CN106332548A - 聚氨酯烧焦抑制剂 - Google Patents
聚氨酯烧焦抑制剂 Download PDFInfo
- Publication number
- CN106332548A CN106332548A CN201580023498.6A CN201580023498A CN106332548A CN 106332548 A CN106332548 A CN 106332548A CN 201580023498 A CN201580023498 A CN 201580023498A CN 106332548 A CN106332548 A CN 106332548A
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- China
- Prior art keywords
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- described derivative
- derivative
- hydroquinone
- tert
- Prior art date
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- Granted
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- 239000003112 inhibitor Substances 0.000 title claims description 11
- 239000004814 polyurethane Substances 0.000 title description 16
- 229920002635 polyurethane Polymers 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims abstract description 87
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims abstract description 46
- 150000002596 lactones Chemical class 0.000 claims abstract description 37
- 239000000654 additive Substances 0.000 claims abstract description 25
- 229920005830 Polyurethane Foam Polymers 0.000 claims abstract description 24
- 239000011496 polyurethane foam Substances 0.000 claims abstract description 24
- 150000002989 phenols Chemical class 0.000 claims abstract description 18
- 230000000996 additive effect Effects 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000006260 foam Substances 0.000 description 29
- -1 lactone compound Chemical class 0.000 description 23
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 16
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 229910002089 NOx Inorganic materials 0.000 description 10
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000002152 alkylating effect Effects 0.000 description 8
- 239000003546 flue gas Substances 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 6
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000003963 antioxidant agent Substances 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000003063 flame retardant Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000011160 research Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000003078 antioxidant effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000006384 oligomerization reaction Methods 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- 150000005846 sugar alcohols Polymers 0.000 description 5
- ALVZNPYWJMLXKV-UHFFFAOYSA-N 1,9-Nonanediol Chemical compound OCCCCCCCCCO ALVZNPYWJMLXKV-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N 1-nonene Chemical compound CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- FXNDIJDIPNCZQJ-UHFFFAOYSA-N 2,4,4-trimethylpent-1-ene Chemical group CC(=C)CC(C)(C)C FXNDIJDIPNCZQJ-UHFFFAOYSA-N 0.000 description 4
- CKPKHTKLLYPGFM-UHFFFAOYSA-N 6,6-dimethylheptane-1,1-diol Chemical compound CC(CCCCC(O)O)(C)C CKPKHTKLLYPGFM-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 238000002845 discoloration Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-UHFFFAOYSA-N 0.000 description 3
- KXPXKNBDCUOENF-UHFFFAOYSA-N 2-(Octylthio)ethanol Chemical compound CCCCCCCCSCCO KXPXKNBDCUOENF-UHFFFAOYSA-N 0.000 description 3
- ZPIRWAHWDCHWLM-UHFFFAOYSA-N 2-dodecylsulfanylethanol Chemical compound CCCCCCCCCCCCSCCO ZPIRWAHWDCHWLM-UHFFFAOYSA-N 0.000 description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000002485 combustion reaction Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- BVUXDWXKPROUDO-UHFFFAOYSA-N 2,6-di-tert-butyl-4-ethylphenol Chemical compound CCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 BVUXDWXKPROUDO-UHFFFAOYSA-N 0.000 description 2
- DKCPKDPYUFEZCP-UHFFFAOYSA-N 2,6-di-tert-butylphenol Chemical class CC(C)(C)C1=CC=CC(C(C)(C)C)=C1O DKCPKDPYUFEZCP-UHFFFAOYSA-N 0.000 description 2
- MGWGWNFMUOTEHG-UHFFFAOYSA-N 4-(3,5-dimethylphenyl)-1,3-thiazol-2-amine Chemical compound CC1=CC(C)=CC(C=2N=C(N)SC=2)=C1 MGWGWNFMUOTEHG-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 2
- 229940038384 octadecane Drugs 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- DIVDFFZHCJEHGG-UHFFFAOYSA-N oxidopamine Chemical compound NCCC1=CC(O)=C(O)C=C1O DIVDFFZHCJEHGG-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 2
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 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 2
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 2
- FKFOHTUAFNQANW-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl) octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FKFOHTUAFNQANW-UHFFFAOYSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products 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 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ICKWICRCANNIBI-UHFFFAOYSA-N 2,4-di-tert-butylphenol Chemical class CC(C)(C)C1=CC=C(O)C(C(C)(C)C)=C1 ICKWICRCANNIBI-UHFFFAOYSA-N 0.000 description 1
- OPLCSTZDXXUYDU-UHFFFAOYSA-N 2,4-dimethyl-6-tert-butylphenol Chemical compound CC1=CC(C)=C(O)C(C(C)(C)C)=C1 OPLCSTZDXXUYDU-UHFFFAOYSA-N 0.000 description 1
- MFZAXZRJGHLULL-UHFFFAOYSA-N 2,4-ditert-butyl-6-[2-(3,5-ditert-butyl-2-hydroxyphenyl)ethyl]phenol Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(CCC=2C(=C(C=C(C=2)C(C)(C)C)C(C)(C)C)O)=C1O MFZAXZRJGHLULL-UHFFFAOYSA-N 0.000 description 1
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
- FLLRQABPKFCXSO-UHFFFAOYSA-N 2,5-ditert-butyl-4-methoxyphenol Chemical compound COC1=CC(C(C)(C)C)=C(O)C=C1C(C)(C)C FLLRQABPKFCXSO-UHFFFAOYSA-N 0.000 description 1
- JFGVTUJBHHZRAB-UHFFFAOYSA-N 2,6-Di-tert-butyl-1,4-benzenediol Chemical compound CC(C)(C)C1=CC(O)=CC(C(C)(C)C)=C1O JFGVTUJBHHZRAB-UHFFFAOYSA-N 0.000 description 1
- VQQLTEBUMLSLFJ-UHFFFAOYSA-N 2,6-ditert-butyl-4-nonylphenol Chemical compound CCCCCCCCCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 VQQLTEBUMLSLFJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 1
- TVLJNSWXEVTWIT-UHFFFAOYSA-N 2-[(3,5-ditert-butyl-4-hydroxyphenyl)methyl]-13-methyltetradecanoic acid Chemical compound CC(C)CCCCCCCCCCC(C(O)=O)CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 TVLJNSWXEVTWIT-UHFFFAOYSA-N 0.000 description 1
- UIXRDRQSWYSVNK-UHFFFAOYSA-N 2-butyl-4,6-dimethylphenol Chemical compound CCCCC1=CC(C)=CC(C)=C1O UIXRDRQSWYSVNK-UHFFFAOYSA-N 0.000 description 1
- AKNMPWVTPUHKCG-UHFFFAOYSA-N 2-cyclohexyl-6-[(3-cyclohexyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound OC=1C(C2CCCCC2)=CC(C)=CC=1CC(C=1O)=CC(C)=CC=1C1CCCCC1 AKNMPWVTPUHKCG-UHFFFAOYSA-N 0.000 description 1
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- GPNYZBKIGXGYNU-UHFFFAOYSA-N 2-tert-butyl-6-[(3-tert-butyl-5-ethyl-2-hydroxyphenyl)methyl]-4-ethylphenol Chemical compound CC(C)(C)C1=CC(CC)=CC(CC=2C(=C(C=C(CC)C=2)C(C)(C)C)O)=C1O GPNYZBKIGXGYNU-UHFFFAOYSA-N 0.000 description 1
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- 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 description 1
- 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 description 1
- MBMUWELGNWWSKI-UHFFFAOYSA-N 4-(oxiran-2-ylmethoxy)phenol Chemical compound C1=CC(O)=CC=C1OCC1OC1 MBMUWELGNWWSKI-UHFFFAOYSA-N 0.000 description 1
- PRWJPWSKLXYEPD-UHFFFAOYSA-N 4-[4,4-bis(5-tert-butyl-4-hydroxy-2-methylphenyl)butan-2-yl]-2-tert-butyl-5-methylphenol Chemical compound C=1C(C(C)(C)C)=C(O)C=C(C)C=1C(C)CC(C=1C(=CC(O)=C(C=1)C(C)(C)C)C)C1=CC(C(C)(C)C)=C(O)C=C1C PRWJPWSKLXYEPD-UHFFFAOYSA-N 0.000 description 1
- FKIOYBLZUCCLTL-UHFFFAOYSA-N 4-butyl-2-tert-butyl-5-methylphenol Chemical compound CCCCC1=CC(C(C)(C)C)=C(O)C=C1C FKIOYBLZUCCLTL-UHFFFAOYSA-N 0.000 description 1
- UXMKUNDWNZNECH-UHFFFAOYSA-N 4-methyl-2,6-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC(C)=CC(CCCCCCCCC)=C1O UXMKUNDWNZNECH-UHFFFAOYSA-N 0.000 description 1
- OILMLWAZYNVPMG-UHFFFAOYSA-N 4-methyl-2-nonylphenol Chemical compound CCCCCCCCCC1=CC(C)=CC=C1O OILMLWAZYNVPMG-UHFFFAOYSA-N 0.000 description 1
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- 101710194180 Alcohol oxidase 1 Proteins 0.000 description 1
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- 244000025254 Cannabis sativa Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 241001161843 Chandra Species 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-UHFFFAOYSA-N Dicyclopentadiene Chemical compound C1C2C3CC=CC3C1C=C2 HECLRDQVFMWTQS-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- DJOWTWWHMWQATC-KYHIUUMWSA-N Karpoxanthin Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1(O)C(C)(C)CC(O)CC1(C)O)C=CC=C(/C)C=CC2=C(C)CC(O)CC2(C)C DJOWTWWHMWQATC-KYHIUUMWSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
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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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- 239000002446 δ-tocopherol Substances 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
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- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
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Abstract
用于抑制聚氨酯泡沫组合物烧焦的添加剂组合物,该添加剂组合物包含衍生的对苯二酚;衍生的内酯;及衍生的酚化合物。聚氨酯泡沫组合物含有此添加剂组合物。
Description
发明的背景
本发明涉及聚氨酯泡沫的抑制烧焦的添加剂。聚氨酯块状型泡沫的制造涉及剧烈的放热反应。延长的反应后热暴露会导致化学变化,这表现为生产的泡沫块的内部变黑并被定义为烧焦。为了抑制不期望的烧焦,制造商添加抗氧化混合物,其通常被称为烧焦抑制剂。烧焦抑制剂通过能降低热诱导的变黑的损害效应的复杂牺牲反应起作用。因此,烧焦抑制剂有效地减少产品损失。
聚氨酯烧焦的概要
在聚氨酯块状型泡沫的制造中,观察到剧烈的放热反应,这导致内部变色1。通常被理解为是多元醇与二-异氰酸酯缩合(凝胶化)反应及“下列反应”的结果2。
方程式1(上方)异氰酸酯的水解
方程式2(下方)异氰酸酯与胺缩合以生成脲
制造商已测量出对应于聚氨酯泡沫基质中形成的组分部分的反应热:氨基甲酸酯(urethane)为约24kcal/mol以及脲为约47kcal/mol。视觉上,因未消散的热产生了在生产的泡沫块的内部中被称为烧焦的变黑的黄色变色。研究者已显示复杂的自由基反应驱动烧焦过程3。已间接测量出降解效果,这显示断链及聚醚多元醇配方组分的氧化4。诸如本发明的配方已用于降低断链及PUR泡沫的一般的化学变化。
环境因素与泡沫变色
氮氧化物诱导的PUR泡沫的变色
聚氨酯泡沫制造商关注于另一PUR泡沫降解现象5。一般来说,热、光、光氧化及NOx烟气(主要为一氧化氮(NO)及二氧化氮(NO2))在泡沫表面上产生黄色或粉红色(方程式3)6。
方程式3:丙烷燃烧
关于氮氧化物烟气,变色已与仓库中升高的NOx水平强烈相关。已有文献探讨了季节性影响。在较冷的月份里,不良通风的仓库趋向于累积更大浓度的由以丙烷为燃料的叉车和煤气燃烧炉产生的NOx烟气7。此影响是可充分理解的。Tompkins和Smith解释了仓库中的多种逸散性排放,如一氧化碳、二手烟、来自新产品的化学废气及废烟气收集8。在较温暖的月份里,工厂运作和汽车排放导致大气中NOx浓度升高而驱动变色9。温暖月份的特点还在于其具有影响NOx烟气浓度及其化学特性的另外因素。依据一些大气研究,NOx持续与氧及水蒸气反应以变成空气传播的硝酸气雾10。显然地,在高湿度条件下发现水合形式的硝酸。一项研究显示,与低湿度条件相比,玻璃纤维中的硝酸颗粒的量在高湿度条件下会大大地增加11。因此,富含NOx烟气的仓库空气可形成酸性气雾。NOx烟气的化学特性复杂,但其对泡沫成分和颜色的影响被广泛接受12、13。相比于其它已知的抗氧化剂烧焦抑制剂,本发明降低在仓库中储存的PUR泡沫中普遍观察到的变色影响。
PUR泡沫的荧光和UV诱导的变色
已进行许多相关研究,显示PUR如何可能促成由光-氧化效应引起的颜色14。Chandra报道短波长(<340nm)照射促进Photo-Fries机制,其中氨基甲酸酯连接被破坏并再结合至芳香环,释放游离的NH2。在较长波长下,有色物质衍生自过氧化氢反应。根据Noack与Schwetlick,所观察到的黄化为芳香环上的暴露的胺官能团氧化的结果(方程式4)。
方程式4:提出的PUR中无胺TDI片段的光-氧化
基于MDI的聚氨酯类似地经由2步途径通过除去氢原子,接着过氧化物形成而成醌15。泡沫组合物中的其它组分能潜在地有助于产生颜色。例如,BHT和烷基化的二苯胺已被报导在暴露于氮氧化物时形成染色的醌化合物(图19)1。相比于其他抗氧化剂烧焦抑制剂,本发明延迟在图3中显示的转化,或其本身较不助于产生光-氧化诱导的色体。
源自聚氨酯泡沫的FOG及VOC逸散
关于室内(家庭、车辆、工作场所)空气质量的关注在全世界范围内持续增长,进而对潜在有害的挥发性物质设立立法管制。包括所有添加剂供应商在内的聚氨酯泡沫部门已朝着减少或消除不符合规定的产品的策略方向前进。对于汽车内部,已开发特定测试来测量塑料、橡胶和聚氨酯材料中的总挥发物含量。目前由德国汽车协会设立的可接受的方法为VDA278,其采用热解吸GC分析法来测定挥发性有机物含量(VOC)和汽车装饰材料的雾化可能性16。此方法测量范围高达n-C20的挥发性有机化合物(在90℃下从样品中脱附30分钟),以及从n-C16至n-C32的半挥发性重化合物(FOG值)(在120℃下从样品中脱附60分钟)。接着,所报道的值与产品说明书进行比较,由此判定合格或不合格。也可采用重量法,其可用作筛选工具来表征此处呈现的有机液体的挥发性17。
发明内容
本发明涉及用于制备聚氨酯泡沫的添加剂液体混合组合物,该添加剂包含
A:衍生的对苯二酚;
B:衍生的内酯;和
C:衍生的酚化合物。
衍生的对苯二酚(A)组分选自下列化合物:
二-叔丁基-对苯二酚(DTBHQ)、叔丁基对苯二酚(TBHQ)、2-甲基-5-异丙基对苯二酚,和优选化合物2,5-二-叔戊基-对苯二酚(DTAHQ);
美国专利第2758119号所描述的烷基化的对苯二酚单缩水甘油醚,通过参考引用方式并入本文;
美国专利第4209648号所阐述的单辛基化对苯二酚,通过参考引用方式并入本文;
通过使包含对苯二酚和选自壬烯及2,2,4-三甲基-1-戊烯的烯烃的组合在65℃至低于烯烃沸点的温度下在Friedel-Crafts催化剂的存在下进行反应而制备的对苯二酚产品;其中当烯烃为壬烯时烯烃与对苯二酚的摩尔比为1:1至10:1,以及当烯烃为2,4,4-三甲基-1-戊烯时摩尔比为1.5:1至3:1,如美国专利第4209648号所述,通过参考引用方式并入本文;以及
上述化合物的任一组合。
衍生的内酯化合物(B)组分选自在美国专利第7390912与7601853号及美国专利公开第20060135792号所描述的内酯稳定剂或其混合物,通过参考引用方式均并入本文,且优选地为可商购产品 AOX-1。内酯稳定剂通常被描述为聚合的或寡聚的内酯抗氧化剂,例如,聚(氧化烯)链取代的3-芳基苯并呋喃酮或聚(己内酯)链取代的3-芳基苯并呋喃酮。
特别优选的内酯公开于美国专利第7390912号中,其被描述为聚合的内酯化合物。
其中R1和R3独立地选自H、F、Cl、Br、I、C1-C20烷基、C1-C20环烷基、C1-C20烷氧基、C7-C20苯烷基及苯基;q为1至20的正整数,且t为0至20的正整数,且q+t等于或大于3。
衍生的酚化合物(C)通常包括在第4位被脂肪族、芳香族或脂肪族-芳香族部分取代的(2,6-二-叔丁基)苯酚,任选地具有杂原子O、N、S和P的组合;及其混合物。此类化合物的具体的代表实例包括但不限于:2,6-二-叔-丁基-4-壬基苯酚、2,4-二辛基甲硫基-6-甲基苯酚,4,6-双(辛基甲硫基)-o-甲酚、异十三烷基-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯、异-辛基-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯。许多其它固态或液态形式的酚可以混合或单独地用于组合物中,并包括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-4-n-丁基苯酚、2,6-二-叔-丁基-4-异丁基苯酚、2,6-二环戊基-4-甲基苯酚、2-(α-甲基环己基)-4,6-二甲基苯酚、2,6-二-十八烷基-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二-叔丁基-4-甲氧基甲基苯酚、在侧链中为直链或支链的壬基酚,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、2,4-二辛基甲硫基-6-叔-丁基苯酚、2,4-二辛基甲硫基-6-甲基苯酚、2,4-二辛基甲硫基-6-乙基苯酚、2,6-二-十二烷基甲硫基-4-壬基苯酚、2,6-二-叔-丁基-4-甲氧基苯酚、2,5-二-叔-丁基对苯二酚、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-羟基苯基硬脂酸酯、双(3,5-二-叔-丁基-4-羟基苯基)己二酸酯、α-生育酚、β-生育酚、γ-生育酚、δ-生育酚、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-壬基苯基]、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-n-十二烷基巯基丁烷、乙二醇双[3,3-双(3’-叔-丁基-4’-羟基苯基)丁酸酯]、双(3-叔-丁基-4-羟基-5-甲基-苯基)二环戊二烯、双[2-(3’-叔-丁基-2’-羟基-5’-甲基苄基)-6-叔-丁基-4-甲基苯基]对苯二甲酸酯、1,1-双(3,5-二甲基-2-羟基苯基)丁烷、2,2-双(3,5-二-叔-丁基-4-羟基苯基)丙烷、2,2-双(5-叔-丁基-4-羟基-2-甲基苯基)-4-n-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、β-(3,5-二-叔-丁基-4-羟基苯基)-丙酸与一元醇或多元醇的酯,该醇如甲醇、乙醇、n-辛醇、i-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、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟基乙基)异氰脲酸酯、N,N’-双(羟基乙基)草酰胺、3-硫杂十一烷醇(3-thiaundecanol)、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷-2,6,7-三氧杂二环[2,2,2]辛烷,β-(5-叔-丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇的酯,该醇如甲醇、乙醇、n-辛醇、i-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、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟基乙基)异氰脲酸酯、N,N’-双(羟基乙基)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-羟基甲基-1-磷-2,6,7-三氧杂二环[2,2,2]辛烷;3,9-双[2-{3-(3-叔-丁基-4羟基-5-甲基苯基)丙酰氧基}-1,1-二甲基乙基]-2,4,8-10-四氧杂螺[5.5]十一烷、β-(3,5-二环己基-4-羟基苯基)丙酸与一元醇或多元醇的酯,该醇如甲醇、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、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟基乙基)异氰脲酸酯、N,N’-双(羟基乙基)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-羟基甲基-1-磷-2,6,7-三氧杂二环[2,2,2]辛烷;3,5-二-叔-丁基-4-羟基-苯基-乙酸与一元醇或多元醇的酯,该醇如甲醇、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、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟基乙基)异氰脲酸酯、N,N’-双(羟基乙基)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-羟基甲基-1-磷-2,6,7-三氧杂二环[2,2,2]辛烷;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)己二酰胺、N,N’-双(3,5-二-叔-丁基-4-羟基苯基丙酰基)丙二酰胺、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(XL-1,由Uniroyal供应)及它们的混合物。优选化合物为异-辛基-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯和C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯的混合物。
烧焦抑制剂配方的优选范围以配方的重量百分比计包括:
约1-25%A组对苯二酚,优选约5-15%;
约5-25%B组内酯,如 AOX-1;优选约5-15%;
约70-90%C组酚化合物,优选约75-85%。
所述配方在聚氨酯泡沫中的优选范围为约0.001-5pbw;更优选为约0.2-3.5pbw;最优选为约0.2-0.5pbw。
示例性的烧焦抑制剂配方,实施例1,包含约10%的2,5-二-叔-戊基-对苯二酚(A组);约10%的市售的聚合或寡聚的内酯产品 AOX-1,其被认为是内酯的混合物(B组);以及约80%的3-(3,5-二-叔-丁基-4-羟基苯基)丙酸异-辛酯(C组)。本文所述的所有百分比为重量百分比。
以下显示典型的泡沫配方(表1,泡沫A)。在随后的一些实例中,也采用非燃性阻燃剂配方以证明新的混合物相比于现有技术(表1,泡沫B)的效力。
检测程序如下所述。
利用不同的抗氧化剂包制备泡沫以评估新的混合物相比于对照的“基准”的性能。
通过将蛋糕盒大小的泡沫暴露于微波加热以评估烧焦性能。该盒状泡沫经历微波加热8分钟或依照日常情况所需-根据湿度有时延长或缩短。(微波炉:通用电子家用微波炉;Mod.Num.JE1860GB001;KW:1.55;VAC/HZ:120/60.8min;在30%功率的微波中)。在炉中在短的固化周期(2分钟)之后,将生产的泡沫冷却至室温,然后检查内部烧焦区域。从各个样本切割出泡沫样品并评估变色。将经微波的泡沫的烧焦区域中的黑化程度进行定量评估。利用Technidyne Corp.Brightimeter Micro S4M收集δE值。
实施例
在聚氨酯泡沫配方中检测本发明的混合物(表1)。
检测包括与3个市售产品的比较,将该市售产品作为新混合物的性能的基准(表2)。
实施例C3对应于本发明烧焦抑制剂的组分B,其为在US7,390,912B2中表述的市售混合物并被供货商描述为聚合或寡聚的内酯抗氧化剂,已知为 AOX-1,可购自Milliken Chemical.。
实施例C4为液体烧焦抑制剂,其可购自Vanderbilt Chemical,LLC并被描述于US5219892,其含有烷基化的二苯胺和烷基化的酚化合物,特别是(a)四[亚甲基(3,5-二-叔-丁基-4-羟基氢化肉桂酸盐/酯)]甲烷和(b)二苯胺与二异丁烯的反应产物,其中胺与二异丁烯的摩尔比为1:1.1至1:2.5。稳定剂组合物可包含第三协同组分、吩噻嗪或吩噻嗪的某些烷基衍生物。
实施例C5为可通过Ciba Specialty Chemicals购买的产品,称为PUR68,其被认为是依照美国专利第5356966号的教导,且推测包含衍生的内酯及其他抗氧化剂,但不知确切的组成。
实施例C6由衍生的苯酚异十三烷基-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯(80%)和 AOX-1内酯(实施例C3)(20%)组成。对照混合物采用近似于美国专利7247658(实施例4)中所教导的组分的比例。
实施例C7由衍生的苯酚异-辛基-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯(9%);二苯胺与二异丁烯的反应产物,其中胺与二异丁烯的摩尔比为1:1.1至1:2.5(14%);市售的聚合或寡聚的内酯产品 AOX-1(34%);和 3260 2-(2’-羟基-3’-t-丁基-5’-甲基苯基)-5-氯苯并三唑(43%)(由Songwon生产并可购自VanderbiltChemicals,LLC)组成。对照混合物采用美国专利7601853B2(添加剂包BB)中所教导的组分的比例。
实施例8
实施例8包含2,5-二-叔-戊基-对苯二酚(10%)和市售的聚合或寡聚的内酯产品 AOX-1(10%)及C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯的混合物( 13-15(Addivant USA,LLC),CAS:171090-93-0)。
如下面表2和表2A中所述,在泡沫组合物中的相同载量水平(0.2pbw)下,实施例1的本发明混合物产生更少的变色,如减少的dE测量值所示。
另一轮的关于比较本发明混合物与两种来自最接近的现有技术(US7,390,912B2)的内酯组合物的测试显示本发明混合物(实施例1)更显著地减少烧焦(表3)。我们在此注意到实施例C7是酚、烷基化的二苯胺、聚合的内酯和苯并三唑的组合,当混合时其不会形成液体混合物,这与实施例1不同,其确实形成液体——在商业应用上非常理想的特征。
其它系列证明本发明配方在不存在阻燃剂的情况下持续减少烧焦。尤其是,本发明混合物的总重量低于现有的配方,然而显示更低的烧焦(表4)。
气体褪色研究
环境因素及泡沫变色
泡沫制造业者已意识到氮氧化物烟气的影响,并当今共同公开信息公告提醒消费者变色问题,同时指出新产品以减轻此影响18。为模拟PUR泡沫暴露于NOx烟气,开发称为气体褪色的检测,其中首先使用简单实验设备来捕获所产生的燃烧烟气并将材料暴露于此燃烧烟气19。对此,制造业者开始提供安装在本生灯上的烟气室,该本生灯位于带有样本转盘的附件中。将样本暴露于被捕获的燃烧烟气一段规定长度的时间20。在我们的评估中,将样本置于该室内,并使用比色法测量定期检查。
在此研究中,检查2个浓度水平,比较本发明混合物与现有技术配方(C7)。在较高浓度(3.5pbw)下,相比于现有技术配方(dE=7.05),本发明混合物产生明显更少的变色(dE=4.81),并且在较低浓度(0.5pbw)下,也证实了相比于现有技术的显而易见的优势。应注意的是,所选定的水平(3.5pbw)被引用在C7所衍生的专利中,因此用作实施例1的有用对照组(表5)。
比较实施例1与C4(酚/ADPA混合物)的气体褪色评价以及光褪色研究
在工业配方中常用的2个水平下,将实施例1(本发明混合物)与常用的酚/ADPA混合物进行比较。此外,用在PUR泡沫中使用的阻燃剂(根据表1,泡沫A)修饰该配方。HF-5和HF-4阻燃剂分别为专卖的磷酯混合物及非-卤素磷酯,可购自ICL IndustrialProducts。显示的数据超过试验运行的长度,这具有某些兴趣。发现本发明配方独立于阻燃剂的类型在整个试验期(2小时)中产生更少的显色(表6)。
比较实施例1与C4(酚/ADPA混合物)的光褪色评价。
最后,将泡沫样本暴露于一般荧光下并监测6天。将本发明混合物与ADPA/酚混合物(C4)比较,在整个试验期间本发明混合物在两个选择的浓度下显示更低的变色(表7)。
组分vs混合物的评价
为了证明本发明混合物比其单独组分显示了真实的协同作用,测定来自实施例1中的各个组分的烧焦性能。还对生产的泡沫进行气体褪色研究(表8)。使用2种工具评价该混合物的性能,包括简单平均值及加权平均值,基于混合物中特定组分的浓度计算加权平均值。各组分显示了不同水平的性能,由最深内部至最浅内部,如下所示:衍生的酚PH-1(23.24)>衍生的内酯AOX-1(8.88)>对苯二酚HQ-1(4.14)。假设各组分对混合物的最终烧焦性能的影响相同,则预测的dE值为x假设各组分根据其在混合物组成中存在的重量进行影响,则预测的值为事实上,混合物低于简单平均值和加权平均值二者,因此显示出真实的协同作用(dE=5.47)。烟气室结果显示类似的趋势,但也许更另人惊讶的是,变色不仅在与预测的平均值的比较中是最低的,而且低于所有的测量值(表8),这再次证实混合物的真实的协同作用。
配方调整
对混合物中的组分的相对浓度进行调整并评价(表9)。在此系列的实验中,发现不论是增加内酯、对苯二酚或两者的浓度,与实施例1相比,通常导致烧焦性能的改善(A-C)。增加酚并减少内酯和对苯二酚,相比于实施例1,导致烧焦性能的降低(D)。然而,增加对苯二酚的浓度导致液体不稳定性,而在混合物制成后数日内形成沉淀。对成功的市售产品的一个要求就是它尽可能地长时间保持液体状,其意味着某些调整的混合物是较不有利的。
挥发性考虑
如上所讨论的,期望降低聚氨酯泡沫中发现的组分的挥发性。Gossner et al.解释“从现有技术中已知聚氨酯泡沫能逸散挥发性有机组成成分(VOC),此逸散通常是不期望的。这些逸散是可(检测的)…”21。本发明可被调整为使用较高分子量的烷基化的酚化合物,其潜在性地降低化合物的挥发性。为了证明此事,制备实施例8,除了替换为更高分子量的酚(即,C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯的混合物(13-15))以外,与实施例1相同。首先,类似于实施例1,对经修饰的混合物实施例8实施观察(表10)。
如烧焦抑制剂包的使用者所优选的,可调整配方以降低逸散或VOC。相比于实施例1,经调整的组合物实施例8在检测时间中显示更低的挥发性。利用热重量分析法(ASTME2008)测量随时间而产生的重量损失,显示在2种混合物中的显著差异(表11)。如所预期地,在整个试验运行期间,更高的分子量组分有助于降低重量损失(实施例1vs实施例8)。
在评述检测结果时,注意如下。
当与其单一组分相比较时,实施例1混合物在相同重量基础上比其组分更大程度地减少烧焦,这证明真实的协同作用。US7,390,912 B2中鉴定的内酯抗氧化剂(实施例C3)比使用该内酯混合物的本发明组合物(实施例1)更差地减少烧焦。本发明混合物的其它抗氧化剂组分比该混合物(实施例1)也更差地减少烧焦。此外,如上所讨论的,所测试的在C3(0.5pbw)的评价中使用的内酯的载量水平(charge level)远大于实施例1(0.05pbw)的混合物中的内酯水平(level)。还发现关于现有技术C3的“内酯”专利家族中公开的其它混合物如C6及C7比本发明混合物产生更多的烧焦。
实施例C5为市售的内酯组合物-尽管制造商未公开其确切的配方。在这里,本发明配方(实施例1)在相同的载量水平下产生更少的烧焦。
实施例1也不含烷基化的二苯胺(使用于实施例C4中)及其母起始材料二苯胺。在许多产品中及在欧洲,DPA是不期望的23。因此,实施例1在提供改善的烧焦减少的同时还降低对健康的关注。因此,本发明还包括加入添加剂配方的聚氨酯泡沫,其不具有或基本不具有二苯胺。相较于烷基化的二苯胺混合物,如C4,本发明配方在暴露于NOx烟气和常见荧光时也促成更少的显色。
虽然实施例1证明本发明混合物比数个现有技术或商业组合物更好地减少烧焦,但其可经修饰以减少在各个市场部门中关注的可能的挥发性。
参考文献
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Claims (14)
1.用于抑制聚氨酯泡沫组合物烧焦的添加剂组合物,所述添加剂包含:
约1-25重量%的衍生的对苯二酚;
约5-25重量%的衍生的内酯;和
约70-90重量%的衍生的酚化合物。
2.如权利要求1所述的添加剂组合物,其包含:
约5-15重量%的所述衍生的对苯二酚;
约5-20重量%的所述衍生的内酯;和
约70-85重量%的所述衍生的酚化合物。
3.如权利要求1所述的添加剂组合物,其包含:
约10重量%的所述衍生的对苯二酚;
约10-20重量%的所述衍生的内酯;和
约70-80重量%的所述衍生的酚化合物。
4.如权利要求1所述的添加剂组合物,其中
所述衍生的对苯二酚为2,5-二-叔-戊基-对苯二酚;
所述衍生的内酯为:
其中R1和R3独立地选自H、F、Cl、Br、I、C1-C20烷基、C1-C20环烷基、C1-C20烷氧基、C7-C20苯烷基和苯基;q为1至20的正整数,且t为0至20的正整数,且其中q+t等于或大于3;以及
所述衍生的酚化合物为(a)异十三烷基-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯或(b)C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯的混合物。
5.如权利要求4所述的添加剂组合物,其包含:
约5-15重量%的所述衍生的对苯二酚;
约5-20重量%的所述衍生的内酯;和
约70-85重量%的所述衍生的酚化合物。
6.如权利要求5所述的添加剂组合物,其包含:
约10重量%的所述衍生的对苯二酚;
约10-20重量%的所述衍生的内酯;和
约70-80重量%的所述衍生的酚化合物。
7.聚氨酯泡沫组合物,其包含约0.001-5pbw的烧焦抑制剂添加剂组合物,所述添加剂组合物以所述总添加剂的重量计包含:
约1-25%的衍生的对苯二酚;
约5-25%的衍生的内酯;和
约70-90%的衍生的酚化合物。
8.如权利要求7所述的聚氨酯泡沫组合物,其中所述添加剂组合物以约0.2-3.5pbw存在。
9.如权利要求7所述的聚氨酯泡沫组合物,其中所述添加剂组合物以约0.2-0.5pbw存在。
10.如权利要求9所述的聚氨酯泡沫组合物,其中所述添加剂组合物包含:
约5-15重量%的所述衍生的对苯二酚;
约5-20重量%的所述衍生的内酯;和
约70-85重量%的所述衍生的酚化合物。
11.如权利要求8所述的聚氨酯泡沫组合物,其中所述添加剂组合物包含:
约10重量%的所述衍生的对苯二酚;
约10-20重量%的所述衍生的内酯;和
约70-80重量%的所述衍生的酚化合物。
12.如权利要求7所述的聚氨酯泡沫组合物,其中
所述衍生的对苯二酚为2,5-二-叔-戊基-对苯二酚;
所述衍生的内酯为:
其中R1和R3独立地选自H、F、Cl、Br、I、C1-C20烷基、C1-C20环烷基、C1-C20烷氧基、C7-C20苯烷基和苯基;q为1至20的正整数,且t为0至20的正整数,且其中q+t等于或大于3;以及
所述衍生的酚化合物为(a)异十三烷基-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯或(b)C-13至C-15醇酯-3-(3,5-二-叔-丁基-4-羟基苯基)丙酸酯的混合物。
13.如权利要求12所述的聚氨酯泡沫组合物,其中所述添加剂组合物包含:
约5-15重量%的所述衍生的对苯二酚;
约5-20重量%的所述衍生的内酯;和
约70-85重量%的所述衍生的酚化合物。
14.如权利要求13所述的聚氨酯泡沫组合物,其中所述添加剂组合物包含:
约10重量%的所述衍生的对苯二酚;
约10-20重量%的所述衍生的内酯;和
约70-80重量%的所述衍生的酚化合物。
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GB2579405B (en) | 2018-11-30 | 2022-09-14 | Si Group Switzerland Chaa Gmbh | Antioxidant compositions |
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