CN1371409A - 基于改性醇酸树脂的快干型高固体含量涂料 - Google Patents
基于改性醇酸树脂的快干型高固体含量涂料 Download PDFInfo
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- CN1371409A CN1371409A CN00812016A CN00812016A CN1371409A CN 1371409 A CN1371409 A CN 1371409A CN 00812016 A CN00812016 A CN 00812016A CN 00812016 A CN00812016 A CN 00812016A CN 1371409 A CN1371409 A CN 1371409A
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- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/06—Unsaturated polyesters having carbon-to-carbon unsaturation
- C09D167/07—Unsaturated polyesters having carbon-to-carbon unsaturation having terminal carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
- C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
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- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31935—Ester, halide or nitrile of addition polymer
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- Wood Science & Technology (AREA)
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Abstract
本发明描述了基于丙烯酸酯官能化的醇酸树脂的常温氧化固化组合物。还描述了制备基于丙烯酸酯官能化的醇酸树脂的常温氧化固化组合物的方法。这类常温氧化固化组合物可用于例如快干型高固体含量油漆或瓷漆组合物或制剂。
Description
交叉引用的相关申请
根据35U.S.C.§119(e)，本申请要求1999年6月25日申请的US临时申请60/140,788的优先权，该申请的全文在此引入作为参考。
发明背景
发明领域
本发明涉及含有丙烯酸酯官能化的醇酸树脂的常温氧化固化组合物。本发明还涉及制备含有丙烯酸酯官能化的醇酸树脂的常温氧化固化组合物的方法。这类组合物用于制备快干型高固体含量涂料，例如瓷漆。
相关技术描述
近年来，在涂料工业中花费了大量努力以开发低或零VOC含量涂料配方。对工业涂料VOC含量的限制的规定激励研究和开发以探索在降低从工业溶剂型涂料操作如汽车、家电、普通金属、家具等中的溶剂挥发方面的新技术。然而，尽管降低有机溶剂型组合物的步骤带来健康和安全效果，但这些低VOC涂料组合物仍必须达到或超过溶剂型组合物所期望的性能标准。
醇酸树脂是用于常温固化的溶剂型涂料的最常用的粘合剂之一。传统溶剂型醇酸树脂的抵抗性经醇酸树脂薄膜的自氧化交联产生。在醇酸树脂的不饱和脂肪酸或油中的活性亚甲基在空气中被氧化而得到氢过氧化物，其随后分解产生用于各种交联机理的自由基时，就发生交联。该氧化交联过程通常通过加入催干剂，例如钴、锆、钙和锰的各种盐加速。然而，虽然醇酸树脂已经以及继续具有应用前途，但它们具有相对缓慢的“干燥”和/或固化时间，尤其在室温下。已经对醇酸树脂作了各种改性以尝试解决这类问题。
一种这类尝试包括将醇酸树脂与乙烯基化合物如苯乙烯或甲基丙烯酸甲酯按自由基反应聚合以产生乙烯基-醇酸树脂共聚物或乙烯基醇酸树脂。乙烯基醇酸树脂通常具有较高的分子量和较高Tg，因此，生产具有降低的消粘时间(溶剂蒸发)的涂料。然而，这类涂料的全干时间(膜的氧化)却由于与乙烯基化合物共聚的结果而降低醇酸树脂中的不饱和程度而变长。此外，含有乙烯基醇酸树脂的油漆配方由于乙烯基醇酸树脂增加的分子量和Tg而需要更大量的溶剂。
JP48085628描述了使用丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯或其衍生物的改性醇酸树脂。含有-CO2H基团和20-80油长的干性油改性醇酸树脂在阻聚剂存在下用丙烯酸缩水甘油酯、甲基丙烯酸缩水甘油酯或其衍生物处理。所得到的树脂与光敏剂或光引发剂混合以得到用UV照射硬化的涂料组合物。然而，这些树脂组合物不适合于常温氧化固化的高固体含量涂料的应用。
因此在现有技术中仍存在对在成膜时能够进行交联的改性或官能化的醇酸树脂的需要，该树脂可用于制备常温氧化固化、快干型和高固体含量的具有低VOC的涂料。这类涂料会显示出高VOC涂料的性能和优点。
发明概述
本发明通过提供包含丙烯酸酯官能化的醇酸树脂、至少一种催干剂和有机溶剂的常温氧化固化组合物来满足该需要。丙烯酸酯官能化的醇酸树脂是经非自由基反应用丙烯酸缩水甘油酯改性的醇酸树脂，其中丙烯酸缩水甘油酯的缩水甘油基部分是反应部分以使得所得到的醇酸树脂含有末端活性丙烯酸酯基团或部分。该丙烯酸酯官能化的醇酸树脂显示杰出的全干时间(through-dry time)性能。此外，本发明的丙烯酸酯官能化的醇酸树脂显示以前只有通过增加醇酸树脂的分子量和Tg才能改善的杰出的消粘时间性能。由于通常加入醇酸树脂组合物和/或配制剂的VOC的量直接与醇酸树脂的分子量和Tg有关，本发明含有丙烯酸酯官能化的醇酸树脂的组合物或配制剂将需要更少的VOC。
本发明还涉及制备常温氧化固化组合物的方法，其包含使丙烯酸酯官能化的醇酸树脂在有机溶剂存在下与至少一种催干剂接触的步骤。发明详述
本发明提供了常温氧化固化组合物，其包含丙烯酸酯官能化的醇酸树脂、至少一种催干剂和有机溶剂。在本发明的优选实施方案中，常温氧化固化组合物含有基于组合物总重量约50-约85重量％的丙烯酸酯官能化的醇酸树脂，基于组合物总重量约10-约50重量％的有机溶剂和基于组合物总重量约0.01-1.0重量％的至少一种催干剂。根据本发明，常温氧化固化组合物显示改善的消粘时间和全干时间，可用于具有降低的VOC和快速全干时间和消粘时间的瓷漆组合物。
丙烯酸酯官能化的醇酸树脂是含有末端反应性丙烯酸酯基团或部分的醇酸树脂。丙烯酸酯官能化的醇酸树脂是羟基官能醇酸树脂、酸酐和缩水甘油基部分是反应活性部分的丙烯酸缩水甘油酯的反应产物。在本发明的优选实施方案中，丙烯酸酯官能化的醇酸树脂包含(a)基于总组合物约79-约95摩尔％的羟基官能醇酸树脂；(b)基于总组合物约2-约8摩尔％的酸酐和(c)基于总组合物约3-约13摩尔％的丙烯酸缩水甘油酯的反应产物，每个组分在下文描述。
羟基官能醇酸树脂可以是现有技术中已知的含有羟基官能度的任何醇酸树脂。羟基官能醇酸树脂可以通过使二醇、多元醇、二酸、单官能酸和脂肪酸、脂肪族酯或天然产的部分皂化油反应，任选地在催化剂存在下反应制备。羟基官能醇酸树脂优选是(a)基于总组合物0-约30摩尔％的二醇、(b)基于总组合物约10-约40摩尔％的多元醇、(c)基于总组合物约20-约40摩尔％的二酸、(d)基于总组合物0-约10摩尔％的单官能酸、(e)基于总组合物约10-约40摩尔％的脂肪酸、脂肪族酯或天然油和任选的(f)催化剂的反应产物。羟基官能醇酸树脂的每种组分的合适实例包括现有技术中已知的物质，包括，但不限于，如下讨论的物质。《表面涂布用树脂》(Resinsfor Surface Coatings)，1卷，127页，由P.K.T.Oldring和G.Hayward编辑，SITA Technology，London，UA。
脂肪酸、脂肪族酯或天然产的部分皂化油可以是现有技术中已知用于形成醇酸树脂的任何脂肪酸、脂肪族酯或天然产的部分皂化油。在优选实施方案中，使用至少一种一元脂肪酸、脂肪族酯或天然产的部分皂化油，其选自如下式(I)、(II)和(III)：
在式(I)、(II)和(III)中，R是饱和或不饱和C8-C20烷基。更优选R是如下不饱和C18烷基之一：
亚油基
亚麻基
油基
在另一实施方案中，一元脂肪酸或脂肪族酯油可以通过使油或脂肪酸与多元醇反应制备。合适的油的实例包括向日葵油、低芥酸菜子油、脱氢蓖麻油、椰子油、玉米油、棉籽油、鱼油、亚麻子油、奥气油、大豆油、桐油、动物脂、蓖麻油、猪油、棕榈仁油、花生油、紫苏子油、红花油、动物脂油、核桃油等。单独的脂肪酸或作为油的组分的合适实例包括，但不限于，牛油酸、大豆酸、肉豆蔻酸、亚麻子酸、巴豆酸、versatic酸、椰油酸、妥尔油脂肪酸(例如PAMOLYN 200，商业上由Hercules获得)、松香酸、新癸酸、新戊酸、异硬脂酸、12-羟基硬脂酸、棉籽酸等。
用于制备羟基官能醇酸树脂本身或一元脂肪酸或脂肪族酯的多元醇优选选自脂族、脂环族和芳基烷基多元醇。多元醇的合适实例包括，但不限于，三羟甲基丙烷(TMP)、季戊四醇(PE)、三羟甲基乙烷、赤藓醇、threitol、二季戊四醇、山梨糖醇、甘油等。多元醇优选是三羟甲基丙烷(TMP)或季戊四醇(PE)。
除多元醇之外，二醇也可用于制备羟基官能醇酸树脂。合适二醇的实例包括，但不限于，新戊二醇(NPG)、乙二醇、丙二醇、二甘醇、三甘醇、四甘醇、五甘醇、六甘醇、七甘醇、八甘醇、九甘醇、十甘醇、1，3-丙二醇、2，4-二甲基-2-乙基-己-1，3-二醇、2，2-二甲基-1，2-丙二醇、2-乙基-2-丁基-1，3-丙二醇、2-乙基-2-异丁基-1，3-丙二醇、1，3-丁二醇、1，4-丁二醇、1，5-戊二醇、1，6-己二醇、2，2，4-四甲基-1，6-己二醇、硫代二乙醇、1，2-环己烷二甲醇、1，3-环己烷二甲醇、1，4-环己烷二甲醇、2，2，4-三甲基-1，3-戊二醇、2，2，4-四甲基-1，3-环丁烷二醇、对-二甲苯二醇、羟基新戊酰基羟基新戊酸酯、1，10-癸二醇和氢化双酚A。二醇优选是新戊二醇(NPG)。
羟基官能醇酸树脂的二酸或二羧酸和单官能或一元羧酸组分可以是现有技术中用于形成醇酸树脂的已知的任何二酸或单官能酸。二羧酸可以是例如间苯二甲酸、邻苯二甲酸酐(邻苯二甲酸)、对苯二甲酸、己二酸、四氯邻苯二甲酸酐、十二烷二酸、癸二酸、壬二酸、1，4-环己烷二羧酸、1，3-环己烷二羧酸、马来酸酐、富马酸、琥珀酸酐、琥珀酸、2，6-萘二羧酸或戊二酸等。二羧酸优选是间苯二甲酸、邻苯二甲酸酐或邻苯二甲酸。单官能酸还可以使用，例如苯甲酸、乙酸、丙酸和丁酸。
任选地，催化剂可用于促进羟基官能醇酸树脂的形成。催化剂可以是现有技术中用于形成醇酸树脂已知的任何催化剂。催化剂优选是酸催化剂，例如FASCAT 4100。加入的催化剂量促进形成如上所述的羟基官能醇酸树脂，并且可通过本领域技术人员理解的常规试验测定。催化剂优选以基于反应物量约0.01-1.00重量％的量加入。
羟基官能醇酸树脂可在约170-230℃、更优选180-220℃和最优选190-210℃的温度下制备。在本发明的优选实施方案中，羟基官能醇酸树脂具有约80-约180mg KOH/g的羟值，0-约10mg KOH/g的酸值，数均分子量约700-约2000，Tg低于约25℃。
合适的酸酐包括现有技术中的已知物质。合适酸酐的实例包括，但不限于，偏苯三酸酐、邻苯二甲酸酐、马来酸酐和富马酸酐，优选使用偏苯三酸酐。
丙烯酸缩水甘油酯可以是含有环氧或缩水甘油基部分的任何取代或未取代的丙烯酸酯，当所述部分与羟基官能醇酸树脂和酸酐反应时将产生如上所述的能够在固化过程中进行交联的丙烯酸酯官能化的醇酸树脂。根据本发明，在与羟基官能醇酸树脂和酸酐反应时，丙烯酸缩水甘油酯的缩水甘油基部分显示比丙烯酸酯部分更大的反应性，即与羟基官能醇酸树脂和酸酐进行反应的是缩水甘油基部分。用于丙烯酸缩水甘油酯的丙烯酸酯部分的合适取代基包括C1-C18烷基以形成几种类型的化合物，例如烷基丙烯酸酯(例如甲基丙烯酸酯)和巴豆酸酯。丙烯酸缩水甘油酯优选甲基丙烯酸缩水甘油酯。
丙烯酸酯官能化的醇酸树脂的制备是：使各自如上所述的羟基官能醇酸树脂与酸酐反应以制备羧基官能醇酸树脂和如上所述使羧基官能醇酸树脂与丙烯酸缩水甘油酯反应以生产丙烯酸酯官能化的醇酸树脂。丙烯酸酯官能化的醇酸树脂可在约100-170℃、更优选约115-165℃，最优选约125-155℃的温度范围内反应。
在本发明的优选实施方案中，丙烯酸酯官能化的醇酸树脂通过如下步骤制备：使如上所述的(a)0-约30摩尔％二醇，(b)约10-约40摩尔％多元醇，(c)约20-约40摩尔％二酸，(d)0-约10摩尔％单官能酸在催化剂存在下在约180-220℃下反应直至冷凝物(水)的收集停止以形成中间体醇酸树脂；使中间体醇酸树脂与如上所述的约10-约40摩尔％脂肪酸、脂肪族酯或天然产的部分皂化油在约190-220℃下反应直至获得低于约5的酸值以形成羟基官能醇酸树脂；使羟基官能醇酸树脂与如上所述的约2-约8摩尔％酸酐在约150-165℃下反应约2-6小时直至得到透明反应混合物并从而形成如上所述的羧基官能醇酸树脂；和使羧基官能醇酸树脂与如上所述的约3-约12摩尔％丙烯酸缩水甘油酯在约125-155℃下反应直至得到低于约5的酸值，从而形成如上所述的所希望的丙烯酸酯官能化的醇酸树脂。
根据本发明，在最终常温氧化固化组合物中所需的有机溶剂的量被降低，因为如上所述丙烯酸酯官能化的醇酸树脂显示较低的Tg值。有机溶剂可以是任何合适的溶剂。合适有机溶剂的实例包括，但不限于，二甲苯、苯、甲苯和溶剂油。有机溶剂优选是二甲苯。本发明的常温氧化固化组合物具有通常大于约70％的高固体含量。
本发明的常温固化组合物的催干剂可以是本领域已知的任何催干剂。合适催干剂的实例包括，但不限于，钴、锆、钙、锌和锰的各种盐，催干剂优选是钴催干剂。还可以使用催干剂的混合物，即催干剂体系。
在本发明的优选实施方案中，如上所述的常温氧化固化组合物还可以含有至少一种颜料以形成常温氧化固化瓷漆组合物。颜料优选以基于组合物总重量约30-约60重量％的量存在。合适的颜料的实例包括在表面涂料领域的技术人员已知的那些物质。例如，颜料可以是典型的有机或无机颜料，尤其是在Colour Index，3d Ed.，2d Rev.，1982中描述的物质，American Association of Textile Chemistsand Colorists与Society of Dyers and Colourists合作出版。合适的颜料的其它实例包括，但不限于，如下：二氧化钛、重晶石、粘土或碳酸钙，CI颜料白6(二氧化钛)；CI颜料红101(氧化铁红)；CI颜料黄42，CI颜料蓝15，15∶1，15∶2，15∶3，15∶4(铜酞菁)；CI颜料红49∶1和CI颜料红57∶1。颜料优选是二氧化钛。着色剂，例如酞菁蓝、钼铬橙或碳黑也可加入常温氧化固化瓷漆组合物中。
常温氧化固化组合物，优选常温氧化固化瓷漆组合物可涂覆在基底上，并用本领域已知的技术固化(例如通过在金属板上喷涂3-4密耳的湿涂层，并在150℃强制空气烘箱中加热30分钟)。基底可以是任何常规的基底，例如纸、聚酯膜如聚乙烯或聚丙烯，金属如铝或钢，玻璃，聚氨酯弹性体、底涂的(涂漆的)基底等。本发明的常温氧化固化组合物可在室温下固化(常温固化)。
本发明的常温氧化固化组合物还可含有至少一种涂料添加剂以例如提高组合物的干燥效率。合适的涂料添加剂的实例包括，但不限于，流平和流动控制剂，例如硅氧烷、碳氟化合物或纤维素；增量剂；增塑剂；平光剂；颜料湿润和分散剂；紫外线(UV)吸收剂；UV光稳定剂；消泡和防沫剂；抗沉降剂，防流挂和增稠剂；防结皮剂；防浮剂和防泛剂；和腐蚀抑制剂。这类添加剂的具体实例可在RawMaterials Index中找到，National Paint & CoatingsAssociation，1500 Rhode Island Avenue，N.W.，Washington，D.C.20005出版。这类添加剂的其它实例可在US5,371,148中找到。
平光剂的实例包括，但不限于，合成二氧化硅，由DayisonChemical Division of W.R.Grace & Company作为SYLOID获得；聚丙烯，由Hercules Inc.，作为HERCOFLAT获得；合成硅酸盐，由J.M.Huber Corporation作为ZEOLEX获得。
分散剂的实例包括，但不限于，二(十三烷基)磺基琥珀酸酯钠、二(2-乙基己基)磺基琥珀酸酯钠、二己基磺基琥珀酸酯钠、二环己基磺基琥珀酸酯钠、二戊基磺基琥珀酸钠、二异丁基磺基琥珀酸钠、异癸基磺基琥珀酸二钠、磺基琥珀酸的乙氧基化醇半酯的二钠、烷基酰氨基聚乙氧基磺基琥珀酸二钠、N-(1，2-二羧基乙基)-N-十八烷基磺基琥珀酰胺酸(sulfosuccinnamate)四钠、N-辛磺基琥珀酰胺酸二钠、硫酸化乙氧基化壬基酚、2-氨基-2-甲基-1-丙醇等。
粘度、悬浮和流动控制剂的实例包括，但不限于，聚氨基酰胺磷酸盐、聚胺酰胺的高分子量羧酸盐和不饱和脂肪酸的亚烷基胺盐，均由BYK Chemie U.S.A.作为ANTI TERRA获得。其它实例包括，但不限于，聚硅氧烷共聚物、聚丙烯酸盐溶液、纤维素酯、羟基乙基纤维素、羟基丙基纤维素、聚酰胺蜡、聚烯烃蜡、羟基丙基甲基纤维素、聚环氧乙烷等。
若干专用防沫剂是商业可获得的，包括，但不限于，BuckmanLaboratories Inc.的BUBREAK；BYK Chemie，U.S.A.的BYK；Henkel Corp./Coating Chemicals的FOAMASTER和NOPCO；DrewIndustrial Division of Ashland Chemical Company的DREWPLUS；Troy Chemical Corporation的TRYSOL和TROYKYD以及Union Carbide Corporation的SAG。
UV吸收剂和UV光稳定剂的实例包括，但不限于，取代的二苯酮，取代的苯并三唑、受阻胺和受阻苯甲酸盐，由Amercan CyanamidCompany作为CYASORB UV获得，和二乙基-3-乙酰基-4-羟基-苄基-膦酸盐、4-十二烷氧基-2-羟基二苯酮和间苯二酚单苯甲酸酯。
溶剂的实例是已知的，包括但不限于，乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、异丁醇、乙二醇单丁基醚、丙二醇正丁基醚、丙二醇甲基醚、丙二醇单丙基醚、二丙二醇甲基醚、二甘醇单丁基醚、三甲基戊二醇单异丁酸酯、乙二醇单辛基醚、双丙酮醇、TEXANOL酯醇(Eastman Chemical Company)等。这类溶剂还可包括活性溶剂，例如邻苯二甲酸二烯丙基酯，SANTOLINK XI-100聚缩水甘油基烯丙基醚，由Monsanto获得，和在US5,349,026和5,371,148中描述的其它物质。
本发明还提供了制备常温氧化固化组合物的方法，其包含使各自如上所述的丙烯酸酯官能化的醇酸树脂与至少一种催干剂在有机溶剂存在下接触的步骤。丙烯酸酯官能化的醇酸树脂可如上所述制备。优选丙烯酸酯官能化的醇酸树脂树脂与至少一种以约0.01-1.0重量％存在的催干剂在有机溶剂中反应。
给出如下实施例用于举例说明本发明。然而，应理解本发明并不受这些实施例中描述的具体条件或详细说明的限制。
本发明的各种涂料组合物的实施例使用如下的上述未描述的物质：
PAMOLYN 200妥尔油脂肪酸，由Hercules Incorporated ofWilmington，Delaware出售
FASCAT 4100酯化反应催化剂，由M& T Chemicals of Rahway，New Jersey出售
FC-430是碳氟化合物添加剂，由3M Corp of St.Paul，Minnesota出售
CEM-All钙是羧酸钙，由OM Group of Cleveland，Ohio出售。
如下方法用于评价本发明制备的涂料和薄膜。
消粘棉试验：如果薄膜表面在与脱脂棉纤维接触时不拉出纤维，涂层被认为消粘。
全干拇指试验：如果用拇指在薄膜表面上按压和扭转而没有影响(未起皱)涂层，则认为其全干。
硝基清漆消粘试验：将一片1×4英寸的铝金属条弯曲得到1×1英寸的基底，并且其角度要使得5g重物正好足以保持基底而不倾倒。该金属条被放置在涂料薄膜上，并将钢圆筒(500g重，1英寸直径)放置在基底上45秒钟。如果圆筒重量被除去铝条马上倾倒，薄膜被认为硝基清漆消粘。
实施例
如以下实施例中所述，合成羟基官能醇酸树脂1和2，随后用甲基丙烯酸缩水甘油酯(GMA)改性以分别形成丙烯酸酯官能化的醇酸树脂1和2。羟基官能醇酸树脂1在改性过程之前在二甲苯中切成70％固体含量以降低粘度，而具有较低Tg(从而较低粘度)的羟基官能醇酸树脂2直接用于改性。实施例1：制备羟基官能醇酸树脂1
在带有机械搅拌器、蒸汽夹套分凝器、迪安-斯达克榻分水器、氮气入口和水冷凝器的三颈圆底烧瓶中加入新戊二醇(NPG)(53.89g，0.52mol)、三羟甲基丙烷(TMP)(139.87g，1.04mol)、间苯二甲酸(IPA)(201.82g，1.22mol)、苯甲酸(BA)(30.37g，0.25mol)和FASCAT 4100(Atochem)(0.32g)。使混合物在180-220℃反应直至得到47.5g冷凝物(水)。在混合物冷却后，加入PAMO LYN200(Hercules)(209.06g，0.72mol)和FASCAT 4100(0.32g)。使反应在190-220℃下持续进行直至达到1.8的酸值。使得到的树脂冷却到120℃，加入二甲苯(246g)以得到含有70％固体的树脂溶液。实施例2：制备丙烯酸酯官能化的醇酸树脂1
向装有机械搅拌器、水冷凝器和氮气入口的三颈圆底烧瓶中加入实施例1的羟基官能醇酸树脂1(300g，70％)和偏苯三酸酐(TMA)(8.9g，0.046mol)。反应混合物在150℃下搅拌6小时，随后冷却到110℃。随后加入甲基丙烯酸缩水甘油酯(GMA)(13.1g，0.092mol)。在150℃下持续反应1.5小时得到酸值2.9的透明树脂。实施例3：制备羟基官能醇酸树脂2
在带有机械搅拌器、蒸汽夹套分凝器、迪安-斯达克榻分水器、氮气入口和水冷凝器的三颈圆底烧瓶中加入新戊二醇(NPG)(97.80g，0.94mol)、季戊四醇(PE)(70.14g，0.52mol)、间苯二甲酸(IPA)(36.60g，0.22mol)、邻苯二甲酸酐(PA)(107.22g，0.72mol)和FASCAT 4100(0.30g)。使混合物在190-200℃反应直至得到19.5g冷凝物(水)。在混合物冷却后，加入PAMOLYN 200(295.77g，1.02mol)和FASCAT 4100(0.30g)。使反应在200℃下持续进行直至达到0.9的酸值。得到的树脂被分离纯净(100％固体)。实施例4：制备丙烯酸酯官能化的醇酸树脂2
向装有机械搅拌器、水冷凝器和氮气入口的三颈圆底烧瓶中加入实施例3的羟基官能醇酸树脂2(210g)和偏苯三酸酐(TMA)(8.9g，0.046mol)。反应混合物在165℃下搅拌3.5小时，随后冷却到110℃。随后加入甲基丙烯酸缩水甘油酯(GMA)(13.1g，0.092mol)。在160℃下持续反应2小时得到酸值2.9的透明树脂。将得到的树脂冷却到120℃，加入二甲苯(57g)得到含有80％固体的树脂溶液。实施例5：瓷漆涂料组合物
首先通过使用Dispermat混合器(BYK-Chemie)混合实施例2的丙烯酸酯官能化的醇酸树脂1(16.23g，在二甲苯中71.8％)、TiO(Du Pont，Ti-Pure R-900，35.00g)、FC-430(3M，0.16g(在异丙醇中20％))直至获得Hegman7+的粒度，以制备颜料色浆。随后，在研磨料中加入附加的丙烯酸酯官能化的醇酸树脂1(32.46g，71.8％)、钴催干剂(6％，NUODEX，Tenneco Chemicals)、CEM-All钙(4％，OM Group)和二甲苯(7.05g)。将混合物进一步搅拌得到均匀白色油漆。
类似于实施例5，制备分别基于实施例1和3的羟基官能醇酸树脂1和2以及实施例4的丙烯酸酯官能化的醇酸树脂2的瓷漆涂料组合物。调节每种瓷漆的溶剂含量得到可应用的粘度。实施例6：薄膜干燥时间
为比较它们的干燥时间，高固体含量的瓷漆涂料组合物用(a)羟基官能醇酸树脂1；(b)羟基官能醇酸树脂2；(c)丙烯酸酯官能化的醇酸树脂1和(d)丙烯酸酯官能化的醇酸树脂2配制。得到的瓷漆具有如下％固体：
(a)羟基官能醇酸树脂1：75％；
(b)羟基官能醇酸树脂2：91％；
(c)丙烯酸酯官能化的醇酸树脂1：75％；和
(d)丙烯酸酯官能化的醇酸树脂2：84％。
如表格I中所示，基于丙烯酸酯官能化的醇酸树脂的瓷漆组合物的各种干燥时间比基于羟基官能醇酸树脂的瓷漆组合物的时间短得多。配制羟基官能醇酸树脂2以用于比较用途，仅仅是因为它的粘度太低，因而不适合于涂料应用。
表I
羟基官能醇酸树脂和丙烯酸酯官能化的醇酸树脂的干燥时间
消粘：棉试验；全干：拇指试验；硝基清漆消粘：测量45秒。
| 薄膜试验 | 羟基官能醇酸树脂1 | 丙烯酸酯官能化的醇酸树脂1 | 羟基官能醇酸树脂2 | 丙烯酸酯官能化的醇酸树脂2 |
| 消粘时间 | 2.5小时 | 1.5小时 | 4天 | 4小时 |
| 全干 | 8天 | 3小时 | 10天 | 7小时 |
| 硝基清漆消粘 | ＞6天 | 30小时 | 几周 | 6天 |
应理解上述讨论和实施例仅仅作为某些优选实施方案的详细描述。对本领域技术人员来说，显然可作出各种改变例和等价例，而不违背本发明的精神和范围。所有以上讨论或引用的专利、杂志文章和其它文献列为本文参考文献被引入。
Claims (20)
1.常温氧化固化组合物，其包含：
(a)丙烯酸酯官能化的醇酸树脂，其包含如下组分的反应产物：
(i)羟基官能醇酸树脂；
(ii)酸酐；和
(iii)丙烯酸缩水甘油酯
其中所述丙烯酸缩水甘油酯的缩水甘油基部分是反应活性部分，并且所述反应产物含有末端反应性丙烯酸酯部分；
(b)至少一种催干剂；和
(c)有机溶剂。
2.权利要求1的常温氧化固化组合物，其中
(a)基于总组合物所述丙烯酸酯官能化的醇酸树脂以约50重量％-约85重量％的量存在；
(b)基于总组合物所述催干剂以约0.01重量％-约1.0重量％的量存在；和
(c)基于总组合物所述有机溶剂以约10重量％-约50重量％的量存在。
3.权利要求1的常温氧化固化组合物，其中所述丙烯酸酯官能化的醇酸树脂包含如下组分的反应产物：
(a)基于总组合物约79摩尔％-约95摩尔％的所述羟基官能醇酸树脂；
(b)基于总组合物约2摩尔％-约8摩尔％的所述酸酐；和
(c)基于总组合物约3摩尔％-约13摩尔％的所述丙烯酸缩水甘油酯。
4.权利要求1的常温氧化固化组合物，其中所述羟基官能醇酸树脂包含如下组分的反应产物：
(a)基于总组合物0摩尔％-约30摩尔％的二醇；
(b)基于总组合物约10摩尔％-约40摩尔％的多元醇；
(c)基于总组合物约20摩尔％-约40摩尔％的二酸；
(d)基于总组合物0摩尔％-约10摩尔％的单官能酸；和
(e)基于总组合物约10摩尔％-约40摩尔％的脂肪酸、脂肪族酯或天然产的部分皂化油。
5.权利要求4的常温氧化固化组合物，其中所述二醇是新戊二醇，所述多元醇是三羟甲基丙烷或季戊四醇，所述二酸是间苯二甲酸、间苯二甲酸酐或邻苯二甲酸和所述单官能酸是苯甲酸。
6.权利要求1的常温氧化固化组合物，其中所述催干剂选自钴、锆、钙、锌和锰的盐。
7.权利要求1的常温氧化固化组合物，其中所述羟基官能醇酸树脂具有约80-约180mg KOH/g的羟值。
8.权利要求1的常温氧化固化组合物，其中所述丙烯酸缩水甘油酯是甲基丙烯酸缩水甘油酯。
9.权利要求1的常温氧化固化组合物，其还包含至少一种选自流动控制剂、增量剂、增塑剂、平光剂、颜料湿润剂、颜料分散剂、紫外线(UV)吸收剂、UV光稳定剂、着色颜料、着色剂、消泡剂、防沫剂、抗沉降剂、防流挂剂、增稠剂、防结皮剂、防浮剂、防泛剂和腐蚀抑制剂的添加剂。
10.常温氧化固化瓷漆组合物，其包含：
(a)丙烯酸酯官能化的醇酸树脂，其包含如下组分的反应产物：
(i)羟基官能醇酸树脂；
(ii)酸酐；和
(iii)丙烯酸缩水甘油酯
其中所述丙烯酸缩水甘油酯的缩水甘油基部分是反应活性部分，并且所述反应产物含有末端反应性丙烯酸酯部分；
(b)至少一种催干剂；
(c)有机溶剂；和
(d)至少一种颜料。
11.权利要求10的常温氧化固化瓷漆组合物，其中所述颜料以基于组合物总重量约30重量％-约60重量％的量存在。
12.权利要求11的常温氧化固化瓷漆组合物，其还包含至少一种选自流动控制剂、增量剂、增塑剂、平光剂、颜料湿润剂、颜料分散剂、紫外线(UV)吸收剂、UV光稳定剂、着色颜料、着色剂、消泡剂、防沫剂、抗沉降剂、防流挂剂、增稠剂、防结皮剂、防浮剂、防泛剂和腐蚀抑制剂的添加剂。
13.制备常温氧化固化组合物的方法，其包含步骤：
使丙烯酸酯官能化的醇酸树脂与至少一种催干剂在有机溶剂存在下接触。
14.权利要求13的制备常温氧化固化组合物的方法，其还包含步骤：
使羟基官能醇酸树脂与酸酐反应以形成羧基官能醇酸树脂；和
使所述羧基官能醇酸树脂与丙烯酸缩水甘油酯的缩水甘油基部分反应以形成丙烯酸酯官能化的醇酸树脂。
15.权利要求14的制备常温氧化固化组合物的方法，其还包含步骤：
在催化剂存在下在约190-220℃温度下使(a)基于总组合物0-约30摩尔％二醇；(b)基于总组合物约10-约40摩尔％多元醇；(c)基于总组合物约20-约40摩尔％二酸；和(d)基于总组合物0-约10摩尔％单官能酸反应以形成中间体聚酯树脂；
在约190-220℃温度下使中间体聚酯树脂与基于总组合物约10-约40摩尔％脂肪酸、脂肪酸酯或天然产的部分皂化油任选地在催化剂存在下反应以形成羟基官能醇酸树脂直至获得低于约5的酸值；
在约150-165℃温度下使羟基官能醇酸树脂与基于总组合物约2-约8摩尔％酸酐反应以形成羧基官能醇酸树脂；和
在约125-155℃温度下使羧基官能醇酸树脂与基于总组合物约3-约12摩尔％丙烯酸缩水甘油酯反应以形成丙烯酸酯官能化的醇酸树脂，其中所述丙烯酸缩水甘油酯的缩水甘油基部分是反应活性部分。
16.权利要求15的方法，其中所述二醇是新戊二醇，所述多元醇是三羟甲基丙烷或季戊四醇，所述二酸是间苯二甲酸、间苯二甲酸酐或邻苯二甲酸和所述单官能酸是苯甲酸。
17.权利要求15的方法，其中所述丙烯酸缩水甘油酯是甲基丙烯酸缩水甘油酯。
18.涂布有权利要求1的常温氧化固化组合物的基底。
19.涂布有权利要求10的常温氧化固化瓷漆组合物的基底。
20.涂布有权利要求12的常温氧化固化瓷漆组合物的基底。
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| CN100372899C (zh) * | 2005-11-29 | 2008-03-05 | 天津市精英有机聚合物有限公司 | 镜背漆树脂及其幕淋涂料 |
| CN100372900C (zh) * | 2005-11-29 | 2008-03-05 | 天津市精英有机聚合物有限公司 | 镜背漆树脂及其幕淋涂料 |
| CN101531755B (zh) * | 2009-04-13 | 2011-06-15 | 湖南湘江涂料集团有限公司 | 有机酸盐改性水性醇酸树脂及其制备方法 |
| CN102603991A (zh) * | 2012-01-18 | 2012-07-25 | 海洋化工研究院 | 船舶内舱用环保型水性防护装饰涂料 |
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| US7060745B2 (en) | 2002-04-12 | 2006-06-13 | Resolution Specialty Materials Llc | Waterborne acrylate-functionalized alkyd coating compositions |
| US6780523B2 (en) | 2002-04-12 | 2004-08-24 | Eastman Chemical Company | Waterborne acetoacetate-functionalized alkyd coating compositions |
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| US6794049B2 (en) | 2002-04-12 | 2004-09-21 | Eastman Chemical Company | Fast-dry, high solids coating compositions based on acetoacetate-functionalized alkyd resins |
| BR0309739A (pt) * | 2002-05-03 | 2005-02-22 | Valspar Sourcing Inc | Composição de revestimento, composição de resina alquìdica, e, substrato revestido |
| US6946509B2 (en) | 2002-09-20 | 2005-09-20 | Resolution Specialty Materials Llc | Acrylate-functional alkyd resins having improved dry time |
| US20050145138A1 (en) * | 2003-12-30 | 2005-07-07 | Council Of Scientific And Industrial Research | Oxygen barrier material for packaging |
| US7256226B2 (en) * | 2004-03-15 | 2007-08-14 | Hexion Specialty Chemicals, Inc. | Storage-stable acrylate-functional alkyd resin compositions |
| US7141109B1 (en) | 2004-06-03 | 2006-11-28 | Velasquez Louis R | Paint medium and method of production |
| US7566759B2 (en) * | 2005-10-27 | 2009-07-28 | Georgia-Pacific Chemicals Llc | Non-aqueous coating formulation of low volatility |
| US7371792B2 (en) | 2005-12-20 | 2008-05-13 | Ppg Industries Ohio, Inc. | Stain compositions and related coated substrates |
| CA2673067C (en) * | 2006-12-29 | 2012-05-15 | The Sherwin-Williams Company | Pretreatment and stain system |
| CN101407698B (zh) * | 2007-10-09 | 2012-01-25 | 上海涂料有限公司技术中心 | 水性气干型涂料用复合催干剂 |
| EP2159235B1 (en) * | 2008-08-05 | 2010-12-29 | Rohm and Haas Company | Aqueous polymeric dispersion and method for providing improved adhesion |
| SG184275A1 (en) | 2010-03-31 | 2012-11-29 | Nuplex Resins Bv | Waterborne hybrid polymer dispersion |
| US9540538B2 (en) | 2011-06-01 | 2017-01-10 | Synres B.V. | Drier for alkyd resin compositions |
| US20130034741A1 (en) * | 2011-08-04 | 2013-02-07 | Ppg Industries Ohio, Inc. | Branched polyester polymers comprising isophthalic acid and coatings comprising the same |
| HUE052479T2 (hu) | 2011-09-26 | 2021-04-28 | Ppg Europe B V | Bevonó kompozíció és alkalmazása |
| CN102746464A (zh) * | 2012-05-29 | 2012-10-24 | 兰州理工大学 | 醇酸丙烯酸接枝共聚物及其制备方法 |
| CN104262595A (zh) * | 2014-09-16 | 2015-01-07 | 田清峰 | 水性醇酸树脂合成工艺 |
| CN105669961A (zh) * | 2016-02-02 | 2016-06-15 | 成都杰晟蜀邦新材料科技有限公司 | 一种高支化高固低粘的醇酸树脂及其制备方法 |
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- 2000-06-16 EP EP00939929A patent/EP1194493B2/en not_active Expired - Lifetime
- 2000-06-16 DE DE2000617743 patent/DE60017743T3/de not_active Expired - Lifetime
- 2000-06-16 AT AT00939929T patent/ATE287935T1/de not_active IP Right Cessation
- 2000-06-16 WO PCT/US2000/016608 patent/WO2001000741A1/en active IP Right Grant
- 2000-06-16 JP JP2001506743A patent/JP4426144B2/ja not_active Expired - Fee Related
- 2000-06-16 BR BRPI0011931-8A patent/BR0011931B1/pt not_active IP Right Cessation
- 2000-06-16 MX MXPA01013200A patent/MXPA01013200A/es not_active Application Discontinuation
- 2000-06-16 CN CNB008120161A patent/CN1221620C/zh not_active Expired - Fee Related
- 2000-06-16 US US09/596,269 patent/US6548601B1/en not_active Expired - Lifetime
- 2000-06-16 ES ES00939929T patent/ES2234623T5/es not_active Expired - Lifetime
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN100372899C (zh) * | 2005-11-29 | 2008-03-05 | 天津市精英有机聚合物有限公司 | 镜背漆树脂及其幕淋涂料 |
| CN100372900C (zh) * | 2005-11-29 | 2008-03-05 | 天津市精英有机聚合物有限公司 | 镜背漆树脂及其幕淋涂料 |
| CN100372882C (zh) * | 2005-12-07 | 2008-03-05 | 江苏三木集团有限公司 | 快干醇酸树脂及制备方法 |
| CN101531755B (zh) * | 2009-04-13 | 2011-06-15 | 湖南湘江涂料集团有限公司 | 有机酸盐改性水性醇酸树脂及其制备方法 |
| CN102603991A (zh) * | 2012-01-18 | 2012-07-25 | 海洋化工研究院 | 船舶内舱用环保型水性防护装饰涂料 |
| CN105400393A (zh) * | 2015-11-27 | 2016-03-16 | 太仓新浏精密五金有限公司 | 一种专用于铁基五金件的速干型树脂涂料 |
| CN110229282A (zh) * | 2019-05-07 | 2019-09-13 | 武汉双虎涂料有限公司 | 一种gma接枝型水性丙烯酸改性醇酸树脂及其制备方法 |
| CN110527413A (zh) * | 2019-09-25 | 2019-12-03 | 广东衡光新材料科技有限公司 | 一种丙烯酸改性的水性醇酸分散体及其制备方法和应用 |
| CN110527413B (zh) * | 2019-09-25 | 2021-08-24 | 广东衡光新材料科技有限公司 | 一种丙烯酸改性的水性醇酸分散体及其制备方法和应用 |
| CN111440298A (zh) * | 2020-06-08 | 2020-07-24 | 常州广树化工科技有限公司 | 一种芳环与杂环改性的水性醇酸树脂及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0011931A (pt) | 2002-03-19 |
| ES2234623T3 (es) | 2005-07-01 |
| US6534598B2 (en) | 2003-03-18 |
| ES2234623T5 (es) | 2009-06-09 |
| MXPA01013200A (es) | 2002-06-04 |
| BR0011931B1 (pt) | 2010-12-28 |
| DE60017743D1 (de) | 2005-03-03 |
| JP2003503578A (ja) | 2003-01-28 |
| DE60017743T2 (de) | 2005-12-29 |
| US20020183453A1 (en) | 2002-12-05 |
| JP4426144B2 (ja) | 2010-03-03 |
| EP1194493A1 (en) | 2002-04-10 |
| US6548601B1 (en) | 2003-04-15 |
| EP1194493B2 (en) | 2009-03-04 |
| CN1221620C (zh) | 2005-10-05 |
| WO2001000741A1 (en) | 2001-01-04 |
| ATE287935T1 (de) | 2005-02-15 |
| DE60017743T3 (de) | 2009-07-16 |
| EP1194493B1 (en) | 2005-01-26 |
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