CN1045269A - 用酸质子化后可用水稀释的聚合反应产物 - Google Patents
用酸质子化后可用水稀释的聚合反应产物 Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/14—Polycondensates modified by chemical after-treatment
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- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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Abstract
聚合反应产物，它在用酸质子化后可用水稀释，并适于以水性分散液的形式作为添加剂而用于电涂层浴中，它由下列组分制成：A)含有一级和/或二级氨基的丁二烯/丙烯腈共聚物，B)平均分子量为140-10,000且每分子平均含1.5-3个环氧基的环氧化合物，组分A)的量为每摩尔组分B)的环氧基1.05摩尔或更多组分A)的一级和/或二级氨基。
Description
本发明涉及一种聚合反应产物，该聚合反应产物在用酸质子化后可用水稀释，并可由下列化合物制备：
A.含有一级和/或二级氨基的丁二烯/丙烯腈共聚物，和
B.平均分子量为140-10，000并且每个分子平均有1.5-2.5个环氧基团的环氧树脂，
组份（A）的量是每摩尔组份（B）的环氧基团有1.05摩尔或更多的组份（A）的一级和/或二级氨基。
本发明还涉及本发明聚合反应产物的制备方法，含有该反应产物的水性分散液，以及该水性分散液在电涂浴中的应用。
US-A-4 432 850公开了聚环氧化物与聚亚氧烷基聚胺的反应产物，该产物在水中质子化和分散后可作为添加剂用于普通电涂浴中，据称它们可改善涂层的流动性和挠性。
EP-A-253 404同样涉及可加到普通电涂浴中的水性分散液。这些分散液含有多羟基化合物或芳族二酚的二环氧甘油醚与单或双官能苯酚的反应产物，它们剩余的环氧基团可全部或部分转化为阳离子基团。这便产生了改善的防腐性能的厚涂层。
此外，DE-A-3 639 570公开了用于电涂浴的粘合剂，它是由胺端基丁二烯/丙烯腈共聚物与部分失活的环氧树脂反应得到的。
阴极电涂层应同时具有下列基本性能：良好的耐腐蚀性和良好的弹性。
先有技术体系常常只具有这两种性能的一种性能，即具有较好防腐性的涂层弹性较差，而弹性好的涂层防腐性差。
本发明的目的是提供一种可满足这两种要求的体系。
用本文开始所述的聚合反应产物可达到这个目的，将丁二烯/丙烯腈共聚物与环氧树脂反应可制得该聚合反应产物，它在质子化后可用水稀释，因而能在水中制成分散液用作普通电涂浴中的添加剂。
适用的组分（A）的是丁二烯/丙烯腈共聚物，其中丙烯腈含量为5-45%（重量），较好为10-30%（重量），丁二烯含量为55-95%（重量），较好为70-90%（重量），每个分子平均含1.4-3.0个一级和/或二级氨基，还可含有三级氨基。共聚物的平均分子量（Mn）优选为500-15，000，较好为2，000-8，000。
含氨基共聚物可由例如含羧基丁二烯/丙烯腈共聚物与二胺反应制备。这种含氨基丁二烯/丙烯腈共聚物多半可买到。
另外，含氨基丁二烯/丙烯腈共聚物可由丁二烯/丙烯腈共聚物部分氢化制备，或通过向含环氧基的丁二烯/丙烯腈共聚物中加入一级胺来制备。
适用的组分（B）是环氧化合物，它的分子量（对聚合物为Mn）为140-10，000，每分子平均含1.5-3个环氧基，最好2个环氧基。
较好的环氧化合物是脂肪族二元醇如丁二醇或己二醇的缩水甘油醚，或平均含有两个或更多酚羟基的多酚的缩水甘油醚，它们可通过在碱存在下按常用方法用表囟代醇醚化而制得。适用的苯酚化合物的例子是2，2-双（4-羟苯基）丙烷（双酚A）、4，4′-二羟基二苯酮、4，4′-二羟基二苯砜、1，1-双（4-羟苯基）乙烷、1，1-双（4-羟苯基）异丁烷、2，2-双（4-羟基叔丁基苯基）丙烷、双（2-羟基萘基）甲烷和1，5-二羟基萘。
在某些情况下，需要用分子量较高的芳族环氧树脂。它们可如下制备，将上述二缩水甘油醚与多酚如2，2-双（4-羟苯基）丙烷反应，然后再使所得产物与表氯醇反应制成多缩水甘油醚。
还可以用例如氧化乙烯、氧化丙烯、四氢呋喃或其它环醚聚合制得多羟基化合物而使用这种类型的多羟基化合物的二缩水甘油醚。
组分（A）和组分（B）的量一般用这样的方法确定，即每摩尔组分（B）的环氧基用1.05-20摩尔，最好1.2-4.0摩尔含氨基丁二烯-丙烯腈共聚物的NH基。
反应一般是在有机溶剂或溶剂混合物中将丁二烯/丙烯腈共聚物（A）与环氧树脂（B）反应，该溶剂不仅对氨基是惰性的而且对环氧基也是惰性的，反应在20-150℃，最好在50-110℃下进行。反应时间至多可为20小时。
所得聚合反应产物的胺值为25-170mg KOH/g固体物，最好为40-100mg KOH/g固体物。
环氧基-胺反应完成后，氨基可全部或部分用酸中和，并加入水使质子化的树脂分散。适用的酸是磷酸，但最好使用有机酸如甲酸、乙酸、丙酸或乳酸。也可向水/酸混合物中加入树脂。然后可将有机溶剂蒸出。
所得分散液可加入到普通电涂浴中。一般，所用分散液含15-20%（重量）固体。
这种电涂浴是基于碱性聚合物的，其中碱性基团是一级、二级或三级氨基。也可以使用带是有磷鎓或硫鎓基团的原料树脂。一般，这些原料树脂还含有其它官能团，如羟基或不饱和双键。
适用的这类原料树脂是分子量较好为2，000-200，000的聚合物，例如氨基丙烯酸酯和氨基甲基丙烯酸酯树脂、聚加合物如氨基聚亚胺酯树脂和聚缩合物如氨基环氧树脂。
有较好防腐性能的底涂层最好是用氨基环氧树脂作原料树脂来制备的氨基环氧树脂叙述在例如EP-A-134 983 EP-A-165 556、EP-A-167 029、DE-A-3 422 457和DE-A-3 444 410。
氨基环氧树脂是按一般方法将含环氧基的树脂与饱和和/或不饱和一级和/或二级胺或氨基醇反应而制得的。适用的环氧树脂是每个分子平均含1.5-3个，较好为2个环氧基的化合物，其平均分子量为300-6，000。、最好是使用分子中平均为2个羟基的多酚的缩水甘油醚，最适用的酚组分是2，2-双（4-羟苯基）丙烷（双酚A）。
分子量较高的环氧树脂是这样制备的，即将上述二缩水甘油醚与多酚如2，2-双（4-羟苯基）丙烷反应，然后所得产物与表氯醇反应，得到多缩水甘油醚。
氨基环氧树脂还可用饱和或不饱和多元羧酸如己二酸、富马酸或二聚脂肪酸改性。
还可以使用已与半封闭异氰酸酯反应并有自交联性能的原料树脂。这种树脂有例如在EP-A-273 247和US4 692 503上所述。
如果碱性树脂不含有任何自交联基团，则需要在制备分散液之前加入交联剂。
对这原料树脂适用的交联剂是例如在DE-A-3 311 514上所述的脲缩合产物，或DE-A-3 422 457所述的苯酚曼尼期碱。EP-A-134 983还提及封闭异氰酸酯或氨基塑性树脂如脲甲醛树脂、密胺树脂或苯并胍胺树脂为另一些可用的交联剂。
标准电涂浴也可含有颜料膏和常用助剂。颜料膏可由例如漆浆树脂和颜料如二氧化钛、碳黑或硅酸铝及助剂和分散剂制成。适用的漆浆树脂在例如EP-A-107 089和EP-A-251 772上有所叙述。
涂料薄膜在阴极电涂层上的沉积通常在20-35℃下，最好在26-32℃下进行5-500秒，最好60-300秒，沉积电压为50-500V。被涂层的物件是作为阴极相连的。
然后涂料薄膜在120-210℃下，最好在140-180℃下烘干。
这样制备的涂层同时具有良好的防腐蚀性和高弹性。
实例1-7
本发明聚合反应产物的制备
一般方法
在所有实例中，所用的丁二烯/丙烯腈组分是平均分子量Mn为3500-3800的共聚物，该共聚物可由氨基乙基哌嗪与丙烯腈含量为16%（重量）的羧端基丁二烯/丙烯腈共聚物反应来制备。
在实例1-5中，所用的环氧树脂是环氧当量（EEW）约为840的聚四氢呋喃二缩水甘油醚。在实例6中，用的是聚环氧丙烷二缩水甘油醚（EW约为330）。在实例7中，用的是双酚A二缩水甘油醚（EEW约为188）。
将丁二烯/丙烯腈共聚物溶解在甲苯中，与环氧树脂混合，在80℃下搅拌几小时（参见表Ⅰ），直到环氧值确为0。然后，反应混合物用乙二醇单丁基醚和异丁醇稀释，冷却至40℃。其后加入冰醋酸，接着用1小时时间加入去离子水。
然后，在减压下蒸馏掉一些有机溶剂和水，将固体物放在去离子中。
本试验的详细说明在表Ⅰ中给出。
表Ⅰ
实例 1 2 3 4 5 6 7
Bu/AN共聚物[g] 359.8 359.8 359.8 359.8 359.8 172.9 359.8
环氧树脂[g] 23.1 46.3 52.9 61.7 70.7 27.4 9.2
甲苯［g] 164.1 174.0 176.9 180.6 184.5 85.8 158.1
乙二醇单丁基醚[g] 62.9 68.4 68.2 62.4 59.4 41.4 86.0
异丁醇［g] 97.1 116.0 119.0 112.0 111.0 73.2 125.3
5.9 6.4 6.3 5.8 5.5 3.8 5.5
乙酸［g] 1463 1588 1588 1452 1452 960 2000
水［ml]
反应时间［小时］ 12 10 10 10 11 10 19
固体含量［重量％］ 17 19 17 18 18 18 17
胺值［每克固体物质消耗的KOH毫克数］
65.0 61.2 60.3 58.4 57.4 59.8 59.4电涂浴
A）原料树脂的制备
A1）将5800克的六亚甲基二胺、7250克二聚脂肪酸和1400克亚麻仁脂肪酸的混合物慢慢加热至195℃，同时蒸馏掉形成的水（540克）。然后该混合物冷却至100℃并用5961克甲苯稀释至固体含量为70%（重量）产物的胺值为克固体物质197毫克KOH。
A2）在第二搅拌釜中，将10当量的双酚A二缩水甘油醚和当量为485的表氯醇加热溶解在1039克甲苯和1039克异丁醇的混合溶剂中。将这样形成的溶液冷却至60℃并与300.4克甲基乙醇胺和128克异丁醇混合，在5分钟时间内温度升至78℃。然后，加入A1）制得的1850克缩合产物，混合物在80℃下加热2小时。
B）颜料膏的制备
向525.8克A）所得的粘合剂中加入168.7克丁基乙二醇，600克水和16.5克乙酸。然后加入800克二氧化钛、11克碳黑和50克碱性硅酸铅，该混合物球磨成粒度小于9LM的颗粒。然后，用水稀释至固体含量为47%（重量）
C）交联剂的制备
将1.32千克甲苯、0.42千克三羟甲基丙烷和0.72千克双酚A的混合物在60℃下搅拌，直到形成均匀溶液。该溶液在60℃下加到3.45千克二异氰酸异佛尔酮酯、0.86千克甲苯和0.0034千克二月桂酸二丁锡的热混合物中。该混合物在60℃下存放2小时，然后与2.0千克二丁基胺混合，加入的速度使反应混合物的温度不超过80℃。然后加入1.11千克甲苯，混合物再在80℃下保持1小时。
D）电涂浴的制备
将700克A）所得的粘合剂和300克C）的交联剂用有足够水的19克乙酸溶液分散，形成固体含量为31%（重量）的分散液。然后将有机溶剂共沸蒸馏掉，再用水将分散液调节成固体含量为35%（重量）的分散液。
这样得到的分散液与775克B）所得的颜料膏混合，并与各种量的本发明分散液混合，加水至体积为5000ml。
电涂浴在30℃下搅拌168小时。将由经过磷酸锌处理的钢制试板组成的阴极用120秒钟用涂料薄膜涂层。然后这些涂料薄膜在155℃下烘烤20分钟。
电涂浴的组成、涂层条件和测试结果列于表Ⅱ。
Claims (8)
1、一种聚合反应产物，该产物用酸质子化后用水稀释，并由下列组分制成：
A)含有一级和/或二级氨基的丁二烯/丙烯腈共聚物，
B)平均分子量为140-10，000且每分子平均含1.5-3个环氧基的环氧化合物，
组分A)的量为每摩尔组分B)的环氧基1.05摩尔或更多组分A)的一级和/或二级氨基。
2、按照权利要求1的反应产物，其中组分A）是含氨基的丁二烯/丙烯腈共聚物，该共聚物含有5-45%（重量）丙烯腈为共聚单元，平均有1.5-3个一级和/或二级氨基。
3、按照权利要求1或2的反应产物，其中环氧化合物（组分B）是二元或多元醚醇的缩水甘油醚。
4、含有如权利要求1-3中任一项所述的反应产物的水性分散液。
5、一种制备如权利要求1-3中任一项所述的聚合反应产物的方法，该方法包括使下列组分进行反应，
A）含有一级和/或二级氨基的丁二烯/丙烯腈共聚物，
B）平均分子量为140-10，000且每分子平均含1.5-3个环氧基的环氧化合物，
组分A）的量为每摩尔组分B）的环氧基1.05摩尔或更多组分A）的一级和/或二级氨基。
6、权利要求3所述分散液在电涂浴中作为添加剂的应用。
7、含有如权利要求1-3中任一项所述的聚合反应产物的电涂浴。
8、按照权利要求7的电涂浴，该浴还含有交联剂和颜料膏。
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| US5177125A (en) * | 1989-02-28 | 1993-01-05 | Basf Lacke & Farben Aktiengeselllschaft | Two-phase cathodic electrocoat containing epoxy resin-ATBN adducts |
| KR960014106B1 (ko) * | 1990-06-06 | 1996-10-14 | 바스프 락케+파르벤 악티엔게젤샤프트 | 전기 전도성 기판의 코팅방법, 물-기저 코팅 및 차단된 nco기 함유 교차결합제 |
| US5258460A (en) * | 1990-09-14 | 1993-11-02 | Basf Lacke+ Farben Aktiengesellschaft | Polymeric reaction products |
| DE4135239A1 (de) * | 1991-10-25 | 1993-04-29 | Basf Lacke & Farben | Kationische harze auf basis von copolymerisaten aus butadien und acrylnitril |
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| US4253930A (en) * | 1979-07-16 | 1981-03-03 | Nippon Paint Co., Ltd. | Process for electrodepositing cationic compositions |
| US4432850A (en) * | 1981-07-20 | 1984-02-21 | Ppg Industries, Inc. | Ungelled polyepoxide-polyoxyalkylenepolyamine resins, aqueous dispersions thereof, and their use in cationic electrodeposition |
| FR2589472B1 (fr) * | 1985-10-31 | 1988-02-26 | Charbonnages Ste Chimique | Procede de fabrication de compositions a base de resines epoxy |
| DE3542594A1 (de) * | 1985-12-03 | 1987-06-04 | Basf Lacke & Farben | Durch protonieren mit saeure wasserverduennbares bindemittel, dessen herstellung und verwendung |
| CA1277059C (en) * | 1986-07-18 | 1990-11-27 | Richard A. Hickner | Controlled film build epoxy coatings applied by cathodic electrodeposition |
| IL80391A (en) * | 1986-10-22 | 1992-03-29 | Bromine Compounds Ltd | Process for the preparation of decabromodiphenyl ether with improved thermal stability |
| DE3639570A1 (de) * | 1986-11-20 | 1988-06-01 | Basf Lacke & Farben | Durch protonierung mit saeure wasserverduennbare bindemittel |
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| CN114874413A (zh) * | 2022-02-25 | 2022-08-09 | 上海金力泰化工股份有限公司 | 一种配套薄膜前处理的阴极电泳涂料用分散树脂及其制备方法及应用 |
| CN114874413B (zh) * | 2022-02-25 | 2024-03-01 | 上海金力泰化工股份有限公司 | 一种配套薄膜前处理的阴极电泳涂料用分散树脂及其制备方法及应用 |
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| Publication number | Publication date |
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| AU5019890A (en) | 1990-09-06 |
| BR9000912A (pt) | 1991-10-15 |
| AU620970B2 (en) | 1992-02-27 |
| DE59008990D1 (de) | 1995-06-08 |
| DE3906144A1 (de) | 1990-09-06 |
| CA2009303A1 (en) | 1990-08-31 |
| EP0385300B1 (de) | 1995-05-03 |
| ATE122068T1 (de) | 1995-05-15 |
| CA2009303C (en) | 1999-05-04 |
| JP2733531B2 (ja) | 1998-03-30 |
| CN1041836C (zh) | 1999-01-27 |
| EP0385300A2 (de) | 1990-09-05 |
| US5051160A (en) | 1991-09-24 |
| KR900012957A (ko) | 1990-09-03 |
| KR0173117B1 (ko) | 1999-03-30 |
| EP0385300A3 (de) | 1991-01-02 |
| ES2074484T3 (es) | 1995-09-16 |
| JPH03720A (ja) | 1991-01-07 |
| ZA901466B (en) | 1991-11-27 |
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