CN1165508C - 甲基环氧乙烷二苯甲酰间苯二酚紫外光吸收剂 - Google Patents

甲基环氧乙烷二苯甲酰间苯二酚紫外光吸收剂 Download PDF

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CN1165508C
CN1165508C CNB981035930A CN98103593A CN1165508C CN 1165508 C CN1165508 C CN 1165508C CN B981035930 A CNB981035930 A CN B981035930A CN 98103593 A CN98103593 A CN 98103593A CN 1165508 C CN1165508 C CN 1165508C
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A·K·思莫尼安
G·R·吉勒特
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J·E·皮克特
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Abstract

已制备出环氧化的DBR及其各种衍生物，由于其配伍性和溶解性，它们可用于涂料中。这些涂料可以是丙烯酸、环氧或硅酮硬涂层，它们是热或光固体热固性的或各种溶剂类型的热塑性涂料物质。本发明公开的紫外线吸收剂比单纯的二苯甲酰间苯二酚具有更高分子量及低挥发度的优点，因而具有加工优势。

Description

甲基环氧乙烷二苯甲酰 间苯二酚紫外光吸收剂
本发明涉及具有紫外光吸收性能的二苯甲酰间苯二酚的衍生物，这些化合物的制备方法以及含有这些化合物的涂料组合物。更具体地说，此二苯甲酰间苯二酚化合物包含在桥接的亚甲基桥上与环氧乙烷基团偶合的二苯甲酰的苯二酚及其衍生物。本发明还涉及含有二苯甲酰间苯二酚化合物的涂料组合物，当这些化合物应用于热塑性树脂制品时，可以降低由于曝露于紫外线照射而引起的树脂褪色。
通常，热塑性物质，如聚碳酸酯具有优良的特性，比如透明度好，高易拉伸性，高热挺温度以及尺寸稳定性好。不少热塑性物质是透明的，有些适用于替代汽车、航天及建筑上用的玻璃。然而，这些树脂容易在紫外光照射下老化，其证据就是逐步褪色。其结果是透明度降低、基质的机械性质老化和表面腐蚀。
对热塑性基质，如聚碳酸酯，作为户外用途时，增强其对紫外光的稳定性变得很重要。这就需要用耐久性涂料进行表面处理，这些涂料就含有紫外光吸收剂。耐久性涂料的制备可以在生产过程中同时混入紫外光吸收剂，比如苯并三唑类、二苯甲酮类以及受阻胺光稳定剂。
然而，紫外光吸收化合物，通常称为紫外光吸收剂，为曝露于紫外光下时容易分解或挥发而丧失保护功能以及某些必要的性能。当延长其在阳光、潮湿及热循环条件时，可引起变黄，脱层以及在涂层中形成微小的裂痕，减小其透明性。这些导致了具有很好性能的热塑性物质老化，这些物质起始是由采用紫外光吸收剂来保护的。相应地，需要不断地开发新的更有效的紫外光吸收剂化合物。
人们发现某些4，6-二苯甲酰间苯二酚化合物(DBRs)对于卤代乙烯聚合物具有紫外光吸收性能。二苯甲酰间苯二酚在美国专利2,794,052和2,933,553中作为大宗添加剂。然而，近期二苯甲酰间苯二酚化合物的一个缺点是分子量相对低，例如分子量低于或等于400道尔顿，可导致在热塑物加工过程中挥发掉或引起涂料固化。这可引起对加工设备的污染。通过DBR类化合物增加取代基来增加分子量的努力可减弱紫外光吸收的效果。因此，有必要寻求具有光稳定性以及低挥发性有DBR发色团效果的紫外光吸收剂。
此处描述的为一组由2-(甲基环氧乙烷)-4，6-二苯甲酰间苯二酚衍生的新的紫外光吸收化合物以及含有这些化合物的涂料组合物。
此处描述的是在丙基的2和3位上有氧取代的2-(丙基)-4，6-二苯甲酰间苯二酸衍生物，它们可用在聚甲基丙烯酸甲酯组合物及别的涂料膜中作为紫外光吸收剂。氧取代包括α-甲基环氧乙烷基团，这个基团可以是打开修饰而提供描述于下文的衍生物。
化合物IV和V是二苯甲酰间苯二酚在丙酮/水/酸介质中在加热或不加热的情况下经过环氧化得到的。这些紫外光吸收剂经在聚甲基丙烯酸甲酯涂膜中检测，发现它们对于不稳定的聚碳酸酯膜是良好稳定剂，正如下面可以看到的，当含有化合物I-V的聚甲基丙烯酸甲酯涂料在曝露于氙气之前用于聚碳酸酯，可以减小聚碳酸酯的光化变黄速度。
本发明提供了一类具有紫外光吸收性能及其制备方法的新二苯甲酰间苯二酚组合物。这些新的二苯甲酰间苯二酚衍生物可用于涂料组合物以改善热塑性物质的耐久性。
此发明涉及新的在桥接的2-甲基部分上有环氧乙烷基的经亚甲基桥接的二苯甲酰间苯二酚衍生物，它用作紫外光吸收剂，并具有如下通式：
式中Ar1和Ar2为独立的取代或未取代的单环或多环芳基，R为H或碳数为1-8的脂肪族基团，A为环氧乙烷(环氧化物)基团。环氧乙烷可以开环而提供此处描述的衍生物。
本发明涉及的紫外光吸收剂是在丙基2和3位具有氧取代的2-丙基4，6-二苯甲酰间苯二酚化合物。
本发明所涉及的化合物的制备方法可由下面反应方程式给出：
Figure C9810359300091
为方便起见，这些化合物的化学名称给出如下：
I.2-甲基环氧乙烷-4，6-二苯甲酰间苯二酚
IIA.2-(3-羟基-2-甲氧基丙基)-4，6-二苯甲酰间苯二酚
IIB.2-(2-羟基-3-甲氧基丙基)-4，6-二苯甲酰间苯二酚
III.2-羟基甲基-5-羟基-6，8-二苯甲酰基-2，3-二氢苯并呋喃
IV.2-(2，3-二羟基丙基)-4，6-二苯甲酰间苯二酚
V.2，2-二甲基-5-[(2，6-二羟基-3，5-二苯甲酰基苯基)甲基]-1，3-二氧戊环。
前面描述的新的含甲基环氧的二苯甲酰间苯二酚的衍生物可以用本领域已知的方法掺入作为涂料组合物。此处涂料组合物已含甲基环氧二苯甲酰间苯二酚衍生物及实质透明的基质组合物。这些组合物可用于防止聚合物或制品由于光导致的分解。一般，这些基质包括丙烯酸，氨基甲酸乙酯，三聚氰胺或者它们的混合物。上面提及的涂料用于固体基质表面，形成一层固体基质膜具有抵挡紫外光的作用。这层固基质体膜常称为耐久性物质。通常来说，这层固体基质膜的厚度没有什么限制。然而，它们通常在约0.5-约50微米之间，最好在约3-约10微米之间。在本发明中，固体基质包括如下一些聚合物基质，有丙烯酸聚合物，如聚甲基异丁烯酸甲酯；聚酯，如对苯二酸乙二醇聚合物，对苯二酸丁二醇聚合物，聚酰胺，聚酰亚胺，丙烯腈-苯乙烯共聚物、苯乙烯-丙烯腈-丁二烯共聚物，聚氯乙烯，聚苯乙烯，聚苯乙烯与聚苯撑醚，丁酸酯，聚乙烯及其类似物的调合物。热塑性基质可以含有或不含颜料。另外，以上所说的固体基质可以包括金属基质，涂层表面、玻璃、陶瓷及织物。然而，本发明所涉及的涂料组合物更倾向于用在涂于聚碳酸酯。
本发明的由桥接的亚甲基上的环氧乙烷衍生的桥接亚甲基的二苯甲酰间苯二酚衍生物的制备方法由后面所给的实施例给出。实施例中所有化合物的分子结构均由H-NMR和C13-NMR光谱学及质谱测定予以确认。烯基如2-(烯丙)-4，6-二苯甲酰间苯二酸的烯丙基部分，可以由不同的过酸进行环氧化，其中间氯过苯甲酸是常用的。分子中必须没有氨基或别的易被进攻的基因存在。其它过酸还有过乙酸，过苯甲酸，过三氟乙酸和3，5-二硝基过氧化苯甲酸。另外，在银及加热条件下，也可以用空气进行氧化。
紫外光吸收化合物可以用在任何适合于塑料基质或制品如聚碳酸酯制品的涂料组合物。较优的涂料基质为热塑性丙烯酸，热固性丙烯酸以及硅酮硬质涂层，最佳的涂料组合物为聚甲基丙烯酸甲酯和各种类型的共聚物。
紫外光吸收化合物在涂料组合物中的用量是限定在一个用于防止树脂基质由于紫外辐射引起褪色或分解的有效用量。实质上，对于涂层物质所需要的紫外光吸收剂的有效量至少为在约300-330纳米之间吸收值约为0.3。这就意味着涂料组合物中的紫外光吸收化合物在入射的紫外辐射下至少吸收了50％的紫外光。
吸收公式如下：A＝log(I0/I)
式中：A是吸收值，I0为光线入射强度，I为透射光强度。
稳定的涂料溶液的组成，即涂料物质、紫外光稳定剂、任意其它添加剂，和溶剂含有的紫外线吸收剂占其固体聚合物重量的约1-约40wt％并且最好是约8-约30wt％。涂料中可含有一种或多种紫外光吸收剂。在本发明的实践过程中，比上述提及的含有更高浓度的紫外光吸收剂的光稳定组合物是很有用处的。这些组合物处于本发明所关注的范围之内。
这些紫外光吸收剂被应用于塑料基质或制品的涂料组合物。重要的是涂料组合物附着于物体表面而不损伤其塑料特性，如由于应力所造成的裂缝或裂痕，裂缝的漫延降低了抗冲击能力和抗张强度等。
紫外光吸收剂用于很多树脂，比如聚碳酸酯、聚酯、聚烯烃、聚苯乙烯、聚乙烯中以防止紫外线的侵害，这在文献中已有描述。由于紫外线吸收剂相对于聚合物具有很高的吸收性能，使它具有筛除入射光线中有害部分的能力而发挥作用。作为一种有效的紫外线吸收剂必经满足某些要求。这种吸收剂对一定波长范围的光线必须具有很高的吸收性能，这个波长范围的光线对涂层内的塑料基质或制品是最有危害的。这种吸收剂必须与聚合物和涂料组合物相容。另外，这种吸收剂不应对可见光区或者将传递给基质或制品的某种颜色具有明显的吸收。
通过以下详细的描述，本领域技术人员可以对本发明作更深入更全面的了解，这些描述辅以实施例及化学附图构成了说明的一部分。
实施例1
化合物1-2-(甲基环氧乙烷)-4，6-二苯甲酰间苯二酚的制备。在室温下，将5.6毫摩尔(2g)2-烯丙基-4，6-二苯甲酰间苯二酚和11毫摩尔(0.8g)约50％含量间氯过苯甲酸溶于甲苯中。反应进行1小时。反应混和物用约50ml的Na2CO3/H2O溶液洗3次。对甲苯组分蒸干。余下的黄白色固体在真空炉中于50℃下过夜。收率99％。核磁共振谱为(300MHz，CDCl3为溶剂)：2.7ppm(dd，1H)；2.8ppm(dd，1H)；2.9ppm(dd，1H)；3.0ppm(dd，1H)；3.3ppm(五重峰，1H)。
FD-MS显示母体离子在m/z 374。符合所给结构的计算结果。
实施例2
化合物IIA和IIB的制备。1.3毫摩尔(0.5g)的2-(甲基环氧乙烷)-4，6-二苯甲酰间苯二酚(溶于10ml的甲醇/二氯甲烷溶液中。用浓H2SO4调pH值到1-2。回流加热1个小时。产物用二氯甲烷萃取，然后蒸干二氯甲烷，得到白黄色产品。产品置于真空炉中过夜干燥。NMR及FD-MS(m/z 407)确认产品为两个异构体的混合物(比例大约为4∶1)。
实施例3
化合物III的制备。将1.3mmol(0.5g)的2-(甲基环氧乙烷)-4，6-二苯甲酰间苯二酚和溶于甲醇中的1.3mmol(0.3g)25％甲醇钠在甲醇，水和5滴H2SO4所组成的溶液中混合，在室温下放置5小时。待反应结束，加入二氯甲烷进行萃取。二氯甲烷部分蒸干得到白色固体。粗收率98％。NMR数据为(300MHz，CDCl3为溶剂)：3.15ppm(两双峰，1H)；3.3ppm(dd，1H)；3.75ppm(dd，1H)；3.9ppm(dd，1H)；5.2ppm(五重峰，1H)。FD-MS显示m/z 374，证实化合物III的结构。
实施例4
化合物V的制备。将5.3mmol(2.0g)的2-(甲基环氧乙烷)-4，6-二苯甲酰间苯二酚，5滴硫酸及少于1ml的水在丙酮中混合并在50℃下搅拌5小时。过滤反应液收集沉淀，并用异丙醇冲洗沉淀物，将其在真空炉中于50℃下干燥4小时。粗收率1.6g(66.7％)。核磁共振数据为(300MHz，CDCl3为溶剂)：1.45ppm(d，6H)；3.0，3.3ppm(dd，2H)；3.9，4.1ppm(dd，2H)；4.6ppm(五重峰，1H)。FD-MS显示m/z 431，确认产品V的结构。
实施例5
化合IV的制备。将3.7mmol(1.6g)的化合物V，10滴硫酸和约10ml的水在异丙醇中混合，并让其在100℃条件下搅拌1小时。加水使反应产物沉淀下来，过滤得到黄白色固体产品。粗收率89％(1.3克)。NMR(300MHz，CDCl3为溶剂)，数据为：3.1ppm(dd，2H)；3.6ppm(dd，2H)；4.8ppm(五重峰，1H)。FD-MS显示m/z 392，确认产品的结构。
用于氙弧加速测试膜的制备。
将溶于80.5克2-甲氧基丙醇中的5.33克Elvacite2041(聚甲基丙烯酸甲酯)和14.2克双丙酮醇加入带电动搅拌及加热套的三口瓶中于50℃下搅拌。将25克等分部分的聚合物溶液与0.07克紫外光吸收剂混合形成相当于聚甲基丙烯酸甲酯的重量而言紫外光吸收剂占5wt％的溶液。把制好的溶液在转磨中转动过夜使紫外光吸收剂溶解。然后把溶液在22℃及相对湿度为50％的条件下涂在未加稳定剂的15密耳厚的Lexan膜上。经过15分钟的溶剂闪蒸，然后放入105℃烘炉中烘熔30分钟。
氙弧加速试验是在Weather-Ometer的Ci35a氙弧仪中进行的，使用型号为S硼硅酸盐内外过滤片。辐射强度为在340纳米下0.77瓦每平方米，表盘显示温度在70-73℃，干球管温度为45℃而湿球降低10℃(50％相对湿度下)。周期为160分钟，5分钟一次光中断，15分钟一次光中断喷水。这一周期为在340纳米下每小时累计能量为每平方米2.46千焦。样品在这些条件下曝露420小时。
颜色检测用Gardner XL-835型比色计，结果如下表δYI(delta YI)栏
样品化合物I化合物IIA和IIB化合物III化合物IV化合物V     最終的δYI2.92.73.32.51.9
对照(聚甲基丙烯酸甲酯涂在聚酯膜(PC Film)上) 7.0

Claims (14)

1.一种化合物，该化合物具有下式：
其中Ar1和Ar2独立地为单环或多环芳基，R为H或碳数为1-8的脂肪族基团，A为
Figure C981035930002C2
或 ，或者所述化合物具有下式：
Figure C981035930003C1
2.根据权利要求1的化合物，其具有下式：
3.根据权利要求1的化合物，其具有下式：
Figure C981035930003C3
4.根据权利要求1的化合物，其具有下式：
Figure C981035930004C1
5.根据权利要求1的化合物，其具有下式：
Figure C981035930004C2
6.根据权利要求1的化合物，其具有下式：
Figure C981035930004C3
7.根据权利要求1的化合物，其具有下式：
Figure C981035930005C1
8.一种紫外光吸收涂料组合物，它包含透明基质材料和紫外光吸收化合物，所述紫外光吸收化合物具有下面的结构通式：
其中Ar1和Ar2独立地为单环或多环芳基，R为H或碳数为1-8的脂肪族基团，A为
Figure C981035930006C1
或
Figure C981035930006C2
，或者所述紫外光吸收化合物具有下式：
Figure C981035930006C3
9.根据权利要求8的紫外光吸收涂料组合物，它包含透明基质材料和2-(甲基环氧乙烷)-4，6-二苯甲酰间苯二酚。
10.根据权利要求8的紫外光吸收涂料组合物，它包含透明基质材料和2-(3-羟基-2-甲氧基丙基)-4，6-二苯甲酰间苯二酚。
11.根据权利要求8的紫外光吸收涂料组合物，它包含透明基质材料和2(2-羟基-3-甲氧基丙基)-4，6-二苯甲酰间苯二酚。
12.根据权利要求8的紫外光吸收涂料组合物，它包含透明基质材料和2-羟甲基-5-羟基-6，8-二苯甲酰基-2，3-二氢苯并呋喃。
13.根据权利要求8的紫外光吸收涂料组合物，它包含透明基质材料和2-(2，3-二羟丙基)-4，6-二苯甲酰间苯二酚。
14.根据权利要求8的紫外光吸收涂料组合物，它包含透明基质材料和2，2-二甲基-5-[(2，6-二羟基-3，5-二苯甲酰基苯基)甲基]-1，3-二氧戊环。
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Families Citing this family (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070241340A1 (en) * 2006-04-17 2007-10-18 Pan Shaoher X Micro-mirror based display device having an improved light source
US7857905B2 (en) 2007-03-05 2010-12-28 Momentive Performance Materials Inc. Flexible thermal cure silicone hardcoats
US9329654B2 (en) 2012-10-19 2016-05-03 Dell Products, Lp System and method for one-line power mapping of information handling systems in a datacenter
US9923766B2 (en) 2014-03-06 2018-03-20 Dell Products, Lp System and method for providing a data center management controller
US9430010B2 (en) 2014-03-06 2016-08-30 Dell Products, Lp System and method for server rack power mapping
US10250447B2 (en) 2014-03-06 2019-04-02 Dell Products, Lp System and method for providing a U-space aligned KVM/Ethernet management switch/serial aggregator controller
US9964935B2 (en) 2014-03-06 2018-05-08 Dell Products, Lp System and method for data reporting in a tile management controller
US20150256393A1 (en) 2014-03-06 2015-09-10 Dell Products, Lp System and Method for Providing a Tile Management Controller
US9699933B2 (en) 2014-03-06 2017-07-04 Dell Products, Lp System and method for providing AC jumper management and identifying AC jumper topology
US10122585B2 (en) 2014-03-06 2018-11-06 Dell Products, Lp System and method for providing U-space aligned intelligent VLAN and port mapping
US9958178B2 (en) 2014-03-06 2018-05-01 Dell Products, Lp System and method for providing a server rack management controller
US9423854B2 (en) 2014-03-06 2016-08-23 Dell Products, Lp System and method for server rack power management
US9913399B2 (en) 2015-02-09 2018-03-06 Dell Products, Lp System and method for wireless rack management controller communication
US9578510B2 (en) 2015-02-10 2017-02-21 Dells Products, Lp System and method for wireless handheld device security in a data center environment
US9961074B2 (en) 2015-02-10 2018-05-01 Dell Products, Lp System and method for providing an authentication certificate for a wireless handheld device a data center environment
US9853911B2 (en) 2015-02-19 2017-12-26 Dell Products, Lp System and method for management network activity in a data center environment
US9678552B2 (en) 2015-10-30 2017-06-13 Dell Products, Lp System and method for powering a wireless end point in a server rack of a data center
US10229082B2 (en) 2015-11-09 2019-03-12 Dell Products, Lp System and method for providing wireless communications to a boxed server
US10712792B2 (en) 2015-11-09 2020-07-14 Dell Products, L.P. System and method for provisioning a powered off server in a data center
US10009766B2 (en) 2015-11-09 2018-06-26 Dell Products, Lp System and method for providing a wireless device connection in a server rack of a data center
US9929901B2 (en) 2015-11-10 2018-03-27 Dell Products, Lp System and method for providing proxied virtual wireless end points in a server rack of a data center
US9942935B2 (en) 2015-11-17 2018-04-10 Dell Products, Lp System and method for providing a wireless failover of a management connection in a server rack of a data center
US10216681B2 (en) 2015-12-01 2019-02-26 Dell Products, Lp System and method for managing workloads and hot-swapping a co-processor of an information handling system
US10241555B2 (en) 2015-12-04 2019-03-26 Dell Products, Lp System and method for monitoring a battery status in a server in a data center
US9930771B2 (en) 2015-12-16 2018-03-27 Dell Products, Lp Aperiodic routing to mitigate floquet mode resonances
US10298460B2 (en) 2015-12-21 2019-05-21 Dell Products, Lp System and method for aggregating communication and control of wireless end-points in a data center
US10116744B2 (en) 2016-02-04 2018-10-30 Dell Products, Lp System and method for providing management network communication and control in a data center
US10373283B2 (en) 2016-03-14 2019-08-06 Dell Products, Lp System and method for normalization of GPU workloads based on real-time GPU data

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2900361A (en) * 1955-04-06 1959-08-18 Dow Chemical Co Dibenzoyl resorcinol light stabilizer
US2831026A (en) * 1956-06-04 1958-04-15 Dow Chemical Co Process for granulating dibenzoyl resorcinol
US3094506A (en) * 1959-07-27 1963-06-18 Hooker Chemical Corp Novel compounds and polymeric halogen-containing resins incorporating same
US4054551A (en) * 1975-05-02 1977-10-18 The B. F. Goodrich Company Benzofuranylphenol stabilizers
US4774344A (en) * 1982-09-30 1988-09-27 Amoco Corporation 2,2-bis-phenol dioxolanes monomers
US4691059A (en) * 1985-08-30 1987-09-01 Minnesota Mining And Manufacturing Company Copolymerizable UV stabilizers
US5359069A (en) * 1989-03-21 1994-10-25 Ciba-Geigy Corporation Non-migrating 1-hydrocarbyloxy hindered amine derivatives as polymer stabilizers
GB8925473D0 (en) * 1989-11-10 1989-12-28 Unilever Plc Sunscreen compositions
DE59306309D1 (de) * 1992-04-04 1997-06-05 Hoechst Ag Benzophenon-Verbindungen, Verfahren zu deren Herstellung und ihre Verwendung
US5391795A (en) * 1994-02-18 1995-02-21 General Electric Company Silylated agents useful for absorbing ultraviolet light
ES2131764T3 (es) * 1994-03-04 1999-08-01 Gen Electric Revestimientos utiles para absorber luz ultravioleta.
US5741905A (en) * 1994-07-23 1998-04-21 Ciba Specialty Chemicals Corporation Triazine ultraviolet absorbers useful for improving the sun protection factor of textiles
US5981073A (en) * 1997-01-16 1999-11-09 General Electric Company Compounds based on dibenzoylresorcinol, and related compositions and articles

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