 10
- 238000005562 fading Methods 0.000 abstract description 8
- 238000004040 coloring Methods 0.000 abstract description 3
- 238000006467 substitution reaction Methods 0.000 abstract description 3
- 238000007598 dipping method Methods 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 48
- 239000001993 wax Substances 0.000 description 47
- 229920001577 copolymer Polymers 0.000 description 37
- 239000010410 layer Substances 0.000 description 28
- 239000003381 stabilizer Substances 0.000 description 25
- 229920000642 polymer Polymers 0.000 description 20
- 229920000877 Melamine resin Polymers 0.000 description 18
- 239000004743 Polypropylene Substances 0.000 description 16
- 229920000139 polyethylene terephthalate Polymers 0.000 description 16
- 239000005020 polyethylene terephthalate Substances 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 14
- 235000006708 antioxidants Nutrition 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- 239000000975 dye Substances 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 13
- 229920001684 low density polyethylene Polymers 0.000 description 12
- 239000004702 low-density polyethylene Substances 0.000 description 12
- 229920001155 polypropylene Polymers 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 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 description 10
- 230000008859 change Effects 0.000 description 10
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 9
- 229920000178 Acrylic resin Polymers 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 229920006324 polyoxymethylene Polymers 0.000 description 9
- 239000004925 Acrylic resin Substances 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- 239000004593 Epoxy Substances 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 229920001903 high density polyethylene Polymers 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- 239000004922 lacquer Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- SFRDXVJWXWOTEW-UHFFFAOYSA-N 2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)CO SFRDXVJWXWOTEW-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 229920000180 alkyd Polymers 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 230000015556 catabolic process Effects 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 238000006731 degradation reaction Methods 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 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 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 150000003053 piperidines Chemical group 0.000 description 6
- 238000006068 polycondensation reaction Methods 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- RSOILICUEWXSLA-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(C)C(C)(C)C1 RSOILICUEWXSLA-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
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- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 229920000428 triblock copolymer Polymers 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 230000000007 visual effect Effects 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
- 238000004383 yellowing Methods 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen 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
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Cosmetics (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Lubricants (AREA)
- Detergent Compositions (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/836,100 US6465645B1 (en) | 2001-04-17 | 2001-04-17 | Long chain hindered amines and compositions stabilized therewith |
| PCT/EP2002/003944 WO2002083781A1 (en) | 2001-04-17 | 2002-04-09 | Long chain hindered amines and compositions stabilized therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004525185A true JP2004525185A (ja) | 2004-08-19 |
| JP2004525185A5 JP2004525185A5 (enExample) | 2005-12-22 |
Family
ID=25271240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002582126A Withdrawn JP2004525185A (ja) | 2001-04-17 | 2002-04-09 | 長鎖立体障害アミン及びこれにより安定化された組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (4) | US6465645B1 (enExample) |
| EP (1) | EP1379587B1 (enExample) |
| JP (1) | JP2004525185A (enExample) |
| AT (1) | ATE288460T1 (enExample) |
| DE (1) | DE60202860T2 (enExample) |
| WO (1) | WO2002083781A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008519003A (ja) * | 2004-11-02 | 2008-06-05 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Ｎ−アルコキシアミンの合成方法 |
| WO2009107504A1 (ja) * | 2008-02-29 | 2009-09-03 | 株式会社Adeka | ポリ乳酸樹脂組成物 |
| JP2013543516A (ja) * | 2010-10-20 | 2013-12-05 | ビーエーエスエフ ソシエタス・ヨーロピア | 混合官能化による立体障害アミン型光安定剤 |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6465645B1 (en) * | 2001-04-17 | 2002-10-15 | Ciba Specialty Chemicals Corporation | Long chain hindered amines and compositions stabilized therewith |
| DE60238606D1 (de) * | 2001-06-13 | 2011-01-27 | Basf Se | 4-imin-n-alkoxy- oder oxy-polyalkyl-piperidin-verboren |
| WO2004056931A1 (en) * | 2002-12-20 | 2004-07-08 | Ciba Specialty Chemicals Holding Inc. | Ink-jet ink and recording material |
| US6887917B2 (en) * | 2002-12-30 | 2005-05-03 | 3M Innovative Properties Company | Curable pressure sensitive adhesive compositions |
| US7550599B2 (en) * | 2003-02-26 | 2009-06-23 | Ciba Specialty Chemicals Corporation | Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines |
| CA2517334A1 (en) * | 2003-02-26 | 2004-09-10 | Ciba Specialty Chemicals Holding Inc. | Water compatible sterically hindered alkoxyamines and hydroxy substituted alkoxyamines |
| JP2006519916A (ja) * | 2003-03-05 | 2006-08-31 | イーストマン ケミカル カンパニー | 紫外線吸収性化合物を含むポリマー組成物 |
| US7927703B2 (en) * | 2003-04-11 | 2011-04-19 | 3M Innovative Properties Company | Adhesive blends, articles, and methods |
| US20060254125A1 (en) * | 2005-03-18 | 2006-11-16 | Tully Jo A | Silicone additives for compatabilizing fragrances with wax candles |
| US7491287B2 (en) * | 2006-06-09 | 2009-02-17 | 3M Innovative Properties Company | Bonding method with flowable adhesive composition |
| US7932218B2 (en) * | 2006-07-31 | 2011-04-26 | Ciba Corporation | Lubricant composition |
| EP2276750A2 (en) * | 2008-03-27 | 2011-01-26 | Auckland Uniservices Limited | Substituted pyrimidines and triazines and their use in cancer therapy |
| EP2393876B1 (en) * | 2009-02-04 | 2013-08-14 | Basf Se | N-substituted macrocyclic triazine-hals stabilizers |
| JP5361693B2 (ja) * | 2009-12-11 | 2013-12-04 | 株式会社Ａｄｅｋａ | 太陽電池用封止膜 |
| US9541279B2 (en) * | 2013-06-18 | 2017-01-10 | S. C. Johnson & Son, Inc. | Candle dispenser |
| US10385213B2 (en) | 2014-12-31 | 2019-08-20 | Basf Se | Candle wax compositions stabilized with UV absorbers and select hindered amine light stabilizers |
| WO2017008974A1 (en) | 2015-07-14 | 2017-01-19 | Unilever Plc | Antimicrobial composition |
| CN111747885B (zh) * | 2020-06-22 | 2021-07-27 | 宿迁联盛科技股份有限公司 | 一种光稳定剂中间体及其制备方法 |
| CN115611863B (zh) * | 2022-10-14 | 2023-11-14 | 天津大学浙江绍兴研究院 | 一种多功能三嗪基室温磷光材料及制备方法与应用 |
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| DE2647452A1 (de) | 1975-11-07 | 1977-05-18 | Ciba Geigy Ag | Neue hydroxybenzylmalonsaeure-derivate |
| IT1052501B (it) * | 1975-12-04 | 1981-07-20 | Chimosa Chimica Organica Spa | Composti politriazinici utilizzabili per la stabilizzazione di polimeri sintetici e procedimento per la loro preparazione |
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| EP0005922A1 (en) | 1978-05-19 | 1979-12-12 | SMITH & NEPHEW COSMETICS LIMITED | Lip cosmetic |
| DE2920918A1 (de) | 1979-05-23 | 1980-11-27 | Hoechst Ag | Copolymere substituierter piperidine, ihre herstellung und verwendung |
| DE2933732A1 (de) | 1979-08-21 | 1981-03-26 | Hoechst Ag, 65929 Frankfurt | Alkylierte diazaspirodecane, ihre herstellung und verwendung als lichtschutzmittel |
| EP0036117B1 (de) | 1980-03-14 | 1986-02-05 | Spezial-Papiermaschinenfabrik August Alfred Krupp GmbH & Co | Druckempfindliches Aufzeichnungsmaterial |
| DE3022896A1 (de) * | 1980-06-19 | 1981-12-24 | Hoechst Ag, 6000 Frankfurt | Polytriazinylamine, verfahren zu ihrer herstellung und ihre verwendung als stabilisatoren fuer synthetische polymere |
| DE3027223A1 (de) | 1980-07-18 | 1982-02-11 | Hoechst Ag, 6000 Frankfurt | Triazinylaminotriazine, ihre herstellung und verwendung |
| JPS57137358A (en) | 1981-02-17 | 1982-08-24 | Adeka Argus Chem Co Ltd | Stabilized synthetic resin composition |
| DE3113455A1 (de) | 1981-04-03 | 1982-10-21 | Hoechst Ag, 6000 Frankfurt | Poly-bis-triazinylimide, ihre herstellung, ihre verwendung als lichtschutzmittel fuer polymere sowie die mit ihnen stabilisierten polymeren |
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| JPS6147744A (ja) * | 1984-08-15 | 1986-03-08 | Polyplastics Co | 耐候性ポリアセタ−ル樹脂組成物 |
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| JPH066645B2 (ja) * | 1985-12-11 | 1994-01-26 | 住友化学工業株式会社 | ポリオレフイン組成物 |
| DE3724223A1 (de) | 1987-07-22 | 1989-02-02 | Huels Chemische Werke Ag | Stabilisatorsystem |
| DE3724222A1 (de) | 1987-07-22 | 1989-02-02 | Huels Chemische Werke Ag | Lichtstabilisatoren |
| US5204473A (en) | 1987-09-21 | 1993-04-20 | Ciba-Geigy Corporation | O-substituted N-hydroxy hindered amine stabilizers |
| US4996239A (en) | 1988-09-16 | 1991-02-26 | Neutrogena Corporation | Water resistant cream conditioner |
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| JPH02206642A (ja) * | 1989-02-03 | 1990-08-16 | Sumitomo Chem Co Ltd | スチレン系樹脂フィルム |
| IT1237126B (it) * | 1989-11-07 | 1993-05-18 | Ciba Geigy Spa | Stabilizzanti polimerici contenenti gruppi amminici impediti e gruppi idrossilamminici |
| JPH03278554A (ja) | 1990-03-28 | 1991-12-10 | Nec Corp | チップトレーの構造 |
| CA2151827A1 (en) | 1992-12-16 | 1994-06-23 | Sven Edward Royall | Refined petroleum wax composition |
| JP3278554B2 (ja) | 1995-07-21 | 2002-04-30 | 株式会社新井機械製作所 | 煎餅味付装置 |
| AU708193B2 (en) | 1995-08-29 | 1999-07-29 | Pennzoil Products Company | Transparent gel candles |
| BR9810957A (pt) * | 1997-06-30 | 2000-09-26 | Ciba Sc Holding Ag | "composições retardadoras de chama" |
| US5844026A (en) * | 1997-06-30 | 1998-12-01 | Ciba Specialty Chemicals Corporation | N,N',N''-tris{2,4-bis Hydrocarbyloxy-2,2,6,6-tetra-methylpiperidin-4-yl)alkylamino!-s-triazin-6-yl}-3,3'-ethylenediiminodipropylamines, their isomers and bridged derivatives and polymer compositions stabilized therewith |
| JPH11263884A (ja) | 1998-03-19 | 1999-09-28 | Mitsubishi Kagaku Sanshi Corp | ポリオレフィン管 |
| US5964905A (en) | 1998-05-21 | 1999-10-12 | Sara Lee Corporation | Scented candle gel |
| US6262153B1 (en) | 1998-10-12 | 2001-07-17 | Clariant Finance (Bvi) Limited | Colored wax articles |
| US6166212A (en) * | 1999-05-20 | 2000-12-26 | Ciba Specialty Chemicals Corporation | Process for the synthesis of N-(hydroxyalkoxy) substituted hindered amine stabilizers |
| US6221115B1 (en) * | 2000-02-01 | 2001-04-24 | Ciba Specialty Chemicals Corporation | Candle wax stabilized by a combination of UV absorber plus a selected hindered amine |
| US6296674B1 (en) * | 2000-02-01 | 2001-10-02 | Ciba Specialty Chemicals Corporation | Candle wax stabilized with red-shift benzotriazoles |
| US6465645B1 (en) * | 2001-04-17 | 2002-10-15 | Ciba Specialty Chemicals Corporation | Long chain hindered amines and compositions stabilized therewith |
-
2001
- 2001-04-17 US US09/836,100 patent/US6465645B1/en not_active Expired - Fee Related
-
2002
- 2002-04-09 EP EP02735239A patent/EP1379587B1/en not_active Expired - Lifetime
- 2002-04-09 AT AT02735239T patent/ATE288460T1/de not_active IP Right Cessation
- 2002-04-09 JP JP2002582126A patent/JP2004525185A/ja not_active Withdrawn
- 2002-04-09 WO PCT/EP2002/003944 patent/WO2002083781A1/en not_active Ceased
- 2002-04-09 DE DE60202860T patent/DE60202860T2/de not_active Expired - Fee Related
- 2002-09-06 US US10/236,503 patent/US6755875B2/en not_active Expired - Fee Related
- 2002-09-06 US US10/236,520 patent/US6699298B2/en not_active Expired - Fee Related
-
2003
- 2003-12-18 US US10/740,196 patent/US6875870B2/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008519003A (ja) * | 2004-11-02 | 2008-06-05 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | Ｎ−アルコキシアミンの合成方法 |
| WO2009107504A1 (ja) * | 2008-02-29 | 2009-09-03 | 株式会社Adeka | ポリ乳酸樹脂組成物 |
| JP2009209177A (ja) * | 2008-02-29 | 2009-09-17 | Adeka Corp | ポリ乳酸樹脂組成物 |
| US8293824B2 (en) | 2008-02-29 | 2012-10-23 | Adeka Corporation | Polylactic acid resin composition |
| JP2013543516A (ja) * | 2010-10-20 | 2013-12-05 | ビーエーエスエフ ソシエタス・ヨーロピア | 混合官能化による立体障害アミン型光安定剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE60202860D1 (de) | 2005-03-10 |
| US6755875B2 (en) | 2004-06-29 |
| ATE288460T1 (de) | 2005-02-15 |
| EP1379587B1 (en) | 2005-02-02 |
| US6465645B1 (en) | 2002-10-15 |
| WO2002083781A1 (en) | 2002-10-24 |
| US20030109704A1 (en) | 2003-06-12 |
| DE60202860T2 (de) | 2005-07-07 |
| EP1379587A1 (en) | 2004-01-14 |
| US20030125555A1 (en) | 2003-07-03 |
| US20040138452A1 (en) | 2004-07-15 |
| US6875870B2 (en) | 2005-04-05 |
| US6699298B2 (en) | 2004-03-02 |
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