CN1285685C - 辐射固化性粉末组合物,其粉末清漆和色漆及涂布方法和涂布制品 - Google Patents
辐射固化性粉末组合物,其粉末清漆和色漆及涂布方法和涂布制品 Download PDFInfo
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- CN1285685C CN1285685C CN02814657.3A CN02814657A CN1285685C CN 1285685 C CN1285685 C CN 1285685C CN 02814657 A CN02814657 A CN 02814657A CN 1285685 C CN1285685 C CN 1285685C
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Classifications
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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
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
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Abstract
本发明描述了辐射固化性粉末组合物,它包括10-90wt%的具有0.35-3.50毫当量双键/g树脂的“链内”不饱和度的烯属不饱和聚酯和/或丙烯酸类共聚物,b)10-90wt%的具有乙烯基,烯丙基,(甲基)丙烯酸酯基或者含二酸或酸酐的不饱和基团的烯属不饱和(氢化)聚苯氧基树脂,和c)0-30wt%的烯属不饱和低聚物。
Description
本发明涉及可通过辐射硬化的粉末组合物,它可用作色漆或清漆,包括至少一种具有“链内”不饱和基团的烯属不饱和树脂和至少一种具有可与该烯属不饱和树脂的“链内”不饱和基团和与任选加入到该粘结剂中的烯属不饱和低聚物的官能团反应的烯属不饱和基团的(氢化)聚苯氧基树脂的混合物,该低聚物具有还能够与该烯属不饱和树脂的“链内”不饱和基团反应的官能团。
本发明的粉末组合物尤其适于在金属和热敏感基材上涂布,在低温下熔融和用辐射来固化时,兼备系列性能如良好的流动性和膜硬度,以及突出的耐溶剂性和柔性。这些辐射固化性粉末可以显示改进的柔性和耐化学品性。
粉末涂料在室温下是干燥、精细分开、自由流动的固体材料,与液体涂料相比,在近年来赢得了相当多的欢迎。虽然它们具有许多优点,但目前热固性粉末涂料一般要在至少140℃的温度下固化。在该推荐的温度以下,涂料具有低劣的外观以及低劣的物理和化学性能。由于该限制的缘故,粉末涂料一般没有在涂布热敏感基材如木材和塑料或含有热敏感化合物的组装金属零件中使用。热敏感基材或化合物均要求低固化温度,优选在140℃以下,以避免显著的降解和/或变形。
作为该问题的解决办法,最近已经提出了低温辐射固化性粉末。
不饱和树脂最终与不饱和低聚物联合用作辐射固化性粉末涂料的粘结剂已成为许多专利和专利申请的主题。
尤其,已经深入地说明了由尤其含烯属不饱和基团的聚酯、丙烯酸类共聚物或环氧树脂获得的UV固化性粉末涂料组合物。
US 3,974,303(Kansal Paint Co Ltd.)描述了不同不饱和树脂如含甲基丙烯酰基的聚酯或丙烯酸类共聚物。
EP 2164254(BASF)描述了以不饱和聚酯、丙烯酸类共聚物、环氧树脂和含有不饱和双键的其它聚合物为基础的粉末涂料。
US 4,129,488(SCM Corporation N.Y.)公开了包括特殊空间排列的烯属不饱和聚合物的适于UV固化的粉末色漆涂料。(甲基)丙烯酸不饱和聚合物是按分步法生产的空间特定的环氧-聚酯聚合物,具有1000-10000的数均分子量,为自由流动性粉末提供了适合的结晶度和显示了优异流动性所需的在80-200℃之间的清晰(sharp)熔点。
含有端部甲基丙烯酰基的半结晶聚酯或其与含有端部甲基丙烯酰基的无定形聚酯的共混物已经分别在例如EP 0739922和WO98/18862(UCB)中要求保护。论述了漆性能如流动性,硬度,机械性能,耐溶剂性(MEK)。
如本领域那些技术人员所公知的那样,粉末涂料,不管是热固性的还是辐射固化性的,只有当粘结剂体系是以具有端部反应性基团的树脂为基础时,才具有令人满意的柔性。然而对于这些特定情况,所获得的涂料没有满足耐溶剂性的高要求。
具有“链内”不饱和键,因此在固化时增加了网络密度的粘结剂体系大大地增加了耐溶剂性,然而却使柔性降低。
特征在于粘结剂包括具有含不饱和基团的几个侧链的丙烯酸类共聚物的粉末涂料在WO 93/25596(DSM)中要求保护。
含(甲基)丙烯酰基的丙烯酸类共聚物和含端部甲基丙烯酰基的半结晶聚酯的混合物在WO 98/18874(UCB)中要求保护。
包括不饱和聚酯和具有多个烯丙基、乙烯基或甲基丙烯酸酯官能团的低聚物的混合物作为粘结剂的粉末涂料尤其例如在US 5,763,099和US 5,703,198中要求保护。该不饱和聚酯由多元醇与多羧酸的反应获得,不饱和键通过引入不饱和二酸或相应酸酐来获得。所得涂料显示了良好的流动性,抗划伤性和耐化学品性。
现在已经令人惊奇地发现,以具有“链内”不饱和基团的至少一种烯属不饱和树脂和带有能够与该“链内”不饱和键反应的官能团的至少一种烯属不饱和(氢化)聚苯氧基树脂的特定混合物作为粘结剂的辐射固化性粉末涂料组合物显示了物理性能如平滑度、硬度和耐化学品性与突出的柔性的优异和独特的结合。
该辐射固化性粉末涂料组合物因此尤其可用于诸如卷材涂料和PVC地面材料之类的应用。
本发明的目的是解决例如这里所述的与现有技术有关的一些或全部问题,例如提供能够通过在熔融时的辐射来固化的粉末组合物。
因此,概括地说,根据本发明,提供了辐射固化性粉末涂料组合物,它包括:
a)大约10wt%到大约90wt%的烯属不饱和遥爪聚酯和/或丙烯酸类遥爪共聚物;
b)大约10wt%到大约90wt%的含有至少一个乙烯基、烯丙基、(甲基)丙烯酸酯基;不饱和二酸和/或不饱和酸酐的烯属不饱和非芳族聚氧(polyoxy resin)树脂;和
c)任选的至多大约30wt%的烯属不饱和低聚物。
本发明的另一个方面提供了辐射固化性粉末涂料组合物,它包括:
a)10-90wt%的具有0.35-3.50毫当量的双键/g树脂的“链内”不饱和度的烯属不饱和聚酯和/或丙烯酸类共聚物,
b)10-90wt%的具有乙烯基,烯丙基,(甲基)丙烯酸酯基或者含二酸或酸酐的不饱和基团的烯属不饱和(氢化)聚苯氧基树脂,
c)0-30wt%的具有选自(甲基)丙烯酸酯基、烯丙基、乙烯基或者含有二酸或酸酐的不饱和基团的烯属不饱和低聚物。
本发明的烯属不饱和聚酯可以是无定形或半结晶的,优选是羟基和/或羧酸基团封端的聚酯。
聚酯可以由含有50-95mol%的脂族、环脂族或芳族多元酸和5-50mol%的不饱和多元酸的酸成分与脂族或环脂族多元醇制备。
适合的脂族、环脂族或芳族酸的实例尤其包括:邻苯二甲酸,间苯二甲酸,对苯二甲酸,1,2-环己烷二甲酸,1,3-环己烷二甲酸,1,4-环己烷二甲酸,丁二酸,戊二酸,己二酸,庚二酸,辛二酸,壬二酸,癸二酸,1,12-十二烷二酸,1,2,4-苯三酸,1,2,4,5-苯四酸和它们的酸酐,它们可以单独或作为混合物使用。
用于制备本发明的聚酯的不饱和多元酸可以选自富马酸,马来酸,衣康酸,柠康酸和中康酸,它们可以单独或作为混合物使用。
适合的脂族或环脂族多元醇的实例尤其包括:乙二醇,1,3-丙二醇,1,4-丁二醇,1,5-戊二醇,1,6-己二醇,1,7-庚二醇,1,8-辛二醇,1,9-壬二醇,1,10-癸二醇,1,11-十一烷二醇,1,12-十二烷二醇,2-甲基-1,3-丙二醇,新戊二醇,2-丁基-2-甲基-1,3-丙二醇,新戊二醇的羟基新戊酸酯,1,4-环己二醇,1,4-环己烷二甲醇,氢化双酚A,2,2,4,4-四甲基-1,3-环丁二醇,4,8-双(羟甲基)-三环-[5,2,1,02,6]-癸烷。本发明的聚酯可以根据包括一个或多个反应步骤的工序来制备。
为了制备本发明的聚酯,优选使用装有搅拌器、惰性气体(氮气)进口、连接于水冷冷凝器的蒸馏塔和连接于温度调节器的温度计的普通反应器。
用于制备这些聚酯的酯化条件能够是常用的,即可以反应剂的例如0-1wt%的比例使用普通酯化催化剂,例如由锡衍生的那些,如氧化二丁基锡,二月桂酸二丁基锡或三辛酸二正丁基锡,或由钛衍生的那些,如钛酸四丁酯,以及任选例如以反应剂的0-1wt%的比例添加抗氧化剂,如酚化合物Irganox 1010(Ciba)或Ionol CP(Shell)或者亚膦酸酯或亚磷酸酯类的稳定剂,如亚磷酸三丁酯或亚磷酸三苯酯。
聚酯化一般在从130℃逐渐增加到大约180-250℃的温度下,首先在常压下,然后在该方法的各步骤的最后在减压下进行,保持这些条件,直到获得显示所需羟基和/或酸值的聚酯为止。酯化度通过测定在反应过程中形成的水量和所得聚酯的性能,例如羟基值、酸值、分子量和/或粘度来监控。
该聚酯可以用10-100mg KOH/g和优选25-75mg KOH/g的酸值(AN)和/或羟基值(OHN),800-16 000和优选1 300-8 500的数均分子量,40-85℃的玻璃化转变温度(Tg)(当聚酯是无定形的时),或60-150℃的熔化温度和低于50℃的玻璃化转变温度(当聚酯是半结晶的时),0.2-4.0和优选0.5-2.5毫当量的双键/g聚酯的不饱和度和在200℃下测量的低于50 000mPa·s的ICI锥/板粘度来表征。
这些聚酯进一步能够由二异氰酸酯与(甲基)丙烯酸羟烷基酯和聚酯的端部羟基的反应或由(甲基)丙烯酸缩水甘油酯和聚酯的端部羧基的反应而转化为(甲基)丙烯酰基封端的聚酯。
用于在以上反应中与二异氰酸酯反应的(甲基)丙烯酸羟烷基酯优先选自(甲基)丙烯酸羟乙酯,(甲基)丙烯酸2-或3-羟丙酯,(甲基)丙烯酸2-,3-和4-羟丁酯等。
用于在以上反应中与(甲基)丙烯酸羟烷基酯和含羟基的聚酯反应的二异氰酸酯优先选自1-异氰酸根合-3,3,5-三甲基-5-异氰酸根合甲基环己烷(异佛尔酮二异氰酸酯,IPDI),四甲基二甲苯二异氰酸酯(TMXDI),六亚甲基二异氰酸酯(HDI),三甲基六亚甲基二异氰酸酯,4,4’-二异氰酸根合二环己基甲烷,4,4’-二异氰酸根合二苯基甲烷,它与2,4-二异氰酸根合二苯基甲烷的工业混合物,以及上述二异氰酸酯的高级同系物,2,4-二异氰酸根合甲苯及其与2,6-二异氰酸根合甲苯的工业混合物,以及α,α’-二甲基间异丙烯基苄基异氰酸酯(TMI)的共聚产物。
含有(甲基)丙烯酰基的聚酯能够按以下方法之一制备:
在完成上述缩聚之后,让在反应器中的熔融状态的含羟基或羧基官能团的聚酯冷却到100-160℃的温度,再以例如基于聚酯重量的0.01-1%的比例添加自由基聚合抑制剂,如吩噻嗪或氢醌类抑制剂和用氧气代替氮气。当由含羟基的聚酯起始时,将基本上等当量量的(甲基)丙烯酸羟烷基酯加入到其中。当加入了全部的(甲基)丙烯酸羟烷基酯时,将等当量量的二异氰酸酯缓慢加入到混合物中。能够任选使用羟基/异氰酸酯反应的催化剂。这些催化剂的实例包括有机锡化合物(例如二月桂酸二丁基锡,二马来酸二丁基锡,氧化二丁基锡,辛酸亚锡,1,3-二乙酰氧基-1,1,3,3-四丁基二锡氧烷(distanoxane))。这些催化剂优先以基于聚酯重量的0-1%的量使用。
另外,当由含羧基的聚酯起始时,将基本等当量量的(甲基)丙烯酸缩水甘油酯加入到其中。任选能够使用用于酸/环氧基反应的催化剂。这些催化剂的实例包括胺(例如2-苯基咪唑啉),膦(例如三苯基膦),铵盐(例如溴化四丁基铵或氯化四丙基铵),磷鎓盐(例如溴化乙基三苯基磷鎓或氯化四丙基磷鎓)。这些催化剂优先以基于聚酯重量的0.05-1%的量使用。
反应进程的程度通过测定所得聚酯的性能,例如羟基值,酸值,不饱和度和/或游离(甲基)丙烯酸缩水甘油酯或(甲基)丙烯酸羟烷基酯的含量来监控。
这样获得的不饱和聚酯显示了0.0-2.0毫当量的双键/g聚酯的遥爪(甲基)丙烯酰基不饱和度。
本发明的粉末组合物的烯属不饱和丙烯酸类共聚物由携带官能团的烯属不饱和单体与携带能够与该含烯属不饱和基团的单体的官能团反应的官能团的丙烯酸类共聚物的反应来制备。
携带可反应官能团的丙烯酸类共聚物由40-95mol%的至少一种丙烯酸类或甲基丙烯酸类单体,0-60mol%的至少一种其它烯属不饱和单体和5-60mol%的携带选自环氧基、羧基、羟基或异氰酸酯基团中的官能团的烯属不饱和单体组成。
本发明的粉末组合物的烯属不饱和丙烯酸类共聚物能够按两步法来制备。
在第一步中,以普通聚合方法,如本体聚合,乳液聚合,在有机溶剂的溶液中的聚合制备丙烯酸酯共聚物,其中一定部分的官能化单体共聚,获得了官能化丙烯酸酯共聚物。该官能化单体通常以5-60mol%的量存在,优选是环氧官能化单体,例如以(甲基)丙烯酸缩水甘油酯为基础。然而,还能够使用酸官能化单体,例如以(甲基)丙烯酸为基础,羟基官能化单体,例如以(甲基)丙烯酸羟乙酯为基础,或异氰酸酯官能化单体,例如以出自American Cyanamid的TMI(1-(1-异氰酸根合-1-甲基乙基)-4-(1-甲基乙烯基)苯)或出自Shawo Denko的MOI(甲基丙烯酸2-异氰酸根合乙基酯)为基础。
单体在以单体的0.1-5wt%量的自由基引发剂如过氧化苯甲酰,过氧化叔丁基,过氧化癸酰,偶氮双异丁腈等的存在下共聚。有效用于制备丙烯酸类共聚物的单体是(甲基)丙烯酸甲酯,(甲基)丙烯酸乙酯,(甲基)丙烯酸丙酯,(甲基)丙烯酸正丁酯,(甲基)丙烯酸异丁酯,(甲基)丙烯酸叔丁酯,(甲基)丙烯酸2-乙基己酯,(甲基)丙烯酸硬脂酯,(甲基)丙烯酸十三烷基酯,(甲基)丙烯酸环己酯,(甲基)丙烯酸苄酯,(甲基)丙烯酸苯酯,(甲基)丙烯酸二甲基氨基乙酯,(甲基)丙烯酸二乙基氨基乙酯,聚硅氧烷(甲基)丙烯酸酯和己内酯(甲基)丙烯酸酯。这些单体通常以大约40到大约95mol%的量存在。
其它可共聚的单体能够以0-60mol%的量存在,例如是苯乙烯,α-甲基苯乙烯,乙烯基甲苯,丙烯腈,甲基丙烯腈,乙酸乙烯酯,丙酸乙烯酯,丙烯酰胺,甲基丙烯酰胺,羟甲基甲基丙烯酰胺,氯乙烯,乙烯,丙烯和C4-C20α-烯烃。
在第二步中,进行在由第一步获得的丙烯酸酯共聚物的官能化单体和能够与所述官能化单体反应的含烯属不饱和基团的化合物之间的加成反应。分别能够反应的该化合物例如是(甲基)丙烯酸,马来酸酐,(甲基)丙烯酸(β-甲基)缩水甘油酯,烯丙基缩水甘油醚,MOI,(甲基)丙烯酸羟乙酯,羟丁基乙烯基醚,烯丙醇。
第二步的加成反应能够在本体中或在溶剂中进行。典型溶剂是甲苯,二甲苯,乙酸正丁酯等。能够与官能化丙烯酸酯聚合物反应的含有不饱和基团的化合物在50-150℃的温度下添加。将混合物搅拌几小时。反应过程之后进行滴定。
本发明的粉末组合物的烯属不饱和丙烯酸类共聚物显示了一个或多个以下特性:
用GPC测定的1000-8000和优选2 000-6 000的数均分子量(Mn);
0.35-3.50和优选0.5-2.5毫当量的双键/g的丙烯酸类共聚物的不饱和度;
根据ASTM D4287在200℃下测定的低于50 000mPa·s的ICI锥板熔体粘度;
根据ASTM D3418通过DSC测定的45-100℃的玻璃化转变温度(Tg)。
烯属不饱和(氢化)聚苯氧基树脂可以通过以下途径获得:
(氢化)聚苯氧基树脂的缩水甘油基与单或多官能不饱和羧酸或其酸酐如(甲基)丙烯酸,马来酸,富马酸,衣康酸,柠康酸,中康酸的羧酸基团的反应;
含甲基丙烯酰基、乙烯基或烯丙基的醇如烯丙醇,羟丁基乙烯基醚,(甲基)丙烯酸羟乙酯与酸酐如邻苯二甲酸酐,丁二酸酐的反应产物;和/或
烯丙基或乙烯基缩水甘油醚与二元酸如间苯二甲酸,对苯二甲酸,1,2-环己烷二甲酸,1,3-环己烷二甲酸,1,4-环己烷二甲酸,丁二酸,戊二酸,己二酸,庚二酸,辛二酸,壬二酸,癸二酸,1,12-十二烷二酸的反应产物。
为了制备含烯属不饱和基团的(氢化)聚苯氧基树脂,一般使用装有搅拌器、氧气进口、含烯属不饱和羧酸基团的化合物的进口和连接于温度调节器的温度计的普通反应器。向在100-150℃的温度下放置的环氧树脂以基于环氧树脂重量的例如0.01-1%的比例添加自由基聚合抑制剂。然后将基本上等当量量的含烯属不饱和羧酸基团的化合物加入到熔融的环氧树脂中。任选能够使用用于酸/环氧基反应的催化剂。这些催化剂的实例包括胺(例如2-苯基咪唑啉),膦(例如三苯基膦),铵盐(例如溴化四丁基铵或氯化四丙基铵),磷鎓盐(例如溴化乙基三苯基磷鎓或氯化四丙基磷鎓)。这些催化剂优选以基于环氧树脂重量的0.05-1%的量使用。
反应进程的程度通过测定所得含烯属不饱和基团的树脂的性能,如酸值、羟基值和不饱和度来监控。
在根据本发明的组合物中引入的含烯属不饱和基团的(氢化)聚苯氧基树脂优选显示0.2-6.0,尤其0.5-4.5毫当量的双键/g的树脂的不饱和度,在特别优选的实施方案中,另外显示了一个或多个以下特性:
450-5000,优选650-3500的数均分子量,通过凝胶渗透色谱法(GPC)测定,
30-80℃的根据ASTM D3418通过差示扫描量热法(DSC)测定的玻璃化转变温度(Tg),
低于20 000mPa·s的根据ASTM D4287用锥板式粘度计(称为ICI粘度)在200℃下测定的熔融状态的粘度。
除了携带“链内”不饱和键的烯属不饱和聚酯和/或丙烯酸类共聚物和烯属不饱和(氢化)苯氧基树脂以外,本发明的粉末组合物可以含有至多30wt%的烯属不饱和低聚物。
烯属不饱和低聚物可以选自:
含烯丙基醚-酯基的低聚物,如三羟甲基丙烷二烯丙基醚或季戊四醇三烯丙基醚和多羧酸或酸酐的酯,例如1,2,4-苯三酸酐的三羟甲基丙烷二烯丙基醚的二酯和三酯或己二酸的季戊四醇三烯丙基醚二酯,
含烯丙基和脲烷基团的低聚物,例如由烯丙醇,三羟甲基丙烷二烯丙基醚,季戊四醇三烯丙基醚与异佛尔酮二异氰酸酯,甲苯二异氰酸酯,六亚甲基二异氰酸酯的反应获得的那些,
低聚物如三烯丙基氰脲酸酯,三烯丙基异氰脲酸酯,邻苯二甲酸二烯丙酯,
含乙烯醚基的低聚物如丁基乙烯基醚,环己基二甲醇二乙烯基醚,丁基二乙烯基醚,三甘醇二乙烯基醚,羟丁基乙烯基醚,
具有乙烯基醚和/或烯丙基醚和/或(甲基)丙烯酸酯端基和任选的聚醚、聚酯或聚碳酸酯骨架的聚氨酯低聚物,由羟烷基乙烯基醚,羟烷基烯丙基醚或(甲基)丙烯酸羟烷基酯与多异氰酸酯和任选的羟基官能化低聚物的反应来制备,该低聚物是聚醚,聚酯或聚碳酸酯,
三(2-羟乙基)异氰脲酸酯的三丙烯酸酯和三甲基丙烯酸酯。
上述所有的烯属不饱和无定形和/或半结晶聚酯和/或丙烯酸类共聚物与烯属不饱和(氢化)聚苯氧基树脂与任选的烯属不饱和低聚物可用于在制备可通过UV照射或通过加速电子束固化的粉末组合物中用作粘结剂,所述组合物尤其可以用作清漆和色漆,例如它们适用于根据利用摩擦起电或静电喷枪的沉积技术的应用或根据在流化床中的沉积技术的施涂。该辐射固化性粉末组合物本身能够用作清漆或色漆,或如果需要,该组合物能够通过添加在制备粉末清漆和色漆的中通常使用的其它成分来制备清漆或色漆。
因此,本发明还涉及使用这些组合物获得的粉末清漆或色漆。
最后,本发明还涉及涂布制品,更尤其金属制品的方法,包括通过沉积如通过用摩擦起电或静电喷枪喷涂或通过在流化床中沉积将根据本发明的辐射固化性粉末组合物施涂于所述制品上,随后例如通过在80-150℃的温度下加热例如大约0.5-10分钟来熔融这样获得的涂层和通过UV照射或通过加速电子束固化熔融状态的涂层。
对于根据本发明的粉末组合物用加速电子束的辐射固化,不必要使用光引发剂,鉴于这类辐射本身独自形成了自由基,这足以使固化以极快的速度进行。相反,当根据本发明的粉末组合物用其中波长在200-600nm的辐射(UV辐射)进行光固化时,必需存在至少一种光引发剂。
能够根据本发明使用的光引发剂选自通常用于该目的的那些。
能够使用的适宜光引发剂是芳族羰基化合物,如二苯甲酮及其烷基化或卤化衍生物,蒽醌及其衍生物,噻吨酮及其衍生物,苯偶姻醚,芳族或非芳族α-二酮,苯偶酰二烷基缩醛,乙酰苯衍生物和氧化膦类。
可以适宜的光引发剂例如是2,2’-二乙氧基乙酰苯,2-、3-或4-溴乙酰苯,2,3-戊二酮,羟基环己基苯基酮,苯甲醛,苯偶姻,二苯甲酮,9,10-二溴蒽,2-羟基-2-甲基-1-苯基丙-1-酮,4,4’-二氯二苯甲酮,氧杂蒽酮,噻吨酮,苯偶酰二甲基酮缩醇,氧化二苯基(2,4,6-三甲基苄基)膦等。可以任选地使用光活化剂如三丁基胺,2-(2-氨基乙基氨基)乙醇,环己基胺,二苯基胺,三苄基胺或氨基丙烯酸酯,如仲胺,例如二甲基胺,二乙基胺,二乙醇胺等与多元醇多丙烯酸酯,如三羟甲基丙烷,1,6-己二醇等的二丙烯酸酯的加成产物。根据本发明的粉末组合物能够含有0-15和优选0.5-8重量份的光引发剂/100重量份的在根据本发明的组合物中的粘结剂。
根据本发明的辐射固化性粉末组合物和粉末清漆或色漆分别还能够含有通常用于制备粉末色漆和清漆的各种其它物质。任选加到根据本发明的辐射固化性粉末组合物中,例如为了制备粉末清漆或色漆的其它物质尤其是吸收UV辐射的化合物,如Tinuvin 900(Ciba),位阻胺型光稳定剂(例如出自Ciba的Tinuvin 144),流动性调节剂如Resiflow PV5(Worlee),Modaflow(Monsanto),Acronal 4F(BASF)或Crylcoat 109(UCB),除气剂如苯偶姻等。
能够向根据本发明的辐射固化性粉末组合物进一步添加各种涂布性能改良物质如聚四氟乙烯改性的聚乙烯蜡(例如出自Lubrizol的Lanco Wax TF 1830),聚乙烯蜡(例如出自BYK Chemie的Ceraflour961),聚丙烯蜡(例如出自Lubrizol的Lanco Wax PP1362),聚酰胺蜡(例如出自ELF Atochem的Orgasol 3202D NAT),有机硅氧烷(例如出自Protex的Modarez S304P)等,或它们的共混物。这些改良物质任选以0-10重量份/100重量份的本发明的组合物的粘结剂的量添加。还能够将各种颜料和无机填料加入到根据本发明的辐射固化性粉末组合物中。作为颜料和填料的例子,可以提及金属氧化物,如氧化钛,氧化铁,氧化锌等,金属氢氧化物,金属粉,硫化物,硫酸盐,碳酸盐,硅酸盐,例如硅酸铝,炭黑,滑石,高岭土,重晶石,铁蓝,铅蓝,有机红,有机红,有机栗红等。
这些其它物质以常量使用,应该理解的是,如果根据本发明的辐射固化性粉末组合物用作清漆,应该不要添加具有不透明性能的其它物质。
为了制备本发明的辐射固化性粉末组合物,将全部含有烯属不饱和基团的无定形和/或半结晶聚酯和/或丙烯酸类共聚物和(氢化)聚苯氧基树脂,和/或如果存在的烯属不饱和低聚物,任选的光引发剂,任选的各种通常用于制备粉末色漆和清漆的其它物质,以及任选的涂布性能改良物质干混,例如在转鼓混合机内。然后将混合物在挤出机,例如Buss Ko-Kneter单螺杆挤出机或Werner-Pfleiderer,APV-Baker或Prism型的双螺杆挤出机中在60-150℃的温度下均化。然后将挤出物冷却,研磨和筛分,以便获得其中颗粒粒度优选为10-150μm的粉料。
这样获得的粉末色漆和清漆完全适合于用普通技术,即通过例如在流化床中的沉积或通过用摩擦起电或静电喷枪施涂的公知技术来施涂于所要涂敷的制品上。
在已施涂于所述制品上之后,所沉积的涂层例如在强制循环烘箱内,或利用红外灯在80-150℃的温度下加热例如大约0.5-10分钟的时间,以便使粉末颗粒作为平滑、均匀和连续的涂层在所述制品表面上熔融和铺开。熔融的涂层然后通过辐射,例如由优选至少80-250W/线性cm的中压汞蒸汽UV辐射器,或由现有技术的任何其它公知辐射源在例如大约5-20cm的距离处发出的UV光来固化达足以固化涂层的时间,如1-60秒。
熔融的涂层还能够用优选至少150keV的加速电子束来固化,所用设备的功率与通过聚合固化的组合物层的厚度成正比。
本发明还涉及通过涂布方法部分或完全涂布的制品。
根据本发明的辐射固化性粉末组合物能够施涂于各种的基材,例如金属,纸张,纸板,木材,纤维板,纺织品,塑料,如聚碳酸酯,聚(甲基)丙烯酸酯,聚烯烃,聚苯乙烯,聚(氯乙烯),聚酯,聚氨酯,聚酰胺,共聚物如丙烯腈-丁二烯-苯乙烯(ABS)或乙酸丁酸纤维素等。
根据本发明的辐射固化性粉末组合物还能够配制调色剂组合物,如用于电子照相术的任何干燥或液体调色剂。
本发明的其它方面和特征在权利要求中给出。
以下通过实施例来进一步举例说明本发明,但它们纯粹是本发明的应用的说明。
实施例1:烯属不饱和聚酯的合成
将591.8份的新戊二醇和2.0份的三辛酸二正丁基锡催化剂的混合物投入到普通四颈圆底烧瓶内。
在氮气下搅拌的同时将烧瓶内容物加热到大约140℃的温度。随即在搅拌的同时添加386.4份的对苯二甲酸和257.6份的富马酸以及0.2份的二叔丁基氢醌,再将混合物逐渐加热到225℃的温度。蒸馏从大约190℃开始。在蒸馏出理论水量的大约95%之后,获得了透明聚合物,逐渐施加50mm Hg的真空,直到测得以下特性为止:
酸值3mg KOH/g;羟基值48mg KOH/g;不饱和度2.2meq/g;ICI175 ℃3500mPa·s;Tg骤冷(DSC)48℃;Mn(GPC)2240。
实施例2:烯属不饱和聚苯氧基树脂的合成
步骤1
向普通四颈圆底烧瓶添加1000ml的氯仿和105份的丁二酸酐。将烧瓶内容物加热到55℃,再在氧气下在1小时内逐渐加入120份的4-羟丁基乙烯基醚与0.1份的二叔丁基氢醌。一旦添加完,将混合物在氧气下进一步搅拌另外3小时,直到测得酸值为240-280mg KOH/g和羟基值低于20mg KOH/g为止。然后排空烧瓶内容物,以及在旋转蒸发仪中在50℃和真空下干燥1小时。
步骤2
然后,在氧气下将775份的Araldite GT 7004,双酚A型环氧树脂在普通四颈圆底烧瓶内加热到140℃的温度。随后添加0.8份的溴化乙基三苯基磷鎓并开始添加225份的含有0.2份二叔丁基氢醌的步骤1加合物。添加在3小时内完成。在添加完步骤1加合物之后1小时,获得了具有以下特性的树脂:酸值8mg KOH/g;不饱和度1meq/g;Tg骤冷(DSC)45℃和Mn(GPC)1900。
实施例3:乙烯基醚官能化低聚物的合成
根据如在US 5,703,198的实验2中所述的配方和工序制备乙烯基醚官能化低聚物。
给4L圆筒形反应器装配温度计、搅拌器和回流冷凝器,再装入555份的1,6-己烷二异氰酸酯,0.6份的月桂酸二丁基锡和2L氯仿。在将恒定的氮气流供给该容器的同时,经大约3小时的过程滴加766份的4-羟丁基乙烯基醚,在此期间,将反应混合物加热到大约55℃。在大约8小时之后,形成了沉淀物,过滤,用己烷洗涤,再在真空下干燥。反应产物具有大约90-108℃的熔点范围。
实施例4:未着色粉末色漆、清漆用UV辐射的固化
将510份的实施例1的烯属不饱和聚酯,320份的实施例2的烯属不饱和聚苯氧基树脂和170份的实施例3的烯属不饱和低聚物,25份的Irgacure 2959(α-羟基酮)(Ciba)和10份的BYK 361(BYK Chemie)的混合物在Prism 16mm(L/D=15/1)双螺杆挤出机(购自Prism公司)中在大约70到100℃的温度下均化,将挤出物在Alpine 100 UPZ研磨机(购自Alpine公司)内研磨。最后,将粉料筛分,以便获得10-110μm的粒度。
用静电喷枪在60kV的电压下在未处理的冷轧钢材上以40-100μm的膜厚施涂如上所述的用根据本发明的粘结剂组合物配制的粉料。
所沉积的涂层然后在中红外线/对流炉(Triab)内在140℃的温度下进行熔化大约3分钟的时间,然后用由具有2000mJ/cm2的总UV剂量的160W/cm中压汞蒸汽UV灯泡(Fusion UV Systems Ltd.)发射的紫外线照射。
测试所得粉末涂料,测得了以下结果:
目测评价:良好、平滑和有光泽的外表,没有任何缺陷;
铅笔硬度:3H,根据Wolff-Wilborn的划痕硬度试验仪;
耐MEK性:>200,相当于没有不利影响固化薄膜表面的外观的用浸渍MEK的棉布来回(往复)摩擦运动的次数;
直接冲击:>100kg·cm,抗直接冲击(DI)的值,按kg·cm计,根据ASTM D 2795在冷轧钢上进行;
反向冲击:>100kg·cm,抗反向冲击(RI)的值,按kg·cm计,根据ASTM D 2795在冷轧钢上进行;
T-弯曲:<2T,根据ASTM D4145-83T-弯曲试验;和
粘合力:4-5B,其中
5B:切口的边缘完全平滑;没有一个正方形分离
4B:小片的涂层在交切点分离;低于5%的面积受影响。
在第二个实验中,将实施例4的粉末喷涂在PVC片材上。
将涂层在中红外线/对流炉中在120℃下熔融90秒,然后用由具有2000mJ/cm的总UV剂量的160W/cm中压汞蒸汽UV灯泡(Fusion UVSystems Ltd.)发射的紫外线照射。涂层结果具有良好的外观,良好的耐MEK性(>200次往复MEK摩擦)和在弯曲PVC片材时没有开裂。
实施例4证明,根据本发明的粘结剂组合物能够用作用于其中需要优异柔性和突出的耐溶剂性的终应用,如卷材涂料和PVC地面材料的基材粉末漆。
虽然已经详细和参照其特定实施方案描述了本发明,但本领域的普通技术人员清楚,在不偏离本发明的范围和精神的情况下能够做出许多变化和修改。
Claims (19)
1、辐射固化性粉末组合物,它包括:
a)第一组分,包括10wt%到90wt%的具有0.35-3.50毫当量双键/g“链内”不饱和度的烯属不饱和聚酯和/或丙烯酸类共聚物,
b)第二组分,包括10wt%到90wt%的具有乙烯基,烯丙基,丙烯酸酯基和/或甲基丙烯酸酯基或者含二酸或酸酐的不饱和基团的烯属不饱和聚苯氧基树脂和/或氢化聚苯氧基树脂,
c)第三组分,包括0到30wt%的烯属不饱和低聚物。
2、根据权利要求1的组合物,其中包括烯属不饱和聚酯的第一组分通过让(i)包括50-95mol%的脂族、环脂族或芳族多元酸和5-50mol%的不饱和多元酸的酸组分;与(ii)包括脂族和/或环脂族多元醇的醇组分反应来获得。
3、根据权利要求2的组合物,由包括马来酸、富马酸、衣康酸、柠康酸、中康酸和/或它们的任何混合物的不饱和多元酸获得。
4、根据权利要求2的组合物,其中第一组分包括携带羟基和/或羧酸端基的烯属不饱和聚酯。
5、根据权利要求4的组合物,其中聚酯以至少一种以下性能或它们的任何组合为特征:
(I)10到100mg KOH/g的酸值和/或羟基值;
(II)800到16000道尔顿的数均分子量;
(III)低于50000mPa·s的熔体粘度,在200℃下用锥板方法测定;
(IV)0.2到4.0毫当量的双键/g聚酯的不饱和度;
(V)40到85℃的玻璃化转变温度;和/或
(VI)60到150℃的熔点和低于50℃的玻璃化转变温度。
6、根据权利要求1的组合物,其中第一组分通过让以下物质反应来获得:
(a)二异氰酸酯;丙烯酸羟烷基酯和/或甲基丙烯酸羟烷基酯和烯属不饱和聚酯;或
(b)丙烯酸缩水甘油酯和/或甲基丙烯酸缩水甘油酯和烯属不饱和聚酯。
7、根据权利要求1的组合物,其中第一组分包括通过让以下(a)和(b)反应获得的烯属不饱和丙烯酸类共聚物:
(a)由以下物质获得的带有官能团的丙烯酸类共聚物:
(i)40到95mol%的具有丙烯酸或甲基丙烯酸基的至少一种单体,
(ii)任选的至多60mol%的另一烯属不饱和单体;和
(iii)5到60mol%的具有能够与环氧基、羧酸、羟基和/或异氰酸酯中的一种或多种反应的官能团的烯属不饱和单体;
(b)带有烯属不饱和基团和能够与环氧基、羧酸、羟基和/或异氰酸酯中的一个或多个反应的官能团的单体。
8、根据权利要求1的组合物,其中第一组分包括以至少一项以下性能和它们的任何组合为特征的烯属不饱和丙烯酸类共聚物:
(I)1000到8000道尔顿的数均分子量;
(II)45到100℃的玻璃化转变温度;
(III)0.35到3.50毫当量双键/g丙烯酸类共聚物的不饱和度;和/或
(IV)低于50000mPa·s的熔体粘度,通过锥板法在200℃下测定。
9、根据权利要求1的组合物,其中第一组分包括丙烯酸类共聚物和第三组分包括含有丙烯酸酯基和/或甲基丙烯酸酯基、烯丙基、乙烯基、不饱和二酸和/或不饱和酸酐中的至少一种的烯属不饱和单体,该单体能够与丙烯酸类共聚物的羧酸基、环氧基、异氰酸酯基和/或羟基中的至少一种反应。
10、根据权利要求1的组合物,其中第二组分通过让(a)与(b)反应来获得:
(a)含有至少一个缩水甘油基的聚苯氧基树脂和/或氢化聚苯氧基树脂,
(b)以下物质的反应产物:
(i)含有乙烯基或烯丙基的醇;与酸酐;
(ii)丙烯酸羟烷基酯和/或甲基丙烯酸羟烷基酯与酸酐;和/或
(iii)烯丙基或乙烯基缩水甘油醚与多元酸;或
单或多官能不饱和羧酸和/或其酸酐。
11、根据权利要求1的组合物,其中第二组分以至少一个以下性能和它们的任何组合为特征:
(I)450到5000的数均分子量;
(II)30到80℃的玻璃化转变温度;
(III)0.2到6.0毫当量双键/g树脂的不饱和度;和/或
(IV)低于20000mPa·s的熔体粘度,通过锥板法在200℃下测定。
12、根据权利要求1的组合物,其中第三组分包括含有选自丙烯酸酯基和或甲基丙烯酸酯基、烯丙基、乙烯基、不饱和二酸和/或不饱和酸酐中的至少一个官能团的低聚物。
13、根据权利要求1的组合物,另外包括至多15重量份的光引发剂/100重量份组分(a)、(b)和(c)。
14、根据权利要求1的组合物,另外包括至多10重量份的至少一种有效改进涂布性能的物质/100重量份组分(a)、(b)和(c)。
15、包括根据任意一项前述权利要求的辐射固化性粉末组合物的粉末清漆和/或粉末色漆。
16、用权利要求16的粉末清漆和/或粉末色漆涂布制品的方法,包括以下步骤:
(a)在该制品上沉积该组合物;
(b)熔化这样获得的涂层;和
(c)将熔融的涂层曝露于足以形成固化涂层的辐射。
17、根据权利要求17的方法,其中涂层通过在80到150℃的温度下加热来熔化。
18、根据权利要求17或18的方法,其中固化辐射是UV辐射或加速电子束。
19、用权利要求17-19的任一项的方法部分或完全涂布的制品。
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WO2005108514A1 (en) * | 2004-05-07 | 2005-11-17 | Cytec Surface Specialties, S.A. | Radiation curable low gloss powder coating compositions |
WO2005108513A1 (en) * | 2004-05-07 | 2005-11-17 | Cytec Surface Specialties, S.A. | Radiation curable low gloss powder coating compositions |
CN101379008A (zh) * | 2006-01-31 | 2009-03-04 | 威士伯来源有限公司 | 用于水泥复合制品的涂布系统 |
CA2741749C (en) * | 2008-11-07 | 2016-07-12 | Dsm Ip Assets B.V. | Heat-curable powder coating composition |
CN103030745B (zh) * | 2012-12-07 | 2014-12-24 | 武汉工程大学 | 水性光固化不饱和聚酯及其制备方法 |
CN103013304B (zh) * | 2012-12-07 | 2015-05-06 | 武汉工程大学 | 溶剂共沸制备水性光固化不饱和聚酯的方法 |
CN103012818B (zh) * | 2012-12-21 | 2014-07-09 | 青岛科技大学 | 一种生物基硫化聚酯橡胶粒子及其制备方法 |
CN103589306B (zh) * | 2013-10-24 | 2016-08-31 | 惠州市长润发涂料有限公司 | 一种高渗透性uv底漆 |
SG11201608263PA (en) * | 2014-04-04 | 2016-10-28 | Ppg Ind Ohio Inc | Branched polyester polymers and soft touch coatings comprising the same |
CN104559657A (zh) * | 2014-12-23 | 2015-04-29 | 王新民 | 一种金属用环氧树脂涂料 |
MX2017007830A (es) | 2014-12-24 | 2017-09-18 | Valspar Sourcing Inc | Composiciones de revestimiento libres de estireno para envasar articulos tales como envases de alimentos y bebidas. |
US11981822B2 (en) | 2014-12-24 | 2024-05-14 | Swimc Llc | Crosslinked coating compositions for packaging articles such as food and beverage containers |
EP3237557B1 (en) * | 2014-12-24 | 2020-06-10 | Swimc Llc | Coating compositions for packaging articles such as food and beverage containers |
CN110229317B (zh) * | 2019-06-13 | 2020-05-22 | 华南理工大学 | 高乙烯基官能度的可uv固化不饱和聚酯树脂及其制备方法与应用 |
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NL9200506A (nl) * | 1992-03-19 | 1993-10-18 | Dsm Nv | Bindmiddelsamenstelling voor poedercoatings. |
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