CN101228220A - 使用液体三(单烷基)苯基亚磷酸酯稳定聚烯烃 - Google Patents
使用液体三(单烷基)苯基亚磷酸酯稳定聚烯烃 Download PDFInfo
- Publication number
- CN101228220A CN101228220A CNA2006800267001A CN200680026700A CN101228220A CN 101228220 A CN101228220 A CN 101228220A CN A2006800267001 A CNA2006800267001 A CN A2006800267001A CN 200680026700 A CN200680026700 A CN 200680026700A CN 101228220 A CN101228220 A CN 101228220A
- Authority
- CN
- China
- Prior art keywords
- phenyl
- butyl
- mixture
- acid ester
- phosphorous acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920000098 polyolefin Polymers 0.000 title claims abstract description 33
- 239000007788 liquid Substances 0.000 title claims abstract description 27
- -1 phenyl phosphites Chemical class 0.000 title claims description 198
- 230000006641 stabilisation Effects 0.000 title claims description 8
- 238000011105 stabilization Methods 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims abstract description 86
- 238000000034 method Methods 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 27
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000032683 aging Effects 0.000 claims abstract description 6
- 238000002485 combustion reaction Methods 0.000 claims abstract description 5
- 239000003345 natural gas Substances 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 26
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 26
- VCAFTIGPOYBOIC-UHFFFAOYSA-N phenyl dihydrogen phosphite Chemical class OP(O)OC1=CC=CC=C1 VCAFTIGPOYBOIC-UHFFFAOYSA-N 0.000 claims description 21
- 150000001412 amines Chemical class 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 239000012298 atmosphere Substances 0.000 claims description 7
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical compound C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000004611 light stabiliser Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- 230000009931 harmful effect Effects 0.000 claims description 4
- ZCILGMFPJBRCNO-UHFFFAOYSA-N 4-phenyl-2H-benzotriazol-5-ol Chemical compound OC1=CC=C2NN=NC2=C1C1=CC=CC=C1 ZCILGMFPJBRCNO-UHFFFAOYSA-N 0.000 claims description 3
- PDLPMGPHYARAFP-UHFFFAOYSA-N (3-hydroxy-2-phenylphenyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C=1C(O)=CC=CC=1C(=O)C1=CC=CC=C1 PDLPMGPHYARAFP-UHFFFAOYSA-N 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 abstract description 11
- 150000008301 phosphite esters Chemical class 0.000 abstract description 7
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 abstract description 4
- 230000000087 stabilizing effect Effects 0.000 abstract 2
- 239000007983 Tris buffer Substances 0.000 abstract 1
- 230000002939 deleterious effect Effects 0.000 abstract 1
- 229920001684 low density polyethylene Polymers 0.000 abstract 1
- 239000004702 low-density polyethylene Substances 0.000 abstract 1
- 238000010128 melt processing Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 description 42
- 229910052757 nitrogen Inorganic materials 0.000 description 39
- 239000001301 oxygen Substances 0.000 description 30
- 229910052760 oxygen Inorganic materials 0.000 description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- 239000000654 additive Substances 0.000 description 19
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
- 239000004743 Polypropylene Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 150000002148 esters Chemical class 0.000 description 15
- 229920001155 polypropylene Polymers 0.000 description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 14
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 10
- 150000001721 carbon Chemical group 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 10
- 239000004700 high-density polyethylene Substances 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 9
- 229920001903 high density polyethylene Polymers 0.000 description 9
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 8
- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000002184 metal Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229940059574 pentaerithrityl Drugs 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 7
- 239000004698 Polyethylene Substances 0.000 description 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 7
- 229920000092 linear low density polyethylene Polymers 0.000 description 7
- 239000004707 linear low-density polyethylene Substances 0.000 description 7
- 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 7
- 229920000573 polyethylene Polymers 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 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 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000007859 condensation product Substances 0.000 description 6
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 6
- 230000002349 favourable effect Effects 0.000 description 6
- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical compound C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000004494 ethyl ester group Chemical group 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 4
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 4
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 4
- 125000006309 butyl amino group Chemical group 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- COVMBDWAODLWIB-UHFFFAOYSA-N n'-(2-hydroxyethyl)oxamide Chemical compound NC(=O)C(=O)NCCO COVMBDWAODLWIB-UHFFFAOYSA-N 0.000 description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 4
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
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- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 3
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- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
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- 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 3
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- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 3
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- 238000012360 testing method Methods 0.000 description 3
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- GPOGLVDBOFRHDV-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)O GPOGLVDBOFRHDV-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
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
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- 239000001361 adipic acid Substances 0.000 description 2
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
- C07F9/145—Esters of phosphorous acids with hydroxyaryl compounds
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
- C08K5/526—Esters of phosphorous acids, e.g. of H3PO3 with hydroxyaryl compounds
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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
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Abstract
本发明公开了一种稳定聚烯烃以抵抗熔体加工、热老化和暴露于天然气燃烧产物的有害效果的方法,该方法包括将有效稳定量的式I的三(单烷基)苯基亚磷酸酯或式I的亚磷酸酯的混合物掺入或应用于所述聚烯烃,其中每个R相同或不同并且为直链或支链的1至8个碳原子的烷基,并且其中所述亚磷酸酯或亚磷酸酯混合物在25℃和1个大气压下为液态。还公开了包括聚烯烃和本发明亚磷酸酯或亚磷酸酯混合物以及某些三(单烷基)苯基亚磷酸酯混合物的被稳定的组合物。本发明的液体亚磷酸酯稳定剂尤其与低密度聚乙烯相容。
Description
本发明的目的在于使用某些液体三(单烷基)苯基亚磷酸酯或三(单烷基)苯亚磷酸酯的液体混合物稳定聚烯烃的方法。
有机磷化合物是众所周知的聚合物加工稳定剂(process stabilizer)。例如,Plastics Additives Handbook,第4版,R.Gaechter,H.Mueller编辑,1993,第40-71页,讨论了稳定聚丙烯(PP)和聚乙烯(PE)。
已知的亚磷酸酯和亚膦酸酯稳定剂包括,例如三苯基亚磷酸酯、二苯烷基亚磷酸酯、苯基二烷基亚磷酸酯、三(壬基苯基)亚磷酸酯、三月桂基亚磷酸酯、三-十八烷基亚磷酸酯、二硬脂酰季戊四醇二亚磷酸酯、三(2,4-二叔丁基苯基)亚磷酸酯、双(2,4-二-α-枯基苯基(cumylphenyl))季戊四醇二亚磷酸酯、二异癸基季戊四醇二亚磷酸酯、双(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯(D)、双(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯(E)、双异癸氧基季戊四醇二亚磷酸酯、双(2,4-二-叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯、双(2,4,6-三-叔丁基苯基)季戊四醇二亚磷酸酯、三硬脂酰山梨醇三亚磷酸酯、四(2,4-二-叔丁基苯基)4,4′-亚联苯-二亚膦酸酯(H)、6-异辛氧基-2,4,8,10-四-叔丁基二苯并[d,f][1,3,2]二氧杂磷杂庚环(dioxaphosphepin)(C)、6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯并[d,g][1,3,2]二氧杂磷杂辛环(dioxaphosphocin)(A)、双(2,4-二-叔丁基-6-甲苯基)甲基亚磷酸酯、双(2,4-二-叔丁基-6-甲苯基)乙基亚磷酸酯(G)、2,2’,2”-次氮基[三乙基三(3,3’5,5’-四-叔丁基1-1,1’-联苯-2,2’-基)亚磷酸酯](B)、双(2,4-二-叔丁基苯基)辛基亚磷酸酯、聚(4,4′-{2,2′-二甲基-5,5′-二-叔丁基苯硫醚}辛基亚磷酸酯)、聚(4,4′{-异亚丙基二苯酚}-辛基亚磷酸酯)、聚(4,4′-{异亚丙基双[2,6-二溴苯酚]}-辛基亚磷酸酯)、聚(4,4′-{2,2′-二甲基-5,5′-二-叔丁基苯硫醚}-季戊四醇二亚磷酸酯),
U.S.3,756,906公开了作为聚酯增强橡胶稳定剂的亚磷酸酯。
U.S.5,208,368和U.S.6,576,788涉及制备二苯甲烷二异氰酸酯和聚苯基聚亚甲基聚异氰酸酯混合物的方法。教导了芳基亚磷酸酯作为稳定剂。
GB-A-2 227 490公开了由三氯化磷、联苯和苯酚制备的加工稳定剂混合物。
GB-A-1 298 248教导了制备三过氧化物(tris-peroxides)的方法。三芳基亚磷酸酯是双组分催化剂的一部分。
U.S.3,644,536同样教导了三(α-羟基异丙基)苯的制备方法。三芳基亚磷酸酯是双组分催化剂体系的一部分。
DE-A-2 940 620教导了制备三芳基亚磷酸酯的方法。芳基可以被一个或多个支链烷基或环烷基、芳基或芳烷基取代。三芳基亚磷酸酯可用作聚合物稳定剂。
U.S.5,254,709公开了制备空间位阻芳基亚磷酸酯的方法。
JP-A-7309884公开了制备三烷基苯基亚磷酸酯的方法。
从业人员仍在寻求与商购获得的那些稳定剂相比,与聚烯烃更加相容的亚磷酸酯稳定剂。
现在已经发现某些在环境条件下亚磷酸酯或亚磷酸酯混合物为液状态的三(单烷基)苯基亚磷酸酯,或三(单烷基)苯基亚磷酸酯的混合物与聚烯烃特别相容。三(单烷基)苯基亚磷酸酯或亚磷酸酯混合物是优良的加工稳定剂。
公开了一种稳定聚烯烃以抵抗熔体加工、热老化和暴露于天然气燃烧产物的有害效果的方法,该方法包括将有效稳定量的式I的三(单烷基)苯基亚磷酸酯或式I的亚磷酸酯的混合物掺入或应用于所述聚烯烃:
其中每个R相同或不同并且为直链或支链的1至8个碳原子的烷基,并且其中所述亚磷酸酯或亚磷酸酯混合物在25℃和1个大气压下为液态℃。
还公开了被稳定以抵抗熔体加工、热老化和暴露于天然气燃烧产物的有害效果的聚烯烃组合物,该组合物包括
a)聚烯烃,和
b)有效稳定量的式I的三(单烷基)苯基亚磷酸酯或式I的亚磷酸酯的混合物
其中每个R相同或不同并且为直链或支链的1至8个碳原子的烷基,并且其中所述亚磷酸酯或亚磷酸酯混合物在25℃和1个大气压下为液态。
壬基苯酚的制备例如公开于Faith,Keyes和Clark,IndustrialChemicals,F.A.Lowenheim,M.K.Moran编辑,Wiley-Interscience,NewYork,第4版,1975,第575-578页。参见Merck Index 11,6599。其为制备烷基苯酚的代表。
三(单烷基)苯基亚磷酸酯通过使三当量的单烷基苯酚与三氯化磷在没有氧气的情况下,例如在氮气气氛下,和除酸剂例如三乙胺存在的情况下进行反应来制备。
烷基是直链或支链的,并且例如为甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、戊基、叔戊基、己基、庚基、2,4,4-三甲基戊基、2-乙基己基、正辛基或叔辛基。
烷基是例如直链或支链的1至6个碳原子或1至4个碳原子的烷基。例如,烷基是甲基、乙基、仲丁基、叔戊基或己基。
优选地,每个R是相同或不同的并且为直链或支链的1至6个碳原子的烷基。
这样一种方法是有利的,其中每个R是相同或不同的并且为直链或支链的1至4个碳原子的烷基。
这样的一种方法也是有利的,其中每个R在邻位或对位被取代并且独立地为甲基、乙基、仲丁基、叔戊基或己基。
本发明式I的亚磷酸酯或亚磷酸酯混合物在环境条件,25℃和1个大气压下必须为液态。另外,唯一的限制是每个R是1至8个碳原子的直链或支链的烷基。
这样的一种方法是特别有利的,其中每个R等同并且在邻位或对位被取代。
这样的一种方法是非常特别有利的,其中每个R是仲丁基并且在邻位或对位被取代。
在本发明的式I的亚磷酸酯混合物中,单个组分在纯(分离)状态不必是液体。
例如,纯三-2-叔丁基苯基亚磷酸酯(m.p.66-68℃)和三-4-叔丁基苯基亚磷酸酯(m.p.73-75℃)作为单独的亚磷酸酯被排除在本发明外。但并没有将这些化合物从本发明亚磷酸酯液体混合物中排除。
三-3-叔丁基苯基亚磷酸酯(0.02mm时b.p.193-198℃)和三-2-仲丁基苯基亚磷酸酯(0.01mm时b.p.160-165℃)作为单独的亚磷酸酯被包含在本发明中。
可通过混合两种或更多种纯亚磷酸酯制备,或可使用两种或更多种不同的单烷基酚的混合物由三氯化磷直接制备亚磷酸酯液体混合物。
在本发明的亚磷酸酯混合物中,有至少两种不同的式I的亚磷酸酯。两种亚磷酸酯由于在至少一个苯基上具有不同的烷基或不同取代的烷基而不同。
不同的烷基指链长度不同或具有不同的支化(例如,正丁基、叔丁基、仲丁基)。不同取代指相对于酚羟基的不同位置(例如,间位、对位)。
当然,两种不同的单烷基酚可以具有链长和位置均不相同的烷基,或可以具有支化和位置均不相同的烷基,或可以具有链长和支化均不同的烷基,或可具有链长、支化和位置均不相同的烷基。
有利的是,本发明的亚磷酸酯液体混合物中大约60%或更多的酚基在邻位被取代。例如,大约70%或更多的酚基在邻位被取代,或大约80%或更多的酚基在邻位被取代。剩余的可为例如在对位被取代。
这样的一种方法是有利的,包括掺入或应用式I的亚磷酸酯混合物,其中R基团在邻位或对位并且独立地是甲基、乙基、仲丁基、叔戊基或己基,并且其中大约60%或更多的酚基在邻位被取代。
例如,每个R基是等同的,例如,每个R基为仲丁基,并且在邻位和对位。
例如,亚磷酸酯混合物是以下化合物的混合物。
其中R基是等同的。
这样的一种方法是有利的,包括掺入或应用式I的亚磷酸酯混合物,其中每个R基团是等同的并且在邻位或对位取代,其中大约60%或更多的酚基在邻位被取代。
例如,在本发明的亚磷酸酯混合物中,每个R基是等同的,并且大约60%或更多的酚基在邻位被取代。例如,大约70%或更多的酚基在邻位被取代,或大约80%或更多的酚基在邻位被取代,剩余的在对位被取代。
这样的一种方法是特别有利的,包括掺入或应用式I的亚磷酸酯混合物,其中每个R基团是仲丁基并且在邻位或对位取代,其中大约60%或更多的酚基在邻位被取代。
本发明的亚磷酸酯液体混合物也是本发明的一个主题。
因此,本发明的主题还有式I的三(单烷基)苯基亚磷酸酯的混合物。
其中每个R相同或不同并且为直链或支链的1至8个碳原子的烷基,其中亚磷酸酯混合物在25℃和1个大气压下为液态。
这样一种混合物是有利的,其中每个R是相同或不同并且为直链或支链的1至6个碳原子的烷基。
这样一种混合物是特别有利的,其中每个R是相同或不同并且为直链或支链的1至4个碳原子的烷基。
聚烯烃的实例是:
1.单烯烃和二烯烃的聚合物,例如聚丙烯、聚异丁烯、聚丁-1-烯、聚-4-甲基戊-1-烯、聚异戊二烯或者聚丁二烯,以及环烯烃的聚合物,例如环戊烯或者降冰片烯,聚乙烯(其可以任选被交联),例如高密度聚乙烯(HDPE)、高密度和高分子量聚乙烯(HDPE-HMW)、高密度和超高分子量聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、线型低密度聚乙烯(LLDPE)、(VLDPE)和(ULDPE)。
聚烯烃,即在前述段落中例举的单烯烃的聚合物,例如聚乙烯和聚丙烯可通过不同的,并且尤其是通过以下方法进行制备:
i)自由基聚合反应(通常在高压和升高的温度下进行)。
ii)使用通常包含周期表的IVb、Vb、VIb或VIII族的一种或多于一种金属的催化剂的催化聚合反应。这些金属通常具有一个或多于一个可被p-或s-配位的配体,一般为氧化物、卤化物、醇盐、酯、醚、胺、烷基、烯基和/或芳基。这些金属配合物可以是游离形式或被固定在基材上,一般固定在活性氯化镁、氯化钛(III)、氧化铝或氧化硅上。这些催化剂可以溶于或者不溶于聚合反应介质中。催化剂本身可用于聚合反应或可以进一步使用活化剂,一般为烷基金属、金属氢化物、烷基金属卤化物、金属烷基氧化物或金属烷基烷,所述金属是周期表的Ia、IIa和/或IIIa族元素。活化剂可适宜地用其它酯、醚、胺或甲硅烷基醚基团改性。这些催化剂体系通常称作Phillips、Standard Oil Indiana、Ziegler(-Natta)、TNZ(DuPont)、金属茂或单位点催化剂(SSC)。
2.在1)中提及的聚合物的混合物,例如聚丙烯与聚异丁烯的混合物、聚丙烯与聚乙烯的混合物(例如PP/HDPE,PP/LDPE)和不同种类的聚乙烯的混合物(例如LDPE/HDPE)。
3.单烯烃和二烯烃相互或与其它乙烯基单体的共聚物,例如乙烯/丙烯共聚物、线性低密度聚乙烯(LLDPE)和其与低密度聚乙烯(LDPE)的混合物、丙烯/丁-1-烯共聚物、丙烯/异丁烯共聚物、乙烯/丁-1-烯共聚物、乙烯/己烯共聚物、乙烯/甲基戊烯共聚物、乙烯/庚烯共聚物、乙烯/辛烯共聚物、丙烯/丁二烯共聚物、异丁烯/异戊二烯共聚物、乙烯/丙烯酸烷基酯共聚物、乙烯/甲基丙烯酸烷基酯共聚物、乙烯/乙酸乙烯酯共聚物和它们与一氧化碳的共聚物或者乙烯/丙烯酸共聚物和它们的盐(离子聚合物)以及乙烯与丙烯和二烯,如己二烯、二环戊二烯或亚乙基-降冰片烯的三元聚合物;和这些共聚物相互之间的混合物和与在以上1)中提及的聚合物的混合物,例如聚丙烯/乙烯-丙烯共聚物、LDPE/乙烯-乙酸乙烯酯共聚物(EVA)、LDPE/乙烯-丙烯酸共聚物(EAA)、LLDPE/EVA、LLDPE/EAA和交替或无规聚亚烷基/一氧化碳共聚物的混合物和其与其它聚合物(例如聚酰胺)的混合物。
4.在1)中提及的聚合物与冲击改性剂的混合物,比如乙烯-丙烯-二烯单体共聚物(EPDM)、乙烯与更高的α-烯烃的共聚物(例如乙烯-辛烯共聚物)、聚丁二烯、聚异戊二烯、苯乙烯-丁二烯共聚物、氢化苯乙烯-丁二烯共聚物、苯乙烯-异戊二烯共聚物、氢化苯乙烯-异戊二烯共聚物。这些混合物在工业中通常被称为TPO’s(热塑性聚烯烃)。
本发明的聚烯烃例如为聚丙烯均聚物和共聚物以及聚乙烯均聚和共聚物。例如,聚丙烯、高密度聚乙烯(HDPE)、线型低密度聚乙烯(LLDPE)和聚丙烯无规和冲击(多相)共聚物。本发明优选的聚烯烃包括聚丙烯均聚物、聚丙烯冲击(多相)共聚物、其混合物,和TPO’s,比如聚丙烯均聚物和冲击共聚物与EPDM或者乙烯-α-烯烃共聚物的混合物。
优选地,聚烯烃为聚乙烯、特别是低密度聚乙烯(LDPE)。
熔体加工技术是已知的而且包括例如挤出、共捏合、拉挤成型、注入模制、共挤出、纤维挤出、纤维纺纱、薄膜挤出(流延、吹制、吹塑)、旋转成型等。
可以以0.01%至5%重量,基于聚烯烃的重量,以0.025%至1%重量,以0.05%至0.5%重量,以0.01%至1%,0.01%至0.5%,0.025%至5%,或0.05%至5%重量,基于所要稳定的聚烯烃的重量,的量使用本发明的三(单烷基)苯基亚磷酸酯。例如,基于聚烯烃的重量,本发明的三(单烷基)苯基亚磷酸酯以小于3%重量的水平存在,或基于聚烯烃的重量,以0.01%至2.5%重量,或以0.01%至2%重量的水平存在。
这样的一种方法是有利的,其中基于聚烯烃的重量,以小于大约3%重量的水平掺入或应用亚磷酸酯或亚磷酸酯混合物。
通过已知的方法,例如在成型之前或之后,或也可通过将溶解或分散的稳定剂或稳定剂混合物应用于聚烯烃,随后蒸发或不蒸发溶剂将本发明的三(单烷基)苯基亚磷酸酯和任选的另外添加剂掺入聚烯烃中。还可以母料形式将稳定剂或稳定剂混合物加入到将要稳定的聚烯烃中,母料含有本发明的亚磷酸酯和例如2.5至60%重量浓度的任选添加剂。
还可以在聚合前或聚合期间或交联前加入三(单烷基)苯基亚磷酸酯和任选的另外添加剂。
可以纯形式或包封于蜡、油或聚合物的形式将本发明的三(单烷基)苯基亚磷酸酯和任选的另外添加剂掺入要稳定的聚烯烃中。
还可以将本发明的三(单烷基)苯基亚磷酸酯和任选的另外添加剂喷于将要稳定的聚烯烃上。这能够稀释其他添加剂(例如其他进一步讨论的常规添加剂)或它们的熔融物以使其也能与这些添加剂一起喷于将要稳定的聚烯烃上。在聚合催化剂失活期间通过喷雾加入特别有利,可通过例如用于失活的蒸汽进行喷雾。
在球形聚合的聚烯烃的情况下,例如将本发明稳定剂任选地与其他添加剂一起通过喷雾进行应用是特别有利的。
根据本发明的聚烯烃组合物可用于制备聚烯烃制品。所述聚烯烃制品是例如纺织纤维、无纺纤维、薄膜、薄片或模制品。
另外的稳定剂包括例如位阻酚抗氧剂、羟胺、苯并呋喃酮、其他有机磷稳定剂、空间位阻胺光稳定剂和羟苯基苯并三唑、三-芳基-s-三嗪或羟苯基苯并三唑紫外光稳定剂。
位阻酚抗氧剂包括例如三(3,5-二-叔丁基-4-羟苯甲基)异氰脲酸酯、1,3,5-三-(3,5-二-叔丁基-4-羟苯甲基)-2,4,6-三甲基苯、3,5-二-叔丁基-4-羟苯甲基膦酸单乙基酯的钙盐、季戊四醇四[3-(3,5-二-叔丁基-4-羟苯基)丙酸酯]或辛基(3,5-二-叔丁基-4-羟苯基)丙酸酯。
位阻胺光稳定剂包括例如1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩合物,
N,N′-双(2,2,6,6-四甲基-4-哌啶基(piperidyl))-己二胺与4-叔-辛基氨基-2,6-二氯-1,3,5-三嗪的线性或环状缩合产物,
2-氯-4,6-二-(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪与1,2-双-(3-氨基丙基氨基)乙烷的缩合物,
其中R′是
低聚物化合物,为4,4′-环六亚甲基双(氨基-2,2,6,6-四甲基哌啶)与2,4-二氯-6-[(2,2,6,6-四甲基哌啶-4-基)叔丁基氨基]-s-三嗪的缩合产物,用2-氯-4,6-双(二丁基氨基)-s-三嗪封端,
由1,2-双(3-氨基丙基氨基)乙烷与氰尿酰氯反应获得的产物与(2,2,6,6-四甲基哌啶-4-基)丁基胺反应获得的产物,
其中R′=R或H
并且其中
N,N′-双-(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺与4-吗啉-2,6-二氯-1,3,5-三嗪的线性或环状缩合物,
N,N′-双(1,2,2,6,6-五甲基-4-哌啶基)六亚甲基二胺与4-吗啉-2,6-二氯-1,3,5-三嗪的线性或环状缩合物,
7,7,9,9-四甲基-2-环十一基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷与表氯醇的反应产物,
马来酸酐-C18-C22-α-烯烃-共聚物与2,2,6,6-四甲基-4-氨基哌啶的反应产物,
2,4-双[(1-环己基氧基-2,2,6,6-哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N′-双(3-氨基丙基)乙二胺)的反应产物,
低聚物化合物,为4,4′-环六亚甲基双(氨基-1-丙氧基-2,2,6,6-四甲基哌啶)与2,4-二氯-6-[(1-丙氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-s-三嗪的缩合产物,用2-氯-4,6-双(二丁基氨基)-s-三嗪封端,
低聚物化合物,为4,4′-六亚甲基双(氨基-1,2,2,6,6-五甲基哌啶)与2,4-二氯-6-[(1,2,2,6,6-五甲基哌啶-4-基)叔丁基氨基]-s-三嗪的缩合产物,用2-氯-4,6-双(二丁基氨基)-s-三嗪封端,
其中n是使总分子量高于大约1000g/摩尔的整数。
羟胺稳定剂是例如N,N-二苄基羟胺、N,N-二乙基羟胺、N,N-二辛基羟胺、N,N-二月桂基羟胺、N,N-二-十二烷基羟胺、N,N-二-十四烷基羟胺、N,N-二-十六烷基羟胺、N,N-二-十八烷基羟胺、N-十六烷基-N-十四烷基羟胺、N-十六烷基-N-十七烷基羟胺、N-十六烷基-N-十八烷基羟胺、N-十七烷基-N-十八烷基羟胺、N-甲基-N-十八烷基羟胺或N,N-二(氢化牛脂)羟胺。
氧化胺稳定剂是例如Genox EP(RTM),二(C16-C18)烷基甲基氧化胺,CAS#204933-93-7。
苯并呋喃酮稳定剂是例如3-[4-(2-乙酰氧基乙氧基)苯基]-5,7-二叔丁基苯并呋喃-2-酮、5,7-二叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮、3,3’-双[5,7-二叔丁基-3-(4-[2-羟基乙氧基]苯基)苯并呋喃-2-酮]、5,7-二叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮、3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮、3-(3,5-二甲基-4-新戊酰氧基苯基)-5,7-二叔丁基苯并呋喃-2-酮、3-(3,4-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮或3-(2,3-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮。
另外的有机磷稳定剂是例如以前公开的那些。另外的有机磷稳定剂还例如是在U.S.专利6,541,549中公开的那些。
这些任选的稳定剂以与本发明三(单烷基)苯基亚磷酸酯相同的水平使用。
除三(单烷基)苯基亚磷酸酯和以上任选的添加剂外,还可以使用以下另外的添加剂。例如基于聚烯烃的重量,以0.01%至5%重量的使用水平使用这些另外的添加剂。
1.抗氧剂
1.1.烷基化单酚,例如2,6-二-叔丁基-4-甲基苯酚、2-叔丁基-4,6-二甲基苯酚、2,6-二叔丁基-4-乙基苯酚、2,6-二-叔丁基-4-正丁基苯酚、2,6-二-叔丁基-4-异丁基苯酚、2,6-二环戊基-4-甲基苯酚、2-(α-甲基环己基)-4,6-二甲基-苯酚、2,6-二-十八烷基-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二-叔丁基-4-甲氧基甲基苯酚、侧链是直链或支链的壬基苯酚例如2,6-二-壬基-4-甲基苯酚、2,4-二甲基-6-(1-甲基十一烷-1-基)苯酚、2,4-二甲基-6-(1-甲基十七烷-1-基)苯酚、2,4-二甲基-6-(1-甲基十三烷-1-基)苯酚及其混合物。
1.2.烷硫基甲基苯酚,例如2,4-二辛硫基甲基-6-叔丁基苯酚、2,4-二辛硫基甲基-6-甲基苯酚、2,4-二辛硫基甲基-6-乙基苯酚、2,6-二-十二烷硫基甲基-4-壬基苯酚。
1.3.氢醌和烷基化氢醌,例如2,6-二-叔丁基-4-甲氧基苯酚、2,5-二-叔丁基氢醌、2,5-二-叔戊基氢醌、2,6-二苯基-4-十八烷氧基苯酚、2,6-二-叔丁基氢醌、2,5-二-叔丁基-4-羟基茴香醚、3,5-二-叔丁基-4-羟基茴香醚、3,5-二-叔丁基-4-羟基苯基硬脂酸酯、双(3,5-二-叔丁基-4-羟基苯基)己二酸酯。
1.4.生育酚,例如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚及其混合物(维生素E)。
1.5.羟基化的硫代二苯基醚,例如2,2’-硫代双(6-叔丁基-4-甲基苯酚)、2,2’-硫代双(4-辛基苯酚)、4,4’-硫代双(6-叔丁基-3-甲基苯酚)、4,4’-硫代双(6-叔丁基-2-甲基苯酚)、4,4’-硫代双(3,6-二-仲戊基苯酚)、4,4’-双(2,6-二甲基-4-羟基苯基)-二硫化物。
1.6.亚烷基双酚,例如2,2’-亚甲基双(6-叔丁基-4-甲基苯酚)、2,2’-亚甲基双(6-叔丁基-4-乙基苯酚)、2,2’-亚甲基双[4-甲基-6-(α-甲基环己基)-苯酚]、2,2’-亚甲基双(4-甲基-6-环己基苯酚)、2,2’-亚甲基双(6-壬基-4-甲基苯酚)、2,2’-亚甲基双(4,6-二-叔丁基苯酚)、2,2’-亚乙基双(4,6-二-叔丁基苯酚)、2,2’-亚乙基双(6-叔丁基-4-异丁基苯酚)、2,2’-亚甲基双[6-(α-甲基苄基)-4-壬基苯酚]、2,2’-亚甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4’-亚甲基双(2,6-二-叔丁基苯酚)、4,4’-亚甲基双(6-叔丁基-2-甲基苯酚)、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)丁烷、2,6-双(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、乙二醇双[3,3-双(3-叔丁基-4-羟基苯基)丁酸酯]、双(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯、双[2-(3’-叔丁基-2-羟基-5-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二酸酯、1,1-双(3,5-二甲基-2-羟基苯基)丁烷、2,2-双(3,5-二-叔丁基-4-羟基苯基)丙烷、2,2-双(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基巯基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.7.苄基化合物,例如3,5,3′,5′-四-叔丁基-4,4′-二羟基二苄基醚、十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯、十三烷基-4-羟基-3,5-二-叔丁基苄基巯基乙酸酯、三(3,5-二-叔丁基-4-羟基苄基)胺、1,3,5-三-(3,5-二-叔丁基-4-羟基苄基)-2,4,6-三甲基苯、二(3,5-二-叔丁基-4-羟基苄基)硫化物、3,5-二-叔丁基-4-羟基苄基-巯基乙酸异辛基酯、双-(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫醇对苯二羧酸酯、1,3,5-三-(3,5-二-叔丁基-4-羟基苄基)异氰尿酸酯、1,3,5-三-(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰尿酸酯、3,5-二-叔丁基-4-羟基苄基磷酸二-十八烷基酯和3,5-二-叔丁基-4-羟基苄基-磷酸单乙基酯,钙盐。
1.8.羟苄基化的丙二酸酯,例如二-十八烷基-2,2-双(3,5-二-叔丁基-2-羟基苄基)丙二酸酯、二-十八烷基-2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸酯、二-十二烷巯乙基-2,2-双-(3,5-二-叔丁基-4-羟基苄基)丙二酸酯、双[4-(1,1,3,3-四甲基丁基)苯基]-2,2-双(3,5-二-叔丁基-4-羟基苄基)丙二酸酯。
1.9.芳香羟基苄基化合物,例如1,3,5-三(3,5-二-叔丁基-4-羟基-苄基)-2,4,6-三甲基苯、1,4-双(3,5-二-叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二-叔丁基-4-羟基苄基)苯酚。
1.10.三嗪化合物,例如2,4-双(辛基巯基)-6-(3,5-二-叔丁基-4-羟基-苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二-叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三-(3,5-二-叔丁基-4-羟基苯氧基)-1,2,3-三嗪、1,3,5-三(3,5-二-叔丁基-4-羟基苄基)异氰尿酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰尿酸酯、2,4,6-三-(3,5-二-叔丁基-4-羟基苯基乙基)-1,3,5-三嗪、1,3,5-三(3,5-二叔丁基-4-羟基苯基丙酰基)-六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟基苄基)异氰尿酸酯。
1.11.苄基膦酸酯,例如二甲基-2,5-二-叔丁基-4-羟基苄基膦酸酯、二乙基-3,5-二-叔丁基-4-羟基苄基膦酸酯、二-十八烷基-3,5-二-叔丁基-4-羟基苄基膦酸酯、二-十八烷基-5-叔丁基-4-羟基-3-甲基苄基膦酸酯、3,5-二-叔丁基-4-羟基苄基膦酸单乙酯的钙盐。
1.12.酰基氨基酚,例如4-羟基-月桂酸酰替苯胺、4-羟基-硬脂酸酰替苯胺、2,4-双-辛基巯基-6-(3,5-叔丁基-4-羟基苯胺基)-s-三嗪和辛基-N-(3,5-二-叔丁基-4-羟基苯基)-氨基甲酸酯。
1.13.β-(3,5-二-叔丁基-4-羟基苯基)丙酸与单-或多元醇的酯,所述醇如甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N’-双(羟乙基)草酰胺、3-硫杂十一醇、3-硫杂十五醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与单-或多元醇的酯,所述醇如甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N’-双(羟乙基)草酰胺、3-硫杂十一醇、3-硫杂十五醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷。
1.15.β-(3,5-二环己基-4-羟基苯基)丙酸与单-或多元醇的酯,所述的醇如甲醇、乙醇、正辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十一醇、3-硫代十五醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷。
1.16.3,5-二叔丁基-4-羟基苯基乙酸与单-或多元醇的酯,所述醇如甲醇、乙醇、正辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十一醇、3-硫代十五醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷。
1.17.β-(3,5-二-叔丁基-4-羟基苯基)丙酸的酰胺,例如N,N’-双(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二酰胺、N,N’-双(3,5-二叔丁基-4-羟基苯基丙酰基)三亚甲基二胺、N,N’-双(3,5-二叔丁基-4-羟基苯基丙酰基)酰肼、N,N’-双[2-(3-[3,5-二叔丁基-4-羟基苯基]丙酰氧基)乙基]草酰胺(NaugardXL-1,Uniroyal提供)。
1.18.抗坏血酸(维生素C)
1.19.胺类抗氧剂,例如N,N’-二-异丙基-对苯二胺、N,N’-二仲丁基-对苯二胺、N,N’-双(1,4-二甲基戊基)-对苯二胺、N,N’-双(1-乙基-3-甲基戊基)-对苯二胺、N,N’-双(1-甲基庚基)-对苯二胺、N,N’-二环己基-对苯二胺、N,N’-二苯基-对苯二胺、N,N’-双(2-萘基)-对苯二胺、N-异丙基-N’-苯基-对苯二胺、N-(1,3-二甲基丁基)-N’-苯基-对苯二胺、N-(1-甲基庚基)-N’-苯基-对苯二胺、N-环己基-N’-苯基-对苯二胺、4-(对甲苯氨磺酰基)二苯胺、N,N’-二甲基-N,N’-二仲丁基-对苯二胺、二苯胺、N-烯丙基二苯胺、4-异丙氧基二苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺、辛基化的二苯胺,例如p,p’-二叔辛基二苯胺、4-正丁基氨基苯酚、4-丁酰基氨基苯酚、4-壬酰基氨基苯酚、4-十二酰基氨基苯酚、4-十八酰基氨基苯酚、双(4-甲氧基苯基)胺、2,6-二-叔丁基-4-二甲基氨基-甲酚、2,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基甲烷、N,N,N’,N’-四甲基-4,4’-二氨基二苯基甲烷、1,2-双[(2-甲基苯基)氨基]乙烷、1,2-双(苯基氨基)丙烷、(邻甲苯基)双胍、双[4-(1’,3’-二甲基丁基)苯基]胺、叔辛基化的N-苯基-1-萘胺、单-和二烷基化叔丁基/叔辛基二苯基胺的混合物,单-和二烷基化壬基二苯基胺的混合物,单-和二烷基化十二烷基二苯基胺的混合物,单-和二烷基化异丙基/异己基二苯基胺的混合物,单-和二烷基化叔丁基二苯基胺的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、酚噻嗪、单-和二烷基化叔丁基/叔辛基酚噻嗪的混合物,单-和二烷基化叔辛基酚噻嗪的混合物,N-烯丙基酚噻嗪、N,N,N’,N’-四苯基-1,4-二氨基丁-2-烯、N,N-双(2,2,6,6-四甲基哌啶-4-基-六亚甲基二胺、双(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、2,2,6,6-四甲基哌啶-4-酮、2,2,6,6-四甲基哌啶-4-醇。
2.UV吸收剂和光稳定剂
2.1.2-(2-羟苯基)-2H-苯并三唑,例如已知的市售羟苯基-2H-苯并三唑,公开于美国专利No.3,004,896;3,055,896;3,072,585;3,074,910;3,189,615;3,218,332;3,230,194;4,127,586;4,226,763;4,275,004;4,278,589;4,315,848;4,347,180;4,383,863;4,675,352;4,681,905,4,853,471;5,268,450;5,278,314;5,280,124;5,319,091;5,410,071;5,436,349;5,516,914;5,554,760;5,563,242;5,574,166;5,607,987,5,977,219和6,166,218中的苯并三唑,比如2-(2-羟基-5-甲基苯基)-2H-苯并三唑、2-(3,5-二-叔丁基-2-羟基苯基)-2H-苯并三唑、2-(2-羟基-5-叔丁基苯基)-2H-苯并三唑、2-(2-羟基-5-叔辛基苯基)-2H-苯并三唑、5-氯-2-(3,5-二-叔丁基-2-羟基苯基)-2H-苯并三唑、5-氯-2-(3-叔丁基-2-羟基-5-甲基苯基)-2H-苯并三唑、2-(3-仲丁基-5-叔丁基-2-羟基苯基)-2H-苯并三唑、2-(2-羟基-4-辛基苯基)-2H-苯并三唑、2-(3,5-二-叔戊基-2-羟基苯基)-2H-苯并三唑、2-(3,5-二-α-枯基-2-羟基苯基)-2H-苯并三唑、2-(3-叔丁基-2-羟基-5-(2-(w-羟基-八-(亚乙基氧基)羰基-乙基)-苯基)-2H-苯并三唑、2-(3-十二烷基-2-羟基-5-甲基苯基)-2H-苯并三唑、2-(3-叔丁基-2-羟基-5-(2-辛氧基羰基)乙基苯基)-2H-苯并三唑、十二烷基化的2-(2-羟基-5-甲基苯基)-2H-苯并三唑、2-(3-叔丁基-2-羟基-5-(2-辛氧基羰基乙基)苯基)-5-氯-2H-苯并三唑、2-(3-叔丁基-5-(2-(2-乙基己氧基)-羰基乙基)-2-羟基苯基)-5-氯-2H-苯并三唑、2-(3-叔丁基-2-羟基-5-(2-甲氧基羰基乙基)苯基)-5-氯-2H-苯并三唑、2-(3-叔丁基-2-羟基-5-(2-甲氧基羰基乙基)苯基)-2H-苯并三唑、2-(3-叔丁基-5-(2-(2-乙基己氧基)羰基乙基)-2-羟基苯基)-2H-苯并三唑、2-(3-叔丁基-2-羟基-5-(2-异辛氧基羰基乙基)苯基-2H-苯并三唑、2,2’-亚甲基-二(4-叔辛基-(6-2H-苯并三唑-2-基)苯酚)、2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑、2-(2-羟基-3-叔辛基-5-α-枯基苯基)-2H-苯并三唑、5-氟-2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑、5-氯-2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑、5-氯-2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑、2-(3-叔丁基-2-羟基-5-(2-异辛氧基羰基乙基)苯基)-5-氯-2H-苯并三唑、5-三氟甲基-2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑、5-三氟甲基-2-(2-羟基-5-叔辛基苯基)-2H-苯并三唑、5-三氟甲基-2-(2-羟基-3,5-二-叔辛基苯基)-2H-苯并三唑、3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢肉桂酸甲基酯、5-丁磺酰基-2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑、5-三氟甲基-2-(2-羟基-3-α-枯基-5-叔丁基苯基)-2H-苯并三唑、5-三氟甲基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑、5-三氟甲基-2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑、5-丁磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑和5-苯磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑。
2.2.2-羟基二苯甲酮,例如4-羟基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2’,4’-三羟基和2’-羟基-4,4’-二甲氧基衍生物。
2.3.取代的和未取代的苯甲酸酯,例如4-叔丁基苯基水杨酸酯、水杨酸苯基酯、水杨酸辛基苯基酯、二苯甲酰基间苯二酚、双(4-叔丁苯甲酰基)间苯二酚、苯甲酰基间苯二酚、2,4-二叔丁基苯基3,5-二叔丁基-4-羟基苯甲酸酯、3,5-二叔丁基-4-羟基苯甲酸十六烷基酯、3,5-二叔丁基-4-羟基苯甲酸十八烷基酯、3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯基酯。
2.4.丙烯酸酯和丙二酸酯,例如,α-氰基-α,α-二苯基丙烯酸乙基酯或异辛基酯、α-甲酯基-肉桂酸甲基酯、α-氰基-α-甲基-对甲氧基-肉桂酸甲基酯或丁基酯、α-甲酯基-对甲氧基-肉桂酸甲基酯、N-(β-甲酯基-β-氰基乙烯基)-2-甲基-二氢吲哚、SanduvorPR25,对甲氧基亚苄基丙二酸二甲基酯(CAS#7443-25-6)、和SanduvorPR31,对甲氧基亚苄基丙二酸二(1,2,2,6,6-五甲基哌啶-4-基)酯(CAS#147783-69-5)。
2.5.镍化合物,例如2,2’-硫代二[4-(1,1,3,3-四甲基丁基)苯酚]的镍配合物,例如1∶1或1∶2的配合物,有或无另外配体,例如正丁胺、三乙醇胺或N-环己基二乙醇胺;二丁基二硫代氨基甲酸镍、4-羟基-3,5-二叔丁基苄基膦酸的单烷基酯,如甲酯或乙酯的镍盐;酮肟如2-羟基-4-甲基苯基十一烷基酮肟的镍配合物,有或没有其它另外配体的1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物。
2.6.空间位阻胺稳定剂,例如4-羟基-2,2,6,6-四甲基哌啶、1-烯丙基-4-羟基-2,2,6,6-四甲基哌啶、1-苄基-4-羟基-2,2,6,6-四甲基哌啶、双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯、双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、双(1-辛基氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(1,2,2,6,6-五甲基-4-哌啶基)正丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯、1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物、N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的线性或环状缩合物、三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯、四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷-四羧酸酯、1,1’-(1,2-乙烷二基)-双(3,3,5,5-四甲基哌嗪酮)、4-苯甲酰基-2,2,6,6-四甲基哌啶、4-硬脂基氧基-2,2,6,6-四甲基哌啶、双(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二-叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮、双(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、双(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯、N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉基-2,6-二氯-1,3,5-三嗪的线性或环状缩合物、2-氯-4,6-双(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合物、2-氯-4,6-双(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合物、8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮、3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮、4-十六烷基氧基-和4-十八烷基氧基-2,2,6,6-四甲基哌啶的混合物、N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合产物、1,2-双(3-氨基丙基氨基)己烷和2,4,6-三氯-1,3,5-三嗪的缩合产物以及4-丁基氨基-2,2,6,6-四甲基哌啶(CASReg.No.[136504-96-6])、N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧螺[4,5]癸烷、7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧螺[4,5]癸烷和表氯醇的反应产物、1,1-双(1,2,2,6,6-五甲基-4-哌啶基氧基羰基)-2-(4-甲氧基苯基)乙烯、N,N’-双-甲酰基-N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺、4-甲氧基-亚甲基-丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯、聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷、马来酸酐-α-烯烃共聚物与2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物。
空间位阻胺还可以是在U.S.专利5,980,783中描述的化合物,即组分I-a)、I-b)、I-c)、I-d)、I-e)、I-f)、I-g)、I-h)、I-i)、I-j)、I-k)或I-1)的化合物,尤其是在所述U.S.专利5,980,783的64-72栏中列出的光稳定剂1-a-1、1-a-2、1-b-1、1-c-1、1-c-2、1-d-1、1-d-2、1-d-3、1-e-1、1-f-1、1-g-1、1-g-2或1-k-1。
空间位阻胺还可以是在U.S.专利6,046,304和6,297,299中描述的化合物之一,例如在权利要求10或38或实施例1-12或D-1至D-5中描述的化合物。
2.7.在N-原子被羟基-取代烷氧基取代的空间位阻胺,例如化合物,如1-(2-羟基-2-甲基丙氧基)-4-十八碳酰氧基-2,2,6,6-四甲基哌啶、1-(2-羟基-2-甲基丙氧基)-4-十六碳酰氧基-2,2,6,6-四甲基哌啶、1-氧基-4-羟基-2,2,6,6-四甲基哌啶与叔戊醇的碳游离基的反应产物、1-(2-羟基-2-甲基丙氧基)-4-羟基-2,2,6,6-四甲基哌啶、1-(2-羟基-2-甲基丙氧基)-4-氧代-2,2,6,6-四甲基哌啶、双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)癸二酸酯、双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6四甲基哌啶-4-基)己二酸酯、双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯、双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)戊二酸酯和2,4-双{N-[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]-N-丁基氨基}-6-(2-羟基乙基氨基)-s-三嗪。
2.8.草酰胺,例如4,4’-二辛基氧基草酰替苯胺、2,2’-二乙氧基草酰替苯胺、2,2’-二辛氧基-5,5’-二叔丁基草酰替苯胺、2,2’-双十二烷基氧基-5,5’-二叔丁基草酰替苯胺、2-乙氧基-2’-乙基草酰替苯胺、N,N’-双(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙草酰替苯胺和其与2-乙氧基-2’-乙基-5,4’-叔丁草酰替苯胺的混合物,邻-和对-甲氧基-二取代的草酰替苯胺的混合物和邻-和对-乙氧基-二取代的草酰替苯胺的混合物。
2.9.三-芳基-邻羟基苯基-s-三嗪,例如已知的商业三-芳基-邻羟基苯基-s-三嗪和例如公开于美国专利No.3,843,371;4,619,956;4,740,542;5,096,489;5,106,891;5,298,067;5,300,414;5,354,794;5,461,151;5,476,937;5,489,503;5,543,518;5,556,973;5,597,854;5,681,955;5,726,309;5,736,597;5,942,626;5,959,008;5,998,116;6,013,704;6,060,543;6,187,919;6,242,598和6,468,958的三嗪,例如4,6-二-(2,4-二甲基苯基)-2-(2-羟基-4-辛基氧基苯基)-s-三嗪,Cyasorb1164,CytecCorp,4,6-二-(2,4-二甲基苯基)-2-(2,4-二羟基苯基)-s-三嗪,2,4-二(2,4-二羟基苯基)-6-(4-氯苯基)-s-三嗪,2,4-二[2-羟基-4-(2-羟基乙氧基)苯基]-6-(4-氯苯基)-s-三嗪,2,4-二[2-羟基-4-(2-羟基-4-(2-羟基乙氧基)苯基)-6-(2,4-二甲基苯基)-s-三嗪,2,4-二[2-羟基-4-(2-羟基乙氧基)苯基]-6-(4-溴苯基)-s-三嗪,2,4-二[2-羟基-4-(2-乙酰氧基乙氧基)苯基]-6-(4-氯苯基)-s-三嗪,2,4-二(2,4-二羟基苯基)-6-(2,4-二甲基苯基)-s-三嗪,2,4-二(4-联苯基)-6-(2-羟基-4-辛基氧基羰基乙叉基氧基苯基)-s-三嗪,2-苯基-4-[2-羟基-4-(3-仲-丁基氧基-2-羟基丙基氧基)苯基]-6-[2-羟基-4-(3-仲-戊基氧基-2-羟基丙基氧基)-苯基]-s-三嗪,2,4-二(2,4-二甲基苯基)-6-[2-羟基-4-(3-苄基氧基-2-羟基-丙基氧基)苯基]-s-三嗪,2,4-二(2-羟基-4-正-丁基氧基苯基)-6-(2,4-二-正-丁基氧基-苯基)-s-三嗪,2,4-二(2,4-二甲基苯基)-6-[2-羟基-4-(3-壬基氧基*-2-羟基-丙基氧基)-5-α-枯基苯基]-s-三嗪(*表示辛基氧基,壬基氧基和癸基氧基基团的混合物),亚甲基二-{2,4-二(2,4-二甲基苯基)-6-[2-羟基-4-(3-丁基氧基-2-羟基丙氧基)苯基]-s-三嗪},在3∶5′,5∶5′和3∶3′位按照5∶4∶1比率桥接的亚甲基桥接二聚体混合物,2,4,6-三(2-羟基-4-异辛基氧基羰基异亚丙基氧基苯基)-s-三嗪,2,4-二(2,4-二甲基苯基)-6-(2-羟基-4-己基氧基-5-α-枯基-苯基)-s-三嗪,2-(2,4,6-三甲基苯基)-4,6-二[2-羟基-4-(3-丁基氧基-2-羟基-丙基氧基)苯基]-s-三嗪,2,4,6-三[2-羟基-4-(3-仲-丁基氧基-2-羟基丙基氧基)-苯基]-s-三嗪,4,6-二-(2,4-二甲基苯基)-2-(2-羟基-4-(3-十二烷基氧基-2-羟基丙氧基)-苯基)-s-三嗪和4,6-二-(2,4-二甲基苯基)-2-(2-羟基-4-(3-十三烷基氧基-2-羟基丙氧基)-苯基)-s-三嗪的混合物,4,6-二-(2,4-二甲基苯基)-2-(2-羟基-4-(3-(2-乙基己基氧基)-2-羟基丙氧基)-苯基)-s-三嗪和4,6-二苯基-2-(4-己基氧基-2-羟基苯基)-s-三嗪。
3.金属减活化剂,例如N,N′-二苯基草酰胺,N-水杨基-N′-水杨酰基肼,N,N′-二(水杨酰基)肼,N,N′-二(3,5-二-叔丁基-4-羟基苯基丙酰基)肼,3-水杨酰基氨基-1,2,4-三唑,二(亚苄基)草酰基二酰肼,草酰替苯胺,间苯二甲酰二酰肼,癸二酰基二苯基酰肼,N,N′-二乙酰基己二酰基二酰肼,N,N′-二(水杨酰基)草酰基二酰肼,N,N′-二(水杨酰基)硫代丙酰基二酰肼。
4.亚磷酸酯和亚膦酸酯,例如亚磷酸三苯酯,亚磷酸二苯基烷基酯,亚磷酸苯基二烷基酯,亚磷酸三(壬基苯基)酯,亚磷酸三月桂基酯,亚磷酸三-十八烷基酯,二硬脂基季戊四醇二亚磷酸酯,亚磷酸三(2,4-二-叔丁基苯基)酯,二异癸基季戊四醇二亚磷酸酯,二(2,4-二-叔丁基苯基)季戊四醇二亚磷酸酯,二(2,6-二-叔丁基-4-甲基苯基)-季戊四醇二亚磷酸酯,二异癸基氧基季戊四醇二亚磷酸酯,二(2,4-二-叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯,二(2,4,6-三(叔丁基-苯基)季戊四醇二亚磷酸酯,三硬脂基山梨醇三亚磷酸酯,二亚膦酸四(2,4-二-叔丁基-苯基)4,4′-亚联苯基酯,6-异辛基氧基-2,4,8,10-四-叔丁基-二苯并-[d,f]-1,3,2-二氧杂磷杂庚环,6-氟-2,4,8,10-四-叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂磷杂辛环,亚磷酸二(2,4-二-叔丁基-6-甲基苯基)甲基酯,亚磷酸二(2,4-二-叔丁基-6-甲基苯基)乙基酯,2,2′,2″-次氮基[三乙基三(3,3′,5,5′-四-叔丁基-1,1′-联苯-2,2′-二基)亚磷酸酯],亚磷酸2-乙基己基(3,3′,5,5′-四-叔丁基-1,1′-联苯-2,2′-二基)酯。
尤其优选的是以下亚磷酸酯:
亚磷酸三(2,4-二-叔丁基苯基)酯、亚磷酸三(壬基苯基)酯,
5.羟基胺,例如N,N-二苄基羟基胺,N,N-二乙基羟基胺,N,N-二辛基羟基胺,N,N-二月桂基羟基胺,N,N-双十四烷基羟基胺,N,N-双十六烷基羟基胺,N,N-双十八烷基羟基胺,N-十六烷基-N-十八烷基羟基胺,N-十七烷基-N-十八烷基羟基胺,N-甲基-N-十八烷基羟基胺和衍生自氢化牛脂胺的N,N-二烷基羟基胺。
6.硝酮,例如,N-苄基-α-苯基-硝酮,N-乙基-α-甲基-硝酮,N-辛基-α-庚基-硝酮,N-月桂基-α-十一烷基-硝酮,N-十四烷基-α-十三烷基-硝酮,N-十六烷基-α-十五烷基-硝酮,N-十八烷基-α-十七烷基-硝酮,N-十六烷基-α-十七烷基-硝酮,N-十八基-α-十五烷基-硝酮,N-十七烷基-α-十七烷基-硝酮,N-十八烷基-α-十六烷基-硝酮,衍生自氢化牛脂胺的N,N-二烷基羟基胺所衍生的硝酮。
7.氧化胺,例如公开于U.S.专利No.5,844,029和5,880,191的氧化胺衍生物,二癸基甲基氧化胺,十三烷基氧化胺,三-十二烷基氧化胺和三-十六烷基氧化胺。
8.苯并呋喃酮和吲哚啉酮(indolinone),例如公开于美国专利No.4,325,863、4,338,244、5,175,312、5,216,052、5,252,643、5,369,159、5,356,966、5,367,008、5,428,177或者5,428,162中的那些,或者3-[4-(2-乙酰氧基乙氧基)-苯基]-5,7-二叔丁基苯并呋喃-2-酮、5,7-二叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]-苯并呋喃-2-酮、3,3’-双[5,7-二-叔丁基-3-(4-[2-羟基乙氧基]-苯基)-5,7-苯并呋喃-2-酮]、5,7-二叔丁基-3-(4-乙氧基苯基)-苯并呋喃-2-酮、3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮、3-(3,5-二甲基-4-新戊酰基氧基苯基)-5,7-二-叔丁基苯并呋喃-2-酮、3-(3,4-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮、IrganoxHP-136,CIBA Specialty Chemicals Corp.和3-(2,3-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮。
9.硫代增效剂,例如硫代二丙酸双十二烷基酯或硫代二丙酸二硬脂酰酯。
10.过氧化物清除剂,例如β-硫代二丙酸的酯如月桂基、硬脂基、十四烷基或十三烷基酯,巯基苯并咪唑、或2-巯基苯并咪唑锌盐、二丁基二硫代氨基甲酸锌、二-十八烷二硫化物、季戊四醇四(β-十二烷基巯基)丙酸酯。
11.碱性共稳定剂,例如蜜胺、聚乙烯吡咯烷酮、二氰基二酰胺、三烯丙基氰尿酸酯、脲衍生物、肼衍生物、胺、聚酰胺、聚氨酯、高级脂肪酸的碱金属盐和碱土金属盐,例如硬脂酸钙、硬脂酸锌、二十二烷酸镁、硬脂酸镁、蓖麻酸钠和棕榈酸钾、焦儿茶酸锑或焦儿茶酸锌。
12.成核剂,例如无机物,如滑石粉、金属氧化物如二氧化钛或氧化镁;磷酸盐、碳酸盐或硫酸盐,优选碱土金属的盐;有机化合物,如单-或多羧酸和其盐,如4-叔丁基苯甲酸、己二酸、二苯基乙酸、琥珀酸钠或苯甲酸钠;聚合化合物如离子共聚物(离聚物)。
13.填料和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、玻璃球管、石棉、滑石、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、炭黑、石墨、木屑和其它天然产物的木屑或纤维、合成纤维。
14.分散剂,如聚氧化乙烯蜡或矿物油。
15.其它添加剂,例如增塑剂、润滑剂、乳化剂、颜料、染料、荧光增白剂、流变添加剂、催化剂、流动控制剂、滑动助剂、交联剂、交联促进剂、卤素清除剂、烟雾抑制剂、阻燃剂、抗静电剂、澄清剂如取代的和未取代的二亚苄基山梨醇、苯并嗪酮UV吸收剂如2,2′-对亚苯基-二(3,1-苯并嗪-4-酮)、Cyasorb3638(CAS#18600-59-4)和发泡剂。
基于所要稳定的聚烯烃的总重量,可将这些填料和增强剂(所列第13项),例如滑石、碳酸钙、云母或高岭土以大约0.01%至大约40%重量的浓度加入聚烯烃。
基于所要稳定的聚烯烃的总重量,可将这些填料和增强剂(所列第13项),例如金属氢氧化物,尤其是氢氧化铝或氢氧化镁以大约0.01%至大约60%重量的浓度加入聚烯烃。
可审慎地基于所要稳定的聚烯烃的总重量,将作为填充剂的炭黑以大约0.01%至大约5%重量的浓度加入聚烯烃。
可审慎地基于所要稳定的聚烯烃的总重量,将作为增强剂的玻璃纤维以大约0.01%至大约20%重量的浓度加入聚烯烃。
以下实施例更详细地说明了本发明。除非另有说明,分数和百分数以重量计。
实施例1:使用作为HCl清除剂的三乙胺(TEA)制备三(仲-丁基苯基)亚磷酸酯混合物
于25℃2小时内向保持在氮气氛下的45.0g(0.30摩尔)邻-和对-仲丁基苯酚(70%为邻-仲丁基苯酚,30%为对-仲丁基苯酚;SchenectadyInternational)的混合物和35.7g(0.35摩尔)TEA的300ml二甲苯(异构体混合物)溶液中加入14.5g(0.10摩尔)三氯化磷。将反应物质加热至65℃以确保反应完成,冷却,过滤并减压气提二甲苯。通过HPLC分析剩余的浅黄色液体(95%产率)为仲-丁基苯基亚磷酸酯与仅仅痕量存在的起始酚的混合物;这通过P31-NMR得到确认。
实施例2:制备三(仲-丁基苯基)亚磷酸酯混合物
在40-45℃90分钟内将三氯化磷(98.1g,0.71摩尔)加到含有催化量(1.5g,0.015摩尔)TEA的304.9g(2.03摩尔)仲-丁基苯酚(70%为邻-仲丁基苯酚,30%为对-仲丁基苯酚;Schenectady International)中。喷射氮气除去HCl,将反应物质加热至80℃并在该温度保持4小时。然后使用TEA调节pH≥8,冷却,过滤得到(98%)澄清、几乎无色的液体,为(HPLC)97%三仲丁基亚磷酸酯。
实施例中的制剂使用以下化合物:
实施例3:稳定聚乙烯
将基本不含任何稳定添加剂的薄膜级线性低密度聚乙烯(LL 1018;ExxonMobil)与基础稳定剂(base stabilization)和测试添加剂干混。基础稳定剂包括500ppm酚类抗氧剂,Irganox1076,和800ppm聚合物加工助剂,Dynamar FX-5920A。以1摩尔当量基础(42.5ppm磷)加入测试添加剂。最初在氮气氛下于190℃将该制剂在双螺杆挤出机中熔融复配;相当于零次挤出。然后在260℃将所得挤出物在配备有Maddock混合部件的单螺杆挤出机上多次挤出。收集第一次、第三次和第五次挤出物样品测试。在193℃各以低压、然后高压将0次、第1次、第3次和第5次的挤出物进行压缩模制3分钟,然后冷却来制成板(0,32mm)。测试样品的熔体流动速率保持(根据ASTM-1238;190℃/2.16kg;21.6kg),挤出期间的颜色发展,在60℃暴露于氮氧化物期间的颜色发展(根据ASTM-1925)。结果见下文。添加剂记录为基于聚合物的重量百分数。
制剂亚磷酸酯(ppm) | 没有0 | 亚磷酸酯1657 | 亚磷酸酯2657 | 亚磷酸酯3657 | 亚磷酸酯4657 | 亚磷酸酯5888 | 亚磷酸酯6888 |
熔体流动速率;190℃;2.16kg | |||||||
0第1次第3次第5次 | 0.880.830.760.65 | 1.041.010.970.93 | 1.010.980.880.78 | 1.031.020.970.90 | 0.960.900.750.67 | 1.021.020.950.85 | 1.030.990.880.84 |
熔体流动速率数据;190℃;2.16kg | |||||||
0第1次第3次第5次 | 16.5016.1215.7715.36 | 17.0717.1816.7916.79 | 16.9416.8316.3915.81 | 16.7316.8817.0216.85 | 16.9316.5615.6915.22 | 16.9617.0116.8016.49 | 16.9216.8616.5216.13 |
熔体流动速率;190℃;21.6/2.16kg | |||||||
0第1次第3次第5次 | 18.7119.4520.7423.77 | 16.3616.9317.3718.05 | 16.7817.2218.6920.33 | 16.2316.5917.5018.65 | 17.7218.3620.8622.81 | 16.5716.6617.7719.30 | 16.4917.0818.6919.32 |
由该挤出次数vs熔体流动速率保持表可以看出,与其固体叔丁基对应物相比,液体仲-丁基取代的亚磷酸酯始终提供更好的性能。由于每次比较中浓度等同,并且由于空间位阻大致相同,来自于液态仲-丁基取代的亚磷酸酯的性能益处是明显的。
制剂亚磷酸酯(ppm) | 没有0 | 亚磷酸酯1657 | 亚磷酸酯2657 | 亚磷酸酯3657 | 亚磷酸酯4657 | 亚磷酸酯5888 | 亚磷酸酯6888 |
YI颜色数据;C明度(Illuminant);2°观察者 | |||||||
0第1次第3次第5次 | 2.024.106.998.82 | 1.052.504.666.15 | 1.152.875.036.65 | 1.212.504.936.05 | -0.081.003.253.83 | 0.302.256.107.68 | 1.463.766.457.80 |
由该挤出次数vs黄度指数保持表可以看出,与其固体叔丁基对应物亚磷酸酯2和亚磷酸酯6相比,液体仲-丁基取代的亚磷酸酯1和亚磷酸酯5提供更低的颜色。由于每次比较中浓度等同,并且由于空间位阻大致相同,来自于液态仲-丁基取代的亚磷酸酯的性能益处是明显的。
制剂亚磷酸酯(ppm) | 没有0 | 亚磷酸酯1657 | 亚磷酸酯2657 | 亚磷酸酯3657 | 亚磷酸酯4657 | 亚磷酸酯5888 | 亚磷酸酯6888 |
气体衰退老化;60℃;第1次; | |||||||
0天7天14天21天 | 1.404.506.177.40 | 1.301.722.162.71 | 1.292.272.893.31 | 1.282.083.163.72 | 1.225.718.258.07 | 1.301.712.403.07 | 1.342.312.803.31 |
由该暴露于氮氧化物期间的黄度指数颜色保持表可以看出,与其固体叔丁基对应物相比,液体仲-丁基取代的亚磷酸酯始终提供更低的颜色。由于每次比较中浓度等同,并且由于空间位阻大致相同,来自于液态仲-丁基取代的亚磷酸酯的性能益处是明显的。
实施例4:粘度
如下测量粘度:Peltier板,40mm钢锥(steel cone),2°角2℃/min攀升(ramp),切变应力=10Pa。
样品ID | 粘度(mPa·s) | |||||
2℃ | 20℃ | 40℃ | 60℃ | 80℃ | 100℃ | |
P7 | 140,000 | 10,800 | 1250 | 254 | 79.1 | 33.5 |
P8 | 1,119 | 199 | 51.6 | 19.9 | 10.0 | -- |
亚磷酸酯3 | 1,486 | 244 | 58.1 | 21.9 | 10.9 | 6.6 |
P7是三-壬基苯基亚磷酸酯
P8是70%亚磷酸酯1/30%亚磷酸酯3
本发明的亚磷酸酯P8和亚磷酸酯3比非本发明的亚磷酸酯P7粘度小得多。更低的粘度更容易处理。
例如本发明化合物在20℃所显示的粘度小于大约1000mPa·秒,或在20℃小于大约750mPa·秒,或在40℃小于大约150mPa.秒或在40℃小于大约135mPa.秒,在TA Instruments AR-2000N锥/板粘度计上测量:40mm 2°钢锥与珀耳帖板,10Pa恒定剪切应力;2℃/min,温度由0℃攀升至100℃。
Claims (8)
2.根据权利要求1的方法,其中每个R等同并且在邻位或对位被取代。
3.根据权利要求1的方法,其中每个R是仲丁基并且在邻位或对位被取代。
4.根据权利要求1的方法,其包括掺入或应用式I的亚磷酸酯混合物,其中R基团在邻位或对位并且独立地是甲基、乙基、仲丁基、叔戊基或己基,并且其中大约60%或更多的酚基在邻位被取代。
5.根据权利要求1的方法,其包括掺入或应用式I的亚磷酸酯混合物,其中每个R基团是等同的并且在邻位或对位被取代,其中大约60%或更多的酚基在邻位被取代。
6.根据权利要求1的方法,其包括掺入或应用选自受阻酚抗氧剂、羟胺、苯并呋喃酮、其他有机磷稳定剂、空间位阻胺光稳定剂和羟苯基苯并三唑、三芳基-s-三嗪或羟苯基二苯甲酮紫外光稳定剂的另外的稳定剂。
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- 2006-07-12 DK DK06792495.1T patent/DK1910455T3/da active
- 2006-07-12 WO PCT/EP2006/064118 patent/WO2007009916A1/en not_active Application Discontinuation
- 2006-07-12 ES ES06792495T patent/ES2390090T3/es active Active
- 2006-07-12 EP EP06792495A patent/EP1910455B1/en active Active
- 2006-07-12 JP JP2008521936A patent/JP5236466B2/ja active Active
- 2006-07-12 CA CA2615555A patent/CA2615555C/en active Active
- 2006-07-12 CN CN200680026700.1A patent/CN101228220B/zh active Active
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Cited By (15)
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CN102421738A (zh) * | 2009-07-31 | 2012-04-18 | 科聚亚公司 | 由复合烃物流形成亚磷酸烷基化芳基酯组合物的方法 |
CN102428090A (zh) * | 2009-07-31 | 2012-04-25 | 科聚亚公司 | 固体亚磷酸烷基芳基酯组合物及其制备方法 |
CN102471357A (zh) * | 2009-07-31 | 2012-05-23 | 科聚亚公司 | 固体烷基芳基亚磷酸酯组合物和制备其方法 |
CN106800671A (zh) * | 2009-07-31 | 2017-06-06 | 爱迪文特瑞士有限公司 | 固体亚磷酸烷基芳基酯组合物及其制备方法 |
CN104508031A (zh) * | 2012-08-02 | 2015-04-08 | 艾得文瑞士有限公司 | 亚磷酸酯组合物 |
CN104508031B (zh) * | 2012-08-02 | 2020-10-16 | 瑞士新集团有限公司 | 亚磷酸酯组合物 |
CN106574090A (zh) * | 2014-08-05 | 2017-04-19 | 巴斯夫欧洲公司 | 作为稳定剂的3‑苯基‑苯并呋喃‑2‑酮二亚磷酸酯衍生物 |
CN106574090B (zh) * | 2014-08-05 | 2019-11-19 | 巴斯夫欧洲公司 | 作为稳定剂的3-苯基-苯并呋喃-2-酮二亚磷酸酯衍生物 |
CN106317453B (zh) * | 2015-07-10 | 2018-10-26 | 奕益实业有限公司 | 液态含磷稳定剂及其制法 |
CN109689792A (zh) * | 2016-08-30 | 2019-04-26 | 巴斯夫欧洲公司 | 用于生橡胶的液体抗氧化剂组合物 |
CN109689792B (zh) * | 2016-08-30 | 2022-03-29 | 巴斯夫欧洲公司 | 用于生橡胶的液体抗氧化剂组合物 |
CN108570173B (zh) * | 2017-03-14 | 2020-07-14 | 中国科学院化学研究所 | 一种为聚合物提供抗氧化性的组合物及其应用 |
CN108570173A (zh) * | 2017-03-14 | 2018-09-25 | 中国科学院化学研究所 | 一种为聚合物提供抗氧化性的组合物及其应用 |
CN111448201A (zh) * | 2017-07-06 | 2020-07-24 | 巴斯夫欧洲公司 | 包含苯并呋喃酮和受阻胺光稳定剂的稳定化聚烯烃组合物 |
CN109096728A (zh) * | 2018-08-28 | 2018-12-28 | 方金婷 | 一种阻燃型塑料薄膜的制备方法及其应用 |
Also Published As
Publication number | Publication date |
---|---|
US7468410B2 (en) | 2008-12-23 |
EP1910455B1 (en) | 2012-08-08 |
EP1910455A1 (en) | 2008-04-16 |
CA2615555A1 (en) | 2007-01-25 |
DK1910455T3 (da) | 2012-11-19 |
WO2007009916A1 (en) | 2007-01-25 |
CA2615555C (en) | 2014-01-07 |
JP2009503134A (ja) | 2009-01-29 |
JP5236466B2 (ja) | 2013-07-17 |
ES2390090T3 (es) | 2012-11-06 |
CN101228220B (zh) | 2012-12-12 |
US20070021537A1 (en) | 2007-01-25 |
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