CN117836371A - 双组分环氧树脂胺官能化胶乳组合物 - Google Patents
双组分环氧树脂胺官能化胶乳组合物 Download PDFInfo
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- CN117836371A CN117836371A CN202280057100.0A CN202280057100A CN117836371A CN 117836371 A CN117836371 A CN 117836371A CN 202280057100 A CN202280057100 A CN 202280057100A CN 117836371 A CN117836371 A CN 117836371A
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- diglycidyl ether
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/44—Amides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/4261—Macromolecular compounds obtained by reactions involving only unsaturated carbon-to-carbon bindings
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- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1515—Three-membered rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
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Abstract
本发明涉及一种包含热固性化合物和用氨基烷基酯基团官能化的聚合物颗粒的水性分散体的组合物。该组合物可用作双组分水性固化体系，并且可有效地在工业涂层应用中提供耐腐蚀性和耐起泡性。
Description
背景技术
本发明涉及双组分组合物，其包含环氧树脂和用胺基官能化的胶乳。该组合物在工业涂层应用中可用于涂覆基材，尤其是金属表面。
用于工业应用的双组分水性可固化组合物包含环氧树脂和固化剂，通常为聚胺或羧酸官能化胶乳，其充当交联剂以在将涂层施涂到基材上之后为所述涂层提供硬度。羧酸官能化丙烯酸胶乳提供具有伴随的耐变黄性的UV稳定涂层，但需要较长的固化时间并且形成具有相对较差的耐腐蚀性的涂层。另一方面，聚胺固化剂快速固化并且提供相对可接受的耐腐蚀性，但耐UV性较差。
因此，在双组分水性环氧树脂组合物领域中发现提供快速固化时间、耐UV性和耐腐蚀性的调配物将是有利的。
发明内容
本发明通过提供一种组合物解决了本领域的需求，该组合物包含以下的水性分散体：a)热固性化合物；和b)用以下类型的氨基烷基酯基团官能化的聚合物颗粒：
其中R为H或C1-C6烷基。
本发明的组合物可用作双组分水性固化体系，其在工业涂层应用中尤其有效。
具体实施方式
本发明是一种组合物，该组合物包含以下的水性分散体：a)热固性化合物；和b)用结构I的氨基烷基酯基团官能化的聚合物颗粒：
其中R为H或C1-C6烷基。
如本文所用，术语“热固性化合物”是指用至少两个环氧乙烷基团官能化的一种或多种化合物。合适的热固性化合物的类别的示例包括环氧酚醛树脂、二缩水甘油醚、三缩水甘油醚或四缩水甘油醚和二缩水甘油酯、三缩水甘油酯或四缩水甘油酸酯。具有至少两个环氧乙烷基团的化合物的示例包括双酚A的二缩水甘油醚、双酚F的二缩水甘油醚、1,4-丁二醇二缩水甘油醚、1,6-己二醇二缩水甘油醚、邻苯二甲酸的二缩水甘油酯、1,4-环己烷二甲醇二缩水甘油醚、1,3-环己烷二甲醇二缩水甘油醚、六氢邻苯二甲酸的二缩水甘油酯、环氧酚醛树脂和它们的组合以及它们的水性分散体。可商购获得的热固性化合物是D.E.R.TM331液体环氧树脂(陶氏化学公司(The Dow Chemical Company)或其附属公司的商标)。
一方面，将热固性化合物并入(吸收)到分散在水中的聚合物颗粒(胶乳颗粒)中以形成丙烯酸-环氧杂化物(AEH)。在一种优选的AEH中，热固性化合物完全或几乎完全并入胶乳颗粒中，其中小于1重量％的游离热固性化合物保留在水相中。合适的胶乳的示例包括基于丙烯酸、苯乙烯-丙烯酸、苯乙烯-丁二烯、氨基甲酸酯、酯、烯烃、氯乙烯、乙烯乙酸乙烯酯和聚乙酸乙烯酯的胶乳，其中丙烯酸和苯乙烯-丙烯酸胶乳是优选的。聚合物颗粒优选地具有如通过动态光散射测量的在80nm，优选地150nm至500nm，优选地至350nm范围内的平均粒度。
适于制备丙烯酸胶乳的单体包括丙烯酸甲酯、丙烯酸乙酯、丙烯酸丁酯、丙烯酸2-乙基己酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丁酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸环己酯、甲基丙烯酸叔丁酯、丙烯酸环己酯、丙烯酸叔丁酯和它们的组合。
并入热固性化合物的聚合物颗粒的特征还在于含有抗聚结官能团，所述抗聚结官能团是指与环氧乙烷基团(和酯基团，如果存在的话)充分不具有反应性使得胶乳颗粒在60℃热老化稳定10天的亲水性基团。本文中使用的术语“在60℃热老化稳定10天”是指在60℃热老化稳定10天的胶乳的粒度比此类热老化研究之前的粒度增加不超过30％。基于热固性化合物和聚合物颗粒的重量，聚合物颗粒中并入的热固性化合物的浓度通常在15重量％、或20重量％、或25重量％、或30重量％至60重量％、或至55重量％的范围内。
可使用包含抗聚结官能团的单体(抗聚结单体)将抗聚结官能团并入到聚合物颗粒中，但也可通过接枝并入此类基团。认为抗聚结基团是有效的，因为其在热老化条件下是亲水的并且不与环氧乙烷基反应。此类基团的一般类别包括酰胺基、乙酰乙酰氧基和强质子酸，所述强质子酸具有小于4的pKa，其pH经调节以形成其共轭碱。
抗聚结单体的具体示例包括丙烯酰胺、甲基丙烯酸磷酸乙酯、苯乙烯磺酸钠、甲基丙烯酸乙酰乙酰氧基乙酯和丙烯酰胺基-甲基-丙烷磺酸盐。由这些单体形成的对应的抗聚结官能团(也被称为结构单元)如下所示：
虚线是指抗聚结官能单体与聚合物的连接点。应当注意，甲基丙烯酸磷酸乙酯和丙烯酰胺基-甲基-丙烷磺酸基团优选地主要以它们的共轭碱形式(即，盐形式)存在。优选的抗聚结基团是甲基丙烯酸磷酸乙酯盐基团。
基于聚合物颗粒的重量，胶乳颗粒中的抗聚结官能团的浓度通常在0.5重量％或1重量％至10重量％或至5重量％的范围内。这些颗粒可包含一定量的不抗聚结的含羧酸官能团，条件是浓度足够低以致于不破坏这些颗粒的热老化稳定性。优选地，基于具有抗聚结官能团的聚合物颗粒的重量，具有抗聚结官能团的聚合物颗粒中的羧酸官能化的浓度小于5重量％、或小于3重量％、或小于1重量％。
尽管不受理论束缚，但据信抗聚结基团可有效地稳定聚合物，因为这些基团在热老化条件下既是亲水性的又是对环氧基团不具有反应性的。在抗聚结基团由包含强质子酸基团(甲基丙烯酸磷酸乙酯、苯乙烯磺酸钠和丙烯酰胺基-甲基-丙烷磺酸)的单体产生的情况下，已经发现通过将胶乳的pH调节至高于聚质子酸(如甲基丙烯酸磷酸乙酯)的第一pKa或高于单质子酸(如苯乙烯磺酸和丙烯酰胺基-甲基-丙烷磺酸)的pKa的水平来实现胶体和热老化稳定性。如果pH太低，酸催化的环氧乙烷开环可发生-在较高pH下，此类机理不可用，并且共轭碱在热老化条件下是非亲核的。
聚合物颗粒的分散体有利地与热固性化合物组合，如US 8,658,742 B2第8栏第48-67行中所述。
用结构I的氨基烷基酯基团官能化的聚合物颗粒的分散体有利地在两个步骤中制备。在第一步骤中，制备用羧酸基团官能化的聚合物颗粒的水性分散体(羧酸官能化胶乳)。羧酸官能化胶乳优选地是丙烯酸胶乳或苯乙烯-丙烯酸胶乳，其除了包含一种或多种丙烯酸酯和甲基丙烯酸酯(包括以上列出的那些)和/或苯乙烯的结构单元之外，还包含羧酸单体，如丙烯酸、甲基丙烯酸或衣康酸的结构单元。如本文所用，指定单体的术语“结构单元”是指单体在聚合之后的残余物。例如，甲基丙烯酸的结构单元如下所示：
其中虚线表示结构单元与聚合物主链的连接点。
在第二步骤中，使羧酸官能化的胶乳与环状亚胺接触以形成用结构I的氨基烷基酯基团官能化的聚合物颗粒的水性分散体：
其中R为H或C1-C6烷基；优选地H或甲基。
用氨基烷基酯基团官能化的聚合物颗粒的分散体(氨基烷基酯官能化胶乳)优选地用氨基烷基酯基团和羧酸基团或它们的盐二者官能化；以及任选地用如上所述的包含强质子酸基团的单体官能化。氨基烷基酯基团与羧酸基团或它们的盐的摩尔:摩尔比通常在95:5、或80:20至5:95、或至30:70、或至55:45。
使包含用氨基烷基酯基团官能化的聚合物颗粒的分散体的组合物(组分A)与分散在水性介质中的热固性化合物或包含AEH的组合物(组分B)接触，以形成双组分热固性组合物。组分A还可包括其他材料，如乳浊颜料、消泡剂、聚结剂、表面活性剂、粘合促进剂、流变改性剂、溶剂和着色剂。当以AEH的形式使用时，组分B可包含选自与组分A相同的列表的另外的材料。
已经发现，与不包含用氨基烷基酯基团官能化的聚合物颗粒的双组分组合物相比，由该双组分混合物制备的涂层表现出优越的耐腐蚀性和耐起泡性。
实施例
中间体实施例1-丙烯酸-环氧杂化物分散体的制备
将苯乙烯-丙烯酸胶乳(46.0％固体，丙烯酸乙基己酯/苯乙烯/甲基丙烯酸甲酯/丙烯腈/甲基丙烯酸磷酸乙酯胶乳，其中Tg为40℃，如通过差示扫描量热法测量的，并且z平均粒度为130nm，如通过动态光散射测量的)添加到配备有浆式搅拌机、温度计、N2入口和回流冷凝器的5-L四颈圆底烧瓶(釜)中。将胶乳在N2下加热至60℃。通过混合DI水(314.53g)、Disponil AFX 4070表面活性剂(70％，120g)和D.E.R.331液体环氧树脂(800g)制备环氧乳液。将该乳液用顶置式搅拌器搅拌10分钟，并且然后使用Cat X520手持式均化器(16,000rpm)均化60秒。在2分钟内将环氧乳液添加到釜中并用DI水(234g)冲洗。将釜中的内容物搅拌60分钟，然后冷却至室温并过滤以去除任何凝结物。所得杂化物分散体具有51.9％的固体含量、7.2的pH和147nm的粒度。
中间体实施例2-羧酸官能化胶乳的分散体的制备
将DI水(1363.05g)、Disponil FES-32表面活性剂(FES-32，31％活性，8.82g)和4-羟基-TEMPO(5％，0.45g)添加到配备有桨式搅拌器、温度计、N2入口和回流冷凝器的5-L四颈圆底烧瓶(釜)中。将釜在N2下加热至85℃。通过混合DI水(440.64g)、FES-32(31％，44.09g)、丙烯酸2-乙基己酯(EHA，686.19g)、甲基丙烯酸甲酯(MMA，568.80g)、苯乙烯(451.44g)和甲基丙烯酸(MAA，72.23g)制备单体乳液(ME)。将单体乳液的一部分(3％，68.45g)装到釜中并用DI水(20g)冲洗。将过硫酸铵溶液(APS，6.36g在40g DI水中)添加到釜中，并用去离子水(10g)冲洗。观察到放热，并使放热在峰值温度下保持5分钟。将ME的剩余部分在120分钟内进料到釜中，其中温度设定为85℃，其中在第一个20分钟内以50％速率进料。同时，在120分钟内进料APS的溶液(2.73g在120g DI水中)，其中在第一个20分钟内以50％的速率进料。进料完成后，用DI水(90g)冲洗添加容器，并将反应物冷却至70℃。在冷却的同时，将七水合硫酸铁(0.15％溶液，12.12g)和VERSENETM螯合剂(1.0％溶液，1.90g，陶氏化学公司或其附属公司的商标)的溶液添加到釜中。在70℃，将叔丁基过氧化氢的追踪溶液(t-BHP，70％溶液，3.13g在40g DI水中)添加到釜中，同时在30分钟内添加异抗坏血酸的溶液(IAA，2.19g在40g DI水中)。在完成追逐剂(chaser)的添加后，通过添加氢氧化铵(30％，26.50g)将反应混合物中和至pH 7。然后，将釜中的内容物冷却至室温并过滤以去除任何凝结物。所得分散体具有44.9％的固体含量、7.1的pH和85nm的粒度。
中间体实施例3-羧酸官能化胶乳的分散体的制备
将DI水(1363.05g)、FES-32(31％，8.82g)和4-羟基-TEMPO(5％，0.45g)添加到配备有桨式搅拌器、温度计、N2入口和回流冷凝器的5-L四颈圆底烧瓶(釜)中。将釜在N2下加热至85℃。通过混合DI水(440.64g)、FES-32(31％，44.09g)、EHA(704.25g)、MMA(M478.51g)、苯乙烯(451.44g)和MAA(144.46g)来制备ME。将ME的一部分(3％，68.45g)装到釜中并用DI水(20g)冲洗。将APS的溶液(6.36g在40g DI水中)添加到釜中并用DI水(10g)冲洗。观察到放热，并使放热在峰值温度下保持5分钟。将ME的剩余部分在120分钟内进料到釜中，其中温度设定为85℃，其中在第一个20分钟内以50％速率进料。同时，在120分钟内进料APS的溶液(2.73g在120g DI水中)，其中在第一个20分钟内以50％的速率进料。进料完成后，用DI水(90g)冲洗添加容器，并将反应物冷却至70℃。在冷却的同时，将七水合硫酸铁(0.15％溶液，12.12g)和VERSENETM螯合剂(1.0％溶液，1.90g)的溶液添加到釜中。在70℃，将t-BHP的追踪溶液(70％溶液，3.13g在40g DI水中)添加到釜中，同时在30分钟内添加IAA的溶液(2.19g在40g DI水中)。在完成追逐剂(chaser)的添加后，通过添加氢氧化铵(30％，24.50g)将反应混合物中和至pH 7。然后，将釜中的内容物冷却至室温并过滤以去除任何凝结物。所得分散体具有44.7％的固体含量、7.0的pH和84nm的粒度。
中间体实施例4-胺官能化胶乳的分散体(50:50)的制备
将中间体实施例2(1000g，0.209mol MAA)装入到装配有搅拌器、温度计、冷凝器和加料漏斗的反应器中。在25℃搅拌下，在10分钟内将丙烯亚胺(19.85g，30wt％在水中，0.104mol)添加到反应器中。在30分钟内将该混合物加热至50℃，并将反应温度保持在50℃，持续60分钟。然后，将反应器的温度升高至80℃，并保持在该温度，持续60分钟。然后，将反应器逐渐冷却至25℃。分散体产物具有50:50的胺与羧酸官能化的摩尔:摩尔比，以及44.6％的固体含量。
中间体实施例5-胺官能化胶乳的分散体(75:25)的制备
重复用于制备中间体4的方法，不同之处在于使用29.77g的丙烯亚胺。分散体产物具有75:25的胺与羧酸官能化的摩尔:摩尔比，以及44.4％的固体含量。
中间体实施例6-胺官能化胶乳的分散体(50:50)的制备
将中间体实施例3(1000g，0.209mol MAA)装入到装配有搅拌器、温度计、冷凝器和加料漏斗的反应器中。在25℃搅拌下，在10分钟内将丙烯亚胺(39.57g，30wt％在水中，0.104mol)添加到反应器中。在30分钟内将该混合物加热至50℃，并将反应温度保持在50℃，持续60分钟。然后，将反应器的温度升高至80℃，并保持在该温度，持续60分钟。然后，将反应器逐渐冷却至25℃。分散体产物具有50:50的胺与羧酸官能化的摩尔:摩尔比，以及44.2％的固体含量。
表1示出了使用中间体2和其胺官能化衍生物(中间体4和5)的双组分调配物。包含中间体2(无胺官能化)的A部分调配物是比较例1和2。包含中间体4的A部分调配物是实施例1和2，并且包含中间体实施例5的A部分调配物是实施例3。
表1-双组分调配物
脱气剂是指Tego Airex 902w脱气剂；乙二醇醚是指DOWANOLTMDPnB乙二醇醚；聚结剂是指Optifilm 400聚结剂；表面活性剂是指TRITONTMHW1000表面活性剂；流变改性剂是指ACRYSOLTMRM-12W流变改性剂；粘合促进剂是指XIAMETERTMOFS-6020粘合促进剂；(DOWANOL、TRITON、ACRYSOL和XIAMETER都是陶氏化学公司或其附属公司的商标)。通过混合表2中所示的组分制备颜料研磨物A：
表2-颜料研磨物A
| 颜料研磨物A | |
| 组分 | Wt％ |
| 去离子水 | 17％ |
| 乙二醇醚 | 10.91％ |
| 聚结剂 | 3.97％ |
| 氨(28％) | 0.66％ |
| 消泡剂 | 0.43％ |
| 分散剂 | 2.73％ |
| 表面活性剂 | 0.57％ |
| Ti-Pure R-706TiO2 | 63.73％ |
| 总计 | 100％ |
消泡剂是指Tego Foamex 1488消泡剂；分散剂是指TAMOLTM681分散剂；并且TiO2是指Ti-Pure R-706TiO2；
表3示出了使用中间体3和其胺官能化衍生物(中间体6)的双组分调配物。包含中间体3(无胺官能化)的A部分调配物是比较例3和4。包含中间体6的A部分调配物是实施例4和5。
表3-双组分调配物
耐盐雾腐蚀性
使用ASTM方法B117 4进行耐盐雾性。该测试被设计成通过使涂覆的板暴露于稀盐溶液雾来确定涂层的耐腐蚀性。将涂层以2密耳至3密耳的干涂层厚度施涂到磷酸盐处理的钢板上，并在测试之前在环境条件下固化至少7天。首先将固化的经涂覆的板用胶带缠绕背面和边缘，并刻划“X”切口，使其穿过涂层到基材上。然后，将板暴露在盐雾室中。对于每种调配物，在500小时暴露后评估两个经涂覆的板。ASTM D714用于测量现场气泡和划线气泡。对于起泡评级，数字指示从0至10的起泡大小等级，其中10表示没有起泡，并且0表示最极端起泡。评级8表示肉眼容易看到的最小起泡大小。起泡等级中的字母后缀示出频率，如下：D＝稠密；MD＝中等稠密；M＝中等；F＝少量。使用ASTM D610测量耐腐蚀性。评级数指示在板的未刻划区域上的局部生锈水平，其中10表示没有局部生锈，并且0表示最极端生锈。表4展示了由表1的实施例和比较例调配物制备的涂层的盐雾评级。
表4-调配物的盐雾评级
表5展示了由表3的实施例和比较例调配物制备的涂层的盐雾评级。
表5-调配物的盐雾评级
这些数据说明了含有胺官能化粘结剂的调配物在现场腐蚀，尤其是在现场气泡和划线气泡方面的改进。
Claims (9)
1.一种组合物，所述组合物包含以下的水性分散体：a)热固性化合物；
和b)用以下类型的氨基烷基酯基团官能化的聚合物颗粒：
其中R为H或C1-C6烷基。
2.根据权利要求1所述的组合物，其中所述热固性化合物是环氧酚醛树脂、或二缩水甘油醚、三缩水甘油醚或四缩水甘油醚、或二缩水甘油酯、三缩水甘油酯或四缩水甘油酯、或它们的组合。
3.根据权利要求1所述的组合物，其中所述热固性化合物是二缩水甘油醚，所述二缩水甘油醚是双酚A的二缩水甘油醚、双酚F的二缩水甘油醚、1,4-丁二醇二缩水甘油醚或1,6-己二醇二缩水甘油醚或它们的组合。
4.根据权利要求1所述的组合物，其中所述热固性化合物是双酚A的二缩水甘油醚，所述双酚A的二缩水甘油醚并入到用抗聚结基团官能化的胶乳聚合物颗粒中；其中基于所述热固性化合物和所述胶乳聚合物颗粒的重量，所述胶乳聚合物颗粒中并入的双酚A的二缩水甘油醚的浓度在15重量％至60重量％的范围内。
5.根据权利要求1至4中任一项所述的组合物，其中R为CH3。
6.根据权利要求1所述的组合物，其中所述用氨基烷基酯基团官能化的聚合物颗粒也用羧酸基团或它们的盐官能化，其中氨基烷基酯基团与羧酸基团或它们的盐的摩尔:摩尔比在95:5至5:95的范围内。
7.根据权利要求5所述的组合物，其中所述用氨基烷基酯基团官能化的聚合物颗粒也用羧酸基团或它们的盐官能化，其中氨基烷基酯基团与羧酸基团或它们的盐的摩尔:摩尔比在80:20至45:55的范围内。
8.根据权利要求7所述的组合物，其中所述用氨基烷基酯基团官能化的聚合物颗粒也用包含强质子酸基团或它们的盐的单体官能化。
9.根据权利要求7所述的组合物，其中所述用氨基烷基酯基团官能化的聚合物颗粒也用甲基丙烯酸磷酸乙酯或其盐官能化。
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