TWI464206B - 低殘餘醛含量之聚醚多元醇、聚酯多元醇及聚胺酯 - Google Patents
低殘餘醛含量之聚醚多元醇、聚酯多元醇及聚胺酯 Download PDFInfo
- Publication number
- TWI464206B TWI464206B TW095113627A TW95113627A TWI464206B TW I464206 B TWI464206 B TW I464206B TW 095113627 A TW095113627 A TW 095113627A TW 95113627 A TW95113627 A TW 95113627A TW I464206 B TWI464206 B TW I464206B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- bis
- butyl
- hydrogen
- group
- Prior art date
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- 229920000570 polyether Polymers 0.000 title claims abstract description 45
- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 43
- 229920005862 polyol Polymers 0.000 title claims abstract description 41
- 150000003077 polyols Chemical class 0.000 title claims abstract description 39
- 239000004814 polyurethane Substances 0.000 title claims abstract description 37
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 37
- 229920005906 polyester polyol Polymers 0.000 title claims abstract description 29
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims 2
- 239000000203 mixture Substances 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 18
- 239000000356 contaminant Substances 0.000 claims abstract description 18
- ACZGCWSMSTYWDQ-UHFFFAOYSA-N 3h-1-benzofuran-2-one Chemical class C1=CC=C2OC(=O)CC2=C1 ACZGCWSMSTYWDQ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002530 phenolic antioxidant Substances 0.000 claims abstract description 12
- -1 bis(2,4-di-tertiary butyl- 6-methylphenyl)ethyl Chemical group 0.000 claims description 62
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 235000019260 propionic acid Nutrition 0.000 claims description 5
- 230000000996 additive effect Effects 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 239000004611 light stabiliser Substances 0.000 claims description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
- QLMGIWHWWWXXME-UHFFFAOYSA-N 2-(3,5-ditert-butyl-4-hydroxyphenyl)acetic acid Chemical compound CC(C)(C)C1=CC(CC(O)=O)=CC(C(C)(C)C)=C1O QLMGIWHWWWXXME-UHFFFAOYSA-N 0.000 claims description 2
- DBHUTHZPCWZNRW-UHFFFAOYSA-N 3-(3,5-dicyclohexyl-4-hydroxyphenyl)propanoic acid Chemical compound OC=1C(C2CCCCC2)=CC(CCC(=O)O)=CC=1C1CCCCC1 DBHUTHZPCWZNRW-UHFFFAOYSA-N 0.000 claims description 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 claims 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 22
- 239000003963 antioxidant agent Substances 0.000 abstract description 11
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical class OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 abstract description 8
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 28
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 21
- 229920001228 polyisocyanate Polymers 0.000 description 20
- 239000005056 polyisocyanate Substances 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 150000001299 aldehydes Chemical class 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- 239000003381 stabilizer Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 12
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- 235000006708 antioxidants Nutrition 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000012948 isocyanate Substances 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 10
- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical group C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 239000006260 foam Substances 0.000 description 8
- 238000005187 foaming Methods 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 6
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 6
- 230000003078 antioxidant effect Effects 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
- 125000002704 decyl 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])* 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- KPSSIOMAKSHJJG-UHFFFAOYSA-N neopentyl alcohol Chemical compound CC(C)(C)CO KPSSIOMAKSHJJG-UHFFFAOYSA-N 0.000 description 6
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-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
- 229960003742 phenol Drugs 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 5
- BJFLSHMHTPAZHO-UHFFFAOYSA-N benzotriazole Chemical compound [CH]1C=CC=C2N=NN=C21 BJFLSHMHTPAZHO-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 4
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 241000208340 Araliaceae Species 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 4
- 235000003140 Panax quinquefolius Nutrition 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 229920005830 Polyurethane Foam Polymers 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 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 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000008434 ginseng Nutrition 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 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
- 239000011496 polyurethane foam Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- KGRVJHAUYBGFFP-UHFFFAOYSA-N 2,2'-Methylenebis(4-methyl-6-tert-butylphenol) Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)O)=C1O KGRVJHAUYBGFFP-UHFFFAOYSA-N 0.000 description 3
- 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
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 3
- UKJARPDLRWBRAX-UHFFFAOYSA-N n,n'-bis(2,2,6,6-tetramethylpiperidin-4-yl)hexane-1,6-diamine Chemical compound C1C(C)(C)NC(C)(C)CC1NCCCCCCNC1CC(C)(C)NC(C)(C)C1 UKJARPDLRWBRAX-UHFFFAOYSA-N 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- SRENRFDRXNVMKN-UHFFFAOYSA-N n-butyl-n-phenylaniline Chemical group C=1C=CC=CC=1N(CCCC)C1=CC=CC=C1 SRENRFDRXNVMKN-UHFFFAOYSA-N 0.000 description 3
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 125000002924 primary amino group Chemical group [H]N([H])* 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-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 2
- MQQKTNDBASEZSD-UHFFFAOYSA-N 1-(octadecyldisulfanyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCCSSCCCCCCCCCCCCCCCCCC MQQKTNDBASEZSD-UHFFFAOYSA-N 0.000 description 2
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ODJQKYXPKWQWNK-UHFFFAOYSA-L 3-(2-carboxylatoethylsulfanyl)propanoate Chemical compound [O-]C(=O)CCSCCC([O-])=O ODJQKYXPKWQWNK-UHFFFAOYSA-L 0.000 description 2
- JNRLEMMIVRBKJE-UHFFFAOYSA-N 4,4'-Methylenebis(N,N-dimethylaniline) Chemical group C1=CC(N(C)C)=CC=C1CC1=CC=C(N(C)C)C=C1 JNRLEMMIVRBKJE-UHFFFAOYSA-N 0.000 description 2
- UOMXLEWVJZEVGP-UHFFFAOYSA-N 4-tert-butyl-n-phenylaniline Chemical compound C1=CC(C(C)(C)C)=CC=C1NC1=CC=CC=C1 UOMXLEWVJZEVGP-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
- ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QFOHBWFCKVYLES-UHFFFAOYSA-N Butylparaben Chemical compound CCCCOC(=O)C1=CC=C(O)C=C1 QFOHBWFCKVYLES-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethanediamine Natural products NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- KEQFTVQCIQJIQW-UHFFFAOYSA-N N-Phenyl-2-naphthylamine Chemical compound C=1C=C2C=CC=CC2=CC=1NC1=CC=CC=C1 KEQFTVQCIQJIQW-UHFFFAOYSA-N 0.000 description 2
- NLVRDRNMXBKPIH-UHFFFAOYSA-N OP(O)OP(O)O.OCC(C)(CO)C Chemical compound OP(O)OP(O)O.OCC(C)(CO)C NLVRDRNMXBKPIH-UHFFFAOYSA-N 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
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- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
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- 239000011709 vitamin E Substances 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 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
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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
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
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Description
本發明係關於防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之方法,其包括在該聚醚多元醇、聚酯多元醇或聚胺酯中併入有效量之(a)酚類抗氧化劑、與(b)一個或多個選自(i)胺類抗氧化劑、(ii)苯并呋喃-2-酮與(iii)亞磷酸酯或亞膦酸酯、或(iv)其混合物中的化合物。
酚類抗氧化劑作為聚醚多元醇、聚酯多元醇或聚胺酯之安定劑之用途為已知的,例如:H.Zweifel;塑膠添加劑手冊,第五版,Hanser出版公司,慕尼黑,88-109頁(2001)。
已知的安定劑無法滿足安定劑在每個方面被要求達到之高度要求,特別是關於貯存期限、吸水性、對水解之敏感性、加工穩定性、顏色特性、揮發性、轉移行為,在防光之相容性與改善上。此外,來自汽車工業之強烈需求需要顯著降低揮發性有機化合物(VOC)及尤其是氣體排放(FOG)的量。氣體排放通常也與「霧化」現象有關,當揮發之揮發性物質濃縮在汽車擋風玻璃上導致在窗戶上的沈積物。此外,寢具、傢俱與地毯底布發泡體之最終消費者也對撓性板材發泡體之製造商施加壓力。共添加劑例如像催化劑、介面活性劑、阻焰劑、抗氧化劑促成了聚胺酯發泡體之排放。VOC之主要來源為如聚矽氧烷介面活性劑與胺觸媒之添加劑。汽車工業目前正聚焦在降低及/或去除有關特定化學品(其係作為塑膠汽車零件生產之原料或是其降解產物)的排放物上。指標化學品例如為醛類,醛類舉例而言像甲醛、乙醛、丙醛;甲苯與苯乙烯。我們也發現來自聚醚多元醇、聚酯多元醇或聚胺酯之降解產物也可為例如甲醛、乙醛、丙醛之醛類。
我們頃發現包括酚類抗氧化劑與第二共穩定劑之穩定劑混合物在降低在聚醚多元醇與由其產生之聚胺酯中之甲醛與乙醛程度展現了極佳的功效。
本發明因此係關於防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之方法,其包括在該聚醚多元醇、聚酯多元醇或聚胺酯中併入有效量之a)酚類抗氧化劑b)一或多個化合物選自(i)胺類抗氧化劑、(ii)苯并呋喃-2-酮、及(iii)亞磷酸酯或亞膦酸酯、或(iv)其混合物
作為成分(a)之較佳酚類抗氧化劑為式I之化合物
其中R1
為氫或C1
-C4
烷基,n為1、2、3或4,X為亞甲基、或Y為氫或-NH-;及,如果n為1,X為,其中Y連接至R2
,及R2
為C1
-C2 5
烷基;與,如果n為2 X為,其中Y連接至R2
,且R2
為C2
-C1 2
伸烷基,被氧或硫中斷之C4
-C1 2
伸烷基;或,如果Y為-NH-,R2
為額外的直接鍵;及,如果n為3,X是亞甲基或,其中該伸乙烯基連接至R2
,且R2
為或,及,如果n為4,X為,其中Y連接至R2
,且R2
為C4
-C1 0
烷四基。
具有高至25個碳原子之烷基為支鏈或非支鏈之基,例如甲基、乙基、丙基、異丙基、正丁基、二級丁基、異丁基、三級丁基、2-乙基丁基、正戊基、異戊基、1-甲基戊基、1,3-二甲基丁基、正己基、1-甲基己基、正庚基、異庚基、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、十一基、1-甲基十一基、十二基、1,1,3,3,5,5-六甲基己基、十三基、十四基、十五基、十六基、十七基、十八基、二十基或二十二基。R1
之較佳的定義為甲基及三級丁基。R2
之特別較佳的定義為C1
-C2 0
烷基,尤其為C1
-C1 8
烷基,例如:C4
-C1 8
烷基。R2
之特別較佳的定義為C8
-C1 8
烷基,尤其為C1 4
-C1 8
烷基,例如:C1 8
烷基。
C2
-C1 2
伸烷基為支鏈或非支鏈之基,例如伸乙基、伸丙基、四亞甲基、五亞甲基、六亞甲基、七亞甲基、八亞甲基、十亞甲基或十一亞甲基。R2
之較佳的定義為,例如:C2
-C1 0
伸烷基,尤其是C2
-C8
伸烷基。R2
之尤其較佳的定義為,例如:C4
-C8
伸烷基,尤其是C4
-C6
伸烷基,例如:六亞甲基。
被氧或硫中斷之C4
-C1 2
伸烷基可被中斷一次或多次且為例如:-CH2
-O-CH2
-CH2
-O-CH2
-、-CH2
-(O-CH2
-CH2
-)2
O-CH2
-、-CH2
-(O-CH2
-CH2
-)3
O-CH2
-、-CH2
-(O-CH2
-CH2
-)4
O-CH2
-,-CH2
CH2
-O-CH2
-CH2
-O-CH2
CH2
-或-CH2
CH2
-S-CH2
-CH2
-。R2
之較佳的定義為,例如:被氧或硫中斷之C4
-C1 0
伸烷基,尤其是被氧或硫中斷之C4
-C8
伸烷基,例如:被氧或硫中斷之C4
-C6
伸烷基。R2
之尤其較佳的定義為-CH2
CH2
-O-CH2
-CH2
-O-CH2
CH2
-或-CH2
CH2
-S-CH2
-CH2
-。
具有4至10個碳原子的烷四基為,例如:(新戊四基),,,,或,新戊四基為較佳者。
成分(a)也可包括不同的空間位阻之式I酚的混合物。
一種防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之感興趣的方法包括酚類抗氧化劑作為成分(a)至少有一種式I化合物,其中,如果n為1,則R2
為C1
-C2 0
烷基。
一種防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之方法較佳為包括作為成分(a)之至少一種式I化合物,其中如果n為2,R2
為C2
-C8
伸烷基,被氧或硫中斷之C4
-C8
伸烷基;或者,如果Y為-NH-,則R2
為額外的直接鍵;及,如果n為3,X為亞甲基,R2
為,及,如果n為4,R2
為C4
-C8
烷四基。
同樣較佳之防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之方法為包括作為成分(a)之至少一種式I化合物,其中R1
為甲基或三級丁基,n為1、2、3或4,X為亞甲基或,Y為氫或-NH-;及,如果n為1,R2
為C8
-C1 8
烷基;及,如果n為2,R2
為C4
-C6
伸烷基,或為被氧中斷之C4
-C6
伸烷基;及,如果n為3,X為亞甲基,R2
為,及,如果n為4,R2
為C4
-C6
烷四基。
一種防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之感興趣的方法包括作為成分(a)之下述酚類抗氧化劑:1.1.烷化單酚
,例如2,6-二三級丁基-4-甲基酚、2-三級丁基-4,6-二甲基酚、2,6-二三級丁基-4-乙基酚、2,6-二三級丁基-4-正丁基酚、2,6-二三級丁基-4-異丁基酚、2,6-二環戊基-4-甲基酚、2-(α-甲基環己基)-4,6-二甲基酚、2,6-二-十八基-4-甲基酚、2,4,6-三環己基酚、2,6-二-三級丁基-4-甲氧基甲基酚、壬基酚,其為直鏈或在支鏈分枝,例如:2,6-二壬基-4-甲基酚、2,4-二甲基-6-(1’-甲基十一-1’-基)酚、2,4-二甲基-6-(1’-甲基十七-1’-基)酚、2,4-二甲基-6-(1’-甲基三癸-1’-基)酚與其混合物。
1.2.烷基硫甲基酚
,例如2,4-二辛基硫甲基-6-三級丁基酚、2,4-二辛基硫甲基-6-甲基酚、2,4-二辛基硫甲基-6-乙基酚、2,6-二-十二基硫甲基-4-壬基酚。
1.3.對苯二酚與烷化對苯二酚
,例如2,6-二三級丁基-4-甲氧基酚、2,5-二三級丁基對苯二酚、2,5-二三級戊基對苯二酚、2,6-二苯基-4-十八基氧基酚、2,6-二三級丁基對苯二酚、2,5-二三級丁基-4-羥基苯甲醚、3,5-二三級丁基-4-羥基苯甲醚、硬脂酸3,5-二三級丁基-4-羥基苯酯、己二酸雙(3,5-二三級丁基-4-羥基苯基)酯。
1.4.生育酚
,例如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚與其混合物(維生素E)。
1.5.羥基化硫代二苯醚
,例如2,2’-硫代雙(6-三級丁基-4-甲基酚)、2,2’-硫代雙(4-辛基酚)、4,4’-硫代雙(6-三級丁基-3-甲基酚)、4,4’-硫代雙(6-三級丁基-2-甲基酚)、4,4’-硫代雙(3,6-二二級戊基酚),二硫化4,4’-雙(2,6-二甲基-4-羥基苯基)。
1.6.亞烷基雙酚
,例如2,2’-亞甲基雙(6-三級丁基-4-甲基酚)、2,2’-亞甲基雙(6-三級丁基-4-乙基酚)、2,2’-亞甲基雙[4-甲基-6-(α-甲基環己基)酚]、2,2’-亞甲基雙(4-甲基-6-環己基酚)、2,2’-亞甲基雙(6-壬基-4-甲基酚)、2,2’-亞甲基雙(4,6-二三級丁基酚)、2,2’-亞乙基雙(4,6-二三級丁基酚)、2,2’-亞乙基雙(6-三級丁基-4-異丁基酚)、2,2’-亞甲基雙[6-(α-甲基苯甲基)-4-壬基酚]、2,2’-亞甲基雙[6-(α,α-二甲基苯甲基)-4-壬基酚]、4,4’-亞甲基雙(2,6-二三級丁基酚)、4,4’-亞甲基雙(6-三級丁基-2-甲基酚)、1,1雙(5-三級丁基-4-羥基-2-甲基苯基)丁烷、2,6-雙(3-三級丁基-5-甲基-2-羥基苯甲基)-4-甲基酚、1,1,3-參(5-三級丁基-4-羥基-2-甲基苯基)丁烷、1,1-雙(5-三級丁基-4-羥基-2-甲基苯基)-3-正十二基硫醇基丁烷、雙[3,3-雙(3’-三級丁基-4’-羥基苯基)丁酸]乙二醇酯、雙(3-三級丁基-4-羥基-5-甲基苯基)二環戊二烯、雙[2-(3’-三級丁基-2’-羥基-5’-甲基苯甲基)-6-三級丁基-4-甲基苯基]對苯二甲酸酯、1,1-雙(3,5-二甲基-2-羥基苯基)丁烷、2,2-雙(3,5-二三級丁基-4-羥基苯基)丙烷、2,2-雙(5-三級丁基-4-羥基-2-甲基苯基)-4-正十二基硫醇基丁烷,1,1,5,5-四(5-三級丁基-4-羥基-2-甲基苯基)戊烷。
1.7. O-、N-與S-苯甲基化合物
,例如3,5,3’,5’-四三級丁基-4,4’-二羥基二苯甲基醚、十八基-4-羥基-3,5-二甲基苯甲基硫醇基乙酸酯、三癸基-4-羥基-3,5-二三級丁基苯甲基硫醇基乙酸酯、參(3,5-二三級丁基-4-羥基苯甲基)胺、雙(4-三級丁基-3-羥基-2,6-二甲基苯甲基)二硫對苯二甲酸酯、雙(3,5-二三級丁基-4-羥基苯甲基)硫、異辛基-3,5-二三級丁基-4-羥基苯甲基硫醇基乙酸酯。
1.8.羥基苯甲基化丙二酸酯
,例如二(十八基)-2,2-雙(3,5-二三級丁基-2-羥基苯甲基)丙二酸酯、二(十八基)-2-(3-三級丁基-4-羥基-5-甲基苯甲基)丙二酸酯、二(十二基)硫醇基乙基-2,2-雙(3,5-二三級丁基-4-羥基苯甲基)丙二酸酯、雙[4-(1,1,3,3-四甲基丁基)苯基]-2,2-雙(3,5-二三級丁基-4-羥基苯甲基)丙二酸酯。
1.9.芳香族羥基苯甲基化合物
,例如1,3,5-參(3,5-二三級丁基-4-羥基苯甲基)-2,4,6-三甲基苯、1,4-雙(3,5-二三級丁基-4-羥基苯甲基)-2,3,5,6-四甲基苯、2,4,6-參(3,5-二三級丁基-4-羥基苯甲基)酚。
1.10.三 化合物
,例如2,4-雙(辛基硫醇基)-6-(3,5-二三級丁基-4-羥基苯胺)-1,3,5-三、2-辛基硫醇基-4,6-雙(3,5-二三級丁基-4-羥基苯胺)-1,3,5-三、2-辛基硫醇基-4,6-雙(3,5-二三級丁基-4-羥基苯氧基)-1,3,5-三、2,4,6-參(3,5-二三級丁基-4-羥基苯氧基)-1,2,3-三、1,3,5-參(3,5-二三級丁基-4-羥基苯甲基)三聚異氰酸酯、1,3,5-參(4-三級丁基-3-羥基-2,6-二甲基苯甲基)三聚異氰酸酯、2,4,6-參(3,5-二三級丁基-4-羥基苯基乙基)-1,3,5-三、1,3,5-參(3,5-二三級丁基-4-羥基丙醯基)-六氫-1,3,5-三、1,3,5-參(3,5-二環己基-4-羥基苯甲基)三聚異氰酸酯。
1.11.苯甲基膦酸酯
,例如二甲基-2,5-二三級丁基-4-羥基苯甲基膦酸酯、二甲基-3,5-二三級丁基-4-羥基苯甲基膦酸酯、二(十八基)-3,5-二三級丁基-4-羥基苯甲基膦酸酯、二(十八基)-5-三級丁基-4-羥基-3-甲基苯甲基膦酸酯、3,5-二三級丁基-4-羥基苯甲基膦酸之單乙酯之鈣鹽。
1.12.醯基胺基酚
,例如4-羥基十二醯苯胺、4-羥基十八醯苯胺,N-(3,5-二三級丁基-4-羥基苯基)胺甲酸辛酯。
1.13. β-(3,5-二三級丁基-4-羥基苯基)丙酸
與一元與多元醇之酯類
,例如與甲醇、乙醇、正辛醇、異辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二乙二醇、二乙二醇、三乙二醇、新戊四醇、參(羥基乙基)三聚異氰酸酯、N,N’-雙(羥基乙基)乙二醯二胺、3-硫十二醇、3-硫十五醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷酸-2,6,7-三氧二環[2.2.2]辛烷。
1.14. β-(5-三級丁基-4-羥基-3-甲基苯基)丙酸
與一元與多元醇之酯類
,例如與甲醇、乙醇、正辛醇、異辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二乙二醇、二乙二醇、三乙二醇、新戊四醇、參(羥基乙基)三聚異氰酸酯、N,N’-雙(羥基乙基)乙二醯二胺、3-硫十二醇、3-硫十五醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷酸-2,6,7-三氧二環[2.2.2]辛烷;3,9-雙[2-{3-(3-三級丁基-4-羥基-5-甲基苯基)丙醯氧}-1,1-二甲基乙基]-2,4,8,10-四氧雜螺[5.5]十一烷。
1.15. β-(3,5-二環己基-4-羥基苯基)丙酸
與一元與多元醇之酯類
,例如與甲醇、乙醇、辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二乙二醇、二乙二醇、三乙二醇、新戊四醇、參(羥基乙基)三聚異氰酸酯、N,N’-雙(羥基乙基)乙二醯二胺、3-硫十二醇、3-硫十五醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷酸-2,6,7-三氧二環[2.2.2]辛烷。
1.16. 3,5-二-三級丁基-4-羥基苯基乙酸
與一元與多元醇之酯類
,例如與甲醇、乙醇、辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二乙二醇、二乙二醇、三乙二醇、新戊四醇、參(羥基乙基)三聚異氰酸酯、N,N’-雙(羥基乙基)乙二醯二胺、3-硫十二醇、3-硫十五醇、三甲基己二醇、三羥甲基丙烷、4-羥基甲基-1-磷酸-2,6,7-三氧二環[2.2.2]辛烷。
1.17. β-(3,5-二三級丁基-4-羥基苯基)丙酸之醯胺
例如N,N’-雙(3,5-二三級丁基-4-羥基苯基丙醯基)六亞甲基二醯胺、N,N’-雙(3,5-二三級丁基-4-羥基苯基丙醯基)三亞甲基二醯胺、N,N’-雙(3,5-二三級丁基-4-羥基苯基丙醯基)醯肼、N,N’-雙[2-(3-[3,5-二三級丁基-4-羥基苯基]丙醯基氧基)乙基]乙二醯二胺(NaugardXL-1,由Uniroyal提供)。
同樣感興趣的方法包括作為成分(a)之至少一種式I化合物,其中式I化合物為式Ia,Ib或Ic之化合物。
Irganox 1135、Irganox 1076與Irganox 1010為Ciba Specialty Chemicals Inc之受保護的商業名稱。
在該新穎方法中作為成分(a)之式I化合物為已知的,且在某些例子中為商業上可獲得的。式I化合物之合適的製備方法可見於例如,US專利3,330,859或3,960,928。
較佳的作為成分(b)(i)之胺類抗氧化劑為式II之化合物
其中R2 5
為C1
-C1 8
烷基、苯基-C1
-C4
烷基、C5
-C1 2
環烷基、苯基、萘基;各經如下取代之苯基或萘基:C1
-C1 2
烷基或C1
-C1 2
烷氧基或苯甲基或α,α-二甲基苯甲基,R2 6
為苯基、萘基;各經如下取代之苯基或萘基:C1
-C1 2
烷基或C1
-C1 2
烷氧基或苯甲基或α,α-二甲基苯甲基,或R2 5
與R2 6
形成式III之基
其中R2 7
與R2 8
為氫或C1
-C1 8
烷基,R2 9
為氫,及R2 7
與R2 9
一起形成式之基。
一種感興趣的防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之方法包含胺類抗氧化劑作為成分(b)(i)之至少一種式II之化合物
其中R2 5
與R2 6
形成式III之基
其中R2 7
及R2 8
為C6
-C1 2
烷基,R2 9
為氫,或成分(b)(i)為二苯胺與二異丁烯反應所獲得之工業的混合物,包括α)二苯胺β)4-三級丁基-二苯胺γ)下列組群之化合物i)4-三級丁基二苯胺,ii)4,4’-二三級丁基二苯胺,iii)2,4,4’-參三級丁基二苯胺,δ)下列組群之化合物i)4-三級丁基-4'-三級辛基二苯胺,ii),o,o’、m,m’或p,p’-二三級辛基二苯胺,iii)2,4-二三級丁基-4'-三級辛基二苯胺,ε)下列組群之化合物i)4,4’-三級辛基二苯胺,ii)2,4-二三級辛基-4'-三級丁基二苯胺,及其中存在不超過5重量%之成分α)、8到15重量%之成分β)、24到32重量%之成分γ)、23到34重量%之成分δ)及21到34重量%之成分ε)。
烷基取代基可含有高至18個碳原子。這樣的取代之典型的實例為甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一基、十二基、十四基、十六基或十八基及相對應的支鏈的異構物,較佳的是,三級丁基、異辛基及異十二基。
一種防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之特別感興趣的方法包含下列胺類抗氧化劑作為成分(b)(i):一種防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之感興趣的方法包括作為成分(b)(i)之下列的胺類抗氧化劑:N,N’-二異丙基對苯二胺、N,N’-二-二級丁基對苯二胺、N,N’-雙(1,4-二甲基戊基)對苯二胺、N,N’-雙(1-乙基-3-甲基戊基)對苯二胺、N,N’-雙(1-甲基庚基)對苯二胺、N,N’-二環己基對苯二胺、N,N’-二苯基對苯二胺、N,N’-雙(2-萘基)對苯二胺、N-異丙基-N’-苯基對苯二胺、N-(1,3-二甲基丁基)-N’-苯基對苯二胺、N-(1-甲基庚基)-N’-苯基對苯二胺、N-環己基-N’-苯基對苯二胺、4-(對甲苯胺磺醯基)二苯胺、N,N’-二甲基-N,N’-二二級丁基對苯二胺、二苯胺、N-烯丙基二苯胺、4-異丙氧二苯胺、N-苯基-1-萘基胺、N-(4-三級辛基苯基)-1-萘基胺、N-苯基-2-萘基胺、辛基化之二苯胺,例如p,p’-二三級辛基二苯胺、4-正丁基胺基酚、4-丁醯基胺基酚、4-壬醯基胺基酚、4-十二醯基胺基酚、4-十八醯基胺基酚、雙(4-甲氧基苯基)胺、2,6-二三級丁基-4-二甲基胺甲基酚、2,4’-二胺基二苯基甲烷、4,4’-二胺基二苯基甲烷、N,N,N’,N’-四甲基-4,4’-二胺基二苯基甲烷、1,2-雙[(2-甲基苯基)胺基]乙烷、1,2-雙(苯基胺基)丙烷、(鄰甲苯基)二胍、雙[4-(1’,3’-二甲基丁基)苯基]胺、三級辛基化N-苯基-1-萘基胺、單與二烷基化之三級丁基/三級辛基二苯基胺之混合物、單與二烷基化之壬基二苯基胺之混合物、單與二烷基化之十二基二苯基胺之混合物、單與二烷基化之異丙基/異己基二苯基胺之混合物、單與二烷基化之三級丁基二苯基胺之混合物、2,3-二氫-3,3-二甲基-4H-1,4-苯并噻、啡噻、單與二烷基化之三級丁基/三級辛基啡噻之混合物、單與二烷基化之三級辛基啡噻之混合物、N-烯丙基啡噻,N,N,N’,N’-四苯基-1,4-二胺基丁-2-烯。
以上所提及之胺類抗氧化劑為已知的化合物,它們之中許多為商業上可獲得的。
以下的化合物為特別合適在根據本發明之方法中作為成分(b)(ii)之苯并呋喃-2-酮安定劑之實例:3-[4-(2-乙醯氧基乙氧基)苯基]-5,7-二三級丁基苯并呋喃-2-酮、5,7-二三級丁基-3-[4-(2-十八醯基氧乙氧基)苯基]苯并呋喃-2-酮、3,3’-雙[5,7-二三級丁基-3-(4-[2-羥基乙氧基]苯基)苯并呋喃-2-酮]、5,7-二三級丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮、3-(4-乙醯氧基-3,5-二甲基苯基)-5,7-二三級丁基苯并呋喃-2-酮、3-(-3,5-二甲基-4-新戊醯氧基苯基)-5,7-二三級丁基-苯并呋喃-2-酮、5,7-二三級丁基-3-苯基苯并呋喃-2-酮、5,7-二三級丁基-3-(3,4-二甲基苯基)苯并呋喃-2-酮,5,7-二三級丁基-3-(2,3-二甲基苯基)苯并呋喃-2-酮或5-三級辛基-3-(2-乙醯基-5-三級辛基苯基)苯并呋喃-2-酮。
一種防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之感興趣的方法為包含苯并呋喃-2-酮安定劑作為成分(b)(ii)之至少一種式IV之化合物
其中R9
為氫或C1
-C8
烷基,R1 0
為C1
-C1 2
烷基,R1 1
為氫、C1
-C4
烷基或C2
-C8
烷醯基,R1 2
為氫或C1
-C8
烷基,R1 3
為氫、C1
-C4
烷基或C1
-C4
烷氧基,及R1 4
為氫或C1
-C1 2
烷基。
C2
-C8
烷醯基為例如乙醯基、丙醯基、丁醯基、戊醯基、己醯基、庚醯基或辛醯基。乙醯基為較佳的。
特別較佳的苯并呋喃-2-酮安定劑為例如5,7-二三級丁基-3-苯基苯并呋喃-2-酮、5,7-二三級丁基-3-(3,4-二甲基苯基)苯并呋喃-2-酮,5,7-二三級丁基-3-(2,3-二甲基苯基)苯并呋喃-2-酮或5-三級辛基-3-(2-乙醯基-5-三級辛基苯基)苯并呋喃-2-酮。
式IV之苯并呋喃-2-酮安定劑為在文獻中已知,且在例如U.S.5,516,920中所揭示。
一種感興趣之防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之方法為包含亞磷酸酯或亞膦酸酯作為成分(b)(iii)之至少一種式V、VI,VII或VIII之化合物
其中n’為數字2且y’為數字1、2或3;A’為C2
-C1 8
伸烷基、對伸苯基或對伸聯苯基,E’,如果y’為1,則為C1
-C1 8
烷基、-OR’1
或氟;E’,如果y’為2,則為伸聯苯基,E’,如果y’為3,則為N(CH2
CH2
O-)3
,R’1
、R’2
、R’3
互相獨立為C1
-C1 8
烷基、C7
-C9
苯基烷基、環己烷基,苯基或經1到3個具有總數1到18個碳原子之烷基取代之苯基;R’1 4
為氫或C1
-C9
烷基,R’1 5
為氫或甲基,X’為一直接鍵,Y’為氧,Z’為一直接鍵結或-CH(R’1 6
)-,及R’1 6
為C1
-C4
烷基。
同樣有興趣之防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之方法包括作為成分(b)(iii)之至少一種式V、VI,VII或VIII之亞磷酸酯或亞膦酸酯,其中n’為數字2且y’為數字1’或3;A’為對伸聯苯基、E’,如果y’為1,為C1
-C1 8
烷氧基或氟,E’,如果y’為3,為N(CH2
O-)3
,R’1
、R’2
、R’3
互相獨立為C1
-C1 8
烷基或經2到3個具有總數2到12個碳原子之烷基取代之苯基;R’1 4
為甲基或三級丁基;R’1 5
為氫;X’為直接鍵;Y’為氧,且Z’為直接鍵、亞甲基或-CH(CH3
)-。
特別較佳之防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之方法包括作為成分(b)(iii)之至少一種式IX之亞磷酸酯
其中R1
及R2
為互相獨立地為氫、C1
-C8
烷基、環己基或苯基,及R3
及R4
互相獨立地為氫或C1
-C4
烷基。
下列化合物為在該新穎方法中特別適合作為成分(b)(iii)之有機亞磷酸酯與亞膦酸酯之實例。
亞磷酸三苯酯、亞磷酸二苯基烷基酯、亞磷酸苯基二烷基酯、亞磷酸參(壬基苯基)酯、亞磷酸三月桂酯、亞磷酸三十八基酯、二亞磷酸二硬脂基新戊四醇酯、亞磷酸參(2,4-二三級丁基苯基)酯(Irgafos168,Ciba Specialty Chemicals Inc.)、二亞磷酸二異癸基新戊四醇酯、二亞磷酸雙(2,4-二三級丁基苯基)新戊四醇酯(式D)、二亞磷酸雙(2,6-二三級丁基-4-甲基苯基)新戊四醇酯(式E)、二亞磷酸雙異癸基氧基新戊四醇酯、二亞磷酸雙(2,4-二三級丁基-6-甲基苯基)新戊四醇酯、二亞磷酸雙(2,4,6-三三級丁基苯基)新戊四醇酯、三亞磷酸三硬脂基葡萄糖醇酯、4,4’-聯苯二亞膦酸肆(2,4-二三級丁基苯基)酯(IrgafosP-EPQ,Ciba Specialty Chemicals Inc.,式H)、6-異辛基氧基-2,4,8,10-四三級丁基-12H-二苯[d,g]-1,3,2-二氧雜磷(phosphocin)(式C)、6-氟-2,4,8,10-四三級丁基-12-甲基二苯-[d,g]-1,3,2-二氧雜磷(式A)、亞磷酸雙(2,4-二三級丁基-6-甲基苯基)甲酯、亞磷酸雙(2,4-二三級丁基-6-甲基苯基)乙酯(式G)。
特別較佳者為下列之亞磷酸酯與亞膦酸酯:亞磷酸參(2,4-二三級丁基苯基)酯(Irgafos168,Ciba Specialty Chemicals Inc.),亞磷酸參(壬基苯基)酯。
非常特別較佳者為亞磷酸參(2,4-二三級丁基苯基)酯[Irgafos168,Ciba Specialty Chemicals Inc.]、亞磷酸雙(2,4-二三級丁基-6-甲基苯基)乙酯[Irgafos38,Ciba Specialty Chemicals Inc.,式(G)]、二亞磷酸雙(2,4-二三級丁基苯基)新戊四醇酯[Irgafos126,Ciba Specialty Chemicals Inc.,式(D)]、肆(2,4-二三級丁基苯基)-4,4’-聯苯二亞膦酸酯[IrgafosP-EPQ,Ciba Specialty ChemicalsInc.,式(H)]。
以上所提及之有機亞磷酸酯與亞膦酸酯係為已知的化合物;它們之中許多為商業上可獲得的。
成分(a)與(b)同樣被用於聚胺酯之生產,尤其是製備撓性聚胺酯發泡體。在本文中從其製備之新穎產物被有效地保護以防止降解並具有低含量醛污染物。特別地,可防止在發泡體製備期間之過早硫化現象。較佳而言,將亞磷酸酯如例如亞磷酸二苯異癸酯(DPDP)或亞磷酸苯基二異癸酯(PDDP)作為抗氧化劑與抗過早硫化劑系統,在發泡作用先前的混合之前端,以相對的高濃度(高到1.5重量%,以聚醚多元醇為基礎)後添加至鹼安定之聚醚多元醇。
所獲得之聚胺酯,例如,藉由將包含末端羥基之聚醚、聚酯及聚丁二烯與脂肪族或芳香族聚異氰酸酯反應。
具有末端羥基之聚醚及聚酯為已知的,且其製備係例如,藉由將環氧化物,例如環氧乙烷、環氧丙烷、環氧丁烷、四氫呋喃、氧化苯乙烯或表氯醇,例如在BF3
存在下,與其自身聚合,或是藉由這些環氧化物,單獨或呈混合物或連續地,與含有反應性氫原子之起始成分(例如水、醇、氨或胺,例如乙二醇、丙1,3-與1,2-二醇、三羥甲基丙烷、4,4’-二羥基二苯基丙烷、苯胺、乙醇胺或乙二胺)之加成反應。根據本發明蔗糖聚醚亦為合適的。在許多例子中,較佳者為那些主要(高至90重量%,以所有存在在聚醚之OH基為基礎)含有一級OH基的聚醚。此外,經乙烯聚合物修飾之聚醚(其形成係例如,藉由在聚醚存在下聚合苯乙烯與丙烯腈)是合適的,如同含有OH基之聚丁烯。
這些化合物一般具有40之分子量且為多元羥基化合物,尤其是含有從二到八個羥基的化合物,尤其是那些分子量從800到10000,較佳從1000到6000者,例如含有至少2,一般為2到8,但是較佳為2到4個羥基之聚醚,如同已知用於製備均相聚胺酯與多孔的聚胺酯者。
使用含有至少二個異氰酸酯反應性氫原子之前述化合物(特別是具有分子量400-100000)之混合物當然是適合的。
合適的聚異氰酸酯為脂肪族、環脂肪族、芳基脂肪族(araliphatic)、芳香族及雜環聚異氰酸酯,例如二異氰酸乙二酯、二異氰酸1,4-四亞甲基酯、二異氰酸1,6-六亞甲基酯、二異氰酸1,12-十二烷基酯、1,3-二聚異氰酸環丁烷基酯、1,3-與1,4-二異氰酸環己烷酯及這些異構物之任何合適混合物,1-異氰酸基-3,3,5-三甲基-5-異氰酸基甲基環己烷、二異氰酸2,4-與2,6-六氫甲苯酯以及這些異構物之任何合適的混合物、二異氰酸六氫-1,3-及/或-1,4-伸苯酯、二異氰酸全氫-2,4’及/或-4,4’-二苯基甲烷酯、二異氰酸1,3-及1,4-伸苯酯、二異氰酸2,4-及2,6-甲苯酯、以及這些異構物之任何合適的混合物、2,4’-及/或4,4’-二異氰酸二苯基甲烷酯、1,5-二異氰酸萘酯、4,4’,4”-三異氰酸三苯基甲烷酯、可藉由苯胺-甲醛縮合反應接著光氣作用所獲得之多元苯基-多元亞甲基聚異氰酸酯,間與對異氰酸基苯基磺醯基異氰酸酯、全氯化芳基聚異氰酸酯、含有碳二醯亞胺基之聚異氰酸酯、含有脲基甲酸酯基之聚異氰酸酯、含有異三聚氰酸酯基之聚異氰酸酯、含氨基甲酸乙酯基之聚異氰酸酯、含有醯化脲基之聚異氰酸酯、含有縮二脲基之聚異氰酸酯、含有酯基之聚異氰酸酯、前述提及之異氰酸酯與縮乙醛之反應產物及含有聚合脂肪酸基之聚異氰酸酯。
亦可使用含有該等異氰酸酯基的蒸餾殘餘物本身或溶解於一或多種以上提及之聚異氰酸酯,其係得自於工業製備異氰酸酯之過程中。此外另可使用以上提及之聚異氰酸酯之任何合適的混合物。
特別較佳者一般為工業上可立即獲得之聚異氰酸酯,例如:2,4-與2,6-甲苯二異氰酸酯與這些異構物(“TDI”)之任何合適的混合物、經由苯胺-甲醛之縮合反應後接著光氣作用所製備之多元苯基-多元亞甲基-聚異氰酸酯(“crude MDI”)及含有碳二醯亞胺、氨基甲酸乙酯、脲基甲酸酯、異三聚氰酸酯、尿素或縮二脲基之聚異氰酸酯(“修飾之聚異氰酸酯”)。
聚胺酯發泡體較佳是由液體起始成分製備,將要與彼此互相反應之該等起始材料在一步法中混合在一起,或者首先製備由多元醇與過量聚異氰酸酯形成之含NCO基預加成物,並典型地藉由與水反應發泡。
在發泡體之製備中,發泡經常是在模具中進行。在此例子中,反應混合物係被置於模具中。合適的模具材料為金屬,典型為鋁,或塑膠,典型為環氧樹脂。在模具中,發泡反應混合物發泡並形成模製物品。可進行發泡模製致使模製具有多孔的表面結構或,二者擇一地,致使模製具有緊密的外殼與多孔的核心。基於此關聯性,可將足量之發泡反應混合物置放入模具以得到確實充填模具之發泡體。然而,亦可將較以發泡體填滿模具內部所需為多之發泡反應混合物置入模具。因此,在後者的例子中,操作是在過量充填下進行。
在發泡模製之例子中,已知的外部脫模劑,典型地為矽油,經常被伴隨使用。然而,亦可使用所謂的內部脫模劑,視需要與外部脫模劑混合。其亦可使用冷熟化發泡。或者,該發泡體當然可以藉由嵌段發泡或已知的雙運輸帶方法製備。這些方法可用於製備撓性、半撓性或硬性聚胺酯發泡體。該發泡體被發現已知的實用性為這類產品,例如在傢俱與汽車工業上之床墊與墊襯物以及傢俱之製造,例如用於汽車工業,與最終作為隔音組成物與作為隔熱與隔絕低溫之組成物,例如在建築區或在冷藏工業,或在紡織工業,例如作為肩墊。
成分(a)較佳是以從0.01到10%的量添加到要被安定化之聚醚多元醇、聚酯多元醇或聚胺酯,特別是從0.01到5%,例如從0.01到2%,以要被安定化之聚醚多元醇、聚酯多元醇或聚胺酯之重量計。
成分(b)較佳是以從0.01到10 %的量添加到要被安定化之聚醚多元醇、聚酯多元醇或聚胺酯,特別是從0.01到5%,例如從0.01到2%,以要被安定化之聚醚多元醇、聚酯多元醇或聚胺酯之重量計。
除成分(a)與成分(b)之外,該防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之新穎方法可包括另外的共安定劑(添加劑),例如下列:
2.1. 2-(2’-羥基苯基)-苯並三唑
,例如2-(2’-羥基-5-甲基苯基)-苯并三唑、2-(3’,5’-二三級丁基-2’-羥基苯基)苯并三唑、2-(5’-三級丁基-2’-羥基苯基)苯并三唑、2-(2’-羥基-5’-(1,1,3,3,-四甲基丁基)苯基)苯并三唑、2-(3’,5’-二三級丁基-2’-羥基苯基)-5-氯-苯并三唑、2-(3’-三級丁基-2’-羥基-5’-甲基苯基)-5-氯-苯并三唑、2-(3’-二級丁基-5’-三級丁基-2’-羥基苯基)苯并三唑、2-(2’-羥基-4’-辛基氧基苯基)苯并三唑、2-(3’,5’-二三級戊基-2’-羥基苯基)苯并三唑、2-(3’,5’-雙-(α,α-二甲基苯甲基)-2’-羥基苯基)苯并三唑、2-(3’-三級丁基-2’-羥基-5’-(2-辛基氧基羰基乙基)苯基)-5-氯-苯并三唑、2-(3’-三級丁基-5’-[2-(2-乙基己基氧基)羰基乙基]-2’-羥基苯基)-5-氯-苯并三唑、2-(3’-三級丁基-2’-羥基-5’-(2-甲氧基羰基乙基)苯基)-5-氯-苯并三唑、2-(3’-三級丁基-2’-羥基-5’-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3’-三級丁基-2’-羥基-5’-(2-辛基氧基羰基乙基)苯基)苯并三唑、2-(3’-三級丁基-5’-[2-(2-乙基己基氧基)羰基乙基]-2’-羥基苯基)苯并三唑、2-(3’-十二基-2’-羥基-5’-甲基苯基)苯并三唑、2-(3’-三級丁基-2’-羥基-5’-(2-異辛基氧基羰基乙基)苯并三唑、2,2’-亞甲基-雙[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基酚];2-[3’-三級丁基-5’-(2-甲氧基羰基乙基)-2’-羥基苯基]-2H-苯并三唑與聚乙二醇300轉酯反應產物;,其中R=3’-三級丁基-4’-羥基-5’-2H-苯并三唑-2-基苯基、2-[2’-羥基-3’-(α,α-二甲基苯甲基)-5’-(1,1,3,3-四甲基丁基)-苯基]-苯并三唑,2-[2’-羥基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苯甲基)-苯基]苯并三唑。
2.2. 2-羥基二苯基酮
,例如4-羥基、4-甲氧基、4-辛氧基、4-癸氧基、4-十二氧基、4-苄氧基,4,2’,4’-三羥基與2’-羥基-4,4’-二甲氧基衍生物。
2.3.經取代及未經取代之苯甲酸之酯類
,例如柳酸4-三級丁基苯酯、柳酸苯酯、柳酸辛基苯酯、二苯甲醯間苯二酚、雙(4-三級丁基苯甲醯)間苯二酚、苯甲醯間苯二酚、3,5-二三級丁基-4-羥基苯甲酸-2,4-二三級丁基苯酯、3,5-二三級丁基-4-羥基苯甲酸十六酯、3,5-二三級丁基-4-羥基苯甲酸酸十八酯、3,5-二三級丁基-4-羥基苯甲酸-2-甲基-4,6-二三級丁基苯酯。
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-二苯基丙烯酸異辛酯、α-甲氧甲醯基桂皮酸甲酯、α-氰基-β-甲基-p-甲氧基桂皮酸甲酯、α-氰基-β-甲基-對甲氧基桂皮酸丁酯、α-甲氧甲醯基-對甲氧基桂皮酸甲酯、N-(β-甲氧甲醯基-β-氰基乙烯基)-2-甲基吲哚啉、四(α-氰基-β,β-二苯基)丙烯酸新戊酯。
2.5.鎳化合物
,例如2,2’-硫-雙[4-(1,1,3,3-四甲基丁基)酚]之鎳錯合物,如1:1或1:2錯合物,具有或不具額外的配位基如正丁基胺、三乙醇胺或N-環己基二乙醇胺、二丁基二硫胺甲酸鎳,4-羥基-3,5-二三級丁基苄膦酸之單烷基酯(例如:甲酯或乙酯)之鎳鹽、酮肟之鎳錯合物,例如:2-羥基-4-甲基苯基十一基酮肟,具有或不具額外配位基之1-苯基-4-十二醯基-5-羥基吡唑之鎳錯合物。
2.6.空間位阻之胺
,例如雙(2,2,6,6-四甲基-4-六氫吡啶基)癸二酸酯、雙(2,2,6,6-四甲基-4-六氫吡啶基)琥珀酸酯、雙(1,2,2,6,6-五甲基-4-六氫吡啶基)癸二酸酯、雙(1-辛氧基-2,2,6,6-四甲基-4-六氫吡啶基)癸二酸酯、正丁基-3,5-二三級丁基-4-羥基苯甲基丙二酸雙(1,2,2,6,6-五甲基-4-六氫吡啶基酯)、1-(2-羥基乙基)-2,2,6,6-四甲基-4-羥基六氫吡啶與琥珀酸之縮合物、N,N’-雙(2,2,6,6-四甲基-4-六氫吡啶基)六亞甲二胺與4-三級辛基胺基-2,6-二氯-1,3,5-三之線型或環化縮合物、參(2,2,6,6-四甲基-4-六氫吡啶基)氮基乙酸酯、肆(2,2,6,6-四甲基-4-六氫吡啶基)-1,2,3,4-丁四羧酸酯、1,1’-(1,2-乙二基)-雙(3,3,5,5-四甲基4-六氫吡酮)、4-苯甲醯基-2,2,6,6-四甲六氫吡啶、4-十八氧基-2,2,6,6-四甲六氫吡啶、雙(1,2,2,6,6-五甲基六氫吡啶基)-2-正丁基-2-(2-羥基-3,5-二三級丁基苯甲基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮螺[4,5]癸-2,4-二酮、雙(1-辛氧基-2,2,6,6-四甲基-4-六氫吡啶基)癸二酸二酯、雙(1-辛氧基-2,2,6,6-四甲基-4-六氫吡啶基)丁二酸二酯、N,N’-雙(2,2,6,6-四甲基-4-六氫吡啶基)六亞甲二胺與4-嗎福啉代-2,6-二氯-1,3,5-三之線型或環化縮合物、2-氯-4,6-雙(4-正丁基胺基-2,2,6,6-四甲基六氫吡啶基)-1,3,5-三與1,2-雙(3-胺基丙基胺基)-乙烷之縮合物、2-氯-4,6-二(4-正丁基胺基-1,2,2,6,6-五甲基六氫吡啶基)-1,3,5-三與1,2-雙(3-胺基丙基胺基)-乙烷之縮合物、8-乙醯基-3-十二基-7,7,9,9-四甲基-1,3,8-三氮螺[4,5]癸-2,4-二酮、3-十二基-1-(2,2,6,6-四甲基-4-六氫吡啶基)吡咯啶-2,5-二酮、3-十二基-1-(1,2,2,6,6-五甲基-4-六氫吡啶基)吡咯啶-2,5-二酮、4-十六基氧-與4-十八基氧-2,2,6,6-四甲基六氫吡啶之混合物、N,N’-雙(2,2,6,6-四甲基-4-六氫吡啶基)六亞甲二胺與4-環己基胺基-2,6-二氯-1,3,5-三之縮合物、1,2-雙(3-胺基丙基胺基)-乙烷與2,4,6-三氯-1,3,5-三之縮合物,如同4-丁基胺基-2,2,6,6-四甲基六氫啶(CAS Reg.No.[136504-96-6]);1,6-己二胺與2,4,6-三氯-1,3,5-三之縮合物,如同N,N’-二丁基胺與4-丁基胺基-2,2,6,6-四甲基六氫吡啶(CAS Reg.No.[192268-64-7]);N-(2,2,6,6-四甲基-4-六氫吡啶基)-正十二基丁二醯亞胺、N-(1,2,2,6,6-五甲基-4-六氫吡啶基)-正十二基丁二醯亞胺、2-十一基-7,7,9,9-四甲基-1-氧雜-3,8-二氮-1-氧基-螺[4,5]癸烷、7,7,9,9-四甲基-2-環十一基-1-氧-3,8-二氮-4-側氧基-螺[4,5]癸烷與表氯醇之反應產物、1,1-雙(1,2,2,6,6-五甲基-4-六氫吡啶基氧羰基)-2-(甲氧苯基)乙烯、N,N’-雙甲醯基-N,N’-雙(2,2,6,6-四甲基-4-六氫吡啶基)六亞甲基二胺、4-甲氧基亞甲基丙二酸與1,2,2,6,6-五甲基-4-六氫吡啶之二酯、聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-六氫吡啶基)]矽氧烷、順丁烯二酸酐-α-烯烴共聚物與2,2,6,6-四甲基-4-胺基六氫吡啶或1,2,2,6,6-五甲基-4-胺基六氫吡啶之反應產物、2,4-雙[N-(1-環己基氧基-2,2,6,6-四甲基六氫吡啶-4-基)-N-丁基胺基]-6-(2-羥基乙基)胺基-1,3,5-三、1-(2-羥基-2-甲基丙氧基)-4-十八醯基氧基-2,2,6,6-四甲基六氫吡啶、5-(2-乙基己醯基)氧甲基-3,3,5-三甲基-2-嗎福啉酮、Sanduvor(Clariant;CAS Reg.No.106917-31-1)、5-(2-乙基己醯基)氧甲基-3,3,5-三甲基-2-嗎福啉酮、2,4-雙[(1-環己基氧基-2,2,6,6-六氫吡啶-4-基)丁基胺基-6-氯-s-三與N,N’-雙(3-胺基丙基)乙二胺之反應產物、1,3,5-參(N-環己基-N-(2,2,6,6-四甲基-六氫吡-3-酮-4-基)胺基)-s-三、1,3,5-參(N-環己基-N-(1,2,2,6,6-五甲基-六氫吡-3-酮-4-基)胺基)-s-三。
2.7.草醯胺
,例如4,4’-二辛基氧基草醯二苯胺、2,2’-二乙氧基草醯二苯胺、2,2’-二辛基氧基-5,5’-二三級丁基草醯二苯胺、2,2’-二十二基氧基-5,5’-二三級丁基草醯二苯胺、2-乙氧基-2’-乙基草醯二苯胺、N,N’-雙(3-二甲基胺基丙基)草醯胺,2-乙氧基-5-三級丁基-2’-乙基草醯二苯胺及其與2-乙氧基-2’-乙基-5,4’-二三級丁基草醯二苯胺之混合物,鄰-與對氧基-二取代之草醯二苯胺之混合物與鄰-與對-乙氧基-二取代之草醯二苯胺之混合物。
2.8. 2-(2-羥基苯基)-1,3,5-三 ,例如2,4,6-參(2-羥基-4-辛基氧苯基)-1,3,5-三、2-(2-羥基-4-辛基氧基苯基)-4,6-雙(2,4-二甲基苯基)-1,3,5-三、2-(2,4-二羥基苯基)-4,6-雙(2,4-二甲基苯基)-1,3,5-三、2,4-雙(2-羥基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三、2-(2-羥基-4-辛氧基苯基)-4,6-雙(4-甲基苯基)-1,3,5-三、2-(2-羥基-4-十二基氧基苯基)-4,6-雙(2,4-二甲基苯基)-1,3,5-三、2-(2-羥基-4-三癸基氧基苯基)-4,6-雙(2,4-二甲基苯基)-1,3,5-三、2-[2-羥基-4-(2-羥基-3-丁基氧基丙氧基)苯基]-4,6-雙(2,4-二甲基)-1,3,5-三、2-[2-羥基-4-(2-羥基-3-辛基氧基丙氧基)苯基]-4,6-雙(2,4-二甲基)-1,3,5-三、2-[4-(十二基氧基/三癸基氧基-2-羥基丙氧基)-2-羥基苯基]-4,6-雙(2,4-二甲基苯基)-1,3,5-三、2-[2-羥基-4-(2-羥基-3-十二基氧基丙氧基)苯基]-4,6-雙(2,4-二甲基苯基)-1,3,5-三、2-(2-羥基-4-己氧基)苯基-4,6-二苯基-1,3,5-三、2-(2-羥基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三、2,4,6-參[2-羥基-4-(3-丁氧基-2-羥基丙氧基)苯基]-1,3,5-三、2-(2-羥基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三、2-{2-羥基-4-[3-(2-乙基己基-1-氧基)-2-羥基丙氧基]苯基}-4,6-雙(2,4-二甲基苯基)-1,3,5-三,2,4-參(4-[2-乙基己基氧基]-2-羥基苯基)-6-(4-甲氧基苯基)-1,3,5-三。
3.金屬衍生物
,例如N,N’-二苯基草醯胺、N-柳醛基-N’-柳醯肼、N,N’-雙(柳醯基)肼、N,N’-雙(3,5-二三級丁基-4-羥基苯基丙醯基)肼、雙(亞苄基)草醯基二醯肼、草醯二苯胺、間苯二醯二醯肼、N,N’-雙(柳醯基)草醯二醯肼,N,N’-雙(柳醯基)硫丙醯基二醯肼。
4.羥胺
,例如N,N’-二苯甲基羥胺、N,N’-二乙基羥胺、N,N’-二辛基羥胺、N,N’-二月桂基羥胺、N,N’-二-十四基羥胺、N,N’-二-十六基羥胺、N,N’-二-十八基羥胺、N-十六基-N-十八基羥胺、N-十六基-N-十八基羥胺、N-十七基-N-十八基羥胺、衍生自氫化牛脂胺之N,N’-二烷基羥胺。
5.硝酮(Nitrones)
,例如,N-苯甲基-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-十一基硝酮、N-十四基-α-十三基硝酮、N-十六基-α-十五基硝酮、N-十八基-α-十七基硝酮、N-十六基-α-十七基硝酮、N-十八基-α-十五基硝酮、N-十七基-α-十七基硝酮、N-十八基-α-十六基硝酮,衍生自來自於氫化牛脂胺之N,N’-二烷基羥胺之硝酮。
6.硫增效劑(Thiosynergists)
,例如硫二丙酸二月桂酯、硫二丙酸二肉豆蔻酯(dimistryl thiodipropionate)、硫二丙酸二硬脂酸酯或二硫化二(硬脂基)。
7.過氧化物捕捉劑
,例如β-硫二丙酸之酯,例如月桂基、硬脂基、肉豆蔻基或十三基酯、硫醇基苯並咪唑或2-硫醇基苯並咪唑之鋅鹽、二丁基二硫胺基甲酸鋅、二硫化二(十八基),肆(β-十二基硫醇基)丙酸新戊四醇酯。
8.基本的共安定劑
,例如三聚氰胺、聚乙烯四氫吡咯烷酮、雙氰胺、三聚氰脲酸三烯丙酯、尿素衍生物、肼衍生物、胺、聚醯胺、聚胺酯、高級脂肪酸之鹼金屬鹽與鹼土金屬鹽,例如硬脂酸鈣、硬脂酸鋅、二十二酸鎂、硬脂酸鎂,蓖麻酸鈉與軟脂酸鉀、鄰苯二酸銻或鄰苯二酸鋅。
9.填充劑與加強劑
,例如碳酸鈣、矽酸鹽、玻璃纖維、玻璃珠、石棉、滑石、高嶺土、雲母、硫酸鋇、金屬氧化物與氫氧化物、碳黑、石墨、木材粉及其他天然物之粉或纖維,合成纖維。
10.其他的添加劑
,例如增塑劑、潤滑劑、乳化劑、顏料、流變學添加劑、催化劑、流量控制劑、光亮劑、防焰劑、抗靜電劑與發泡劑。
共安定劑係以,例如0.01到10%之濃度加入,其相對於欲被安定之聚醚多元醇、聚酯多元醇及聚胺酯總重量。
較佳之另外的添加劑為光安定劑(表之項目2)。
本發明之較佳的標的亦為成分(a)與成分(b)之混合物用以防止聚醚多元醇、聚酯多元醇或聚胺酯之醛類污染物形成的用途。
以下之實例更詳細地說明本發明。份與百分比為以重量計。
在表1所指示之安定劑混合物以表1所指示之量溶解於160公克之聚醚多元醇[Petol 46-3MB(RTM)(具有一級羥基之三效聚醚多元醇;羥數目48毫克KOH/公克,水含量少於0.1%,酸數目少於0.1毫克KOH/公克)]。聚醚多元醇在80℃下被儲存在烘箱數天。藉由定期地取出樣品來測量甲醛、乙醛與丙醛之形成數量。將這些樣品以二硝基苯基肼-乙腈溶液(DNPH-乙腈溶液)處理。形成的甲醛-DNPH、乙醛-DNPH及丙醛-DNPH藉由HPLC方法,使用Alltima C18 5微米管柱[4.6×250毫米]在30℃之管柱溫度與含有60%乙腈與40%水之流動相而定量地測量。溶劑流量為1.2毫升/分鐘。結果總結在表1與2。
a)比較樣品。
b)根據本發明之實施例。
c)Irganox 1135(RTM)(Ciba specialty Chemical Inc.)為式AO-1之酚類抗氧化劑。
d)混合物1為2份Irganox 1135c )
與1份Irganox 5057h )
之混合物。
e)混合物2為7份Irganox 1135c )
、1份Irgafos 38i )
與1份Irganox HP 136j )
之混合物。
f)混合物3為10份Irganox 1135c )
、3份Irganox 5057h )
與1份PS-1k )
之混合物。
g)混合物4為7份Irganox 1135c )
、1份Irgafos 38i )
與1份PS-1k )
之混合物。
h)Irganox 5057(RTM)(Ciba Speciality Chemicals Inc.)為胺類抗氧化劑且為二苯基胺與二異丁烯之反應所獲得之工業混合物,包括α)二苯胺;β)4-三級丁基二苯胺;γ)下列組群之化合物i)4-三級辛基二苯胺,ii)4,4’-二三級丁基二苯胺,iii)2,4,4’-參-三級丁基二苯胺,δ)下列組群之化合物i)4-三級丁基-4’-三級辛基二苯胺,ii)o,o’,m,m’或p,p’-二三級辛基二苯胺,iii)2,4-二三級丁基-4’-三級辛基二苯胺,ε)下列組群之化合物i)4,4’-二三級辛基二苯胺,ii)2,4-二三級辛基-4’-三級丁基二苯胺,及其中存在不超過5重量%之成分α)、8到15重量%之成分β)、24到32重量%之成分γ)、23到34重量%之成分δ)及21到34重量%之成分ε)。
i)Irgafos 38(RTM)(Ciba specialty Chemical Inc.)為亞磷酸雙(2,4-二三級丁基-6-甲基苯基)乙酯。
j)Irganox HP 136(RTM)(Ciba specialty Chemical Inc.)為約85重量份的式IVa化合物與約15重量份的式IVb化合物之混合物。
k)PS-1為式IVc之3-(2-乙醯基-5-異辛基苯基)-5-異辛基苯并呋喃-2-酮。
Claims (4)
- 一種成分(a)與(b)的混合物於防止在聚醚多元醇、聚酯多元醇或聚胺酯中形成醛類污染物之用途,其包括於該聚醚多元醇、聚酯多元醇或聚胺酯中併入有效量之(a)酚類抗氧化劑,(b)以下二者之混合物(ii)苯并呋喃-2-酮及(iii)亞磷酸雙(2,4-二-三級丁基-6-甲基苯基)乙酯;其中作為成分(a)之酚類抗氧化劑為式I之化合物
- 根據申請專利範圍第1項之用途,其中成分(b)(ii)為式IV之化合物
- 根據申請專利範圍第1項之用途,另包括除了成分(a)與(b)外之另外的添加劑。
- 根據申請專利範圍第3項之用途,包括作為另外的添加劑之光安定劑。
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2010
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Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW399079B (en) * | 1995-05-12 | 2000-07-21 | Ciba Sc Holding Ag | Polyether polyol and polyurethane compositions protected against oxidation and core scorching |
Also Published As
Publication number | Publication date |
---|---|
US20110054220A1 (en) | 2011-03-03 |
ATE428748T1 (de) | 2009-05-15 |
US20090182078A1 (en) | 2009-07-16 |
WO2006111492A3 (en) | 2006-12-28 |
ES2322776T3 (es) | 2009-06-26 |
EP1874853A2 (en) | 2008-01-09 |
JP2008536991A (ja) | 2008-09-11 |
JP5107898B2 (ja) | 2012-12-26 |
EP1874853B2 (en) | 2012-07-04 |
EP1874853B1 (en) | 2009-04-15 |
DE602006006304D1 (de) | 2009-05-28 |
WO2006111492A2 (en) | 2006-10-26 |
CN101163735A (zh) | 2008-04-16 |
US7879928B2 (en) | 2011-02-01 |
TW200708548A (en) | 2007-03-01 |
ES2322776T5 (es) | 2012-11-20 |
CN101163735B (zh) | 2011-12-07 |
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