ITMI20090168A1 - Nuove ammine stericamente impedite e loro uso come stabilizzanti per polimeri - Google Patents
Nuove ammine stericamente impedite e loro uso come stabilizzanti per polimeri Download PDFInfo
- Publication number
- ITMI20090168A1 ITMI20090168A1 IT000168A ITMI20090168A ITMI20090168A1 IT MI20090168 A1 ITMI20090168 A1 IT MI20090168A1 IT 000168 A IT000168 A IT 000168A IT MI20090168 A ITMI20090168 A IT MI20090168A IT MI20090168 A1 ITMI20090168 A1 IT MI20090168A1
- Authority
- IT
- Italy
- Prior art keywords
- group
- butyl
- branched
- tert
- bis
- Prior art date
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- 239000003381 stabilizer Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000000463 material Substances 0.000 claims abstract description 25
- 238000000034 method Methods 0.000 claims abstract description 12
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- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
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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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- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000019359 magnesium stearate 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
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000006078 metal deactivator Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 239000012764 mineral filler Substances 0.000 description 1
- GXFQBBOZTNQHMW-UHFFFAOYSA-N n'-(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound CC1(C)CC(NCCCCCCN)CC(C)(C)N1 GXFQBBOZTNQHMW-UHFFFAOYSA-N 0.000 description 1
- DTSDBGVDESRKKD-UHFFFAOYSA-N n'-(2-aminoethyl)propane-1,3-diamine Chemical compound NCCCNCCN DTSDBGVDESRKKD-UHFFFAOYSA-N 0.000 description 1
- JSOQEHPVNDFMMV-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine;4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine Chemical compound ClC1=NC(Cl)=NC(N2CCOCC2)=N1.C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 JSOQEHPVNDFMMV-UHFFFAOYSA-N 0.000 description 1
- ZQMPWXFHAUDENN-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)ethane-1,2-diamine Chemical compound CC1=CC=CC=C1NCCNC1=CC=CC=C1C ZQMPWXFHAUDENN-UHFFFAOYSA-N 0.000 description 1
- DHXOCDLHWYUUAG-UHFFFAOYSA-N n,n-didodecylhydroxylamine Chemical compound CCCCCCCCCCCCN(O)CCCCCCCCCCCC DHXOCDLHWYUUAG-UHFFFAOYSA-N 0.000 description 1
- RGONOPKACWKIQP-UHFFFAOYSA-N n,n-dioctadecylhydroxylamine;n-hexadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCC.CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCCC RGONOPKACWKIQP-UHFFFAOYSA-N 0.000 description 1
- WQAJFRSBFZAUPB-UHFFFAOYSA-N n,n-dioctylhydroxylamine Chemical compound CCCCCCCCN(O)CCCCCCCC WQAJFRSBFZAUPB-UHFFFAOYSA-N 0.000 description 1
- VQLURHRLTDWRLX-UHFFFAOYSA-N n-(4-hydroxyphenyl)nonanamide Chemical compound CCCCCCCCC(=O)NC1=CC=C(O)C=C1 VQLURHRLTDWRLX-UHFFFAOYSA-N 0.000 description 1
- SAVBPLYIBMOJIH-UHFFFAOYSA-N n-(4-methylpentyl)-n-phenylaniline Chemical class C=1C=CC=CC=1N(CCCC(C)C)C1=CC=CC=C1 SAVBPLYIBMOJIH-UHFFFAOYSA-N 0.000 description 1
- ZLUHLPGJUZHFAR-UHFFFAOYSA-N n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]naphthalen-1-amine Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=CC2=CC=CC=C12 ZLUHLPGJUZHFAR-UHFFFAOYSA-N 0.000 description 1
- UBINNYMQZVKNFF-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine oxide Chemical compound C=1C=CC=CC=1C=[N+]([O-])CC1=CC=CC=C1 UBINNYMQZVKNFF-UHFFFAOYSA-N 0.000 description 1
- DARUEKWVLGHJJT-UHFFFAOYSA-N n-butyl-1-[4-[4-(butylamino)-2,2,6,6-tetramethylpiperidin-1-yl]-6-chloro-1,3,5-triazin-2-yl]-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCC)CC(C)(C)N1C1=NC(Cl)=NC(N2C(CC(CC2(C)C)NCCCC)(C)C)=N1 DARUEKWVLGHJJT-UHFFFAOYSA-N 0.000 description 1
- BLBLVDQTHWVGRA-UHFFFAOYSA-N n-butyl-3-[4-[4-(butylamino)-1,2,2,6,6-pentamethylpiperidin-3-yl]-6-chloro-1,3,5-triazin-2-yl]-1,2,2,6,6-pentamethylpiperidin-4-amine Chemical compound CCCCNC1CC(C)(C)N(C)C(C)(C)C1C1=NC(Cl)=NC(C2C(N(C)C(C)(C)CC2NCCCC)(C)C)=N1 BLBLVDQTHWVGRA-UHFFFAOYSA-N 0.000 description 1
- GPKWXXQPBCDHKB-UHFFFAOYSA-N n-butyl-3-[4-[4-(butylamino)-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-3-yl]-6-chloro-1,3,5-triazin-2-yl]-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)C(C=2N=C(N=C(Cl)N=2)C2C(N(OC3CCCCC3)C(C)(C)CC2NCCCC)(C)C)C(NCCCC)CC(C)(C)N1OC1CCCCC1 GPKWXXQPBCDHKB-UHFFFAOYSA-N 0.000 description 1
- UUCRMZLZCRYFFW-UHFFFAOYSA-N n-butyl-4-(4,6-dichloro-1,3,5-triazin-2-yl)-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound N=1C(Cl)=NC(Cl)=NC=1C1(NCCCC)CC(C)(C)NC(C)(C)C1 UUCRMZLZCRYFFW-UHFFFAOYSA-N 0.000 description 1
- SYJJVZNFBSDXJV-UHFFFAOYSA-N n-butyl-4-[4-[4-(butylamino)-2,2,6,6-tetramethylpiperidin-4-yl]-6-chloro-1,3,5-triazin-2-yl]-2,2,6,6-tetramethylpiperidin-4-amine Chemical compound N=1C(Cl)=NC(C2(CC(C)(C)NC(C)(C)C2)NCCCC)=NC=1C1(NCCCC)CC(C)(C)NC(C)(C)C1 SYJJVZNFBSDXJV-UHFFFAOYSA-N 0.000 description 1
- LRUUZFQPCUFYPV-UHFFFAOYSA-N n-dodecyldodecan-1-imine oxide Chemical compound CCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCC LRUUZFQPCUFYPV-UHFFFAOYSA-N 0.000 description 1
- GBMIPYGHTZRCRH-UHFFFAOYSA-N n-ethylethanimine oxide Chemical compound CC[N+]([O-])=CC GBMIPYGHTZRCRH-UHFFFAOYSA-N 0.000 description 1
- ZRPOKHXBOZQSOX-UHFFFAOYSA-N n-heptadecyl-n-octadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCCCN(O)CCCCCCCCCCCCCCCCC ZRPOKHXBOZQSOX-UHFFFAOYSA-N 0.000 description 1
- GCDJFNYVSDFWDB-UHFFFAOYSA-N n-hexadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC GCDJFNYVSDFWDB-UHFFFAOYSA-N 0.000 description 1
- HQYHEBGVNAJVAA-UHFFFAOYSA-N n-hexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCNO HQYHEBGVNAJVAA-UHFFFAOYSA-N 0.000 description 1
- ZXGDIORKSOYRMQ-UHFFFAOYSA-N n-octadecylheptadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCC ZXGDIORKSOYRMQ-UHFFFAOYSA-N 0.000 description 1
- MCMMSXFAWOGWQE-UHFFFAOYSA-N n-octadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC MCMMSXFAWOGWQE-UHFFFAOYSA-N 0.000 description 1
- CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-UHFFFAOYSA-N 0.000 description 1
- IMXRBCGZTVENAC-UHFFFAOYSA-N n-phenyl-n-(2,4,4-trimethylpentan-2-yl)aniline Chemical class C=1C=CC=CC=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 IMXRBCGZTVENAC-UHFFFAOYSA-N 0.000 description 1
- SNWVRVDHQRBBFG-UHFFFAOYSA-N n-phenyl-n-(2,4,4-trimethylpentan-2-yl)naphthalen-1-amine Chemical compound C=1C=CC2=CC=CC=C2C=1N(C(C)(C)CC(C)(C)C)C1=CC=CC=C1 SNWVRVDHQRBBFG-UHFFFAOYSA-N 0.000 description 1
- SLYJXPKHTZCZOG-UHFFFAOYSA-N n-tetradecyltetradecan-1-imine oxide Chemical compound CCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCC SLYJXPKHTZCZOG-UHFFFAOYSA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- RNVAPPWJCZTWQL-UHFFFAOYSA-N octadecyl 3,5-ditert-butyl-4-hydroxybenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 RNVAPPWJCZTWQL-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine 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
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920005629 polypropylene homopolymer 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
- 239000001294 propane Substances 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 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
- 229940074404 sodium succinate Drugs 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000008117 stearic acid Substances 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
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 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
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000019149 tocopherols Nutrition 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
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 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
- 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
- 150000003672 ureas Chemical class 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 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
- 239000004711 α-olefin 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
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)
- Hydrogenated Pyridines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
NUOVE AMMINE STERICAMENTE IMPEDITE E LORO USO COME
STABILIZZANTI PER POLIMERI
La presente invenzione riguarda composti polipiperidinici in grado di conferire ai materiali polimerici, in particolare alle poliolefine, una elevata stabilità contro la fotodegradazione e l'azione ossidativa dell'aria. L'invenzione riguarda anche i procedimenti di preparazione dei composti secondo l'invenzione.
È ben noto che i materiali polimerici sono soggetti a deterioramento per azione del calore, della luce e dell'aria, fattori che provocano perdita delle proprietà meccaniche, scolorimenti ed altri effetti indesiderati.
Per la stabilizzazione dei materiali polimerici, principalmente contro le radiazioni UV della luce solare, sono state proposte varie classi di composti come per esempio benzofenomi e benzotriazoli. Questi composti conferiscono ai polimeri una stabilità accettabile, ma non ancora sufficiente per le esigenze pratiche con particolare riferimento alle fibre, film e raffia a base di polimeri olefinici.
I derivati delle polialchilpiperidine, comunemente denominati HALS (Hindered Amines Light Stabilizers), sono efficaci per la stabilizzazione dei materiali polimerici e numerosi sono i brevetti, quali ad esempio US 4.477.615 ed US 4.086.204, che ne descrivono la preparazione, l'impiego ed i risultati ottenuti.
Tuttavia tali stabilizzanti noti non danno sempre risultati del tutto soddisfacenti e i materiali polimerici permangono soggetti all'indesiderato deterioramento per azione del calore, della luce e dell'aria, con le negative conseguenze sopra menzionate. Inoltre un ulteriore svantaggio dei composti stabilizzanti secondo la tecnica nota à ̈ che la loro sintesi richiede l'impiego di costose sostanze di base che quindi rendono la loro preparazione dispendiosa.
Sussiste pertanto la necessità di mettere a disposizione dell'industria composti polipiperidinici in grado di conferire ai materiali polimerici, in particolare alle poliolefine, una elevata stabilità contro la fotodegradazione e l'azione ossidativa dell'aria.
Scopo della presente invenzione à ̈ proprio quello di fornire nuovi composti polipiperidinici in grado di conferire ai materiali polimerici le migliorate caratteristiche di stabilità sopra menzionate. Tale scopo viene conseguito con i composti polipiperidinici le cui caratteristiche principali sono specificate nella rivendicazione 1, e con i procedimenti per la loro fabbricazione le cui caratteristiche sono specificate nelle rivendicazione 9 e 10. Altre caratteristiche dell'invenzione sono specificate nelle restanti rivendicazioni.
Un altro scopo della presente invenzione à ̈ di ottenere composti polipiperidinici più economici.
Un vantaggio offerto dall'invenzione à ̈ quello che, grazie all'uso di molecole del tipo
Cl
NN
N N N
Pi R<1>R2 R3
in particolare se il gruppo NR<2>R<3>Ã ̈ morfolina, nella sintesi degli HALS la preparazione di questi diventa meno dispendiosa.
Ulteriori vantaggi e caratteristiche dei composti e del metodo secondo la presente invenzione risulteranno evidenti agli esperti del ramo dalla seguente dettagliata descrizione ed dagli annessi esempi di alcune loro forme realizzative.
Secondo la presente invenzione à ̈ possibile conferire ai materiali polimerici una stabilità particolarmente elevata contro la fotodegradazione e l'azione ossidativa dell'aria risultano mediante l'impiego di HALS aventi la generale formula generale(I):
A
N N
N (CH2<)>mN
N xy
(CH2<)>n(CH2<)>n
NH NH (I)
NN N N
NNNN N N
2 3
Pi R1
R<2>R<3>Pi R<1>R<R>
nella quale x può assumere i valori zero ed 1;
y à ̈ compreso tra 1 e 10;
m ed n possono essere anche uguali ed assumono i valori da 2 a 8;
A può rappresentare un gruppo NPiR<1>o un gruppo NR<2>R<3>
;
Pi rappresenta il seguente gruppo
<H3C>CH3
H2C C
CH NR4 (II)
H2C C
H3C CH3
;
in cui R<4>= H oppure gruppo alchilico lineare o ramificato C1-C4oppure un gruppo OR<5>in cui R<5>= H oppure gruppo alchilico lineare o ramificato C1-C8; R<1>= H oppure gruppo alchilico lineare o ramificato C1-C4;
Nella formula (II) R<2>e R<3>nel gruppo NR<2>R<3>, diverso dal gruppo NPiR<1>, possono essere anche uguali e rappresentano idrogeno, gruppi alchilici lineari o ramificati C1-C8, un gruppo cicloalchile avente da 5 a 12 atomi di carbonio, oppure possono assieme all'atomo di azoto formare un anello eterociclico da 5 a 7 membri, eventualmente contenente altri eteroatomi ad esempio O, ed in particolare il gruppo NR<2>R<3>può essere la morfolina.
È stato osservato che i composti secondo la formula (I), in cui m=2 ed n =3 risultano quelli che conferiscono ai materiali polimerici una migliore stabilità contro la fotodegradazione e l'azione ossidativa dell'aria.
È stato inoltre trovato che la stabilità viene ulteriormente migliorata se R1à ̈ butile ed un ulteriore miglioramento viene ottenuto se R<4>nel gruppo Pi à ̈ idrogeno.
Ulteriori miglioramenti sono conseguibili impiegando i composti secondo la formula (I), in cui R<2>ed R<3>formano insieme all'atomo di azoto un anello morfolinico.
Ancora ulteriori miglioramenti della stabilità dei materiali polimerici possono essere ottenuti se x=0 ed y=1 ed i gruppi terminali sono H,ed ancora di più con i composti in cui x=1 ed A=NPiR<1>o,in alternativa, se x=1 ed A=NR<2>R<3>.
I composti di formula (I) possono essere ottenuti mediante un procedimento consistente nel far reagire un'ammina avente la seguente formula generale
NH2-(CH2)n-NH-(CH2)m-NH-(CH2)n-NH2(III) in cui m e n sono come sopra definiti,
con un derivato avente la seguente formula generale
Cl
N N
(IV)
N N N
Pi R<1>R2 R3
in cui Pi, R1, R2e R3sono come sopra definiti.
Si ottiene così una HALS di formula (I) in cui, x = 0, y = 1, i gruppi terminali sono atomi di idrogeno ed e m, n, Pi R<1>, R<2>e R<3>sono come sopra definiti e il quale può essere rappresentato dalla seguente formula semplificata :
R1 R1
Pi N<N>Pi
N N
N<NH>(CH2)n<NH>(CH2)m<NH>(CH2)n<NH>N
N N
R3 R3
N
R2 (V) N
R2.
La HALS di formula (V), essendo un esempio dei composti secondo la formula (I), à ̈ in grado di conferire ai materiali polimerici una elevata stabilità contro la fotodegradazione e l'azione ossidativa dell'aria.
Un'alternativa all'esempio sopra descritto à ̈ quella di far reagire il composto di formula (V) con composti aventi la seguente formula:
A
N N
(VI)
Cl N<Cl>
in cui A ha il significato sopra descritto.
La HALS di formula (V) può essere convertita in altri prodotti rientranti nella formula (I) in cui x = 1, y = 1-10 ed m, n, Pi, R<1>, R<2>ed R<3>hanno i significati sopra definiti.
I gruppi terminali della HALS di formula (I) possono essere H, OH, OR con R=alchile o un gruppo amminico, in particolare un gruppo amminico derivato dalla formula (V).
Gli indici m e n hanno preferibilmente i valori di 2 e 3 rispettivamente.
Le quantità di HALS secondo la presente invenzione occorrenti per una efficace stabilizzazione dei materiali polimerici dipende da diversi fattori, quali il tipo e le caratteristiche del materiale polimerico da stabilizzare, l'uso a cui à ̈ destinato tale materiale, l'intensità delle radiazioni e la durata dell'esposizione a cui si prevede debba essere sottoposto.
In una sua particolare forma realizzativa la presente invenzione consiste nell'aggiungere al materiale polimerico da stabilizzare i composti della formula (I) in quantità comprese tra da 0,01 e 5 % in peso rispetto al materiale polimerico, preferibilmente da 0,1 a 1,0 %. Risultati particolarmente vantaggiosi si ottengono se il materiale polimerico à ̈ poliolefinico.
In ulteriori forme realizzative della presente invenzione, la summenzionata composizione comprende, come stabilizzanti per materiale poliolefinico, oltre alle HALS di formula (I), anche altre HALS monomeriche, polimeriche o macromolecolari di diversa natura.
I polimeri che possono essere vantaggiosamente stabilizzati secondo la presente invenzione sono polietilene, polipropilene, polistirene, polibutadiene, polisoprene, e loro copolimeri, polivinilcloruro, polivinilidencloruro e loro copolimeri, polivinilacetato e suoi copolimeri, in particolare con etilene; poliesteri come il polietilentereftalato; poliammidi come il Nylon 6 e 6,6; poliuretani.
I composti della presente invenzione possono essere incorporati nei materiali polimerici con qualsiasi metodo noto per miscelare additivi e materiali polimerici, per esempio mediante:
- miscelazione con il polimero, che può essere sotto forma di polvere o granulato in una miscelatore adatto allo scopo o un estrusore;
- aggiunta sotto forma di soluzione o sospensione in un solvente opportuno e successivo allentamento del solvente dal polimero, che può essere in forma di polvere, granulato o sospensione, dopo intima miscelazione;
- addizione al polimero durante la preparazione di quest'ultimo, per esempio nell'ultimo stadio della preparazione.
I composti di formula (I) possono essere aggiunti al materiale polimerico da stabilizzare, e, oltre ad HALS di altro tipo come sopra menzionate, anche antiossidanti a base di fenoli, ammine, fosfiti; assorbitori di radiazioni UV a base di benzofenoni, benzotriazoli; stabilizzanti al nichel; plastificanti, lubrificanti, agenti antistatici, antifiamma, inibitori di corrosione, deattivatori di metalli, cariche minerali quali biossido di titanio, ossido di alluminio e simile. Alcuni esempi di tali additivi sono i seguenti:
A. ANTIOSSIDANTI
1. Fenoli alchilati, come per esempio: 2,6-di-ter-butil-4-metilfenolo; 2-ter-butil-4,6-di-metilfenolo; 2,6-di-ter-butil-4-etilfenolo; 2,6-di-ter-butil-4-butilfenolo; 2,6-di-terbutil-4-isobutilfenolo; 2,6-di-ciclopentil-4-metilfenolo; 2-(α-metilcicloesil)-4,6-dimetilfenolo; 2,6-di-octadecil-4-metilfenolo; 2,4,6-tricicloesilfenolo; 2,6-di-ter-butil-4-metossimetilfenolo; nonilfenoli lineari e ramificati, per esempio 2,6-di-nonil-4-metilfenolo; 2,4-di-metil-6-(1’-metilundecil)fenolo; 2,4-di-metil-6-(1’-eptadecil)fenolo e loro miscele.
2. Alchil-tiometilfenoli, come per esempio: 2,4-di-octil-tiometil-6-ter-butilfenolo; 2,4-di-octil-tiometil-6-metilfenolo; 2,4-di-octil-tiometil-6-etilfenolo; 2,6-didodeciltiometil-4-nonilfenolo.
3. Idrochinoni e idrochinoni alchilati, come per esempio: 2,6-di-ter-butil-4-metossifenolo; 2,5-di-ter-butil-idrochinone; 2,5-di-ter-amil-idrochinone; 2,6-difenil-4-octadecilossifenolo; 2,6-di-ter-butil-idrochinone; 2,5-di-ter-butil-4-idrossianisolo; 3,5-di-ter-butil-4-idrossianisolo; 3,5-di-ter-butil-4-idrossifenil stearato; bis(3,5-di-ter-butil-4-idrossifenil)adipato.
4. Tocoferoli, per esempio α-tocoferolo; γ-tocoferolo; β-tocoferolo; Î ́-tocoferolo e loro miscele (vitamina E).
5. Tiodifenil eteri idrossilati, come per esempio: 2,2’-tiobis(6-ter-butil-4-metilfenolo); 2,2’-tiobis(4-octilfenolo); 4,4’-tiobis(6-ter-butil-3-metilfenolo); 4,4’-tiobis(6-ter-butil-2-metilfenolo); 4,4’-bis(2,6-di-metil-4-idrossifenil)disolfuro.
6. Alchilidene bisfenoli, come per esempio: 2,2’-metilenebis(6-ter-butil-4-metilfenolo); 2,2’-metilenebis(6-ter-butil-4-etilfenolo); 2,2’-metilene-bis(4-metil-6-(αmetilcicloesil)fenolo); 2,2’-metilenebis(4-metil-6-cicloesilfenolo); 2,2’-metilenebis(6 nonil-4-metilfenolo); 2,2’-metilenebis-(4,6-di-ter-butilfenolo); 2,2’-etilidenebis(4,6-diter-butilfenolo); 2,2’-etilidenebis(6-ter-butil-4-isobutilfenolo); 2,2’-metilenebis(6-(αmetilbenzil)-4-nonilfenolo); 2,2’-metilenebis(6-(α-α-dimetilbenzil)-4-nonilfenolo); 4,4’-metilenebis(2,6-di-ter-butilfenolo); 4,4’-metilenebis(6-ter-butil-2-metil-fenolo); 1,1-bis(5-ter-butil-4-idrossi-2-metilfenil)butano; 2,6-bis(3-ter-butil-5-metil-2-idrossibenzil)-4-metilfenolo; 1,1,3-tris(5-ter-butil-4-idrossi-2-metilfenil)butano; 1,1-bis(5-ter-butil-4-idrossi-2-metilfenil)-3-n-dodecil-mercaptobutano; etilenglicole bis(3,3-bis(3’-ter-butil-4’-idrossifenil)-butirrato); bis(2-(3’-ter-butil-2’-idrossi-5’-metilbenzil)-6-ter-butil-4-metilfenil)tereftalato; bis(3-ter-butil-4-idrossi-5-metilfenil)diciclopentadiene; 1,1-bis-(3,5-dimetil-2-idrossifenil)butano; 2,2-bis-(3,5-diter-butil-4-idrossifenil)propano; 2,2-bis-(5-ter-butil-4-idrossi-2-metilfenil)-4-n-dodecilmercaptobutano; 1,1,5,5-tetra-(5-ter-butil-4-idrossi-2-metilfenil)pentano.
7. O-, N-e S-benzil derivati come per esempio: 3,5,3’,5’-tetra-ter-butil-4-4’-diidrossidibenzil etere; octadecil-4-idrossi-3,5-dimetilbenzil-mercapto acetato; tridecil-4-idrossi-3,5-di-ter-butil-benzilmercapto acetato; tri(3,5-di-ter-butil—4-idrossibenzil)ammina; bis(4-ter-butil-3-idrossi-2,6-dimetilbenzil)ditiotereftalato; bis(3,5-di-ter-butil-4-idrossibenzil)disolfuro; isooctil-3,5-di-ter-butil-4-idrossibenzilmercaptoacetato.
8. Malonati contenenti il gruppo idrossibenzilico come per esempio: dioctadecil-2,2-bis-(3,5-di-ter-butil-2-idrossibenzil)malonato; dioctadecil-2-(3-ter-butil-4-idrossi-5-metilbenzil)malonato; di-dodecilmercaptoetil-2,2-bis-(3,5-di-ter-butil-4-idrossibenzil)malonato; bis(4-(1,1,3,3-tetrametilbutil)-fenil)-2,2-bis-(3,5-di-ter-butil-4-idrossibenzil)malonato.
9. Composti aromatici idrossibenzilici, come per esempio: 1,3,5-tris-(3,5-di-terbutil-4-idrossibenzil)-2,4,6-trimetilbenzene; 1,4-bis-(3,5-di-ter-butil-4-idrossibenzil)-2,3,5,6-tetrametilbenzene; 2,4,6-tris-(3,5-di-ter-butil-4-idrossibenzil)-fenolo.
10. Derivati triazinici, come per esempio: 2,4-bis(octilmercapto)-6-(3,5-di-terbutil-4-idrossianilino)-1,3,5-triazina; 2-octilmercapto-4-6-bis(3,5-di-ter-butil-4-idrossianilino)-1,3,5-triazina; 2-octilmercapto-4-6-bis(3,5-di-ter-butil-4-idrossifenossi)-1,3,5-triazina; 2,4,6-tris(3,5-di-ter-butil-4-idrossi-fenossi)-1,3,5-triazina; 1,3,5-tris-(3,5-di-ter-butil-4-idrossibenzil)-isocianurato; 1,3,5-tris-(4-ter-butil-3-idrossi-2,6dimetilbenzil)isocianurato; 2,4,6-tris(3,5-di-ter-butil-4-idrossifeniletil)-1,3,5-triazina; 1,3,5-tris-(3,5-di-ter-butil-4-idrossifenilpropionil)-esaidro-1,3,5-triazina; 1,3,5-tris-(3,5-dicicloesil-4-idrossibenzil)isocianurato.
11. Benzilfosfonati, come per esempio: dimetil-2,5-di-ter-butil-4-idrossibenzilfosfonato; dietil-3,5-di-ter-butil-4-idrossibenzilfosfonato; dioctadecil-3,5-di-ter-butil-4-idrossibenzilfosfonato; dioctadecil-5-ter-butil-4-idrossi-3-metilbenzilfosfonato; il sale di calcio dell’estere monoetilico dell’acido 3,5-di-ter-butil-4-idrossibenzilfosfonico.
12. Acilamminofenoli, quali la 4-idrossianilide dell’acido laurico, la 4-idrossianilide dell’acido stearico, l’octil N-(3,5-di-ter-butil-4-idrossifenil)carbammato.
13. Esteri dell’acido β-(3,5-di-ter-butil-4-idrossifenil)propionico con alcoli mono o poliidrici come per esempio: metanolo, etanolo, n-ottanolo, iso-ottanolo, octadecanolo; 1,6-esandiolo; 1,9-nonandiolo; glicole etilenico; 1,2-propandiolo; glicole neopentilico; glicole tiodietilenico; glicole dietilenico; glicole trietilenico; pentaeritritolo; tri-(idrossietil)isocianurato; N,N’-bis(idrossietil)ossammide; 3-tioundecanolo; 3-tiopentadecanolo; trimetilesandiolo; trimetilolopropano; 4-idrossimetil-1-fosfo-2,6,7-triossabiciclo(2.2.2)ottano.
14. Esteri dell’acido β-(5-ter-butil-4-idrossi-3-metilfenil)propionico con alcoli mono o poliidrici come per esempio: metanolo, etanolo, n-ottanolo, iso-ottanolo, octadecanolo; 1,6-esandiolo; 1,9-nonandiolo; glicole etilenico; 1,2-propandiolo; glicole neopentilico; glicole tiodietilenico; glicole dietilenico; glicole trietilenico; pentaeritritolo; tri-(idrossietil)isocianurato; N,N’-bis(idrossietil)ossammide; 3-tioundecanolo; 3-tiopentadecanolo; trimetilesandiolo; trimetilolopropano; 4-idrossimetil-1-fosfo-2,6,7-triossabiciclo(2.2.2)ottano.
15. Esteri dell’acido β-(3,5-dicicloesil-4-idrossifenil)propionico con alcoli mono o poliidrici come per esempio: metanolo, etanolo, n-ottanolo, iso-ottanolo, octadecanolo; 1,6-esandiolo; 1,9-nonandiolo; glicole etilenico; 1,2-propandiolo; glicole neopentilico; glicole tiodietilenico; glicole dietilenico; glicole trietilenico; pentaeritritolo; tri-(idrossietil)isocianurato; N,N’-bis(idrossietil)ossammide; 3-tioundecanolo; 3-tiopentadecanolo; trimetilesandiolo; trimetilolopropano; 4-idrossimetil-1-fosfo-2,6,7-triossabiciclo(2.2.2)ottano.
16. Esteri dell’acido 3,5-di-ter-butil-4-idrossifenil acetico con alcoli mono o poliidrici come per esempio: metanolo, etanolo, n-ottanolo, iso-ottanolo, octadecanolo; 1,6-esandiolo; 1,9-nonandiolo; glicole etilenico; 1,2-propandiolo; glicole neopentilico; glicole tiodietilenico; glicole dietilenico; glicole trietilenico; pentaeritritolo; tri-(idrossietil)isocianurato; N,N’-bis(idrossietil)ossammide; 3-tioundecanolo; 3-tiopentadecanolo; trimetilesandiolo; trimetilolopropano; 4-idrossimetil-1-fosfo-2,6,7-triossabiciclo(2.2.2)ottano.
17. Ammidi dell’acido β-(3,5-di-ter-butil-4-idrossifenil)propionico come per esempio: N,N’-bis-(3,5-di-ter-butil-4-idrossifenilpropionil)-esametilendiammide; N,N’-bis-(3,5-di-ter-butil-4-idrossifenilpropionil)-trimetilendiammide; N,N’-bis-(3,5-di-terbutil-4-idrossifenilpropionil)-idrazide; N,N’-bis-(2-(3-(3,5-di-ter-butil-4-idrossifenil)propionilossi)etil)-ossammide.
18. Acido ascorbico (vitamina C).
19. Antiossidanti amminici come per esempio: N,N’-di-isopropil-pfenilendiammina; N,N’-di-sec-butil-p-fenilendiammina; N,N’-bis(1,4-dimetil-pentil)-pfenilendiammina; N,N’-bis(1-etil-3-metilpentil)-p-fenilendiammina; N,N’-bis(1-metileptil)-p-fenilendiammina; N,N’-dicicloesil-p-fenilendiammina; N,N’-difenil-pfenilendiammina; N,N’-bis-(2-naftil)-p-fenilendiammina; N-isopropil-N’-fenil-pfenilendiammina; N-(1,3-dimetil-butil)-N’-fenil-p-fenilendiammina; N-(1-metileptil)-N’-fenil-p-fenilen-diammina; N-cicloesil-N’-fenil-p-fenilendiammina, 4-(ptoluensulfamoil)-difenilammina; N,N’-dimetil-N,N’-di-sec-butil-p-fenilendiammina; difenilammina; N-allil-difenilammina; 4-isopropossidifenilammina, N-fenil-1-naftilammina; N-(4-ter-ottilfenil)-1-naftilammina; N-fenil-2-naftilammina; p,p’-di-terottil-difenilammina; 4-n-butil-aminofenolo; 4-butirril-aminofenolo; 4-nonanoilaminofenolo; 4-dodecanoil-aminofenolo; 4-octadecanoil-aminofenolo; bis(4-metossifenil)ammina; 2,6-di-ter-butil-4-dimetilaminometilfenolo; 2,4’-diaminodifenilmetano; 4,4’-diaminodifenil-metano; N,N,N’,N’-tetrametil-4,4’-diaminodifenilmetano; 1,2-bis-((2-metilfenil)amino)etano; 1,2-bis-(fenilamino)propano; o-tolil-biguanide; bis-(4-(1’,3’-dimetilbutil)fenil)amina; ter-ottil-N-fenil-1-naftilammina; miscele di ter-butil / ter-ottil-difenilammine dialchilate; miscele di mono e di-alchil nonildifenilammine; miscele di mono e di-alchil dodecildifenilammine; miscele di mono e di-alchil isopropil/isoesildifenilammine; miscele di mono e di-alchil ter-butildifenilammine; 2,3-diidro-3,3-dimetil-4H-1,4-benzotiazina; fenotiazina; miscele di mono e dialchil ter-butil/ter-octilfenotiazine, miscele di mono e dialchil ter-ottilfenotiazine; N-allilfenotiazina; N,N,N’,N’-tetrafenil-1,4-diamino-2-butene; N,N’-bis-(2,2,6,6-tetrametil-piperidil-4-esametilendiammina; bis(2,2,6,6-tetrametilpiperid-4-il)sebacato; 2,2,6,6-tetrametilpiperid-4-one; 2,2,6,6-tetrametilpiperid-4-olo.
B. UV ADSORBERS E STABILIZZANTI LUCE
1. 2-(2’- idrossifenil)benzotriazoli, come per esempio: 2-(2’- idrossi-5-metilfenil)benzotriazolo; 2-(3’,5’-di-ter-butil-2’-idrossifenil)benzotriazolo; 2-(5’-terbutil-2’-idrossifenil)benzotriazolo; 2-(2’-idrossi-5’-(1,1,3,3-tetrametilbutil)fenil)benzotriazolo; 2-(3’,5’-di-ter-butil-2’-idrossifenil)-5-clorobenzotriazolo; 2-(3’-ter-butil-2’-idrossi-5’-metilfenil)-5-cloro-benzotriazolo; 2-(3’-secbutil-5’-ter-butil-2’-idrossifenil)benzotriazolo; 2-(2’-idrossi-4’-octilossifenil)benzotriazolo; 2-(3’,5’-di-ter-amil-2’-idrossifenil)-benzotriazolo; 2-(3’,5’-bis-(α,α-dimetilbenzil)-2’-idrossifenil)benzotriazolo; 2-(3’-ter-butil-5’-(2-(2-etilesilossi)-carboniletil)-2’-idrossifenil)-5-cloro-benzotriazolo; 2-(3’-ter-butil-2’-idrossi-5’-(2-octilossicarboniletil)fenil)-5-cloro-benzotriazolo; 2-(3’-ter-butil-2’-idrossi-5’-(2-metossicarboniletil)fenil)-5-cloro-benzotriazolo; 2-(3’-ter-butil-2’-idrossi-5’-(2-metossicarbonil-etil)fenil)-benzotriazolo; 2-(3’-ter-butil-2’-idrossi-5’-(2-octilossicarbonil-etil)fenil)-benzotriazolo; 2-(3’-ter-butil-5’-(2-(2-etilesilossi)-carboniletil)-2’-idrossifenil)-benzotriazolo; 2-(3’-dodecil-2’-idrossi-5’-metilfenil)-benzotriazolo; 2-(3’-ter-butil-2’-idrossi-5’-(2-isooctilossicarboniletil)-fenilbenzotriazolo; 2,2’-metilene-bis-(4-(1,1,3,3-tetrametilbutil)-6-benzotriazol-2-ilfenolo); il prodotto di transesterificazione del 2-(3’-ter-butil-5’-(2-metossicarboniletil)-2’-idrossifenil)-2H-benzotriazolo con polietilenglicole 300; (R-CH2-CH2-COO-CH2-CH2-)2-dove R può essere: 3’-ter-butil-4’-idrossi-5’-2H-benzotriazol-2-ilfenil; 2-(2’-idrossi-3’-(α,α-dimetilbenzil)-5’-(1,1,3,3-tetrametilbutil)-fenil)benzotriazolo; 2-(2’-idrossi-3’-(1,1,3,3-tetrametilbutil)-5’-(α,α-dimetilbenzil) fenil)benzotriazolo.
2. 2-idrossibenzofenoni, come per esempio i 4-idrossi; 4-metossi; 4-octilossi; 4-decilossi; 4-dodecilossi; 4-benzilossi; 4,2’,4’-tri-idrossi e 2’-idrossi-4,4’-dimetossi derivati.
3. Esteri degli acidi benzoici sostituiti e non sostituiti, come per esempio: 4-terbutil-fenil-salicilato; fenil salicilato; octilfenil salicilato; dibenzoil resorcinolo; bis-(4-ter-butil-benzoil)-resorcinolo; benzoil resorcinolo; 2,4-di-ter-butilfenil 3,5-di-ter-butil-4-idrossibenzoato; esadecil 3,5-di-ter-butil-4-idrossibenzoato; octadecil 3,5-di-ter-butil-4-idrossi-benzoato; 2-metil-4,6-di-ter-butilfenil 3,5-di-ter-butil-4-idrossibenzoato:
4. Acrilati, come per esempio: etil α-ciano-β,β-difenilacrilato; isooctil α-cianoβ,β-difenilacrilato; metil α-carbometossicinnamato; metil α-ciano-β-metil-p-metossi.cinnamato; butil α-ciano-β-metil-p-metossi-cinnamato; metil α-carbometossi-p-metossicinnamato e N-(β-carbometossi-β-cianovinil)-2-metilindolina.
5. Derivati del nichel come per esempio: complessi 1:1 o 1:2 del nichel con 2,2’-tio-bis-(4-(1,1,3,3-tetrametilbutil)fenolo, con o senza leganti quali la n-butilammina, la trietanolammina o la N-cicloesildietanolammina; nichel dibutiltiodicarbammato; sali di nichel di mono-alchil esteri (per esempio metil o etil esteri) dell’acido 4-idrossi-3,5-diter-butilbenzilfosfonico; complessi del nichel con le cheto-ossime, per esempio con la 2-idrossi-4-metilfenil undecil-cheto-ossima; complessi del nichel con 1-fenil-4-lauroil-5-idrossi-pirazolo, con o senza leganti addizionali.
6. Ammine stericamente impedite, come per esempio: il prodotto di condensazione della 2,4-dicloro-6-(4-n-butilammino-2,2,6,6-tetrametil-4-piperidil)-1,3,5-triazina con il prodotto di condensazione della 2-cloro-4,6-bis-(4-n-butilammino-2,2,6,6-tetrametil-4-piperidil)-1,3,5-triazina con 1,2 bis (3-aminopropilamino) etano CAS RN=136504-96-6; bis (2,2,6,6-tetrametil-4-piperidil)sebacato CAS RN=52829-07-9; bis (2,2,6,6-tetrametil-4-piperidil)succinato; bis (1,2,2,6,6-pentametil-4-piperidil)sebacato CAS RN=41556-26-7; (1,2,2,6,6-pentametil-4-piperidil)metil sebacato CAS RN=82919-37-7; bis (1-octilossi-2,2,6,6-tetrametil-4-piperidil)sebacato CAS RN=129757-67-1; bis (1,2,2,6,6-pentametil-4-piperidil) n-butil-3,5-di-ter-butil-4-idrossibenzilmalonato; il prodotto di condensazione dell’1-(2-idrossietil)-2,2,6,6-tetrametil-4-idrossipiperidina con l’acido succinico CAS RN=65447-77-0; condensati ciclici o lineari della N,N’-bis-(2,2,6,6-tetrametil-4-piperidil)esametilendiammina con la 4-ter-octilammino-2,6-dicloro-1,3,5-triazina CAS RN=71878-19-8; tris(2,2,6,6-tetrametil-4-piperidil)nitrilotriacetato; tetra(2,2,6,6-tetrametil-4-piperidil)-1,2,3,4-butantetracarbossilato; 1,1’-(1,2-etanediil)-bis(3,3,5,5-tetrametilpiperazinone); 4-benzoil-2,2,6,6-tetrametilpiperidina; 4-stearilossi-2,2,6,6-tetrametil-piperidina CAS RN=167078-06-0; bis(1,2,2,6,6-pentametil-4-piperidil)-2-n-butil-2-(idrossi-3,5-di-terbutilbenzil)malonato CAS RN=63843-89-0; 3-n-octil-7,7,9,9-tetrametil-1,3,8-triazaspiro(4,5)decan-2,4-dione; bis(1-octilossi-2,2,6,6-tetrametilpiperidil)sebacato; bis(1-octilossi-2,2,6,6-tetrametil-piperidil)succinato; condensati ciclici o lineari della N,N’-bis-(2,2,6,6-tetrametil-4-piperidil)esametilendiammina con la 4-morfolino-2,6-dicloro-1,3,5-triazina CAS RN=82451-48-7; condensati ciclici o lineari della N,N’-bis-(1,2,2,6,6-pentametil-4-piperidil)-esametilendiammina con la 4-morfolino-2,6-dicloro-1,3,5-triazina CAS RN=193098-40-7; il prodotto di condensazione della 2-cloro-4,6-bis(4-n-butilamino-2,2,6,6-tetrametilpiperidil)-1,3,5-triazina con 1,2-bis(3-amino-propilamino)etano; il prodotto di condensazione della 2-cloro-4,6-bis(4-n-butilamino-1,2,2,6,6-pentametilpiperidil)-1,3,5-triazina con 1,2-bis(3-aminopropilamino)etano CAS RN=106990-43-6; 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; miscela di 4-esadecilossi- e 4-octadecilossi-2,2,6,6-tetrametilpiperidina; prodotto di condensazione di N,N’-bis-(2,2,6,6-tetrametil-4-piperidil)esametilendiammina con 4-cicloesilammino-2,6-dicloro-1,3,5-triazina; N-(2,2,6,6-tetrametil-4-piperidil)n-dodecilsuccinimmide;
2-undecil-7,7,9,9-tetrametil-1-osso-3,8-diazo-4-osso-spiro(4,5)decano; prodotto di condensazione di 7,7,9,9-tetrametil-2-cicloundecil-1-osso-3,8-diazo-4-ossospiro(4,5)decano con epicloridrina; 1,1-bis(1,2,2,6,6-pentamentil-4-piperidilossicarbonil)-2-(4-metossifenil)etene; N,N’-bis-formil-N,N’-bis(2,2,6,6-tetrametil-4-piperidil)esametilendiammina; diestere dell’acido 4-metossi-metilenmalonico con la 1,2,2,6,6-pentametil-4-idrossipiperidina; poli(metilpropil-3-ossi-4-(2,2,6,6-tetrametil-4-piperidil))-silossano; prodotto di reazione del copolimero acido maleico/alfa-olefine con 2,2,6,6-tetrametil-4-aminopiperidina o 1,2,2,6,6-pentametil-4-amino-piperidina; prodotto di condensazione di 2-cloro-4,6-bis-(4-n-butilammino-1-cicloesilossi-2,2,6,6-tetrametilpiperidinil)-1,3,5-triazina con 1,2-bis-(3-amminopropilammino)-etano; prodotto di condensazione della 1,6-esandiammina-bis(2,2,6,6-tetrametil-4-piperidil)- con il prodotto di condensazione della 2,4,6-tricloro-1,3,5-triazine con di-n-butilammina e N-butil-2,2,6,6-tetrametil-4-piperidinammina CAS RN=192268-64-7; derivati del 7-oxa-3,20-diaza-dispiro-(5.1.11.2)-eneicosanone identificati dai CAS RN 64338-16-5; 85099-51-0; 85099-50-9; 202483-55-4; prodotto di reazione della 2,2,6,6-tetrametil-4-piperidina con il polimero ottenibile per copolimerizzazione dell’anidride maleica con alcheni C20-24 CAS RN=152261-33-1; prodotti descritti in EP 782994.
7. Ossammidi, come per esempio: 4,4’-diottilossi-ossalanilide; 2,2’-dietossi-ossalanilide; 2,2’-diottilossi-5,5’-di-ter-butil-ossalanilide; 2,2’-didodecilossi-5,5’-di-ter-butil-ossalanilide; 2-etossi-2’-etilossi-ossalanilide; N,N’-bis(3-dimetilamminopropil)ossalanilide; 2-etossi-2’-etil-5,4’-di-ter-butil-ossalanilide; miscele di ossalanilidi o- e p- metossi disostituite e miscele di ossalanilidi o- e p- etossi disostituite.
8. 2-(2-idrossifenil)-1,3,5-triazine, come per esempio: 2,4,6-tris(2-idrossi-4-octilossifenil)-1,3,5-triazina; 2-(2-idrossi-4-octilossifenil)-4,6-bis(2,4-dimetilfenil)-1,3,5-triazina; 2,4-bis(2-idrossi-4-propilossifenil)-6-(2,4-dimetilfenil)-1,3,5-triazina; 2-(2-idrossi-4-octilossifenil)-4,6-bis-(4-metil-fenil)-1,3,5-triazina; 2-(2-idrossi-4-dodecilossifenil)-4,6-bis-(2-4-dimetil-fenil)-1,3,5-triazina; 2-(2-idrossi-4-tridecilossifenil)-4,6-bis-(2-4-dimetil-fenil)-1,3,5-triazina; 2-(2-idrossi-4-(2-idrossi-3-butilossi-propossi)fenil)-4,6-bis(2,4-dimetil)-1,3,5-triazina; 2-(2-idrossi-4-(2-idrossi-3-octilossi-propossi)-fenil)-4,6-bis(2,4-dimetil)-1,3,5-triazina; 2-(4-(dodecilossi/tridecilossi-2-idrossipropossi)-2-idrossifenil)-4,6-bis(2,4-dimetilfenil)-1,3,5-triazina; 2-(2-idrossi-4-(2-idrossi-3-dodecilossi-propossi)fenil)-4,6-bis(2,4-dimetilfenil)-1,3,5-triazina; 2-(2-idrossi-4-esilossi)fenil-4,6-difenil-1,3,5-triazina; 2-(2-idrossi-4-metossifenil)-4,6-difenil-1,3,5-triazina; 2,4,6-tris(2-idrossi-4-(3-butossi-2-idrossi-propossi)fenil-1,3,5-triazina; 2-(2-idrossifenil)-4-(4-metossifenil)-6-fenil-1,3,5-triazina; 2-(2-idrossi-4-(3-(2-etilesil-1-ossi)-2-idrossipropilossi)fenil)-4,6-bis(2,4-dimetilfenil)-1,3,5-triazina.
C. DEATTIVATORI METALLICI
Per esempio: N,N’-difenilossammide; N-salicilal-N’-salicilol-idrazina; N,N’bis(salicilol)idrazina; N,N’-bis(3,5-di-ter-butil-4-idrossifenilpropionil)idrazina; 3-salicilolamino-1,2,4-triazolo; bis(benzilidene)ossalil diidrazide; ossalanilide; isoftaloil diidrazide; sebacoil bisfenilidrazide; N,N’-diacetiladipoil diidrazide; N,N’-bis(saliciloil)ossalil diidrazide; N,N’-bis(saliciloil)tiopropionil diidrazide.
D. FOSFITI E FOSFONITI
Per esempio: trifenil fosfito; difenil alchil fosfiti; fenil dialchil fosfiti; tris(nonilfenil)fosfito; trilauril fosfito; trioctadecil fosfito; distearil pentaeritritol difosfito; tris(2,4-di-ter-butil-fenil) fosfito; diisodecil pentaeritritol difosfito; bis(2,4-diter-butilfenil) fosfito; diisodecil pentaeritritol difosfito; bis(2,4-di-ter-butilfenil) pentaeritritol difosfito; bis(2,6-di-ter-butil-4-metilfenil)-pentaeritritol difosfito; diisodecilossi-pentaeritritol difosfito; bis-(2,4-di-ter-butil-6-metilfenil)pentaeritritol difosfito; bis(2,4,6-tris(ter-butilfenil)pentaeritritol difosfito; tristearil sorbitol trifosfito; bis(2,4-di-ter-butil-6-metilfenil) metil fosfito; bis(2,4-di-ter-butil-6-metilfenil) etil fosfito; 2,2’,2’’-nitrilo(trietiltris(3,3’,5,5’-tetra-ter-butil-1,1’-bifenil-2,2’-idil) fosfito); 2-etilesil (3,3’,5,5’-tetra-ter-butil-1,1’-bifenil-2,2’-idil) fosfito); tetra(2,4-di-tert-butilfenil) 4-4’-bifenilene difosfonito.
E. IDROSSILAMMINE
Per esempio: N,N-dibenzilidrossilammina; N,N-dietilidrossilammina; N,N-dioctilidrossilammina; N,N-dilaurilidrossil-ammina; N,N-ditetradecilidrossilammina; N,N-diesadecilidrossilammina; N,N-dioctadecilidrossilammina; N-esadecil-N-octadecilidrossilammina; N-eptadecil-N-octadecilidrossilammina; N,N-dialchilidrossilammine derivate dalle ammine di sego idrogenato.
F. NITRONI
Per esempio: N-benzil-alfa-fenil-nitrone; N-etil-alfa-metil-nitrone; N-octil-alfaeptil-nitrone; N-lauril-alfa-undecil-nitrone;N-tetradecil-alfa-tridecil-nitrone; N-esadecilalfa-pentadecil-nitrone; N-octadecil-alfa-pentadecil-nitrone; N-eptadecil-alfa-eptadecilnitrone; N-octadecil-alfa-esadecil-nitrone; nitroni derivati da N,N-dialchilidrossilammine ottenute da ammine di sego idrogenato.
G. DERIVATI TIOSINERGICI
per esempio dilauril tiodipropionato o stearil tiodipropionato.
H. AGENTI ANTI PEROSSIDI
Per esempio esteri dell’acido tiodipropionico con gli alcoli laurilico, stearilico, miristico o tridecilico; mercaptobenzimidazolo o il sale di zinco del 2-mercaptobenzimidazolo; dibutilditiocarbammato di zinco; dioctadecil disolfuro; pentaeritritolo tetrakis(β-dodecilmercapto)propionato.
I. STABILIZZATORI DI POLIAMMIDE
Per esempio i sali di rame in combinazione con ioduri e/o composti fosforati e sali del manganese bivalente.
L. CO-STABILIZZANTI BASICI
Per esempio: melammina; polivinilpirrolidone; diciandiammide; triallilcianurato; derivati dell’urea; derivati dell’idrazina; ammine; poliammidi; poliuretani; sali di metalli alcalini e alcalino terrosi degli acidi grassi superiori come stearato di calcio, stearato di zinco, beenato di magnesio, stearato di magnesio, sodio ricinoleato, potassio palpitato, sali di antimonio o zinco del pirocatecolo.
M. AGENTI ENUCLEANTI
Per esempio: sostanze inorganiche quali talco; ossidi metallici come il biossido di titanio o l’ossido di magnesio; fosfati, carbonati o solfati o sali di metalli alcalino terrosi; composti organici come acidi mono o policarbossilici e i loro sali, per esempio acido 4-ter-butilbenzoico, acido adipico, acido difenilacetico, succinato di sodio; benzoato di sodio; composti polimerici come i copolimeri anionici.
N. BENZOFURANONI E INDOLINONI
Per esempio quelli descritti in USP 4.325.863; USP 4.338.244; USP 5.175.312; USP 5.216.052; USP 5.252.643; DE-A-4316611; DE-A-4316622; DE A-4316876; EP-A-0589839; EP-A-0591102; 3-(4-(2-acetoetossi)fenil)-5,7-di-terbutil-benzofuran-2-one; 5,7-di-ter-butil-3-(4-(2-stearoilossietossi)fenil)benzofuran-2-one; 3,3’-bis(5,7-di-ter-butil-3-(4-(2-idrossietossi)fenil)benzofuran-2-one); 5,7-di-ter-butil-3-(4-etossifenil)benzofuran-2-one; 3-(4-acetossi-3,5-dimetilfenil)-5,7-di-ter-butilbenzofuran-2-one; 3-(3,5-dimetil-4-pivaloilossifenil)-5,7-di-ter-butil-benzofuran-2-one; 3-(2,3-di-metilfenil)-5,7-di-ter-butil-benzofuran-2-one.
O. PIEMPITIVI E AGENTI RINFORZANTI
Per esempio: calcio carbonato; silicati; fibre di vetro; asbesto; talco; caolino; mica; bario solfato; ossidi e idrossidi metallici, carbon black; grafite; farina di legno o di fibre o altri prodotti naturali; fibre sintetiche.
P. ALTRI ADDITIVI
Per esempio plastificanti, lubrificanti, emulsionanti, pigmenti, modificatori di reologia; catalizzatori; agenti per il controllo di flusso; candeggianti ottici; agenti antifiamma; agenti antistatici, agenti rigonfianti.
L’invenzione verrà ora ulteriormente descritta con maggior dettaglio facendo riferimento agli esempi operativi qui sotto riportati:
Esempio 1
Una HALS di struttura (I) con m = 2, n = 3, x = 0, y = 1, R<1>= n-butile, Pi = residuo 2,2,6,6-tetrametil-4-piperidinico, NR<2>R<3>= residuo morfolinico e gruppi terminali H venne preparata con la seguente procedura. 0,2 moli di cloruro di cianurile vennero sciolte in 240 ml di xilene. Dopo raffreddamento a 10°C si aggiunsero in 30’ sotto agitazione 0,2 moli di N-(2,2,6,6-tetrametil-4-piperidinil)-butilammina, mantenendo la temperatura tra 10 e 15°C. Si aggiunsero poi 46 g di acqua e 0,216 moli di sodio idrossido come soluzione acquosa al 30%. Si scaldò sotto agitazione fino a 60°C mantenendo questa temperatura per 30’, dopodiché venne rimossa la fase acquosa. La soluzione venne raffreddata a 0°C ed in 30’ vennero gocciolate 0,2 moli di morfolina, mantenendo la temperatura tra 0 e 5°C. Al termine dell’aggiunta la miscela venne riscaldata a 70-80°C e dopo 30’ di agitazione si aggiunsero 46 g di acqua e 0,216 moli di sodio idrossido come soluzione acquosa al 30%. Dopo 30’ ad 85°C si interruppe l’agitazione e si rimosse la fase acquosa.
La soluzione xilenica ottenuta, contenente 0,2 moli di un composto di formula generale (IV) con R<1>= n-butile, Pi = residuo 2,2,6,6-tetrametil-4-piperidinico ed NR<2>R<3>= residuo morfolinico, venne addizionata con 0,1 moli di N,N’-bis(amminopropil)-etilendiammina, corrispondente ad una ammina di formula generale (II) con m = 2 ed n = 3; venne neutralizzata l’acidità con il quantitativo equivalente di alcali e si portò la soluzione a bollore allontanando per distillazione l’acqua formatasi. Terminata la raccolta di acqua si proseguì la distillazione raggiungendo gradualmente 140°C in caldaia e raccogliendo ca.110 ml di xilene in 3 ore. Si raffreddò a 80°C, si aggiunsero 120 ml di acqua e dopo 30’ di agitazione a 80-90°C si scaricò la fase acquosa.
Si ottennero così 241 g di una soluzione xilenica che, dopo filtrazione per la rimozione di eventuali parti indisciolte, venne portata a secco per distillazione del solvente sotto vuoto, ottenendo per raffreddamento del fuso 92 grammi di prodotto solido (HALS1).
Esempio 2
Una HALS costituita da una miscela di oligomeri di struttura (I) con x = 1, y = 1-10, m = 2, n = 3, R<1>= n-butile, Pi = residuo 2,2,6,6-tetrametil-4-piperidinico, NR<2>R<3>= residuo morfolinico ed A = residuo di N-(2,2,6,6-tetrametil-4-piperidinil)-butilammina venne preparata con la seguente procedura.
In un reattore vennero gocciolati, alla temperatura di 15-20°C, 0,08 moli di N-(2,2,6,6-tetrametil-4-piperidinil)-butilammina in una soluzione di 0,08 moli di cloruro di cianurile in 156 ml di xilene. Dopo neutralizzazione con l’equivalente quantità di alcali venne rimossa la fase acquosa, ottenendo una soluzione xilenica di 0,08 moli di composto di formula VI con A = residuo di N-(2,2,6,6-tetrametil-4-piperidinil)-butilammina.
Separatamente, con la procedura descritta nel precedente esempio 1, vennero preparati 240 g di soluzione xilenica di 0,1 mol del composto di formula (V) denominato HALS1.
Le due soluzioni vennero unite e la miscela risultante venne riscaldata a ricadere per 5 ore in presenza di 0,17 moli di sodio idrossido al 30%, allontanando per distillazione l’acqua di reazione.
La soluzione venne poi raffreddata a 80°C, lavata con 140 ml di acqua distillata e, dopo filtrazione per rimuovere eventuali parti indisciolte, venne portata a secco per distillazione del solvente sotto vuoto, ottenendo per raffreddamento del fuso 115 grammi di prodotto solido (HALS2).
Esempio 3
Una HALS costituita da una miscela di oligomeri di struttura (I) con x = 1, y = 1-10, m = 2, n = 3, R<1>= n-butile, Pi = residuo 2,2,6,6-tetrametil-4-piperidinico, NR<2>R<3>= residuo morfolinico ed A = residuo di morfolina venne preparata con la seguente procedura.
In un reattore vennero gocciolati, alla temperatura di 0-5°C, 0,08 moli di morfolina in una soluzione di 0,08 moli di cloruro di cianurile in 156 ml di xilene. Dopo neutralizzazione con l’equivalente quantità di alcali venne rimossa la fase acquosa, ottenendo una soluzione xilenica di 0,08 moli di composto di formula VI con A = residuo di morfolina.
Separatamente, con la procedura descritta nel precedente esempio 1, vennero preparati 240 g di soluzione xilenica di 0,1 mol del composto di formula (V) denominato HALS 1.
Le due soluzioni vennero unite e la miscela risultante venne riscaldata a ricadere per 5 ore in presenza di 0,17 moli di sodio idrossido al 30%, allontanando per distillazione l’acqua di reazione.
La soluzione venne poi raffreddata a 80°C, lavata con 140 ml di acqua distillata e, dopo filtrazione per rimuovere eventuali parti indisciolte, venne portata a secco per distillazione del solvente sotto vuoto, ottenendo per raffreddamento del fuso 105 grammi di prodotto solido (HALS 3).
Esempio 4
Venne effettuato un test applicativo per valutare la stabilizzazione alla luce di una fibra poliolefinica, in particolare polipropilenica. In questo esempio e in quello successivo, le denominazioni HALS 1, HALS 2 ed HALS 3 indicano rispettivamente i composti preparati secondo gli esempi 1, 2, e 3.
1000 parti in peso di polipropilene omopolimero in polvere non stabilizzato (Indice di fluidità : ca. 10-12 g / 10’ a 230˚C – 2,16 kP) vennero mescolate in un mescolatore da laboratorio con 0,75 parti in peso di Calcio Stearato, 0,50 parti in peso di tris-(2,4-di-ter-butil-fenil) fosfito, 0,50 parti in peso di 1,3,5-tris-(3,5-di-ter-butil-4-idrossibenzil) isocianurato e 1,5 parti in peso degli stabilizzanti HALS 1, 2 o3 come da successiva Tabella 1.
La mescola a secco venne estrusa in estrusore da laboratorio a 230°C e granulata. Il granulato venne trasformato in filato multibava a titolo 480/60 dtex (rapporto di stiro 1:3) mediante filatura, utilizzando un estrusore da laboratorio ad una temperatura massima di 260°C.
Il filato venne esposto in un Weather-Ometer (WOM Ci65) secondo ISO 4892. La resistenza alla luce venne seguita prelevando periodicamente i campioni trattati e sottoponendoli a valutazione di resistenza a trazione mediante controllo del carico a rottura. Quale parametro per paragonare la resistenza alla luce dei campioni venne utilizzato il t50definito come “tempo di esposizione in WOM, espresso in ore, ad un Carico a Rottura pari al 50% del valore iniziale†.
I risultati sperimentali ottenuti sono riassunti in Tabella 1.
TABELLA 1. Stabilità alla luce di filato multibava PP 480/60 dtex
Stabilizzazione<t>50<ore WOM>
Senza stabilizzante luce 300
0,15% HALS 1 1270
0,15% HALS 2 1410
0,15% HALS 3 1235
Esempio 5
Venne effettuato un test applicativo per valutare la stabilizzazione alla luce di film di Polietilene a bassa densità (LDPE).
1000 parti in peso di LDPE non stabilizzato (Indice di fluidità : ca. 0,6 g/10’ a 190°C – 2,16 kP) vennero mescolate in un mescolatore da laboratorio con 0,30 parti in peso di n-octadecil-3-(3’,5’-di-ter-butil-4-idrossifenil)-propionato ed 1,50 parti in peso degli stabilizzanti HALS 1, 2 o 3 come da successiva Tabella 2.
La mescola a secco venne estrusa in estrusore da laboratorio a 230°C e granulata.
Il granulato venne trasformato in film a spessore finale pari a 150 µm ca. mediante estrusione in bolla con estrusore da laboratorio munito di testa rotante, ad una temperatura massima di 230°C.
Provini ricavati dal film di cui sopra, dopo montaggio su appositi supporti, vennero esposti in un Weather-Ometer (WOM Ci35A) secondo ISO 4892 (ciclo 102/18’).
La resistenza alla luce venne seguita prelevando periodicamente i campioni trattati e sottoponendoli al controllo dell’Indice di Carbonile mediante misure FT-IR.
Quale parametro per paragonare la resistenza alla luce dei campioni venne utilizzato il t0,10definito come “tempo di esposizione in WOM, espresso in ore, necessario alla crescita dell’Indice di Carbonile ad un valore 0,10†.
I risultati sperimentali ottenuti sono riassunti in Tabella 2
TABELLA 2. Stabilità alla luce di film soffiato LDPE a spessore 150 µm
Stabilizzazione T0,10ore WOM Senza stabilizzante luce 250
0,15% HALS 1 3750
0,15% HALS 2 3900
0,15% HALS 3 3650
Claims (14)
- RIVENDICAZIONI 1. Composti stabilizzanti di formula generale (I) A N N N (CH2<)>mN N xy (CH2<)>n(CH2<)>n NH NH (I) NN N N NNNN N N Pi R1 R<2>R<3>Pi R<1>R2<R>3 nella quale x può esserezero ed 1; y à ̈ compreso tra 1 e 10; m ed n possono esser anche uguali fra di loro, assumono i valori da 2 a 8; A rappresenta un gruppo NPiR1 oppure un gruppo NR2R3; e Pi rappresenta il gruppo di formula (II) <H3C>CH3 H2C C CH NR4 (II) H2C C H3C CH3 in cui: a sua volta R4 = H oppure gruppo alchilico lineare o ramificato C1-C4oppure un gruppo OR5 in cui R5 = H oppure gruppo alchilico lineare o ramificato C1-C8; R1 = H oppure gruppo alchilico lineare o ramificato C1-C4; R2 e R3 possono essere uguali e rappresentano idrogeno, gruppi alchilici lineari o ramificati C1-C8, un gruppo cicloalchile avente da 5 a 12 atomi di carbonio, oppure possono assieme all'atomo di azoto formare un anello eterociclico da 5 a 7 membri, contenente altri eteroatomi come O.
- 2. Composti secondo la rivendicazione 1, in cui m=2 ed n =3.
- 3. Composti secondo le rivendicazioni 1 e 2, in cui R<1>Ã ̈ butile.
- 4. Composti secondo le rivendicazioni da 1 a 3, in cui nel gruppo Pi, rappresentato dalla formula (II), R4 = H.
- 5. Composti secondo le rivendicazioni a 1 a 4, in cui R<2>ed R<3>formano insieme all'atomo di azoto un anello morfolinico.
- 6. Composti secondo le rivendicazione da 1 a 5, in cui x=0 ed y=1 ed i gruppi terminali sono H.
- 7. Composti secondo le rivendicazione da 1 a 5, in cui x=1 ed A=NPiR<1>.
- 8. Composti secondo le rivendicazione da 1 a 5, in cui x=1 ed A=NR<2>R<3>.
- 9. Procedimento per la preparazione dei composti secondo la rivendicazione 1, aventi la seguente formula generale R1 R1 Pi N<N>Pi N N N<NH>(CH2)n<NH>(CH2)m<NH>(CH2)n<NH>N N N R3 R3 N R2 (V) N R2 consistente nel far reagire ammine aventi la seguente formula NH2-(CH2)n-NH-(CH2)m-NH-(CH2)n-NH2(III) in cui m e n sono anche uguali fra di loro ed assumono i valori da 2 a 8, con composti aventi la seguente formula Cl N N (IV) N N N Pi R<1>R2 R3 in cui Pi rappresenta il gruppo avente la seguente formula <H3C>CH3 H2C C <CH>NR4 (II) H2C C H3C CH3 in cui R4 = H oppure un gruppo alchilico lineare o ramificato C1-C4oppure un gruppo OR5 in cui R5 = H oppure gruppo alchilico lineare o ramificato C1-C8; R1 = H oppure gruppo alchilico lineare o ramificato C1-C4; R2 e R3 possono essere anche uguali e rappresentano idrogeno, gruppi alchilici lineari o ramificati C1-C8, un gruppo cicloalchile avente da 5 a 12 atomi di carbonio, oppure possono assieme all'atomo di azoto formare un anello eterociclico da 5 a 7 membri, contenente altri eteroatomi come O;
- 10. Procedimento la preparazione dei composti di formula (I) con x =1 ed y = 1-10 consistente nel far reagire composti della seguente formula generale R1 R1 Pi N<N>Pi N N N<NH>(CH2)n<NH>(CH2)m<NH>(CH2)n<NH>N N N R3 R3 N (V) N R2 R2 in cui m ed n possono esser anche uguali fra di loro, assumono i valori da 2 a 8 ed in cui Pi rappresenta il gruppo avente la formula <H3C>CH3 H2C C CH NR4 (II) H2C C H3C CH3 in cui R4 = H oppure un gruppo alchilico lineare o ramificato C1-C4oppure un gruppo OR5 in cui R5 = H oppure gruppo alchilico lineare o ramificato C1-C8; R1 = H oppure gruppo alchilico lineare o ramificato C1-C4; R2 e R3 possono essere uguali e rappresentano idrogeno, gruppi alchilici lineari o ramificati C1-C8, un gruppo cicloalchile avente da 5 a 12 atomi di carbonio, oppure possono assieme all'atomo di azoto formare un anello eterociclico da 5 a 7 membri, contenente altri eteroatomi come O con composti aventi formula (VI) A N N (VI) Cl N<Cl> in cui A rappresenta un gruppo NPiR1 oppure un gruppo NR2R3.
- 11. Composizione comprendente un materiale polimerico ed i composti secondo la rivendicazione 1, caratterizzato dal fatto di comprendere da 0,01% a 5% di uno o più composti secondo la rivendicazione 1.
- 12. Composizione secondo la rivendicazione 11, in cui il materiale polimerico à ̈ scelto dal gruppo di polietilene, polipropilene, polistirene, polibutadiene, polisoprene, e loro copolimeri, polivinilcloruro, polivinilidencloruro e loro copolimeri, polivinilacetato e suoi copolimeri, in particolare con etilene; poliesteri come il polietilentereftalato; poliammidi come il Nylon 6 e 6,6; poliuretani.
- 13. Composizione secondo la rivendicazione 11, in cui il materiale polimerico à ̈ poliolefinico.
- 14. Composizione secondo la rivendicazione 11, comprendente inoltre anche altre HALS monomeriche, polimeriche o macromolecolari.
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ITMI2009A000168A IT1393333B1 (it) | 2009-02-09 | 2009-02-09 | Nuove ammine stericamente impedite e loro uso come stabilizzanti per polimeri |
AT10152928T ATE549372T1 (de) | 2009-02-09 | 2010-02-08 | Sterisch gehinderte amine und ihre verwendung als polymer-stabilisatoren |
US12/702,083 US8404765B2 (en) | 2009-02-09 | 2010-02-08 | Sterically hindered amines and use thereof as polymer stabilizers |
EP10152928A EP2216364B9 (en) | 2009-02-09 | 2010-02-08 | Sterically hindered amines and use thereof as polymer stabilizers |
ES10152928T ES2384370T3 (es) | 2009-02-09 | 2010-02-08 | Aminas impedidas estéricamente y utilización de las mismas como estabilizantes de polímeros |
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CN110643036B (zh) * | 2019-08-23 | 2021-09-17 | 惠生(泰州)新材料科技有限公司 | 一种共聚耐高温尼龙及其制备方法和用途 |
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IT1403086B1 (it) | 2010-10-28 | 2013-10-04 | 3V Sigma Spa | Nuove ammine stericamente impedite polimeriche e loro uso come stabilizzanti per polimeri |
US11767616B2 (en) | 2017-08-18 | 2023-09-26 | Glen Raven, Inc. | Acrylic compositions including a hindered amine light stabilizer and methods of making and using the same |
US10214836B1 (en) * | 2017-08-18 | 2019-02-26 | Glen Raven, Inc. | Acrylic compositions including a hindered amine light stabilizer and methods of making and using the same |
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GB2349642A (en) * | 1996-07-12 | 2000-11-08 | Ciba Sc Holding Ag | Stabilizer mixtures for polyolefins |
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IT1052501B (it) | 1975-12-04 | 1981-07-20 | Chimosa Chimica Organica Spa | Composti politriazinici utilizzabili per la stabilizzazione di polimeri sintetici e procedimento per la loro preparazione |
GB2042562B (en) | 1979-02-05 | 1983-05-11 | Sandoz Ltd | Stabilising polymers |
IT1152192B (it) | 1982-05-19 | 1986-12-31 | Apital Prod Ind | Composti per stabilizzare i polimeri |
US5175312A (en) | 1989-08-31 | 1992-12-29 | Ciba-Geigy Corporation | 3-phenylbenzofuran-2-ones |
IT1246170B (it) * | 1990-07-24 | 1994-11-16 | Ciba Geigy Spa | Composizione stabilizzante per polipropilene comprendente composti triazinici contenenti gruppi piperidinici e composti metallici |
US5252643A (en) | 1991-07-01 | 1993-10-12 | Ciba-Geigy Corporation | Thiomethylated benzofuran-2-ones |
TW206220B (it) | 1991-07-01 | 1993-05-21 | Ciba Geigy Ag | |
TW260686B (it) | 1992-05-22 | 1995-10-21 | Ciba Geigy | |
GB2267490B (en) | 1992-05-22 | 1995-08-09 | Ciba Geigy Ag | 3-(Carboxymethoxyphenyl)benzofuran-2-one stabilisers |
NL9300801A (nl) | 1992-05-22 | 1993-12-16 | Ciba Geigy | 3-(acyloxyfenyl)benzofuran-2-on als stabilisatoren. |
MX9305489A (es) | 1992-09-23 | 1994-03-31 | Ciba Geigy Ag | 3-(dihidrobenzofuran-5-il)benzofuran-2-onas, estabilizadores. |
TW255902B (it) | 1992-09-23 | 1995-09-01 | Ciba Geigy | |
EP0782994B1 (en) | 1995-12-04 | 2003-02-05 | Ciba SC Holding AG | Block oligomers containing 2,2,6,6-tetramethyl-4-piperidyl groups as stabilizers for organic materials |
-
2009
- 2009-02-09 IT ITMI2009A000168A patent/IT1393333B1/it active
-
2010
- 2010-02-08 US US12/702,083 patent/US8404765B2/en not_active Expired - Fee Related
- 2010-02-08 EP EP10152928A patent/EP2216364B9/en not_active Not-in-force
- 2010-02-08 AT AT10152928T patent/ATE549372T1/de active
- 2010-02-08 ES ES10152928T patent/ES2384370T3/es active Active
Patent Citations (4)
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US4331586A (en) * | 1981-07-20 | 1982-05-25 | American Cyanamid Company | Novel light stabilizers for polymers |
GB2349642A (en) * | 1996-07-12 | 2000-11-08 | Ciba Sc Holding Ag | Stabilizer mixtures for polyolefins |
EP0835873A1 (en) * | 1996-10-14 | 1998-04-15 | Ciba Speciality Chemicals Holding Inc. | Mixtures of trisubstituted and tetrasubstituted polyalkylpiperidinylaminotriazine tetraamine compounds |
WO1999029684A1 (en) * | 1997-12-08 | 1999-06-17 | Cytec Technology Corp. | Morpholino end-capped, hindered amine substituted aminotriazine and their use as light stabilizers |
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CN110643036B (zh) * | 2019-08-23 | 2021-09-17 | 惠生(泰州)新材料科技有限公司 | 一种共聚耐高温尼龙及其制备方法和用途 |
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IT1393333B1 (it) | 2012-04-20 |
EP2216364A1 (en) | 2010-08-11 |
EP2216364B9 (en) | 2012-08-15 |
ES2384370T3 (es) | 2012-07-04 |
US20100204371A1 (en) | 2010-08-12 |
EP2216364B1 (en) | 2012-03-14 |
ATE549372T1 (de) | 2012-03-15 |
US8404765B2 (en) | 2013-03-26 |
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