MXPA99010923A - 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
- MXPA99010923A MXPA99010923A MXPA/A/1999/010923A MX9910923A MXPA99010923A MX PA99010923 A MXPA99010923 A MX PA99010923A MX 9910923 A MX9910923 A MX 9910923A MX PA99010923 A MXPA99010923 A MX PA99010923A
- Authority
- MX
- Mexico
- Prior art keywords
- carbon atoms
- formula
- alkyl
- substituted
- unsubstituted
- Prior art date
Links
- 239000011368 organic material Substances 0.000 title claims description 17
- 239000003381 stabilizer Substances 0.000 title description 26
- -1 N-(2,2,6,6-tetramethyl-4-piperidyl)-butylamino Chemical group 0.000 claims abstract description 164
- 150000001875 compounds Chemical class 0.000 claims abstract description 113
- 238000006243 chemical reaction Methods 0.000 claims abstract description 69
- 239000002904 solvent Substances 0.000 claims abstract description 33
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 24
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 18
- 150000002978 peroxides Chemical class 0.000 claims abstract description 18
- 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 9
- 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 350
- 125000000217 alkyl group Chemical group 0.000 claims description 146
- 239000000203 mixture Substances 0.000 claims description 103
- 239000000047 product Substances 0.000 claims description 98
- 125000002947 alkylene group Chemical group 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 33
- 239000004743 Polypropylene Substances 0.000 claims description 32
- 229920001155 polypropylene Polymers 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 24
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 24
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 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 16
- 239000002184 metal Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical group CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 14
- JKQOBWVOAYFWKG-UHFFFAOYSA-N molybdenum trioxide Inorganic materials O=[Mo](=O)=O JKQOBWVOAYFWKG-UHFFFAOYSA-N 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
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 239000004698 Polyethylene (PE) Substances 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 9
- 238000000354 decomposition reaction Methods 0.000 claims description 9
- 229920000573 polyethylene Polymers 0.000 claims description 9
- 230000000087 stabilizing Effects 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 claims description 7
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tBuOOH Chemical group CC(C)(C)OO CIHOLLKRGTVIJN-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
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 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 description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 229920001059 synthetic polymer Polymers 0.000 claims description 5
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N Tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
- 230000015556 catabolic process Effects 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- 230000004059 degradation Effects 0.000 claims description 4
- 238000006731 degradation reaction Methods 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
- 125000001183 hydrocarbyl group Chemical group 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
- 230000003252 repetitive Effects 0.000 claims description 4
- 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- HGCIXCUEYOPUTN-UHFFFAOYSA-N Cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 150000001924 cycloalkanes Chemical class 0.000 claims description 2
- 150000001925 cycloalkenes Chemical class 0.000 claims description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical group [H]* 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
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 claims 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N Cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atoms Chemical group 0.000 claims 1
- 239000004914 cyclooctane Substances 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 57
- 229920001577 copolymer Polymers 0.000 description 38
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- 229920000642 polymer Polymers 0.000 description 23
- 239000000243 solution Substances 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 14
- 239000005977 Ethylene Substances 0.000 description 13
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 239000000835 fiber Substances 0.000 description 12
- 239000000155 melt Substances 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 11
- 229920002647 polyamide Polymers 0.000 description 11
- 239000007864 aqueous solution Substances 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 229920001684 low density polyethylene Polymers 0.000 description 10
- 239000004702 low-density polyethylene Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000008096 xylene Substances 0.000 description 10
- 239000000654 additive Substances 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical group OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N Diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 8
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 238000005227 gel permeation chromatography Methods 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 239000000049 pigment Substances 0.000 description 8
- 239000004417 polycarbonate Substances 0.000 description 8
- 229920000122 Acrylonitrile butadiene styrene Polymers 0.000 description 7
- CJZGTCYPCWQAJB-UHFFFAOYSA-L Calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 7
- 239000004721 Polyphenylene oxide Substances 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 239000004700 high-density polyethylene Substances 0.000 description 7
- 229920002866 paraformaldehyde Polymers 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- JKIJEFPNVSHHEI-UHFFFAOYSA-N tris(2,4-ditert-butylphenyl) phosphite Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 7
- WXZMFSXDPGVJKK-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L Sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 235000013539 calcium stearate Nutrition 0.000 description 6
- 239000008116 calcium stearate Substances 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 229920000098 polyolefin Polymers 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 239000012265 solid product Substances 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 229920000877 Melamine resin Polymers 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 239000003963 antioxidant agent Substances 0.000 description 5
- 235000006708 antioxidants Nutrition 0.000 description 5
- 238000009826 distribution Methods 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 239000004707 linear low-density polyethylene Substances 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- MGNCLNQXLYJVJD-UHFFFAOYSA-N Cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 4
- UKJARPDLRWBRAX-UHFFFAOYSA-N N,N'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 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
- 206010054107 Nodule Diseases 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
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N Triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 4
- 238000010533 azeotropic distillation Methods 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000019256 formaldehyde Nutrition 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920001707 polybutylene terephthalate Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N t-BuOH Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- 229940113165 trimethylolpropane Drugs 0.000 description 4
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (-)-propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 3
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 3
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 3
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
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- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- HDHOHQHZKXFKOS-UHFFFAOYSA-M ethyl benzene hydroperoxide Chemical compound [O-]O.CCC1=CC=CC=C1 HDHOHQHZKXFKOS-UHFFFAOYSA-M 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
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- 235000019197 fats Nutrition 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N fumaric acid Chemical compound OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 235000010382 gamma-tocopherol Nutrition 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 229920000578 graft polymer Polymers 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229920005555 halobutyl Polymers 0.000 description 1
- 125000004968 halobutyl group Chemical group 0.000 description 1
- 125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 125000005647 linker group Chemical group 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 235000011160 magnesium carbonates Nutrition 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 239000004137 magnesium phosphate Substances 0.000 description 1
- 235000010994 magnesium phosphates Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- OBQVOBQZMOXRAL-UHFFFAOYSA-L magnesium;docosanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O OBQVOBQZMOXRAL-UHFFFAOYSA-L 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-L maleate(2-) Chemical compound [O-]C(=O)\C=C/C([O-])=O VZCYOOQTPOCHFL-UPHRSURJSA-L 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000004701 medium-density polyethylene Substances 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 125000005394 methallyl group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- UJRDRFZCRQNLJM-UHFFFAOYSA-N methyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=CC=CC3=N2)=C1O UJRDRFZCRQNLJM-UHFFFAOYSA-N 0.000 description 1
- VRBLLGLKTUGCSG-UHFFFAOYSA-N methyl 3-[3-tert-butyl-5-(5-chlorobenzotriazol-2-yl)-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OC)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O VRBLLGLKTUGCSG-UHFFFAOYSA-N 0.000 description 1
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- 125000004492 methyl ester group Chemical group 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
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- 239000005445 natural product Substances 0.000 description 1
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- 229920001194 natural rubber Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
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- IXVLEAZXSJJKFR-UHFFFAOYSA-N octadecyl 2-[(4-hydroxy-3,5-dimethylphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CSCC1=CC(C)=C(O)C(C)=C1 IXVLEAZXSJJKFR-UHFFFAOYSA-N 0.000 description 1
- RNVAPPWJCZTWQL-UHFFFAOYSA-N octadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RNVAPPWJCZTWQL-UHFFFAOYSA-N 0.000 description 1
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- NTTIENRNNNJCHQ-UHFFFAOYSA-N octyl N-(3,5-ditert-butyl-4-hydroxyphenyl)carbamate Chemical compound CCCCCCCCOC(=O)NC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NTTIENRNNNJCHQ-UHFFFAOYSA-N 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- 150000002894 organic compounds Chemical class 0.000 description 1
- YIKSCQDJHCMVMK-UHFFFAOYSA-N oxalic acid diamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- GYHHZMUNWLCUAH-UHFFFAOYSA-N phenothiazine Chemical compound C1=CC=C2[N]C3=CC=CC=C3SC2=C1 GYHHZMUNWLCUAH-UHFFFAOYSA-N 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
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- 238000001782 photodegradation Methods 0.000 description 1
- 125000005498 phthalate group Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 239000001739 pinus spp. Substances 0.000 description 1
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- 229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
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- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- VLYFRFHWUBBLRR-UHFFFAOYSA-L potassium;sodium;carbonate Chemical compound [Na+].[K+].[O-]C([O-])=O VLYFRFHWUBBLRR-UHFFFAOYSA-L 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L propanedioate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000003014 reinforcing Effects 0.000 description 1
- 238000000518 rheometry Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-M stearate Chemical compound CCCCCCCCCCCCCCCCCC([O-])=O QIQXTHQIDYTFRH-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000006488 t-butyl benzyl group Chemical group 0.000 description 1
- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- NZNAAUDJKMURFU-UHFFFAOYSA-N tetrakis(2,2,6,6-tetramethylpiperidin-4-yl) butane-1,2,3,4-tetracarboxylate Chemical compound C1C(C)(C)NC(C)(C)CC1OC(=O)CC(C(=O)OC1CC(C)(C)NC(C)(C)C1)C(C(=O)OC1CC(C)(C)NC(C)(C)C1)CC(=O)OC1CC(C)(C)NC(C)(C)C1 NZNAAUDJKMURFU-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000003878 thermal aging Methods 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- 235000008170 thiamine pyrophosphate Nutrition 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 125000002640 tocopherol group Chemical group 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- 229930003799 tocopherols Natural products 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- INNSFNJTGFCSRN-UHFFFAOYSA-N tridecyl 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methylsulfanyl]acetate Chemical compound CCCCCCCCCCCCCOC(=O)CSCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 INNSFNJTGFCSRN-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- CNUJLMSKURPSHE-UHFFFAOYSA-N trioctadecyl phosphite Chemical compound CCCCCCCCCCCCCCCCCCOP(OCCCCCCCCCCCCCCCCCC)OCCCCCCCCCCCCCCCCCC CNUJLMSKURPSHE-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 238000005429 turbidity Methods 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 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
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 229930003231 vitamins Natural products 0.000 description 1
- 239000011089 white board Substances 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
- 239000002478 γ-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 stoichiometric ratio to obtain a compound of formula (&ggr;);2) reacting the compound of formula (&bgr;) with the compound of formula (&ggr;) in a molar ratio of 0.4:1 to 0.75:1;3) reacting the end groups of formula (&dgr;), being present in the product of the reaction 2) with e.g. dibutylamine in a molar ratio of 2:1.7 to 2:3;the reactions 1) to 3) being carried out in an organic solvent in the presence of an inorganic base;and 4) transferring the groups of formula (G-I) being present in the product of the reaction (3) to groups of formula (G-II), said transfer being carried out by reacting the product of the reaction (3) 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.
Description
BLOCK OLIGOMERS CONTAINING GROUPS
l-HIDROCARBILOXI-2,2, 6, 6 -TETRAMETIL-4 -PIPERIDILO,
AS STABILIZERS FOR ORGANIC MATERIALS
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, thermostabilizers and oxidation stabilizers for organic materials, particularly polymers. synthetic, 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 U.S. Pat. No. 4,086,204, No. 4,331,586, No. 4,335,242, No. 4,234,707, No. 4,459,395,
No. 4,492,791, No. 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 that is obtained by 1) reacting a compound of the formula (OI) B with a compound of the formula (ß)
in a stoichiometric ratio, to obtain the compound of the formula (y);
2) reacting the compound of the formula (ß) with the compound of the formula (y) in a molar ratio of 0.4: 1 to 0.75: 1, preferably 0.5: 1 to 0.75: 1, in particular 0.5: 1; 3) react the extreme groups of the formula (d)
• Cl
present in the reaction product 2) with a compound of the formula (e) AH '(e) in a molar ratio of 2 (end group): 1.7 to 2: 3, preferably 2: 2 to 2: 2.6, in particular 2: 2 to 2: 2.4; reactions 1) to 3) are carried out in an organic solvent in the presence of an inorganic base; and 4) transfer the groups of the formula (G-I)
present in the reaction product 3) with groups of the formula (G-II);
the transfer is carried out by reacting product of reaction 3) with a hydroperoxide in a hydrocarbon solvent, in the presence of a peroxide decomposition catalyst; R1 is a hydrocarbyl radical or -0-R] _ is oxyl; R2 is alkylene with 2 to 12 carbon atoms, alkenylene with 4 to 12 carbon atoms, cycloalkylene with 5 to 7 carbon atoms, cycloalkylene with 5 to 7 carbon atoms. carbon-di (alkylene with 1 to 4 carbon atoms), alkylene with 1 to 4 carbon atoms-di (cycloalkylene with 5 to 7 carbon atoms), phenylendi (alkylene with 1 to 4 carbon atoms) or alkylene with 4 at 12 carbon atoms interrupted by 1,4-piperazindiyl, -O- or > N-XX with Xx which is acyl with 1 to 12 carbon atoms or (C 1 -C 12 alkoxy) carbonyl or has one of the definitions of R 4 given below; or R2 is a group of the formula (I-a), (I-b) or (I-c);
C H,
with m which is 2 or 3, X2 is alkyl with 1 to 18 carbon atoms, cycloalkyl with
to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenyl that is unsubstituted or substituted by
1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; and the X3 radicals independently of each other are alkylene with 2 to 12 carbon atoms; A is -OR3, -N (R4) (R5) or a group of the formula (II);
R3, R4 and R5, which are identical or different, are alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms. carbon; alkenyl with 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl having 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (C1-C4 alkyl) amino or a group of the formula (III);
/ \ Y N (ni; \ /
with Y which is -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 alkyl groups having 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl, a group of the formula (GI), or alkyl with 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (alkyl with 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 (G-L) to the groups of the formula (G-II) can be carried out for example analogously to the method described in the patent of the USA No. 4,921,962 which is incorporated herein by reference. The meaning of Rx depends on the hydrocarbon solvent used in reaction 4). Rx is preferably a hydrocarbyl radical having 5 to 18 carbon atoms. R? it is in particular alkenyl with 5 to 18 carbon atoms, alkynyl with 5 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms unsubstituted or substituted by alkyl with 1 to 4 carbon atoms; cycloalkenyl with 5 to 12 carbon atoms unsubstituted or substituted by alkyl with 1 to 4 carbon atoms: a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms or phenylalkyl with 1 to 9 carbon atoms unsubstituted or substituted in the phenyl per alkyl with 1 to 4 carbon atoms: and the hydrocarbon solvent in reaction 4) accordingly depends on R 1 r alkane with 5 to 18 carbon atoms, alkene with 5 to 18 carbon atoms, alkyne with 5 a 18 carbon atoms, cycloalkane with 5 to 12 carbon atoms unsubstituted or substituted by alkyl having 1 to 4 carbon atoms; cycloalkene with 5 to 12 carbon atoms unsubstituted or substituted by alkyl with 1 to 4 carbon atoms: a bicyclic or tricyclic hydrocarbon having 6 to 10 carbon atoms or phenylalkan with 7 to 9 carbon atoms unsubstituted or substituted in the phenyl by alkyl with 1 to 4 carbon atoms. According to a further preferred embodiment
Ri is heptyl, octyl, cyclohexyl, methylcyclohexyl, cyclooctyl, cyclohexenyl, -methylbenzyl or 1,2,3,4-tetrahydronaphtenyl and the hydrocarbon solvent in the reaction 4) dependent on Rl, heptane, octane, cyclohexane, cyclooctane methylcyclohexane, cyclohexene, ethylbenzene or tetralin. According to a particularly preferred embodiment, R1 is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 4) is dependent on Rx, 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, hexadecyl and octadecyl. R? it is preferably alkyl having 6 to 12 carbon atoms, in particular heptyl or octyl. R 4, R 5 and R 6 are preferably alkyl with 1 to 8 carbon atoms, in particular alkyl with 1 to 4 carbon atoms. An example of alkyl with 2 to 4 carbon atoms substituted by -OH is 2-hydroxyethyl. Examples of alkyl with 2 to 4 carbon atoms substituted by alkoxy with 1 to 8 carbon atoms, preferably by alkoxy with 1 to 4 carbon atoms, in particular methoxy or ethoxy, are 2-methoxyethyl, 2-ethoxyethyl, 3- methoxypropyl, 3-ethoxypropyl, 3-butoxypropyl, 3-octoxypropyl and 4-methoxybutyl. Examples of alkyl having 2 to 4 carbon atoms substituted by di (C1-C8 alkyl) amino, preferably by dimethylamino or diethylamino, are 2-dimethylaminoethyl, 2-diethylaminoethyl, 3-dimethylaminopropyl, 3-diethylaminopropyl, -dibutylaminopropyl and 4-diethylaminobutyl. The group of the formula (III) preferably is
/ \ NO \ / Preferred examples of alkyl having 2 to 4 carbon atoms substituted by a group of formula (III) are groups of the formula / \ / \ YN (CH,), .- N (CH? ^ - \ / The group or 1 \ /
it is particularly preferred. Examples of cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 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 6 to 10 carbon atoms is 1,2,3,4-tetrahydronaphtenyl. A preferred example of cycloalkenyl with 5 to 12 carbon atoms unsubstituted or substituted by alkyl with 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 wherein the carbon atom in the 1-position is saturated, allyl is particularly preferred and preferred. An example of alkynyl is pentynyl or octynyl.
Examples of phenyl substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms are methylphenyl, dimethylphenyl, trimethylphenyl, t-butylphenyl, di-t-butylphenyl, 3,5-di. -t-butyl-4-methylphenyl, methoxyphenyl, ethoxyphenyl and butoxyphenyl. Example of phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 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 with 1 to 8 carbon atoms and benzoyl are preferred. Acetyl is especially preferred. Examples of (C 1 -C 12 alkoxy) -carbonyl 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, octamethylene, decamethylene and dodecamethylene. R2 for example is alkylene with 2 to 8 carbon atoms or alkylene with 4 to 8 carbon atoms, in particular alkylene with 2 to 6 carbon atoms, preferably hexamethylene. An example of alkenylene with 4 to 12 carbon atoms is 3-hexenylene. An example of cycloalkylene with 5 to 7 carbon atoms is cyclohexylene. Examples of alkylene with 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl are
/ \ CH2CH2- N I I N- • CH-CH, \ /
/ \ CH, CH, CH, - N Nr > - CH2CH2CH2 - / Examples of alkylene with 4 to 12 carbon atoms interrupted by -O-, for example 1, 2 or 3 -O-, are
3-oxapentan-l, 5-diyl, 4-oxaheptan-l, 7-diyl, 3,6-dioxaoctan-l, 8-diyl, 4,7-dioxadecan-l, 10-diyl,
4,9-dioxadodecan-1, 12-diyl, 3,6, 9-trioxaundecan-1, 11-diyl and 4,7, 10-trioxatridecan-1, 13-diyl. Examples of alkylene with 4 to 12 carbon atoms interrupted by > N-XX are -CH2CH2CH2-N (X1) -CH2CH2-N (Xx) -CH2CH2CH2-, in particular -CH2CH2CH2-N (CH3) -CH2CH2-N (CH3) -CH2CH2CH2-. An example of cycloalkylene with 5 to 7 carbon atoms-di (alkylene with 1 to 4 carbon atoms) is cyclohexylenedimethylene. Examples of alkylene with 1 to 4 carbon atoms-di (cycloalkylene with 5 to 7 carbon atoms) are methylenedicyclohexylene and isopropylidenedicyclohexylene. An example of phenylenedi (alkylene with 1 to 4 carbon atoms) is phenylenedimethylene. In the compound of the formula (y), R is preferably a group of the formula (G-I). A product is preferred wherein R2 is alkylene with 2 to 12 carbon atoms, cycloalkylene with 5 to 7 carbon atoms, cycloalkylene with 5 to 7 carbon atoms-di (alkylene with 1 to 4 carbon atoms), alkylene with 1 at 4 carbon atoms-di (cycloalkylene with 5 to 7 carbon atoms), phenylendi (alkylene with 1 to 4 carbon atoms) or alkylene with 4 to 12 carbon atoms interrupted by -Oo >N-XX with Xt which is acyl with 1 to 12 carbon atoms or (C 1 -C 12 alkoxy) carbonyl or has one of the definitions of R 4; or R2 is a group of the formula (I-b); R3 R4 and R5 / < 3 are identical or different, are alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 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 having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups having 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; or a group of the formula (G-I). Also preferred is a product wherein R2 is alkylene with 2 to 10 carbon atoms, cyclohexylene (cyclohexylene) (alkylene with 1 to 4 carbon atoms), alkylene cyclopexy with 1 to 4 carbon atoms or phenylene (alkylene with 1 to 4 carbon atoms). carbon atoms), -R3, R4 and R5, which are identical or different are alkyl having 1 to 12 carbon atoms, cycloalkyl with 5 to 7 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; benzyl which is unsubstituted or substituted on phenyl by alkyl with 1 to
4 carbon atoms; or -N (R4) (R5) is additionally a group of the formula (III); and 'R6 is alkyl with 1 to 12 carbon atoms, cycloalkyl with
to 7 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; benzyl which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; or a group of the formula (G-I). Also preferred is a product wherein R2 is alkylene with 2 to 8 carbon atoms; R3, R4 and R5, which are identical or different, are alkyl with 1 to 8 carbon atoms, cyclohexyl which is unsubstituted or substituted by methyl; phenyl which is unsubstituted or substituted by methyl; benzyl or -N (R4) (R5) is further 4 -morpholinyl; and R6 is alkyl with 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 wherein
Rx is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 4) depends on Rl f octane or cyclohexane;
R2 is alkylene with 2 to 6 carbon atoms; A is -N (R4) (R5) or a group of the formula (II); R4 and R5, which are identical or different, are alkyl with 1 to
8 carbon atoms; or -N (R4) (R5) is further 4 -morpholinyl; X is > NR6;
R6 is alkyl with 1 to 8 carbon atoms; and B has one of the meanings given for A. Also particularly preferred is a product wherein Rx is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 4) is, depending on Rl octane or cyclohexane; R2 is alkylene with 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 with 1 to
8 carbon atoms; B is a group of the formula (II); X is > NR6; R6 is alkyl with 1 to 8 carbon atoms. The organic solvent used in the reactions
1), 2) and 3) in particular is 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 methyl ethyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl amyl ketone, ethyl butyl ketone, di-n-propyl ketone, methyl hexyl ketone and ethyl amyl ketone. Ketones essentially insoluble in water, are preferred. Preferred solvents are toluene, xylene, methyl butyl ketone and methyl isobutyl ketone. Xylene and methyl isobutyl ketone are particularly preferred. Examples of the inorganic base employed in the present process are sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate. Sodium hydroxide is preferred. Reactions 1) to 3) are preferably carried out in an inert atmosphere, in particular under nitrogen. Depending on the solvent, the reaction 1) for example is carried out at a temperature of 10 ° to 90 ° C, preferably 20 ° to 90 ° C, in particular 50 ° to 85 ° C. Reaction 2) is conveniently carried out in a closed system at a temperature of, for example, 110 ° to 200 ° C, preferably 130 ° to 190 ° C, in particular 150 ° to 160 ° C. When the reaction mixture is heated to the desired temperature, the pressure increases, since the reaction is carried out in a closed system. Due to the low boiling points of the solvents used, generally a pressure of 3 to 8 bar, for example 4 to 6 bar, is measured in the reactor. Reaction 3) is also conveniently carried out in a closed system 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 normally of 3 to 8 bar, for example 4 to 6 bar, is again measured in the reactor. If desired, after finishing the reaction 3), the compound of the formula (e) and optionally the unreacted starting materials can be removed from the final mixture by distillation or by using usual purification techniques. The product of the reaction 3) is conveniently isolated before the reaction 4) follows. The peroxide decomposition catalyst used in the reaction 4, for example is a carbonyl metal, 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, hexacarbonyl molybdenum, 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 4) 2 to 8 moles, preferably 3 to 6 moles, of the hydroperoxide, 0.001 to 0.1 mole, preferably 0.005 to 0.05 mole, of the peroxide decomposition catalyst and 5 to 30 moles, preferably 10 to 20 moles, of the hydrocarbon solvent are applied, for example, per mole of the hindered amine portion of the formula (GI)
present in the product of reaction 3). The transfer of the hindered amine portion of the formula (G-I) to the groups of the formula hydrocarbyl
for example it is carried out from 75 ° to 160 ° C, preferably
100 ° to 150 ° C. When in reaction 4) the hindered amine portions of the formula (G-I) are first treated with aqueous hydroperoxide in the presence of the peroxide decomposition catalyst in an inert organic solvent
(for example analogously to the method described in U.S. Patent No. 4,691,015), the initial reaction product that is obtained in a relatively short time is the corresponding N-oxyl intermediate (-ORx = oxyl) which is highly colored , and that can be isolated per se. A preferred further embodiment of the invention is therefore related to a product that is obtained according to the above reactions 1) to 4), wherein the radical -0-Rx is oxyl and the hydrocarbon solvent in reaction 4) is an inert organic solvent, preferably toluene or 1,2-dichloroethane. When the organic solvent in reaction 4) is a hydrocarbon having a labile hydrogen atom, when there is a sufficient molar excess of the hydroperoxide beyond that required to convert the amine to the corresponding N-oxyl derivative, and when the reaction mixture it is heated to moderate temperatures (preferably 100 ° to 150 ° C) for an additional period, an additional reaction is carried out between the N-oxyl compound (either prepared in situ from the original amine or used as the starting intermediate initial in the process) and the hydrocarbon solvent to give the corresponding N-hydrocarbyloxy derivative. The original reaction mixture in reaction 4) is colorless, but becomes highly colored, as the N-oxyl intermediate is formed. This color disappears, as the N-oxyl compound becomes the colorless N-hydroxycarbyloxy product. This process in this way essentially has an interconstructed color indicator to show the extent of the reaction. When the reaction mixture becomes colorless, it shows that the color N-oxyl intermediate has been completely converted to the N-hydrocarbyloxy product. An embodiment of this invention is also a product that is obtained by hydrogenation of the product of reaction 4), wherein -0RX in 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 PtOz, as described for example in the patent of the USA No. 4,691,015. If desired, the product obtained in reaction 4) 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) Residual peroxide decomposes and the solvent partially evaporates. 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) Residual peroxide decomposes and the solvent evaporates at elevated temperature to obtain a melt. 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 mix the hot melt with solvent, heat to bring any solids to the solution and then cool to obtain a precipitate. d) Residual peroxide decomposes and the solvent evaporates at elevated temperature to obtain a melt. The melt is dissolved in an inert solvent, such as one of the above, with or without heating and the resulting solution can be concentrated by distillation of some of the excess solvent. The solution is then mixed with a second solvent, such as one of the above, at a temperature such that the product precipitates. The solid is collected by filtration and dried. More specifically, the product obtained from reaction 4) is preferably purified as follows:
After the reaction is complete 4) the crude reaction mixture is cooled to 50 ° C and treated with 20% aqueous sodium sulfite, until the residual peroxide concentration falls below 0.5%. The aqueous layer is separated, 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 on heating in vacuo. In general, the starting materials used in the process described above are known. In the case that they are not commercially available, they can be prepared analogously by known methods. The compound of the formula (OI) 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 (OI) the same solvent and the same inorganic base as in the reactions indicated above 1) to 3). If desired, after the preparation of the starting material of the formula (), the reaction 1) can immediately follow without isolation of the compound of the formula (OI). Some starting materials of the formula (ß) are for example described in OA-95/21 157, US-A-4 316 837 and US-A-4 743 688. A further embodiment of this invention is a product that is obtained by the above reactions 1) -3). Products where the nitrogen atom in the group
is substituted by alkyl having 1 to 8 carbon atoms, hydroxyalkyl with 2 to 8 carbon atoms, O, -OH, hydrocarbyloxy with 1 to 18 carbon atoms (for example, alkoxy with 1 to 18 carbon atoms or cycloalkoxy with 5 ~ to 12 carbon atoms), -CH2CN, alkenyl with 3 to 6 carbon atoms, alkynyl with 3 to 6 carbon atoms, phenylalkyl with 7 to 9 carbon atoms, unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; or acyl with 1 to 8 carbon atoms, can be prepared in analogy to the above reactions 1) to 3), using the appropriate starting materials. The nitrogen atom is preferably replaced by alkyl with 1 to 4 carbon atoms, in particular methyl. Those starting materials that contain a group of the formula
- hydrocarbyl
they can be prepared, for example in a manner analogous to the methods described in US Pat. Nos. 4,921,962, 5,021,577 and 5,204,473. The reaction product 3) is not a simple specific compound but a compound with a molecular weight distribution. Polydispersity indicates the molecular weight distribution of a polymeric compound. In the present application, the polydispersity is the weight average molecular weight ratio C *? ) and numerical average (f ^ n). A value of ^ w / lvín equal to 1 means that the compound is monodisperse and that it only has a molecular weight and no molecular weight distribution. A narrow molecular weight distribution is characterized by a polydispersity (Mw / I n) close to 1. A preferred product of reaction 3) 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 notable that the product of reaction 3) contains, for example, less than 5 mol%, in particular less than 2 mol% or less than 1 mol%, of linear by-products that are not extremely finished by a portion of the formula
B
During reactions 1) and 2), a cyclic compound of the formula
B B
It can be formed as a by-product. This compound is known from the U.S. patent. No. 4,442,250 may be present in an amount for example less than 15 mol% in the product of reaction 3). "The product of reaction 3) is preferably a mixture containing a monodisperse compound of the formula (MI), a monodisperse compound of the formula (M-II) and a monodisperse compound of the formula (M-III), the compounds only differ in the number of repetitive units,
The radicals A, B, R and R2 are as defined above and the total amount of the compound of the formula (MI) is 15 to 45 mol%, for example 20 to 45 mol% or 25 to 45 mol% or 30 to 45% mol or 30 to 40 mol%, the total amount of the compound of the formula (M-II) is 15 to 35 mol%, for example 15 to 30 mol% or 15 to 25 mol% or 20 to 25 mol%, and the total amount of the compound of the formula (Mill) is 3 to 18 mol%, for example 3 to 12 mol% or 5 to 12 mol%, with respect to the total mixture ( = 100% in mol). A mixture that additionally contains a monodisperse compound of the formula (M-IV) is preferred.
and wherein the total amount of the compound of the formula (M-IV) is 1 to 15 mol%, for example 1 to 10 mol% mol 5 mol%, relative to the total mixture (= 100 mol%) . Reaction 4) is related in particular to the transfer of the groups of the formula (G-I)
present in the mixture containing the compounds of the formulas (M-I), (M-II), (M-III) and optionally (M-IV) to groups of the formula (G-II).
After transfer the amounts of the compounds shown below of the formulas (PI), (P-II), (P-III) and optionally (P-IV) in the product of reaction 4) correspond to the amounts of the initial compounds shown above of the formulas (MI), (M-II), (M-III) and optionally (M-IV), since the main structure of those compounds is not affected during the reaction. Accordingly, 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) and a monodisperse compound of the formula (P-III), the compounds only differ in the number of repetitive units.
the total amount of the compound of the formula (PI) is 15 to 45% mol, for example 20 to 45% mol or 25 to 45% mol or 30 to 45% mol or 30 to 40 mol%, the total amount of the compound of the formula (P-II) 'is 15 to 35 mol%, for example 15 to 30 mol% or 15 to 25 mol% or 20 to 25 mol% and the total amount of the compound of the formula (P-III) is 3 to 18% mol, for example 3 to 12 mol% or 5 to 12 mol%, relative to the total mixture (= 100 mol%); and R1 is hydrogen, a hydrocarbyl radical or -O-Rx is oxyl; R 2 is alkylene with 2 to 12 carbon atoms, alkenylene with 4 to 12 carbon atoms, cycloalkylene with 5 to 7 carbon atoms, cycloalkylene with 5 to 7 carbon atoms-di (alkylene with 1 to 4 carbon atoms), C 1 -C 4 -alkylene (cycloalkylene with 5 to 7 carbon atoms), phenylendi (C 1 -C 4 -alkylene) or C 4 -C 12 -alkylene interrupted by 1,4-piperazindyiyl, - O- or > N-XX with X x which is acyl with 1 to 12 carbon atoms or (C 1 -C 12 alkoxy) carbonyl or having one of the definitions of R 4 given below; or R2 is a group of the formula (I-a), (I-b) or (I-c);
C H -B- H, (I-b) O
O X,
with m being 2 or 3, X 2 is alkyl having 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; and the X3 radicals independently of each other are alkylene with 2 to 12 carbon atoms; A * is -OR3, -N (R4) (R5) or a group of the formula (G-IV);
R3, R4 and R5, which are identical or different, are alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms. carbon; alkenyl with 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl having 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (C1-C4 alkyl) amino or a group of the formula (III);
/ \ Y N (III) \ /
with what it is. -O-, -CH2-, -CH2CH2- or > N-CH3; and R3 is additionally hydrogen or -N (R4) (R5) is further a group of the formula (III); X * is -O- or > N-R6 *; R6 * is alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups having 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyl groups with 1-4 carbon atoms; tetrahydrofurfuryl, a group of the formula (G-II),
or alkyl having 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (C1-C4 alkyl) 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 *. A mixture that additionally contains a monodisperse compound of the formula (P-IV) is preferred.
wherein the radicals A *, B *, R *, Ri and R2 are as defined above and the total amount of the compound of the formula (P-IV) is 1 to 15 mol%, for example 1 to 10% in mol or 1 to 5 mol%, with respect to the total mixture (= 100 mol%). Those mixtures are preferred where Rj. is octyl or cyclohexyl; R2 is alkylene with 2 to 6 carbon atoms; R * is a group of the formula (G-II); A * is -N (R4) (R5); R4 and R5 * 3u < s are identical or different, they are alkyl with 1 to
8 carbon atoms; B * is a group of the formula (G-IV); X * is > NR6 *; and R6 * is alkyl with 1 to 8 carbon atoms. In the mixtures according to this invention, the radical R can act as a linking group between two or more compounds of the formulas (P-I), (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 Rx * can be deduced from the meaning of Rx. The only difference between these two radicals is that Rx * has one or two additional valences. In this manner, R1 as cyclohexyl corresponds to R? * As cyclohexanediyl or cyclohexantriyl and Rx as octyl corresponds to Rx * as octandiyl or octantriil. The products of this invention as well as the mixtures described are very effective in improving the resistance to light, heat and oxidation of organic materials, especially synthetic polymers and copolymers. In particular, a low pigment interaction as well as a very good color are observed in polypropylene, especially polypropylene fibers, in particular in the presence of flame retardants as well as low density polyethylene (LDPE) films for agricultural use. It is also notable that the product of this invention as well as the mixtures described are themselves flame 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 cycloolefin polymers, for example of cyclopentene or norbornene, polyethylene (which can optionally be interlaced) for example high density polyethylene (HDPE), high density and high molecular weight polyethylene (HDPE-HM), high density polyethylene and ultra high molecular weight (HDPE) -UHMW), medium density polyethylene (MDPE), low density polyethylene (LDPE), linear low density polyethylene (LLDPE), (VLDPE) and (ULDPE). Polyolefins, ie the polymers of monoolefins exemplified in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by different and especially by the following methods: a) radical polymerization (normally with high pressure and high temperature). b) catalytic polymerization using a catalyst that normally contains one or more than one metal of groups IVb, Vb, VIb or VIII of the Periodic Table. These metals usually have one or more than one ligand, typically oxides, halides, alcoholates, esters, ethers, amines, alkyls, alkenyls and / or aryls which may be p- or d-coordinated. These metal complexes can be in the free form or fixed in substrates, typically in activated magnesium chloride, titanium (III) chloride, alumina or silicon oxide. These catalysts can be soluble or insoluble in the polymerization medium. The catalysts can themselves be used in the polymerization or additional activators, typically metal alkyls, metal hydrides, metal alkyl halides, alkyl, metal oxides or metal alkyloxanes can be used, metals are elements of the groups la and / or Illa of the Periodic Table. Activators can >; conveniently modified with additional ester, ether amine or silyl ether groups. These catalyst systems are usually referred to as Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC). 2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyisobutylene, polypropylene with polyethylene (for example PP / HDPE, PP / LDPE) and mixtures of different types of polyethylene (for example LDPE / 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 / but-1-ene copolymers, propylene / isobutylene copolymers, ethylene / but-1-ene copolymers, ethylene / hexene copolymers, ethylene / methylpentene copolymers, ethylene / heptene copolymers, copolymers of ethylene / octene, propylene / butadiene copolymers, 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 its salts (ionomers) as well as terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene or ethylidene norbornene; and mixtures of these copolymers with each other and with the polymers mentioned in 1) above, for example "copolymers of polypropylene / ethylene-propylene, copolymers of LDPE / ethylene-vinyl acetate (EVA), copolymers of LDPE / ethylene-acrylic acid (EAA) , LLDPE / EVA, LLDPE / EAA and random or alternating carbon monoxide / polyalkylene copolymers and their mixtures with other polymers, for example polyamides 4.-Hydrocarbon resins (eg C5-C9) _ including hydrogenated modifications (eg example tackifying agents) 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 methacrylate, styrene / butadiene / alkyl acrylate, styrene / butadiene / alkyl methacrylate, styrene / maleic anhydride, styrene / acrylonitrile / methyl acrylate; high impact strength and another polymer, for example a polyacrylate, a diene polymer or 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 polybutyl adiin-e-t-ene or polybutadiene-acrylonitrile copolymers; 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 their mixtures with the copolymers listed under 6), for example mixtures of copolymers known as ABS, MBS, ASA or AES polymers. 8. Halogen-containing polymers such as polychloroprene, chlorinated rubbers, chlorinated and brominated copolymers of isobutylene-isoprene (halobutyl rubber), chlorinated or sulfochlorinated polyethylene, copolymers of ethylene and chlorinated ethylene, homo- and epichlorohydrin copolymers, especially polymers of compounds of vinyl containing halogen, for example polyvinyl chloride, polyvinylidene chloride, polyvinyl fluoride, polyvinylidene fluoride, as well as their copolymers such as vinyl chloride / vinylidene chloride, vinyl chloride / vinyl acetate or vinylidene chloride / vinyl acetate. 9. Polymers derived from α, β-unsaturated acids and their derivatives such as polyacrylates and polymethacrylates, -polymethyl methacrylates, polyacrylamides and polyacrylonitriles, modified against impact with butyl acrylate. 10. Copolymers of the monomers mentioned under 9) with each other or with other unsaturated monomers, for example acrylonitrile / butadiene copolymers, acrylonitrile / alkyl acrylate copolymers, acrylonitrile / alkoxyalkyl acrylate or acrylonitrile / vinyl halide copolymers or acrylonitrile / alkyl terpolymers methacrylate / butadiene. 11. Polymers derived from unsaturated alcohols and amines or the acyl derivatives or their acetals, for example polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyral, polyallyl phthalate or polyallyl melamine; as well as its copolymers with olefins mentioned in 1) above. 12. Homopolymers and copolymers of cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide their copolymers with bisglycidyl ethers. 13. Polyacetals such as polyoxymethylene and those 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.
. Polyurethanes derived from polyethers terminated with hydroxyl, polyesters or polybutadienes on the one hand and aliphatic or aromatic polyisocyanates on the other, as well as their precursors. 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 m-xylene diamine and adipic acid; polyamides prepared from hexamethylenediamine and isophthalic and / or terephthalic acid and with or without an elastomer as a modifier, for example poly-2,4,4-trimethylhexamethylene terephthalamide or poly-m-phenylene isophthalamide; and also block copolymers of the aforementioned polyamides with polyolefins, olefin copolymers, ionomers or grafted or chemically bonded elastomers; or with polyethers, for example with polyethylene glycol, polypropylene glycol or polytetra methylene glycol; as well as polyamides or copolyamides modified with EPDM or ABS; and polyamides condensed during processing (RIM polyamide systems). 17. Polyureas, polyimides, polyamide-imides, polyetherimides, polyesterimides, polyhydantoins and polybenzimidazoles. 18. Polyesters derived from dicarboxylic acids and diols and / or hydroxycarboxylic acids or the corresponding lactones, for example polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate and polyhydroxybenzoates, as well as block copolyethers derived from polyether derivatives with hydroxyl; and also poly esters modified with polycarbonates or MBS. 19. Polycarbonates and polyester carbonates. 20. Polysulfones, polyether sulfones and polyether ketones.
21. Interlaced polymers derived from aldehydes on the one hand and phenols, ureas and melamines on the other hand, such as phenol / formaldehyde resins, urea / formaldehyde resins and melamine / formaldehyde resins.
22. Alkyd resins drying and not drying. 23. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols and vinyl compounds as crosslinking agents and also halogen-containing modifications thereof with low flammability. 24. Interlaxable acrylic resins which are derived from substituted acrylates, for example epoxy acrylates, urethane acrolates or polyester acrylates. 25. Alkyd resins, polyester resins and acrylate resins entangled with melamine resins, urea resins, isocyanates, isocyanurates, polyisocyanates or epoxy resins. 26. Interlaced epoxy resins derived from aliphatic, cycloaliphatic, heterocyclic or aromatic glycidyl compounds, for example products of diglycidyl ester of bisphenol A and bisphenol F, which are entangled with customary hardeners such as anhydrides or amines, with or without accelerators. 27. Natural polymers such as cellulose, rubber, gelatin and chemically modified homologous derivatives thereof, for example cellulose acetates, cellulose propionate and cellulose butyrates or cellulose ethers such as methyl cellulose; as well as turpentine resins and their derivatives. 28. Mixtures of the aforementioned polymers (polyblends), for example PP / EPDM, polyamide / EPDM or ABS, PVC / EVA, 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 or PBT / PET / PC. 29. Organic materials of natural and synthetic origin, which are pure monomeric compounds or mixtures of these compounds, for example mineral oils, animal and vegetable fats, waxes and oils or oils, fats and waxes based on synthetic esters (for example phthalates, adipates, phosphates or trimellitrates) and also mixtures of synthetic esters with mineral oils in proportions by weight, typically those used as centrifugation compositions, as well as aqueous emulsions of these materials. 30. Aqueous emulsions of natural or synthetic rubber, for example networks or latices or natural latex of butadiene / carboxylated styrene copolymers. The invention in this way also relates to a composition comprising an organic material susceptible to light, heat or oxidation induced degradation and a product or mixture according to this invention. The organic material is preferably a synthetic polymer, more particularly one selected from the aforementioned groups. Polyolefins are preferred and polyethylene and polypropylene are particularly preferred. A further emment of this invention is a method for stabilizing an organic material against light, heat or oxidation induced degradation, which comprises incorporating into the organic material a product or a mixture in accordance with this invention. The product or mixture according to this invention can be used in various proportions depending on the nature of the material to be stabilized, the end use and the presence of other additives. In general, it is appropriate to use, for example
0. 01 to 5% by weight of the product or mixture according to the invention, with respect to the weight of the material to be stabilized, preferably 0.05 to 2%, in particular 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 interlacing of the materials. In addition, they can be incorporated into the polymeric materials in the pure form or encapsulated in waxes, oils or polymers. In general, the product or mixture according to this invention can be incorporated into the polymeric materials by various processes, such as dry mixing in the form of a powder, or wet mixing in the form of solutions or suspensions or also in the form of a masterbatch containing the product or mixture according to this invention in a concentration of 2.5 to 25% by weight; in these operations, the polymer can be used in the form of powders, granules, solutions, suspensions or in the form of latices. The materials stabilized with the product or mixture according to this invention can be used for the production of molded parts, films, tapes, monofilaments, fibers, surface coatings and the like. If desired, other conventional additives for synthetic polymers, such as antioxidants, UV absorbers, nickel stabilizers, pigments, fillers, plasticizers, corrosion inhibitors and metal deactivators, can be added to the organic materials containing the product or the mixture of 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-di-methylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6 -di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopenr.-4-methylphenol, 2- (methyl-cyclohexyl) -4,6- dime-ilphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, nonylphenols which are linear or branched in the secondary chains, for example 2. , 6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1 '-methylundec-1'-yl) phenol, 2,4-di-methyl-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-buty1hydroquinone, 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-hydroxyphenyl stearate, bis- (3, 5-di-tert-butyl-4-hydroxyphenyl) adipate.
1. 4. Tocopherols, for example oi-tocopherol, β-tocopherol, gamma-tocopherol, d-tocopherol and their mixtures (Vitamin E). 1.5T Hydroxylated thiodiphenyl ethers, for example 2,2'-t-iobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'-thiobis (6-tert. butyl-3-methylphenol), 4,4'-t-iobis (6-tert-butyl-2-methylphenol), 4,4'-thiobis- (3,6-di-sec-amyl phenol), 4, 4'-bis (2,6-dimethyl-4-hydroxyphenyl) sulphide. 1.6. Alkylidenebisols, for example 2, 2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethyl-enol), 2,2'-methylenebis [ 4-methyl-6- (a-methylcyclohexyl) phenol], 2,2'-methylenebis (4-methyl-6-cyclohexyl) enol), 2,2'-methylenebis (6 -nonyl-4-methyl-1-enol), , 2 '-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidebisbis (4,6-di-tert-butylphenol), 2,2 * -ethylidebis (6-tert-butyl-4-) isobutyl-enol), 2'-2-methylenebis [6- (o-methylbenzyl) -4 -nonyl phenol], 2,2'-methylenebis [6- (a, a-dimethylbenzyl) -4-nonylphenol], 4, 4 '-methylenebis (2,6-di-tert-butyl-enol), 4,4'-methylenebis (6-tert-butyl-2-methylphenol), 1, 1-bis (5-tert-butyl-4-hydroxy-2-methyl-phenyl) -butane, 2,6-bis (3-tert-butyl-5-methyl-2-hydroxybenzyl) -4-methyl-enol, 1, 1, 3 -tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy-2-methyl-phenyl) -3- n-dodecylmercapto-butane, ethylene glycol bis [3, 3-bis (3'-tert-butyl-4'-hydroxyphenyl) bu or], bis (3-tert-butyl-4-hydroxy-5-methyl) phenyl) -dicyclopentadiene, bis [2- (3'-tert-butyl-2'-hydroxy-5'-methylbenzyl) -6-tert-butyl-4-methylphenyl] -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-methyl-ethyl-enyl) -ethane. 1.7. O-, N- and S-benzyl compounds, for example 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl-4-hydroxy-3, 5-di-tert-butylbenzylmercaptoacetate, tris (3, 5-di-tert-butyl-4-hydroxybenzyl) amine, bis (4-tert-butyl-3-hydroxy-2, 6- dimethylbenzyl) dithioterephthalate, bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate. 1.8. Hydroxybenzyl 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-dodecylmercaptoetyl-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-hydroxybenzyl) malonate. 1.9. Aromatic hydroxybenzyl compounds, for example
1, 3,5-tris- (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethyl-benzene, 1,4-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-bu-4-hydroxyphenoxy) ) -1,3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyfen i) -1,2,3-triazine, 1,3,5-tris- (3, 5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1, 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. Benzilfosfonatos, for example dimethyl-2, 5-di-tert-butyl-4 -hidroxibenzilfosfonato, diethyl-3, 5-di-tert-butyl-4-hidroxibenzilfosfonato, dioctadecil3, 5-di-tert-butyl-4-hidroxibenzilfosfonato, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, the calcium salt of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid monoethyl ester. 1.12. Acylaminophenols, for example 4-hydroxylauranylide, 4-hydroxysteatenylidene, octyl N- (3,5-di-tert-butyl-4-hydroxyphenyl) -carbamate. 1.13. Esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, , 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, trimethylhexandiol, trimethylol propane, 4-hydroxymethyl-l-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane. 1.14. Esters of β- (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-hexane diol, 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, trimethylhexandiol, trimethylolpropane, 4-hydroxymethyl-l-phospha-2, 6, 7-trioxabicyclo [2.2.2] octane. 1.15. Esters of ß- acid (3, 5-dicyclohexyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols, eg with methanol, ethanol, 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, 7-trioxabicyclo [2.2.2] octane. 1.16. Esters of 3,5-di-tert-butyl-4-hydroxyphenyl acetic acid with mono- or polyhydric alcohols for example with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonandiol, 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-phospha-2,6,6-trioxabicyclo [2.2.2] octane. 1.17. Amides of ß- (3,5-di-tert-butyl-4-hydroxy-enyl) -propionic acid, for example N, N'-bis (3, 5-di-tert-buyl-4-hydroxyl) -phenylpr opionyl) hexamethylene-di amide, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenyl-propionyl) trimethylene diamide, N, N'-bis (3 , 5-di-tert-butyl-4-hydroxy-phenylpropionyl) 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 O 1.19.Amino antioxidants, for example
N, N '-di-isopropyl-p-phenylenediamine, N, N' -di-sec-butyl-p-p-enylenediamine, 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 '-f-enyl-p-p-eneylenediamine, N- (1,3-dimethylbutyl) -N'-p-en-p-enylenediamine, N- (1-methylheptyl) -N'-phenyl-p-phenylenediamine, N-cyclohexyl-N '-f-enyl-p-p-eneylenediamine, 4- (p-toluenesulfamoyl) diphenylamine,
N, N'-dimethyl-N, N'-di-sec-butyl-p-phenylenediamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydifenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octyl) enyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine, for example p, p'-di-tert-octyldifenylamine, 4-n-butylaminofenol,
4-butyrylaminophenol, 4-nonanoylaminophenol,
4 - . 4-dodecane and lamino phenol, 4-acetylamino-phenol, 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'-dimet i lbutyl) f eni] amine, N-phenyl-1-naphthylamine tert-octylated, a mixture of mono- and dialkylated ter-butyl / tert-octyldiphenylamines, a mixture of mono- and dialkylated nonyl diphenylamines, a mixture of mono- and dialkylated dodecyldiphenyl-amines, a mixture of mono- and dialkylated isopropyl / -isohexyldiphenylamines, a mixture of mono- and dialkylated ter-butyldiphenylamines, 2,3-dihydro-3, 3-dimethyl-4H-l, 4-benzothiazine, phenothiazine, a mixture of tert-butyl / tert-octylphenothiazines mono- and dialkylated, a mixture of tert-octyl-phenothiazines mono- and di-alkyl, N- al 1 f ene ti az ina, N, N, N ', N' -tetraphenyl-l, 4-diaminobut-2-ene, N, N-bis- (2,2,6,6-tetramethyl-piperid-4-yl) -hexamet ilendiamine, bis (2, 2, 6, 6-tetramethylpiperid-4-yl) -sebacate, 2,2,6,6-tetramethylpiperidine -4-one, 2,2,6,6-tetramethylpiperidin-4-ol. 2. 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- (51-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'-octyloxyphenyl) benzotriazole, 2- (3', 5'-di-ter-amyl- 2'-hydroxyphenyl) benzotriazole, 2- (3 ', 5'-bis- (oi, o'-dimethylbenzyl) -2'-hydroxyphenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy) 5 '- (2-octyloxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-5' - [2- (2-ethylhexyloxy) -carbonylethyl] -2'-hydroxy-phenyl) - 5-chloro-benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '- (2-methoxycarbonylethyl) phenyl) -5-chloro-benzotriazole, 2- (3'-tert-butyl-2' -hidr oxy-5 '- (2-methoxycarbonylethyl) -phenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5' - (2-octyloxycarbonylethyl) phenyl) -benzotriazole, 2- (3'-ester) -butyl-5 • - [2- (2-ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl) benzotriazole, 2- (3'-dodecyl-2'-hydroxy-5'-methylphenyl) benzotriazole, 2- (3 '- tert-butyl-2'-hydroxy-5 '- (2-isooctyloxycarbonylethyl) phenylbenzotriazole, 2,2'-methylenebis- [4- (1,1,3,3-tetramethylbutyl) -6-benzotriazol-2-ylphenol]; the transesterification product 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' - ( c, a-dimethylbenzyl) -5 '- (1,1,3,3-tetramethylbutyl) -phenyl] benzotriazole; 2- [2'-Hydroxy-3 '- (1,1,3,3-tetramet-l-butyl) -5' - (, -dimet-l-benzyl) -phenyl] -benzotriazole. 2.2. 2-Hydroxybenzofeonases, for example the derivatives of 4-hydroxy, 4-methoxy, 4-octyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4, 2 ', 4' -trihydroxy and 2'-hydroxy-4, 4'-dimethoxy.
2. 3. Substituted and unsubstituted benzoic acid esters, such as for example 4-tert-butyl-phenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoyl resorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoyl resorcinol, 2, 4-di-tert-butylphenyl 3,5-ditert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3,5-di-tert-butyl-4-hydroxybenzoate , 2-methyl-4,6-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate. 2.4. Acrylates, for example ethyl O-cyano-β, β-diphenylacrylate, isooctyl oí-cyano-β, β-diphenylacrylate, methyl α-carbomethoxycinnamate, methyl oí-cyano-β-methyl-p-methoxy-cinnamate, butyl a-cyano -β-methyl-p-methoxy-cinnamate, methyl a-carbomethoxy-p-methoxycinnamate and N- (β-carbomethoxy-β-cyanovinyl) -2-methylindoline. 2.5. Nickel compounds, nickel compounds, for example 2, 2'-thio-bis- [4- (1,1,3,3-tetramethyl-butyl) phenol] nickel complexes, such as the complex 1: 1 or 1: 2, with or without additional ligands such as n-butylamine, triethanolamine or N-c iclohexildiet anolamine, nickel dibutyldithiocarbamate, nickel salts of monoalkyl esters, for example the methyl or ethyl ester of 4-hydroxy-3, 5 -di-tert-butylbenzylphosphonic acid, nickel complexes of ketoximes, for example 2-hydroxy-4-methylphenyl undecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands. 2.6. Sterically hindered amines, for example bis (2, 2, 6, 6-tetramethyl-4-piperidyl) sebacate, bis (2, 2, 6, 6-tetramethyl-4-piperidyl) succinate, bis (1, 2, 2, 6,6-pentamethyl-4-piperidyl) sebacate, bis (l-octyloxy-2, 2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1, 2, 2, 6, 6 -pentamethyl-4- piperidyl) -n-butyl-3, 5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1- (2-hydroxyethyl) -2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, condensates linear or cyclic N, N'-bis (2, 2, 6, 6 - tetrame il -4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1,3,5-triazine, tris ( 2, 2, 6, 6-tetramethyl-4-piperidyl) nitrilotriacetate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butane-tetra-carboxylate, 1,1 '- (1,2-ethanediyl) -bis (3,3,5,5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-etrame-ilpiperidine, 4-stearyloxy-2, 2,6,6- tetramethylpiperidine, bis (1,2,2,6,6-pentamethylpiperidyl) -2-n-butyl-2- (2-hydroxy-3) , 5-di-tert-butyl-benzyl) 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) sebacate, 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-morpholin-2,6-dichloro-1,3,5-triazine, the condensate of 2-chloro-4,6-bis (4- n-but ilamino -2, 2,6,6-tetramethoxypiperidyl) -1,3,5-triazine and 1,2-bis (3-aminopropylamino) ethane, the condensate of 2-chloro-4,6-di- (4 - n-but i lamino -1, 2,2,6,6-pentamethylpiperidyl) -1, 3, 5-triazine and 1,2-bis- (3-aminopropylamino) ethane, 8-aracetyl-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) pyrrolidine -2, 5-dione, 3-dodecyl-l- (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 p 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-1-oxa-3,8-diaza-4 -oxo-spiro [4, 5] -decane, a reaction product of 7,7,9,9-tetramethyl-2 - cycloundecyl-1-oxa-3, 8-diaza-4-oxospiro- [4,5] -decane and epichlorohydrin, 1, 1-bis (1, 2, 2, 6, 6-pentamethyl-4-piperidyloxycarbonyl) -2 - (4-methoxy-phenyl) ethene,
N, N'-bis-fbrmil-N, N'-bis (2, 2, 6,6-tetramethyl-4-piperidyl) hexamethyl-amine, diester of 4-methoxy-meth i-malonic acid with 1, 2, 2 , 6, 6 -pent amet-il-4-hydroxypiperidine, poly [methylpropyl-3 -oxy-4- (2,2,6,6-tetramethyl-4-piperidyl)] -siloxane, reaction product of anhydride copolymer of maleic acid α-olefin 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'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxyanilide, 2,2'-didodecyloxy-5, 5'-di- ter-butoxyanilide, 2-ethoxy-2'-ethyloxanilide, 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 oxanilides o and p-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-tridecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy) 3-but i loxi -propoxy) -phenyl] -4,6-bis (2,4-dimethyl) -1,3,5-triazine, 2 - [2-hydroxy-4 - (2-hydroxy-3-oct iloxy-propyloxy) phenyl] -4,6-bis (2,4-dimethyl) -1,3,5-triazine, 2- [4- (dodecyloxy / tridecyloxy-2-hydroxypropoxy) -2-hydroxy-phenyl] - 4, 6-bis (2,4-di methylphenyl) -1,3,5-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-) methoxyphenyl) -4,6-diphenyl-1,3,5-triazine, 2,4,6-tris [2-hydroxy-4- (3-butoxy-2-hydroxy-propoxy) phenyl] -1,3,5 -triazine, 2- (2-hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1,3,5-triazine, 2-. { 2-hydroxy-4- [3- (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 '-salicyloyl hydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-ter) -butyl-4-hydroxyphenylpropionyl) hydrazine, 3-salicylamino-1,4-triazole, bis (benzilidene) oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenylhydrazide, N, N'-diacetyladipyl dihydrazide, N, '-bis ( salicyloyl) oxalyl dihydrazide, N, N'-bis (salicyloyl) -thiopropionyl dihydrazide. 4. Phosphites and phosphonites, for example triphenyl phosphite, diphenyl alkyl phosphites, phenyl dialkyl phosphites, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecyl pentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) -pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) -pentaerythritol diphosphite, diisodecyloxypentaerythritol diphosphite, bis (2, 4 -di- tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tris (tert-butylphenyl) pentaerythritol diphosphite, tristearyl sorbitol triphosphite, tetrakis (2,4-di-tert-butylphenyl) 4,4'-biphenylene diphosphonyl, 6-isooctyloxy-2, 4,8, 10-tetra-tert-butyl-12H-dibenz [d, g] -1,3,2-dioxaphosphozin, 6-fluor-2, 4,8, 10-tetra -tert-butyl-12-methyl-dibenz [d,] -1, 3, 2-dioxaphosphocino, bis (2,4-di-tert-butyl-6-methylphenyl) methyl phosphite, 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, N-dioctadecylhydroxylamine, N-hexadecyl-N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N, N -dialkylhydroxylamine derived from hydrogenated tallow amine. 6. Nitrones, for example, N-benzyl-a-phenyl-nitrona, N-ethyl-a-methyl-nitrona, N-octyl-a-heptyl-nitrone, N-lauryl-cc-undecyl-nitrone, N-tetradecyl -a-tridecyl-nitrone, N-hexadecyl-a-pentadecyl-nitrona, N-octadecyl-oi-heptadecyl-nitrone, N-hexadecyl-a-heptadecyl-nitrone, N-ochatadecyl-a-pentadecyl-nitrone, N-heptadecyl α-heptadecyl-nitrone, N-octadecyl-oí-hexadecyl-nitrona, nitrone derived from N, N-dialkyl hydroxylamine derived from hydrogenated tallow amine. 7. Thiosineraists, for example, dilauryl thiodipropionate or distearyl thiodipropionate. 8. Peroxide scavengers, for example ß-thiodipropionic acid esters, for example lauryl, stearyl, myristyl-O tridecyl ester, mercaptobenzimidazole or the zinc salt of 2-mercapto benzimidazole, zinc dibutyldithiocarbamate, dioctadecyl disulfide, tetrakis pentaerythritol tetrakis (β-dodecyl mercapto) 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, polyvinyl pyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example stearate calcium, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony pyrocatechol or zinc pyrocatechol. 11. Nucleating agents, for example inorganic substances such as talcum, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates, 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 reinforcing agents, for example calcium carbonate, silicates, glass fibers, glass bulbs, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, sawdust and flours or fibers of other natural products, synthetic fibers. 13. Other additives, for example plasticizers, lubricants, emulsifiers, pigments, rheology additives, catalysts, flow control agents, optical brighteners, flameproofing agents, antistatic agents and blowing agents. 14. Benzofuranones and indolinones, for example those described in U.S. Patents. No. 4,325,863; No. 4,338,244; No. 5,175,312; No. 5,216,052; No. 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-butyl-benzofuran-2 -one, 5,7-di-ter -butyl -3- [4 - (2-stearoyloxyethoxy) phenyl] benzofuran-2-one, 3,3'-bis [5,7-di-tert-butyl -3- (4- [2-hydroxyethoxy] phenyl) benzofuran-2-one], 5, 7-di-tert -bu il -3- (4-ethoxyphenyl) bromo-2-one-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-benzofura-2-one, 3- (3, 4- dimethylphenyl) -5,7-di-tert-butyl-benzofuran-2-one, 3- (2,3-dimethylphenyl) -5,7-di-tert-butyl-benzofuran-2-one. The weight ratio of the product or the mixture according to this invention to the conventional additives may for example be 1: 0.5 to 1: 5. The products or mixtures of this invention can also be used as stabilizers, especially as light stabilizers, for almost all materials known in the photographic reproduction art and other reproduction techniques such as described for example in Research Disclosure 1990, 31429 ( pages 474 to 480). The invention is illustrated in more detail by the following Examples. All parts and percentages are given 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 starting material described in Example IA
is characterized by a numerical average molecular weight Mp
and the polydispersity Mw / Mn
The GPC (Gel Permeation Chromatography) is used as an analytical procedure to separate molecules by their difference in size and obtain averages
of molecular weight * -Mw * n) or information regarding the
molecular weight distribution of the polymers. The technique is well known and is described for example in "Modern Size" - Exclusion Liquid
Chromatography "(" Liquid Chromatography by Exclusion of Modern Size ") by W. Yan and colleagues, edited by
J. Wiley & Sons, N.Y., E.U.A. 1979, pages 4-8, 249-283 and
315-340. The GPC analysis shown in the following
Examples are carried out with an HPLC instrument, type MRTSP AS-1000, equipped with a MRUV 1000 UV / VIS detector having a wavelength of 250 nm. A mixed gel "GPC-SS-250 x 7.7 mm x 3/8" MRValco-Microgel-3 is used as a column.
The eluent (flow: Iml / min) is tetrahydrofuran-MRUvasol for spectroscopy (MRMerck-l .00016) + 0.02 mol / L diethanolamine (MRFluka 31590). 0.5 G of the sample to be examined is dissolved in 100 ml of eluent. The injection volume is 20 μL and the chromatogram period is 15 minutes. Example 1-1: Preparation of the product of the formula
To a solution of 221.2 g (1.2 moles) of cyanuric chloride in 1286 g of xylene, under stirring and nitrogen atmosphere, 254.8 g (1.2 moles) of N- (2, 2, 6, 6-tetramethyl-4-piperidyl) -n-Butylamine is added for 3 hours, maintaining the temperature at about 30 ° C during the addition. A thick but well stirrable suspension is obtained, which is maintained above the mentioned temperature for an additional 15 minutes. Subsequently, a mixture of 176.3 g of an aqueous solution of 30% NaOH (% w / v) and 200 ml of water is added for 1 hour at about 30 ° C.
The reaction mixture is maintained at about 30 ° C for a further 2.5 hours. During this time, all the solids are dissolved and an emulsion is formed. Then, the basic aqueous solution is separated. The remaining xylene solution is heated to 50 ° C and 236.8 g (0.6 mol) of N, N'-bis (2, 2, 6,6-tetramethyl-4-piperidyl-l, 6-hexanediamine in 200 g of water They are added for 2 hours, Subsequently, 176.3 g of an aqueous solution of 30% NaOH (% w / v) are added during 2 hours, during the addition, the temperature is maintained at approximately 50 ° C. Then the temperature is increased by 1 hour at about 80 ° C. The reaction mixture is kept under stirring at 80 ° C. for a further 1.5 hours.The aqueous basic solution is separated at about 80 ° C. and 380 g of xylene are removed by vacuum distillation (68-). 82 ° C / 200-120 mbar) to the organic solution, which is maintained at about 80 ° C, 118.4 g (0.3 mol) of N, N'-bis (2, 2, 6, 6-tetramethyl-4-piperidyl) -1,6-hexanediamine are added during 5 minutes. Subsequently, the reaction mixture is stirred for 5 minutes and 92 g of an aqueous solution of 30% NaOH (% w / v) are added at about 80 ° C for 5 minutes. Then, the reaction mixture is transferred to a pressure reactor. 300 g of water and 170 g of xylene are added and after closing the reactor and after making inert with nitrogen, the temperature is raised to 160 ° C for 2 hours. The mixture is maintained at 160 ° C for 9 hours under 5.4 bar pressure. After cooling to 60 ° C, 89.0 g (0.69 mol) of di-n-butylamine are added for 5 minutes and subsequently 86.4 g of a 30% aqueous solution of NaOH (% w / v) are added for 5 minutes. After closing the reactor again, the mixture is heated at 160 ° C for 1 hour and maintained at 160 ° C for 4 hours under 5 bar pressure. After cooling to 60 ° C, 130 g of xylene and 150 g of water are added. The mixture is heated to 90 ° C under stirring. The aqueous solution is separated. The organic phase is washed twice with 400 g of water and dried azeotropically. The solution is cooled to approximately 30 ° C, filtered and concentrated in vacuo. (125-230 ° C / 350-l mbar). Upon cooling, the product melt gives a solid. The melting point of the product obtained is 133-137 ° C. (by GPC = gel permeation chromatography)
= 2200 g / mol = 1.6 Mw / Mn The GPC analysis showed a chromatogram as in Figure 1. Analysis of the product obtained: Compound with n '= 1: 39% mol Compound with n' = 3: 20 mol% Compound with n '= 5: 9.3% mol Compound with n' = 7: 4.4% mol Example 1-2: Preparation of the product of the formula
To a solution of 55.3 g (0.3 mol) of cyanuric chloride in 250 ml of methyl isobutyl ketone which is maintained at about 5 ° C, 63.7 g (0.3 mol) of N- (2, 2, 6, 6-tetramethyl-4) -piperidinyl) -n-butylamine are added, maintaining the temperature at about 5 ° C during the addition. Then, 40 ml of water are added together with an aqueous solution of 30% NaOH (% w / v).
After the addition, the mixture is heated to room temperature and 59.2 g (0.15 mol) of N, N'-bis (2,2,6,6-tetramethyl-4-piperidinyl) -1,6-hexandiamine in
125 ml of methyl isobutyl ketone are added at room temperature. The mixture is then heated to 60 ° C and after an addition of more than 40 ml of water, it is maintained at 60 ° C for 1 hour. 40 G of an aqueous solution of 30% NaOH (% w / v) are added and the mixture is heated to 70 ° C. After 1/2 hour, 200 ml of methyl isobutyl ketone and 30 ml of water are distilled off at 70 ° C with slight vacuum. To the organic mixture maintained at 70 ° C, 29.6 g (0.075 mol) of N, N '- (2, 2, 6, 6-tetramethyl-4-piperidinyl) -1,6-hexanediamine are added and 20 g Additional 30% aqueous NaOH solution (% w / v) are added. Then, the reaction mixture is transferred to a pressure reactor. 50 ml of methyl isobutyl ketone and 40 ml of water are added and after closing the reactor and subjecting it to inertia with nitrogen, the temperature is raised to 160CC. The mixture is maintained at 160 ° C for 4 hours under 6 bar pressure. After cooling to 60 ° C, 36.6 g (0.17 mol) of N- (2,2,6,6-tetramethyl-4-piperidinyl) -n-butylamine are added together with 20 g of an aqueous solution of 30% NaOH. % (% p / v). After closing the reactor again, the mixture is heated to 140 ° C and maintained at 140 ° C for 4 hours under 5 bar pressure. After cooling to 50 ° C, 125 ml of methyl isobutyl ketone and 100 ml of water are added. The basic aqueous solution is separated and the organic phase is washed once with 100 ml of water. The organic phase is concentrated under vacuum at 220 ° C / 20 mbar. After cooling, the fusion product gives a solid with m.p. = 172-174 ° C. (per GPC) = 2080 g / mol Mn
= 1.52 Mw / Mn The GPC analysis showed a chromatogram as in Figure 2. The analysis of the obtained product: Compound with n '= 1 31% mol Compound with n' = 3 23% mol Compound with n '= 5 5% mol Compound with n '= 7 1 mol% Example 1: Preparation of the product of the formula A mechanically stirred 1.0-L four-necked flask was charged with 40.0 g (0.16 mol) of the product according to 1-1, 0.40 g of Mo03 and 320 ml of cyclohexane. The mixture is heated to reflux. 82.4 G
(0.64 mol) of 70% t-butylhydroperoxide are added in 30 minutes. Water was collected by azeotropic distillation and the reflux is continued for one hour. The reaction mixture is transferred to a magnetically stirred glass pressure bottle and heated at 130 ° C for 5 hours. The reaction mixture is cooled to 70 ° C and Mo03 is filtered off. The filtrate is washed with a solution of 20 g of Na 2 SO 3 in 100 ml of H 2 O for one hour at 60 ° C. The phases are separated, the organic phase is dried over MgSO4 and the total volume is reduced to 100 ml. The solution is drowned in 500 ml of methanol at 5 ° C. The precipitate is filtered and dried at 52.8 g (95% theory). The product obtained has a melting range of 140 ° -170 ° C.
-H NMR: 0.85-2.40 ppm (complex mixture); 3.25-3.35 ppm
(s, broad, NCH2); 3.62 ppm (s, broad, NOCH); 4.90-5.40 ppm (broad, NCH). ^ C NMR: 81.8 ppm (NOCH); 165 ppm (triazine C) The ratio of protons to 3.25, 3.62 and 4.90 ppm is 2: 1: 1. Example 1-A: Preparation of the product of the formula
A mixture of 885 g (3.54 moles) of product from Example 1-1, 6000 g (71.4 moles) of cyclohexane and 2.2 g of molybdenum trioxide, it is heated to reflux. A solution of 3360 g of 70% aqueous t-butyl hydroperoxide (26.1 moles) is added to the reflux mixture for 1-2 hours and water is removed by azeotropic distillation. The reaction mass is transferred to a pressure reactor and heated at 125 ° C to 2.1-3.5 bar (30-50 psig) until the red color is discharged. The crude reaction mass is cooled and treated with aqueous sodium sulfite to destroy the residual peroxide. The aqueous layer is separated and the organic layer is concentrated under reduced pressure to a melt which is fed slowly into cold methanol to obtain after filtration a whitish solid product. Average transmission values (10% toluene): 425 nm = 21.8%; 450 nm = 37.4%; 475 nm = 62.6% Example 1-B: Preparation of the product of the formula
The procedure of Example 1-A is repeated, except that during processing, the melt obtained after cyclohexane is removed, diluted with t-butyl alcohol and concentrated to 50% solids. The solution is cooled and the cold methanol is added rapidly to produce, after filtration, a whitish solid product. Average transmission values (10% toluene): 425 nm = 57.0%; 450 nm = 71.5%; 475 nm = 79.7% Example 2: Preparation of the product of the formula
A 4-neck round bottom flask with 1.0 L capacity, mechanically agitated, is charged with 40.0 g (0.160 mol) of the product according to Example 1-1, 0.40 g of Mo03 and 320 ml of n-octane. The mixture is heated to reflux and 82.4 g (0.640 mol) of t-butylhydroperoxide are added within 30 minutes. Water is removed by azeotropic distillation and reflux is continued for 90 minutes. The reaction mixture is transferred to a magnetically stirred pressure bottle and heated at 135 ° C for 3 hours. Mo03 is filtered and the filtrate is washed with a solution of 20 g of Na 2 SO 3 in 100 ml of H 2 O for 30 minutes at 60 ° C. The phases are separated, the organic phase is washed with 100 ml of water and then with 100 ml of saturated NaCl. The organic phase is dried over MgSO and then evaporated to 100 ml of total volume. The solution is drowned in 500 ml of methanol at 5 ° C. The precipitate, a soft crystal, is dried for 1 hour in a vacuum oven of 55 CC. The product, now a hard glass, is broken with a mortar and then dried at 47.4 g (78% theory). The product has a melting range of 95-120 ° C. H NMR: 0.82-2.40 ppm (complex mixture); 3.25-3.40 ppm
(s, broad, NCH2); 3.60 - 3.92 ppm (complex,
NOCH and NCH2 of NC4H9); 4.90-5.40 ppm (complex,
NCH). -C NMR: 78.6-83.4 ppm (three peaks, NOCH); 165 ppm (triazine C) The ratio of protons to 3.25 and 4.90 is 2: 1. Example 2 -A: Preparation of the product of the formula
A mixture of 1304 g (5.21 moles) of the product of Example 1-1, 10.3 kg (90.2 moles) of octane and 4.0 g of molybdenum trioxide is heated to reflux. A solution of 3873 g of 70% aqueous t-butyl hydroperoxide (30.1 moles) is added to the reflux mixture for 1-2 hours and water is removed by azeotropic distillation. The reaction mass is heated to reflux at atmospheric pressure until the red color is discharged. The crude reaction mass is cooled and treated with aqueous sodium sulfite to destroy the residual peroxide. The aqueous layer is divided and the organic layer is concentrated under reduced pressure to a melt which is fed slowly into cold methanol to obtain after filtration a whitish solid product. Average transmission values (10% xylene): 425 nm = 39.3%; 450 nm = 75.1%; 475 nm = 87.3% Example 2-B: Preparation of the product of the formula
The procedure of Example 2-A is repeated, except that during processing, the melt obtained after octane is removed, diluted with t-butyl alcohol and concentrated to 50% solids. The solution is cooled and the cold methanol is added rapidly to result after filtration, a whitish solid product. Average transmission values (10% toluene): 425 nm = 59.8%; 450 nm = 82.5%; 475 nm = 91.2% Example I-A: Light stabilizing action 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 calcium monoethyl 3,5-di-t-butyl-4-hydroxybenzyl phosphonate, g of calcium stearate and 2.5 g of titanium dioxide are mixed in a slow mixer with 1000 g of polypropylene powder having a melt index = 12 g / 10 minutes (measured at 230 ° C and 2.16 kg). The mixtures are extruded at 200-230 ° C to obtain polymer granules which are then converted into fibers using a pilot type apparatus (MRLeonard-Sumirago (VA), Italy) and which operates under the following conditions: Extruder Temperature: 230-245 Head temperature: 255-260 Stretching ratio: 1: 3.5 Linear density: 11 dtex per. filament
The fibers prepared in this way are exposed, after mounting on a white board, on a 65 WR Weather-O-Meter (ASTM D2565-85) weathermeter with a black panel temperature of 63 ° C. For samples taken after various times of exposure to light, the residual toughness is measured using a constant speed tensiometer and the exposure time in hours required to make half the initial tenacity (T50), then calculated. Table 1: T50 Stabilizer at Hours Compound of Example 1-1 3490 The compound listed in Table 1 shows good light stabilizing activity in polypropylene fibers. Example I-B: Interaction of pigment in polypropylene plates. 5.625 g of the stabilizer shown in Table 2, 13,500 g of Pigment Blue 15"Flush" (50% blend in polyethylene) and 25,875 g of polypropylene powder (having a melt index of approximately 14, measured at 230 ° C and 2.16 Kg) are added to fill an internal MRHaake mixer at room temperature (MRHaake Buchler Rheochord System 40 using a 60 cc 3-piece Re-mixer with cam blades). The cam blades rotate at 5 RPM (revolutions per minute). A ram closes the bowl with a weight of 5 kg. The temperature is increased to 180 ° C and maintained at 180 ° C. The total time is 30 minutes. The mixture is removed while it is at 180 ° C after 30 minutes and cooled to room temperature. The mixture thus obtained - called the "concentrate" - will be used again. 0.900 g of this concentrate, 3,600 g of titanium dioxide "Flush" (mixture at 50% in polyethylene) and 40,500 g of polypropylene powder (which has a melting index of approximately 14 measured at 230 ° C and 2.16 Kg) Add to a mixing bowl "HAAKE" at 160 ° C. Cam blades rotate at 20 RPM. A ram closes the bowl under a weight of 5 kg. The temperature is increased to 170 ° C and the RPM increases to 125. The total time is 30 minutes. The molten mixture is removed at 170 ° C, transferred to a hand tool at room temperature and transformed into a round plate of 1 mm x 25 mm in diameter. The mixture thus obtained is called "relaxed product" and the plate "relaxed product plate". The color difference,? E (CIÉ color difference equation), of the relaxed product plate of sample containing the stabilizer indicated in Table 2 against relaxed control product plate without stabilizer is measured. The measurement was made using an Applied Color Systems Spectrophotometer Model CS-5 (E.U.A.). The measurement parameters used are 400-700 nm - scanning, small area vision, reflectance, illuminated D65, observer at 10 degrees. The above processing conditions are designed to simulate the manufacture of concentrates (master batches) of pigments and stabilizers and the subsequent relaxed product (dilution) in finished plastic articles. A high value of dE indicates pigment agglomeration and poor dispersion. A deE of 0.5 or less will not be noticeable as different to the naked eye. Table 2: Stabilizer E Compound of Example 1-1 0.5 The stabilizer listed in Table 2 shows low pigment interaction in polypropylene plates. This is advantageous. Example I-C; Light stabilizing action in polypropylene tapes. 1 g of each of the compounds listed in Table 3, 1 g of tris [2,4-di-tert-butylphenyl] phosphite, 0.5 g of pentaerythritol tetrakis [3- (3, 5-di-tert-butyl- 4-hydroxyphenyl) propionate] and 1 g of calcium stearate are mixed in a turbomixer with 1000 g of polypropylene powder having a melt index of 2.1 (measured at 230 ° C and 2.16 Kg). The mixtures are extruded at 200-220 ° C to give polymer granules that are subsequently converted to stretched tapes with a thickness of 50 μm and with a width of 2.5 mm, using a semi-industrial type apparatus.
(MRLeonard-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 are assembled in a white card or on a white card and expose a
Intermeter (Weather-O-Meter) 65 WR (ASTM D 2565-85) with a black panel temperature of 63 ° C. The residual tenacity is measured by a constant speed tensometer, in a sample taken after several times of exposure to light; from this, the exposure time (in hours) required to halve the initial tenacity (T50) is measured.
Table 3: Stabilizer T5_, n0 in hours
Compound of Example 1-1 3170 The compound listed in Table 3 shows a good light stabilizing activity in polypropylene tapes. Example I-D: Antioxidant action in polypropylene plates. 1 g of each of the compounds listed in Table 4 and 1 g of calcium stearate are mixed in a slow mixer with 1000 g of polypropylene powder having a melt index of 4.3 (measured at 230 ° C and 2.16 Kg). The mixtures are extruded at 200-220 ° C to give polymer granules which are then converted into 1 mm thick plates by injection molding at 220 ° C. The plates are then punched using a DIN 53451 mold and the specimens obtained are exposed in an air oven with forced circulation which is maintained at a temperature of 135 ° C. The specimens are checked at regular intervals by bending them 180 ° C in order to determine the time (in hours) required to fracture them. Table 4: Stabilizer Time in hours
required for fractures
Compound of Example 1-1 1830 The compound listed in Table 4 is a good antioxidant in polypropylene plates. Example I-E: Color of polypropylene plates after aging in the oven. 5 g of each of the compounds listed in Table 5, 1 g of tris [2,4-di-tert-butylphenyl] phosphite, 1 g of pentaerythritol tetrakis [3- (3,5-di-tert-butyl) 4-hydroxyphenyl) propionate] and 1 g of calcium stearate are mixed in a slow mixer with 1000 g of polypropylene powder having a Melt Index of 2.1 (measured at 230 ° C and 2.16 Kg). The mixtures are extruded twice at 200-220 ° C to give polymer granules which are then converted into 1 mm thick plates by molding with pressure at 230 ° C for 6 minutes. The plates are then exposed for seven days in an air oven with forced circulation maintained at 120 ° C. After oven exposure, the Yellowness Index (YI = Yellowness Index) of the plates is measured according to ASTM D 1925 by the MRMINOLTA CR 210 chromometer (MINOLTA - Japan). Table 5: Stabilizer YI according to ASTM D 1925
Example Compound 1-1 18.7 The polypropylene plates stabilized with the compound listed in Table 5 have good Yellowness index after aging in the furnace. Example I-F: Rotational molding. Linear low density polyethylene (Copolymer-Hexene, MRQuantum MP635-661, MI = 6.5 dg / min, density = 0.935 g / cm3), which contains 0.05% zinc stearate, 0.05% pentaerythritol tetrakis [3 - (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate] and 0.10% tris [2,4-di-tert-butylphenyl] phosphite, dry mix with 0.17% of the compound of Example 1-1 and then formulated in fusion at 234 ° C in nodules. The fully formulated and pelleted resin is ground to a powder using a Model 50 Spray (Reduction Engineering) (particle size between 100 mesh and 35 mesh). The ground resin is placed in a cast aluminum mold (40.64 x 40.64 x 15.24 cm (16 x 16 x 6 inches)) that is rotated biaxially in a gas-fired oven in a rotational molder at laboratory scale (FSP M20 MRClamshell) Processing conditions are either: 15 minutes at 288 ° C (= Condition 1) or 12 minutes at 316 ° C (= Condition 2). a) Color determination Molded boxes are cut into 5.08 x 5.08 cm (2 x 2 inches) plates and exposed in a Blue M forced-draft oven at 120 ° C. The Yellowness Index is determined in an Applied Color spectrophotometer
Systems by the reflectance mode according to ASTM D
1925. Samples containing the compound of Example 1-1 exhibit low color after molding and after thermal aging. b) UV stabilizing activity Other 5.08 x 5.08 cm (2 x 2 inches) plates from molded boxes are exposed in a MRAtlas xenon arc weathermeter (Xenon-Arc-Weather-O-Meter) in accordance with ASTM G26. at 63 ° C pbt, 0.35 kW / cm2 a
340 nm. Samples are tested periodically for a change in impact resistance, using a Tower of
Drop Model 825.0 of MRDynatup. The failure in this test is determined by the observation of the loss of impact resistance of the plates. The longer this property loss takes to occur, the more effective the stabilizing system is. Plates containing the compound of Example 1-1 exhibit good light stabilizing activity as determined by the above criteria. Example A: Pigmented thermoplastic olefin nodules
(TPO) are prepared by preparing a polyolefin mixture (polypropylene containing an ethylene-propylene copolymer; MRPolytrope TPP 518-01 from MRA Schulman, Inc.; Akron, Ohio, USA) with the additives listed below in an extruder single spindle MRSuperior / MPM 1"with a general spindle for all purpose (24: 1 L / D) at 200 ° C, cooled in a water bath and pelletized .Before extrusion and molding, the additives are mixed in dry mixed in a drum dryer Additives: 0.25% * 'of MRRed 3B (Pigment Red 177, color index 65300), 0.2% *' of 2- (2 '-hydroxy-3', 5 '-di-ter-amylphenyl ) benztriazole, 0.2% * 'of bis (l-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate, calcium stearate O.l, approximately 10% * of talc and the stabilizers listed in Table 6
* 'percent by weight based on polyolefin mixture The resulting nodules are molded into 1524 mm thick plates (5.08 x 5.08 cm (2 x 2 inches)) at approximately 190 ° C in an MRBOY 30M Injection Molding Machine . The test plates are mounted on metal racks and exposed on an M65mm Xenon Are
(Weather-O-Meter) at black panel temperature of 70 ° C, 0.55 W / m2 at 340 nanometers and 50% relative humidity with intermittent light / dark cycles and water spray (MRSociety of Automotive Engineers (MRSociedad de Ingenieros Automotive - SAE J 1960 Test Procedure Exterior Automobile Conditions.) Brightness measurements of the test specimens are performed on a 60 ° MRBYK-GARDNER Turbidity / Brightness Meter according to ASTM D 523. The results are shown in the Table 6. Table 6: Stabilizers Gloss retention after hours, weathermeter 0 hours 0 hours (= 0 kJ / m2"») • = 2500 kJ / m2 **> 0.05% * 'pentaerythritol tetrakis [3- (3 , 5-di-tert-butyl-4-hydroxyphenyl) -propionate], 0.05% * 'tris [2,4-di-tert-butylphenyl] -phosphite, 100.0% 90.5% Q.20% * of the compound of Example 1
0. 05% * 'pentaerythritol tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) -propionate], 0.05% *' tris [2,4-di-tert-butylphenyl] -phosphite, 100.0% 91.9 % Stabilizers Gloss retention after hours, weathermeter 0 hours 0 hours (? = 0 kJ / m2 ** ')' (? = 2500 J / m2"') 0.20% *' of the compound of Example 2 0.05% * 'of di (hydrogenated tallow) -hydroxylamine 0.20% *) of the compound of Example 1 100.0% 87.3%
0. 05% *) of di (hydrogenated tallow) -hydroxylamine 0.20% * 'of the compound of Example 2 100.0% 88.0%
* 'percent by weight based on the mixture of polyolefins **' refers to incident energy expressed as kJ / m2 measured at 340 nm The formulations containing the stabilizers listed in Table 6 show much greater resistance to photodegradation than those without the stabilizers. Unstabilized test specimens fail rapidly under UV exposure established above. Example B: Polypropylene with fiber grade containing 0.05% by weight of calcium stearate and 0.05% by weight of di (hydrogenated tallow) hydroxylamine as base stabilization, dry mix with the stabilizer indicated in Table 7 and then formulated in fusion at 234 ° C in nodules. The fully formulated and pelleted resin is then centrifuged at 246 ° C or 274 ° C in fibers using a model MRHills laboratory fiber extruder. The 41 filament spinning wick is stretched at a ratio of 1: 3.2 to give a final denier of 615/41. "Socks are knitted" from the stabilized polypropylene in a MRLawson-Hemphill Analysis Weaver and exposed in an MRAtlas (Xenon-Arc-Weather-Ometer) weathermeter using Auto Interior conditions SAE J1885 at 89 ° C bpt, 0.55 kW / cm2 at 340 nm without dew cycle. Failure in this test is determined by observing the physical failure of the sock when it is "scraped" with a blunt glass rod. The longer this catastrophic failure takes, the stabilizer is more effective. The results are given in Table 7.
Table 7 Stabilizer Failure Time Catastrophic Failure Time Catastrophic Fiber Centrifugal Fiber at 246 ° C Centrifuged at 274 ° C
None 192 hours 96 hours
0. 25% by weight of the compound of Example 1 600 hours 408 hours
0. 25% by weight of the compound of Example 2 600 hours 408 hours
Claims (31)
- CLAIMS 1. A product obtained by 1) reacting a compound of the formula (OI); with a compound of the formula (ß); in a stoichiometric ratio to obtain a compound of the formula (y): 2) react the compound of the formula (ß) with the compound of the formula (y) in a molar proportion of0. 4: 1 to 0.75: 1; 3) reacting the end groups of the formula (d) present in the reaction product 2) with a compound of the formula (e) A-H (e) in a molar ratio of 2: 1.7 to 2: 3; reactions 1) to 3) are carried out in an organic solvent in the presence of an inorganic base; and 4) transfer the groups of the formula (G-I) present in the reaction product 3) to groups of the formula (G-II); the transfer is carried out by reacting the product of the reaction 3) with a hydroperoxide in a hydrocarbon solvent, in the presence of a peroxide decomposition catalyst; Rx is a hydrocarbyl radical or -O-Rx is oxyl; R 2 is alkylene with 2 to 12 carbon atoms, alkenylene with 4 to 12 carbon atoms, cycloalkylene with 5 to 7 carbon atoms, cycloalkylene with 5 to 7 carbon atoms-di (alkylene with 1 to 4 carbon atoms), alkylene with 1 to 4 carbon atoms-di (cycloalkylene with 5 to 7 carbon atoms), phenylene di (alkylene with 1 to 4 carbon atoms) or alkylene with 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl, -O- or > N-XX with X? which is acyl with 1 to 12 carbon atoms or (alkoxy with 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), ( Ib) or (Ic); C - S - C H "I H2 with m being 2 or 3, X 2 is alkyl having 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; and the X3 radicals independently of each other are alkylene with 2 to 12 carbon atoms; A is -0R3, -N (R4) (R5) or a group of the formula (II): R3, R4 and R5, which are identical or different, are alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; alkenyl with 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl or C2-4 alkyl which is substituted in the 2, 3 or 4 position by -OH, C1-C8 alkoxy, di (C1-C4 alkyl) -amino or a group of the formula (III): / \ Y N (III) with Y which is -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 are alkyl with 1 to 18 carbon atoms, alkenyl with 3 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenylalkyl having 7 to 9 carbon atoms which is unsubstituted 0 substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl, a group of the formula (GI), or alkyl having 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (alkyl with 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.
- 2. A product according to claim 1, characterized in that R2 is alkylene with 2 to 12 carbon atoms, cycloalkylene with 5 to 7 carbon atoms, cycloalkylene with 5 to 7 atoms carbon-di (alkylene with 1 to 4 carbon atoms), alkylene with 1 to 4 carbon atoms-di (cycloalkylene with 5 to 7 carbon atoms), phenylendi (alkylene with 1 to 4 carbon atoms) or alkylene with 4 to 12 carbon atoms interrupted by -O- or > N-XX with X x which is acyl with 1 to 12 carbon atoms or (C 1 -C 12 alkoxy) carbonyl or having one of the definitions of R 4; or R2 is a group of the formula (I-b); R3, R4 and R5 which are identical or different are alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which are unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 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 having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups having 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 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 with 2 to 10 carbon atoms, cyclohexylene, cyclohexylendi (alkylene with 1 to 4 carbon atoms), alkylene with 1 to 4 carbon atoms-dicyclohexylene or phenylene (alkylene with 1 to 4 carbon atoms); R3, R4 and R5 which are identical or different are alkyl with 1 to 12 carbon atoms, cycloalkyl with 5 to 7 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; benzyl which is unsubstituted or substituted on the phenyl by alkyl having 1 to 4 carbon atoms; or -N (R4) (R5) is additionally a group of the formula (III); and R6 is alkyl with 1 to 12 carbon atoms, cycloalkyl with 5 to 7 carbon atoms which is unsubstituted or substituted by 1, 2 or 3, alkyl with 1 to 4 carbon atoms; benzyl which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 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 with 2 to 8 carbon atoms; R3, R4 and R5, which are identical or different, are alkyl with 1 to 8 carbon atoms, cyclohexyl which is unsubstituted or substituted by methyl; phenyl which is unsubstituted or substituted by methyl; benzyl or -N (R4) (R5) is additionally 4-morpholinyl; and R6 are alkyl with 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 Rx is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 4) depending on R is octane or cyclohexane; R2 is alkylene with 2 to 6 carbon atoms; A is -N (R4) (R5) or a group of the formula (II); R4 and R5 which are identical or different are alkyl with 1 to 8 carbon atoms; or -N (R4) (R5) is further 4-morpholinyl; X is > NR6; R6 is alkyl with 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 R1 is octyl or cyclohexyl, and the hydrocarbon solvent in reaction 4) depending on R1 # is octane or cyclohexane; R2 is alkylene with 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 with 1 to 8 carbon atoms; B is a group of the formula (II); X is > NR6; R6 are alkyl with 1 to 8 carbon atoms.
- 8. A product according to claim 1, characterized in that the organic solvent in reactions 1) to 3) is an aromatic hydrocarbon or an aliphatic ketone and the inorganic base is a sodium hydroxide, potassium hydroxide, sodium carbonate or Potassium carbonate.
- 9. A product according to claim 1, characterized in that the reaction 1) is carried out at a temperature of 10 ° C to 90 ° C, reaction 2) is carried out at a temperature of 110 ° C to 200 ° C. ° C and reaction 3) is carried out at a temperature of 110 ° C to 180 ° C.
- 10. A product according to claim 1, characterized in that the reactions 2) and 3) are carried out under pressure.
- 11. A product according to claim 1, characterized in that R? is alkyl with 5 to 18 carbon atoms, alkenyl with 5 to 18 carbon atoms, alkynyl with 5 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms unsubstituted or substituted by alkyl with 1 to 4 carbon atoms; cycloalkenyl with 5 to 12 carbon atoms unsubstituted or substituted by alkyl with 1 to 4 carbon atoms; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms or phenylalkyl with 7 to 9 carbon atoms unsubstituted or substituted on the phenyl by alkyl having 1 to 4 carbon atoms; and the hydrocarbon solvent in reaction 4) depending on R 1 f is alkane with 5 to 18 carbon atoms, alkene with 5 to 18 carbon atoms, alkyne with 5 to 18 carbon atoms, cycloalkane with 5 to 12 carbon atoms without replace or substituted by alkyl with 1 to 4 carbon atoms; cycloalkene with 5 to 12 carbon atoms unsubstituted or substituted by alkyl with 1 to 4 carbon atoms; a bicyclic or tricyclic hydrocarbon having 6 to 10 carbon atoms or phenylalkan with 7 to 9 carbon atoms unsubstituted or substituted on the phenyl by alkyl having 1 to 4 carbon atoms.
- 12. A product according to claim 1, characterized in that Rx is heptyl, octyl, cyclohexyl, methylcyclohexyl, cyclooctyl, cyclohexenyl, α-methylbenzyl or 1, 2, 3, 4-tetrahydronaphtenyl and the hydrocarbon solvent in reaction 4) depending on Rl. f is heptane, octane, cyclohexane, methylcyclohexane, cyclooctane, cyclohexene, ethylbenzene or tetralin.
- 13. A product according to claim 1, characterized in that R1 is octyl or cyclohexyl and the hydrocarbon solvent of reaction 4) is depending on Rlf is octane or cyclohexane.
- 14. A product according to claim 1, characterized in that the radical -O-R] is oxyl and the hydrocarbon solvent in reaction 4) is an inert organic solvent.
- 15. A product according to claim 1, characterized in that the peroxide decomposition catalyst is a metal carbonyl, metal oxide, metal acetylacetonate or metal alkoxide wherein the metal is selected from groups IVb, Vb, VIb , VIIb and VIII of the Periodic Table.
- 16. A product according to claim 1, characterized in that the hydroperoxide is t-butyl hydroperoxide and the peroxide decomposition catalyst is Mo03.
- 17. A product according to claim 1, characterized in that per mole of group of the formula (G-I) present in the product of the reaction 3) 2 to 8 moles of the hydroperoxide, 0.001 to 0.1 mole of the peroxide decomposition catalyst and 5 to 30 moles of the hydrocarbon solvent, are applied.
- 18. A product obtained 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).
- 19. A mixture containing a monodisperse compound of the formula (P-I), a monodisperse compound of the formula (P-II) and a monodisperse compound of the formula (P-III), the compounds only differ in the number of repeating units, the total amount of the compound of the formula (PI) is 15 to 45 mol%, the total amount of the compound of the formula (P-III) is 15 to 35 mol% and the total amount of the compound of the formula (P-III) ) is 3 to 18% mol, with respect to the total mixture; and Rx is hydrogen, a hydrocarbyl radical or -0-R? _ is oxyl; R2, is alkylene with 2 to 12 carbon atoms, alkenylene with 4 to 12 carbon atoms, cycloalkylene with 5 to 7 carbon atoms, cycloalkylene with 5 to 7 carbon atoms-di (alkylene with 1 to 4 carbon atoms) , C 1 -C 4 -alkylene (cycloalkylene with 5 to 7 carbon atoms), phenylendi (C 1 -C 4 -alkylene) or C 4 -C 12 -alkylene interrupted by 1,4-piperazindiyl , -O - or > N-XX with Xx which is acyl with 1 to 12 carbon atoms or (C 1 -C 12 alkoxy) carbonyl or has one of the definitions of R 4 given below; or R2 is a group of the formula (I-a), (I-b) or (I-c), - H (I -b) C - C - c - H, I H " with m being 2 or 3, X 2 is alkyl having 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; and the X3 radicals independently of each other are alkylene with 2 to 12 carbon atoms; A * is -OR3, -N (R4) (R5) or a group of the formula (G-IV); R3, R4 and R5 which are identical or different, are alkyl having 1 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; alkenyl with 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl having 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (C1-C4 alkyl) amino or a group of the formula (III); / \ N-: ni) \ / with Y which is -O-, -CH2-, -CH2CH2 - or > N-CH3; and R3 further is hydrogen or -N (R4) (R5) is further a group of the formula (III); X * is -O - or > N-R6 *; R6 * is alkyl with 1 to 18 carbon atoms, alkenyl with 3 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms. carbon; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted on the phenyl 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl, a group of the formula (G-II), or alkyl having 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (C1-C4 alkyl) 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 *.
- 20. A mixture according to claim 19, characterized in that it additionally contains a monodisperse compound of the formula (P-IV), the total amount of the compound of the formula (P-IV) is 1 to 15 mol%, based on the total mixture.
- 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, heat or oxidation induced degradation which comprises incorporating into the organic material a product according to claim 1.
- 25. A product that is obtained by 1) reaction of a compound of the formula (OÍ) Cl. N.ClCl (a) N. N B in a stoichiometric ratio to obtain a compound of the formula (y- I); 2) reacting the compound of the formula (β-I) with the compound of the formula (β-I) in a molar ratio of 0.4: 1 to 0.75: 1; 3) react the extreme groups of the formula (d) present in the reaction product 2) with a compound of the formula (e) A-H (e) in a molar ratio of 2: 1.7 to 2: 3; reactions 1) to 3) are carried out in an organic solvent in the presence of an inorganic base; Z is hydrogen, alkyl with 1 to 8 carbon atoms, hydroxyalkyl with 2 to 8 carbon atoms, OR; -OH, hydrocarbyloxy with 1 to 18 carbon atoms, -CH2CN, alkenyl with 3 to 6 carbon atoms, alkynyl with 3 to 6 carbon atoms, phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; or acyl with 1 to 8 carbon atoms; R 2 is alkylene with 2 to 12 carbon atoms, alkenylene with 4 to 12 carbon atoms, cycloalkylene with 5 to 7 carbon atoms, cycloalkylene with 5 to 7 carbon atoms-di (alkylene with 1 to 4 carbon atoms), C 1 -C 4 -alkylene (cycloalkylene with 5 to 7 carbon atoms), phenylenedi (C 1 -C 4 -alkylene) or alkylene with 4 to 12 carbon atoms interrupted by 1,4-piperazindiyl, -O- or > N-XX with Xx that is acyl with 1 • at 12 carbon atoms or (C 1 -C 12 alkoxy) carbonyl or has one of the definitions of R 4 given below except for hydrogen; or R2 is a group of the formula (I-a), (I-b) or (I-c); C- C H "H" (I-b) X, with m which is 2 or 3, X2 is alkyl with 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alc xi with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; and the X3 radicals independently of each other are alkylene with 2 to 12 carbon atoms; A is -0R3, -N (R4) (R5) or a group of the formula (II-1); O O X, > X, o or ai-i: R3, R4 and R5, which are identical or different, are hydrogen, alkyl having 1 to 18 carbon atoms, cycloalkyl with 5 to 12 carbon atoms, which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; alkenyl with 3 to 18 carbon atoms, phenyl which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms or alkoxy with 1 to 4 carbon atoms; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl or alkyl having 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (C1-C4 alkyl) amino or a group of the formula (III); / \ Y N-:? N: \ with And that e_s -O-, -CH2-, -CH2CH2- or > N-CH 3, or -N (R 4) (R 5) is additionally a group of the formula (III); X is -O- or > N-R6; R6 is hydrogen, alkyl having 1 to 18 carbon atoms, alkenyl having 3 to 18 carbon atoms, cycloalkyl having 5 to 12 carbon atoms which is unsubstituted or substituted by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms. carbon; phenylalkyl with 7 to 9 carbon atoms which is unsubstituted or substituted in the phenyl by 1, 2 or 3 alkyl groups with 1 to 4 carbon atoms; tetrahydrofurfuryl, a group of the formula (IV-1), or alkyl having 2 to 4 carbon atoms which is substituted in the 2, 3 or 4 position by -OH, alkoxy with 1 to 8 carbon atoms, di (C1-C4 alkyl) 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, characterized in that it has a polydispersity M ^ / MR "of 1-1 to 1-7-
- 29. A mixture containing a monodisperse compound of the formula (M-II-a), a monodisperse compound of the formula (M-II-a) and a monodisperse compound of the formula (M-III-a), the compounds differ only in the number of repetitive units, the radicals A, B, R, Z and R2 are as defined in claim 25 and the total amount of the compound of the formula (MIa) is 15 to 45 mol%, the total amount of the compound of the formula (M- II-a) is 15 to 35 mol% and the total amount of the compound of the formula (M-III-a) is 3 to 18 mol%, relative to the total mixture (= 100 mol%).
- 30. A mixture according to claim 29, characterized in that Z is hydrogen or alkyl having 1 to 4 carbon atoms; R2 is alkylene with 2 to 6 carbon atoms; R is a group of the formula (IV-1); A is -N (R4) (R5); R4 and R5 which are identical or different are alkyl with 1 to 8 carbon atoms; B is a group of the formula (II-1); X is > NR6; R6 is alkyl with 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 OF THE INVENTION A product that is obtained by 1) reacting a compound of the formula (OI) Cl N Cl N N N B with a compound of the formula (ß¡ in a stoichiometric ratio to obtain a compound of the formula (Y); 2) react the compound of the formula (ß) with the compound of the formula (y) in a molar proportion of0. 4: 1 to 0.75: 1; 3) react the end groups of the formula (d) present in the reaction product 2), with for example dibutylamine in a molar ratio of 2: 1.7 to 2: 3; reactions 1) to 3) are carried out in an organic solvent in the presence of an inorganic base; and 4) transfer the groups of the formula present in the reaction product 3) to groups of the formula , the transfer is carried out by reacting the product of reaction 3) with a hydroperoxide in a hydrocarbon solvent in the presence of a peroxide decomposition catalyst; R1 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.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP97810329.9 | 1997-05-27 | ||
EP97810325.7 | 1997-05-27 |
Publications (1)
Publication Number | Publication Date |
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MXPA99010923A true MXPA99010923A (en) | 2000-09-04 |
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