CN117203253A - 羟基官能硫醚化合物及其在可固化组合物中的用途 - Google Patents
羟基官能硫醚化合物及其在可固化组合物中的用途 Download PDFInfo
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- CN117203253A CN117203253A CN202280031151.6A CN202280031151A CN117203253A CN 117203253 A CN117203253 A CN 117203253A CN 202280031151 A CN202280031151 A CN 202280031151A CN 117203253 A CN117203253 A CN 117203253A
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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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- 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
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/50—Multilayers
- B05D7/52—Two layers
- B05D7/53—Base coat plus clear coat type
- B05D7/536—Base coat plus clear coat type each layer being cured, at least partially, separately
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
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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
- C08G18/003—Polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen
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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
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- C08G18/22—Catalysts containing metal compounds
- C08G18/227—Catalysts containing metal compounds of antimony, bismuth or arsenic
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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
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- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
-
- 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
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- C08G18/4676—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing sulfur
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Abstract
本发明涉及具有式(I)的羟基官能硫醚化合物，其中Z为n价烃基，任选含有一个或多个选自醚结构部分、硫醚结构部分和异氰脲酸酯结构部分的结构部分；R1为线性或支化亚烷基；R2选自CH2CH(OH)CH2和CH(CH2OH)CH2；R3为线性或支化烷基；m＝0或1；以及n＝2‑10。本发明进一步提供了一种生产该化合物的方法，一种含有该化合物的可热固化组合物以及羟基官能硫醚化合物在可热固化组合物中作为反应性稀释剂的用途。进一步提供了多层涂层，其中至少一层由该组合物形成，如此多层涂敷的基材以及一种生产该多层涂层的方法。
Description
本发明涉及羟基官能化合物、其制备及其在可热固化组合物中的用途以及该类组合物。本发明进一步涉及多层涂层，其中至少一层由该组合物形成，如此涂敷的基材以及一种生产该多层涂层的方法。
技术背景
商业涂料组合物通常可以归入物理干燥和化学交联涂料组合物之下。在化学交联涂料组合物中区分为可辐射固化涂料组合物，其中借助辐射如UV辐射引发交联，和可热固化涂料组合物，其中通常通过优选聚合物质的自交联或带有官能基团的聚合物与带有与上述聚合物的官能基团反应的官能基团的所谓交联剂的交联实现交联，由此形成固化的，即交联的涂层。
本发明属于后一类型的热交联涂料组合物领域。它们可以配制成单包装或双包装组合物，在这二者中用交联剂交联基本聚合物质。
在该类现有技术组合物中，聚合物基料通常带有羟基，而交联剂属于游离或封闭型二异氰酸酯和/或多异氰酸酯组或者属于氨基塑料树脂如蜜胺-甲醛树脂组。
在许多情况下，待用交联剂交联的聚合物主基料基本决定了该涂料组合物的粘度并且因此限制了可能的施用方法。为了克服该问题，通常利用低分子量物质，后者与其中仅使用较高分子量聚合物基料的体系相比易于降低粘度。由于需要将该类低分子量物质并入交联网络中，它们通常带有也对交联剂中所含反应性基团呈反应性的基团。由于其粘度降低效果，即稀释效果及其反应性，该类低分子量物质也称为反应性稀释剂。
除了它们在降低可交联组合物的粘度中的用途外，它们还可以用于增加组合物的固体含量，由此替代有机挥发性成分如有机溶剂。因此，该类组合物与通常包含显著更高量的挥发性有机化合物—所谓的VOC的传统组合物相比更为环境友好。
WO 2013/072481 A1公开了可以作为多元醇，即甘油与羧酸缩水甘油酯的反应产物得到的反应性稀释剂。如此得到的反应性稀释剂包含对选自多异氰酸酯、氨基塑料树脂或三嗪类如TACT的交联剂呈反应性的羟基。反应性稀释剂和交联剂的该组合可以用于适合作为涂料组合物、粘合剂和密封剂的组合物，特别是进一步含有羟基官能聚合物的那些中。WO 2013/072481A1中公开的涂料组合物具有良好的流平性能。
还已知在可固化双包装组合物中将硫醇官能反应性稀释剂与羟基官能基料一起或单独使用，因为已知硫醇基团以及羟基与带有异氰酸酯基团的交联剂反应。在这类情况下构建含有硫尿烷基团的聚合物网络。在该类反应中将含有两个或更多个硫醇基团的化合物与羟基官能基料一起使用通常加快反应速率，但也降低气泡形成，甚至在厚层中降低气泡形成，由此得到改进的固化产品。该类低分子量聚硫醇例如可以由Bruno BockChemische Fabrik GmbH&Co.KG，Marschacht，德国以商品名得到。
在再一现有技术方法中，使上述低分子量聚硫醇直接与聚环氧化物反应，由此产生含有硫醚连接和羟基的交联网络。
然而，在上述施用体系二者中，将具有游离硫醇基团的化合物用于交联反应中。该类组分通常具有异味并且要在目标体系重避免。
本发明的目的是要提供一类新的反应性稀释剂。然而，本发明的另一目的是要提供产生具有优异的耐化学性和抗划伤性的固化网络的可交联组合物。该类组合物应进一步显示流平性能和抗流挂性之间的良好平衡，优选在更高膜厚下，这二者通常是竞争性性能。
概述
上述目的通过提供具有式(I)的羟基官能硫醚化合物实现：
其中
Z为n价烃基，任选含有一个或多个选自醚结构部分、硫醚结构部分和异氰脲酸酯结构部分的结构部分；
R1为线性或支化亚烷基；
R2选自CH2CH(OH)CH2和CH(CH2OH)CH2；
R3为线性或支化烷基；
m＝0或1；和
n＝2-10。
上述式(I)的羟基官能硫醚化合物在本文中也表示为“本发明羟基官能硫醚化合物”或“本发明反应性稀释剂”。
本发明的另一目的是一种生产本发明羟基官能硫醚化合物的方法，其中使一种或多种物质Z-[O(C＝O)R1)m-SH]n与一种或多种式(II)的物质反应：
并且在m＝1的情况下该一种或多种物质Z-[O(C＝O)R1)m-SH]n可以通过使一种或多种物质Z[OH]n与n种物质HOOC-R1-SH反应而得到；其中Z、R1、R3、m和n如对本发明羟基官能硫醚化合物所定义。
上述生产本发明羟基官能硫醚化合物的方法在本文中也表示为“本发明生产方法”。
本发明的另一目的是一种可热固化组合物，包含：
(A)一种或多种本发明羟基官能硫醚化合物；和
(B)一种或多种对该一种或多种羟基官能硫醚(A)的羟基呈反应性的交联剂。
上述可热固化组合物在本文中也表示为“本发明可热固化组合物”或者仅表示为“本发明可固化组合物”。
本发明的再一目的是本发明羟基官能硫醚在可热固化组合物中作为反应性稀释剂的用途。
上述用途在本文中也表示为“本发明用途”。
本发明进一步提供了一种包含至少两个涂层的多层涂层，其中至少一层由可热固化组合物形成，以及如此涂敷的基材，在本文中表示为“本发明多层涂层”和“本发明多层涂敷基材”。
本发明的另一目的是一种在基材上生产本发明多层涂层的方法，该方法包括下列步骤：
(i)在基材上施用至少一种底涂层组合物而形成底涂层并随后
(ii)在该底涂层组合物上施用至少一种面漆组合物而形成面漆层，然后
(iii)在20-200℃范围内的温度下固化完全固化的涂层，
其中至少一种底涂层组合物或至少一种面漆组合物为本发明可热固化组合物。
详细说明
在下文中通过参考优选特征和实施方案更详细描述本发明。
式(I)的羟基官能硫醚化合物
优选在式(I)的羟基官能硫醚化合物中，
Z为含有2-16个碳原子的n价烃基，其任选含有一个或多个醚结构部分和/或一个或多个硫醚结构部分；和/或
R1为含有1-6个碳原子的线性或支化亚烷基；和/或
R2选自CH2CH(OH)CH2和CH(CH2OH)CH2；和/或
R3为1-16个碳原子的线性或支化烷基；和/或
m＝0或1；和/或n＝2-8。
应强调的是在前一段落中由“和/或”分隔的优选限制是相互独立的并且这些限制中的每一个可以独立地与另一个或上面在大字标题“概述”下发现的式(I)的更宽定义结合。然而，特别优选所有上述限制在本发明羟基官能硫醚化合物的一个实施方案中结合，即“和/或”由“和”替代。
甚至更优选该n价烃基Z含有2-10个碳原子；和/或该线性或支化亚烷基R1含有1-3个碳原子，如1、2或3个碳原子；和/或该线性或支化烷基R3含有1-10个，优选3-9个碳原子；和/或n＝2-6。再有，由“和/或”分隔的这些限制是相互独立的并且这些限制中的每一个可以独立地与另一个或者上述实施方案中的任一个结合。然而，特别优选在本段中的所有限制在本发明羟基官能硫醚化合物的一个实施方案中结合，即“和/或”由“和”替代。
在本发明羟基官能硫醚化合物的任一种中，R2优选为CH2CH(OH)CH2。
若在上面的式(I)中m＝1，则Z优选为n价烃基或含有一个或多个醚结构部分的n价烃基；同时，若在上面的式(I)中m＝0，则Z优选为含有一个或多个硫醚结构部分的n价烃基。
在本发明的所有实施方案中，n价烃基Z优选为包括脂环族烃基的脂族烃基，最优选饱和脂族烃基。n价烃基Z的优选实例如下。上述烃基可以任选含有一个或多个选自醚结构部分、硫醚结构部分和异氰脲酸酯结构部分的结构部分。
对于n＝2，基团Z优选为具有2-10个，更优选2-8个，最优选2-6个，如2、3或4个碳原子的线性或支化亚烷基；或者具有4-10个，更优选4-8个，最优选4-6个碳原子的线性或支化亚烷基醚基团。
对于n＝3，基团Z优选选自H2C-CH-CH2、
对于n＝4，基团Z优选选自
对于n＝6，基团Z优选为
最优选式(I)中的基团R3-C(＝O)O为三烷基乙酸酯基团，甚至更优选衍生于新癸酸的所谓新癸酰基。本文中新癸酸表示具有共同结构式C10H20O2、分子量为172.26g/mol且CAS号为26896-20-8的羧酸或羧酸混合物。新癸酸的共同性能是它们可以归入在键合于COOH基团的碳上具有3个烷基的通用术语“三烷基乙酸”。新癸酸通常包括2,2,3,5-四甲基己酸、2,4-二甲基-2-异丙基戊酸、2,5-二甲基-2-乙基己酸、2,2-二甲基辛酸和2,2-二乙基己酸。
生产式(I)的羟基官能硫醚化合物的方法
上面所定义的羟基官能硫醚化合物可以通过使(a)一种或多种物质Z-[O(C＝O)R1)m-SH]n与(b)一种或多种式(II)的物质反应而生产：
其中Z、R1、R3、m和n如对本发明羟基官能硫醚化合物所定义。
在该反应中，SH基团引起存在于式(II)中的环氧乙烷环开环，由此形成残基R2。在大多数情况下，开环导致残基R2为CH2CH(OH)CH2，因此含有仲OH基团。然而，在一些情况下开环导致形成含有伯OH基团的残基CH(CH2OH)CH2，其中在目标化合物中“CH”结构部分通常键合于相邻S原子且该结构部分的末端CH2基团键合于相邻O原子。然而，这两种反应均导致形成易于与本发明可热固化组合物中的相应交联剂反应的OH基团。
在m＝1的情况下，该一种或多种物质Z-[O(C＝O)R1)m-SH]n可以通过使一种或多种物质Z[OH]n与n种物质HOOC-R1-SH反应而得到；其中Z、R1、m和n如对本发明羟基官能硫醚化合物所定义。然而，多种其中m＝1的式Z-[O(C＝O)R1)m-SH]n的物质由Bruno BockChemische Fabrik GmbH&Co.KG，Marschacht，德国以商品名市购。
典型且优选的物质Z[OH]n例如是具有2-10个碳原子的亚烷基二醇，如乙二醇、丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、新戊二醇、2-丁基-2-乙基-1,3-丙二醇和二羟甲基环己烷；二甘醇、三甘醇、二丙二醇、三丙二醇、甘油、双甘油、三羟甲基丙烷、三羟甲基乙烷、糖醇、异氰脲酸三羟乙基酯、二(三羟甲基丙烷)、季戊四醇和二(季戊四醇)。
典型且优选的物质HOOC-R1-SH是巯基乙酸、2-巯基丙酸、3-巯基丙酸或巯基丁酸如3-巯基丁酸。
该一种或多种式(II)的物质是支化或线性链烷酸(R3COOH)，优选支化链烷酸的缩水甘油酯，其中R3如对本发明羟基官能硫醚化合物所定义。优选该一种或多种式(II)的物质是三烷基乙酸的缩水甘油酯，甚至更优选新癸酸的缩水甘油酯。该类物质例如以商品名E10由Hexion，Inc.市购。
该一种或多种物质Z-[O(C＝O)R1)m-SH]n和该一种或多种式(II)的物质之间的反应优选在存在在该反应中呈惰性的有机溶剂下进行。该类溶剂例如是烃类，如溶剂石脑油。优选将该一种或多种物质Z-[O(C＝O)R1)m-SH]n称入反应容器中并且在搅拌的同时缓慢加入该一种或多种式(II)的物质。优选在惰性气体气氛如氮气气氛下进行该反应。通常无需加热反应混合物。进行该反应直到已经消耗基本所有硫醇基团。该反应可以在催化剂存在下进行，优选碱如叔胺或四甲基胍作为催化剂。
可热固化组合物
可热固化组合物可以是单包装组合物或双包装组合物。它们优选为溶剂基涂料组合物。
如教科书“Rompp Lexikon Lacke und Druckfarben”，Thieme，1998所定义的术语“单包装组合物”是指与下面所述的双包装组合物相反，以它们在一种组合物中含有基础树脂和交联剂而不会在成分之间具有过早反应的方式生产和供应的组合物，特别是涂料组合物。反应优选通过加热或烘烤引起。
本文所用术语“双包装组合物”是指包含至少两个包装的组合物，特别是涂料组合物，各包装在储存条件下稳定，但含有在混合之后相互反应的成分。该至少两个包装中的任一个单独地通常不易提供合适的涂层、粘合剂层或密封剂。在本发明中优选组合物为双包装组合物。
本发明可热固化组合物包含一种或多种本发明羟基官能硫醚化合物；以及一种或多种对该一种或多种羟基官能硫醚化合物的羟基呈反应性的交联剂。可热固化组合物可以进一步含有额外基料，例如选自聚合物多元醇或典型的添加剂。此外，可以含有有机溶剂和/或着色剂和填料。
可热固化组合物优选为涂料组合物、粘合剂组合物或密封剂组合物，最优选涂料组合物。
交联剂(B)
二异氰酸酯和多异氰酸酯
当本发明可热固化组合物为双包装组合物时，二异氰酸酯和/或多异氰酸酯中所含异氰酸酯基团为游离异氰酸酯基团。
最优选用于本发明可热固化双包装组合物中的交联剂是二异氰酸酯和/或多异氰酸酯。如本文所定义的多异氰酸酯平均具有大于两个游离异氰酸酯基团。
尽管本发明的二异氰酸酯和/或多异氰酸酯可以是芳族多异氰酸酯如甲苯二异氰酸酯及其二聚体、三聚体和聚合物，但更优选在本发明的可热固化双包装组合物中使用脂族二异氰酸酯和/或脂族多异氰酸酯。不太优选使用芳族多异氰酸酯，因为由包含芳族多异氰酸酯的涂料得到的涂层倾向于不利地泛黄。因此，不太优选在涂料中使用芳族二异氰酸酯和/或芳族多异氰酸酯。
脂族二异氰酸酯和脂族多异氰酸酯分别在本文中应理解为是在分子中具有至少两个游离异氰酸酯基团，具体为至少三个游离异氰酸酯基团，即在室温(25℃)下未被封闭的异氰酸酯基团的化合物。术语“脂族多异氰酸酯”还理解为脂族二异氰酸酯的二聚体、三聚体和聚合物。其实例是六亚甲基二异氰酸酯(HDI)的二聚体、三聚体和聚合物，包括例如其二氮杂环丁二酮类以及更特别是其异氰脲酸酯类和亚氨基二嗪二酮类，其中亚氨基二嗪二酮类最合适，若需要特别低的粘度的话。
在本文中术语“脂族”还包括术语“脂环族”，如更具体为异佛尔酮二异氰酸酯(IPDI)及其二聚体、三聚体和聚合物，或者环己烷(二烷基异氰酸酯)以及还有其二聚体、三聚体和聚合物。
优选的脂族未封闭多异氰酸酯是HDI的三聚体，例如作为来自BASF SE(德国Ludwigshafen)的Basonat HI 100、来自Bayer Material Science AG(德国Leverkusen)的N 3300和/>XP 2410或者来自Perstorp AB(瑞典Perstorp)的HDT和HDB以及还有来自Asahi Kasei Chemicals，Kawasaki，日本的商品名为TLA、/>TKA或/>MHG的类似产品。
当本发明的可热固化组合物为单包装组合物时，二异氰酸酯和/或多异氰酸酯中所含异氰酸酯基团不是游离的，而是封闭型异氰酸酯基团。在使游离异氰酸酯基团与封闭剂反应之后，通常可以将所有上述二异氰酸酯和多异氰酸酯用作所谓的封闭型二异氰酸酯和封闭型多异氰酸酯。
用于制备封闭型二异氰酸酯和封闭型多异氰酸酯的封闭剂例如为：
i.酚类、吡啶醇类、苯硫酚类和巯基吡啶类，优选选自苯酚、甲酚、二甲酚、硝基苯酚、氯酚、乙基苯酚、叔丁基苯酚、羟基苯甲酸、该酸的酯、2,5-二叔丁基-4-羟基甲苯、苯硫酚、甲基苯硫酚和乙基苯硫酚；
ii.醇类和硫醇类，醇类优选选自甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、叔丁醇、正戊醇、叔戊醇、月桂醇、乙二醇单甲基醚、乙二醇单乙基醚、乙二醇单丙基醚、乙二醇单丁基醚、二甘醇单甲基醚、二甘醇单乙基醚、二甘醇单丙基醚、二甘醇单丁基醚、丙二醇单甲基醚、甲氧基甲醇、2-(羟基乙氧基)苯酚、2-(羟基丙氧基)苯酚、乙醇酸、乙醇酸酯、乳酸、乳酸酯、羟甲基脲、羟甲基蜜胺、双丙酮醇、氯乙醇、溴乙醇、1,3-二氯-2-丙醇、1,4-环己基二甲醇或乙酰氰醇，并且硫醇类优选选自丁基硫醇、己基硫醇、叔丁基硫醇、叔十二烷基硫醇；
iii.肟类，优选选自四甲基环丁烷二酮的酮肟、甲基正戊基酮肟、甲基异戊基酮肟、甲基3-乙基庚基酮肟、甲基2,4-二甲基戊基酮肟、甲基乙基酮肟、环己酮肟、甲基异丙基酮肟、甲基异丁基酮肟、二异丁基酮肟、甲基叔丁基酮肟、二异丙基酮肟和2,2,6,6-四甲基环己酮的酮肟的酮肟类；或者醛肟类，优选选自甲醛肟、乙醛肟；
iv.酰胺类、环状酰胺类和酰亚胺类，优选选自内酰胺，如ε-己内酰胺、δ-戊内酰胺、γ-丁内酰胺或β-丙内酰胺；酸酰胺类如乙酰苯胺、乙酰茴香胺酰胺(acetoanisidinamide)、丙烯酰胺、甲基丙烯酰胺、乙酰胺、硬脂酰胺或苯甲酰胺；以及酰亚胺类如琥珀酰亚胺、邻苯二甲酰亚胺或马来酰亚胺；
v.咪唑类和脒类；
vi.吡唑类和1,2,4-三唑类，如3,5-二甲基吡唑和1,2,4-三唑；
vii.胺类和亚胺类，如二苯胺、苯基萘胺、二甲苯胺、N-苯基二甲苯胺、咔唑、苯胺、萘胺、丁胺、二丁胺、丁基苯胺和乙烯亚胺；
viii.咪唑类如咪唑或2-乙基咪唑；
ix.脲类如脲、硫脲、亚乙基脲、亚乙基硫脲或1,3-二苯基脲；
x.活性亚甲基化合物，如丙二酸二烷基酯如丙二酸二乙酯，乙酰乙酸酯；和
xi.其他如异羟肟酸酯，例如甲基丙烯酰异羟肟酸苄基酯(BMH)或甲基丙烯酰异羟肟酸烯丙酯，以及氨基甲酸酯如N-苯基氨基甲酸苯基酯或2-唑烷酮。
其他交联剂
还可以使用分别不同于上述游离和封闭型二异氰酸酯和多异氰酸酯的交联剂。就此而言尤其有利的是在与游离或封闭型二异氰酸酯和/或游离或封闭型多异氰酸酯相同的温度范围内，即在20-200℃范围内与反应性稀释剂或其他基料发生固化反应的那些。该类交联剂的实例包括如WO 2008/074489、WO 2008/074490和WO 2008/074491所述类型的含有甲硅烷基的组分。
用于单包装涂料的其他优选交联剂是具有活性羟甲基、甲基烷氧基或丁基烷氧基的氨基塑料交联剂以及封闭型多异氰酸酯交联剂，它们例如对羟基呈反应性。
氨基塑料或氨基树脂描述于Encyclopedia of Polymer Science andTechnology，第1卷，第752-789页(1985)中。氨基塑料通过使活化氮与更低分子量醛反应，任选与醇(优选具有1-4个碳原子的一元醇如甲醇、异丙醇、正丁醇、异丁醇等)进一步反应以形成醚基团而得到。活性氮的优选实例是活性胺如蜜胺、苯并胍胺、环己基羰基胍胺和乙酰胍胺；脲类，包括脲本身、硫脲、亚乙基脲、二羟基亚乙基脲和脒基脲；甘脲；酰胺类，如双氰胺；以及具有至少一个伯氨基甲酸酯基团或至少两个仲氨基甲酸酯基团的氨基甲酸酯官能化合物。使该活性氮与更低分子量醛反应。该醛可以选自甲醛、乙醛、巴豆醛、苯甲醛或用于制造氨基塑料树脂的其他醛，但优选甲醛和乙醛，尤其是甲醛。活性氮基团至少部分用该醛羟烷基化并且可以完全羟烷基化；优选将活性氮完全羟烷基化。该反应例如可以如作为参考引入本文的美国专利3,082,180所教导的那样由酸催化。
其他聚合物基料(C)
除了该一种或多种本发明羟基官能硫醚化合物和交联剂外，不同于上述羟基官能硫醚化合物和交联剂的其他聚合物基料可以含于本发明可热固化组合物中。
在优选含于本发明可热固化组合物中的其他聚合物基料中，特别优选羟基官能聚合物基料，即“聚合物多元醇”。优选聚合物多元醇不含硫。
“聚合物多元醇”在本文中是指具有至少两个羟基的多元醇，术语“聚合物”在本文还包括术语“低聚物”。低聚物在本文中由至少三个单体单元构成。
优选聚合物多元醇具有>500Da，具体为800-100,000Da，更具体为1,000-50,000Da的重均分子量Mw，这使用聚苯乙烯标样借助GPC(凝胶渗透色谱法)测定。甚至更优选聚合物多元醇是重均分子量为1,000-10,000Da的那些。
优选聚合物多元醇具有30-350mg KOH/g，更优选80-250mg KOH/g，特别优选100-180mg KOH/g的羟值(OH数)。羟值表示等同于在乙酰化时由1g物质所结合的乙酸量的氢氧化钾mg数。使该样品与乙酸酐-吡啶沸腾以用于测定并将所得酸用氢氧化钾溶液滴定(DIN53240-2)。
聚合物多元醇优选选自包含聚(甲基)丙烯酸系多元醇、聚酯多元醇、聚醚多元醇、聚醚-聚酯多元醇和聚氨酯多元醇的组或者由其构成的组。
优选聚合物多元醇为聚(甲基)丙烯酸酯多元醇。本文所用术语“聚(甲基)丙烯酸酯”不仅是指聚丙烯酸酯而且还指聚甲基丙烯酸酯以及还有包含甲基丙烯酸酯和/或甲基丙烯酸和丙烯酸酯和/或丙烯酸二者的聚合物。除了丙烯酸、甲基丙烯酸和/或丙烯酸酯和/或甲基丙烯酸酯外，聚(甲基)丙烯酸酯还可以包含其他烯属不饱和单体。在一个或多个实施方案中，由其得到聚(甲基)丙烯酸酯的单体为单烯属不饱和单体。“聚(甲基)丙烯酸酯多元醇”是指含有至少两个羟基的聚(甲基)丙烯酸酯。它们可以在一步或多步中制备。它们还可以以例如无规聚合物、梯度共聚物、嵌段共聚物或接枝聚合物的形式存在。
聚(甲基)丙烯酸酯多元醇中的羟基通过在聚合反应中使用羟基官能单体而引入该聚合物中。使用的聚(甲基)丙烯酸酯多元醇的含羟基单体优选选自(甲基)丙烯酸羟烷基酯，如更具体为丙烯酸2-羟基乙基酯、甲基丙烯酸2-羟基乙基酯、丙烯酸2-羟基丙基酯、甲基丙烯酸2-羟基丙基酯、丙烯酸3-羟基丙基酯、甲基丙烯酸3-羟基丙基酯、丙烯酸3-羟基丁基酯、甲基丙烯酸3-羟基丁基酯以及尤其还有丙烯酸4-羟基丁基酯和/或甲基丙烯酸4-羟基丁基酯。尤其还可以有利地使用由工业制备得到的混合物。因此，例如工业制备的甲基丙烯酸羟基丙基酯由约20-30％甲基丙烯酸3-羟基丙基酯和70-80％甲基丙烯酸2-羟基丙基酯构成。
作为合成聚(甲基)丙烯酸酯多元醇的其他单体，可以使用(甲基)丙烯酸烷基酯，如丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸丙酯、甲基丙烯酸丙酯、丙烯酸异丙酯、甲基丙烯酸异丙酯、丙烯酸丁酯、甲基丙烯酸丁酯、丙烯酸异丁酯、甲基丙烯酸异丁酯、丙烯酸叔丁酯、甲基丙烯酸叔丁酯、丙烯酸戊酯、甲基丙烯酸戊酯、丙烯酸己酯、甲基丙烯酸己酯、丙烯酸乙基己基酯、甲基丙烯酸乙基己基酯、丙烯酸3,3,5-三甲基己基酯、甲基丙烯酸3,3,5-三甲基己基酯、丙烯酸硬脂基酯、甲基丙烯酸硬脂基酯、丙烯酸月桂基酯或甲基丙烯酸月桂基酯，丙烯酸环烷基酯和/或甲基丙烯酸环烷基酯，如丙烯酸环戊基酯、甲基丙烯酸环戊基酯、丙烯酸异冰片基酯、甲基丙烯酸异冰片基酯或者尤其是丙烯酸环己酯和/或甲基丙烯酸环己酯。
作为合成聚(甲基)丙烯酸酯多元醇的其他单体，可以使用乙烯基芳族烃类，如乙烯基甲苯、α-甲基苯乙烯或者尤其是苯乙烯，丙烯酸或甲基丙烯酸的酰胺类或腈类，乙烯基酯或乙烯基醚以及尤其还有少量的丙烯酸和/或甲基丙烯酸。
进一步可能的是使用通过使用含羟基或羧基的单体制备的聚(甲基)丙烯酸酯多元醇，其中该聚合单体的至少一部分OH和/或COOH基团用含有单环氧乙烷基团的单体如上面所定义的式(II)的物质改性。该类改性例如描述于Z.W.J.Wicks，F.N.Jones，S.P.Pappas和D.A.Wicks，Organic Coatings-Science and technology，Hoboken，New Jersey:Wiley，2007；或H.Petit，N.Henry，A.Krebs，G.Uytterhoeven和F.de Jong，“Ambient cure highsolids acrylic resins for automotive refinish clear coat applications”，Progress in Organic Coatings，第41-49页，2001；以及WO 2003/011923A1(见第8页和随后页的实施例)中。
代替或者除了聚(甲基)丙烯酸酯多元醇外，还可以使用聚酯多元醇。聚酯多元醇在这里是带有至少两个羟基的聚酯。
在联合使用聚(甲基)丙烯酸酯多元醇和聚酯多元醇的情况下，这两种组分可以单独制备或者通过在聚酯多元醇组分或其在合适溶剂中的溶液中原位聚合聚(甲基)丙烯酸酯多元醇而制备。
该类聚(甲基)丙烯酸系多元醇中的羟基可以通过使这些与缩水甘油酯，如上面式(II)化合物至少部分反应而进一步改性。还可以使用尿素晶体改性的聚(甲基)丙烯酸系多元醇。
合适的聚酯多元醇例如描述于EP-A-0 994 117和EP-A-1 273 640中。尤其可以通过缩聚而由多元醇和多羧酸或其酸酐得到本领域普通技术人员已知的合适聚酯多元醇。
特别适合作为可以用于缩聚反应以生产聚酯多元醇的多元醇或多元醇混合物是多羟基醇及其混合物，该醇类具有至少两个，优选至少三个羟基。在一个或多个实施方案中，所用多元醇混合物或所用多元醇包含或者为至少一种含有至少三个羟基的多官能多元醇。合适的具有至少三个羟基的多官能多元醇选自三羟甲基丙烷(TMP)、三羟甲基乙烷(TME)、甘油、季戊四醇、糖醇、二-三羟甲基丙烷、二季戊四醇、双甘油、异氰脲酸三羟乙基酯及其混合物。在一个具体实施方案中，用于制备聚酯多元醇的多元醇仅由具有多于三个羟基的多官能多元醇构成。在另一具体实施方案中，用于制备聚酯多元醇的多元醇混合物包含至少一种具有至少三个羟基的多官能多元醇和至少一种二醇。合适二醇的实例包括乙二醇、丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、新戊二醇、2-丁基-2-乙基-1,3-丙二醇、二甘醇、二丙二醇、更高级聚醚二醇、二羟甲基环己烷和上述多元醇的混合物。
适合制备聚酯多元醇的多羧酸或其酸酐为例如邻苯二甲酸、邻苯二甲酸酐、间苯二甲酸、对苯二甲酸、偏苯三甲酸、偏苯三酸酐、均苯四甲酸、均苯四酸二酐、四氢邻苯二甲酸、1,2-、1,3-或1,4-环己烷二甲酸、1,2-环己烷二甲酸酐、三环癸烷二甲酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、马来酸、马来酸酐、富马酸、衣康酸、中康酸、柠康酸、二聚脂肪酸及其混合物。
当本发明涂料组合物除了可以归入聚合物多元醇的术语之下的基料外进一步包含额外的基料时，这些其他基料可以与涂料的其他组分反应或者对所述组分呈化学惰性。
该类基料可以包括物理干燥基料，即对其他漆成分呈化学惰性的基料，例如醋酸丁酸纤维素(CAB)、聚酰胺或聚乙烯醇缩丁醛。
添加剂
此外，可热固化组合物还可以包含其他典型添加剂，特别是不同于上述组分的涂料用添加剂。任何添加剂不同于前文所述基料(A)、(B)和(C)。
合适的涂料添加剂的实例为：
-尤其是UV吸收剂，如2-(2-羟基苯基)苯并三唑类、2-羟基二苯甲酮类、羟苯基-s-三嗪类和草酰二苯胺类；
-尤其是光稳定剂，如已知为HALS化合物(“受阻胺光稳定剂”；这些为2,2,6,6-四甲基哌啶衍生物；例如作为292由BASF SE市购)的那些，苯并三唑类，如羟苯基烷基苯并三唑，或草酰二苯胺类；
-自由基清除剂；
-滑爽添加剂；
-阻聚剂；
-消泡剂；
-反应性稀释剂，更具体为仅通过与其他成分和/或水反应而变为反应性的反应性稀释剂，如唑烷类(如/>)或天冬氨酸酯；
-润湿和分散剂，如硅氧烷、含氟化合物、羧酸单酯、磷酸酯、聚丙烯酸及其共聚物或者聚氨酯；
-助粘剂；
-流动控制剂，尤其是基于聚丙烯酸酯的那些。在本文优选使用的是丙烯酸乙基己基酯和丙烯酸乙酯的共聚物。这些共聚物优选具有非常低的TG，相对非极性并且具有低OH数；
-成膜助剂如纤维素衍生物；
-流变控制添加剂，如由专利WO 94/22968、EP-A-0 276 501、EP-A-0 249
201或WO 97/12945已知的添加剂；例如如EP-A-0 008 127所公开的交联聚合物微粒；无机页硅酸盐如蒙脱石类型的硅酸铝镁、页硅酸钠镁和页硅酸钠镁氟锂；硅石如具有离子性和/或缔合基团的合成聚合物，如聚(甲基)丙烯酰胺、聚(甲基)丙烯酸、聚乙烯基吡咯烷酮、苯乙烯-马来酸酐共聚物或乙烯-马来酸酐共聚物及其衍生物，或者疏水改性乙氧基化尿烷，或聚丙烯酸酯；以及
-阻燃剂。
着色剂和填料
本发明可热固化组合物可以进一步包含着色剂如可溶性染料、颜料或填料。若将可热固化组合物用作透明涂料组合物，则它们不含或基本不含不透明颜料和填料。然而，可以使用基于二氧化硅、氧化铝或氧化锆的纳米颗粒形式的填料(进一步的详情参考Lexikon“Lacke und Druckfarben”Georg Thieme Verlag，Stuttgart，1998，第250-252页)。
溶剂
组合物尤其还可以包含溶剂。合适的溶剂包括所有典型的漆溶剂，如更具体为芳族烃类或乙酸丁酯。
溶剂优选为极性有机溶剂和/或芳族溶剂。有用的溶剂是酮类、酯类、乙酸酯类、非质子酰胺类、非质子亚砜类和非质子胺类、脂族和/或芳族溶剂。具体有用溶剂的实例包括酮类，如丙酮、甲基乙基酮、甲基戊基酮、甲基异丁基酮，酯类，如乙酸乙酯、乙酸丁酯、乙酸戊酯、乙氧基丙酸乙酯、乙二醇丁基醚乙酸酯、丙二醇单甲基醚乙酸酯，脂族和/或芳族烃类，如甲苯、二甲苯、溶剂石脑油和矿油精，醚类，如二醇醚类如丙二醇单甲基醚，醇类，如乙醇、丙醇、异丙醇、正丁醇、异丁醇和叔丁醇或烷氧基链烷醇，如甲氧基丙醇或二丙二醇单甲基醚，含氮化合物，如N-甲基吡咯烷酮和N-乙基吡咯烷酮以及这些的组合。
可热固化组合物中各组分的量和比率
优选本发明羟基官能硫醚化合物基于该组合物中基料的总重量以0.1-70重量％，更优选1-50重量％，最优选2-30重量％或者甚至更好的是3-15重量％的量存在于本发明可热固化组合物中。基料的量(即基料含量)为该组合物的固体含量减去颜料和填料的量。固体含量确定为在将该组合物在130℃下干燥60分钟之后1g该组合物留下的部分。颜料和填料的量为该组合物中所用颜料和填料的称重干燥量。在无颜料和无填料组合物，如透明涂料组合物中，基料含量等于固体含量。
其他成分如交联剂(B)、其他聚合物基料(C)、添加剂、着色剂、填料和溶剂的量范围内并不特别重要。交联剂(B)的量范围通常由本发明羟基官能硫醚化合物和其他聚合物基料(C)的选取量得到。若涂料组合物例如包含颜料和填料，则可能需要使用添加剂如润湿和分散剂来保持颜料和填料分散。由于本发明羟基官能硫醚化合物也用作溶剂(反应性稀释剂)，通常可以改变并且优选减少非反应性溶剂的量。
当本发明羟基官能硫醚化合物的比例基于基料的总重量小于0.1重量％时，本发明的效果通常小。
本发明的可热固化双包装组合物优选在紧临其施用之前通过混合各组分而制备，因为交联剂的反应性基团，优选二异氰酸酯和/或多异氰酸酯的游离异氰酸酯基团与本发明羟基官能硫醚化合物和任选聚合物多元醇中存在的羟基之间的交联反应甚至可以在室温下进行。羟基官能硫醚化合物和若存在的话，聚合物多元醇的初步混合通常没有问题。在各种情况下，该可固化组合物的相互呈反应性的成分应在紧临该组合物，如该涂料组合物、粘合剂或密封剂的施用之前混合，以确保尽可能少发生不希望的反应。
羟基官能硫醚化合物的用途
本发明羟基官能硫醚化合物可以在可热固化组合物中用作反应性稀释剂，所述组合物优选选自涂料组合物、粘合剂和密封剂。因此，该用途为本发明的另一目的。
若用于涂料组合物中，则优选将本发明涂料组合物用作多层涂层中的最上层油漆涂层。特别优选将它用作汽车涂装中的透明涂层。因为本发明组合物甚至在低温下化学固化，它们可以用于汽车修补中。多层涂层、其生产方法以及如此涂敷的基材
本发明进一步提供了一种包含至少两个涂层，优选至少三个涂层的多层涂层。将涂层分配于已涂底漆或未涂底漆的基材上，其中该底涂层和/或优选最上层涂层由本发明可热固化涂料组合物形成。若对基材涂底漆，则该底漆优选为电沉积底漆，更具体为阴极电沉积底漆。涂底漆之前尤其还可以进行转化涂层步骤如磷化处理以形成转化涂层。
在涂底漆或未涂底漆的基材上例如可以施用常规头二道混合底漆涂料。在该头二道混合底漆涂料(若存在的话)上可以施用一个或多个底涂层，后者可以由任何常规底涂层组合物形成。在汽车修补的情况下，所述底涂层通常是纯粹物理干燥的那些或者借助交联剂热固化的那些或者热和光化固化或仅光化固化的那些。另一可能性是对头二道混合底漆涂料提供底涂层的性能或者相反地对底涂层提供头二道混合底漆性能，结果是仅施用一个头二道混合底漆涂层或者仅施用一个底涂层可能就够了。头二道混合底漆涂料通常作为头二道混合底漆涂层施用并且至少一种底涂层组合物作为底涂层施用。适合作为头二道混合底漆涂料和适合作为底涂层组合物的是所有商业头二道混合底漆或底涂层材料，更优选用于汽车修补中的那些。尽管该底涂层材料可以是本发明的可热固化组合物，但更优选施用的最后涂层是作为面漆，具体作为透明面漆(透明涂层)的本发明可热固化涂料组合物。
本发明额外提供了一种生产本发明多层涂层的方法，包括下列步骤：
(i)将至少一种底涂层组合物施用于未被处理或预处理的、任选电沉积涂敷和/或头二道混合底漆涂敷的基材而形成底涂层并随后
(ii)将至少一种面漆组合物，优选呈透明涂层组合物的形式，施用于该底涂层组合物上而形成面漆层，优选透明涂层，然后
(iii)在20-200℃范围内的温度下固化尚未完全固化的涂层。
其中至少一种底涂层组合物或至少一种面漆组合物为本发明可热固化组合物。优选仅面漆组合物为本发明可热固化组合物。
作为头二道混合底漆涂料和底涂层组合物可以使用常规商业头二道混合底漆和底涂层组合物。
各涂层通过本领域普通技术人员熟知的常规涂装方法施用。优选通过气动喷涂和/或静电喷涂施用组合物和涂料。
该底涂层组合物在头二道混合底漆层上的施用和/或该面漆组合物在底涂层上的施用可以通过湿碰湿施用，即其中前一层在施用该涂料组合物之前尚未固化或尚未完全固化的施用进行。因此，在施用一种或多种底涂层组合物之前，该头二道混合底漆可以仅仅在室温下晾干或者替换地，可以将其在升高的温度下干燥。干燥也可以通过IR辐射进行。
上面就头二道混合底漆涂料体系、晾干和/或干燥所作评述也同样适用于该一个或多个底涂层。
代替湿碰湿施用，另一可能性是在施用面漆组合物之前固化该头二道混合底漆层和/或底涂层或任何其他涂层。常规头二道混合底漆和/或常规底涂层组合物可以进行热固化、光化辐射固化或热固化和光化辐射固化的组合。
由本发明可热固化组合物形成的涂层，例如底涂层或透明涂层的固化在至多200℃的温度下，更具体在室温(即25℃)至150℃的温度下，非常具体在30-100℃的温度下进行。
在本发明可热固化组合物为单包装组合物的情况下，固化温度优选为超过100℃至200℃，更优选110-190℃，最优选120-180℃，时间为5-30分钟，更优选10-25分钟。
在本发明可热固化组合物为双包装组合物的情况下，固化温度优选为20-130℃，更优选40-100℃，最优选60-90℃，时间为5-30分钟，更优选10-25分钟。
本发明额外提供了一种涂有本发明多层涂层的基材。
合适的基材尤其包括金属基材，如汽车车身及其部件，但还可以使用塑料基材，优选用于汽车生产中的那些。
实施例
在下文中借助工作实施例和对比例进一步解释本发明。下表中所给量为按重量或重量百分数计的量，除非另有规定。
测试程序
固体含量
固体含量根据DIN EN ISO 3251通过将大约1g样品在130℃下干燥60分钟而测量。
流挂
抗流挂性的测定通过将该涂料以层厚为10-50μm的楔形物施用于以电沉积涂层打底并且涂有底涂层的板上而进行。该底涂层在施用透明涂层配制剂之前固化。流挂在板中的孔上发生，模仿车身的边缘。流挂的被测变量是层厚，在该层厚下流挂长度达到3mm和10mm长。
更详细地，类似于DIN EN ISO 28199-1第8.2部分(版本A)准备尺寸为57cm×20cm的穿孔钢板(根据DIN EN ISO 28199-1，第8.1部分，版本A)，后者涂有固化的阴极电沉积漆(来自BASF Coatings GmbH的800)和固化的市售水基底涂层材料(来自BASF Coatings GmbH的ColorBrite)。然后以目标膜厚(干燥材料的膜厚)为10-50μm的楔形物形式在单次施用中以基于DIN EN ISO28199-1，第8.3部分的方法静电施用该透明涂层材料。在室温(25℃)下10分钟的晾干时间之后，将所得透明涂膜在强制空气烘箱中于80℃下固化30分钟。将钢板在直立的同时晾干并固化。
流挂在每种情况下根据DIN EN ISO 28199-3，第4部分测定。流挂的被测变量是层厚，在该层厚下流挂长度达到3mm和10mm长。
流平性
流平性的被测变量是通过用Byk WaveScan测量得到的值。长波值应模仿波长为1.2-12mm的结构体的视觉外观。短波值应模仿波长为0.3-1.2mm的结构体的视觉外观。测量在固化涂层的37.5±2.5μm膜厚下进行。
耐化学性
耐化学性根据DIN EN ISO 2812-5(2018年12月)对树胶、1％氢氧化钠溶液和1％硫酸溶液测试。测试温度为36-78℃，测试时间为15分钟。
抗划伤性
抗划伤性用AMTEC-Kistler装置测试，模仿工业洗车设施。在试验之前、在试验之后清洁各板之后并再次在60℃下再流平2小时之后测量20°光泽度。DIN EN ISO 20566DE(2013)。根据DIN EN ISO 2813(2015)测量光泽度。
材料
羟基官能硫醚化合物A1-A5的制备
羟基官能硫醚化合物通过使表1中所示硫醇与新癸酸缩水甘油酯(E-10)在四甲基胍作为催化剂存在下反应而合成，基于该混合物的固体含量。所有量为重量份。该反应通过在氮气气氛下将该硫醇和部分SN II(使用的话)放入装有温度控制装置和回流冷凝器的三颈玻璃烧瓶中而进行。在45分钟的时间内在搅拌和不加热下通过滴液漏斗滴加该新癸酸缩水甘油酯。使用残留量的SN II将45分钟之后留在滴液漏斗中的任何新癸酸缩水甘油酯冲洗到反应混合物中。在该反应过程中达到的最大反应温度(Tmax)也示于表1中。
表1
对比反应性稀释剂(CRD)的制备
向装有两个进料容器、回流冷凝器和搅拌元件的呈压力设计的不锈钢反应器加入溶剂石脑油。向进料容器之一加入1340g丙烯酸2-乙基己基酯和495g丙烯酸2-羟基乙基酯的单体混合物。向第二烧瓶加入自由基引发剂(例如过氧化二叔丁基)在溶剂石脑油中的溶液。在2.5绝对巴的压力下将反应器进料加热至150℃。当达到该温度时，开启引发剂进料；整个进料时间为270分钟。开启引发剂进料之后5分钟开始单体进料并且在240分钟内供入。在两种进料结束之后将该批料在150℃下再保持60分钟，然后将其冷却并排出。用溶剂石脑油将该树脂溶液的固体含量调节为66.5％±1％。
可热固化涂料组合物的制备
通过将A包装(即可交联基料包装)与B包装(即包含交联剂的基料包装)均匀混合而得到可热固化组合物。
A包装通过均匀混合表2A中所示成分而得到。所给数字按重量份计并且所用成分及其固体含量在本发明的“材料”部分找到。
表2A
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B包装通过均匀混合表2B中所示成分而得到。所给数字按重量份计并且所用成分及其固体含量在本发明的“材料”部分找到。
表2B
在表2C中找到A包装和B包装的混合比以及最终涂料组合物的测定固体含量。
表2C
可热固化涂料组合物的施用
除了流平和流挂板外，通过气动喷涂将实施例E1-E5和对比例C1的黑色底涂层和透明涂层施用于电沉积涂敷钢板上。在晾干10分钟之后，将该底涂层在80℃下烘干10分钟。在晾干10分钟之后将透明涂层在80℃下固化30分钟。该透明涂层厚度为30±5μm。
对于流平性和流挂试验，将黑色底涂层以恒定层厚施用于大的电沉积涂敷钢板上。在晾干10分钟之后，将该底涂层在80℃下烘干10分钟。通过用旋转雾化器静电施用而以10-50μm厚度的楔形物层厚施用实施例E1-E5和对比例C1的透明涂层。在垂直晾干10分钟之后将透明涂层在80℃下垂直固化30分钟。除了垂直固化的板之外，还在以水平位置晾干并固化(晾干和固化条件相同)的板上测量流平性。
结果
所有实施例—发明例和对比例—显示出优异的耐化学性。对于树胶，发现对涂层的首次影响的温度对于所有实施例为36℃。所有实施例的相应温度对于硫酸(1重量％水溶液)为55±1℃且对于氢氧化钠(1重量％水溶液)为55.5±1.5℃。
所有实施例—发明例和对比例—在进行划伤测试之前显示出优异的光泽度。所有实施例的光泽度在89.5±0.5光泽度单位范围内。在该试验之后清洁各板之后，所有实施例的光泽度单位在72.5±3.5范围内并且再次在60℃下再流平2小时之后光泽度值为73.5±2.5，由此表明良好平衡的再流平性能。
因此，耐化学性和抗划伤性完全可以与含有对比无硫反应性稀释剂的组合物竞争。
然而，对于发明例E1-E5就其流挂性能而言发现与对比例C1相比存在显著改进，同时维持优异的流平性能。结果示于表3中。
表3
在流挂试验中的厚度值越高，抗流挂性越好。在3mm流道长度下的厚度与对比例的33μm相比为38.5±1.5μm，层厚显著改进大约17％。在10mm流道长度下的厚度值与对比例的仅46μm相比为大约51.5±0.5μm，仍有大约12％的改进。
短波和长波值越小，流平性越好。所有短波值(垂直)的平均值为约13.5±1.5，而对比例为15；而所有短波值(水平)的平均值为约14±1，因此与为14的对比例大致相同。所有长波值(垂直)的平均值为约12±1，因此与为12的对比例大致相同；所有长波值(水平)的平均值为约8±1，而对比例的值为7。
Claims (15)
1.一种具有式(I)的羟基官能硫醚化合物：
其中
Z为n价烃基，任选含有一个或多个选自醚结构部分、硫醚结构部分和异氰脲酸酯结构部分的结构部分；
R1为线性或支化亚烷基；
R2选自CH2CH(OH)CH2和CH(CH2OH)CH2；
R3为线性或支化烷基；
m＝0或1；和
n＝2-10。
2.根据权利要求1的羟基官能硫醚化合物，其特征在于所述n价烃基Z含有2-16个碳原子；和/或所述线性或支化亚烷基R1含有1-6个碳原子；和/或所述线性或支化烷基R3含有1-16个碳原子；和/或n＝2-8。
3.根据权利要求3的羟基官能硫醚化合物，其特征在于所述n价烃基Z含有2-10个碳原子；和/或所述线性或支化亚烷基R1含有1-3个碳原子；和/或所述线性或支化烷基R3含有1-10个碳原子。
4.根据权利要求4的羟基官能硫醚化合物，其特征在于所述n价烃基Z含有2-10个碳原子；和/或R2为CH2CH(OH)CH2；和/或所述线性或支化烷基R3含有1-9个碳原子；和/或n＝2-6。
5.根据权利要求1-4中任一项的羟基官能硫醚化合物，其特征在于Z为n价烃基或含有一个或多个醚结构部分的n价烃基；以及m＝1。
6.根据权利要求1-4中任一项的羟基官能硫醚化合物，其特征在于Z为含有一个或多个硫醚结构部分的n价烃基；以及m＝0。
7.一种生产如权利要求1-6中任一项所定义的羟基官能硫醚的方法，其特征在于使(a)一种或多种物质Z-[O(C＝O)R1)m-SH]n与(b)一种或多种式(II)的物质反应：
以及
(c)在m＝1的情况下所述一种或多种物质Z-[O(C＝O)R1)m-SH]n可以通过使一种或多种物质Z[OH]n与n种物质HOOC-R1-SH反应而得到；其中Z、R1、R3、m和n如权利要求1-6中任一项所定义。
8.一种可热固化组合物，包含：
(A)一种或多种如权利要求1-6中任一项所定义的羟基官能硫醚；和(B)一种或多种对所述一种或多种羟基官能硫醚(A)的羟基呈反应性的交联剂。
9.根据权利要求8的可热固化组合物，其中至少一种交联剂选自游离二异氰酸酯、封闭型二异氰酸酯、游离多异氰酸酯、封闭型多异氰酸酯和氨基塑料树脂。
10.根据权利要求8或9的可热固化组合物，进一步包含(C)一种或多种聚合物多元醇。
11.根据权利要求8-10中任一项的可热固化组合物，其特征在于所述组合物选自涂料组合物、粘合剂组合物或密封剂组合物。
12.如权利要求1-6中任一项所定义的羟基官能硫醚在可热固化组合物中作为反应性稀释剂的用途。
13.一种包含至少两个涂层的多层涂层，其特征在于至少一层由如权利要求8-11中任一项所定义的可热固化组合物形成。
14.一种多层涂敷基材，其特征在于它用如权利要求13所定义的多层涂层涂敷。
15.一种在基材上生产多层涂层的方法，其特征在于所述方法包括下列步骤：
(i)在基材上施用至少一种底涂层组合物而形成底涂层并随后
(ii)在所述底涂层组合物上施用至少一种面漆组合物而形成面漆层，然后
(iii)在20-200℃范围内的温度下固化完全固化的涂层，
其中至少一种底涂层组合物或至少一种面漆组合物为如权利要求8-11中任一项所定义的可热固化组合物。
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| PCT/EP2022/061299 WO2022229304A1 (en) | 2021-04-28 | 2022-04-28 | Hydroxyl-functional thioether compounds and their use in curable compositions |
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| US3082180A (en) | 1960-10-04 | 1963-03-19 | American Cyanamid Co | Modified melamine-formaldehyde resin for decorative laminating and process for preparing same |
| DE2835451C2 (de) | 1978-08-12 | 1985-10-24 | Saarbergwerke AG, 6600 Saarbrücken | Verfahren zum Verfestigen von Kohle und/oder Gestein im Bergbau |
| EP0249201A3 (en) | 1986-06-10 | 1989-07-19 | Union Carbide Corporation | High solids sag resistant cycloaliphatic epoxy coatings containing low molecular weight high tg organic polymeric sag resisting additives |
| NO170944C (no) | 1987-01-24 | 1992-12-30 | Akzo Nv | Fortykkede, vandige preparater, samt anvendelse av slike |
| US5128424A (en) * | 1991-07-18 | 1992-07-07 | Japan Synthetic Rubber Co., Ltd. | Epoxy resin, mercato curing agent and polysulfide adduct |
| DE4310413A1 (de) | 1993-03-31 | 1994-10-06 | Basf Lacke & Farben | Nichtwäßriger Lack und Verfahren zur Herstellung einer zweischichtigen Decklackierung |
| AU7390296A (en) | 1995-10-06 | 1997-04-28 | Cabot Corporation | Aqueous thixotropes for waterborne systems |
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| EP1283226A1 (en) | 2001-07-31 | 2003-02-12 | Resolution Research Nederland B.V. | Hydroxyl-functional copolymer and coating compositions formed therewith |
| US9353287B2 (en) | 2006-12-19 | 2016-05-31 | Basf Coatings Gmbh | Coating agents having high scratch resistance and weathering stability |
| ES2666364T3 (es) | 2011-11-17 | 2018-05-04 | Basf Coatings Gmbh | Uso de diésteres de glicerina como diluyentes reactivos y materiales de recubrimiento que los contienen |
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