CN114573820B - 一种耐候涂料用聚酯树脂 - Google Patents
一种耐候涂料用聚酯树脂 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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- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/445—Block-or graft-polymers containing polysiloxane sequences containing polyester sequences
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- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/123—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/137—Acids or hydroxy compounds containing cycloaliphatic rings
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Abstract
本发明涉及一种耐候涂料用聚酯树脂,属于聚氨酯材料技术领域,包括以下原料:新戊二醇、1,6‑己二醇、三羟甲基丙烷、对苯二甲酸、六氢苯酐、二胺化合物、催化剂、稳定剂。本发明首先利用新戊二醇、1,6‑己二醇、三羟甲基丙烷、对苯二甲酸和六氢苯酐作为聚酯树脂的主要合成底物,经过一锅法合成聚酯的预聚物链,并控制上述底物的重量份,使获得的聚酯预聚物链中含有端羧基,然后利用该端羧基和自制的二胺化合物中氨基的反应,使最终获得的聚酯分子链中含有POSS结构和受阻胺结构,利用POSS结构的耐高温特性,以及受阻胺吸收自由基的特性,进而使获得的聚酯树脂具有优异的耐候性能。
Description
技术领域
本发明属于聚氨酯材料技术领域,具体地,涉及一种耐候涂料用聚酯树脂。
背景技术
耐候涂料由于其优异的耐候性能,广泛用于建筑物、户外用器材以及汽车领域,其可以在基底表面形成一层良好的耐候层,以提高基底的耐光照、防水、防腐等性能,起到保护基底的作用。耐候涂料分为溶剂性涂料和粉末涂料。其中,相较于溶剂型涂料,粉末涂料是一种无挥发溶剂的固体粉末状涂料,具有无溶剂、低污染、材料利用率高、能量消耗低等优点,是目前市场上发展涂料类型。粉末涂料的原理是利用树脂与固化剂加热后发生交联反应,形成不熔的坚硬涂层,温度高时,该涂层只能发生分解,而不会像热塑性树脂涂层那样发生软化,因而具有较强的机械性能。粉末涂料包括基底树脂、颜填料、助剂(如抗氧化剂、耐黄剂、流平剂等),其中,基底树脂包括聚酯树脂、环氧树脂、聚丙烯酸酯树脂等。而聚酯树脂粉末涂料与其他类型粉末涂料相比,具有独特的性质,例如,由于聚酯树脂带有极性基团,所以上粉率比环氧树脂高,烘烤过程中不易泛黄,光泽度高,流平性好,漆膜丰满,颜色浅等。如中国专利CN109181504A公开的耐候性能优异的粉末涂料用聚酯树脂制备方法,原料包括PET纺织废料浆块、1,6-己二醇、3-甲基-1,5-戊二醇、催化剂、1,4-环己烷二甲酸、聚对苯二甲酸丁二醇酯和固化促进剂。该发明使用PET纺织废料浆块作为主要成分,只需对聚酯树脂产品进行压滤处理,并实现物尽其用,该发明的聚酯树脂生产的粉末涂料,可使工件表面具有高光泽、高流平和高储存性等优点,能够满足特殊工件对表面具有高光泽或高流平的要求,但是,该发明提供的聚酯树脂仅仅依靠聚对苯二甲酸丁二醇酯的引入,来提高聚酯树脂的耐候性,该种聚酯树脂在耐人工气候老化性试验中,只能达到800h合格,无粉化、起泡、开裂、剥落等异常现象,其耐候性有待提高。而决定聚酯粉末涂料耐候性的关键仍是基体树脂。因此,提供一种耐候性能高的粉末涂料用聚酯树脂是目前聚酯树脂需要解决的技术问题。
发明内容
本发明的目的在于提供一种耐候涂料用聚酯树脂,以解决背景技术中的提到的技术问题。
本发明的目的可以通过以下技术方案实现:
一种耐候涂料用聚酯树脂,包括以下重量份原料:新戊二醇10-25份、1,6-己二醇7-18份、三羟甲基丙烷6-14份、对苯二甲酸40-80份、六氢苯酐2-4份、二胺化合物5-16份、催化剂1-3份、稳定剂1-3份。
进一步地,所述催化剂为钛酸四丁酯、醋酸钴、醋酸锑按照质量比2:1:1混合组成。
进一步地,所述稳定剂为磷酸三甲酯、磷酸三苯酯、邻苯二酚磷酸酯、三乙基磷酸酯中的一种。
进一步地,所述二胺化合物通过以下步骤制成:
步骤A、将双角3-氯丙基POSS和三乙胺溶于二甲苯中,然后冰水浴中搅拌下,滴加2,2,6,6-四甲基哌啶胺,滴加速度为2-3滴/秒,滴加完全后,升至室温搅拌反应3h,水洗,分液,有机相旋蒸,得接枝3-氯丙基POSS,其中,双角3-氯丙基POSS、三乙胺、2,2,6,6-四甲基哌啶胺的摩尔比为1:2.1-2.3:0.8-1;
在上述反应中,利用双角3-氯丙基POSS中的氯基和2,2,6,6-四甲基哌啶胺中的氨基反应,再通过控制双角3-氯丙基POSS和2,2,6,6-四甲基哌啶胺摩尔比,使得双角3-氯丙基POSS分子中的一个氯基与2,2,6,6-四甲基哌啶反应,还剩余有氯基,得接枝3-氯丙基POSS,因此,接枝3-氯丙基POSS的分子结构中接枝有2,2,6,6-四甲基哌啶的分子结构,即接枝3-氯丙基POSS的分子结构中含有受阻胺的结构;
步骤B、将4-羟基苯甲醛溶解于二甲基亚砜中,然后加入碳酸钾和碘化钾,升温至110-120℃,滴加接枝3-氯丙基POSS,滴加速度为2-3滴/秒,滴加完全后,反应8h,结束反应,将反应混合物倒入去离子水中,5℃保温放置30min,然后过滤,取滤饼并用去离子水洗涤2-4次,真空干燥,得苯甲醛衍生物,其中,4-羟基苯甲醛、二甲基亚砜、碳酸钾和接枝3-氯丙基POSS的用量比为0.01mol:15-20mL:0.01mol:0.01mol,碘化钾的加入质量为4-羟基苯甲醛质量的0.4-1%;
在上述反应中,利用酚羟基的Williamson反应,通过4-羟基苯甲醛中的酚羟基和接枝3-氯丙基POSS中的氯基反应,使得接枝3-氯丙基POSS结构接入4-羟基苯甲醛的分子结构中,得苯甲醛衍生物;
步骤C、将苯甲醛衍生物、苯胺和苯胺盐酸盐混合后,然后在氮气保护下,升温至110-120℃,反应2h,然后升温至145-150℃,反应1.5h,结束反应,降温至50-60℃,减压蒸馏出过量的苯胺,加入盐酸将剩余物质溶解,过滤,取滤液并用氢氧化钠溶液中和至滤液pH为7,静置陈化,待陈化完全后,过滤,滤饼用去离子水洗涤2-4次,真空干燥,得二胺化合物,其中,苯甲醛衍生物、苯胺的摩尔比为1:4-6,苯胺盐酸盐加入的质量为苯胺质量的0.7-1%。
在上述反应中利用苯甲醛衍生物中的醛基和苯基化合物在苯胺盐酸盐存在下发生的缩合反应,生成二胺化合物,且该二胺化合物的分子结构式如下所示。
进一步地,所述双角3-氯丙基POSS通过以下步骤制成:
将八苯基POSS钠盐溶于无水四氢呋喃中,然后转移至三口烧瓶中,再在氮气保护下加入三乙胺,0℃冰浴搅拌反应1h,滴加3-氯丙基甲基二氯硅烷的四氢呋喃溶液,滴加速度为1-2滴/秒,滴加完全后,0℃冰浴反应4h,然后升温至室温反应20h,反应结束后过滤,旋干滤液后过柱分离(二氯甲烷:石油醚的体积比为1:2),真空干燥至恒重,得双角3-氯丙基POSS,其中,八苯基POSS钠盐、三乙胺、3-氯丙基甲基二氯硅烷的质量比为78-80:20-26:44-53。
在上述反应中,利用3-氯丙基甲基二氯硅烷中的硅-氯键的水解,然后与八苯基POSS钠盐中的硅氧键形成键连,得双角3-氯丙基POSS,且该双角3-氯丙基POSS的分子结构式如下所示。
一种耐候涂料用聚酯树脂,包括以下步骤制成:
步骤一、向带分馏冷凝器的反应器中加入新戊二醇、1,6-己二醇、三羟甲基丙烷加热至100-130℃,使得各原料熔融,并保温搅拌20-30min;然后加入对苯二甲酸、六氢苯酐及催化剂,通氮气升温至165-185℃,并保温搅拌反应2-3h,得反应液;
步骤二、向步骤一获得的反应液中加入二胺化合物,并升温至240-250℃,保温反应1-2h后,升温至260-270℃,并在0.090-0.095MPa真空下进行缩聚反应200-240min,降温至160-180℃时,加入稳定剂,搅拌20-30min,降温,出料,得一种耐候涂料用聚酯树脂。
本发明的有益效果:
本发明首先利用新戊二醇、1,6-己二醇、三羟甲基丙烷、对苯二甲酸和六氢苯酐作为聚酯树脂的主要合成底物,经过一锅法合成聚酯的预聚物链,并控制上述底物的重量份,使获得的聚酯预聚物链中含有端羧基,然后利用该端羧基和自制的二胺化合物中氨基的反应,使最终获得的聚酯分子链中含有POSS结构和受阻胺结构,利用POSS结构的耐高温特性,以及受阻胺吸收自由基的特性,进而使获得的聚酯树脂具有优异的耐候性能。
具体实施方式
下面将结合本发明实施例,对本发明实施例中的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有作出创造性劳动前提下所获得的所有其它实施例,都属于本发明保护的范围。
实施例1
八苯基POSS钠盐的制备:
向装有150mL异丙醇的单颈烧瓶中依次加入37g苯基三甲氧基硅烷、3.2g去离子水和4.2g片状氢氧化钠,然后加热回流4h后,将温度降至室温,并反应20h,旋蒸出异丙醇,得白色固体,并将白色固体真空干燥,得八苯基POSS钠盐。
实施例2
双角3-氯丙基POSS的制备:
将78g实施例1制备八苯基POSS钠盐溶于100mL无水四氢呋喃中,然后转移至三口烧瓶中,再在氮气保护下加入20g三乙胺,0℃冰浴搅拌反应1h,滴加50mL含有44g 3-氯丙基甲基二氯硅烷的四氢呋喃溶液,滴加速度为1滴/秒,滴加完全后,0℃冰浴反应4h,然后升温至室温反应20h,反应结束后过滤,旋干滤液后过柱分离(二氯甲烷:石油醚的体积比为1:2),真空干燥至恒重,得双角3-氯丙基POSS。
实施例3
双角3-氯丙基POSS的制备:
将80g实施例1制备的八苯基POSS钠盐溶于100mL无水四氢呋喃中,然后转移至三口烧瓶中,再在氮气保护下加入26g三乙胺,0℃冰浴搅拌反应1h,滴加50mL含有53g 3-氯丙基甲基二氯硅烷的四氢呋喃溶液,滴加速度为2滴/秒,滴加完全后,0℃冰浴反应4h,然后升温至室温反应20h,反应结束后过滤,旋干滤液后过柱分离(二氯甲烷:石油醚的体积比为1:2),真空干燥至恒重,得双角3-氯丙基POSS。
实施例4
二胺化合物的制备:
步骤A、将0.1mol实施例2制备的双角3-氯丙基POSS和0.21mol三乙胺溶于100mL二甲苯中,然后冰水浴中搅拌下,滴加0.8mol 2,2,6,6-四甲基哌啶胺,滴加速度为2滴/秒,滴加完全后,升至室温搅拌反应3h,水洗,分液,有机相旋蒸,得接枝3-氯丙基POSS;
步骤B、将0.01mol 4-羟基苯甲醛溶解于15mL二甲基亚砜中,然后加入0.01mol碳酸钾和碘化钾,升温至110℃,滴加0.01mol接枝3-氯丙基POSS,滴加速度为2滴/秒,滴加完全后,反应8h,结束反应,将反应混合物倒入去离子水中,5℃保温放置30min,然后过滤,取滤饼并用去离子水洗涤2次,真空干燥,得苯甲醛衍生物,其中,碘化钾的加入质量为4-羟基苯甲醛质量的0.4%;
步骤C、将0.01mol苯甲醛衍生物、0.04mol苯胺和苯胺盐酸盐混合后,然后在氮气保护下,升温至110℃,反应2h,然后升温至145℃,反应1.5h,结束反应,降温至50℃,减压蒸馏出过量的苯胺,加入盐酸将剩余物质溶解,过滤,取滤液并用氢氧化钠溶液中和至滤液pH为7,静置陈化,待陈化完全后,过滤,滤饼用去离子水洗涤2次,真空干燥,得二胺化合物,其中,苯胺盐酸盐加入的质量为苯胺质量的0.7%。
实施例5
二胺化合物的制备:
步骤A、将0.1mol实施了例3制备的双角3-氯丙基POSS和0.23mol三乙胺溶于100mL二甲苯中,然后冰水浴中搅拌下,滴加0.1mol 2,2,6,6-四甲基哌啶胺,滴加速度为2-3滴/秒,滴加完全后,升至室温搅拌反应3h,水洗,分液,有机相旋蒸,得接枝3-氯丙基POSS;
步骤B、将0.01mol 4-羟基苯甲醛溶解于20mL二甲基亚砜中,然后加入0.01mol碳酸钾和碘化钾,升温至120℃,滴加0.01mol接枝3-氯丙基POSS,滴加速度为2-3滴/秒,滴加完全后,反应8h,结束反应,将反应混合物倒入去离子水中,5℃保温放置30min,然后过滤,取滤饼并用去离子水洗涤4次,真空干燥,得苯甲醛衍生物,其中,碘化钾的加入质量为4-羟基苯甲醛质量的1%;
步骤C、将0.01mol苯甲醛衍生物、0.06mol苯胺和苯胺盐酸盐混合后,然后在氮气保护下,升温至120℃,反应2h,然后升温至150℃,反应1.5h,结束反应,降温至60℃,减压蒸馏出过量的苯胺,加入盐酸将剩余物质溶解,过滤,取滤液并用氢氧化钠溶液中和至滤液pH为7,静置陈化,待陈化完全后,过滤,滤饼用去离子水洗涤4次,真空干燥,得二胺化合物,其中,苯胺盐酸盐加入的质量为苯胺质量的1%。
实施例6
一种耐候涂料用聚酯树脂的制备:
步骤一、准备包括以下重量份原料:新戊二醇10份、1,6-己二醇7份、三羟甲基丙烷6份、对苯二甲酸40份、六氢苯酐2份、实施例4制备的二胺化合物5份、催化剂1份、稳定剂1份;所述催化剂为钛酸四丁酯、醋酸钴、醋酸锑按照质量比2:1:1混合组成;所述稳定剂为磷酸三甲酯;
步骤二、向带分馏冷凝器的反应器中加入新戊二醇、1,6-己二醇、三羟甲基丙烷加热至100℃,使得各原料熔融,并保温搅拌20min;然后加入对苯二甲酸、六氢苯酐及催化剂,通氮气升温至165℃,并保温搅拌反应3h,得反应液;
步骤三、向步骤二获得的反应液中加入实施例4制备的二胺化合物,并升温至240℃,保温反应2h后,升温至260℃,并在0.090MPa真空下进行缩聚反应240min,降温至160℃时,加入稳定剂,搅拌30min,降温,出料,得一种耐候涂料用聚酯树脂。
实施例7
一种耐候涂料用聚酯树脂的制备:
步骤一、准备包括以下重量份原料:新戊二醇15份、1,6-己二醇12份、三羟甲基丙烷10份、对苯二甲酸60份、六氢苯酐3份、实施例5制备的二胺化合物11份、催化剂2份、稳定剂2份;所述催化剂为钛酸四丁酯、醋酸钴、醋酸锑按照质量比2:1:1混合组成;所述稳定剂为磷酸三苯酯;
步骤二、向带分馏冷凝器的反应器中加入新戊二醇、1,6-己二醇、三羟甲基丙烷加热至130℃,使得各原料熔融,并保温搅拌30min;然后加入对苯二甲酸、六氢苯酐及催化剂,通氮气升温至185℃,并保温搅拌反应2h,得反应液;
步骤三、向步骤二获得的反应液中加入实施例5制备的二胺化合物,并升温至250℃,保温反应1h后,升温至260℃,并在0.095MPa真空下进行缩聚反应200min,降温至180℃时,加入稳定剂,搅拌20min,降温,出料,得一种耐候涂料用聚酯树脂。
实施例8
一种耐候涂料用聚酯树脂的制备:
步骤一、准备包括以下重量份原料:新戊二醇25份、1,6-己二醇18份、三羟甲基丙烷14份、对苯二甲酸80份、六氢苯酐4份、实施例4制备的二胺化合物16份、催化剂3份、稳定剂3份;所述催化剂为钛酸四丁酯、醋酸钴、醋酸锑按照质量比2:1:1混合组成;所述稳定剂为三乙基磷酸酯;
步骤二、向带分馏冷凝器的反应器中加入新戊二醇、1,6-己二醇、三羟甲基丙烷加热至130℃,使得各原料熔融,并保温搅拌30min;然后加入对苯二甲酸、六氢苯酐及催化剂,通氮气升温至185℃,并保温搅拌反应3h,得反应液;
步骤三、向步骤二获得的反应液中加入实施例4制备的二胺化合物,并升温至250℃,保温反应2h后,升温至270℃,并在0.095MPa真空下进行缩聚反应240min,降温至180℃时,加入稳定剂,搅拌20min,降温,出料,得一种耐候涂料用聚酯树脂。
对比例1
二胺化合物的制备:与实施例4相比,删除步骤A,并将步骤B中接枝3-氯丙基POSS替换成实施例2制备的双角3-氯丙基POSS,其余实施例4相同。
对比例2
一种耐候涂料用聚酯树脂的制备:与实施例6相比,二胺化合物为对比例1制备,其余与实施例6相同。
对比例3
一种耐候涂料用聚酯树脂的制备:与实施例7相比,将二胺化合物替换成对苯二胺,其余与实施例7相同。
对比例4
一种耐候涂料用聚酯树脂的制备:与实施例8相比,将二胺化合物替换成三乙胺,其余与实施例8相同。
实施例9
将实施例6-8和对比例2-4获得的聚酯树脂进行测试,测试的性能包括软化点和玻璃化转变温度,其中,软化点测定按照GB/T 27808进行检测,玻璃化转变温度测定按照GB/T19466.2进行检测,测试结果如表1所示。
表1
从表1中的数据中可以看出,实施例6-8获得的聚酯树脂的热稳定性优于对比例3-4获得的聚酯树脂。
实施例10
将实施例6-8和对比例2-4获得的聚酯树脂分别与TGIC、流平剂、钛白粉、硫酸钡、碳酸钙、安息香按照固定配比称好后混匀,用螺杆挤出机熔融分别挤出、压片、破碎,然后将片料粉碎过筛制成粉末涂料。粉末涂料采用静电喷枪喷涂在0.8mm厚的除锈、除油的金属板上,涂层厚度60μm,在200℃下固化10min,得涂层,其中,聚酯树脂试样、TGIC、流平剂、钛白粉、硫酸钡、碳酸钙、安息香质量配比为300g:26g:124g:46g:46g:3.5g:2.4g。最后进行涂层的性能测试,包括涂层的外观、硬度、耐候性能进行测试,外观使用目测固化的涂层是否平整,是否存在褶皱、气孔等;硬度按照标准GB/T6739进行测试,使用铅笔来测试是否可以对涂层划出痕迹或划伤涂膜;耐候性能测试按照标准ASTM G155进行测试,按照氙弧灯老化试验,试验温度为35±2℃,测试结果见表2。
表2
外观 | 硬度 | 耐候性能测试 | |
实施例6 | 平整 | 3H | 1100h通过 |
实施例7 | 平整 | 3H | 1100h通过 |
实施例8 | 平整 | 3H | 1100h通过 |
对比例2 | 平整 | 3H | 1000h通过 |
对比例3 | 平整 | 2H | 900h通过 |
对比例4 | 平整 | 2H | 800h通过 |
从表2中的数据中可以看出,实施例6-8获得的聚酯树脂的耐候性能优于对比例2-4获得的聚酯树脂。
在说明书的描述中,参考术语“一个实施例”、“示例”、“具体示例”等的描述意指结合该实施例或示例描述的具体特征、结构、材料或者特点包含于本发明的至少一个实施例或示例中。在本说明书中,对上述术语的示意性表述不一定指的是相同的实施例或示例。而且,描述的具体特征、结构、材料或者特点可以在任何的一个或多个实施例或示例中以合适的方式结合。
以上内容仅仅是对本发明所作的举例和说明,所属本技术领域的技术人员对所描述的具体实施例做各种各样的修改或补充或采用类似的方式替代,只要不偏离发明或者超越本权利要求书所定义的范围,均应属于本发明的保护范围。
Claims (1)
1.一种耐候涂料用聚酯树脂,其特征在于:包括以下原料:新戊二醇、1,6-己二醇、三羟甲基丙烷、对苯二甲酸、六氢苯酐、二胺化合物、催化剂、稳定剂;
各原料的重量份具体如下:新戊二醇10-25份、1,6-己二醇7-18份、三羟甲基丙烷6-14份、对苯二甲酸40-80份、六氢苯酐2-4份、二胺化合物5-16份、催化剂1-3份、稳定剂1-3份;
所述二胺化合物包括以下步骤制成:
将八苯基POSS钠盐溶于无水四氢呋喃中,再在氮气保护下加入三乙胺,0℃冰浴搅拌反应1h,滴加3-氯丙基甲基二氯硅烷的四氢呋喃溶液,滴加完全后,0℃冰浴反应4h,然后升温至室温反应20h,反应结束后过滤,旋干滤液后过柱分离,真空干燥至恒重,得双角3-氯丙基POSS;
所述八苯基POSS钠盐、三乙胺、3-氯丙基甲基二氯硅烷的质量比为78-80:20-26:44-53;
将双角3-氯丙基POSS和三乙胺溶于二甲苯中,然后冰水浴中搅拌下,滴加2,2,6,6-四甲基哌啶胺,滴加速度为2-3滴/秒,滴加完全后,升至室温搅拌反应3h,水洗,分液,有机相旋蒸,得接枝3-氯丙基POSS;
所述双角3-氯丙基POSS、三乙胺、2,2,6,6-四甲基哌啶胺的摩尔比为1:2.1-2.3:0.8-1;
将4-羟基苯甲醛溶解于二甲基亚砜中,然后加入碳酸钾和碘化钾,升温至110-120℃,滴加接枝3-氯丙基POSS,滴加速度为2-3滴/秒,滴加完全后,反应8h,结束反应,将反应混合物倒入去离子水中,5℃保温放置30min,然后过滤,取滤饼并用去离子水洗涤,真空干燥,得苯甲醛衍生物;
所述4-羟基苯甲醛、二甲基亚砜、碳酸钾和接枝3-氯丙基POSS的用量比为0.01mol:15-20mL:0.01mol:0.01mol;
将苯甲醛衍生物、苯胺和苯胺盐酸盐混合后,然后在氮气保护下,升温至110-120℃,反应2h,然后升温至145-150℃,反应1.5h,结束反应,经后处理,得二胺化合物。
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