CN1934153A - 聚氨酯分散体制备中的新溶剂 - Google Patents
聚氨酯分散体制备中的新溶剂 Download PDFInfo
- Publication number
- CN1934153A CN1934153A CNA2005800084773A CN200580008477A CN1934153A CN 1934153 A CN1934153 A CN 1934153A CN A2005800084773 A CNA2005800084773 A CN A2005800084773A CN 200580008477 A CN200580008477 A CN 200580008477A CN 1934153 A CN1934153 A CN 1934153A
- Authority
- CN
- China
- Prior art keywords
- acid
- group
- alkyl
- ring
- glycol
- 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.)
- Pending
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- 239000002904 solvent Substances 0.000 title abstract description 19
- 238000002360 preparation method Methods 0.000 claims abstract description 15
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 76
- -1 alkyl pyrrolidone Chemical compound 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 38
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 32
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- 238000000034 method Methods 0.000 claims description 23
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- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 15
- 239000012948 isocyanate Substances 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 150000002513 isocyanates Chemical class 0.000 claims description 12
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical class [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-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
- 238000009966 trimming Methods 0.000 description 4
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
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- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 150000003863 ammonium salts Chemical class 0.000 description 3
- 229910052728 basic metal Inorganic materials 0.000 description 3
- 150000003818 basic metals Chemical class 0.000 description 3
- UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 150000004985 diamines Chemical group 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 3
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- 238000006460 hydrolysis reaction Methods 0.000 description 3
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- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
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- 125000004122 cyclic group Chemical group 0.000 description 2
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 238000004332 deodorization Methods 0.000 description 2
- WAIJESVQRKHMJR-UHFFFAOYSA-N dibutyltin;2-ethylhexanoic acid Chemical compound CCCC[Sn]CCCC.CCCCC(CC)C(O)=O WAIJESVQRKHMJR-UHFFFAOYSA-N 0.000 description 2
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- 238000004821 distillation Methods 0.000 description 2
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- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
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- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
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- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
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- 125000000468 ketone group Chemical group 0.000 description 2
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- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid group Chemical group C(CCCCCCC(=O)O)(=O)O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 2
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 2
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
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- 235000006408 oxalic acid Nutrition 0.000 description 1
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- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- FHHJDRFHHWUPDG-UHFFFAOYSA-N peroxysulfuric acid Chemical compound OOS(O)(=O)=O FHHJDRFHHWUPDG-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 208000026435 phlegm Diseases 0.000 description 1
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- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
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- 229960000380 propiolactone Drugs 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
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- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
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- 229960002675 xylitol Drugs 0.000 description 1
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- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
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Abstract
N-(环)烷基基吡咯烷酮作为溶剂在制备聚氨酯分散体的方法中的应用。
Description
本发明涉及N-(环)烷基吡咯烷酮作为制备聚氨酯分散体方法中所用的溶剂。
聚氨酯分散体在工业上通常利用称作“预聚物混合技术”的方法来制备。在这种方法中聚氨酯首先在有机溶剂通常N-甲基吡咯烷酮中被制备,所得聚氨酯溶液然后被分散在水中。在其分散在水中的过程中和/或分散在水中之后,随后聚氨酯可具有进一步通过扩链而增加的摩尔质量。
根据所用溶剂的沸点,即使在蒸馏除去的情况下,溶剂仍然或多或少地残留在分散体中,影响聚氨酯分散体的性能。
由于并非所有的溶剂是毒理学上不会招致反对的,因此所用的溶剂应该是尽可能无毒的。
在N-烷基吡咯烷酮中制备聚氨酯以及它们随后的分散一般参考例如US 2004/28826、US 6,437,041、US 6,069,218、US 5,908,895、US 5,760,123、US 5,681,622、US 5,354,808、US 5,308,389、DE 44 13 562和EP-A1 663 412。然而,给定的和所用的溶剂基本上仅是N-甲基吡咯烷酮,EP-A1 663 412中也提到了N-环己基吡咯烷酮。
因此关于在预聚物混合技术中使用N-(环)烷基吡咯烷酮,所引用的文献并没有公开任何技术教导。
US 6,632,858、US 6,455,611、US 5,969,002、US 4,977,207和CH 690 331描述了在N-甲基吡咯烷酮中制备聚氨酯且随后加入更高的N-烷基吡咯烷酮如N-乙基吡咯烷酮作为仅在分散在水中之后的添加剂。更高的N-烷基吡咯烷酮仅被加入到完成的含水分散体中,以便调节最终产物的性能。
以上方法的缺点是分散体的制备需要使用第二溶剂,该溶剂或者是—如果该溶剂比水更易挥发—则必须通过相当大的努力由蒸馏除去,或者是导致了最终产物中不想要的、增加的溶剂含量。
EP-B1 891 399公开了烷基基团中具有8-18个碳原子的N-烷基吡咯烷酮作为混入(与其它化合物一起)聚氨酯的表面活性剂以用于去除涂料。
这里的N-烷基吡咯烷酮并非作为溶剂而是作为表面活性物质。
本发明的目的是提供通过预聚物混合技术来制备聚氨酯分散体所用的溶剂,其对所得聚氨酯分散体的性能具有有益的影响。
本发明的目的是通过一种制备聚氨酯分散体的方法来实现的,该方法包括在具有含2到6个碳原子的(环)烷基基团的N-(环)烷基吡咯烷酮的存在下于分散之前制备聚氨酯。
本文中短语“(环)烷基”用于指代烷基和/或环烷基.
根据本发明适当的N-(环)烷基吡咯烷酮是那些具有脂肪族(开链)或脂环族(脂环的,环的)烃基,优选开链、支化的或未支化的烃基的N-(环)烷基吡咯烷酮,含有2到6个碳原子、优选2到5、更优选2到4、特别是2到3且最特别是2个碳原子。
适当的环烷基的例子是环戊基和环己基。
适当的烷基的例子是乙基、异丙基、正丙基、正丁基、异丁基、仲丁基、叔丁基和正己基。
优选的基团是环己基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基、叔丁基,特别优选乙基和正丁基,非常特别优选乙基。
基于聚氨酯,N-(环)烷基吡咯烷酮的量一般是1-100重量%,优选10-100重量%。
根据本发明所用的N-(环)烷基吡咯烷酮当然也可以以与一种或多种其它适当溶剂的混合物的形式来使用。
根据本发明含水的聚氨酯分散体通过如下步骤来制备:
I.通过使下列物质反应
a)至少一种具有4到30个碳原子的多官能异氰酸酯,
b)二醇,其中
b1)10到100mol%,基于二醇(b)的总量,具有500到5000的
分子量和
b2)0到90mol%,基于二醇(b)的总量,具有60到500g/mol的
分子量,
c)如果适当,除了二醇(b)之外,另外的多官能化合物,其含有为醇
羟基基团或者伯或仲胺基团的反应性基团以及
d)除了单体(a)、(b)和(c)之外的单体,其含有至少一个异氰酸酯基团
或者至少一个与异氰酸酯反应的基团,额外地带有至少一个亲水
基团或者一个潜在亲水基团由此使得聚氨酯可分散在水中,
以在N-(环)烷基吡咯烷酮存在的情况下形成聚氨酯和
II.随后将聚氨酯分散在水中
III.如果适当,在步骤II之后或者在步骤II的过程中,可加入聚胺。
适当的单体(a)包括通常用于聚氨酯化学中的聚异氰酸酯,例如脂肪族的、芳香族的和脂环族的二异氰酸酯和多异氰酸酯,脂肪族烃基含有例如4到12个碳原子,脂环族或者芳香族烃基含有例如6到15个碳原子或者芳脂族烃基含有例如7到15个碳原子,具有至少1.8、优选1.8到5且更优选2到4的NCO官能度,还有它们的异氰尿酸酯、缩二脲、脲基甲酸酯和(脲二酮)uretdione。
二异氰酸酯优选具有4到20个碳原子的异氰酸酯。常用的二异氰酸酯的例子是脂肪族二异氰酸酯如四亚甲基二异氰酸酯,六亚甲基二异氰酸酯(1,6-二异氰酸酯己烷),八亚甲基二异氰酸酯,十亚甲基二异氰酸酯,十二亚甲基二异氰酸酯,十四亚甲基二异氰酸酯,赖氨酸二异氰酸酯的酯,四甲基亚二甲苯基二异氰酸酯,三甲基己烷二异氰酸酯或者四甲基己烷二异氰酸酯,脂环族二异氰酸酯例如1,4-、1,3-或1,2-二异氰酸酯环己烷,4,4’-或2,4’-二(异氰酸酯环己基)甲烷的顺/顺、反/反、顺/反异构体,1-异氰酸酯-3,3,5-三甲基-5-(异氰酸酯甲基)环己烷(异佛尔酮二异氰酸酯),2,2-双(4-异氰酸酯环己基)丙烷,1,3-或者1,4-双(异氰酸酯甲基)环己烷或2,4-或2,6-二异氰酸酯-1-甲基环己烷,和芳香族二异氰酸酯如2,4-或2,6-亚甲苯基二异氰酸酯和它们的异构体混合物,间-或者对-亚二甲苯基二异氰酸酯,2,4’-或4,4’-二异氰酸酯二苯基甲烷和它们的异构体混合物,1,3-或1,4-亚苯基二异氰酸酯,1-氯代-2,4-亚苯基二异氰酸酯,1,5-亚萘基二异氰酸酯,二亚苯基4,4’-二异氰酸酯,4,4’-二异氰酸酯-3,3’-二甲基二苯基,3-甲基二苯基甲烷4,4’-二异氰酸酯,1,4-二异氰酸酯苯或苯基4,4’-二异氰酸酯。
也可以存在所述二异氰酸酯的混合物。
优选脂肪族和脂环族二异氰酸酯,特别优选异佛尔酮二异氰酸酯,六亚甲基二异氰酸酯,间-四甲基亚二甲苯基二异氰酸酯(m-TMXDI)和1,1-亚甲基双[4-异氰酸酯]环己烷(H12MDI)。
适当的聚异氰酸酯包括含有异氰尿酸酯基团的聚异氰酸酯,uretdione二异氰酸酯,含有缩二脲基团的聚异氰酸酯,含有尿烷基团或者脲基甲酸酯基团的聚异氰酸酯,含有二嗪三酮(oxadiazinetrione)基团的聚异氰酸酯,直链或支化的C4-C20-亚烷基二异氰酸酯、总共具有6到20个碳原子的二异氰酸酯或者总共具有8到20个碳原子的芳香族二异氰酸酯的uretonimine改性的聚异氰酸酯,或者它们的混合物。
可被使用的二异氰酸酯和聚异氰酸酯具有10到60重量%的异氰酸酯基团(如NCO计算,分子量=42)含量,基于二异氰酸酯和聚异氰酸酯(混合物),更优选15到60重量%,非常优选20到55重量%。
优选脂肪族和/或脂环族二异氰酸酯和聚异氰酸酯,分别例如上述的脂肪族和脂环族二异氰酸酯,或者它们的混合物。
优选
1)含有异氰尿酸酯基团且由芳香族、脂肪族和/或脂环族二异氰酸酯形成的聚异氰酸酯。本文中特别优选相应的脂肪族和/或脂环族异氰酸酯-异氰尿酸酯,特别是基于六亚甲基二异氰酸酯和异佛尔酮二异氰酸酯的那些物质。存在的异氰尿酸酯特别是三异氰酸酯烷基或者三异氰酸酯环烷基异氰尿酸酯,它们表示二异氰酸酯的环状三聚体,或者是与它们的含有多于一个异氰尿酸酯环的同系物的混合物。异氰酸酯-异氰尿酸酯一般具有10到30重量%、特别是15到25重量%的NCO含量,且平均NCO官能度为3到4.5。
2)具有芳香族、脂肪族和/或脂环族连接的异氰酸酯基团、优选Uretdione脂肪族和/或脂环族连接的异氰酸酯基团的Uretdione二异氰酸酯,特别是那些从六亚甲基二异氰酸酯或者异佛尔酮二异氰酸酯衍生得到。
Uretdione二异氰酸酯是二异氰酸酯的环状二聚产物。配方中Uretdione二异氰酸酯可作为唯一成分被使用或者与其它聚异氰酸酯、特别是1)中给定的聚异氰酸酯的混合物形式被使用。
3)含有缩二脲基团且具有芳香族、脂环族和/或脂肪族、优选脂环族和/或脂肪族连接的异氰酸酯基团的聚异氰酸酯,特别是三(6-异氰酸酯己基)缩二脲或者他与更高同系物的混合物。这些含有缩二脲基团的聚异氰酸酯一般具有18到22重量%的NCO含量,且平均NCO官能度为3到4.5。
4)含有尿烷和/或脲基甲酸酯基团且具有芳香族、脂肪族和/或脂环族、优选脂肪族和/或脂环族连接的异氰酸酯基团的聚异氰酸酯,如可通过如使过量的六亚甲基二异氰酸酯或者异佛尔酮二异氰酸酯与多元醇如三羟甲基丙烷、新戊二醇、季戊四醇、1,4-丁二醇、1,6-己二醇、1,3-丙二醇、乙二醇、二甘醇、甘油、1,2-二羟基丙烷或者它们的混合物反应而得到的。这些含有尿烷和/或脲基甲酸酯基团的聚异氰酸酯一般具有12到20重量%的NCO含量,且平均NCO官能度为2.5到3。
5)含有二嗪三酮基团的聚异氰酸酯,优选由六亚甲基二异氰酸酯或者异佛尔酮二异氰酸酯衍生得到的。这种含有二嗪三酮基团的聚异氰酸酯可由二异氰酸酯和二氧化碳来制备。
Uretonimine-改性的聚异氰酸酯。
6)聚异氰酸酯1)到6)可以混合物的形式被使用,适当时包括与二异氰酸酯的混合物。
这些异氰酸酯的特别有意义的混合物是二异氰酸酯甲苯和二异氰酸酯二苯基甲烷的各自结构同分异构体的混合物,特别适合的是由20mol%2,4-二异氰酸酯甲苯和80mol%2,6-二异氰酸酯甲苯组成的混合物。特别有利的是芳香族异氰酸酯如2,4-二异氰酸酯甲苯和/或2,6-二异氰酸酯甲苯与脂肪族或脂环族异氰酸酯如六亚甲基二异氰酸酯或者IPDI的混合物,脂肪族的与芳香族异氰酸酯的优选混合比例是4∶1到1∶4。
作为化合物(a)也可能使用除了自由异氰酸酯基团之外,还带有被封闭的异氰酸酯基团如uretdione或者尿烷基团的异氰酸酯。
如果合适也可以使用那些只带有一个异氰酸酯基团的异氰酸酯。一般来说它们的分数不超过10摩尔%,基于单体的总摩尔量。单异氰酸酯通常带有其它官能团如烯烃基团或者羰基基团并用作引入聚氨酯的官能团,这使得其被分散和/或交联或者进行另外的聚合物类似的反应。适用于这个目的单体包括如异丙烯基-α,α-二甲基苯甲基异氰酸酯(TMI)。
理想地合适的二醇(b)是那些具有约500至5000、优选约1000至3000g/mol的相对高分子量的二醇(b1)。
特别地,二醇(b1)是聚酯多元醇,它们描述在例如UllmannsEncyklopdie der technischen Chemie,4th Edition,Vol.19,pp.62 to 65中。优选使用通过使二元醇与二元羧酸反应得到的聚酯多元醇。代替游离的聚羧酸,也可以使用相应的聚羧酸酸酐或者相应的更低醇的聚羧酸酯,或者它们的混合物,以制备聚酯多元醇。聚羧酸可以是脂肪族的、脂环族的、芳脂族的、芳香族的或者杂环的并可以未取代的或者被如卤素原子取代的,和/或饱和或不饱和的。例子是辛二酸、壬二酸、邻苯二甲酸和间苯二甲酸,邻苯二甲酸、四氢邻苯二甲酸、六氢邻苯二甲酸、四氯邻苯二甲酸、内亚甲基四氢邻苯二甲酸、戊二酸和马来酸酸酐,马来酸、富马酸和二聚脂肪酸。优选通式为HOOC-(CH2)y-COOH的二羧酸,其中y是1到20的数,优选2到20的偶数,例子如琥珀酸、己二酸、癸二酸和十二烷二羧酸。
适当的多元醇的例子是乙二醇,1,2-丙二醇,1,3-丙二醇,1,3-丁二醇,1,4-丁二醇,1,4-丁炔二醇,1,5-戊二醇,新戊二醇,双(羟基甲基)环己烷如1,4-双(羟基甲基)环己烷,2-甲基-1,3-丙二醇以及此外的二乙二醇,三甘醇,四甘醇,聚乙二醇,二丙二醇,聚丙二醇,二丁二醇和聚丁二醇。优选新戊二醇和通式为HO-(CH2)x-OH的醇,其中x是1到20的数,优选2到20的偶数。这种醇的例子是乙二醇,1,4-丁二醇,1,6-己二醇,1,8-辛二醇,和1,12-十二烷二醇。
还适当的是聚碳酸酯二醇,正如例如通过使光气与过量的被称为作为聚酯多元醇合成成分的低分子量醇反应而得到的。
基于内酯的聚酯二醇也是适当的,这些是内酯的均聚物或者共聚物,优选内酯与适当的二官能起始物分子的羟基终端的加合物。适当的内酯优选是那些由通式为HO-(CH2)z-COOH的羟基羧酸衍生得到的,其中z是1到20,优选3到19的奇数。例子是ε-己内酯,β-丙内酯,γ-丁内酯和/或甲基ε-己内酯,以及它们的混合物。适当的起始物成分的例子是以上引用作为聚酯多元醇合成成分的低分子量二元醇。特别优选ε-己内酯的对应聚合物。较低的聚酯二醇或者聚醚二醇也可用作制备内酯聚合物的起始物。也可应用与内酯相应的羟基羧酸所对应的、化学等价的缩聚物,来代替内酯的聚合物。
另外适当的单体(b1)是聚醚二醇。它们特别是通过以下反应得到的:在例如BF3存在下,环氧乙烷、环氧丙烷、环氧丁烷、四氢呋喃、氧化苯乙烯或者表氯醇与其自身的加聚,或者这些化合物,单独地或者以混合物的形式或者先后地,加成反应到含有活性氢的起始物成分上,这些起始物成分例如醇或者胺,例子是水,乙二醇,1,2-丙二醇,1,3-丙二醇,2,2-双(4-羟基二苯基)丙烷或者苯胺。特别优选分子量为500到5000g/mol、特别是为1000到4500g/mol的聚四氢呋喃。
聚酯二醇和聚醚二醇也可以0.1∶1到1∶9的比例以混合物使用。
不仅二醇(b1)可用作二醇(b),分子量为约50到500、优选为60到200g/mol的低分子量二醇(b2)也可用作二醇(b)。
用作单体(b2)的化合物特别是制备聚酯多元醇所提及的短链烷二醇的合成成分,优选具有2到12个碳原子的和偶数碳原子的未支化二醇,以及1,5-戊二醇和新戊二醇。
基于二醇(b)的总量,二醇(b1)的比例优选10到100mol%,基于二醇(b)的总量,二醇(b2)的比例优选0到90mol%。特别优选的比例是0.2∶1到5∶1,特别是0.5∶1到2∶1。
与二醇(b)不同的单体(c),一般用于交联或者扩链。它们通常是具有多于两个官能度的非芳香族醇,具有2或更多伯和/或仲氨基基团的胺,以及既带有一个或多个醇羟基基团也带有一个或多个伯和/或仲氨基基团的化合物。
可用于使一定程度的交联或支化发生的、具有多于两个官能度的醇,例如是三羟甲基丁烷、三羟甲基丙烷、三羟甲基乙烷、季戊四醇、甘油、糖醇、如山梨糖醇、甘露醇、双甘油、苏糖醇、赤藻糖醇、福寿糖醇(核醣醇)、阿拉伯糖醇(lyxitol)、木糖醇、卫矛醇(半乳糖醇)、麦芽糖醇或Isomalt、或者糖。
还适当的是除了羟基基团之外还带有另外的与异氰酸酯反应基团的单醇,如具有一个或多个伯和/或仲氨基基团的单醇,其一个例子是单乙醇胺。
具有两个或多个伯和/或仲氨基基团的聚胺可用于预聚物混合技术中,特别是当在水存在的情况下发生扩链和/或交联(步骤III)时,因为与醇或者水相比,胺通常与异氰酸酯更快地反应。当需要交联聚氨酯或高分子量聚氨酯的含水分散体时,这通常是必要的。在这样的情况下所采用的方法是制备含有异氰酸酯基团的预聚物,以在水中快速分散它们并然后通过加入具有两个或多个与异氰酸酯反应的氨基基团的化合物以使它们进行扩链或交联。
适用于这个目的的胺一般是分子量为32至500g/mol,优选60至300g/mol的多官能胺,它们含有至少两个伯氨基、两个仲氨基或者一个伯氨基和一个仲氨基。其例子是二胺如二氨基乙烷,二氨基丙烷,二氨基丁烷,二氨基己烷,哌嗪,2,5-二甲基哌嗪,氨基-3-氨甲基-3,5,5-三甲基环己烷(异佛尔酮二胺,IPDA),4,4’-二氨基-二环己基甲烷,1,4-二氨基环己烷,氨乙基乙醇胺,肼,水合肼,或者三胺如二亚乙基三胺或者1,8-二氨基-4-氨基-甲基辛烷或者更高的胺如三亚乙基四胺,四亚乙基五胺或者聚合的胺如聚亚乙基胺,与氢化聚丙烯腈或者至少部分地水解的聚-N-亚乙基甲酰胺,每种情况下各具有最高2000、优选最高1000g/mol的分子量。
胺也可以封闭的形式使用,如以相应的酮亚胺(参见,例如CA-1 129 128),甲酮连氮(参见例如US-A 4 269 748)或者胺盐(参见US-A 4 292 226)的形式。正如US-A 4 192 937中实施例所用的,唑烷也是封闭的聚胺,其可用于制备用于扩链预聚物的聚氨酯。当使用这种封闭的聚胺时,它们通常在没有水的情况下与预聚物混合并且该混合物随后与分散体水或其一部分混合,使得相应的聚胺通过水解被释放。
优选使用二胺与三胺的混合物,特别优选异佛尔酮二胺和二亚乙基三胺的混合物。
聚胺的分数可最高10、优选最高8mol%且更优选最高5mol%,基于组分(b)和(c)的总量。
步骤I中制备的聚氨酯可含有一般最高10、优选最高5重量%的未反应的NCO基团。
步骤I制备的聚氨酯中NCO基团与聚胺中伯与仲氨基基团之和的摩尔比率通常在步骤III中被选择以使其在3∶1和1∶3之间、优选2∶1和1∶2之间、更优选1.5∶1和1∶1.5之间且非常优选1∶1。
用于链终止的另外一种可能性是使用少量—即,优选,基于组分(b)和(c),少于10mol%的量—的单醇。它们主要用于限制聚氨酯的分子量。例子是甲醇、乙醇、异丙醇、正丙醇、正丁醇、异丁醇、仲丁醇、叔丁醇、乙二醇单甲醚、乙二醇单乙醚、1,3-丙二醇单甲醚、正己醇、庚醇、正辛醇、正癸醇、正十二烷醇(月桂醇)和2-乙基己醇。
为了使聚氨酯可分散在水中,它们不仅由组分(a)、(b)和(c)合成,而且还由组分(d)形成,该组分(d)不同于组分(a)、(b)和(c)并带有至少一个异氰酸酯基团或者至少一个与异氰酸酯反应的基团,且另外含有至少一个亲水基团或者可转化成亲水基团的基团。在下文中,术语“亲水基团或者潜在亲水基团”被简写为“(潜在)亲水基团”。与用于构建聚合物主链的单体的官能团相比,该(潜在)亲水基团与异氰酸酯的反应要慢得多。该(潜在)亲水基团可以是非离子的或者优选离子的即阳离子或阴离子的、亲水基团,或者可以是潜在离子的亲水基团,特别优选阴离子亲水基团或者潜在阴离子亲水基团。
通常设定具有(潜在)亲水基团的组分作为组分(a)、(b)、(c)和(d)总量一小部分的比例,使得(潜在)亲水基团的摩尔数量,基于所有单体(a)到(d)的重量数量,为30到1000、优选50到500且更优选80到300mmol/kg。
适当的非离子亲水基团的例子包括优选由5到100、更优选10到80重复的环氧乙烷单元组成的混合的或者纯的聚乙二醇醚。聚乙二醇醚也可含有环氧丙烷单元。此时环氧丙烷单元不应该超过50重量%、优选30重量%,基于混合物的聚乙二醇醚的重量。
环氧丙烷单元的量通常是0到10重量%,优选0到6重量%,基于所有组分(a)到(d)的总重量。
含有非离子亲水基团的优选单体是带有终端醚化的聚乙二醇基的二异氰酸酯和聚乙二醇。这种类型的二异氰酸酯以及它们的制备方法在专利US 3 905 929和US 3 920 598中给出了。
离子亲水基团特别是,阴离子基团如以其碱金属或铵盐形式的磺酸盐、羧酸盐和磷酸盐基团,以及阳离子基团如铵基团,特别是质子化的叔氨基基团或者季铵基团。
含有潜在阴离子基团的适当单体通常是脂肪族的、脂环族的、芳脂族的或芳香族的单羟基羧酸和二羟基羧酸,它们带有至少一个醇羟基基团或一个伯或仲氨基基团。
这样的化合物例如由通式表示:
RG-R4-DG
其中
RG是至少一个与异氰酸酯反应的基团,
DG是至少一个活泼的分散基团和
R4是含有1到20个碳原子的脂肪族、脂环族或芳香族基团。
RG的例子是-OH,-SH,-NH2或-NHR5,其中R5可以是甲基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基、叔丁基、环戊基或环己基。
这种成分优选例如巯基乙酸、巯基丙酸、硫醇乳酸、巯基琥珀酸、甘氨酸、亚氨基二乙酸、肌氨酸、丙氨酸、β-丙氨酸、亮氨酸、异亮氨酸、氨基丁酸、羟基乙酸、羟基特戊酸、乳酸、羟基琥珀酸、羟基癸酸、二羟甲基丙酸、二羟甲基丁酸、乙二胺三乙酸、羟基十二烷酸、羟基十六烷酸、12-羟基硬脂酸、氨基萘羧酸、羟基乙烷磺酸、羟基丙烷磺酸、巯基乙烷磺酸、巯基丙烷磺酸、氨基甲烷磺酸、牛磺酸、氨基丙烷磺酸以及它们的碱金属、碱土金属或铵盐,特别优选所述的单羟基羧酸和单羟基磺酸以及单氨基羧酸和单氨基磺酸。
非常特别优选二羟基烷基羧酸,特别是具有3到10个碳原子的那些,以及如US-A 3 412 054中所描述的。特别优选下述通式的化合物
HO-R1-CR3(COOH)-R2-OH
其中R1和R2各为C1-至C4-亚烷基(alkanediyl)单元且R3是C1-至C4-烷基单元。特别优选二羟甲基丁酸,尤其是二羟甲基丙酸(DMPA)。
也适合的是相应的二羟基磺酸和二羟基膦酸如2,3-二羟基丙烷膦酸以及其中至少一个羟基基团被氨基基团代替的相应的酸,例子为下式的那些
H2N-R1-CR3(COOH)-R2-NH2
其中R1、R2和R3可以具有与以上限定的相同的意义。
其它适当的是分子量大于500到10000g/mol并具有至少2个羧酸酯基团的二羟基化合物,它们在DE-A 4 140 486中已经描述。它们可通过使二羟基化合物与四羧酸二酐如均苯四酸二酐或环戊烷四羧酸二酐以2∶1至1.05∶1的摩尔比进行加聚反应而得到。优选适合的二羟基化合物是作为扩链剂列出的单体(b2)以及二醇(b1)。
潜在离子的亲水基团特别是,可通过简单的中和、水解或季铵化反应而被转化成上述离子亲水基团的那些,由此例子是酸基团、酸酐基团或者叔氨基基团。
例如在Ullmanns Ecyklopdie der technischen Chemie,4th edition,Volume 19,pp.311-313和如DE-A 1 495 745中详细描述了离子单体(d)或潜在离子单体(d)。
具有叔氨基基团的单体特别是具有特定实践意义的潜在阳离子单体(d),例子如下:三(羟基烷基)胺,N,N’-二(羟基烷基)胺,N-羟基烷基-二烷基胺,三(氨基烷基)胺,N,N’-二(氨基烷基)烷基胺和N-氨基烷基-二烷基胺,由2到6个碳原子彼此独立形成的这些叔胺的烷基和亚烷基单元。还适当的是含有叔氮原子和优选两个终端羟基基团的聚醚,如可通过以常规方式烷氧基化例如具有两个连接到胺氮原子上的氢原子的胺(例子是甲基胺,苯胺)与N,N’-二甲基肼而得到的。这种聚醚一般具有500和6000g/mol之间的分子量。
这些叔胺,或者与酸优选强无机酸如磷酸、硫酸或盐酸或者强有机酸如甲酸、乙酸或乳酸作用,或者通过与适当的季铵化剂如C1至C6烷基卤化物例如溴化物或氯化物、或二-C1到C6烷基硫酸酯或二-C1到C6烷基碳酸酯反应,而被转化成铵盐。
具有与异氰酸酯反应的氨基基团的适当单体(d)包括氨基羧酸如赖氨酸、β-丙氨酸,在DE-A2034479中说明的、脂肪族二伯二胺与α,β-不饱和羧酸如N-(2-氨基乙基)-2-氨基乙烷羧酸的加成产物,还有由2到6个碳原子构成亚烷基单元的对应的N-氨基烷基氨基烷基羧酸。
当使用含有潜在离子基团的单体时,在异氰酸酯聚合加成之前或过程中,但优选其聚合加成之后,它们可被转化成离子形式,因为离子单体通常只是非常少地溶解在反应混合物中。特别优选阴离子亲水基团是碱金属或铵离子作为反离子的它们的盐的形式。
这些特定的化合物中,优选羟基羧酸,特别优选二羟基烷基酸酸,非常优选α,α-二(羟基甲基)羧酸,特别是二羟甲基丁酸和二羟甲基丙酸,尤其是二羟甲基丙酸。
在一个可选择的实施方式中,聚氨酯可以不仅含有非离子亲水基团,还含有离子的亲水基团,优选同时含有非离子亲水基团和阴离子亲水基团。
在聚氨酯化学领域中,如何通过选择共反应单体的分数(fraction)并通过选择每摩尔反应性官能团的算术平均数目来调整聚氨酯的分子量是常识。
通常选择组分(a)、(b)、(c)和(d)以及它们各自的摩尔数量使得比率A∶B为0.5∶1到2∶1,优选0.8∶1到1.5,特别优选0.9∶1到1.2∶1。非常优选比率A∶B尽可能地接近1∶1,其中
A)是异氰酸酯基团的摩尔数量且
B)为羟基基团的摩尔数量与在加成反应中能够与异氰酸酯反应的官能团的摩尔数量的和。
除了组分(a)、(b)、(c)和(d)之外,使用只含有一个反应性基团的单体,其量通常最高15mol%,优选最高8mol%,基于(a)、(b)、(c)和(d)的总数量。
组分(a)到(d)的加聚通常在20到180℃的反应温度、优选50到150℃,在大气压力下发生。
所需的反应时间通常从几分钟到几个小时。在聚氨酯化学领域中,反应时间如何被多种参数如温度、单体浓度和单体反应性影响是已知的。
为了加速二异氰酸酯的反应,可以使用常规的催化剂。原则上适当的那些是聚氨酯化学中常用的所有催化剂。
这些是,例如,有机胺,特别是叔脂肪族、脂环族或芳香族的胺,和/或路易斯酸的有机金属化合物。适当的路易斯酸的有机金属化合物的例子包括锡化合物,如有机羧酸的锡(II)盐如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)和月桂酸锡(II),以及有机羧酸的二烷基锡(IV)盐,如二乙酸二甲基锡、二乙酸二丁基锡、二丁酸二丁基锡、双(2-乙基己酸)二丁基锡、二月桂酸二丁基锡、马来酸二丁基锡、二月桂酸二辛锡和二乙酸二辛锡。金属络合物如铁、钛、铝、锆、镁、镍和钴的乙酰丙酮化物也是可能的。另外的金属催化剂在Blank等人的Progress in Organic Coatings,1999,第35卷,第19-29页中有所描述。
优选的路易斯酸的有机金属化合物是双乙酸二甲基锡、二丁酸二丁基锡、双(2-乙基己酸)二丁基锡、二月桂酸二丁基锡、二月桂酸二辛基锡、乙酰丙酮化锆和2,2,6,6-四甲基-3,5-庚烷二酮化锆。
还有铋和钴催化剂,以及铯盐,可用作催化剂。适当的铯盐包括其中使用如下阴离子的那些化合物:F-、Cl-、ClO-、ClO3 -、ClO4 -、Br-、I-、IO3 -、CN-、OCN-、NO2 -、NO3 -、HCO3 -、CO3 2-、S2-、SH-、HSO3 -、SO3 2-、HSO4 -、SO4 2-、S2O2 2-、S2O4 2-、S2O5 2-、S2O6 2-、S2O7 2-、S2O8 2-、H2PO2-、H2PO4 -、HPO4 2-、PO4 3-、P2O7 4-、(OCnH2n+1)-、(CnH2n-1O2)-、(CnH2n-3O2)-和(Cn+1H2n-2O4)2-,n表示1到20的数。
优选羧酸铯,其中阴离子符合式(CnH2n-1O2)-和(Cn+1H2n-2O1)2-,n为1到20。特别优选含有通式为(CnH2n-1O2)-的单羧酸阴离子的铯盐,其中n表示1到20的数。本文中特别应提到甲酸盐、乙酸盐、丙酸盐、己酸盐和2-乙基己酸盐。
适当的聚合装置包括搅拌槽,特别是当使用溶剂以确保低粘度和有效的除去热时。
如果反应在大的适当的设备中进行,则由于通常高的粘度和通常短的反应时间,特别包括挤出机,尤其是自清洁多螺杆挤出机。
在预聚物混合技术中带有异氰酸酯基团的预聚物首先被制备。这种情况下,选择组分(a)到(d)使得以上限定的比率A∶B高于1.0至3,优选1.05至1.5。预聚物首先分散在水中并通过使异氰酸酯基团与带有多于2个与异氰酸酯反应的氨基基团的胺反应而同时和/或随后交联,或者用带有多于2个与异氰酸酯反应的氨基基团的胺来扩链预聚物。扩链也可在没有胺加入时加入。在这种情况下异氰酸酯基团水解成胺基团,与预聚物中残留的异氰酸酯基团反应并由此延长链。
利用MalvernAutosizer 2 C通过动态光散射测定的根据本发明制备的分散体的平均粒度(z-均)对本发明并不是关键的,通常<1000nm,优选<500nm,更优选<200nm且非常优选在20和低于200nm之间。
分散体通常具有10到75%的固体含量,优选20到65%,按重量计算,且具有10到500mPas的粘度(在20℃的温度和250s-1的剪切速率下测定)。
对于某些应用,通过例如稀释分散体从而将分散体调整到不同的固体含量、优选较低的固体含量,可能是合理的。
根据本发明制备的分散体可另外地与所引用应用中典型的其它成分混合,例如表面活性剂、去污剂、染料、颜料、色转移抑制剂和荧光增白剂。
如果需要,在制备之后,分散体可进行物理除臭。
物理除臭可涉及到利用蒸汽、含氧气体优选空气、氮气或超临界二氧化碳,例如在如DE-B 12 48 943所述的搅拌容器中,或者在如DE-A 196 21 027所述的逆流塔中,洗提分散体。
制备聚氨酯时通常选择本发明的N-(环)烷基吡咯烷酮的量使得最终分散体中的分数不超过30%、优选不多于25%、更优选不多于20%且非常优选不多于15%,按重量计算。
本发明的含水聚氨酯配方有利地适用于涂布和粘合基底。适当的基底是木材,薄木片,纸,卡纸,纸板,纺织品,皮革,无纺织品,塑料、玻璃、陶瓷、矿物建筑材料和未涂层或涂层的金属的表面。它们用于例如在制备膜或薄片时,用于浸渍纺织品或皮革,作为分散剂,作为颜料研磨剂,作为底漆,作为粘合促进剂,作为疏水化剂,作为洗衣去垢剂添加剂或作为化妆品配方的添加剂,或者用于制备模制物或者制备水凝胶。
在它们用作涂料的情形中,聚氨酯分散体可特别用作汽车整修或大型车辆整修领域中的底漆,表面涂料,着色外涂层材料和clearcoat材料。该涂料特别适用于需要特别高的应用可靠性、外部风化稳定性、光学质量、耐溶剂性、耐化学性和耐水性的应用中,如汽车汽车整修或大型车辆整修。
本发明的、在N-(环)烷基吡咯烷酮存在的情况下制备的聚氨酯产生了至少一个下面的优点:
-减少溶剂的需要。
-分散体更易于通过喷射或通过喷嘴施涂,因为在喷射工具上的结垢或者污染减少了。
-例如比N-甲基吡咯烷酮有更低的毒性。
-预聚物溶液具有更低的毒性。
-聚氨酯分散体的流变学的改善。
-基底或添加剂的润湿行为的改善。
-暴露于光和/或热下时更少泛黄。
-分散体的更强的抗冻性。
-所得膜的改善的柔性、特别是较低温度的挠性。
-所得膜的更好的光泽。
正如现有技术已知的,随后加入的N-烷基吡咯烷酮仅用于调整最终分散体的物理参数,然而本发明的、在N-(环)烷基吡咯烷酮存在的情况下制备的聚氨酯产生了不可能通过随后加入而实现的、与制备聚氨酯相关的优点。对这点而言一种可能的原因可能是本发明制备的聚氨酯通过膨胀例如整个横截面上而吸收了N-(环)烷基吡咯烷酮,而对于随后加入,最多只有表面吸收发生。
本发明还提供了包括至少一种本发明聚合物分散体的涂料组合物,还有用该涂料组合物涂布的物件。
除非另外声明,否则本说明书中所用的ppm图和百分比涉及的是重量百分比和按重量计算的ppm。
Claims (14)
1.一种制备聚氨酯分散体的方法,包括在N-(环)烷基吡咯烷酮存在的情况下在分散之前制备聚氨酯,该N-(环)烷基吡咯烷酮具有含2到6个碳原子的(环)烷基。
2.根据权利要求1的方法,包括以下步骤:
I.通过在N-(环)烷基吡咯烷酮存在的情况下使下列物质反应
a)至少一种具有4到30个碳原子的多官能异氰酸酯,
b)以下的二醇
b.1)10到100mol%,基于二醇(b)的总量,具有500到5000的分子量和
b.2)0到90mol%,基于二醇(b)的总量,具有60到500g/mol的分子量,
c)如果适当,除了二醇(b)之外,另外的多官能化合物,其含有为醇羟基基团或者伯或仲胺基团的反应性基团以及
d)除了单体(a)、(b)和(c)之外的单体,其含有至少一个异氰酸酯基团或者至少一个与异氰酸酯反应的基团,额外地带有至少一个亲水基团或者一个潜在亲水基团从而使得聚氨酯可分散在水中,来制备聚氨酯和
II.随后将聚氨酯分散在水中
III.如果适当,在步骤II之后或者在步骤II的过程中,可加入聚胺。
3.根据权利要求2的方法,其中至少一种羟基羧酸用作成分(d)。
4.根据权利要求3的方法,其中至少一种二羟基烷基羧酸用作成分(d)。
5.根据权利要求3的方法,其中至少一种α,α-二(羟基甲基)羧酸用作成分(d)。
6.根据权利要求3的方法,其中二羟甲基丁酸和/或二羟甲基丙酸用作成分(d)。
7.根据权利要求3的方法,其中二羟甲基丙酸用作成分(d)。
8.根据上述权利要求中任一项的方法,其中非离子亲水和离子亲水基团都用作成分(d)。
9.根据上述权利要求中任一项的方法,其中在至少一种铯盐存在的情况下制备聚氨酯。
10.根据上述权利要求中任一项的方法,其中(环)烷基是环己基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基或叔丁基。
11.根据上述权利要求中任一项的方法,其中(环)烷基是乙基或正丁基。
12.根据上述权利要求中任一项的方法,其中N-(环)烷基吡咯烷酮是N-乙基吡咯烷酮。
13.根据上述权利要求中任一项的聚氨酯分散体的用途,用于涂布或粘接木材、薄木片、纸、卡纸、纸板、纺织品、皮革、无纺织品、塑料表面、玻璃、陶瓷、矿物建筑材料和未涂层的金属或涂层的金属。
14.具有含2到6个碳原子的(环)烷基的N-(环)烷基吡咯烷酮在聚氨酯制备中的用途。
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CN102459383A (zh) * | 2009-06-10 | 2012-05-16 | 巴斯夫欧洲公司 | 用于生产聚氨酯分散体的新溶剂 |
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CN106459361A (zh) * | 2014-06-10 | 2017-02-22 | 巴斯夫欧洲公司 | 含有酰基吗啉的聚合物分散体 |
CN107207693A (zh) * | 2015-02-06 | 2017-09-26 | 塔明克公司 | 水性聚氨酯分散体 |
CN110799562A (zh) * | 2017-06-26 | 2020-02-14 | 艾德凡斯化学公司 | 使用己内酰胺衍生的溶剂的聚氨酯分散体的方法和组合物 |
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WO2007131929A1 (de) | 2006-05-16 | 2007-11-22 | Basf Se | Verfahren zur kontinuierlichen herstellung von n-ethyl-2-pyrrolidon (nep) |
ATE554743T1 (de) | 2007-09-19 | 2012-05-15 | Bubbles & Beyond Gmbh | Reinigungsmittel zur entfernung von farbschichten von oberflächen, verfahren zur herstellung des mittels und verfahren zur reinigung |
US8796472B2 (en) | 2008-12-04 | 2014-08-05 | Basf Se | Mixtures of itaconic acid or itaconic acid derivatives and primary amines for producing 1,3- and 1,4-alkyl methyl pyrrolidones |
DE102009014380A1 (de) | 2009-03-26 | 2010-10-07 | Bubbles And Beyond Gmbh | Verfahren und Zusammensetzung zum Reinigen von Gegenständen |
DE102010031301A1 (de) | 2009-07-17 | 2011-01-20 | Basf Se | Verwendung von 1,3-Dimethylpyrrolidon und/oder 1,4-Dimethylpyrrolidon |
US8653015B2 (en) * | 2011-04-13 | 2014-02-18 | American Sterilizer Company | Environmentally friendly, multi-purpose refluxing cleaner |
BE1020269A5 (nl) * | 2012-01-17 | 2013-07-02 | Taminco | Gebruik van vervangende oplosmiddelen voor n-methylpyrrolidon (nmp). |
US20160208097A1 (en) | 2015-01-15 | 2016-07-21 | Rohm And Haas Electronic Materials Llc | Polyimide compositions and methods |
ES2743790T3 (es) | 2016-08-24 | 2020-02-20 | Henkel Ag & Co Kgaa | Promoción de la adhesión plástica para adhesivos de poliuretano 2K |
CN110183369A (zh) * | 2019-05-23 | 2019-08-30 | 安徽京控环境技术服务有限公司 | 一种从废脱漆剂中分离提纯n-甲基吡咯烷酮的方法 |
JP2023515360A (ja) * | 2020-02-14 | 2023-04-13 | アンガス ケミカル カンパニー | 低毒性nmp代替物およびその調製方法 |
KR20230085970A (ko) * | 2021-12-07 | 2023-06-15 | 주식회사 비제이바이오켐 | 덱스트린 다당류 폴리머 유도체의 제조방법 |
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US3965350A (en) * | 1972-01-24 | 1976-06-22 | Air Products And Chemicals, Inc. | Dye penetrant method for detecting flows |
DE2250169A1 (de) * | 1972-10-13 | 1974-04-25 | Metallgesellschaft Ag | Verfahren zur entschwefelung technischer brenngase und synthesegase |
US4422906A (en) * | 1981-09-17 | 1983-12-27 | Masami Kobayashi | Process for direct gold plating of stainless steel |
DE3207404A1 (de) * | 1982-03-02 | 1983-09-08 | Metallgesellschaft Ag, 6000 Frankfurt | Verfahren zur entfernung von aromatischen verbindungen aus kohlenwasserstoffen |
DE3704350A1 (de) * | 1987-02-12 | 1988-08-25 | Henkel Kgaa | Wasserverduennbare ueberzugsmittel |
US5777131A (en) * | 1995-11-21 | 1998-07-07 | Basf Corporation | Post manufacture process for improving the properties of lactones and substituted lactams |
DE19636382A1 (de) * | 1996-09-09 | 1998-03-12 | Bayer Ag | Pigmentpräparationen für den Ink-Jet-Druck |
DE19746327C1 (de) * | 1997-10-21 | 1999-04-08 | Herberts & Co Gmbh | Wäßrige Überzugsmittel, ihre Herstellung und Verwendung |
GB9806789D0 (en) * | 1998-03-31 | 1998-05-27 | Zeneca Ltd | Composition |
US5985040A (en) * | 1998-09-21 | 1999-11-16 | Electrochemicals Inc. | Permanganate desmear process for printed wiring boards |
DE10149268A1 (de) * | 2001-10-05 | 2003-04-17 | Basf Ag | Verwendung von vernetzbaren Polyurethan-Blockcopolymeren als Dispergierbinderadditive für Pigmentdruck und die Pigmentfärbung |
US6699829B2 (en) * | 2002-06-07 | 2004-03-02 | Kyzen Corporation | Cleaning compositions containing dichloroethylene and six carbon alkoxy substituted perfluoro compounds |
-
2004
- 2004-03-15 DE DE200410012751 patent/DE102004012751A1/de not_active Withdrawn
-
2005
- 2005-03-14 WO PCT/EP2005/002681 patent/WO2005090447A2/de not_active Application Discontinuation
- 2005-03-14 CN CNA2005800084773A patent/CN1934153A/zh active Pending
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CN102459383A (zh) * | 2009-06-10 | 2012-05-16 | 巴斯夫欧洲公司 | 用于生产聚氨酯分散体的新溶剂 |
CN102459383B (zh) * | 2009-06-10 | 2015-08-26 | 巴斯夫欧洲公司 | 用于生产聚氨酯分散体的溶剂 |
CN103597407A (zh) * | 2011-07-11 | 2014-02-19 | 富士胶片株式会社 | 感光性组合物 |
CN103289712A (zh) * | 2012-02-24 | 2013-09-11 | Jsr株式会社 | 液晶配向剂、液晶配向膜及液晶显示元件 |
CN103289712B (zh) * | 2012-02-24 | 2016-08-24 | Jsr株式会社 | 液晶配向剂、液晶配向膜及液晶显示元件 |
CN106459361A (zh) * | 2014-06-10 | 2017-02-22 | 巴斯夫欧洲公司 | 含有酰基吗啉的聚合物分散体 |
CN107207693A (zh) * | 2015-02-06 | 2017-09-26 | 塔明克公司 | 水性聚氨酯分散体 |
CN107207693B (zh) * | 2015-02-06 | 2021-03-26 | 塔明克公司 | 水性聚氨酯分散体 |
CN110799562A (zh) * | 2017-06-26 | 2020-02-14 | 艾德凡斯化学公司 | 使用己内酰胺衍生的溶剂的聚氨酯分散体的方法和组合物 |
CN110799562B (zh) * | 2017-06-26 | 2022-12-16 | 艾德凡斯化学公司 | 使用己内酰胺衍生的溶剂的聚氨酯分散体的方法和组合物 |
US11542360B2 (en) | 2017-06-26 | 2023-01-03 | Advansix Resins & Chemicals Llc | Methods and compositions for polyurethane dispersions using caprolactam-derived solvents |
US12024584B2 (en) | 2017-06-26 | 2024-07-02 | Advansix Resins & Chemicals Llc | Methods and compositions for polyurethane dispersions using caprolactam-derived solvents |
Also Published As
Publication number | Publication date |
---|---|
WO2005090447A2 (de) | 2005-09-29 |
WO2005090447A3 (de) | 2006-05-04 |
DE102004012751A1 (de) | 2005-10-06 |
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