CN111410738A - 胺类自催化聚醚多元醇的制备方法 - Google Patents
胺类自催化聚醚多元醇的制备方法 Download PDFInfo
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- CN111410738A CN111410738A CN202010294311.9A CN202010294311A CN111410738A CN 111410738 A CN111410738 A CN 111410738A CN 202010294311 A CN202010294311 A CN 202010294311A CN 111410738 A CN111410738 A CN 111410738A
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- polyether polyol
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- autocatalysis
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- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 113
- 229920000570 polyether Polymers 0.000 title claims abstract description 113
- 229920005862 polyol Polymers 0.000 title claims abstract description 103
- 150000003077 polyols Chemical class 0.000 title claims abstract description 103
- 150000001412 amines Chemical class 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 30
- 229920000642 polymer Polymers 0.000 claims abstract description 24
- 238000005844 autocatalytic reaction Methods 0.000 claims abstract description 23
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims abstract description 12
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 11
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- 150000001875 compounds Chemical class 0.000 claims abstract description 10
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 9
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 9
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 claims abstract description 7
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- 238000007670 refining Methods 0.000 claims abstract description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
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- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 229930006000 Sucrose Natural products 0.000 claims description 4
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 claims description 4
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 3
- 229930195725 Mannitol Natural products 0.000 claims description 3
- 239000000594 mannitol Substances 0.000 claims description 3
- 235000010355 mannitol Nutrition 0.000 claims description 3
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 claims description 3
- 239000000600 sorbitol Substances 0.000 claims description 3
- 235000010356 sorbitol Nutrition 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- PHLZUDXEBCQHKM-UHFFFAOYSA-N (3,4-difluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C(F)=C1 PHLZUDXEBCQHKM-UHFFFAOYSA-N 0.000 claims description 2
- PQXWYQZQCWWMDQ-UHFFFAOYSA-N (4-fluoro-3-methylphenyl)methanamine Chemical compound CC1=CC(CN)=CC=C1F PQXWYQZQCWWMDQ-UHFFFAOYSA-N 0.000 claims description 2
- IRMXPESEXLQKHG-UHFFFAOYSA-N 1-benzothiophen-4-amine Chemical compound NC1=CC=CC2=C1C=CS2 IRMXPESEXLQKHG-UHFFFAOYSA-N 0.000 claims description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 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 claims description 2
- QYMUENUCKRLOTB-UHFFFAOYSA-N 2-n,2-n-dimethylbutane-1,2-diamine Chemical compound CCC(CN)N(C)C QYMUENUCKRLOTB-UHFFFAOYSA-N 0.000 claims description 2
- NFWPZNNZUCPLAX-UHFFFAOYSA-N 4-methoxy-3-methylaniline Chemical compound COC1=CC=C(N)C=C1C NFWPZNNZUCPLAX-UHFFFAOYSA-N 0.000 claims description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- 229960001413 acetanilide Drugs 0.000 claims description 2
- XXWCODXIQWIHQN-UHFFFAOYSA-N butane-1,4-diamine;hydron;dichloride Chemical compound Cl.Cl.NCCCCN XXWCODXIQWIHQN-UHFFFAOYSA-N 0.000 claims description 2
- PJHQPFRPACFPPM-UHFFFAOYSA-N chembl113822 Chemical compound OC1=CC(N)=CC=C1C1=NC2=CC=CC=C2S1 PJHQPFRPACFPPM-UHFFFAOYSA-N 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- 229930182478 glucoside Natural products 0.000 claims description 2
- 150000008131 glucosides Chemical class 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 2
- OBYVIBDTOCAXSN-UHFFFAOYSA-N n-butan-2-ylbutan-2-amine Chemical compound CCC(C)NC(C)CC OBYVIBDTOCAXSN-UHFFFAOYSA-N 0.000 claims description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 claims description 2
- 229920000768 polyamine Polymers 0.000 claims description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- RAUWPNXIALNKQM-UHFFFAOYSA-N 4-nitro-1,2-phenylenediamine Chemical compound NC1=CC=C([N+]([O-])=O)C=C1N RAUWPNXIALNKQM-UHFFFAOYSA-N 0.000 claims 1
- 229920005830 Polyurethane Foam Polymers 0.000 abstract description 8
- 239000011496 polyurethane foam Substances 0.000 abstract description 8
- 239000012855 volatile organic compound Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 description 62
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- 229910052757 nitrogen Inorganic materials 0.000 description 18
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- 239000000178 monomer Substances 0.000 description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 239000006260 foam Substances 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 229910001220 stainless steel Inorganic materials 0.000 description 6
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- 238000002425 crystallisation Methods 0.000 description 5
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- 150000003141 primary amines Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
- C08G65/2621—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups
- C08G65/2624—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aliphatic amine groups
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
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- C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
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- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2618—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen
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- C08G65/2627—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing nitrogen containing amine groups containing aromatic or arylaliphatic amine groups
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Abstract
本发明涉及一种聚醚多元醇的制备方法，具体涉及一种胺类自催化聚醚多元醇的制备方法。包括如下步骤：(1)采用化合物A、化合物B及化合物C组成的混合物作为起始剂，与环氧丙烷进行开环聚合，合成自催化聚醚多元醇的低聚物；(2)以自催化聚醚多元醇低聚物作为基础聚醚，以碱金属水溶液作为催化剂，先与环氧丙烷进行开环聚合，然后再用环氧乙烷进行封端，制得自催化聚醚多元醇粗聚物；(3)将自催化聚醚多元醇粗聚物进行精制处理，得到胺类自催化聚醚多元醇。采用该聚醚多元醇用于聚氨酯泡沫制品生产时，可显著减少下游制品加工过程中胺类催化剂的用量，不仅可以有效降低制品挥发性有机物的含量，同时还可以为生产企业有效降低生产成本。
Description
技术领域
本发明涉及一种聚醚多元醇的制备方法，具体涉及一种胺类自催化聚醚多元醇的制备方法。
背景技术
随着聚氨酯工业制造技术的发展，人们对聚氨酯泡沫制品的要求逐渐从单一的物理性能指标，逐渐转向对产品环保性能、功能化等综合性能的要求。大多数聚氨酯泡沫制品在发泡过程中都会用到催化剂，其中，胺类催化剂是聚氨酯制品中常用的一类催化剂。胺类催化剂在聚氨酯泡沫制备过程中只是催化发泡，并不参与发泡反应，泡沫制备完成后，此类小分子胺类催化剂会逐渐渗透、迁移到泡沫制品的表面，而后逐渐扩散到环境中。汽车内饰材料大多数为聚氨酯制品，释放出的胺类小分子催化剂会导致汽车挡风玻璃雾化以及严重的新车异味现象，家具行业也存在此类问题。因此，聚氨酯泡沫制品中胺类小分子催化剂引发的安全环保问题受到人们越来越多的关注。
发明内容
针对现有技术的不足，本发明的目的是提供一种胺类自催化聚醚多元醇的制备方法，采用该方法制备的聚醚具有较好的自催化作用，采用其制备聚氨酯泡沫制品，发泡过程中能够减少或者不用胺类催化剂，降低VOC排放。
本发明所述的胺类自催化聚醚多元醇的制备方法，包括如下步骤：
(1)采用化合物A、化合物B及化合物C组成的混合物作为起始剂，在0～0.4MPa压力，80～140℃下，与环氧丙烷进行开环聚合，合成自催化聚醚多元醇的低聚物；
(2)以自催化聚醚多元醇低聚物作为基础聚醚，以碱金属水溶液作为催化剂，在0～0.5MPa压力，80～130℃下，先与环氧丙烷进行开环聚合，然后再用环氧乙烷进行封端，制得自催化聚醚多元醇粗聚物；
(3)将自催化聚醚多元醇粗聚物进行精制处理，得到胺类自催化聚醚多元醇产品；
其中，所述的化合物A为多元胺类化合物；优选地，所述的化合物A为N,N-二甲基-1,3-丙二胺、N,N-二乙基乙二胺、N-乙酰基乙二胺、3-氨基吡唑、5-氨基-2-苯并噻唑-2-基-苯酚、4-甲氧基-3-甲基苯胺、苯胺、3,4-二氟苄胺、己二胺、N-[1-(氨基甲基)丙基]-N,N-二甲胺、甲乙胺、正丁胺、N-[3-(三甲氧基硅基)丙基]乙二胺、4-氨基苯并噻吩、4-氟-3-甲基苄胺、N,N-二乙基对苯二胺、4-硝基邻苯二胺、1,4-丁二胺二盐酸盐、乙酰苯胺、二苯胺、N-甲基苯胺、4,4'-硫代二苯胺、正戊胺、正己胺、二仲丁胺、正辛胺、甲胺、乙胺或二异丙胺中的一种或几种按照任意比例组成的混合物。
所述的化合物B为乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇、三丙二醇、甘油或三羟甲基丙烷中的一种；
所述的化合物C为季戊四醇、木糖醇、山梨醇、甘露醇、蔗糖或葡萄糖甙中的一种。
所述的化合物A、化合物B与化合物C的摩尔比为0.5～1:1:0.5～1。
所述的自催化聚醚多元醇的低聚物其数均分子量为400～500。
所述的碱金属为甲醇钠、乙醇钠、氢氧化钾或氢氧化钠中的一种或几种按照任意比例组成的混合物。
所述的碱金属水溶液的浓度为30～50wt％。
所述碱金属加入量为胺类自催化聚醚多元醇产品质量的0.8～10‰。
所述的环氧乙烷的用量为胺类自催化聚醚多元醇产品质量的5～25％。
所述的胺类自催化聚醚多元醇产品其数均分子量为1000～8000。
与现有的技术相比，本发明的有益效果如下：
1、本发明通过分子结构设计，在聚醚多元醇制备过程中以伯胺类小分子化合物作为起始剂，合成了分子结构中含有叔胺基团的自催化聚醚多元醇。发泡验证表明，本发明所制备的胺类自催化聚醚多元醇具有较好的自催化作用，可有效减少发泡过程中胺类催化剂的用量，降低泡沫制品中胺类挥发性物质的含量，从而有效降低制品中挥发性有机物的含量，从而起到保护环境的效果。
2、本发明所制备的具有自催化活性的胺类自催化聚醚多元醇用于聚氨酯泡沫的制备时，能够部分或全部取代小分子胺类催化剂，减少下游聚氨酯泡沫中胺类催化剂的用量，可为生产企业有效降低生产成本。
3、本发明分子结构设计中，在聚醚多元醇分子结构中引入叔胺基团的同时，还引入了高官能度起始剂，增加产物官能度，使得目标产物在下游应用过程中具有较好的力学性能。
4、本发明所述制备方法，科学合理、简单易行。
具体实施方式
下面结合具体实施例对本发明作进一步阐述，但本发明并不限于以下实施例。
所述方法如无特别说明，均为常规方法。
所述原材料如无特别说明，均能从公开商业途径而得。
实施例1
所述的胺类自催化聚醚多元醇的制备方法，由以下步骤组成：
(1)自催化聚醚多元醇低聚物的制备
在5L的不锈钢反应釜中加入102g N,N-二甲基-1,3-丙二胺、92g甘油及342g蔗糖(三种原料的摩尔比为1:1:1)，进行氮气置换，测反应釜内含氧量低于80ppm。升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为120±2℃，压力为-0.1～0.3MPa，连续加入967g环氧丙烷，内压反应90分钟，随后脱单体30分钟，即可制得数均分子量为500的自催化聚醚多元醇低聚物。
(2)自催化聚醚多元醇粗聚物的制备
反应釜内加入268g上述自催化聚醚多元醇低聚物作为基础聚醚，然后加入32.49g30wt％氢氧化钾水溶液(催化剂的质量百分含量为3‰)，升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为120±2℃，压力为-0.1～0.3MPa，向反应釜内连续加入2818g环氧丙烷，随后内压反应30分钟，内压反应温度120±2℃。保持釜内温度为120±2℃，压力为0.18～0.3MPa，向反应釜内加入163g环氧乙烷进行封端聚合反应，随后进行内压反应，内压反应温度为120±2℃，随后脱单体30分钟，即可制得自催化聚醚多元醇粗聚物。
(3)自催化聚醚多元醇的精制
上述自催化聚醚多元醇粗聚物经过中和、吸附、结晶、干燥、过滤，即可制得自催化聚醚多元醇，Mn＝6000。
实施例2
所述的胺类自催化聚醚多元醇的制备方法，由以下步骤组成：
(1)自催化聚醚多元醇低聚物的制备
在5L的不锈钢反应釜中加入44g N,N-二乙基乙二胺、76g丙二醇及91g山梨醇(三种原料的摩尔比为0.5:1:0.5)，进行氮气置换，测反应釜内含氧量低于80ppm。升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为82±2℃，压力为-0.1～0.4MPa，连续加入590g环氧丙烷，内压反应90分钟，随后脱单体30分钟，即可制得数均分子量为455的自催化聚醚多元醇低聚物。
(2)自催化聚醚多元醇粗聚物的制备
反应釜内加入200g上述自催化聚醚多元醇低聚物作为基础聚醚，然后加入40g50wt％氢氧化钾水溶液和40g 50wt％氢氧化钠水溶液的混合物(催化剂的质量百分含量为10‰)，升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为82±2℃，压力为-0.1～0.4MPa，向反应釜内连续加入2545g环氧丙烷，随后内压反应30分钟，内压反应温度130±2℃。保持釜内温度为115±2℃，压力为0.18～0.3MPa，向反应釜内加入1000g环氧乙烷进行封端聚合反应，随后进行内压反应，内压反应温度为115±2℃，随后脱单体30分钟，即可制得自催化聚醚多元醇粗聚物。
(3)自催化聚醚多元醇的精制
上述自催化聚醚多元醇粗聚物经过中和、吸附、结晶、干燥、过滤，即可制得自催化聚醚多元醇，Mn＝8000。
实施例3
所述的胺类自催化聚醚多元醇的制备方法，由以下步骤组成：
(1)自催化聚醚多元醇低聚物的制备
在5L的不锈钢反应釜中加入58g己二胺、62g乙二醇及136g季戊四醇(三种原料的摩尔比为0.5:1:1)，进行氮气置换，测反应釜内含氧量低于80ppm。升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为110±2℃，压力为-0.1～0.3MPa，连续加入868g环氧丙烷，内压反应90分钟，随后脱单体30分钟，即可制得数均分子量为450的自催化聚醚多元醇低聚物。
(2)自催化聚醚多元醇粗聚物的制备
反应釜内加入1800g上述自催化聚醚多元醇低聚物作为基础聚醚，然后加入10.67g30wt％甲醇钠水溶液(催化剂的质量百分含量为0.8‰)，升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为110±2℃，压力为-0.1～0.3MPa，向反应釜内连续加入1800g环氧丙烷，随后内压反应30分钟，内压反应温度110±2℃。保持釜内温度为110±2℃，压力为0.18～0.3MPa，向反应釜内加入400g环氧乙烷进行封端聚合反应，随后进行内压反应，内压反应温度为110±2℃，随后脱单体30分钟，即可制得自催化聚醚多元醇粗聚物。
(3)自催化聚醚多元醇的精制
上述自催化聚醚多元醇粗聚物经过中和、吸附、结晶、干燥、过滤，即可制得自催化聚醚多元醇，Mn＝1000。
实施例4
所述的胺类自催化聚醚多元醇的制备方法，由以下步骤组成：
(1)自催化聚醚多元醇低聚物的制备
在5L的不锈钢反应釜中加入36.5g正丁胺及36.5g苯胺的混合物、106g二乙二醇及182g甘露醇(正丁胺及苯胺的混合物：乙二胺：季戊四醇的摩尔比为1:1:0.5)，进行氮气置换，测反应釜内含氧量低于80ppm。升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为105±2℃，压力为-0.1～0.3MPa，连续加入713g环氧丙烷，内压反应90分钟，随后脱单体30分钟，即可制得数均分子量为500的自催化聚醚多元醇低聚物。
(2)自催化聚醚多元醇粗聚物的制备
反应釜内加入667g上述自催化聚醚多元醇低聚物作为基础聚醚，然后加入44.4g45％氢氧化钠水溶液，升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为115±2℃，压力为-0.1～0.3MPa，向反应釜内连续加入2733g环氧丙烷，随后内压反应30分钟，内压反应温度105±2℃。保持釜内温度为125±2℃，压力为0.18～0.3MPa，向反应釜内加入600g环氧乙烷进行封端聚合反应，随后进行内压反应，内压反应温度为125±2℃，随后脱单体30分钟，即可制得自催化聚醚多元醇粗聚物。
(3)自催化聚醚多元醇的精制
上述自催化聚醚多元醇粗聚物经过中和、吸附、结晶、干燥、过滤，即可制得自催化聚醚多元醇，Mn＝3000。
对比例1
所述的聚醚多元醇的制备方法，由以下步骤组成：
(1)聚醚多元醇低聚物的制备
在5L的不锈钢反应釜中加入92g甘油及342g蔗糖(两种原料的摩尔比为1:1)，进行氮气置换，测反应釜内含氧量低于80ppm。升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为120±2℃，压力为-0.1～0.3MPa，连续加入566g环氧丙烷，内压反应90分钟，随后脱单体30分钟，即可制得数均分子量为500的聚醚多元醇低聚物。
(2)聚醚多元醇粗聚物的制备
反应釜内加入268g上述自催化聚醚多元醇低聚物作为基础聚醚，然后加入32.49g30％氢氧化钾水溶液(催化剂的质量百分含量为3‰)，升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为120±2℃，压力为-0.1～0.3MPa，向反应釜内连续加入2786g环氧丙烷，随后内压反应30分钟，内压反应温度120±2℃。保持釜内温度为120±2℃，压力为0.18～0.3MPa，向反应釜内加入161g环氧乙烷进行封端聚合反应，随后进行内压反应，内压反应温度为120±2℃，随后脱单体30分钟，即可制得对比例1所述聚醚多元醇粗聚物。
(3)聚醚多元醇的精制
上述对比例1聚醚多元醇粗聚物经过中和、吸附、结晶、干燥、过滤，即可制得对比例聚醚多元醇，Mn＝6000。
对比例2
所述的聚醚多元醇的制备方法，由以下步骤组成：
(1)聚醚多元醇低聚物的制备
在5L的不锈钢反应釜中加入102g N,N-二甲基-1,3-丙二胺和92g甘油(两种原料的摩尔比为1:1)，进行氮气置换，测反应釜内含氧量低于80ppm。升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为120±2℃，压力为-0.1～0.3MPa，连续加入806g环氧丙烷，内压反应90分钟，随后脱单体30分钟，即可制得数均分子量为500的聚醚多元醇低聚物。
(2)聚醚多元醇粗聚物的制备
反应釜内加入268g上述自催化聚醚多元醇低聚物作为基础聚醚，然后加入32.49g30％氢氧化钾水溶液(催化剂的质量百分含量为3‰)，升温至105℃，进行氮气鼓泡减压脱水。保持釜内温度为120±2℃，压力为-0.1～0.3MPa，向反应釜内连续加入2818g环氧丙烷，随后内压反应30分钟，内压反应温度120±2℃。保持釜内温度为120±2℃，压力为0.18～0.3MPa，向反应釜内加入163g环氧乙烷进行封端聚合反应，随后进行内压反应，内压反应温度为120±2℃，随后脱单体30分钟，即可制得聚醚多元醇粗聚物。
(3)聚醚多元醇的精制
上述聚醚多元醇粗聚物经过中和、吸附、结晶、干燥、过滤，即可制得对比例聚醚多元醇，Mn＝6000。
将实施例1-4和对比例1所制备的聚醚多元醇，分别按照表1和表2发泡配方(表1和表2发泡配方中除胺类催化剂A-33用量存在差异之外，其它内容完全相同。发泡环境温度为25℃，发泡物料温度为25℃)进行发泡验证，实验结果如表3所示。
表1实施例1-4及对比例2发泡配方
表2对比例1发泡配方
表3实施例1-4和对比例1发泡实验结果
| 项目 | 实施例1 | 实施例2 | 实施例3 | 实施例4 | 对比例1 |
| 起发时间(s) | 6 | 8 | 7 | 8 | 13 |
| 凝胶时间(s) | 56 | 59 | 58 | 61 | 73 |
| 催化剂用量(g) | 0.1 | 0.1 | 0.1 | 0.1 | 1 |
| 挥发性有机物含量(μgC/g) | 14 | 19 | 15 | 17 | 58 |
将实施例1-4和对比例2所制备的聚醚多元醇分别按照表1发泡配方进行发泡并检测泡沫力学性能，实验结果如表4所示。
表4实施例1-4和对比例2泡沫力学性能检测结果
| 编号 | 实施例1 | 实施例2 | 实施例3 | 实施例4 | 对比例2 |
| 65％压陷硬度/kg.f | 59.1 | 58.6 | 57.8 | 57.1 | 50.1 |
| 25％压缩硬度/kg.f | 18.9 | 17.8 | 17.5 | 17.3 | 14.3 |
Claims (9)
1.一种胺类自催化聚醚多元醇的制备方法，其特征在于：包括如下步骤：
(1)采用化合物A、化合物B及化合物C组成的混合物作为起始剂，在0～0.4MPa压力，80～140℃下，与环氧丙烷进行开环聚合，合成自催化聚醚多元醇的低聚物；
(2)以自催化聚醚多元醇低聚物作为基础聚醚，以碱金属水溶液作为催化剂，在0～0.5MPa压力，80～130℃下，先与环氧丙烷进行开环聚合，再用环氧乙烷进行封端，制得自催化聚醚多元醇粗聚物；
(3)将自催化聚醚多元醇粗聚物进行精制处理，得到胺类自催化聚醚多元醇产品；
其中，所述的化合物A为多元胺类化合物；
所述的化合物B为乙二醇、二乙二醇、三乙二醇、丙二醇、二丙二醇、三丙二醇、甘油或三羟甲基丙烷中的一种；
所述的化合物C为季戊四醇、木糖醇、山梨醇、甘露醇、蔗糖或葡萄糖甙中的一种。
2.根据权利要求1所述的胺类自催化聚醚多元醇的制备方法，其特征在于：所述的化合物A为N,N-二甲基-1,3-丙二胺、N,N-二乙基乙二胺、N-乙酰基乙二胺、3-氨基吡唑、5-氨基-2-苯并噻唑-2-基-苯酚、4-甲氧基-3-甲基苯胺、苯胺、3,4-二氟苄胺、己二胺、N-[1-(氨基甲基)丙基]-N,N-二甲胺、甲乙胺、正丁胺、N-[3-(三甲氧基硅基)丙基]乙二胺、4-氨基苯并噻吩、4-氟-3-甲基苄胺、N,N-二乙基对苯二胺、4-硝基邻苯二胺、1,4-丁二胺二盐酸盐、乙酰苯胺、二苯胺、N-甲基苯胺、4,4'-硫代二苯胺、正戊胺、正己胺、二仲丁胺、正辛胺、甲胺、乙胺或二异丙胺中的一种或几种按照任意比例组成的混合物。
3.根据权利要求1所述的胺类自催化聚醚多元醇的制备方法，其特征在于：所述的化合物A、化合物B与化合物C的摩尔比为0.5～1:1:0.5～1。
4.根据权利要求1所述的胺类自催化聚醚多元醇的制备方法，其特征在于：所述的自催化聚醚多元醇的低聚物其数均分子量为400～500。
5.根据权利要求1所述的胺类自催化聚醚多元醇的制备方法，其特征在于：所述的碱金属为甲醇钠、乙醇钠、氢氧化钾或氢氧化钠中的一种或几种按照任意比例组成的混合物。
6.根据权利要求1所述的胺类自催化聚醚多元醇的制备方法，其特征在于：所述的碱金属水溶液的浓度为30～50wt％。
7.根据权利要求1所述的胺类自催化聚醚多元醇的制备方法，其特征在于：所述的碱金属加入量为胺类自催化聚醚多元醇产品质量的0.8～10‰。
8.根据权利要求1所述的胺类自催化聚醚多元醇的制备方法，其特征在于：所述的环氧乙烷的用量为胺类自催化聚醚多元醇产品质量的5～25％。
9.根据权利要求1所述的胺类自催化聚醚多元醇的制备方法，其特征在于：所述的胺类自催化聚醚多元醇产品其数均分子量为1000～8000。
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| CN113651951A (zh) * | 2021-09-03 | 2021-11-16 | 山东一诺威新材料有限公司 | 海绵用自催化聚醚多元醇及其制备方法 |
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