CN116253868A - 高官能度醇胺聚醚多元醇的制备方法 - Google Patents
高官能度醇胺聚醚多元醇的制备方法 Download PDFInfo
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- CN116253868A CN116253868A CN202211563580.6A CN202211563580A CN116253868A CN 116253868 A CN116253868 A CN 116253868A CN 202211563580 A CN202211563580 A CN 202211563580A CN 116253868 A CN116253868 A CN 116253868A
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- polyether polyol
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- alkylene oxide
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- 239000004721 Polyphenylene oxide Substances 0.000 title claims abstract description 58
- 229920000570 polyether Polymers 0.000 title claims abstract description 58
- -1 alcohol amine Chemical class 0.000 title claims abstract description 51
- 150000003077 polyols Chemical class 0.000 title claims abstract description 49
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- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 30
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 30
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 26
- 239000003054 catalyst Substances 0.000 claims abstract description 19
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- 238000006243 chemical reaction Methods 0.000 claims description 65
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
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- VOZKAJLKRJDJLL-UHFFFAOYSA-N 2,4-diaminotoluene Chemical compound CC1=CC=C(N)C=C1N VOZKAJLKRJDJLL-UHFFFAOYSA-N 0.000 claims description 5
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
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- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 5
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 3
- 239000000391 magnesium silicate Substances 0.000 description 3
- 229910052919 magnesium silicate Inorganic materials 0.000 description 3
- 235000019792 magnesium silicate Nutrition 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 229920005883 amine-based polyether polyol Polymers 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
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- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- AYRXSINWFIIFAE-SCLMCMATSA-N Isomaltose Natural products OC[C@H]1O[C@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)[C@@H](O)[C@@H](O)[C@@H]1O AYRXSINWFIIFAE-SCLMCMATSA-N 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
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- DLRVVLDZNNYCBX-RTPHMHGBSA-N isomaltose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-RTPHMHGBSA-N 0.000 description 1
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Abstract
本发明属于化学合成技术领域，具体涉及高官能度醇胺聚醚多元醇的制备方法，包括以下步骤：（1）在反应器中加入氨水和环氧烷烃进行自催化反应；（2）在步骤（1）所得物质中加入氨水和环氧烷烃进行自催化反应，得到醇胺化合物；（3）在醇胺化合物中加入高官能度起始剂和催化剂，加入环氧烷烃进行聚合反应，脱除水分，得到中间体聚醚多元醇；（4）在中间体聚醚多元醇中加入环氧烷烃进行聚合反应；（5）脱除未反应单体。本发明原料成本低廉，具有较高性价比，所制备的高官能度醇胺聚醚多元醇与戊烷互溶性高，用本发明产品制备的硬质聚氨酯泡沫导热系数低，尺寸稳定性高。
Description
技术领域
本发明属于化学合成技术领域，具体涉及高官能度醇胺聚醚多元醇的制备方法。
背景技术
聚氨酯是家用冰箱生产过程中唯一使用的保温材料，这种材料可提高冰箱总体节能效果，满足环保的需要。并且，聚氨酯保温材料注入冰箱内衬与金属外壳间空隙后，可以将这两层材料牢固结合，提高电器物流结构的强度和刚性。
随着环保要求越来越高，氢氟烃类发泡剂正在逐步被戊烷类发泡剂所替代，但在戊烷发泡剂体系中，通常存在发泡剂与其他组份相容性差的问题，继而影响制品性能。同时，低导快脱性能是制约冰箱组合料领域技术水平发展的关键，高官能度产品和特种胺产品的应用能够显著提升泡沫的脱模、导热性能和戊烷互溶性，是这个领域的发展方向。但由于特种胺原料普遍成本较高，直接采购成品作为起始剂组合料添加或参与聚合反应会大大提高产品的成本，降低组合聚醚市场竞争力。
通常情况下，提升家电用组合聚醚性能可以从两方面着手，一是对组合聚醚整体配方体系进行优化筛选，包括使用性能优良但成本较高的发泡剂或者硅油等助剂，但此种在非主体聚醚方面增强性能的方式往往带来成本增加，且效果微弱。例如，专利CN103665296B公开了一种低温低导聚氨酯泡沫、原料组合物、组合聚醚的制备方法，该方法使用1,1,1,3,3-五氟丙烷（又称HFC-245fa）作为物理发泡剂，该发泡剂性能优良，但成本较高，同时所得聚氨酯泡沫导热系数较全水和141b体系虽有改善，距行业内最佳水平仍有一定差距。
专利CN106008954B公开了一种胺基聚醚多元醇的制备方法，采用醇胺和甲苯二胺作为混合起始剂，在氢氧化钾催化条件下得到胺基聚醚多元醇，该方法中三乙醇胺、三异丙醇胺和甲苯二胺等胺类起始剂成本较高，不具备性价比优势。
发明内容
本发明要解决的技术问题是提供一种高官能度醇胺聚醚多元醇的制备方法，原料成本低廉，具有较高性价比，所制备的高官能度醇胺聚醚多元醇与戊烷互溶性高，用本发明产品制备硬质聚氨酯制品导热系数低，尺寸稳定性高。
本发明所述的高官能度醇胺聚醚多元醇的制备方法，包括以下步骤：
（1）在反应器中加入氨水和环氧烷烃进行自催化反应；
（2）在步骤（1）所得物质中加入氨水和环氧烷烃进行自催化反应，得到醇胺化合物；
（3）在醇胺化合物中加入高官能度起始剂和催化剂，加入环氧烷烃进行聚合反应，至反应器中压力不再下降，真空脱除水分，得到中间体聚醚多元醇；
（4）在中间体聚醚多元醇中加入环氧烷烃进行聚合反应，至反应器中压力不再下降；
（5）真空脱除未反应单体。
所用氨水浓度为25%~28%；
步骤（1）与步骤（2）中氨水的质量比为1:1；步骤（1）中环氧烷烃与氨水中氨的摩尔比为（0.5~5）：1，优选3:1；步骤（2）中环氧烷烃与氨水中氨的摩尔比为（0.5~5）：1，优选3:1。
按质量份数计：氨水为1~5份；高官能度起始剂为1~30份；催化剂为0.1~1份；步骤（3）和步骤（4）中的环氧烷烃之和为25~80份；
其中，步骤（3）中环氧烷烃的质量占步骤（3）与步骤（4）环氧烷烃质量之和的5%~30%。
高官能度起始剂为官能度不小于四的起始剂；高官能度起始剂为多元醇或胺类化合物，选自蔗糖、葡萄糖、麦芽糖、异麦芽糖、木糖醇、山梨醇、季戊四醇、乙二胺、苯二胺和甲苯二胺中的一种或多种。
环氧烷烃为环氧乙烷、环氧丁烷、环氧丙烷或环氧氯丙烷中的一种或多种。
催化剂为碱金属类催化剂和/或胺类催化剂；
当催化剂包含碱金属类催化剂时，还需对其进行脱除处理：将步骤（5）所得物依次进行中和处理、吸附处理、脱水干燥和减压抽滤，得到精制聚醚多元醇；
脱除具体步骤为：向步骤（5）所得物中加入酸，80~90℃下搅拌0.5~1h进行中和处理，加入吸附剂，80~90℃下搅拌0.5~1h进行吸附处理，经脱水干燥、减压抽滤，即得精制高官能度醇胺聚醚多元醇。
催化剂选自氢氧化钾、氢氧化钠、二甲胺、三甲胺、N，N-二甲基环己胺和2,4,6-三(二甲氨基甲基)苯酚中的一种或多种，优选氢氧化钾。
步骤（1）和步骤（2）的反应温度为20~60℃，反应时间为30~300min，压力为0.3~0.4MPa。
步骤（3）的反应温度为70~100℃，反应时间为30~300min；步骤（4）的反应温度为90~120℃，反应时间为30~300min。
与现有技术相比，本发明的有益效果是：
1、本发明采用氨水作为起始剂的一部分，原材料价格低廉，使产品具有较高性价比；
2、本发明产品具备较高官能度，分子结构中存在大量胺基官能团，与戊烷类发泡剂互溶性高，所制得的硬质聚氨酯泡沫具有导热系数低，尺寸稳定性高的优点；
综上所述，本发明从主体聚醚方面对家电组合聚醚进行性能提升，优于业内常见的从助剂方面提升性能的方案，且达到的效果更好，成本更低。
具体实施方式
下面将结合实施例，对本发明的技术方案进行清楚、完整地描述。
在实际操作中，温度控制允许有2℃的波动温差。实施例和对比例中用到的所有原料除特殊说明外，均为市购。
实施例1
（1）在负压下，将50g氨水抽入反应釜中，搅拌升温至40℃，向反应釜中缓慢通入120g环氧丙烷，在压力0.3MPa下反应180min；
（2）在负压下，再将50g氨水抽入反应釜中，然后向反应釜中缓慢通入120g环氧丙烷，在温度40℃，压力0.3MPa下反应180min，得到醇胺化合物；
（3）向醇胺化合物中依次加入150g蔗糖，2.8g氢氧化钾，氮气置换三次后将反应釜抽成负压，搅拌升温至85℃，缓慢通入50g环氧丙烷，反应90min，至反应釜压力不再下降；
（4）真空脱除水分后，向反应釜内缓慢通入580g环氧丙烷，在110℃下反应150min，至反应釜压力不再下降；
（5）真空脱除未反应的单体，得到粗制高官能度醇胺聚醚多元醇；
（6）脱除碱金属类催化剂；向粗制高官能度醇胺聚醚多元醇中加入7g浓度为70%的磷酸，80℃下搅拌1h后加入1g硅酸镁和0.5g硅酸铝组成的吸附剂，搅拌0.5h后脱水干燥、减压抽滤，即得精制高官能度醇胺聚醚多元醇。
实施例2
（1）在负压下，将100g氨水抽入反应釜中，搅拌升温至50℃，向反应釜中缓慢通入305g环氧乙烷，在压力0.3MPa下反应90min；
（2）在负压下，再将100g氨水抽入反应釜中，然后向反应釜中缓慢通入305g环氧乙烷，在温度50℃，压力0.3MPa下反应90min，得到醇胺化合物；
（3）向醇胺化合物中依次加入305g山梨醇，20gN,N-二甲基环己胺，氮气置换三次后将反应釜抽成负压，搅拌升温至75℃，缓慢通入100g环氧丙烷，反应150min，至反应釜压力不再下降；
（4）真空脱除水分后，向反应釜内缓慢通入1400g环氧丙烷，在100℃下反应180min，至反应釜压力不再下降；
（5）真空脱除未反应的单体，即得到高官能度醇胺聚醚多元醇。
实施例3
（1）在负压下，将100g氨水抽入反应釜中，搅拌升温至60℃，向反应釜中缓慢通入400g环氧氯丙烷，在压力0.4MPa下反应200min；
（2）在负压下，再将100g氨水抽入反应釜中，然后向反应釜中缓慢通入400g环氧氯丙烷，在温度60℃，压力0.4MPa下反应200min，得到醇胺化合物；
（3）向醇胺化合物中依次加入250g甲苯二胺，5.5g氢氧化钠，氮气置换三次后将反应釜抽成负压，搅拌升温至90℃，缓慢通入230g环氧丙烷，反应150min，至反应釜压力不再下降；
（4）真空脱除水分后，向反应釜内缓慢通入900g环氧丙烷，在120℃下反应150min，至反应釜压力不再下降；
（5）真空脱除未反应的单体，得到粗制高官能度醇胺聚醚多元醇；
（6）脱除碱金属类催化剂；向粗制高官能度醇胺聚醚多元醇中加入13g浓度为70%的磷酸（酸用量），90℃下搅拌1h后加入3g硅酸镁和1.5g硅酸铝组成的吸附剂（配比和用量须注明），搅拌1h后脱水干燥、减压抽滤，即得精制高官能度醇胺聚醚多元醇。
实施例4
（1）在负压下，将100g氨水抽入反应釜中，搅拌升温至30℃，向反应釜中缓慢通入280g环氧丙烷，在压力0.4MPa下反应120min；
（2）在负压下，再将100g氨水抽入反应釜中，然后向反应釜中缓慢通入280g环氧乙烷，在温度30℃，压力0.4MPa下反应120min，得到醇胺化合物；
（3）向醇胺化合物中依次加入350g葡萄糖，25g二甲胺，氮气置换三次后将反应釜抽成负压，搅拌升温至80℃，缓慢通入400g环氧氯丙烷，反应200min，至反应釜压力不再下降；
（4）真空脱除水分后，向反应釜内缓慢通入980g环氧氯丙烷，在110℃下反应240min，至反应釜压力不再下降；
（5）真空脱除未反应的单体，即得到高官能度醇胺聚醚多元醇。
实施例5
（1）在负压下，将100g氨水抽入反应釜中，搅拌升温至20℃，向反应釜中缓慢通入478g环氧丁烷，在压力0.3MPa下反应300min；
（2）在负压下，再将100g氨水抽入反应釜中，然后向反应釜中缓慢通入478g环氧丁烷，在温度20℃，压力0.3MPa下反应300min，得到醇胺化合物；
（3）向醇胺化合物中依次加入1200g季戊四醇，20g三甲胺，氮气置换三次后将反应釜抽成负压，搅拌升温至100℃，缓慢通入1600g环氧氯丙烷，反应300min，至反应釜压力不再下降；
（4）真空脱除水分后，向反应釜内缓慢通入2100g环氧氯丙烷，在90℃下反应30min，至反应釜压力不再下降；
（5）真空脱除未反应的单体，即得到高官能度醇胺聚醚多元醇。
实施例6
（1）在负压下，将100g氨水抽入反应釜中，搅拌升温至45℃，向反应釜中缓慢通入48g环氧丙烷，在压力0.4MPa下反应30min；
（2）在负压下，再将100g氨水抽入反应釜中，然后向反应釜中缓慢通入48g环氧丙烷，在温度45℃，压力0.4MPa下反应30min，得到醇胺化合物；
（3）向醇胺化合物中依次加入200g麦芽糖，25g2,4,6-三(二甲氨基甲基)苯酚，氮气置换三次后将反应釜抽成负压，搅拌升温至70℃，缓慢通入500g环氧丙烷，反应30min，至反应釜压力不再下降；
（4）真空脱除水分后，向反应釜内缓慢通入940g环氧丙烷，在120℃下反应300min，至反应釜压力不再下降；
（5）真空脱除未反应的单体，即得到高官能度醇胺聚醚多元醇。
对比例1
向反应釜中依次加入150g二乙二醇，130g甘油，2.8g氢氧化钾，氮气置换三次后将反应釜抽成负压，搅拌升温至85℃，缓慢通入50g环氧丙烷，反应90min，至反应釜压力为负压；再向反应釜内缓慢通入550g环氧丙烷，在110℃下反应150min，至反应釜压力不再下降，得到粗制高官能度醇胺聚醚多元醇；
真空脱除未反应的单体，向所得粗制高官能度聚醚多元醇中加入7g浓度为70%的磷酸，80℃下搅拌1h后加入1g硅酸镁和0.5g硅酸铝组成的吸附剂，搅拌0.5h后脱水干燥、减压抽滤，即得精制高官能度聚醚多元醇。
性能指标：
聚醚多元醇所用测试标准及方法为：
羟值：按照GB/T12008.3-1989《聚醚多元醇中羟值测定方法》进行测试；
粘度：按照GB/T12008.7-2010《塑料 聚醚多元醇 第7部分：粘度的测定》进行测试；
环戊烷互溶性测试方法为：25℃下向100g聚醚多元醇中多次少量加入环戊烷并使其充分混合，观察混合体系状态直至出现轻微浑浊，可得到100份聚醚所能溶解的环戊烷份数即戊烷互溶性。
实施例1~6和对比例1所得聚醚多元醇的性能指标见下表1。
表1实施例1~6和对比例1的高官能度聚醚多元醇性能指标
将实施例1~6和对比例1所得聚醚多元醇按表2所示配方进行配料，采取以下制备方法，得到硬质聚氨酯泡沫样品，将样品进行性能检测，结果见表3。
硬质聚氨酯泡沫样品制备方法：在环境温度25℃，模具温度45℃条件下，按表2中配方准确称取物料，于500mL烧杯中配制成组合料，取50份上述组合料与60份异氰酸酯PM200充分搅拌，待体系均匀时停止搅拌，将搅拌后的物料倒入恒温发泡成型模具中，待泡沫经过发泡、熟化、固化后将其从模具中取出，得到聚氨酯硬质泡沫样品。
表2硬质聚氨酯泡沫样品配方
聚氨酯硬质泡沫样品所用测试标准及方法为：
导热性能：将上述所得聚氨酯硬质泡沫切割为20*20*2.5（cm）尺寸的样块，进行导热性能测试，测试方法为GB/T10295-2008《绝热材料稳态热阻及有关特性的测定 热流计法》。
尺寸稳定性能：将聚氨酯硬质泡沫切割为100*100*25（cm）尺寸的样块，分别在80℃和-30℃下放置48h，测定泡沫收缩率，进行尺寸稳定性能测试。
表3实施例1~6和对比例1所制备硬质聚氨酯泡沫样品的性能
从表1和表3中可以看出，本发明环戊烷互溶性相比常规产品提升明显；采用常规配方，搭配常规发泡剂制备聚氨酯泡沫，本发明制备的样品导热系数可达到19mW/m·K以下，相比对比例1性能明显更加优异；本发明聚醚多元醇制备的聚氨酯硬质泡沫样品在高温和低温下的尺寸稳定性更高。
Claims (10)
1.一种高官能度醇胺聚醚多元醇的制备方法，其特征在于，包括以下步骤：
（1）在反应器中加入氨水和环氧烷烃进行自催化反应；
（2）在步骤（1）所得物质中加入氨水和环氧烷烃进行自催化反应，得到醇胺化合物；
（3）在醇胺化合物中加入高官能度起始剂和催化剂，加入环氧烷烃进行聚合反应，脱除水分，得到中间体聚醚多元醇；
（4）在中间体聚醚多元醇中加入环氧烷烃进行聚合反应；
（5）脱除未反应单体。
2.根据权利要求1所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，步骤（1）与步骤（2）中氨水的质量比为1:1；步骤（1）中环氧烷烃与氨水中氨的摩尔比为（0.5~5）：1；步骤（2）中环氧烷烃与氨水中氨的摩尔比为（0.5~5）：1。
3.根据权利要求1所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，按质量份数计：氨水为1~5份；高官能度起始剂为1~30份；催化剂为0.1~1份；步骤（3）和步骤（4）中的环氧烷烃之和为25~80份；
其中，步骤（3）中环氧烷烃的质量占步骤（3）与步骤（4）环氧烷烃质量之和的5%~30%。
4.根据权利要求1所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，高官能度起始剂为官能度不小于四的起始剂。
5.根据权利要求4所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，高官能度起始剂为多元醇或胺类化合物，选自蔗糖、葡萄糖、麦芽糖、异麦芽糖、木糖醇、山梨醇、季戊四醇、乙二胺、苯二胺和甲苯二胺中的一种或多种。
6.根据权利要求1所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，环氧烷烃为环氧乙烷、环氧丁烷、环氧丙烷或环氧氯丙烷中的一种或多种。
7.根据权利要求1所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，催化剂为碱金属类催化剂和/或胺类催化剂；
当催化剂包含碱金属类催化剂时，还需对其进行脱除处理：将步骤（5）所得物依次进行中和处理、吸附处理、脱水干燥和减压抽滤，得到精制聚醚多元醇。
8.根据权利要求7所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，催化剂选自氢氧化钾、氢氧化钠、二甲胺、三甲胺、N，N-二甲基环己胺和2,4,6-三(二甲氨基甲基)苯酚中的一种或多种。
9.根据权利要求1所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，步骤（1）和步骤（2）的反应温度为20~60℃，反应时间为30~300min，压力为0.3~0.4MPa。
10.根据权利要求1所述的高官能度醇胺聚醚多元醇的制备方法，其特征在于，步骤（3）的反应温度为70~100℃，反应时间为30~300min；步骤（4）的反应温度为90~120℃，反应时间为30~300min。
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1644604A (zh) * | 2004-12-30 | 2005-07-27 | 锦化化工（集团）有限责任公司 | 低氟硬泡用聚醚多元醇的制备方法 |
| CN109306057A (zh) * | 2018-09-29 | 2019-02-05 | 山东诺威新材料有限公司 | Ocf专用聚醚多元醇的制备方法 |
-
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1644604A (zh) * | 2004-12-30 | 2005-07-27 | 锦化化工（集团）有限责任公司 | 低氟硬泡用聚醚多元醇的制备方法 |
| CN109306057A (zh) * | 2018-09-29 | 2019-02-05 | 山东诺威新材料有限公司 | Ocf专用聚醚多元醇的制备方法 |
Non-Patent Citations (1)
| Title |
|---|
| 宋启煌: "《精细化工工艺学》", 31 December 1995, 北京：化学工业出版社, pages: 72 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117402347A (zh) * | 2023-12-15 | 2024-01-16 | 山东一诺威新材料有限公司 | 环境友好型自催化聚醚多元醇及其制备方法 |
| CN117402347B (zh) * | 2023-12-15 | 2024-05-10 | 山东一诺威新材料有限公司 | 环境友好型自催化聚醚多元醇及其制备方法 |
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