NL9300634A - NEW PIPERIDINE-TRIAZINE CO-OLIGOMERS FOR USE AS STABILIZERS IN ORGANIC MATERIALS. - Google Patents
NEW PIPERIDINE-TRIAZINE CO-OLIGOMERS FOR USE AS STABILIZERS IN ORGANIC MATERIALS. Download PDFInfo
- Publication number
- NL9300634A NL9300634A NL9300634A NL9300634A NL9300634A NL 9300634 A NL9300634 A NL 9300634A NL 9300634 A NL9300634 A NL 9300634A NL 9300634 A NL9300634 A NL 9300634A NL 9300634 A NL9300634 A NL 9300634A
- Authority
- NL
- Netherlands
- Prior art keywords
- alkyl
- group
- alkylene
- piperidyl
- tert
- Prior art date
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- 239000011368 organic material Substances 0.000 title claims description 10
- 239000003381 stabilizer Substances 0.000 title description 9
- YPSLATCYOGSFDU-UHFFFAOYSA-N piperidine;triazine Chemical compound C1CCNCC1.C1=CN=NN=C1 YPSLATCYOGSFDU-UHFFFAOYSA-N 0.000 title description 4
- -1 tetrahydrofurfuryl Chemical group 0.000 claims description 159
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 37
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 16
- 239000004743 Polypropylene Substances 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 239000004698 Polyethylene Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 229920000573 polyethylene Polymers 0.000 claims description 9
- 229920001155 polypropylene Polymers 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 125000003031 C5-C7 cycloalkylene group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 229920001059 synthetic polymer Polymers 0.000 claims description 6
- 241001104043 Syringa Species 0.000 claims description 5
- 235000004338 Syringa vulgaris Nutrition 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 229920000098 polyolefin Polymers 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims description 3
- 230000000087 stabilizing effect Effects 0.000 claims description 3
- 125000005065 undecenyl group Chemical group C(=CCCCCCCCCC)* 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims 2
- 238000006731 degradation reaction Methods 0.000 claims 2
- 230000000306 recurrent effect Effects 0.000 claims 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
- 125000002993 cycloalkylene group Chemical group 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 47
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 36
- 229920001577 copolymer Polymers 0.000 description 33
- 150000001875 compounds Chemical class 0.000 description 26
- 229920000642 polymer Polymers 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 14
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- WVYWICLMDOOCFB-UHFFFAOYSA-N 4-methyl-2-pentanol Chemical compound CC(C)CC(C)O WVYWICLMDOOCFB-UHFFFAOYSA-N 0.000 description 10
- 239000004952 Polyamide Substances 0.000 description 10
- 229920002647 polyamide Polymers 0.000 description 10
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000011572 manganese Substances 0.000 description 9
- 239000008096 xylene Substances 0.000 description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- 238000007069 methylation reaction Methods 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 239000012964 benzotriazole Substances 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 230000011987 methylation Effects 0.000 description 7
- 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 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000835 fiber Substances 0.000 description 6
- 239000004417 polycarbonate Substances 0.000 description 6
- 229920006324 polyoxymethylene Polymers 0.000 description 6
- 229920006380 polyphenylene oxide Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 229920002554 vinyl polymer Polymers 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical group CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 0 C*(**(*)C(NC(*)*1)NC1(C)C1CCCC1)C1CC(C)(C)N(C)C(C)(C)C1 Chemical compound C*(**(*)C(NC(*)*1)NC1(C)C1CCCC1)C1CC(C)(C)N(C)C(C)(C)C1 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 239000005038 ethylene vinyl acetate Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229920001897 terpolymer Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 2
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 2
- UCJDCGANFAKTKA-UHFFFAOYSA-N 2,4-dimethyl-1,3,5-triazine Chemical compound CC1=NC=NC(C)=N1 UCJDCGANFAKTKA-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 125000005250 alkyl acrylate group Chemical group 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 150000004681 metal hydrides Chemical class 0.000 description 1
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- 125000005394 methallyl group Chemical group 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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- 235000014593 oils and fats Nutrition 0.000 description 1
- 125000001117 oleyl 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])=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
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000003431 oxalo group Chemical group 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960000969 phenyl salicylate Drugs 0.000 description 1
- ZPNJBTBYIHBSIG-UHFFFAOYSA-N phenyl-(2,2,6,6-tetramethylpiperidin-4-yl)methanone Chemical compound C1C(C)(C)NC(C)(C)CC1C(=O)C1=CC=CC=C1 ZPNJBTBYIHBSIG-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000012994 photoredox catalyst Substances 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
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920003251 poly(α-methylstyrene) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002312 polyamide-imide Polymers 0.000 description 1
- 229920002480 polybenzimidazole Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
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- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 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
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 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
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- 125000005591 trimellitate group Chemical group 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
- 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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0273—Polyamines containing heterocyclic moieties in the main chain
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/02—Polyamines
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
- C08L79/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
Nieuwe pjperidine-triazine co-ollgomeren voor gebruik als stabilisatoren in organische materialen.New piperidine triazine co-olgomers for use as stabilizers in organic materials.
De onderhavige uitvinding heeft betrekking op nieuwe piperidine-triazine co-oligomeren, voor hun gebruik als licht-stabilisatoren, warra-te-stabilisatoren en oxidatie-stabilisatoren in organische materialen, in het bijzonder synthetische polymeren, en op organische materialen die aldus zijn gestabiliseerd.The present invention relates to novel piperidine triazine co-oligomers, for their use as light stabilizers, heat stabilizers and oxidation stabilizers in organic materials, especially synthetic polymers, and to organic materials thus stabilized.
De stabilisatie van synthetische polymeren door triazine-oligomeren en -co-oligomeren met verbindingen die 2,2,6,6-tetramethylpiperidinegroe-pen bezitten is beschreven in verschillende octrooischriften, in het bijzonder in de hierna volgende octrooischriften US-A-4.086.204, US-A-4.315-859. USrA-4.331.586, US-A-4.335.242, US-A-4.4l2.020, US-A- 4.459.395. US-A-4.477.615, US-A-4.547.548, EP-A-II7.229 en EP-A-0217.149 en JP-A-Sho-63.196.654.The stabilization of synthetic polymers by triazine oligomers and co-oligomers with compounds possessing 2,2,6,6-tetramethylpiperidine groups has been described in several patents, in particular in the following patents US-A-4,086,204 , US-A-4,315-859. USrA-4,331,586, US-A-4,335,242, US-A-4,412,020, US-A-4,459,395. US-A-4,477,615, US-A-4,547,548, EP-A-II7,229 and EP-A-0217,149 and JP-A-Sho-63,196,654.
De onderhavige uitvinding heeft betrekking op nieuwe piperidine-triazine co-oligomeren met de terugkerende eenheden met de formules (Ia) en (Ib)The present invention relates to novel piperidine triazine co-oligomers having the recurring units of formulas (Ia) and (Ib)
met een gemiddeld molecuulgewicht van 1000 tot 20.000 en een (Ia):(Ib) verhouding van 4:1 tot 1:4, waarin Rx een -0R5, -SR5 ofwith an average molecular weight of 1000 to 20,000 and an (Ia) :( Ib) ratio of 4: 1 to 1: 4, wherein Rx is -0R5, -SR5 or
** groep is, waarin R5, R6 en R7 gelijk of verschillend kunnen zijn en een waterstofatoom, een Ci-Cl8 alkyl, C5-C12 cycloalkyl welke ongesubstitueerd is of 1, 2 of 3 maal gesubstitueerd is door een Ci-C/, alkylgroep; C3-Cl8 alkenyl, fenyl welke niet gesubstitueerd is of 1, 2 of 3 maal gesubstitueerd door een C^-C* alkyl of alkoxy; C?-C9 fenylalkyl welke niet gesubstitueerd is of 1, 2 of 3 maal gesubstitueerd op de fenylgroep door een C1-Cil alkyl; tetrahydrofurfuryl, l,2,2,6,6-pentamethyl-4-piperi- dyl of 02-0ή alkyl gesubstitueerd op de 2, 3 of 4-positie door een C^-Cg alkoxy, door een di^-C*, alkyl)amino of door een groep met formule (II)** group in which R5, R6 and R7 may be the same or different and a hydrogen atom, a C 1 -C 18 alkyl, C 5 -C 12 cycloalkyl which is unsubstituted or 1, 2 or 3 times substituted by a C 1 -C 8 alkyl group ; C 3 -C 18 alkenyl, phenyl which is unsubstituted or 1, 2 or 3 times substituted by a C 1 -C 8 alkyl or alkoxy; C 1 -C 9 phenylalkyl which is unsubstituted or 1, 2 or 3 times substituted on the phenyl group by a C 1 -C 11 alkyl; tetrahydrofurfuryl, 1,2,6,6,6-pentamethyl-4-piperidyl or O 2 -Oή alkyl substituted in the 2, 3 or 4 position by a C 1 -C 8 alkoxy, by a di 1 -C *, alkyl) amino or by a group of formula (II)
(II) waarin A een directe binding, -0-, -CH2-, -CH2CH2- of >N-CH3, of Rx is een groep met formule (II) of een van de groepen met de formules (Illa)-(IIIc)(II) wherein A is a direct bond, -0-, -CH2-, -CH2CH2- or> N-CH3, or Rx is a group of formula (II) or one of the groups of formulas (Illa) - (IIIc )
(lila) (Illb) (IIIC) waarin R8 is C1-Cia alkyl, cycloalkyl welke niet gesubstitueerd is of 1, 2 of driemaal gesubstitueerd door een Cj-C*, alkylgroep; C7-Cg fenyl-alkyl welke niet gesubstitueerd is of 1, 2 of driemaal gesubstitueerd in de fenylgroep door een Οχ-Οή alkylgroep; of 1,2,2,6,6-pentamethyl-^-pipe-ridyl, m is een geheel getal van 2 tot 6, n is nul of 1, X is -0- of >N-CH3 en R? heeft dezelfde betekenis als Rg of een waterstofatoom, R2 heeft dezelfde betekenis als R8 of een waterstofatoom, R3 is een C2-C12 alky-leen, ϋή-012 alkyleen onderbroken door 1, 2 of 3 zuurstofatomen of door een groep >N-CH3; C5-C7 cycloalkyleen, C5-C7 cycloakyleendi(C1-C/, alky- leen), Cj-C/, alkyleendi(C5-C? cycloalkyleen), C2-Ci, alkyleendi(C5-C7 cyclo-alkyleen) of fenyleendimethyleen en is C2-C12 alkyleen, Cz,-C12 alkyleen onderbroken door 1, 2 of 3 zuurstofatomen; 2-hydroxytrimethyleen, fenyleendimethyleen, carbonyl, C2-C15 diacyl, Ci,-C15 dicarbamoyl, een groep -(CH2)p-C0- waarin p een geheel getal is van 1 tot 10, of een groep -C00-Rlo-00C~waarin R10 dezelfde betekenis heeft als R3.(lilac) (Illb) (IIIC) wherein R 8 is C 1 -C 7 alkyl, cycloalkyl which is unsubstituted or 1, 2 or 3 times substituted by a C 1 -C * alkyl group; C7-C8 phenyl alkyl which is unsubstituted or 1, 2 or three times substituted in the phenyl group by a Οχ-Οή alkyl group; or 1,2,2,6,6-pentamethyl - ^ - pipe-ridyl, m is an integer from 2 to 6, n is zero or 1, X is -0- or> N-CH3 and R? has the same meaning as Rg or a hydrogen atom, R2 has the same meaning as R8 or a hydrogen atom, R3 is a C2-C12 alkylene, ϋή-012 alkylene interrupted by 1, 2 or 3 oxygen atoms or by a group> N-CH3; C5-C7 cycloalkylene, C5-C7 cycloakylene di (C1-C /, alkylene), C 1 -C 3, alkylene di (C5-C 7 cycloalkylene), C2-C 1, alkylene di (C5-C7 cycloalkylene) or phenylene dimethylene and C 2 -C 12 alkylene, C 2 -C 12 alkylene is interrupted by 1, 2 or 3 oxygen atoms; 2-hydroxytrimethylene, phenylene dimethylene, carbonyl, C2-C15 diacyl, C1, -C15 dicarbamoyl, a group - (CH2) p-C0- where p is an integer from 1 to 10, or a group -C00-R10 -00C ~ where R10 has the same meaning as R3.
De co-oligomeren volgens de uitvinding kunnen verschillende eind-standige groepen bezitten, afhankelijk van het soort en de moleculaire verhoudingen van de gebruikte reagentia bij de bereiding.The co-oligomers of the invention may have different terminal groups depending on the type and molecular proportions of the reagents used in the preparation.
De eindstandige groep gebonden aan de triazinering van formule (Ia) - in het gevolg aangeduid als Xx - is bijvoorbeeld in het bijzonder Cl, OH, ONa, OK of een groep Rx of een groepFor example, the terminal group bound to the triazine ring of formula (Ia) - consequently referred to as Xx - is in particular Cl, OH, ONa, OK or a group Rx or a group
en de eindstandige groep gebonden aan het stikstofatoom van formule (Ia) of (Ib) is bijvoorbeeld een methylgroep of een groepand the terminal group bonded to the nitrogen atom of formula (Ia) or (Ib) is, for example, a methyl group or a group
waarin dezelfde betekenis als boven bezit, of een groep -R^OH.which has the same meaning as above, or a group -R ^ OH.
De verschillende groepen Rlt R2, R3 en R4 van de formules (Ia) en (Ib), kunnen in elk geval gelijk of verschillend zijn.The different groups R1, R2, R3 and R4 of the formulas (Ia) and (Ib) can in any case be the same or different.
Voorbeelden van alkylgroepen met niet meer dan 18 koolstofatomen zijn methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, tert-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl en oc-tadecyl.Examples of alkyl groups with no more than 18 carbon atoms are methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, pentyl, 2-pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, tert-octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl and octadecyl.
Voorbeelden van 02-0ή alkyl gesubstitueerd door C^-Cg alkoxy, bij voorkeur door C1-Ci alkoxy, in het bijzonder oethoxy of ethoxy, zijn 2-methoxyethyl, 2-ethoxyethyl, 3~methoxypropyl, 3-ethoxypropyl, 3~bu- toxypropyl, 3~octoxypropyl en 4-methoxybutyl.Examples of O 2 -O 4 alkyl substituted by C 1 -C 6 alkoxy, preferably by C 1 -C 6 alkoxy, especially oethoxy or ethoxy, are 2-methoxyethyl, 2-ethoxyethyl, 3-methoxypropyl, 3-ethoxypropyl, 3-buoxy toxypropyl, 3-octoxypropyl and 4-methoxybutyl.
Voorbeelden van C2-Ch alkyl gesubstitueerd door d± (0Χ—C/, alkyl)ami-no, bij voorkeur door dimethylamino of diëthylamino, zijn 2-dimethylami-noethyl, 2-diëthylaminoethyl, 3”dimethylaminoproyl, 3“diëthylaminopropyl, 3-dibutylaminopropyl en 4-diëthylaminobutyl.Examples of C 2 -C 6 alkyl substituted by d ± (0Χ-C /, alkyl) amino, preferably by dimethylamino or diethylamino, are 2-dimethylaminoethyl, 2-diethylaminoethyl, 3 "dimethylaminoproyl, 3" diethylamino-propyl, 3- dibutylaminopropyl and 4-diethylamino butyl.
Een representatief voorbeeld van C2-C^, alkylgroep gesubstitueerd door een groep met formule (II) is de groep met de formuleA representative example of C 2 -C 7 alkyl group substituted by a group of formula (II) is the group of formula
heeft de voorkeur.is preferred.
Voorbeelden van niet-gesübstitueerde of gesubstitueerde C5-C12-cy-cloalkyl zijn cyclopentyl, methylcyclopentyl, dimethylcyclpentyl, cyclo-hexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, tert-butylcyclohexylf cyclo-octyl, cyclodecyl en cyclododecyl. Niet-gesubsti-tueerd of 01-0ήalkyl gesubstitueerd cyclohexyl heeft de voorkeur.Examples of unsubstituted or substituted C5 -C12 cycloalkyl are cyclopentyl, methylcyclopentyl, dimethylcyclpentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, tert-butylcyclohexylcycloecyl, cyclodecyl, cyclodecyl. Unsubstituted or O 1 -alkyl substituted cyclohexyl is preferred.
Voorbeelden van alkenyl zijn allyl, 2-methylallyl, butenyl, hexenyl, decenyl, undecenyl of oleyl. Allyl heeft de voorkeur. Het koolstof atoom in positie 1 is bij voorkeur verzadigd.Examples of alkenyl are allyl, 2-methylallyl, butenyl, hexenyl, decenyl, undecenyl or oleyl. Allyl is preferred. The carbon atom in position 1 is preferably saturated.
Voorbeelden van gesubstitueerde fenylgroepen zijn methylfenyl, dimethylfenyl, trimethylfenyl, tert-butylfenyl, di-tert-butylfenyl, 3,5~ di-tert-butyl-4-methylfenyl, methoxyfenyl en ethoxyfenyl.Examples of substituted phenyl groups are methylphenyl, dimethylphenyl, trimethylphenyl, tert-butylphenyl, di-tert-butylphenyl, 3,5-di-tert-butyl-4-methylphenyl, methoxyphenyl and ethoxyphenyl.
Voorbeelden van fenylalkylgroepen welke niet gesubstitueerd of gesubstitueerd zijn op de fenylgroep zijn benzyl, methylbenzyl, dimethyl-benzyl, trimethylbenzyl, tert-butylbenzyl en 2-fenylethyl. Benzyl heeft de voorkeur.Examples of phenylalkyl groups which are unsubstituted or substituted on the phenyl group are benzyl, methylbenzyl, dimethylbenzyl, trimethylbenzyl, tert-butylbenzyl and 2-phenylethyl. Benzyl is preferred.
Voorbeelden van C2-C12 alkyleengroepen zijn ethyleen, propyleen, trimethyleen, tetramethyleen, pentamethyleen, 2,2-dimethyltrimethyleen, hexamethyleen, trimethylhexamethyleen, octamethyleen, decamethyleen en dodecamethyleen. 'Examples of C 2 -C 12 alkylene groups are ethylene, propylene, trimethylene, tetramethylene, pentamethylene, 2,2-dimethyltrimethylene, hexamethylene, trimethylhexamethylene, octamethylene, decamethylene and dodecamethylene. '
Voorbeelden van Ci,-C12 alkyleengroep onderbroken door 1, 2 of 3 zuurstofatomen zijn 3“°x&pentaan-l,5-diyl, 4-oxaheptaan-l,7-diyl, 3.6- dioxaoctaan-1,8-diyl, 4,7-dioxadecaan-l,10-diyl, 4,9~dioxadodecaan-1,12- diyl en 3.6,9“trioxaundecaan-l,ll-diyl.Examples of C 1 -C 12 alkylene group interrupted by 1, 2 or 3 oxygen atoms are 3 ° x x & pentane-1,5-diyl, 4-oxaheptane-1,7-diyl, 3,6-dioxaoctane-1,8-diyl, 4.7 -dioxadecane-1,110-diyl, 4,9-dioxadodecane-1,12-diyl and 3,6,9 "trioxaundecane-1,11-diyl.
Een representatief voorbeeld van een C/(-C12 alkyleengroep en R3 en R10 onderbroken door een groep >N-CH3 is de groepA representative example of a C / (- C12 alkylene group and R3 and R10 interrupted by a group> N-CH3 is the group
Representatieve voorbeelden van groepen met 1 of 2 C5-C7 cycloalky-leengroepen zijn cyclohexyleen, methylcyclohexyleen, cyclohexyleendime-thyleen, methyleendicyclohexyleen en isopropylideendicyclohexyleen.Representative examples of groups with 1 or 2 C5-C7 cycloalkylene groups are cyclohexylene, methylcyclohexylene, cyclohexylene dimethylene, methylene dicyclohexylene and isopropylidene dicyclohexylene.
Representatieve voorbeelden van C2-C15 diacyl R^ zijn oxalyl, malo-nyl, ethylmalonyl, butylmalonyl, benzylmalonyl, succinyl, glutaryl, adi-poyl, trimethyladipoyl, sebacoyl, oxydiacetyl, cyclohexaandicarbonyl, ftaaloyl, isoftaloyl en tereftaloyl C2-C15 alkaandioyl niet-gesubstitueerd of gesubstitueerd door benzyl; C^-C15 alkaandioyl waarin de alkaangroep is onderbroken door een zuurstofatoom; (C5-C7 cycloalkaan)dicarbonyl, ftaaloyl, isoftaaloyl en tereftaaloyl hebben de voorkeur.Representative examples of C 2 -C 15 diacyl R 4 are oxalyl, malonyl, ethylmalonyl, butylmalonyl, benzylmalonyl, succinyl, glutaryl, adi-poyl, trimethyladipoyl, sebacoyl, oxydiacetyl, cyclohexanediocyl, isophthaloyl, C2-isophthaloyl, C2-isophthaloyl C2 or substituted by benzyl; C 1 -C 15 alkanedioyl in which the alkane group is interrupted by an oxygen atom; (C5-C7 cycloalkane) dicarbonyl, phthaloyl, isophthaloyl and terephthaloyl are preferred.
,(C2-C13 alkyleen)dicarbamoyl,, (C2-C13alkylene) dicarbamoyl,
Representatieve voorbeelden van Ci,-C15 dicarbamoyl R* zijn hexame-thyleendicarbamoyl, trimethylhexamethyleendicarbamoyl, cyclohexyleendi-carbamoyl, fenyleendicarbamoyl, toluyleendicarbamoyl of een groep ofRepresentative examples of C 1 -C 15 dicarbamoyl R * are hexamethylenedicarbamoyl, trimethylhexamethylenedicarbamoyl, cyclohexylene dicarbamoyl, phenylenedicarbamoyl, toluylenedicarbamoyl or a group or
C5-C7 cycloalkyleen)dicarbamoyl, fenyleendicarbamoyl, toluyleendicarbamoyl en de groepen hebben de voorkeur.C5-C7 cycloalkylene) dicarbamoyl, phenylenedicarbamoyl, toluylenedicarbamoyl and the groups are preferred.
De co-oligomeren die de voorkeur bezitten hebben de steeds terugkerende eenheden met de formules *(Ia) en (Ib) met een gemiddeld molecuulge-wicht van 1000 tot 10.000 en een (Ia):(Ib) verhouding van 3:1 tot 1:3, waarin R1 is een groep -0R5,. -SR5 ofThe preferred co-oligomers have the recurring units of formulas * (Ia) and (Ib) with an average molecular weight of 1000 to 10,000 and a (Ia) :( Ib) ratio of 3: 1 to 1 : 3, where R1 is a group -0R5 ,. -SR5 or
waarin r5 , R6 en R7 gelijk of verschillend kunnen zijn en een waterstofatoom, 0χ-0ι6 alkyl, C5-Cg cycloalkyl welke niet gesubstitueerd is of 1, 2 of 3 maal gesubstitueerd door alkyl; C3-C12 alkenyl, fenyl welke niet gesubstitueerd is of 1 of 2 of 3 maal gesubstitueerd door C,-C/, alkyl of Cj^-C/, alkoxy; benzyl welke niet gesubstitueerd is of mono-, twee of driemaal gesubstitueerd op de fenylgroep door een C^-C/, alkyl; tetrahydro-furfuryl, 1,2,2,6,6-pentamethyl-4-piperidyl of C2-C3 alkyl gesubstitueerd op de 2- of 3”POsitie door C^-Ci, alkoxy, door di^-C^ alkyljamino of een groep met formule (II) waarin A is een directe binding, -0-, -CH2- of -CH2CH2-, of Rx is de groep met formule (II) of een van de groepen met de formules (IlIa)-(IIIc) waarin R8 is C1-C12 alkyl, C5-C8 cycloalkyl welke niet gesubstitueerd of 1, 2 of 3 maal gesubstitueerd door alkyl; benzyl welke niet is gesubstitueerd of 1, 2 of 3 maal gesubstitueerd op de fenyl door Cj-C/, alkyl; of 1,2,2,6,6-pentamethyl-4~piperidyl, m is 2, 3 of k, n is nul of 1, X is -0- of >N-CH3 en R9 heeft dezelfde betekenis als Rg of waterstofatoom, R2 heeft dezelfde betekenis als R8 of waterstofatoom, R3 is C2-C10 alkyleen, Ci,-C10 alkyleen onderbroken door 1, 2, of 3 zuurstofatomen of een >N-CH3-groep; cyclohexyleen, cyclohexyleendimethy-leen, methyleendicyclohexyleen, isopropylideendieyclohexyleen of feny-leendimethyleen en R4 is C2-C10 alkyleen, 0ή-010 alkyleen onderbroken door 1, 2 of 3 zuurstofatomen; 2-hydroxytrimethyleen, fenyleendimethyleen, carbonyl, C2-Ci0 diacyl, C/,-C12 dicarbamoyl, een groep -(CH2)pC0- waarin p is een geheel getal van 1 tot 5. of een groep -C00-Rlo-00C- waarin R10 de bovenvermelde betekenis van R3 bezit.wherein r5, R6, and R7 may be the same or different and a hydrogen atom, Oχ-O6 alkyl, C5-C8 cycloalkyl which is unsubstituted or 1, 2 or 3 times substituted by alkyl; C 3 -C 12 alkenyl, phenyl which is unsubstituted or substituted 1 or 2 or 3 times by C 1 -C 3 alkyl or C 1 -C 3 alkoxy; benzyl which is unsubstituted or mono-, substituted two or three times on the phenyl group by a C 1 -C 18 alkyl; tetrahydrofurfuryl, 1,2,2,6,6-pentamethyl-4-piperidyl or C 2 -C 3 alkyl substituted at the 2- or 3 ”position by C 1 -C 1, alkoxy, by di-C 1 -alkyl amino or group of formula (II) in which A is a direct bond, -0-, -CH2- or -CH2CH2-, or Rx is the group of formula (II) or one of the groups of formulas (IlIa) - (IIIc) wherein R8 is C1 -C12 alkyl, C5 -C8 cycloalkyl which is unsubstituted or 1, 2 or 3 times substituted by alkyl; benzyl which is unsubstituted or substituted 1, 2 or 3 times on the phenyl by C 1 -C 6 alkyl; or 1,2,2,6,6-pentamethyl-4-piperidyl, m is 2, 3 or k, n is zero or 1, X is -0- or> N-CH3 and R9 has the same meaning as Rg or hydrogen atom R 2 has the same meaning as R 8 or hydrogen atom, R 3 is C 2 -C 10 alkylene, C 1 -C 10 alkylene interrupted by 1, 2, or 3 oxygen atoms or a> N-CH 3 group; cyclohexylene, cyclohexylene dimethylene, methylene dicyclohexylene, isopropylidene diyclohexylene or phenylene dimethylene and R4 is C2-C10 alkylene, O-010 alkylene interrupted by 1, 2 or 3 oxygen atoms; 2-hydroxytrimethylene, phenylenedimethylene, carbonyl, C 2 -C 10 diacyl, C /, - C 12 dicarbamoyl, a group - (CH 2) pCO - where p is an integer from 1 to 5. or a group -C00-R 10 -00C- where R10 has the above-mentioned meaning of R3.
De eo-oligomeren die in het bijzonder de voorkeur bezitten omvatten steeds terugkomende eenheden met de formules (Ia) en (Ib) met een gemiddeld molecuulgewicht van 1000 tot 8000 en een (Ia): (Ib) verhouding van 2:1 tot 1;3. waarin Rx is een groep -0R5, -SR5 ofParticularly preferred eol oligomers include recurring units of formulas (Ia) and (Ib) with an average molecular weight of 1000 to 8000 and a (Ia): (Ib) ratio of 2: 1 to 1; 3. where Rx is a group -0R5, -SR5 or
waarin R5 is Cx-C12 alkyl, cyclohexyl welke niet gesubstitueerd is of 1, 2 of 3 maal gesubstitueerd door CX-CA alkyl; allyl, undecenyl, fenyl, benzyl, tetrahydrofurfuryl of 1,2,2,6,6-pentamethyl-4-piperidyl, R6 en R? welke gelijk of verschillend kunnen zijn hebben de bovenvermelde betekenis voor R5 of zijn waterstofatoom of C2-C3 alkyl gesubstitueerd in de 2-of 3_POSitie door Ci-Ci, alkoxy, door dimethylamino, door diëthylamino of door een 4-morfolinylgroep, of Rx is 4-morfolinyl of een van de groepen met de formules (lila)-(IIIc) waarin R8 is 0χ-08 alkyl, cyclohexyl welke niet gesubstitueerd is of 1, 2 of 3 maal gesubstitueerd door CX-CA alkyl; benzyl of l,2,2,6,6-pentamethyl-4-piperidyl, m is 2 of 3» n is nul of 1, X is -0- of >N-CH3 en R9 heeft dezelfde betekenis als R8 of waterstof, R2 heeft dezelfde betekenis als Rg of waterstof, R3 is C2-Cg alkyleen, C8-C10 alkyleen onderbroken door 2 of 3 zuurstofatomen; cyclohexyleendimethy-leen, methyleendicyclohexyleen of fenyleendimethyleen en Ri, is C2-Cg alkyleen, C^-Cg alkyleen onderbroken door 1 of 2 zuurstofatomen; 2-hydroxytri-methyleen, fenyleendimethyleen, carbonyl, C2-Cg diacyl, Ci,-C10 dicarba-moyl, een groep -(CH2)pC0- waarin p is 1, 2 of 3. of een groep -COO-R10-00C- waarin R10 de bovenvermelde betekenis van R3 bezit.wherein R5 is Cx-C12 alkyl, cyclohexyl which is unsubstituted or 1, 2 or 3 times substituted by CX-CA alkyl; allyl, undecenyl, phenyl, benzyl, tetrahydrofurfuryl or 1,2,2,6,6-pentamethyl-4-piperidyl, R 6 and R 6 which may be the same or different have the above meaning for R 5 or its hydrogen atom or C 2 -C 3 alkyl substituted in the 2 or 3 position by C 1 -C 1, alkoxy, by dimethylamino, by diethylamino or by a 4-morpholinyl group, or Rx is 4 morpholinyl or one of the groups of the formulas (IIIa) - (IIIc) wherein R 8 is 0χ-08 alkyl, cyclohexyl which is unsubstituted or 1, 2 or 3 times substituted by CX-CA alkyl; benzyl or 1,2,2,6,6-pentamethyl-4-piperidyl, m is 2 or 3 »n is zero or 1, X is -0- or> N-CH3 and R9 has the same meaning as R8 or hydrogen, R2 has the same meaning as Rg or hydrogen, R3 is C2-C8 alkylene, C8-C10 alkylene interrupted by 2 or 3 oxygen atoms; cyclohexylene dimethylene, methylene dicyclohexylene or phenylene dimethylene and R 1, C 2 -C 8 alkylene, C 1 -C 8 alkylene is interrupted by 1 or 2 oxygen atoms; 2-hydroxy-trimethylene, phenylenedimethylene, carbonyl, C 2 -C 6 diacyl, C 1 -C 10 dicarbamoyl, a group - (CH 2) pCO- where p is 1, 2 or 3. or a group -COO-R10-00C- wherein R10 has the above-mentioned meaning of R3.
De co-oligomeren van bijzonder belang zijn die met de terugkerende eenheden met de formules (Ia) en (Ib) met een gemiddeld molecuulgewicht van 1500 tot 6000 en een (Ia):(Ib) verhouding van 2:1 tot 1:2, waarin Rx is een groep -0R5 ofThe co-oligomers of particular interest are those with the recurring units of formulas (Ia) and (Ib) with an average molecular weight of 1500 to 6000 and a (Ia) :( Ib) ratio of 2: 1 to 1: 2, where Rx is a group -0R5 or
waarin R5 is Ci-Cg alkyl, cyclohexyl, allyl, benzyl, tetrahydrofurfuryl of l^^.ö.ó-pentamethyl-^-piperidyl, R6 en R7 welke gelijk of verschillend kunnen zijn hebben de betekenis van R5 of waterstof, of R2 is 4-morfolynyl of één van de groepen met de formules (lila)-(IIIc) waarin Rg is l,2,2,6,6-pentamethyl-4-piperidyl, m is 2, n is nul of 1, X is -0- of >N-CH3 en Rg is waterstof of l,2,2,6,6-pentamethyl-4-piperidyl, R2 is waterstof, methyl of l^^.G.G-pentamethyl-^-piperidyl, R3 is C2-Cg alkyleen, C6-C10 alkyleen onderbroken door 2 of 3 zuurstofatomen; cyclohexy-leendimethyleen, methyleendicyclohexyleen of fenyleendimethyleen, en Ri, is C2-Cg alkyleen, 2-hydroxytrimethyleen, fenyleendimethyleen, C2-Cg diacyl, -CH2C0- of een groep -C00-Rlo-00C- waarin R10 is Cz,-C6 alkyleen.wherein R 5 is C 1 -C 8 alkyl, cyclohexyl, allyl, benzyl, tetrahydrofurfuryl or 1, -6-pentamethyl-1-piperidyl, R 6 and R 7 which may be the same or different have the meaning of R 5 or hydrogen, or R 2 4-morpholynyl or one of the groups of formulas (lilac) - (IIIc) wherein Rg is 1,2,6,6,6-pentamethyl-4-piperidyl, m is 2, n is zero or 1, X is - O- or> N-CH3 and Rg is hydrogen or 1,2,6,6,6-pentamethyl-4-piperidyl, R2 is hydrogen, methyl or GG-pentamethyl-1-piperidyl, R3 is C2- C6 alkylene, C6-C10 alkylene interrupted by 2 or 3 oxygen atoms; cyclohexylenedimethylene, methylenedicyclohexylene or phenylene dimethylene, and R 1 is C 2 -C 6 alkylene, 2-hydroxy trimethylene, phenylenedimethylene, C 2 -C 8 diacyl, -CH 2 CO 3 - or a group -C00-R 10 O-00C- where R 10 is C 2 -C 6 alkylene.
Die co-oligomeren van bijzonder belang zijn die met terug kerende eenheden van de formules (Ia) en (Ib) met een gemiddeld molecuulgewicht van 2000 tot 5000 en een (Ia): (Ib) verhouding van 1:1 tot 1:2, waarin Rx is de groep -0R5 ofThose co-oligomers of particular interest are those with recurring units of formulas (Ia) and (Ib) with an average molecular weight of 2000 to 5000 and a (Ia): (Ib) ratio of 1: 1 to 1: 2, where Rx is the group -0R5 or
waarin R5 is C1-Ci, alkyl of tetrahydrofurfuryl, Rg en R7 welke gelijk of verschillend kunnen zijn zijn C1-Cg alkyl, cyclohexyl of 1,2,2,6,6-penta-methyl-4-piperidyl of R6 kan ook waterstof zijn, of Rx is 4-morfolinyl of een groep met formule (lila) waarin n is nul, R2 is 1,2,2,6,6-pentame-thyl-4-piperidyl, R3 is een groep -(CH2)2-6“ of -(CH2)3-0-(CH2)2.^-0-(CH2)3-en R4 is 2-hydroxytrimethyleen.wherein R5 is C1 -C1 alkyl or tetrahydrofurfuryl, R8 and R7 which may be the same or different are C1 -C8 alkyl, cyclohexyl or 1,2,2,6,6-penta-methyl-4-piperidyl or R6 may also be hydrogen or Rx is 4-morpholinyl or a group of formula (lilac) wherein n is zero, R2 is 1,2,2,6,6-pentamethyl-4-piperidyl, R3 is a group - (CH2) 2 -6 'or - (CH2) 3 -O- (CH2) 2. -O- (CH2) 3 - and R4 is 2-hydroxy trimethylene.
De verbindingen volgens de onderhavige uitvinding kunnen bereid worden op algemeen bekende werkwijzen, bijvoorbeeld door N-methylering van de overeenkomstige co-oligomere verbindingen die 2,2,6,6-tetramethyl-piperidinegroepen bevatten, met één van de algemeen bekende N-methyle-ringswerkwijzen, bijvoorbeeld door omzetten van de 2,2,6,6-tetramethylpi-peridineverbindingen met formaldehyde en mierezuur, waarbij de omzetting plaats vindt in water of in een aromatisch koolwaterstofoplosmiddel, of door omzetting van hun met formaldehyde en waterstof in aanwezigheid van een hydrogeneringskatalysator zoals Pt, Pd of Ni, zoals beschreven in US-A-4.459.395, EP-A-319.48O en EP-A-365.469.The compounds of the present invention can be prepared by well-known methods, for example, by N-methylation of the corresponding co-oligomeric compounds containing 2,2,6,6-tetramethyl-piperidine groups with one of the well-known N-methyl- ringing processes, for example by reacting the 2,2,6,6-tetramethylpiperidine compounds with formaldehyde and formic acid, the conversion taking place in water or in an aromatic hydrocarbon solvent, or by reacting them with formaldehyde and hydrogen in the presence of a hydrogenation catalyst such as Pt, Pd or Ni, as described in US-A-4,459,395, EP-A-319.48O and EP-A-365,469.
De co-oligomeren die niet gemethyleerd zijn op de 1-plaats van de 2,2,6,6-tetramethylpiperidinegroepen kunnen bereid worden op algemeen bekende wijze, bijvoorbeeld zoals beschreven in US-A-4.547.548·The co-oligomers that are not methylated in the 1-position of the 2,2,6,6-tetramethylpiperidine groups can be prepared in a well known manner, for example as described in US-A-4,547,548 ·
De co-oligomeren volgens de onderhavige uitvinding zijn zeer efficiënt in het verbeteren van de lichtstabiliteit, warmtestabiliteit en oxidatiestabiliteit van organische verbindingen, in het bijzonder synthetische polymeren, bijvoorbeeld polyolefinen.The co-oligomers of the present invention are very efficient in improving the light stability, heat stability and oxidation stability of organic compounds, especially synthetic polymers, for example polyolefins.
De opmerkelijke licht stabiliserende werking in polypropyleen, in het bijzonder in de vorm van vezels, is in het bijzonder verrassend.The remarkable light stabilizing action in polypropylene, especially in the form of fibers, is particularly surprising.
Voorbeelden van organische verbindingen die gestabiliseerd kunnen worden zijn: 1. Polymeren van mono-olefinen en diolefinen, bijvoorbeeld polypropyleen, polyisobutyleen, polybut-l-een, poly-4-methylpent-l-een, poly-isopreen of polybutadieen, als ook polymeren van cyclo-olefinen, bijvoorbeeld van cyclopenteen of norborneen, polyethyleen (welke eventueel crosslinked kan zijn), bijvoorbeeld polyethyleen (HDPE) met hoge dichtheid, polyethyleen (LDPE) met lage dichtheid, polyethyleen (LLDPE) met lage lineaire dichtheid, polyethyleen (BLDPE) met vertakte lage dichtheid.Examples of organic compounds that can be stabilized are: 1. Polymers of mono-olefins and diolefins, for example polypropylene, polyisobutylene, polybut-1-ene, poly-4-methylpent-1-ene, polyisoprene or polybutadiene, as well as polymers of cycloolefins, for example of cyclopentene or norbornene, polyethylene (which may optionally be crosslinked), for example high density polyethylene (HDPE), low density polyethylene (LDPE), low linear density polyethylene (LLDPE), polyethylene (BLDPE) with branched low density.
Polyolefinen, dat wil zeggen de polymeren van mono-olefinen die in de voorgaande alinea bedoeld zijn, 21 jn bij voorkeur polyethyleen en polypropyleen, kunnen bereid worden op verschillende, en in het bijzonder op de volgende, methoden; a) radicale polymerisatie (onder normale en hoge druk en bij verhoogde temperaturen).Polyolefins, that is, the polymers of mono-olefins referred to in the preceding paragraph, preferably polyethylene and polypropylene, can be prepared by various, and in particular by, the following methods; a) radical polymerization (under normal and high pressure and at elevated temperatures).
b) katalytische polymerisatie met een katalysator die normaliter één of meer dan één van de metalen van de groepen IVb, Vb, VIb of VIII van het periodiek systeem bevat. Deze metalen hebben gewoonlijk één of meer dan één ligand, in het bijzonder oxiden, halegoniden, alco-holaten, esters, ethers, aminen, alkylgroepen, alkenylgroepen en/of arylgroepen die hetzij it- of σ' -gecoördineerd kunnen zijn. Deze metaalcomplexen kunnen in vrije vorm aanwezig zijn of gebonden op substraten, in het bijzonder op geactiveerd magnesiumchloride, titanium (III) chloride, aluminium of siliciumoxide. Deze katalysatoren kunnen oplosbaar of niet oplosbaar zijn in het polymerisatieme-dium. De katalysatoren kunnen als zodanig of in combinatie met andere activatoren gebruikt worden bij de polymerisatie. Voorbeelden van andere activatoren zijn metaalalkylen, metaalhydriden, metaal-alkylhalogeniden, metaalalkyloxiden of metaalalkyloxanen, genoemde metalen kunnen elementen zijn van de groepen Ia, Ha en/of lila van het periodiek systeem. De activatoren kunnen gemakkelijk gemodificeerd zijn met ester, ether, amine of silylethergroepen. Deze kata-lysatorsystemen worden gewoonlijk aangeduid als Philips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metalloceen of enkele plaats katalysatoren (SSC).b) catalytic polymerization with a catalyst normally containing one or more of the metals of groups IVb, Vb, VIb or VIII of the periodic table. These metals usually have one or more than one ligand, especially oxides, halides, alcoholates, esters, ethers, amines, alkyl groups, alkenyl groups and / or aryl groups which can be either it or σ 'coordinated. These metal complexes can be in free form or bonded to substrates, in particular to activated magnesium chloride, titanium (III) chloride, aluminum or silicon oxide. These catalysts can be soluble or insoluble in the polymerization medium. The catalysts can be used as such or in combination with other activators in the polymerization. Examples of other activators are metal alkyls, metal hydrides, metal alkyl halides, metal alkyl oxides or metal alkyl oxanes, said metals may be elements of groups Ia, Ha and / or lilac of the periodic table. The activators can be easily modified with ester, ether, amine or silyl ether groups. These catalyst systems are commonly referred to as Philips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene or single site catalysts (SSC).
2. Mengsels van de polymeren genoemd onder 1), bijvoorbeeld mengsels van polypropyleen met polyisobutyleen, polypropyleen met polyethyleen (bijvoorbeeld PP/HDPE, PP/LDPE) en mengsels van verschillende typen polyethyleen (bijvoorbeeld LDPE/HDPE).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- Copolymeren van mono-olefinen en diolefinen met elkaar of met andere vinylmonomeren, bijvoorbeeld ethyleen/propyleencopolymeren, polyethyleen (LLDPE) met lage lineaire dichtheid en mengsels daarvan met polyethyleen (LDPE) met lage dichtheid, propyleen/but-l-een copolymeren, propyleen/isobutyleencopolymeren, ethyleen/but-l-een copolymeren, ethy-leen/hexeen copolymeren, ethyleen/methylpenteen copolymeren, ethy-leen/hepteen copolymeren, ethyleen/octeen copolymeren, propyleen/buta-dieen copolymeren, isobutyleen/isopropeen copolymeren, ethyleen/acryla-taat copolymeren, ethyleen/alkylmethacrylaat copolymeren, ethyleen/vinyl-acetaat copolymeren en hun copolymeren met koolmonoxide of ethyleen/-acrylzuurcopolymeren en hun zouten (ionomeren), als ook terpolymeren van ethyleen met propyleen en een dieen zoals hexadieen, dicyclopentadieen of ethylideen-norborneen; en mengsels van dergelijke copolymeren met elkaar en met polymeren genoemd in 1), bijvoorbeeld polypropyleen/ethyleen-pro-pyleen copolymeren, LDPE/ethyleen-vinylacetaat copolymeren (EVA), LDPE/-ethyleen-acrylzuur copolymeren (EAA), LLDPE/EVA, LLDPE/EAA en alternerende of random polyalkyleen/koolmonoxide copolymeren en mengsels daarvan met andere polymeren, bijvoorbeeld polyamiden.3- Copolymers of mono-olefins and diolefins with each other or with other vinyl monomers, for example ethylene / propylene copolymers, low linear density polyethylene (LLDPE) and mixtures thereof with low density polyethylene (LDPE), propylene / but-1-one copolymers, propylene / isobutylene copolymers, ethylene / but-1-one copolymers, ethylene / hexene copolymers, ethylene / methylpentene copolymers, ethylene / heptene copolymers, ethylene / octene copolymers, propylene / buta-diene copolymers, isobutylene / isopropene copolymers / acrylate copolymers, ethylene / alkyl methacrylate copolymers, ethylene / vinyl acetate copolymers and their copolymers with carbon monoxide or ethylene / acrylic acid copolymers and their salts (ionomers), as well as terpolymers of ethylene with propylene and a diene such as hexadiene, dicyclopentadiene norbornene; and mixtures of such copolymers with each other and with polymers mentioned in 1), for example polypropylene / ethylene-propylene copolymers, LDPE / ethylene-vinyl acetate copolymers (EVA), LDPE / ethylene-acrylic acid copolymers (EAA), LLDPE / EVA, LLDPE / EAA and alternating or random polyalkylene / carbon monoxide copolymers and mixtures thereof with other polymers, for example polyamides.
4. Koolwaterstofharsen (bijvoorbeeld C5-C9) omvattende waterstofmo-dificaties daarvan (bijvoorbeeld kleefmiddelen) en mengsels van polyalky- leen en zetmeel.Hydrocarbon resins (e.g. C5-C9) comprising hydrogen modifications thereof (e.g. adhesives) and mixtures of polyalkylene and starch.
5. Polystyreen, poly(p-methylstyreen), poly(a-methylstyreen).5. Polystyrene, poly (p-methylstyrene), poly (α-methylstyrene).
6. Copolymeren van styreen of α-methylstyreen met diënen van acryl-derivaten, bijvoorbeeld styreen/butadieen, styreen/acrylonitril, sty-reen/alkylmethacrylaat, styreen/butadieen/alkylacrylaat, styreen/buta-dieen/alkylmethacrylaat, styreen-maleïnezuuranhydride, styreen/acryloni-trll/methylacrylaten; mengsels met hoge slagsterkte van styreencopolyme-ren en een ander polymeer, bijvoorbeeld een polyacrylaat, een dieenpoly-meer of een ethyleen/propyleen/dieenterpolymeer; en blokpolymeren van styreen zoals styreen/butadieen/styreen, styreen/isopreen/styreen, sty-reen/ethyleen/butyleen/styreen of styreen/ethyleen/propyleen/styreen.6. Copolymers of styrene or α-methylstyrene with dienes of 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 acrylates; high impact blends of styrene copolymers and another polymer, for example a polyacrylate, a diene polymer or an ethylene / propylene / diene terpolymer; and styrene block polymers such as styrene / butadiene / styrene, styrene / isoprene / styrene, styrene / ethylene / butylene / styrene or styrene / ethylene / propylene / styrene.
7. Graftcopolymeren van styreen of α-methylstyreen, bijvoorbeeld styreen op polybutadieen, styreen op polybutadieen-styreen of polybuta-dieen-acrylonitrilcopolymeren; styreen en acrylonitril (of methacryloni-tril) op butadieen; styreen, acrylonitril en methylmethacrylaat op polybutadieen; styreen en malelnezuuranhydride op polybutadieen; styreen, acrylonitril en maleïnezuuranhydride of maleïmide op polybutadieen; styreen en maleïmide op polybutadieen; styreen en alkylacrylaten of metha-crylaten op polybutadieen; styreen en acrylonitril op ethyleen/propy-leen/dieenterpolymeren; styreen en acrylonitril op polyalkylacrylaten of polyalkylmethacrylaten, styreen en acrylonitril op acrylaat/butadieenco-polymeren, als ook mengsels daarvan met de copolymeren genoemd onder 6), bijvoorbeeld het copolymeermengsels bekend als ABS, MBS, ASA of AES polymeren .7. Graft copolymers of styrene or α-methylstyrene, for example styrene on polybutadiene, styrene on polybutadiene-styrene or polybutadiene-acrylonitrile copolymers; styrene and acrylonitrile (or methacrylonitrile) on butadiene; styrene, acrylonitrile and methyl methacrylate on polybutadiene; styrene and maleic anhydride on polybutadiene; styrene, acrylonitrile and maleic anhydride or maleimide on polybutadiene; styrene and maleimide on polybutadiene; styrene and alkyl acrylates or methacrylates on polybutadiene; styrene and acrylonitrile on ethylene / propylene / diene terpolymers; styrene and acrylonitrile on polyalkyl acrylates or polyalkyl methacrylates, styrene and acrylonitrile on acrylate / butadiene copolymers, as well as mixtures thereof with the copolymers mentioned under 6), for example the copolymer mixtures known as ABS, MBS, ASA or AES polymers.
8. Halogeen-bevattende polymeren zoals polychloropreen, gechlori-neerde rubbers, gechlorineerde of gesulfochlorineerd polyethyleen, copolymeren van ethyleen en gechloreerd ethyleen, epichloorhydrin homo- en copolymeren, in het bijzonder polymeren van halogeen-bevattende vinylver-bindingen, bijvoorbeeld polyvinylchloride, polyvinylideenchloride, poly-vinylfluoride, polyvinylideenfluoride, als ook copolymeren daarvan zoals vinylchloride/vinylideenchloride, vinylchloride/vinylacetaat of vinyli-deenchloride/vinylacetaatcopolymeren.8. Halogen-containing polymers such as polychloroprene, chlorinated rubbers, chlorinated or sulfochlorinated polyethylene, copolymers of ethylene and chlorinated ethylene, epichlorohydrin homo- and copolymers, in particular polymers of halogen-containing vinyl compounds, for example polyvinyl chloride, polyvinylidene chloride, poly vinyl fluoride, polyvinylidene fluoride, as well as copolymers thereof such as vinyl chloride / vinylidene chloride, vinyl chloride / vinyl acetate or vinylidene chloride / vinyl acetate copolymers.
9. Polymeren afgeleid van α,β-onverzadigde zuren en derivaten daarvan zoals polyacrylaten en polymethacrylaten; polymethylmethacrylaten, polyacrylamiden en polyacrylonitrillen, inwendig gemodificeerd met butyl-acrylaat.9. Polymers derived from α, β-unsaturated acids and derivatives thereof such as polyacrylates and polymethacrylates; polymethyl methacrylates, polyacrylamides and polyacrylonitriles, internally modified with butyl acrylate.
10. Copolymeren van de monomeren genoemd onder 9) met elkaar of met andere onverzadigde monomeren, bijvoorbeeld acrylonitril/butadieencopoly-meren, acrylonitril/alkylacrylaatcopolymeren, acrylonitril/alkoxyalkyl- acrylaten of acrylonitril/vinylhalidecopolymeren of acrylonitril/alkylme-thacrylaat/butadieenterpolymeren.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 acrylates or acrylonitrile / vinyl halide copolymers or acrylonitrile / alkylmethyl-thacrylate polymers.
11. Polymeren afgeleid van onverzadigde alcoholen en aminen van de acylderivaten of acetalen daarvan, bijvoorbeeld polyvinylalcohol, polyvi-nylacetaat, polyvinylstearaat, polyvinylbenzoaat, polyvinylmaleaat, poly-vinylbutyraat, polyallylftalaat of polyallylmelamine; als ook hun copoly-meren met olefinen genoemd in 1) boven.11. Polymers derived from unsaturated alcohols and amines of the acyl derivatives or acetals thereof, for example polyvinyl alcohol, polyvinyl acetate, polyvinyl stearate, polyvinyl benzoate, polyvinyl maleate, polyvinyl butyrate, polyallyl phthalate or polyallyl melamine; as well as their copolymers with olefins mentioned in 1) above.
12. Homopolymeren en copolymeren van cyclische ethers zoals polyal-kyleenglycolen, polyethyleenoxide, polypropyleenoxide of copolymeren daarvan met bisglycidylethers.12. Homopolymers and copolymers of cyclic ethers such as polyalkylene glycols, polyethylene oxide, polypropylene oxide or copolymers thereof with bisglycidyl ethers.
13. Polyacetalen zoals polyoxymethyleen en dipolyoxymethylenen welke ethyleenoxide als comonomeer bevatten; polyacetalen gemodificeerd met thermoplastische polyurethanen, acrylaten of MBS.13. Polyacetals such as polyoxymethylene and dipolyoxymethylenes containing ethylene oxide as a comonomer; polyacetals modified with thermoplastic polyurethanes, acrylates or MBS.
14. Polyfenyleenoxiden en sulfiden, en mengsels van polyfenyleen-oxiden met styreenpolymeren of polyamiden.14. Polyphenylene oxides and sulfides, and mixtures of polyphenylene oxides with styrene polymers or polyamides.
15. Polyurethanen afgeleid van polyethers, polyesters of polybuta-diënen met eindstandigde hydroxylgroepen aan de ene kant en alifatische of aromatische polyisocyanaten aan de andere kant als ook precursors daarvan.15. Polyurethanes derived from polyethers, polyesters or polybutadienes having terminal hydroxyl groups on the one hand and aliphatic or aromatic polyisocyanates on the other as well as precursors thereof.
16. Polyamiden en copolyamiden afgeleid van diaminen en dicarbonzu-ren en/of van aminocarbonzuren van de overeenkomstige lactamen, bijvoorbeeld polyamide 4, polyamide 6, polyamide 6/6, 6/10, 6/9. 6/12. 4/6, 12/12, polyamide 11, polyamide 12, aromatische polyamiden uitgaande van m-xyleendiamine en adipinezuur; polyamiden bereid uit hexamethyleendiami-ne en isoftaal of/en tereftaalzuur en met of zonder een elastomeer als modificator, bijvoorbeeld poly-2,4,4-trimethylhexamethyleen tereftaalami-de of poly-m-fenyleenisoftaalamide; en ook blokcopolymeren van de eerder genoemde polyamiden met polyolefinen, olefincopolymeren, ionomeren of chemisch gebonden of geënte elastomeren; of met polyethers, bijvoorbeeld met polyethyleenglycol, polypropyleenglycol of polytetramethyleenglycol; als ook polyamiden van copolyamiden gemodificeerd met EPDM of ABS; en polyamiden gecondenseerd tijdens de omzetting (RIM polyamidesystemen).16. Polyamides and copolyamides derived from diamines and dicarboxylic acids and / or from amino carboxylic acids of 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 or / and 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 chemically bonded or grafted elastomers; or with polyethers, for example with polyethylene glycol, polypropylene glycol or polytetramethylene glycol; as well as polyamides of copolyamides modified with EPDM or ABS; and polyamides condensed during the conversion (RIM polyamide systems).
17. Polyurea, polyimiden, polyamide-imiden en polybenzimidazolen, 18. Polyesters afgeleid van dicarbonzuren en diolen en/of van hy-droxycarbonzuren van de overeenkomstige lactonen, bijvoorbeeld polyethyleen tereftalaat, polybutyleentereftalaat, poly-1,4-dimethylolcyclohexaan-tereftalaat en polyhydroxybenzoaten, als ook blokcopolyetheresters afgeleid van polyethers met eindstandige hydroxylgroepen; en ook polyesters gemodificeerd met polycarbonaten of MBS.17. Polyureas, polyimides, polyamideimides and polybenzimidazoles, 18. Polyesters derived from dicarboxylic acids and diols and / or from hydroxycarboxylic acids of the corresponding lactones, for example polyethylene terephthalate, polybutylene terephthalate, poly-1,4-dimethylolcyclohexane terephthalate and polyhydroxybenzoates, as well as block copolyether esters derived from hydroxyl-terminated polyethers; and also polyesters modified with polycarbonates or MBS.
19. Polycarbonaten en polyestercarbonaten.19. Polycarbonates and Polyester Carbonates.
20. Polysulfonen, polyethersulfonen en polyetherketonen.20. Polysulfones, polyether sulfones and polyether ketones.
21. Crossllnked polymeren afgeleid van aldehyden aan de ene kant en fenolen, urea en melaminen aan de andere kant, zoals fenol/formaldehyde-harsen, urea/formaldehydharsen en melamine/formaldehydharsen.21. Cross-linked polymers derived from aldehydes on the one hand and phenols, urea and melamines on the other, such as phenol / formaldehyde resins, urea / formaldehyde resins and melamine / formaldehyde resins.
22. Drogende en niet drogende alkydharsen.22. Drying and non-drying alkyd resins.
23. Onverzadigde polyesterharsen afgeleid van copolyesters van verzadigde en onverzadigde dicarbonzuren met polyhydrische alcoholen en vinylverbindingen als crosslinked middelen, en ook halogeen-bevattende modificaties daarvan met lage brandbaarheid.23. Unsaturated polyester resins derived from copolyesters of saturated and unsaturated dicarboxylic acids with polyhydric alcohols and vinyl compounds as crosslinked agents, and also halogen-containing modifications thereof with low flammability.
2k. Crosslinkbare acrylharsen afgeleid van gesubstitueerde acryla-ten, bijvoorbeeld epoxyacrylaten, urethaanacrylaten of polyesteracryla-ten.2k. Crosslinkable acrylic resins derived from substituted acrylates, for example epoxy acrylates, urethane acrylates or polyester acrylates.
25. Alkydharsen, polyesterharsen en acrylaatharsen crosslinked met melamineharsen, ureaharsen, polyisocyanaten of epoxyharsen.25. Alkyd resins, polyester resins and acrylate resins crosslinked with melamine resins, urea resins, polyisocyanates or epoxy resins.
26. Crosslinked epoxyharsen afgeleid van polyepoxiden, bijvoorbeeld van bisglycidylethers of van cycloalifatische diëpoxiden.26. Cross-linked epoxy resins derived from polyepoxides, for example from bisglycidyl ethers or from cycloaliphatic dipoxides.
27. Natuurlijke polymeren zoals cellulose, rubber, gelatine en chemisch gemodificeerde homologe derivaten daarvan, bijvoorbeeld cellulo-seacetaten, cellulosepropionaten en cellulosebutyraten, of de cellulose-ethers zoals methylcellulose; als ook rosinen en hun derivaten.27. Natural polymers such as cellulose, rubber, gelatin and chemically modified homologous derivatives thereof, for example cellulose acetates, cellulose propionates and cellulose butyrates, or the cellulose ethers such as methyl cellulose; as well as rosins and their derivatives.
28. Mengsels van de boven genoemde polymeren (polyblends), bijvoorbeeld PP/EPDM, polyamide/EPDM of ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrylaten, POM/thermoplastiseh PUR, PC/thermoplastisch PUR, POM/acrylaat, POM/MBS, PPO/MBS, PPO/HIPS, PPO/PA 6.6 en copolymeren, PA/HDPE, PA/PP, PA/PPO.28. Blends of the above mentioned 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 / thermoplastic PUR, PC / thermoplastic PUR, POM / acrylic, POM / MBS, PPO / MBS, PPO / HIPS, PPO / PA 6.6 and copolymers, PA / HDPE, PA / PP, PA / PPO.
29. Natuurlijke en synthetische organische stoffen welke zuiver monomere verbindingen of mengsels van dergelijke verbindingen zijn, bijvoorbeeld minerale olies, dierlijke en plantaardige vetten, olie en vetten, of oliën, vetten en wassen gebaseerd op synthetische esters (bijvoorbeeld ftalaten, adipaten, fosfaten of trimellitaten) en ook mengsels van synthetische esters met minerale oliën in elke gewichtsverhouding, typisch die gebruikt als smeercomposities, als ook waterige emulsies van dergelijke materialen.29. Natural and synthetic organics which are pure monomeric compounds or mixtures of such compounds, for example mineral oils, animal and vegetable fats, oils and fats, or oils, fats and waxes based on synthetic esters (for example phthalates, adipates, phosphates or trimellitates ) and also mixtures of synthetic esters with mineral oils in any weight ratio, typically those used as lubricating compositions, as well as aqueous emulsions of such materials.
30. Waterige emulsies van natuurlijk of synthetisch rubber, bijvoorbeeld natuurlijk latex of latices van gecarboxyleerd styreen/buta-dieencopolymeren.30. Aqueous emulsions of natural or synthetic rubber, for example natural latex or latices of carboxylated styrene / butadiene copolymers.
De verbindingen volgens de onderhavige uitvinding kunnen gemengd worden met de organische stoffen in verschillende verhoudingen afhanke lijk van de aard van de verbinding die gestabiliseerd moet worden, het gebruik en de aanwezigheid van andere toevoegsels.The compounds of the present invention can be mixed with the organics in different proportions depending on the nature of the compound to be stabilized, the use and the presence of other additives.
In het algemeen is het geschikt om bijvoorbeeld 0,01 tot 5 gew.2 van de verbindingen volgens de uitvinding toe te passen, betrokken op het gewicht van de verbinding die gestabiliseerd moet worden, bij voorkeur tussen 0,05 en 1%.In general, it is suitable to use, for example, 0.01 to 5 wt. 2 of the compounds of the invention, based on the weight of the compound to be stabilized, preferably between 0.05 and 1%.
De verbindingen volgens de onderhavige uitvinding kunnen in het algemeen toegevoegd worden aan de polymere stoffen voor, gedurende of na de polymerisatie of crosslinking van de genoemde stoffen.The compounds of the present invention can generally be added to the polymeric substances before, during or after the polymerization or cross-linking of said substances.
De verbindingen volgens de onderhavige uitvinding kunnen in de polymere stoffen worden ingebouwd, bijvoorbeeld in zuivere vorm of inge-kapseld in wassen, oliën of polymeren.The compounds of the present invention can be incorporated into the polymeric materials, for example, in pure form or encapsulated in waxes, oils or polymers.
De verbindingen volgens de onderhavige uitvinding kunnen in de polymere stoffen ingebouwd worden op verschillende wijzen, zoals door het droog mengen in poedervorm of het nat mengen in de vorm van oplossingen of suspensies als ook in de vorm van een masterbatch; bij dergelijke werkwijzen kan het polymeer gebruikt worden in poedervorm, granulaten, oplossingen, suspensies of in de vorm van latices.The compounds of the present invention can be incorporated into the polymeric substances in various ways, such as by dry powder mixing or wet mixing in the form of solutions or suspensions as well as in the form of a master batch; in such processes, the polymer can be used in powder form, granules, solutions, suspensions or in the form of latices.
De met de produkten volgens de onderhavige uitvinding gestabiliseerde materialen kunnen gebruikt worden voor het maken van mallen, films, magneetbanden, monofilamenten, vezels, oppervlakte coatings en dergelijke.The materials stabilized with the products of the present invention can be used to make molds, films, magnetic tapes, monofilaments, fibers, surface coatings and the like.
Indien gewenst kunnen andere conventionele toevoegsels voor synthetische polymeren zoals antioxidantia, UV absorptiemiddelen, nikkelstabi-lisatoren, pigmenten, vulmaterialen, weekmakers, antistatische middelen, vlamvertragers, smeermiddelen, corrosieremmers en metaaldesactivatoren toegevoegd worden aan de mengsels van de verbindingen volgens de onderhavige uitvinding met de organische materialen.If desired, other conventional synthetic polymer additives such as antioxidants, UV absorbers, nickel stabilizers, pigments, fillers, plasticizers, anti-static agents, flame retardants, lubricants, corrosion inhibitors and metal deactivators can be added to the mixtures of the compounds of the present invention with the organic materials.
Specifieke voorbeelden van toevoegsels welke gemengd met de verbindingen met formule (I) gebruikt kunnen worden zijn: 1. Antioxidantia 1.1 Gealkvleerde monofenolen. bijvoorbeeld 2,6-di-tert-butyl-4-methylfe-nol, 2-tert-butyl-4,6-dimethylfenol, 2,6-di-tert-butyl-4-ethylfenol, 2,6-di-tert-butyl-4-n-butylfenol, 2,6-di-tert-butyl-4-isobutylfenol, 2,6- dicyclopentyl-4-methylfenol, 2-(α-methylcyclohexyl)-4,6-dimethylfenol, 2,6-dioctadecyl-4-methylfenol, 2,4,6-tricyclohexylfenol, 2,6-di-tert- butyl-4-methoxymethylfenol, 2,6-di-nonyl-4-methylfenol, 2,4-dimethyl-6- (1'-methylundec-1'-yl)fenol, 2,4-dimethyl-6-{1 *-methylheptadec-1'-yl)fenol, 2,4-dimethyl-6-(1'-methyltridec-1'-yl)fenol en mengsels daarvan.Specific examples of additives which can be used in admixture with the compounds of formula (I) are: 1. Antioxidants 1.1 Alkylated monophenols. for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6-di-tert -butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2- (α-methylcyclohexyl) -4,6-dimethylphenol, 2.6 -dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- ( 1'-methylundec-1'-yl) phenol, 2,4-dimethyl-6- {1 * -methylheptadec-1'-yl) phenol, 2,4-dimethyl-6- (1'-methyltridec-1'- yl) phenol and mixtures thereof.
1.2 Alkvlthiomethvlfenolen. bijvoorbeeld 2,4-dioctylthiomethyl-6-tert-butylfenol, 2,4-dioctylthiomethyl-6-methylfenol, 2,4-diocty1thiomethy1-6-ethylfenol, 2,6-di-dodecylthiomethyl-4-nonylfenol.1.2 Alkylthiomethylphenols. 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 Hvdrochinonen en gealkvleerde hvdrochinonen. bijvoorbeeld 2,6-di-tert-butyl-4-methoxyfenol, 2,5-di-tert-butylhydrochinon, 2,5~di-tert-amylhydrochinon, 2,6-difenyl-4-octadecyloxyfenol, 2,6-di-tert-butylhydro-chinon, 2,5-di-tert-butyl-4-hydroxyanisool, 3.5“di-tert-butyl-4-hydroxy-anisool, 3 * 5-di-tert-butyl-4-hydroxyfenylstearaat, bis-(3,5"di-tert-bu-tyl-4-hydroxyfenyl)adipaat.1.3 Hydroquinones and alkrohydroquinones. for example 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol, 2,6-di -tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3.5 "di-tert-butyl-4-hydroxy-anisole, 3 * 5-di-tert-butyl-4-hydroxyphenyl stearate, bis - (3.5 "di-tert-butyl-4-hydroxyphenyl) adipate.
1.4 Gehvdroxvleerde thiodifenvlethers. bijvoorbeeld 2,2'-thiobis(6-tert-butyl-4-methylfenol), 2,2'-thiobis(4-octylfenol), 4,4'-thiobis(6-tert-butyl-3-methylfenol), 4,4'-thiobis(6-tert-butyl-2-methylfenol), 4,4'-thiobis-(3,6-di-sec-amylfenol), 4,4'-bis-(2,6-dimethyl-4-hydroxyfe-nyl)disulfide.1.4 Hydroxylated thiodiphenyl ethers. for example 2,2'-thiobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'-thiobis (6-tert-butyl-3-methylphenol), 4 , 4'-thiobis (6-tert-butyl-2-methylphenol), 4,4'-thiobis (3,6-di-sec-amylphenol), 4,4'-bis- (2,6-dimethyl-) 4-hydroxyphenyl) disulfide.
1.5 Alkvlideenbisfenolen. bijvoorbeeld 2,2'-methyleenbis(6-tert-butyl-4-methylfenol), 2,2'-methyleenbis(6-tert-butyl-4-ethylfenol), 2,2'-methy-leenbis[4-methyl-6-(α-methylcyclohexyl)fenol], 2,2'-methyleenbis(4-me-thyl-6-cyclohexylfenol), 2,2'-methyleenbis(6-nonyl-4-methylfenol), 2,2'-methyleenbis(4,6-di-tert-butylfenol), 2,2'-ethylideenbis(4,6-di-tert-butylfenol), 2,2'-ethylideenbis(6-tert-butyl-4-isobutylfenol), 2,2'-me-thyleenbis[6-(a-methylbenzyl)-4-nonylfenol], 2,2'-methyleenbis[6-(a,a-dimethylbenzyl)-4-nonylfenol], 4,4'-methyleenbis(2,6-di-tert-butylfenol), 4,4'-methyleenbis{6-tert-butyl-2-methylfenol), 1,1-bis(5-tert-butyl-4-hydroxy-2-methylfenyl)butaan, 2,6-bis-(3_tert-butyl-5-methyl-2-hydroxy-benzyl)-4-methylfenol, 1,1,3”tris(5-tert-butyl-4-hydroxy-2-methylfe-nyl)butaan, 1,1-bis(5-tert-butyl-4-hydroxy-2-methyl-fenyl)-3-n-dodecyl-mercaptobutaan, ethyleenglycol bis[3,3“bis(3'-tert-butyl-4'-hydroxyfe-nyl)butyraat], bis{3~tert-butyl-4-hydroxy-5-methyl-fenyl)dicyclopen-tadieen, bis[2-(3'-tert-butyl-2'-hydroxy~5'-methylbenzyl)-6-tert-butyl-4-methylfenyl]tereftalaat, 1,1-bis-(3.5-dimethyl-2-hydroxyfenyl)butaan, 2,2-bis-(3,5“di-tert-butyl-4-hydroxyfenyl)propaan, 2,2-bis-(5-tert-butyl-4-hydroxy2-methylfenyl)-4-n-dodecylmercaptobutaan, 1,1,5,5"tetra-(5"tert-butyl-4-hydroxy2-methylfenyl)pentaan.1.5 Alkylidene bisphenols. for example 2,2'-methylene bis (6-tert-butyl-4-methylphenol), 2,2'-methylene bis (6-tert-butyl-4-ethylphenol), 2,2'-methylene bis [4-methyl- 6- (α-methylcyclohexyl) phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (6-nonyl-4-methylphenol), 2,2'-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidene bis (4,6-di-tert-butylphenol), 2,2'-ethylidene bis (6-tert-butyl-4-isobutylphenol), 2, 2'-methylene bis [6- (a-methylbenzyl) -4-nonylphenol], 2,2'-methylenebis [6- (a, a-dimethylbenzyl) -4-nonylphenol], 4,4'-methylenebis (2 , 6-di-tert-butylphenol), 4,4'-methylenebis {6-tert-butyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis- (3-tert-butyl-5-methyl-2-hydroxy-benzyl) -4-methylphenol, 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-dodecyl-mercaptobutane, ethylene glycol bis [3,3 "bis (3'-tert-butyl-4) 1-hydroxyphenyl) butyrate], bis {3-tert-butyl-4-hydroxy-5-methyl-phenyl) dicyclopentadiene, bis [2- (3'-tert-butyl-2'-h ydroxy-5'-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis- (3,5-dimethyl-2-hydroxyphenyl) butane, 2,2-bis- (3,5 "di- tert-butyl-4-hydroxyphenyl) propane, 2,2-bis- (5-tert-butyl-4-hydroxy2-methylphenyl) -4-n-dodecyl mercaptobutane, 1,1,5,5 "tetra- (5" tert -butyl-4-hydroxy2-methylphenyl) pentane.
Ui 0-. N- en S-benzylverbindingen, bijvoorbeeld 3’5’3’,5'-tetra-tert-butyl-4,4'-dihydroxydibenzylether, octadecyl-4-hydroxy-3,5-dimethylben-zylmercaptoacetaat, tris-(3,5“di“tert-butyl-4-hydroxybenzyl)amine, bis(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)dithiotereftalaat, bis(3.5-di-tert-butyl-4-hydroxybenzyl)sulfide, iso-octyl-3,5“di-tert-butyl-4-hy-droxybenzylmercaptoacetaat.Onion 0-. N- and S-benzyl compounds, for example 3'5'3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercaptoacetate, 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, iso-octyl-3,5 "di-tert-butyl-4-hydroxybenzyl mercaptoacetate.
1.7 Hvdroxv gebenzvleerde malonaten. bijvoorbeeld dioctadecyl-2,2-bis-(3.5-di-tert-butyl-2-hydroxybenzyl)-malonaat, di-octadecyl-2-(3“tert-butyl-4-hydroxy-5-methylbenzyl)-malonaat, di-dodecylmercaptoethyl-2,2-bis-(3.5-di-tert-butyl-4-hydroxybenzyl)malonaat, bis-[4-{1,1,3.3-tetrame-thylbutyl)fenyl]-2,2-bis(3,5-di-tert-buyl-4-hydroxybenzyl)malonaat.1.7 Hvdroxv benzylated malonates. for example dioctadecyl-2,2-bis- (3,5-di-tert-butyl-2-hydroxybenzyl) malonate, di-octadecyl-2- (3 "tert-butyl-4-hydroxy-5-methylbenzyl) malonate, di dodecyl mercaptoethyl-2,2-bis- (3,5-di-tert-butyl-4-hydroxybenzyl) malonate, bis- [4- {1,1,3,3-tetramethylbutyl) phenyl] -2,2-bis (3 .5-di-tert-buyl-4-hydroxybenzyl) malonate.
1.8 Aromatische hvdroxvbenzvlverbindingen. bijvoorbeeld l,3.5-tris-(3.5" di-tert-butyl-4-hydroxybenzyl)-2,4,6-trimethylbenzeen, 1,4-bis(3.5-di-tert-butyl-4-hydroxybenzyl)-2,3,5.6-tetramethylbenzeen, 2,4,6-tris(3,5" di-tert-butyl-4-hydroxybenzyl)fenol.1.8 Aromatic hydrogen compounds. for example 1,3,5-tris- (3,5 "di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 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.
1.9 Triazineverbindingen. bijvoorbeeld 2,4-bis(octylmercapto)-6-(3.5-di-tert-butyl-4-hydrpxyanilino)-1,3,5"triazine, 2-octylmercapto-4,6-bis(3,5” di-tert-butyl-4-hydroxyanilino)-1,3,5-triazine, 2-octylmercapto-4,6-bis-(3,5"di-tert-butyl-4-hydroxyfenoxy)-1,3» 5“triazine, 2,4,6-tris{3,5“di-tert-butyl-4-hydroxyfenoxy)-1,2,3“triazine, 1,3,5"tris-(3,5”di-tert-bu-tyl-4-hydroxybenzyl)isocyanuraat, 1,3,5“tris(4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl)-isocyanuraat, 2,4,6-tris{3»5-di-tert-butyl-4-hydroxyfe-nylethyl)-1,3,5“triazine, 1,3,5-tris(3,5"di-tert-butyl-4-hydroxyfenylpro-pionyl)-hexahydro-1,3,5“triazine, 1,3,5”tris(3,5”dicylohexyl-4-hydroxy-benzyl)isocyanuraat.1.9 Triazine compounds. for example 2,4-bis (octyl mercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5 "triazine, 2-octyl mercapto-4,6-bis (3,5" di- tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octyl mercapto-4,6-bis- (3,5 "di-tert-butyl-4-hydroxyphenoxy) -1,3» 5 "triazine , 2,4,6-tris {3,5 "di-tert-butyl-4-hydroxyphenoxy) -1,2,3" triazine, 1,3,5 "tris- (3,5" di-tert-bu -tyl-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-hydroxyphenyl-propionyl) -hexahydro-1,3, 5 "triazine, 1,3,5" tris (3.5 "dicylohexyl-4-hydroxy-benzyl) isocyanurate.
1.10 Benzvlfosfonaten. bijvoorbeeld dimethyl-2,5-di-tert-butyl-4-hydroxy-benzylfosfonaat, diethyl-3,5-di-tert-butyl-4-hydroxybenzylfosfonaat, dioctadecyl-3,5~di-tert-butyl-4-hydroxy3-methylbenzylfosfonaat, het cal-ciumzout van de monoethylester van 3,5”di“tert-butyl-4-hydroxybenzylfos-fonzuur.1.10 Benzyl phosphonates. for example dimethyl-2,5-di-tert-butyl-4-hydroxy-benzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4-hydroxy3 -methylbenzylphosphonate, the calcium salt of the monoethyl ester of 3.5 "di" tert-butyl-4-hydroxybenzylphosphonic acid.
1.11 Acvlaminofenolen. bijvoorbeeld 4-hydroxylaurinilide, 4-hydroxystea-ranilide, octyl N-(3»5~di-tert-butyl-4-hydroxyfenyl)carbamaat.1.11 Acvlaminophenols. for example, 4-hydroxylaurinilide, 4-hydroxystearanilide, octyl N- (3, 5-di-tert-butyl-4-hydroxyphenyl) carbamate.
1.12 Esters van B-(3.S-di-tert-butvl-4-hvdroxvfenvl)oronionzuur met mono- of polyhydrische alcoholen, bijvoorbeeld met methanol, ethanol, octadeca-nol, 1,6-hexaandiol, 1,9-nonaadiol, ethyleenglycol, 1,2-propaandiol, neopentylglycol, thiodiethyleenglycol, diethyleenglycol, triethyleenglycol, pentaerythritol, tris(hydroxyethyl)isocyanuraat, N,N'-bis(hydroxyethyl )oxamide, 3-tbiaundecanol, 3"thiapentadecanol, trimethylhexaandiol, trimethylpropaan, 4-hydroxymethyl-1-fosfa-2,6,7_trioxabicyclo[2.2.2]oc-taan.1.12 Esters of B- (3.S-di-tert-butyl-4-hydroxylphenyl) oronionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonaadiol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-tbiaundecanol, 3 "thiapentadecanol, trimethylhexanediol, trimethylhexanediol, trimethylethylane -1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.
1.1S Esters van B-f’ï-tert-butvl-^-hvdroxv-^-methvlfenvl^propionzuur met mono- of polyhydrische alcoholen, bijvoorbeeld met methanol, ethanol, oetadecanol, 1,6-hexaandiol, 1,9-nonaadiol, ethyleenglycol, 1,2-propaan-diol, neopentylglycol, thiodiethyleenglycol, diethyleenglycol, triethy-leenglycol, pentaerythritol, tris(hydroxyethyl)isocyanuraat, Ν,Ν’-bis-(hydroxyethyl)oxamide, 3~thiaundecanol, 3~thiapentadecanol, trimethylhexaandiol , trimethylolpropaan, 4-hydroxymethyl-l-fosfa-2,6,7“trioxabicy-clo[2.2.2]octaan.1.1S Esters of β-tert-butyl - - - - hydroxyl - - - methylphenyl, propionic acid with mono- or polyhydric alcohols, for example with methanol, ethanol, octadecanol, 1,6-hexanediol, 1,9-nonaadiol, ethylene glycol, 1,2-propane diol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, Ν, Ν'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentheanediol, 3-thiapentheanediol trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.
1.14 Esters van β-(λ.5-dicvclohexvl-4-hvdroxvfenvl)-propionzuur met mono-of polyhydrische alcoholen, bijvoorbeeld met methanol, octadecanol, 1,6-hexaandiol, 1,9-nonaandiol, ethyleenglycol, 1,2-propaandiol, neopentylglycol, thiodiethyleenglycol, diethyleenglycol, triethyleenglycol, pentaery thritol , tris(hydroxyethyl)isocyanuraat, N,N’-bis(hydroxyethyl)oxa-mide, 3~thiaundecanol, 3~thiapentadecanol, trimethylhexaandiol, trimethylolpropaan , 4-hydroxymethyl-l-fosfa-2,6,7~trioxabicyclo[2.2.2]octaan.1.14 Esters of β- (λ.5-dicvclohexvl-4-hvdroxvfenvl) -propionic acid with mono or polyhydric alcohols, for example with methanol, 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 -2,6,7-trioxabicyclo [2.2.2] octane.
1.15 Esters van 5.5-di-tert-butvl-4-hvdroxvfenvlaziinzuur met mono- of polyhydrische alcoholen, bijvoorbeeld met methanol, octadecanol, 1,6-hexaandiol, l,9~nonaandiol, ethyleenglycol, 1,2-propaandiol, neopentylglycol, thiodiethyleenglycol, diethyleenglycol, triethyleenglycol, pentaery thritol , tris(hydroxyethyl)isocyanuraat, N,N'-bis(hydroxyethyl)oxa-mide, 3"thiaundecanol, 3"thiapentadecanol, trimethylhexaandiol, trimethylpropaan , 4-hydroxymethyl-l-fosfa-2,6,7_trioxabicyclo[2.2.2]octaan.1.15 Esters of 5.5-di-tert-butyl-4-hydroxylphenyllazic acid with mono- or polyhydric alcohols, for example with methanol, 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, trimethylpropane, 4-hydroxymethyl-1-phospha-2,6 .7_trioxabicyclo [2.2.2] octane.
1.16 Amiden van β-Π. 5-di-tert-butvl-4-hvdroxvfenvl)propionzuur bijvoorbeeld N,N'-bis(3,5“di~tert-butyl-4-hydroxyfenylpropionyl)hexamethyleendi-amine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyfenylpropionyl)trimethyleendi-amine, N,N'-bis(3 * 5 ~di -tert-butyl-4-hydroxyfenylpropionyl)hydrazine.1.16 Amides of β-Π. 5-di-tert-butyl-4-hydroxylphenyl) propionic acid e.g. N, N'-bis (3,5 "di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylenediamine, N, N'-bis (3,5- di-tert-butyl-4-hydroxyphenylpropionyl) trimethylene diamine, N, N'-bis (3 * 5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine.
2. UV absorotiemiddelen en licht stabilisatoren 2.1 2-(2 *-hvdroxvfenvl)-benzotriazolen. bijvoorbeeld 2-(2'-hydroxy-5'-methylfenyl)-benzotriazool, 2-(3'5'-di-tert-butyl-2'-hydroxyfenyl)benzo-triazool, 2-{5'-tert-butyl-2'-hydroxyfenyl)benzotriazool, 2-(2'-hydrpxy-5'-(1,1,3.3"tetramethylbutyl)fenyl)benzotriazool, 2-(3',5'-di-tert-butyl-2'-hydroxyfenyl)-5-chloor-benzotriazool, 2-(3' - tert-butyl-2'-hydroxy-5’-methylfenyl)-5-chloor-benzotriazool, 2-(3' -sec-butyl-5'-tert-butyl-2'-hydroxyf enyl)benzotriazool, 2-(2 *-hydroxy-4'-octyloxyfenyl)benzotriazool, 2-(3,5'-di-tert-amyl-2*-hydroxyfenyl)benzotriazool, 2-(3’,5'-bis-(α,α-dimethylbenzyl)-2'-hydroxyfenyl)benzotriazool, mengsels van 2-(3'-tert-butyl-2' -hydroxy-5'-(2-octyloxycarbonylethyl)fenyl)-5-chloor-benzotriazool , 2-(3'-tert-butyl-5'-[2-(2-ethylhexyloxy)-carbonylethyl]-2'-hydroxy-fenyl)-5-chloor-benzotriazool, 2-(3'-tert-butyl-2’-hydroxy-5'-(2-methoxy-carbonylethyl)fenyl)-5-chloor-benzotriazool, 2-(3' - tert-butyl-2'-hydroxy-5'-(2-methoxycarbonylethyl)fenyl)benzotriazool, 2-(3'-tert-butyl- 2’-hydroxy-5' “(2-octyloxycarbonylethyl)fenyl)benzotriazool, 2-(3'“tert-butyl-5'-[2-(2-ethylhexyloxy)carbonylethyl]-2'-hydroxyfenyl)benzotriazool, 2-(3'-dodecyl-2’-hydroxy-5'-methylfenyl)-benzotriazool, en 2-(3'-tert-butyl -2 '-hydroxy-51~(2-isooctyloxycarbonylethyl)fenylbenzotriazool, en 2' (3' -tert-butyl-2' -hydroxy-5' - (2-isooctyloxycarbonylethyl) f enylbenzotriazool , 2,2'-methyleen-bis[4-(1,1,3% 3”tetramethylbutyl)-6-benzotriazool-2-ylfenol]; het transesterficatieprodukt van 2-[3'-tert-butyl-5'-(2-methoxycarbonylethyl) -2'-hydroxyfenyl]-2H-benzotriazool met polyethyleen-glycol 300; [R-CH2CH2-C00(CH2)3]2-, waarin R = 3'"tert-butyl-4'-hydroxy-5'-2H-benzotriazool-2-ylfenyl.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) benzo-triazole, 2- {5'-tert-butyl- 2'-hydroxyphenyl) benzotriazole, 2- (2'-hydrpxy-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-tert-amyl-2 * -hydroxyphenyl) benzotriazole, 2- (3 5'-bis- (α, α-dimethylbenzyl) -2'-hydroxyphenyl) benzotriazole, mixtures of 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-methoxy-carbonylethyl) phenyl) -5-chlorobenzotriazole, 2- (3' - tert-butyl-2'-hydroxy-5 '- (2- methoxycarbonylethyl) phenyl) benzotriazole, 2- (3'-tert-butyl-2'-hydroxy-5 '"(2-oc tyloxycarbonylethyl) phenyl) benzotriazole, 2- (3 '' tert-butyl-5 '- [2- (2-ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl) benzotriazole, 2- (3'-dodecyl-2'-hydroxy- 5'-methylphenyl) -benzotriazole, and 2- (3'-tert-butyl -2 '-hydroxy-51 ~ (2-isooctyloxycarbonylethyl) phenylbenzotriazole, and 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-CH 2 CH 2 -C00 (CH 2) 3] 2-, wherein R = 3 '"tert-butyl-4'-hydroxy-5'-2H-benzotriazol-2-ylphenyl.
2.2 2-hvdroxvbenzofenonen. bijvoorbeeld het 4-hydroxy, 4-methoxy- 4-oc-tyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2',4'-trihydroxy en 2'-hydroxy-4,4’-dimethoxyderivaten.2.2 2-hydroxyl benzophenones. for example, the 4-hydroxy, 4-methoxy-4-oc-tyloxy, 4-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ', 4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivatives.
2Λ Esters van gesubstitueerde en niet gesubstitueerde benzoëzuren zoals bijvoorbeeld 4-tert-butylfenylsalicylaat, fenylsalicylaat, octylfenylsa-licylaat, dibenzoylresorcinol, bis(4-tert-butylbenzoyl)resorcinol, ben-zoylresorcinol, 2,4-di-tert-butylfenyl 3·5-di-tert-butyl-4-hydroxybenzo-aat, hexadecyl 3%5"di-tert-butyl-4-hydroxybenzoaat, octadecyl 3»5"di-tert-butyl-4-hydroxybenzoaat, 2-methyl-4,6-di-tert-butylfenyl 3,5-di-tert-butyl-4-hydroxybenzoaat.2Λ Esters of substituted and unsubstituted benzoic acids such as, for example, 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoylresorcinol, 2,4-di-tert-3-tert-butyl -di-tert-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 Acrvlaten. bijvoorbeeld ethyl a-cyaan-β,β-difenylacrylaat, iso-octyl a-cyaan-β,β-di-fenylacrylaat, methyl ct-carbomethoxycinnamaat, methyl a- cyaan-B-methyl-p-methoxycinnamaat, butyl a-cyaan-B-p-methoxycinnamaat, methyl α-carbomethoxy-p-methoxycinnamaat en N-(B-carbomethoxy-B-cyaanvi-nyl)-2-methylindoline.2.4 Acrvaten. for example ethyl α-cyano-β, β-diphenyl acrylate, iso-octyl α-cyano-β, β-di-phenyl acrylate, methyl ct-carbomethoxycinnamate, methyl α-cyano-B-methyl-p-methoxycinnamate, butyl α-cyano- Bp-methoxycinnamate, methyl α-carbomethoxy-p-methoxycinnamate and N- (B-carbomethoxy-B-cyanovinyl) -2-methylindoline.
2.5 Nikkelverbindingen. bijvoorbeeld nikkelcomplexen van 2,2'-thio-bis-[4-(1,1,3,3-tetraaethylbutyl)fenol], zoals het Ijl of 1j2 complex, met of zonder additionele liganden zoals n-butylamine, triethanolamine of N-cyclohexyldiethanolamine, nikkeldibutyldithiocarbamaat, nikkelzouten van de monoalkylesters, b.v. de methyl- of ethylester van 4-hydroxy-3»5"di-tert-butylbenzylfosfonzuur, nikkelcomplexen van ketoximen, b.v. van 2-hydroxy-4-methylfenyl imdecylketoxime, nikkelcomplexen van l-fenyl-4-lauroyl-5-hydroxypyrazool met of zonder additionele liganden.2.5 Nickel compounds. for example nickel complexes of 2,2'-thio-bis- [4- (1,1,3,3-tetraaethylbutyl) phenol], such as the Ijl or 1j2 complex, with or without additional ligands such as n-butylamine, triethanolamine or N- cyclohexyldiethanolamine, nickel dibutyl dithiocarbamate, nickel salts of the monoalkyl esters, eg the methyl or ethyl ester of 4-hydroxy-3 »5" di-tert-butylbenzylphosphonic acid, nickel complexes of ketoximes, eg of 2-hydroxy-4-methylphenyl imdecylketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole with or without additional ligands.
2.6 Sterisch gehinderde aminen. bijvoorbeeld bis(2,2,6,6-tetramethyl-piperidyl)sebacaat, bis(2,2,6,6-tetramethylpiperidyl)succinaat, bis-(1,2,2,6,6-pentamethylpiperidyl)sebacaat, bis(l,2,2,6,6-pentamethylpipe-ridyln-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonaat, het condensaat van 1-(2-hydroxyethyl)-2,2,6,6-tetramethyl-4-hydroxypiperidine en succine zuur, het condensaat van N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)hexame-thyleendiamine en 4-tert-octylamino-2,6-dichloor-l.3.5-triazine, tris-(2,2,6,6-tetramethyl-4-piperidyl) nitrilotriaceaat, tetrakis(2,2,6,6-tetramethyl-4-piperidyl)-1,2,3,4-butaan-tetracarboxylaat, 1,1’-(1,2-ethaandiyl)bis(3.3.5.5~tetramethylpiperazinon), 4-benzoyl-2,2,6,6-tetra-methylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis-(1,2,2,6,6-pentamethylpiperidyl)-2-n-butyl-2-(2-hydroxy~3,5-di-tert-bu-tylbenzyl)malonaat, 3-n-octyl-7,7,9,9"tetramethyl-1,3,8-triazaspi-ro[4.5]decaan-2,4-dion, bis(l-octyloxy-2,2,6,6-tetramethylpiperidyl)sebacaat , bis(l-octyloxy-2,2,6,6-tetramethylpiperidyl)succinaat, het condensaat van N,N'-bis-(2,2,6,6-tetramethyl-4-piperidyl)hexaanmethyleendiamine en 4-morfolino-2,6-dichloor-l,3,5_triazine, het condensaat van 2-chloor- 4,6-bis(4-n-butylamino-2,2,6,6-tetramethylpiperidyl)-1,3,5“triazine en 1,2-bis(3-aminopropylamino)-ethaan, het condensaat van 2-chloor-4,6-di-(4-n-butylamino-l,2,2,6,6-pentamethylpiperidyl)-1,3,5~triazine en 1,2-bis-(3-aminopropylamino)ethaan, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro[4.5]decaan-2,4-dion-3~dodecyl-l- (2,2,6,6-tetramethyl-4-piperidyl)pyrrolidin-2,5-dion, 3“dodecyl-l-(1,2,2,6,6-pentamethyl-4-pipe-ridyl)pyrrolidine-2,5-dion.2.6 Sterically hindered amines. for example, bis (2,2,6,6-tetramethyl-piperidyl) sebacate, bis (2,2,6,6-tetramethylpiperidyl) succinate, bis- (1,2,2,6,6-pentamethylpiperidyl) sebacate, bis ( 1,2,6,6,6-pentamethylpiperidyln-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, the condensate of 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl -4-hydroxypiperidine and succinic acid, the condensate of N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2,6-dichloro-1. 3,5-triazine, tris- (2,2,6,6-tetramethyl-4-piperidyl) nitrilotriacate, tetrakis (2,2,6,6-tetramethyl-4-piperidyl) -1,2,3,4-butane- tetracarboxylate, 1,1 '- (1,2-ethanediyl) bis (3.3.5.5-tetramethylpiperazinone), 4-benzoyl-2,2,6,6-tetra-methylpiperidine, 4-stearyloxy-2,2,6,6 -tetramethylpiperidine, bis- (1,2,2,6,6-pentamethylpiperidyl) -2-n-butyl-2- (2-hydroxy-3,5-di-tert-butylbenzyl) malonate, 3-n- octyl-7,7,9,9 "tetramethyl-1,3,8-triazaspi-ro [4.5] decane-2,4-dione, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethylpiperidy l) succinate, the condensate of N, N'-bis- (2,2,6,6-tetramethyl-4-piperidyl) hexanomethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine, the condensate of 2-chloro-4,6-bis (4-n-butylamino-2,2,6,6-tetramethylpiperidyl) -1,3,5 "triazine and 1,2-bis (3-aminopropylamino) ethane, the condensate of 2-chloro-4,6-di- (4-n-butylamino-1,2,6,6,6-pentamethylpiperidyl) -1,3,5-triazine and 1,2-bis- (3-aminopropylamino) ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decane-2,4-dione-3-dodecyl-1- (2,2,6 6-tetramethyl-4-piperidyl) pyrrolidin-2,5-dione, 3 "dodecyl-1- (1,2,2,6,6-pentamethyl-4-piperidyl) pyrrolidine-2,5-dione.
2.7 Oxamiden. bijvoorbeeld 4,4'-dioctyloxyoxanilide, 2,2'-dïoctyloxy- 5.5*-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2’-ethoxanilide, N,N'-bis(3-dimethy1aminopropy1)oxamide, 2-ethoxy-5-tert-butyl-2*-ethoxanilide en zijn mengsel met 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide en mengsels van ortho- en paramethoxy-digesubstitueerde oxaniliden en mengsels van o- en p-ethoxy-digesubstitu-eerde oxaniliden.2.7 Oxamides. for example 4,4'-dioctyloxyoxanilide, 2,2'-dioctyloxy-5,5 * -di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethoxanilide , N, N'-bis (3-dimethylamino-propyl) oxamide, 2-ethoxy-5-tert-butyl-2 * -ethoxanilide and its mixture with 2-ethoxy-2'-ethyl-5,4'-di-tert- butoxanilide and mixtures of ortho and paramethoxy disubstituted oxanilides and mixtures of o- and p-ethoxy disubstituted oxanilides.
2^8 2-(2-hvdroxyfenvl)-1.3.5-triazinen. bijvoorbeeld 2,4,6-tris(2-hy-droxy-4-octyloxyfenyl)-1,3,5-triazine, 2-(2-hydroxy-4-octyloxyfenyl)-4,6-bis(2,4-dimethylfenyl)-1,3.5“triazine, 2-(2,4-dihydroxyfenyl)-4,6-bis-{2,4-dimethylfenyl)-1,3.5“triazine, 2,4-bis(2-hydroxy-4-propyloxyfenyl)-6-(2,4-dimethylfenyl)-1,3.5~triazine, 2-(2-hydroxy-4-octyloxyfenyl)-4,6-bis(4-methylfenyl)-1,3.5~triazine, 2-(2-hydroxy-4-dodecyloxyfenyl)-4,6-bis(2,4-dimethylfenyl)-1,3.5~triazine, 2-[2-hydroxy-4-(2-hydroxy-3~bu-toxy-propoxy)fenyl]-4,6-bis(2,4-dimethyl)-1,3,5-triazine, 2-[2-hydroxy-4-(2-hydroxy-3-octyloxy-propyloxy) fenyl]-4,6-bis (2,4-dimethyl )-1,3,5-tria-zine.2 ^ 8 2- (2-hydroxyphenyl) -1,3.5-triazines. for example 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (2,4- dimethylphenyl) -1,3.5 "triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis- {2,4-dimethylphenyl) -1,3.5" triazine, 2,4-bis (2-hydroxy-4 -propyloxyphenyl) -6- (2,4-dimethylphenyl) -1,3.5-triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (4-methylphenyl) -1,3.5-triazine, 2 - (2-hydroxy-4-dodecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3.5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-butoxy) propoxy) phenyl] -4,6-bis (2,4-dimethyl) -1,3,5-triazine, 2- [2-hydroxy-4- (2-hydroxy-3-octyloxy-propyloxy) phenyl] -4 6-bis (2,4-dimethyl) -1,3,5-triazine.
2.. Metaaldesactivatoren. bijvoorbeeld Ν,Ν’-difenyloxamide, N-salicylal-N'-salicyloylhydrazine, N,N'-bis(salicyloyl)hydrazine, N,N'-bis(3,5-di-tert-butyl-4-hydroxyfenylpropionyl)hydrazine, 3-salicyloylamino-l,2,4-triazool, bis(benzylideen)oxalyl dihydrazide, oxanilide, isoftaaloyldihy-drazide, sebacoylbisfenylhydrazide, N,N'-di-acetyladipoyldihydrazide, N,N'-bis(salicyloyl)oxalyldihydrazide, N,N'-bis(salicyloyl)-thiopropio-nyldihydrazide.2 .. Metal deactivators. for example, Ν, Ν'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N, N'-bis (salicyloyl) hydrazine, N, N'-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hydrazine , 3-salicyloylamino-1,2,4-triazole, bis (benzylidene) oxalyl dihydrazide, oxanilide, isophthaloyl dihydrazide, sebacoyl bisphenyl hydrazide, N, N'-di-acetyladipoyldihydrazide, N, N'-bis (salicyloyl) oxalyldihydraz N'-bis (salicyloyl) -thiopropionyl dihydrazide.
4. Andere fosfieten en fosfonieten. bijvoorbeeld trifenylfosfiet, dife-nylalkylfosfiet, fenyldialkylfosfiet, tris(nonylfenyl)fosfiet, trilauryl-fosfiet, trioctadecylfosfiet, distearylpentaerythritoldifosfiet, tris-(2,4-di-tert-butylfenyl)fosfiet, diisodecylpentaerythritoldifosfiet, bis(2,4-di-tert-butylfenyl)-pentaerythritoldifosfiet, bis(2,6-di-tert-butyl-4-methylf enyl)-pentaerythritoldifosfiet, diisodecyloxypentaerythri-toldifosfiet, bis(2,4-di-tert-butyl-6-methylfenyl)pentaerythritoldifos-f iet, bis(2,4,6-tris(tert-butylfenyl)pentaerythritoldifosfiet, tristea-rylsorbitoltrifosfiet, tetrakis(2,4-di-tert-butylfenyl)4,4'-bifenyleendi-f osf oniet, 6-iso-octyloxyl-2,4,8,10-tetra-tert-butyl-12H-dibenz[d,g]- 1,3,2-dioxafosfocin, 6-fluoro-2,4,8,10-tetra-butyl-12-methyl-di-benz[d.g.]-l,3.2-dioxafosfocin, bis(2,4-di-tert-butyl-6-methylfenyl)me-thylfosfiet, bis(2,4-di-tert-butyl-6-methylfenyl)ethylfosfiet.4. Other phosphites and phosphonites. for example, triphenylphosphite, diphenylalkylphosphite, phenyl dialkylphosphite, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearylpentaerythritol diphosphite (2,4-di-tert-butylphenylphenyl) phosphite butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) -pentaerythritol diphosphite, diisodecyloxypentaerythri-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 diphosphite, 6-iso-octyloxyl-2 4,8,10-tetra-tert-butyl-12H-dibenz [d, g] - 1,3,2-dioxaphosphocin, 6-fluoro-2,4,8,10-tetra-butyl-12-methyl- di-benz [dg] -1,2,2-dioxaphosphocin, bis (2,4-di-tert-butyl-6-methylphenyl) methyl phosphite, bis (2,4-di-tert-butyl-6-methylphenyl) ethyl phosphite .
5,- Peroxide weevangers. bijvoorbeeld esters van B-thiodipropionzuur, bijvoorbeeld de lauryl, stearyl, myristyl of tridecylesters, mercaptoben-zimidazool of het zinkzout van 2-mercaptobenzimidazool, zinkdibutyldithi-ocarbamaat, dioctadecyldisulfide, pentaerythritoltetrakis(B-dodecylmer-cap to)propionaat.5, - Peroxide weighers. for example esters of B-thiodipropionic acid, for example the lauryl, stearyl, myristyl or tridecyl esters, mercaptoben-zimidazole or the zinc salt of 2-mercaptobenzimidazole, zinc dibutyl dithiocarbamate, dioctadecyl disulfide, pentaerythritol tetlethyl propetylis (capododetro) tetrakis.
è.. Polvamidestabilisatoren. bijvoorbeeld koperzouten samen met jodiden en/of fosforverbindingen en zouten van tweewaardig mangaan.è .. Polamide stabilizers. for example copper salts together with iodides and / or phosphorus compounds and salts of divalent manganese.
2· Basische co-stabilisatoren. bijvoorbeeld melamine, polyvinylpyrroli-don, dicyaandiamide, triallylcyanuraat, ureumderivaten, hydrazinederiva-ten, aminen, polyamiden, polyurethanen, alkalimetaalzouten en aardalkali-metaalzouten van hogere vetzuren bijvoorbeeld calciumstearaat, zinkstea-raat, magnesiumbehenaat, magnesiumstearaat, waterstofricinoleaat en kali-umpalmitaat, antimoon pyrocatecholaat of tinpyrocatecholaat.2 · Basic co-stabilizers. for example, melamine, polyvinylpyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example, calcium stearate, zinc stearate, magnesium stearate, potassium kali-amicric acid, or tin pyrocatecholate.
8. Neerslag vormende middelen, bijvoorbeeld, 4-tert-butylbenzoëzuur, adipinezuur, difenylazijnzuur.8. Precipitating agents, for example, 4-tert-butyl benzoic acid, adipic acid, diphenylacetic acid.
9.. Vulmiddelen en versterkingsmiddelen. bijvoorbeeld calciumcarbonaat, silicaten, glasvezels, asbest, talk, kaoline, mica, bariumsulfaat, me-taaloxiden en hydroxiden, koolstof, grafiet.9 .. Fillers and reinforcing agents. for example, calcium carbonate, silicates, glass fibers, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon, graphite.
10. Andere teovoegsels. bijvoorbeeld weekmakers, smeermiddelen, emulgeer-middelen, pigmenten, optische bleekmiddelen, vlam vertragende middelen, antistatische middelen en opblaasmiddelen.10. Other suffixes. for example, plasticizers, lubricants, emulsifiers, pigments, optical brighteners, flame retardants, anti-static agents and blowing agents.
11. Benzofuranonen en indolinonen. bijvoorbeeld die beschreven in US-A-4.325.863 of US-A-4.338.244.11. Benzofuranones and Indolinones. for example, those described in US-A-4,325,863 or US-A-4,338,244.
De verbindingen volgens de uitvinding kunnen ook gebruikt worden als stabilisatoren, in het bijzonder als lichtstabilisatoren, voor bijna alle materialen bekend in de fotografische reproduktie en andere repro-duktietechnieken, zoals bijvoorbeeld beschreven in Research Disclosure 1990, 31429 (blz. 474 tot 480).The compounds of the invention can also be used as stabilizers, especially as light stabilizers, for almost all materials known in photographic reproduction and other reproduction techniques, such as described, for example, in Research Disclosure 1990, 31429 (pp. 474 to 480).
Verschillende voorbeelden van de bereiding en het gebruik van de co-oligomeren omvattende terugkerende eenheden met de formules (Ia) en (Ib) worden voor een gedetailleerdere illustratie van de onderhavige uitvinding beschreven; deze voorbeelden worden later als illustratie gegeven en houden geen enkele beperking in.Several examples of the preparation and use of the co-oligomers comprising recurring units of formulas (Ia) and (Ib) are described for a more detailed illustration of the present invention; these examples are given as illustrations later on and do not limit them in any way.
De verbindingen beschreven in de voorbeelden 1, 3» 4, 7 en 8 hebben betrekking op een bij voorkeur toegepaste uitvoeringsvorm van de onderhavige uitvinding.The compounds described in Examples 1, 3, 4, 7 and 8 relate to a preferred embodiment of the present invention.
Voorbeeld 1: 20,8 g (0,1 mol) van 2,4-dichloor-6-isopropoxy-l,3,5“triazi-ne, 9,3 g (0,1 mol) van epichloorhydrine, 82,9 (0,21 mol) van N.N'-bis-(2,2,6,6-tetramethyl-4-piperidyl)-1,6-hexaandiamine en 100 ml 4-methyl-2-pentanol worden 1 uur op 80° verwarmd en dan nog 8 uren onder reflux, 12 g (0,3 mol) NaOH wordt gedurende de laatste 6 uren van de reactie langzaam toegevoegd.Example 1: 20.8 g (0.1 mol) of 2,4-dichloro-6-isopropoxy-1,3,5 "triazine, 9.3 g (0.1 mol) of epichlorohydrin, 82.9 (0.21 mol) of N, N'-bis- (2,2,6,6-tetramethyl-4-piperidyl) -1,6-hexanediamine and 100 ml of 4-methyl-2-pentanol are stirred at 80 for 1 hour ° C and then under reflux for another 8 hours, 12 g (0.3 mol) of NaOH is slowly added during the last 6 hours of the reaction.
Nadat de toevoeging van het NaOH volledig was, wordt het reactie-mengsel nog 2 uren onder reflux verwarmd. Het water van de reactie en het grootste gedeelte van 4-methyl-2-pentanol worden vervolgens afgedestilleerd; 400 ml xyleen wordt toegevoegd en 100 ml oplosmiddel wordt langzaam afgedestilleerd om het 4-methyl-2-pentanol volledig te verwijderen.After the addition of the NaOH was complete, the reaction mixture is heated under reflux for an additional 2 hours. The water of the reaction and most of the 4-methyl-2-pentanol are then distilled off; 400 ml of xylene are added and 100 ml of solvent are slowly distilled off to completely remove the 4-methyl-2-pentanol.
Een mengsel dat 21,2 g (0,46 mol) mierezuur en 14,4 g (0,48 mol) methanol-vrij 30% formaldehyde bevat wordt in 3 uur aan de aldus verkregen xyleenoplossing toegevoegd, verwarmd tot 110°C, met simultane azeo-tropische verwijdering van het toegevoegde water en het water van de reactie.A mixture containing 21.2 g (0.46 mol) formic acid and 14.4 g (0.48 mol) methanol-free 30% formaldehyde is added over 3 hours to the xylene solution thus obtained, heated to 110 ° C, with simultaneous azeo-tropical removal of the added water and the water from the reaction.
Het mengsel wordt afgekoeld tot 70°C, 'een oplossing van 3 g NaOH in 60 ml water wordt toegevoegd, en het mengsel wordt nog 30 minuten geroerd. De waterige laag wordt afgescheiden, en de organische fase wordt gewassen met water, gedroogd boven Na2S0^ en afgedampt onder verminderde druk.The mixture is cooled to 70 ° C, a solution of 3 g of NaOH in 60 ml of water is added, and the mixture is stirred for an additional 30 minutes. The aqueous layer is separated, and the organic phase is washed with water, dried over Na2SO4 and evaporated under reduced pressure.
Dit geeft een produkt met een smeltpunt van 77~85°C en met een gemiddeld molecuulgewicht van Mn = 2800.This gives a product with a melting point of 77 ~ 85 ° C and an average molecular weight of Mn = 2800.
Voorbeeld 2; Door toepassing van de werkwijze beschreven in voorbeeld 1, wordt een produkt verkregen met een smeltpunt van j8-88°C en een gemiddeld molecuulgewicht van Mn = 3800 door omzetting van 22,2 g (0,1 mol) 2-butoxy-4,6-dichloor-l,3,5~triazine, 9,3 g (0,1 mol) epichloorhydrine en 78,9 g (0,2 mol) N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-l,6-hexaandiamine in 100 ml 4-methyl-2-pentanol en aansluitende methylering in xyleen met mierezuur/formaldehydmengsel zoals aangegeven in voorbeeld 1.Example 2; By using the method described in Example 1, a product is obtained with a melting point of 8-88 ° C and an average molecular weight of Mn = 3800 by conversion of 22.2 g (0.1 mol) 2-butoxy-4, 6-dichloro-1,3,5-triazine, 9.3 g (0.1 mol) epichlorohydrin and 78.9 g (0.2 mol) N, N'-bis (2,2,6,6-tetramethyl -4-piperidyl) -1,6-hexanediamine in 100 ml 4-methyl-2-pentanol and subsequent methylation in xylene with formic acid / formaldehyde mixture as indicated in Example 1.
Voorbeeld 3: Door toepassing van de werkwijze beschreven in voorbeeld 1, wordt een verbinding verkregen met een smeltpunt van 103-112°C en een gemiddeld molecuulgewicht van Mn = 3500 door omzetting van 22,1 g (0,1 mol) 2,4-dichloor-6-diethylamino-l,3.5~triazine, 9.3 g (0,1 mol) epi-chloorhydrine en 78,9 g (0,2 mol) N,N'-bis(2,2,6,6-tetramethyl-4-piperi-dyl)-l,6-hexaandiamine in 100 ml 4-methyl-2-pentanol en aansluitende methylering in xyleen met het mierezuur/formaldehydmengsel zoals aangegeven in voorbeeld 1.Example 3: Using the method described in Example 1, a compound is obtained with a melting point of 103-112 ° C and an average molecular weight of Mn = 3500 by conversion of 22.1 g (0.1 mol) 2.4 -dichloro-6-diethylamino-1,3,5-triazine, 9.3 g (0.1 mol) epi-chlorohydrin and 78.9 g (0.2 mol) N, N'-bis (2,2,6,6- tetramethyl-4-piperidyl) -1,6-hexanediamine in 100 ml of 4-methyl-2-pentanol and subsequent methylation in xylene with the formic acid / formaldehyde mixture as indicated in Example 1.
Voorbeeld 4: Door toepassing van de werkwijze beschreven in voorbeeld 1 wordt een verbinding verkregen met een smeltpunt van 110-117eC en een gemiddeld molecuulgewicht van Mn = 4000 door omzetting van 27,7 g (0,1 mol) 2,4-dichloor-6-octylamino-l,3,5*triazine, 9,3 g (0,1 mol) epichloor-hydrine en 78,9 g (0,2 mol) N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)- 1,6-hexaandiamine in 100 ml 4-methyl-2-pentanol en aansluitende methyle-ring in xyleen met het mierezuur/formaldehydmengsel zoals aangegeven in voorbeeld 1.Example 4: Using the method described in Example 1, a compound is obtained with a melting point of 110-117 ° C and an average molecular weight of Mn = 4000 by conversion of 27.7 g (0.1 mol) of 2,4-dichloro- 6-octylamino-1,3,5 * triazine, 9.3 g (0.1 mol) epichlorohydrin and 78.9 g (0.2 mol) N, N'-bis (2,2,6,6 -tetramethyl-4-piperidyl) - 1,6-hexanediamine in 100 ml of 4-methyl-2-pentanol and subsequent methylation in xylene with the formic acid / formaldehyde mixture as indicated in Example 1.
Voorbeeld 5; Door toepassing van de werkwijze beschreven in voorbeeld 1 wordt een verbinding verkregen met een smeltpunt van 94-102°C en een gemiddeld molecuulgewicht van Mn = 4100 door omzetting van 24,7 g (0,1 mol) 2,4-dichloor-6-cyclohexylamino-l,3,5“triazine, 18,5 g (0,2 mol) epichloorhydrine en 118,4 g (0,3 mol) N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-!,6-hexaandiamine in 150 ml 4-methyl-2-pentanol en aansluitende methylering in xyleen met een mengsel dat 31,8 g (0,69 mol) mierezuur en 72,1 g (0,72 mol) methanol-vrij 30# /formaldehyde bevat.Example 5; By using the method described in example 1, a compound is obtained with a melting point of 94-102 ° C and an average molecular weight of Mn = 4100 by conversion of 24.7 g (0.1 mol) 2,4-dichloro-6 -cyclohexylamino-1,3,5-triazine, 18.5 g (0.2 mol) epichlorohydrin and 118.4 g (0.3 mol) N, N'-bis (2,2,6,6-tetramethyl- 4-piperidyl) -!, 6-hexanediamine in 150 ml of 4-methyl-2-pentanol and subsequent methylation in xylene with a mixture containing 31.8 g (0.69 mol) formic acid and 72.1 g (0.72 mol) ) contains methanol-free 30 # / formaldehyde.
Voorbeeld 6; Door toepassing van de werkwijze beschreven in voorbeeld 1 wordt een verbinding verkregen met een smeltpunt van 75-84 eC en een gemiddeld molecuulgewicht van Mn = 2200 door omzetting van 25 g (0,1 mol) 2,4-dichloor-6-tetrahydrofurfuryloxy-l,3,5“triazine, 9,3 g (0,1 mol) epichloorhydrine en 88,8 g (0,225 mol) N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-!,6-hexaandiamine in 110 ml 4-methyl-2-pentanol en aansluitende methylering in xyleen met het mierezuur/formaldehydmengsel zoals aangegeven in voorbeeld 1.Example 6; By using the method described in example 1, a compound is obtained with a melting point of 75-84 eC and an average molecular weight of Mn = 2200 by conversion of 25 g (0.1 mol) 2,4-dichloro-6-tetrahydrofurfuryloxy- 1,3,5-triazine, 9.3 g (0.1 mol) epichlorohydrin and 88.8 g (0.225 mol) N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) - 6-hexanediamine in 110 ml of 4-methyl-2-pentanol and subsequent methylation in xylene with the formic acid / formaldehyde mixture as indicated in Example 1.
Voorbeeld 7: Door toepassing van de werkwijze beschreven in voorbeeld 1 wordt een verbinding verkregen met een smeltpunt van 100-103°C en een gemiddeld molecuulgewicht van Mn = 2000 door omzetting van 18,7 g (0,05 mol) 2,4-dichloor-6-[N-(2,2,6,6-tetramethyl-4-piperidyl)-piperazine]-l,3,5”triazine, 4,6 g (0,05 mol) epichloorhydrine en 41,4 g (0,105 mol) N,N'-bis(2,2,6,6-tetramethyl-4-piperidyl)-l,6-hexaandiamine in 75 ml 4-methyl-2-pentanol en aansluitende methylering in xyleen met het miere-zuur/formaldehydmengsel zoals aangegeven in voorbeeld 1.Example 7: Using the method described in Example 1, a compound with a melting point of 100-103 ° C and an average molecular weight of Mn = 2000 is obtained by conversion of 18.7 g (0.05 mol) 2.4- dichloro-6- [N- (2,2,6,6-tetramethyl-4-piperidyl) -piperazine] -1,3,5 ”triazine, 4.6 g (0.05 mol) epichlorohydrin and 41.4 g (0.105 mol) N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) -1,6-hexanediamine in 75 ml of 4-methyl-2-pentanol and subsequent methylation in xylene with the mere acid / formaldehyde mixture as indicated in example 1.
Voorbeeld 8; Door toepassing van de werkwijze beschreven in voorbeeld 1 wordt een verbinding verkregen met een smeltpunt van 105-109eC en een gemiddeld molecuulgewicht van Mn = 3150 door omzetting van 11,7 g (0,05 mol) 2,4-dichloor-6-morfoline-l,3f5~triazine, 4,6 g (0,05 mol) epichloor-hydrine en 4l,4 g (0,105 mol) N,N’-bis(2,2,6,6-tetramethyl-4-piperidyl)- 1,6-hexaandiamine in 75 ml 4-methyl-2-pentanol en aansluitende methylering in xyleen met het mierezuur/formaldehydemengsel zoals aangegeven in voorbeeld 1.Example 8; Using the method described in Example 1, a compound with a melting point of 105-109eC and an average molecular weight of Mn = 3150 is obtained by conversion of 11.7 g (0.05 mol) of 2,4-dichloro-6-morpholine -1,3f5-triazine, 4.6 g (0.05 mole) epichlorohydrin and 4l, 4 g (0.105 mole) N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) 1,6-hexanediamine in 75 ml of 4-methyl-2-pentanol and subsequent methylation in xylene with the formic acid / formaldehyde mixture as indicated in Example 1.
In de voorbeelden werd het gemiddeld molecuulgewicht bepaald met behulp van een dampdrukosmometer (®Gonotec) zoals beschreven in EP-A-255.990.In the examples, the average molecular weight was determined using a vapor pressure osmometer (®Gonotec) as described in EP-A-255,990.
Voorbeeld 9: (Licht stabiliserende werking in polypropyleenvezels) 2,5 g van elk van de produkten aangegeven in tabel 1, 1 g tris(2,4-di-tert-butylfenyl)-fosfiet, 0,5 g calciummonoethyl-3,5~di-tert-butyl-4-hydroxybenzylfosfonaat, 1 g calciumstearaat en 2,5 g titaandioxide werden in een langzame menger gemengd met 1000 g polypropyleenpoeder met een smeltindex = 12 g/10 minuten (berekend bij 230°C en 2,16 kg).Example 9: (Light stabilizing effect in polypropylene fibers) 2.5 g of each of the products shown in Table 1, 1 g of tris (2,4-di-tert-butylphenyl) phosphite, 0.5 g of calcium monoethyl-3,5 ~ di-tert-butyl-4-hydroxybenzylphosphonate, 1 g calcium stearate and 2.5 g titanium dioxide were mixed in a slow mixer with 1000 g polypropylene powder with a melt index = 12 g / 10 minutes (calculated at 230 ° C and 2.16 kg ).
De mengsels werden bij 200-230°C geëxtrudeerd waardoor polymere granulaten werden verkregen welke vervolgens werden omgezet in vezels, met een pilot-type apparaat (®Leonard-Sumirago(VA) Italy) onder de volgende omstandigheden:The blends were extruded at 200-230 ° C to yield polymeric granulates which were then converted to fiber using a pilot type device (®Leonard-Sumirago (VA) Italy) under the following conditions:
extrudertemperatuur : 200-230°Cextruder temperature: 200-230 ° C
koptemperatuur j 255"260eCcup temperature j 255 "260eC
strekverhouding : 1 : 3*5 telling : 11 dtex per filamentstretch ratio: 1: 3 * 5 count: 11 dtex per filament
De aldus bereide vezels werden blootgesteld opgestapeld op een witte kaart, in een model 65 WR Weather-O-Meter (ASTM D2565-85) met een zwart paneel temperatuur van 63°C.The fibers thus prepared were exposed stacked on a white card, in a model 65 WR Weather-O-Meter (ASTM D2565-85) with a black panel temperature of 63 ° C.
De rest taaiheid wordt berekend op monsters genomen na verschillende tijden aan de blootstelling van het licht door middel van een contante snelheid tensometer en de blootstellingstijd in uren (T50) nodig om de begintaaiheid te halveren wordt vervolgens berekend.The residual toughness is calculated on samples taken after different times of exposure of the light by means of a constant velocity tensometer and the exposure time in hours (T50) required to halve the initial toughness is then calculated.
Vezels bereid onder dezelfde omstandigheden als boven aangegeven, maar zonder het toevoegen van de stabilisatoren volgens de uitvinding, worden ter vergelijking getest.Fibers prepared under the same conditions as indicated above, but without adding the stabilizers of the invention, are tested for comparison.
De verkregen resultaten worden gegeven in tabel 1.The results obtained are given in Table 1.
TABEL 1TABLE 1
Stabilisator T50_iuur}.Stabilizer T50_iuur}.
Geen 190Not 190
Verbinding van voorbeeld 1 20Ö0Compound of Example 1 20O0
Verbinding van voorbeeld 2 1980Compound of Example 2 1980
Verbinding van voorbeeld 3 20^0Compound of Example 3 20 ^ 0
Verbinding van voorbeeld 4 2000Connection of Example 4 2000
Verbinding van voorbeeld 5 1970Compound of Example 5 1970
Verbinding van voorbeeld 6 2010Connection of example 6 2010
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ITMI920904A IT1254689B (en) | 1992-04-14 | 1992-04-14 | PIPERIDIN-TRIAZINIC COOLIGOMERS SUITABLE FOR USE AS STABILIZERS FOR ORGANIC MATERIALS. |
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IT1052501B (en) * | 1975-12-04 | 1981-07-20 | Chimosa Chimica Organica Spa | POLYTHRIAZIN COMPOUNDS USABLE FOR THE STABILIZATION OF SYNTHETIC POLYMERS AND PROCEDURE FOR THEIR PREPARATION |
IT1123083B (en) * | 1976-11-26 | 1986-04-30 | Chimosa Chimica Organica Spa | PIPERIDINE DERIVATIVES OF 1,3,5 TRIAZINE AS STABILIZERS FOR SYNTHETIC POLYMERS THAT INCLUDE THEM AND PROCEDURE FOR THEIR PREPARATION |
US4315859A (en) * | 1979-01-15 | 1982-02-16 | Ciba-Geigy Corporation | 1,3,5-Triazines containing at least one piperidine radical |
DE2933078A1 (en) * | 1979-08-16 | 1981-03-26 | Hoechst Ag, 65929 Frankfurt | NEW TRIAZINE DERIVATIVES, THEIR PRODUCTION AND THEIR USE AS STABILIZERS FOR SYNTHETIC POLYMERS |
IT1151035B (en) * | 1980-07-31 | 1986-12-17 | Chimosa Chimica Organica Spa | PIPERIDYL-DERIVATIVES OF TRIAZINIC COPOLYMERS, PROCESSES FOR THEIR PREPARATION AND STABILIZED COMPOSITIONS THAT INCLUDE THEM |
US4412020A (en) * | 1981-07-20 | 1983-10-25 | American Cyanamid Company | Novel light stabilizers for polymers |
IT1193659B (en) * | 1983-02-04 | 1988-07-21 | Chimosa Chimica Organica Spa | PIPERIDYL TRIAZIN COMPOUNDS USEFUL AS STABILIZERS FOR SYNTHETIC POLYMERS |
IT1164214B (en) * | 1983-05-09 | 1987-04-08 | Chimosa Chimica Organica Spa | POLYMERIC COMPOUNDS CONTAINING PIPERIDINIC RADICALS, PROCESS FOR THEIR PREPARATION AND USE AS STABILIZERS FOR SYNTHETIC POLYMERS |
IT1163814B (en) * | 1983-07-19 | 1987-04-08 | Chimosa Chimica Organica Spa | POLYMERIC COMPOUNDS CONTAINING PIPERIDINIC AND TRIAZINIC RADICALS, PROCESS FOR THEIR PREPARATION AND USE AS STABILIZERS FOR SYNTHETIC POLYMERS |
JPS6250342A (en) * | 1985-08-30 | 1987-03-05 | Adeka Argus Chem Co Ltd | Stabilized high-molecular material composition |
IT1231329B (en) * | 1989-07-28 | 1991-11-28 | Ciba Geigy Spa | PIPERIDIN PIPERAZIN COMPOUNDS SUITABLE FOR USE AS STABILIZERS FOR ORGANIC MATERIALS |
IT1237129B (en) * | 1989-11-10 | 1993-05-18 | Valerio Borzatta | PIPERIDIN TRIAZINIC COMPOUNDS SUITABLE FOR USE AS STABILIZERS FOR ORGANIC MATERIALS. |
IT1237541B (en) * | 1989-12-28 | 1993-06-08 | Ciba Geigy | PIPERIDIN TRIAZIN COMPOUNDS SUITABLE FOR USE AS STABILIZERS FOR ORGANIC MATERIALS |
IT1248839B (en) * | 1990-06-13 | 1995-01-30 | Ciba Geigy Spa | NEW PIPERIDIN-TRIAZINIC COOLIGOMERS SUITABLE FOR USE AS STABILIZERS FOR ORGANIC MATERIALS |
IT1243374B (en) * | 1990-07-27 | 1994-06-10 | Ciba Geigy Spa | PIPERIDIN TRIAZIN COMPOUNDS CONTAINING TETRAIDROFURANIC OR TETRAIDROPYRANIC GROUPS SUITABLE FOR USE AS STABILIZERS FOR ORGANIC MATERIALS |
IT1243433B (en) * | 1990-10-03 | 1994-06-10 | Ciba Geigy Spa | PIPERIDIN TRIAZIN COMPOUNDS SUITABLE FOR USE AS STABILIZERS FOR ORGANIC MATERIALS |
IT1251467B (en) * | 1991-07-12 | 1995-05-15 | Ciba Geigy Spa | NEW TETRAMETHYLPIPERIDINE COMPOUNDS SUITABLE FOR USE AS STABILIZERS FOR ORGANIC MATERIALS. |
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ES2069465A1 (en) | 1995-05-01 |
GB2266531B (en) | 1996-03-13 |
DE4312066A1 (en) | 1993-10-21 |
ITMI920904A0 (en) | 1992-04-14 |
GB2266531A (en) | 1993-11-03 |
BE1006266A3 (en) | 1994-07-05 |
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