CN109251299A - 可聚合型高分子紫外线吸收剂的用途及包含其的用以形成聚氨酯树脂的组成物 - Google Patents

可聚合型高分子紫外线吸收剂的用途及包含其的用以形成聚氨酯树脂的组成物 Download PDF

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CN109251299A
CN109251299A CN201810602400.8A CN201810602400A CN109251299A CN 109251299 A CN109251299 A CN 109251299A CN 201810602400 A CN201810602400 A CN 201810602400A CN 109251299 A CN109251299 A CN 109251299A
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polyalcohol
ultraviolet absorbing
absorber
absorbing agent
alcohol
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张光钦
林瑞基
魏久泰
蔡喻明
柯子衡
周德纲
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Everlight Chemical Industrial Corp
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Everlight Chemical Industrial Corp
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Abstract

一种可聚合型高分子紫外线吸收剂的用途，其用于聚氨酯树脂的制备上，其中可聚合型高分子紫外线吸收剂由：具有一可反应活性氢的紫外线吸收剂及一具有三个‑NCO官能基的多异氰酸酯(Polyisocyanate)反应而得。除此之外，本发明还提供一种包含前述聚合型高分子紫外线吸收剂的用以形成聚氨酯树脂的组成物。

Description

可聚合型高分子紫外线吸收剂的用途及包含其的用以形成聚 氨酯树脂的组成物
技术领域
本发明关于一种可聚合型高分子紫外线吸收剂的用途及包含其的用以形成聚氨酯树脂的组成物，其中可聚合型高分子紫外线吸收剂除了可解决聚氨酯树脂黄变的问题外，更具有低迁移性。
背景技术
聚氨酯树脂本身虽具有优良物性，但容易受光、热影响使其黄变，进而造成劣化。例如，聚氨酯树脂中的芳香族异氰酸盐(如TDI、MDI等)，长期受到紫外光的影响之下会引发光降解而造成断键，随之又产生了带有发射基团的有色物质而导致颜色变黄。
目前欲解决聚氨酯树脂容易黄变问题，所添加的紫外线吸收剂属于小分子，小分子型的紫外线吸收剂容易因长时间接触到高温或接触到有机溶剂(油相)物时，导致会有迁移(migration)的问题，造成小分子型的紫外线吸收剂被溶出而损失。
有鉴于此，目前亟需发展一种紫外线吸收剂，其除了可解决聚氨酯树脂容易黄变问题外，更具有低迁移率，而不会因溶出而损失，以延长聚氨酯树脂耐黄变的时间。
发明内容
本发明的主要目的在于提供一种可聚合型高分子紫外线吸收剂的用途及包含其的用以形成聚氨酯树脂的组成物，其用于聚氨酯树脂的制备上，以解决聚氨酯树脂容易黄变的问题。
本发明提供一种可聚合型高分子紫外线吸收剂的用途，其用于聚氨酯树脂的制备上，其中可聚合型高分子紫外线吸收剂由：具有一可反应活性氢的紫外线吸收剂及一具有三个-NCO官能基的多异氰酸酯(Polyisocyanate)反应而得。
在本发明的一实施例中，可聚合型高分子紫外线吸收剂更由：所述具有一可反应活性氢的紫外线吸收剂、所述具有三个-NCO官能基的多异氰酸酯及一双醇或多元醇(Polyol)反应而得。
因此，本发明的可聚合型高分子紫外线吸收剂可如下式(I)所示：
其中，A衍生自一可反应活性氢的紫外线吸收剂；
B衍生自一具有三个-NCO官能基的多异氰酸酯；
C衍生自一双醇或多元醇；以及
n为0～3。
当式(I)中的n为0时，可聚合型高分子紫外线吸收剂由：具有一可反应活性氢的紫外线吸收剂及一具有三个-NCO官能基的多异氰酸酯反应而得；其中，可反应活性氢与多异氰酸酯的其中一个-NCO官能基反应。当式(I)中的n为1时，可聚合型高分子紫外线吸收剂由：所述具有一可反应活性氢的紫外线吸收剂、所述具有三个-NCO官能基的多异氰酸酯及一双醇或多元醇反应而得；其中，可反应活性氢与多异氰酸酯的其中一个-NCO官能基反应，而双醇或多元醇的-OH官能基与另一个-NCO官能基反应。当式(I)中的n为2或3时，可聚合型高分子紫外线吸收剂由：多个具有一可反应活性氢的紫外线吸收剂、多个具有三个-NCO官能基的多异氰酸酯及多个双醇或多元醇反应而得；其中，可反应活性氢与多异氰酸酯的其中一个-NCO官能基反应，而双醇或多元醇的-OH官能基与另一个-NCO官能基反应。
相较于目前解决聚氨酯树脂黄变问题的小分子紫外线吸收剂，本发明的可聚合型高分子紫外线吸收剂的分子量明显大于现有所使用的小分子紫外线吸收剂。由于本发明所使用的可聚合型高分子紫外线吸收剂具有较大分子量且具有能与聚氨酯树脂单体、寡聚物或聚合物反应的-NCO官能基，故于聚氨酯树脂的反应过程中，能当作添加剂一同参与反应。因此，本发明的可聚合型高分子紫外线吸收剂除了可解决聚氨酯树脂黄变的情形外，更能解决小分子紫外线吸收剂容易因长时间接触到高温或接触到有机溶剂(油相)物时产生的迁移(migration)问题。
在本发明中，可聚合型高分子紫外线吸收剂的重量平均分子量可小于5000；且较佳的介于1100至2500的范围。
在本发明中，紫外线吸收剂并无特别限制，仅需具有一可反应的活性氢，所述可反应的活性氢选自：-OH、-NH2及-NH-所组成的群组。更具体地，所述紫外线吸收剂选自：苯并三唑类(Benzotriazole)紫外线吸收剂、二苯酮类(Benzophenone)紫外线吸收剂、三嗪类(Triazine)紫外线吸收剂、草酰苯胺类(Oxanilide)紫外线吸收剂及氰基丙烯酸酯类(Cyanoacrylate)紫外线吸收剂所组成的群组。在本发明的一实施例中，紫外线吸收剂为苯并三唑类紫外线吸收剂。
在本发明中，多异氰酸酯具有三个-NCO官能基。据此，紫外线吸收剂与多异氰酸酯进行反应后，紫外线吸收剂的可反应的活性氢连接至多异氰酸酯的其中一个-NCO官能基。由于多异氰酸酯尚剩余两个-NCO官能基，故在聚氨酯树脂的合成过程中，可参与反应并可避免聚合中断的情形产生，而无法得到具有预期分子量的聚氨酯树脂。在此，所述多异氰酸酯选自：六亚甲基二异氰酸酯三聚物(hexamethylene diisocyanate trimer；HDITRIMER)、六亚甲基二异氰酸酯缩二脲(Hexamethylenediisocyanate biuret；HDB)及其混合物所组成的群组。在本发明的一实施例中，多异氰酸酯为HDI TRIMER或HDB。
在本发明中，双醇或多元醇包含两个以上的-OH官能基，据此，双醇或多元醇与多异氰酸酯进行反应后，双醇或多元醇的-OH官能基连接至多异氰酸酯的-NCO官能基。在此，双醇或多元醇选自：阴离子型双醇或多元醇、阳离子型双醇或多元醇、非离子型双醇或多元醇及其混合物所组成的群组。更具体地，阴离子型双醇或多元醇选自：2，2-双(羟甲基)丁酸(2，2-Bis(hydroxymethyl)butyric acid；DMBA)、2，2-双(羟甲基)丙酸(2，2-Bis(hydroxymethyl)propionic acid；DMPA)、1，4-丁二醇-2-磺酸钠(1，4-butanediol-2-Sodium)及其混合物所组成的群组。阳离子型双醇或多元醇选自：N-甲基二乙醇胺(N-methyldiethanolamine；MDEA)、三乙醇胺(Triethanolamine)及其混合物所组成的群组。非离子型双醇选自：乙二醇(EG)、丙二醇(PG)、丁二醇(BD)、己二醇(HD)、一缩乙二醇(DEG)、二丙二醇(DPG)及新戊二醇(NPG)所组成的群组。非离子型多元醇为非离子型聚醚多元醇或非离子型聚酯多元醇，其中所述非离子型聚醚多元醇选自：聚四氢氟喃醚二元醇(PTMEG)、聚环氧乙烷二元醇(PEG)、聚环氧丙烷二元醇(PPG)及其共聚物所组成的群组，所述非离子型聚酯多元醇由双酸与双醇酯化聚合的多元醇，所述双酸选自：己二酸(AA)、癸二酸(SA)、对苯二甲酸(TPA)、间苯二甲酸(IPA)、邻苯二甲酸酐(PA)以及其混合物所组成的群组，所述双醇选自：乙二醇(EG)、丙二醇(PG)、丁二醇(BD)、己二醇(HD)、新戊二醇(NPG)、一缩乙二醇(DEG)、二丙二醇(DPG)及其混合物所组成的群组。在本发明的一实施例中，双醇或多元醇为聚环氧乙烷二元醇。
除此之外，本发明还提供一种用以形成聚氨酯树脂的组成物，包括：一包含两个以上-NCO官能基的单体、寡聚物或聚合物；以及前述的可聚合型高分子紫外线吸收剂。在此，可聚合型高分子紫外线吸收剂的含量并无特殊限制，只要能够达到解决聚氨酯树脂容易黄变的问题的目的即可。在本发明的一实施例中，可聚合型高分子紫外线吸收剂的含量占组成物总重量的1wt％至30wt％、或2wt％至20wt％。
在本发明中，聚氨酯树脂的种类并无特殊限制，例如，为一反应型聚氨酯或一热塑型聚氨酯。
附图说明
图1为在反应型聚氨酯中添加不同的紫外线吸收剂的UVA有效量及耐黄变级数关系图；
图2为于热塑型聚氨酯中添加不同的紫外线吸收剂的UVA有效量及耐黄变级数关系图；
图3为在热塑型聚氨酯中添加不同剂量的紫外线吸收剂的UVA有效量及耐黄变级数关系图。
具体实施方式
以下通过特定的具体实施例说明本发明的实施方式，本领域技术人员通过本说明书所公开的内容轻易地了解本发明的其他优点与功效。本发明也通过其他不同的具体实施例加以施行或应用，本说明书中的各项细节也可针对不同观点与应用，在不悖离本创作的精神下进行各种修饰与变更。
除非文中另有说明，否则说明书及所附申请专利范围中所使用的单数形式(一)及(所述)包括一或多个个体。
除非文中另有说明，否则说明书及所附申请专利范围中所使用的术语(或)通常包括(及/或)的含义。
本文所使用的术语(重量平均分子量)，利用凝胶渗透层析(GPC)溶剂：四氢呋喃(THF)，所测定的换算成聚苯乙烯的重量平均分子量(Mw)的值。
详细的制备方法在后文的实施例中描述，也可使用与实施例类似的方法制备可聚合型高分子紫外线吸收剂。本发明的可聚合型高分子紫外线吸收剂的制备方法(例如：合成方法、反应条件、顺序等)及使用材料，并不限于本文中所提及到的。
本发明将通过实施例更具体地说明，但所述等实施例并非用于限制本发明的范畴。除非特别指明，于下列实施例与比较例中用于表示成份含量以及物质量的(％)以重量为基准。
化合物1的制备
取620gα-[3-[3-(2H-苯并三唑-2-基)-5-(1，1-二甲基乙基)-4-羟苯基]-1-酮基丙基]-ω-羟基聚(酮基-1，2-乙烷二基)(α-[3-[3-(2H-Benzotriazol-2-yl)-5-(1，1-dimethylethyl)-4-hydroxyphenyl]-1-oxopropyl]-ω-hydroxypoly(oxo-1，2-ethanediyl)，台湾永光化学工业股份有限公司，Eversorb 80(EV80))置于反应瓶中，进行真空除水。在降温至60℃后，将504.6g THDI(HDI trimer，CORONA HX；TOSOH)加入反应瓶中，在氮气环境下升温至70～75℃进行反应。当滴定NCO反应官能基摩尔数达反应终点后(自由NCO％＝6.53±0.65％)即完成反应，而得到化合物1。
化合物2的制备
取620g EV80及150g PEG-300(ORIENTAL UNION CHEMICAL CO.)分别置于两个反应瓶中，进行真空除水。降温至60℃后，将504.6g THDI(CORONA HX；TOSOH)加入反应瓶中，在氮气环境下升温至70～75℃进行反应。滴定NCO反应官能基摩尔数，当自由NCO％达～6.53％，加入PEG300继续反应；当滴定NCO反应官能基摩尔数达反应终点后(free NCO％＝3.76±0.37％)即完成反应，得到化合物2。
化合物3的制备
取620g EV80置于反应瓶中，进行真空除水。在降温至60℃后，将423.4g六亚甲基二异氰酸酯缩二脲(Hexamethylene diisocyanate biuret,HDB-100；AN FONG)加入反应瓶中，在氮气环境下升温至70～75℃进行反应。当滴定NCO反应官能基摩尔数达反应终点后(free NCO％＝6.53±0.65％)即完成反应，得到化合物3。
反应型聚氨酯(polyurethane reactive；PUR)的制备
将700g聚醇(200g DAHINOL P-213(ZAND SHIN POLYMER Co.)及500g AR-U2010B1(YONG SHUN CHEMICAL Co.))混合置入反应瓶中，搅拌均匀后进行真空除水。而后，加入300g异氰酸酯(50g44M(covestro)及250g TAKENATETM D-110N(MitsuiChemicals))，在氮气环境下升温至60～85℃进行反应。当滴定NCO反应官能基摩尔数达反应终点后(自由NCO％＝3.6±0.4％)即完成反应。最后，加入化合物1、化合物2或化合物3搅拌均匀即得成品。
在此，将所制得的反应型聚氨酯进行UV光照射及色差分析，以评估其耐黄变的功效。其中，UV光照射条件为，UVA-340nm、60℃、照度0.89W/m2/nm、时间20小时。此外，将所制得的反应型聚氨酯进行迁移验证分析；其将所制得的反应型聚氨酯泡于甲苯(toluene)中，超声波震荡1小时；而后，再以前述相同的方法，进行UV光照射及色差分析，以评估其耐黄变的功效。
迁移验证分析及耐黄变的功效评估结果如下表1及图1所示。在图1中，显示比较例1-1、比较例1-2及实施例1-1(添加化合物1)的评估结果。
表1实验结果对比
热塑型聚氨酯(thermoplastic polyurethane；TPU)的制备
将2000g聚醇(2000(INVISTA))与4.5g增链剂(1，4-Butanediol)混合置入反应瓶中，取125g异氰酸酯(44M(covestro))并置入另一个反应瓶，将两者进行真空除水。除完水灌氮气进入，并准备冰块水浴，移到搅拌装置旁准备进行反应。先倒入聚醇与增链剂，接着在冰浴下分三段加入44M，且化合物2伴随44加入的第一与第二段时一起加入。将样品倒入容器中进行后烤：在60℃烘箱内隔夜，可获得TPU料块。
而后，将上述的TPU料块进行粉碎；并进行熔融射出成型，可获得TPU试片。
在此，以前述相同方法进行UV光照射及色差分析与迁移验证分析。迁移验证分析及耐黄变的功效评估结果如下表2、图2及图3所示。于图2中，显示比较例2-2及实施例2-2(添加化合物2)的评估结果。
表2实验结果对比
在表1及表2中，比较例1-2及比较例2-2所使用的Tinuvin 384结构式如下所示。
如表1、表2、图1至图3的结果所示，由UV光照射及色差分析测试结果得知，添加5wt％的化合物1、2或3(可聚合型高分子紫外线吸收剂)、或5wt％小分子UVA(Tinuvin 384)在PUR或TPU中，都可有效提升耐黄变级数至3.5级以上。经由溶剂浸泡及超声波震荡的迁移测试后，添加5wt％的化合物1、2或3(可聚合型高分子紫外线吸收剂)的PUR或TPU，耐黄变级数仍可维持在3级以上，但添加5wt％小分子UVA的PUR或TPU，耐黄变级数则下降至2级以下。由上述结果证实，添加本发明的可聚合型高分子紫外线吸收剂在PUR或TPU中，可明显提升PUR或TPU的耐黄变性；且本发明的可聚合型高分子紫外线吸收剂兼具低迁移性(lowmigration)。
本发明的可聚合型高分子紫外线吸收剂除了可应用于前述PUR及TPU外，也可应用于其他种类的聚氨酯(PU)上，例如：PU发泡体。此外，本发明的可聚合型高分子紫外线吸收剂的应用领域并无特殊限制，用于如涂布、接着、密封、弹性体等四大领域的树酯、或其他需要PU的领域上。
上述实施例仅为了方便说明而举例而已，本发明所主张的权利范围自应以申请专利范围所述为准，而非仅限于上述实施例。

Claims (13)

1.一种可聚合型高分子紫外线吸收剂的用途，其用于聚氨酯树脂的制备上，其中所述可聚合型高分子紫外线吸收剂由：具有一可反应活性氢的紫外线吸收剂及一具有三个-NCO官能基的多异氰酸酯(Polyisocyanate)反应而得。
2.根据权利要求1所述的用途，其中所述可聚合型高分子紫外线吸收剂的重量平均分子量小于5000。
3.根据权利要求1所述的用途，其中所述可反应活性氢选自：-OH、-NH2及-NH-所组成的群组。
4.根据权利要求1所述的用途，其中所述紫外线吸收剂选自：苯并三唑类(Benzotriazole)紫外线吸收剂、二苯酮类(Benzophenone)紫外线吸收剂、三嗪类(Triazine)紫外线吸收剂、草酰苯胺类(Oxanilide)紫外线吸收剂及氰基丙烯酸酯类(Cyanoacrylate)紫外线吸收剂所组成的群组。
5.根据权利要求1所述的用途，其中所述多异氰酸酯选自：六亚甲基二异氰酸酯三聚物(hexamethylene diisocyanate trimer；HDI TRIMER)、六亚甲基二异氰酸酯缩二脲(Hexamethylenediisocyanate biuret；HDB)及其混合物所组成的群组。
6.根据权利要求1所述的用途，其中所述可聚合型高分子紫外线吸收剂由：所述具有一可反应活性氢的紫外线吸收剂、所述具有三个-NCO官能基的多异氰酸酯(Polyisocyanate)及一双醇或多元醇(Polyol)反应得到。
7.根据权利要求6所述的用途，其中所述双醇或多元醇选自：阴离子型双醇或多元醇、阳离子型双醇或多元醇、非离子型双醇或多元醇及其混合物所组成的群组。
8.根据权利要求7所述的用途，其中所述阴离子型双醇或多元醇选自：2，2-双(羟甲基)丁酸(2，2-Bis(hydroxymethyl)butyric acid；DMBA)、2，2-双(羟甲基)丙酸(2，2-Bis(hydroxymethyl)propionic acid；DMPA)、1，4-丁二醇-2-磺酸钠(1，4-butanediol-2-Sodium)及其混合物所组成的群组。
9.根据权利要求7所述的用途，其中所述阳离子型双醇或多元醇选自：N-甲基二乙醇胺(N-methyldiethanolamine；MDEA)、三乙醇胺(Triethanolamine)及其混合物所组成的群组。
10.根据权利要求7所述的用途，其中所述非离子型双醇选自：乙二醇(EG)、丙二醇(PG)、丁二醇(BD)、己二醇(HD)、一缩乙二醇(DEG)、二丙二醇(DPG)及新戊二醇(NPG)所组成的群组，所述非离子型多元醇为非离子型聚醚多元醇或非离子型聚酯多元醇，其中所述非离子型聚醚多元醇选自：聚四氢氟喃醚二元醇(PTMEG)、聚环氧乙烷二元醇(PEG)、聚环氧丙烷二元醇(PPG)及其共聚物所组成的群组，所述非离子型聚酯多元醇由双酸与双醇酯化聚合的多元醇，所述双酸选自：己二酸(AA)、癸二酸(SA)、对苯二甲酸(TPA)、间苯二甲酸(IPA)、邻苯二甲酸酐(PA)以及其混合物所组成的群组，所述双醇选自：乙二醇(EG)、丙二醇(PG)、丁二醇(BD)、己二醇(HD)、新戊二醇(NPG)、一缩乙二醇(DEG)、二丙二醇(DPG)及其混合物所组成的群组。
11.根据权利要求1所述的用途，其中所述聚氨酯树脂为一反应型聚氨酯或一热塑型聚氨酯。
12.一种用以形成聚氨酯树脂的组成物，包括：
一包含两个以上-NCO官能基的单体、寡聚物或聚合物；以及
一可聚合型高分子紫外线吸收剂，其由：具有一可反应活性氢的紫外线吸收剂及一具有三个-NCO官能基的多异氰酸酯(Polyisocyanate)反应而得。
13.根据权利要求12所述的组成物，其中所述可聚合型高分子紫外线吸收剂的含量占组成物总重量的1wt％至30wt％。
CN201810602400.8A 2017-07-12 2018-06-12 可聚合型高分子紫外线吸收剂的用途及包含其的用以形成聚氨酯树脂的组成物 Pending CN109251299A (zh)

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