CN101511913A - 作为稳定剂的液体聚合物亚磷酸酯和亚膦酸酯 - Google Patents
作为稳定剂的液体聚合物亚磷酸酯和亚膦酸酯 Download PDFInfo
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- CN101511913A CN101511913A CNA2007800330955A CN200780033095A CN101511913A CN 101511913 A CN101511913 A CN 101511913A CN A2007800330955 A CNA2007800330955 A CN A2007800330955A CN 200780033095 A CN200780033095 A CN 200780033095A CN 101511913 A CN101511913 A CN 101511913A
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- Prior art keywords
- compound
- formula
- butyl
- alkyl
- polymer
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- 239000003381 stabilizer Substances 0.000 title claims abstract description 11
- 239000007788 liquid Substances 0.000 title abstract description 22
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 title description 10
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 title 1
- 229920000642 polymer Polymers 0.000 claims abstract description 59
- 239000011368 organic material Substances 0.000 claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims description 116
- 239000000203 mixture Substances 0.000 claims description 77
- 239000000463 material Substances 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001301 oxygen Substances 0.000 claims description 23
- 229910052760 oxygen Inorganic materials 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
- 239000005864 Sulphur Substances 0.000 claims description 15
- 239000000654 additive Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 230000000996 additive effect Effects 0.000 claims description 13
- 229920001059 synthetic polymer Polymers 0.000 claims description 11
- 239000003963 antioxidant agent Substances 0.000 claims description 10
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 10
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 235000006708 antioxidants Nutrition 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000012545 processing Methods 0.000 claims description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000002530 phenolic antioxidant Substances 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 abstract description 2
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract 1
- -1 isobutyl- Chemical group 0.000 description 142
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 47
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 37
- 150000002148 esters Chemical class 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- 239000000126 substance Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 239000002585 base Substances 0.000 description 24
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 19
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 17
- 150000001408 amides Chemical class 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
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- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- 239000004743 Polypropylene Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 12
- 238000005227 gel permeation chromatography Methods 0.000 description 12
- 229960003742 phenol Drugs 0.000 description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 11
- 229920002554 vinyl polymer Polymers 0.000 description 11
- 238000004679 31P NMR spectroscopy Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000853 adhesive Substances 0.000 description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
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- 125000003118 aryl group Chemical group 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- 229920000715 Mucilage Polymers 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 239000000835 fiber Substances 0.000 description 8
- 239000004700 high-density polyethylene Substances 0.000 description 8
- 239000011572 manganese Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 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 8
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 229920001903 high density polyethylene Polymers 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 239000004417 polycarbonate Substances 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali 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
- 239000011248 coating agent Substances 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-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
- WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 5
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- 229920000092 linear low density polyethylene Polymers 0.000 description 5
- 239000004707 linear low-density polyethylene Substances 0.000 description 5
- 239000000314 lubricant Substances 0.000 description 5
- 229940017219 methyl propionate Drugs 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 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 5
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- 230000009182 swimming Effects 0.000 description 5
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
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- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
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- 150000002576 ketones Chemical class 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 4
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- 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 4
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- KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 4
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- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
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- IJRHDFLHUATAOS-DPMBMXLASA-M sodium ricinoleate Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O IJRHDFLHUATAOS-DPMBMXLASA-M 0.000 description 1
- 229940074404 sodium succinate Drugs 0.000 description 1
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- 239000004408 titanium dioxide Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- 230000009466 transformation Effects 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
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- 235000019154 vitamin C Nutrition 0.000 description 1
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- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
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- 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
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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Abstract
公开了式(I)的新颖的液体聚合物化合物,其中通用符号如权利要求1中所定义,该化合物作为稳定剂用于保护有机材料抗氧化、热或者光引起的降解。
Description
本发明涉及新颖的液体聚合物亚磷酸酯和亚膦酸酯,涉及包含有机材料优选合成聚合物以及所述的新颖的液体聚合物亚磷酸酯和亚膦酸酯的组合物,以及涉及其用于稳定有机材料抗氧化、热或者光引起的降解的用途。
有机亚磷酸酯和亚膦酸酯是工业上已知的用于合成聚合物例如诸如聚烯烃中作为共稳定剂、次要抗氧化剂和加工稳定剂。由于它们易于处理以及在合成聚合物中这些化合物优异的相容性,因此液体亚磷酸酯或者亚膦酸酯在工业上是特别优选的。亚磷酸三壬基苯基酯(TNPP)已经被广泛的用于这种用途。但是,最近已经发现TNPP的转化产物如例如壬基苯酚在动物体内是激素活性的。由于越来越大的卫生和食品工业压力,塑料制造商很想要逐步淘汰这种液体稳定剂。
已经发现了新的在室温为液体的聚合物亚磷酸酯和亚膦酸酯,其能够代替TNPP来稳定有机材料抗氧化、热或者光引起的降解。
本发明所以涉及式I的聚合物化合物,
其中
L是-X-R4-Y-,
R1是氢或者C1-C4烷基,
R2是氢或者甲基,
R5是氢或者C1-C8烷基,
m是0或者1,和
n是2-100的整数。
具有高到25个碳原子的烷基是支化的或者未支化的基团,例如甲基,乙基,丙基,异丙基,正丁基,仲丁基,异丁基,叔丁基,2-乙基丁基,正戊基,异戊基,1-甲基戊基,1,3-二甲基丁基,正己基,1-甲基己基,正庚基,异庚基,1,1,3,3-四甲基丁基,1-甲基庚基,3-甲基庚基,正辛基,2-乙基己基,1,1,3-三甲基己基,1,1,3,3-四甲基戊基,壬基,癸基,十一烷基,1-甲基十一烷基,十二烷基,1,1,3,3,5,5-六甲基己基,十三烷基,十四烷基,十五烷基,十六烷基,十七烷基,十八烷基,二十烷基或者二十二烷基。
具有2-25个碳原子的链烯基是支化的或者未支化的基团例如诸如,丙烯基,2-丁烯基,3-丁烯基,异丁烯基,正2,4-戊二烯基,3-甲基-2-丁烯基,正2-辛烯基,正2-十二碳烯基,异十二碳烯基,油基,正2-十八碳烯基或者正4-十八碳烯基。
用氧、硫或者中断的C2-C25烷基是例如CH3-O-CH2CH2-,CH3-S-CH2CH2-,CH3-N(CH3)-CH2CH2-,CH3-O-CH2CH2-O-CH2CH2-,CH3-(O-CH2CH2-)2O-CH2CH2-,CH3-(O-CH2CH2-)3O-CH2CH2-或者CH3-(O-CH2CH2-)4O-CH2CH2-。
C5-C12环烷基是例如环戊基,环己基,环庚基,环辛基,环壬基,环癸基,环十一烷基或者环十二烷基。优选环己基。
C1-C24亚烷基是支化的或者未支化的基团,例如亚甲基,亚乙基,亚丙基,三亚甲基,四亚甲基,五亚甲基,六亚甲基,七亚甲基,八亚甲基,十亚甲基,十二亚甲基或者十八亚甲基。
C2-C24亚链烯基是例如亚乙烯基,甲基亚乙烯基,辛烯基亚乙基或者十二碳烯基亚乙基。C2-C8亚链烯基是优选的。
用氧、硫或者中断的C2-C24亚烷基是例如-CH2-O-CH2-,-CH2-S-CH2-,-CH2-N(CH3)-CH2-,-CH2-O-CH2CH2-,-CH2CH2-O-CH2CH2-,-CH2CH2-O-CH2CH2-O-CH2CH2-,-CH2CH2-(O-CH2CH2-)2O-CH2CH2-,-CH2CH2-(O-CH2CH2-)3O-CH2CH2-,-CH2CH2-(O-CH2CH2-)4O-CH2CH2-,-CH2CH2-S-CH2CH2-或者-CH2CH2-N(CH3)-CH2CH2-。
优选的是式I的化合物,其中
R2是氢或者甲基,
R5是氢或者C1-C8烷基。
非常令人感兴趣的是式I的化合物,其中
R3是C1-C18烷基、C2-C18链烯基;用氧、硫或者中断的C2-C18烷基;或者C5-C8环烷基,
R5是氢或者C1-C8烷基。
优选式I的聚合物化合物,其中R2是氢。
同样优选式I的聚合物化合物,其中R3是C1-C8烷基。
特别优选式I的聚合物化合物,其中X与Y相同并且是-O-。
特别令人感兴趣的是式I的聚合物化合物,其中
L是-X-R4-Y-,
R1是氢或者叔丁基,
R2是氢,
R3是C1-C8烷基,
R5是氢或者甲基,
X是-O-,
Y是-O-,
m是1,和
n是2-50的整数。
该新颖的式I的聚合物化合物可以通过本身已知的方式来制备。
本发明此外涉及一种优选的制备式I的聚合物化合物的方法,其包括将式II的化合物或者式II的化合物的混合物与式III的化合物或者式III的化合物的混合物进行反应,
其中的通用符号定义同上,
H-L-H (III)
其中L是定义同上。
该反应是在熔融态或者是在合适的有机的、极性的或者非极性的非质子溶剂中进行的。该反应优选是在碱存在下,在-20℃到溶剂的沸点的温度,特别是20-150℃温度进行的。
碱例如胺也可以同时用作溶剂。
碱可以以不同的量使用,从化学计量的催化量直到超出所用的式II化合物或者式III化合物的摩尔量的几倍。如果合适,则在该反应中形成的氯化氢通过碱转化为氯化物,其可以通过过滤和/或用合适的水性或者固体相清洗而除去;这里还可以使用第二种的、水不混溶的溶剂。产物通过蒸发有机相和干燥残留物而方便的分离。
进行反应所用的合适的溶剂包括烃(例如均三甲基苯,甲苯,二甲苯,己烷,戊烷或者其它石油醚馏分),卤代烃(例如二-或者三氯甲烷,1,2-二氯乙烷,1,1,1-三氯乙烷或者氯苯),醚(例如二乙醚,二丁醚或者四氢呋喃),酮(例如丙酮,乙基甲基酮,二乙酮,甲基丙基酮或者环己酮),此外还有乙腈,醋酸丁酯,二甲基甲酰胺,二甲基亚砜或者N-甲基吡咯烷酮。
合适的碱包括伯、仲和特别是叔胺(例如三甲胺,三乙胺,三丁胺,N,N-二甲基苯胺,N,N-二乙基苯胺或者吡啶),氢化物(例如氢化锂,氢化钠或者氢化钾)或者醇盐(例如甲氧基钠)。
如果将氢化物(例如氢化钠,硼氢化钠或者氢化铝锂),碱金属,碱金属氢氧化物或者甲氧基钠用作碱,则可以首先形成式III化合物相应的醇盐;在与式II的化合物反应之前,通过蒸馏(例如与甲苯的共沸混合物)除去所形成的任何反应产物(例如水或者甲醇)。
式I的聚合物化合物的结构组成取决于反应条件,例如溶剂或者反应温度,和式II和III化合物的摩尔混合比和浓度。例如液体低聚物亚磷酸酯的粘度可以通过分子量,共聚单体成分和式III化合物的混合物来调整。如果目标是低粘度的液体亚磷酸酯或者亚膦酸酯,则优选使用式III的低分子量和/或长链化合物和/或式III化合物几种分子的混合物。另一方面,如果目标是高粘度的液体亚磷酸酯或者亚膦酸酯,则优选使用式III的高分子量、短链化合物和/或式III的单一分子的化合物。
式II的化合物和式III的化合物二者可以以过量的摩尔来使用。但是,优选将式III的化合物过量使用。优选的式II和III化合物的摩尔混合比是1.9:1-1:1.9,特别优选1.05:1-1:1.8,尤其是1:1.1-1:1.3。
式I的聚合物化合物的分子量分布取决于分子量,组成和合成路径。通常,对于目标性能来说分子量分布不是关键所在,但是对于特定的应用来说优选的是窄分子量分布(Mw/Mn<5)或者双峰或者多峰分布。
本发明所以还涉及聚合物产物,其通过将式II的化合物或者式II的化合物的混合物与式III的化合物或者式III的化合物的混合物进行反应来获得。
制备式II和III的化合物是已知的。
其中m=1的式II的化合物是已知的或者可以通过本身已知的方法来制备,例如如DE-A-3928291或者由R.A.Bartlett等人J.Amer.Chem.Soc.109(19),5699(1987)中所述。
其中m=0的式II的化合物同样是本身已知的或者可以通过本身已知的方法来制备,例如如Org.SynthesesColl.第IV卷784(1963)和由T.WeII等人,Helv.Chim.Acta 1952,1412,或者F.Nief等人,Tetrahedron47(33),6673(1991)中所述。
制备新颖的式I的聚合物化合物所需的式II的化合物可以类似于上述文献方法所述来原位制备,并进一步不进行分离而与式III的化合物进行反应来得到式I的聚合物化合物。
在式I的重复结构单元中的L可以具有相同或者不同的含义。
如果式III的化合物过量使用,则式I的聚合物化合物的端基(如下式IV所示)
主要是羟基基团或者胺基团,其如果需要可以容易的通过已知的方法被衍生。例如这些端基可以依靠酰基卤(例如羧酸酰卤或者磷酸卤化物(phosphoric acid halide),或者酸酐)进行酯化;与异氰酸酯反应来得到氨基甲酸酯;与异硫氰酸酯反应来得到硫代氨基甲酸酯;或者与磺酰卤以及例如亚硫酰氯反应来得到卤化物。
如果式II的化合物过量使用,则式I的聚合物化合物的端基在某些情况中还可以带有反应性基团。
氯原子可以用另外的亲核试剂例如酚类、醇类、胺类、硫醇类或者亚磷酸二烷基酯通过已知的氢氯酸消去方法来取代。合适的醇类是C1-C8烷醇例如甲醇,乙醇,正丙醇或者正丁醇。
为了调节式I的聚合物亚磷酸酯或者亚膦酸酯的分子量,有用的是用上述亲核试剂来部分的替换H-L-H。在这种情况中,分子量的调节是通过端基封闭和停止增长的聚合物链的分子量增加来进行的。该另外的亲核试剂的量取决于目标分子量以及式II和式III化合物的比例。优选小于20mol%的式III是用亲核试剂取代的。
本发明优选涉及式V的聚合物化合物:
其中L、R0、R1、R2、R3、m和n定义同上,
或者此外,端基E1和E2一起形成直接键(成环化合物);和
R10是C1-C8烷基。
特别优选给出的是式V的聚合物化合物,其中端基E1是氢,端基E2是-L-H,在其中L定义同上。
式I的新颖的液体化合物适于稳定有机材料来抗氧化、热或者光引起的降解。
这样的材料示例性的例子是:
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,聚乙烯基环己烷,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(其任选是可以交联的),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),线性低密度聚乙烯(LLDPE),(VLDPE)和(ULDPE)。
聚烯烃(即上一段中示例性的单烯烃的聚合物(优选聚乙烯和聚丙烯))可以通过不同的,特别是通过下面的方法来制备:
a)自由基聚合(通常在高压和高温下)。
b)使用催化剂的催化聚合,该催化剂通常含有一个或多个元素周期表第IVb,Vb,VIb或者VIII族的金属。这些金属通常具有一个或多个配位体,典型的是氧化物,卤化物,醇化物,酯类,醚类,胺类,烷基,链烯基和/或芳基,其可以是π-或者σ-配位的。这些金属络合物可以处于游离态或者固定在基底上,典型的是固定在活化的氯化镁,氯化钛(lll),氧化铝或氧化硅上。这些催化剂在聚合介质中是可溶的或者是不溶的。催化剂可以本身用于聚合中,或者进一步可以使用活化剂,典型的是烷基金属,氢化金属,金属烷基卤化物,金属烷基氧化物或者金属烷基噁烷,所述的金属是元素周期表第Ia,IIa和/或IIIa族的元素。活化剂可以方便的用另外的酯、醚、胺和甲硅烷基醚基团来改性。这些催化剂体系通常称为菲利普类催化剂,Standard Oil Indiana催化剂,齐格勒(-纳塔)催化剂,TNZ(杜邦),茂金属或单中心催化剂(SSC)。
2.在1)中提到的聚合物的混合物,例如聚丙烯和聚异丁烯的混合物,聚丙烯和聚乙烯(例如PP/HDPE,PP/LDPE)的混合物和不同类型的聚乙烯的混合物(例如LDPE/HDPE)。
3.单烯烃和二烯烃彼此或者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)及其与低密度聚乙烯(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,乙烯/乙烯基环己烷共聚物,乙烯/环烯烃共聚物(例如乙烯/降冰片烯如COC),乙烯/1-烯烃共聚物,这里该1-烯烃是原位产生的;丙烯/丁二烯共聚物,异丁烯/异戊二烯共聚物,乙烯/乙烯基环己烯共聚物,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/乙酸乙烯酯共聚物或者乙烯/丙烯酸共聚物和它们的盐(离聚物)以及乙烯与丙烯以及二烯例如己二烯、二环戊二烯或者亚乙基-降冰片烯的三元共聚物;和这样的共聚物彼此的混合物或者这样的共聚物与上面的1)中提到的聚合物的混合物,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和交替的或无规的聚亚烷基/一氧化碳共聚物及其与其它聚合物例如聚酰胺的混合物。
4.烃树脂(例如C5-C9),包括其氢化改性物(例如增粘剂)和聚亚烷基与淀粉的混合物。
1)-4)的均聚物和共聚物可以具有任何立体结构,包括间同立构,全同立构,半全同立构或无规立构;其中无规立构聚合物是优选的。还包括立体嵌段聚合物。
5.聚苯乙烯,聚(对-甲基苯乙烯),聚(α-甲基苯乙烯)。
6.芳族均聚物和共聚物,其源自乙烯基芳族单体,包括苯乙烯,α-甲基苯乙烯,乙烯基甲苯的所有异构体,尤其是对乙烯基甲苯,乙基苯乙烯、丙基苯乙烯、乙烯基联苯、乙烯基萘和乙烯基蒽的所有异构体,以及它们的混合物。均聚物和共聚物可以具有任何立体结构,包括间同立构,全同立构,半全同立构或无规立构;其中无规立构聚合物是优选的。还包括立体嵌段聚合物。
6a.包括上述乙烯基芳族单体和选自乙烯,丙烯,二烯,腈类,酸类,马来酸酐类,马来酰亚胺类,乙酸乙烯酯和氯乙烯或丙烯酸系衍生物和它们的混合物中的共聚单体的共聚物,例如苯乙烯/丁二烯,苯乙烯/丙烯腈,苯乙烯/乙烯(共聚物),苯乙烯/甲基丙烯酸烷基酯,苯乙烯/丁二烯/丙烯酸烷基酯,苯乙烯/丁二烯/甲基丙烯酸烷基酯,苯乙烯/马来酸酐,苯乙烯/丙烯腈/丙烯酸甲酯,高抗冲击强度的苯乙烯共聚物和另一种聚合物如聚丙烯酸酯、二烯烃聚合物或乙烯/丙烯/二烯烃三元共聚物的混合物;以及苯乙烯的嵌段共聚物,如苯乙烯/丁二烯/苯乙烯,苯乙烯/异戊二烯/苯乙烯,苯乙烯/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。
6b.衍生自在6)中提及的聚合物的氢化获得的氢化芳族聚合物,尤其包括通过氢化无规立构聚苯乙烯制备的聚环己基乙烯(PCHE),常常称之为聚乙烯基环己烷(PVCH)。
6c.衍生自在6a)中提及的聚合物的氢化获得的氢化芳族聚合物。
均聚物和共聚物可以具有任何立体结构,包括间同立构,全同立构,半全同立构或无规立构;其中无规立构聚合物是优选的。还包括立体嵌段聚合物。
7.乙烯基芳族单体如苯乙烯或α-甲基苯乙烯的接枝共聚物,例如聚丁二烯上接枝苯乙烯,聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物上接枝苯乙烯;聚丁二烯上接枝苯乙烯和丙烯腈(或甲基丙烯腈);聚丁二烯上接枝苯乙烯、丙烯腈和甲基丙烯酸甲酯;聚丁二烯上接枝苯乙烯和马来酸酐;聚丁二烯上接枝苯乙烯、丙烯腈和马来酸酐或马来酰亚胺;聚丁二烯上接枝苯乙烯和马来酰亚胺;聚丁二烯上接枝苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯;乙烯/丙烯/二烯烃三元共聚物上接枝苯乙烯和丙烯腈;聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上接枝苯乙烯和丙烯腈;丙烯酸酯/丁二烯共聚物上接枝苯乙烯和丙烯腈,以及它们与6)中所列举的共聚物的混合物,例如称为ABS、MBS、ASA或AES聚合物的共聚物混合物。
8.含卤素的聚合物类,如聚氯丁二烯,氯化橡胶,异丁烯-异戊二烯的氯化和溴化共聚物(卤代丁基橡胶),氯化或氯磺化聚乙烯,乙烯和氯化乙烯的共聚物,表氯醇均-或共聚物,尤其含卤素的乙烯基化合物的聚合物,例如聚氯乙烯,聚偏二氯乙烯,聚氟乙烯,聚偏二氟乙烯,以及它们的共聚物,如氯乙烯/偏二氯乙烯,氯乙烯/乙酸乙烯酯或偏二氯乙烯/乙酸乙烯酯共聚物。
9.由α,β-不饱和酸和其衍生物得到的聚合物,如聚丙烯酸酯类和聚甲基丙烯酸酯类;聚甲基丙烯酸甲酯类,聚丙烯酰胺类和聚丙烯腈类,其用丙烯酸丁酯进行冲击改性。
10.在9)中提到的单体相互之间的或与其它不饱和单体的共聚物,例如丙烯腈/丁二烯共聚物,丙烯腈/丙烯酸烷基酯共聚物,丙烯腈/丙烯酸烷氧基烷基酯或丙烯腈/卤代乙烯共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
11.由不饱和醇类和胺类或其酰基衍生物或缩醛类得到的聚合物,例如聚乙烯醇,聚乙酸乙烯酯,聚硬脂酸乙烯酯,聚苯甲酸乙烯酯,聚马来酸乙烯酯,聚乙烯醇缩丁醛,聚邻苯二甲酸烯丙酯或聚烯丙基蜜胺;以及它们与1)中提到的烯烃的共聚物。
12.环醚的均聚物和共聚物,如聚亚烷基二醇,聚环氧乙烷,聚环氧丙烷或它们与双缩水甘油基醚的共聚物。
13.聚缩醛类,如聚甲醛和含有环氧乙烷作为共聚单体的那些聚甲醛;用热塑性聚氨酯类、丙烯酸酯类或MBS改性的聚缩醛类。
14.聚苯醚和聚苯硫醚,以及聚苯醚与苯乙烯聚合物或聚酰胺的混合物。
15.由一方面羟基封端的聚醚、聚酯或聚丁二烯与另一方面脂族或芳族多异氰酸酯衍生而来的聚氨酯,以及它的前体。
16.由二胺和二羧酸和/或由氨基羧酸或相应的内酰胺衍生而来的聚酰胺和共聚酰胺,例如聚酰胺4,聚酰胺6,聚酰胺6/6,6/10,6/9,6/12,4/6,12/12,聚酰胺11,聚酰胺12,以间-亚二甲苯基二胺和己二酸为原料的芳族聚酰胺;从六亚甲基二胺和间苯二甲酸或/和对苯二甲酸制备的并且有或没有弹性体作为改性剂的聚酰胺,例如聚对苯二甲酰(2,4,4-三甲基亚己基)二胺或聚间苯二甲酰间亚苯基二胺;还有上述聚酰胺与聚烯烃,烯烃共聚物,离聚物或化学键连接的或接枝的弹性体的嵌段共聚物;或与聚醚类,如聚乙二醇、聚丙二醇或聚丁二醇的嵌段共聚物;以及用EPDM或ABS改性的聚酰胺或共聚酰胺;和在加工过程中缩合的聚酰胺(RIM聚酰胺体系)。
17.聚脲类,聚酰亚胺类,聚酰胺-酰亚胺类,聚醚酰亚胺类,聚酯酰亚胺类,聚乙内酰脲类和聚苯并咪唑类。
18.由二羧酸和二醇和/或由羟基羧酸或相应的内酯衍生而来的聚酯,例如聚对苯二甲酸乙二醇酯,聚对苯二甲酸丁二醇酯,聚对苯二甲酸1,4-二羟甲基环己烷酯,聚萘二甲酸亚烷基二醇酯(PAN)和聚羟基苯甲酸酯,以及由羟基封端的聚醚衍生而来的嵌段共聚醚酯;还有用聚碳酸酯或MBS改性的聚酯类。
19.聚碳酸酯和聚酯碳酸酯。
20.聚砜,聚醚砜和聚醚酮。
21.交联的聚合物,其衍生自一方面醛类以及另一方面酚类,脲类和蜜胺,例如酚醛树脂,脲醛树脂和蜜胺甲醛树脂。
22.干性和非干性醇酸树脂。
23.不饱和聚酯树脂,其衍生自饱和的和不饱和的二羧酸与多羟基醇和作为交联剂的乙烯基化合物的共聚酯,以及其含卤素的低可燃性的改性物。
24.衍生自取代的丙烯酸酯的可交联的丙烯酸系树脂,例如环氧丙烯酸酯类,氨基甲酸酯丙烯酸酯类或者聚酯丙烯酸酯类。
25.与蜜胺树脂类、脲树脂类、异氰酸酯类、异氰脲酸酯类、多异氰酸酯类或者环氧树脂类交联的醇酸树脂类、聚酯树脂类和丙烯酸酯树脂类。
26.交联的环氧树脂,其衍生自脂肪族、环脂族、杂环或芳族的缩水甘油基化合物,例如双酚A和双酚F的二缩水甘油醚产物,其是与常规的硬化剂例如酸酐或者胺交联的,使用或者不使用促进剂。
27.天然聚合物,如纤维素、橡胶、明胶和它们的化学改性的同源衍生物,例如乙酸纤维素,丙酸纤维素和丁酸纤维素,或纤维素醚类,如甲基纤维素;以及松香和它的衍生物。
28.上述聚合物的共混物和合金(高分子共混物),例如PP/EPDM,聚酰胺/EPDM或ABS,PVC/EVA,PVC/ABS,PVC/MBS,PC/ABS,PC/聚酯,PBTP/ABS,PC/ASA,PC/PBT,PVC/CPE,PVC/丙烯酸酯类,POM/热塑性PUR,PC/热塑性PUR,POM/丙烯酸酯,POM/MBS,PPO/HIPS,PPO/PA6.6和共聚物,PA/HDPE,PA/PP,PA/PPO,PBT/PC/ABS或PBT/PET/PC。
29.天然存在的和合成的有机材料,其是纯的单体化合物或者这样的化合物的混合物,例如矿物油,动物和植物脂肪,油和蜡,或者基于合成的酯类(例如邻苯二甲酸酯类、己二酸酯类,磷酸酯类或者偏苯三酸酯类)以及合成的酯与矿物油的任何重量比的混合物的油,脂肪和蜡,典型的是这样用作纺丝纺纱组合物的这些,以及这样的材料的水性乳液。
30.天然或者合成橡胶的水性乳液,例如羧基化苯乙烯/丁二烯共聚物的天然乳胶。
因此本发明另外的目标是组合物,其包含a)受到氧化、热或者光易于引起降解的有机材料,和b)至少一种式I的聚合物化合物或者至少一种通过将式II的化合物或者式II的化合物的混合物与式III的化合物或者式III的化合物的混合物进行反应来获得的聚合物产物。
待保护的有机材料优选是天然的、半合成的或者优选合成聚合物。特别优选给出的是热塑性聚合物,尤其是聚烯烃,特别是聚丙烯和聚乙烯。
特别的重点应当放在该新颖的式I的聚合物化合物抗热和氧化降解的作用,特别在加热时,如在热塑性塑料加工中发生的降解。该新颖的式I的聚合物化合物所以非常适用作加工稳定剂。
式I的聚合物化合物优选以下面的量加入到待稳定的有机材料中:0.01-10%,例如0.01-5%,优选0.025-3%,特别是0.025-1%,基于待稳定的有机材料的重量。
除了液体式I的聚合物化合物之外,该新颖的组合物可以包含另外添加剂,例如诸如下面的:
1.抗氧化剂
1.1.烷基化一元酚类,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-双十八烷基-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,壬基苯酚,其侧链是直链或支链的例如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)苯酚以及它们的混合物。
1.2.烷基硫基甲基酚类,例如2,4-二辛基硫基甲基-6-叔丁基苯酚,2,4-二辛基硫基甲基-6-甲基苯酚,2,4-二辛基硫基甲基-6-乙基苯酚,2,6-双十二烷基硫基甲基-4-壬基苯酚。
1.3.氢醌类或烷基化氢醌类,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-羟基苯甲醚,3,5-二叔丁基-4-羟基苯甲醚,硬脂酸3,5-二叔丁基-4-羟基苯基酯,己二酸双(3,5-二叔丁基-4-羟基苯基)酯。
1.4.生育酚类,例如α-生育酚,β-生育酚,γ-生育酚,δ-生育酚和它们的混合物(维生素E)。
1.5.羟基化硫代二苯基醚类,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。
1.6.亚烷基双酚类,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,双[3,3-双(3′-叔丁基-4′-羟基苯基)丁酸]乙二醇酯,双(3-叔丁基-4-羟基-5-甲基-苯基)双环戊二烯,对苯二甲酸双[2-(3′-叔丁基-2′-羟基-5′-甲基苄基)-6-叔丁基-4-甲基苯基]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.O-,N-和S-苄基化合物类,例如3,5,3′,5′-四叔丁基-4,4′-二羟基二苄基醚,4-羟基-3,5-二甲基苄基巯基乙酸十八烷基酯,4-羟基-3,5-二叔丁基苄基巯基乙酸十三烷基酯,三(3,5-二叔丁基-4-羟基苄基)胺,二硫代对苯二甲酸双(4-叔丁基-3-羟基-2,6-二甲基苄基)酯,双(3,5-二叔丁基-4-羟基苄基)硫,3,5-二叔丁基-4-羟基苄基巯基乙酸异辛基酯。
1.8.羟苄基化丙二酸酯类,例如,2,2-双-(3,5-二叔丁基-2-羟基苄基)丙二酸二(十八烷基)酯,2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸二(十八烷基)酯,2,2-双(3,5-二叔丁基-4-羟基苄基)丙二酸二(十二烷基巯基乙基)酯,2,2-双(3,5-二叔丁基-4-羟基苄基)丙二酸双[4-(1,1,3,3-四甲基丁基)苯基]酯。
1.9.芳族羟苄基化合物类,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。
1.10.三嗪化合物类,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)异氰脲酸酯,1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)-异氰脲酸酯,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)异氰脲酸酯。
1.11.苄基膦酸酯类,例如2,5-二叔丁基-4-羟基苄基膦酸二甲酯,3,5-二叔丁基-4-羟基苄基膦酸二乙酯,3,5-二叔丁基-4-羟基苄基膦酸二(十八烷基)酯,5-叔丁基-4-羟基-3-甲基苄基膦酸二(十八烷基)酯,3,5-二叔丁基-4-羟基苄基膦酸的单乙酯的钙盐。
1.12.酰基氨基酚类,例如4-羟基月桂酰苯胺,4-羟基硬脂酰苯胺,N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.13.β-(3,5-二叔丁基-4-羟基苯基)丙酸的酯类,构成酯的有单羟基或多羟基醇类,例如甲醇,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,硫二甘醇,二甘醇,三甘醇,季戊四醇,异氰脲酸三(羟基乙基)酯,N,N′-双(羟乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸的酯类,构成酯的有单羟基或多羟基醇类,例如甲醇,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,硫二甘醇,二甘醇,三甘醇,季戊四醇,异氰脲酸三(羟基乙基)酯,N,N′-双(羟乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷;3,9-双[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}-1,1-二甲基乙基]-2,4,8,10-四氧杂螺[5.5]十一烷。
1.15.β-(3,5-二环己基-4-羟基苯基)丙酸的酯类,构成酯的有单羟基或多羟基醇类,例如甲醇,乙醇,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,硫二甘醇,二甘醇,三甘醇,季戊四醇,异氰脲酸三(羟基乙基)酯,N,N′-双(羟乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.16.3,5-二叔丁基-4-羟基苯基乙酸的酯类,构成酯的有单羟基或多羟基醇类,例如甲醇,乙醇,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,硫二甘醇,二甘醇,三甘醇,季戊四醇,异氰脲酸三(羟乙基)酯,N,N′-双(羟乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,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)丙酸的酰胺类,例如N,N′-双(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二胺,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)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 XL-1,由Uniroyal提供)。
1.18.抗坏血酸(维生素C)
1.19.胺类抗氧化剂,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′-双环己基对苯二胺、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)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、辛基化二苯胺、例如对,对′-二叔辛基二苯胺、4-正丁基氨基苯酚、4-丁酰基氨基苯酚、4-壬酰氨基苯酚、4-十二烷酰氨基苯酚、4-十八烷酰氨基苯酚、双(4-甲氧基苯基)胺、2,6-二叔丁基-4-二甲基氨基甲基苯酚、2,4′-二氨基二苯甲烷、4,4′-二氨基二苯甲烷、N,N,N′,N′-四甲基-4,4′-二氨基二苯甲烷、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)缩二胍、双[4-(1′,3′-二甲基丁基)苯基]胺、叔辛基化N-苯基-1-萘胺、单和二烷基化叔丁基/叔辛基二苯胺的混合物、单和二烷基化壬基二苯胺的混合物、单和二烷基化十二烷基二苯胺的混合物、单和二烷基化异丙基/异己基二苯胺的混合物、单和二烷基化叔丁基二苯胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单和二烷基化叔丁基/叔辛基吩噻嗪的混合物、单和二烷基化叔辛基-吩噻嗪的混合物、N-烯丙基吩噻嗪、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-酚。
2.UV吸收剂和光稳定剂
2.1.2-(2′-羟基苯基)苯并三唑类,例如2-(2′-羟基-5′-甲基苯基)-苯并三唑、2-(3′,5′-二叔丁基-2′-羟苯基)苯并三唑、2-(5′-叔丁基-2′-羟苯基)苯并三唑、2-(2′-羟基-5′-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3′,5′-二叔丁基-2′-羟苯基)-5-氯-苯并三唑、2-(3′-叔丁基-2′-羟基-5′-甲基苯基)-5-氯-苯并三唑、2-(3′-仲丁基-5’-叔丁基-2′-羟苯基)苯并三唑、2-(2′-羟基-4′-辛氧基苯基)苯并三唑、2-(3′,5′-二叔戊基-2′-羟苯基)苯并三唑、2-(3′,5′-双(α,α-二甲基苄基)-2′-羟苯基)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-苯并三唑、2-(3′-叔丁基-5’-[2-(2-乙基己氧基)-羰基乙基]-2′-羟苯基)-5-氯-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-苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-辛氧基羰基乙基)苯基)苯并三唑、2-(3′-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2′-羟苯基)苯并三唑、2-(3′-十二烷基-2′-羟基-5′甲基苯基)苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-异辛氧基羰基乙基)苯基苯并三唑、2,2’-亚甲基双[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3′-叔丁基-5’-(2-甲氧基羰基乙基)-2′-羟苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物;其中R=3′-叔丁基-4′-羟基-5′-2H-苯并三唑-2-基苯基,2-[2′-羟基-3′-(α,α-二甲基苄基)-5’-(1,1,3,3-四甲基丁基)-苯基]苯并三唑;2-[2′-羟基-3′-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)-苯基]苯并三唑。
2.2.2-羟基二苯甲酮类,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的酯类,例如水杨酸4-叔丁基-苯基酯,水杨酸苯酯,水杨酸辛基苯酯,二苯甲酰基间苯二酚,双(4-叔丁基苯甲酰基)间苯二酚,苯甲酰基间苯二酚,3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯基酯,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.丙烯酸酯类,例如α-氰基-β,β-二苯基丙烯酸乙酯,α-氰基-β,β-二苯基丙烯酸异辛酯,α-甲氧羰基肉桂酸甲酯,α-氰基-β-甲基-对甲氧基肉桂酸甲酯,α-氰基-β-甲基-对甲氧基肉桂酸丁酯,α-甲氧羰基-对甲氧基肉桂酸甲酯和N-(β-甲氧羰基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5.镍化合物类,例如2,2′-硫代-双-[4-(1,1,3,3-四甲基丁基)苯酚]的镍配合物,如1:1或1:2配合物,有或没有另外的配位体如正丁基胺,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(例如甲酯或乙酯)类的镍盐,酮肟例如2-羟基-4-甲基苯基十一烷基酮肟的镍配合物类,1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,有或没有另外的配位体。
2.6、空间位阻胺,例如双(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-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和丁二酸的缩合物、N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺和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、4-十八烷氧基-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)己二胺和4-吗啉代-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-4,6-二-(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-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、4-十六烷氧基-和4-十八烷氧基-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)己二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合物、1,2-双(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪以及4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[136504-96-6]);1,6-己二胺和2,4,6-三氯-1,3,5-三嗪以及N,N-二丁胺和4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[192268-64-7]);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-氧代-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-氧代螺-[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-甲氧苯基)乙烯、N,N′-双甲酰基-N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺、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。
2.7.草酰胺,例如4,4′-二辛氧基草酰替苯胺、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′-乙基草酰替苯胺和其与2-乙氧基2′-乙基-5,4′-二叔丁基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。
2.8.2-(2-羟苯基)-1,3,5-三嗪类,例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-双(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷基氧基-2-羟基丙氧基)-2-羟苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪、2-(2-羟苯基)-4-(4-甲氧苯基)-6-苯基-1,3,5-三嗪、2-{2-羟基-4-[3-(2-乙基己基-1-氧基)-2-羟基丙氧基]苯基}-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-乙基乙氧基)苯基]-4,6-二苯基-1,3,5-三嗪。
3.金属钝化剂,例如N,N′-二苯基草酰胺、N-水杨醛-N′-水杨酰肼、N,N′-双(水杨酰)肼、N,N′-双(3,5-二叔丁基-4-羟基苯基丙酰基)肼、3-水杨酰氨基-1,2,4-三唑、双(亚苄基)草酰二酰肼、草酰替苯胺、间苯二甲酰二酰肼、癸二酰二苯基酰肼、N,N′-双乙酰己二酰二酰肼、N,N′-双(水杨酰)草酰二酰肼、N,N′-双(水杨酰)硫代丙酰二酰肼。
4.亚磷酸酯类和亚膦酸酯类,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、三(壬基苯基)亚磷酸酯、三(十二烷基)亚磷酸酯、三(十八烷基)亚磷酸酯、二硬脂基季戊四醇二亚磷酸酯、三(2,4-二叔丁基苯基)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、双(2,4-二-枯基苯基)季戊四醇二亚磷酸酯、双(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、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、三硬脂基山梨糖醇三亚磷酸酯、四(2,4-二叔丁基苯基)4,4′-亚联苯基二亚膦酸酯、6-异辛基氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂磷杂环辛烯、双(2,4-二叔丁基-6-甲基苯基)甲基亚磷酸酯、双(2,4-二叔丁基-6-甲基苯基)乙基亚磷酸酯、6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂磷杂环辛烯、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]、2-乙基己基(3,3′,5,5′-四叔丁基-1,1′-联苯-2,2′-二基)亚磷酸酯、5-丁基-5-乙基-2-(2,4,6-三叔丁基苯氧基)-1,3,2-二氧杂磷杂环丙烷。
5.膦类,例如1,3-双(二苯基膦基)-2,2-二甲基丙烷。
6.羟基胺类,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-双十二烷基羟基胺、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、衍生自氢化牛脂胺的N,N-二烷基羟基胺。
7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-十八烷基-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N,N-二烷基羟基胺(其衍生自氢化牛脂胺)的硝酮。
8硫增效剂,例如硫代二丙酸二月桂酯或者硫代二丙酸二硬脂基酯。
9.过氧化物清除剂,例如β-硫代二丙酸的酯类,例如月桂基、硬脂基、十四烷基或十三烷基酯类,巯基苯并咪唑或2-巯基苯并咪唑的锌盐,二丁基二硫代氨基甲酸锌,二(十八烷基)二硫,四(β-十二烷基巯基)丙酸季戊四醇酯。
10.聚酰胺稳定剂,例如铜盐组合碘化物和/或磷化合物以及二价锰的盐。
11.碱性共稳定剂,例如三聚氰胺,聚乙烯吡咯烷酮,双氰胺,氰脲酸三烯丙酯,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,蓖麻油酸钠和棕榈酸钾,邻苯二酚锑或邻苯二酚锌。
12.成核剂,例如无机物质,如滑石,金属氧化物类如二氧化钛或氧化镁,磷酸盐、碳酸盐或硫酸盐,优选其碱土金属盐;有机化合物如单或多羧酸类和它们的盐类,例如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”)。尤其优选的是1,3:2,4-双(3’,4’-二甲基苄叉基)山梨糖醇,1,3:2,4-二(对甲基二苄叉基)山梨糖醇,和1,3:2,4-二(苄叉基)山梨糖醇。
13.填料和增强剂,例如碳酸钙,硅酸盐,玻璃纤维,玻璃珠,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,木粉和其它天然产物的粉末或纤维,合成纤维。
14.其它添加剂,例如增塑剂,润滑剂,乳化剂,颜料,流变助剂,催化剂,流动调节剂,荧光增白剂,耐焰剂,抗静电剂,发泡剂和红外线(IR)吸收剂(adsorbex)。
优选的IR吸收剂是例如颜料,染料或者有机金属化合物。这样的颜料的例子是例如公开在JP-A-2003221523中。IR吸收性染料的例子公开在例如JP-A-2003327865或者EP-A-1306404中。IR吸收性有机金属化合物例如公开在EP-A-1266931或者化学文摘(Chemical Abstract)117;112529中。
15.苯并呋喃酮类和二氢吲哚酮类,例如公开在US4,325,863;US4,338,244;US5,175,312;US5,216,052;US5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839,EP-A-0591102或者EP-A-1291384中的那些或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,3-(2,3-二甲基苯基)-5,7-二叔丁基-苯并呋喃-2-酮或者3-(2-乙酰-5-异辛基苯基)-5-异辛基-苯并呋喃-2-酮。
该另外的添加剂典型的使用浓度是0.01-10%,基于待稳定的材料的总重量。
新颖的式I的液体聚合物化合物可以与酚抗氧化剂,光稳定剂和/或加工稳定剂一起使用。
组份(b)和如果需要的另外的添加剂可以通过已知的方法在配混之前或者配混过程中混入到合成聚合物中例如通过挤出,共挤出或者否则通过将溶解的或者分散的化合物施用到合成聚合物中,如果适宜,随后缓慢蒸发溶剂。
本发明还涉及一种母料或者浓缩物形式的组合物,其包含5-90重量%的量的组份(a)和5-80重量%的量的组份(b)。
组份(b)和如果需要的另外的添加剂还可以聚合之前或者聚合过程中或者在交联之前加入。
组份(b)(带有或者不带有另外的添加剂)可以以纯的形式或者装入到蜡、油或者聚合物中的胶囊的形式来加入到合成聚合物中。
组份(b)(带有或者不带有另外的添加剂)还可以喷涂到合成聚合物上。可以稀释其它的添加剂(例如上述的常规添加剂)或者它们的熔融物,目的是使它们也能够与这些添加剂一起喷涂到聚合物上。在聚合物催化剂去活化过程中通过喷涂加入是特别有利的,可以使用例如用于去活化的蒸汽来进行喷涂。
在球形方式聚合的聚烯烃的情况中,有利的是例如通过喷涂来施用组份(b)(带有或者不带有其它添加剂)。
以这种方式制备的合成聚合物能够以广泛的多种形式使用,例如作为泡沫、薄膜、纤维、带子、模塑组合物,作为型材或者作为涂料的基料,特别是粉末涂料,粘合剂、腻子或者特别是作为厚层聚烯烃模塑品,该模塑品长期与萃取性介质接触,例如诸如液体或者气体用的管道,薄膜,纤维,土工膜,带子,型材或者槽子。
优选的厚层聚烯烃模塑品的层厚度是1-50mm,特别是1-30mm,例如2-10mm。
根据本发明的组合物可以有利的用于制备不同的成型制品。例子是:
I-1)漂浮装置,海上应用,浮桥,浮标,用于甲板,码头,船舶,皮船(kayak),桨和海滩加固件的塑料材(lumber)。
I-2)汽车应用,特别是缓冲器,仪表盘,电池,后面和前面衬里,车蓬下面的模塑零件,帽子架板,行李箱衬里,内衬,空气囊包皮,配件(灯)用电子模塑品,仪表盘玻璃,顶灯玻璃,仪器盘,外部衬里,车内装潢,汽车灯,大灯,停车灯,尾灯,停止灯,内饰和外饰;门板;储气罐;前侧玻璃;后窗;坐椅靠背,外壳,导线绝缘,密封用挤出型材,覆层,柱套,底盘零件,排气系统,燃料过滤器/填充物,燃料泵,燃料箱,车身侧面模塑件,可转换车顶,外镜,外饰,扣件/固定件,前舱(front end module),玻璃,铰链,车锁系统,货架/行李架,加压/脚踩零件,密封件,侧面冲击保护,消音器/隔音器和汽车遮阳篷。
I-3)道路交通装置,特别是标志牌,路标牌,汽车附件,警示三角,医用盒,头盔,轮胎。
I-4)用于飞机,铁路,机动车(汽车,摩托车)的装置,包括器具。
I-5)用于航天应用特别是火箭和卫星的装置,例如返回护罩。
I-6)用于建筑和设计,采矿应用,静音系统,街道避难所和掩体的装置。
II-1)一般的器具,盒子和覆盖物以及电/电子装置(个人电脑,电话,便携电话,打印机,电视机,音频和视频装置),花盆,卫星电视锅,和面板(panel)装置。
II-2)用于其它材料例如钢或者纺织品的护套。
II-3)用于电子工业特别是绝缘插头,尤其是计算机插头的装置,电和电子零件盒,印刷板,和电子数据存储用材料例如芯片,支票卡或者信用卡。
II-4)电器,特别是清洗机器,甩干机(tumbler),炉子(微波炉),洗碗机,混合器和熨斗。
II-5)灯用的罩子(例如路灯,灯罩)。
II-6)电线和电缆应用(半导体,绝缘和电缆套)。
II-7)冷凝器,冰箱,加热装置,空调,电子包封,半导体,咖啡机和真空清洁器用的箔片。
III-1)技术制品例如钝齿轮(齿轮),滑动配件,隔离器,螺杆,螺钉,把手和球形手柄。
III-2)动叶片,通风设备和风车翼,太阳能装置,游泳池,游泳池罩,池衬垫,池塘衬垫,壁厨,衣柜,隔离墙,板条墙,可折叠墙,屋顶,百叶窗(例如辊子百叶窗),配件,管道、套管和传送带之间的连接件。
III-3)卫生制品,特别是淋浴室,马桶,盖子和水槽。
III-4)卫生保健制品,特别是尿布(婴儿,成人失禁),妇女卫生用品,浴帘,刷子,垫子,浴盆,移动厕所,牙刷和床用便盆。
III-5)用于水,废水和化学品的管道(十字连通的或者不是),电线和电缆保护管,气体、油和污水用的管道,排水材料,下水管和排水系统。
III-6)任何几何形状(窗玻璃)和壁板的型材。
III-7)玻璃替代品,特别是挤出的或者共挤出的板,建筑玻璃(整体式、双或者多层),飞行器,学校,挤出片材,用于建筑玻璃、火车、运输、卫生制品、和温室的窗膜。
III-8)板(墙壁,切肉板),挤压涂料(照相纸,利乐无菌枕(tetrapack)和管道涂层),筒舱,木头替代品,塑料材,复合木板,墙壁,表面,家具,装饰片,楼面覆面层(内和外使用),地板,隔板道板和面砖。
III-9)入口和出口多支管。
III-10)水泥-,混凝土-,复合材料应用和覆盖物,壁板和覆层,扶手,扶栏,厨房台面,屋顶,屋顶片材,面砖和防水毡布。
IV-1)板(墙壁,切肉板),盘子,人造草,阿斯特洛草皮(astroturf),露天运动场(运动)用人造覆盖物,露天运动场(运动)用人造地板,和条带。
IV-2)机织织物,连续的和切断的纤维(地毯/卫生制品/土工布/单丝;过滤器;抹布/窗帘(遮光帘)/医学应用),散纤维(例如长袍/防护服应用),网状物,绳子,电缆,线,灯芯绒,丝,座位安全带,衣服,内衣裤,手套;靴子;胶靴,贴身内衣,外衣,游泳衣,运动装,雨伞(女用阳伞,遮阳伞),降落伞,滑翔降落伞,帆篷,“气圈绸”,野营制品,帐篷,气床垫,太阳床,吨(bulk)袋和袋子。
IV-3)隔膜、绝缘体、覆盖物和封条,其用于屋顶,隧道,仓库,池塘,仓库,墙顶隔膜,土工膜,游泳池,窗帘(遮光帘)/遮阳板,遮阳篷,天篷,壁纸,食品包装和包装材料(柔性的和坚固的),药品包装(柔性的和坚固的),气袋/安全带,胳膊垫和枕头,地毯,中央控制台,仪表板,驾驶室,门,空中控制台舱,门饰,船首缆,内部灯,内镜,包裹架,后行李罩,坐椅,驾驶杆,方向盘,纺织品和箱子装饰。
V)薄膜(包装,仓库,层压品,农业园艺,温室,覆根物,隧道,饲料储存间),货物包装,游泳池,垃圾袋,壁纸,拉伸膜,酒椰(raffia),脱盐膜,电池和连接器。
VI-1)食品包装和包装材料(柔性和坚固的),瓶子。
VI-2)存储系统例如盒子(板条箱),皮箱,箱柜,家用箱子,货盘,架子,轨道,螺丝盒,包裹和罐头。
VI-3)药筒,注射器,医学应用,用于任何运送的容器,垃圾筐和垃圾箱,垃圾袋,箱筐,灰尘箱,箱柜衬里,带轮子的箱,一般容器,用于水/废水/化学品/气体/油/汽油/柴油的槽子;槽子衬里,盒子,板条箱,电池盒,水槽,医学装置例如活塞,眼科用具,诊断装置,和医学泡罩包装。
VII-1)挤压涂料(照相纸,利乐无菌枕和管道涂层),任何种类的家用制品(例如用具,热水瓶/衣帽钩),紧固系统例如插头,电线和电缆夹子,拉链,闭合器,锁子和吸合锁扣。
VII-2)承载装置,休闲制品例如运动和健康装置,体操垫,滑雪靴,溜冰鞋,雪橇,滑雪板(big foot),运动表面(例如网球场);用于瓶子的螺旋盖、盖子和塞子,以及罐头。
VII-3)一般家具,发泡制品(软垫,冲击吸收器),泡沫材料,海绵,盖碗布,垫子,花园椅子,露天运动场座位,台子,长沙发椅,玩具,建筑工具箱(木板/图/球),剧场,滑动装置和游戏车辆。
VII-4)用于光学和磁数据存储的材料。
VII-5)厨房用品(吃、喝、烹饪、储存)。
VII-6)CD、盒式磁带和录像带盒;DVD电子产品,任何种类的办公用品(圆珠笔,邮票和印泥,鼠标,架子,轨道),任何体积和容量的瓶子(饮料,清洁剂,化妆品包括香水),和胶带。
VII-7)鞋袜(鞋子/鞋袜底),鞋垫,鞋罩,粘合剂,结构粘合剂,食品盒(水果,蔬菜,肉,鱼),合成纸,瓶子标签,长沙发椅,人造关节(人用),印刷板(柔性印刷),印刷线路板和显示工艺。
VII-8)填充聚合物装置(滑石,粉笔,陶土(高岭土),硅灰石,颜料,炭黑,TiO2,云母,纳米复合材料,白云石,硅酸盐,玻璃,石棉)。
非常令人感兴趣的是包含作为组份(a)的纤维和织物的组合物,其用于无纺医学织物和相关的服装(外科长袍,帷帘,绷带),建筑织物(房屋包缠料,屋顶,游泳池包缠料)和家具(地毯,亚麻台布,浴帘)。
特别感兴趣的是包含作为组份(a)的纤维和无纺布的组合物。
因此,本发明一种另外的实施方案涉及一种成型制品,特别是薄膜,管道,型材,瓶子,槽子或者容器,如上所述的含有纤维的组合物。
本发明一种另外的实施方案涉及一种含有上述组合物的模塑制品。该模塑具体是通过注塑、吹塑、压塑、滚塑或者搪塑或者挤塑来完成的。
如上所述,待保护的有机材料优选是有机聚合物,特别是合成聚合物。特别有利的是保护热塑性材料特别是聚烯烃。具体的,应当强调的是式I的聚合物化合物作为加工稳定剂(热稳定剂)的优异效力。为此目的,它们有利的是在其加工之前或者过程中加入到聚合物中。但是,其它聚合物(例如弹性体)或者润滑剂或者液压油也可以被稳定来抗降解,例如光产生的或者热氧化性降解。弹性体列于上述的可能的有机材料清单中。
合适的润滑剂和液压油是基于例如矿物油或者合成油或者其混合物。该润滑剂对于本领域技术人员来说是已知的并描述于相关的专门文献中,例如在Dieter Klamann的“Schmiermittelstoffe und verwandteProdukte”[Lubricants and Related Products](Verlag Chemie,Weinheim,1982)中,在Schewe-Kobek的“Das Schmiermittel-Taschenbuch”[TheLubricant Handbook](Dr.Alfred Hüthig-Verlag,Heidelberg,1974)和在“Ullmanns Enzyklopadie der technischen Chemie”[Ullmann′sEncyclopedia of Industrial Chemistry],第13卷第85-94页(Verlag Chemie,Weinheim,1977)中。
本发明的一种优选的实施方案因此是式I的液体聚合物化合物或者通过将式II的化合物或者式II的化合物的混合物与式III的化合物或者式III的化合物的混合物进行反应来获得的聚合物产物的用途,其用于保护有机材料抗氧化,热或者光引起的降解。
该新颖的式I的液体聚合物化合物是以显著优异的水解稳定性和有利的颜色行为(即在加工过程中有机材料的低的变色)而著称的。
用式I的聚合物化合物稳定的有机材料获得了特别好的抗光诱导降解的保护。
本发明所以还涉及一种稳定有机材料抗氧化、热或者光引起的降解的方法,其包括将至少一种式I的聚合物化合物或者至少一种通过将式II的化合物或者式II的化合物的混合物与式III的化合物或者式III的化合物的混合物进行反应来获得的聚合物产物混入到所述的材料中,或者施用到所述的材料。
在稳定有机材料的方法中,优选的液体式I的聚合物化合物和任选的另外的添加剂与所述的用于组合物的这些是相同的。
下面的实施例进一步说明本发明。份数或者百分比指的是重量。
进一步概括地陈述如下:
为了除去氧气和水份,在使用之前将全部的聚合容器抽空和用氩气吹扫。然后将反应混合物在氩气氛下聚合。在聚合反应开始时,全部的起始材料是均匀溶解的。转化率的测定是使用过滤从聚合物亚磷酸酯或者亚膦酸酯中除去未反应的单体或者盐,并真空干燥(0.002托)至少60分钟来进行的。然后称重所得到的液体。聚合物亚磷酸酯和亚膦酸酯的表征是通过31P-NMR,使用BRUKER AVANCE200 INSTRUMENT和凝胶渗透色谱法(GPC)来进行的。后者是使用FLUX INSTRUMENTS的RHEOS4000来进行的。四氢呋喃(THF)被用作溶剂并以1ml/min的速度泵入。将两个色谱柱依次放置:Polymer INSTRUMENTS,Shropshire,英国的型号Pigel 5μm混合的-C。测量在40℃进行。该色谱柱用低多分散性的聚苯乙烯(Mn为200-2000000道尔顿)来校准。检测使用ERCATECH AG的RI-Detector ERC-7515A在30℃进行。
实施例1:化合物101的制备。
在装备有机械搅拌器、滴液漏斗、冷凝器和温度计的三颈圆底烧瓶中加入溶解在240ml甲苯中的31.25g(0.08mol)的3-(3,5-二-叔丁基-4-羟基-苯基)丙酸异辛酯和22.3ml(0.16mol)的三乙胺。将该溶液搅拌并加热到50℃。将7.0g(0.08mol)的PCI3在40ml甲苯中的溶液在50℃逐滴加入到该反应混合物中。反应混合物变为黄色悬浮液。在50℃搅拌一整夜之后,在203ppm的31P-NMR的信号显示PCl3已经完全反应。
在50℃向该悬浮液中逐滴加入9.45g(0.08mol)的1,6-己二醇和22.3ml(0.16mol)三乙胺的混合物。4小时后,31P-NMR显示离析物(信号在205ppm)已经完全反应,并且出现了141-143ppm(聚合物亚磷酸酯)的信号。为了除去全部可能的氯端基,加入1ml甲醇并将该反应混合物搅拌30分钟。在过滤沉淀物(铵盐)之后,将滤出液使用旋转蒸发器在40℃进行浓缩。残留物溶解在庚烷中,再次过滤和蒸发得到化合物101,其是黄色液体。分子量大约是10000g/mol,通过GPC测定。
实施例2:化合物102的制备。
化合物102类似于实施例1的化合物101来制备,使用3-(3,5-二-叔丁基-4-羟基苯基)丙酸甲酯代替相应的异辛基酯。化合物102是一种黄色液体,分子量大约是9000g/mol(通过GPC测量)。
实施例3:化合物103的制备。
在装备有机械搅拌器、滴液漏斗、冷凝器和温度计的三颈圆底烧瓶中加入溶解在240ml甲苯中的23.39g(0.08mol)的3-(3,5-二-叔丁基-4-羟基-苯基)丙酸甲酯和22.3ml(0.16mol)的三乙胺。将该溶液搅拌并加热到50℃。将7.0g(0.08mol)的PCl3在40ml甲苯中的溶液在50℃逐滴加入到该反应混合物中。反应混合物变为黄色悬浮液。在50℃搅拌一整夜之后,在205ppm的31P-NMR的信号显示PCl3已经完全反应。
在50℃向该悬浮液中逐滴加入9.45g(0.08mol)的N-甲基二乙醇胺和22.3ml(0.16mol)三乙胺的混合物。4小时后,31P-NMR显示反应完成,并且出现138-142ppm的信号(聚合物亚磷酸酯)。为了除去全部可能的氯端基,加入1ml甲醇并将该反应混合物搅拌30分钟。在过滤沉淀物(铵盐)之后,将滤出液使用旋转蒸发器在40℃进行浓缩。残留物溶解在庚烷中,再次过滤和蒸发得到化合物103,其是黄色液体。分子量大约是3000g/mol,通过GPC测定。
实施例4:化合物104的制备。
化合物104类似于实施例1的化合物101来制备,使用3-(3-叔丁基-4-羟基苯基)丙酸甲酯代替3-(3,5-二-叔丁基-4-羟基苯基)丙酸异辛酯。化合物104是一种黄色液体,分子量大约是25000g/mol(通过GPC测量)。
实施例5:化合物105的制备。
化合物105类似于实施例3的化合物103来制备,使用3-(3-叔丁基-4-羟基苯基)丙酸甲酯代替3-(3,5-二-叔丁基-4-羟苯基)丙酸甲酯。化合物105是一种白色液体,分子量大约是1400g/mol(通过GPC测量)。
实施例6:化合物106-110的制备。
下面的低聚物亚磷酸酯类似于前述的实施例1-5来制备:
(106)[Mn(g/mol)8900]
(107)[Mn(g/mol)2400]
(108)[Mn(g/mol)2100]
实施例7:化合物111的制备。
在25°-30℃和40分钟内向139.0g(1000mmol)三氯化磷、6.0g(60mmol)N-甲基吡咯烷酮在30g甲苯中的溶液中逐滴加入103.7g(500mmol)2,4-二-叔丁基苯酚在70g甲苯中的溶液。将所形成的溶液加热到30℃并用氮气鼓泡另外2.5小时。将反应冷却到环境温度,在60℃真空(150mmHg)除去多余的三氯化磷。然后在所形成的二氯亚磷酸酯(phosphorodichloridite)溶液中加入112g(1100mmol)三乙胺,随后过滤除去任何的固体。在该滤出液中逐滴加入100g(500mmol)的PEG200,同时保持反应温度在50℃以下。加入后,使该反应混合物搅拌另外30min。然后加入总共6.0g(100mmol)的异丙醇到该混合物中并搅拌另外15分钟。过滤反应物质,将滤出液在70°-75℃真空浓缩来得到黄色的粘浆料(化合物111)。31P NMR(400MHz)(苯-d6)(ppm):135.GPC:MW=26638。
实施例8:化合物112的制备。
重复实施例7的程序,使用72.4g(525mmol)的三氯化磷、4.0g(12mmol)的四丁基溴化铵、103.4g(500mmol)的2,4-二-叔丁基苯酚、103g(1020mmol)的三乙胺、120g(400mmol)的PEG300、6.0g(100mmol)异丙醇和总共110g的甲苯。收集黄色的粘浆料(化合物112)。31PNMR(400MHz)(苯-d6)(ppm):147.GPC:MW=4668。
实施例9:化合物113的制备。
重复实施例7的程序,使用35.3g(260mmol)的三氯化磷、72.1g(250mmol)的3,5-二-叔丁基-4-羟基苯丙酸甲酯、103g(1020mmol)的三乙胺、50g(250mmol)的PEG200、4.0(67mmol)的异丙醇和总共300g甲苯。收集黄色的粘浆料(化合物113)。31P NMR(400MHz)(苯-d6)(ppm):156.GPC:MW=5458。
实施例10:化合物114的制备。
重复实施例7的程序,使用140.1g(1000mmol)的三氯化磷、6.3g(64mmol)的N-甲基吡咯烷酮、121g(500mmol)的3-叔丁基-4-羟基苯丙酸甲酯、113g(1020mmol)的三乙胺、100g(500mmol)的PEG200、6.0g(100mmol)异丙醇和总共175g甲苯。收集黄色的粘浆料(化合物114)。31P NMR(400MHz)(苯-d6)(ppm):147.GPC:MW=6312。
实施例11:化合物115的制备。
重复实施例7的程序,使用27.5g(200mmol)的三氯化磷、0.49g(5mmol)的N-甲基吡咯烷酮、23.6g(100mmol)的3-叔丁基-4-羟基苯丙酸甲酯、30.4g(300mmol)的三乙胺、15g(100mmol)的三甘醇、0.60g(10mmol)的异丙醇和总共200g甲苯。收集黄色的粘浆料(化合物115)。31P NMR(300MHz)(苯-d6)(ppm):137.GPC:MW=6845。
实施例12:化合物116的制备。
重复实施例7的程序,使用27.5g(200mmol)的三氯化磷、0.49g(5mmol)的N-甲基吡咯烷酮、23.6g(100mmol)的3-叔丁基-4-羟基苯丙酸甲酯、30.4g(300mmol)的三乙胺、10.6g(100mmol)的二甘醇、0.60g(10mmol)的异丙醇和总共200g甲苯。收集黄色的粘浆料(化合物116)。31P NMR(300MHz)(苯-d6)(ppm):137.GPC:MW=3891。
实施例13:化合物117的制备
重复实施例7的程序,使用35.3g(260mmol)的三氯化磷、72.1g(250mmol)的3,5-二叔丁基-4-羟基苯丙酸甲酯、51.0g(510mmol)的三乙胺、38g(250mmol)的三甘醇、4.0g(67mmol)的异丙醇和总共300g甲苯。收集黄色的粘浆料(化合物117)。31P NMR(300MHz)(苯-d6)(ppm):158.GPC:MW=1187。
实施例14:化合物118的制备。
重复实施例7的程序,使用69.5(500mmol)的三氯化磷、3.0g(30mmol)的N-甲基吡咯烷酮、51.8(250mmol)的2,4-二叔丁基苯酚、56.8(560mmol)的三乙胺、37.5(250mmol)的三甘醇、3.0g(50mmol)的异丙醇和总共110g甲苯。收集黄色的粘浆料(化合物118)。GPC:MW=27045。
实施例15:多次挤出的聚丙烯的稳定性。
将1.3kg聚丙烯粉末[Profax6501(RTM)](其已经用0.025%的Irganox1076(RTM)[3-[3,5-二-叔丁基-4-羟基苯基]丙酸正十八烷基酯]进行了预稳定,具有在230℃/2.16kg测量的熔融指数3.2)与0.05%的Irganox 1010(RTM)[四[3-(3,5-二-叔丁基-4-羟基苯基)丙酸季戊四醇酯]、0.05%的硬脂酸钙、0.03%的二氢铝碳酸镁(dihydrotalcite)[DHT4A(RTM),Kyowa Chemical Industry co.,Ltd.,Mg4.5Al2(OH)13CO3·3.5H2O]和0.05%的根据表1的式I化合物进行共混。然后将该共混物在具有20mm料筒直径和400mm长度的挤出机中以100rpm挤出,3个加热区调整为下面的温度:260℃,270℃,280℃。将挤出物通过水浴牵引使其冷却,然后造粒。将该粒料重复挤出。在3次挤出之后测量熔融指数(230℃/2.16kg)。熔融指数的大幅增加表明了明显的链降解,即差的稳定性。结果汇总在表1中。
表1:
实施例 | 式I的化合物 | 3次挤出之后的熔融指数 |
15aa) | 无 | 19.0 |
15bb) | 化合物101 | 8.2 |
15cb) | 化合物102 | 7.9 |
15db) | 化合物103 | 8.0 |
15eb) | 化合物104 | 8.1 |
15fb) | 化合物105 | 7.9 |
a)对比实施例。
b)根据本发明的实施例。
实施例16:多次挤出的线性低密度聚乙烯的稳定性。
将1kg金属茂催化的乙烯/己烷线性低密度聚乙烯粉末[1的熔融指数(190℃/2.16kg);0.918的密度](其没有任何的添加剂)与基础稳定体系进行干混,该体系包含0.05%的Irganox 1076(RTM)[3-[3,5-二-叔丁基-4-羟基苯基]丙酸正十八烷基酯]和0.08%的聚合物加工助剂、DynamarFX-5920A(RTM)。然后向该基础稳定体系中加入等摩尔浓度的表2的化合物。然后将这个充分共混的混合物在具有25.4mm料筒直径和400mm长度的挤出机中在氮气下以30rpm挤出,加热区调整到使熔体温度为190℃。将挤出物通过水浴牵引使其冷却,然后造粒。然后将该零通过的粒子在同样的挤出机中以30rpm重复挤出5次,开放到空气,并将加热区调整到使熔体温度为260℃。在5次挤出之后测量熔融指数(190℃/2.16kg)。熔融指数的降低表明分子量增加或者交联,即差的稳定性。结果汇总在表2中。
表2:
实施例 | 式I的化合物 | 在开放到空气260℃第1次挤出之后的熔融指数 | 在开放到空气260℃第3次挤出之后的熔融指数 | 在开放到空气260℃第5次挤出之后的熔融指数 |
16aa) | 没有 | 0.89 | 0.81 | 0.75 |
16bb) | 106 | 1.01 | 0.98 | 0.93 |
16cb) | 107 | 1.03 | 1.01 | 0.95 |
16db) | 108 | 1.04 | 1.01 | 0.98 |
16eb) | 109 | 1.01 | 0.98 | 0.96 |
16fb) | 110 | 1.00 | 0.95 | 0.88 |
a)对比实施例。
b)根据本发明的实施例。
实施例17:线性低密度聚乙烯二次挤出的颜色稳定性。
将实施例16的零通过的挤出物压塑成为1mm的薄膜。将一组放入气体褪色室中,并曝露于60℃的氮氧化物中;另一组放入没有氮氧化物的60℃的烘箱中作为对照。每七天测量一次颜色,这里颜色变深表示聚合物和酚抗氧化剂缺乏适当的保护;即差的稳定性。结果汇总在表3和4中。
表3:
实施例 | 式I的化合物 | 在60℃的气体褪色室中0天之后的黄度指数 | 在60℃的气体褪色室中14天之后的黄度数 | 在60℃的气体褪色室中28天之后的黄度指数 |
17aa) | 没有 | 1.16 | 9.07 | 14.27 |
17bb) | 106 | 1.20 | 3.03 | 9.39 |
17cb) | 107 | 1.53 | 4.95 | 10.01 |
17db) | 108 | 1.41 | 7.83 | 14.75 |
17eb) | 109 | 1.10 | 4.23 | 11.06 |
17fb) | 110 | 1.42 | 7.75 | 14.53 |
表4
实施例 | 式I的化合物 | 在60℃的烘箱中老化0天之后的黄度指数 | 在60℃的烘箱中老化14天之后的黄度指数 | 在60℃的烘箱中老化28天之后的黄度指数 |
17ga) | 没有 | 1.35 | 1.66 | 1.94 |
17hb) | 106 | 1.07 | 1.28 | 1.37 |
17ib) | 107 | 1.41 | 1.76 | 2.13 |
17jb) | 108 | 1.41 | 2.10 | 2.52 |
17kb) | 109 | 1.18 | 1.32 | 1.41 |
17lb) | 110 | 1.32 | 1.82 | 2.26 |
a)对比实施例。
b)根据本发明的实施例。
Claims (18)
4.根据权利要求1的化合物,其中R2是氢。
5.根据权利要求1的化合物,其中R3是C1-C8烷基。
7.根据权利要求1的化合物,其中X和Y是-O-。
11.一种组合物,其包含
a)受到氧化、热或者光易于引起降解的有机材料,和
b)至少一种根据权利要求1的式I的聚合物化合物或者至少一种根据权利要求9的聚合物产物。
12.根据权利要求11的组合物,其包含除了组份(a)和(b)之外的另外的添加剂。
13.根据权利要求12的组合物,其中该另外的添加剂选自酚抗氧化剂、光稳定剂和加工稳定剂。
14.根据权利要求11的组合物,其中组份(a)是天然的、半合成的或者合成聚合物。
15.根据权利要求11的组合物,其中组份(a)是热塑性聚合物。
16.根据权利要求11的组合物,其中组份(b)以0.01-10%的量而存在,基于组份(a)的重量。
17.一种用于稳定有机材料抗氧化、热或者光引起的降解的方法,其包括将至少一种权利要求1所定义的式I的聚合物化合物或者至少一种权利要求10的聚合物产物混入到所述的材料中,或者施用到所述的材料。
18.根据权利要求1的式I的聚合物化合物或者权利要求10所定义的聚合物产物的用途,其作为稳定剂用来保护有机材料抗氧化、热或者光引起的降解。
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CN (1) | CN101511913B (zh) |
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CA (1) | CA2662035A1 (zh) |
DE (1) | DE602007007789D1 (zh) |
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CN113651849A (zh) * | 2021-07-23 | 2021-11-16 | 江苏常青树新材料科技股份有限公司 | 聚合型无酚、低味的亚磷酸酯及其制备方法 |
CN114616264A (zh) * | 2019-09-06 | 2022-06-10 | 弗劳恩霍夫应用研究促进协会 | 低聚物或聚合物、组合物、低聚物或聚合物的用途和中间体 |
CN114805105A (zh) * | 2022-05-20 | 2022-07-29 | 唐山科澳化学助剂有限公司 | 一种抗氧剂1098的合成工艺 |
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JP5771630B2 (ja) * | 2010-02-19 | 2015-09-02 | ドーヴァー ケミカル コーポレイション | アルキルフェノールを含まない液体高分子ホスファイトポリマー安定剤 |
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US8981042B2 (en) | 2010-02-19 | 2015-03-17 | Dover Chemical Corporation | Cycloaliphatic polyphosphite polymer stabilizers |
US9855682B2 (en) | 2011-06-10 | 2018-01-02 | Columbia Insurance Company | Methods of recycling synthetic turf, methods of using reclaimed synthetic turf, and products comprising same |
US9745425B2 (en) | 2012-06-22 | 2017-08-29 | Dover Chemical Corporation | Cycloaliphatic polyphosphite |
MX2016003734A (es) | 2013-09-27 | 2016-08-04 | Basf Se | Composiciones de poliolefina para materiales de construccion. |
US9470008B2 (en) * | 2013-12-12 | 2016-10-18 | Crystal Lagoons (Curacao) B.V. | System and method for maintaining water quality in large water bodies |
US11472928B2 (en) | 2018-02-14 | 2022-10-18 | Dover Chemical Corporation | Use of a polymeric polyphosphite as a polymer processing aid |
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CN114616264A (zh) * | 2019-09-06 | 2022-06-10 | 弗劳恩霍夫应用研究促进协会 | 低聚物或聚合物、组合物、低聚物或聚合物的用途和中间体 |
CN114616264B (zh) * | 2019-09-06 | 2024-03-01 | 弗劳恩霍夫应用研究促进协会 | 低聚物或聚合物、组合物、低聚物或聚合物的用途和中间体 |
CN113651849A (zh) * | 2021-07-23 | 2021-11-16 | 江苏常青树新材料科技股份有限公司 | 聚合型无酚、低味的亚磷酸酯及其制备方法 |
CN114805105A (zh) * | 2022-05-20 | 2022-07-29 | 唐山科澳化学助剂有限公司 | 一种抗氧剂1098的合成工艺 |
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