CA2605987C - Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams - Google Patents
Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams Download PDFInfo
- Publication number
- CA2605987C CA2605987C CA2605987A CA2605987A CA2605987C CA 2605987 C CA2605987 C CA 2605987C CA 2605987 A CA2605987 A CA 2605987A CA 2605987 A CA2605987 A CA 2605987A CA 2605987 C CA2605987 C CA 2605987C
- Authority
- CA
- Canada
- Prior art keywords
- hydroxyl
- copolyester
- fatty acid
- acid
- fatty acids
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 28
- 239000011496 polyurethane foam Substances 0.000 title claims description 28
- 239000004814 polyurethane Substances 0.000 title abstract description 26
- 229920002635 polyurethane Polymers 0.000 title abstract description 25
- 229920005906 polyester polyol Polymers 0.000 title description 11
- 125000003198 secondary alcohol group Chemical group 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 180
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 155
- 239000000194 fatty acid Substances 0.000 claims abstract description 155
- 229930195729 fatty acid Natural products 0.000 claims abstract description 155
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 150
- 229920001634 Copolyester Polymers 0.000 claims abstract description 110
- 229920005862 polyol Polymers 0.000 claims abstract description 102
- 150000003077 polyols Chemical class 0.000 claims abstract description 101
- 150000002148 esters Chemical class 0.000 claims abstract description 91
- 239000003999 initiator Substances 0.000 claims abstract description 51
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 10
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract description 10
- 239000000203 mixture Substances 0.000 claims description 88
- 239000003054 catalyst Substances 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 27
- 229920000570 polyether Polymers 0.000 claims description 25
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 21
- 239000004604 Blowing Agent Substances 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000005056 polyisocyanate Substances 0.000 claims description 18
- 229920001228 polyisocyanate Polymers 0.000 claims description 18
- 239000004094 surface-active agent Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 12
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 claims description 11
- 150000002513 isocyanates Chemical class 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 7
- 229920001577 copolymer Polymers 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 6
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 claims description 5
- 229960003656 ricinoleic acid Drugs 0.000 claims description 5
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- ULQISTXYYBZJSJ-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O ULQISTXYYBZJSJ-UHFFFAOYSA-N 0.000 claims 2
- -1 poly(ethylene oxide) Polymers 0.000 abstract description 36
- 229920003171 Poly (ethylene oxide) Polymers 0.000 abstract description 4
- 239000006260 foam Substances 0.000 description 60
- 238000000034 method Methods 0.000 description 41
- 238000006243 chemical reaction Methods 0.000 description 30
- 238000009472 formulation Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- 239000003570 air Substances 0.000 description 16
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 15
- RVWOWEQKPMPWMQ-UHFFFAOYSA-N methyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OC RVWOWEQKPMPWMQ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- 239000000463 material Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 229920001296 polysiloxane Polymers 0.000 description 11
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 11
- 235000015112 vegetable and seed oil Nutrition 0.000 description 11
- 239000008158 vegetable oil Substances 0.000 description 11
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 10
- 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 description 10
- 229920000642 polymer Polymers 0.000 description 9
- 239000004359 castor oil Substances 0.000 description 8
- 229960001777 castor oil Drugs 0.000 description 8
- 235000019438 castor oil Nutrition 0.000 description 8
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 8
- 239000003549 soybean oil Substances 0.000 description 8
- 235000012424 soybean oil Nutrition 0.000 description 8
- 150000003512 tertiary amines Chemical class 0.000 description 8
- 239000012974 tin catalyst Substances 0.000 description 8
- 239000004970 Chain extender Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 6
- 239000004971 Cross linker Substances 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 239000003925 fat Substances 0.000 description 6
- 235000019197 fats Nutrition 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 239000013518 molded foam Substances 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 6
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 5
- 230000001413 cellular effect Effects 0.000 description 5
- 239000000470 constituent Substances 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- MWFOVBOCPFXQMF-UHFFFAOYSA-L dibutyl-chloro-[dibutyl(chloro)stannyl]oxystannane Chemical compound CCCC[Sn](Cl)(CCCC)O[Sn](Cl)(CCCC)CCCC MWFOVBOCPFXQMF-UHFFFAOYSA-L 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- 239000005642 Oleic acid Substances 0.000 description 4
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 4
- 229940113120 dipropylene glycol Drugs 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 229920005604 random copolymer Polymers 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 150000003335 secondary amines Chemical group 0.000 description 4
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical group NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000005187 foaming Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000012970 tertiary amine catalyst Substances 0.000 description 3
- 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 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000019737 Animal fat Nutrition 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- 241000390166 Physaria Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000002666 chemical blowing agent Substances 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 229940043237 diethanolamine Drugs 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 229920002239 polyacrylonitrile Polymers 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 229920005903 polyol mixture Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920003226 polyurethane urea Polymers 0.000 description 2
- 238000010107 reaction injection moulding Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000003333 secondary alcohols Chemical group 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229960004418 trolamine Drugs 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- VACHUYIREGFMSP-UHFFFAOYSA-N (+)-threo-9,10-Dihydroxy-octadecansaeure Natural products CCCCCCCCC(O)C(O)CCCCCCCC(O)=O VACHUYIREGFMSP-UHFFFAOYSA-N 0.000 description 1
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- OFLPOBPCVHNRMF-UHFFFAOYSA-N 1,2-nonadecanediol Chemical compound CCCCCCCCCCCCCCCCCC(O)CO OFLPOBPCVHNRMF-UHFFFAOYSA-N 0.000 description 1
- VGHSXKTVMPXHNG-UHFFFAOYSA-N 1,3-diisocyanatobenzene Chemical compound O=C=NC1=CC=CC(N=C=O)=C1 VGHSXKTVMPXHNG-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- JPFGKGZYCXLEGQ-UHFFFAOYSA-N 1-(4-methoxyphenyl)-5-methylpyrazole-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C(C)=C(C(O)=O)C=N1 JPFGKGZYCXLEGQ-UHFFFAOYSA-N 0.000 description 1
- DTZHXCBUWSTOPO-UHFFFAOYSA-N 1-isocyanato-4-[(4-isocyanato-3-methylphenyl)methyl]-2-methylbenzene Chemical compound C1=C(N=C=O)C(C)=CC(CC=2C=C(C)C(N=C=O)=CC=2)=C1 DTZHXCBUWSTOPO-UHFFFAOYSA-N 0.000 description 1
- AZKSXXWROJGHGN-UHFFFAOYSA-N 12-hydroxyoctadecanoic acid Chemical compound CCCCCCC(O)CCCCCCCCCCC(O)=O.CCCCCCC(O)CCCCCCCCCCC(O)=O AZKSXXWROJGHGN-UHFFFAOYSA-N 0.000 description 1
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G2110/00—Foam properties
- C08G2110/0083—Foam properties prepared using water as the sole blowing agent
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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)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Polyesters Or Polycarbonates (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67634805P | 2005-04-29 | 2005-04-29 | |
| US60/676,348 | 2005-04-29 | ||
| PCT/US2006/016173 WO2006118995A1 (en) | 2005-04-29 | 2006-04-27 | Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2605987A1 CA2605987A1 (en) | 2006-11-09 |
| CA2605987C true CA2605987C (en) | 2013-11-05 |
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| CA2605987A Expired - Fee Related CA2605987C (en) | 2005-04-29 | 2006-04-27 | Polyester polyols containing secondary alcohol groups and their use in making polyurethanes such as flexible polyurethane foams |
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| EP (1) | EP1877463B1 (enExample) |
| JP (1) | JP5345387B2 (enExample) |
| KR (1) | KR101224302B1 (enExample) |
| CN (1) | CN101166776B (enExample) |
| AR (1) | AR056335A1 (enExample) |
| AT (1) | ATE483744T1 (enExample) |
| AU (1) | AU2006242495B2 (enExample) |
| BR (1) | BRPI0613186A2 (enExample) |
| CA (1) | CA2605987C (enExample) |
| DE (1) | DE602006017354D1 (enExample) |
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| MX (1) | MX2007013464A (enExample) |
| MY (1) | MY148327A (enExample) |
| RU (1) | RU2413738C2 (enExample) |
| WO (1) | WO2006118995A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US8293808B2 (en) | 2003-09-30 | 2012-10-23 | Cargill, Incorporated | Flexible polyurethane foams prepared using modified vegetable oil-based polyols |
| WO2007111828A2 (en) * | 2006-03-23 | 2007-10-04 | Dow Global Technologies Inc. | Low density, natural oil based polyurethane foam without silicone based cell stabilizing additive |
| EP2125958A4 (en) * | 2007-03-02 | 2012-08-29 | Proprietect Lp | DISAPPEARED ISOCYANATE BASED POLYMER |
| US20090029097A1 (en) * | 2007-06-11 | 2009-01-29 | Riddle Dennis L | Flooring products and methods |
| PL2167563T3 (pl) * | 2007-07-12 | 2013-10-31 | Dow Global Technologies Llc | Polimery utwardzalne w temperaturze pokojowej ich prekursory |
| CN101802039A (zh) * | 2007-07-12 | 2010-08-11 | 陶氏环球技术公司 | 弹性体的预聚物和聚合物 |
| WO2009058368A1 (en) * | 2007-11-01 | 2009-05-07 | Cargill, Incorporated | Natural oil-derived polyester polyols and polyurethanes made therefrom |
| EP2242793B1 (en) * | 2008-02-08 | 2017-08-16 | Dow Global Technologies LLC | Polyurethane foam comprising a water-redispersible polymer powder |
| CN102124042A (zh) * | 2008-03-20 | 2011-07-13 | 陶氏环球技术有限责任公司 | 由基于天然油的多元醇制得的预聚物 |
| CN102272187A (zh) * | 2008-03-20 | 2011-12-07 | 陶氏环球技术有限责任公司 | 聚醚天然油多元醇及其聚合物 |
| EP2276786A2 (en) * | 2008-05-09 | 2011-01-26 | Dow Global Technologies Inc. | Natural oil based polyol blends |
| US20110166245A1 (en) * | 2008-07-30 | 2011-07-07 | Mitsui Chemicals, Inc. | Polyester polyol composition for polyurethane, composition for polyurethane foam, polyurethane resin, and polyurethane foam |
| JP5540093B2 (ja) * | 2009-07-01 | 2014-07-02 | バイエル・マテリアルサイエンス・アクチェンゲゼルシャフト | ポリエステルポリオールを含む第２級ヒドロキシル末端基を有するポリウレタンポリマーの製造方法 |
| US8846776B2 (en) | 2009-08-14 | 2014-09-30 | Boral Ip Holdings Llc | Filled polyurethane composites and methods of making same |
| US9481759B2 (en) | 2009-08-14 | 2016-11-01 | Boral Ip Holdings Llc | Polyurethanes derived from highly reactive reactants and coal ash |
| US9932457B2 (en) | 2013-04-12 | 2018-04-03 | Boral Ip Holdings (Australia) Pty Limited | Composites formed from an absorptive filler and a polyurethane |
| US10138341B2 (en) | 2014-07-28 | 2018-11-27 | Boral Ip Holdings (Australia) Pty Limited | Use of evaporative coolants to manufacture filled polyurethane composites |
| US10414859B2 (en) | 2014-08-20 | 2019-09-17 | Resinate Materials Group, Inc. | High recycle content polyester polyols |
| JP7579240B2 (ja) * | 2018-09-28 | 2024-11-07 | ダウ グローバル テクノロジーズ エルエルシー | ポリ（ブチレンオキシド）ポリオールをベースにしたポリウレタンキャストエラストマー、およびポリウレタンキャストエラストマーを作製するための方法 |
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| US2759953A (en) | 1955-09-07 | 1956-08-21 | Hogan B Knight | Addition of organic acids to the double bond of unsaturated fatty compounds |
| FR1165085A (fr) | 1957-03-19 | 1958-10-17 | Bayer Ag | Procédé pour la production de matières synthétiques de poids moléculaire élevé |
| GB1469531A (en) | 1973-06-25 | 1977-04-06 | Ici Ltd | Carboxylic acid-alkylene oxide adducts |
| US3914189A (en) * | 1974-03-15 | 1975-10-21 | Tenneco Chem | Method for production of polyurethane foam using oxazolines as catalysts |
| GB1572913A (en) * | 1977-01-24 | 1980-08-06 | Indian Space Res Org | Production of polyols containing basic nitrogen |
| EP0000424B1 (en) * | 1977-07-12 | 1984-02-01 | Imperial Chemical Industries Plc | Linear or branched ester-ether block copolymers and their use as surfactants either alone or in blends with conventional surfactants |
| GB1572931A (en) | 1978-05-23 | 1980-08-06 | Hirst & Sons Ltd B | Playgrounds apparatus |
| US4267081A (en) * | 1978-10-23 | 1981-05-12 | Ameron, Inc. | High solids polyurethane coatings |
| EP0106491A3 (en) * | 1982-09-07 | 1985-12-04 | HENKEL CORPORATION (a Delaware corp.) | Hydroxymethyl polyols |
| US4534907A (en) | 1982-09-07 | 1985-08-13 | Henkel Corporation | Alkoxylated polyester polyols |
| EP0164817B1 (en) * | 1984-03-21 | 1991-01-23 | Imperial Chemical Industries Plc | Surfactant |
| EP0513964A3 (en) * | 1991-05-14 | 1993-04-07 | Mitsui Toatsu Chemicals, Inc. | (polyurethane) elastomer and process for producing it (with a specific releasing agent) |
| DE4203215A1 (de) * | 1992-02-05 | 1993-08-12 | Bayer Ag | Verfahren zur herstellung von formkoerpern |
| DE4400465A1 (de) * | 1993-07-12 | 1995-01-19 | Bayer Ag | Neue Mischungen und ihre Verwendung als Bindemittel zur Herstellung von Verbundmaterialien |
| DE4331228A1 (de) * | 1993-09-15 | 1995-03-16 | Henkel Kgaa | Estergruppenhaltige Blockpolymere als Entschäumer für wäßrige Systeme |
| US5427704A (en) | 1994-01-28 | 1995-06-27 | The Lubrizol Corporation | Triglyceride oils thickened with estolides of hydroxy-containing triglycerides |
| DE4409043A1 (de) * | 1994-03-17 | 1995-09-21 | Bayer Ag | Verfahren zur Herstellung von gegebenenfalls zellförmigen Polyurethanen |
| BR9504838A (pt) | 1994-11-15 | 1997-10-07 | Lubrizol Corp | Ester de poliol composição de óleo lubrificante |
| DE19636688A1 (de) | 1996-09-10 | 1998-03-12 | Clariant Gmbh | Neue polymere Acetale von Hydroxycarbonsäuren und deren Derivaten und Verfahren zu ihrer Herstellung |
| US6018063A (en) | 1998-11-13 | 2000-01-25 | The United States Of America As Represented By The Secretary Of Agriculture | Biodegradable oleic estolide ester base stocks and lubricants |
| DE19816308A1 (de) | 1998-04-11 | 1999-10-14 | Henkel Kgaa | Rheologisches Additiv |
| US6180686B1 (en) | 1998-09-17 | 2001-01-30 | Thomas M. Kurth | Cellular plastic material |
| JP4104229B2 (ja) * | 1998-11-06 | 2008-06-18 | 株式会社Ａｄｅｋａ | 水系ポリウレタン樹脂組成物 |
| DE19905989A1 (de) * | 1999-02-13 | 2000-08-17 | Bayer Ag | Feinzellige, wassergetriebene Polyurethanhartschaumstoffe |
| JP4090035B2 (ja) | 2003-02-06 | 2008-05-28 | 竹本油脂株式会社 | 合成繊維用紡糸油剤及び合成繊維の処理方法 |
| AU2004234367B2 (en) * | 2003-04-25 | 2008-09-11 | Dow Global Technologies, Inc. | Vegetable oil based polyols and polyurethanes made therefrom |
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2006
- 2006-04-27 BR BRPI0613186-7A patent/BRPI0613186A2/pt active Search and Examination
- 2006-04-27 MX MX2007013464A patent/MX2007013464A/es active IP Right Grant
- 2006-04-27 DK DK06751736.7T patent/DK1877463T3/da active
- 2006-04-27 DE DE602006017354T patent/DE602006017354D1/de active Active
- 2006-04-27 EP EP06751736A patent/EP1877463B1/en not_active Not-in-force
- 2006-04-27 KR KR1020077027755A patent/KR101224302B1/ko not_active Expired - Fee Related
- 2006-04-27 AT AT06751736T patent/ATE483744T1/de not_active IP Right Cessation
- 2006-04-27 US US11/918,633 patent/US7750108B2/en not_active Expired - Fee Related
- 2006-04-27 JP JP2008509156A patent/JP5345387B2/ja not_active Expired - Fee Related
- 2006-04-27 RU RU2007144199/05A patent/RU2413738C2/ru not_active IP Right Cessation
- 2006-04-27 CN CN2006800146030A patent/CN101166776B/zh not_active Expired - Fee Related
- 2006-04-27 WO PCT/US2006/016173 patent/WO2006118995A1/en not_active Ceased
- 2006-04-27 AU AU2006242495A patent/AU2006242495B2/en not_active Ceased
- 2006-04-27 CA CA2605987A patent/CA2605987C/en not_active Expired - Fee Related
- 2006-04-28 MY MYPI20061997A patent/MY148327A/en unknown
- 2006-04-28 AR ARP060101738A patent/AR056335A1/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008539324A (ja) | 2008-11-13 |
| ATE483744T1 (de) | 2010-10-15 |
| BRPI0613186A2 (pt) | 2010-12-21 |
| DE602006017354D1 (de) | 2010-11-18 |
| JP5345387B2 (ja) | 2013-11-20 |
| AU2006242495B2 (en) | 2011-01-20 |
| RU2413738C2 (ru) | 2011-03-10 |
| CN101166776B (zh) | 2011-05-04 |
| MX2007013464A (es) | 2008-01-21 |
| DK1877463T3 (da) | 2011-01-10 |
| WO2006118995A1 (en) | 2006-11-09 |
| AR056335A1 (es) | 2007-10-03 |
| US7750108B2 (en) | 2010-07-06 |
| KR20080013955A (ko) | 2008-02-13 |
| MY148327A (en) | 2013-03-29 |
| CA2605987A1 (en) | 2006-11-09 |
| AU2006242495A1 (en) | 2006-11-09 |
| EP1877463A1 (en) | 2008-01-16 |
| EP1877463B1 (en) | 2010-10-06 |
| KR101224302B1 (ko) | 2013-01-21 |
| US20090264546A1 (en) | 2009-10-22 |
| CN101166776A (zh) | 2008-04-23 |
| RU2007144199A (ru) | 2009-06-10 |
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Legal Events
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| EEER | Examination request | ||
| MKLA | Lapsed |
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| MKLA | Lapsed |
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