JP4417450B2 - ポリアルキル−1−オキサ−ジアザスピロデカン化合物をベースとする相乗安定剤混合物 - Google Patents
ポリアルキル−1−オキサ−ジアザスピロデカン化合物をベースとする相乗安定剤混合物 Download PDFInfo
- Publication number
- JP4417450B2 JP4417450B2 JP22918398A JP22918398A JP4417450B2 JP 4417450 B2 JP4417450 B2 JP 4417450B2 JP 22918398 A JP22918398 A JP 22918398A JP 22918398 A JP22918398 A JP 22918398A JP 4417450 B2 JP4417450 B2 JP 4417450B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- hydrogen atom
- independently
- atom
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims description 172
- 239000003381 stabilizer Substances 0.000 title claims description 93
- 230000002195 synergetic effect Effects 0.000 title description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 315
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 100
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
- 229910052799 carbon Inorganic materials 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000002947 alkylene group Chemical group 0.000 claims description 33
- 239000000126 substance Substances 0.000 claims description 27
- 229920000642 polymer Polymers 0.000 claims description 20
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000011368 organic material Substances 0.000 claims description 13
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 10
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000004611 light stabiliser Substances 0.000 claims description 9
- -1 octamethylene, hexamethylene Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229920000768 polyamine Polymers 0.000 claims description 9
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 claims description 8
- 239000004594 Masterbatch (MB) Substances 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 7
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 6
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 6
- 125000005447 octyloxy group Chemical group [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])O* 0.000 claims description 6
- 239000000049 pigment Substances 0.000 claims description 6
- 239000011787 zinc oxide Substances 0.000 claims description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
- 239000005977 Ethylene Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical group [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 claims description 3
- 239000008116 calcium stearate Substances 0.000 claims description 3
- 235000013539 calcium stearate Nutrition 0.000 claims description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000155 melt Substances 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical group OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004814 1,1-dimethylethylene group Chemical group [H]C([H])([H])C([*:1])(C([H])([H])[H])C([H])([H])[*:2] 0.000 claims description 2
- 125000004816 2,2-dimethylethylene group Chemical group [H]C([H])([H])C([*:2])(C([H])([H])[H])C([H])([H])[*:1] 0.000 claims description 2
- YHCGGLXPGFJNCO-UHFFFAOYSA-N 2-(2H-benzotriazol-4-yl)phenol Chemical class OC1=CC=CC=C1C1=CC=CC2=C1N=NN2 YHCGGLXPGFJNCO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- CYHYIIFODCKQNP-UHFFFAOYSA-N 5,7-ditert-butyl-3-(3,4-dimethylphenyl)-3h-1-benzofuran-2-one Chemical compound C1=C(C)C(C)=CC=C1C1C(C=C(C=C2C(C)(C)C)C(C)(C)C)=C2OC1=O CYHYIIFODCKQNP-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 150000001851 cinnamic acid derivatives Chemical class 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000003438 dodecyl group Chemical group [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])* 0.000 claims description 2
- 230000009931 harmful effect Effects 0.000 claims description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000000395 magnesium oxide Substances 0.000 claims description 2
- 235000019359 magnesium stearate Nutrition 0.000 claims description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- ITUWQZXQRZLLCR-UHFFFAOYSA-N n,n-dioctadecylhydroxylamine Chemical group CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCCC ITUWQZXQRZLLCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 125000004437 phosphorous atom Chemical group 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 150000003018 phosphorus compounds Chemical class 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 24
- 239000006097 ultraviolet radiation absorber Substances 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 2
- 239000002530 phenolic antioxidant Substances 0.000 claims 2
- UDATXMIGEVPXTR-UHFFFAOYSA-N 1,2,4-triazolidine-3,5-dione Chemical compound O=C1NNC(=O)N1 UDATXMIGEVPXTR-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 239000012760 heat stabilizer Substances 0.000 claims 1
- 229910000000 metal hydroxide Inorganic materials 0.000 claims 1
- 150000004692 metal hydroxides Chemical class 0.000 claims 1
- 229910044991 metal oxide Inorganic materials 0.000 claims 1
- 150000004706 metal oxides Chemical class 0.000 claims 1
- NDGRWYRVNANFNB-UHFFFAOYSA-N pyrazolidin-3-one Chemical class O=C1CCNN1 NDGRWYRVNANFNB-UHFFFAOYSA-N 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- SWZOQAGVRGQLDV-UHFFFAOYSA-N 4-[2-(4-hydroxy-2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]-4-oxobutanoic acid Chemical compound CC1(C)CC(O)CC(C)(C)N1CCOC(=O)CCC(O)=O SWZOQAGVRGQLDV-UHFFFAOYSA-N 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 230000000087 stabilizing effect Effects 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000004743 Polypropylene Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 229920001684 low density polyethylene Polymers 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 239000000057 synthetic resin Substances 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- 239000002966 varnish Substances 0.000 description 4
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000006096 absorbing agent Substances 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000002989 phenols Chemical class 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000004383 yellowing Methods 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000010426 asphalt Substances 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- RDYMFSUJUZBWLH-SVWSLYAFSA-N endosulfan Chemical compound C([C@@H]12)OS(=O)OC[C@@H]1[C@]1(Cl)C(Cl)=C(Cl)[C@@]2(Cl)C1(Cl)Cl RDYMFSUJUZBWLH-SVWSLYAFSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- ORECYURYFJYPKY-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;2,4,6-trichloro-1,3,5-triazine;2,4,4-trimethylpentan-2-amine Chemical compound CC(C)(C)CC(C)(C)N.ClC1=NC(Cl)=NC(Cl)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 ORECYURYFJYPKY-UHFFFAOYSA-N 0.000 description 2
- FDAKZQLBIFPGSV-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)NC(C)(C)C1 FDAKZQLBIFPGSV-UHFFFAOYSA-N 0.000 description 2
- QUAMTGJKVDWJEQ-UHFFFAOYSA-N octabenzone Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C(=O)C1=CC=CC=C1 QUAMTGJKVDWJEQ-UHFFFAOYSA-N 0.000 description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- VPYDVGWWXAYRPP-UHFFFAOYSA-N 1-[2-[[4,6-bis[cyclohexyl-[2-(3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]amino]-1,3,5-triazin-2-yl]-cyclohexylamino]ethyl]-3,3,5,5-tetramethylpiperazin-2-one Chemical compound O=C1C(C)(C)NC(C)(C)CN1CCN(C=1N=C(N=C(N=1)N(CCN1C(C(C)(C)NC(C)(C)C1)=O)C1CCCCC1)N(CCN1C(C(C)(C)NC(C)(C)C1)=O)C1CCCCC1)C1CCCCC1 VPYDVGWWXAYRPP-UHFFFAOYSA-N 0.000 description 1
- IVVLFHBYPHTMJU-UHFFFAOYSA-N 2,2,4,4-tetramethyl-7-oxa-3,20-diazadispiro[5.1.11^{8}.2^{6}]henicosan-21-one Chemical compound C1C(C)(C)NC(C)(C)CC21C(=O)NC1(CCCCCCCCCCC1)O2 IVVLFHBYPHTMJU-UHFFFAOYSA-N 0.000 description 1
- YAGPRJYCDKGWJR-UHFFFAOYSA-N 2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxy-n,n-bis[2-(2,4,8,10-tetratert-butylbenzo[d][1,3,2]benzodioxaphosphepin-6-yl)oxyethyl]ethanamine Chemical compound O1C2=C(C(C)(C)C)C=C(C(C)(C)C)C=C2C2=CC(C(C)(C)C)=CC(C(C)(C)C)=C2OP1OCCN(CCOP1OC2=C(C=C(C=C2C=2C=C(C=C(C=2O1)C(C)(C)C)C(C)(C)C)C(C)(C)C)C(C)(C)C)CCOP(OC1=C(C=C(C=C11)C(C)(C)C)C(C)(C)C)OC2=C1C=C(C(C)(C)C)C=C2C(C)(C)C YAGPRJYCDKGWJR-UHFFFAOYSA-N 0.000 description 1
- JLZIIHMTTRXXIN-UHFFFAOYSA-N 2-(2-hydroxy-4-methoxybenzoyl)benzoic acid Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1C(O)=O JLZIIHMTTRXXIN-UHFFFAOYSA-N 0.000 description 1
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 1
- GUCMKIKYKIHUTM-UHFFFAOYSA-N 3,3,5,5-tetramethyl-1-[2-(3,3,5,5-tetramethyl-2-oxopiperazin-1-yl)ethyl]piperazin-2-one Chemical compound O=C1C(C)(C)NC(C)(C)CN1CCN1C(=O)C(C)(C)NC(C)(C)C1 GUCMKIKYKIHUTM-UHFFFAOYSA-N 0.000 description 1
- SSADPHQCUURWSW-UHFFFAOYSA-N 3,9-bis(2,6-ditert-butyl-4-methylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C)=CC(C(C)(C)C)=C1OP1OCC2(COP(OC=3C(=CC(C)=CC=3C(C)(C)C)C(C)(C)C)OC2)CO1 SSADPHQCUURWSW-UHFFFAOYSA-N 0.000 description 1
- WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 description 1
- OWXXKGVQBCBSFJ-UHFFFAOYSA-N 6-n-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[2-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]-[3-[[4,6-bis[butyl-(1,2,2,6,6-pentamethylpiperidin-4-yl)amino]-1,3,5-triazin-2-yl]ami Chemical compound N=1C(NCCCN(CCN(CCCNC=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)C=2N=C(N=C(N=2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC(N(CCCC)C2CC(C)(C)N(C)C(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)N(C)C(C)(C)C1 OWXXKGVQBCBSFJ-UHFFFAOYSA-N 0.000 description 1
- 0 CC(C(*)NC(C)(C1)C(C)=C)C1N* Chemical compound CC(C(*)NC(C)(C1)C(C)=C)C1N* 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- BEIOEBMXPVYLRY-UHFFFAOYSA-N [4-[4-bis(2,4-ditert-butylphenoxy)phosphanylphenyl]phenyl]-bis(2,4-ditert-butylphenoxy)phosphane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(C=1C=CC(=CC=1)C=1C=CC(=CC=1)P(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)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 BEIOEBMXPVYLRY-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- CMXLJKWFEJEFJE-UHFFFAOYSA-N bis(1,2,2,6,6-pentamethylpiperidin-4-yl) 2-[(4-methoxyphenyl)methylidene]propanedioate Chemical compound C1=CC(OC)=CC=C1C=C(C(=O)OC1CC(C)(C)N(C)C(C)(C)C1)C(=O)OC1CC(C)(C)N(C)C(C)(C)C1 CMXLJKWFEJEFJE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000000071 blow moulding Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 230000002262 irrigation Effects 0.000 description 1
- 238000003973 irrigation Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- VVNXEADCOVSAER-UHFFFAOYSA-N lithium sodium Chemical compound [Li].[Na] VVNXEADCOVSAER-UHFFFAOYSA-N 0.000 description 1
- 239000010721 machine oil Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OLBWDGJTEXRJLY-UHFFFAOYSA-N tetradecyl 3-(2,2,4,4-tetramethyl-21-oxo-7-oxa-3,20-diazadispiro[5.1.11^{8}.2^{6}]henicosan-20-yl)propanoate Chemical compound O1C2(CCCCCCCCCCC2)N(CCC(=O)OCCCCCCCCCCCCCC)C(=O)C21CC(C)(C)NC(C)(C)C2 OLBWDGJTEXRJLY-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
-
- 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
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/353—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/20—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing nitrogen and oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Printing Methods (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19735255A DE19735255B4 (de) | 1997-08-14 | 1997-08-14 | Synergistisches Stabilisatorgemisch auf Basis von Polyalkyl-1-oxa-diazaspirodecan-Verbindungen und dessen Verwendung |
| DE19735255:3 | 1997-08-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JPH11148073A JPH11148073A (ja) | 1999-06-02 |
| JPH11148073A5 JPH11148073A5 (enExample) | 2005-11-04 |
| JP4417450B2 true JP4417450B2 (ja) | 2010-02-17 |
Family
ID=7838968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22918398A Expired - Fee Related JP4417450B2 (ja) | 1997-08-14 | 1998-08-13 | ポリアルキル−1−オキサ−ジアザスピロデカン化合物をベースとする相乗安定剤混合物 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6174940B1 (enExample) |
| JP (1) | JP4417450B2 (enExample) |
| KR (1) | KR100581157B1 (enExample) |
| BE (1) | BE1012749A3 (enExample) |
| CH (1) | CH693906A5 (enExample) |
| DE (1) | DE19735255B4 (enExample) |
| ES (1) | ES2153748B1 (enExample) |
| FR (1) | FR2767322B1 (enExample) |
| GB (1) | GB2328210B (enExample) |
| IT (1) | IT1302019B1 (enExample) |
| NL (1) | NL1009876C2 (enExample) |
| TW (1) | TW580512B (enExample) |
| ZA (1) | ZA987248B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0982356A3 (en) * | 1998-08-28 | 2001-11-07 | Clariant Finance (BVI) Limited | Improved stabilized coatings |
| IT1318423B1 (it) * | 2000-03-24 | 2003-08-25 | Great Lakes Chemical Europ | Miscele stabilizzanti per polimeri organici. |
| GB0009965D0 (en) * | 2000-04-25 | 2000-06-14 | Clariant Int Ltd | Synergistic stabilizer compositions comprising copolymers of ethylene with hin dered amine moieties containing acrylate or methacrylate comonomers |
| AU2001273985B2 (en) * | 2000-05-11 | 2006-03-09 | Ciba Specialty Chemicals Holding Inc. | Process for the staining of wood with aqueous wood stains |
| TW539711B (en) * | 2000-05-31 | 2003-07-01 | Ciba Sc Holding Ag | Stabilizer mixtures |
| AU6601001A (en) * | 2000-05-31 | 2001-12-11 | Ciba Sc Holding Ag | Stabilizer mixtures |
| GB2378952B (en) * | 2000-05-31 | 2004-04-21 | Ciba Sc Holding Ag | Stabiliser mixtures |
| TWI226351B (en) * | 2000-07-14 | 2005-01-11 | Clariant Int Ltd | Synergistic mixtures of phosphorus-containing compounds for stabilizing polymers |
| GB0019465D0 (en) * | 2000-08-09 | 2000-09-27 | Clariant Int Ltd | Synergistic stabilizer for color stable pigmented thermoplastic polyners in prolonged contact with water |
| GB0104371D0 (en) * | 2001-02-22 | 2001-04-11 | Clariant Int Ltd | Color improving stabilizing compositions comprising leucine |
| DE10204690A1 (de) * | 2002-02-06 | 2003-08-07 | Clariant Gmbh | Verfahren zur Herstellung synergistischer Stabilisatormischungen |
| US20030225191A1 (en) * | 2002-04-12 | 2003-12-04 | Francois Gugumus | Stabilizer mixtures |
| JP4615309B2 (ja) | 2002-05-17 | 2011-01-19 | オセラ・ホールディング・インコーポレイテッド | 白内障および他の眼球疾患の進行の改善 |
| US7825134B2 (en) | 2003-05-19 | 2010-11-02 | Othera Holding, Inc. | Amelioration of cataracts, macular degeneration and other ophthalmic diseases |
| KR20090089314A (ko) * | 2006-11-27 | 2009-08-21 | 시바 홀딩 인코포레이티드 | 풍화에 대하여 안정화된 역청 또는 아스팔트 조성물 |
| DE102017220555A1 (de) * | 2017-11-17 | 2019-05-23 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verbindungen mit stabilisierender Wirkung, Verfahren zu deren Herstellung, Zusammensetzung enthaltend diese stabilisierenden Verbindungen, Verfahren zur Stabilisierung einer organischen Komponente sowie Verwendung von stabilisierenden Verbindungen |
| US20220259410A1 (en) | 2019-07-10 | 2022-08-18 | Clariant International Ltd | Stabilizer composition for silyl-modified polymer sealants |
| EP3808818A1 (de) | 2019-10-15 | 2021-04-21 | Clariant International Ltd | Teilverseifte reiskleiewachsoxidate |
| PL4045597T3 (pl) | 2019-10-15 | 2024-06-24 | Clariant International Ltd | Produkty utleniania wosku z otrębów ryżowych o niskich liczbach kwasowych |
| EP3808819A1 (de) | 2019-10-15 | 2021-04-21 | Clariant International Ltd | Helle reiskleiewachsoxidate mit einem hohen esteranteil |
| TW202237726A (zh) | 2021-01-12 | 2022-10-01 | 瑞士商克萊瑞特國際股份有限公司 | 用於矽基改質聚合物密封劑之穩定劑組成物 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9100257D0 (en) | 1991-01-07 | 1991-02-20 | Sandoz Ltd | Improvements in or relating to organic compounds |
| CH648036A5 (de) | 1980-12-24 | 1985-02-28 | Sandoz Ag | 1-oxa-3,8-diaza-4-oxo-spiro-(4,5)-decan-verbindungen. |
| DE3104294A1 (de) * | 1981-02-07 | 1982-08-19 | Hoechst Ag, 6000 Frankfurt | Substituierte diazaspirodecane, ihre herstellung, ihre verwendung als stabilisatoren fuer organische polymere, sowie die so stabilisierten polymeren |
| EP0080431B1 (de) | 1981-10-16 | 1986-09-24 | Ciba-Geigy Ag | Synergistisches Gemisch von niedermolekularen und hochmolekularen Polyalkylpiperidinen |
| DE3541664A1 (de) | 1985-11-26 | 1987-06-11 | Hoechst Ag | Oligomere diazaspirodecane, ihre herstellung und ihre verwendung als lichtschutzmittel fuer polymere |
| US4863981A (en) | 1986-06-30 | 1989-09-05 | Ciba-Geigy Corporation | Synergistic mixture of stabilizers |
| JP2582385B2 (ja) | 1987-12-11 | 1997-02-19 | 旭電化工業株式会社 | 安定化された合成樹脂組成物 |
| DE3919691A1 (de) | 1989-06-16 | 1990-12-20 | Hoechst Ag | Polymere polyalkyl-1-oxa-diazaspirodecane |
| JP2803300B2 (ja) | 1990-03-14 | 1998-09-24 | 住友化学工業株式会社 | 安定化されたポリプロピレン樹脂組成物 |
| GB9211602D0 (en) | 1992-06-02 | 1992-07-15 | Sandoz Ltd | Improvements in or relating to organic compounds |
| US6077889A (en) | 1993-03-24 | 2000-06-20 | Solvay Engineered Polymers | Light stabilizer packages for partial paint applications |
| CA2127334A1 (en) | 1993-07-02 | 1995-01-03 | Edward A. Bourbonais | Synergistic combination of uv light stabilizers for use with organic polymers |
| TW307785B (enExample) * | 1994-04-05 | 1997-06-11 | Ciba Sc Holding Ag | |
| DE4423055A1 (de) | 1994-07-01 | 1996-01-11 | Hoechst Ag | Polyalkylpiperidin-Verbindungen |
| DE4423054A1 (de) | 1994-07-01 | 1996-01-04 | Hoechst Ag | Polyalkylpiperidin-Verbindungen |
| ES2148464T5 (es) | 1994-10-28 | 2005-06-16 | Ciba Specialty Chemicals Holding Inc. | Mezcla de estabilizadores sinergicos. |
| EP0709426B2 (de) * | 1994-10-28 | 2005-01-05 | Ciba SC Holding AG | Synergistisches Stabilisatorgemisch |
| TW358820B (en) * | 1995-04-11 | 1999-05-21 | Ciba Sc Holding Ag | Synergistic stabilizer mixture |
| DE19820157B4 (de) * | 1997-05-13 | 2010-04-08 | Clariant Produkte (Deutschland) Gmbh | Neue Verbindungen auf Basis von Polyalkyl-1-oxa-diazaspirodecan-Verbindungen |
-
1997
- 1997-08-14 DE DE19735255A patent/DE19735255B4/de not_active Expired - Lifetime
-
1998
- 1998-08-10 BE BE9800596A patent/BE1012749A3/fr not_active IP Right Cessation
- 1998-08-12 CH CH01662/98A patent/CH693906A5/de not_active IP Right Cessation
- 1998-08-12 ES ES009801740A patent/ES2153748B1/es not_active Expired - Lifetime
- 1998-08-12 IT IT1998MI001888A patent/IT1302019B1/it active IP Right Grant
- 1998-08-13 TW TW087113337A patent/TW580512B/zh not_active IP Right Cessation
- 1998-08-13 US US09/133,389 patent/US6174940B1/en not_active Expired - Lifetime
- 1998-08-13 ZA ZA987248A patent/ZA987248B/xx unknown
- 1998-08-13 FR FR9810379A patent/FR2767322B1/fr not_active Expired - Fee Related
- 1998-08-13 JP JP22918398A patent/JP4417450B2/ja not_active Expired - Fee Related
- 1998-08-13 GB GB9817658A patent/GB2328210B/en not_active Expired - Fee Related
- 1998-08-14 NL NL1009876A patent/NL1009876C2/nl not_active IP Right Cessation
- 1998-08-14 KR KR1019980032972A patent/KR100581157B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ITMI981888A0 (it) | 1998-08-12 |
| ZA987248B (en) | 1999-02-15 |
| ITMI981888A1 (it) | 2000-02-12 |
| GB9817658D0 (en) | 1998-10-07 |
| JPH11148073A (ja) | 1999-06-02 |
| BE1012749A3 (fr) | 2001-03-06 |
| CH693906A5 (de) | 2004-04-15 |
| US6174940B1 (en) | 2001-01-16 |
| FR2767322A1 (fr) | 1999-02-19 |
| ES2153748A1 (es) | 2001-03-01 |
| FR2767322B1 (fr) | 2001-07-27 |
| DE19735255A1 (de) | 1999-02-18 |
| GB2328210B (en) | 2001-06-06 |
| NL1009876A1 (nl) | 1999-02-16 |
| DE19735255B4 (de) | 2007-08-23 |
| KR19990023593A (ko) | 1999-03-25 |
| NL1009876C2 (nl) | 2000-11-07 |
| IT1302019B1 (it) | 2000-07-20 |
| ES2153748B1 (es) | 2001-09-01 |
| KR100581157B1 (ko) | 2006-11-30 |
| TW580512B (en) | 2004-03-21 |
| GB2328210A (en) | 1999-02-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4417450B2 (ja) | ポリアルキル−1−オキサ−ジアザスピロデカン化合物をベースとする相乗安定剤混合物 | |
| CN105399730B (zh) | 位阻胺稳定剂 | |
| JPS6335658B2 (enExample) | ||
| RU2180906C2 (ru) | Стабилизированные кристаллические полимеры пропилена для получения термосвариваемых волокон | |
| JPH08509031A (ja) | ポリプロピレン繊維のための着色の少ない加工、熱および光安定剤系 | |
| CA1085085A (en) | Aza-adamantane compound stabilizers for organic polymer compositions | |
| JP4370000B2 (ja) | ポリアルキル−1−オキサジアザスピロデカン化合物をベースとする化合物 | |
| SU484694A3 (ru) | Композици на основе синтетического полимера | |
| US20090182077A1 (en) | Composition for stabilizing polyolefin polymers | |
| US4451400A (en) | Phosphazenes useful as stabilizers in polymers | |
| EP0065169A1 (de) | Poly-bis-triazinylaminotriazinylamine, ihre Herstellung, ihre Verwendung als Lichtschutzmittel für Kunststoffe und mit ihnen stabilisierte Kunststoffe | |
| US3883477A (en) | Compositions stabilized with 1,4-disubstituted-7-azabicyclo (2.2.1) heptane-2,5 or 2, 6-dicarboxylic acid esters | |
| JPH02187437A (ja) | 耐光性の改善された高分子材料組成物 | |
| GB2156359A (en) | Composition for heat and light stabilisation of polymers | |
| SU423308A3 (enExample) | ||
| JPH0772236B2 (ja) | オリゴマ−性ジアザオキサスピロデカン、それらの製造方法および重合体用光保護剤としてのそれらの用途 | |
| WO1994017082A1 (en) | Hydrolytically stable pentaerythritol diphosphites | |
| US4104254A (en) | Method for stabilization of UV sensitive plastics with substituted 1,3-oxazolidine | |
| SU379098A1 (ru) | Стабилизированная композиция на основе синтетического полимера | |
| SU859398A1 (ru) | Полимерна композици | |
| US4829111A (en) | Stabilizer composition for synthetic resin and synthetic resin composition containing the same | |
| JPS6031876B2 (ja) | 有機材料用安定剤 | |
| JPS6195071A (ja) | 安定化された高分子材料組成物 | |
| JPH1017551A (ja) | N−β−シアノエチル−2,2,6,6−テトラメチルピペリジン化合物、及びそれを含む高分子組成物 | |
| EP0040321A1 (en) | Substituted bis-imidazolidines and their use as stabilizers for polymers |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050812 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050812 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20070828 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20071009 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080108 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080111 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20080208 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20080214 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080307 |
|
| A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20090428 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090828 |
|
| A911 | Transfer to examiner for re-examination before appeal (zenchi) |
Free format text: JAPANESE INTERMEDIATE CODE: A911 Effective date: 20090918 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20091110 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20091126 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121204 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20121204 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20131204 Year of fee payment: 4 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |