ITMI971892A1 - Miscele di stabilizzanti - Google Patents
Miscele di stabilizzanti Download PDFInfo
- Publication number
- ITMI971892A1 ITMI971892A1 IT97MI001892A ITMI971892A ITMI971892A1 IT MI971892 A1 ITMI971892 A1 IT MI971892A1 IT 97MI001892 A IT97MI001892 A IT 97MI001892A IT MI971892 A ITMI971892 A IT MI971892A IT MI971892 A1 ITMI971892 A1 IT MI971892A1
- Authority
- IT
- Italy
- Prior art keywords
- mixture
- tert
- butyl
- bis
- stabilizers according
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 65
- 239000003381 stabilizer Substances 0.000 title claims description 38
- -1 benzoic acid ester Chemical class 0.000 claims description 81
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 229920000098 polyolefin Polymers 0.000 claims description 17
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical group O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 239000000049 pigment Substances 0.000 claims description 13
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 claims description 11
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052725 zinc Inorganic materials 0.000 claims description 11
- 239000011701 zinc Substances 0.000 claims description 11
- 239000004743 Polypropylene Substances 0.000 claims description 10
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 239000004698 Polyethylene Substances 0.000 claims description 8
- 229920000573 polyethylene Polymers 0.000 claims description 8
- 229920001155 polypropylene Polymers 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- HWRLEEPNFJNTOP-UHFFFAOYSA-N 2-(1,3,5-triazin-2-yl)phenol Chemical compound OC1=CC=CC=C1C1=NC=NC=N1 HWRLEEPNFJNTOP-UHFFFAOYSA-N 0.000 claims description 5
- FJGQBLRYBUAASW-UHFFFAOYSA-N 2-(benzotriazol-2-yl)phenol Chemical compound OC1=CC=CC=C1N1N=C2C=CC=CC2=N1 FJGQBLRYBUAASW-UHFFFAOYSA-N 0.000 claims description 5
- 239000000395 magnesium oxide Substances 0.000 claims description 5
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 5
- 159000000003 magnesium salts Chemical class 0.000 claims description 5
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 4
- 239000000347 magnesium hydroxide Substances 0.000 claims description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 4
- 239000004408 titanium dioxide Substances 0.000 claims description 4
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 238000006731 degradation reaction Methods 0.000 claims description 3
- 235000019359 magnesium stearate Nutrition 0.000 claims description 3
- 239000011787 zinc oxide Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229920005606 polypropylene copolymer Polymers 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 claims description 2
- 229910021511 zinc hydroxide Inorganic materials 0.000 claims description 2
- 229940007718 zinc hydroxide Drugs 0.000 claims description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 claims 1
- 125000005595 acetylacetonate group Chemical group 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 23
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- 150000002148 esters Chemical class 0.000 description 10
- 229920001684 low density polyethylene Polymers 0.000 description 9
- 239000004702 low-density polyethylene Substances 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000004700 high-density polyethylene Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920001903 high density polyethylene Polymers 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 4
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- YEWBOZCFGXOUQW-UHFFFAOYSA-N 2,6,7-trioxa-1-phosphabicyclo[2.2.2]octan-4-ylmethanol Chemical compound C1OP2OCC1(CO)CO2 YEWBOZCFGXOUQW-UHFFFAOYSA-N 0.000 description 4
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 4
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 150000001450 anions Chemical class 0.000 description 4
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 150000005846 sugar alcohols Polymers 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 3
- 235000012245 magnesium oxide Nutrition 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- FPQJEXTVQZHURJ-UHFFFAOYSA-N n,n'-bis(2-hydroxyethyl)oxamide Chemical compound OCCNC(=O)C(=O)NCCO FPQJEXTVQZHURJ-UHFFFAOYSA-N 0.000 description 3
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 2
- BUGAMLAPDQMYNZ-UHFFFAOYSA-N 1-(2,4,4-trimethylpentan-2-yl)-10h-phenothiazine Chemical class S1C2=CC=CC=C2NC2=C1C=CC=C2C(C)(C)CC(C)(C)C BUGAMLAPDQMYNZ-UHFFFAOYSA-N 0.000 description 2
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 2
- BWJKLDGAAPQXGO-UHFFFAOYSA-N 2,2,6,6-tetramethyl-4-octadecoxypiperidine Chemical compound CCCCCCCCCCCCCCCCCCOC1CC(C)(C)NC(C)(C)C1 BWJKLDGAAPQXGO-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- ZMWRRFHBXARRRT-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(N2N=C3C=CC=CC3=N2)=C1O ZMWRRFHBXARRRT-UHFFFAOYSA-N 0.000 description 2
- ZSSVCEUEVMALRD-UHFFFAOYSA-N 2-[4,6-bis(2,4-dimethylphenyl)-1,3,5-triazin-2-yl]-5-(octyloxy)phenol Chemical compound OC1=CC(OCCCCCCCC)=CC=C1C1=NC(C=2C(=CC(C)=CC=2)C)=NC(C=2C(=CC(C)=CC=2)C)=N1 ZSSVCEUEVMALRD-UHFFFAOYSA-N 0.000 description 2
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 2
- SAEZGDDJKSBNPT-UHFFFAOYSA-N 3-dodecyl-1-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)N(C)C(C)(C)C1 SAEZGDDJKSBNPT-UHFFFAOYSA-N 0.000 description 2
- FBIXXCXCZOZFCO-UHFFFAOYSA-N 3-dodecyl-1-(2,2,6,6-tetramethylpiperidin-4-yl)pyrrolidine-2,5-dione Chemical compound O=C1C(CCCCCCCCCCCC)CC(=O)N1C1CC(C)(C)NC(C)(C)C1 FBIXXCXCZOZFCO-UHFFFAOYSA-N 0.000 description 2
- UWSMKYBKUPAEJQ-UHFFFAOYSA-N 5-Chloro-2-(3,5-di-tert-butyl-2-hydroxyphenyl)-2H-benzotriazole Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(N2N=C3C=C(Cl)C=CC3=N2)=C1O UWSMKYBKUPAEJQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229920010126 Linear Low Density Polyethylene (LLDPE) Polymers 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 229920002367 Polyisobutene Polymers 0.000 description 2
- JWUXJYZVKZKLTJ-UHFFFAOYSA-N Triacetonamine Chemical compound CC1(C)CC(=O)CC(C)(C)N1 JWUXJYZVKZKLTJ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 2
- 239000012964 benzotriazole Substances 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- FQUNFJULCYSSOP-UHFFFAOYSA-N bisoctrizole Chemical compound N1=C2C=CC=CC2=NN1C1=CC(C(C)(C)CC(C)(C)C)=CC(CC=2C(=C(C=C(C=2)C(C)(C)CC(C)(C)C)N2N=C3C=CC=CC3=N2)O)=C1O FQUNFJULCYSSOP-UHFFFAOYSA-N 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/014—Stabilisers against oxidation, heat, light or ozone
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- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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- 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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
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- 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
- C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
- C08K5/353—Five-membered rings
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/30—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing heterocyclic ring with at least one nitrogen atom as ring member
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2217—Oxides; Hydroxides of metals of magnesium
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2217—Oxides; Hydroxides of metals of magnesium
- C08K2003/222—Magnesia, i.e. magnesium oxide
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2217—Oxides; Hydroxides of metals of magnesium
- C08K2003/2224—Magnesium hydroxide
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- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2296—Oxides; Hydroxides of metals of zinc
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Description
DESCRIZIONE dell'invenzione industriale
Questa invenzione riguarda una miscela di stabilizzanti contenente A) un certo composto amminico che presenta impedimenti starici, B) un composto del magnesio con un composto dello zinco e C) una sostanza che assorbe i raggi ultravioletti e/o un pigmento, riguarda l'impiego di questa miscela di stabilizzanti per stabilizzare una poliolefina nei confronti di una degradazione provocata dalla luce e riguarda la poliolefina così stabilizzata.
Parecchie miscele di stabilizzanti sono state già descritte nelle tecniche precedenti, per esempio, in US-A-4.929.652, US-A-5.037.870, EP-A-290.388, EP-A-468.923 e EP-A-690.094.
Sebbene esistano già numerosi sistemi di stabilizzanti, sussiste ancora la necessità di far migliorare ulteriormente la stabilità alla luce di una poliolefina.
In particolare, questa invenzione riguarda una miscela di stabilizzanti contenente
A)
(Al) almeno un composto avente la formula (I)
(I)
in cui R1 è idrogeno, C1-C8alchile, -Ο' , -OH, C1-C18alcossi, C3-C12cicloalcossi, -CH2CN, C3-C6alchenile, C7-C9fenilalchile, C7-C9fenilalchile sostituito su un radicale fenile con C1-C8alchile; oppure C1-C8acile, R2 , R3 , R5 e R6 , indipendentemente l'uno dall'altro, sono idrogeno, C1-C30alchile, C5-C12cicloalchile oppure fenile,
R4 è idrogeno, C1-C30alchile, C5-C12cicloalchile, C7-C8-fenilalchile, fenile oppure un gruppo avente la formula (II),
(II
in cui R7 ha uno dei significati indicati per R1 , e ni è un numero compreso tra 1 e 50; oppure
(A2) almeno un composto avente le formule (Illa) e (Illb)
(Illa)
(Illb)
in cui n2 e n2* sono un numero compreso tra 2 e 50;
B) ossido di magnesio, idrossido di magnesio, ossido di zinco, idrossido di zinco oppure un sale organico di zinco o di magnesio; e
C)
(Cl) una sostanza che assorbe i raggi ultravioletti oppure
(C2) un pigmento oppure
(C3) una sostanza che assorbe i raggi ultravioletti e un pigmento;
con la condizione che, quando il componente A) è almeno un composto avente le formule (Illa) e (Illb), il componente B) sia ossido di magnesio, idrossido di magnesio oppure un sale organico di zinco oppure di magnesio .
In generale, quando il componente A) è almeno un composto di formula (Illa) e (Illb), il componente B) è preferibilmente un sale organico di zinco oppure di magnesio .
Esempi di alchile avente fino a 30 atomi di carbonio sono metile, etile, propile, isopropile, nbutile, sec-butile, isobutile, terz-butile, 2-etilbutile, n-pentile, isopentile, 1-metilpentile, 1,3-dimetilbutile, n-esile, 1-metilesile, n-eptile, isoeptile, 1,1,3,3-tetrametilbutile, 1-metileptile, 3-metileptile, n-ottile, 2-etilesile, 1,1,3-trimetilesile, 1,1,3,3-tetrametilpentile, nonile, decile, undecile, 1-metilundecile, dodecile, 1,1,3,3,5,5-esametilesile, tridecile, tetradecile, pentadecile, esadecile, eptadecile, ottadecile, eicosile, docosile e triacontile. Uno dei significati preferiti di R3 e R6 è C1-C4alchile, in particolare metile. Uno dei significati preferiti di R2 e R5 è C1-C25alchile, in particolare C15-C2Salchile, per esempio C18-C22alchile. Uno dei significati preferiti di R4 è C1-.C2salchile, in particolare C10-C20alchile, per esempio ottadecile. Uno dei significati preferiti di Ri e R7 è C1-C4alchile, in particolare metile.
Esempi di C1-C18alcossi sono metossi, etossi, propossi, isopropossi, butossi, isobutossi, pentossi, isopentossi, esossi, eptossi, ottossi, decilossi, dodecilossi, tetradecilossi, esadecilossi e ottadecilossi. R1 e R7 possono essere per esempio C6-C12alcossi, in particolare eptossi oppure ottossi.
Esempi di C5-C12cicloalchile sono ciclopentile, cicloesile, cicloeptile, cicloottile e ciclododecile. Si preferisce C5-C8cicloalchile, in particolare si preferisce cicloesile.
Esempi di C5-C12cicloalcossi sono ciclopentossi, cicloesossi, cicloeptossi, cicloottossi, ciclodecilossi e ciclododecilossi . Si preferisce C6-Cecicloalcossi, in particolare si preferiscono ciclopentossi e cicloesossi.
Esempi di C3-C6alcheniie sono allile, 2-metallile, butenile, pentenile ed esenile. Si preferisce allile. L'atomo di carbonio in posizione 1 è preferibilmente saturo.
C7-C9fenilalchìle, che è non sostituito oppure sostituito con C1-C4alchile sul radicale fenilico è, per esempio, benzile, feniletile, metilbenzile, dimetilbenzile, trimetilbenzile oppure terz-butilbenzile. Si preferisce benzile.
Ci-C8acile è preferibilmente C1-C8alcanoile, C3-C8alchenoile oppure benzoile. Esempi sono formile, acetile, propionile, butirrile, pentanoile, esanoile, ottanoile, benzoile, acriloile e crotonile. Si preferisce acetile.
ni è preferibilmente un numero compreso tra 1 e 25,in particolare tra 1 e 20 oppure tra 1 e 10.
n2 e n2* , indipendentemente l'uno dall'altro, sono preferibilmente 2 fino a 25, in particolare 2 fino a 20 oppure 2 fino a 10.
R1 e R7 , indipendentemente l'uno dall'altro, sono preferibilmente idrogeno, C1-C4alchile, -OH, C6-C12alcossi, C5-C8cicloalcossi, allile, benzile oppure acetile, in particolare,idrogeno oppure metile.
I composti descritti come componente A) sono essenzialmente noti (in alcuni casi sono reperibili in commercio) e possono venire preparati mediante procedimenti noti, per esempio come descritto in DD-A-262 439 (Derwent 89-122983/17, Chemical Abstracts 111:58 964u), WO-A-94/12 544 (Derwent 94-177 274/22) e in US-A-4 340 534.
I composti di formule (Illa) e (Illb) possono venire ottenuti insieme sotto forma di miscela e inoltre possono venire impiegati come tali nella nuova miscela di stabilizzanti . Il rapporto (IIIa):(IIIb) è, per esempio, compreso tra 20:1 e 1:20 oppure tra 1:10 e 10:1.
Il componente A) è preferibilmente <®>UVINUL 5050 H, <®>LICHTSCHUTZSTOFF UV 31 oppure <®>HOSTAVIN N 30.
I significati dei gruppi terminali che saturano le valenze libere nei composti di formule (I), (Illa) e (Illb) dipendono dai procedimenti adottati per la loro preparazione. I gruppi terminali possono anche venire modificati dopo la preparazione dei composti.
Nei composti di formula (I), il gruppo terminale legato all'anello della 2,5-diossopirrolidina è, per esempio, idrogeno, e il gruppo terminale legato al radicale -C(R5) (R6)- è, per esempio,
Nei composti di formula (Illa), il gruppo terminaie legato all'azoto può essere, per esempio, idrogeno e il gruppo terminale legato al radicale 2-idrossipropilene può essere, per esempio, un gruppo
Nei composti di formula (Illb), il gruppo terminale legato al radicale dimetilene può essere, per esempio, -OH, e il gruppo terminale legato all'ossigeno può essere, per esempio, idrogeno. I gruppi terminali possono anche essere radicali di polieteri.
Una forma di realizzazione preferita di questa invenzione riguarda una miscela di stabilizzanti nella quale il componente A) è almeno un composto di formule (Illa) e (Illb).
Miscele di stabilizzanti preferite sono quelle nelle quali
R2 e R5 , indipendentemente l'uno dall'altro sono Ci-C25alchile oppure fenile,
R3 e R6 , indipendentemente l'uno dall'altro sono idrogeno oppure C1-C4alchile, e
R4 è C1-C25alchile oppure è un gruppo avente la formula (II).
Miscele di stabilizzanti particolarmente preferite sono quelle nelle quali il composto di formula (I) è
in cui R1 è idrogeno oppure metile, e ni è un numero compreso tra 1 e 25.
Il sale organico di zinco oppure di magnesio definito nel componente B) è preferibilmente un composto avente la formula MeL2 in cui Me è zinco oppure magnesio e L è un anione di un acido organico oppure di un enolo. L'acido organico può essere, per esempio, un acido solfonico, acido solfinico, acido fosfonico oppure acido fosfinico, ma preferibilmente è un acido carbossilico. L'acido può essere alifatico, aromatico, aralifatico oppure cicloalifatico; esso può essere lineare oppure ramificato; esso può essere sostituito con gruppi ossidrilici oppure con gruppi alcossilici; esso può essere saturo oppure insaturo e preferibilmente contiene 1 fino a 24 atomi di carbonio.
Esempi di acidi diquesto tipo sono gli acidi formico, acetico, propionico, butirrico, isobutirrico, capronico, 2-etilcapronico, caprilico, caprinico, laurico, paimitico, stearico, beenico, oleico, lattico, ricinoleico, 2-etossipropionico, benzoico, salicilico, 4-butilbenzoico, toluico, 4-dodecilbenzoico, fenilacetico, naftilacetico, cicloesancarbossilico, 4-butilcicloesancarbossilico oppure cicloesilacetico. L'acido carbossilico può anche essere una miscela tecnica di acidi carbossilici, per esempio, miscele tecniche di acidi grassi come miscele di acidi benzoici alchilati.
Esempi di acidi organici contenenti zolfo oppure fosforo sono gli acidi metansolfonico, etansolfonico, a,α-dimetiletansolfonico, n-butansolfonico, n-dodecansolfonico, benzensolfonico, toluensolfonico, 4-nonilbenzensolfonico, 4-dodecilbenzensolfonico oppure cicloesansolfonico, dodecansolfinico, benzensolfonico oppure naftalensolfinico, acido butilfosfonico, acido fenilfosfonico, monometil oppure monoetil fenilfosfonato, monobutilbenzilfosfonato, acido dibutilfosfinico oppure acido difenilfosfinico.
Se L è un anione enolato, preferibilmente esso è un anione di un composto β-dicarbonilico oppure di un o-acilfenolo . Esempi di composti β-dicarbonilici sono acetilacetone, benzoilacetone, dibenzoilmetano, etil acetoacetato, butil acetoacetato, lauril acetoacetato oppure α-acetilcicloesanone. Esempi di o-acilfenoli sono 2-acetilfenolo, 2-butirroilfenolo, 2-acetil-lnaftolo, 2-benzoilfenolo oppure aldeide salicilica. Preferibilmente, 1'enolato è l'anione di un composto β-dicarbonilico avente 5 fino a 20 atomi di carbonio.
Esempi preferiti del componente B) sono acetato, laurato e stearato di magnesio, formiato, acetato, enantato, laurato e stearato di zinco e acetilacetonato di zinco e acetilacetonato di magnesio.
In una forma di realizzazione preferita di questa invenzione, il componente B), sotto forma di sale organico di zinco oppure di magnesio, preferibilmente, è un acetilacetonato oppure un monocarbossilato alifatico avente per esempio 1 fino a 24 atomi di carbonio.
La sostanza che assorbe i raggi ultravioletti nel componente C) è preferibilmente un 2-(2'-idrossifenil)benzotriazolo, un 2-ìdrossibenzofenone, un estere dell'acido benzoico sostituito oppure non sostituito, un acrilato, una ossammide, una 2—{2— idrossifenil)-1,3,5-triazina, un monobenzoato del resorcinolo oppure una formammidina.
Il 2-(2'-idrossifenil)-benzotriazolo è per esempio 2-{2'-idrossi-5'-metilfenil)-benzotriazolo, 2-(3',5'-di-terz-butil-2'-idrossi-fenil)-benzotriazolo, 2- (5'-terz-butil-2'-idrossi-fenil)-benzotriazolo, 2-(2'-idrossi-5'-(1,1,3,3-tetrametil-butil)fenil)-benzotriazolo, 2- (3',5'-di-terz-butil-2'-idrossifenil)-5-cloro-benzotriazolo, 2- (3'-terz-butil-2’-idrossi-51-metilfenil)-5-cloro-benzotriazolo, 2-(3'-secbutil-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 costituita da 2-(3'-terzbutil-2 '-idrossi-5’-(2-ottilossicarbonil-etil)-ferii1)-5-cloro-benzotriazolo, 2—(3'-terz-butil-5'-[2-(2-etilesilossi)-carboniletil]-2'-idrossifenil)-5-cloro-benzotriazolo, 2-(3'-terz-butil-2'-idrossi-5'-(2-metossicarboniletil)fenil)-5-clorobenzotriazolo, 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’ -metilienil)-benzotriazolo, e 2-{3'-terzbutil-2 '-idrossi-5'-(2-isoottilossicarboniletil)fenil-benzotriazolo, 2,2'-metilen-bis[4-(1,1,3,3-tetrametilbutil) -6-benzotriazolo-2-il-fenolo]; oppure prodotto della esterificazione del 2-[3'-terz-butil-5'- (2-metossicarboniletil)-2'-idrossi-fenil]2H-benzotriazolo con polietileneglicole 300; con R = 3'-terz .butil-4'-idrossi-5'-2H-benzotriazolo-2-ilfenile.
Si preferiscono il 2-(3',5'-di-terz-butil-2'-idrossifenil)-5-cloro-benzotriazolo, il 2-(3'-terzbutil-2'-idrossi-5'-metilfenil)-5-cloro-benzotriazolo e il 2- (3',5'-di-terz-amil-2'-idrossifenil)benzotriazolo .
Il 2-idrossibenzofenone è per esempio il 4-idrossi, 4-metossi, 4-ottilossi, 4-decilossi, 4-dodecilossi, 4-benzilossi, 4,2',4'-triidrossi oppure 2 ’idrossi-4,4'-dimetossi derivati.
Si preferisce il 2-idrossi-4-ottilossibenzofenone.
L'estere di un acido benzoico sostituito oppure non sostituito è per esempio il 4-terz-butil-fenil salicilato, fenil salicilato, ottilfenil salicilato, dibenzoil resorcinolo, bis(4-terz-butilbenzoil)resorcinolo, benzoli resorcinolo, 2,4-di-terz-butilfenil 3,5-di-terz-butil-4-idrossibenzoato, esadecil 3,5-diterz-butil-4-idrossibenzoato, ottadecil 3,5-di-terzbitil-4-idrossibenzoato oppure 2-metil-4,6-di-terzbutilfenil 3,5-di-terz-butil-4-idrossibenzoato.
Si preferiscono il 2,4-di-terz-butilfenil 3,5-di-terz-butil-4-idrossibenzoato e l'esadecil 3,5-diterz-butil-4-idrossibenzoato .
L'acrilato è per esempio etil a-ciano-β,β-difenilacrilato, isoottil a-ciano-β,β-difenilacrilato, metil α-carbometossicinnamato, metil a-ciano-p-metilp-metossicinnamato, butil a-ciano-β-metil-p-metossicinnamato, metil a-carbometossi-p-metossicinnamato oppure N- (β-carbometossi-β-cianovinil)-2-metilindolina .
La ossammide è per esempio 4,4'-di-ottilossiossanilide, 2,2'-dietossi-ossanilide, 2,2'-di-ottilossi-5, 5'-di-terz.butossanilide, 2,2’-di-dodecilossi-5,5'-di-terz .butossanilide, 2-etossi-2'-etil-ossanilide, N,N’-bis-(3-dimetilamminopropil)-ossammide, 2-etossi-5-terz .butil-2'-etossanilide o sua miscela con 2-etossi-2 '-etil-5,4'-di-terz.butossanilide, miscele di ossanilidi orto- e para-metossi- disostituite o miscele di ossanilidi o- e p-etossi-disostituite.
La 2-(2-idrossifenil)-1,3,5-triazina, è 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-di-idrossifenil)-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-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-tridecilossifenil)-4,6-bis (2,4-dimetilfenil)-1,3,5-triazina, 2-[2-idrossi-4-(2-idrossi-3-butilossi-propossi)fenil]-4, 6-bis(2,4-dimetilfenil)-1,3,5-triazina, 2-[2-idrossi-4-(2-idrossi-3-ottilossi-propilossi)fenil]-4, 6-bis(2,4-dimetilfenil)-1,3,5-triazina, 2-[4(dodecilossi/tridecilossi-2idrossipropossi)-2-idrossifenil] -4,6-bis(2,4-dimetilfenil)-l,3,5-triazina, 2-[2-idrossi-4-(2-idrossi-3-dodecilossi-propossi) fenil]-4,6-bis-(2,4-dimetil-fenil)-1,3,5-triazina, 2-(2-idrossi-4-esilossi)fenil-4,6-difenil-l,3,5-triazina, 2-(2-idrossi-4-metossifenil)-4,6-difenil-l ,3,5-triazina, 2,4,6-tris-[2-idrossi-4- (3-butossi-2-idrossi-propossi)fenil]-1,3,5-triazina, oppure 2-(2-idrossifenil)-4-(4-metossifenil)-6-fenil-l,3,5-triazina.
Si preferiscono la 2-(2-idrossi-4-ottilossifenil)-4,6-bis (2,4-dimetilfenil)-1,3,5-triazina e la 2- (2-idrossi-4-esilossi)fenil-4,6-difenil-l,3,5-triazina.
Il monobenzoato è per esempio il composto di formula
La formammidina è per esempio il composto di formula
La sostanza che assorbe i raggi ultravioletti nel componente C) è in particolare un
2- (2'-idrossifenil)benzotriazolo, un 2-idrossibenzofenone oppure una 2-(2-idrossifenil)-1,3,5-triazina.
Il componente C) è preferibilmente una sostanza che assorbe i raggi ultravioletti.
Il pigmento nel componente C) può essere un pigmento inorganico oppure un pigmento organico.
Esempi di pigmenti inorganici sono biossido di titanio, ossido dizinco, nero-fumo, solfuro di cadmio, seleniuro di cadmio, ossido di cromo, ossido di ferro, ossido di piombo, ecc.
Esempi di pigmenti organici sono pigmenti azoici, antrachinoni delle ftalocianine, tetracloroisoindolinoni, chinacridoni, isoindoline, perileni, pirrolopirroli (per esempio Pigment Red 254) ecc.
Come pigmento componente C), si possono usare tutti i pigmenti descritti in "Gachter/Miiller:Plastics Additives Handbook, 3a Edizione, Hauser Publishers, Monaco Vienna New York", pag. 647 fino a 659, punti 11.2.1.1 fino a 11.2.4.2.
Un pigmento particolarmente preferito è il biossido di titanio.
Un'ulteriore forma di realizzazione preferita di questa invenzione è una miscela di stabilizzanti contenente
A) un composto avente la formula
oppure almeno un composto avente le formule (IIIa) e (IIIb) in cui n2 e n2*, indipendentemente l'uno dall'altro sono un numero compreso tra 2 e 10;
B) stearato di magnesio oppure stearato di zinco e C) il composto
La miscela di stabilizzante secondo la presente invenzione è utile per stabilizzare poliolefine. Esempi di adatte poliolefine sono riportati qui di seguito .
1. Polimeri di monoolefine e diolefine, per esempio polipropilene, poliisobutilene, polibutene-1, polimetilpentene-1, poliisoprene oppure polibutadiene, come pure polimeri di cicloolefine, per esempio diciclopentene o norbornene; polietilene (che può essere eventualmente reticolato), per esempio polietilene di elevata densità (HDPE), polietilene di elevata densità (HDPE), polietilene elevata densità e di elevato peso molecolare (HDPE-HMW), polietilene di elevata densità e di peso molecolare ultraelevato (HDPE-UHMW), polietilene di media densità (MDPE), polietilene di bassa densità (LDPE), polietilene lineare di bassa densità (LLDPE), polietilene ramificato di bassa densità (BLDPE).
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, ammìne, gruppi alchilici, alchenilici e/o arilici che possono essere π- oppure σ-coordinatì. 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 ulteriori attivatori come per esempio metallo-alchili, idruri di metalli, alchilalogenuri di metalli, alchilossidi di metalli oppure alchilossani di metan i, i metalli essendo elementi dei gruppi la, Ila e/o Illa. 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 al punto 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. Copolimeri di 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, etilene/esene, etilene/etilpen-tene, etilene/eptene, etilene/ottene, propilene/isobutilene, etilene/butene-1, propilene/butadiene, isobutilene/isoprene, etilene/alchil-acrilati, etilene/alchilmetacrìlati, etilene/acetato di vinile o etilene/acido acrilico e loro sali (ionomeri) e terpolimeri di etilene con propilene ed un diene, come esadiene, diciclopentadiene oppure etilidenenorbornene; inoltre miscele di tali copolimeri e loro miscele con i polimeri citati sotto 1), per esempio polipropilene/copolimeri etilene-popilene, LDPE/copolimeri etilene-vinilacetato (ÈVA), LDPE/copolimeri etilene-acido acrilico (EAA), LLDPE/ÈVA e LLDPE/EAA e copolimeri polialchilene/monossido di carbonio strutturati in modo alternato oppure in modo casuale e loro miscele con altri polimeri come per esempio poliammidi .
L’invenzione, pertanto, inoltre riguarda una composizione contenente una poliolefina e la nuova miscela di stabilizzanti.
Le poliolefine elencate sopra sotto il punto 1 sono preferite. Polietilene e polipropilene e anche un copolimero di polietilene oppure di polipropilene sono particolarmente preferiti.
I componenti della nuova miscela di stabilizzanti possono venire aggiunti al materiale da stabilizzare singolarmente oppure mescolati tra loro. Preferibilmente il componente (A) è presente in una quantità di 0,01 fino a 5%, in particolare di 0,05 fino a 1%; il componente (B) preferibilmente è presente in una quantità di 0,005 fino a 1%, in particolare di 0,025 fino a 0,2%; il componente (CI) preferibilmente è presente in una quantità di 0,01 fino a 1%, il componente (C2) preferibilmente è presente in una quantità di 0,01 fino a 10% e il componente (C3) preferibilmente è presente in una quantità di 0,01 fino a 10%. " % " è % in peso, rispetto al materiale da stabilizzare.
II rapporto tra la sostanza che assorbe i raggi ultravioletti e il pigmento nel componente (C3) preferibilmente è 2:1 fino a 1:10.
Il rapporto dei componenti (A):(B) preferibilmente è 30:1 fino a 1:30, per esempio 20:1 fino a 1:20 oppure 20:1 fino a 1:10.
Il rapporto dei componenti (A):(C1) preferibilmente è 1:20 fino a 30:1, per esempio 1:10 fino a 20:1 oppure 1:5 fino a 20:-l.
Il rapporto dei componenti (A):(C2) preferibilmente è 1:30 fino a 30:1, per esempio è 1:20 fino a 20:1 oppure è 1:10 fino a 10:1.
Il rapporto dei componenti (A):(C3) preferibilmente è 1:30 fino a 30:1, per esempio è 1:20 fino a 20:1 oppure è 1:10 fino a 10:1.
La nuova miscela di stabilizzanti oppure i suoi singoli componenti possono venire introdotti nella poliolefina mediante metodi noti, per esempio, prima oppure durante la formatura oppure applicando i composti, sciolti oppure dispersi, alla poliolefina, se necessario con successiva evaporazione del solvente. I singoli componenti della nuova miscela di stabilizzanti possono venire aggiunti ai materiali da stabilizzare sotto forma di polvere, granuli oppure sotto forma di una mescola-madre che contiene questi componenti, per esempio, in una concentrazione compresa tra 2,5% e 25% in peso.
Se si desidera, i componenti della nuova miscela di stabilizzanti possono venire mescolati allo stato fuso tra loro prima di venire incorporati nella poliolefina .
La nuova miscela di stabilizzanti oppure i suoi componenti possono venire aggiunti prima oppure durante la polimerizzazione, oppure prima della reticolazione .
I materiali stabilizzati in questo modo possono venire usati in un'ampia varietà di forme, per esempio, sotto forma di pellicole, fibre, nastri, composizioni per stampaggio, profili oppure leganti per vernici, adesivi oppure mastici.
La poliolefina stabilizzata dell'invenzione può inoltre contenere anche diversi additivi tradizionali, per esempio:
1. Antiossidanti
1.1. Monofenoli alchilati, per esempio, 2,6-diterz.butil-4-metil-fenolo, 2-terz.butil-4,6-dimetilfenolo, 2,6-di-terz .butil-4-etilfenolo, 2,6-diterz.butil-4-n-butilfenolo, 2,6-di-terz.butil-4-isobutilfenolo, 2,6-diciclopentil-4-metilfenolo, 2-(ametilcicloesil)-4,6-dimetilfenolo, 2,6-di-ottadecil-4-metilfenolo, 2,4,6-tri-cicloesilf enolo, 2,6-diterz.butil-4-metossimetilfenolo, nonilfenoli che sono lineari o ramificati, nelle catene laterali come per esempio 2,6-di-nonil-4-metil-fenolo, 2,4-dimetil-6-(1'-metil-undec-1'-il)-fenolo, 2,4-dimetil-6-(1'-metil-eptadec-1 '-il)-fenolo, 2,4-dimetil-6-{l'-metiltridec-1 'il)-fenolo e loro miscele.
1.2. Alchiltiometilfenoli, per esempio, 2,4-diottiltiometil-6-terz-butilfenolo, 2,4-diottiltiometil-6-metilfenolo, 2,4-diottiltiometil-6-etilfenolo, 2,6-di-dodeci1t iometil-4-noni1fenolo.
1.3. Idrochinoni e idrochinonialchilati, per esempio 2,6-di-terz-butil-4-metossi-fenolo, 2,5-di-terz-butilidrochinone, 2,5-di-terz-amilidrochinone, 2,6-difenil-4-ottadecilossif enolo, 2,6-di-terz-butil-idrochione, 2, 5-di-terz-butil-4-idrossianisolo, 3,5-diterz-butil-4-idrossianisolo, 3,5-di-terz-butil-4-idrosifenil-stearato, bis-(3,5-di-terz-butìl-4-idrosifenil)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'-tiobis- (6-terz.butil-4-metilienolo), 2,2’-tiobis-(4-ottilfenolo), 4,4*-tiobis- (6-terz.butil-3-metilfeolo), 4,4'-tiobis-(6-terz.butil-2-metilfenolo), 4,4'tio-bis- (3,6-di-sec-amilfenolo), 4,4'-bis-(2,6-dimeil-4-idrossifenil)-disolfuro.
1.6. Alchiliden-bisfenoli, per esempio 2,2'-metilenbis- (6-terz.butil-4-metilienolo), 2,2’-metilen-bis-(6-terz.butil-4-etilfenolo), 2,2'-metilen-bis-[4-metil-6- (α-metilcicloesil)-fenolo], 2,2'-metilen-bis-(4-metil-6-cicloesilfenolq), 2,2'-metilen-bis-(6-nonil-4-metilfenolo) , 2,2'-metilen-bis-(4,6-di-terz-butilfenolo), 2,2' -etìliden-bis(4,6-di-terz-butilfenolo), 2,2'-etiliden-bis- (4-terz.butil-4-isobutilfenolo), 2,2'-metilen-bis- [6-a-metilbenzil)-4-nonilfenolo], 2,2'-metilen-bis [6-(a,a-dimetilbenzil)-4-nonilfenolo], 4,4'-metilen-bis-(2,6-di-terz-butilfenolo), 4,4'-metilen-bis- (6-terz-butil-2-metilfenolo), 1,1-bis- (5-terz.butil-4-idrossi-2-metil-fenil)-butano, 2,6-bis-(6-terz.butil-5-metil-2-idrossibenzil)-4-metil-fenolo, 1,1,3-tris-(5-terz.butil-4-idrossi-2-metilfenil)-butano, 1,1-bis-(5-terz.butil-4-idrossi-2-metilfenil)-3-n-dodecilmercaptobutano, etileneglicol bis-[3,3-bis-(3'-terz.butil-4'-idrossi-fenil)-butirrato], bis- (3-terz.butil-4-idrossi-5-metilfenil)-diciclopentadiene, bis-[2-(3'-terz.butil-2'-idrossi-5'-metil-benzil)-6-terz .butil-4-metilfe-nil]tereftalato, 1,1-bis-(3,5-dimetil-2-idrossifenil)butano, 2,2-bis- (3,5-di-terz.-butil-4-idrossifenil)-propano, 2,2-bis- (5-terz.-butil-4-idrossi-2-metilfenil)-4-n-dodecilmercapto-butano, 1,1,5,5-tetra-(5-terz-butil-4-idrossi-2-metilfenil)-pentano.
1.7. 0-, N- e S-benzilcomposti, per esempio, 3,5,3',5'-tetra-terz-butil-4,4 ’-diidrossidibenziletere, ottadecil-4-idrossi-3, 5-dimetilbenzil-mercapto-acetato, tridecil-4-idrossi-3, 5-di-terz-butilbenzil mercaptoacetato, tris-(3,5-di-terz-butil-4-idrossibenzil)-ammina, bis- (4-terz-butil-3-idrossi-2,β-dimetil-benzil)-ditio-tereftalato, bis- (3,5-diterz-butìl-4-idrossibenzil)-solfuro, isoottil-3,5-diterz-buti1-4-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-térz-butil-4-idrossibnzil)-maionato, bis- [4-(1,1,3,3-tetrametilbutil)-fenili-2,2-bis- (3,5-diterz-butil-4-idrossibenzil)-maionato .
1.9. Composti idrossibenzil-aromatici, per esempio 1,3,5-tris-(3,5-di-terz-butil-4-idrossibenzil)-2,4,6-trimetil-benzene, 1,4-bis- (3,5-di-terz-butil-4-idrossibenzil)-2,3,5,6-tetrametilbenzene, 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-idrossi-anilino)-1,3,5-triazina, 2-ottilmercapto-4;6-bis-(3,5-diterz-butil-4-idrossianilino)-1, 3,5-triazina, 2-ottilmercapto-4,6-bis- (3,5-di-terz-butil-4-idrossi-fenossi)-1,3,5-triazina, 2,4,6-tris-(3,5-di-terz-butil-4-idrossifenossi)-1,2,3-triazina, 1,3,5-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-idrossifenilpropìonil )-esaidro-1,3,5-triazina, 1,3,5-tris- (3,5-dicicloesil)-4-idrossibenzil)-isocianurato.
Ί.ΐΊ.Benzilfosfonati, per esempio dimetil-2,5-di-terzbutil-4-idrossibenzilfosfonato, dietil-3,5-di-terzbutil-4-idrossibenzilfosfonato, diottadecil-3,5-diterz-butil-4-idrossibenzilfosfonato, diottadecil-5-terz-butil-4-idrossi-3-metilbenzilfosfonato, sale di Ca del monoetilestere dell'acido 3,5-di-terz-butil-4-idrossibenzil-fosfonico .
1.12._ Acilamininofenoli, per esempio 4-idrossilauranilide, 4-idrossistearanilide N-(3,5-diterz-butil-4-idrossifenil)-carbammato .
1.13. Esteri dell'acido β-(3,5-di-terz.butil-4-idrossifenil)-propionico con alcoli monoossodrilici oppure poliossidrilici, come per esempio con metanolo, etanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, glicole etilenico, 1,2-propandiolo, glicole neopentilico, tiodietilene glicole, dietilene glicole, trietilene glicole, pentaeritritolo, tris-(idrossietil) isocianurato, Ν,Ν'-bis(idrossietil)ossammide, 3-tiaundecanolo, 3-tiapentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-l-fosfa-2,6,7-triossabiciclo [2.2.2]-ottano.
1.14. Esteri dell’acido β-(5-terz.butil-4-idrossi-3-metilfenil)-propionico con alcoli monoossidrilici oppure poliossidrilici come per esempio con metanolo, etanolo, n-ottanolo, i-ottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, glicole etilenico, 1,2-propandiolo, neopentil glicol, tiodietilene glicol, dietilene glicole, trietilene glicole, pentaeritritolo, tris- (idrossietil)-isocianurato, N,N'-bis (idrossietil)-ossammide, 3-tiaundecanolo, 3-tiapentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-l-fosfa-2,6,7-triossabiciclo [2.2.2]-ottano.
1.15. Esteri dell'acido β-(3,5-dicicloesil-4-idrossifenil)-propionico, con alcooli monoossidrilici oppure poliossidrilici come per esempio con metanolo, etanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, glicole etilenico, 1,2-propandiolo, glicole neopentilico, tiodietilene glicole, dietilene glicole, trietilene glicole, pentaeritritolo, tris-(idrossietil)-isocianurato, N,N'-bis(idrossietil)ossammide, 3-tiaundecanolo, 3-tiapentadecanolo, trimetil-esandiolo, trimetilolpropano, 4-idrossimetil-l-fosfa-2,6,7-triossabiciclo [2.2.2]-ottano.
1.16. Esteri dell'acido 3,5-di-terz-butil-4-idrossifenilacetico, con alcoli monoossidrilici oppure poliossidrilici come per esempio con metanolo, etanolo, ottanolo, ottadecanolo, 1,6-esandiolo, 1,9-nonandiolo, etilen glicol, 1,2-propandiolo, neopentil glicol, tiodietilene glicole, dietilene glicole, trietilene glicole, pentaeritritolo, tris-(idrossietil)-isocianurato, N,N'-bis (idrossietil)-ossammide, 3-tiaundecanolo, 3-tiapentadecanolo, trimetilesandiolo, trimetilolpropano, 4-idrossimetil-l-fosfa-2,6,7-triossabiciclo [2.2.2]-ottano.
1.17. Ammidi dell’acido 3~(3,5-di-terz-butil-4-idrossifenil)-propionico come per esempio N,N'-bis-(3,5-di-terz.butil-4-idrossifenilpropionil)-esame tilendiammina, Ν,Ν'-bis- (3,5-di-terz.butil-4-idrossifenilpropionil)-trimetilendiammina, Ν,Ν'-bis-(3,5-di-terzbutil-4-idrossifenilpropionil)- idrazina.
1.18. Acido ascorbico (vitamina C).
1.19 Antiossidanti amminici, come per esempio Ν,Ν'-di-isopropil-p-fenilendiammina, N,N'-di-sec.-butil-pfenilendiammina, N, N'-bis{1,4-dimetil-pentil)-pfenilendiammina, N,N'-bis(l-etil-3-metil-pentil)-pfenilendiammina, N,N'-bis(1-metil-eptil)-p-fenilendiammina, N,N '-dicicloesil-p-fenilendiammina, N,N’-difenil-p-fenilendiammina, N,N'-di-(2-naftil)-p-fenilendiammina, N-isopropil-N'-fenil-p-fenilendiammina, N- (1,3-dimetilbutil)-N'-fenil-p-fenilendiammina, N- (1-metil-eptil)-N'-fenil-p-fenilendiammina, N-cicloesil-N'-fenil-p-fenilendiammina, 4-(p-toluenesolfammoil)-difenilammina, N,N'-dimetil-N,N’-di-secbutil-p-fenilendiammina, difenilammina, N-allildifenilammina, 4-isopropossi-difenilammina, N-fenil-1-naftilammina, N- (4-terz-ottilfenil)-1-naftilammina, N-fenil-2-naftilammina, difenilammina ottilata, per esempio p,p'-di-terz-ottil-difenilammina, 4-nbutilamminofenolo, 4-butirril-ammino-fenolo, 4-nonanoilammino-fenolo, 4-dodecanoil-ammino-fenolo, 4-ottadecanoil-ammino-fenolo, di-(4-metossi-fenil)-ammina, 2,6-di-terz-butil-4-dimetil-ammino-metilfenolo, 2,4'-diammino-difenilmetano, 4,4 ’-diamminodifenil-metano, Ν,Ν,N’,N'-tetrametil-4, 4'-diamminodifenilmetano, 1,2-di-[(2-metil-fenil)-animino]-etano, 1,2-di- (fenilaminino)-propano, (o-tolil)-biguanide, di-[4-(1',3'-dimetil-butil)-fenil]ammina, N-fenil-1-naftil-ammina terz-ottilata, miscela di terz-butil-/terz-ottildifenilammine mono- e dialchilate, miscela di nonildifenilammine mono- e dialchilate, miscela di dodecildifenilammine mono- e dialchilate, miscela di isopropil/isoesil-difenilammine monoalchilate e dialchilate, miscela di terz-butildifenilammine monoalchilate e dialchilate, 2,3-diidro-3,3-dimetil-4H-l,4-benzotiazina, fenotiazina, miscela di terzbutil/terz-ottil-fenotiazine mono- e dialchilate, miscela di terz-ottilfenotiazine mono- e dialchilate, N-allilfenotiazina, Ν,Ν,Ν' ,N’-tetrafenil-1,4-diamminobut-2-ene, N,N-bis-(2,2,6,6-tetrametil-piperidin-4-il)-esametilendiammina, bis- (2,2,6,6-tetrametilpiperidin-4-il)-sebacato, 2,2,6,6-tetrametilpiperidin-4-one, 2,2,6,6-tetrametilpiperidin-4-olo.
2. Agenti che assorbono la luce UV ed agenti fotostabilizzanti
2.1. Composti del nichel, come per esempio, complessi con il nichel del 2,2T-tio-bis-[4-{1,1,3,3-tetrametilbutil)-fenolo], come il complesso 1:1 o 1:2, eventualmente con leganti addizionali come n-butilammina, trietanoìammina o N-cicloesil-dietanolammina, dibutilditiocarbammato di nichel, sali del nichel del-1'acido 4-idrossi-3,5-di-terz.butilbenzilfosfonico, esteri monoalchilici, come l'estere metilico, etilico o butilico, complessi di nichel con chetossime, come 2-idrossi-4-metil-fenil-undecilchetossima, complessi del nichel con l-fenil-4-lauroil-5-idrossipirazolo eventualmente con leganti -addizionali.
2.2. Animine stericamente impedite, come per esempio bis- (2,2,6,6-tetrametilpiperidil)sebacato, bis-(2,2,6,6-tetrametilpiperidil)succinato, bis-(1,2,2, 6. 6-pentametilpiperidil)sebacato, bis-(1-ottilossi-2.2.6. 6-tetrametilpiperidil)sebacato, bis(1,2,2,6,6-pentametilpiperidil) -n-butil-3,5-di-terz.butil-4-idrossibenzil-malonato, prodotto di condensazione ottenuto da l-idrossietil-2,2,6,6-tetrametil-4-idrossipiperidina e dall'acido succinico, prodotto di condensazione ottenuto da N,N'-bis-(2,2,6,6-tetrametilpiperidil)-esametilendiaminina e dalla 4-terz-ottilammino-2,6-dicloro-l, 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-butanotetracarbossilato, 1,1'(1,2-etan-diil)-bis-(3,3,5,5-tetrametilpiperazinone), 4-benzoil-2,2,6,6-tetrametilpiperidina, 4-stearilossi-2,2,6,6-tetrametilpiperidina, bis-(1,2,2,6,6-pentametilpiperidil)2-n-butil-2- (2-idrossi-3,5-di-terz-butil-benzil)-maionato, 3-n-ottil-7,7,9,9-tetrametil-l,3,8-triazaspiro [4.5]decan-2,4-dione, bis-(l-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-pìperidil)-esametilendiammina e 4-morfolino-2,6-dicloro-1,3,5-triazina, prodotto di condensazione di 2-cloro-4,6-di- (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-butilammino-l,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-triaza-spiro- [4.5]-decan-2,4-dione, 3-dodecil-1- (2,2,6,6-tetrametil-4-piperidil)pirrolidin--2,5-dione, 3-dodecil-l- (1,2,2,6,6-pentametil-4-piperidil)-pirrolidin-2,5-dione, miscela di 4-esadecilossi- e 4-stearilossi-2,2,6,6-tetrametilpiperidina, prodotto di condensazione di Ν,Ν'-bis(2,2,6,6-tetrametil-4-piperidil)esametilendiammina e di 4-cicloesilammino-2,6-dicloro-l,3,5-triazina, N-(2,2,6,6-tetrametil-4-piperidil)n-dodecil-succinimmide, N- (1,2,2,6,6-pentametil-4-piperidil)n-dodecilsuccinimmide, 2-undecil-7, 7,9,9-tetrametil-l-ossa3.8-diaza-4-osso-spiro [4.5]decano, prodotto di reazione di 7,7,9,9-tetrametil-2-cicloundecil-l-ossa-3.8-diaza-4-ossospiro [4.5]-decano e di epicloridrina.
3. Disattivatori di metalli, come per esempio Ν,Ν'-difenilossammide, N-salicilal-N'-saliciloilidrazina, Ν,Ν'-bis- (saliciloil)idrazina, Ν,Ν'-bis-(3,5-di-terz. butil-4-idrossifenilpropionil )-idrazina, 3-saliciloilammino-1,2,4-triazolo, bis(benziliden)-ossalildiidrazide ossanilide, isoftaloil-diidrazide, sebacoil-bis-fenilidrazide, N,N'-diaceti1-adipoildiidrazide, N,N'-bis-(saliciloil)-ossalil-diidrazide, Ν,Ν'-bis- (saliciloil)-tiodipropionil-diidrazide.
4. Fosfiti e fosfoniti, come per esempio, trifenilfosfito, difenilalchil fosfiti, fenildialchil fosfiti, tris (nonilfenil)fosfito, trilaurilfosfito, triottadecilfosfito, distearil-pentaeritritolo difosfito, tris- (2,4-di-terz.butilfenil)fosfito, diisodecilpentaeritritolo difosfito, bis-(2,4-di-terz.butilfenil) pentaeritritolo difosfito, bis-(2,6-di-terz-butil-4-metilfenil)-pentaeritritolo difosfito, bisisodecilossi-pentaeritritolo difosfito, bis-(2,4-diterz-butil-6-metilfenil)-pentaeritritolo difosfito, bis-2,4,6-tri-terz-butilfenil)-pentaeritritolo difosfito, tristearil-sorbitolo trifosfito, tetrakis-(2,4-di-terz.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-tetraterz-butil-12-metil-dibenzo [d,g]-1,3,2-diossafosfocina, bis- (2,4-di-terz-butil-6-metilfenil)-metilfosfito, bis- (2,4-di-terz-butil-6-metilfenil)-etilfosfito.
5. Idrossilammine, per esempio, N,N-dibenzilidrossilammina, N,N-dietilidrossilammina, N,N-diottilidrossilammina, N,N-dilaurilidrossilammina, N,N-ditetradecilidrossilanunina, N,N-diesadecilidrossilammina, N,N-diottadecilidrossilammina, N-esadecil-N-ottadecilidrossilammina, N-eptadecil-N-ottadecilidrossilammina, N,N-dialchilidrossilammina ottenuta da animine grasse del sego idrogenate.
6. Nitroni, per esempio, N-benzil-alfa-fenil nitrone, N-etil-alfa-metil nitrone, N-ottilalfa-eptil nitrone, N-lauril-alfa-undecil nitrone, N-tetradecil-alfatridecil nitrone, N-esadecil-alfa-pentadecil nitrone, N-ottadecil-alfa-eptadecilnitrone, N-esadecil-alfaeptadecil nitrone, N-ottadecil-alfa-pentadecil nitrone, N-eptadecil-alfa-eptadecil nitrone, N-ottadecilalfa-esadecil nitrone, nitrone derivato da N,N-dialchilidrossilammina derivata da ammina di sego idrogenata.
7. Composti tiosinerqici, come per esempio dilauril tiodipropionato,
8. Composti che distruggono i perossidi, come per esempio esteri dell'acido β-tiodipropionico, per esempio gli esteri laurilico, stearilico, miristilico o tridecilico, mercapto-benzimidazolo o il sale di zinco di 2-mercaptobenzimidazolo, dibutilditiocarbammato di zinco,-diottadecildisolfuro, pentaeritritol tetrakis-(β-dodecilmercapto)-propionato.
9. Agenti co-stabilizzanti basici, come per esempio, melammina, polivinilpirrolidone, diciandiammide, triallil cianurato, derivati di urea, derivati di idrazina, ammine, poliammidi, poliuretani, sali di metallo alcalino e sali di metallo alcalino terroso di acidi grassi superiori per esempio stearato di calcio, stearato di zinco, beenato di magnesio, stearato di magnesio, ricinoleato di sodio, palmitato di potassio, pirocatecolato di antimonio oppure pirocatecolato di stagno.
10. Agenti di nucleazione, come per esempio, sostanze inorganiche, per esempio talco, ossidi di metalli come biossido di titanio oppure ossido di magnesio, fosfati, carbonati oppure solfati, preferibilmente di metalli alcalino-terrosi; composti organici come acidi monocarbossilici oppure policarbossilici e anche loro sali come per esempio acido 4-terzbutilbenzoico, acido adipico, acido difenilacetico, succinato di sodio oppure benzoato di sodio; composti polimeri come per esempio copolimeri ionici ( "ionomeri").
11. Cariche e agenti di rinforzo, come per esempio carbonato di calcio, silicati, fibre di vetro, sfere di vetro, amianto, talco,- caolino, mica, solfato di bario, ossidi e idrossidi di metalli, nero-fumo, grafite, segatura e polveri oppure fibre di altri prodotti naturali, fibre sintetiche.
12. Ulteriori additivi, come per esempio plastificanti, lubrificanti, emulsionanti, pigmenti, additivi reologici, catalizzatori, agenti ausiliari dello stendimento, agenti sbiancanti ottici, agenti di protezione nei confronti della fiamma, agenti antistatici, propellenti.
13. 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-4315511, DE-A-4316622, DE-A-4316876, EP-A-0589839 oppure EP-A-0591102, oppure 3-[4-(2-acetossietossi)fenil]-5,7-diterz-butil-benzofuran-2-one, 5,7-di-terz-butil-3-[4-(2-stearoilossietossi)fenil]benzofuran-2-one, 3,3'-bis[5,7-di-terz-butil-3- (4-[2-idrossietossi]-fenil)-benzofuran-2-one], 5,7-di-terz-butil-3- (4-etossifenil)-benzofuran-2-one, 3-(4-acetossi-3,5-dimetilfenil)-5,7-di-terz-butil-benzofuran-2-one, 3-(3,5-dimetil-4-pivaloilossifenil)-5,7-di-terz-butil-benzofuran-2-one.
Il rapporto in peso tra la quantità totale di componenti A), B) e C) e gli additivi tradizionali può essere per esempio compresa tra 1:0,1 e 1:5.
L'invenzione inoltre riguarda l'impiego della nuova miscela di stabilizzanti per stabilizzare una poliolefina nei confronti di una degradazione provocata dalla luce.
L'esempio che segue illustra l'invenzione più dettagliatamente. Tutte le percentuali e le parti sono espresse in peso, a meno che non venga diversamente indicato.
Esempio 1: Stabilizzazione nei confronti della luce in pellicole di omopolimero di polipropilene.
100 parti di polvere di polipropilene non stabilizzato (indice di flusso allo stato fuso: circa 2,4 g/10 minuti, misurato a 230°C/2160 g) vengono omogeneizzate a 200°C per 10 minuti in un plastografo di Brabender con 0,05 parti di pentaeritritil-tetrakis-3-(3,5-di-terz.butil-4-idrossi fenil)propionato, 0,05 parti di tris-(2,4-di-terz-butilfenil)-fosfito e una miscela di stabilizzanti indicata nella Tabella 1. Il prodotto così ottenuto viene sottoposto a stampaggio mediante compressione in una pressa da laboratorio tra due fogli di alluminio per 6 minuti a 260°C ottenendo così una pellicola avente uno spessore di 0,5 mm e viene immediatamente raffreddata a temperatura ambiente in una pressa raffreddata con acqua. Provini di 60 mm x 25 mm vengono tagliati da queste pellicole di 0,5 mm e vengono sottoposti a esposizione in un apparecchio WEATHER-OMETER Ci 65 (temperatura del pannello nero 63±2°C, senza spruzzatura di acqua).
Periodicamente, si rimuovono questi provini dall'apparecchio di esposizione e si misura il loro contenuto in gruppi carbonilici usando uno spettrofotometro nell'infrarosso.
Il tempo di esposizione corrispondente alla formazione di un assorbimento del carbonile di 0,1 e una misura dell'efficienza della miscela di stabilizzante. I valori ottenuti sono riassunti nella Tabella 1.
Tabella 1:
Miscela di stabilizzanti Tempo per ottenere assorbimento del carbonile 0,1 in ore 0,05% di (A), 0,1% di stearato di zinco e 0,5% di TiO2
(rutilo) 1470 Confronto:
Miscela di stabilizzanti secondo US-A-4929 652
(0,05% di (XX), 0,1% di stearato
di zinco e 0,5% di TiO2 (rutilo) 1230 Fotostabilizzanti usati:
Fotostabilizzante (A) :
Miscela dei composti
(llla)
(lllb)
in cui il valore medio di n2 è circa 3,9 e il valore medio di n2* è circa 4,2 e il rapporto tra (Illa) e (Illb) è circa 4:1.
Fotostabilizzante (XX):
Il valore medio di n è 5,1.
Claims (15)
- RIVENDICAZIONI 1.Unamisceladi stabilizzantichecontiene A) (Al)almeno un composto di formula (I) (I) in cui R1 è idrogeno, Ci-C8alchile, -0' , -OH, Ci-C18alcossi, C5-C12cicloalcossi, -CH2CN, C3-C8alchenile, C7-C9fenilalchile, C7-C9fenilalchile che è sostituito su un radicale fenile con Ci-C^alchile; oppure C1-C8acile, R2 , R3 , R5 e R6 , indipendentemente l'uno dall'altro, sono idrogeno, C1-C30alchile, C5-C12cicloalchile oppure fenile, R4 è idrogeno, C1-C30alchile, Cs~Ci2cicloalchile, C7-C8-fenilalchile, fenile oppure un gruppo di formula (II), (II) in cui R7 ha uno dei significati indicati per R1 . e ni è un numero compreso tra 1 e 50; oppure (A2) almeno un composto avente le formule (Illa) e (IIIb) (Illa) (lllb) in cui n2 e n2* sono un numero compreso tra 2 e 50; B) ossido di magnesio, idrossido di magnesio, ossido di zinco, idrossido di zinco oppure un sale organico di zinco o di magnesio; e C) (Cl) una sostanza che assorbe i raggi ultravio-letti oppure (C2) un pigmento oppure (C3) una sostanza che assorbe i raggi ultravioletti e un pigmento; con la condizione che, quando il componente A) è almeno un composto di formule (Illa) e (Illb), il componente B) è un ossido di magnesio, un idrossido di magnesio oppure un sale organico di zinco oppure di magnesio.
- 2. Una miscela di stabilizzanti secondo la rivendicazione 1 in cui il componente A) è almeno un composto di formule (Illa) e (IIIb).
- 3. Una miscela di stabilizzanti secondo la rivendicazione 1 in cui R1 e R7 , indipendentemente l'uno dall'altro, sono idrogeno, C1-C4alchile, -OH, C6-C12alcossi, C3-C8cicloalcossi, allile, benzile oppure acetile.
- 4. Una miscela di stabilizzanti secondo la ri-vendicazione 1 in cui Ri e R7 , indipendentemente l'uno dall'altro sono idrogeno oppure metile.
- 5. Una miscela di stabilizzanti secondo la rivendicazione 1 in cui R2 e R5 , indipendentemente l’uno dall'altro, sono Ci-Gualchile oppure fenile. R-, e R« , indipendentemente l’uno dall'altro, sono idrogeno oppure C1-C4aichile. e R4 è C1-C2 alchile oppure un gruppo di formula
- 6. Una miscela di stabilizzanti secondo la rivendicazione 1 in cui il composto di formula (I) è ;in cui R1 è idrogeno oppure metile, e n1 è un numero compreso tra 1 e 25.
- 7. Miscela di stabilizzanti secondo la rivendicazione 1 in cui il sale organico di zinco oppure di magnesio è un acetilacetonato oppure un monocarbossilato alifatico.
- 8. Una miscela di stabilizzanti secondo la rivendicazione 1 in cui la sostanza che assorbe la luce UV è un 2-(2 '-idrossifenil)benzotriazolo, un 2-idrossibenzofenone, un estere dell'acido benzoico sostituito oppure non sostituito, un acrilato, una ossammide, una 2- (2-idrossifenil)-1,3,5-triazina, un monobenzoato di resorcionolo oppure una formammidina.
- 9. Una miscela di stabilizzanti secondo la rivendicazione 1 in cui la sostanza che assorbe la luce UV è un 2-(2'-idrossifenil)benzotriazolo, un 2-idrossibenzofenone oppure una 2-(2-idrossifenil)-1,3,5-triazina.
- 10. Una miscela di stabilizzanti secondo la rivendicazione 1 in cui il pigmento è biossido di titanio.
- 11. Una miscela di stabilizzanti secondo la rivendicazione 1 che contiene come componente C) una sostanza che assorbe la luce UV.
- 12. Una miscela di stabilizzanti secondo la rivendicazione 1 che contiene A) un composto di formula ;oppure almeno un composto di formule (Illa) e (Illb) in cui n2 e n2* , indipendentemente l'uno dall'altro sono un numero compreso tra 2 e 10; B) stearato di magnesio oppure stearato di zinco e C) il composto
- 13. Una composizione che contiene una poliolefina e una miscela di stabilizzanti secondo la rivendicazione 1.
- 14. Una composizione secondo la rivendicazione 13 in cui la poliolefina è polietilene oppure polipropilene oppure un copolimero di polietilene oppure polipropilene.
- 15. Un metodo per stabilizzare una poliolefina contro una degradazione provocata dalla luce, che consiste nell 'aggiungere alla poliolefina una miscela di stabilizzanti secondo la rivendicazione 1.
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AU2001233764A1 (en) * | 2000-02-22 | 2001-09-03 | Ciba Specialty Chemicals Holding Inc. | Stabilizer mixtures for polyolefins |
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US20030225191A1 (en) * | 2002-04-12 | 2003-12-04 | Francois Gugumus | Stabilizer mixtures |
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US20070238814A1 (en) * | 2006-04-10 | 2007-10-11 | Basf Corporation | Method of making coating compositions |
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US20100190878A1 (en) * | 2008-12-24 | 2010-07-29 | Sumitomo Chemical Company, Limited | Polyolefin resin composition and foam molded article |
SA116370295B1 (ar) * | 2015-02-20 | 2016-12-06 | باسف اس اى | رقائق، وأشرطة وفتائل أحادية من البولي أوليفين مثبتة للضوء |
CN112409516B (zh) * | 2019-08-22 | 2022-04-08 | 中国石油化工股份有限公司 | 氯乙烯聚合终止剂及制备方法和应用 |
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GB9100257D0 (en) | 1991-01-07 | 1991-02-20 | Sandoz Ltd | Improvements in or relating to organic compounds |
DE690094C (de) * | 1938-08-30 | 1940-04-17 | Wilhelm Liepelt | Trainingsgeraet |
DE2941004A1 (de) | 1979-10-10 | 1981-04-23 | Hoechst Ag, 6000 Frankfurt | Ether auf polyalkyl-1-oxa-diazaspirodecanbasis |
DE3104294A1 (de) * | 1981-02-07 | 1982-08-19 | Hoechst Ag, 6000 Frankfurt | Substituierte diazaspirodecane, ihre herstellung, ihre verwendung als stabilisatoren fuer organische polymere, sowie die so stabilisierten polymeren |
IT1215455B (it) | 1987-05-05 | 1990-02-14 | Ciba Geigy Spa | Composizione stabilizzante per polietilene comprendente composti contenenti gruppi piperidinici e composti metallici |
DE3871855D1 (de) * | 1987-05-05 | 1992-07-16 | Ciba Geigy Ag | Gegen lichtschaedigung stabilisierte polyolefine. |
DE3871854D1 (de) | 1987-05-05 | 1992-07-16 | Ciba Geigy Ag | Stabilisierung von organischen polymeren gegen lichtabbau. |
US4866136A (en) * | 1987-08-12 | 1989-09-12 | Pennwalt Corporation | Process for producing polymer bound hindered amine light stabilizers |
DE3919691A1 (de) * | 1989-06-16 | 1990-12-20 | Hoechst Ag | Polymere polyalkyl-1-oxa-diazaspirodecane |
IT1246170B (it) | 1990-07-24 | 1994-11-16 | Ciba Geigy Spa | Composizione stabilizzante per polipropilene comprendente composti triazinici contenenti gruppi piperidinici e composti metallici |
DE4239437A1 (de) | 1992-11-24 | 1994-05-26 | Basf Ag | Maleinsäureimid-alpha-Olefin-Copolymerisate und ihre Verwendung als Lichtschutzmittel und Stabilisatoren für organisches Material |
JPH09510485A (ja) | 1994-03-22 | 1997-10-21 | チバ−ガイギー アクチェンゲゼルシャフト | Hdpeの安定化方法 |
IT1269828B (it) | 1994-05-24 | 1997-04-15 | 3V Sigma Spa | Composizioni per la stabilizzazione di polimeri sintetici |
IT1269953B (it) | 1994-06-27 | 1997-04-16 | Ciba Geigy Spa | Films di poliolefine o copolimeri di olefine con migliorata stabilita' alla luce e resistenza agli insetticidi |
FR2725451B1 (fr) | 1994-10-06 | 1998-04-17 | Sandoz Sa | Nouvelle composition stabilisante pour les matieres polymeres |
EP0709426B2 (de) * | 1994-10-28 | 2005-01-05 | Ciba SC Holding AG | Synergistisches Stabilisatorgemisch |
DE59508533D1 (de) | 1994-10-28 | 2000-08-10 | Ciba Sc Holding Ag | Synergistisches Stabilisatorgemisch |
TW357174B (en) | 1995-01-23 | 1999-05-01 | Ciba Sc Holding Ag | Synergistic stabilizer mixture |
TW401437B (en) | 1995-02-10 | 2000-08-11 | Ciba Sc Holding Ag | Synergistic stabilizer mixture |
JP3065246B2 (ja) | 1995-03-10 | 2000-07-17 | 富士化学工業株式会社 | ハロゲン含有樹脂用安定剤、その製造法及びハロゲン含有樹脂組成物 |
TW358820B (en) | 1995-04-11 | 1999-05-21 | Ciba Sc Holding Ag | Synergistic stabilizer mixture |
TW360678B (en) | 1995-05-03 | 1999-06-11 | Ciba Sc Holding Ag | Synergistic stabilizer mixture for polyolefins |
TW438850B (en) | 1995-09-15 | 2001-06-07 | Ciba Sc Holding Ag | Stabilization of polyolefin composition in permanent contact with extracting media |
TW464670B (en) * | 1996-08-07 | 2001-11-21 | Ciba Sc Holding Ag | Stabilizer mixtures containing a hindered amine |
-
1997
- 1997-06-25 TW TW086108869A patent/TW464670B/zh not_active IP Right Cessation
- 1997-07-31 US US08/903,933 patent/US6566427B1/en not_active Expired - Lifetime
- 1997-08-01 KR KR1019970036854A patent/KR100471951B1/ko not_active IP Right Cessation
- 1997-08-01 GB GB9716205A patent/GB2316409B/en not_active Expired - Fee Related
- 1997-08-01 BE BE9700655A patent/BE1011447A3/fr active
- 1997-08-01 GB GB0018561A patent/GB2348880B/en not_active Expired - Fee Related
- 1997-08-04 DE DE19733717A patent/DE19733717B4/de not_active Expired - Fee Related
- 1997-08-05 FR FR9710007A patent/FR2752241B1/fr not_active Expired - Fee Related
- 1997-08-05 CA CA002212553A patent/CA2212553C/en not_active Expired - Fee Related
- 1997-08-05 ES ES009701741A patent/ES2134732B1/es not_active Expired - Lifetime
- 1997-08-06 IT IT97MI001892A patent/IT1293824B1/it active IP Right Grant
- 1997-08-06 NL NL1006730A patent/NL1006730C2/nl not_active IP Right Cessation
- 1997-08-07 JP JP9225698A patent/JPH1077462A/ja active Pending
-
2003
- 2003-03-24 US US10/395,623 patent/US7026380B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR19980018297A (ko) | 1998-06-05 |
US6566427B1 (en) | 2003-05-20 |
ES2134732A1 (es) | 1999-10-01 |
DE19733717B4 (de) | 2013-04-18 |
BE1011447A3 (fr) | 1999-09-07 |
TW464670B (en) | 2001-11-21 |
GB2316409A (en) | 1998-02-25 |
GB0018561D0 (en) | 2000-09-13 |
GB2316409B (en) | 2000-09-20 |
FR2752241A1 (fr) | 1998-02-13 |
GB9716205D0 (en) | 1997-10-08 |
GB2348880B (en) | 2000-12-13 |
KR100471951B1 (ko) | 2005-08-05 |
DE19733717A1 (de) | 1998-02-12 |
US20050075424A1 (en) | 2005-04-07 |
CA2212553C (en) | 2007-10-23 |
GB2348880A (en) | 2000-10-18 |
IT1293824B1 (it) | 1999-03-10 |
CA2212553A1 (en) | 1998-02-07 |
ES2134732B1 (es) | 2000-05-16 |
NL1006730A1 (nl) | 1998-02-12 |
FR2752241B1 (fr) | 2001-06-29 |
NL1006730C2 (nl) | 1999-03-15 |
JPH1077462A (ja) | 1998-03-24 |
US7026380B2 (en) | 2006-04-11 |
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