ITMI970184A1 - Bisfenoli sostituiti con gruppi di norbornene come antiossidanti - Google Patents
Bisfenoli sostituiti con gruppi di norbornene come antiossidanti Download PDFInfo
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- ITMI970184A1 ITMI970184A1 IT97MI000184A ITMI970184A ITMI970184A1 IT MI970184 A1 ITMI970184 A1 IT MI970184A1 IT 97MI000184 A IT97MI000184 A IT 97MI000184A IT MI970184 A ITMI970184 A IT MI970184A IT MI970184 A1 ITMI970184 A1 IT MI970184A1
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- butyl
- tert
- bis
- copolymers
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- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical compound OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 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 1
- MCPKSFINULVDNX-UHFFFAOYSA-N drometrizole Chemical compound CC1=CC=C(O)C(N2N=C3C=CC=CC3=N2)=C1 MCPKSFINULVDNX-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- BXOUVIIITJXIKB-UHFFFAOYSA-N ethene;styrene Chemical group C=C.C=CC1=CC=CC=C1 BXOUVIIITJXIKB-UHFFFAOYSA-N 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 235000010382 gamma-tocopherol Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- NZYMWGXNIUZYRC-UHFFFAOYSA-N hexadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NZYMWGXNIUZYRC-UHFFFAOYSA-N 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 229920006270 hydrocarbon resin Polymers 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 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
- 150000003951 lactams Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- OBQVOBQZMOXRAL-UHFFFAOYSA-L magnesium;docosanoate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC([O-])=O OBQVOBQZMOXRAL-UHFFFAOYSA-L 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 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
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- NYBDEQVBEYXMHK-UHFFFAOYSA-N methyl prop-2-enoate;5-phenylpenta-2,4-dienenitrile Chemical compound COC(=O)C=C.N#CC=CC=CC1=CC=CC=C1 NYBDEQVBEYXMHK-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 125000001421 myristyl 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])[H] 0.000 description 1
- HYONQIJZVYCWOP-UHFFFAOYSA-N n',n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1N(CCCCCCN)C1CC(C)(C)NC(C)(C)C1 HYONQIJZVYCWOP-UHFFFAOYSA-N 0.000 description 1
- YIMHRDBSVCPJOV-UHFFFAOYSA-N n'-(2-ethoxyphenyl)-n-(2-ethylphenyl)oxamide Chemical compound CCOC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC YIMHRDBSVCPJOV-UHFFFAOYSA-N 0.000 description 1
- ZJFPXDGPJMHQMW-UHFFFAOYSA-N n,n'-bis[3-(dimethylamino)propyl]oxamide Chemical compound CN(C)CCCNC(=O)C(=O)NCCCN(C)C ZJFPXDGPJMHQMW-UHFFFAOYSA-N 0.000 description 1
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
- YCTMJCLDNXNRPL-UHFFFAOYSA-N n-butyl-2,2,6,6-tetramethyl-1-(1,3,5-triazin-2-yl)piperidin-4-amine Chemical compound CC1(C)CC(NCCCC)CC(C)(C)N1C1=NC=NC=N1 YCTMJCLDNXNRPL-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- 150000002848 norbornenes Chemical group 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- SLVKLHBQRNOOOJ-UHFFFAOYSA-N octadecyl 3-(4-hydroxy-3,5-dimethylphenyl)-2-sulfanylpropanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(S)CC1=CC(C)=C(O)C(C)=C1 SLVKLHBQRNOOOJ-UHFFFAOYSA-N 0.000 description 1
- XQAABEDPVQWFPN-UHFFFAOYSA-N octyl 3-[3-(benzotriazol-2-yl)-5-tert-butyl-4-hydroxyphenyl]propanoate Chemical compound CC(C)(C)C1=CC(CCC(=O)OCCCCCCCC)=CC(N2N=C3C=CC=CC3=N2)=C1O XQAABEDPVQWFPN-UHFFFAOYSA-N 0.000 description 1
- IIGMITQLXAGZTL-UHFFFAOYSA-N octyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCC IIGMITQLXAGZTL-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 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
- 150000002978 peroxides Chemical class 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 230000003711 photoprotective effect Effects 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
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001627 poly(4-methyl styrene) Polymers 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920002239 polyacrylonitrile 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
- 229920001748 polybutylene 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
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920005996 polystyrene-poly(ethylene-butylene)-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
- 239000005033 polyvinylidene chloride Substances 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
- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 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 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 239000011115 styrene butadiene Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 235000019149 tocopherols Nutrition 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-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
- 239000001226 triphosphate Substances 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
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 238000005406 washing Methods 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
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic, containing six-membered aromatic rings and other rings, with unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Description
DESCRIZIONE dell 'Invenzione industriale
La presente invenzione riguarda composti aventi le formule I e II descritte qui di seguito, riguarda composizioni che li contengono ed il loro impiego per la stabilizzazione di materiale organico.
Dalla letteratura sono noti norborneni sostituiti con un gruppo fenolico (US 4.301.306; US 4.355.148) .
EP 466.263 descrive bisfenoli sostituiti con un gruppo del norbornene, in particolare para-parabisfenoli, per esempio il composto
(bisfenolo N)
Inoltre, esiste la necessità di agenti stabilizzanti efficaci per sostanze organiche sensibili nei confronti di una degradazione termica, ossidativa oppure provocata dalla luce.
Si sono ora trovati bisfenoli sostituiti con gruppi di norbornene, specifici, aventi le formule I e II
in cui Ri indica metile oppure H, preferibilmente H, R2 indica H oppure metile, preferibilmente H,
R3 indica H oppure C1-C4-alchile, preferibilmente H, R4 indica C1-C5-alchile, preferibilmente t-butile, R5 indica C1-C5-alchile, preferibilmente metile oppure t-butile, e
il gruppo Z indica CH2 oppure 0, preferibilmente CH2.
I composti sono adatti in particolare come antiossidanti per polimeri dello stirolo.
Si preferiscono composti di formula I oppure II, in cui Ri indica H,
R2 indica H,
R3 indica H,
R4 indica t-butile,
R5 indica metile oppure t-butile, e
il gruppo Z indica CH2.
Particolarmente preferiti sono quei composti di formule I e II, in cui Z indica CH2 e/o R1 indica H. Del tutto particolarmente preferito è il composto
Alchile, a seconda del numero di atomi di carbonio indicato, indica per esempio metile, etile, n-propile, iso-propile, n-, i-, sec.- oppure t-butile oppure pentile.
Gli atomi di carbonio caratterizzati con * nelle formule, indicano atomi di carbonio asimmetrici. Di regola, si tratta di miscele di diastereoisomeri (eso/endo) dei composti conformi all'invenzione. I diastereoisomeri possono venire separati però, se necessario, anche secondo metodi noti (per esempio mediante co-cristallizzazione oppure mediante cromatografia). Qui di seguito di rinuncia alla caratterizzazione degli atomi di carbonio asimmetrici.
Una particolarità di sostanze organiche consiste nel fatto che esse si decompongono facilmente sotto l'influsso di calore, di luce oppure di una irradiazione, sotto l'influsso di un carico meccanico (in particolare per effetto di sollecitazioni di taglio) e sotto l'influsso di reagenti chimici (in particolare l'ossigeno atmosferico).
I composti di formula I e/o II sono adatti per la stabilizzazione di materiale organico, in particolare di polimeri, specialmente di (co)polimeri dello stirolo, come polistirolo, ABS (acrilonitrilebutadiene-stirolo), IPS (polistirene con elevata resistenza agli urti, copolimero ad innesto stirolo su polibutadiene) , MBS (metacrilonitrilebutadiene-stirolo) e SBS (stirolo-butadiene-stirolo). Essi agiscono in particolare come antiossidanti.
L'invenzione riguarda pertanto anche composizioni contenenti un prodotto organico sensibile nei confronti di una degradazione ossidativa, termica e/o provocata dalla luce e almeno un composto di formula I e/o II. In queste composizioni, i composti conformi all'invenzione sono contenuti opportunamente in quantità di 0,01 fino a 10, per esempio 0,05 fino a 5, preferibilmente 0,05 fino a 3, però in particolare 0,1 fino a 2% in peso. Può trattarsi di uno o più di questi composti, e le indicazioni di percentuali in peso si riferiscono alla quantità totale di questi composti. Base per il calcolo è il peso totale della sostanza organica senza i composti di formula I e II.
Esempi di sostanze organiche da stabilizzare sono: 1. Polimeri di monoolefine e di diolefine, per esempio polipropilene, poliisobutilene, polibutene-1, poli-4-metilpentene-1, poliisoprene oppure polibutadiene e anche polimeri di cicloolefine, come per esempio di ciclopentene o norbornene o diciclopentadiene; inoltre polietilene (che può essere eventualmente reticolato), per esempio polietilene di elevata densità (HDPE), polietilene di bassa densità (LDPE), polietilene lineare di bassa densità (LLDPE), polietilene ramificato di bassa densità (VLDPE).
Poliolefine, ossia polimeri di monoolefine come vengono citati come esempi nel capoverso precedente, in particolare polietilene e polipropilene possono venire preparati secondo diversi procedimenti, in particolare secondo i seguenti metodi:
a) mediante polimerizzazione a radicali (eventualmente ad alta pressione e ad alta temperatura).
b) per mezzo di un catalizzatore in cui il catalizzatore contiene usualmente uno o più metalli del gruppo IVb, Vb, VIb oppure Vili. Questi metalli possiedono usualmente uno o più ligandi come ossidi, alogenuri, alcolati, esteri, eteri, ammine, gruppi alchilici, alchenilici e/o arilici che possono essere π- oppure σ-coordinati. Questi complessi di metalli possono essere liberi oppure possono essere fissati su un supporto come per esempio su cloruro di magnesio attivato, cloruro di titanio(III), ossido di alluminio oppure ossido di silicio. Questi catalizzatori possono essere solubili oppure insolubili nel mezzo di polimerizzazione. I catalizzatori possono essere attivi come tali nella polimerizzazione oppure si possono impiegare ulteriore attivatori come per esempio metalloalchili, idruri di metalli, alchilalogenuri di metalli, alchilossidi di metalli oppure alchilossani di metalli, i metalli essendo elementi dei gruppi la, IIa e/o IIIa. Gli attivatori possono essere modificati per esempio con ulteriori gruppi di esteri, eteri, ammine oppure gruppi di sililetere. Questi sistemi di catalizzatori vengono indicati usualmente come catalizzatori Phillips, Standard Oil Indiana, Ziegler (-Natta), TNZ (DuPont), metallocene oppure catalizzatori a sito singolo (SSC).
2. Miscele dei polimeri citati sotto 1), per esempio miscele di polipropilene con poliisobutilene, polipropilene con polietilene (per esempio PP/HDPE, PP/LDPE) e miscele di diversi tipi di polietilene (per esempio LDPE/HDPE).
3. Copolìmeri dì monoolefine e diolefine tra di loro oppure con altri monomeri vinilici come per esempio copolimeri etilene-propilene, polietilene lineare di bassa densità (LLDPE) e miscele di questo con polietilene di bassa densità (LDPE), copolimeri propilene-butene-1, copolimeri propilene-isobutilene, copolimeri etilene-butene-1, copolimeri etileneesene, copolimeri etilene-metilpentene, copolimeri etilene-eptene, copolimeri etilene-ottene, copolimeri propilene-butadiene, copolimeri isobutilene-isoprene, copolimeri etilene-alchilacrilato, copolimeri etilene-alchilmetacrilato, copolimeri etilenevinilacetato e loro copolimeri con monossido di carbonio oppure copolimeri etilene-acido acrilico e loro sali (ionomeri), e anche terpolimeri di etilene con propilene e con un diene, come esadiene, diciclopentadiene oppure etilidennorbornene, inoltre miscele di tali copolimeri tra di loro e con i polimeri citati sotto 1), per esempio polipropilene/ copolimeri etilene-propilene, LDPE/copolimeri etilene-vinilacetato, LDPE/copolimeri etilene-acido acrilico, LLDPE/copolimeri etilene-vinil acetato, LLDPE/copolimeri etilene-acido acrilico e copolimeri polialchilene/monossido di carbonio strutturati in modo alternato oppure in modo statistico e loro miscele con altri polimeri come per esempio poliammidi.
4. Resine di idrocarburi (per esempio C5-C9) ivi comprese loro modificazioni idrogenate (per esempio resine adesivanti) e miscele di polialchileni e di amido.
5. Polistirolo, poli-(p-metilstirolo), poli-(ametilstirolo.
6. Copolimeri dello stirolo oppure dell'ametilstirolo con dieni oppure con derivati acrilici come per esempio copolimeri stirolo-butadiene, stirolo-acrilonitrile, stirolo-alchilmetacrilato, stirolo-butadiene-alchilacrilato e -metacrilato, stirolo-anidride dell'acido maleico, stiroloacrilonitrile-metilacrilato; miscele dotate di elevata resilienza ottenute da copolimeri dello stirolo e da un altro polimero come per esempio un poliacrilato, un polimero dienico oppure un terpolimero etilene-propilene-diene; e anche copolimeri a blocco dello stirolo come per esempio stirolo-butadiene-stirolo (SBS), stirolo-isoprenestirolo, stirolo-etilene/butilene-stirolo oppure stirolo-etilene/propilene-stirolo.
7. Copolimeri ad innesto dello stirolo oppure della α-metilstirolo come per esempio stirolo su polibutadìene, stirolo su copolimeri polibutadienestirolo oppure polibutadiene-acrilonitrile, stirolo e acrilonitrile (oppure metacrilonitrile) su polibutadìene; stirolo, acrilonitrile e metilmetacrilato su polibutadìene; stirolo e anidride dell'acido maleico su polibutadìene; stirolo, acrilonitrile e anidride dell'acido maleico oppure immide dell'acido maleico su polibutadìene; stirolo e immide dell'acido maleico su polibutadìene, stirolo e alch.il acrilati oppure alchil metacrilati su polibutadìene, stirolo e acrilonitrile su terpolimeri etilene-propilene-diene, stirolo e acrilonitrile su polialchilacrilati o polialchilmetacrilati, stirolo e acrilonitrile su copolimeri di acrilato-butadiene, e anche loro miscele con i copolimeri citati sotto 6), come sono noti per esempio come cosiddetti polimeri ABS-, MBS-, ASA- oppure AES.
8. Polimeri contenenti alogeni come per esempio policloroprene, cloro-caucciù polietilene clorurato o clorosolfonato, copolimeri di etilene e di etilene clorurato, omopolimeri e copolimeri della epicloroidrina, in particolare polimeri ottenuti da composti vinilici contenenti alogeni, come per esempio polivinilcloruro, polivinilidencloruro, polivinilfluoruro, polivinilidenfluoruro; e anche loro copolimeri come vinilcloruro-vinilidencloruro, vinilcloruro-vinilacetato oppure vinilidenclorurovinilacetato .
9. Polimeri che derivano da acidi α,β-non saturi e da loro derivati, come poliacrilati e polimetacrilati, poiimetilmetacrilati, poliacrilammidi e poliacrilonitrili modificati per la resistenza agli urti con butilacrilato.
10. Copolimeri dei monomeri citati sotto 9) tra loro oppure con altri monomeri non saturi, come per esempio, copolimeri acrilonitrile-butadiene, copolimeri acrilonitrile-alchilacrilato, copolimeri acrilonitrile-alcossialchilacri lato, copolimeri acrilonitrile-vinilalogenuro oppure terpolimeri acrilonitrile-alchilmetacri lato-butadiene.
11. Polimeri che derivano da alcoli e ammine non saturi oppure da loro acilderivati oppure acefali come alcol polivinilico, polivinilacetato, polivinilstearato, polivinilbenzoato, polìvinilmaleato, polivinilbutirrale, poliallilftalato, poliallilmelammina; e anche loro copolimeri con olefine citate nel punto 1.
12. Omopolimeri e copolimeri di eteri ciclici, come polialchilenglicoli, polietilenossido, poliproprilenossido oppure loro copolimeri con bisglicidileteri .
13. Poliacetali, come il poliossimetilene e anche quei poliossimetileni che contengono comonomeri come per esempio etilenossido; poliacetali che sono modificati con poliuretani, acrilati oppure con MBS termoplastici .
14. Polifenilenossidi e -solfuri e loro miscele con polimeri dello stirolo oppure con poliammidi.
15. Poliuretani che derivano da un lato da polieteri, poliesteri e polibutadieni con gruppi idrossìlicì terminali e dall'altro lato derivano da poliisocianati alifatici oppure aromatici e anche loro precursori.
16. Poliammidi e copoliammidi che derivano da diammine e da acidi bicarbossilici e/o da acidi amminocarbossilici oppure dai corrispondenti lattami come la poliammide 4, poliammide 6, poliammide 6/6, 6/10, 6/9, 6/12, 4/6, 12/12, poliammide 11, poliammide 12, poliammidi aromatiche ottenute partendo da m-xilolo, da una diammina e dall'acido adipico; poliammidi preparate da esametilendiammina e da acido isoftalico e/o acido tereftalico ed eventualmente da un elastomero come agente modificante, per esempio poli-2,4,4-trimetilesametilen-tereftalammide, poli-mfenilen-isoftalammide, copolimeri a blocco delle poliammìdi citate in precedenza con poliolefine, copolimeri di olefine, ionomeri oppure elastomeri legati oppure innestati chimicamente; oppure con polieteri come per esempio con polietilenglicol, polipropilenglicol oppure politetrametilenglicol, e inoltre poliammìdi oppure copoliammidi modificate con EPDM oppure con ABS; e anche poliammìdi condensate durante la lavorazione (sistemi di poliammìdi RIM).
17. Poliuree, poliimmidi, poliammido-immidi e polibenzimmidazoli .
18. Poliesteri che derivano da acidi bicarbossilici e da dialcoli e/o da acidi idrossicarbossilici oppure dai corrispondenti lattoni, come polietilentereftalato, polibutilentereftalato, poli-1,4-dimetilolcicloesan-tereftalato, poliidrossibenzoati e anche polieteri-esteri a blocco che derivano da polieteri con gruppi ossidrilici terminali; inoltre poliesteri modificati con policarbonati oppure con MBS.
19. Policarbonati e poliesteri-carbonati.
20. Polisolfoni, polieteri-solfoni e polieterichetoni.
21. Polimeri reticolati che derivano da un lato da aldeidi e dall'altro lato da fenoli, urea e melammina come resine fenolo-formaldeide, ureaformaldeide e melammina-formaldeide.
22. Resine alchidiche essiccative e non essiccative .
23. Resine di poliesteri non saturi che derivano da copoliesteri di acidi bicarbossilici saturi e non saturi con alcoli plurivalenti e anche composti vinilici come agenti di reticolazione, e anche loro varianti difficilmente combustibili, contenenti alogeni.
24. Resine acriliche reticolabili che derivano da esteri dell'acido acrilico sostituiti come per esempio da eposssiacrilati, uretano-acrilati oppure poliesteri-acrilati .
25. Resine alchidiche, resine di poliesteri e resine di acrilato che sono reticolate con resine di melammina, resine ureiche, poliisocianati oppure resine epossidiche.
26. Resine epossidiche reticolate che derivano da poliepossidi, per esempio bis-glicidileteri oppure da diepossidi cicloalifatici.
27. Polimeri naturali come cellulosa, caucciù naturale, gelatina e anche loro derivati chimicamente trasformati polimero-omologhi come acetati, propionati e butirrati di cellulosa, e anche gli eteri della cellulosa come metilcellulosa; e anche resine della colofonia e derivati.
28. Miscele (polimiscele) dei polimeri citati sopra come per esempio PP/EPDM, poliammide/EPDM oppure ABS, PVC/EVA, PVC/ABS, PVC/MBS, PC/ABS, PBTP/ABS, PC/ASA, PC/PBT, PVC/CPE, PVC/acrilati, POM/PUR termoplastico, PC/PUR termoplastico, POM/acrilato, POM/MBS, PPO/HIPS, PPO/PA 6.6 e copolimeri, PA/HDPE, PA/PP, PA/PPO.
29. Emulsioni acquose di caucciù naturali oppure sintetici, per esempio latice di caucciù naturale oppure latici di copolimeri stirolo/butadiene carbossilati.
30. Sostanze organiche naturali e sintetiche, che rappresentano composti monomeri puri oppure loro miscele, per esempio oli minerali, grassi, oli e cere animali oppure vegetali, oppure oli, cere e grassi a base di esteri sintetici (per esempio ftalati, adipati, fosfati oppure trimellitati) e anche miscele di esteri sintetici con oli minerali, in qualsiasi rapporto in peso, come vengono impiegati per esempio in qualità di preparati per filatura, e anche loro emulsioni acquose.
Si preferiscono sostanze che presentano doppi legami, poiché, così, si può utilizzare il vantaggio dell'inserimento chimico nel substrato.
Tali substrati sono per esempio elastomeri. Come tali si prendono in considerazione per esempio:
1. Polidieni, per esempio polibutadiene, poliisoprene oppure policloroprene; copolimeri a blocchi, per esempio stirolo/butadiene/stirolo, stirolo/ isoprene/stirolo oppure copolimeri acrilonitril/butadiene.
2. Copolimeri di mono- e di di-olefine tra loro oppure con altri monomeri vinilici, per esempio copolimeri etilene-alchilacrilato, copolimeri etilene-alchilmetacrilato, copolimeri etilene-vinilacetato e anche terpolimeri di etilene con propilene e con un diene, come esadiene, diciclopentadiene oppure etilidennorbornene.
3. Polimeri contenenti alogeni, per esempio policloroprene, cloro-caucciù, polietilene clorurato oppure clorosolfonato, omopolimeri e copolimeri di epicloridrina, copolimeri di clorotrifluoroetilene, polimeri di composti vinilici contenenti alogeni, per esempio polivinilidencloruro, polivinilidenfluoruro; e anche loro copolimeri, come vinil-cloruro, viniliden-cloruro, vinilcloruro-vinilacetato oppure vinilidencloruro-vinilacetato .
4. Poliuretani che derivano, da un lato da polieteri, poliesteri e polibutadiene con gruppi ossidrilici terminali e, d'altro canto, da poliisocianati alifatici oppure aromatici e anche loro prodotti precursori.
5. Caucciù naturale.
6. Miscele (polimiscele) dei suddetti polimeri).
7. Emulsioni acquose di caucciù naturali oppure sintetici, come per esempio latice di caucciù naturale oppure latici di copolimeri stirolo/butadiene carbossilati.
Eventualmente, questi elastomeri sono presenti sotto forma di latici e possono venire stabilizzati come tali. Si possono stabilizzare anche vulcanizzati .
Si preferiscono composizioni che contengono, come elastomero, un polidiene, come caucciù di polibutadiene .
L'introduzione nei prodotti organici può venire effettuata per esempio mediante miscelazione dei composti conformi all'invenzione oppure di loro miscele ed eventualmente di ulteriori additivi secondo i metodi usuali nella tecnica. Se si tratta di polimeri, in particolare polimeri sintetici, l'incorporazione può venire effettuata prima oppure durante la formatura oppure mediante applicazione dei composti, sciolti oppure dispersi, sul polimero, eventualmente con successiva evaporazione del solvente. Nel caso di elastomeri, questi possono venire stabilizzati anche sotto forma di latici. Un'ulteriore possibilità preferita dell'impiego dei composti conformi all'invenzione consiste nella loro aggiunta nella preparazione di miscele di gomma, insieme con gli altri componenti usuali della miscela e insieme con ingredienti secondo le tecniche usuali, per esempio in miscelatori Banbury, in miscelatori a cilindri oppure in apparecchi di estrusione con miscelazione. In particolare, la presenza dei composti di formula I e/o II nel corso del processo di miscelazione e anche durante la successiva formatura e durante la reazione di reticolazione (vulcanizzazione per ottenere l'articolo di gomma pronto per l'impiego) e durante l'impiego dell'articolo finito, provoca un collegamento chimico con l'elastomero/polimero. Si può mettere in evidenza ciò per esempio analiticamente per mezzo del più elevato contenuto residuo di additivo, misurato sull'azoto residuo, in confronto con composti non inseribili. Oggetto dell'invenzione, pertanto, sono in particolare composizioni nelle quali composti di formula I e/o II sono inseriti in un elastomero/ polimero oppure sono chimicamente legati con questo. I composti conformi all'invenzione oppure loro miscele possono venire aggiunti alle resine sintetiche da stabilizzare anche sotto forma di una mescola-madre che contiene questi composti per esempio in una concentrazione di 2,5-25% in peso.
Opportunamente, l'incorporazione dei composti di formule I e II può venire effettuata secondo i seguenti metodi:
sotto forma di emulsione oppure di dispersione (per esempio α latici o a polimeri in emulsione) .
Sotto forma di miscela secca durante la miscelazione di componenti additivi o di miscele di polimeri,
mediante aggiunta diretta nell'apparecchiatura di lavorazione (per esempio apparecchi di estrusione, miscelatori interni, ecc.)
sotto forma di soluzione oppure di massa fusa. Composizioni di polimeri conformi all'invenzione possono venire impiegate in diverse forme oppure possono venire lavorate ottenendo così diversi prodotti, per esempio sotto forma di fogli, fibre, piccoli nastri, composizioni da stampaggio, profilati oppure sotto forma di leganti per vernici, adesivi oppure mastici. Oltre ai composti conformi all'invenzione oppure a loro miscele, le composizioni conformi all'invenzione, in particolare quando contengono polimeri organici, preferibilmente sintetici, possono contenere ancora ulteriori additivi noti allo specialista, per esempio:
1. Antiossidanti
1.1 Monofenoli alchilati per esempio, 2,6-ditert .-butil-4-metilfenolo, 2-tert.-butil-4,6-dimetilfenolo, 2,6-di-tert .butil-4-etilfenolo, 2,6-di-tert .butil-4-n-butilfenolo, 2,6-di-tert.butil-4-iso-butilfenolo, 2,6-di-ciclopentil-4-metilfenolo, 2-(α-metilcicloesil)-4,6-dimetilfenolo, 2,6-diottadecil-4-metilfenolo, 2,4,6-tri-cicloesilfenolo, 2,6-di-tert.butil-4-metossimetilfenolo, 2,6-di-nonil-4-metilfenolo, 2,4-dimetil-6- (1'-metil-undec-1'-il)-fenolo, 2,4-dimetil-6- (1'-metil-eptadec-1'-il)-fenolo, 2,4-dimetil-6- (1'-metil-tridec-1'-il)-fenolo e loro miscele.
1.2. Alchiltiometilfenoli, per esempio, 2,4-diottiltiometil-6-terz-butilfenolo, 2,4-di-ottiltiometil-6-metilfenolo, 2,4-di-ottiltiometil-6-etilfenolo, 2,6-di-dodeciltiometil-4-nonilfenolo.
1.3. Idrochinoni e idrochinoni alchilati per esempio 2,6-di-tert.butil-4-metossifenolo, 2,5-ditert .butil-idrochinone, 2,5-di-tert.amil-idrochinone, 2,6-difenil-4-ottadecilossifenolo, 2, 6-di-terz-butilidrochinone, 2,5-di-terz-butil-4-idrossianisolo, 3,5-di-terz-butil-4-idrossianisolo, 3,5-di-terz-butil-4-idrossif enil-stearato, bis-{3,5-di-terz-butil-4-idrossifenil)adipato.
1.4. Tocoferoli, per esempio α-tocoferolo, βtocoferolo, γ-tocoferolo, δ-tocoferolo e loro miscele (vitamina E).
1.5 Tiodifenileteri idrossilati, per esempio 2,2'-tio-bis- (6-tert.butil-4-metilfenolo), 2,2'-tiobis- (4-ottilfenolo), 4,4'-tio-bis-(6-tert.butil-3-metilfenolo) , 4,4'-tio-bis-(6-tert.butil-2-metilfenolo) , 4,4'-tio-bis-(3,6-di-sec-amilfenolo), 4,4'-bis- (2,6-dimetil-4-idrossifenil)-disolfuro.
1.6 Alchiliden-bisfenoli, per esempio, 2,2'-metilen-bis- (6-tert.butil-4-metilfenolo), 2,2'-metilen-bis- {6-tert.butil-4-etilfenolo), 2,2'-metilen-bis- [4-metil-6-(α-metilcicloesil)-fenolo], 2,2'-metilen-bis- (4-metil-6-cicloesilfenolo), 2,2'-metilen-bis- (6-nonil-4-metilfenolo), 2,2'-metilenbis- (4,6-di-terz.butilfenolo), 2,2'-etiliden-bis-(4,6-di-terz.butilfenolo), 2,2'-etiliden-bis-(6-tert .butil-4-isobutilfenolo), 2,2'-metilen-bis-[6-(ametilbenzil)-4-nonilfenolo] , 2,2'-metilen-bis-[6(α,α-dimetilbenzil)-4-nonilfenolo], 4,4'-metilen-bis-{2,6-di-tert.butilfenolo), 4,4'-metilen-bis-(6-tert .butil-2-metilfenolo), 1,1-bis-(5-tert.butil-4-idrossi-2-raetilfenil)-butano, 2,6-di-(3-tert.butil-5-metil-2-idrossibenzil) -4-metilfenolo, 1,1,3-tris-(5-tert.butil-4-idrossi-2-metilfenil) -butano, 1,1-bis-(5-tert.butil-4-idrossi-2-metil-fenil)-3-n-dodecilmercaptobutano, etileneglicol-bis-[3,3-bis-(3'-tert .butil-4'-idrossifenil)-butirrato], bis-(3-tert.-butil-4-idrossi-5-metil-fenil) -diciclopentadiene, bis- [2-(3'-tert.buti1-2'-idrossi-5'-metil-benzil)-6-tert .butil-4-metil-fenil]-tereftalato, 1,1-bis-(3,5-dimetil-2-idrossifenil) -butano, 2,2-bis-(3,5-ditert.-butil-4-idrossifenil )-propano, 2,2-bis-(5-tert.-butil-4-idrossi-2-metil-fenil) -4-n-dodecilmercapto-butano, 1,1,5,5-tetra-(5-terz.-butil-4-idrossi-2-metilfenil)-pentano .
1.7. O-, N- e S-benzilcomposti, per esempio 3,5,3',5'-tetra-terz.-butil-4, 4'-diidrossi-dibenzìletere, ottadecil-4-idrossi-3, 5-dimetilbenzil-mercaptoacetato, tris-(3,5-di-terz.-butil-4-idrossibenzil)-ammina, bis- (4-tert.-butil-3-idrossi-2,6-dimetilbenzil)-ditiotereftalato, bis- (3,5-di-terz.-butil-4-idrossibenzil)-solfuro, isoottil-3,5-di-terz.-butil-4-idrossibenzil-mercaptoacetato .
1.8. Maionati idrossibenzilati, per esempio diottadecil-2,2-bis- (3,5-di-terz.butil-2-idrossibenzil)-maionato, di-ottadecil-2-(3-terz-butil-4-idrossi-5-metilbenzil)-maionato, di-dodecilmercaptoetil-2,2-bis- (3,5-di-terz-butil-4-idrossibenzil)-maionato, di-[4-(1,1,3,3-te trametilbutil)-fenil]-2,2-bis-(3,5-di-terz-butil-4-idrossibenzil )-maionato.
1.9. Composti idrossibenzil-aromatici, per esempio 1,3,5-tris-(3,5-di-terz-butiì-4-idrossibenzil)-2,4,6-trimetilbenzolo, 1,4-bis-(3,5-di-terzbutil-4-idrossibenzil)-2, 3,5,6-tetrametilbenzolo, 2,4,6-tris- (3,5-di-terz-butil-4-idrossibenzil)-fenolo .
1.10. Composti triazinici, per esempio 2,4-bisottilmercapto-6- (3,5-di-terz-butil-4-idrossianilino)-1,3,5-triazina, 2-ottilmercapto-4,6-bis-(3,5-diterz.-butil4-idrossianilino) -1,3,5-triazina, 2-ottilm.ercapto-4,6-bis-(3,5-di-terz-butil-4-idrossifenossi)-1,3,5-triazina, 2,4,6-tris-(3,5-di-terz-butil-4-idrossifenossi)-1,2,3-triazina, l,3,5-tris-(3,5-diterz-butil-4-idrossibenzil)-isocianurato, 1,3,5-tris-(4-terz-butil-3-idrossi-2,6-dimetilbenzil)-isocianurato, 2,4,6-tris-(3,5-di-terz-butil-4-idrossifeniletil)-1,3,5-triazina, 1,3,5-tris-(3,5-di-terz-butil-4-idrossifenilpropionil)-esaidro-1, 3,5-triazina, 1.3.5-tris- (3,5-dicicloesil-4-idrossibenzil)-isocianurato .
1.11. Benzilfosfonati per esempio dimetil-2,5-di-terz-butil-4-idrossibenzilfosfonato, dìetil-3,5-di-terz-butil-4-idrossibenzilfosfonato, diottadecil-3.5-di-terz-butil-4-idrossibenzilfosfonato, diottadecil-5-terz-butil-4-idrossi-3-metilbenzilfosfonato, sale di calcio della monoetil-estere dell'acido 3,5-di-terz-butil-4-idrossibenzil fosfonico.
1.12. Acilamininofenoli, per esempio 4-idrossianilide dell'acido laurico, 4-idrossi-anilide dell'acido stearico, estere ottilico dell'acido N-(3,5-di-terz-butil-4-idrossifenil)-carbammico.
1.13 Esteri dell'acido β-(3,5-di-tert.butil-4-idrossifenil)-propionico con alcoli monovalenti oppure plurivalenti, come per esempio con metanolo, etanolo, ottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, etilenglicole, 1,2-propandiolo, neopentilglicol, tiodietilenglicol, dietileneglicol, trietileneglicol, pentaeritrite, tris-(idrossietil)-isocianurato, Ν,Ν' -bis-(idrossietil)-diammide dell'acido ossalico, 3-tiaundecanolo, 3-tiapentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-1-fosfa-2,6,7-triossabiciclo [2.2.2]-ottano.
1.14. Esteri dell'acido β-(5-tert.butil-4-idrossi-3-metilfenil)-propionico con alcoli monovalenti oppure plurivalenti, come per esempio con metanolo, etanolo, ottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, etilenglicol, 1,2-propandiolo, neopentilglicol, tiodietileneglicol, dietilenglicol, trietileneglicol, pentaeritrite, tris- (idrossi)etil-isocianurato, N,N'-bis-(idrossietil)-diammide dell'acido ossalico, 3-tiaundecanolo, 3-tiapentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-1-fosfa-2,6,7-triossabiciclo-[2.2.2]-ottano.
1.15. Esteri dell'acido β-(3,5-dicicloesil-4-idrossifenil)-propionico con alcoli monovalenti oppure plurivalenti come per esempio con metanolo, etanolo, ottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, etilenglicol, 1,2-propandiolo, neopentilglicol, tiodietilenglicol, dietilenglicol, trietilenglicol, pentaeritrite, tris-(idrossi)etilisocianurato, Ν,Ν' -bis-(idrossietil)-diammide dell'acido ossalico, 3-tiaundecanolo, 3-tiapentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-l-fosfa-2,6,7-triossabiciclo [2.2.2]-ottano.
1.16. Esteri dell'acido 3,5-di-terz-butil-4idrossi-fenilacetico con alcoli monovalenti oppure plurivalenti come per esempio con metanolo, etanolo, ottanolo, ottadecanolo, 1, 6-esandiolo, 1,9-nonandiolo, etilenglicol, 1,2-propandiolo, neopentilglicol, tiodietilenglicol, dietilenglicol, trietilenglicol, pentaeritrite, tris-(idrossietil)-isocianurato, Ν,Ν'-bis-(idrossietil)-diammide dell'acido ossalico, 3-tiaundecanolo, 3-tiapentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-1-fosfa-2, 6,7-triossabiciclo[2.2.2]-ottano .
1.17. Ammidi dell'acido β-(3,5-di-tert.butil-4-idrossifenil)-propionico come per esempio, N,N'-bis-(3,5-di-tert.butil-4-idrossifenilpropionil)-esametilenediammina, N,N'-bis-(3,5-di-tert.butil-4-idrossifenilpropionil)-trimetilenediammina, Ν,Ν'-bis-(3,5-di-tert.butil-4-idrossifenilpropionil)-idrazina.
2. Agenti che assorbono la luce UV ed agenti fotoprotettori
2.1. 2- (2'-idrossifenil)-benzotriazoli, come, per esempio, 2-(2'-idrossi-5'-metilfenil)benzotriazolo, 2- (3',5'-di-terz-butil-2'-idrossifenil) benzotriazolo, 2- (5'-terz-butil-2'-idrossifenil)-benzotriazolo, 2- (2'-idrossi-5'-(1,1,3,3-tetrametilbutil)fenil]-benzotriazolo, 2-(3',5'-di-terz.butil2'-idrossifenil)-5-cloro-benzotriazolo, 2-(3'-terzbutil-2'-idrossi-5'-metilfenil) -5-clorobenzotriazolo 2- (3'-sec-butil-5'-terz-butil-2'-idrossifenil)-benzotriazolo, 2-(2'-idrossi-4'-ottossifenil)-benzotriazolo, 2- (3',5'-di-terz-amil-2'-idrossifenil)-benzotriazolo, 2-(3',5'-bis(α,α-dimetilbenzil) -2' -idrossifenil)benzotriazolo, miscela di 2-(3'-terzbutil-2'-idrossi-5'- (2-ottilossicarboniletil)fenil)-5-cloro-benzotriazolo, 2-(3'-terz-butil-5'-[2-(2-etilesilossi)carboniletil] -2' -idrossifenil)-5-clorobenzotriazolo, 2-(3'-terz-butil-2'-idrossi-5'-(2-metossicarboniletil) fenil)-5-cloro-benzotriazolo, 2-(3'-terz-butil-2'-idrossi-5'-(2-metossicarboniletil) fenil)-benzotriazolo, 2-(3'-terz-butil-2'-idrossi-5'-(2-ottilossicarboniletil)fenil)-benzotriazolo, 2-(3'-terz-butil-5'- [2-(2-etilesilossi)carboniletil]-2'-idrossifenil)-benzotriazolo, 2-(3'-dodecil-2'-idrossi-5'-metilfenil)-benzotriazolo e 2-(3'-terz-butil-2'-idrossi-5'- (2-isoottilossicarboniletil)fenil-benzotriazolo, 2,2'-metilen-bis [4-(1,1,3,3-tetrametilbutil)-6-benzotriazol-2-il-fenolo] ; prodotto di transesterificazione di 2-[3'-terz-butil-5'-(2-metossicarboniletil)-2'-idrossi-fenil]-benzotriazolo con polietilenglicol 300; [R-CH2CH2-COO(CH2)3]2 con R = 3'-terz-butil-4’-idrossi-5 '-2H-benzotriazol-2-il-fenile.
2.2. 2-idrossibenzofenoni, come per esempio, il 4-idrossi-, 4-metossi-, 4-ottossi-, 4-decilossi-, 4-dodecilossi-, 4-benzilossi-, 4,2',4'-triidrossi-, 2'-idrossi-4,4'-dimetossi-derivato .
2.3. Esteri di acidi benzoici eventualmente sostituiti, come per esempio, 4-tert.butil-fenilsalicilato, fenilsalicilato, ottilfenil-salicilato, dibenzoilresorcina, bis-(4-tert.-butilbenzoil)-resorcina, benzoilresorcina, estere 2,4-ditert.butilfenilico dell'acido 3,5-di-tert.butil-4-idrossibenzoico, estere esadecilico dell'acido 3,5-di-tert.butil-4-idrossibenzoico, estere ottadecilico dell'acido 3,5-di-tert-butil-4-idrossibenzoico, estere 2-metil-4,6-di-tert-butil-fenilico dell'acido 3,5-di-tert-4-idrossibenzoico .
2.4. Acrilati, come per esempio, estere etilico oppure estere isoottìlìco dell'acido α-ciano-β,βdifenilacrilico, estere metilico dell'acido acarbometossi-cinnamico, estere metilico oppure estere butilico dell'acido a-ciano--metil-p-metossicinnamico, estere metilico dell'acido a-carbometossip-metossi-cinnamico, N-β-carbometossiβ-cianovinil) -2-metil-indolna.
2.5. Composti del nichel, come per esempio, complessi con il nichel del 2,2'-tio-bis-[4-(1, 1, 3,3tetrametilbutil)-fenolo] , come il complesso 1:1 oppure il complesso 1:2, eventualmente con ulteriori ligandi come n-butil-ammina, trietanolammina, oppure N-cicloesil-dietanolammina, dibutilditiocarbammato di nichel, sali di nichel di esteri monoalchilici dell'acido 4-idrossi-3,5-di-tert.-butilbenzilfosfonico come dell'estere metilico oppure etilico, complessi del nichel di chetossime, come della 2-idrossi-4-metil-fenil-undecilchetonossima, complessi con il nichel del 1-fenil-4-lauroil-5-idrossipirazolo eventualmente con ulteriori ligandi.
2.6 Ammine dotate di impedimento sierico, come per esempio, bis-(2,2,6,6-tetrametil-piperidil)-sebacato, bis-(2,2,6,6-tetrametilpipèridil)-succinato, bis- (1,2,2,6,6-pentametilpiperidil)-sebacato, bis (1,2,2,6,6-pentametilpiperidil)-estere dell'acido n-butil-3,5-di-tert .buti1-4-idrossibenzil-maionico, prodotto di condensazione ottenuto da 1-idrossietil-2,2,6,6-tetrametil-4-idrossipiperidina e dall'acido succinico, prodotto di condensazione ottenuto da Ν,Ν'-bis- (2,2,6,6-tetrametil-4-piperidil)-esametilendiammina e dalla 4-tert.ottilammino-2,6-dicloro-1,3,5-s-triazina, tris-(2,2,6,6-tetrametil-4-piperidil)-nitrilotriacetato, tetrakis-(2,2,6,6-tetrametil-4-piperidil)-1,2,3,4-butantetranoato, 1,1'(1,2-etandiil)-bis-(3,3,5,5-tetrametilpiperazinone), 4-benzoil-2,2,6, 6-tetrametilpiperidina, 4-stearilossi-2,2,6,6-tetrametil-piperidina, bis-(l,2,2,6,6-pentametilpiperidil)-2-n-butil-2- (2-idrossi-3,5-diterz .-butil-benzil)-maionato, 3-n-ottil-7,7,9,9-tetrametil-1,3,8-triazaspiro [4.5]decan-2,4-dione, bis- (1-ottilossi-2,2,6,6-tetrametilpiperidil)-sebacato, bis- (1-ottilossi-2,2,6,6-tetrametilpiperidil)-succinato, prodotto di condensazione di N,N-bis-(2,2,6,6-tetrametil-4-piperidil)-esametilendiammina e 4-morfolino-2,6-dicloro-1, 3,5-triazina, prodotto di condensazione di 2-cloro-4,6-(4-n-butilammino-2.2.6.6-tetrametilpiperidil) -1,3,5-triazina e di 1,2-bis- (3-amminopropilammino)etano, prodotto di condensazione di 2-cloro-4,6-di-(4-n-butilairanino-1.2.2.6.6-pentametilpiperidil) -1,3,5-triazina e di 1,2-bis- (3-ammino-propilammino)-etano, 8-acetil-3-dodecil-7,7,9,9-tetrametil-1 ,3,8-triazaspiro-[4.5] decan-2,4-dione, 3-dodecil-1-(2,2,6,6-tetrametil-4-piperidil)pirrolidin-2,5-dione, 3-dodecil-1-(1,2,2,6,6-pentametil-4-piperidil)-pirrolidin-2,5-dione.
2.7. Diammidi dell'acido ossalico, come per esempio, 4,4'-di-ottilossi-ossanilide, 2, 2' -dietossiossanilide, 2,2'-di-ottilossi-5, 5'-di-tert.butilossanilide, 2, 2' -di-dodecilossi-5,5'-di-tert.butilossanilide, 2-etossi-2'-etil-ossanilide, N,N'-bis-(3-dimetilamminopropil)-ossalammide, 2-etossi-5-tert.-butil-2'-etil-ossanilide e una sua miscela con 2-etossi-2'-etil-5,4'-di-tert .butilossanilide, miscele di ossanilidi orto e para metossi- e anche o- e petossi-di-sostituite .
2.8. 2-(2-idrossifenil)-1,3,5-triazine, come per esempio 2, 4,6-tris(2-idrossi-4-ottilossifenil)-1,3,5-triazina, 2- (2-idrossi-4-ottilossifenil)-4,6-bis- (2,4-dimetilfenil)-1,3,5-triazina, 2-(2,4-diidrossifenil)-4,6-bis (2,4-dimetilfenil)-1,3,5-triazina, 2,4-bis- (2-idrossi-4-propossifenil)-6-(2,4-dimetilfenil)-1,3,5-triazina, 2-(2-idrossi-4-ottilossifenil)-4,6-bis (4-metilfenil)-1,3,5-triazina, 2-(2-idrossi-4-dodecilossifenil)-4,6-bis(2,4-dimetilfenil)-1,3,5-triazina, 2-[2-idrossi-4-(2-idrossi-3-butilossi-propilossi)fenil]-4, 6-bis(2,4-bis{2,4-dimetilfenil)-1,3,5-triazina, 2-[2-idrossi-4-(2-idrossi-3-ottilossi-propossi )fenil]-4,6-bis(2,4-dimetilfenil)-1,3,5-triazina.
3. Disattivatori di metalli, come per esempio, Ν,Ν'-difenil diammide dell'acido ossalico, N-salicilal-N'-saliciloilidrazina, N,N'-bis-(saliciloil)-idrazina, Ν,Ν'-bis- (3,5-di-tert.butil-4-idrossifenilpropionil)-idrazina, 3-saliciloilammino-l,2,4-triazolo, bis-(benziliden)-diidrazide dell'acido ossalico, ossanilide, diidrazide dell'acido isoftalico, bis-fenilidrazide dell'acido sebacico, N,N'-diacetil-diidrazide dell'acido adipico, Ν,Ν'-bis-saliciloil-diidrazide dell'acido ossalico, Ν,Ν'-bis-saliciloil-diidrazide dell'acido tiopropionico.
4. Fosfiti e fosfoniti, come per esempio, trifenilfosfito, difenilalchilfosfiti, fenildialchilfosfiti, tris-(nonilfenil)-fosfito, trilaurilfosfito, triottadecilfosfito, distearil-pentaeritritedifosfito, tris- (2,4-di-tert.butilfenil)-fosfito, diisodecilpentaeritrite-difosfito, bis-(2,4-di-tert.butilfenil)-pentaeritrite-difosf ito, bis-(2,6-di-terzbutil-4-metilfenil)-pentaeritritedifosf ito, bisisodecilossi-pentaeritritedifosf ito, bis-(2,4-diterz-butil-6-metilfenil)-pentaeritritedifosf ito, bis-(2,4,6-tri-terz-butilfenil)-pentaeritritedifosfito, tristearil-sorbite-trifosf ito, tetrakis-(2,4-ditert .butilfenil)-4,4'-bifenilen-difosfonito, 6-isoottilossi-2,4,8,10-tetra-terz-butil-12H-dibenzo [d,g]-1,3,2-diossafosfocina, 6-fluoro-2,4,8,10-tetra-terzbutil-12-metil-dibenzo [d,g]1,3,2-diossafosfocina, bis- (2,4-di-tert-butil-6-metilfenil)-metilfosfito, bis- (2,4-di-tert-butil-6-metilfenil)-etilfosfito.
5. Composti che distruggono i perossidi, come per esempio esteri dell'acido β-tio-dipropionico, per esempio l'estere laurilico, stearilico, miristilico oppure tridecilico, mercaptobenzimmidazolo, il sale di zinco del 2-mercaptobenzimmidazolo, dibutilditiocarbammato di zinco, diottadecildisolfuro, pentaeritrite-tetrakis- (B-dodecilmercapto)-propionico.
6. Agenti stabilizzanti di poliammidi, come per esempio sali di rame in combinazione con ioduri e/o con composti del fosforo e sali del manganese bivalente .
7. Agenti co-stabilizzanti basici, come per esempio melammina, polivinilpirrolidone, diciandiammide, tri-allilcianurato, derivati dell'urea, derivati dell 'idrazina, ammine, poliammidi, poliuretani, sali di metalli alcalini, e di metalli alcalino-terrosi di acidi grassi superiori, per esempio stearato di calcio, stearato di zinco, beenato di magnesio, stearato di magnesio, ricinoleato di sodio, palmitato di potassio, pirocatechinato di antimonio oppure pirocatechinato di stagno.
8. Agenti di nucleazione, come per esempio acido 4-terz.butilbenzoico, acido adipico, acido difenilacetico.
9. Cariche e agenti di rinforzo, come per esempio carbonato di calcio, silicati, fibre di vetro, amianto, talco, caolino, mica, solfato di bario, ossidi e idrossidi di metalli, nerofumo, grafite .
10. Altri additivi, come per esempio plastificanti, lubrificanti, agenti emulsionanti, pigmenti, agenti sbiancanti ottici, agenti di protezione nei confronti della fiamma, agenti antistatici, propellenti.
11. Benzofuranoni oppure indolinoni, come per esempio sono descritti in US-A-4325863, US-A-4338244, US-A-5175312, US-A-5216052, US-A-5252643, DE-A-4316611, DE-A-4316622, DE-A-4316876, EP-A-0589839 oppure EP-A-0591102 oppure 3-[4-(2-acetossietossi)fenil]-5,7-di-tert-butil-benzofuran-2-one, 5.7-di-tert-butil-3- [4-(2-stearoilossietossi)fenil]-benzofuran-2-one, 3,3'-bis[5,7-di-tert-butil-3-(4-[2-idrossietossi]-fenil)-benzofuran-2-one] , 5,7-di-tertbutil-3- (4-etossifenil)benzofuran-2-one, 3-(4-acetossi-3,5-dimetilfenil)-5,7-di-tert-butil-benzofuran-2-one, 3- (3,5-dimetil-4-pivaloilossi-fenil)-5.7-di-tert-butil-benzofuran-2-one .
Un ulteriore oggetto dell'invenzione è l'impiego di composti di formule I e II per la stabilizzazione di materiale organico contro una degradazione ossidativa, termica e/o attinica.
Si preferisce l’impiego di composti secondo le formule I e II come stabilizzanti in polimeri sintetici, naturali, oppure semisintetici.
L’invenzione pertanto consiste anche in un procedimento per la stabilizzazione di materiale organico, in particolare di polimeri naturali, sintetici oppure semisintetici, caratterizzato dal fatto che a questo materiale si aggiungono come stabilizzanti composti di formule I oppure II oppure si applicano su di esso.
I composti di formula I e/o II possono venire preparati secondo o in analogia a procedimenti noti. Se si fa condensare per esempio l'aldeide biciclica III con un fenolo alchilato IVa oppure IVb
si ottengono i composti di formule I e II. La condensazione viene effettuata per esempio come descritto in EP 466263 e può venire catalizzata con una adatta base, come KOH oppure NaOH. Il rapporto molare IVa(b):III opportunamente è circa 2:1.
Un'ulteriore possibilità è la catalisi con acidi di Brónsted oppure con acidi di Lewis, per esempio oppure acido p-toluensolfonico.
Gli esempi che seguono illustrano più dettagliatamente l'invenzione. In essi e nel resto della descrizione e anche nelle rivendicazioni, le indicazioni dì parti e di percentuali si riferiscono al peso, a meno che non venga diversamente indicato.
Esempio 1:
Ad una soluzione di 83,03 g (1,48 moli) di KOH in 1,2 1 di MeOH si aggiungono 243,09 g (1,48 moli) di 2-t-butil-6-metilfenolo sotto raffreddamento e sotto azoto. Quindi, si aggiungono goccia a goccia 90,41 g (0,74 moli) di norbornen-5-aldeide in 300 mi di MeOH. Dopo riscaldamento per 16 ore sotto riflusso si porta a pH 6 con 110 mi di HC1 concentrato. Dopo successivo trattamento mediante filtrazione, lavaggio, anidrificazione con MgS04 ed evaporazione del solvente, si ottengono 91,0 g (28,4% del teorico) del composto di cui sopra, che viene ricristallizzato da esano.
P.f. 156°C
Analisi: cale, (trov.): C 83,28 (83,14) H 9,32 (9,44) Esempio di impiego: Stabilizzazione di terpolimero acrilonitrile/butadiene/stirolo (ABS) analisi termogravimetrica
1000 parti di polvere di ABS non stabilizzata (polibutadiene ~ 25%) vengono mescolate a fondo con 100 parti di cicloesano contenenti 2,5 parti dell’agente stabilizzante indicato nella tabella I. Il solvente viene allontanato sotto vuoto a 40°C/N2.
Nell'apparecchio Mettler DTA2000 per misurazioni termogravimetriche, si determina la dipendenza dalla temperatura nell'ossidazione di 5 g di polvere di ABS stabilizzato su una piccola bacinella di alluminio nel flusso di ossigeno (50 ml/min) a 180°C.
Si osserva una caratteristica variazione della temperatura, quando avviene la reazione di degradazione esotermica del polimero. Il tempo t fino al massimo della reazione esotermica è una misura per la stabilità termica del polimero. Quanto più lungo è questo tempo, tanto migliore è la stabilità termica.
I risultati rappresentati nella tabella I che segue indicano la superiorità del composto conforme all'invenzione in confronto al composto bisfenolo N.
<1 >Composto secondo EP 466263, esempio 1, di formula
Claims (12)
- RIVENDICAZIONI 1. Composti di formula I oppure II,
- in cui R1 indica metile oppure H, R2 indica H oppure metile, R3 indica H oppure C1-C4-alchile, R4 indica C1-C3-alchile, R5 indica C1-C3-alchile, e il gruppo Z indica CH2 oppure O. 2. Composti di formula I oppure II secondo la rivendicazione 1, in cui R1 indica H, R2 indica H, R3 indica H, R4 indica t-butile, R5 indica metile oppure t-butile, e il gruppo Z indica
- 3. Composti secondo la rivendicazione 2, in cui R1 indica H.
- 4. Composti secondo la rivendicazione 2, in cui Z indica CH2.
- 5. Composto secondo la rivendicazione 2 di formula:
- 6. Composizioni contenenti un prodotto organico sensibile nei confronti di una degradazione ossidativa, termica e/o provocata dalla luce e almeno un composto di formula I oppure II secondo la rivendicazione 1.
- 7. Composizione secondo la rivendicazione 6, in cui il prodotto organico è un polimero organico, preferibilmente sintetico.
- 8. Composizione secondo la rivendicazione 7, in cui il prodotto organico è un (co)polimero dello stirolo.
- 9. Procedimento per la stabilizzazione di un prodotto organico sensibile nei confronti di una degradazione ossidativa, termica e/o provocata dalla luce, caratterizzato dal fatto che, a questo, si aggiunge un composto di formula I oppure II, come descritto nella rivendicazione 1.
- 10. Procedimento secondo la rivendicazione 9, in cui il prodotto organico è un polimero.
- 11. Procedimento secondo la rivendicazione 10, in cui il prodotto organico è un polimero oppure un copolimero dello stirolo.
- 12. Impiego dei composti di formule I e II secondo la rivendicazione 1, come stabilizzanti in un prodotto organico sensibile nei confronti di una degradazione ossidativa, termica e/o provocata dalla luce.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH25696 | 1996-02-01 | ||
US08/789,894 US5852090A (en) | 1996-02-01 | 1997-01-29 | Norbornene-substituted bisphenol antioxidants |
Publications (2)
Publication Number | Publication Date |
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ITMI970184A1 true ITMI970184A1 (it) | 1998-07-31 |
IT1302985B1 IT1302985B1 (it) | 2000-10-18 |
Family
ID=25684049
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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IT1997MI000184A IT1302985B1 (it) | 1996-02-01 | 1997-01-31 | Bisfenoli sostituiti con gruppi di norbornene come antiossidanti |
Country Status (6)
Country | Link |
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US (1) | US5852090A (it) |
JP (1) | JPH09227433A (it) |
DE (1) | DE19703225A1 (it) |
FR (1) | FR2744443B1 (it) |
GB (1) | GB2309694B (it) |
IT (1) | IT1302985B1 (it) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10115222A1 (de) * | 2001-03-28 | 2002-10-10 | Clariant Gmbh | Hochmolekulare, vernetzte Polyvinylbutyrale, Verfahren zu deren Herstellung sowie deren Verwendung |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3355414A (en) * | 1961-09-14 | 1967-11-28 | Eastman Kodak Co | Thermosetting polyesters |
US3714122A (en) * | 1970-07-20 | 1973-01-30 | Goodyear Tire & Rubber | Antioxidants and age resistant polymeric compositions |
US3930047A (en) * | 1974-03-11 | 1975-12-30 | Dynapol Corp | Fat or oil composition stabilized with polystyrlphenol antioxidant |
US4301306A (en) * | 1980-03-27 | 1981-11-17 | The B. F. Goodrich Company | Norbornenyl phenolic compounds |
US4355148A (en) * | 1980-09-18 | 1982-10-19 | The B. F. Goodrich Company | Norbornene polymers containing bound phenolic antioxidant |
EP0466263B1 (en) * | 1990-07-10 | 1996-09-25 | Dsm N.V. | Polymerizable antioxidant and olefin polymers containing bound antioxidant |
US5017727A (en) * | 1990-07-10 | 1991-05-21 | Copolymer Rubber & Chemical Corporation | Polymerizable antioxidant composition |
US5157164A (en) * | 1990-07-10 | 1992-10-20 | Copolymer Rubber & Chemical Corp. | Polymerizable antioxidant composition |
DE19718288A1 (de) * | 1996-05-03 | 1997-11-27 | Ciba Geigy Ag | Stabilisierte Zusammensetzung und polymere Antioxidantien |
-
1997
- 1997-01-27 GB GB9701610A patent/GB2309694B/en not_active Expired - Fee Related
- 1997-01-29 US US08/789,894 patent/US5852090A/en not_active Expired - Fee Related
- 1997-01-29 DE DE19703225A patent/DE19703225A1/de not_active Withdrawn
- 1997-01-30 FR FR9701001A patent/FR2744443B1/fr not_active Expired - Fee Related
- 1997-01-31 JP JP9033062A patent/JPH09227433A/ja active Pending
- 1997-01-31 IT IT1997MI000184A patent/IT1302985B1/it active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
US5852090A (en) | 1998-12-22 |
IT1302985B1 (it) | 2000-10-18 |
FR2744443A1 (fr) | 1997-08-08 |
GB2309694B (en) | 2000-02-16 |
FR2744443B1 (fr) | 1999-02-19 |
GB9701610D0 (en) | 1997-03-19 |
GB2309694A (en) | 1997-08-06 |
DE19703225A1 (de) | 1997-08-07 |
JPH09227433A (ja) | 1997-09-02 |
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