MXPA99010888A - Block oligomers containing 1-hydrocarbyloxy-2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials - Google Patents
Block oligomers containing 1-hydrocarbyloxy-2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materialsInfo
- Publication number
- MXPA99010888A MXPA99010888A MXPA/A/1999/010888A MX9910888A MXPA99010888A MX PA99010888 A MXPA99010888 A MX PA99010888A MX 9910888 A MX9910888 A MX 9910888A MX PA99010888 A MXPA99010888 A MX PA99010888A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- formula
- substituted
- alkyl
- unsubstituted
- Prior art date
Links
- 239000003381 stabilizer Substances 0.000 title claims abstract description 20
- 239000011368 organic material Substances 0.000 title claims abstract description 18
- -1 N-(2,2,6, 6-tetramethyl-4-piperidyl)-butylamino Chemical group 0.000 claims abstract description 170
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 238000006243 chemical reaction Methods 0.000 claims abstract description 60
- 239000002904 solvent Substances 0.000 claims abstract description 34
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 25
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 150000002978 peroxides Chemical class 0.000 claims abstract description 16
- 239000003960 organic solvent Substances 0.000 claims abstract description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000007529 inorganic bases Chemical class 0.000 claims abstract description 8
- 229920001059 synthetic polymer Polymers 0.000 claims abstract description 8
- 230000003647 oxidation Effects 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- 229920000098 polyolefin Polymers 0.000 claims abstract description 7
- 239000004611 light stabiliser Substances 0.000 claims abstract description 5
- 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 abstract description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N Dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 377
- 125000000217 alkyl group Chemical group 0.000 claims description 154
- 239000000203 mixture Substances 0.000 claims description 84
- 239000000047 product Substances 0.000 claims description 84
- 125000002947 alkylene group Chemical group 0.000 claims description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
- 125000003545 alkoxy group Chemical group 0.000 claims description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 24
- 239000004743 Polypropylene Substances 0.000 claims description 23
- 229920001155 polypropylene Polymers 0.000 claims description 19
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 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 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 15
- 239000002184 metal Substances 0.000 claims description 15
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 125000002347 octyl 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])[H] 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 239000004698 Polyethylene (PE) Substances 0.000 claims description 9
- 229920000573 polyethylene Polymers 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Inorganic materials O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 0.000 claims description 7
- 125000004450 alkenylene group Chemical group 0.000 claims description 6
- 230000000875 corresponding Effects 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 230000003252 repetitive Effects 0.000 claims description 5
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tBuOOH Chemical group CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910044991 metal oxide Inorganic materials 0.000 claims description 4
- 150000004706 metal oxides Chemical class 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 230000000737 periodic Effects 0.000 claims description 4
- 230000000087 stabilizing Effects 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (Z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 3
- CPBZARXQRZTYGI-UHFFFAOYSA-N 3-cyclopentylpropylcyclohexane Chemical compound C1CCCCC1CCCC1CCCC1 CPBZARXQRZTYGI-UHFFFAOYSA-N 0.000 claims description 3
- RXKJFZQQPQGTFL-UHFFFAOYSA-N Dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 150000001925 cycloalkenes Chemical class 0.000 claims description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 3
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 3
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 230000004059 degradation Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 2
- WJTCGQSWYFHTAC-UHFFFAOYSA-N Cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 150000001345 alkine derivatives Chemical class 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 239000004914 cyclooctane Substances 0.000 claims description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 2
- NAHBVNMACPIHAH-HLICZWCASA-N P-II Chemical compound C([C@H]1C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H]2CSSC[C@H](NC(=O)[C@H](CC=3C=CC=CC=3)NC(=O)CNC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=3C=CC(O)=CC=3)NC2=O)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CSSC[C@@H](C(=O)N1)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O)=O)C(C)C)C1=CC=CC=C1 NAHBVNMACPIHAH-HLICZWCASA-N 0.000 claims 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- POECFFCNUXZPJT-UHFFFAOYSA-M sodium;carbonic acid;hydrogen carbonate Chemical compound [Na+].OC(O)=O.OC([O-])=O POECFFCNUXZPJT-UHFFFAOYSA-M 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 59
- 229920001577 copolymer Polymers 0.000 description 42
- 229920000642 polymer Polymers 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- 239000005977 Ethylene Substances 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 13
- 150000002148 esters Chemical class 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- 239000004952 Polyamide Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 8
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 239000011572 manganese Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 229920000122 Acrylonitrile butadiene styrene Polymers 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 229920001684 low density polyethylene Polymers 0.000 description 6
- 239000004702 low-density polyethylene Substances 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920002866 paraformaldehyde Polymers 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- AQSJGOWTSHOLKH-UHFFFAOYSA-N Phosphite Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (-)-propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N 1,6-Hexanediol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N Adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N CC(CCCCC(O)O)(C)C Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- FPQJEXTVQZHURJ-UHFFFAOYSA-N N,N'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 4
- 229940117969 NEOPENTYL GLYCOL Drugs 0.000 description 4
- 229960004063 Propylene glycol Drugs 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N Stearyl alcohol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N Thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
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- ALVZNPYWJMLXKV-UHFFFAOYSA-N nonane-1,9-diol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
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- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
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- QHZOMAXECYYXGP-UHFFFAOYSA-N ethene;prop-2-enoic acid Chemical compound C=C.OC(=O)C=C QHZOMAXECYYXGP-UHFFFAOYSA-N 0.000 description 3
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- 150000002367 halogens Chemical class 0.000 description 3
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- 150000003672 ureas Chemical class 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium(0) Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 150000003700 vitamin C derivatives Chemical class 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon(0) Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc;N,N-dibutylcarbamodithioate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
Abstract
A product obtainable by 1) reacting a compound of formula (&agr;) with a compound of formula (&bgr;) in a molar ratio of 1.2:1 to 1.4:1;2) reacting the end groups of formula (&ggr;) being present in the product of the reaction 1) with e.g. dibutylamine in a molar ratio of 2:1.7 to 2:3;the reactions 1) and 2) being carried out in an organic solvent in the presence of an inorganic base;and 3) transferring the groups of formula (G-I) being present in the product of the reaction 2) to groups of formula (G-II), said transfer being carried out by reacting the product of the reaction 2) with a hydroperoxide in a hydrocarbon solvent in the presence of a peroxide decomposing catalyst;R1 is in particular a hydrocarbyl radical, B is e.g. N-(2,2,6, 6-tetramethyl-4-piperidyl)-butylamino, R is e.g. 2,2,6,6-tetramethyl-4-piperidyl and R2 is e.g. hexamethylene. The products obtained are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials in particular synthetic polymers such as polyolefins.
Description
BLOCK OLIGOMETERS CONTAINING GROUPS 1- HYDROCARBlLOXl-2.2.ß.ß-TETRAMETIL-4-PIPERIDILO AS STABILIZERS FOR ORGANIC MATERIALS
DESCRIPTION
Background and field of the invention
The present invention relates to specific block oligomers containing 1-hydrocarbyloxy-2, 2, 6, 6-tetramethyl-4-piperidyl groups, to their use as light stabilizers, heat stabilizers and anti-light stabilizers. oxidation for organic materials, particularly synthetic polymers, and the organic materials thus stabilized. The invention also relates to intermediate products. The stabilization of synthetic polymers with 2, 2, 6,6-tetramethylpiperidine derivatives has been described, for example, in US-A-4 086 204, US-A-4 331 586, US-A-4 335 242, US Pat. -A-4 234 707, US-A-4 459 395, US-A-4 492 791, US-A-5 204 473, EP-A-53 775, EP-A-357 223, EP-A-377 324, EP-A-462 069, EP-A-782 994 and GB-A-2 301 106. The present invention relates in particular to a product obtainable
1) reacting a product of the formula
(to)
with a compound of the formula (ß)
in a molar ratio of 1.2: 1 to 1.4: 1, preferably of 1.25: 1 to 1.4: 1 or 1.3: 1 to 1.4: 1, in particular of 1.3: 1 to 1.36: 1, for example 1.33: 1; 2) by reacting the end groups of the formula (?)
being present in the product of reaction 1) with a compound of the formula (?)
A-H (?)
in a molar ratio of 2 (end group): 1.7 up
2: 3, preferably 2: 2 to 2: 2.6, in particular 2: 2 a
2: 2.4; reactions 1) and 2) are carried out in an organic solvent in the presence of an inorganic base; and 3) transferring the groups of the formula (G-I)
which are present in the reaction product 2) to the groups of the formula (G-II);
the transfer is carried out by reacting the reaction product 2) with a hydroperoxide in a
hydrocarbon solvent in the presence of a catalyst that decomposes peroxide; Ri is a hydrocarbyl radical or -0-R? it is oxyl; R 2 is alkylene of 2 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, cycloalkylene of 5 to 7 carbon atoms, cycloalkarylene of 5 to 7 carbon atoms (alkylene of 1 to 4 carbon atoms), alkylene of 1 to 4 carbon atoms - (cycloalkylene of 5 to 7 carbon atoms), phenylendi (alkylene of 1 to 4 carbon atoms) or alkylene of 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl, -O- or > N-X? Xi being acyl of 1 to 12 carbon atoms or (C 1 -C 12 alkoxy) carbonyl or having one of the definitions of R given below; or R2 is a group of the formula (I-a), (I-b) or (I-c);
-CH, -CH-OH; (I-b) I or i c = or X.
with m being 2 or 3, X 2 being alkyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3, alkyl of 1 to 4 carbon atoms; phenyl that is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxys of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; and the X3 radicals being independently from each other alkylene of 2 to 12 carbon atoms; A is -0R3, -N (R4) (R5) or a group of the formula (II);
R3, R4, which are identical or different, are alkyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1,
2 or 3 alkyls of 1 to 4 carbon atoms; alkenyl of 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms
0 alkoxy of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy
1 to 8 carbon atoms, di (C 1-4 alkyl) amino or a group of the formula (III);
with Y being -O-, -CH2-, -CH2CH2 - or > N-CH3; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III); X is -O- or > N-R6; R6 is alkyl of 1 to 18 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on phenyl by 1, 2 or 3 alkyls from 1 to 4
carbon atoms; tetrahydrofurfuryl, a group of the formula (GI), or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy of 1 to 8 carbon atoms, di (alkyl of 1 to 4 carbon atoms) amino or a group of the formula (III); R has one of the meanings given for R6; and B has one of the meanings given for A. The transfer of the groups of the formula (GI) to the groups of the formula (G-II) can be carried out, for example, analogously to the method described in US Pat. A-4, 921, 962 which is incorporated herein by reference. The meaning of Ri depends on the hydrocarbon solvent used in the reaction 3). R t is preferably a hydrocarbyl radical having from 5 to 18 carbon atoms. Ri is in particular alkyl of 5 to 18 carbon atoms, alkenyl of 5 to 18 carbon atoms, alkynyl of 5 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms unsubstituted or substituted by alkyl of 1 to 4 carbon atoms. carbon; cycloalkenyl of 5 to 12 carbon atoms unsubstituted or substituted by alkyl of 1 to 4 carbon atoms; a bicyclic or tricyclic hydrocarbyl having from 6 to 10 carbon atoms or phenylalkyl from 7 to
9 carbon atoms unsubstituted or substituted on the phenyl by alkyl of 1 to 4 carbon atoms; and the hydrocarbon solvent in reaction 3) is, accordingly, depending on Ri, alkane of 5 to 18 carbon atoms, alkene of 5 to 18 carbon atoms, alkyne of 5 to 18 carbon atoms, cycloalkane of 5 to 12 carbon atoms unsubstituted or substituted by alkyl of 1 to 4 carbon atoms; cycloalkene of 5 to 12 carbon atoms unsubstituted or substituted by alkyl of 1 to 4 carbon atoms; a bicyclic or tricyclic hydrocarbon having 6 to 10 carbon atoms or phenylalkan of 7 to 9 carbon atoms unsubstituted or substituted on the phenyl by alkyl of 1 to 4 carbon atoms. Therefore, an additional preferred form of -Ri is heptyl, octyl, cyclohexyl, ethylcyclohexyl, cyclooctyl, cyclohexenyl, α-methylbenzyl or 1, 2, 3, 4-tetrahydronaphtenyl, and the hydrocarbon solvent in reaction 3) is, depending on Ri, heptane, octane, cyclohexane, ethylcyclohexane, cyclooctane, cyclohexene, ethylbenzene or tetralin. According to a particularly preferred embodiment Rx is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 3) is, depending on Ri, octane or cyclohexane.
Examples of alkyl not containing more than 18 carbon atoms are methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, t-butyl, pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, t -octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl and octadecyl, Ri is preferably alkyl of 6 to 12 carbon atoms, in particular heptyl or octyl. R4, R5 and R6 are preferably alkyl of 1 to 8 carbon atoms, in particular alkyl of 1 to 4 carbon atoms. An example of alkyl substituted by -OH is 2-hydroxyethyl. Examples of alkyl of 2 to 4 carbon atoms substituted by alkoxy of 1 to 8 carbon atoms, preferably by alkoxy of 1 to 4 carbon atoms, in particular methoxy or ethoxy, is 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl , 3-ethoxypropyl, 3-butoxypropyl, 3-octoxypropyl and 4-methoxybutyl. Examples of alkyl of 2 to 4 carbon atoms substituted by di (C 1 -C 4) alkyl amino, preferably by dimethylamino or diethylamino, are 2-dimethylaminoethyl, 2-diethylaminoethyl, 3-di-ethylaminopropyl, 3-diethylaminopropyl, -dibutylaminopropyl and 4-diethylaminobutyl.
The group of the formula (III) is preferably
/ \ DO NOT \ /
Preferred examples of alkyl of 2 to 4 carbon atoms substituted by a group of the formula (III) are groups of the formula / \ Y N- - (CH2 The group \ / / \ or 1 - (CH2) - is particularly prereferred. Examples of cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms are cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, t-butylcyclohexyl, cyclooctyl, cyclodecyl and cyclododecyl Unsubstituted or substituted cyclohexyl is preferred A preferred example of a bicyclic or tricyclic hydrocarbyl having from 6 to 10 carbon atoms is 1,2,3,4-tetrahydronaphtenyl A preferred example of cycloalkenyl of 5 to 12 carbon atoms unsubstituted or substituted by alkyl of 1 to 4 carbon atoms is cyclohexenyl Examples of alkenyl containing no more than 18 carbon atoms are allyl, 2-methylallyl, butenyl,
hexenyl, undecenyl and octadecenyl. Alkenyls are preferred in which the carbon atom in the 1- position is saturated, and allyl is particularly preferred. An example of alkynyl is pentynyl or octynyl. Examples of phenyl substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxies of 1 to 4 carbon atoms are methylphenyl, dimethylphenyl, trimethylphenyl, t-butylphenyl, di-t-butylphenyl, 3,5-diol. t-butyl-4-methylphenyl, methoxyphenyl, ethoxyphenyl and butoxyphenyl. Examples of phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms are benzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, t-butylbenzyl and 2-phenylethyl. Benzyl is preferred. Examples of acyl (aliphatic, cycloaliphatic or aromatic) containing no more than 12 carbon atoms are formyl, acetyl, propionyl, butyryl, pentanoyl, hexanoyl, heptanoyl, octanoyl and benzoyl. Alkanoyl of 1 to 8 carbon atoms and benzoyl are preferred. Acetyl is especially preferred. Examples of carbonyl (alkoxy of 1 to 12 carbon atoms) are methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, butoxycarbonyl, pentoxycarbonyl, hexoxycarbonyl, heptoxycarbonyl, octoxycarbonyl,
nonyloxycarbonyl, decyloxycarbonyl, undecyloxycarbonyl and dodecyloxycarbonyl. Examples of alkylene containing no more than 12 carbon atoms are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, ethylene octa, decamethylene and dodecamethylene. R 2 is, for example, alkylene of 2 to 8 carbon atoms or alkylene of 4 to 8 carbon atoms, in particular alkylene of 2 to 6 carbon atoms, preferably hexamethylene. An example of alkenylene of 4 to 12 carbon atoms is 3-hexenylene. An example of cycloalkylene of 5 to 7 carbon atoms is cyclohexylene. Examples of alkyls of 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl are
/ \ -CH2CH2- N I I N-CH2CH2- \ /
Examples of alkyls of 4 to 12 carbon atoms interrupted by -O-, for example, 1, 2 or 3 -O-, are 3-oxapentane-1, 5-diyl, 4-oxaheptane-1, 7-diyl, 3,6-dioxaoctane-1,8-diyl, 4,7-dioxadecane-1, 10-diyl, 4,9-dioxadodecane-1, 12-diyl, 3,6,9-trioxaundecane-1, 11-diyl and 4.7, 10-trioxatridecane-1, 13-diyl.
Examples of alkylene of 4 to 12 carbon atoms interrupted by > N-X? are -CH2CH2CH2-N (Xx) -CH2CH2-N (Xi) -CH2CH2CH2-, in particular -CH2CH2CH2-N (CH3) -CH2CH2-N (CH3) -CH2CH2CH2. "An example of cycloalkylenei of 5 to 7 carbon atoms (alkylene of 1 to 4 carbon atoms) is cyclohexylenedimethylene Examples of alkylene of 1 to 4 carbon atoms (cycloalkylene of 5 to 7 carbon atoms) are methylenedicyclohexylene and isopropylidenedicyclohexylene. An example of phenylendi (C 1 -C 4 alkylene) is phenylene ethylene In the compound of the formula (β), R is preferably a group of the formula (GI) A product in which R 2 is alkylene is preferred from 2 to 12 carbon atoms, cycloalkylene of 5 to 7 carbon atoms, cycloalkarylene of 5 to 7 carbon atoms (alkylene of 1 to 4 carbon atoms), alkylene of 1 to 4 carbon atoms (cycloalkylene of 5 to 7) carbon atoms), phenylendi (alkylene of 1 to 4 carbon atoms) or alkylene of 4 to 12 carbon atoms interrupted by -O- or >N-Xa with X being acyl of 1 to 12 carbon atoms or (alkoxy of 1 to 12 carbon atoms) carbonyl or having one of
the definitions of R4; or R2 is a group of the formula (I-b); R3, R4 and R5, which are identical or different, are alkyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxys of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III); R6 is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; or a group of the formula (G-I). Also preferred is a product wherein R2 is alkylene of 2 to 10 carbon atoms, cyclohexylene, cyclohexylendi (alkylene of 1 to 4 carbon atoms), alkylene of 1 to 4 carbon atoms-
dicyclohexylene or phenylendi (alkylene of 1 to 4 carbon atoms); 3f and 5A, which are identical or different, are alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 7 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; benzyl which is unsubstituted or substituted on the phenyl by alkyl of 1 to 4 carbon atoms; or -N (R4) (R5) is additionally a group of the formula (III); and R6 is alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 7 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; benzyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; or a group of the formula (G-I). Further preferred is a product in which R2 is alkylene of 2 to 8 carbon atoms; R3, R4 and R5, which are identical or different, are alkyl of 1 to 8 carbon atoms, cyclohexyl which is unsubstituted or substituted by methyl; phenyl that is unsubstituted or substituted by methyl; benzyl or -N (R4) (R5) is further 4-morpholinyl; Y
R6 is alkyl of 1 to 8 carbon atoms, cyclohexyl which is unsubstituted or substituted by methyl; benzyl or a group of the formula (G-I). Particularly preferred is a product in which Ri is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 3) is, depending on Rx, octane or cyclohexane; R2 is alkylene of 2 to 6 carbon atoms; A is -N (R4) (R5) or a group of the formula (II); R and s / which are identical or different, are alkyl of 1 to 8 carbon atoms; or -N (R4) (Rs) is further 4-morpholinyl; X is > NR6; Re is alkyl of 1 to 8 carbon atoms; and B has one of the meanings given for A.
Also particularly preferred is a product in which Ri is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 3) is, depending on Ri, octane or cyclohexane; R2 is alkylene of 2 to 6 carbon atoms; R is a group of the formula (G-I); A is -N (R4) (R5);
R4 and R5 / which are identical or different, are alkyl of 1 to 8 carbon atoms; B is a group of the formula (II); X is > NR6; Rs is alkyl of "1 to 8 carbon atoms The organic solvent used in reactions 1) and 2) is in particular an aromatic hydrocarbon or an aliphatic ketone Examples of an aromatic hydrocarbon are toluene, xylene, trimethylbenzene, isopropylbenzene, diisopropylbenzene and t-butylbenzene Examples of an aliphatic ketone are ethylethyl ketone, methyl butyl ketone, methyl isobutyl ketone, ethylamyl ketone, ethyl butyl ketone, di-n-propyl ketone, methyl hexyl ketone, and ethylamyl ketone.Cels which are essentially insoluble in water are preferred.The preferred solvents are toluene, xylene, methylbutyl ketone, and methyl isobutyl ketone. Particularly preferred are xylene and methyl isobutyl ketone Examples of the inorganic base used in the present process are sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, sodium hydroxide is preferred.
Reactions 1) and 2) are preferably carried out in an inert atmosphere, in particular under nitrogen. The reagents of the formulas () and (ß) are usually added together in a reactor at a temperature of 10 ° to 60 ° C. Depending on the solvent, the temperature is, for example, subsequently increased to
80 ° to 85 ° C. Then, after closing the reactor, the temperature can be further increased to, for example, 110 ° to 220 ° C, preferably 150 ° to 160 ° C. Since the reaction is carried out in a closed system, the pressure increases with temperature. Generally, a pressure of 3 to 8 bars is measured in the reactor, for example, 4 to 6 bars. Due to the low boiling point of the solvents used, also the reaction 2) is conveniently carried out in a closed system. Depending on the solvent, the reaction 2) can be carried out at a temperature of, for example, 110 ° to 180 ° C, preferably
130 ° to 170 ° C, in particular 140 ° to 160 ° C. Due to the high temperature, a pressure of normally 3 to 8 bars, for example, 4 to 6 bars, is again measured in the reactor. If desired, after the completion of the reaction 2), the compound of the formula (d) and optionally unreacted raw material can be removed from the mixture
final by distillation or using common purification techniques. The product of reaction 2) is conveniently isolated before reaction 3) proceeds. The peroxide decomposing catalyst used in reaction 3) is, for example, a metal carbonyl, metal oxide, metal acetylacetonate or a metal alkoxide wherein the metal is selected from groups IVb, Vb, VIb, VIIb and VIII of the periodic table , preferably vanadium (III) acetylacetonate, cobalt carbonyl, chromium (VI) oxide, titanium (IV) isopropoxide, titanium tetrabutoxide, molybdenum hexacarbonyl, molybdenum trioxide and the like. The most preferred catalyst is Mo03. Suitable hydroperoxides are t-butyl hydroperoxide, t-amyl hydroperoxide, t-hexyl hydroperoxide, t-octyl hydroperoxide, ethylbenzene hydroperoxide, tetralin hydroperoxide or eumeno
(= isopropylbenzene) hydroperoxide. The most preferred hydroperoxide is t-butyl hydroperoxide. In reaction 3) from 2 to 8 moles, preferably 3 to 6 moles, of the hydroperoxide, 0.001 to 0.1 moles, preferably 0.005 to 0.05 moles, of the peroxide decomposing catalyst and 5 to 30 moles, preferably 10 to 10 moles, are applied. 20 moles, of solvent
hydrocarbon, for example, per mole of the hindered amine portion of the formula (G-I)
being present in the reaction product 2). The transfer of the hindered amine portions of the formula (G-I) to the groups of the formula
it is carried out, for example at 75 ° to 160 ° C, preferably 100 ° to 150 ° C. When in reaction 3) the hindered amine portions of the formula (GI) are first treated with aqueous hydroperoxide in the presence of the peroxide decomposing catalyst in an inert organic solvent (for example analogously to the method described in US-A-4) 691 015), the initial reaction product obtained in
a relatively short time is the corresponding N-oxyl intermediate (-ORi = oxyl) which is very colorful and can be isolated per se. A further preferred embodiment of this invention therefore relates to a product available in accordance with the above reactions 1) to 3) in which the radical -O-Ri is oxyl and the hydrocarbon solvent in reaction 3) is an organic solvent inert, preferably toluene or 1,2-dichloroethane. When the organic solvent in reaction 3) is a hydrocarbon having a labile hydrogen atom, when a sufficient molar excess of hydroperoxide remains beyond what is needed to convert the amine to the corresponding N-oxyl derivative, and when the The reaction mixture is heated to moderate temperatures (preferably 100 ° to 150 ° C) for an additional period, an additional reaction takes place between the N-oxyl compound (either prepared in situ from the original amine or used as the initial starter in the process) and the hydrocarbon solvent to give the corresponding N-hydrocarbyloxy derivative. The original reaction mixture in reaction 3) is colorless, but becomes very colorful as the N-oxyl intermediate is formed. This color disappears as the N-oxyl compound becomes the
colorless product N-hydrocarbyloxy. In this way, this process essentially has a color indicator on it to show the magnitude of the reaction. When the reaction mixture becomes colorless, it shows that the colorful intermediate N-oxyl has been completely converted to the N-hydrocarbyloxy product. An embodiment of this invention is also an available product by hydrogenating the reaction product 3), wherein -ORi in the formula (G-II) is oxyl, to obtain a product with groups of the formula (G-III).
The hydrogenation is carried out according to known methods, for example in an organic solvent, for example methanol or ethanol, in the presence of a hydrogenation catalyst, preferably palladium on carbon or Pt02, as described for example in the US document. -A-4 691 015. If desired, the product obtained in the reaction
3) It can be purified by one of the following methods:
a) Residual peroxide is decomposed and the solvent is evaporated to obtain a crude solid product. The solid is stirred with an inert solvent such as cyclohexane, octane, hexane, petroleum ether, xylene, toluene, acetone, methyl ethyl ketone, ethyl acetate, butyl acetate, t-butyl alcohol, t-amyl alcohol, isopropyl alcohol, ethanol , methanol, chloroform, dichloromethane, acetonitrile, diethyl ether, dibutyl ether and / or water. The mixture can be heated while stirring. After stirring, the mixture is cooled and the solid product is collected by filtration and dried. b) The residual peroxide decomposes and the solvent evaporates partially. The residue is filtered to obtain a solid which is washed with an inert solvent such as one of the above, which can be cooled and then dried. c) The residual peroxide decomposes and the solvent evaporates at elevated temperature to obtain a fusion. The hot melt is mixed with an inert solvent, such as one of the above, which can be cooled and the resulting precipitate is collected by filtration and dried. Variations of this procedure include mixing the hot melt with solvent and then cooling the mixture to obtain a precipitate, or mixing the hot melt with solvent, heating to carry
any solid to solution, and cool to obtain then a precipitate. d) The residual peroxide decomposes and the solvent evaporates at elevated temperature to obtain a fusion. The melt is dissolved in an inert solvent, such as any of the above, with or without heating, and the resulting solution can be concentrated by distilling off some of the excess solvent. The solution is then mixed with a second solvent, such as one of those described above, at a temperature such that the product precipitates. The solid is collected by filtration and dried. More specifically, the product obtained in reaction 3) is preferably purified as follows: After reaction 3) is complete, the crude reaction mixture is cooled to 50 ° C and treated with 20% aqueous solution of Sodium sulfite until the concentration of residual peroxide is below 0.5%. The aqueous layer is unfolded, and the organic layer is concentrated by heating the product solution under reduced pressure. The crude product is dissolved in excess t-butyl alcohol, and the solvent is removed by heating the solution under reduced pressure until the concentration of solids is 50%. This solution is added slowly
to cold methanol. The resulting precipitate is filtered, washed with methanol, and dried by heating under vacuum. In general, the starting materials used in the above described process are known. In the event that they are not commercially available, they can be prepared in accordance with known methods. The compound of the formula () can be prepared, for example, by reacting cyanuric chloride with a compound B-H in a stoichiometric ratio in the presence of an organic solvent and an inorganic base. It is appropriate to use for the preparation of the compound of the formula (a) the same solvent and the same inorganic base as in the reactions 1) to 2) indicated above. If desired, after preparation of the starting material of the formula (a), the reaction 1) can follow immediately without isolation of the compound of the formula (a). Some starting materials of the formula (ß) are described, for example, in documents W0-A-95/21 157, US-A-4 316 837 and US-A-4 743 688. An additional embodiment of this invention it is a product available from the previous reactions 1) and 2). Products in which the nitrogen atom in the group
it is substituted by alkyl of 1 to 8 carbon atoms, hydroxyalkyl of 2 to 8 carbon atoms, 0, -OH, hydrocarbyloxy of 1 to 8 carbon atoms (for example alkoxy of 1 to 8 carbon atoms or cycloalkoxy of 5 to 12 carbon atoms), -CH2CN, alkenyl of 3 to 6 carbon atoms, alkynyl of 3 to 6 carbon atoms, phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted in phenyl by 1, 2 or 3 alkyls from 1 to 4 carbon atoms; or acyl of 1 to 8 carbon atoms, can be prepared in analogy to the above reactions 1) and 2), using appropriate starting materials. The nitrogen atom is preferably substituted by alkyl of 1 to 4 carbon atoms, in particular methyl. Those starting materials that contain a group of the formula
hydrocarbon
they can be prepared, for example, analogously to the methods described in US-A-4 921 962, US-A-5 021 577 and US-A-5 204 473. The product of reaction 2) is not a single compound specific but a compound with a molecular weight distribution. Polydispersity indicates the molecular weight distribution of a polymeric compound. In the present application, polydispersity is the ratio of molecular weights average weight (Mw) and average number (Mn). A value of Mw / Mn equal to 1 signifies that the compound is monodisperse and has only a molecular weight and not a molecular weight distribution. A narrow molecular weight distribution is characterized by a polydispersity (Mw / Mh) close to 1. A preferred product of reaction 2) has a polydispersity of 1.1 to 1.7, for example 1.1 to 1.6 or 1.3 to 1.7, in particular 1.3 to 1.6. It is important to note that the product of the reaction 2) contains, for example, less than 5 mol%, in particular less than 2 mol% or less than 1 mol%, of linear sub-pipelines which are not crowned at the end by a portion of the formula
During reactions 1) a cyclic compound of the formula can be formed as a by-product
That compound which is known from US-A-4 442 250 can be present in an amount of less than 8 mol% in the product of reaction 2). The product of reaction 2) can be preferably described as a mixture containing a monodisperse compound of the formula (MI), a monodisperse compound of the formula (M-II), a monodisperse compound of the formula (M-III) and a monodisperse compound of the formula
(M-IV), the compounds differ only in the number of repetitive units,
the radicals A, B, R and R2 being as defined above and the total amount of the compounds of the formulas (MI), (M-II), (M-III) and (M-IV) being 40 to 70% mol, in particular 50 to 65 mol%, relative to the total mixture. The proportion of the compounds (MI) to (M-II), (MI) to (M-III) and (MI) to (M-IV) in molar% can be, for example, 0.6: 1 to 1.6: 1 or 0.6: 1 to 1.4: 1. Reaction 3) is related in particular to the transfer of the groups of the formula (G-I)
being present in the mixture containing the compounds of the formulas (M-I), (M-II), (M-III) and (M-IV) to groups of the formula (G-II).
After the transfer the amounts of the compounds shown below the formulas (P-I), (P-II),
(P-III) and (P-IV) in the product of reaction 3) correspond to the amounts of the initial compounds shown above of formulas (M-I), (M-II), (M-III) and
(M-IV), since the main structure of these compounds is not affected during the reaction. Therefore, a further embodiment of this invention is a mixture containing a monodisperse compound of the formula (PI), a monodisperse compound of the formula (P-II), a monodisperse compound of the formula (P-III) and a compound monodisperse of the formula
(P-IV), such compounds differ only in the number of repetitive units,
being from 40 to 70 mol% the total amount of the compounds of the formulas (PI), (P-II), (P-III) and (P-IV), in particular 50 to 65 mol%, relative to the total mix; Y
Ri is hydrogen, a hydrocarbyl radical or -0-Rx is oxyl; R 2 is alkylene of 2 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, cycloalkylene of 5 to 7 carbon atoms, cycloalkarylene of 5 to 7 carbon atoms (alkylene of 1 to 4 carbon atoms), alkylene of 1 to 4 carbon atoms- (cycloalkylene of 5 to 7 carbon atoms), phenylendi (alkylene of 1 to 4 carbon atoms) or alkylene of 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl, -O- or > N-XX with Xt being acyl of 1 to 12 carbon atoms or (C 1 -C 12 alkoxy) carbonyl or having one of the definitions of R given below; or R2 is a group of the formula (I-a), (I-b) or (I-c);
-CH - CH - CH2- (I-b) O I c = o * 2
with m being 2 or 3, where X 2 is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxys of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; and the X3 radicals being independently from each other alkylene of 2 to 12 carbon atoms; A * is -OR3, -N (R) (R5) or a group of the formula (G-IV);
R3? R. and s which are identical or different, are alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is
unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; alkenyl of 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxys of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy of 1 to 8 carbon atoms, di (alkyl of 1 to 4 carbon atoms) amino or a group of the formula (III);
with Y being -O -, -CH2 -, -CH2CH2 - or > N-CH3; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III); X * is -O - or > N-R6 *; R6 * is alkyl of 1 to 18 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3
alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl, a group of the formula (G-II),
or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy of 1 to 8 carbon atoms, di (alkyl of 1 to 4 carbon atoms) amino or a group of the formula (III); R * has one of the meanings given for R6 *; and B * has one of the meanings given for A *. The proportion of the compounds (PI) to (P-II), (PI) to (P-III) and (PI) to (PIV) in molar% can be, for example, 0.6: 1 to 1.6: 1 or 0.6 : 1 to 1.4: 1. Preferred are those mixtures in which Ri is octyl or cyclohexyl; R2 is alkylene of 2 to 6 carbon atoms; R * is a group of the formula (G-II); A * is -N (R4) (R5);
R4 and Rs, which are identical or different, are alkyl of 1 to 8 carbon atoms; B * is a group of the formula (G-IV); X * is > NR6 *; and R6 * is alkyl of 1 to 18 carbon atoms. In the mixtures according to this invention, the radical Rx can act as a linking group between two or more compounds of the formulas (PI), (P-II), (P-III) and / or (P-IV) . In this case, bridges of the formula are formed
(L-I)
between the indicated compounds. The meaning of Ri * can be deduced from the meaning of Ri. The only difference between these two radicals is that Ri * has one or two additional valences. Thus, Ri as cyclohexyl corresponds to Ri * as cyclohexanediyl or cyclohexantriyl and Ri as octyl corresponds to Ri * as octandiyl or octantriil. The products of this invention as well as the described mixtures are very effective improving the resistance to light, heat and oxidation of materials
organic, especially synthetic polymers and copolymers. In particular, a pigment interaction is observed as well as a very good coloration in polypropylene, especially in polypropylene fibers, in particular in the presence of fire retardants as well as in low density polyethylene (LDPE) films for agricultural use. It is especially noteworthy that the product of this invention as well as the mixtures described are fire retardants. Examples of organic materials that can be stabilized are:
1. Polymers of monoolefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for example of cyclopentene or norbornene, polyethylene (which can optionally be have crossed link), for example high density polyethylene (HDPE), high molecular weight polyethylene and high density (HDPE-APM), high density polyethylene and ultra high molecular weight
(HDPE-PUAPM), medium density polyethylene (PEDM), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (PEMBD) and (PEUBD). The polyolefins, ie the polymers of monoolefins that are exemplified in the preceding paragraph,
preferably polyethylene and polypropylene, can be prepared by different methods and especially by the following methods: a) radical polymerization (usually under elevated pressure and at elevated temperature). b) catalytic polymerization using a catalyst that normally contains one or more metals of groups IVb, Vb, VIb or VIII of the periodic table. These metals usually have one or more ligands, typically oxides, halides, alcoholates, esters, ethers, amines, alkalis, alkenyls and / or aryls which may be coordinated. These metal complexes may be in free form or fixed in substrates, typically on activated magnesium chloride, titanium (III) chloride, alumina or silicon oxide. These catalysts can be soluble or insoluble in the polymerization medium. The catalysts may be used alone in the polymerization or other activators may be used, typically metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyloxanes, where the metals are elements of the groups la, lía and / or Illa of the periodic table. Activators can be modified conveniently
with additional ester, ether, amino or silyl groups. These catalyst systems are usually referred to as Phillips, Standard Oil Indian, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (CSS). 2. Mixtures of the polymers mentioned in 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP / HDPE, PP / PEBD) and mixtures of different types of polyethylene (PEBD / HDPE). 3. Copolymers of monoolefins and diolefins with one another or with other vinyl monomers, for example ethylene / propylene copolymers, linear low density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene copolymers / but-1-ene, propylene / isobutylene copolymers, ethylene / but-1-ene copolymers, ethylene / hexene copolymers, ethylene / methylpentene copolymers, ethylene / heptene copolymers, ethylene / octene copolymers, propylene copolymers / butadiene, isobutylene / isoprene copolymers, ethylene / alkyl acrylate copolymers, ethylene / alkyl methacrylate copolymers, ethylene / vinyl acetate copolymers and their copolymers with carbon monoxide or ethylene / acrylic acid copolymers and their salts ( ionomers) as well as terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene or
ethyldiene-norbornene; and mixtures of said copolymers with each other and with the polymers mentioned in 1), for example copolymers of polypropylene / ethylene-propylene, copolymers of PEBD / ethylene-vinyl acetate (EAV), copolymers of PEBD / ethylene-acrylic acid (EAA), PELBD / EAV, PELBD / EAA and alternative or random copolymers of polyalkylene / carbon monoxide and mixtures thereof with other polymers, for example polyamides. 4. Hydrocarbon resins (for example from 5 to 9 carbon atoms) including hydrogenated modifications thereof (for example, thickeners) and mixtures of polyalkylenes and starch. 5. Polystyrene, poly (p-methylstyrene), poly (α-methylstyrene). 6. Copolymers of styrene or α-methylstyrene with dienes or acrylic derivatives, for example styrene / butadiene, styrene / acrylonitrile, styrene / alkyl ratacrilate, styrene / butadiene / alkyl acrylate, styrene / butadiene / alkyl methacrylate, styrene / anhydride maleic, styrene / acrylonitrile / methyl acrylate; mixtures of high impact resistant styrene copolymers and another polymer, for example a polyacrylate, a diene polymer and an ethylene / propylene / diene terpolymer; and styrene block copolymers such as styrene / butadiene / styrene,
styrene / isoprene / styrene, styrene / ethylene / butylene / styrene or styrene / ethylene / propylene / styrene. 7. Styrene or α-methylstyrene graft copolymers, for example styrene in polybutadiene, styrene in polybutadiene-styrene or copolymers of polybutadiene-acrylonitrile; styrene and acrylonitrile (or methacrylonitrile) in polybutadiene; styrene, acrylonitrile and methyl methacrylate in polybutadiene; styrene and maleic anhydride in polybutadiene; styrene, acrylonitrile and maleic anhydride or maleimide in polybutadiene; styrene and maleimide in polybutadiene; styrene and alkyl acrylates or methacrylates in polybutadiene; styrene and acrylonitrile in ethylene / propylene / diene terpolymers; styrene and acrylonitrile in polyalkyl acrylates or polyalkyl methacrylates, styrene and acrylonitrile in acrylate / butadiene copolymers, as well as mixtures thereof with the copolymers listed in 6), for example blends of copolymers known as ABS polymers, MBS, ASA or AES. 8. Halogen-containing polymers such as polychloroprene, chlorinated rubbers, chlorinated or brominated isobutylene-isoprene copolymers (halobutyl rubber), chlorinated or sulfochlorinated polyethylene, copolymers of ethylene and chlorinated ethylene, homo- and epichlorohydrin copolymers, especially polymers of compounds of vinyl containing halogens, for example polyvinyl chloride, chloride
polyvinylidene, polyvinyl fluoride, polyvinylidene fluoride, as well as copolymers thereof such as copolymers of vinyl chloride / vinylidene chloride, vinyl chloride / vinyl acetate or vinylidene chloride / vinyl acetate. 9. Polymers derived from α, β-unsaturated acids and derivatives thereof such as polyacrylates and polymethacrylates; polymethyl methacrylates, polyacrylamides and polyacrylonitriles modified on impact with butyl acrylate. 10. Copolymers of the monomers mentioned in 9) with each other or with other unsaturated monomers, for example copolymers of acrylonitrile / butadiene, copolymers of acrylonitrile / alkyl acrylate, copolymers of acrylonitrile / alkoxyalkyl acrylate or copolymers of acrylonitrile / vinyl halide or acrylonitrile / alkyl methacrylate / butadiene terpolymers. 11. Polymers derived from unsaturated alcohols and amides or the acyl derivatives or acetals thereof, for example polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate or polyallylamine; as well as its copolymers with the olefins mentioned in 1).
12. Homopolymers and copolymers of cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or copolymers thereof with bisglycidyl ethers. 13. Polyacetals such as polyoxyethylene and the polyoxymethylenes containing ethylene oxide as a comonomer; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS. 14. Polyphenylene oxides and sulphides, and mixtures of polyphenylene oxides with styrene polymers or polyamides. 15. Polyurethanes derived from hydroxyl-terminated polyethers, polyesters or polybutadienes, on the one hand, and aliphatic or aromatic polyisocyanates, on the other hand, as well as precursors thereof. 16. Polyamides and copolyamides derived from diamines and dicarboxylic acids and / or aminocarboxylic acids or the corresponding lactams, for example polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9, 6/12, 4/6 , 12/12, polyamide 11, polyamide 12, aromatic polyamides starting from diamine of m-xylene and adipic acid; polyamides prepared from hexamethylenediaraine and isophthalic and / or terephthalic acid and with or without an elastomer as a modifier, for example poly-2,4,4-trimethylhexamethyleneterephthalamide or poly-m-
phenylene isophthala ida; and also block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers and chemically bonded or grafted elastomers; or with polyethers, for example with polyethylene glycol, polypropylene glycol or polytetramethylene glycol; as well as polyamides or copolyamides modified with EPDM or ABS; and polyamides condensed during processing (RIM polyamide systems). 17. Polyureas, polyimides, polyamidimides and polyetherimides, polydantoins and polybenzimidazoles. 18. Polyesters derived from dicarboxylic acids and diols and / or from hydroxycarboxylic acids or the corresponding lactones, for example polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate and polyhydroxybenzoates, as well as block copolyether ester derivatives of hydroxyl terminated polyethers; and also polyesters modified with polycarbonates or MBS. 19. Polycarbonates and polyester carbonates. 20. Polysulfones, polyether sulfones and polyether ketones. 21. Crosslinked polymers derived from aldehydes, on the one hand, and phenols, ureas and melamines, on the other, such as phenol / formaldehyde resins, urea / formaldehyde resins and melamine / formaldehyde resins.
22. Drying and non-drying alkyd resins. 23. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols and vinyl compounds as cross-lng agents, and also halogen-containing modifications of low flammability. 24. Acrylic resins capable of cross-lng derived from substituted acrylates, for example epoxy acrylates, urethane acrylates or polyester acrylates. 25. Alkyd resins, polyester resins and acrylate resins with cross-lng with melamine resins, urea resins, isocyanate resins, isocyanurates, polyisocyanates or epoxy. 26. Cross-ld epoxiresins derived from aliphatic, cycloaliphatic, heterocyclic or glycidoaromatic compounds. 27. Natural polymers such as cellulose, rubber, gelatin and chemically modified homologous derivatives thereof, for example cellulose acetates, cellulose propionates and cellulose butyrates, or cellulose ethers such as methylcellulose; as well as rosins and their derivatives. 28. Mixtures of the aforementioned polymers (poly ezclas), for example PP / EPDM, polia ida / EPDM or ABS,
PVC / EAV, PVC / ABS, PVC / MBS, PC / ABS, PBTP / ABS, PC / ASA, PC / PBT, PVC / CPE, PVC / acrylates, POM / PUR thermoplastic, PC / PUR thermoplastic, POM / acrylate, POM / MBS, PPO / HIPS, PPO / PA 6.6 and copolymers, PA / HDPE, PA / PP, PA / PPO, PBT / PC / ABS Oo PBT / PET / PC. 29. Natural and synthetic organic materials which are pure monomeric compounds or mixtures of said compounds, for example mineral oils, animal and vegetable fats, oils and waxes, or oils, fats and waxes based on synthetic esters (for example phthalates, adipates, phosphates or trimellitates) and also mixtures of synthetic esters with mineral oils in any proportion by weight, those such as spinning compositions as well as aqueous emulsions of said materials are typically used. 30. Aqueous emulsions of natural or synthetic rubber, for example natural latex or carboxylated styrene / butadiene copolymer latex. The invention also relates to a composition comprising an organic material that is susceptible to light-induced or oxidative degradation and a product or mixture in accordance with the present invention. The organic material is preferably a synthetic polymer, more particularly one selected from the groups mentioned above. Preferred
polyolefins and polyethylene and polypropylene are particularly preferred. A further embodiment of this invention is a method for stabilizing an organic material against degradation induced by light, heat or oxidation, which comprises incorporating into the organic material a product or a mixture in accordance with the present invention. The product or mixture according to the present invention can be used in various proportions depending on the nature of the material to be stabilized, the end use to which it will be used and the presence of other additives. In general, it is appropriate to use, for example, from 0.01 to 5% by weight of the product or mixture according to the present invention, relative to the weight of the material to be stabilized, preferably 0.05 to
2%, in particular from 0.05 to 1%. The product or mixture according to this invention can be added, for example, to the polymeric materials before, during or after the polymerization or cross-lng of the materials. In addition, they can be incorporated into the polymeric materials in pure form or they can be encapsulated in waxes, oils or polymers. In general, the product or mixture according to this invention can be incorporated into the
polymeric materials by means of various processes, such as dry blending in the form of powder, or wet mixing in the form of solutions or suspensions or else in the form of a process of standard batches containing the product or mixture according to this invention in a concentration of 2.5 to 25% by weight; in such operations, the polymer can be used in the form of powder, granules, solutions, suspensions or in the form of cross-links. The materials stabilized with the product or mixture according to this invention can be used for the production of castings, films, tapes, monofilaments, fibers, surface coatings and the like. If desired, other conventional additives can be added for the synthetic polymers, such as antioxidants, UV light absorbers, nickel stabilizers, pigments, fillers, plasticizers, corrosion inhibitors and metal deactivators, to the organic materials containing the product or the mixture according to this invention. Particular examples of conventional additives are: 1. Antioxidants 1.1. Alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-dihydrogen
tert-butyl-4-ethylphenol, 2,6-diter-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dichloropentyl-4-methylphenol, 2- (a) -methylcyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are linear or branched at end of the chain, for example, 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1 '-methylundec-1'-yl) phenol, 2,4-dimethyl-6- ( 1 '-methylheptadec-1' -yl) phenol, 2,4-dimethyl-6- (1'-methyltridec-1'-yl) phenol and mixtures thereof. 1.2. , Alkyltiomethylphenols, for example 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol. 1.3. Hydroquinones and alkylated hydroquinones, for example 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol , 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-stearate -hydroxyphenyl, bis- (3,5-di-tert-butyl-4-hydroxyphenyl) adipate. 1.4 Tocopherols. For example α-tocopherol, β-tocopherol, α-tocopherol, d-tocopherol, and their mixtures (vitamin E). 1.5. Hydroxylated thiodiphenyl ethers, for example 2, 2'-thiobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-)
octylphenol), 4,4'-thiobis (6-tert-butyl-3-methylphenol), 4,4'-thiobis (6-tert-butyl-2-methylphenol), 4,4'-thiobis- (3,6) di-sec-amylphenol), 4,4'-bis- (2,6-dimethyl-4-hydroxyphenyl) disulfide. 1.6. Alkylidenebisphenols, for example 2,2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), 2,2'-methylenebis [4-methyl] -6- (α-methyl-cyclohexyl) phenol], 2, 2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (6-nonyl-4-methylphenol), 2'2'- methylenebis (4,6-di-tert-butylphenol), 2, 2'-ethylenebis (4,6-di-tert-butylphenol), 2, 2'-ethylenebis (6-tert-butyl-4-isobutylphenol), 2 , 2'-methylenebis [6- (a-methylbenzyl) -4-nonylphene-nol], 2,2'-methylenebis [6- (a, a-dimethylbenzyl) -4-nonylphenol], 4, 4'-methylenebis ( 2,6-di-tert-butylphenol), 4,4'-methylenebis (6-tert-butyl 2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2, 6-bis (3-tert-butyl-5-methyl-2-hydroxybenzyl) -4-methylphenol, 1, 1, 3-tris (5-tert-butyl-4-hydroxy-2-ethylphenyl) butane , 1, 1-bis (5-tert-butyl-4-hydroxy-2-methyl-phenyl) -3-n-dodecyl mercaptobutane, bis [3,3-bis (3'-tert-butyl-4'-hydroxyphenyl) butyrate] of ethylene glycol, bis (3-tert-butyl-4-hydroxy-5-methyl-phenyl) dicyclopentadie no, bis [2- (3'-tert-butyl-2'-hydroxy-5'-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis- (3, 5-dimethyl- 2-hydroxyphenyl) butane, 2,2-bis- (3,5-di-tert-butyl-4-hydroxyphenyl) propane, 2,2-bis- (5-tert-butyl-4-hydroxy-2-)
methylphenyl) -4-n-dodecyl mercaptobutane, 1,1,5,5-tetra- (5-tert-butyl-4-hydroxy-2-methylphenyl) pentane. 1.7. O-, N- and S-benzyl compounds, for example 3, 5, 3 '5' -tetra-tert-butyl-4,4 '-dihydroxydibenzylether, octa-decyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl -4-hydroxy-3, 5-di-tert-butylbenzylmercaptoacetate, tris- (3, 5-di-tert-butyl-4-hydroxybennyl) amine, bis (4-tert-butyl-3-hydroxy-2, 6- dimethylbenzyl) dithio-terephthalate, bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate. 1.8. Hydroxybenzylated malonates, for example dioctadecyl-2,2-bis- (3,5-di-tert-butyl-2-hydroxybenzyl) -malonate, di-octadecyl-2- (3-tert-butyl-4-hydroxy-5-) methylbenzyl) -malonate, di-dodecyl mercaptoethyl-2, 2-bis- (3,5-di-tert-butyl-4-hydroxybenzyl) malonate, bis [4- (1,1,3,3-tetramethylbutyl) phenyl] - 2, 2-bis (3,5-di-tert-butyl-4-hydroxy-benzyl) -alonate. 1.9. Hydroxybenzyl aromatic compounds, eg 1,3, 5-tris- (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1, -bis (3, 5-di) -tert-butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) phenol. 1.10. Triazine compounds, for example 2,4-bis (octylmercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3, 5-di-tert-butyl-4-)
hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2,4,6- tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, , 3, 5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenylethyl) -1, 3, 5-triazine, 1,3,5-tris (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) -hexahydro-1,3,5-triazine, 1,3,5-tris (3, 5 -dicyclohexyl-4-hydroxybenzyl) isocyanurate. 1.11. Benzylphosphonates, for example dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4- hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of the 3,5-di-tert-butyl-4-hydroxybenzylphosphonic onoethyl ester. 1.12. Acylaminophenols, for example 4-hydroxylauranilide, 4-hydroxystearanilide, N- (3, 5-di-tert-butyl-4-hydroxyphenyl) carbamate octyl. 1.13. Esters of ß- (3,5-di-tert-butyl-4-hydrocyphenyl) propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol , 1, 9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide,
3-tiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane. 1.14. Esters of ß- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol , 1, 9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2,6,6-trioxabicyclo [2.2.2] octane. 1.15. Esters of ß- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1, 2 -propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phosphate 2, 6, 7-trioxabicyclo [2.2.2] octane. 1.16. Esters of 3,5-ditertiary butyl-4-hydroxyphenyl) acetic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, octadecanol, 1,6-hexanediol,
1, 9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol , trimethylolpropane, 4-hydroxymethyl-l-phospha-2,6,6-trioxabicyl [2.2.2] octane. 1.17. Amides of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid for example N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylenediamine, N, N'-bis (3, 5-di-tert-butyl-4-hydroxyphenylpropionyl) trimethylene diamine, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazide, N, N'-bis [2 - (3- [3,5-di-tert-butyl-4-hydroxyphenyl] propionyloxy) ethyl] oxamide (Naugard® XL-1 provided by Uniroyal). 1.18. Ascorbic acid (vitamin C). 1.19. Amine antioxidants. For example N, N'-di-isopropyl-p-phenylenediamine, N, N '-di-sec-butyl-p-phenylenediamine, N, N'-bis (1,4-dimethylpentyl) -p-phenylenediamine, N, N '-bis (l-ethyl-3-methylpentyl) -p-phenylenediamine, N, N'-bis (1-methylheptyl) -p-phenylenediamine, N, N' -dicyclohexyl-p-phenylenediamine, N, N '- diphenyl-p-phenylenediamine, N, N'-bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N '-phenyl-p-phenylenediamine, N- (1,3-dimethylbutyl) -N'-phenyl- p-phenylenediamine, N- (1-methylheptyl) -N '-phenyl-p-phenylenediamine, N-cyclohexyl-N' -phenyl-p-phenylenediamine, 4-
(p-toluenesulfamoyl) diphenylamine, N, N '-dimethyl-N, N' -di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N- ( 4-tert-octylphenyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, for example p, p '-di-tert-octyldiphenylamine, 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4 -dodecanoylamino-phenol, 4-octadecanoylaminophenol, bis (4-methoxyphenyl) amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4'-diaminodiphenylmethane, 4,4'-diaminodiphenylmethane, N, N, N ', N'-tetramethyl-4,4'-diaminodiphenylmethane, 1,2-bis [(2-methylphenyl) amino] ethane, 1,2-bis (phenylamino) propane, (o-tolyl) biguanide, bis [4-] (1 ', 3' -dimethylbutyl) phenyl] amine, tert-octylated N-phenyl-1-naphthylamine, a mixture of tert-butyl / tert-octyl diphenylamines mono and di alkylated, a mixture of mono and dialkylated nonildiphenylamines, a mixture of mono- and dialkylated dodecyldiphenylamines, a mixture of diisopropyl / isohexyldiphenylamines m and dialkylated, a mixture of mono- and dialkylated tert-butyldiphenylamines, a mixture of tert-bitul mono- and dialkylated diphenylamines, 2,3-dihydro-3, 3-dimethyl-4H-l, 4-benzothiazine, phenothiazine, a mixture of tert-butyl / tert-octylphenothiazines mono- and dialkylated, a mixture of mono- and dialkylated tert-octyl-phenothiazines, N-allylphenothiazine, N, N, N ', N'-tetraphenyl-1,4-diaminobut-2-ene, N , N-bis (2, 2, 6, 6
tetramethyl-piperid-4-yl-hexamethylenediamine, bis (2, 2, 6, 6-tetramethylpiperid-4-yl) sebacate, 2,2,6,6-tetramethylpiperidin-4-one, 2,2,6,6- tetramethylpiperidin-4-ol.
UV absorbers and light stabilizers 2.1 2- (2'-hydroxyphenyl) benzotriazoles, for example 2- (2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (3 ', 5'-di-tert butyl-2 '-hydroxyphenyl) benzotriazole, 2- (5'-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-5' - (1,1,3,3-tetramethylbutyl) phenyl) benzotriazole, 2- (3 ', 5'-di-tert-butyl-2'-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3' -tert-butyl-2'-hydroxy-5'-methylphenyl) - 5-chloro-benzotriazole, 2- (3'-sec-butyl-5 '-tert-butyl-2'-hydroxyphenyl) benzotriazole, 2- (2'-hydroxy-4'-octiloxifenil) benzotriazole, 2- (3' , 5'-di-tert-amyl-2 '-hydroxyphenyl) benzotriazole, 2- (3'-5'-bis- (a, a-dimethylbenzyl) -2'-hydroxyphenyl) benzotriazole, 2- (3'-ester) -butyl-2 '-hydroxy-5' - (2-octyloxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-5 '- [2- (2-ethylhexyloxy) -carbonylethyl] - 2 '-hydroxyphenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5' - (2-methoxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3 '-tert-butyl-2'-hydroxy-5' - (2-methoxycarbonylethyl) phenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-octyloxycarbonylethyl) phenyl) benzotriazole, 2- (3 '-
tert-butyl-5 '- [2- (2-ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl) benzotriazole, 2- (3'-dodecyl-2'-hydroxy-5'-methylphenyl) benzotriazole, and 2- (3 '-tert-butyl-2'-hydroxy-5'- (2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2'-methylene-bis [4- (1, 1,3, 3-tetramethylbutyl) -6-benzotriazol-2- ilfenol], the product of the transesterification of 2- [3'-tert-butyl-5 '~ (2-methoxycarbonylethyl) -2'-hydroxyphenyl] -2H-benzotriazole with polyethylene glycol 300; [R-CH2CH2-COO-CH2CH2] 2, wherein R = 3'-tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl, 2- [2'-hydroxy-3 '- (a, a-dimethylbenzyl) -5' - (1, 1, 3, 3-tetramethylbutyl) -phenyl] benzotriazole; 2- [2'-hydroxy-3 '- (1,1,3,3-tetramethylbutyl) -5' - (aa-dimethylbenzyl) -phenyl) ] benzotriazole 2.2. 2-Hydroxybenzophenones, for example 'the derivatives 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4, 2', 4 '-trihydroxy and '-hydroxy-4,4'-dimethoxy 2.3 Esters of unsubstituted and substituted benzoic acids, c Such as 4-tert-butylphenylsalicylate, phenylsalicylate, octylphenylsalicylate, dibenzoylresorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoylresorcinol, 3,5-di-tert-buty-4-hydroxybenzoate 2,4-di-tert-butylphenyl, 3,5 hexadecyl-di-tert-butyl-4-hydroxybenzoate, octadecyl 3, 5-di-tert-butyl-4-hydroxybenzoate, 3,5-di-tert-butyl-4-hydroxybenzoate 2-methyl-4,6-hydroxybenzoate -di-tert-butylphenyl.
2. 4, Acrylates, for example a-cyano-β, ethyl β-diphenylacrylate, α-cyano-β, isooctyl β-diphenylacrylate, methyl a-carbomethoxycinnamate, methyl a-cyano-β-methyl-p-methoxycinnamate, butyl a-cyano-β-methyl-p-methoxycinnamate, methyl α-carbomethoxy-p-methoxycinnamate and N- (β-carbomethoxy-β-cyanovinyl) 2-methylindoline. 2.5. Nickel compounds, for example 2, 2'-thio-bis [4- (1, 1, 3, 3-tetramethylbutyl) phenol] nickel complexes, such as the 1: 1 or 1: 2 complex, with or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel dibuldithiocarbamate, nickel salts of monoalkyl esters, for example the methyl or ethyl ester of 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid, nickel complexes of ketoxy ace, for example of 2-hydroxy-4-methylphenyl undecylketoxime, l-phenyl-4-lauroyl-5-hydroxypyrazole nickel complexes, with or without additional ligands. 2.6. Spherically hindered amines, for example bis (2,2,6,6-tetramethyl-piperidyl) sebasate, bis (2,2,6 / 6-tetramethyl-piperidyl) succinate, bis (1, 2, 2, 6, 6 pentamethyl-piperidyl) sebasate, bis (1,2,3,6-pentamethyl-piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensates of N, N'-bis (2,2,6,6-tetramethyl-4-piperidylhexamethylenediamine and 4-tert.
octylamino-2,6-dichloro-l, 3, 5-triazine, tris (2, 2, 6, 6-tetramethyl-4-piperidyl) nitriloacetate, tetrakis (2, 2, 6,6-tetramethyl-4-piperidyl) -1,2,3, 4-butane-tetracarboxylate, 1,1 '- (1,2-ethanediyl) -bis (3, 3, 3, 5, 5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6 -tetramethylpiperidine, 4-stearyloxy-2, 2,6,6,6-tetramethylpiperidine, bis (1,2,2,6,6-pentamethylpiperidyl) -2-n-butyl-2- (2-hydroxy-3,5-di) -tert-butylbenzyl) malonate, 3-n-octyl-7, 7, 9, 9-tetramethyl-l, 3,8-triazaspiro [4.5] decan-2,4-dione, bis (l-octyloxy-2, 2 , 6,6-tetramethylpiperidyl) sebasate, bis (l-octyloxy-2,2,6,6-tetramethylpiperidyl) succinate, linear or cyclic condensates of N, N'-bis- (2,2,6,6-tetramethyl- 4-piperidyl) hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, the condensate of 2-chloro-4,6-bis (4-n-butylamino-2,2,6,6 -tetramethylpiperidyl) -1, 3, 5-triazine and 1,2-bis (3-aminopropylamino) ethane, the condensate of 2-chloro-4,6-di- (4-n-butylamino-l, 2,2, 6, 6-pentamethylpiperidyl) -1,3,5-tria zina and 1,2-bis- (3-aminopropylamino) ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-l, 3,8-triazaspiro [4.5] decan-2, 4- - dione, 3-dodecyl-l- (2,2,6,6-tetramethyl-4-piperidyl) pyrrolidin-2, 5-dione, 3-dodecyl-1- (2, 2, 6, 6-pentamethyl-4-) piperidyl) pyrrolidin-2, 5-dione, a mixture of 4-hexadecyloxy- and 4-stearyloxy-2,2,6,6-tetramethylpiperidine, a condensation product of N, N'-bis (2, 2, 6, 6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, a condensation product of 1,2-
bis (3-aminopropylamino) ethane and 2,4,6-trichloro-1,3,5-triazine as well as 4-butylamino-2, 2,6,6-tetramethylpiperidine (CAS Reg. No. [136504-96- 6]); N- (2,2,6,6-tetramethyl-4-piperidyl) -n-dodecyl succinimide, N- (1,2,2,6,6-pentamethyl-4-piperidyl) -n-dodecyl succinimide, 2-undecyl- 7, 7, 9, 9-tetramethyl-l-oxa-3,8-diaza-4-oxo-spiro [4, 5] decane, a product of the reaction of 7,7,9,9-tetramethyl-2- cycloundecyl-l-oxa-3, 8-diaza-4-oxospiro [4, 5] decane and epichlorohydrin, 1, 1-bis (1, 2, 2, 6, 6-pentamethyl-4-piperidyloxycarbonyl) -2- ( 4-methoxyphenyl) ethene, N, N'-bis-formyl-N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine, diester of 4-methoxy-methylene-malonic acid with 1 , 2, 2, 6, 6-pentamethyl-4-hydroxypiperidine, poly [methylpropyl-3-oxy-4- (2, 2, 6, 6-tetramethyl-4-piperidyl)] siloxane, reaction product of anhydride copolymer α-olefin of maleic acid with 2, 2, 6,6-tetramethyl-4-aminopiperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine. 2.7. Oxamides, for example, 4,4'-dioctyloxyoxanilide, 2,2 '-dioctyloxy-5, 5'-di-tert-butoxyanilide, 2,2'-didodecyloxy-5, 5'-di-tert-butoxyanilide, 2- ethoxy-2'-ethoxyanilide, N, N'-bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxyanilide and its mixture with 2-ethoxy-2'-ethyl-5,4 '-di-tert-butoxyanilide, mixtures of ortho-
and para-methoxy-disubstituted and mixtures of o- and p-ethoxy-disubstituted oxanilides. _ __ 2.8. 2- (2-Hydroxyphenyl) -1,3,5-triazines, for example 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine 2- (2-hydroxy) 4-octyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1 , 3, 5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1, 3, 5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) ) -4,6-bis (4-methylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3, 5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-butyloxy-propoxy) phenyl] -4,6-bis (2,4-dimethyl-1,3,5-triazine, 2- [ 2-hydroxy-4- (2-hydroxy-3-octyloxy-propyloxy) phenyl] -4,6-bis (2,4-dimethyl) -1,3,5-triazine, 2- [dodecyloxy / tridecyloxy-2- hydroxypropoyl) -2-hydroxy-phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,4-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-dodecyloxy-propoxy ) phenyl] -4,6-bis [2,4-dimethylphenyl-1,3,5-triazine, 2- (2-hydroxy-4-hexyloxy) phenyl-4,6-diphenyl-1,3,5-triazine 2- (2-hydroxy-4-met) oxyphenyl) -4,6-diphenyl-1,3,5-triazine, 2,4,6-tris [2-hydroxy-4- (3-botoxi-2-hydroxy-proppoxy) phenyl] -1,3,5 . triazine, 2- (2-hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1,3,5-triazine, 2-. { 2-hydroxy-4- [3-2 (2-ethylhexyl-1-oxy) -2-hydroxypropyloxy] phenyl} -4, 6.bis (2,4-dimethylphenyl) -1, 3, 5-triazine.
3. Metal deactivators, for example N, N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-tert-butyl-4) -hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-l, 2,4-triazole, bis (benzylidene) oxalyldihydrazide, oxanilide, isophthaloidihydrazide, sebazoylbisphenylhydrazide, N, N'-di-acetyl-dipoyldihydrazide, N, N'-bis (salicyloyl) oxalyldihydrazide, N , N'-bis (salicyloyl) thiopropionyl-dihydrazide. 4. Phosphites and phosphonites, for example triphenyl phosphite, diphenylalkyl phosphites, phenyldialkyl phosphites, tri (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distetea-rilpentaerythritol diphosphite, tris (2, 4-di) phosphite -tert-butylphenyl), diisodecylpentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) -pentaerythritol diphosphite, diisodecycloxypentaerythritol diphosphite diphosphite of bis (2,4-di-tert-butyl-6-methylphenyl) pentaerythritol, diphosphite of bis (2,4,6-tris (tert-butylphenyl) pentaerythritol, tripteraphite of triesterailsorbitol, tetrakis diphosphonite (2, 4) -diter-butylphenyl) -4,4 '-biphenylene, 6-isooctyloxy-2,4,8,10-tetra-tert-butyl-12H-dibenz [d, g] -1, 3, 2-dioxaphosphocin, 6- fluoro-2,4,8,10-tetra-tert-butyl-12-methyl-dibenz [d, g] -1,3,2-dioxaphosphocin, bis (2,4-di-tert-butyl-6-methylphenyl) Methylphosphi-
to, bis (2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite, 2,2 ', 2"-nitrile [triethyltris (3, 3', 5, 5 '-tetra-tert-butyl-1, 1 '-biphenyl-2,2'-diyl) phosphite], 2-ethylhexyl (3, 3', 5, 5 '-tetra-tert-butyl-1, 1-biphenyl-2,2'-diyl) phosphite 5. Hydroxylamines, for example, N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioctylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydroxylamine, N, N-dihexadecylhydroxylamine, N, -dioctadecylhydroxylamine, N hexadecyl-N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N-octadecyl-hydroxylamine, N, N-dialkylhydroxylamine derived from hydrogenated tallow amine 6. Nitrones, for example, N-benzyl-alpha-phenyl-nitron, N-ethyl-alpha-methyl-nitron, N-octyl-alpha-heptyl-nitron, N-lauryl-alpha-undecyl-nitron, N-tetradecyl-alpha -tridyl-nitron, N-hexadecyl-alpha-pentadecyl-nitron, N-octadecyl-alpha-heptadecyl-nitron, N-hexadecyl-alpha-heptadecyl-nitron, N-ocatadecyl-alpha-pentadecyl-nitron, N-heptadecyl-alpha-heptadecyl-nitron, N-octadecyl-alpha-hexadecyl l-nitron, nitron derivative of N, N-di alkylhydroxylamine derived from hydrogenated tallow amine. 7. Thiosynthetics, for example, lauryl thiodipropionate or distearyl thiodipropionate. 8. Peroxide purifiers, for example esters of β-thiodipropionic acid, for example esters of
lauryl, stearyl, myristyl or tridecyl esters, mercaptobenzimidazole or the zinc salt of 2-mercaptobenzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, pentaerythritol tetrakis (β-dodecylmercapto) propionate. 9. Polyamide stabilizers, for example, copper salts in combination with iodides and / or phosphorus compounds and salts of divalent manganese. 10. Basic co-stabilizers, for example, melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids eg stearate of calcium, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinolate and potassium palmitate, antimony pyrocatechol or tin pyrocatechollate. 11. Foraging agents for cores, for example, inorganic substances such as talc, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of, preferably, alkaline earth metals; organic compounds such as mono- or polycarboxylic acids and their salts, for example, 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate;
polymeric compounds such as ionic copolymers (ionomers). 12. Fillers and reordering agents, for example, calcium carbonate, silicates, glass fibers, glass bulbs, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, flour wood and flours or fibers of other natural products, synthetic fibers. 13. Other additives, for example, plasticizers, lubricants, emulsifiers, pigments, rheolytic additives, catlizasores, flow control agents, optical brighteners, fireproofing agents, antistatic agents and blowing agents. 14. Benzofuranones and indolinones, for example those described in US 4,325,863; US
4,338,244; US 5,175,312; U.S. 5,216,052; U.S. 5,252,643; DE-A-4316611; DE-A-4316622; DE-A-4316876; EP-A-0589839 or EP-A-0591102 or 3- [4- (2-acetoxyethoxy) phenyl] -5,7-di-tert-butylbenzofuran-2-one, 5,7-di-tert-butyl-3 - [4- (2-stearoyloxyethoxy) phenyl] benzofuran-2-one, 3,3 '-bis [5,7-di-tert-butyl-3- (4- [2-hydroxyethoxy] phenyl) benzofuran-2- ona], 5, 7-di-tert-butyl-3- (4-ethoxyphenyl) benzofuran-2-one, 3- (4-acetoxy-3,5-dimethylphenyl) -5,7-di-tert-butyl- benzofuran-2-one, 3- (3,5-dimethyl-4-pivaloyloxyphenyl) -5,7-di-tert-butyl-benzofuran-2-one, 3, (3,4-dimethylphenyl) -5, 7- di-tert-butyl-benzofuran-2-
ona, 3- (2,3-di-methylphenyl) -5,7-di-tert-butyl-benzofuran-2-one. The weight ratio of the product or mixture according to this invention to conventional additives can be, for example, 1: 0.5 to 1: 5. The products or mixtures of this invention can also be used as stabilizers, especially as stabilizers against light, for almost all materials known in the art of photographic reproduction and other reproduction techniques such as, for example, what is described in Research Disclosure 1990 , 31429 (pages 474 to 480). The invention is illustrated in more detail by means of the following examples. All percentages are by weight, unless otherwise indicated. In the structural formulas of the following examples, n 'indicates that there are repetitive units in the molecules and the products obtained are not uniform. The intermediary described in Example IA is characterized by the number average molecular weight Mr. and the polydispersity Mw / Mn. CPG (gel permeation chromatography) is used as an analytical procedure to separate molecules by their difference in size and obtain weights.
average molecular weight (Mw, Mn) or information on the molecular weight distribution of polymers. The technique is well known and described, for example, in 'Modern Size - Exclusion Liquid Chromatography' by W.W.Yan et al., Edited by J. Wiley & amp;; Sons, N.Y., USA, 1979, pages 4-8, 249-283 and 315-340. The CPG analysis shown in the following examples is carried out with an HPLC instrument, type ®TSP AS-1000, equipped with a UV / VIS ®UV 1000 detector having a wavelength of 250 nm. A mixed gel GPC-SS-250 x 7.7 mm x 3/8"®Valco-Microgel-3 is used as the column The eluent (flow: lml / min) is tetrahydrofuran-®Uvasol for spectroscopy (®Merck-l .00016 ) + 0.02 mol / L diethanolamine (®Fluka 31590) 0.5 g of the sample to be tested was dissolved in 100 ml of the eluent, the injection volume is 20 μl and the chromatogram period is 15 min.
Example 1:
A) Preparation of the product of the formula
To a solution of 221.2 g (1.2 moles) of cyanide chloride in 1286 g of xylene, under stirring and nitrogen atmosphere, 254.8 g were added for more than 2 hours.
(1.2 moles) of N- (2, 2, 6, 6-tetramethyl-4-piperidyl) -n-butylamine, maintaining the temperature of approximately
° C during the addition. A thick but sufficiently stirrable suspension was obtained, which was maintained at the indicated temperature for a further 15 minutes. Subsequently, a mixture of 176.3 g of an aqueous solution of 30% NaOH (% w / v) was added and 200 g of water were added for 2 hours maintaining the temperature at about 30 ° C. A thin suspension was obtained, which was maintained for 2.5 hours at the indicated temperature. Then, the aqueous basic solution was separated and the reaction mixture was added at 53 ° C at 57 ° C for 2 hours, under stirring, to a mixture of 300 g of water, 355.2
g (0.9 moles) of N, N'-bis (2, 2, 6, 6-tetramethyl-4-piperidyl) -1,6-hexandiamine and 268.3g of an aqueous solution of 30% NaOH (% w / v) . 30 g of xylene was added and the reaction mixture was maintained above the aforementioned temperature for 1 hour. Thereafter, the reaction mixture was heated at 80 ° C for 1 hour and maintained at that temperature for an additional hour. 380 g of xylene are distilled under vacuum (68-82 ° C / 200-120 mbar). Then, 170 g of xylene and 200 g of water were added and, after closing the reactor and causing an inert environment with nitrogen, the temperature was raised to 160 ° C for more than 2 hours. The mixture was maintained at 160 ° C for 6 hours under 5.4 bars of pressure. After cooling to 60 ° C, 89.Og (0.69 mole) of di-n-butylamine and 86.4 g of an aqueous solution of 30% NaOH (% w / v) were added. After closing the reactor again, the mixture was heated to 160 ° C for more than 1 hour and maintained at 160 ° C for more than 4 hours under a pressure of 5 bars. After cooling to 60 ° C, 130 g of xylene and 150 g of water were added. The mixture is heated to 92 ° C under stirring. Then, the aqueous solution was separated. The organic phase was washed twice with 400 g of water, filtered at 80 ° C and concentrated under vacuum (125-230 ° C / 350-1 mbar). During cooling, the product of
fusion provided a solid with a melting point of 133 to 137 ° C.
Mn (per CPG = gel permeation chromatography) = 2060 g / mol Mw / Mn = 1.55
The CPG analysis showed a chromatogram like the one in Figure 1.
Proportion of the main components alone in the product obtained:
Compound with n '' = l: compound with n '= 2 1.07: 1 Compound with n' = l: compound with n '= 3 0.81: 1 Compound with n' = l: compound with n '= 4 0.99: 1
The total amount (sum) of the four solid main components ((n '= l), (n' = 2), (n '= 3), (n' = 4)) in the polydispersed product obtained is 60.4 mol% . B) Preparation of the product of the formula
A 100 ml, four-necked flask was mechanically shaken with 4 g (0.016 moles) of the product in accordance with A), 0.04 g of Mo03 and 32 ml of cyclohexane. The mixture was heated to reflux. Within 30 minutes, 8.24 g (0.064 mole) of 70% t-butylhydroperoxide was added. The water was collected by azeotropic distillation and the reflux was continued for one hour. The reaction mixture was transferred to a magnetically stirred pressure glass bottle and heated at 130 ° C for 5 hours. The reaction mixture was cooled to 70 ° C and the M0O3 was filtered. The filtrate was washed with a solution of 2 g of Na 2 SO 3 in 10 ml of H 2 O for one hour at 60 ° C. The phases were separated, the organic phase was dried over MgSO4 and the total volume was reduced to about 10 ml. The
solution was flooded in 50 ml of methanol at 5 ° C. The precipitate was filtered and dried.
Yield: 5.57 g.
Fusion range: 129-152 ° C.
XH NMR: 0.85-2.4 ppm (complex mixture); 3.2-3.45 ppm (s, width, NCH2); 3.55-3.70 ppm (s, width, NOCH); 4.9-5.4 ppm (s, width, NCH). The proportion of protons at 3.2 ppm, 3.55 ppm and 4.9 ppm is 2: 1: 1.
13 C NMR: 82 ppm (NOC); 165 ppm (triazine C)
Example 2: Preparation of the product of the formula
Into a mechanically stirred 4-neck round bottom flask of 100 ml, 4 g (0.016 mole) of the product were loaded according to example IA), 0.04 g Mo03 and 32 ml n-octane. The mixture was heated to reflux and within 30 minutes 10.3 g (0.08 mole) of 70% t-butylhydroperoxide were added. The water was removed by azeotropic distillation and the reflux was continued for 6 hours. The Mo03 was filtered and the filtrate was washed with a solution of 2 g of Na2S03 in 10 ml of H20 for 30 minutes at 60 ° C. The phases were separated and the organic phase was washed with water and 10 ml of saturated NaCl solution, dried over MgSO4 and then evaporated to a volume of about 10 ml. The solution was flooded in 50 ml of methanol at 5 ° C. The precipitate, a soft glass, was dried under vacuum at 55 ° C, crushed with a mortar and then dried again under vacuum.
Yield: 5.53 g.
Melting range: 96-118 ° C.
XH NMR: 0.85-2.4 ppm (complex mixture); 3.15-3.55 ppm (s, width, NCH2); 3.65-3.9 ppm (s, width, NOCH); 4.9-5.4 ppm (s, width, NCH). The proportion of protons at 3.15 ppm, 3.65 ppm and 4.9 ppm is 2: 1: 1.
13 C NMR: 78-84 ppm (NOC, isomer mixture in C 8 H 7); 165 ppm (triazine C).
Example I: Stabilization action against light in polypropylene fibers.
2. 5 g of the stabilizer shown in Table 1, 1 g of tris (2,4-di-t-butylphenyl) phosphite, 1 g of 3,5-di-t-butyl-4-hydroxybenzyl monoethyl calcium phosphonate, g of calcium stearate and 2.5 g of titanium dioxide were mixed in a slow mixer with 1000 g of polypropylene powder with a melt index = 12 g / 10 min (measured at 230 ° C and 2.16 kg). The mixtures were extruded at 200-230 ° C to obtain polymer granules which subsequently
They were converted into fibers using a pilot type apparatus (®Leonard-Sumirago (VA), Italy) and operating under the following conditions:
Extruder temperature: 230-245 ° C. Head temperature: 255-260 ° C. Stretching ratio: 1: 3.5. Linear density: 11 dtex per filament,
The fibers prepared in this manner were exposed, after assembly in white cardboard, in a WR Wheather-O-Metere (ASTM D2565-85) with a black board temperature of 63 ° C. For samples taken after several hours of exposure to light, the residual tenacity was measured using a constant-velocity tensometer, and then the exposure time in hours needed for half the initial tenacity (T50) was calculated.
TABLE 1
Stabilizer T50 in hours Composite of the example ÍA 2740
The compound listed in Table 1 shows a good light stabilizing activity in polypropylene fibers.
Example II: Stabilizing action against light in polypropylene tapes. In a turbo mixer, 1 g of each of the compounds listed in Table 2, 1 g of tris [2,4-di-tert-butylphenyl] phosphite, 0.5 g of tetrakis [3- (3, 5-di- tert-butyl-4-hydroxyphenyl) propionate] of pentaerythritol and 1 g of calcium stearate with 1000 g of polypropylene powder with a melt index of 2.1 (measured at 230 ° C and 2.16 Kg). The mixtures were extruded at 200-220 ° C to give polymer granules which were subsequently converted into stretched tapes 50 μm thick and 2.5 mm wide, using a type of semi-industrial device (®Leonard-Sumirago (VA) - Italy ) and working under the following conditions:
Extruder temperature: 210-230 ° C Head temperature: 240-260 ° C Stretch ratio: 1: 6
The tapes prepared in this way were mounted on a white card and exposed in a Weather-O-Meter 65 WR (ASTM D 2565-85) with a black board temperature of 63 ° C. The residual tenacity was measured, by means of a constant speed tensometer, in a sample taken after several exposure to light, from which the exposure time (in hours) required to divide the tenacity was measured. initial (T50).
TABLE 2
Stabilizer Tso in hours
Composite of the example ÍA > 1990
The compound listed in Table 2 shows a good activity in the stabilization against light in polypropylene tapes. Example III: Interaction of the pigment in polypropylene plates.
. 625 g of the stabilizer shown in Table 3, 13,500 g of Pigmento Azul 15 ^ Flush "(mixture of 50% in polyethylene) and 25,875 g of polypropylene powder (having a melting index of approximately 14 measured at 230 ° C and
2. 16 Kg) were added to fill an internal ®Haake mixer at room temperature (®Haake Buchler Rheochord System 40 using a 60 c.c. 3 piece mixer with eccentric blades). The eccentric blades were turned at 5 RPM (revolutions per minute). A ram closed the bowl under a weight of 5 kg. The temperature was increased to 180 ° C and held at 180 ° C. The total time was 30 minutes. The mixture was removed while it was at 180 ° C after 30 minutes and cooled to room temperature. The mixture thus obtained called the "concentrate" was again used: 0.900 g of this concentrate, 3,600 g of NFlush titanium dioxide (50% polyethylene mixture), and 40,500 g of polypropylene powder (with a melt index). of approximately 14 measured at 230 ° C and 2.16 Kg) were added to a mixing bowl ®HAAKE at 160 ° C. The eccentric blades were turned at 20 RPM. A ram closed the bowl under a weight of 5 kg. The temperature was increased to 170 ° C and the RPM was increased to 125. The total time was 30 minutes. The molten mixture was removed at 170 ° C, transferred to a hand tool at room temperature and transformed into a 1 mm x 25 mm round plate.
diameter. The mixture obtained was called 'decrease' and the plate 'decrease plate.' The color difference, delta E (CIÉ color difference equation), of the sample reduction plate containing the stabilizer indicated in Table 3 against the control decrease plate without the stabilizer was measured. The measurement was made using an Applied Color Systems spectrometer model CS-5 (USAAA). The measurement parameters used were 400 - 700 nm - scanning, small viewing area, reflectance, D65 illumination, 10 degree observer. The above process conditions were designed to simulate the manufacture of the concentrates
(standard lots) of pigments and stabilizers and the subsequent decrease (dilution) in the finished plastic articles. A high delta E indicates agglomeration of the pigment and poor dispersion. A delta E of 0.5 or less can not be distinguished by the eye. TABLE 3
Delta E Stabilizer Composed of Example 1A 0.8
Example IV:
Pigmented thermoplastic olefin pellets (OTP) were prepared by blending a polyolefin blend (polypropylene containing an ethylene-propylene copolymer; ® Polytrope TPP 518-01 from A. A. Schulman, Inc.; Akron, Ohio, USA) with The additives listed below on a single 1"® Super Screw / MPM screw extruder with a general purpose screw (24: 1 L / D) at 200 ° C, cooling in a water bath and pelletising. molding, the additives were dried and mixed in a drum dryer.
Additives: 0.25% * of ®Red 3B (Pigment Red 177, colorimetric index 65300), 0.05% * 'of tetrakis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate] of pentaerythritol, 0.05 % * 'of tris [2, 4-di-tert-butylphenyl] phosphite, 0.2% *' of 2- (2'-hydroxy-3 ', 5'-di-tert-a-ylphenyl) benzotriazole, 0.2% *' of bis (l-octyloxy-2, 2,6,6-tetramethyl-4-piperidyl) sebacate, 0.1% * 'of calcium stearate, about 10% * of talc and 0.2% * of the compound of Example IB or 2.
* 'percent by weight based on the mixture of polyolefins
The resulting pellets were molded into 2"x 2" and 1,524 mm thick platelets at approximately 190 ° C on an ®BOY 30M injection molding machine. The test plates were mounted in metal frames and exposed in a Weather-O-Meter ® Atlas Ci65 Xenon Arc at a temperature of 70 ° C black board, 0.55 W / m2 at 340 nanometers and 50% relative humidity with intermittent light / dark cycles and water spray (test procedure of the ®Sociedad de Ingenieros Automotrices - SAE J 1960 - exterior automotive conditions). The specimens were tested at intervals of approximately 625 kilojoules by performing color measurements in a spectrophotometer of Applied Color Systems in reflectance mode in accordance with ASTM D 2244-79. Brightness measurements were made on a ®BYK-GARDNER mist / gloss meter at 60 ° in accordance with ASTM D 523. The stabilized samples showed good gloss retention and good resistance to color change upon exposure to UV.
Claims (31)
1. An affordable product 1) by reacting a product of the formula a with a compound of the formula (ß) in a molar ratio of 1.2: 1 to 1.4: 1; 2) by reacting the end groups of the formula (?) - Ax. _. pN - cl w which are present in the reaction product 1) with a compound of the formula (d)
A-H (d) in a molar ratio of 2: 1.7 to 2: 3; reactions 1) and 2) being carried out in an organic solvent in the presence of an inorganic base; and 3) transferring the groups of the formula (G-I) which are present in the reaction product 2) to the groups of the formula (G-II); such transfer is carried out by reacting the reaction product 2) with a hydroperoxide in a hydrocarbon solvent in the presence of a peroxide decomposing catalyst; Ri is a hydrocarbyl radical or -0-R? it is oxyl; R2 is alkylene of 2 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, cycloalkylene of 5 to 7 carbon atoms, cycloalkarylene of 5 to 7 carbon atoms (alkylene of 1 to 4 carbon atoms), alkylene of 1 to 4 carbon atoms - (cycloalkylene of 5 to 7 carbon atoms), phenylendi ( alkylene of 1 to 4 carbon atoms) or alkylene of 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl, -0- or > N-X? with Xi being acyl of 1 to 12 carbon atoms or (alkoxy of 1 to 12 carbon atoms) carbonyl or having one of the definitions. of R4 given below; or R2 is a group of the formula (I-a), (I-b) or (I-c); with m being 2 or 3,
X 2 being alkyl of 1 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3, alkyls of 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; and the X3 radicals being independently from each other alkylene of 2 to 12 carbon atoms; A is -0R3, -N (R4) (R5) or a group of the formula
(ID;
R3, R and R5, which are identical or different, are alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; alkenyl of 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy of 1 to 8 carbon atoms, di (C1-C4 alkyl) amino or a group of the formula (III); with Y being -0 -, -CH2-, -CH2CH2 - or > N-CH3; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III); X is -0 - or > N-R6; Rβ is alkyl of 1 to 18 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms' which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl, a group of the formula (GI), or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy of 1 to 8 carbon atoms, di (alkyl of 1 to 4 carbon atoms) amino or a group of the formula (III); R has one of the meanings given for R6; Y
B has one of the meanings given for A. 2. A product according to claim 1, characterized in that R2 is alkylene of 2 to 12 carbon atoms, cycloalkylene of 5 to 7 carbon atoms, cycloalkylene of 5 to 7 carbon atoms. carbon (alkylene of 1 to 4 carbon atoms), alkylene of 1 to 4 carbon atoms (cycloalkylene of 5 to 7 carbon atoms), phenylendi (alkylene of 1 to 4 carbon atoms) or alkylene of 4 to 12 carbon atoms carbon interrupted by -O - or >; N-X? with Xi being acyl of 1 to 12 carbon atoms or (alkoxy of 1 to 12 carbon atoms) carbonyl or having one of the definitions of R 4; or R2 being a group of the formula (I-b); R3, R and R5, which are identical or different, are alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III);
R6 is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3, alkyls of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; or a group of the formula (G-I) 3. A product according to claim 1, characterized in that R is a group of the formula (G-I). 4. A product according to claim 1, characterized in that R2 is alkylene of 2 to 10 carbon atoms, cyclohexylene, cyclohexylendi (alkylene of 1 to 4 carbon atoms), alkylene of 1 to 4 carbon atoms-dicyclohexylene or phenylene (alkylene of 1 to 4 carbon atoms); 3/4 and R5? which are identical or different, are alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 7 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; benzyl which is unsubstituted or substituted on phenyl by alkyl of 1 to 4 carbon atoms carbon; or -N (R4) (R5) is additionally a group of the formula (III); and R6 is alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 to 7 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; benzyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; or a group of the formula (G-I). 5. A product according to claim 1, characterized in that R2 is alkylene of 2 to 8 carbon atoms; R3, R4 and s, which are identical or different, are alkyl of 1 to 8 carbon atoms, cyclohexyl which is unsubstituted or substituted by methyl; phenyl that is unsubstituted or substituted by methyl; benzyl or -N (R4) (R) is further 4-morpholinyl; and R6 is alkyl of 1 to 8 carbon atoms, cyclohexyl which is unsubstituted or substituted by methyl; benzyl or a group of the formula (G-I). 6. A product according to claim 1, characterized in that Ri is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 3) is, depending on Ri, octane or cyclohexane; R2 is alkylene of 2 to 6 carbon atoms;
A is -N (R4) (R5) or a group of the formula (II); R4 and Rs, which are identical or different, are alkyl of 1 to 8 carbon atoms; or -N (R) (R5) is further 4-morpholinyl; X is > NR6; R6 is alkyl of 1 to 8 carbon atoms; and B has one of the meanings given for A. 7. A product according to claim 1, characterized in that Ri is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 3) is, depending on Ri, octane or cyclohexane; R2 is alkylene of 2 to 6 carbon atoms; R is a group of the formula (G-I); A is -N (R4) (R5); R and 5? which are identical or different, are alkyl of 1 to 8 carbon atoms; B is a group of the formula (II); X is > NR6; R6 is alkyl of 1 to 8 carbon atoms. 8. A product according to claim 1, characterized in that the organic solvent used in reactions 1) and 2) is in particular an aromatic hydrocarbon or an aliphatic ketone and the base
Inorganic is sodium hydroxide, potassium hydroxide, sodium carbonate or potassium carbonate. 9. A product according to claim 1, characterized in that during the course of the reaction 1) the temperature rises from 10 ° to 85 ° C at the beginning and up to 110 ° to 220 ° C at the end.
10. A product according to claim 1, characterized in that the reaction 2) is carried out at a temperature of 110 ° to 180 ° C.
11. A product according to claim 1, characterized in that the reactions 1) and 2) are carried out under pressure.
12. A product according to claim 1, characterized in that Ri is alkyl of 5 to 18 carbon atoms, alkenyl of 5 to 18 carbon atoms, alkynyl of 5 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms unsubstituted or substituted by alkyl of 1 to 4 carbon atoms; cycloalkenyl of 5 to 12 carbon atoms unsubstituted or substituted by alkyl of 1 to 4 carbon atoms; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms or phenylalkyl of 7 to 9 carbon atoms unsubstituted or substituted on the phenyl by alkyl of 1 to 4 carbon atoms; Y the hydrocarbon solvent in reaction 3) is, depending on Ri, alkane of 5 to 18 carbon atoms, alkene of 5 to 18 carbon atoms, alkyne of 5 to 18 carbon atoms, cycloalkane of 5 to 12 unsubstituted carbon atoms or substituted by alkyl of 1 to 4 carbon atoms; cycloalkene of 5 to 12 carbon atoms unsubstituted or substituted by alkyl of 1 to 4 carbon atoms; a bicyclic or tricyclic hydrocarbon having 6 to 10 carbon atoms or phenylalkan of 7 to 9 carbon atoms unsubstituted or substituted on the phenyl by alkyl of 1 to 4 carbon atoms.
13. A product according to claim 1, characterized in that Ri is heptyl, octyl, cyclohexyl, methylcyclohexyl, cyclooctyl, cyclohexenyl, α-methylbenzyl or 1,2,3,4-tetrahydronaphtenyl, and the hydrocarbon solvent in the reaction 3. ) is, depending on Ri, heptane, octane, cyclohexane, methylcyclohexane, cyclooctane, cyclohexene, ethylbenzene or tetralin.
14. A product according to claim 1, characterized in that Ri is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 3) is, depending on Ri, octane or cyclohexane.
15. A product according to claim 1, characterized in that the radical -O-Ri is oxyl and the hydrocarbon solvent in reaction 3) is an inert organic solvent.
16. A product according to claim 1, characterized in that the peroxide decomposing catalyst is a metallic carbonyl, metal oxide, metallic acetylacetonate or a metal alkoxide wherein the metal is selected from groups IVb, Vb, VIb, VIIb and VIII of the periodic table.
17. A product according to claim 1, characterized in that the hydroperoxide is t-butyl hydroperoxide and the catalyst that decomposes peroxide is Mo03.
18. A product according to claim 1, characterized in that per mole of the group of the formula (G-I) which is present in the reaction product 2) apply from 2 to 8 moles of the hydroperoxide, 0.001 to 0.1 mole of the peroxide decomposing catalyst and from 5 to 30 moles of the hydrocarbon solvent.
19. An affordable product by hydrogenating a product according to claim 1, characterized in that -ORi in the formula (G-II) is oxyl to obtain a corresponding product with groups of the formula (G-III).
20. A mixture containing a monodisperse compound of the formula (P-I), a monodisperse compound of the formula (P-II), a monodisperse compound of the formula (P-III) and a monodisperse compound of the formula (P-IV), the compounds only differ in the number of repetitive units, the total amount of the compounds of the formulas (P-I), (P-II), (P-III) and (P-IV) being from 40 to 70 mol%, relative to the total mixture; Y Ri is hydrogen, a hydrocarbyl radical or -0-R? it is oxyl; R 2 is alkylene of 2 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, cycloalkylene of 5 to 7 carbon atoms, cycloalkarylene of 5 to 7 carbon atoms (alkylene of 1 to 4 carbon atoms), alkylene of 1 to 4 carbon atoms- (cycloalkylene of 5 to 7 carbon atoms), phenylendi (alkylene of 1 to 4 carbon atoms) or alkylene of 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl, -O- or > N-X? with Xi being acyl of 1 to 12 carbon atoms or (alkoxy of 1 to 12 carbon atoms) carbonyl or having one of the definitions of R given below; or R2 is a group of the formula (I-a), (I-b) or (I-c); -CH2-CH-CH2- (I-b) I or C = 0 I x. with m being 2 or 3, where X 2 is alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3, alkyls of 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxys of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; and the X3 radicals being independently from each other alkylene of 2 to 12 carbon atoms; A * is -0R3, -N (R4) (R5) or a group of the formula (G-IV); 3 / R4 and Rsf which are identical or different, are alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; alkenyl of 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxys of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl of 2 to 4 carbon atoms which is substituted in position 2, 3 or 4 by -OH, alkoxy of 1 to 8 carbon atoms, di (alkyl of 1 to 4 carbon atoms) amino or a group of the formula (III); where Y is -0 -, -CH2 -, -CH2CH2 - or > N-CH3; and R3 is further hydrogen or -N (R4) (R5) is further a group of the formula (III); X * is _0 - or > N-R6 *; R6 * is alkyl of 1 to 18 carbon atoms, alkenyl of 3 to 8 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by -1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl, a group of the formula (G-II), or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy of 1 to 8 carbon atoms, di (alkyl of 1 to 4 carbon atoms) amino or a group of the formula (III); R * has one of the meanings given for R6 *; And B * has one of the meanings given for A *.
21. A composition containing an organic material susceptible to degradation induced by light, heat or oxidation and a product according to claim 1.
22. A composition according to claim 21, characterized in that the organic material is a synthetic polymer.
23. A composition according to claim 21, characterized in that the organic material is polyethylene or polypropylene. 24. A method for stabilizing an organic material against light-induced degradation, heat or oxidation comprising incorporating into the organic material a product in accordance with claim 1. 25. A product available by 1) reacting a product of the formula ( to) with a compound of the formula (ß-1) in a molar ratio of 1.2: 1 to 1.4: 1; 2) by reacting the end groups of the formula (?) which are present in the reaction product 1) with a compound of the formula (d)
A-H (d) in a molar ratio of 2: 1.7 to 2: 3, reactions 1) and 2) are carried out in an organic solvent in the presence of an inorganic base; Z is hydrogen, alkyl of 1 to 8 carbon atoms, hydroxyalkyl of 2 to 8 carbon atoms, 0 ', -OH, hydrocarbyloxy of 1 to 18 carbon atoms, -CH2CN, alkenyl of 3 to 6 carbon atoms, alkynyl from 3 to 6 carbon atoms, phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; or acyl of 1 to 8 carbon atoms; R2 is alkylene of 2 to 12 carbon atoms, alkenylene of 4 to 12 carbon atoms, cycloalkylene of 5 to 7 carbon atoms, cycloalkylene of 5 to 7 carbon atoms di (alkylene of 1 to 4 - carbon atoms), alkylene of 1 to 4 carbon atoms (cycloalkylene of 5 to 7 carbon atoms), phenylendi (alkylene of 1 to 4 carbon atoms) or alkylene of 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl, -0- or > N-X? with Xt being acyl of 1 to 12 carbon atoms or (alkoxy of 1 to 12 carbon atoms) carbonyl or having one of the definitions of R given below except hydrogen; or R2 is a group of the formula (I-a), (I-b) or (I-c); with m being 2 6 3, with X 2 being alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms being unsubstituted or substituted with 1, 2 or 3, alkyls of 1 to 4 carbon atoms; phenyl that is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxys of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; and the X3 radicals being independently from each other alkylene of 2 to 12 carbon atoms; A is -0R3, -N (R4) (R5) or a group of the formula (ii-D;
R3 / R4 and s which are identical or different, are hydrogen, alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; alkenyl of 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms or alkoxies of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2, 6 3 alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy of 1 to 8 carbon atoms, di (C1-C4 alkyl) amino or a group of the formula (III); with Y being -0 -, -CH2-, -CH2CH2 - or > N-CH3; or -N (R) (R5) is additionally a group of the formula (III); X is -0 - or > N-R6; R6 is hydrogen, alkyl of 1 to 18 carbon atoms, alkenyl of 3 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; phenylalkyl of 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyls of 1 to 4 carbon atoms; tetrahydrofurfuryl, a group of the formula (IV-1), or alkyl of 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy of 1 to 8 carbon atoms, di (alkyl of 1 to 4 carbon atoms) amino or a group of the formula (III); R has one of the meanings given for R6; and B has one of the meanings given for A.
26. A product according to claim 25, characterized in that Z is hydrogen.
27. A product according to claim 25 characterized in that R4, R5 and R6 are different from hydrogen.
28. A product according to claim 25, having a polydispersity Mw / Mn of 1. 1 to 1.7.
29. A mixture containing a monodisperse compound of formula (M-I-a), a monodisperse compound of the formula (M-II-a), a monodisperse compound of the formula (M-III-a) and a monodisperse compound of the formula (M-IV-a), the compounds differ only in the number of repetitive units, the radicals A, B, R, Z and R2 being as defined in claim 25 and the total amount of the compounds of the formulas (MIa), (M-II-a), (M-Ill-a) and (M-IV-a) from 40 to 70 mol%, relative to the total mixture.
30. A mixture according to claim 29 characterized in that Z is hydrogen or alkyl of 1 to 4 carbon atoms; R2 is alkylene of 2 to 6 carbon atoms; R is a group of the formula (IV-1); A is -N (R4) (R5); R and R5, which are identical or different, are alkyl of 1 to 8 carbon atoms; B is a group of the formula (II-1); X is > NR6; R6 is alkyl of 1 to 8 carbon atoms.
31. A mixture according to claim 30 characterized in that Z is hydrogen; R2 is hexamethylene; R4, R5 and R6 are butyl, SUMMARY An affordable product 1) by reacting a product of formula (a) N ^ yN with a compound of the ß formula in a molar ratio of 1.2: 1 at 1.4: 1; 2) by reacting the end groups of the formula (?) that are present in the product of reaction 1) with for example, dibutylamine in a molar ratio of 2: 1.7 to 2: 3; reactions 1) and 2) are carried out in an organic solvent in the presence of an inorganic base; and 3) transferring the formula groups the A r the transfer is carried out by reacting the reaction product 2) with a hydroperoxide in a hydrocarbon solvent in the presence of a catalyst that decomposes peroxide; Ri is in particular a hydrocarbyl radical, B is, for example, N- (2, 2, 6, 6-tetramethyl-4-piperidyl) -butylamino, R is, for example, 2,2,6,6-tetramethyl-4- piperidyl and R2 is, for example, hexamethylene. The products obtained are useful as light stabilizers, heat stabilizers and oxidation stabilizers for organic materials, in particular synthetic polymers such as polyolefins.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP97810330.7 | 1997-05-27 | ||
EP97810331.5 | 1997-05-27 |
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MXPA99010888A true MXPA99010888A (en) | 2000-09-04 |
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