CN116547333A - 芳族聚酯多元醇化合物 - Google Patents
芳族聚酯多元醇化合物 Download PDFInfo
- Publication number
- CN116547333A CN116547333A CN202180081271.2A CN202180081271A CN116547333A CN 116547333 A CN116547333 A CN 116547333A CN 202180081271 A CN202180081271 A CN 202180081271A CN 116547333 A CN116547333 A CN 116547333A
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- China
- Prior art keywords
- polyester polyol
- aromatic polyester
- compound
- acid
- polyol compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 101
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 77
- 229920005906 polyester polyol Polymers 0.000 title claims abstract description 63
- 239000002253 acid Substances 0.000 claims abstract description 34
- -1 aromatic acid compound Chemical class 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000011541 reaction mixture Substances 0.000 claims abstract description 17
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 13
- 238000005886 esterification reaction Methods 0.000 claims abstract description 12
- 125000004990 dihydroxyalkyl group Chemical group 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 23
- 229920005862 polyol Polymers 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 claims description 10
- 230000032050 esterification Effects 0.000 claims description 7
- ARSRBNBHOADGJU-UHFFFAOYSA-N 7,12-dimethyltetraphene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C)=C(C=CC=C1)C1=C2C ARSRBNBHOADGJU-UHFFFAOYSA-N 0.000 claims description 6
- VFZRZRDOXPRTSC-UHFFFAOYSA-N DMBA Natural products COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000004604 Blowing Agent Substances 0.000 claims description 4
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 3
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims description 3
- TXSZYEYDDYBUSU-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)hexanoic acid Chemical compound CCCCC(CO)(CO)C(O)=O TXSZYEYDDYBUSU-UHFFFAOYSA-N 0.000 claims description 3
- UHAMPPWFPNXLIU-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)pentanoic acid Chemical compound CCCC(CO)(CO)C(O)=O UHAMPPWFPNXLIU-UHFFFAOYSA-N 0.000 claims description 3
- JPRONANUKIXQSE-UHFFFAOYSA-N 3,3,3-trihydroxypropanoic acid Chemical compound OC(=O)CC(O)(O)O JPRONANUKIXQSE-UHFFFAOYSA-N 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- XFNOOUURNRHBLL-UHFFFAOYSA-N OCC1(CO)C=CC=CC1CC(O)=O Chemical compound OCC1(CO)C=CC=CC1CC(O)=O XFNOOUURNRHBLL-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 229920005830 Polyurethane Foam Polymers 0.000 claims 1
- 239000011496 polyurethane foam Substances 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 57
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 21
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 21
- 150000003077 polyols Chemical class 0.000 description 18
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 235000011187 glycerol Nutrition 0.000 description 10
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 10
- 239000006260 foam Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000004364 calculation method Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920000582 polyisocyanurate Polymers 0.000 description 7
- 239000011495 polyisocyanurate Substances 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 238000005809 transesterification reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000004698 Polyethylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 125000001165 hydrophobic group Chemical group 0.000 description 3
- 125000005702 oxyalkylene group Chemical group 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical class CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- HOVAGTYPODGVJG-UVSYOFPXSA-N (3s,5r)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol Chemical compound COC1OC(CO)[C@@H](O)C(O)[C@H]1O HOVAGTYPODGVJG-UVSYOFPXSA-N 0.000 description 2
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
- XAVMMNWPOYCFPU-UHFFFAOYSA-N 2-[bis(2-hydroxyethyl)amino]ethanolate;propan-2-olate;titanium(4+) Chemical compound [Ti+4].CC(C)[O-].CC(C)[O-].OCCN(CCO)CC[O-].OCCN(CCO)CC[O-] XAVMMNWPOYCFPU-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- 229930091371 Fructose Natural products 0.000 description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001283 Polyalkylene terephthalate Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 159000000032 aromatic acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- PFURGBBHAOXLIO-UHFFFAOYSA-N cyclohexane-1,2-diol Chemical compound OC1CCCCC1O PFURGBBHAOXLIO-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HOVAGTYPODGVJG-UHFFFAOYSA-N methyl beta-galactoside Natural products COC1OC(CO)C(O)C(O)C1O HOVAGTYPODGVJG-UHFFFAOYSA-N 0.000 description 2
- YRHYCMZPEVDGFQ-UHFFFAOYSA-N methyl decanoate Chemical compound CCCCCCCCCC(=O)OC YRHYCMZPEVDGFQ-UHFFFAOYSA-N 0.000 description 2
- NUKZAGXMHTUAFE-UHFFFAOYSA-N methyl hexanoate Chemical compound CCCCCC(=O)OC NUKZAGXMHTUAFE-UHFFFAOYSA-N 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 description 2
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N methyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
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- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-UHFFFAOYSA-N 0.000 description 1
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 1
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- 239000004215 Carbon black (E152) Substances 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
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- VPLDWFOUVJAARM-UHFFFAOYSA-N OCC1(CO)C=CC=CC1C(O)=O Chemical compound OCC1(CO)C=CC=CC1C(O)=O VPLDWFOUVJAARM-UHFFFAOYSA-N 0.000 description 1
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
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Abstract
一种制备芳族聚酯多元醇化合物的方法,其中所述方法包括在酯化反应条件下使包含如下组分的反应混合物反应:(i)芳族酸化合物;(ii)脂族二醇化合物;(iii)二羟基烷基链烷酸化合物;(iv)任选的疏水化合物、含至少三个羟基的多羟基化合物或它们的组合;和其中所述芳族聚酯多元醇化合物在25℃下为液体和羟基值为约30‑600。
Description
相关申请的交叉引用
本申请要求2020年12月3日提交的美国临时专利申请No.63/120,993的优先权。上述申请在此通过参考引入。
技术领域
本发明通常涉及一种芳族聚酯多元醇化合物及其制备方法。
背景技术
相比于在建筑和工业行业中应用的其它解决方案,由于其优越的密封和绝缘特性,聚氨酯(“PU”)和聚异氰脲酸酯(“PIR”)基泡沫产品广泛地应用于这些行业中。这些泡沫产品是由异氰酸酯化合物和异氰酸酯反应性化合物的反应形成的,所述反应可能在催化剂或其它添加剂存在或不存在的情况下发生。
配制PU或PIR基泡沫组合物的配制者对其组合物中应用的异氰酸酯反应性化合物通常有具体的要求。这些要求包括羟基值、官能度、粘度、芳基含量、发泡剂溶解性和其它特性。配制者对于异氰酸酯反应性化合物的选择将取决于多种因素,例如泡沫组合物的可加工性和所产生的PU或PIR泡沫产品的所需机械和结构性能。
因此,仍然需要一种聚酯多元醇化合物,其具有PU或PIR基泡沫组合物可能需要的某些特性。
具体实施方式
正如本文所使用,“芳族聚酯多元醇组合物”指包含组分(i)-(iv)的反应混合物。
正如本文所使用,“生物可再生含量”指芳族聚酯多元醇化合物中来自生物来源的可再生材料占芳族聚酯多元醇化合物总质量的比例,可应用ASTM D6866来测量。
正如本文所使用,“疏水化合物”指至少含有非极性有机部分的化合物或该类化合物的混合物。疏水化合物通常不溶于水,且含有至少一个能够被酯化或转酯的官能团(如单羧酸基、单羧酸酯基、羟基或它们的组合)。
正如本文所使用,“包括”和类似术语指"包括但不限于"。
正如本文所使用,“单羧酸基”和“单羧酸酯基”指在疏水化合物中存在的羧酸部分是单酸。
正如本文所使用,“多个”指两个或更多个,而术语"数字"指1或大于1的整数。
正如本文所使用,“回收含量”指相对于芳族聚酯多元醇化合物的总质量,芳族聚酯多元醇化合物中回收的芳族酸/酯和回收的脂族二醇化合物的比例。
除非另有明确说明,否则所有的数字,如表示数值、范围、量或百分比的数字,即使没有明确出现"约",也应理解为在前面冠有"约"。复数包含单数,反之亦然。
当提到任何数值范围时,这些范围应理解为包括所述范围最小值和最大值之间的每个数值和/或分数。例如,"1至10"或"1-10"的范围打算包括所述最小值1和所述最大值10之间(且包括1和10)的所有子范围,即最小值大于或等于1和最大值小于或等于10。
除非本文另有说明,否则所提及的任何化合物也应包括这种化合物的任何异构体(例如立体异构体)。
除非本文另有说明,否则所提及的任何化合物也应包括这种化合物的任何异构体(例如立体异构体)。
除非本文另有说明,否则“分子量”指按凝胶渗透色谱法测量的重均分子量(Mw)。
制备芳族聚酯多元醇化合物的方法
本发明涉及一种制备芳族聚酯多元醇化合物的方法。所述方法包括在在酯化反应条件下使包含如下组分的反应混合物发生反应:
(i)芳族酸化合物;
(ii)脂族二醇化合物;
(iii)通式I的二羟基烷基链烷酸化合物:
通式I:
其中R为氢、C1-C8烷基(直链或支链)、C1-C8羟基烷基、C1-C12芳基或C1-C12脂环基,其中R1、R2分别独立地为氢、甲基或乙基;和
(iv)任选的含至少三个羟基的多羟基化合物、疏水化合物或它们的组合;
其中所述芳族聚酯多元醇化合物在25℃下为液体和羟基值为约30-600。
本发明的芳族聚酯多元醇化合物通过将下文更详细描述的组分(i)-(iv)放入反应容器中,并使反应混合物在50-300℃的温度下经历酯化/转酯反应条件1-24小时(如3-10小时)的时间段。在一些实施方案中,两个或更多个组分(i)-(iv)可以相互预反应形成中间产物。然后向反应容器中引入所述中间产物和其余组分,并经历酯化/转酯反应条件形成芳族聚酯多元醇化合物。可以从过程中移除反应的任何挥发性副产物(如水或甲醇),从而使酯交换反应完成。虽然芳族聚酯多元醇化合物的合成可以在减压或加压条件下实施,但反应通常在接近常压的条件下实施。
合成过程中可以应用酯化/转酯催化剂来加快反应速率。合适的酯化/转酯催化剂的实例包括锡催化剂(例如可由Arkema,Inc.获得的FAST Cat催化剂)、钛催化剂(例如可由Dork Ketal Chemical LLC获得的TYZOR TBT催化剂、TYZOR TE催化剂)、碱催化剂(如氢氧化钠、氢氧化钾、醇钠和醇钾)、酸催化剂(如硫酸、磷酸、盐酸、磺酸)、酶或它们的组合。以芳族聚酯多元醇组合物的总重量计,酯化/转酯催化剂的存在量可以为0.001-0.2wt%。
组分(i):芳族酸化合物
可用作组分(i)的合适芳族酸化合物包括对苯二甲酸、邻苯二甲酸酐、邻苯二甲酸、间苯二甲酸、2,6-萘二羧酸、偏苯三酸酐、均苯三酸酐、均苯四酸二酐、偏苯四酸二酐、邻苯二甲酸、间苯二甲酸、对苯二甲酸和2,6-萘二羧酸的甲基酯、或它们的组合。
可作为组分(i)的其它化合物还包括更复杂的成分,如制备上文所列化合物的侧线物流、废物和/或残渣、芳族羧酸副产物(BACA)或它们的组合。
可用作组分(i)的其它化合物还包括聚对苯二甲酸亚烷基酯聚合物(如聚对苯二甲酸乙二醇酯(PET)、聚对苯二甲酸丁二醇酯(PBT)、聚对苯二甲酸丙二醇酯(PTT)、乙二醇改性的聚对苯二甲酸乙二醇酯(PETG))、对苯二甲酸和1,4-环己烷二甲醇的共聚物(PCT)、聚萘二甲酸乙二醇酯(PEN)或它们的组合。
这些聚合物中的任何一种都可以由废弃的回收或使用过的物品中获得,包括摄影胶片、X射线胶片、合成纤维、在软饮料行业中广泛使用的塑料瓶或其它相关容器、在其它产品生产过程中产生的回收材料(如那些由聚对苯二甲酸亚烷基酯聚合物制成的材料)或它们的组合。例如,rPET和/或rPTT可以来自消费后的塑料瓶或其它相关容器废物流,也可以来自工业或消费后的地毯。在这些实施方案中,rPET可能含有少量的有机和/或无机异物(如纸张、染料、其它塑料、玻璃或金属)。在某些实施方案中,rPET和/或rPTT可以为片状或粒状形式。也可以应用源自PET和/或PTT的低聚物材料。这些材料可以任选在催化剂的存在下,在可使PET和/或PTT部分解聚的反应条件下,通过使PET和/或PTT与一种或多种二醇反应来制备。
以芳族聚酯多元醇组合物的总重量计,组分(i)的存在量可以为5-70wt%(例如10-50wt%或15-45wt%)。
组分(ii):脂族二醇化合物
可用作组分(ii)的合适脂族二醇化合物包括具有如下结构的化合物:OH–R–OH
其中R为选自如下的二价基团:(i)含2-12个碳原子的亚烷基基团(带或不带烷基分支);或(ii)如下结构的基团:
-[(R′O)n–R′]–
其中R′为含2-4个碳原子的亚烷基,n为1-10的整数。
可用作组分(ii)的合适脂族二醇化合物的实例包括:乙二醇;二乙二醇;三乙二醇;四乙二醇;丙二醇;二丙二醇;三丙二醇;丁二醇;1,4丁二醇;新戊二醇;由环氧乙烷、环氧丙烷或其组合缩合而成的含2-4个亚烷基基团的聚(氧亚烷基)多元醇;2-甲基-2,4-戊二醇;1,6-己二醇;1,2-环己二醇;或它们的组合。
以芳族聚酯多元醇组合物的总重量计,组分(ii)的存在量可以为5-60wt%(例如10-50wt%或15-45wt%)。
组分(iii):二羟基烷基链烷酸
可用作组分(III)的二羟基烷基链烷酸化合物具有通式I所示的结构:
通式I:
其中R为氢、C1-C8烷基(直链或支链)、C1-C8羟基烷基、C1-C12芳基或C1-C12脂环基。实例包括氢、甲基、乙基、异丙基、羟基甲基、羟基乙基、苯基、甲苯基、萘基、环戊基、环己基。优选为甲基、乙基、丙基、丁基、苯基和甲苯基。
其中R1、R2分别独立地为氢、C1-C8烷基(直链或支链)。实例包括氢、甲基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、正己基、正庚基、正辛基。
可用作组分(iii)的二羟基烷基链烷酸化合物的实例包括:2,2-二(羟基甲基)丙酸(DMPA);2,2-二(羟基甲基)丁酸(DMBA);2,2-二(羟基甲基)戊酸(DMPTA);2,2-二(羟基甲基)己酸(DMHA);2,2,2-三羟基甲基乙酸(TMAA);和2,2-二(羟基甲基)苯甲酸和2,2-二(羟基甲基)甲苯酸;或它们的组合。
以芳族聚酯多元醇组合物的总重量计,组分(iii)的存在量可以为0.1-30wt%(例如0.5-25wt%或1-15wt%)。
组分(iv):任选的添加剂
组分(iv)可以包括含至少三个羟基的多羟基化合物、疏水化合物或它们的组合。
可用作组分(iv)的合适多羟基化合物包括含3-8个羟基的低分子量化合物。合适的多羟基化合物的实例包括:甘油;烷氧基化的甘油;1,1,1-三羟基甲基丙烷、1,1,1-三羟基甲基乙烷;季戊四醇;二季戊四醇;蔗糖;烷氧基化的蔗糖;甲基葡萄糖苷;烷氧基化的甲基葡萄糖苷;葡萄糖;烷氧基化的葡萄糖;果糖;烷氧基化的果糖;山梨醇;烷氧基化的山梨醇;乳糖;烷氧基化的乳糖;甘露醇;二甘油;赤藓糖醇;木糖醇;或它们的组合.
在某些实施方案中,可用作组分(iv)的疏水化合物包括那些由芳族酸衍生的化合物。合适的疏水化合物的实例包括:羧酸(如脂肪酸化合物,如己酸、辛酸、2-乙基己酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、硬脂酸、油酸、亚油酸、亚麻酸和蓖麻油酸化合物);羧酸的低级烷醇酯(如脂肪酸甲酯化合物,如己酸甲酯、辛酸甲酯、癸酸甲酯、月桂酸甲酯、肉豆蔻酸甲酯、棕榈酸甲酯、油酸甲酯、硬脂酸甲酯、亚油酸甲酯和亚麻酸甲酯);脂肪酸烷醇酰胺(如妥尔油脂肪酸二乙醇酰胺、月桂酸二乙醇酰胺和油酸单乙醇酰胺);甘油三酯(如脂肪和油,如蓖麻油、椰子油(包括精白椰油)、玉米油、棉籽油、亚麻籽油、橄榄油、棕榈油、棕榈仁油、花生油、大豆油、葵花籽油、妥尔油、牛油以及天然油或官能化(如环氧化)天然油的衍生物);烷基醇(如每个分子含4-18个碳原子的醇,如癸醇、油醇、十六烷醇、异癸醇、十三烷醇、月桂醇和混合C12-C14醇);或它们的组合。
以芳族聚酯多元醇组合物的总重量计,组分(iv)的存在量可以为0-30wt%(例如0-20wt%或0-15wt%)。
其它添加剂
芳族聚酯多元醇反应混合物还可以包含少量染料、抗氧化剂、紫外线稳定剂、酸清除剂或它们的组合。以芳族聚酯多元醇组合物的总重量计,这些添加剂的存在量可以≤1wt%(例如≤0.5wt%)。
在某些实施方案中,也可应用非离子表面活性剂化合物作添加剂。这些非离子表面活性剂可包含一个或多个疏水部分和一个或多个亲水部分。但非离子表面活性剂不包含在受到水溶液或水分散体影响时解离成阳离子或阴离子的任何部分。虽然几乎任何的非离子表面活性剂化合物均可以使用,但合适的表面活性剂为每个分子平均含4-200个单独的氧亚烷基基团的聚氧亚烷基表面活性剂化合物,其中所述氧亚烷基基团选自氧亚乙基、氧亚丙基或它们的组合。以芳族聚酯组合物的总重量计,非离子表面活性剂化合物的存在量可以为0-20wt%。
芳族聚酯多元醇的特征
本发明的芳族聚酯多元醇化合物表现出与通常用于PU和PIR泡沫组合物的组分如烃类发泡剂(如戊烷、HFC基发泡剂)的相容性,同时具有低粘度、高官能度和高的芳基含量特性。
在某些实施方案中,芳族聚酯多元醇化合物的计算数均官能度为1.7-4(例如2-3.5或2.2-3),和平均羟基值为30-600(例如50-500或100-450)。应注意所述羟基值考虑了可能存在的游离二元醇。芳族聚酯多元醇的羟基值可以应用ASTM-D4274测量。
在一些实施方案中,芳族聚酯多元醇化合物在25℃下应用Brookfield DV-II粘度计测量的粘度为200-50,000厘泊(cps)(例如1,000-20,000cp或1,500-10,000cp)。在某些实施方案中,芳族聚酯多元醇化合物的粘度低于按照相同的羟基值、芳基含量和计算官能度但不应用组分(iii)而制备的对应多元醇化合物的粘度。
在某些实施方案中,以芳族聚酯多元醇化合物的总重量计,芳族聚酯多元醇化合物的生物可再生含量为至少10%(例如≥25%或≥40%)。在合成芳族聚酯多元醇化合物中可以应用的合适生物可再生材料包括植物衍生的天然油和这些油的脂肪酸组分。生物可再生含量可以应用ASTM D6866测量。
在一些实施方案中,以芳族聚酯多元醇化合物的总重量计,芳族聚酯多元醇化合物的回收含量为至少10%(例如≥25%或≥40%)。
调整
虽然已经详细描述了本发明的具体实施方案,但本领域技术人员应理解在考虑本发明总体教导下,可以开发出对于这些细节的各种调整和替代方案。因此,这里公开的设置只是示例性的,和不限制本发明的范围,本发明范围由所附权利要求及其全部等价方案的总范围来给出。因此,上文所列的任何特征和/或元素均可以以任何方式相互组合且仍在本发明范围内。
实施例
组分:
DEG:可由Equistar Chemicals,LP获得的二乙二醇。
DMBA:可由MilliporeSigma获得的二羟基甲基丁酸。
DMPA:可由MilliporeSigma获得的二羟基甲基丙酸。
甘油:可由Terra Biochem LLC获得。
PE:可由Perstorp Polyols Inc公司获得的季戊四醇。
PTA:可由Grupo Petrotemex获得的纯对苯二甲酸。
SBO:可由Archer Daniels Midland Company获得的精制大豆油。
TEG:可由Dow Chemical Company获得的三乙二醇。
TTEG:可由Dow Chemical Company获得的四乙二醇。
TYZOR TE:可由Dorf Ketal Specialty Catalyst LLC获得的(三乙醇胺酸根)异丙醇钛在异丙醇中的80wt%溶液。
分析和测试:
在实施例中提到了如下术语:
酸值:按标准滴定技术(如ASTM D4662)确定的残余酸测量值。
芳基含量:在最终多元醇产品中苯二基的重量百分比,由多元醇合成中应用的含苯环原料计算得出。
FN:多元醇的官能度,指每个分子中OH基团的平均数,定义为由多元醇原料组合物计算的一定量多元醇产品中OH基团摩尔数和分子摩尔数的比。
疏水基含量:由多元醇合成中应用的疏水化合物原料计算的最终多元醇产品中脂族链基团的重量百分比。
OH值:羟基值,其为通过标准滴定技术(如ASTM D4274)确定的OH基团量的测量值。
粘度:应用Brookfield粘度计(如Brookfield DV-II粘度计)测量的动态粘度。
多元醇-1(对比例)
将264g PTA、10.9g PE、82g甘油、110g TTEG、139g TEG、89g DEG和62g SBO加入500mL的圆筒状玻璃反应器中。在~0.3-0.5升/分钟(LPM)氮气流量下,将反应混合物加热至240℃。然后温度保持在240℃下和收集冷凝水。当顶部温度降至低于70℃(~4小时后),加入0.7g Tyzor TE。然后在240℃下加热反应,直到酸值低于2.0mg KOH/g(~2小时后)。然后将反应冷却至室温,并测量初始的OH值。然后根据计算向反应器中加入DEG,从而将OH值调节至计算的350mg KOH/g,同时在80℃下搅拌混合物30分钟。然后将最终的多元醇-1冷却至室温,测量酸值、OH值和粘度。
多元醇-1A(本发明)
将264g PTA、8.1g DMPA、89g甘油、110g TTEG、136g TEG、89g DEG和62g SBO加入500mL的圆筒状玻璃反应器中。在~0.3-0.5升/分钟(LPM)氮气流量下,将反应混合物加热至240℃。然后温度保持在240℃下和收集冷凝水。当顶部温度降至低于70℃(~4小时后),加入0.7g Tyzor TE。然后在240℃下加热反应,直到酸值低于2.0mg KOH/g(~2小时后)。然后将反应冷却至室温,并测量初始的OH值。然后根据计算向反应器中加入DEG,从而将OH值调节至计算的350mg KOH/g,同时在80℃下搅拌混合物30分钟。然后将最终的多元醇-1A冷却至室温,测量酸值、OH值和粘度。
多元醇-1B(本发明)
将264g PTA、24.3g DMPA、78g甘油、90g TTEG、111g TEG、132g DEG和62g SBO加入500mL的圆筒状玻璃反应器中。在~0.3-0.5升/分钟(LPM)氮气流量下,将反应混合物加热至240℃。然后温度保持在240℃下和收集冷凝水。当顶部温度降至低于70℃(~4小时后),加入0.7g Tyzor TE。然后在240℃下加热反应,直到酸值低于2.0mg KOH/g(~2小时后)。然后将反应冷却至室温,并测量初始的OH值。然后根据计算向反应器中加入DEG,从而将OH值调节至计算的350mg KOH/g,同时在80℃下搅拌混合物30分钟。然后将最终的多元醇-1B冷却至室温,测量酸值、OH值和粘度。
多元醇-1C(本发明)
将264g PTA、23.9g DMBA、80g甘油、90g TTEG、111g TEG、130g DEG和62g SBO加入500mL的圆筒状玻璃反应器中。在~0.3-0.5升/分钟(LPM)氮气流量下,将反应混合物加热至240℃。然后温度保持在240℃下和收集冷凝水。当顶部温度降至低于70℃(~4小时后),加入0.7g Tyzor TE。然后在240℃下加热反应,直到酸值低于2.0mg KOH/g(~2小时后)。然后将反应冷却至室温,并测量初始的OH值。然后根据计算向反应器中加入DEG,从而将OH值调节至计算的350mg KOH/g,同时在80℃下搅拌混合物30分钟。然后将最终的多元醇-1C冷却至室温,测量酸值、OH值和粘度。
多元醇-2(对比例)
将259g PTA、21.2g PE、77g甘油、108g TTEG、167g TEG、64g DEG和61g SBO加入500mL的圆筒状玻璃反应器中。在~0.3-0.5升/分钟(LPM)氮气流量下,将反应混合物加热至240℃。然后温度保持在240℃下和收集冷凝水。当顶部温度降至低于70℃(~4小时后),加入0.7g Tyzor TE。然后在240℃下加热反应,直到酸值低于2.0mg KOH/g(~2小时后)。然后将反应冷却至室温,并测量初始的OH值。然后根据计算向反应器中加入DEG,从而将OH值调节至计算的350mg KOH/g,同时在80℃下搅拌混合物30分钟。然后将最终的多元醇-2冷却至室温,测量酸值、OH值和粘度。
多元醇-2A(本发明)
将266g PTA、8.1g DMPA、102g甘油、118g TTEG、136gTEG、67g DEG和61g SBO加入500mL的圆筒状玻璃反应器中。在~0.3-0.5升/分钟(LPM)氮气流量下,将反应混合物加热至240℃。然后温度保持在240℃下和收集冷凝水。当顶部温度降至低于70℃(~4小时后),加入0.7g Tyzor TE。然后在240℃下加热反应,直到酸值低于2.0mg KOH/g(~2小时后)。然后将反应冷却至室温,并测量初始的OH值。然后根据计算向反应器中加入DEG,从而将OH值调节至计算的350mg KOH/g,同时在80℃下搅拌混合物30分钟。然后将最终的多元醇-2A冷却至室温,测量酸值、OH值和粘度。
多元醇-2B(本发明)
将265g PTA、24.3g DMPA、91g甘油、93g TTEG、133g TEG、93g DEG和61g SBO加入500mL的圆筒状玻璃反应器中。在~0.3-0.5升/分钟(LPM)氮气流量下,将反应混合物加热至240℃。然后温度保持在240℃下和收集冷凝水。当顶部温度降至低于70℃(~4小时后),加入0.7g Tyzor TE。然后在240℃下加热反应,直到酸值低于2.0mg KOH/g(~2小时后)。然后将反应冷却至室温,并测量初始的OH值。然后根据计算向反应器中加入DEG,从而将OH值调节至计算的350mg KOH/g,同时在80℃下搅拌混合物30分钟。然后将最终的多元醇-2B冷却至室温,测量酸值、OH值和粘度。
多元醇特性的总结
表1:
多元醇 | 多元醇-1 | 多元醇-1A | 多元醇-1B | 多元醇-1C |
DMPA(每100份最终多元醇) | 0.0 | 1.15 | 3.47 | |
DMBA(每100份最终多元醇) | 0.0 | 3.42 | ||
酸值(mg KOH/g) | 0.8 | 1.0 | 1.4 | 0.8 |
OH值(mg KOH/g) | 350.8 | 349.6 | 352.0 | 347.5 |
官能度(数基) | 2.50 | 2.50 | 2.50 | 2.50 |
疏水基含量(%) | 7.14 | 7.10 | 7.06 | 7.09 |
芳基含量(%) | 17.29 | 17.25 | 17.22 | 17.27 |
粘度(25℃,cPs) | 4,699 | 4,359 | 3,669 | 4,181 |
表2:
多元醇 | 多元醇-2 | 多元醇-2A | 多元醇-2B |
DMPA(每100份最终多元醇) | 0.00 | 1.15 | 3.43 |
酸值(mg KOH/g) | 1.1 | 0.8 | 1.1 |
OH值(mg KOH/g) | 354.0 | 353.3 | 357.3 |
官能度(数基) | 2.56 | 2.60 | 2.58 |
疏水基含量(%) | 6.97 | 7.02 | 6.96 |
芳基含量(%) | 16.97 | 17.41 | 17.18 |
粘度(25℃,cPs) | 5,939 | 5,419 | 4,799 |
由表1和表2可以看出,本发明的多元醇与对比多元醇相比粘度更低,同时保持了与对比多元醇类似的特性(如酸值、OH值、官能度、疏水基含量和芳基含量)。本发明多元醇的低粘度提高了这些化合物与用于制备聚氨酯和聚异氰脲酸酯基泡沫的其它组分的混合能力。更好的混合通常会改善泡沫产品的性能(如尺寸稳定性、导热性、抗压强度)。
Claims (23)
1.一种制备芳族聚酯多元醇化合物的方法,其中所述方法包括在酯化反应条件下使包含如下组分的反应混合物反应:
(i)芳族酸化合物;
(ii)脂族二醇化合物;
(iii)通式I的二羟基烷基链烷酸化合物:
通式I:
其中R为氢、C1-C8烷基(直链或支链)、C1-C8羟基烷基、C1-C12芳基或C1-C12脂环基,和其中R1、R2分别独立地为氢、C1-C8烷基(直链或支链);和
(iv)任选的疏水化合物、含至少三个羟基的多羟基化合物或它们的组合;
其中所述芳族聚酯多元醇化合物在25℃下为液体和羟基值为约30-600。
2.根据权利要求1所述的方法,其中R1和R2中至少一个为氢。
3.根据权利要求1所述的方法,其中R为氢、乙基、甲基、羟基甲基、C1-C3烷基或苯基。
4.根据权利要求1所述的方法,其中组分(iii)包括:2,2-二(羟基甲基)丙酸(DMPA);2,2-二(羟基甲基)丁酸(DMBA);2,2-二(羟基甲基)戊酸(DMPTA);2,2-二(羟基甲基)己酸(DMHA);2,2,2-三羟基甲基乙酸(TMAA);和2,2-二(羟基甲基)苯基乙酸和2,2-二(羟基甲基)甲苯基乙酸;或它们的组合。
5.根据权利要求1所述的方法,其中所述芳族聚酯多元醇化合物以其总重量计的生物可再生含量为至少10wt%。
6.根据权利要求1所述的方法,其中所述芳族聚酯多元醇化合物以其总重量计的回收含量为至少10wt%。
7.根据权利要求1所述的方法,其中所述芳族聚酯多元醇化合物在25℃下的粘度为约200-150,000厘泊。
8.根据权利要求1所述的方法,其中所述芳族聚酯多元醇化合物的酸值为约0.1-10mgKOH/g。
9.根据权利要求1所述的方法,其中所述芳族聚酯多元醇化合物的粘度低于按照相同的羟基值、芳基含量和计算官能度但不应用组分(iii)而制备的对应多元醇化合物的粘度。
10.根据权利要求1所述的方法,其中所述芳族聚酯多元醇化合物包括约1.5-3.5的平均官能度、约30-600的平均羟基值和约0.1-10的酸值,和在约25℃下的所得粘度为约200-50000厘泊。
11.根据权利要求1所述的方法,其中所述酯化反应条件包括在温度为约50-300℃下使反应混合物反应约1-24小时。
12.根据权利要求1所述的方法,其中所述反应混合物还包含(vi)酯化催化剂化合物,和其中所述酯化催化剂化合物占反应混合物重量约0.001-0.2wt%。
13.一种芳族聚酯多元醇化合物,其中所述芳族聚酯多元醇化合物为包含如下组分的反应混合物的反应产物:
(i)芳族酸化合物;
(ii)脂族二醇化合物;
(iii)通式I的二羟基烷基链烷酸化合物:
通式I:
其中R为氢、C1-C8烷基(直链或支链)、C1-C8羟基烷基、C1-C12芳基或C1-C12脂环基,和其中R1、R2分别独立地为氢、C1-C8烷基(直链或支链);和
(v)任选的疏水化合物、含至少三个羟基的多羟基化合物或它们的组合;
其中所述芳族聚酯多元醇化合物在25℃下为液体和羟基值为约30-600。
14.根据权利要求13所述的芳族聚酯多元醇化合物,其中R1和R2中至少一个为氢。
15.根据权利要求13所述的芳族聚酯多元醇化合物,其中R为氢、乙基、甲基、羟基甲基、C1-C3烷基或苯基。
16.根据权利要求13所述的芳族聚酯多元醇化合物,其中组分(iii)包括:2,2-二(羟基甲基)丙酸(DMPA);2,2-二(羟基甲基)丁酸(DMBA);2,2-二(羟基甲基)戊酸(DMPTA);2,2-二(羟基甲基)己酸(DMHA);2,2,2-三羟基甲基乙酸(TMAA);和2,2-二(羟基甲基)苯基乙酸和2,2-二(羟基甲基)甲苯基乙酸;或它们的组合。
17.根据权利要求13所述的芳族聚酯多元醇化合物,其中所述芳族聚酯多元醇化合物以其总重量计的生物可再生含量为至少10wt%。
18.根据权利要求13所述的芳族聚酯多元醇化合物,其中所述芳族聚酯多元醇化合物以其总重量计的回收含量为至少10wt%。
19.根据权利要求13所述的芳族聚酯多元醇化合物,其中所述芳族聚酯多元醇化合物在25℃下的粘度为约200-150,000厘泊。
20.根据权利要求13所述的芳族聚酯多元醇化合物,其中所述芳族聚酯多元醇化合物的酸值为约0.1-10mg KOH/g。
21.根据权利要求13所述的芳族聚酯多元醇化合物,其中所述芳族聚酯多元醇化合物的粘度低于按照相同的羟基值、芳基含量和计算官能度但不应用组分(iii)而制备的对应多元醇化合物的粘度。
22.根据权利要求13所述的芳族聚酯多元醇化合物,其中所述芳族聚酯多元醇化合物包括约1.5-3.5的平均官能度、约30-600的平均羟基值和约0.1-10的酸值,和在约25℃下的所得粘度为约200-50000厘泊。
23.一种聚氨酯泡沫组合物,包含:
(a)异氰酸酯化合物;
(b)芳族聚酯多元醇化合物,其为如下组分的酯化反应产物:
(i)芳族酸化合物;
(ii)脂族二醇化合物;
(iii)通式I的二羟基烷基链烷酸化合物:
通式I:
其中R为氢、C1-C8烷基(直链或支链)、C1-C8羟基烷基、C1-C12芳基或C1-C12脂环基,和其中R1、R2分别独立地为氢、C1-C8烷基(直链或支链);和
(iv)任选的疏水化合物、含至少三个羟基的多羟基化合物或它们的组合;
其中所述芳族聚酯多元醇化合物在25℃下为液体和羟基值为约30-600;和
(c)任选的发泡剂;和
(d)任选的辅助化合物和添加剂。
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