CA2885423C - Improved stability of polyurethane polyol blends containing halogenated olefin blowing agent - Google Patents
Improved stability of polyurethane polyol blends containing halogenated olefin blowing agent Download PDFInfo
- Publication number
- CA2885423C CA2885423C CA2885423A CA2885423A CA2885423C CA 2885423 C CA2885423 C CA 2885423C CA 2885423 A CA2885423 A CA 2885423A CA 2885423 A CA2885423 A CA 2885423A CA 2885423 C CA2885423 C CA 2885423C
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- CA
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- Prior art keywords
- polyol
- mix composition
- foam
- mix
- composition
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 209
- 229920005862 polyol Polymers 0.000 title claims abstract description 136
- 150000003077 polyols Chemical class 0.000 title claims abstract description 136
- 239000004604 Blowing Agent Substances 0.000 title claims abstract description 51
- 229920002635 polyurethane Polymers 0.000 title description 27
- 239000004814 polyurethane Substances 0.000 title description 27
- 150000001336 alkenes Chemical class 0.000 title description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 118
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 claims abstract description 111
- 239000006260 foam Substances 0.000 claims abstract description 107
- 239000003963 antioxidant agent Substances 0.000 claims abstract description 85
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 65
- 229920001187 thermosetting polymer Polymers 0.000 claims abstract description 26
- 239000012948 isocyanate Substances 0.000 claims abstract description 20
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 19
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 17
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 150000001412 amines Chemical class 0.000 claims description 55
- -1 ether amine Chemical class 0.000 claims description 39
- 229910052751 metal Inorganic materials 0.000 claims description 30
- 239000002184 metal Substances 0.000 claims description 30
- 239000004094 surface-active agent Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 150000002148 esters Chemical class 0.000 claims description 23
- 229920001296 polysiloxane Polymers 0.000 claims description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 150000007942 carboxylates Chemical class 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 12
- 239000003063 flame retardant Substances 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- 229910052718 tin Inorganic materials 0.000 claims description 9
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 8
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims description 8
- 150000001298 alcohols Chemical class 0.000 claims description 7
- 229910052797 bismuth Inorganic materials 0.000 claims description 7
- 150000002576 ketones Chemical class 0.000 claims description 7
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 claims description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 6
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 6
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 5
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 239000001569 carbon dioxide Substances 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 5
- 239000011777 magnesium Substances 0.000 claims description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002524 organometallic group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 4
- 150000008109 benzenetriols Chemical class 0.000 claims description 4
- 239000001273 butane Substances 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 229920001400 block copolymer Polymers 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 3
- 150000004986 phenylenediamines Chemical class 0.000 claims description 3
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 claims description 3
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 claims description 2
- QAZYYQMPRQKMAC-FDGPNNRMSA-L calcium;(z)-4-oxopent-2-en-2-olate Chemical compound [Ca+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O QAZYYQMPRQKMAC-FDGPNNRMSA-L 0.000 claims description 2
- NDWWLJQHOLSEHX-UHFFFAOYSA-L calcium;octanoate Chemical compound [Ca+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O NDWWLJQHOLSEHX-UHFFFAOYSA-L 0.000 claims description 2
- FJDJVBXSSLDNJB-LNTINUHCSA-N cobalt;(z)-4-hydroxypent-3-en-2-one Chemical compound [Co].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FJDJVBXSSLDNJB-LNTINUHCSA-N 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- AKTIAGQCYPCKFX-FDGPNNRMSA-L magnesium;(z)-4-oxopent-2-en-2-olate Chemical compound [Mg+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AKTIAGQCYPCKFX-FDGPNNRMSA-L 0.000 claims description 2
- GMDNUWQNDQDBNQ-UHFFFAOYSA-L magnesium;diformate Chemical compound [Mg+2].[O-]C=O.[O-]C=O GMDNUWQNDQDBNQ-UHFFFAOYSA-L 0.000 claims description 2
- HPBJPFJVNDHMEG-UHFFFAOYSA-L magnesium;octanoate Chemical compound [Mg+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O HPBJPFJVNDHMEG-UHFFFAOYSA-L 0.000 claims description 2
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 claims description 2
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 150000001555 benzenes Chemical class 0.000 claims 1
- 150000008110 hydroxyquinols Chemical class 0.000 claims 1
- 150000003000 phloroglucinols Chemical class 0.000 claims 1
- 150000003232 pyrogallols Chemical class 0.000 claims 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001491 aromatic compounds Chemical class 0.000 abstract description 4
- 125000001424 substituent group Chemical group 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 abstract description 3
- 235000006708 antioxidants Nutrition 0.000 description 74
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000011495 polyisocyanurate Substances 0.000 description 17
- 229920000582 polyisocyanurate Polymers 0.000 description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 238000007664 blowing Methods 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 238000009472 formulation Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 230000000087 stabilizing effect Effects 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 7
- 229920013701 VORANOL™ Polymers 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000032683 aging Effects 0.000 description 7
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000006071 cream Substances 0.000 description 6
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 230000001627 detrimental effect Effects 0.000 description 5
- 238000005187 foaming Methods 0.000 description 5
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 238000010792 warming Methods 0.000 description 5
- 229920001174 Diethylhydroxylamine Polymers 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- FVCOIAYSJZGECG-UHFFFAOYSA-N diethylhydroxylamine Chemical compound CCN(O)CC FVCOIAYSJZGECG-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 238000005829 trimerization reaction Methods 0.000 description 4
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 3
- LDTMPQQAWUMPKS-OWOJBTEDSA-N (e)-1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)\C=C\Cl LDTMPQQAWUMPKS-OWOJBTEDSA-N 0.000 description 3
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 3
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229960004337 hydroquinone Drugs 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 3
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 3
- CFNJLPHOBMVMNS-UHFFFAOYSA-N pentyl butyrate Chemical compound CCCCCOC(=O)CCC CFNJLPHOBMVMNS-UHFFFAOYSA-N 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 239000010936 titanium Substances 0.000 description 3
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- NOPJRYAFUXTDLX-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-3-methoxypropane Chemical compound COC(F)(F)C(F)(F)C(F)(F)F NOPJRYAFUXTDLX-UHFFFAOYSA-N 0.000 description 2
- LOOCNDFTHKSTFY-UHFFFAOYSA-N 1,1,2-trichloropropyl dihydrogen phosphate Chemical compound CC(Cl)C(Cl)(Cl)OP(O)(O)=O LOOCNDFTHKSTFY-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 description 2
- YSAANLSYLSUVHB-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]ethanol Chemical compound CN(C)CCOCCO YSAANLSYLSUVHB-UHFFFAOYSA-N 0.000 description 2
- LSYBWANTZYUTGJ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl-methylamino]ethanol Chemical compound CN(C)CCN(C)CCO LSYBWANTZYUTGJ-UHFFFAOYSA-N 0.000 description 2
- CCJKFLLIJCGHMO-UHFFFAOYSA-N 2-[diethoxyphosphorylmethyl(2-hydroxyethyl)amino]ethanol Chemical compound CCOP(=O)(OCC)CN(CCO)CCO CCJKFLLIJCGHMO-UHFFFAOYSA-N 0.000 description 2
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 2
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical class FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/10—Block- or graft-copolymers containing polysiloxane sequences
- C08J2383/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Emergency Medicine (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| US201261704626P | 2012-09-24 | 2012-09-24 | |
| US61/704,626 | 2012-09-24 | ||
| PCT/US2013/060510 WO2014047230A1 (en) | 2012-09-24 | 2013-09-19 | Improved stability of polyurethane polyol blends containing halogenated olefin blowing agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2885423A1 CA2885423A1 (en) | 2014-03-27 |
| CA2885423C true CA2885423C (en) | 2020-09-22 |
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| CA2885423A Active CA2885423C (en) | 2012-09-24 | 2013-09-19 | Improved stability of polyurethane polyol blends containing halogenated olefin blowing agent |
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| EP (1) | EP2898038A4 (enExample) |
| JP (1) | JP6441220B2 (enExample) |
| KR (1) | KR102090467B1 (enExample) |
| CN (1) | CN104685021B (enExample) |
| BR (1) | BR112015006376B1 (enExample) |
| CA (1) | CA2885423C (enExample) |
| IN (1) | IN2015DN02388A (enExample) |
| MX (1) | MX372874B (enExample) |
| WO (1) | WO2014047230A1 (enExample) |
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| CN106750482A (zh) | 2011-03-11 | 2017-05-31 | 阿科玛股份有限公司 | 包含卤代烯烃发泡剂的聚氨酯多元醇共混物的改善的稳定性 |
| CN113897181A (zh) | 2013-01-25 | 2022-01-07 | 特灵国际有限公司 | 制冷剂添加剂和组合物 |
| BR112017007389B1 (pt) | 2014-10-13 | 2022-07-19 | Evonik Operations Gmbh | Composição de catalisador e seu uso, processo para produzir poliuretano e espuma de poliuretano |
| EP3984986A1 (en) | 2015-05-21 | 2022-04-20 | The Chemours Company FC, LLC | Hydrofluorination of 1233xf to 244bb by sbf5 |
| WO2017048334A1 (en) * | 2015-09-18 | 2017-03-23 | Arkema Inc. | Polyol pre-mixes having improved shelf life |
| JP6643936B2 (ja) * | 2016-03-29 | 2020-02-12 | 株式会社Adeka | ポリウレタンフォームの製造方法 |
| JP6951012B2 (ja) * | 2016-05-16 | 2021-10-20 | 積水ソフランウイズ株式会社 | 硬質ポリウレタンフォーム用ポリオール組成物、及び硬質ポリウレタンフォームの製造方法 |
| US20180022884A1 (en) * | 2016-07-25 | 2018-01-25 | Honeywell International Inc. | Polyester polyol compositions containing hfo-1336mzzm (z) |
| MX2019001122A (es) * | 2016-07-29 | 2019-09-09 | Arkema Inc | Pre-mezclas de poliol que tienen mejor vida util. |
| EP3601394A1 (en) * | 2017-03-24 | 2020-02-05 | INVISTA Textiles (U.K.) Limited | Polyol compositions for foam insulation |
| CN108727551A (zh) * | 2017-04-19 | 2018-11-02 | 科思创德国股份有限公司 | 一种硬质聚氨酯泡沫及其制备方法与应用 |
| BR112020003914A2 (pt) * | 2017-09-05 | 2020-09-08 | Huntsman Petrochemical Llc | pré-mistura de poliol, métodos para formar uma pré-mistura de poliol e para formar uma espuma de poliuretano ou poliisocianurato, espuma, e, formulação de poliuretano |
| US10525663B2 (en) | 2017-09-28 | 2020-01-07 | Johns Manville | Foam insulation with improved low temperature properties |
| US10563033B2 (en) * | 2017-09-28 | 2020-02-18 | Johns Manville | Foam insulation with enhanced fire and smoke performance |
| GB2579405B (en) | 2018-11-30 | 2022-09-14 | Si Group Switzerland Chaa Gmbh | Antioxidant compositions |
| JP7749306B2 (ja) * | 2019-02-27 | 2025-10-06 | 旭有機材株式会社 | ポリオール薬液組成物 |
| MX2021010317A (es) | 2019-02-28 | 2022-01-19 | Evonik Operations Gmbh | Composicion de amina util para hacer sistemas de espuma de poliuretano estables. |
| US10851196B2 (en) * | 2019-04-29 | 2020-12-01 | Covestro Llc | Rigid polyurethane foams suitable for use as panel insulation |
| US12134676B2 (en) | 2019-04-29 | 2024-11-05 | Covestro Llc | Rigid polyurethane foams suitable for use as panel insulation |
| JP2023519336A (ja) | 2020-03-27 | 2023-05-10 | ハンツマン ペトロケミカル エルエルシー | ポリウレタン発泡体用の酸ブロックアルキルアミノピリジン触媒 |
| BR112023002689A2 (pt) * | 2020-08-14 | 2023-03-14 | Huntsman Int Llc | Formulação de poliuretano, método para produzir um material de poliuretano, e, material de poliuretano |
| DE102021202103A1 (de) | 2021-03-04 | 2022-09-08 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung eingetragener Verein | Verwendung einer Stabilisatorzusammensetzung zur Stabilisierung von halogenfreien thermoplastischen Kunststoff-Recyclaten, eine Stabilisatorzusammensetzung, ein Masterbatch oder Konzentrat, eine stabilisierte Kunststoffzusammensetzung, hier ein Verfahren zur Stabilisierung von halogenfreien thermoplastischen Kunststoff-Recyclaten sowie Verwendung von Zusammensetzungen |
| CN113604029B (zh) * | 2021-07-26 | 2023-01-13 | 高州市铭顺劳保制品有限公司 | 一种阻燃慢回弹记忆海绵及其制备方法 |
| KR20230170860A (ko) | 2022-06-11 | 2023-12-19 | 김청준 | 스트랩 아령 |
| US11827735B1 (en) | 2022-09-01 | 2023-11-28 | Covestro Llc | HFO-containing isocyanate-reactive compositions, related foam-forming compositions and flame retardant PUR-PIR foams |
| CN116120631B (zh) * | 2023-02-03 | 2025-06-13 | 天津利安隆新材料股份有限公司 | 抗老化剂组合物及其应用和抗老化高分子材料 |
| KR102620840B1 (ko) * | 2023-03-17 | 2024-01-04 | 정대영 | 재활용 ｐｅｔ 및 변성 이소시아네이트를 사용한 단열재용 고분자 조성물의 제조 방법 및 그 시스템 |
| AU2024301505A1 (en) * | 2023-07-26 | 2026-01-22 | Huntsman Petrochemical Llc | Catalysts having an electron withdrawing group and their use in polyurethane formulations |
| WO2025027093A1 (en) | 2023-08-03 | 2025-02-06 | Evonik Operations Gmbh | Closed cell polyurethane foam spray additives for improving adhesion under low temperature conditions |
| KR20250139025A (ko) * | 2024-03-14 | 2025-09-23 | 한화솔루션 주식회사 | 이소시아네이트 화합물 장기보관용 첨가제, 이를 포함하는 이소시아네이트 혼합물 및 이를 이용한 이소시아네이트 화합물 보관방법 |
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| US3772218A (en) * | 1971-10-12 | 1973-11-13 | Scott Paper Co | Flexible,open-cell,non-discoloring polyurethane foam |
| EP0516020A2 (de) * | 1991-05-28 | 1992-12-02 | Hoechst Aktiengesellschaft | Stabilisierung von Dichlortrifluorethan enthaltenden Mischungen |
| US5395859A (en) | 1991-06-21 | 1995-03-07 | Alliedsignal Inc. | Catalysts which stabilize hydrohalocarbon blowing agent in polyisocyanurate foam formulations during polymerization |
| JPH05156063A (ja) * | 1991-12-04 | 1993-06-22 | Central Glass Co Ltd | ハロゲン化炭化水素の安定化方法 |
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| JPH08291089A (ja) * | 1995-04-19 | 1996-11-05 | Daikin Ind Ltd | １，１，１，２，３，３−ヘキサフルオロプロパン及び１，１，１，３，３−ペンタフルオロプロパンの分解抑制方法及び分解抑制剤 |
| US5470501A (en) * | 1995-05-08 | 1995-11-28 | Basf Corporation | Processability of hydrocarbon blown, polyisocyanate based foams through use of a compatibilizing agent |
| AU2003258977A1 (en) | 2002-07-02 | 2004-01-23 | Stepan Company | Polyisocyanurate foams with improved thermal stability |
| US7485729B2 (en) | 2004-08-12 | 2009-02-03 | King Industries, Inc. | Organometallic compositions and coating compositions |
| SG166810A1 (en) * | 2005-11-01 | 2010-12-29 | Du Pont | Methods for making foams using blowing agents comprising unsaturated fluorocarbons |
| KR101477485B1 (ko) * | 2007-06-27 | 2014-12-30 | 알케마 인코포레이티드 | 안정화된 하이드로클로로플루오로올레핀과 하이드로플루오로올레핀 |
| JP2009013247A (ja) * | 2007-07-03 | 2009-01-22 | Central Glass Co Ltd | 安定化された硬質ポリウレタンフォーム用プレミックス |
| US20100216904A1 (en) * | 2009-02-24 | 2010-08-26 | E. I. Du Pont De Nemours And Company | Foam-forming compositions containing mixtures of 2-chloro-3,3,3-trifluoropropene and at least one hydrofluoroolefin and their uses in the preparation of polyisocyanate-based foams |
| DE102009028061A1 (de) * | 2009-07-29 | 2011-02-10 | Evonik Goldschmidt Gmbh | Verfahren zur Herstellung von Polyurethanschaum |
| CA2773366C (en) * | 2009-09-09 | 2018-03-06 | Arkema Inc. | Improved polyurethane foaming processes and foam properties using halogenated olefin blowing agent |
| US10113046B2 (en) | 2009-10-23 | 2018-10-30 | Arkema Inc | Tetrafluorobutene blowing agent compositions for polyurethane foams |
| DE102009053224A1 (de) | 2009-11-06 | 2011-07-14 | Bayer MaterialScience AG, 51373 | Verfahren zur Herstellung eines Polyurethanschaums und hieraus erhältlicher Polyurethanschaum |
| CA2797679A1 (en) * | 2010-04-28 | 2011-11-03 | Arkema Inc. | Method of improving stability of polyurethane polyol blends containing halogenated olefin blowing agent |
| HUE049760T2 (hu) * | 2012-02-02 | 2020-10-28 | Arkema Inc | Halogénezett olefineket tartalmazó poliol-keverékek tárolási idejének javítása az aktív komponensek kapszulázásával |
-
2013
- 2013-09-19 CA CA2885423A patent/CA2885423C/en active Active
- 2013-09-19 JP JP2015533165A patent/JP6441220B2/ja active Active
- 2013-09-19 EP EP13839776.5A patent/EP2898038A4/en not_active Withdrawn
- 2013-09-19 IN IN2388DEN2015 patent/IN2015DN02388A/en unknown
- 2013-09-19 CN CN201380049718.3A patent/CN104685021B/zh active Active
- 2013-09-19 US US14/430,289 patent/US10308783B2/en active Active
- 2013-09-19 BR BR112015006376-4A patent/BR112015006376B1/pt active IP Right Grant
- 2013-09-19 MX MX2015003696A patent/MX372874B/es active IP Right Grant
- 2013-09-19 WO PCT/US2013/060510 patent/WO2014047230A1/en not_active Ceased
- 2013-09-19 KR KR1020157007474A patent/KR102090467B1/ko active Active
-
2019
- 2019-04-11 US US16/381,093 patent/US20190233605A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CA2885423A1 (en) | 2014-03-27 |
| JP6441220B2 (ja) | 2018-12-19 |
| BR112015006376B1 (pt) | 2022-01-25 |
| US10308783B2 (en) | 2019-06-04 |
| CN104685021A (zh) | 2015-06-03 |
| EP2898038A4 (en) | 2016-04-27 |
| US20190233605A1 (en) | 2019-08-01 |
| IN2015DN02388A (enExample) | 2015-09-04 |
| JP2015529738A (ja) | 2015-10-08 |
| EP2898038A1 (en) | 2015-07-29 |
| CN104685021B (zh) | 2018-04-13 |
| BR112015006376A2 (pt) | 2017-07-04 |
| US20150197614A1 (en) | 2015-07-16 |
| MX2015003696A (es) | 2015-07-23 |
| KR102090467B1 (ko) | 2020-03-18 |
| MX372874B (es) | 2020-07-07 |
| KR20150063392A (ko) | 2015-06-09 |
| WO2014047230A1 (en) | 2014-03-27 |
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Effective date: 20180913 |