CN1142956C - 利用叔戊基过氧化自由基引发剂制备接枝多元醇的方法 - Google Patents
利用叔戊基过氧化自由基引发剂制备接枝多元醇的方法 Download PDFInfo
- Publication number
- CN1142956C CN1142956C CNB008056501A CN00805650A CN1142956C CN 1142956 C CN1142956 C CN 1142956C CN B008056501 A CNB008056501 A CN B008056501A CN 00805650 A CN00805650 A CN 00805650A CN 1142956 C CN1142956 C CN 1142956C
- Authority
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- China
- Prior art keywords
- amyl peroxy
- defined method
- radical initiator
- content
- olefinic
- 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.)
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- -1 t-amyl peroxy free radical Chemical class 0.000 title claims abstract description 110
- 229920005862 polyol Polymers 0.000 title claims abstract description 73
- 150000003077 polyols Chemical class 0.000 title claims abstract description 72
- 239000003999 initiator Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims description 51
- 230000008569 process Effects 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 69
- 239000000178 monomer Substances 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 86
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 55
- 238000002360 preparation method Methods 0.000 claims description 33
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 27
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 25
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 23
- 229920000570 polyether Polymers 0.000 claims description 16
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 15
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 15
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 14
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 10
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- 125000002947 alkylene group Chemical group 0.000 description 24
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 18
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- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 10
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- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 6
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- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
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- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 4
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- 229910052698 phosphorus Inorganic materials 0.000 description 4
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- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
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- 239000010695 polyglycol Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920005903 polyol mixture Polymers 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
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- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
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- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- VCZQFJFZMMALHB-UHFFFAOYSA-N tetraethylsilane Chemical compound CC[Si](CC)(CC)CC VCZQFJFZMMALHB-UHFFFAOYSA-N 0.000 description 1
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- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- NNBZCPXTIHJBJL-MGCOHNPYSA-N trans-decalin Chemical compound C1CCC[C@@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-MGCOHNPYSA-N 0.000 description 1
- CMHHITPYCHHOGT-UHFFFAOYSA-N tributylborane Chemical compound CCCCB(CCCC)CCCC CMHHITPYCHHOGT-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical class NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
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- VNTDZUDTQCZFKN-UHFFFAOYSA-L zinc 2,2-dimethyloctanoate Chemical compound [Zn++].CCCCCCC(C)(C)C([O-])=O.CCCCCCC(C)(C)C([O-])=O VNTDZUDTQCZFKN-UHFFFAOYSA-L 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
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Abstract
本发明涉及采用叔戊基过氧化化合物作为自由基引发剂的接枝多元醇。新颖的接枝多元醇是通过在自由基引发剂和优选的链转移剂的存在下、在多元醇组合物中聚合至少一种单体而制备的。所得接枝多元醇继而可用于与多异氰酸酯反应,制备聚氨酯产品。
Description
本发明涉及采用叔戊基过氧化化合物作为自由基引发剂制备接枝多元醇的方法。这些接枝多元醇可用于聚氨酯泡沫的生产。本发明还涉及在聚氧化亚烷基聚醚多元醇中的低粘度接枝聚合物分散系。
更确切地,本发明涉及通过这样一种方法制备的接枝聚合物分散系,该方法采用烯属不饱和单体或单体混合物在含有有效量诱导不饱和度的多元醇混合物中的自由基聚合作用,其中该聚合作用是在包含叔戊基过氧化化合物的自由基引发剂的存在下进行的。这种改进方法出产稳定的、低粘度的、不沉淀接枝聚合物分散系。
现有技术、例如美国专利Nos.3,652,639、3,875,258、3,950,317和美国专利Nos.Re.28,715、29,014和33,291教导了可用于聚氨酯制备的接枝聚合物分散系的制备,即在多元醇的存在下进行烯属不饱和单体的聚合作用。上述专利公开了各种制备接枝聚合物分散系的方法。美国专利No.3,931,092教导了聚合固体的制备,即在自由基引发剂和有机溶剂的存在下进行聚合。所用溶剂浓度为约1份至19份,以每份羟基末端有机化合物的重量计,该化合物具有可聚合的碳双键。美国专利No.3,953,393教导了接枝共聚物分散系的制备,即采用烷基硫醇链转移剂,浓度为0.1至2重量%,基于乙烯基单体的重量而言。
已经发现多元醇中稳定的聚合物分散系在聚氨酯的制备中具有广泛的商业用途。这些分散系已知在接枝或聚合物多元醇贸易中有利于处理,尤其提高聚氨酯产品的坚固性,通常以承重或模数表示。为了改善代表技术现状的产品,人们已经做出了很多努力。针对增加分散在多元醇中的聚合物的量已经做了努力,明显的益处是能够生产更坚固的聚氨酯。已经发现了两个主要障碍:所得分散系的粘度太高了和/或在所用单体混合物中使用了相对高水平的丙烯腈。
另外,如果能够制备在较少附聚作用方面表现更好的稳定性的聚合物多元醇,那么这将是可取的。稳定性对多元醇在用于制备聚氨酯泡沫之前的保存期限来说是重要的,因为如果不稳定的话,很多聚合物多元醇趋向于发生相分离。相对低的粘度和小的粒径对高质量多元醇来说也是重要的,以便在大体积泡沫生产设备中易于充气。
Shah的美国专利No.4,148,840和Van Cleve等的美国专利4,242,249描述了预先形成的聚合物多元醇在SAN分散系多元醇的合成中作为分散系稳定剂的用途。美国专利No.4,148,840描述了在25℃下粘度小于40,000cP的、预先形成的聚合物多元醇稳定剂。不过,这些材料是粘性的分散系或半固体,趋向于难以加工。
Shook等的美国专利No.4,172,825涉及生产具有高聚合物含量的聚合多元醇的方法。该参考文献描述了制备聚合物多元醇的方法,该方法采用过氧化叔丁基作为自由基引发剂。不过,所得聚合物多元醇的粘度趋向于高于由本发明所提供的那些。
Ramlow等的美国专利Nos.4,327,005和4,334,049教导了苯乙烯/烯丙醇共聚物的烯化氧加合物作为预先形成的聚合物多元醇稳定剂。该稳定剂可以采取接枝共聚物分散系或微细粉碎的固体聚合物的形式。
进而,Pizzini等在美国专利No.3,652,639中描述了丙烯腈与不饱和多元醇的接枝共聚物的用途,该接枝共聚物是均相的透明液体,可以直接用于柔性聚氨酯泡沫的制备。不饱和多元醇是这样获得的,即具有烯属不饱和度和羟基、羧基或环氧基的有机化合物与多元醇反应。大量其他专利也教导了丙烯酰基盖帽的不饱和多元醇与苯乙烯和丙烯腈共聚生产聚合物多元醇的用途。这些专利包括美国专利Nos.4,460,715、4,477,603、4,640,935、4,513,124、4,394,491和4,390,645。
最近,国际公开No.WO 87/03886和美国专利No.4,745,153教导了在含有活性氢的化合物作为溶剂的存在下,乙烯基末端多元醇加合物单独或与烯属不饱和的单体或单体混合物的均聚或共聚作用,和它们作为预先形成的分散剂的用途。
在已知的限度内,相关领域还没有单独或组合教导或提示能够利用叔戊基类自由基引发剂生产高度稳定的、低粘度接枝多元醇,特别是与半连续或连续的过程有关。
本发明涉及接枝聚合物分散系的制备方法。改进后的方法采用至少一种烯属不饱和单体在多元醇混合物中的自由基聚合作用,该混合物含有有效量、优选为小于0.1摩尔每摩尔多元醇混合物的诱导不饱和度,其中自由基引发剂包含叔戊基过氧化化合物。此外,已经发现,改进的分散系可以这样制备,采用在聚醚酯多元醇-聚氧化亚烷基聚醚多元醇混合物中的原子团聚合作用,该混合物含有小于0.1摩尔诱导不饱和度每摩尔多元醇混合物,其中该不饱和部分是含有异构化马来酸酯的聚醚酯多元醇。
优选地,所用叔戊基过氧化化合物选自由叔戊基过氧化(2-乙基己酸酯)、1,1-双(叔戊基过氧化)环己烷及其混合物组成的组。另外,本发明涉及用于接枝多元醇生产的自由基引发剂,生产优选地利用连续的接枝反应器进行,还涉及生产接枝多元醇的方法,其中样本之间的粘度性质没有巨大差异。
按照用于聚氨酯泡沫制备的稳定接枝聚合物分散系的改进制备方法,改进之处包括在有效量自由基引发剂的存在下、在不饱和多元醇混合物中进行烯属不饱和单体或单体混合物的聚合作用,该多元醇混合物含有有效量的诱导不饱和度,优选为小于0.1摩尔诱导不饱和度每摩尔多元醇混合物,其中该自由基引发剂包含叔戊基过氧化化合物。在发明的另一种实施方式中,在有效量自由基引发剂的存在下、烯属不饱和单体或单体混合物在含有不饱和度的多元醇混合物(优选地含有0.1摩尔不饱和度每摩尔多元醇混合物)中的聚合作用采用这样的改进方法,该方法包括在多元醇混合物中进行聚合作用,该多元醇混合物采用聚醚酯多元醇作为混合物的一部分,该聚醚酯多元醇是通过聚氧化亚烷基聚醚多元醇与马来酸酐和烯化氧的反应而制备的。这种聚醚酯多元醇通过本领域技术人员熟知的方法异构化。这些方法包括加热或异构化催化剂,例如吗啉、二丁胺、二乙胺、二乙醇胺、硫醇等。
具有诱导不饱和度的多元醇在下文中称之为“大分子单体”。可以采用链转移剂作为反应慢化剂。聚合反应可以在25℃与180℃之间、优选为80℃与140℃之间的温度下进行。在本发明的一种实施方式中,多元醇混合物含有小于约0.1摩尔、优选为约0.001至约0.09摩尔不饱和度每摩尔多元醇混合物。一般来说,多元醇混合物具有有效量的诱导不饱和度,这里应当被定义为约0.001至约0.2摩尔诱导不饱和度每摩尔多元醇混合物。
可用于聚醚酯多元醇制备的烯化氧包括环氧乙烷、环氧丙烷、环氧丁烷、环氧戊烷和这些氧化物的混合物。
一般来说,本发明的接枝聚合物分散系在25℃下的粘度小于20,000cP,优选地在25℃下的粘度为2000至15,000cP,固体含量为约30至约70重量%,优选为约40至约60重量%,基于聚合物分散系的总重量而言。自然,随着接枝聚合物分散系的固体含量增加,分散系的粘度也增加。
可以采用的链转移剂如下:乙酸、溴乙酸、氯乙酸、二溴乙酸乙酯、碘乙酸、三溴乙酸、三溴乙酸乙酯、三氯乙酸、三氯乙酸乙酯、丙酮、对溴苯乙腈、对硝基苯乙炔、烯丙醇、2,4,6-三硝基苯胺、对乙炔基茴香醚、2,4,6-三硝基茴香醚、偶氮苯、苯甲醛、对氰基苯甲醛、2-丁基苯、溴苯、1,3,5-三硝基苯、苯并、三硝基苯甲酸乙酯、苯偶姻、苄腈、苯并芘、三丁基硼烷、1,4-丁二醇、3,4-环氧-2-甲基-1-丁烯、叔丁醚、异氰基叔丁烷、1-苯基丁炔、对甲酚、对溴枯烯、二苯并并四苯、对二噁烷、五苯基乙烷、乙醇、1,1-二苯基乙烯、乙二醇、乙醚、芴、N,N-二甲基甲酰胺、2-庚烯、2-己烯、异丁醛、溴代丙二酸二乙酯、溴代三氯甲烷、二溴乙烷、二碘甲烷、萘、1-萘酚、2-萘酚、油酸甲酯、2,4,4-三苯基-1-戊烯、4-甲基-2-戊烯、2,6-二异丙基苯酚、苯基醚、苯膦、二乙膦、二丁膦、三氯化磷、1,1,1-三溴丙烷、二烷基邻苯二甲酸酯、1,2-丙二醇、3-膦基丙腈、1-丙醇、焦儿茶酚、焦没食子酚、硬脂酸甲酯、四乙基硅烷、三乙基硅烷、二溴
、α-溴苯乙烯、α-甲基苯乙烯、四苯基琥珀腈、2,4,6-三硝基甲苯、对甲苯胺、N,N-二甲基对甲苯胺、α-氰基对甲苯腈、α,α’-二溴对二甲苯、2,6-二甲苯酚、二乙基锌、二硫代二乙酸、二硫代二乙酸乙酯、4,4’-二硫代双邻氨基苯甲酸、苯硫醇、邻乙氧基苯硫醇、2,2,-二硫代双苯并噻唑、苄硫醚、1-十二烷硫醇、乙硫醇、1-己硫醇、1-萘硫醇、2-萘硫醇、1-辛硫醇、1-庚硫醇、2-辛硫醇、1-十四烷硫醇、α-甲苯硫醇、异丙醇、2-丁醇、四溴化碳和十二烷基叔硫醇。优选的链转移剂是2-丙醇和2-丁醇。
所用链转移剂将取决于所用特定的单体或单体混合物和这些混合物的摩尔比。所用链转移剂的浓度可以是0.1至30重量%,优选为5至20重量%,基于单体的重量而言。
可以与本发明大分子单体结合使用的、基本上不含烯属不饱和度的代表性多元醇是本领域技术人员熟知的。它们通常是通过烯化氧或烯化氧混合物的催化缩合作用制备的,与具有至少两个活性氢原子的有机化合物的制备同时进行或先后进行,例如参见美国专利Nos.1,922,459、3,190,927和3,346,557。代表性多元醇包括含有多羟基的聚酯、聚氧化亚烷基聚醚多元醇、多羟基末端的聚氨酯聚合物、含有多羟基的磷化合物、和多元聚硫酯、聚缩醛、脂族多元醇与硫醇、氨、胺的烯化氧加合物及其混合物,胺包括芳族、脂族和杂环胺.还可以使用含有上述定义类别内2个或更多不同基团的化合物的烯化氧加合物,例如含有氨基和羟基的氨基醇。而且,可以使用含有一个SH基和一个OH基的化合物以及含有氨基和SH基的化合物的烯化氧加合物。一般来说,多元醇的当量将从100至10,000不等,优选为1000至3000。
可以使用任何适合的羟基末端聚酯,它们例如是从多羧酸和多元醇制备的。可以使用任何适合的多羧酸,例如草酸、丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、巴西基酸、它普酸、马来酸、富马酸、戊烯二酸、α-氢粘康酸、β-氢粘康酸、α-丁基-α-乙基戊二酸、α,β-二乙基琥珀酸、间苯二甲酸、对苯二甲酸、连苯三酸和1,4-环己烷二羧酸。可以使用任何适合的多元醇,包括脂族的和芳族的,例如乙二醇、丙二醇、亚丙基二醇、1,2-丁二醇、1,3-丁二醇、1,4-丁二醇、1,2-戊二醇、1,4-戊二醇、1,5-戊二醇、1,6-己二醇、1,7-庚二醇、甘油、1,1,1-三羟甲基丙烷、1,1,1-三羟甲基乙烷、1,2,6-己三醇、α-甲基葡糖苷、季戊四醇和山梨糖醇。在术语“多元醇”内还包括从苯酚衍生的化合物,例如2,2-双(4-羟基苯基)丙烷,即公知的双酚A。
含有羟基的聚酯也可以是聚酯酰胺,例如通过在聚酯的制备试剂中包括一些胺或氨基醇而获得。因此,聚酯酰胺可以通过缩合氨基醇(例如乙醇胺)与上述多羧酸而获得,或者它们可以利用组成含有羟基的聚酯的相同组分与仅一部分二胺组分(例如乙二胺)加以制备。
可以使用任何适合的聚氧化亚烷基聚醚多元醇,例如烯化氧或烯化氧混合物与多元醇的聚合产物。可以使用任何适合的多元醇,例如上文公开的用在羟基末端聚酯制备中的那些。可以使用任何适合的烯化氧,例如环氧乙烷、环氧丙烷、环氧丁烷、环氧戊烷和这些氧化物的混合物。聚氧化亚烷基聚醚多元醇可以从其他原料制备,例如四氢呋喃和烯化氧-四氢呋喃混合物;环氧卤丙烷,例如环氧氯丙烷;以及芳基烯化氧(aralkylene oxide),例如氧化苯乙烯。聚氧化亚烷基聚醚多元醇可以具有伯羟基或仲羟基。聚醚多元醇包括聚氧化乙二醇、聚氧化丙二醇、聚氧化丁二醇、聚丁二醇;嵌段共聚物,例如聚氧化丙二醇与聚氧化乙二醇的组合、聚-1,2-氧化丁二醇与聚氧化乙二醇的组合、聚-1,4-氧化丁二醇与聚氧化乙二醇的组合;无规共聚二醇,从两种或更多烯化氧的掺合物制成或者通过先后加入两种或更多烯化氧而制成。聚氧化亚烷基聚醚多元醇可以通过任何已知方法制备,例如公开在Wurtz,1959,《化学工艺学百科全书》Vo1.7,pp.257-262中的方法,由Interscience Publishers,Inc.(1951)出版,或者公开在美国专利No.1,922,459中的方法。优选的聚醚包括三羟甲基丙烷、甘油、季戊四醇、蔗糖、山梨糖醇、丙二醇和2,2’-(4,4’-羟基苯基)丙烷的烯化氧加成产物及其掺合物,当量为100至5000。
可以与烯化氧缩合的适合的多元聚硫醚包括硫二甘醇的缩合产物或二羧酸的反应产物,例如上文关于用任何其他适合的硫醚二醇制备含有羟基的聚酯所公开的那些。
可以使用的含有多羟基的磷化合物包括公开在美国专利No.3,639,542中的那些化合物。优选的含有多羟基的磷化合物是从烯化氧和含有相当于约72%至约95% P2O5的含磷酸制备的。
可以与烯化氧缩合的适合的聚缩醛包括甲醛或其他适合的醛与二元醇或上文公开的烯化氧的反应产物。
可以与烯化氧缩合的适合的脂族硫醇包括含有至少两个SH基的烷硫醇,例如1,2-乙二硫醇、1,2-丙二硫醇、1,3-丙二硫醇和1,6-己二硫醇;烯硫醇,例如2-丁烯-1,4-二硫醇;和炔硫醇,例如3-己炔-1,6-二硫醇。
可以与烯化氧缩合的适合的胺包括芳族胺,例如苯胺、邻氯苯胺、对氨基苯胺、1,5-二氨基萘、亚甲基二苯胺、苯胺与甲醛的缩合产物、和2,3-、2,6-、3,4-、2,5-与2,4-二氨基甲苯;脂族胺,例如甲胺、三异丙醇胺、乙二胺、1,3-二氨基丙烷、1,3-二氨基丁烷和1,4-二氨基丁烷。
本发明还可以采用含有酯基的多元醇。这些多元醇是通过烯化氧与有机二羧酸酐和含有反应性氢原子的化合物的反应而制备的。这些多元醇及其制备方法的更广泛讨论可以参见美国专利Nos.3,585,185、3,639,541和3,639,542。
用在本发明中的不饱和多元醇或大分子单体可以通过任何常规多元醇(例如上述的那些)与有机化合物的反应加以制备,该有机化合物具有烯属不饱和度和羟基、羧基、酸酐、异氰酸酯或环氧基,或其他与含活性氢基团反应性基团,或者它们可以通过采用有机化合物作为常规多元醇制备中的反应剂加以制备,该有机化合物具有烯属不饱和度和羟基、羧基、酸酐或环氧基,或其他与含活性氢基团反应性基团。这类有机化合物的代表包括不饱和的-羧酸与多羧酸和酸酐,例如马来酸与酸酐、富马酸、巴豆酸与酸酐、丙烯基、琥珀酸酐、丙烯酸、丙烯酰氯、丙烯酸或异丁烯酸羟乙酯和卤代马来酸与酸酐;不饱和多元醇,例如2-丁烯-1,4-二醇、甘油烯丙醚、三羟甲基丙烷烯丙醚、季戊四醇烯丙醚、季戊四醇乙烯醚、季戊四醇二烯丙醚和1-丁烯-3,4-二醇;不饱和环氧化物,例如1-乙烯基环己烯-3,4-环氧化物、丁二烯一氧化物、乙烯基缩水甘油醚(1-乙烯氧基-2,3-环氧丙烷)、异丁烯酸缩水甘油酯和3-烯丙氧基环氧丙烷(烯丙基缩水甘油醚)。如果采用多羧酸或酸酐将不饱和度结合在多元醇中,那么优选的是使不饱和多元醇与烯化氧、优选为环氧乙烷或环氧丙烷反应,在用于本发明之前用羟基取代羧基。烯化氧的用量使不饱和多元醇的酸值减小到约5或以下。
在本发明的一种实施方式中,在有效量异构化催化剂的存在下,在80℃至120℃的温度范围下,使马来酸化的大分子单体异构化一个半小时至三小时,这些是本领域技术人员所熟知的。催化剂的使用浓度一般大于0.01重量%,基于大分子单体的重量而言。
在采用选自二价金属盐与氧化物的催化剂制备聚醚酯多元醇时,催化剂的浓度可以采用0.005至0.5重量%,基于多元醇混合物的重量而言。温度采用75℃至175℃。用于制备大分子单体的多元醇当量可以从1000至10,000不等,优选为2000至6000。
二价金属可以采用:乙酸锌、氯化锌、氧化锌、新癸酸锌、氯化锡、环烷酸钙、氯化钙、氧化钙、乙酸钙、环烷酸铜、乙酸镉、氯化镉、氯化镍、氯化锰和乙酸锰。
某些上述催化剂、例如环烷酸钙促进马来酸酯在大分子单体的制备期间异构化为富马酸酯结构,而其他催化剂、例如氯化锌抑制这种异构化作用,它是有效的聚合作用催化剂。
如上所述,本发明的接枝聚合物分散系是通过烯属不饱和单体或烯属不饱和单体混合物在上述多元醇中的就地聚合作用而制备的。可以用在本发明中的代表性烯属不饱和单体包括丁二烯、异戊二烯、1,4-戊二烯、1,6-己二烯、1,7-辛二烯、苯乙烯、α-甲基苯乙烯、2-甲基苯乙烯、3-甲基苯乙烯与4-甲基苯乙烯、2,4-二甲基苯乙烯、乙基苯乙烯、异丙基苯乙烯、丁基苯乙烯、苯基苯乙烯、环己基苯乙烯、苄基苯乙烯等;取代的苯乙烯,例如氰基苯乙烯、硝基苯乙烯、N,N-二甲氨基苯乙烯、乙酰氧基苯乙烯、4-乙烯基苯甲酸甲酯、苯氧基苯乙烯、对乙烯基苯基氧等;丙烯酸取代的丙烯酸单体,例如丙烯腈、丙烯酸、异丁烯酸、丙烯酸甲酯、丙烯酸2-羟乙酯、异丁烯酸甲酯、异丁烯酸环己基酯、异丁烯酸苄基酯、异丁烯酸异丙酯、异丁烯酸辛酯、异丁烯腈、α-乙氧基丙烯酸乙酯、α-乙酰氨基丙烯酸甲酯、丙烯酸丁酯、丙烯酸2-乙基己基酯、丙烯酸苯基酯、异丁烯酸苯基酯、N,N-二甲基丙烯酰胺、N,N-二苄基丙烯酰胺、N-丁基丙烯酰胺、异丁烯酰甲酰胺等;乙烯基酯、乙烯基醚、乙烯基酮等,例如乙酸乙烯酯、丁酸乙烯酯、乙酸异丙烯酯、甲酸乙烯酯、丙烯酸乙烯酯、异丁烯酸乙烯酯、甲氧基乙酸乙烯酯、苯甲酸乙烯酯、乙烯基甲苯、乙烯基萘、乙烯基甲基醚、乙烯基乙基醚、乙烯基丙基醚、乙烯基丁基醚、乙烯基2-乙基己基醚、乙烯基苯基醚、乙烯基2-甲氧基乙基醚、甲氧基丁二烯、乙烯基2-丁氧基乙基醚、3,4-二氢-1,2-吡喃、2-丁氧基-2’-乙烯氧基二乙基醚、乙烯基甲基酮、乙烯基乙基酮、膦酸乙烯酯、乙烯基苯基酮、乙烯基乙基砜、N-甲基-N-乙烯基乙酰胺、N-乙烯基吡咯烷酮、乙烯基咪唑、二乙烯基亚砜、二乙烯基砜、乙烯基磺酸钠、乙烯基磺酸甲酯、N-乙烯基吡咯等;富马酸二甲酯、马来酸二甲酯、马来酸、巴豆酸、富马酸、衣康酸、衣康酸一甲酯、异丁烯酸叔丁氨基乙基酯、异丁烯酸二甲氨基乙基酯、丙烯酸缩水甘油酯、烯丙醇、衣康酸乙二醇单酯、乙烯基吡啶等。
可以使用任何已知的可聚合单体,上文列举的化合物是适用于本发明的单体的例证而非限制。优选地,单体选自由丙烯腈、苯乙烯及其混合物组成的组。
用在聚合反应中的烯属不饱和单体的量一般为25%至70%,优选为40%至60%,基于产物的总重量而言。聚合作用发生在约25℃与180℃之间的温度下,优选为80℃至140℃。优选的是至少25至90重量%、更优选为约40与75重量%之间的所用单体是苯乙烯或4-甲基苯乙烯。一般来说,在本发明的方法中将采用约0.1重量%至约3.0重量%、优选为约0.3至约1.0重量%的自由基引发剂,基于所用单体的总重量而言。在本发明的方法中,自由基引发剂包含叔戊基过氧化化合物。适合的叔戊基过氧化化合物包括叔戊基过氧化新癸酸酯、叔戊基过氧化新戊酸酯、叔戊基过氧化-2-乙基己酸酯、1,1-二(叔戊基过氧化)-3,3,5-三甲基环己烷、2,2-[4,4-二(叔戊基过氧化环己基)丙烷]、1,1-二(叔戊基过氧化)环己烷、叔戊基过氧化-2-甲基苯甲酸酯、1,1-二(叔戊基过氧化)-3,5,5-三甲基环己烷、2,2-二(叔戊基过氧化)丁烷、二叔戊基二过氧化壬二酸酯、叔戊基过氧化异丙基碳酸酯、叔戊基过氧化苯甲酸酯、叔戊基过氧化乙酸酯、正丁基-4,4-二(叔戊基过氧化)戊酸酯、二叔戊基二过氧化邻苯二甲酸酯、二(2-叔戊基过氧化异丙基)苯、2,5-二甲基-2,5-二(叔戊基过氧化)己烷、1,4-二(2-叔戊基过氧化异丙基)苯、过氧化叔戊基枯基、过氧化二叔戊基、氢过氧化叔戊基、叔戊基过氧化二乙基乙酸酯、叔戊基过氧化异丁酸酯、叔戊基过氧化-2-乙基己基碳酸酯、叔戊基过氧化硬脂酰碳酸酯、叔戊基过氧化(2-乙基己酸酯)和1,1-双(叔戊基过氧化)环己烷。这些叔戊基过氧化化合物可以单独使用,或者可以彼此结合使用。
在本发明的优选实施方式中,自由基引发剂选自由叔戊基过氧化(2-乙基己酸酯)和1,1-双(叔戊基过氧化)环己烷及其混合物组成的组。更优选地,本发明的自由基引发剂组合物将包括一定量的叔戊基过氧化(2-乙基己酸酯)和1,1-双(叔戊基过氧化)环己烷。当彼此结合使用时,叔戊基过氧化(2-乙基己酸酯)与1,1-双(叔戊基过氧化)环己烷的重量比一般将为约1∶10至约1∶2,更优选为约1∶4至约1∶3。
在其他自由基引发剂与上述叔戊基过氧化化合物结合用在本发明方法中的有限程度上,可以采用的其他自由基引发剂是熟知的自由基型乙烯基聚合作用引发剂,例如过氧化物、过硫酸盐、过硼酸盐、过碳酸盐、偶氮化物等。它们包括过氧化氢、过氧化二苯甲酰、过氧化乙酰、氢过氧化苯甲酰、氢过氧化叔丁基、过氧化二叔丁基、过氧化月桂酰、过氧化丁酰、氢过氧化二异丙基苯、氢过氧化枯烯、氢过氧化对薄荷烷、过氧化二乙酰、过氧化二-α-枯基、过氧化二丙基、过氧化二异丙基、过氧化异丙基叔丁基、过氧化丁基叔丁基、过氧化二糠酰、过氧化双(三苯甲基)、过氧化双(对甲氧基苯甲酰)、过氧化对一甲氧基苯甲酰、过氧化红烯、驱蛔萜、过苯甲酸叔丁酯、二乙基过氧化对苯二酸酯、氢过氧化丙基、氢过氧化异丙基、氢过氧化正丁基、氢过氧化叔丁基、氢过氧化环己基、氢过氧化反式十氢萘、氢过氧化α-甲基苄基、氢过氧化α-甲基-α-乙基苄基、氢过氧化四氢萘、氢过氧化三苯甲基、氢过氧化二苯甲基、α,α’-偶氮双(2-甲基庚腈)、1,1’-偶氮双(环己烷腈)、4,4’-偶氮双(4-氰基戊酸)、2,2’-偶氮双(异丁腈)、1-叔丁基偶氮-1-氰基环己烷、过琥珀酸、二异丙基过氧化二碳酸酯、2,2’-偶氮双(2,4-二甲基戊腈)、2-叔丁基偶氮-2-氰基-4-甲氧基-4-甲基戊烷、2,2’-偶氮双-2-甲基丁烷腈、2-叔丁基偶氮-2-氰基丁烷、1-叔戊基偶氮-1-氰基环己烷、2,2’-偶氮双(2,4-二甲基-4-甲氧基戊腈)、2,2’-偶氮双-2-甲基丁腈、2-叔丁基偶氮-2-氰基-4-甲基戊烷、2-叔丁基偶氮-2-异丁腈、叔丁基过氧化异丙基碳酸酯等;还可以使用引发剂的混合物。优选的引发剂是2,2’-偶氮双(2-甲基丁腈)、2,2’-偶氮双(异丁腈)、2,2’-偶氮双(2,4-二甲基戊腈)、2-叔丁基偶氮-2-氰基-4-甲氧基-4-甲基戊烷、2-叔丁基偶氮-2-氰基-4-甲基戊烷、2-叔丁基偶氮-2-氰基丁烷和过氧化月桂酰。
关于接枝聚合物分散系和用于制备接枝聚合物分散系的方法的一般说明列在美国专利US RE 33,291、4,690,956、4,689,354、4,458,038、4,4550,194和4,661,531中,引用在此作为参考文献。
用在本发明中的聚氨酯泡沫一般是在其他含有多羟基的组分、链延长剂、催化剂、表面活性剂、稳定剂、染剂、填充剂和色素的存在下,通过接枝聚合物分散系与有机多异氰酸酯的反应而制备的。泡沫聚氨酯塑料的适合制备方法公开在美国专利No.Re.24,514中,引用在此作为参考文献,以及配合使用的适合机械。当加入水作为发泡剂时,可以使用相应量的过量异氰酸酯与水反应,生成二氧化碳。有可能利用预聚物工艺进行聚氨酯塑料的制备,其中过量有机多异氰酸酯在第一步中与本发明的多元醇反应,制得具有游离异氰酸酯基的预聚物,然后在第二步中与水和/或其他多元醇反应,制得泡沫。或者,各组分可以在单一的操作步骤中反应,即公知的制备聚氨酯的“单步”工艺。此外,可以使用下列发泡剂代替水:低沸点烃,例如戊烷、己烷、庚烷、戊烯和庚烯;偶氮化物,例如偶氮六氢苯二甲腈;卤代烃,例如二氯二氟甲烷、三氯氟甲烷、二氯二氟乙烷、二氯乙烯和二氯甲烷。
可以采用的有机多异氰酸酯包括芳族、脂族和脂环族多异氰酸酯及其组合。这些类型的代表是二异氰酸酯,例如间亚苯基二异氰酸酯、2,4-甲苯二异氰酸酯、2,6-甲苯二异氰酸酯、2,4-与2,6-甲苯二异氰酸酯的混合物、六亚甲基二异氰酸酯、四亚甲基二异氰酸酯、环己烷-1,4-二异氰酸酯、六氢甲苯二异氰酸酯(和异构体)、萘-1,5-二异氰酸酯、1-甲氧基苯基-2,4-二异氰酸酯、4,4’-二苯基甲烷二异氰酸酯、4,4’-亚联苯二异氰酸酯、3,3乙二甲氧基-4,4’-联苯二异氰酸酯、3,3’-二甲基-4,4’-联苯二异氰酸酯和3,3’-二甲基二苯基甲烷二异氰酸酯;三异氰酸酯,例如4,4’,4”-三苯基甲烷三异氰酸酯和甲苯2,4,6-三异氰酸酯;四异氰酸酯,例如4,4’-二甲基二苯基甲烷-2,2’,5,5’-四异氰酸酯;和聚合的多异氰酸酯,例如聚亚甲基聚亚苯基多异氰酸酯。鉴于它们的可利用性和性质,尤其有用的是甲苯二异氰酸酯、4,4’-二苯基甲烷二异氰酸酯和聚亚甲基聚亚苯基多异氰酸酯。
在本发明的组合物中还可以使用粗的多异氰酸酯,例如通过甲苯二胺混合物的光气化作用所得粗的甲苯二异氰酸酯或通过粗的二苯基甲烷二胺的光气化作用所得粗的二苯基甲烷异氰酸酯。优选的或粗的异氰酸酯公开在美国专利No.3,215,652中。
如上所述,接枝多元醇可以与本领域常用的另一种含有多羟基的组分结合采用。在可用于本发明的聚氨酯泡沫制备中可以采用上述用于接枝多元醇制备的任何含有多羟基的组分。
可以用在聚氨酯泡沫制备中的链延长剂包括具有至少两个携带活性氢原子的官能团的那些化合物,例如水、肼、伯与仲二胺、氨基醇、氨基酸、羟基酸、二醇或其混合物。一组优选的链延长剂包括水、乙二醇、1,4-丁二醇和比水更容易与预聚物反应的伯与仲二胺,例如亚苯二胺、1,4-环己烷双(甲胺)、乙二胺、二亚乙基三胺、N-(2-羟基丙基)乙二胺、N,N’-二(2-羟基丙基)乙二胺、哌嗪和2-甲基哌嗪。
可以使用任何适合的催化剂,包括叔胺,例如三亚乙基二胺、N-甲基吗啉、N-乙基吗啉、二乙基乙醇胺、N-椰油吗啉(cocomorpholine)、1-甲基-4-二甲氨基乙基哌嗪、3-甲氧基丙基二甲胺、N,N,N’-三甲基异丙基丙二胺、3-二乙氨基丙基二乙胺、二甲基苄胺等。其他适合的催化剂例如氯化亚锡、二丁基锡二-2-乙基己酸酯、氧化亚锡,以及其他有机金属化合物,例如公开在美国专利No.2,846,408中。
表面活性剂一般是根据本发明的高级聚氨酯泡沫制备所必要的,因为在没有它的存在下,泡沫会崩溃或含有非常大的不均匀空泡。已经发现大量表面活性剂是令人满意的。非离子表面活性剂是优选的。其中,已经发现诸如熟知的有机硅氧聚合物等非离子表面活性剂是特别可取的。其他有效的、尽管不是优选的表面活性剂包括长链醇的聚乙二醇醚,长链烷基硫酸酯、烷基磺酸酯与烷基芳基磺酸的叔胺或烷醇胺盐。
已经发现当在聚氨酯泡沫产品的制备中使用本发明的接枝聚合物分散系时,优选地将阻燃剂化合物结合在泡沫产品中,以赋予阻燃性。可以采用的阻燃剂是:五溴二苯醚、二溴丙醇、三(β-氯丙基)磷酸酯、2,2-双(溴乙基)1,3-丙二醇、四(2-氯乙基)亚乙基二磷酸酯、三(2,3-二溴丙基)磷酸酯、三(β-氯乙基)磷酸酯、三(1,2-二氯丙基)磷酸酯、双(2-氯乙基)2-氯乙基磷酸酯、三氧化钼、钼酸铵、磷酸铵、三甲苯基磷酸酯、六溴环十二烷和二溴乙基二溴环己烷。阻燃剂化合物的浓度可以采用5至25份每100份多元醇混合物。
下列实施例阐述本发明的本性,不被解释为限制发明。除非另有指示,所有份数均以重量份给出。
实施例
多元醇A 是多元醇C中的30%(1∶1丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)。
多元醇B 是三羟甲基丙烷引发的环氧丙烷、环氧乙烷加合
物,含有环氧乙烷帽,羟基数为25。
多元醇C 是三羟甲基丙烷引发的环氧丙烷、环氧乙烷加合
物,含有环氧乙烷帽,羟基数为35。
多元醇D 是多元醇C中的50%(1∶1丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)。
多元醇E 是多元醇C中的50%(1∶2丙烯腈/苯乙烯)分散
系,使用USP 90 PX。
多元醇G 是多元醇C中的45%(1∶2丙烯腈/苯乙烯)分散
系,使用USP 90 PX。
多元醇H 是甘油引发的环氧丙烷、环氧乙烷加合物,含有
12.5wt%环氧乙烷(混杂)和环氧丙烷帽,羟基数
为51。
多元醇J 是多元醇H中的43%(1∶2丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)。
多元醇K 是多元醇H中的50%(1∶2丙烯腈/苯乙烯)分散
系,使用USP 90 PX。
多元醇L 是多元醇H中的50%(1∶2丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)和USP 90
PX。
多元醇M 是多元醇H中的50%(1∶2丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)和USP 90
PX。
多元醇N 是多元醇H中的50%(1∶1丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)和USP 90
PX。
多元醇O 是多元醇H中的50%(1∶1丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)。
多元醇P 是丙二醇引发的环氧丙烷加合物,羟基数为145。
多元醇Q 是多元醇P中的60%(45∶55丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)和USP 90
PX。
多元醇R 是多元醇P中的60%(45∶55丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)和USP 90
PX。
多元醇S 是多元醇P中的60%(45∶55丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)和USP 90
PX。
多元醇T 是多元醇P中的60%(45∶55丙烯腈/苯乙烯)分散
系,使用2,2’-偶氮双(2-甲基丁烷腈)和USP 90
PX。
多元醇X 是多元醇H中的43%(1∶2丙烯腈/苯乙烯)分散
系,使用VAZO 67。
多元醇W 是多元醇H中的50%(1∶2丙烯腈/苯乙烯)分散
系,使用USP 90 PX。
VAZO 67 是2,2’-偶氮双(2-甲基丁烷腈)聚合作用引发剂,
商业上可从E.I.DuPont Co.获得。
USP 90 PX 是80%1,1’-双(叔戊基过氧化)环己烷的2,2’,4-
三甲基-1,3-戊二醇异丁酸酯溶液,可从Witco
Corporation获得。
LUPERSOL 575 是叔戊基过氧化(2-乙基己酸酯),可从Lucidol,
Inc.获得。
DC-5043 是聚硅氧烷表面活性剂,可从Dow Corning
Corporation获得。
DEOA-LF 是含有15%水的二乙醇胺,可从Union Carbide
Corporation获得。
Dabco 33 LV 是33%三亚乙基三胺的二丙二醇溶液,可从Air
Products Corporation获得。
Niax A-1 是胺催化剂,由Union Carbide Corp.制造。
T-12 是有机锡催化剂,由Air Products Corp.制造。
AB 100 是氯化磷酸酯阻燃剂,商业上可从Albright &
Wilson,Inc.获得。
大分子单体A 是含有富马酸酯的聚醚多元醇,通过三羟甲基丙烷
/环氧丙烷加合物(具有4.8%环氧乙烷帽,羟基数
为25)与马来酸酐在环烷酸钙催化剂的存在下反
应而制得,具有环氧丙烷帽。代表性合成操作描述
在美国专利RE 33,291栏11操作A中。
大分子单体B 是含有富马酸酯的聚醚多元醇,通过甘油/环氧丙
烷加合物(具有25%环氧乙烷结构,其中20%是混
杂的,5%是帽,羟基数为25)与马来酸酐在环烷
酸钙催化剂的存在下反应而制得,具有环氧丙烷
帽。代表性合成操作描述在美国专利RE 33,291
栏11操作A中。
大分子单体C 是含有1-(1-异氰酸基-1-甲基乙基)-3-(1-甲基
乙烯基)苯加合物的聚醚多元醇,通过蔗糖/二丙二
醇引发的聚醚多元醇环氧丙烷加合物(具有5%环
氧乙烷帽,羟基数为25)的反应而制得。代表性
合成操作描述在美国专利5,093,412中。
利用300ml流通式反应器在压力下以连续方式制备本发明的接枝多元醇。反应器是满负荷工作的,也就是不存在液面上部空间。最初含有多元醇或接枝多元醇。在启动期,弃去泵出反应器的物料,直至生成所需的产物。由多元醇、大分子单体、单体、反应慢化剂和自由基引发剂组成的反应混合物进入反应器底部,通过弹簧阀与已经在反应器顶部的物料混合。反应器内的压力保持在60-120psi,反应温度为140-160℃。
粗产物离开反应器后,不再处于压力下。收集后,在玻璃烧瓶内、在<0.1mmHg压力和125℃下汽提最少30分钟,以除去挥发物,例如未反应的单体。加入抗氧化剂使最终产物稳定,冷却,贮存在适当容器内。
一旦得到所需的接枝多元醇,即制备如表1-4所述的各种泡沫样本,将多异氰酸酯组合物按所需指数引入具有一定物理性质的接枝多元醇组合物中,例如所要分析的密度、拉伸强度、伸长率和撕裂强度。
下表1-4证明,按照本发明的教导,采用叔戊基过氧化化合物作为自由基引发剂的接枝多元醇与使用叔丁基过氧化化合物作为自由基引发剂而制备的接枝多元醇相比,粘度更低,分散稳定性显著更好。
表1
接枝聚合物固体水平为20%、密度为1.8磅每立方英尺的泡沫 | |||||||
泡沫编号 | 1 | 2 | 3 | 4 | 5 | 6 | 7 |
组分,pbw | |||||||
多元醇A | 65 | 65 | |||||
多元醇B | 35 | 35 | 35 | 35 | 35 | 35 | 35 |
多元醇C | 25 | 25 | 25 | 25 | 25 | ||
多元醇D | 40 | 40 | |||||
多元醇E | 40 | 40 | |||||
多元醇G | 40 | ||||||
DC-5043 | 0.8 | 0.8 | 0.8 | 0.8 | 0.8 | 0.8 | 0.8 |
DEOA-LF | 1.6 | 1.6 | 1.6 | 1.6 | 1.6 | 1.6 | 1.6 |
DABCO 33LV | 0.12 | 0.12 | 0.12 | 0.12 | |||
NIAX A-1 | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 | 0.04 |
T-12 | 0.06 | 0.06 | 0.06 | 0.06 | 0.06 | 0.06 | 0.06 |
AB-100 | 4.0 | 4.0 | 4.0 | 4.0 | 4.0 | 4.0 | 4.0 |
水 | 3.0 | 3.0 | 3.0 | 3.0 | 3.0 | 3.0 | 3.0 |
TDI | 40.51 | 40.51 | 40.51 | 40.51 | 40.51 | 40.51 | 40.51 |
TDI指数 | 105 | 105 | 105 | 105 | 105 | 105 | 105 |
接枝聚合物固体% | 20 | 20 | 20 | 20 | 20 | 20 | 20 |
泡沫性质: | |||||||
密度,pcf | 1.82 | 1.76 | 1.74 | 1.86 | 1.75 | 1.68 | 1.65 |
拉伸强度,psi | 22 | 19 | 21 | 24 | 28 | 19 | 24 |
潮湿老化后的拉伸强度,psi | 21 | 16 | 22 | 21 | 27 | 22 | 25 |
伸长率,% | 152 | 127 | 138 | 161 | 146 | 111 | 148 |
撕裂强度,pi | 2.9 | 1.8 | 3.2 | 2.8 | 3.4 | 2.4 | 3.2 |
表2
接枝多元醇: | A D E G | |||
成分: | ||||
载体多元醇:多元醇C | 67 | 42.39 | 47.36 | 47.36 |
丙烯腈 | 15.5 | 15.94 | 14.64 | 14.64 |
苯乙烯 | 15.5 | 31.87 | 29.27 | 29.27 |
大分子单体类型 | A | B | B | B |
大分子单体量 | 1.24 | 2.15 | 1.98 | 1.98 |
反应慢化剂类型 | 十二烷硫醇 | 2-丙醇 | 2-丙醇 | 2-丙醇 |
反应慢化剂量 | 0.31 | 7.17 | 6.58 | 6.58 |
VAZO 67(自由基引发剂) | 0.31 | 0.48 | - | 0.09 |
USP 90 PX(自由基引发剂) | - | - | 0.18 | 0.09 |
表3
接枝多元醇: | J | K | L | M | N | O |
成分: | ||||||
载体多元醇:多元醇H | 54.71 | 41.96 | 41.96 | 41.96 | 41.96 | 41.68 |
丙烯腈 | 14.33 | 15.94 | 15.94 | 15.94 | 15.94 | 15.94 |
苯乙烯 | 28.67 | 31.87 | 31.87 | 31.87 | 31.87 | 31.87 |
大分子单体类型 | A | A | A | A | A | A |
大分子单体量 | 1.61 | 2.87 | 2.87 | 2.87 | 2.87 | 2.87 |
反应慢化剂类型 | 十二烷硫醇 | 2-丙醇 | 2-丙醇 | 2-丙醇 | 2-丙醇 | 2-丙醇 |
反应慢化剂量 | 0.43 | 7.17 | 7.17 | 7.17 | 7.17 | 7.17 |
VAZO 67(自由基引发剂) | 0.25 | - | 0.05 | 0.095 | 0.04 | 1.48 |
USP 90 PX(自由基引发剂) | - | 0.19 | 0.14 | 0.095 | 0.15 | - |
表4
接枝多元醇: | Q | R | S | T | W | X |
成分: | ||||||
载体多元醇:多元醇P | 31.45 | 31.45 | 31.45 | 31.11 | 41.94 | 46.93 |
丙烯腈 | 25.34 | 25.34 | 25.34 | 25.34 | 15.94 | 22.35 |
苯乙烯 | 30.97 | 30.97 | 30.97 | 30.97 | 31.87 | 27.35 |
大分子单体类型 | B | B | B | B | A | C |
大分子单体量 | 3.38 | 3.38 | 3.38 | 3.38 | 2.87 | 2.48 |
反应慢化剂类型 | 2-丙醇 | 2-丙醇 | 2-丙醇 | 2-丙醇 | 2-丙醇 | 2-丁醇/水 |
反应慢化剂量 | 8.45 | 8.45 | 8.45 | 8.45 | 7.17 | 9.92/0.58 |
VAZO 67(自由基引发剂) | 0.17 | 0.17 | - | 0.34 | - | 0.33 |
USP 90 PX(自由基引发剂) | 0.25 | 0.25 | 0.42 | 0.42 | 0.24 | - |
根据本发明的接枝聚合物分散系还可以在半间歇式反应器内制备。对适合的反应器进行下列操作。反应剂及其水平如下表5所述。装入1升四颈RB烧瓶内,将反应混合物加热至反应温度。通过Kenics静态混合器加入单体和多元醇混合物,反应指定时间。反应阶段之后,在约1mmHg下真空汽提混合物达30分钟。反应温度为125℃,单体加入时间为210分钟,多元醇/LUPERSOL 575加入时间为220分钟;反应时间为30分钟;搅拌是在300rpm下进行的。
下表5证明,按照本发明的教导,采用叔戊基过氧化化合物作为自由基引发剂的接枝多元醇与使用叔丁基过氧化化合物作为自由基引发剂而制备的接枝多元醇相比,粘度更低。不过,也正如所阐述的,当采用叔戊基化合物时,基本上需要较少的引发剂。
表5
多元醇 | 加入时间(min) | |||||||||||
实施例 | MAC(g) | 装料(g) | 进科(g) | RX MOD(g) | AN(g) | STY(g) | LUPERSOL(g) | 反应温度(℃) | MON | 多元醇 | 粘度mPas,25℃ | 乙烯基wt% |
1 | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 1.50 | 125 | 210 | 220 | 5240 | 38.64 |
2 | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 1.80 | 125 | 210 | 220 | 6160 | 38.66 |
3 | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 1.20 | 125 | 210 | 220 | 5440 | 38.58 |
4 | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 1.50 | 125 | 210 | 220 | 5460 | 38.34 |
5 | 9.00a | 171.0 | 180.0b | 1.20f | 80.0 | 160.0 | 1.50 | 125 | 210 | 220 | 3860 | 38.30 |
6 | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 0.60 | 125 | 210 | 220 | 3850 | 37.67 |
7 | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 0.60 | 125 | 210 | 220 | 3490 | 37.02 |
8 | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 0.90 | 125 | 210 | 220 | 4440 | 37.87 |
9 | 9.00a | 171.0 | 180.0b | 2.40f | 160.0 | 80.0 | 1.20 | 125 | 210 | 220 | 3990 | 38.96 |
10 | 12.00a | 138.0 | 150.0j | 3.00c | 100.0 | 200.0 | 1.50 | 125 | 240 | 250 | 3420 | 48.29 |
11k | 12.00a | 138.0 | 150.0j | 3.00f | 200.0 | 100.0 | 1.50 | 125 | 240 | 250 | 2750 | 49.03 |
12 | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 1.50 | 125 | 210 | 220 | 5580 | 38.86 |
13g | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 1.50 | 125 | 210 | 220 | 6600 | 38.50 |
14g | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 0.90 | 125 | 210 | 220 | 5280 | 38.27 |
15g | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 0.60 | 125 | 210 | 220 | 4220 | 37.71 |
多元醇 | 加入时间(min) | |||||||||||
16g | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 1.20 | 125 | 210 | 220 | 5100 | 37.81 |
17g | 9.00a | 171.0 | 180.0b | 2.40c | 80.0 | 160.0 | 1.80 | 125 | 210 | 220 | 8860 | 38.50 |
18g | 9.00a | 171.0 | 180.0b | 2.40f | 160.0 | 80.0 | 1.20 | 125 | 210 | 220 | 5920 | 38.76 |
19g | 12.00a | 138.0 | 150.0j | 3.00c | 100.0 | 200.0 | 1.50 | 125 | 240 | 250 | 3240 | 48.35 |
20g,k | 12.00a | 138.0 | 150.0j | 3.00f | 200.0 | 100.0 | 1.50 | 125 | 240 | 250 | 3250 | 48.78 |
a)大分子单体A
b)多元醇H
c)1-十二烷硫醇
f)溴三氯甲烷
g)叔丁基过氧化辛酸酯
j)多元醇P
k)烧瓶侧壁上累积的固体
尽管显而易见的是,所公开的发明的优选实施方式预计充分达到所述目的,不过不言而喻的是,发明容许修饰、修改和改变而不背离其精神。
Claims (30)
1、稳定的低粘度接枝聚合物分散系的制备方法,包括在有效量自由基引发剂的存在下,在含有有效量诱导不饱和度的多元醇的混合物中聚合至少一种烯属不饱和的单体,其中所述自由基引发剂包含1,1-双(叔戊基过氧化)环己烷或1,1-双(叔戊基过氧化)环己烷与叔戊基过氧化(2-乙基己酸酯)的混合物。
2、如权利要求1所定义的方法,其中所述烯属不饱和的单体的含量为25wt%至70wt%,基于所有组分的总重量而言。
3、如权利要求1所定义的方法,其中所述烯属不饱和的单体或单体混合物的含量为40wt%至60wt%,基于所有组分的总重量而言。
4、如权利要求1所定义的方法,其中所述自由基引发剂的含量为0.1wt%至3.0wt%,基于所述烯属不饱和的单体的重量而言。
5、如权利要求1所定义的方法,其中所述自由基引发剂的含量为0.3wt%至1.0wt%,基于所述烯属不饱和的单体的重量而言。
6、如权利要求1所定义的方法,其中所述自由基引发剂包含叔戊基过氧化(2-乙基己酸酯)与1,1-双(叔戊基过氧化)环己烷的掺合物,其中叔戊基过氧化(2-乙基己酸酯)与1,1-双(叔戊基过氧化)环己烷的重量比为1∶10至1∶2。
7、如权利要求6所定义的方法,其中该重量比是1∶4至1∶3。
8、如权利要求1所定义的方法,其中所述多元醇混合物的含量为30wt%至75wt%,基于所有组分的总重量而言。
9、如权利要求1所定义的方法,其中所述多元醇混合物的含量为40wt%至60wt%,基于所有组分的总重量而言。
10、如权利要求1所定义的方法,其中所述接枝聚合物分散系在25℃下的平均粘度为2000至15,000cP,固体含量为40至60%,基于分散系的总重量而言。
11、如权利要求1所定义的方法,其中每摩尔所述多元醇混合物中含有0.001至0.09摩尔不饱和度。
12、稳定的低粘度、高固体含量接枝聚合物分散系的制备方法,所述方法包括在有效量反应慢化剂和自由基引发剂的存在下,在多元醇混合物中就地聚合至少一种烯属不饱和的单体,每摩尔所述多元醇混合物中含有0.001至0.09摩尔诱导不饱和度,其中所述自由基引发剂包含1,1-双(叔戊基过氧化)环己烷或1,1-双(叔戊基过氧化)环己烷与叔戊基过氧化(2-乙基己酸酯)的混合物。
13、如权利要求12所定义的方法,其中所述烯属不饱和的单体的含量为25wt%至70wt%,基于所有组分的总重量而言。
14、如权利要求12所定义的方法,其中所述烯属不饱和的单体或单体混合物的含量为40wt%至60wt%,基于所有组分的总重量而言。
15、如权利要求12所定义的方法,其中所述自由基引发剂的含量为0.1wt%至3.0wt%,基于所述烯属不饱和的单体的重量而言。
16、如权利要求12所定义的方法,其中所述自由基引发剂的含量为0.3wt%至1.0wt%,基于所述烯属不饱和的单体的重量而言。
17、如权利要求12所定义的方法,其中所述自由基引发剂包含叔戊基过氧化(2-乙基己酸酯)与1,1-双(叔戊基过氧化)环己烷的掺合物,其中叔戊基过氧化(2-乙基己酸酯)与1,1-双(叔戊基过氧化)环己烷的重量比为1∶10至1∶2。
18、如权利要求17所定义的方法,其中该重量比是1∶4至1∶3。
19、如权利要求12所定义的方法,其中所述多元醇混合物的含量为30wt%至75wt%,基于所有组分的总重量而言。
20、如权利要求12所定义的方法,其中所述多元醇混合物的含量为40wt%至60wt%,基于所有组分的总重量而言。
21、如权利要求12所定义的方法,其中所述接枝聚合物分散系在25℃下的平均粘度为2000至15,000cP,固体含量为40至60%,基于分散系的总重量而言。
22、如权利要求12所定义的方法,其中所述单体选自由苯乙烯与丙烯腈的掺合物组成的组。
23、如权利要求12所定义的方法,其中所述多元醇混合物包含异构化的含有马来酸酯的大分子单体。
24、如权利要求12所定义的方法,其中所述多元醇混合物包含从含有富马酸酯不饱和度的化合物制备的大分子单体。
25、稳定的低粘度接枝聚合物分散系的制备方法,所述方法包括在自由基引发剂的存在下,在(b)多元醇混合物中聚合(a)至少一种烯属不饱和的单体,(b)包含(1)当量为100至10,000的聚氧化亚烷基聚醚多元醇;和(2)含有有效量诱导不饱和度的大分子单体,其中所述自由基引发剂包含1,1-双(叔戊基过氧化)环己烷或1,1-双(叔戊基过氧化)环己烷与叔戊基过氧化(2-乙基己酸酯)的混合物。
26、如权利要求25所定义的方法,其中所述烯属不饱和的单体或单体混合物的含量为40wt%至60wt%,基于所有组分的总重量而言。
27、如权利要求25所定义的方法,其中所述自由基引发剂的含量为0.3wt%至1.0wt%,基于所述烯属不饱和的单体的重量而言。
28、如权利要求25所定义的方法,其中所述自由基引发剂包含叔戊基过氧化(2-乙基己酸酯)与1,1-双(叔戊基过氧化)环己烷的掺合物,其中叔戊基过氧化(2-乙基己酸酯)与1,1-双(叔戊基过氧化)环己烷的重量比为1∶4至1∶3。
29、如权利要求25所定义的方法,其中所述多元醇混合物的含量为40wt%至60wt%,基于所有组分的总重量而言。
30、如权利要求25所定义的方法,其中每摩尔所述多元醇混合物含有0.001至0.09摩尔不饱和度。
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US09/283,492 | 1999-04-01 | ||
US09/283,492 US6172164B1 (en) | 1999-04-01 | 1999-04-01 | Process for making graft polyols using t-amyl peroxy free radical initiator |
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CN1142956C true CN1142956C (zh) | 2004-03-24 |
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US (1) | US6172164B1 (zh) |
EP (1) | EP1192198B1 (zh) |
JP (1) | JP2002541279A (zh) |
KR (1) | KR20010110479A (zh) |
CN (1) | CN1142956C (zh) |
AT (1) | ATE241654T1 (zh) |
AU (1) | AU4105700A (zh) |
CA (1) | CA2367215C (zh) |
DE (1) | DE60003035T2 (zh) |
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- 1999-04-01 US US09/283,492 patent/US6172164B1/en not_active Expired - Fee Related
-
2000
- 2000-03-16 AT AT00920505T patent/ATE241654T1/de not_active IP Right Cessation
- 2000-03-16 ES ES00920505T patent/ES2199812T3/es not_active Expired - Lifetime
- 2000-03-16 CN CNB008056501A patent/CN1142956C/zh not_active Expired - Fee Related
- 2000-03-16 JP JP2000609477A patent/JP2002541279A/ja not_active Withdrawn
- 2000-03-16 KR KR1020017012531A patent/KR20010110479A/ko not_active Application Discontinuation
- 2000-03-16 CA CA002367215A patent/CA2367215C/en not_active Expired - Fee Related
- 2000-03-16 WO PCT/EP2000/002334 patent/WO2000059971A1/en not_active Application Discontinuation
- 2000-03-16 EP EP00920505A patent/EP1192198B1/en not_active Expired - Lifetime
- 2000-03-16 AU AU41057/00A patent/AU4105700A/en not_active Abandoned
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN106008841A (zh) * | 2015-03-25 | 2016-10-12 | 株式会社Jsp | 复合树脂颗粒及其制造方法 |
CN106008841B (zh) * | 2015-03-25 | 2020-03-31 | 株式会社Jsp | 复合树脂颗粒及其制造方法 |
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Publication number | Publication date |
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ES2199812T3 (es) | 2004-03-01 |
US6172164B1 (en) | 2001-01-09 |
CA2367215A1 (en) | 2000-10-12 |
DE60003035D1 (de) | 2003-07-03 |
AU4105700A (en) | 2000-10-23 |
WO2000059971A1 (en) | 2000-10-12 |
ATE241654T1 (de) | 2003-06-15 |
CA2367215C (en) | 2005-10-04 |
DE60003035T2 (de) | 2004-05-19 |
JP2002541279A (ja) | 2002-12-03 |
CN1347426A (zh) | 2002-05-01 |
KR20010110479A (ko) | 2001-12-13 |
EP1192198A1 (en) | 2002-04-03 |
EP1192198B1 (en) | 2003-05-28 |
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