DE2621841A1 - Lichtschutzmittel fuer polymere - Google Patents
Lichtschutzmittel fuer polymereInfo
- Publication number
- DE2621841A1 DE2621841A1 DE19762621841 DE2621841A DE2621841A1 DE 2621841 A1 DE2621841 A1 DE 2621841A1 DE 19762621841 DE19762621841 DE 19762621841 DE 2621841 A DE2621841 A DE 2621841A DE 2621841 A1 DE2621841 A1 DE 2621841A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- alkyl
- group
- hydrogen
- diethyl
- 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.)
- Pending
Links
- 229920000642 polymer Polymers 0.000 title claims description 37
- 239000011814 protection agent Substances 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 claims description 112
- -1 oxyl radical Chemical class 0.000 claims description 59
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 150000001875 compounds Chemical class 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 239000000203 mixture Substances 0.000 claims description 18
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 17
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000000304 alkynyl group Chemical group 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 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 10
- 239000002253 acid Substances 0.000 claims description 9
- 229920000620 organic polymer Polymers 0.000 claims description 9
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- IRTDZPQZEJNODN-UHFFFAOYSA-N 2-(2,6-diethyl-2,3,6-trimethylpiperidin-1-yl)ethanol Chemical compound CCC1(C)CCC(C)C(C)(CC)N1CCO IRTDZPQZEJNODN-UHFFFAOYSA-N 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 239000000654 additive Substances 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920000098 polyolefin Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- HBAFEGSROZTNSU-UHFFFAOYSA-N 2,6-diethyl-1,2,3,6-tetramethylpiperidine Chemical compound CCC1(C)CCC(C)C(C)(CC)N1C HBAFEGSROZTNSU-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 229940116351 sebacate Drugs 0.000 claims description 2
- 125000006839 xylylene group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000003381 stabilizer Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 150000003053 piperidines Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical class O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- PUVUYZAAQWYJNL-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethylpiperidine Chemical compound CCC1(C)CCC(C)C(C)(CC)N1 PUVUYZAAQWYJNL-UHFFFAOYSA-N 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- TUOLXKNMFCOMGN-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethylpiperidin-4-one Chemical compound CCC1(C)CC(=O)C(C)C(C)(CC)N1 TUOLXKNMFCOMGN-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000005062 Polybutadiene Substances 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 3
- 229920002857 polybutadiene Polymers 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- PLWSZFMXEYJTBC-UHFFFAOYSA-N 2,4,6-triethyl-2,6-dimethyl-1,5-dihydropyrimidine Chemical compound CCC1=NC(C)(CC)NC(C)(CC)C1 PLWSZFMXEYJTBC-UHFFFAOYSA-N 0.000 description 2
- 125000006040 2-hexenyl group Chemical group 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000005644 Wolff-Kishner reduction reaction Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000011888 foil Substances 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000000400 lauroyl group Chemical group O=C([*])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
- 239000004611 light stabiliser Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000003230 pyrimidines Chemical class 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 1
- 125000000349 (Z)-3-carboxyprop-2-enoyl group Chemical group O=C([*])/C([H])=C([H])\C(O[H])=O 0.000 description 1
- RMCLVYNUTRHDDI-UHFFFAOYSA-N 1,1-dichloroethene;ethenyl acetate Chemical compound ClC(Cl)=C.CC(=O)OC=C RMCLVYNUTRHDDI-UHFFFAOYSA-N 0.000 description 1
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical group CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 description 1
- WWCXAOLNAZVDRO-UHFFFAOYSA-N 1,2,6-trimethyl-2,6-bis(3-methylbutyl)-3-(2-methylpropyl)piperidine Chemical compound CC(C)CCC1(C)CCC(CC(C)C)C(C)(CCC(C)C)N1C WWCXAOLNAZVDRO-UHFFFAOYSA-N 0.000 description 1
- TZBHXFDZLPOJJP-UHFFFAOYSA-N 1-(2,6-diethyl-2,3,6-trimethylpiperidin-1-yl)prop-2-en-1-one Chemical compound CCC1(C)CCC(C)C(C)(CC)N1C(=O)C=C TZBHXFDZLPOJJP-UHFFFAOYSA-N 0.000 description 1
- VZVZDOSRDNIPPE-UHFFFAOYSA-N 1-benzyl-2,6-diethyl-2,3,6-trimethylpiperidine Chemical compound CCC1(C)CCC(C)C(C)(CC)N1CC1=CC=CC=C1 VZVZDOSRDNIPPE-UHFFFAOYSA-N 0.000 description 1
- VMKOFRJSULQZRM-UHFFFAOYSA-N 1-bromooctane Chemical compound CCCCCCCCBr VMKOFRJSULQZRM-UHFFFAOYSA-N 0.000 description 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- GNZMGASPLNRJGQ-UHFFFAOYSA-N 2,2,6,6-tetraethyl-3,5-dimethylpiperidin-4-one Chemical compound CCC1(CC)NC(CC)(CC)C(C)C(=O)C1C GNZMGASPLNRJGQ-UHFFFAOYSA-N 0.000 description 1
- BZTFDXXMSUZENV-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethyl-1-octylpiperidine Chemical compound CCCCCCCCN1C(C)(CC)CCC(C)C1(C)CC BZTFDXXMSUZENV-UHFFFAOYSA-N 0.000 description 1
- IADHPFZMSTVIBT-UHFFFAOYSA-N 2,6-diethyl-2,3,6-trimethyl-1-prop-2-enylpiperidine Chemical compound CCC1(C)CCC(C)C(C)(CC)N1CC=C IADHPFZMSTVIBT-UHFFFAOYSA-N 0.000 description 1
- SFURCKGWKWKOKM-UHFFFAOYSA-N 2,6-dimethyl-2,4,6-tripropyl-1,5-dihydropyrimidine Chemical compound CCCC1=NC(C)(CCC)NC(C)(CCC)C1 SFURCKGWKWKOKM-UHFFFAOYSA-N 0.000 description 1
- GJGFENJRNFZYNX-UHFFFAOYSA-N 2,6-dimethyl-2,4,6-tris(3-methylbutyl)-1,5-dihydropyrimidine Chemical compound CC(C)CCC1=NC(C)(CCC(C)C)NC(C)(CCC(C)C)C1 GJGFENJRNFZYNX-UHFFFAOYSA-N 0.000 description 1
- DWDMKXDEQXXIFL-UHFFFAOYSA-N 2,6-dimethyl-2,6-bis(2-methylpropyl)-3-propan-2-ylpiperidine Chemical compound CC(C)CC1(C)CCC(C(C)C)C(C)(CC(C)C)N1 DWDMKXDEQXXIFL-UHFFFAOYSA-N 0.000 description 1
- YTGKLFVCBRRIOI-UHFFFAOYSA-N 2,6-dimethyl-2,6-bis(3-methylbutyl)-3-(2-methylpropyl)piperidin-4-one Chemical compound CC(C)CCC1(C)CC(=O)C(CC(C)C)C(C)(CCC(C)C)N1 YTGKLFVCBRRIOI-UHFFFAOYSA-N 0.000 description 1
- SWFYJVHMIMYMQS-UHFFFAOYSA-N 2-(2,6-diethyl-2,3,6-trimethylpiperidin-1-yl)-1-phenylethanol Chemical compound CCC1(C)CCC(C)C(C)(CC)N1CC(O)C1=CC=CC=C1 SWFYJVHMIMYMQS-UHFFFAOYSA-N 0.000 description 1
- SNEKFYDBFBZQHE-UHFFFAOYSA-N 2-(2,6-diethyl-2,3,6-trimethylpiperidin-1-yl)ethyl benzoate Chemical compound CCC1(C)CCC(C)C(C)(CC)N1CCOC(=O)C1=CC=CC=C1 SNEKFYDBFBZQHE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- TVPNYABWDJUJJV-UHFFFAOYSA-N 2-ethyl-1,2,5-trimethyl-1-azaspiro[5.5]undecane Chemical compound CN1C(CC)(C)CCC(C)C11CCCCC1 TVPNYABWDJUJJV-UHFFFAOYSA-N 0.000 description 1
- YRSOHBFPOGJHFQ-UHFFFAOYSA-N 2-ethyl-2,5,6-trimethyl-1-(2-phenylethyl)piperidine Chemical compound CCC1(C)CCC(C)C(C)N1CCC1=CC=CC=C1 YRSOHBFPOGJHFQ-UHFFFAOYSA-N 0.000 description 1
- 125000003816 2-hydroxybenzoyl group Chemical group OC1=C(C(=O)*)C=CC=C1 0.000 description 1
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- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB23352/75A GB1496844A (en) | 1975-05-28 | 1975-05-28 | Stabilization of polymers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2621841A1 true DE2621841A1 (de) | 1976-12-16 |
Family
ID=10194277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762621841 Pending DE2621841A1 (de) | 1975-05-28 | 1976-05-17 | Lichtschutzmittel fuer polymere |
Country Status (6)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9969864B2 (en) | 2013-07-08 | 2018-05-15 | Basf Se | Light stabilizers |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4210578A (en) * | 1975-05-28 | 1980-07-01 | Ciba-Geigy Corporation | 4-Siloxy derivatives of polyalkylated piperidines |
| US4292237A (en) * | 1977-11-14 | 1981-09-29 | The B. F. Goodrich Company | Polymeric ultraviolet light stabilizers containing hindered alkyl amines |
| JPS60197775A (ja) | 1984-03-21 | 1985-10-07 | Adeka Argus Chem Co Ltd | 熱硬化性合成樹脂塗料組成物 |
| EP0518197B1 (en) * | 1991-06-03 | 1994-12-21 | Mitsubishi Chemical Corporation | Piperidine derivatives |
| US5260443A (en) * | 1991-06-03 | 1993-11-09 | Mitsubishi Petrochemical Company Limited | Piperidine derivatives as photostabilizer |
| EP0559611B1 (de) * | 1992-03-05 | 1999-11-17 | Ciba SC Holding AG | Stabilisierung von Pyrrolopyrrolpigmenten |
| EP0559613B1 (de) * | 1992-03-05 | 1999-12-15 | Ciba SC Holding AG | Stabilisierung von organischen Pigmenten |
| ES2111887T3 (es) * | 1993-02-23 | 1998-03-16 | Ciba Geigy Ag | Dicetopirrolopirroles que contienen grupos nitroxilo. |
| EP0638616A1 (de) * | 1993-08-13 | 1995-02-15 | Ciba-Geigy Ag | Pigmentsalze |
| CH693416A5 (de) | 1998-03-09 | 2003-07-31 | Ciba Sc Holding Ag | 1-Alkoxypolyalkylpiperidinderivate und ihre Verwendung als Polymerisationsregler. |
| TW546311B (en) * | 1999-11-25 | 2003-08-11 | Ciba Sc Holding Ag | Composition and method for color improvement of nitroxyl containing polymers |
| ATE499375T1 (de) | 2000-05-19 | 2011-03-15 | Basf Se | Verfahren zur kontrollierten erhöhung des molekulargewichts von polyethylen und polyethylenmischungen |
| ATE490993T1 (de) | 2006-10-02 | 2010-12-15 | Borealis Tech Oy | Polyolefinzusammensetzung mit verbesserter resistenz gegenüber cio2-enthaltenden wasser |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE565983A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| NL101733C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1957-02-13 | |||
| US3103542A (en) * | 1959-11-25 | 1963-09-10 | Natural rubber stabilized with alkyl | |
| FR1274238A (fr) | 1959-11-25 | 1961-10-20 | Ici Ltd | Application de composés hétérocycliques alkyl-substitués comme agents anti-ozone |
| NL154241C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1971-01-29 | 1900-01-01 | ||
| US3992390A (en) * | 1971-11-30 | 1976-11-16 | Brian Holt | Esters of piperidinols |
| GB1398412A (en) * | 1972-07-28 | 1975-06-18 | Ciba Geigy Ag | Piperidine derivatives |
| GB1398413A (en) * | 1972-07-28 | 1975-06-18 | Ciba Geigy Ag | Piperidine derivatives |
| US3998784A (en) * | 1972-07-28 | 1976-12-21 | Ciba-Geigy Corporation | Compositions stabilized with piperidine derivatives |
| US3975357A (en) * | 1973-04-19 | 1976-08-17 | Sankyo Company Limited | Stabilized synthetic polymer compositions |
| CH589056A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-12-10 | 1977-06-30 | Ciba Geigy Ag |
-
1975
- 1975-05-28 GB GB23352/75A patent/GB1496844A/en not_active Expired
-
1976
- 1976-05-17 DE DE19762621841 patent/DE2621841A1/de active Pending
- 1976-05-19 US US05/687,823 patent/US4131599A/en not_active Expired - Lifetime
- 1976-05-21 CH CH645076A patent/CH602844A5/xx not_active IP Right Cessation
- 1976-05-26 FR FR7615927A patent/FR2312533A1/fr active Granted
- 1976-05-27 JP JP51061551A patent/JPS51142046A/ja active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9969864B2 (en) | 2013-07-08 | 2018-05-15 | Basf Se | Light stabilizers |
Also Published As
| Publication number | Publication date |
|---|---|
| US4131599A (en) | 1978-12-26 |
| CH602844A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-08-15 |
| FR2312533B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1978-11-17 |
| FR2312533A1 (fr) | 1976-12-24 |
| JPS51142046A (en) | 1976-12-07 |
| GB1496844A (en) | 1978-01-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |