CN101163735B - 低残余醛含量的聚醚多元醇、聚酯多元醇和聚氨基甲酸酯 - Google Patents
低残余醛含量的聚醚多元醇、聚酯多元醇和聚氨基甲酸酯 Download PDFInfo
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- CN101163735B CN101163735B CN2006800130329A CN200680013032A CN101163735B CN 101163735 B CN101163735 B CN 101163735B CN 2006800130329 A CN2006800130329 A CN 2006800130329A CN 200680013032 A CN200680013032 A CN 200680013032A CN 101163735 B CN101163735 B CN 101163735B
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- component
- alkyl
- phenyl
- butyl
- tertiary butyl
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- 229920000570 polyether Polymers 0.000 title claims abstract description 48
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 40
- 239000004814 polyurethane Substances 0.000 title claims abstract description 39
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 39
- 229920005906 polyester polyol Polymers 0.000 title claims abstract description 33
- 229920005862 polyol Polymers 0.000 title abstract description 4
- 150000003077 polyols Chemical class 0.000 title abstract description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title description 20
- 239000000203 mixture Substances 0.000 claims abstract description 50
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 12
- 239000002530 phenolic antioxidant Substances 0.000 claims abstract description 10
- -1 4-octyl Chemical group 0.000 claims description 137
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 88
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 36
- 239000001301 oxygen Substances 0.000 claims description 31
- 229910052760 oxygen Inorganic materials 0.000 claims description 31
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 150000001412 amines Chemical class 0.000 claims description 17
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 15
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 claims description 13
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 claims description 3
- DMLLDZGHGNLZNW-UHFFFAOYSA-N 4-octyl-n-phenylaniline Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=CC=CC=C1 DMLLDZGHGNLZNW-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 238000005516 engineering process Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229960004279 formaldehyde Drugs 0.000 claims 2
- 235000019256 formaldehyde Nutrition 0.000 claims 2
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 239000000356 contaminant Substances 0.000 abstract 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract 1
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 description 29
- 229910052757 nitrogen Inorganic materials 0.000 description 27
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 24
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000005056 polyisocyanate Substances 0.000 description 19
- 229920001228 polyisocyanate Polymers 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 11
- 230000002265 prevention Effects 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 10
- 235000006708 antioxidants Nutrition 0.000 description 10
- 239000012964 benzotriazole Substances 0.000 description 9
- 239000006260 foam Substances 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical group [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 7
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 7
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 239000005864 Sulphur Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 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
- MBAUOPQYSQVYJV-UHFFFAOYSA-N octyl 3-[4-hydroxy-3,5-di(propan-2-yl)phenyl]propanoate Chemical compound OC1=C(C=C(C=C1C(C)C)CCC(=O)OCCCCCCCC)C(C)C MBAUOPQYSQVYJV-UHFFFAOYSA-N 0.000 description 6
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 5
- CYHYIIFODCKQNP-UHFFFAOYSA-N 5,7-ditert-butyl-3-(3,4-dimethylphenyl)-3h-1-benzofuran-2-one Chemical compound C1=C(C)C(C)=CC=C1C1C(C=C(C=C2C(C)(C)C)C(C)(C)C)=C2OC1=O CYHYIIFODCKQNP-UHFFFAOYSA-N 0.000 description 5
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- QYSPWTBYSZPOCJ-UHFFFAOYSA-N 1-hydroxypentadecane-3-sulfonic acid Chemical compound CCCCCCCCCCCCC(CCO)S(O)(=O)=O QYSPWTBYSZPOCJ-UHFFFAOYSA-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
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-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
- 229920005830 Polyurethane Foam Polymers 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 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
- 229940035422 diphenylamine Drugs 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 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
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000011496 polyurethane foam Substances 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- 229940057402 undecyl alcohol Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- GQBHYWDCHSZDQU-UHFFFAOYSA-N 4-(2,4,4-trimethylpentan-2-yl)-n-[4-(2,4,4-trimethylpentan-2-yl)phenyl]aniline Chemical compound C1=CC(C(C)(C)CC(C)(C)C)=CC=C1NC1=CC=C(C(C)(C)CC(C)(C)C)C=C1 GQBHYWDCHSZDQU-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 3
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 230000003078 antioxidant effect Effects 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 3
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 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
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- KWUZCAVKPCRJPO-UHFFFAOYSA-N n-ethyl-4-(6-methyl-1,3-benzothiazol-2-yl)aniline Chemical compound C1=CC(NCC)=CC=C1C1=NC2=CC=C(C)C=C2S1 KWUZCAVKPCRJPO-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000012855 volatile organic compound Substances 0.000 description 3
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 3
- GPOGLVDBOFRHDV-UHFFFAOYSA-N (2-nonylphenyl) dihydrogen phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(O)O GPOGLVDBOFRHDV-UHFFFAOYSA-N 0.000 description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 2
- 0 *c(cc1C2c3c(*=C)c(*)c(*)c(*=C)c3)cc(*)c1OC2=C Chemical compound *c(cc1C2c3c(*=C)c(*)c(*)c(*=C)c3)cc(*)c1OC2=C 0.000 description 2
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-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
- 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 2
- SLUKQUGVTITNSY-UHFFFAOYSA-N 2,6-di-tert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 SLUKQUGVTITNSY-UHFFFAOYSA-N 0.000 description 2
- ZFABKRKKUNPJSL-UHFFFAOYSA-N 2-octylphenol 2H-thiazine Chemical compound S1NC=CC=C1.C(CCCCCCC)C1=C(C=CC=C1)O ZFABKRKKUNPJSL-UHFFFAOYSA-N 0.000 description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
- BKZXZGWHTRCFPX-UHFFFAOYSA-N 2-tert-butyl-6-methylphenol Chemical compound CC1=CC=CC(C(C)(C)C)=C1O BKZXZGWHTRCFPX-UHFFFAOYSA-N 0.000 description 2
- DKHJONPHCWFBAX-UHFFFAOYSA-N 3-butyl-3h-1-benzofuran-2-one Chemical group C1=CC=C2C(CCCC)C(=O)OC2=C1 DKHJONPHCWFBAX-UHFFFAOYSA-N 0.000 description 2
- SXGXVOZDLWXVKM-UHFFFAOYSA-N 3-dodecylpyrrolidine-2,5-dione Chemical compound CCCCCCCCCCCCC1CC(=O)NC1=O SXGXVOZDLWXVKM-UHFFFAOYSA-N 0.000 description 2
- FEPGXTZVICYACM-UHFFFAOYSA-N 4-butyl-3-phenyl-3H-1-benzofuran-2-one Chemical group C1=2C(CCCC)=CC=CC=2OC(=O)C1C1=CC=CC=C1 FEPGXTZVICYACM-UHFFFAOYSA-N 0.000 description 2
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- MSGFMKMFGGXSTO-UHFFFAOYSA-N C(C)(C)(C)C=1C=C(C(=CC1O)CN)CCCC Chemical compound C(C)(C)(C)C=1C=C(C(=CC1O)CN)CCCC MSGFMKMFGGXSTO-UHFFFAOYSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- Polymers & Plastics (AREA)
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- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明描述了预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的方法,其包含向所述聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中结合入有效量的a)酚类抗氧剂,b)一种或者多种选自以下的化合物(i)胺类抗氧化剂,(ii)苯并呋喃-2-酮,和(iii)亚磷酸酯或者亚膦酸酯,或者(iv)其混合物。
Description
本发明涉及预防在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的方法,包括向所述聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中结合入有效量的(a)酚类抗氧剂,和(b)一种或者多种选自以下的化合物:(i)胺类(aminic)抗氧化剂,(ii)苯并呋喃-2-酮,和(iii)亚磷酸酯或者亚膦酸酯,或者(iv)其混合物。
酚类抗氧剂作为聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯的稳定剂的用途是已知的,例如,参见H.Zweifel;Plastic AdditivesHandbook,第五版,Hanser Publishers,Munich,p88-109(2001)。
已知的稳定剂并不能在各方面都满足稳定剂需要满足的高要求,特别是关于储存寿命、吸水性、对水解敏感性、加工稳定性、色彩性能、挥发性、迁移行为、兼容性和防止光线中的改善方面。另外,在汽车工业中强烈需要显著降低挥发性有机化合物(VOC)并且特别是气态排放物(FOG)的量。气态排放物通常还与“成雾”现象相关,其中被蒸发的挥发性物质可能会在汽车风板上浓缩,从而导致在窗口产生沉积。此外,被褥、家具和地毯垫面泡沫的最终用户还向弹性海绵板的生产商施加压力。比如催化剂、表面活性剂、阻燃剂、抗氧化剂的辅助添加剂会促进聚氨基甲酸酯泡沫的排放。VOC的主要来源是比如硅酮表面活性剂和胺催化剂的添加剂。当前,汽车工业集中在降低和/或消除与某些或者用作生产塑料汽车部件的原材料或者为其降解产物的化学品相关的排放。目标化学品例如为醛,比如,例如为甲醛、乙醛、丙醛;甲苯和苯乙烯。我们还发现,聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯的降解产物也可以是醛,比如,例如为甲醛、乙醛或者丙醛。
现在,我们发现,包含酚类抗氧剂和第二共稳定剂的稳定剂混合物在降低聚醚多元醇及其形成的聚氨基甲酸酯中甲醛和乙醛水平方面表现出极其优异的效力。
因此,本发明涉及预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中醛式污染物形成的方法,其包含向所述聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中结合入有效量的
a)酚类抗氧剂,
b)一种或者多种选自以下的化合物
(i)胺类抗氧化剂,
(ii)苯并呋喃-2-酮,和
(iii)亚磷酸酯或者亚膦酸酯,或者
(iv)其混合物。
优选作为组分(a)的酚类抗氧剂为式I化合物
其中
R1为氢或者C1-C4烷基,
n为1、2、3或者4,
Y为氢或者-NH-;和
如果n为1,
R2为C1-C25烷基;和,
如果n为2,
R2为C2-C12亚烷基、被氧或者硫中断的C4-C12亚烷基;或者,如果Y为-NH-,则R2另外是直接键;和,
如果n为3,
如果n为4,
R2为C4-C10烷烃四基。
具有直至25个碳原子的烷基为支链或者直链基团,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。R1优选定义为甲基和叔丁基。R2的特别优选的定义为C1-C20烷基,特别是C1-C18烷基,例如C4-C18烷基。R2的特别优选的定义为C8-C18烷基,特别是C14-C18烷基,例如C18烷基。
C2-C12亚烷基是支链或者直链基团,例如亚乙基、亚丙基、四亚甲基、五亚甲基、六亚甲基、七亚甲基、八亚甲基、十亚甲基或者十二亚甲基。R2的优选定义为,例如,C2-C10亚烷基,特别是C2-C8亚烷基。R2的特别优选定义为,例如,C4-C8亚烷基,特别是C4-C6亚烷基,例如六亚甲基。
被氧或者硫中断的C4-C12亚烷基可以被中断一次或者多次,并且为例如,-CH2-O-CH2CH2-O-CH2-、-CH2-(O-CH2CH2-)2O-CH2-、-CH2-(O-CH2CH2-)3O-CH2-、-CH2-(O-CH2CH2-)4O-CH2-、-CH2CH2-O-CH2CH2-O-CH2CH2-或者-CH2CH2-S-CH2CH2-。R2的优选定义为,例如,被氧或者硫中断的C4-C10亚烷基,特别是被氧或者硫中断的C4-C8亚烷基,例如被氧或者硫中断的C4-C6亚烷基。R2的特别优选定义为-CH2CH2-O-CH2CH2-O-CH2CH2-或者-CH2CH2-S-CH2CH2-。具有4~10个碳原子的烷烃四基为,例如,(季戊基), 或者优选季戊基。
组分(a)还可以包含不同的式I空间位阻酚的混合物。
所涉及的预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中醛式污染物形成的方法包括,作为组分(a)的至少一种式I化合物的酚类抗氧剂,其中,如果n为1,则R2为C1-C20烷基。
预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中醛式污染物形成的优选方法,包括作为组分(a)的至少一种式I化合物,其中
如果n为2,
则R2为C2-C8亚烷基、被氧或者硫中断的C4-C8亚烷基;或者,如果Y为NH,则R2另外为直接键;和,
如果n为3,
则X为亚甲基,
如果n为4,
则R2为C4-C8烷烃四基。
同样预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中醛式污染物形成的优选方法,包括作为组分(a)的至少一种式I化合物,其中
R1为甲基或者叔丁基,
n为1、2、3或者4,
Y为氢或者-NH-;和,
如果n为1,
则R2为C8-C18烷基;和,
如果n为2,
则R2为C4-C6亚烷基,或者为被氧中断的C4-C6亚烷基;和,
如果n为3,
则X为亚甲基,
R2为和,
如果n为4,
则R2为C4-C6烷烃四基。
所考虑的预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中醛式污染物形成的方法,包括作为组分(a)的以下酚类抗氧剂:
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-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、侧链为直链或者支链的壬基苯酚(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.烷基硫代甲基苯酚,例如2,4-二辛基硫代甲基-6-叔丁基苯酚、2,4-二辛基硫代甲基-6-甲基苯酚、2,4-二辛基硫代甲基-6-乙基苯酚、2,6-二-十二烷基硫基甲基-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-羟基苯甲醚、3,5-二叔丁基-4-羟基苯甲醚、3,5-二叔丁基-4-羟苯基硬脂酸酯、二(3,5-二叔丁基-4-羟苯基)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.羟基化硫代二苯基醚,例如2,2’-硫代二(6-叔丁基-4-甲基苯酚)、2,2’-硫代二(4-辛基苯酚)、4,4’-硫代二(6-叔丁基-3-甲基苯酚)、4,4’-硫代二(6-叔丁基-2-甲基苯酚)、4,4’-硫代二(3,6-二-仲戊基苯酚)、4,4’-二(2,6-二甲基-4-羟苯基)二硫化物。
1.6.亚烷基二苯酚,例如2,2’-亚甲基二(6-叔丁基-4-甲基苯酚)、2,2’-亚甲基二(6-叔丁基-4-乙基苯酚)、2,2’-亚甲基二[4-甲基-6-(α-甲基环己基)苯酚]、2,2’-亚甲基二(4-甲基-6-环己基苯酚)、2,2’-亚甲基二(6-壬基-4-甲基苯酚)、2,2’-亚甲基二(4,6-二叔丁基苯酚)、2,2’-亚乙基二(4,6-二叔丁基苯酚)、2,2’-亚乙基二(6-叔丁基-4-异丁基苯酚)、2,2’-亚甲基二[6-(α-甲基苄基)-4-壬基苯酚]、2,2’-亚甲基二[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4’-亚甲基二(2,6-二叔丁基苯酚)、4,4’-亚甲基二(6-叔丁基-2-甲基苯酚)、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)丁烷、2,6-二(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、1,1-二(5-叔丁基-4-羟基-2-甲基-苯基)-3-正十二烷基巯基丁烷、乙二醇二[3,3-二(3’-叔丁基-4’-羟苯基)丁酸酯]、二(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯、二[2-(3’-叔丁基-2’-羟基-5’-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二甲酸酯、1,1-二-(3,5-二甲基-2-羟苯基)丁烷、2,2-二(3,5-二叔丁基-4-羟苯基)丙烷、2,2-二(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷巯基丁烷、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-苄基化金物,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、双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯、双(3,5-二-叔丁基-4-羟基-苄基)硫化物、异辛基-3,5-二-叔丁基-4-羟基苄基巯基乙酸酯。
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、二-十二烷基巯基乙基-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,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。
1.1 2.酰氨基酚,例如4-羟基月桂苯胺(hydroxylauranilide)、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)异氰脲酸酯、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-2,6,7-三氧二环[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)异氰脲酸酯、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-2,6,7-三氧二环[2.2.2]辛烷;3,9-双[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰基氧基)-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)丙酸与单-或多元醇的 酯,所述的醇如与甲醇、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)异氰脲酸酯、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-2,6,7-三氧二环[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、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)异氰脲酸酯、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-2,6,7-三氧二环[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)三亚甲基二酰胺、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)。
同样优选包含至少一种式I化合物作为组分(a)的方法,其中式I化合物为式Ia、Ib或者Ic化合物。
Irganox 1135、Irganox 1076和Irganox 1010是Ciba SpecialtyChemicals Inc的受保护商品名。
在新颖方法中作为组分(a)的式I化合物是已知的,并且有时可以商业获得。式I化合物的可能制备方法可以发现于,例如美国专利3,330,859或者3,960,928中。
优选作为组分(b)(i)的胺类抗氧化剂为式II化合物
其中
R25为C1-C18烷基、苯基-C1-C4烷基、C5-C12环烷基、苯基、萘基;其均被C1-C12烷基或者C1-C12烷氧基或者苄基或者α,α-二甲基苄基取代的苯基或者萘基,
R26为苯基、萘基;均被C1-C12烷基或者C1-C12烷氧基或者苄基或者α,α-二甲基苄基取代的苯基和萘基,或者
R25和R26形成式III的基团
其中
R27和R28为氢或者C1-C18烷基,
R29为氢,和
预防在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的优选方法包括作为组分(b)(i)的至少一种式II化合物的胺类抗氧化剂
其中
R25和R26形成式III的基团
其中
R27和R28为C6-C12烷基,
R29为氢,或者组分(b)(i)为通过二苯胺与二异丁烯反应获得的技术混合物,包括
α)二苯胺;
β)4-叔丁基二苯胺;
γ)以下组的化合物
i)4-叔辛基二苯胺,
ii)4,4’-二叔丁基二苯胺,
iii)2,4,4’-三叔丁基二苯胺,
δ)以下组的化合物
i)4-叔丁基-4’-叔辛基二苯胺,
ii)o,o’、m,m’或者p,p’-二叔辛基二苯胺,
iii)2,4-叔丁基-4’-叔辛基二苯胺,
ε)以下组的化合物
i)4,4’-二叔辛基二苯胺,
ii)2,4-叔辛基-4’-叔丁基二苯胺,和其中存在不超过按重量计5%的组分α),按重量计8~15%的组分β),按重量计24~32%的组分γ),按重量计23~34%的组分δ)和按重量计21~34%的组分ε)。
烷基取代基可以含有直至18个碳原子。所述取代基的一般实例为甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十六烷基或者十八烷基和相应的支化异构体,优选叔丁基、异-辛基和异-十二烷基。
预防在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的特别优选方法包括作为组分(b)(i)的以下胺类抗氧化剂:
预防在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的优选方法,其中包括作为组分(b)(i)的以下胺类抗氧化剂:
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、辛烷化的二苯胺(例如p,p’-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、4-十二烷酰基氨基苯酚、4-十八烷酰基氨基苯酚、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。
上述胺类抗氧化剂是已知的化合物;它们大多数可以商业获得。
以下化合物是特别适于在根据本发明的方法中作为组分(b)(ii)的苯并呋喃-2-酮稳定剂的实例: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’-二[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;5,7-二-叔丁基-3-苯基-苯并呋喃-2-酮;5,7-二-叔丁基-3-(3,4-二甲基苯基)-苯并呋喃-2-酮;5,7-二-叔丁基-3-(2,3-二甲基苯基)-苯并呋喃-2-酮或者5-叔辛基-3-(2-乙酰基-5-叔辛基苯基)-苯并呋喃-2-酮。
预防在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的优选方法包括作为组分(b)(ii)的至少一种式IV化合物的苯并呋喃-2-酮稳定剂
其中
R9为氢或者C1-C8烷基,
R10为C1-C12烷基,
R11为氢、C1-C4烷基或者C2-C8烷酰基,
R12为氢或者C1-C8烷基,
R13为氢、C1-C4烷基或者C1-C4烷氧基,和
R14为氢或者C1-C12烷基。
C2-C8烷酰基为,例如乙酰基、丙酰基、丁酰基、戊酰基、己酰基、庚酰基或者辛酰基。优选乙酰基。
特别优选的苯并呋喃-2-酮稳定剂为,例如,5,7-二-叔丁基-3-苯基-苯并呋喃-2-酮;5,7-二-叔丁基-3-(3,4-二甲基苯基)-苯并呋喃-2-酮;5,7-二-叔丁基-3-(2,3-二甲基苯基)-苯并呋喃-2-酮或者5-叔辛基-3-(2-乙酰基-5-叔辛基苯基)-苯并呋喃-2-酮。
式IV的苯并呋喃-2-酮稳定剂在文献中是已知的,并且其公开于例如U.S.5,516,920中。
预防在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的优选方法包括作为组分(b)(iii)的至少一种式V、VI、VII或者VIII化合物的亚磷酸酯或者亚膦酸酯
其中
n’为数字2,和y’为数字1、2或者3;
A’为C2-C18亚烷基、对-亚苯基或者对-亚联苯基,
如果y’为1,则E’为C1-C18烷基、-OR’1或者氟;
如果y’为2,则E’为对-亚联苯基,
如果y’为3,则E’为N(CH2CH2O-)3,
R’1、R’2和R’3彼此独立地为C1-C18烷基、C7-C9苯基烷基、环己基、苯基或者被1~3个总共具有1~18个碳原子的烷基取代的苯基;
R’14为氢或者C1-C9烷基,
R’15为氢或者甲基;
X’为直接键,
Y’为氧,
Z’为直接键或者-CH(R’16)-,和
R’16为C1-C4烷基。
同样优选的是预防在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的方法,其中包括作为组分(b)(iii)的至少一种式V、VI、VII或者VIII化合物的亚磷酸酯或者亚膦酸酯,其中
n’为数字2,和y’为数字1或者3;
A’为对-亚联苯基,
如果y’为1,则E’为C1-C18烷氧基或者氟,
如果y’为3,则E’为N(CH2CH2O-)3,
R’1、R’2和R’3彼此独立地为C1-C18烷基或者为被2或者3个总共具有2~12个碳原子的烷基取代的苯基;
R’14为甲基或者叔丁基;
R’15为氢;
X’为直接键;
Y’为氧;和
Z’为直接键、亚甲基或者-CH(CH3)-。
预防在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的特别优选方法,包括作为组分(b)(iii)的至少一种式IX的亚磷酸酯
其中
R1和R2彼此独立地为氢、C1-C8烷基、环己基或者苯基,和
R3和R4彼此独立地为氢或者C1-C4烷基。
以下化合物是特别适于在所述新颖方法中作为组分(b)(iii)的有机亚磷酸酯和亚膦酸酯的实例。
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、二亚磷酸二硬脂酰季戊四醇酯、亚磷酸三-(2,4-二叔丁基苯基)酯(Irgafos168,Ciba Specialty Chemicals Inc.)、二亚磷酸二异癸基季戊四醇酯、二亚磷酸酯二(2,4-二叔丁基苯基)季戊四醇(式D)、二亚磷酸二(2,6-二叔丁基-4-甲基苯基)季戊四醇酯(式E)、二亚磷酸二异癸氧基-季戊四醇酯、二亚磷酸二(2,4-二叔丁基-6-甲基苯基)季戊四醇酯、二亚磷酸二(2,4,6-三叔丁基苯基)季戊四醇酯、三亚磷酸三硬脂基山梨醇酯、四(2,4-二叔丁基苯基)4,4’-二亚苯基二亚磷酸酯(IrgafosP-EPQ,Ciba Specialty Chemicals Inc.,式H)、6-异辛氧基-2,4,8,10-四-叔丁基-12H-二苯并[d,g]-1,3,2-二氧磷杂八环(dioxaphosphocin)(式C)、6-氟-2,4,8,10-四-叔丁基-12-甲基二苯并[d,g]-1,3,2-二氧磷杂八环(式A)、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(式G)。
特别优选以下亚磷酸酯和亚膦酸酯:
非常特别优选亚磷酸三(2,4-二-叔丁基苯基)酯[Irgafos168,Ciba Specialty Chemicals Inc.]、亚磷酸二(2,4-二-叔丁基-6-甲基苯基)乙基酯[Irgafos38,Ciba Specialty Chemicals Inc.,式(G)]、二亚磷酸二(2,4-二-叔丁基苯基)季戊四醇酯[Irgafos126,CibaSpecialty Chemicals Inc.,式(D)]或者四(2,4-二-叔丁基苯基)-4,4’-二亚苯基二亚磷酸酯[IrgafosP-EPQ,Ciba Specialty ChemicalsInc.,式(H)]。
上述有机亚磷酸酯和亚膦酸酯是已知的化合物;它们中的多数可以商业获得。
组分(a)和(b)同样用于聚氨基甲酸酯生产,特别是用于制备弹性聚氨基甲酸酯泡沫。在此上下文中,由此形成的新颖产品可以有效防止降解并且具有低醛污染物含量。特别是,在泡沫形成期间还避免了烧焦。优选,在以相对较高的浓度(基于聚醚多元醇按重量计直至1.5%)起泡沫之前,在混料头将亚磷酸酯(比如,例如为亚磷酸二苯基异癸基酯(DPDP)或者亚磷酸苯基二异癸基酯(PDDP)作为抗氧化剂或者抗焦剂体系后加入到碱稳定的聚醚多元醇中。
聚氨基甲酸酯通过以下方式获得,例如,使含有末端羟基基团的聚醚、聚酯和聚丁二烯与脂族或者芳香聚异氰酸酯反应。
具有末端羟基基团的聚醚和聚酯是已知的并且通过以下方式进行制备,例如,通过例如在BF3存在下,使比如环氧乙烷、环氧丙烷、环氧丁烷、四氢呋喃、苯乙烯氧化物或者环氧氯丙烷的环氧化物与其自身聚合,或者通过这些环氧化物单独或者作为混合物进行加成反应,或者顺序与含有活泼氢原子的原料组分进行加成反应,所述含有活泼氢原子的原料组分比如水、醇、氨或者胺,例如乙二醇、丙1,3-和1,2-二醇、三羟甲基丙烷、4,4’-二羟基二苯基丙烷、苯胺、乙醇胺或者乙二胺。根据本发明,蔗糖聚醚同样是适宜的。在大多数情形中,优选主要(基于存在于聚醚中的所有OH基团,按重量计直至90%)含有伯OH基团的那些聚醚。此外,比如,例如为在聚醚存在下通过苯乙烯和丙烯腈聚合而形成的乙烯基聚合物改性的聚醚也是适宜的,比如,含有OH基团的聚丁二烯。
这些化合物的分子量通常为40并且为多羟基化合物,特别是含有2~8个羟基的化合物,特别是分子量为800~10000的那些化合物,优选1000~6000,例如含有至少2个,通常为2~8个,不过优选2~4个羟基的聚醚,它们对于制备均质聚氨基甲酸酯和多孔聚氨基甲酸酯是已知的。
当然可以使用上述含有至少两个异氰酸酯-活泼氢原子的化合物的混合物,特别是分子量为400-10000的化合物。
适宜的聚异氰酸酯为脂族、环脂族、芳脂族、芳香和杂环聚异氰酸酯,例如亚乙基二异氰酸酯、1,4-四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、1,12-十二烷二异氰酸酯、环丁烷1,3-二异氰酸酯、环己烷1,3-和-1,4-二异氰酸酯以及这些异构体的任何期望混合物、1-异氰酸基-3,3,5-三甲基-5-异氰酸基甲基环己烷、2,4-和2,6-六氢亚甲苯基二异氰酸酯以及这些异构体的任何期望混合物、六氢-1,3-和/或1,4-亚苯基二异氰酸酯、全氢-2,4’-和/或-4,4’-二苯基甲烷二异氰酸酯、1,3-和1,4-亚苯基二异氰酸酯、2,4-和2,6-苯亚甲基二异氰酸酯以及这些异构体的任何期望混合物、二苯基甲烷2,4’-和/或-4,4’二异氰酸酯、亚萘基1,5-二异氰酸酯、三苯甲烷4,4’,4"-三异氰酸酯、通过苯胺-甲醛缩合和随后光气化反应获得的聚苯基-聚亚甲基聚异氰酸酯、间和对-异氰酸基苯基磺酰基异氰酸酯、全氯化芳基聚异氰酸酯、含有碳二亚胺基团的聚异氰酸酯、含有脲基甲酸酯基团的聚异氰酸酯、含有异氰脲酸酯基团的聚异氰酸酯、含有氨基甲酸酯基团的聚异氰酸酯、含有酰化脲基团的聚异氰酸酯、含有缩二脲基团的聚异氰酸酯、含有酯基的聚异氰酸酯、上述异氰酸酯与缩醛的反应产物和含有聚合脂肪酸基团的聚异氰酸酯。
还可以使用在工业制备异氰酸酯过程中获得的含有异氰酸酯基团的蒸馏残余物,因为它们是或者溶于一种或者多种上述聚异氰酸酯。另外可以使用上述聚异氰酸酯的任何期望的混合物。
通常特别优选可以轻易工业获得的聚异氰酸酯,例如2,4-和2,6-亚苯甲基二异氰酸酯和这些异构体的任何期望混合物(“TDI”)、通过苯胺-甲醛缩合和随后进行光气化反应获得的聚苯基-聚亚甲基-聚异氰酸酯(“粗MDI”),和含有碳二亚胺、氨基甲酸酯、脲基甲酸酯、异氰脲酸酯、脲或者缩二脲基团的聚异氰酸酯(“改性聚异氰酸酯”)。
优选聚氨基甲酸酯泡沫由液体原料组分制备,或者使原料彼此混合以一次性的方式反应,或者首先制备由多元醇和过量聚异氰酸酯形成的含有NCO基团的预加合物和随后进行起泡沫,一般通过与水反应起泡沫。
在泡沫制备中,通常在铸模中发泡。在这种情形中,将反应混合物置于铸模中。适宜的铸模材料为金属,一般为铝,或者塑料,一般为环氧树脂。在铸模中,使可以发泡的反应混合物起泡沫和形成模制品。可以进行泡沫成型,从而使得模制品具有多孔表面结构,或者使得模制品具有密集表面和多孔核。关于这一点,可以向铸模中投入充分量的可发泡反应混合物,以使得获得的泡沫精确地填充铸模。然而,还可以将多于用泡沫填充铸模内部所需的更多可发泡反应混合物置入铸模中。因此,在后一种情形中,所述操作过载进行。
在泡沫成型的情形中,通常还伴随使用已知的外脱模剂,一般为硅酮油类。然而,还可以使用所谓的内脱模剂,其任选与外脱模剂混合。还可以使用冷固化的泡沫。所述泡沫当然可以另外通过阻断发泡或者通过已知的双传送带方法进行制备。这些方法可以用于制备弹性、半弹性或者硬聚氨基甲酸酯泡沫。这些泡沫在对于所述产品已知的应用中具有应用,例如在家具和汽车工业中作为垫子和室内装饰,以及用于制造比如用于汽车工业中的配件,和最后作为隔声组合物和作为热绝缘和低温绝缘的组合物,例如在建筑部门或者在冷冻工业中,或者在纺织工业中例如作为垫肩。
基于欲进行稳定的聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯的重量,优选以0.01~10%的量将组分(a)加入到欲进行稳定的聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中,特别是0.01~5%,例如0.01~2%。
基于欲进行稳定的聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯的重量,优选以0.01~10%的量将组分(b)加入到欲进行稳定的聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中,特别是0.01~5%,例如0.01~2%。
除了组分(a)和(b)之外,用于预防醛式污染物在聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成的新颖方法可以进一步包括共稳定剂(添加剂),比如,例如以下:
1.抗坏血酸(维生素C)
2.UV吸收剂和光稳定剂
2.1.2-(2’-羟苯基)苯并三唑,例如2-(2’-羟基-5’-甲苯基)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’-辛基氧基苯基)苯并三唑、2-(3’,5’-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-乙基己基-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’-羟基苯基)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’-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物;[R-CH2-CH2-COO-CH2CH-]2,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,例如水杨酸4-叔丁基苯基酯、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,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-甲酯基肉桂酸甲酯、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-甲酯基-对甲氧基肉桂酸甲酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚、四(α-氰基-β,β-二苯基丙烯酸)新戊酯。
2.5.镍化合物,例如2,2’-硫代-双[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;单烷基酯如4-羟基-3,5-二叔丁基苄基磷酸甲酯或乙酯的镍盐;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.立体受阻胺,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)硝基三醋酸酯、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-硬脂酰氧基-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、4-十六烷氧基和4-硬脂酰氧基-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-1,3,5-三嗪及4-丁基氨基-2,2,6,6-四甲基哌啶(CASReg.No.[136504-96-6])的缩合物;1,6-六亚甲基二胺和2,4,6-三氯-1,3,5-三嗪及N,N-二丁基胺和4-丁基氨基-2,2,6,6-四甲基哌啶(CAS Reg.No.[192268-64-7])的缩合物;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-烷基-7,7,9,9-四甲基-1-氧-3,8-二氮杂-4-氧-螺-[4.5]癸烷、7,7,9,9-四甲基-2-环十一烷-1-氧杂-3,8-二氮杂-4-氧-螺-[4.5]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,2,4-二[N-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)-N-丁氨基]-6-(2-羟乙基)氨基-1,3,5-三嗪、1-(2-羟基-2-甲基丙氧基)-4-十八酰氧基-2,2,6,6-四甲基哌啶、5-(2-乙基己酰基)氧基甲基-3,3,5-三甲基-2-吗啉酮、Sanduvor[Clariant;CAS Reg.No.106917-31-1]、5-(2-乙基己酰基)氧基甲基-3,3,5-三甲基-2-吗啉酮、2,4-二[(1-环己基氧基-2,2,6,6-哌啶-4-基)丁氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)乙二胺的反应产物、1,3,5-三(N-环己基-N-(2,2,6,6-四甲基哌嗪-3-酮-4-基)氨基)-s-三嗪、1,3,5-三(N-环己基-N-(1,2,2,6,6-五甲基哌嗪-3-酮-4-基)氨基)-s-三嗪。
2.7.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’-二叔丁草酰替苯胺、2,2’-双十二烷基氧基-5,5’-二叔丁草酰替苯胺、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。
2.8.2-(2-羟基苯基)-1,3,5-三嗪,例如2,4,6-三(2-羟基-4-辛基氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛基氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙基氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛基氧基苯基)-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-4-十三烷基氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁基氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛基氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷基氧基丙氧基)苯基]-4,6-双(2,4-二甲基-苯基)-1,3,5-三嗪、2-(2-羟基-4-己基氧基)苯基-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧基苯基)-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-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪、2-{2-羟基-4-[3-(2-乙基己基-1-氧基)-2-羟基丙基氧基]苯基}-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-二(4-[2-乙基己氧基]-2-羟苯基)-6-(4-甲氧基苯基)-1,3,5-三嗪。
3.金属去活化剂,例如N,N’-二苯基草酰胺、N-水杨醛-N’-水杨酰基肼、N,N’-双(水杨酰基)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、癸二酰二苯酰肼、N,N’-二乙酰己二酰二酰肼、N,N’-双(水杨酰基)草酰基二酰肼、N,N’-双(水杨酰基)硫代丙酰基二酰肼。
4.羟胺,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-十八烷基羟胺、N-十七烷基-N-十八烷基羟胺、由氢化牛油脂肪胺衍生得到的N,N-二烷基羟胺。
5.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、衍生自氢化的牛油脂肪胺的N,N-二烷基羟胺的硝酮。
6.硫代增效剂,例如硫代二丙酸二-十二烷基酯、硫代二丙酸dimistryl酯、硫代二丙酸二硬脂酰酸酯或二硬脂酰基二硫化物。
7.过氧化物清除剂,例如β-硫代二丙酸的酯如月桂基、硬脂酰基、十四烷基或十三烷基酯,巯基苯并咪唑或2-巯基苯并咪唑的锌盐、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。
8.碱性共稳定剂,例如蜜胺、聚乙烯吡咯烷酮、二氰基二酰胺、三烯丙基氰脲酸酯、脲衍生物、肼衍生物、胺、聚酰胺、聚氨基甲酸酯、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、二十二碳酸镁、硬脂酸镁、蓖麻酸钠和棕榈酸钾、焦儿茶酸锑或焦儿茶酸锌。
9.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。
10.其它添加剂,例如成塑剂、润滑剂、乳化剂、颜料、流变学添加剂、催化剂、流动控制剂、荧光增白剂、耐焰剂、抗静电剂和流动剂。
相对于欲进行稳定的聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯的总重量,所述共稳定剂以例如0.01~10%的浓度加入其中。
优选其它添加剂为光-稳定剂(上述列举的条目2)。
本发明的优选目标还是组分(a)和(b)的混合物预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的用途。
以下实施例更详细地说明了本发明。份数和百分比都以重量计。
实施例1:聚醚多元醇的稳定。
将如表1中所述的稳定剂混合物以如表1中所示的量溶于160g聚醚多元醇[Petol 46-3MB(RTM)(具有伯羟基的三功能聚醚多元醇;羟基数48mg KOH/g,含水量小于0.1%,酸值小于0.1mg KOH/g)]中。将聚醚多元醇贮存到80℃的烘箱中几天。通过周期性提取样品,对形成的甲醛、乙醛和丙醛的量进行测量。这些样品用二硝基苯肼-乙腈溶液(DNPH-乙腈溶液)进行处理。形成的甲醛-DNPH、乙醛-DNPH和丙醛-DNPH通过HPLC方法进行定量测量,所述HPLC方法使用Alltima C 18 5μm柱[4.6×250mm],在30℃的柱温和含有60%乙腈和40%水的流动相中进行。溶剂流速为1.2ml/分钟。所得结果概括于表1和2中。
表1:
实施例 | 稳定剂 | 数天之后的甲醛(ppm) | 数天之后的乙醛(ppm) | 数天之后的丙醛(ppm) | ||||||
0 | 2 | 5 | 0 | 2 | 5 | 0 | 2 | 5 | ||
1aa) | 无 | 1.2 | 6.8 | 18 | 3.6 | 24 | 99 | 2.8 | 4.1 | 11 |
1ba) | 0.1%Irganox 1135c) | 1.6 | 2.5 | 5.4 | 3.7 | 6.6 | 13 | 2.7 | 2.6 | 2.5 |
1cb) | 0.1%混合物1d) | 1.4 | 1.7 | 1.8 | 3.6 | 4.3 | 4.6 | 2.7 | 2.5 | 2.5 |
1db) | 0.1%混合物2e) | 1.2 | 2.4 | 4.6 | 3.4 | 5.6 | 11 | 2.7 | 2.6 | 2.5 |
1eb) | 0.1%混合物3f) | 1.4 | 2.3 | 2.7 | 3.9 | 5.6 | 6.3 | 2.7 | 2.4 | 2.4 |
1fb) | 0.1%混合物4g) | 1.4 | 2.9 | 7.2 | 3.4 | 6.5 | 17 | 2.6 | 2.5 | 2.4 |
表2:
实施例 | 稳定剂 | 数天之后的甲醛(ppm) | 数天之后的乙醛(ppm) | ||
0 | 15 | 0 | 15 | ||
1ga) | 无 | 0.3 | 20 | 1.7 | 84 |
1hb) | 0.1%混合物1d) | 0.3 | 1.0 | 1.8 | 3.1 |
1ib) | 0.1%混合物3f) | 0.4 | 1.7 | 1.9 | 5.2 |
a)对比实施例。
b)根据本发明的实施例。
c)Irganox 1135(RTM)(Ciba Specialty Chemicals Inc.)为式AO-1的酚类抗氧剂。
d)混合物1为2份Irganox 1135c)和1份Irganox 5057h)的混合物。
e)混合物2为7份Irganox 1135c)、1份Irgafos 38i)和1份Irganox HP 136j)的混合物。
f)混合物3为10份Irganox 1135c)、3份Irganox 5057h)和1份PS-1k)的混合物。
g)混合物4为7份Irganox 1135c)、1份Irgafos 38i)和1份PS-1k)的混合物。
h)Irganox 5057(RTM)(Ciba Spehialty Chemicals Inc.)为胺类抗氧化剂,并且是通过二苯胺与二异丁烯反应获得的技术混合物,包括
α)二苯胺;
β)4-叔丁基二苯基胺;
γ)以下组的化合物
i)4-叔辛基二苯基胺,
ii)4,4’-二叔丁基二苯基胺,
iii)2,4,4’-三叔丁基二苯基胺,
δ)以下组的化合物
i)4-叔丁基-4’-叔辛基二苯基胺,
ii)o,o’、m,m’或者P,P’-二叔辛基二苯基胺,
iii)2,4-二叔丁基-4’-叔辛基二苯基胺,
ε)以下组的化合物
i)4,4’-二叔辛基二苯基胺,
ii)2,4-二叔辛基-4’-叔丁基二苯基胺,和其中存在不多于按重量计5%的组分α),按重量计8~15%的组分β),按重量计24~32%的组分γ),按重量计23~34%的组分δ)和按重量计21~34%的组分ε。
i)Irgafos 38(RTM)(Ciba Specialty Chemicals Inc.)为亚磷酸二(2,4-二叔丁基-6-甲基苯基)乙基酯。
j)Irganox HP 136(RTM)(Ciba Specialty Chemicals Inc.)是约85重量份数的式IVa化合物和约15重量份数的式IVb化合物的混合物。
k)PS-1为式IVc的3-(2-乙酰基-5-异辛基苯基)-5-异辛基苯并呋喃-2-酮。
Claims (6)
1.一种预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物的方法,包含向所述聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中结合入
a)酚类抗氧剂,其为式Ia的化合物:
b)作为组分(b)(i)的胺类抗氧化剂,该组分(b)(i)为通过二苯胺与二异丁烯反应获得的技术混合物,包括
α)二苯胺;
β)4-叔丁基二苯胺;
γ)以下组的化合物
i)4-叔辛基二苯胺,
ii)4,4’-二叔丁基二苯胺,
iii)2,4,4’-三叔丁基二苯胺,
δ)以下组的化合物
i)4-叔丁基-4’-叔辛基二苯胺,
ii)o,o’、m,m’或者p,p’-二叔辛基二苯胺,
iii)2,4-叔丁基-4’-叔辛基二苯胺,
ε)以下组的化合物
i)4,4’-二叔辛基二苯胺,
ii)2,4-叔辛基-4’-叔丁基二苯胺,和
其中存在不超过按重量计5%的组分α),按重量计8~15%的组分β),按重量计24~32%的组分γ),按重量计23~34%的组分δ)和按重量计21~34%的组分ε)
其中基于聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯的重量,组分(a)以0.01~10%的量存在;基于聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯的重量,组分(b)以0.01~10%的量存在。
2.根据权利要求1的方法,其中包括作为组分(b)(ii)的式IV化合物
其中
R9为氢或者C1-C8烷基,
R10为C1-C12烷基,
R11为氢、C1-C4烷基或者C2-C8烷酰基,
R12为氢或者C1-C8烷基,
R13为氢、C1-C4烷基或者C1-C4烷氧基,和
R14为氢或者C1-C12烷基。
3.根据权利要求1的方法,其中包括作为组分(b)(iii)的式V、VI、VII或者VIII化合物
其中
n’为数字2,和y’为数字1、2或者3;
A’为C2-C18亚烷基、对-亚苯基或者对-亚联苯基,
如果y’为1,则E’为C1-C18烷基、-OR’1或者氟;
如果y’为2,则E’为对-亚联苯基,
如果y’为3,则E’为N(CH2CH2O-)3,
R’1、R’2和R’3彼此独立地为C1-C18烷基、C7-C9苯基烷基、环己基、苯基或者被1~3个总共具有1~18个碳原子的烷基取代的苯基;
R’14为氢或者C1-C9烷基,
R’15为氢或者甲基;
X’为直接键,
Y’为氧,
Z’为直接键或者-CH(R’16)-,和
R’16为C1-C4烷基。
4.根据权利要求1的方法,除了组分(a)和(b)之外,此外还包括其它添加剂。
5.根据权利要求4的方法,包括作为其它添加剂的光-稳定剂。
6.如权利要求1-5任一项所述的组分(a)和(b)的混合物的用途,用于预防聚醚多元醇、聚酯多元醇或者聚氨基甲酸酯中形成醛式污染物。
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PCT/EP2006/061529 WO2006111492A2 (en) | 2005-04-19 | 2006-04-11 | Polyether polyols, polyester polyols and polyurethanes of low residual aldehyde content |
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JP (1) | JP5107898B2 (zh) |
CN (1) | CN101163735B (zh) |
AT (1) | ATE428748T1 (zh) |
DE (1) | DE602006006304D1 (zh) |
ES (1) | ES2322776T5 (zh) |
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ES2322776T3 (es) | 2009-06-26 |
US20090182078A1 (en) | 2009-07-16 |
US7879928B2 (en) | 2011-02-01 |
ES2322776T5 (es) | 2012-11-20 |
ATE428748T1 (de) | 2009-05-15 |
CN101163735A (zh) | 2008-04-16 |
US20110054220A1 (en) | 2011-03-03 |
EP1874853B1 (en) | 2009-04-15 |
JP5107898B2 (ja) | 2012-12-26 |
JP2008536991A (ja) | 2008-09-11 |
DE602006006304D1 (de) | 2009-05-28 |
TW200708548A (en) | 2007-03-01 |
EP1874853B2 (en) | 2012-07-04 |
EP1874853A2 (en) | 2008-01-09 |
WO2006111492A2 (en) | 2006-10-26 |
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TWI464206B (zh) | 2014-12-11 |
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