CN102277081B - 具有改进性能的水可乳化的异氰酸酯 - Google Patents
具有改进性能的水可乳化的异氰酸酯 Download PDFInfo
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- CN102277081B CN102277081B CN201110111349.9A CN201110111349A CN102277081B CN 102277081 B CN102277081 B CN 102277081B CN 201110111349 A CN201110111349 A CN 201110111349A CN 102277081 B CN102277081 B CN 102277081B
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- weight
- acid ester
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- isocyanuric acid
- hexamethylene
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 23
- 239000012948 isocyanate Substances 0.000 title description 14
- 150000002513 isocyanates Chemical class 0.000 title description 14
- 239000000203 mixture Substances 0.000 claims abstract description 48
- -1 isocyanuric acid ester Chemical class 0.000 claims abstract description 42
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 24
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims abstract description 23
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 239000005058 Isophorone diisocyanate Substances 0.000 claims abstract description 13
- 239000003995 emulsifying agent Substances 0.000 claims abstract description 13
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims abstract description 11
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- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 claims description 5
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- 125000000217 alkyl group Chemical group 0.000 claims description 4
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 3
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
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- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
- WSFQLUVWDKCYSW-UHFFFAOYSA-M sodium;2-hydroxy-3-morpholin-4-ylpropane-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)CC(O)CN1CCOCC1 WSFQLUVWDKCYSW-UHFFFAOYSA-M 0.000 description 1
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- 239000001117 sulphuric acid Substances 0.000 description 1
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- 150000003512 tertiary amines Chemical class 0.000 description 1
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- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical compound NC(=O)NC(O)=O AVWRKZWQTYIKIY-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
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
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Abstract
本发明涉及一种制备包含以下组分的混合物的方法:(A)1,6‑己二异氰酸酯(HDI)的异氰脲酸酯和/或缩二脲;(B)1‑异氰酸酯基‑3,5,5‑三甲基‑5‑异氰酸酯基甲基环己烷(IPDI)的异氰脲酸酯;(C)至少一种乳化剂,和(D)任选地溶剂。
Description
技术领域
本发明涉及一种制备水可乳化的异氰酸酯的方法以及它们的用途。
背景技术
水可乳化的多异氰酸酯作为交联剂被加入到水性聚合物分散体中,并且其已经在文献中广泛描述。在水中的乳化性是通过将多异氰酸酯和亲水性分子反应得到的乳化剂和多异氰酸酯混合带来的。
通常使用的亲水性分子包括非离子性亲水分子,例如聚氧化烯醇。
EP-A2 206 059描述了水可分散的多异氰酸酯配方,包括脂族多异氰酸酯和脂族多异氰酸酯与非离子的含有至少一种包含至少10个氧化乙烯单元的聚醚链的单羟基或多羟基聚亚烷基醚醇乳化剂的反应产物。作为合适的多异氰酸酯,给出了脂族和脂环族二异氰酸酯的大量例子,更优选基于1,6-己二异氰酸酯(HDI)的异氰脲酸酯和缩二脲和/或基于1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)的异氰脲酸酯。
EP-A1 540 985同样描述了多异氰酸酯混合物,但是在这种情况下聚醚链具有从5.0-9.9的平均氧化乙烯含量。
EP-A2 486 881描述了非水性脂族多异氰酸酯配方,包括选自脂族多异氰酸酯的多异氰酸酯,并包括足够保证脂族多异氰酸酯分散性含量的芳族或脂族二异氰酸酯与在聚醚链中具有至少8个氧化乙烯单元的单羟基或多羟基聚亚烷基醚醇的反应产物。
DE-A1 199 58 170描述了聚醚-改性的水可分散的多异氰酸酯混合物,其已经被单羟基聚氧化烯聚醚醇改性。非常特别优选的是具有基于HDI、IPDI和/或4,4’-双(异氰酸酯环己基)甲烷的异氰脲酸酯结构的多异氰酸酯或多异氰酸酯混合物。
DE-A1 198 22 890描述了水性双组分聚氨酯涂料体系,它的固化剂组分是由聚氧化烯聚醚醇与按脂族或脂环族方式连接的异氰酸酯基团(优选基于HDI、IPDI和/或4,4’-双(异氰酸酯环己基)甲烷的异氰脲酸酯结构)在脲基甲酸酯化条件下制备。经由脲基甲酸酯基团的聚醚链的主要连接物也可通过DE-A1 198 47077获知。
描述的非离子乳化剂包括聚乙烯吡咯烷酮-改性的多异氰酸酯(EP-A2 754713)。
也被用作活性分散单元的是含有羧酸基团的聚氧化烯醚,如在DE-A1 100 07820和DE-A1 41 13 160中描述的,或聚醚酯醇(EP-A1 728 785)。
DE-A1 40 01 783描述了多异氰酸酯混合物,其具有1-23重量%含量的缩脲二酮,含有为了分散性而化学连接的羧基。
此外,含有羧基的化合物被描述为乳化剂(EP-A2 548 669)、叔氨基和/或铵基团(EP-A1 582 166和EP-A1 531 820)、磷酸(DE-A1 197 24 199)或磺酸(EP-A1 703 255)的酸酯。
描述的多异氰酸酯混合物的一个缺点是它们不能达到使用它们获得的涂层在硬度上的需要。
为了改善分散性,水可乳化的异氰酸酯可以溶解在有机溶剂中,例如碳酸酯或内酯,如在EP-1 697 424中描述的。
从“Lackharze”[用于涂层的树脂(Resms for Coatings)](由D.Stoye和W.Freitag,Hanser编著,1996,195页)中,可以获知IPDI三聚体,其赋予涂层树脂一个相对高水平的硬度,甚至达到脆性的地步,为了降低硬度,它经常以与HDI衍生物的共混物使用。
WO2004/22624描述了水可乳化的基于1,6-己撑二异氰酸酯的多异氰酸酯与基于异佛尔酮二异氰酸酯的多异氰酸酯的混合物,其不仅表现出高硬度,还表现了良好的水可乳化性。
然而,采用这些涂层物质所得的涂层的干燥性能是不足的。
用户需要水可乳化的异氰酸酯具有如下性能:
1、异氰酸酯应当易于乳化:必须使用强制装置例如高剪切搅拌装置是不赞成的;
2、乳液应该是精细的,因为否则,例如光泽可能被破坏,或者可能出现浑浊。
3、对涂层而言,经常需要一个高的最终硬度。
4、最终硬度应该尽快获得。
发明内容
本发明的一个目的是提供一种制备水可乳化的多异氰酸酯的方法,该多异氰酸酯表现出改善的可乳化性能,并且采用它可以制备同时具有高硬度、硬度增长迅速和提高的可乳化性的涂层。后者应当比已有技术中类似的混合物干燥更快。我们发现这个目的可以通过一种制备包含如下组分的混合物的方法实现:
(A)1,6-己二异氰酸酯(HDI)的异氰脲酸酯和/或缩二脲;
(B)1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)的异氰脲酸酯;
(C)至少一种乳化剂,可通过1,6-己二异氰酸酯(HDI)的异氰脲酸酯和/或缩二脲和/或1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)的异氰脲酸酯与包含至少一个对异氰酸酯基有反应性的基团和至少一个亲水基团的组分(C1)反应得到;
(D)任选地,溶剂,
在此方法中,在第一步中,至少部分的异氰脲酸酯(B)与包含至少一个对异氰酸酯基有反应性的基团和至少一个亲水基团的组分(C1)反应,然后在第二步中,在由第一步所得反应混合物存在下,至少部分1,6-己二异氰酸酯(HDI)的异氰脲酸酯和/或缩二脲与包含至少一个对异氰酸酯基有反应性的基团和至少一个亲水基团的组分(C1)反应。
本发明的混合物证实可容易地乳化,得到精细、稳定的乳液,并能够被用于提供表现出硬度快速提高和具有高的最终硬度的涂层。
多异氰酸酯(A)是1,6-己二异氰酸酯(HDI)的异氰脲酸酯(A1)和/或缩二脲(A2)。按照本发明,这包括那些由式(Ia)和/或(Ib)的化合物和它们的高级同系物组成的多异氰酸酯,其组成含量达到至少50重量%,优选至少66%,更优选至少75%,非常优选至少85%,特别是至少95重量%。
多异氰酸酯的组成,即例如异氰脲酸酯和/或缩二脲和它们的高级同系物的比例,以及平均官能度,在本说明书中是通过采用聚苯乙烯作为标准物、四氢呋喃作为洗脱液的凝胶渗透色谱来测定的。
多异氰酸酯(B)是1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)的异氰脲酸酯。按照本发明,这包括那些由式(II)化合物和它们的高级同系物组成的多异氰酸酯,其组成含量达到至少50重量%,优选至少66%,更优选至少75%,非常优选至少85%,特别是至少95重量%,
其中X是
按照本发明,合适的乳化剂(C)是可通过至少部分上述化合物(A)和/或(B)的一种与至少一种含有至少一个对异氰酸酯基有反应性的基团并含有至少一个亲水基团的化合物(C1)反应得到的化合物。下面将(C1)称作“亲水物”。
异氰酸酯-反应性基团的例子是羟基(-OH)、未取代或单取代的氨基或巯基(-SH),优选羟基。
因此,乳化剂(C)通常包含化学连接形式的组分(C1)。
例如,组分(C1)可以包括在现有技术(如在引言中引用的现有技术)中已知的化合物。
特别地,这些可以是包含至少一个异氰酸酯-反应性基团和以下基团的化合物:
-(C1a)至少一个阳离子性亲水基团;
-(C1b)至少一个阴离子性亲水基团;或
-(C1c)至少一个非离子性亲水基团。
优选的化合物(C1)包含1-3个异氰酸酯-反应性基团和1-3个亲水基团,更优选1-2个异氰酸酯-反应性基团和1-2个亲水基团,并非常优选1个异氰酸酯-反应性基团和1个亲水基团。
化合物(C1a)包含至少一个异氰酸酯-反应性基团和至少一个阳离子性亲水基团或至少一个能转变成阳离子基团的亲水基团,例如是那些在EP-A1 582 166中,尤其是从第5页42行到第8页22行,并特别是从第9页19行到第15页34行那里;或者在EP-A1 531 820中,尤其是从第3页21行到第4页57行那里;或者在DE-A1 42 03 510中,尤其是从第3页49行到第5页35行那里描述的化合物。这些文件以参考文献的形式被明确地引入到本披露内容中。
化合物(C1b)包含至少一个异氰酸酯-反应性基团和至少一个阴离子性亲水基团或至少一个能转变成阴离子基团的亲水基团,例如是在EP-A1 703 255中,尤其是从第3页54行到第4页38行那里;在DE-A1 197 24 199中,尤其是在第3页4-30行那里;在DE-A1 4010 783中,尤其是第3栏3到40行那里;在DE-A141 13 160中,尤其是在第3栏第63行到第4栏第4行那里;以及在EP-A2 548 669中,尤其是从第4页50行到第5页6行那里描述的化合物。这些文件以参考文献的形式被明确地引入到本披露内容中。
化合物(C1c)包含至少一个异氰酸酯-反应性基团和至少一个非离子性亲水基团,是例如在EP-A2 754 713中,尤其是从第3页31到51行那里;在EP-A2206 059中,尤其是在第8页33行到第9页26行那里;在EP-A2 486 881中,尤其是第2页42到54行那里;在EP-A1 540985中,尤其是在第4页43到58行那里;在EP-A1 728 785中,尤其是从第4页55行到第5页54行那里;在EP-A1959 115中,尤其是在第4页23到46行那里;在DE-A1 199 58 170中,尤其是在第4页第22到48行那里;以及在DE-A1 100 07 820中,尤其是从第4页10行到第5页12行那里描述的化合物。这些文件以参考文献的形式被明确地引入到本披露内容中。
亲水物(C1)优选是包含至少一个异氰酸酯-反应性基团和至少一个非离子性亲水基团的化合物(C1c)。
特别优选的亲水物(C1c)是可通过烷氧化合适的起始剂分子获得的聚氧化烯聚醚醇。
用于制备聚氧化烯聚醚一元醇的合适的起始剂分子是硫醇化合物、式R1-O-H的单羟基化合物,或式R2R3N-H的仲单胺,其中,R1、R2和R3彼此独立地分别是C1-C18烷基,不间断的、或被1个或多个氧和/或硫原子和/或被一个或多个取代或未取代的亚氨基中断的C2-C18烷基,或是C6-C12芳基,C5-C12环烷基或含有氧、氮和/或硫原子的五或六元杂环,或者R2和R3一起构成不饱和、饱和或芳香环,其单元是不间断的、或被1个或多个氧和/或硫原子和/或被一个或多个取代或未取代的亚氨基中断的,对于提到的每个基团,都有可能被官能团、芳基、烷基、芳氧基、烷氧基、卤素、杂原子和/或杂环所取代。
优选R1是C1-C4烷基,即甲基、乙基、异丙基、正丙基、正丁基、异丁基、仲丁基或叔丁基;非常优选R1是甲基。
合适的单官能起始剂分子的例子可以是饱和的一元醇,例如甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、异构戊醇、己醇、辛醇和壬醇、正癸醇、正十二醇、正十四醇、正十六醇、正十八醇、环己醇、环戊醇、异构甲基环己醇或羟基甲基环己烷、3-乙基-3-羟基甲基环氧丙烷、或四氢呋喃甲醇;不饱和醇,例如烯丙醇、1,1-二甲基烯丙醇或油醇;芳族醇,例如苯酚、异构甲酚或甲氧基苯酚;芳脂族醇,例如苄基醇、茴香醇或肉桂醇;仲单胺,例如二甲胺、二乙胺、二丙胺、二异丙胺、二正丁胺、二异丁胺、双-(2-乙基己基)胺、N-甲基和N-乙基环己胺或二环己胺;杂环仲胺,例如吗啉、吡咯烷、哌啶或1H-吡唑的;以及氨基醇,例如2-二甲氨基乙醇、2-二乙氨基乙醇、2-二异丙氨基乙醇、2-二丁氨基乙醇、3-(二甲氨基)-1-丙醇或1-(二甲氨基)-2-丙醇。
对于烷氧化反应合适的氧化烯是氧化乙烯、氧化丙烯、氧化异丁烯、乙烯基环氧乙烷和/或氧化苯乙烯,可以以任何顺序或者以混合物形式在烷氧化反应中使用。
优选的氧化烯是氧化乙烯、氧化丙烯和它们的混合物;特别优选的是氧化乙烯。
优选的化合物(C1c)是以使用上面提到类型的饱和脂族或脂环族醇作为起始剂分子制得的聚氧化烯聚醚醇为基础的聚醚醇。非常特别优选的是基于使用烷基中含有1到4个碳原子的饱和脂族醇制得的聚氧化烯聚醚醇的那些聚醚醇。从甲醇起始制得的聚氧化烯聚醚醇是特别优选的。
单羟基聚氧化烯聚醚醇每分子通常平均含有5-35个、优选7-30个、更优选7-25个、非常优选10-22个氧化烯单元,特别是10-22个氧化乙烯单元。
因此,优选的聚醚醇(C1c)是式R1-O-[-Xi-]k-H的化合物,其中,R1如上所定义,k是5-35的整数,优选7-30,更优选7-25,并且特别是10-22,并且
对于i=1到k彼此独立地,每个Xi可以彼此独立地选自-CH2-CH2-O-,-CH2-CH(CH3)-O-,-CH(CH3)-CH2-O-,-CH2-C(CH3)2-O-,-C(CH3)2-CH2-O-,-CH2-CHVin-O-,-CHVin-CH2-O-,-CH2-CHPh-O-和-CHPh-CH2-O-,优选选自-CH2-CH2-O-,-CH2-CH(CH3)-O-和-CH(CH3)-CH2-O-,且更优选-CH2-CH2-O-,其中Ph是苯基且Vin是乙烯基。
作为亲水性合成组分,聚醚醇可以进一步包含少量的其它包含阴离子或阳离子基团的异氰酸酯-反应性化合物,如羧酸根、磺酸根或氨基。然而这是不太优选的。
根据本发明,为制备该混合物,至少部分、优选全部量的起始组分(B)与至少部分的化合物(C1)在40-180℃的温度下反应,优选50-150℃,遵守NCO/OH当量比从1∶1到100∶1,优选1∶1到50∶1,更优选1.5∶1到20∶1。在所得反应混合物的存在下,至少部分、优选全部量的起始化合物(A)与余量的(C1)反应。
这两个步骤中每步的反应时间通常是10分钟到5小时,优选15分钟到4小时,更优选20-180分钟,并非常优选30-120分钟。
为了加快反应,可能在适当的地方使用合适的催化剂。
这些是通常的为了这些目的已知的催化剂,例如是描述在GB-A-0 994 890中的金属羧酸盐、金属螯合物或叔胺类的催化剂,在US-A-3 769 318中描述烷基化剂类的催化剂,或者在例如EPP-A-0 000 194中作为实施例描述的强酸。
特别地,合适的催化剂是锌化合物,例如硬脂酸锌(II)、正辛酸锌(II)、2-乙基-l-己酸锌(II)、环烷酸锌(II)或乙酰丙酮酸锌(II),锡化合物,例如正辛酸锡(II)、2-乙基-l-己酸锡(II)、月桂酸锡(II)、***、二氯二丁基锡、二乙酸二丁基锡、二月桂酸二丁基锡、二马来酸二丁基锡或二乙酸二辛基锡,三(乙酰乙酸乙酯)铝,氯化铁(III)、2-乙基己酸钾、锰化合物、钴化合物、铋化合物、Zn(II)化合物、Zr(IV)化合物或镍化合物,以及强酸,例如三氟乙酸、硫酸、氯化氢、溴化氢、磷酸或高氯酸,或者这些催化剂的任何想要的混合物。
尽管较少优选,在EP-A-0 649 866第4页7行到第5页15行描述的那些催化剂也是本方法的合适的催化剂。
用于本发明方法优选的催化剂是上述类型的锌化合物。非常特别优选采用正碘苯腈辛酸锌(II)、2-乙基-l-己酸锌(II)和/或硬脂酸锌(II)。
在使用时,基于反应物的总重量计,这些催化剂以0.001-5重量%的量使用,优选0.005-1重量%。
用于制备聚氨酯配方的加聚反应可以特别优选在铯盐存在下发生,如在DE10161156中描述的。优选的铯盐是其中使用下列阴离子的化合物: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代表从1到20的数字。
特别优选的化合物是羧酸铯,其中阴离子具有(CnH2n-1O2)-或(Cn+1H2n-2O4)2-的结构式,其中n从1到20。尤其优选的铯盐包含式(CnH2n-1O2)-的单羧酸根阴离子,其中n代表从1到20的数字。这里特别提到可以被制成甲酸盐、乙酸盐、丙酸盐、己酸盐和2-乙基己酸盐。
铯盐的用量是基于每千克无溶剂的反应混合物计的0.01-10mmol铯盐。它们的用量优选是基于每千克无溶剂的反应混合物计的0.05-2mmol铯盐。
铯盐可以以固体形式加入到反应混合物中,但优选以溶解的形式。合适的溶剂是极性的、非质子溶剂或质子溶剂。除水之外,特别合适的是醇;尤其合适的是多元醇,比如也被用作用于聚氨酯的合成单元,例如乙二醇、丙二醇和丁二醇。铯盐的使用使得可能在通常条件下发生加聚反应。
可以以任何想要的方法加入到反应混合物中。因而,例如,可以在实际反应开始之前将催化剂(在使用的场合)混合到多异氰酸酯组分(A)、(B)和/或到混合乳化剂组分(C1)中。也可以在反应中的任何时候,或者在两级反应方法中、氨酯化反应之后(也就是异氰酸酯和羟基完全转变的对应理论NCO含量已经达到)将催化剂添加到反应混合物中。
反应的进程可以通过采用例如滴定法测定的NCO含量来监测。当目标NCO含量已经达到时,反应被终止。对纯热反应方式而言,这可以通过例如冷却反应混合物到室温来完成。然而,在使用上述类型催化剂时,通常通过添加合适的去活化剂来停止反应。合适的去活化剂的例子包括有机或无机酸、相应酸的卤化物和烷基化试剂。可以提到的例子包括磷酸、单氯乙酸、十二烷基苯磺酸、苯甲酰氯、硫酸二甲酯,并且优选磷酸二丁酯以及二-2-乙基己基磷酸盐。基于催化剂的摩尔数,去活化剂可以以1-200mol%的量使用,优选20-100mol%。
所得的多异氰酸酯混合物通常优选具有6.0-23.0重量%的NCO含量,更优选8.5-22.0重量%。
获得的多异氰酸酯混合物通常优选具有在23℃下0.2-20Pas的粘度,更优选0.5-8Pas。
在本说明书中,除非另外指出,粘度是在23℃下、按照DIN EN ISO3219/A.3、在锥板***中、以1000s-1的剪切速度报出的。
本方法可以在合适时在对异氰酸酯基团呈惰性的溶剂(D)中进行。合适的溶剂的例子是本身已知的传统漆溶剂,例如乙酸乙酯、乙酸丁酯、乙二醇单甲基或单乙基醚乙酸酯、1-甲氧基2-乙酸丙酯、3-甲氧基乙酸正丁酯、丙酮、2-丁酮、异丁基甲基酮、4-甲基-2-戊酮、环己酮、环戊酮、甲苯、二甲苯、氯苯、石油溶剂油、相对高取代度的芳族物质,例如以 和名称市售的、丙二醇双乙酸酯、二甘醇二甲醚、双丙甘醇二甲醚、二甘醇乙基和丁基醚乙酸酯、N-甲基吡咯烷酮、N-甲基己内酰胺,并且优选在EP-A1 697 424第4页4到32行指定的碳酸酯或内酯,更优选碳酸二甲酯、碳酸二乙酯、碳酸1,2-亚乙酯、碳酸1,2-亚丙酯,内酯如β-丙内酯、γ-丁内酯、ε-己内酯和ε-甲基己内酯,或这些溶剂的任何想要的混合物。
也可以先在没有溶剂的条件下制备异氰酸酯,然后采用溶剂(D)来吸收由此得到的产品。
无溶剂形式的混合物优选包含:
30-90重量%、优选30-85重量%、更优选50-70重量%的(A),
5-70重量%、优选20-60重量%、更优选30-50重量%的(B),和
5-40重量%、优选5-30重量%的(C1),
(A)、(B)和(C1)的总量为100重量%,并且在每种情况下包括准备制备乳化剂(C)的异氰酸酯(A)和/或(B)。
在本发明的方法中,化合物(C1)按照20∶80到80∶20的重量比与组分(B)和(A)反应,优选30∶70到70∶30,更优选40∶60到60∶40的。在一个优选的方案中,占(C1)总量的至少80重量%被化学连接到组分(A)和(B)上,优选至少85重量%,更优选至少90重量%,非常优选至少95%,并且更加特别是至少98重量%。
基于总的混合物,溶剂(D)可以以0-60重量%的量存在,优选以0-50重量%的量存在。
为制备水性分散体的目的,混合物优选可以被分散在水里;特别优选,混合物被混成水性分散体。
多异氰酸酯配方适用于改性用于基材的水性涂层材料(油漆、防护涂层),所述基材例如是木材、薄木片、纸、纸板、卡纸、纺织品、皮革、无纺布、塑性表面、玻璃、陶器、矿物建筑材料例如水泥模塑和纤维水泥平板、包覆或未包覆金属、胶粘剂或浸渍组合物,该配方适用于染色,例如基于固含量5-40重量%的水分散体或溶液,优选5-20重量%。合适的涂层材料例如包括本来已知的烯属不饱和单体的均聚物或共聚物、或聚氨酯的水分散体,或者天然物质如干酪素的溶液。
基于涂层材料的固含量计,多异氰酸酯配方通常以1-25重量%的含量加入到水性涂层材料中,优选2.5-20重量%。
它们按照已知的方法被应用到基材上,例如以5-50g固体/平方米的速度喷涂。
合适的烯属不饱和单体的均聚物或共聚物的分散体是例如传统的基于具有2-18个、优选2-4个碳原子的羧酸的乙烯基酯(例如特别是乙酸乙烯酯)的均聚物或共聚物的分散体,如果需要,基于烯属不饱和单体总量计具有高达70重量%的其它烯属不饱和单体;和/或具有1-18个、优选1-4个碳原子醇的(甲基)丙烯酸的酯(例如特别是(甲基)丙烯酸的甲酯、乙酯、丙酯、羟乙酯、羟丙酯的均聚物或共聚物),如果需要,具有高达70重量%的其它烯属不饱和单体;和/或具有大约20-60重量%丁二烯含量的丁二烯-苯乙烯共聚物;和/或其它二烯聚合物或共聚物,例如聚丁二烯或丁二烯与如苯乙烯、丙烯腈和/或甲基丙烯腈的其它烯属不饱和单体的共聚物;和/或2-氯1,3-丁二烯聚合物或共聚物的水分散体,如果需要,与具有上面列举类型的其它烯属不饱和单体,即具有大约30-40重量%氯含量(特别是大约36重量%氯含量)的那些。
优选含有90-99.5重量%的丙烯酸或甲基丙烯酸的具有1-4个碳原子的烷醇酯与0.5-10重量%(每种情况均基于共聚物)的在羟基烷基中具有2-20个碳原子的羟基烷基的丙烯酸酯和甲基丙烯酸酯(例如羟基乙基、羟基丙基或羟基丁基的丙烯酸酯或甲基丙烯酸酯)的共聚物的水分散体。这些分散体是本来已知的,且能够通过乳液聚合常规制备(参见Houben-Wey,Methoden der organichen Chemie,第4版,E 20卷,第217页起)。
合适的水性聚氨酯分散体是本来已知类型的那些,如在例如US-A 3,479,310、GB-A 1,076,688、US-A 4,108,814、US-A 4,092,286、DE-A 2 651 505、US-A4,190,566、DE-A 2732 131或DE-A 2 811 148中描述的。
使用的水性分散体可以含有常规的助剂和添加剂。例如这些包括填料,如石英粉、石英砂、高分散二氧化硅、重晶石、碳酸钙、白垩、白云石或滑石,它们经常与合适的润湿剂一起使用,如六偏磷酸钠、萘磺酸、聚丙烯酸的铵或钠盐,润湿剂通常以基于填料计0.2-0.6重量%的量添加。
另外的合适助剂是有机增稠剂,例如基于分散体,以0.01-1重量%的量使用,如纤维素衍生物、藻酸盐、淀粉或淀粉衍生物或聚丙烯酸;或无机增稠剂以基于分散体计0.05-5重量%的量使用,如膨润土。
为了防腐,杀菌剂也可以添加到分散体中。这些通常以基于分散体计0.02-1重量%的量使用。合适的杀菌剂的例子是苯酚或甲酚的衍生物以及有机锡化合物。
浸渍用基材例如是合成或非合成的纤维,和/或包含这些纤维的纺织或无纺织物。
混合物可以被精细地分散在水分散体中。获得的分散体在储存上非常稳定。并且,为了设定分散体的理想的性能或达到应用中理想的性能,需要加入少量的水可乳化多异氰酸酯。
该混合物当然可以含有涂覆工艺的常规的助剂和添加剂。这些包括例如消泡剂、增稠剂、流平助剂、颜料、乳化剂、分散助剂和溶剂。通过加水来设定理想的工艺粘度。
为制备该分散体,在大多数情况下,采用简单的乳化技术,例如用机械搅拌器;或者在很多情况下,简单用手工混合两个组分,就足够来得到具有很好性能的分散体了。然而,也可以应用涉及相对高剪切能量的混合技术,例如喷射分散。
包含该混合物的涂层材料可以特别用作底漆、表面涂料剂、着色罩光漆材料和在汽车部分涂饰或大型车辆喷漆中的透明涂装材料。该涂层材料特别适合于需更特别高的应用可靠性、户外气候稳定性、光学性能、耐溶剂性、耐化学品性和耐水性的应用中,例如汽车涂饰或大型车辆喷漆。
包含该混合物的涂层材料可以以任何各种喷涂法使用,例如空气压、无空气、或静电喷涂方法,使用单组分或双组分的喷射单元,,或通过喷雾、泥刀涂抹、刮刀涂布、刷涂、卷涂、辊涂、浇涂、层压、模型涂覆或共挤出法来使用。
涂料通常在常温条件(也就是不加热涂料的条件下)下干燥和固化。另外,该混合物可以用于制备随后在提高的温度下、例如在40-250℃、优选40-150℃、尤其是40-100℃下干燥和固化施用的涂料。
尽管某些与制备水可乳化的多异氰酸酯有关的出版物,例如DE-A1 40 01783、EP-A2 206 059、EP-A2 486 881、EP-A1 540 985或DE-A1 199 58 170,包括了1,6-己二异氰酸酯(HDI)的异氰脲酸酯和/或缩二脲、1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)的异氰脲酸酯、和在长列的合适的起始异氰酸酯内的乳化剂的混合物,对于技术工人无论如何也不可能从任何上述出版物中推断出任何该混合物同时表现出提高的硬度、提高的硬度增加和迅速乳化性特定的启示。此外,与已有技术相比,该混合物表现出较长的“适用期”,这是其中所有组分都已经被混合后母料仍旧能够使用的时段,并且不会发生例如分离或过早固化。
随后的实施例是用来举例说明本发明的性质,但没有限定它。
实施例
在本说明书中,除非另有所指,份数应该理解为表示重量份。
多异氰酸酯A:
HDI异氰脲酸酯,具有22.2%的NCO含量和在23℃下2800mPa*s的粘度(例如HI 100,来自BASF SE)。
多异氰酸酯B:
IPDI异氰脲酸酯,70%的乙酸丁酯溶液,具有12.1%的NCO含量和在23℃下600mPa*s的粘度(例如IT 170B,来自BASF SE)。
聚醚A:
单官能聚氧化乙烯,从甲醇开始并采用氢氧化钾催化剂制得,具有112的OH值(按照DIN 53240)和500g/mol的分子量。接着采用乙酸中和仍然存在的碱性催化剂残留,并且产品被脱盐处理。同样的步骤也除去了已形成的乙酸钾。
对比实施例1:
DE 103 50 242中实施例2的水分散的官能化HDI基多异氰酸酯。
对比实施例2:
214g多异氰酸酯A、100g多异氰酸酯B和37.5g聚醚A在85℃下反应7.5小时。相应的产品具有14.3%的NCO含量和在23℃下6500mPas的粘度,且只是部分水分散的。
本发明实施例1;
250g多异氰酸酯B和26.25g聚醚A在加入0.068g新癸酸锌(50%的乙酸丁酯溶液)催化剂下反应。在80℃下1小时后,NCO含量是13.2%。然后,加入117g多异氰酸酯A和17.55g聚醚A。相应的产品具有13.25%的NCO含量和在23℃下1770mPas的粘度。
在处理之前,产品以80%的浓度溶解在DMM中。
性能结果:
涂覆配方
100g8311(基于丙烯酸酯,BASF SE的水性多元醇,OH值是120mgKOH/g,42%的水溶液)与作为成膜助剂的1.74g丁基二甘醇乙酸酯和4.25g丁基乙二醇乙酸酯混合。然后用1.05g的50%浓度的二甲基乙胺水溶液将pH值调节到8.5。最后,用5.80g水来调节应用粘度,并加入0.57g340(BYK)消泡剂。
然后将聚异氰酸用分散机引入,且用水调节配方到最终粘度。在室温下得到涂覆材料。
WO 2004/22624 A1的实施例2
将60g(0.246当量的NCO)异氰酸酯B加入到6.7g(0.007mol)具有分子质量1000且从甲醇起始制备的单官能聚氧化乙烯中,将这些组分在130℃下搅拌80分钟。然后将混合物冷却到室温。产品是具有15.2%NCO含量的固体多异氰酸酯(=b1)。纯的亲水化的异氰酸酯b1可以在水中乳化,只有在相当大的机械努力下才得到白色的粗乳状液。
通过在100℃下制备来自WO 2004/22624 A1实施例1的异氰酸酯a1和b1的混合物,得到了容易乳化的产品,它表现出良好的乳化性和在涂层硬度方面好的性能。
Claims (6)
1.一种制备包含以下组分的混合物的方法:
(A)1,6-己二异氰酸酯(HDI)的异氰脲酸酯和/或缩二脲;
(B)1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)的异氰脲酸酯;
(C)至少一种乳化剂,其可通过1,6-己二异氰酸酯(HDI)异氰脲酸酯和/或缩二脲和/或1-异氰酸酯基-3,5,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)的异氰脲酸酯与包含至少一个对异氰酸酯基有反应性的基团和至少一个亲水基团的组分(C1)反应得到;和
(D)任选地,溶剂,
此方法包括:
在第一步中,至少部分的异氰脲酸酯(B)与包含至少一个对异氰酸酯基有反应性的基团和至少一个亲水基团的组分(C1)反应,然后在第二步中,在由第一步所得反应混合物存在下,至少部分1,6-己二异氰酸酯(HDI)的异氰脲酸酯和/或缩二脲与包含至少一个对异氰酸酯基有反应性的基团和至少一个亲水基团的组分(C1)反应。
2.根据权利要求1的方法,其是无溶剂的形式,其中混合物按照如下混合:
30-90重量%的(A)
5-70重量%的(B),和
5-40重量%的(C1),
(A)、(B)和(C1)的总量为100重量%,并且在每种情况下包括用于制备乳化剂(C)的异氰酸酯(A)和/或(B)。
3.根据权利要求1或2的方法,其中组分(C1)包含至少一个异氰酸酯-反应性基团和至少一个非离子性亲水基团。
4.根据权利要求1或2的方法,其中组分(C1)是可通过将至少一种在烷基中具有1-4个碳原子的饱和脂族醇与氧化乙烯、氧化丙烯或它们的混合物反应得到的至少一种聚氧化烯聚醚醇。
5.根据权利要求4的方法,其中聚氧化烯聚醚醇含有按每分子计平均5-35个氧化乙烯单元。
6.根据权利要求1的方法,其中碳酸酯或内酯用作溶剂(D)。
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