CN1186417C - 含有高溶解性的、红移的、光稳定的苯并三唑紫外线吸收剂的稳定化粘合剂组合物和从其制得的层压制品 - Google Patents
含有高溶解性的、红移的、光稳定的苯并三唑紫外线吸收剂的稳定化粘合剂组合物和从其制得的层压制品 Download PDFInfo
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- CN1186417C CN1186417C CNB008070644A CN00807064A CN1186417C CN 1186417 C CN1186417 C CN 1186417C CN B008070644 A CNB008070644 A CN B008070644A CN 00807064 A CN00807064 A CN 00807064A CN 1186417 C CN1186417 C CN 1186417C
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- Prior art keywords
- benzotriazole
- tert
- hydroxy
- trifluoromethyl
- butyl
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- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
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- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
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- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10743—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer containing acrylate (co)polymers or salts thereof
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/10009—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
- B32B17/10036—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising two outer glass sheets
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B17/00—Layered products essentially comprising sheet glass, or glass, slag, or like fibres
- B32B17/06—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
- B32B17/10—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
- B32B17/10005—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
- B32B17/1055—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
- B32B17/10678—Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer comprising UV absorbers or stabilizers, e.g. antioxidants
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/16—Nitrogen-containing compounds
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- F24S23/70—Arrangements for concentrating solar-rays for solar heat collectors with reflectors
- F24S23/82—Arrangements for concentrating solar-rays for solar heat collectors with reflectors characterised by the material or the construction of the reflector
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- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F24—HEATING; RANGES; VENTILATING
- F24S—SOLAR HEAT COLLECTORS; SOLAR HEAT SYSTEMS
- F24S25/00—Arrangement of stationary mountings or supports for solar heat collector modules
- F24S25/60—Fixation means, e.g. fasteners, specially adapted for supporting solar heat collector modules
- F24S2025/601—Fixation means, e.g. fasteners, specially adapted for supporting solar heat collector modules by bonding, e.g. by using adhesives
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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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/40—Solar thermal energy, e.g. solar towers
Landscapes
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- Medicinal Chemistry (AREA)
- Thermal Sciences (AREA)
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- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
通过引入在350-400纳米范围内强烈吸收光的所选择的高溶解性、红移和光稳定的苯并三唑UV吸收剂,使粘合剂组合物获得了抵抗紫外光引起的降解作用的稳定性。也合适的是2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑和2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑与红移苯并三唑的结合物。本发明的另一主题是通式(IIIc)的新型不对称双苯并三唑,其中G2’是具有1-1 2个碳原子的全氟烷基、优选CF3,和其中G2不含所述基团,这些化合物是红移的,并且因不对称结构而特别具有溶解性,并可用于包括汽车涂料、热塑性塑料在内的许多应用中,尤其可用于粘合剂组合物中,它们本身可用于太阳板和其它层压结构体中。所有这些UV吸收剂显示出优异的光稳定性和在粘合剂配制剂中的高溶解性。从这些组合物形成的层压制品包括,例如,日照控制膜,膜和玻璃窗,UV吸收玻璃和玻璃涂料,挡风玻璃,后向反射片材和标志牌,太阳光反射器和光学膜等。
Description
本发明涉及含有有效量的具有提高的溶解度、耐久性和在350-400nm范围内有吸收的苯并三唑UV吸收剂的稳定化粘结剂组合物。本发明的另一个主题是含有有效量的具有提高的溶解度和耐久性的在羟苯基环的邻位被α-异丙苯基或苯基取代的苯并三唑如2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑的稳定化粘合剂组合物。本发明的再一个主题涉及新型不对称的双苯并三唑化合物,它是红移的,因为有不对称性而特别易溶,并可用于许多最终应用中。
发明背景
粘合剂由各种组分如聚合物、增粘剂、蜡和油组成。基于这些成分的粘合剂配制剂容易降解。降解的结果是变色,伸长率损失,拉伸强度的损失,粘性的损失以及在粘度、分子量和分子量分布上的变化。降解能够由长时间暴露于太阳光而引起。太阳光含有波长在290和400纳米之间的不可见紫外线(UV)辐射。这一辐射是引发光降解作用的原因。
紫外光被存在于粘合剂配制剂中的生色团所吸收,而使生色团转变成它们的受激态,进一步进行所不希望的反应。一些聚合物含有强吸收性的生色团作为它们结构的主要部分。其它聚合物含有不希望存在的能构成生色团的杂质如酮和氢过氧化物结构部分和催化剂残基。紫外线辐射被这些生色团吸收后最后导致键断裂、断链和/或交联反应。
粘合剂的光稳定化可通过添加UV吸收剂来实现,它将吸收的能量转化成无害的热量。理想的紫外线吸收剂应该是极其光稳定的并对在290-400纳米范围内、特别在350-400纳米范围内的UV有强吸收。UV吸收剂的类别包括水杨酸酯类,氰基丙烯酸酯类,丙二酸酯类,草酰二苯胺类,二苯甲酮类,s-三嗪类和苯并三唑类。
水杨酸酯类,氰基丙烯酸酯类,丙二酸酯类和草酰二苯胺类主要吸收在该UV范围的较短波长下的UV光。这些化合物在350-400纳米范围内具有很少或几乎没有吸收,这使得它们不适合于在本发明情况下的应用。二苯甲酮吸收在该UV范围的下一半部分,它们在曝光之后因光降解作用而容易泛黄。最近,通过光化学方式已经显示二苯甲酮在乙烯-乙酸乙烯酯密封剂中过早地分解,导致产生了多烯的生色团。从淡黄色到棕色的这一颜色生成不仅是粘结剂体系中非常不希望有的和不好看的,而且还导致粘合剂性能的损失。相比之下,所选择的苯并三唑UV吸收剂是特别有用的,因为它们的提高的光稳定性。
一些聚合物如聚碳酸酯类,聚酯和芳族聚氨酯类含有强吸收性生色团作为它们结构的主要和整体部分。聚(对苯二甲酸乙二醇酯)(PET)和聚(2,6-萘二羧酸乙二醇酯)(PEN)是具体的实例,后者吸收到红色UV区域和尤其需要用于UV保护的红移苯并三唑。US专利No.5,294,473和WO98/34981教导了含有包括一些苯并三唑的UV吸收剂的涂料在稳定PEN膜上的用途。通过增加含有苯并三唑的粘合剂UV屏蔽层,尤其在本发明中描述的那些,可进一步保护在多层构造和制品中的此类聚合物。
2H-苯并三唑UV吸收剂的叙述、制备和用途被描述在美国专利3,004,896;3,055,896;3,072,585;3,074,910;3,189,615;3,230,194;4,127,586;4,226,763;4,278,589;4,315,848;4,383,863;4,675,352;4,681,905和4,853,471中。
在苯并环的5-位上只有氢或卤素的所选择的苯并三唑是光稳定的并可溶于粘合剂配制剂中。一种此类苯并三唑是2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑,如美国专利5,554,760;5,563,242;5,574,166和5,607,987中所述。这些专利被引入本文供参考。尽管这一苯并三唑的吸收没有向着较长UV波长发生红移,但是它是非常光稳定的和令人惊讶地可溶于粘合剂中,这使得它尤其适合于在本发明情况下的应用。
虽然在苯并环的5-位上只有氢的苯并三唑是光稳定的和可用于粘合剂配制剂中,但它们缺乏向着较长UV波长的红移吸光度,而这最适合用于为基材提供更多的保护作用。美国专利No.5,319,091和5,410,071描述了在苯并环的5-位上被烷基-或芳基-磺酰基结构部分取代的苯并三唑的制备方法。美国专利No.5,280,124教导,通过在苯并三唑的苯并环的5-位上引入高级烷基或芳基亚砜或砜,所获得的苯并三唑在近可见区(在350纳米以上)显示出增强的吸收。此类砜取代的产物被显示可用于汽车涂料应用中。另外这样的吸电子基团显著提高汽车涂料中这些苯并三唑UV吸收剂的光稳定性。相当令人惊奇地,这些红移的苯并三唑和尤其不对称取代的苯并三唑能够令人惊讶地可溶于粘合剂中,使得它们尤其适合于在本发明情况下的应用。
现有技术中已知受阻胺光稳定剂与UV吸收剂如苯并三唑的一起使用在许多聚合物组合物中提供优异的稳定作用,正如G.Berner和M.Rembold所总结的,“高固含量涂料的新型光稳定剂(New LightStabilizers for High Solids Coatings)”,Organic Coatings andScience and Technology,第6卷,Dekkar,纽约,第55-85页。
该苯并三唑UV吸收剂代表了特殊类别的如上所述的商购UV吸收剂。只有少数的文献涉及到在苯并环上被芳基或烷基亚砜或磺酰基结构部分的取代。
美国专利No.3,218,332公开了在苯并环的5-位上被低级烷基磺酰基结构部分取代的苯并三唑。然而,这一专利致力于在苯基环的3-位上设置可反应的基团即链烯基,而且与本申请很少相关。美国专利No.5,268,450和5,319,091公开了聚合物组合物和生产取代的芳基硫基和芳基磺酰基苯并三唑的方法,该苯并三唑以共价键连接于聚合物如聚(苯硫醚)上,RYTON,Phillips Petroleum。美国专利No.5,280,124公开了在苯并环的5-位仅仅有高级烷基或芳基亚硫酰基或磺酰基结构部分的苯并三唑,它可用于保护热固性汽车涂料。
日本专利No.92-352228公开了在苯基环的3-位上未被取代或被甲基取代的5-乙基磺酰基苯并三唑用于防尘的聚(氯乙烯)树脂薄膜的UV保护的用途。当在本发明的粘合剂组合物中研究时,这些化合物被发现不易溶解和总体来说对本发明的粘合剂组合物没有用处。相反,当在苯基环的3-位上插入叔烷基时,如此取代的苯并三唑在粘合剂组合物中的溶解度令人惊奇地被增强了。
当与现有技术的化合物相比时,这一在5位上取代的化合物尤其在长波长UV区域(超过350nm)中显示出了增强的宽吸收特性。另外,这一化合物在粘合剂中具有令人惊奇和出乎意料的高溶解度,这使得它们尤其适合用于粘合剂配制剂中。
双苯并三唑如2,2’-亚甲基-双[4-叔辛基-6-(2H-苯并三唑-2-基)酚],TINUVIN360(Ciba)被描述在美国专利No.5,299,521中。尽管是有用的,但这些化合物不是红移的。
德国1,670,951一般性描述了对称和不对称的亚烷基双苯并三唑,但是具体地说仅仅有一些对称的双苯并三唑,它偏出了本发明权利要求的范围。在德国1,670,951中描述的化合物没有被全氟烷基如CF3取代。
美国专利No.4,812,498描述对称双苯并三唑作为聚碳酸酯树脂的稳定剂。该双苯并三唑在结构上是对称的,不含有全氟烷基结构部分,和明显偏出本发明化合物的范围。
EP 924,203 A1描述了各自含有可聚合的结构部分的双苯并三唑化合物,和从其制得的聚合物。这些现有技术的双苯并三唑不是红移的或不含有全氟化烷基。本发明的化合物与这些现有技术的双苯并三唑明显不同。
紫外线对暴露于阳光或其它UV光源的层压制品的影响是此类制品的制造商十分关心的。随着时间的推移,恒定或反复地暴露于UV光能够对在此类制品中使用的染料和/或颜料导致染料和/或颜料褪色,和导致在制品的结构中使用的粘合剂、聚合物或其它材料的降解或破坏。上述的褪色和降解作用缩短了所述制品的使用期限,使得保护它们免受紫外线曝露的措施成为这类制品的制造商的重要事情。
作为UV吸收剂的分子通常是现有技术中已知的。然而,由于以上所讨论的在各种UV吸收剂类别之间的差异,因此这里将讨论的是苯并三唑和含有它们的制品。由于某些苯并三唑的不相容性和低溶解度,需要进一步选择高度可溶解的和在紫外线的350-400纳米区域中提供增强的保护作用的苯并三唑。T.Nagashima等人,J.Non-Cryst.Solids,
178(1994),182,最近报道了紫外线(UV)汽车前挡风玻璃,它在长波长(320-400nm)范围内是UV吸收性的以避免阳光灼晒作用,其成为了重要的议题,因为由于消耗臭氧层而有可能存在皮肤癌的危险。
另外,引入本发明的所选择的苯并三唑的制品可用于保护例如在汽车应用中的内部结构、纺织品和织物免受UV诱发的光降解作用。
国际申请WO97/32225描述了具有反射和偏振元件的PEN膜作为光学膜的用途。
美国专利No.5,770,114公开了可用于电致变色装置中的含有可溶性苯并三唑的稳定化组合物。然而,这些苯并三唑缺乏在350到400纳米区域中的红移吸收。
可从引入高溶解性的、光稳定的和红移的苯并三唑受益的制品包括,但不限于:
(a)后向反射片材和标志牌和保形标记片材,参见WO 97/42261;和US专利No.5,387,458,引入本文供参考;
(b)各种结构体的日照控制膜,参见英国2,012,668;欧洲355,962;和US专利No.3,290,203;3,681,179;3,776,805和4,095,013,引入本文供参考;
(c)耐腐蚀的银镜和太阳光反射器,参见美国专利No.4,645,714,引入本文供参考;
(d)反射性打印标签,参见美国专利No.5,564,843,引入本文供参考;
(e)UV吸收性玻璃和玻璃涂料,参见美国专利No.5,372,889;5,426,204;5,683,804和5,618,626,引入本文供参考;
(f)电致变色装置,参见欧洲752,612 A1;和US专利No.5,239,406;5,523,877和5,770,114,引入本文供参考;
(g)膜/玻璃窗,参见WO 92/01557;日本专利No.75-33286;93-143668;95-3217和96-143831;和US专利No.5,643,676,引入本文供参考;
(h)汽车的挡风玻璃和中间层,参见日本专利No.80-40018;90-192118;90-335037;90-335038;92-110128和94-127591;和US专利No.5,618,863,引入本文供参考;和
(i)光学膜,参见WO 97/32225;和US专利No.4,871,784和5,217,794,引入本文供参考。
详细公开内容
本发明的一个主题是稳定化的粘合剂组合物,它适合作为层压制品或多层结构体中的粘合剂层,它包括
(a)粘合剂;和
(b1)具有通式I,II或III的高度可溶解的、红移的光稳定的苯并三唑
或
(b2)高度可溶解的和光稳定的苯并三唑,它是2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑或2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑;或
(b1)和(b2)的化合物的混合物;
其中
G1和G1’独立地是氢或卤素,
G2和G2’独立地是卤素,硝基,氰基,具有1-12个碳原子的全氟烷基,-COOG3,-P(O)(C6H5)2,-CO-G3,-CO-NH-G3,-CO-N(G3)2,-N(G3)-CO-G3,E3SO-或E3SO2-;或G2’也是氢,
G3是氢,具有1-24个碳原子的直链或支链烷基,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-4个具有1-4个碳原子的烷基取代的该苯基或该苯基烷基,
G6是具有1-12个碳原子的全氟烷基,
G7是氢或具有1-12个碳原子的全氟烷基,
E1是氢,具有1-24个碳原子的直链或支链烷基,具有2-24个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-4个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基;或E1是被一个或两个羟基取代的具有1-24个碳原子的烷基,
E2和E2’独立地是具有1-24个碳原子的直链或支链烷基,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-3个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基;或E2和E2’独立地是被一个或多个-OH、-OCOE11、-OE4、-NCO、-NH2、-NHCOE11、-NHE4或-N(E4)2或它们的混合基团取代的具有1-24个碳原子的所述烷基或具有2-18个碳原子的所述链烯基,其中E4是具有1-24个碳原子的直链或支链烷基;或被一个或多个-O-、-NH-或-NE4-基团或它们的混合基团插入的并能够是未被取代或被一个或多个-OH、-OE4或-NH2基团或它们的混合基团取代的该烷基或链烯基;
n是1或2,
当n是1时,E5是OE6或NE7E8,或
E5是-PO(OE12)2,-OSi(E11)3或-OCO-E11,
或直链或支链C1-C24烷基,它被-O-、-S-或-NE11插入和它能够是未取代的或被-OH或-OCO-E11取代,C5-C12环烷基,它是未被取代的或被-OH取代,直链或支链C2-C18链烯基,它是未被取代的或被-OH取代,C7-C15芳烷基,-CH2-CHOH-E13或缩水甘油基,
E6是氢,直链或支链C1-C24烷基,它是未被取代的或被一个或多个OH、OE4或NH2基团取代,或-OE6是-(OCH2CH2)wOH或-(OCH2CH2)wOE21,其中w是1-12和E21是具有1-12个碳原子的烷基,
E7和E8独立地是氢,具有1-18个碳原子的烷基,被-O-、-S-或-NE11-插入的直链或支链C3-C18烷基,C5-C12环烷基,C6-C14芳基或C1-C3羟基烷基,或E7和E8与N原子一起是吡咯烷,哌啶,哌嗪或吗啉环,
E5是-X-(Z)p-Y-E15
其中
X是-O-或-N(E16)-,
Y是-O-或-N(E17)-,
Z是C2-C12-亚烷基,被1-3个氮原子、氧原子或其混合原子插入的C4-C12-亚烷基,或是C3-C12-亚烷基,亚丁烯基,亚丁炔基,亚环己基或亚苯基,各被羟基取代,
m是0,1或2,
p是1,或当X和Y分别是-N(E16)-和-N(E17)-时p也是0,
E15是基团-CO-C(E18)=C(H)E19或,当Y是-N(E17)-时,与E17一起形成了基团-CO-CH=CH-CO-,其中E18是氢或甲基,和E19是氢,甲基或-CO-X-E20,其中E20是氢,C1-C12烷基或下式的基团
其中符号E1,G2,X,Z,m和p具有以上定义的含义,和E16和E17彼此独立地是氢,C1-C12-烷基,被1-3个氧原子插入的C3-C12烷基,或是环己基或C7-C15芳烷基,并且在Z是亚乙基的情况下E16与E17一起也形成亚乙基,
当n是2时,E5是二价基团-O-E9-O-或-N(E11)-E10-N(E11)-中的一个,
E9是C2-C8亚烷基,C4-C8亚链烯基,C4亚炔基,亚环己基,被-O-或-CH2-CHOH-CH2-O-E14-O-CH2-CHOH-CH2-插入的直链或支链C4-C10亚烷基,
E10是直链或支链C2-C12亚烷基,在它中可插入-O-,亚环己基,或
或E10和E11与两个氮原子一起形成哌嗪环,
E14是直链或支链C2-C8亚烷基,被-O-插入的直链或支链C4-C10亚烷基,亚环烷基,亚芳基或
其中E7和E8独立地是氢,具有1-18个碳原子的烷基或E7和E8一起是具有4-6个碳原子的亚烷基,3-氧杂五亚甲基,3-亚氨基五亚甲基或3-甲基亚氨基五亚甲基,
E11是氢,直链或支链C1-C18烷基,C5-C12环烷基,直链或支链C2-C18链烯基,C6-C14芳基或C7-C15芳烷基,
E12是直链或支链C1-C18烷基,直链或支链C3-C18链烯基,C5-C10环烷基,C6-C18芳基或C7-C15芳烷基,
E13是H,直链或支化C1-C18烷基,它被-PO(OE12)2取代,未被取代的或被OH取代的苯基,C7-C15芳烷基或-CH2OE12,
E3是具有1-20个碳原子的烷基,具有2-20个碳原子的羟烷基,被具有2-9个碳原子的烷氧基羰基取代的烷基,具有3-18个碳原子的链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,具有6-10个碳原子的芳基或被一个或两个具有1-4个碳原子的烷基取代的该芳基或1,1,2,2-四氢全氟烷基,其中全氟烷基结构部分具有6-16个碳原子,和
L是具有1到12个碳原子的亚烷基,2到12个碳原子的烷叉基,苯亚甲基,对-亚二甲苯基,a,a,a’,a’-四甲基-间亚二甲苯基或环烷叉基。
C1-C18烷基能够是线性或支化的。实例是甲基,乙基,丙基,异丙基,丁基,2-丁基,异丁基,叔丁基,戊基,2-戊基,己基,庚基,辛基,2-乙基己基,叔辛基,壬基,癸基,十一烷基,十二烷基,十三烷基,十四烷基,十六烷基和十八烷基。
烷氧基的例子是甲氧基,乙氧基,丙氧基,异丙氧基,丁氧基,异丁氧基,戊氧基,异戊氧基,己氧基,庚氧基或辛氧基。
C2-C18链烯基例如是乙烯基,丙烯基或丁烯基,十二碳烯基或十八碳烯基。
具有5-12个碳原子的环烷基例如是环戊基,环己基和环辛基。
苯基烷基例如是苄基。
优选地,当暴露于光化辐射时,通式I、II或III的苯并三唑(b1)和苯并三唑(b2)显示出增强的耐久性和低的吸光度损失,这可通过在氙弧灯(Xenon Arc)Weather-Ometer中曝照893小时之后低于0.5吸光度单位的吸光度损失或在曝照1338小时之后低于0.8吸光度单位的吸光度损失来证实。
优选的是这样一种组合物,其中通式I的苯并三唑化合物是以下化合物
其中
G1是氢,
G2是氰基,氯,氟,CF3-,-CO-G3,E3SO-或E3SO2-,
G3是具有1-24个碳原子的直链或支链烷基,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-4个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基,
E1是具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-4个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基,
E2是具有1-24个碳原子的直链或支链烷基链,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-3个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基;或E2是被一个或多个-OH、-OCOE11、-OE4、-NCO、-NH2、-NHCOE11、-NHE4或-N(E4)2或它们的混合基团取代的具有1-24个碳原子的所述烷基或具有2-18个碳原子的所述链烯基,其中E4是具有1-24个碳原子的直链或支链烷基;或被一个或多个-O-、-NH-或-NE4-基团或它们的混合基团插入的并能够是未被取代或被一个或多个-OH、-OE4或-NH2基团或它们的混合基团取代的该烷基或链烯基;
E3是具有1-20个碳原子的烷基,具有2-20个碳原子的羟烷基,具有3-18个碳原子的链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,具有6-10个碳原子的芳基或被一个或两个具有1-4个碳原子的烷基取代的该芳基或1,1,2,2-四氢全氟烷基,其中全氟烷基结构部分具有6-16个碳原子;或
是通式I的化合物,其中,
G1是氢,
G2是氯,氟,CF3-,E3SO-或E3SO2-,
E1是氢或具有1-24个碳原子的直链或支链烷基,
E2如以上所定义,和
E3是具有1-7个碳原子的直链或支链烷基。
也优选的是一种组合物,其中苯并三唑化合物是通式IIA的化合物
其中
G1是氢,
G2是CF3-或氟,
E1是氢,具有1-24个碳原子的直链或支链烷基或具有7-15个碳原子的苯基烷基,
E5是-OE6或-NE7E8,或
E5是-X-(Z)p-Y-E15
其中
X是-O-或-N(E16)-,
Y是-O-或-N(E17)-,
Z是C2-C12-亚烷基,被1-3个氮原子、氧原子或其混合原子插入的C4-C12-亚烷基,或是C3-C12-亚烷基,亚丁烯基,亚丁炔基,亚环己基或亚苯基,各被羟基取代,
m是0,1,2或3,
p是1,或当X和Y分别是-N(E16)-和-N(E17)-时p也是0,
E15是基团-CO-C(E18)=C(H)E19或,当Y是-N(E17)-时,与E17一起形成了基团-CO-CH=CH-CO-,其中E18是氢或甲基,和E19是氢,甲基或-CO-X-E20,其中E20是氢,C1-C12烷基或下式的基团
进一步优选的组合物是其中苯并三唑是通式IIIA的化合物的组合物
其中
G6是CF3,
G7是氢或CF3,
E2和E2’独立地是具有1-24个碳原子的直链或支链烷基链,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-3个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基;和
L是具有1到12个碳原子的亚烷基,2到12个碳原子的烷叉基,苯亚甲基,对-亚二甲苯基,a,a,a’,a’-四甲基-间亚二甲苯基或环烷叉基。
更优选的是一种组合物,其中苯并三唑化合物是通式I的化合物
其中
G1是氢,
G2是CF3-,
E1是具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-4个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基,
E2是具有1-24个碳原子的直链或支链烷基链,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基;苯基;或在苯基环上被1-3个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基;或E2是被一个或多个-OH、-OCOE11、-NH2或-NHCOE11或它们的混合基团取代的具有1-24个碳原子的该烷基或具有2-18个碳原子的该链烯基,或者被一个或多个-O-插入的和能够是未取代的或被一个或多个-OH取代的该烷基或链烯基;或
是通式I的化合物,
其中,
G1是氢,
G2是CF3-,
E1是氢,具有1-24个碳原子的直链或支链烷基或具有7-15个碳原子的苯基烷基,和
E2如以上所定义。
也更优选的是一种组合物,其中苯并三唑化合物是通式IIA的化合物
其中
G1是氢,
G2是CF3-,
E1是氢,具有1-24个碳原子的直链或支链烷基或具有7-15个碳原子的苯基烷基,
E5是-OE6或-NE7E8,其中
E6是氢,直链或支链C1-C24烷基,它是未被取代的或被一个或多个OH基团取代,或-OE6是-(OCH2CH2)wOH或-(OCH2CH2)wOE21,其中w是1-12和E21是具有1-12个碳原子的烷基,和
E7和E8独立地是氢,具有1-18个碳原子的烷基,被-O-、-S-或-NE11-插入的直链或支链C3-C18烷基,C5-C12环烷基,C6-C14芳基或C1-C3羟基烷基,或E7和E8与N原子一起是吡咯烷,哌啶,哌嗪或吗啉环。
特别优选的是一种组合物,其中苯并三唑化合物是通式IIIA的化合物
其中
G6是CF3,
G7是氢或CF3,
E2和E2’独立地是具有1-24个碳原子的直链或支链烷基链,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-3个具有1-4个碳原子的烷基取代的所述苯基或所述苯基烷基;和
L是亚甲基。
最优选的是这样一种组合物,其中苯并三唑化合物是以下化合物:
(a)5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑;
(b)5-三氟甲基-2-(2-羟基-5-叔辛基苯基)-2H-苯并三唑;
(c)5-三氟甲基-2-(2-羟基-3,5-二叔辛基苯基)-2H-苯并三唑;
(d)2,2’-亚甲基-双[6-(5-三氟甲基-2H-苯并三唑-2-基)-4-叔辛基酚];
(e)亚甲基-2-[4-叔辛基-6-(2H-苯并三唑-2-基)苯酚]-2’-[4-叔辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚];
(f)3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸;
(g)3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸甲酯;
(h)3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸异辛酯;
(i)5-三氟甲基-2-[2-羟基-5-(3-羟丙基)苯基]-2H-苯并三唑;
(j)5-丁基磺酰基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑;
(k)5-辛基磺酰基-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑;
(l)5-十二烷基磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑;
(m)5-辛基磺酰基-2-(2-羟基-3,5-二-叔辛基苯基)-2H-苯并三唑;
(n)5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑;
(o)5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-壬基苯基)-2H-苯并三唑;
(p)5-三氟甲基-2-[2-羟基-3-α-异丙苯基-5-(2-羟乙基)苯基]-2H-苯并三唑;
(q)5-三氟甲基-2-[2-羟基-3-α-异丙苯基-5-(3-羟丙基)苯基]-2H-苯并三唑;
(r)5-三氟甲基-2-(2-羟基-3,5-二-叔戊基苯基)-2H-苯并三唑;
(s)5-三氟甲基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑;
(t)5-三氟甲基-2-(2-羟基-3-十二烷基-5-甲基苯基)-2H-苯并三唑;
(u)5-三氟甲基-2-[2-羟基-3-叔丁基-5-(3-羟丙基)苯基]-2H-苯并三唑;
(v)5-三氟甲基-2-[2-羟基-3-叔丁基-5-(2-羟乙基)苯基]-2H-苯并三唑;
(w)5-三氟甲基-2-[2-羟基-5-(2-羟乙基)苯基]-2H-苯并三唑;
(x)5-三氟甲基-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑;
(y)5-氟-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑;
(z)5-丁基磺酰基-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑;
(aa)5-丁基磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑;
(bb)5-丁基磺酰基-2-(2-羟基-3,5-二-叔辛基苯基)-2H-苯并三唑;
(cc)5-苯磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑;或
(dd)5-氯-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑。
特别优选的是这样一种组合物,其中苯并三唑是
(a)5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑;
(b)5-三氟甲基-2-(2-羟基-5-叔辛基苯基)-2H-苯并三唑;
(c)5-三氟甲基-2-(2-羟基-3,5-二叔辛基苯基)-2H-苯并三唑;
(g)3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸甲酯;
(j)5-丁基磺酰基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑;
(n)5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑;
(s)5-三氟甲基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑;
(x)5-三氟甲基-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑;
(aa)5-丁基磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑;
(cc)5-苯磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑。
组分(b1)或(b2)的苯并三唑的量优选是0.1-20%,更优选1-10%和最优选2-5%(按重量计),基于粘合剂组合物。
(b1)与(b2)按重量计的相对量优选是75∶25到25∶75,更优选50∶50。
优选的是,组分(a)的粘合剂选自压敏粘合剂,橡胶基粘合剂,溶剂或乳液基粘合剂,热熔粘合剂和天然产物基粘合剂。
合适的树脂选自聚氨酯,聚丙烯酸类,环氧树脂类,酚醛树脂类,聚酰亚胺类,聚(乙烯醇缩丁醛),聚氰基丙烯酸酯类,聚丙烯酸酯类,乙烯/丙烯酸共聚物和它们的盐(离聚物),硅聚合物类,聚(乙烯/乙酸乙烯酯),无规立构聚丙烯,苯乙烯-二烯烃共聚物,聚酰胺,羟基终止的聚丁二烯,聚氯丁二烯,热固性树脂类,尿素甲醛聚合物,聚(乙酸乙烯酯),羧基化苯乙烯/丁二烯共聚物和聚(乙烯醇)。
优选该粘合剂组合物存在于层压或多层结构体中。
优选该层压或多层结构体是选自以下这些:
(a)后向反射片材和标志牌和保形标记片材;
(b)各种构造的日照控制膜;
(c)耐腐蚀的银镜和太阳光反射器;
(d)反射型打印标签;
(e)UV吸收玻璃和玻璃涂料;
(f)电致变色装置;
(g)膜/玻璃窗;
(h)挡风玻璃和中间层;和
(i)光学膜。
更优选该层压或多层结构体是选自以下这些:
(a)后向反射片材和标志牌和保形标记片材;
(b)各种构造的日照控制膜;
(e)UV吸收玻璃和玻璃涂料;
(g)膜/玻璃窗;和
(h)挡风玻璃和中间层。
最优选该层压或多层结构体是选自以下这些:
(b)各种构造的日照控制膜;和
(h)挡风玻璃和中间层。
优选的是这样一些组合物,其中组分(a)的粘合剂是选自以下这些的树脂:
(i)聚氨酯类;
(ii)聚丙烯酸类;
(iii)环氧树脂类;
(iv)酚醛树脂类;
(v)聚酰亚胺类;
(vi)聚(乙烯醇缩丁醛);
(vii)聚氰基丙烯酸酯类;
(viii)聚丙烯酸酯类;
(ix)乙烯/丙烯酸共聚物和它们的盐类(离聚物类);
(x)硅聚合物类;
(xi)聚(乙烯/乙酸乙烯酯);
(xii)无规立构聚丙烯;
(xiii)苯乙烯-二烯共聚物类;
(xiv)聚酰胺类;
(xv)羟基终止的聚丁二烯;
(xvi)聚氯丁二烯;
(xvii)聚(乙酸乙烯酯);
(xviii)羧基化苯乙烯/丁二烯共聚物类;
(xix)聚(乙烯醇);和
(xx)聚酯类。
更优选该粘合剂是选自以下的树脂:聚氨酯类、聚丙烯酸类、环氧树脂类、酚醛树脂类、聚酰亚胺类、聚(乙烯醇缩丁醛)、聚(乙烯醇)、乙烯/乙酸乙烯酯共聚物类、聚烯烃类、天然橡胶、苯乙烯/丁二烯橡胶类、聚丙烯酸酯类、热固性树脂类、乙烯基聚合物类、尿素甲醛聚合物类、苯乙烯聚合物类和聚氰基丙烯酸酯类。
另一优选实施方案是其中组分(a)的粘合剂是选自以下这些的树脂时的情况:聚(乙烯醇缩丁醛)、乙烯/乙酸乙烯酯共聚物类、聚丙烯酸类、聚丙烯酸酯类、天然橡胶、聚氰基丙烯酸酯、聚(乙烯醇)、苯乙烯/丁二烯橡胶、酚醛树脂类、尿素-甲醛聚合物类、环氧树脂类、乙烯基聚合物类、聚氨酯类和苯乙烯嵌段共聚物类。
特别优选的是这样的组合物,其中组分(a)的粘合剂是选自以下这些的树脂:
聚(乙烯醇缩丁醛)、乙烯/乙酸乙烯酯共聚物类、聚丙烯酸化物类、聚丙烯酸酯类、天然橡胶、聚氰基丙烯酸酯、聚(乙烯醇)、苯乙烯/丁二烯橡胶、酚醛树脂类、乙烯基聚合物类、聚氨酯类和苯乙烯嵌段共聚物类。
最优选的是这样一些组合物,其中组分(a)的粘合剂是聚丙烯酸酯。
被苯并三唑稳定的本发明粘合剂还任选含有0.01-10wt%,优选0.025-5wt%,和最优选0.1-3wt%的附加助添加剂如抗氧化剂、其它UV吸收剂、位阻胺、亚磷酸酯或亚膦酸酯、羟胺、硝酮、苯并呋喃-2-酮、硫代协合剂、聚酰胺稳定剂、金属硬脂酸盐、成核剂、填料、增强剂、润滑剂、乳化剂、染料、颜料、荧光增白剂、阻燃剂、抗静电剂、发泡剂等等。
本发明的稳定剂可通过普通的技术,在成型制品制造之前的任何方便阶段中容易地引入到粘合剂组合物中。例如,该稳定剂可与聚合物以干燥粉形式混合,或稳定剂的悬浮液或乳液可以与聚合物的溶液,悬浮液,或乳液混合。
助添加剂的例子给出如下这些。
1.抗氧化剂
1.1.烷基化的一元酚,例如
2,6-二-叔丁基-4-甲基苯酚
2-叔丁基-4,6-二甲苯酚
2,6-二-叔丁基-4-乙基苯酚
2,6-二-叔丁基-4-正丁基苯酚
2,6-二-叔丁基-4-异丁基苯酚
2,6-二-环戊基-4-甲基苯酚
2-(α-甲基环己基)-4,6-二甲苯酚
2,6-二-十八烷基-4-甲基苯酚
2,4,6-三环己基苯酚
2,6-二-叔丁基-4-甲氧基甲基苯酚
1.2.烷基化氢醌,例如,
2,6-二-叔丁基-4-甲氧基苯酚
2,5-二-叔丁基-氢醌
2,5-二-叔戊基-氢醌
2,6-二苯基-4-十八烷氧基苯酚
1.3.羟基化硫代二苯基醚,例如,
2,2’-硫代-双(6-叔丁基-4-甲基苯酚),
2,2’-硫代-双(4-辛基苯酚),
4,4’-硫代-双(6-叔丁基-3-甲基苯酚),
4,4’-硫代-双(6-叔丁基-2-甲基苯酚),
1.4.烷叉基双酚,例如
2,2’-亚甲基-双-(6-叔丁基-4-甲基苯酚)
2,2’-亚甲基-双-(6-叔丁基-4-乙基苯酚)
2,2’-亚甲基-双-(4-甲基-6-(α-甲基环己基)-苯酚],
2,2’-亚甲基-双-(4-甲基-6-环己基苯酚)
2,2’-亚甲基-双-(6-壬基-4-甲基苯酚)
2,2’-亚甲基-双-[6-(α-甲基苄基)-4-壬基苯酚]
2,2’-亚甲基-双-[6-(α,α-二甲基苄基)-4-壬基苯酚]
2,2’-亚甲基-双-(4,6-二-叔丁基苯酚)
2,2’-亚乙基-双(4,6-二-叔丁基苯酚)
2,2’-亚乙基-双(6-叔丁基-4-异丁基苯酚)
4,4’-亚甲基-双-(2,6-二-叔丁基苯酚)
4,4’-亚甲基-双-(6-叔丁基-2-甲基苯酚)
1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-丁烷
2,6-二-(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚
1,1,3-三-(5-叔丁基-4-羟基-2-甲基苯基)-丁烷
1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷
乙二醇双-[3,3-双(3’-叔丁基-4’-羟苯基)-丁酸酯]
二-(3-叔丁基-4-羟基-5-甲基苯基)-双环戊二烯
二-[2-(3-叔丁基-2-羟基-5-甲基-苄基)-6-叔丁基-4-甲基苯基]对苯二甲酸酯。
1.5.苄基化合物,例如,
1,3,5-三-(3,5-二-叔丁基-4-羟基苄基)-2,4,6-三甲苯
二-(3,5-二-叔丁基-4-羟基苄基)硫醚
3,5-二-叔丁基-4-羟基苄基-巯基乙酸异辛基酯
双(4-叔丁基-3-羟基-2,6-二甲苄基)二硫醇对苯二甲酸酯
1,3,5-三-(3,5-二-叔丁基-4-羟基苄基)异氰脲酸酯
1,3,5-三-(4-叔丁基-3-羟基-2,6-二甲苄基)异氰脲酸酯
3,5-二-叔丁基-4-羟基苄基-磷酸双十八烷基酯
3,5-二-叔丁基-4-羟基苄基-磷酸一乙基酯,钙盐
1.6.酰胺基苯酚,例如,
4-羟基-月桂酰苯胺
4-羟基-硬脂酰苯胺
2,4-双-辛基巯基-6-(3,5-叔丁基-4-羟基苯胺基)-s-三嗪
N-(3,5-二-叔丁基-4-羟苯基)-氨基甲酸辛基酯
1.7.β-(3,5-二-叔丁基-4-羟苯基)-丙酸与一羟基或多羟基醇
的酯,例如,
甲醇 二甘醇
十八碳醇 三甘醇
1,6-己二醇 季戊四醇
新戊基二醇 三-羟乙基异氰脲酸酯
硫代二甘醇 二-羟乙基草酸二酰胺
三乙醇胺 三异丙醇胺
1.8.β-(5-叔丁基-4-羟基-3-甲基苯基)-丙酸与一羟基或多羟
基醇类的酯,例如,
甲醇 二甘醇
十八碳醇 三甘醇
1,6-己二醇 季戊四醇
新戊基二醇 三-羟乙基异氰脲酸酯
硫代二甘醇 二-羟乙基草酸二酰胺
三乙醇胺 三异丙醇胺
1.9.β-(3,5-二-叔丁基-4-羟苯基)-丙酸的酰胺,例如,
N,N’-二-(3,5-二-叔丁基-4-羟基苯基丙酰基)-六亚甲基二胺
N,N’-二-(3,5-二-叔丁基-4-羟基苯基丙酰基)-三亚甲基二胺
N,N’-二-(3,5-二-叔丁基-4-羟基苯基丙酰基)-肼
1.10二芳基胺,例如
二苯胺、N-苯基-1-萘基胺、N-(4-叔辛基苯基)-1-萘胺、4,4’-二-叔辛基-二苯胺、N-苯基苄基胺和2,4,4-三甲基戊烯的反应产物、二苯胺和2,4,4-三甲基戊烯的反应产物、N-苯基-1-萘胺和2,4,4-三甲基戊烯的反应产物。
2.UV吸收剂和光稳定剂
2.1.2-(2’-羟苯基)-苯并三唑,例如,5’-甲基-、3’,5’-二-叔丁基-、5’-叔丁基-、5’-(1,1,3,3-四甲基丁基)-、5-氯-3’,5’-二-叔丁基-、5-氯-3’-叔丁基-5’-甲基-、3’-仲丁基-5’-叔丁基-、4’-辛氧基、3’,5’-二-叔戊基-、3’,5’-双-(α,α-二甲基苄基)、3’-叔丁基-5’-(2-(ω-羟基-八(乙烯氧基)羰基-乙基)-、3’-十二烷基-5’-甲基-、和3’-叔丁基-5’-(2-辛基氧基羰基)乙基-和十二烷基化-5’-甲基衍生物。
2.2.2-羟基-二苯甲酮,例如,4-羟基-、4-甲氧基-、4-辛氧基、4-癸氧基-、4-十二烷氧基-、4-苄氧基、4,2’,4’-三羟基-和2’-羟基-4,4’-二甲氧基衍生物。
2.3.任选取代的苯甲酸的酯类,例如,水杨酸苯酯,水杨酸4-叔丁基苯酯,水杨酸辛基苯酯,二苯甲酰基间苯二酚,双-(4-叔丁基苯甲酰基)间苯二酚,苯甲酰基间苯二酚,3,5-二-叔丁基-4-羟基苯甲酸2,4-二-叔丁基苯基酯和3,5-二-叔丁基-4-羟基苯甲酸十六烷基酯。
2.4.丙烯酸酯类,例如,α-氰基-β,β-二苯基丙烯酸乙酯或异辛基酯、α-甲酯基-肉桂酸甲酯、α-氰基-β-甲基-对-甲氧基肉桂酸甲酯或丁基酯、α-甲酯基-对-甲氧基肉桂酸甲酯、N-(β-甲酯基-β-氰基乙烯基)-2-甲基-二氢吲哚。
2.5.镍化合物类,例如,2,2’-硫代-双-[4-(1,1,3,3-四甲基-丁基)苯酚]的镍配合物,如1∶1或1∶2配合比,任选有附加的配位体如正丁基胺,三乙醇胺或N-环己基二乙醇胺,二丁基二硫代氨基甲酸镍,4-羟基-3,5-二叔丁基苄基膦酸的单烷基酯(例如甲酯、乙酯或丁酯)类的镍盐,酮肟例如2-羟基-4-甲基-苯基十一烷基酮肟的镍配合物类,1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,任选有附加的配位体。
2.6.位阻胺类,例如癸二酸双(2,2,6,6-四甲基-哌啶基)酯,癸二酸双(1,2,2,6,6-五甲基-哌啶基)酯,正丁基-3,5-二叔丁基-4-羟基苄基丙二酸双(1,2,2,6,6-五甲基-哌啶基)酯,1-羟乙基-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合产物,N,N’-双(2,2,6,6-四甲基-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-s-三嗪的缩合产物,次氮基三乙酸三(2,2,6,6-四甲基-哌啶基)酯,1,2,3,4-丁烷四羧酸四(2,2,6,6-四甲基-4-哌啶基)酯,1,1’-(1,2-亚乙基)-双-(3,3,5,5-四甲基哌嗪酮),癸二酸双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)酯。
2.7.草酸二酰胺,例如4,4’-二-辛氧基-N,N’-草酰二苯胺,2,2’-二辛氧基-5,5’-二叔丁基-N,N’-草酰二苯胺,2,2’-二(十二烷氧基)-5,5’-二叔丁基-N,N’-草酰二苯胺,2-乙氧基-2’-乙基-N,N’-草酰二苯胺,N,N’-双(3-二甲氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2’-乙基-N,N’-草酰二苯胺和它与2-乙氧基-2’-乙基-5,4’-二叔丁基N,N’-草酰二苯胺的混合物以及邻-和对-甲氧基双取代的以及邻-和对-乙氧基-双取代的N,N’-草酰二苯胺类的混合物。
2.8.羟基苯基-s-三嗪,例如2,6-双-(2,4-二甲基苯基)-4-(2-羟基-4-辛氧基苯基)-s-三嗪;2,6-双-(2,4-二甲基苯基)-4-(2,4-二羟苯基)-s-三嗪;2,4-双(2,4-二羟苯基)-6-(4-氯苯基)-s-三嗪;2,4-双[2-羟基-4-(2-羟基-乙氧基)苯基]-6-(4-氯苯基)-s-三嗪;2,4-双[2-羟基-4-(2-羟基-4-(2-羟基乙氧基)苯基]-6-(2,4-二甲基苯基)-s-三嗪;2,4-双[2-羟基-4-(2-羟基乙氧基)苯基]-6-(4-溴苯基)-s-三嗪;2,4-双(2-羟基-4-(2-乙酰氧基乙氧基)苯基]-6-(4-氯苯基)-s-三嗪,2,4-双(2,4-二羟苯基)-6-(2,4-二甲基苯基)-s-三嗪。
3.金属减活剂,例如,N,N’-二苯基草酰二胺,N-水杨醛-N’-水杨酰基肼,N,N’-双-(水杨酰基)肼,N,N’-双-(3,5-二叔丁基-4-羟基苯基丙酰基)肼,3-水杨酰基氨基-1,2,4-三唑,双(亚苄基)草酰二肼。
4.亚磷酸酯和亚膦酸酯,例如,亚磷酸三苯酯,亚磷酸二苯基烷基酯,亚磷酸苯基二烷基酯,亚磷酸三(壬基苯基)酯,亚磷酸三月桂基酯,亚磷酸三(十八烷基)酯,二亚磷酸二-硬脂基-季戊四醇酯,亚磷酸三-(2,4-二-叔丁基苯基)酯,二亚磷酸双异癸基季戊四醇酯,二亚磷酸二-(2,4,6-三叔丁基苯基)-季戊四醇酯,二亚磷酸二-(2,4-二-叔丁基-6-甲基苯基)-季戊四醇酯,二亚磷酸二-(2,4-二-叔丁基苯基)季戊四醇酯,三亚磷酸三硬脂基-山梨糖醇酯,双亚膦酸四-(2,4-二-叔丁基苯基)4,4’-二亚苯基酯。
5.破坏过氧化物的化合物,例如,β-硫代二丙酸的酯类,例如月桂基、硬脂基、肉豆蔻基或十三烷基酯类,巯基-苯并咪唑,或2-巯基苯并咪唑的锌盐,二硫代氨基甲酸二丁锌盐,双十八烷基二硫化物,四-(β-十二烷基巯基)-丙酸季戊四醇酯。
6.羟胺,例如,N,N-二苄基羟胺,N,N-二乙基羟胺,N,N-二辛基羟胺,N,N-二月桂基羟胺,N,N-双十四烷基羟胺,N,N-双十六烷基羟胺,N,N-双十八烷基羟胺,N-十六烷基-N-十八烷基-羟胺,N-十七烷基-N-十八烷基羟胺,从氢化牛脂胺衍生的N,N-二烷基羟胺。
7.硝酮,例如,N-苄基-α-苯基硝酮,N-乙基-α-甲基硝酮,N-辛基-α-庚基硝酮,N-月桂基-α-十一烷基硝酮,N-十四烷基-α-十三烷基硝酮,N-十六烷基-α-十五烷基硝酮,N-十八烷基-α-十七烷基硝酮,N-十六烷基-α-十七烷基硝酮,N-十八烷基-α-十五烷基硝酮,N-十七烷基-α-十七烷基硝酮,N-十八烷基-α-十六烷基硝酮,从氢化牛脂胺得到的N,N-二烷基羟胺衍生的硝酮。
8.聚酰胺稳定剂,例如铜盐与碘化物和/或磷化合物和二价锰盐的结合物。
9.碱性助稳定剂,例如,蜜胺,聚乙烯吡咯烷酮,双氰胺,氰脲酸三烯丙酯,尿素衍生物,肼衍生物,胺类,聚酰胺,聚氨酯类,高级脂肪酸的碱金属盐和碱土金属盐例如硬脂酸钙,硬脂酸锌,硬脂酸镁,蓖麻醇酸钠和棕榈酸钾,锑焦儿茶酚盐或锌焦儿茶酚盐。
10.成核剂,例如,4-叔丁基-苯甲酸,己二酸,二苯基乙酸。
11.填料和增强剂,例如,碳酸钙,硅酸盐,玻璃纤维,石棉,滑石,高岭土,云母,硫酸钡,金属氧化物和氢氧化物,炭黑,石墨。
12.其它添加剂,例如,增塑剂,润滑剂,乳化剂,颜料,荧光增白剂,防火剂,抗静电剂,发泡剂和硫代协合剂如硫代二丙酸二月桂酯或硫代二丙酸二硬脂基酯。
13.苯并呋喃酮类和二氢吲哚酮类,例如在US-A-4325863,US-A-4338244或US-A-5175312中公开的那些,或3-[4-(2-乙酰氧基乙氧基)苯基]-5,7-二-叔丁基-苯并呋喃-2-酮,5,7-二-叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮,3,3’-双[5,7-二-叔丁基-3-(4-[2-羟基乙氧基]苯基)苯并呋喃-2-酮],5,7-二-叔丁基-3-(4-乙氧基苯基)-苯并呋喃-2-酮,3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮,3-(3,5-二甲基-4-新戊酰氧基苯基)-5,7-二-叔丁基-苯并呋喃-2-酮。
该助稳定剂,除了在13项下列举的苯并呋喃酮以外,例如是以0.01-10%的浓度添加,相对于需要稳定的材料的总重量。
除了组分(a)和(b)以外,进一步优选的组合物还包括其它添加剂,尤其酚类抗氧化剂,光稳定剂或加工稳定剂。
特别优选的添加剂是酚类抗氧化剂(在1项下所列举),空间位阻胺(在2.6项下列举),亚磷酸酯和亚膦酸酯(在4项下所列举),UV吸收剂(在2项下所列举)和过氧化物破坏化合物(在5项下所列举)。
特别优选的附加添加剂(稳定剂)是苯并呋喃-2-酮,例如,在US-A-4 325 863,US-A-4,338 244或US-A-5175312中所述。
特别有益的酚类抗氧化剂选自3,5-二-叔丁基-4-羟基氢化肉桂酸正十八烷基酯,新戊烷四基四(3,5-二-叔丁基-4-羟基氢化肉桂酸酯),3,5-二-叔丁基-4-羟基苄基膦酸二正十八烷基酯,异氰脲酸1,3,5-三(3,5-二-叔丁基-4-羟基苄基)酯,硫代二亚乙基双(3,5-二-叔丁基-4-羟基氢化肉桂酸酯),1,3,5-三甲基-2,4,6-三(3,5-二-叔丁基-4-羟基苄基)苯,3,6-二氧杂八亚甲基双(3-甲基-5-叔丁基-4-羟基氢化肉桂酸酯),2,6-二-叔丁基-对甲酚,2,2’-乙叉基-双(4,6-二-叔丁基苯酚),1,3,5-三(2,6-二甲基4-叔丁基-3-羟基苄基)异氰脲酸酯,1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷,1,3,5-三[2-(3,5-二-叔丁基-4-羟基氢化肉桂酰氧基)乙基]异氰脲酸酯,3,5-二-(3,5-二-叔丁基-4-羟基苄基)酚,六亚甲基双(3,5-二-叔丁基-4-羟基氢化肉桂酸酯),1-(3,5-二-叔丁基-4-羟基苯胺基)-3,5-二(辛硫基)-s-三嗪,N,N’-六亚甲基-双(3,5-二-叔丁基-4-羟基氢化肉桂酰胺),双(乙基3,5-二-叔丁基-4-羟基苄基-磷酸)钙,亚乙基双[3,3-二(3-叔丁基-4-羟苯基)丁酸酯],3,5-二-叔丁基-4-羟基苄基巯基乙酸辛基酯,双(3,5-二-叔丁基-4-巯基氢化肉桂酰基)酰肼,N,N’-双[2-(3,5-二-叔丁基-4-羟基氢化肉桂酰氧基)-乙基]-草酰胺,2,4-双(辛硫基甲基)-6-甲基苯酚,和2,4-双(辛硫基甲基)-6-叔丁基苯酚。
最优选的酚类抗氧化剂是新戊烷四基四(3,5-二-叔丁基-4-羟基氢化肉桂酸酯),3,5-二-叔丁基-4-羟基氢化肉桂酸正十八烷基酯,1,3,5-三-甲基-2,4,6-三(3,5-二-叔丁基-4-羟基苄基)苯,1,3,5-三(3,5-二-叔丁基-4-羟基苄基)异氰脲酸酯,2,6-二-叔丁基-对甲酚,2,2’-乙叉基-双(4,6-二-叔丁基苯酚),2,4-双(辛硫基甲基)-6-甲基苯酚或2,4-双(辛硫基甲基)-6-叔丁基-苯酚。
特别合适的位阻胺化合物选自癸二酸双(2,2,6,6-四甲基哌啶-4-基)酯,癸二酸双(1,2,2,6,6-五甲基哌啶-4-基)酯,二(1,2,2,6,6-五甲基哌啶-4-基)(3,5-二-叔丁基-4-羟基苄基)丁基丙二酸酯,4-苯甲酰基-2,2,6,6-四甲基哌啶,4-硬脂酰氧基-2,2,6,6-四甲基哌啶,3-正-辛基-7,7,9,9-四甲基-1,3,8-三氮杂-螺[4.5]癸烷-2,4-二酮,次氮基三乙酸三(2,2,6,6-四甲基哌啶-4-基)酯,1,2-双(2,2,6,6-四甲基-3-氧代哌嗪-4-基)乙烷,2,2,4,4-四甲基-7-氧杂-3,20-二氮杂-21-氧代二螺[5.1.11.2]廿一烷,2,4-二氯-6-叔辛基氨基-s-三嗪和4,4’-亚己基双(氨基-2,2,6,6-四甲基哌啶)的缩聚产物,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和丁二酸的缩聚产物,4,4’-亚己基双-(氨基-2,2,6,6-四甲基哌啶)和1,2-二溴乙烷的缩聚产物,四(2,2,6,6-四甲基哌啶-4-基)1,2,3,4-丁烷四羧酸酯,四(1,2,2,6,6-五甲基哌啶-4-基)1,2,3,4-丁烷四羧酸酯,2,4-二氯-6-吗啉代-s-三嗪和4,4’-亚己基双(氨基-2,2,6,6-四甲基哌啶)的缩聚产物,N,N’,N”,N-四[(4,6-双(丁基-1,2,2,6,6-五甲基哌啶-4-基)-氨基-s-三嗪-2-基]-1,10-二氨基-4,7-二氮杂癸烷,混合的[2,2,6,6-四甲基哌啶-4-基/b,b,b’,b’-四甲基-3,9-(2,4,8,10-四氧杂螺[5.5]-十一烷)二乙基]1,2,3,4-丁烷四羧酸酯,混合的[1,2,2,6,6-五甲基哌啶-4-基/b,b,b’,b’-四甲基-3,9-(2,4,8,10-四氧杂螺[5.5]十一烷)二乙基]1,2,3,4-丁烷四羧酸酯,1,8-亚辛基双(2,2,6,6-四甲基哌啶-4-羧酸酯),4,4’-亚乙基双(2,2,6,6-四甲基哌嗪-3-酮),N-2,2,6,6-四甲基哌啶-4-基-正十二烷基琥珀酰亚胺,N-1,2,2,6,6-五甲基哌啶-4-基-正十二烷基琥珀酰亚胺,N-1-乙酰基-2,2,6,6-四甲基哌啶-4-基-正十二烷基琥珀酰亚胺,1-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮,癸二酸二-(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)酯,丁二酸二-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)酯,1-辛氧基-2,2,6,6-四甲基-4-羟基-哌啶,聚{[6-叔辛基氨基-s-三嗪-2,4-二基][2-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基]-六亚甲基-[4-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基],2,4,6-三[N-(1-环己基氧基-2,2,6,6-四甲基-哌啶-4-基)-正丁基氨基]-s-三嗪,2-(2-羟乙基)氨基-4,6-双[N-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基]-s-三嗪,1,2-双(3,3,5,5-四甲基哌嗪-2-酮-1-基)乙烷,1,3,5-三{N-环己基-N-[2-(3,3,5,5-四甲基哌嗪-2-酮-1-基)乙基]氨基}-s-三嗪,1,3,5-三{N-环己基-N-[2-(3,3,4,5,5-五甲基哌嗪-2-酮-1-基)乙基]氨基}-s-三嗪,2-4当量的2,4-双[(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与1当量的N,N’-双(3-氨基丙基)乙二胺的反应产物,双[1-(2-羟基-2甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]癸二酸酯,双[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]戊二酸酯和双[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]己二酸酯的混合物,4-羟基-1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶和4-十八烷基氧基-1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶。
最优选的位阻胺化合物是双(2,2,6,6-四甲基哌啶-4-基)癸二酸酯,双(1,2,2,6,6-五甲基哌啶-4-基)癸二酸酯,二(1,2,2,6,6-五甲基哌啶-4-基)(3,5-二-叔丁基-4-羟基苄基)丁基丙二酸酯,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和丁二酸的缩聚产物,2,4-二氯-6-叔辛基氨基-s-三嗪和4,4’-亚己基双(氨基-2,2,6,6-四甲基哌啶)的缩聚产物,N,N’,N”,N-四[(4,6-双(丁基-(1,2,2,6,6-五甲基哌啶-4-基)氨基)-s-三嗪-2-基)-1,10-二氨基-4,7-二氮杂癸烷,二-(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯,二-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)丁二酸酯,1-辛氧基-2,2,6,6-四甲基-4-羟基-哌啶,聚{[6-叔辛基氨基-s-三嗪-2,4-二基][2-(1-环己基氧基-2,2,6,6-四甲基-哌啶-4-基)亚氨基-六亚甲基-[4-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基],2,4,6-三[N-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基]-s-三嗪,2-(2-羟乙基)氨基-4,6-双[N-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基]-s-三嗪,1,2-双(3,3,5,5-四甲基哌嗪-2-酮-1-基)乙烷,1,3,5-三{N-环己基-N-[2-(3,3,5,5-四甲基哌嗪-2-酮-1-基)乙基]氨基}-s-三嗪,1,3,5-三{N-环己基-N-[2-(3,3,4,5,5-五甲基哌嗪-2-酮-1-基)乙基]氨基}-s-三嗪,2-4当量的2,4-双[(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与1当量的N,N’-双(3-氨基丙基)乙二胺的反应产物,双[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]癸二酸酯,双[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]戊二酸酯和双[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]己二酸酯的混合物,4-羟基-1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶或4-十八烷基氧基-1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶。
本发明组合物能够另外含有从苯并三唑类,s-三嗪类,草酰二苯胺类,羟基二苯甲酮类,苯甲酸酯类和α-氰基丙烯酸酯类中选择的另一种UV吸收剂。
下面的任选的组分常常存在于粘合剂配制剂中,在这里仅仅为了说明目的来给出,本意绝不是为了限制整个粘合剂组合物。这些任选的组分包括增塑剂,增粘剂,蜡,石油蜡,弹性体,增粘剂树脂,油,树脂,聚合物,松香,改性松香或松香衍生物,烃类树脂,萜烯树脂,石蜡,微晶蜡,合成的硬蜡和/或聚乙烯蜡。这些辅助添加剂的量是正常在粘合剂配制剂中使用的那些。
虽然在本发明中,本发明的苯并三唑是用于在层压或多层制品的粘合剂和粘合剂层中,但是,如果所述苯并三唑也引入到该制品的其它层,例如有任何染料或颜料存在其中的聚合物膜,不管是直接引入,还是共挤出或从粘合剂层中迁移到该其它层中,则很显然对制品提供同样有益的UV吸收保护作用。
这些聚合物是选自以下的这些:
(1)聚烯烃类;
(2)聚烯烃类的混合物;
(3)单烯烃和二烯烃或其它乙烯基单体的共聚物类;
(4)聚苯乙烯,聚(对-甲基苯乙烯)或聚(α-甲基苯乙烯);
(5)苯乙烯或α-甲基苯乙烯与二烯类或丙烯酸衍生物的共聚物类;
(6)苯乙烯或α-甲基苯乙烯的接枝体共聚物类;
(7)含卤素的聚合物类;
(8)从α,β-不饱和酸和其衍生物形成的聚合物类;
(9)由(8)的单体类彼此或与其它不饱和单体形成的共聚物类;
(10)从不饱和醇和胺类或它们的酰基衍生物或它们的缩醛形成的聚合物类;
(11)聚缩醛类,如聚甲醛和含有环氧乙烷作为共聚单体的那些聚甲醛,用热塑性聚氨酯类、丙烯酸酯或MBS改性的聚缩醛类;
(12)聚氨酯类;
(13)从二胺和二羧酸和/或从氨基羧酸或相应的内酰胺形成的聚酰胺类和共聚酰胺类;
(14)聚脲类或聚酰亚胺类;
(15)从二羧酸类和二醇类和/或从羟基羧酸或相应的内酯形成的聚酯类,尤其聚(对苯二甲酸乙二醇酯)(PET)和聚(2,6-萘二羧酸乙二醇酯)(PEN);
(16)聚碳酸酯类和聚酯碳酸酯类;
(17)聚砜类和聚醚砜类;
(18)从一方面的醛类和另一方面的酚类、脲类和蜜胺类形成的交联聚合物类;
(19)从饱和的及不饱和的二羧酸与多元醇的共聚酯和作为交联剂的乙烯基化合物衍生的不饱和聚酯树脂类;
(20)从取代的丙烯酸酯衍生的可交联的丙烯酸树脂类;
(21)上述聚合物的共混物;
(22)聚硅氧烷类;
(23)聚酮亚胺与不饱和的丙烯酸系聚乙酰基乙酸酯树脂或与不饱和丙烯酸树脂的混合物;
(24)含有烯属不饱和单体或低聚物和多不饱和脂族低聚物的辐射可固化组合物;和
(25)离聚物类(乙烯/丙烯酸和它们的盐的共聚物)。
另外,尤其当本发明粘合剂是聚(乙烯醇缩丁醛)时,该粘合剂可以夹在玻璃如汽车挡风玻璃的两(或多)层之间。
本发明的再一个主题是稳定化的、适合用作层压制品或多层结构体中的粘合剂层的一种粘合剂组合物,它包括
(a)粘合剂;和
(b)以下两组分的结合物:
(1)高度光稳定性的苯并三唑,它是2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑,或红移的苯并三唑,它是5-氯-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑或5-氯-2-(2-羟基-3-叔丁基-5-甲基苯基)-2H-苯并三唑,它们各自在一些粘合剂中具有较低溶解度;和
(2)增溶量的第二种苯并三唑,它在粘合剂中有高溶解度和选自2-(2-羟基-3,5-二-叔丁基-苯基)-2H-苯并三唑,2-(2-羟基-3,5-二-叔戊基苯基)-2H-苯并三唑,2-(2-羟基-5-叔辛基苯基)-2H-苯并三唑,2-(2-羟基-3-仲丁基-5-叔丁基苯基)-2H-苯并三唑,2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑或2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑。
优选地,当暴露于光化辐射时,组分(b)中的苯并三唑混合物显示出增强的耐久性和低的吸光度损失,如在氙弧灯(Xenon Arc)Weather-Ometer中曝照893小时之后低于0.5吸光度单位的吸光度损失或在曝照1338小时之后低于0.8吸光度单位的吸光度损失所证实的。
对于粘合剂的定义和优选条件也适用于上述稳定化的粘合剂组合物。
本发明的又一主题是通式IIIc的化合物
其中
G1和G1’独立地是氢或卤素;
G2是卤素,硝基,氰基,-COOG3,-P(O)(C6H5)2,-CO-G3,-CO-NH-G3,-CON(G3)2,-N(G3)-CO-G3,E3S-,E3SO-或E3SO2-;
G2’是具有1-12个碳原子的全氟烷基;
G3是氢,具有1-24个碳原子的直链或支链烷基,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-4个具有1-4个碳原子的烷基取代的该苯基或该苯基烷基;
E2和E2’独立地是具有1-24个碳原子的直链或支链烷基,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-3个具有1-4个碳原子的烷基取代的该苯基或该苯基烷基;或E2和E2’独立地是被一个或多个-OH、-OCOE11、-OE4、-NCO、-NH2、-NHCOE11、-NHE4或-N(E4)2或它们的混合基团取代的具有1-24个碳原子的该烷基或具有2-18个碳原子的该链烯基,其中E4是具有1-24个碳原子的直链或支链烷基;或被一个或多个-O-、-NH-或-NE4-基团或它们的混合基团插入的并能够是未被取代或被一个或多个-OH、-OE4或-NH2基团或它们的混合基团取代的该烷基或链烯基;或E2和E2’独立地是-(CH2)m-CO-E5;或E2和E2’独立地是下式的基团
-(CH2)m-CO-X-(Z)p-Y-E15
其中
E5是-OE6或-NE7E8,或
E5是-PO(OE12)2,-OSi(E11)3或-OCO-E11,
或直链或支链C1-C24烷基,它被-O-、-S-或-NE11插入和它能够是未取代的或被-OH或-OCO-E11取代,C5-C12环烷基,它是未被取代的或被-OH取代,直链或支链C2-C18链烯基,它是未被取代的或被-OH取代,C7-C15芳烷基,-CH2-CHOH-E13或缩水甘油基,
E6是氢,直链或支链C1-C24烷基,它是未被取代的或被一个或多个OH、OE4或NH2基团取代,或-OE6是-(OCH2CH2)wOH或-(OCH2CH2)wOE21,其中w是1-12和E21是具有1-12个碳原子的烷基,
E7和E8独立地是氢,具有1-18个碳原子的烷基,被-O-、-S-或-NE11-插入的直链或支链C3-C18烷基,C5-C12环烷基,C6-C14芳基或C1-C3羟基烷基,或E7和E8与N原子一起是吡咯烷,哌啶,哌嗪或吗啉环,
X是-O-或-N(E16)-,
Y是-O-或-N(E17)-,
Z是C2-C12-亚烷基,被1-3个氮原子、氧原子或其混合原子插入的C4-C12-亚烷基,或是C3-C12-亚烷基,亚丁烯基,亚丁炔基,亚环己基或亚苯基,各被羟基取代,
m是0,1或2,
p是1,或当X和Y分别是-N(E16)-和-N(E17)-时p也是0,
E15是基团-CO-C(E18)=C(H)E19或,当Y是-N(E17)-时,与E17一起形成了基团-CO-CH=CH-CO-,其中E18是氢或甲基,和E19是氢,甲基或-CO-X-E20,其中E20是氢或C1-C18烷基;
E16和E17彼此独立地是氢,C1-C18-烷基,被1-3个氧原子插入的C3-C12-烷基,或是环己基或C7-C15芳烷基,并且在Z是亚乙基的情况下E16与E17一起也形成亚乙基,
E11是氢,直链或支链C1-C18烷基,C5-C12环烷基,直链或支链C2-C18链烯基,C6-C14芳基或C7-C15芳烷基;
E12是直链或支链C1-C18烷基,直链或支链C3-C18链烯基,C5-C10环烷基,C6-C16芳基或C7-C15芳烷基;
E13是氢,直链或支化C1-C18烷基,它被-PO(OE12)2取代,未被取代的或被OH取代的苯基,C7-C15芳烷基或-CH2OE12;
E3是具有1-20个碳原子的烷基,具有2-20个碳原子的羟烷基,被具有2-9个碳原子的烷氧基羰基取代的烷基,具有3-18个碳原子的链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,具有6-10个碳原子的芳基或被一个或两个具有1-4个碳原子的烷基取代的所述芳基或1,1,2,2-四氢全氟烷基,其中全氟烷基结构部分具有6-16个碳原子;和
L是具有1到12个碳原子的亚烷基,2到12个碳原子的烷叉基,苯亚甲基,对-亚二甲苯基,α,α,α’,α’-四甲基-间亚二甲苯基或环烷叉基。
这些化合物是新颖的和明显不同于现有技术的化合物,因为它们在一个环上被全氟烷基结构部分不对称取代,和另一个环被不同的吸电子结构部分取代。
优选的是通式IIIc的化合物,其中
G1和G1’各自是氢,
G2是氯,苯磺酰基或苯硫基,
G2’是CF3,
E2和E2’独立地是具有1-24个碳原子的直链或支链烷基链,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-3个具有1-4个碳原子的烷基取代的该苯基或该苯基烷基;和
L是具有1到12个碳原子的亚烷基,2到12个碳原子的烷叉基,苯亚甲基,对-亚二甲苯基,α,α,α’,α’-四甲基-间亚二甲苯基或环烷叉基。
更优选的是通式IIIc的化合物,其中
G1和G1’各自是氢,
G2是氯,苯磺酰基或苯硫基,
G2’是CF3,
E2和E2’独立地是具有1-24个碳原子的直链或支链烷基链,具有2-18个碳原子的直链或支链链烯基,具有5-12个碳原子的环烷基,具有7-15个碳原子的苯基烷基,苯基,或在苯基环上被1-3个具有1-4个碳原子的烷基取代的该苯基或该苯基烷基;和
L是亚甲基。
最优选的是下面的化合物
(a)亚甲基-2-[4-叔-丁基-6-(5-苯磺酰基-2H-苯并三唑-2-基)苯酚]-2’-[4-叔-辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚];
(b)亚甲基-2-[4-叔-丁基-6-(5-氯-2H-苯并三唑-2-基)苯酚]-2’-[4-叔-辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚];或
(c)亚甲基-2-[4-叔-丁基-6-(5-苯硫基-2H-苯并三唑-2-基)苯酚]-2’-[4-叔-辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚]。
通式IIIc的化合物作为粘合剂组合物中的稳定剂也是非常有用的。
因此,本发明的再一个主题是适合用作层压制品或多层结构体中的粘合剂层的稳定化粘合剂组合物,它包括
(a)粘合剂;和
(b)通式IIIc的高溶解性的、红移的、光稳定的苯并三唑。
对于粘合剂的定义和优选条件也适用于上述稳定化的粘合剂组合物。通式IIIc的化合物特别适合于这一应用,因为它们兼具红移吸收和非常好的溶解度。
本发明的又一主题是被稳定以抵抗热、氧化或光诱导降解作用的组合物,它包括,
(a)遭受热、氧化或光诱导降解作用的有机材料,和
(b)有效稳定量的通式IIIc的化合物。
优选该有机材料是天然、半合成、合成的热塑性或交联聚合物。
更优选,该聚合物是聚烯烃或聚碳酸酯,尤其聚乙烯或聚丙烯;最尤其是聚丙烯;或该聚合物是苯乙烯类聚合物,ABS,尼龙,聚酯如聚(对苯二甲酸乙二醇酯)或聚(对苯二甲酸丁二醇酯),聚氨酯,丙烯酸酯,橡胶改性苯乙烯类聚合物,聚(氯乙烯),聚(乙烯醇缩丁醛),聚缩醛类(聚甲醛),聚(萘二甲酸乙二醇酯),或其它共混物或共聚物如聚(对苯二甲酸乙二醇/1,4-亚环己基二甲醇酯)PETG或离聚物。
特别优选的是其中的聚合物是聚酯的组合物。
优选该聚酯是聚(对苯二甲酸乙二醇酯),聚(对苯二甲酸丁二醇酯)或聚(萘二甲酸乙二醇酯),或共聚物聚(对苯二甲酸乙二醇/1,4-亚环己基二甲醇酯)PETG。
进一步优选的聚合物是乙烯/丙烯酸的共聚物或它的碱金属、碱土金属或过渡金属盐(离聚物)。
也优选的是这样一种组合物,其中该聚合物是聚烯烃或聚碳酸酯。
尤其该聚烯烃是聚乙烯或聚丙烯,最优选聚丙烯。
被稳定以抵抗热、氧化或光诱导的降解作用的该组合物可另外含有有效稳定量的至少一种其它UV吸收剂,后者选自苯并三唑,s-三嗪,羟基二苯甲酮,α-氰基丙烯酸酯,草酰二苯胺和苯甲酸酯。
优选的是从下面选择的2-羟苯基-2H-苯并三唑:
2-(2-羟基-5-甲基苯基)-2H-苯并三唑;
2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑;
2-(2-羟基-5-叔-丁基苯基)-2H-苯并三唑;
2-(2-羟基-5-叔-辛基苯基)-2H-苯并三唑;
5-氯-2-(2-羟基-3,5-二-叔-丁基苯基)-2H-苯并三唑;
5-氯-2-(2-羟基-3-叔丁基-5-甲基苯基)-2H-苯并三唑;
2-(2-羟基-3-仲-丁基-5-叔-丁基苯基)-2H-苯并三唑;
2-(2-羟基-4-辛氧基苯基)-2H-苯并三唑;
2-(2-羟基-3-十二烷基-5-甲基苯基)-2H-苯并三唑;
2-(2-羟基-3,5-二-叔戊基苯基)-2H-苯并三唑;
2-[2-羟基-3,5-二(α,α-二甲基苄基)苯基]-2H-苯并三唑;
2-[2-羟基-3-(α,α-二甲基苄基)-5-叔辛基苯基]-2H-苯并三唑;
2-{2-羟基-3-叔-丁基-5-[2-(ω-羟基-八(乙烯氧基)羰基)乙基]-苯基}-2H-苯并三唑;和
2-{2-羟基-3-叔-丁基-5-[2-(辛氧基)羰基)乙基]苯基}-2H-苯并三唑。
尤其其它苯并三唑是
2-(2-羟基-3,5-二-叔-戊基苯基)-2H-苯并三唑;
2-[2-羟基-3,5-二(α,α-二甲基苄基)苯基]-2H-苯并三唑;
2-[2-羟基-3-(α,α-二甲基苄基)-5-叔-辛基苯基]-2H-苯并三唑;
2-{2-羟基-3-叔-丁基-5-[2-(ω-羟基-八(乙烯氧基)羰基)乙基]苯基}-2H-苯并三唑;
5-氯-2-(2-羟基-3,5-二-叔-丁基苯基)-2H-苯并三唑;
5-氯-2-(2-羟基-3-叔-丁基-5-甲基苯基)-2H-苯并三唑;
2-(2-羟基-5-叔-辛基苯基)-2H-苯并三唑;或
2-{2-羟基-3-叔-丁基-5-[2-(辛氧基)羰基)乙基]苯基}-2-H-苯并三唑。
被稳定以抵抗热、氧化或光诱导的降解作用的组合物也可含有有效稳定量的位阻胺。
在本发明的另一优选实施方案中,有机材料是选自以下这些的树脂:热固性丙烯酸三聚氰胺树脂,丙烯酸聚氨酯树脂,环氧基羧基树脂,硅烷改性丙烯酸蜜胺,具有用蜜胺交联的氨基甲酸酯侧基的丙烯酸树脂或用含有氨基甲酸酯基团的蜜胺交联的丙烯酸多元醇树脂。
最优选地,该树脂是热固性丙烯酸三聚氰胺树脂或丙烯酸聚氨酯树脂。
在本发明的另一优选实施方案中,该有机材料是记录材料。
根据本发明的记录材料适用于压敏靠模系统,使用微胶囊的照相复制体系,热敏靠模系统,照相材料和墨喷打印。
根据本发明的记录材料突出表现于质量上的出乎意外的改进,尤其对于耐光度而言。
根据本发明的记录材料具有为具体用途的已知结构。它们由常规的载体组成,例如,涂有一层或多层的纸或塑料膜。取决于材料的类型,这些层含有适宜的所需组分,例如对于照相材料的情况,含有卤化银乳胶,染料成色剂,染料等。特别适合于墨喷打印的材料具有对常规载体上的墨水特别有吸收力的层。无涂层的纸也可用于墨喷打印。在这种情况下纸同时用作载体材料和用作墨水吸收层。用于喷墨打印的合适材料是,例如,描述在美国专利No.5,073,448中,该文献被引入本文供参考。
该记录材料也可以是透明的,例如对于投影膜的情况。
通式IIIc的化合物能够早在起毛材料(carder material)的生产中引入该材料中,例如在纸张的生产过程中,被加入到纸浆中。第二种应用方法是用通式IIIc的化合物的水溶液喷涂起毛材料或将该化合物加入到该涂料组合物中。
用于适合于投影的透明记录材料的涂料组合物不能含有任何散射光的颗粒,如颜料和填料。
染料粘结用涂料组合物能够含有许多其它添加剂,例如,抗氧化剂,光稳定剂(还包括不落在本发明的UV吸收剂范围内的UV吸收剂),粘度改进剂,荧光增白剂,生物杀伤剂和/或抗静电剂。
该涂料组合物通常被制备如下:将水溶性组分,例如粘结剂,溶于水中并一起搅拌;固体组分,例如早已描述的填料及其它添加剂,被分散在这一含水介质中;分散理想地利用装置例如超声系统,叶轮搅拌器,均化器,胶体磨,球磨机,砂磨机,高速搅拌器等等来进行。通式IIIc的化合物能够容易地引入该涂料组合物中。
根据本发明的记录材料优选含有1-5000mg/m2,尤其50-1200mg/m2的通式IIIc的化合物。
已经提及,根据本发明的记录材料包括广泛的领域。通式IIIc的化合物能够,例如,用于压敏仿形系统中。它们能够或者被引入到纸张中以保护微囊包封的染料前体避光,或者被引入到显影剂层的粘结剂中以保护在其中形成的染料。
使用利用压力显影的光敏微胶囊的照相复制体系被描述在美国专利Nos.4,416,966;4,483,912;4,352,200;4,535,050;4,535,463;4,551,407;4,562,137和4,608,330;以及在EP-A139,479;EP-A 162,664;EP-A 164,931;EP-A 237,024;EP-A 237,025和EP-A 260,129中。在所有这些体系中,该化合物能够掺入到染料接受层中。然而,该化合物也能够引入到给体层中,为的是保护成色物质免受光的作用。
能够被稳定的照相材料是含有此类染料或其前体的照相用染料和层,例如,照相纸和膜。合适的物质,例如,描述在美国专利No.5,364,749中,该文献被引入本文供参考。通式IIIc的化合物在这里用作紫外线过滤剂以抵抗静电闪光。在彩色照相材料中,成色剂和染料也被保护以防止光化分解。
本发明的通式IIIc的化合物能够用于所有类型的彩色照相材料。例如,它们能够用于彩色纸,彩色反转法纸,直接正色材料,彩色底片,彩色正片,彩色反转片等等。它们尤其优选用于照相的着色材料,后者含有反转基材或形成正色。
彩色摄影记录材料通常在载体上含有感蓝和/或感绿和/或感红的卤化银乳胶层和,如果需要,含有保护层,其中本发明的化合物优选是在感绿或感红层中或在感绿和感红层之间的层中或在卤化银乳胶层之上的层中。
通式IIIc的化合物也能够用于基于光致聚合、光致塑化或微胶囊破裂原理的记录材料中,或对于热敏和光敏的重氮盐的情况,使用具有氧化剂的无色染料或具有路易斯酸的染料内酯。
此外,本发明的化合物能够用于记录材料,后者用于染料扩散转印,热法蜡转移印刷和非矩阵印刷并与静电、电记录、电泳、磁记录和激光-电子照相印刷机和绘图笔一起使用。以上这些当中,用于染料扩散转印的记录材料是优选的,例如在EP-A 507,734中所述。
本发明的通式IIIc的化合物也能够用于油墨,优选用于喷墨打印,例如在美国专利No.5,098,477中所述,该文献被引入本文供参考。
该化合物显示出优异的水解稳定性,处理和贮存稳定性以及当存在于稳定化的组合物中时显示出良好的耐提取性。
本发明的苯并三唑是通过用于制备此类化合物的常规方法制备的。常规的程序包括取代的邻硝基苯胺的重氮化,随后将所形成的重氮盐与取代苯酚偶合和将偶氮苯中间体还原成相应的所需苯并三唑。这些苯并三唑的起始原料是大宗工业产品或能够通过正常的有机合成方法来制备。
下面的实施例用于说明本发明。
实施例A:苯并三唑的使用
实施例A1
UV吸收光谱
各种本发明的苯并三唑在苯基环上被3-α-异丙苯基结构部分和5-叔-辛基基团取代和具有最大吸光度值和给定的波长,参见以下。该紫外谱是在大约20mg/L浓度的乙酸乙酯溶液中测量的。
化合物*
λ最大(nm)
在375(nm)的吸光度
A 345 0.28
B 352 0.40
C 348 0.33
D 362 0.50
E 358 0.42
F 357 0.59
G 354 0.41
*A是2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑。
B是5-氯-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑。
C是5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑。
D是5-苯磺酰基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑。
E是5-甲氧基羰基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑。
F是5-丁基磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑。
G是3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸甲酯。
实施例A2
UV吸收光谱
测定苯并三唑的各种共混物的最大吸光度值和给定的波长,参见以下。该紫外谱是在大约20mg/L浓度的乙酸乙酯溶液中测量的。
化合物的混合物*
λ最大(nm)
在375(nm)的吸光度
B 349 0.39
C 352 0.46
B是2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑(TINUVIN900,Ciba)和5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑按1∶3重量比的混合物。
C是5-氯-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑(TINUVIN327,Ciba)和5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑按1∶3重量比的混合物。
实施例A3
苯并三唑在粘合剂中的溶解度
为了测量这一溶解度,将许多种结构不同的苯并三唑加入到典型的粘合剂GELVA263(Solutia)中,后者是聚丙烯酸酯在乙酸乙酯和己烷的混合物中的44.5%溶液。该聚丙烯酸酯是甲基丙烯酸甲酯,甲基丙烯酸2-乙基己基酯和甲基丙烯酸缩水甘油酯的共聚物。
将试验的苯并三唑溶于5ml的乙酸乙酯、甲苯或乙酸乙酯和甲苯的混合物中。向这一溶液中添加5g的GELVA263,并将2-3ml的所形成溶液加入到各表面玻璃皿中。然后根据一旦溶剂蒸发后所观察到的结晶来评价溶解度。在几个小时之后开始观察,然后继续进行几个星期的时间。
在下表中给出的溶解度值是表明没有后续结晶的迹象时的大约最高浓度。溶解度是以加入到GELVA263中的全部苯并三唑的重量来记录。从这些数据可以清楚地看出,本发明的苯并三唑比现有技术的许多苯并三唑显著更可溶于粘合剂(在这种情况下是GELVA263)中。许多苯并三唑在粘合剂中的使用在过去受到有限溶解度和一些苯并三唑化合物的相容性的限制。通过使用本发明的苯并三唑,该用量能够显著提高来大大增加稳定化保护作用,而这进一步被本发明苯并三唑的光稳定性和红移来加强。
化合物*
商品名或类型
没有结晶的溶解度(%)
A 5-乙基磺酰基 <1
B TINUVIN900 2.0
C TINUVIN327 2.0
D 5-丁基磺酰基 4.0
E 5-CF3 4.0
F 5,5’-CF3 4.0
G 5-丁基磺酰基 8.0
H 5-CF3 8.0
I 5-CF3 8.0
J 5-甲酯基-甲基亚磺酰基 8.0
K 5-苯基磺酰基 11.3
L 5-苯基磺酰基 11.3
M 5-CF3 22.6
N 5-CF3 22.6
O 5-CF3 22.6
P TINUVIN928 22.6
Q 5-氯 22.6
*A是5-乙基磺酰基-2-(2-羟基-5-甲基苯基)-2H-苯并三唑。
B是2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑。
C是5-氯-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑。
D是5-丁基磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑。
E是5-三氟甲基-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑。
F是2,2’-亚甲基-双[6-(5-三氟甲基-2H-苯并三唑-2-基)-4-叔辛基苯酚]。
G是5-丁基磺酰基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑;
H是5-三氟甲基-2-(2-羟基-5-叔辛基苯基)-2H-苯并三唑;
I是3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸甲酯。
J是5-甲氧基羰基亚甲基亚硫酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑。
K是3-(5-苯磺酰基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸甲酯。
L是5-苯磺酰基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑。
M是5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑。
N是5-三氟甲基-2-(2-羟基-3,5-二-叔辛基苯基)-2H-苯并三唑。
O是5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑。
P是2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑。
Q是5-氯-2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑。
实施例A4
苯并三唑共混物在粘合剂中的溶解度
按照实施例3的程序,测定苯并三唑类的各种混合物在GELVA263(Solutia)中的溶解度。结果参见下表。
化合物的混合物*
没有结晶的溶解度(%)
A 22.6
B 22.6
C 22.6
D 22.6
*A是2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑(TINUVIN928,Ciba)和5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑按3∶1重量比的混合物。
B是2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑(TINUVIN900,Ciba)和5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑按1∶3重量比的混合物。
C是5-氯-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑(TINUVIN327,Ciba)和5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑按1∶3重量比的混合物。
D是2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑(TINUVIN928,Ciba)和5-氯-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑(TINUVIN327,Ciba)按3∶1重量比的混合物。
实施例A5
耐候性实验
为了确认各种苯并三唑试验化合物的耐久性和损失率的结果,对在所选择的制品中的粘合剂组合物进行下述试验。
GELVA263(Solutia)粘合剂描述在实施例3中。双轴取向的聚(对苯二甲酸乙二醇酯)(PET)膜是从United States Plastics获得的。
GELVA263用乙酸乙酯稀释减少50%而达到23%的最终树脂固体含量。将试验化合物溶于GELVA263溶液中和一式两份制备样品。在下表中见到的配方是基于总涂料固体量。通过使用Headway ResearchInc.的Photo Resist Spinner(EC101 DT型),在5000rpm下操作10秒,对于每一种配方在1.5英寸玻璃盘施涂了大约8微米涂层。全部配制剂都在Hereaus LUT 6050F型烘箱中接受同样的80℃×3分钟烘烤,在3次空气变化/分钟下操作。
因为甚至在烘烤之后粘合剂仍保持粘性,直接的厚度测量是不可能的。通过在两层PET膜之间形成粘合剂夹层并使用磁感应方法将它们的厚度与没有粘合剂的两层PET膜进行对比,来测定间接膜厚度。
如此获得了旋涂条件。此外,因为旋涂条件对于将粘合剂施涂于玻璃上是没有变化的,可以预计有非常小的厚度变化(如果有的话)。在将它在烘箱中固化之后,在粘合剂上放置一层PET(大约2密耳)和施加压力。
使用Perkin Elmer Lambda 19分光光度计运行UVWINLAB软件来收集吸光度谱图。在240纳米/分钟的速度和2纳米的缝隙宽度下,从400纳米到300纳米之间以半纳米的间隔收集吸光度数据。
在6500W的受控辐照度下进行耐候性试验。周期如下:在不喷射水的情况下3.8小时对直辐照,随后保持一个小时的黑暗。在光照周期中,黑板温度被控制在89℃。在光照周期中腔室(干球)温度是62℃。在光照周期中相对湿度是在50-55%范围内和在黑暗周期中是在95%。在黑暗周期中腔室(干球)温度是38℃。
将试样放置在Xenon Arc Weather-O-meter中,让玻璃面对氙气灯以仿真制品如太阳贴膜。以大约250小时的时间间隔获取UV谱。在500小时获得UV谱图,并将样品旋转以确保所有样品接受同样的耐候性试验条件。
为了跟踪UV吸收剂从该粘合剂组合物中的损失,最初和在耐候性试验之后都测量UV谱。使用基准光束衰减技术,该UV分光光度计线性地测量吸光度,直到5.5吸光度单位。
可以假设,UV吸收剂的降解产物对UV谱图没有贡献。这是通过跟踪在300纳米处的谱带和在大约340纳米处的谱带的吸光度的比率来测试的。在对样品的耐候性试验之后,该比率没有变化。这可以说明,耐候性试验之后的膜的UV谱对应于保留在膜中的UV吸收剂的量,光致降解产物对谱图有很少的贡献(如果有的话)。
在893小时曝照之后的结果给出在下表中。
初始 最终
化合物(%)* 吸光度 吸光度 吸光度损失
I(8%) 2.998 2.048 0.950
II(10%) 2.810 2.013 0.797
III(5%) 1.561 1.241 0.320
IV(10%) 2.181 1.904 0.277
IV(10%) 2.088 1.974 0.114
+V(0.5%)
*%是配方中的重量。
I是2,2’-二羟基-4-甲氧基二苯甲酮。
II是3-(2H-苯并三唑-2-基)-5-叔-丁基-4-羟基氢化肉桂酸辛基酯。
III是2-(2-羟基-3-α-异丙苯基-5-叔-辛基苯基)-2H-苯并三唑。
IV是5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔-辛基苯基)-2H-苯并三唑。
V是双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯。
这些数据清楚地表明,本发明的苯并三唑在粘合剂中是尤其有耐久性的,如在暴露于光化辐射之后吸光度值的低损失速率说明的。本发明的苯并三唑如2-(2-羟基-3-α-异丙苯基-5-叔-辛基苯基)-2H-苯并三唑即使没有红移以及红移的苯并三唑在粘合剂组合物中都远远优于二苯甲酮。而且,苯并三唑与位阻胺稳定剂的结合物提供了相当优异的性能。总之,本发明的苯并三唑既有高的光稳定性,又在粘合剂体系中有出乎意料的高溶解度。
实施例A6
耐候性实验
在类似于实施例5的实验中,将在实施例3中描述的GELVA263(Solutia)粘合剂,它含有8wt%的试验化合物,放置在玻璃片和在实施例4中所述的聚(对苯二甲酸乙二醇酯)(PET)的双轴取向膜之间。该结构体然后按照实施例4中所述暴露于耐候性试验条件中达到947小时。
结果参见下表。各试样还含有0.5%的位阻胺双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯。
初始 最终
化合物(%)* 吸光度 吸光度 吸光度损失
I(8%) 2.88 2.12 0.76
II(8%) 1.73 1.55 0.18
III(8%) 1.46 1.45 0.01
IV(8%) 1.96 1.59 0.37
*%是配方中的重量。
I是2,2’-二羟基-4-甲氧基二苯甲酮。
II是3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔-丁基-4-羟基氢化肉桂酸甲酯。
III是5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔-辛基苯基)-2H-苯并三唑。
IV是2-(2-羟基-3-α-异丙苯基-5-叔-辛基苯基)-2H-苯并三唑。
这些数据清楚地表明,在苯并环的5-位上被吸电子结构部分取代或在苯基环的邻位上被α-异丙苯基结构部分取代的本发明苯并三唑尤其在粘合剂中是有耐久性的,如由暴露于光化辐射之后的吸光度值的低损失速率所示。另外,可以看出,红移的苯并三唑在粘合剂组合物中的表现远远优于二苯甲酮。而且,红移的苯并三唑与位阻胺稳定剂的结合物提供了相当优异的性能。总之,本发明的红移的苯并三唑既有高的光稳定性,又在粘合剂体系中有出乎意料的高溶解度。
实施例A7
挡风玻璃夹层组合体
当含有苯并三唑UV吸收剂的粘合剂组合物被放置在两片玻璃之间时,该组合体类似于典型的挡风玻璃。在这一受限的环境中,苯并三唑稳定剂没有机会通过挥发来逃逸,因为玻璃片为粘合剂中间层提供不透性容器。可溶性苯并三唑稳定剂的光稳定性和耐久性现在是最高的。因为本身的结构导致易挥发性和因此排除了在其它类型应用中使用的苯并三唑UV吸收剂能够用于这种挡风玻璃夹层组合体中,不受损害地获得了耐久和稳定的挡风玻璃结构。
将挡风玻璃或挡风玻璃原型结构暴露于根据实施例5中所述的程序的耐候性试验条件。GELVA263(Solutia)粘合剂被放置在两片玻璃之间和另外含有8wt%的所选择的试验UV吸收剂。该结构体然后按照实施例5中所述暴露于耐候性试验条件中达到1338小时。
结果参见下表。各试样仅仅含有UV吸收剂而没有位阻胺助添加剂。
初始 最终
化合物(%)* 吸光度 吸光度 吸光度损失
I(8%) 2.69 0.85 1.84
II(8%) 2.24 1.54 0.70
III(8%) 1.81 1.02 0.79
IV(8%) 0.35
*%是配方中的重量。
I是2,2’-二羟基-4-甲氧基二苯甲酮。
II是5-三氟甲基-2-(2-羟基-5-叔-辛基苯基)-2H-苯并三唑。
III是3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔-丁基-4-羟基氢化肉桂酸甲酯。
IV是2-(2-羟基-3-α-异丙苯基-5-叔-辛基苯基)-2H-苯并三唑。
这些数据清楚地表明,在苯并环的5-位上被吸电子结构部分取代或在苯基环的邻位上被α-异丙苯基结构部分取代的本发明苯并三唑尤其在粘合剂中是有耐久性的,如由暴露于光化辐射之后的吸光度值的低损失速率所示。另外,可以看出,红移的苯并三唑在粘合剂组合物中的表现远远优于二苯甲酮。总之,本发明的红移的苯并三唑既有高的光稳定性,又在粘合剂体系中有出乎意料的高溶解度。
实施例A8
将如实施例7中所述的挡风玻璃或挡风玻璃原型结构暴露于根据在实施例中所述的程序的耐候性试验条件。GELVA263(Solutia)粘合剂被放置在两片玻璃之间和另外含有8wt%的所选择的试验UV吸收剂。该结构体然后按照实施例5中所述暴露于耐候性试验条件中达到1338小时。
结果参见下表。各试样还含有0.5%的位阻胺双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯。
初始 最终
化合物(%)* 吸光度 吸光度 吸光度损失
I(8%) 3.69 2.89 0.80
II(8%) 2.06 1.85 0.21
III(8%) 1.45 1.21 0.24
IV(8%) 1.84 1.61 0.23
V(8%) 1.34 1.02 0.32
*%是配方中的重量。
I是2,2’-二羟基-4-甲氧基二苯甲酮。
II是5-三氟甲基-2-(2-羟基-5-叔-辛基苯基)-2H-苯并三唑。
III是5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔-辛基苯基)-2H-苯并三唑。
IV是3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔-丁基-4-羟基氢化肉桂酸甲酯。
V是5-正丁基磺酰基-2-(2-羟基-3-α-异丙苯基-5-叔-辛基苯基)-2H-苯并三唑。
这些数据清楚地表明,在苯并环的5-位上被吸电子结构部分取代的本发明苯并三唑尤其在粘合剂中是有耐久性的,如由暴露于光化辐射之后的吸光度值的低损失速率所示。另外,可以看出,红移的苯并三唑在粘合剂组合物中的表现远远优于二苯甲酮。而且,红移的苯并三唑与位阻胺稳定剂的结合物提供了相当优异的性能。总之,本发明的红移的苯并三唑既有高的光稳定性,又在粘合剂体系中有出乎意料的高溶解度。
实施例A9
本发明苯并三唑UV吸收剂能够用于印刷品和照片的膜和硬质塑料保护性覆盖层中以提供优异的光稳定性。
实施例A10
本发明的苯并三唑UV吸收剂能够用于背光式显示器以提供优异的长期的稳定作用。
实施例11
本发明的苯并三唑UV吸收剂能够用于半透明和不透明的橱窗陈列、标志牌和贴纸,其中膜或硬质塑料图形被层压到窗玻璃上以提供优异的长期稳定作用。
实施例A12
本发明的苯并三唑UV吸收剂能够用于在玻璃、金属或塑料基材上使用的透明/带色的抗乱画的膜中以提供优异的长期稳定作用。
实施例A13
本发明的苯并三唑UV吸收剂能够用于在玻璃层或聚碳酸酯层上或之间使用的透明抗割碎或“安全”膜中以提供长期的稳定作用。
实施例A14
本发明的苯并三唑UV吸收剂能够用于例如在汽车、公共汽车、设备及其它外露产品上的涂层表面所用的装饰和保护膜和贴纸中以提供长期的稳定作用。
实施例B:通式IIIc的新型苯并三唑的制备和使用。
实施例B1
5-三氟甲基-2-(2-羟基-3-(二正丁基-氨基甲基-5-叔辛基苯基)-2H-苯并三唑。
在环境温度下将5-三氟甲基-2-(2-羟基-5-叔辛基苯基)-2H-苯并三唑(40.9g,0.104mol),多聚甲醛(3.65g,0.116mol)和二正丁胺(28.2g,0.216mol)加入到压力反应器中。该反应器被密封并将温度升高到160℃。该反应物料在160℃下保持4小时,然后出料。该反应器用甲苯漂洗。甲苯,胺和水通过旋转蒸发来抽提。这一粗曼尼期产物通过使用庚烷/乙酸乙酯梯度作为洗脱剂在硅胶柱上进行色层分离,以除去痕量的未反应的起始苯并三唑中间体。在色层分离之后以93%产率获得了该标题化合物,为黄色油状物。
分析:
1H nmr(CDCl3):δ0.79(s,9H);0.88(t,6H);1.32(m,4H);1.40(s,6H);1.52(m,4H);1.75(s,2H);2.55(t,4H);3.90(s,2H);7.18(d,1H);7.60(dd,1H);7.68(d,1H);8.13(dd,1H):8.35(d,1H)。
质谱:m/z 533(M+H)。
实施例B2
亚甲基-2-[4-叔丁基-6-(5-苯磺酰基-2H-苯并三唑-2-基)苯酚]-2’-[4-叔辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚]
将5-苯磺酰基-2-(2-羟基-5-叔丁基苯基)-2H-苯并三唑(6.8g,0.017mol),甲醇钠(0.99g,0.017mol)和二甲苯(20g,0.187mol)加入到反应烧瓶,然后加热至160℃。在实施例B1中制得的溶于8g二甲苯中的化合物(8.93g,0.0167mol)经过1小时缓慢滴入该反应物料中。在添加结束后,该反应物料被加热至205℃,同时蒸馏出二甲苯,甲醇和二正丁胺。在205℃下1小时之后,该反应物料置于26″Hg真空下三小时。在释放真空之后,反应物料被冷却至100℃,添加50g的二甲苯。该溶液然后用25g的10%盐酸水溶液洗涤。在馏出该溶剂之后获得15.5g的粗产物。它通过使用在庚烷中浓度15%的乙酸乙酯作为洗脱剂,在硅胶上进行色层分离。以6.6g的产量获得了固体形式的标题化合物,它在95-100℃下熔化。
分析:
1H nmr(CDCl3):δ0.72(s,9H);1.35(s,9H);1.42(s,6H);1.76(s,2H);4.31(s,2H);7.44(d,2H);7.55(t,2H);7.61(t,1H);7.68(dd,1H);7.91(dd,1H);8.03(d,2H);8.04(d,1H);8.08(d,1H);8.31(d,1H);8.32(d,2H);8.73(d,1H);11.14(s,1H);11.23(s,1H)。
19F nmr(CDCl3):-68.9ppm。
质谱:m/z 811(M+H)。
实施例B3
亚甲基-2-[4-叔丁基-6-(5-氯-2H-苯并三唑-2-基)苯酚]-2’-[4-叔辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚]
使用实施例B2的程序,用4.5g的5-氯-2-(2-羟基-5-叔丁基-苯基)-2H-苯并三唑代替5-苯磺酰基-2-(2-羟基-5-叔丁基苯基)-2H-苯并三唑并将反应物的同一摩尔比率保持相同,获得了具有32-44℃熔点的8.67g标题化合物。
分析:
1H nmr(CDCl3):δ0.73(s,9H);1.36(s,9H);1.42(s,6H);1.76(s,2H);4.31(s,2H);7.40(d,1H);7.43(d,1H);7.44(dd,1H);7.68(dd,1H);7.89(d,1H);7.94(d,1H);8.08(d,1H);8.29(d,1H);8.32(d,2H);11.23(s,1H);11.29(s,1H)。
19F nmr(CDCl3):-68.9ppm。
质谱:m/z 705(M+H)。
实施例B4
亚甲基-2-[4-叔丁基-6-(5-苯硫基-2H-苯并三唑-2-基)苯酚]-2’-[4-叔辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚]
使用实施例B2的程序,用5.67g的5-苯硫基-2-(2-羟基-5-叔丁基-苯基)-2H-苯并三唑代替5-苯磺酰基-2-(2-羟基-5-叔丁基-苯基)-2H-苯并三唑并将反应物的同一摩尔比率保持相同,获得了具有49-65℃熔点的5.97g标题化合物。
分析:
1H nmr(CDCl3):δ0.72(s,9H);1.34(s,9H);1.41(s,6H);1.75(s,2H);4.30(s,2H);7.34-7.52(m,3H);7.37(d,1H);7.39(dd,1H);7.43(d,1H);7.50(d,2H);7.68(d,1H);7.73(d,1H);7.84(d,1H);8.08(d,1H);8.26(d,1H);8.31(d,1H);8.32(d,1H);11.20(s,1H);11.36(s,1H)。
19F nmr(CDCl3):-68.9ppm。
质谱:m/z 779(M+H)。
实施例B5
2,2-亚甲基-双[6-(5-苯磺酰基-2H-苯并三唑-2-基)4-叔丁基苯酚]
将5-苯磺酰基-2-(2-羟基-5-叔丁基苯基)-2H-苯并三唑(15g,0.037mol),多聚甲醛(0.63g,0.019mol)和二正丁胺(5.0g,0.386mol)加入到反应器中,然后密封。该温度提高到110℃,在此时添加甲醇钠(0.33g,0.0069mol)。该反应混合物然后被加热到205℃和在其中保持三小时。该反应物料然后被冷却到110℃和添加100ml的二甲苯。该反应物料用10%盐酸水溶液中和,有机相用水洗涤两次。二甲苯相滤过一栓塞的硅胶和然后蒸馏。粗曼尼期产物从庚烷中重结晶两次,得到熔点为224-234℃的8.3g标题化合物。
分析:
1H nmr(CDCl3):δ1.40(s,18H);4.30(s,2H);7.50(d,2H);7.55(t,4H);7.61(t,4H);7.91(dd,2H);8.04(m,6H);8.30(d,2H);8.73(d,2H);11.12(s,2H)。
质谱:m/z 827(M+H)。
实施例B6
双苯并三唑在粘合剂中的溶解度
为了测量双苯并三唑UV吸收剂在粘合剂组合物中的溶解度,将该化合物加入到典型的粘合剂GELVA263(Solutia)中,它是聚丙烯酸酯在乙酸乙酯和己烷的混合物中的44.5%溶液。该聚丙烯酸酯是甲基丙烯酸甲酯、甲基丙烯酸2-乙基己基酯和甲基丙烯酸缩水甘油酯的共聚物。
将试验化合物溶于5ml的乙酸乙酯,甲苯或乙酸乙酯和甲苯的混合物中。向该溶液中添加5g的GELVA263。将2-3ml的所获得的溶液放置在表面玻璃皿中。然后根据一旦溶剂蒸发后所观察到的结晶来评价溶解度。在几个小时之后开始观察和然后继续进行几个星期的时间。
在下表中给出的溶解度值是表明没有后续结晶的迹象时的大约最高浓度。溶解度是以加入到GELVA263中的全部双苯并三唑的重量来记录。从这些数据可以清楚地看出,一些本发明的双苯并三唑比现有技术的一些双苯并三唑显著更可溶于粘合剂(在这种情况下是GELVA263)中。许多UV吸收剂在粘合剂组合物中的使用在过去受到有限溶解度和一些UV吸收剂化合物的相容性的限制。
通过使用所选择的本发明双苯并三唑,该UV吸收剂的用量能够显著提高来大大增加由本发明化合物所获得的稳定化保护作用。这进一步通过本发明双苯并三唑的优异光稳定性和红移性质来增强。
化合物* 商品名或类型
没有结晶的溶解度(%)
A 双苯并三唑 0.0
B TINUVIN900 2.0
C TINUVIN327 2.0
D 双苯并三唑 2.0
E 双苯并三唑 4.0
F 双苯并三唑 11.0
G 双苯并三唑 22.0
H 双苯并三唑 22.0
*A是实施例5的、一般性地在德国专利1,670,951中公开的对比用对称双苯并三唑化合物。
B是2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑。
C是5-氯-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑。
D是亚甲基-2-[4-叔辛基-6-(2H-苯并三唑-2-基)苯酚]-2’-[4-叔辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚]。
E是2,2’-亚甲基-双[6-(5-三氟甲基-2H-苯并三唑-2-基)-4-叔辛基苯酚]。
F是实施例3的本发明的不对称双苯并三唑化合物。
G是实施例2的本发明的不对称双苯并三唑化合物。
H是实施例4的本发明的不对称双苯并三唑化合物。
实施例B7
亚甲基-2-[4-(2-甲氧基羰基乙基)-6-(5-氯-2H-苯并三唑-2-基)苯酚]-2’-[4-叔辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚]
按照在实施例B1和B2中所列的一般性合成程序或按照EP924,203A1中所公开的方法,制备标题化合物。
实施例B8-B30
按照在实施例1和2中列出的一般性合成程序,制备下面通式I的化合物。
Ex*
G2
E2
E2’
L
G3或E3
8 F CH3 t-Bu -CH2- -
9 F t-Oc t-Oc -CH2- -
10 Cl Do CH3 m-Xy -
11 Cl t-Bu t-Bu -CH2- -
12 PO(Ph)2 Do Do -CH2- -
13 COOG3 Cu Bu p-Xy CH3
14 COOG3 CH3 CH3 -CH2- Octad
15 COOG3 t-Oc CH3 -CH2- Benz
16 CONHG3 C24H49 Bu -CH2- Bu
17 CON(G3)2 Do Hept -CH2- Al
18 CN t-Oc t-Bu -CH2- -
19 CN Cu Do -CH2- -
20 E3SO CH3 Cu -CH2- Bu
21 E3S CH3 t-Bu -CH2- Do
22 E3SO2 MeOCOEt t-Bu -CH2- Ph
23 E3SO2 MeOCOEt MeOCOEt -CH2- Oc
24 E3SO2 t-Bu t-Bu -CH2- HOEt
25 Cl AlOCOEt CH3 -CH2- -
26 Cl OcOCOEt Oc -CH2- -
27 Cl AlOCOEt AlOCOEt -CH2- -
28 Cl MeAcOEt CH3 -CH2- -
29 Cl Do MeAcOEt -CH2- -
30 Cl HOPr HOPr -CH2- -
*G1总是氢,只是在实施例9中它是F和在实施例10-11中它是Cl。
G1’总是氢,只是在实施例11中它是Cl。
G2’总是CF3,只是在实施例10中它是C8F17和在实施例11中它是C2F5。
Al是烯丙基,AlOCOEt是CH2=CH-CH2OCOCH2CH2,Benz是苄基,Bu是丁基,t-Bu是叔丁基,Cu是α-异丙苯基,Do是十二烷基,Hept是庚基,HOEt是HOCH2CH2,HOPr是HOCH2CH2CH2,MeAcOEt是CH2=C(CH3)COOCH2CH2,MeOCOEt是CH3OCOCH2CH2,Oc是辛基,t-Oc是叔辛基,OCOCOEt是C8H17OCOCH2CH2,Octad是十八烷基,Ph是苯基,m-Xy是α,α,α’,α’-四甲基-m-亚二甲苯基和p-Xy是α,α,α’,α’-四甲基-p-亚二甲苯基。
实施例31
聚碳酸酯
本发明的苯并三唑在热塑性基材中的耐久性是通过将各种试验化合物引入到聚碳酸酯树脂的溶剂流延薄膜中来测定的。将自持型薄膜安放在纸板固定夹中,固定在金属框中,和根据ASTM G26在干燥条件下暴露于Atlas C165 Xenon-arc Weather-Ometer中进行1100和2200小时曝照。通过监测早已描述过的诊断UV吸收的损失来测定UV吸收剂的损失。由膜的颜色变化或物理完整性来测量性能。
在室温下将聚碳酸酯薄片(LEXAN145,General Electric)与1-3wt%(基于聚碳酸酯)的试验苯并三唑一起溶于二氯甲烷中。使用校准的刮涂棒流延膜,制备在干燥之后1密耳厚的膜。
用在苯并环的5-位上被三氟甲基结构部分取代的苯并三唑获得了耐久性的提高。
实施例32
颜料着色的聚缩醛类
下面的实施例显示了对于在苯并环的5-位上被三氟甲基结构部分取代的双苯并三唑而言在颜料着色的聚缩醛配制剂的颜色保护上的改进。
使用Turbula混合器将试验添加剂与聚缩醛类粒料(DELRIN500P NC010,DuPont)干掺混。使用双螺杆挤出机在大约410°F(210℃)的熔化温度下将干掺混物挤出和造粒。该粒料通过使用在410-420°F(204-216℃)下操作的注射模型成形机被模塑加工成试验板(2″×2″×0.060″)。根据汽车试验程序SAE J1885将试验板暴露于Xenon-arc Weather-Ometer。曝露是根据总辐照量测量的,按千焦耳/每平方米(kJ/m2)计。在曝照样品中的颜色变化是通过测量曝照样品的色度,与未曝照样品对比,作为根据ASTM D2244的色差(ΔE)来测定的。
实施例33
聚(对苯二甲酸丁二醇酯)
下面的实施例用于说明在苯并环的5-位上被三氟甲基取代的双苯并三唑在保护聚(对苯二甲酸丁二醇酯)上的优异性能,以光泽保留率衡量。
通过使用Turbula混合器将试验添加剂与聚(对苯二甲酸丁二醇酯)粒料(VALOX315-1001,General Electric)干混合。干混物使用双螺杆挤出机在465-490℃下挤出和造粒。该粒料通过使用在475-515°F(246-268℃)下操作的注射模型成形机被模塑加工成试验板(2″×2″×0.060″)。根据ASTM G26试验方法A将试验板暴露于Xenon arcWeather-Ometer。根据ASTM D523,使用光泽计对未曝照和曝照的样品测量60°光泽度。光泽保留率%=(曝照样品的光泽度/未曝照样品的光泽度)×100。
实施例34
聚苯乙烯
从溶于二氯甲烷中的溶液进行溶剂流延,形成聚苯乙烯膜(从Chevron获得的结晶聚苯乙烯,不含硬脂酸锌和矿物油)。按实施例31中所述,将这些膜暴露于UV光。样品不包含位阻胺稳定剂并在1000小时曝照之后检测颜色变化,检测UV吸收剂的损失和检测物理完整性(开裂或严重的膜破坏)。
实施例35
聚(甲基丙烯酸甲酯)
本发明的苯并三唑在热塑性基材中的耐久性是通过将各种试验化合物引入到聚(甲基丙烯酸甲酯)树脂的溶剂流延薄膜中来测定的。将自持型薄膜安放在纸板固定夹中,固定在金属框中,和根据ASTMG26在干燥条件下暴露于Atlas C165 Xenon-arc Weather-Ometer中进行1100和2200小时曝照。通过监测早已描述过的诊断UV吸收的损失来测定UV吸收剂的损失。性能是由薄膜的颜色或物理完整性,或UV吸收剂在λ最大下的吸光度损失的变化来测量的。
将聚(甲基丙烯酸甲酯)(中等分子量,Aldrich)与1-3wt%(基于PMMA树脂)的试验苯并三唑一起在室温下溶于二氯甲烷中。使用校准的刮涂棒流延膜,制备在干燥之后1密耳厚的膜。
用在苯并环的5-位上被三氟甲基结构部分取代的双苯并三唑获得了耐久性的提高。
实施例36
聚氨酯
将丙烯酸系多元醇(RK4037,DuPont),其在2-庚酮中含量是75%,用于这些实验中。分子量是7000-9000和OH值是145。向595g的该丙烯酸系多元醇中添加26.2g的乙酸丁酯,5.8g的乙酸乙酯和0.4g的50%强度FC 439(流动控制助剂,3M)。将双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯(0.75g TINUVIN123,Ciba),相对于树脂固体的1wt%,加入到该混合物中。向2.43g上述混合物中加入0.9g的DESMODURN-3390(Bayer),脂肪族多异氰酸酯,90%固体。该UV吸收剂被引入到丙烯酸系多元醇组分中。所形成的聚氨酯通过在1000rpm旋涂2秒作为涂层施涂于石英盘上。湿涂层在260°F(127℃)下固化30分钟。
使用Perkin Elmer的λ-9分光光度计,使用2纳米的缝隙宽度以120纳米/分钟的速度,每半纳米收集UV谱图。
损失速率是从1.4密耳厚的涂层测量的。在耐候性试验之前,长波长UV吸收谱带的吸光度是在2.3左右。根据SAE J-1960(室外汽车耐候性试验条件)进行耐候性试验:在340纳米下0.55瓦/平方英寸,使用内部和外部硼硅酸盐过滤器,不喷射水的情况下40’对直曝照;20’光照+正面喷水,60’光照和60’黑暗+背面喷水(冷凝)。在光照周期中黑板温度是70±2℃和在光照周期中相对湿度是50-55%和在黑暗周期中是100%。在大约每200小时之后跟踪长波长吸收谱带的损失。
这一试验显示,本发明的双苯并三唑在聚氨酯膜中当通过低损失速率来判断时是尤其有耐久性的。
实施例37
聚(氯乙烯)
按照实施例31中所述,在温热的四氢呋喃(THF)中进行溶剂流延,形成GEON27(Geon Co.)的聚(氯乙烯)(PVC)膜,然后按照实施例31中所述暴露于Atlas C165 Weather-Ometer。
这一试验显示,本发明的双苯并三唑在聚氯乙烯膜中当通过低损失速率来判断时是尤其有耐久性的。
实施例38
涂料组合物
通过将实验的丙烯酸系多元醇树脂和六甲氧基甲基蜜胺(Resimene747,Monsanto)按60/40的固体比率混合,制备高固含量热固性丙烯酸透明涂料。以0.70wt%添加十二烷基苯磺酸催化剂(Nacure5225;King Industries)。流动助剂Modaflow(Monsanto)以0.25wt%的量加入,形成模型丙烯酸三聚氰胺树脂体系。
该模型透明涂料用二甲苯冲释至26-27秒的粘度(使用Zahn#2杯)和使用普通压力喷涂方法在50psi(3.5kg/cm2)压力下施涂于1″×3″(2.54cm×7.62cm)石英载片上。通过将该载片在260°F(127℃)下烘烤30分钟来进行固化。透明涂料用1wt%的受阻胺光稳定剂,双-(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯,(TINUVIN123,Ciba)来稳定。各种试验苯并三唑UV吸收剂以5mmol%wt的量引入透明涂料中。在石英载片上的薄膜厚度是1.15-1.41密耳(0.029-0.036毫米)。
在Xenon Arc Weather-Ometer中以6500W的控制辐照度,使用内部石英和外部硼硅酸盐S-型过滤器,根据下述条件对石英载片上的膜进行耐候性试验。辐照周期如下:在不喷射水的情况下40分钟对直辐照,随后20分钟光照+正面喷水,接着有60分钟光照和最终有60分钟黑暗+背面喷水(冷凝)。设定值是在340nm,0.55W/M2下1.98kJ/hr。在光照周期中,黑板温度被控制在70±2℃。在光照周期中相对湿度是在50-55%范围内和在黑暗周期中是100%。记录作为氙弧灯耐候性试验时间(小时)的函数的长波长UV谱带的吸光度。
为了跟踪UV吸收剂从透明涂层中的损失,最初和在规则时间间隔的耐候性试验之后都测量UV谱。使用基准光束衰减技术,该UV分光光度计线性地测量吸光度,直到5.5吸光度单位。
可以假设,UV吸收剂的降解产物没有对UV谱图作出贡献。这是通过跟踪在300纳米处的谱带和在大约340纳米处的谱带的吸光度的比率来验证的。在对样品的耐候性试验之后,该比率没有变化。这说明,耐候性试验之后的膜的UV谱对应于保留在膜中的UV吸收剂的量,光致降解剂对谱图有很少的贡献(如果有的话)。
将代表性的双苯并三唑试验化合物以1.93和3wt%之间的浓度引入高固体含量的热固性丙烯酸三聚氰胺树脂中,得到在相同膜厚度中相同摩尔浓度的试验苯并三唑并足以得到大约2.0吸光度单位的起始吸光度。试验样品曝照2000小时。
该试验显示,当通过低损失速率来判断,本发明的双苯并三唑在汽车涂料中是尤其有耐久性的。
Claims (3)
1.稳定化的粘合剂组合物,它存在于层压制品或多层结构体中,其包括
(a)粘合剂树脂,其选自聚(乙烯醇缩丁醛),乙烯/乙酸乙烯酯共聚物类,聚丙烯酸类,聚丙烯酸酯类,天然橡胶,聚氰基丙烯酸酯类,聚(乙烯醇),苯乙烯/丁二烯橡胶,酚醛树脂类,乙烯基聚合物类,聚氨酯类和苯乙烯嵌段共聚物类;和
(b1)基于粘合剂组合物为0.1-20%重量的高溶解性的、红移的光稳定的苯并三唑,该苯并三唑选自:
(a)5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑;
(b)5-三氟甲基-2-(2-羟基-5-叔辛基苯基)-2H-苯并三唑;
(c)5-三氟甲基-2-(2-羟基-3,5-二叔辛基苯基)-2H-苯并三唑;
(d)2,2′-亚甲基双[6-(5-三氟甲基-2H-苯并三唑-2-基)-4-叔辛基酚];
(e)亚甲基-2-[4-叔辛基-6-(2H-苯并三唑-2-基)苯酚]-2′-[4-叔辛基-6-(5-三氟甲基-2H-苯并三唑-2-基)苯酚];
(f)3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸;
(g)3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸甲酯;
(h)3-(5-三氟甲基-2H-苯并三唑-2-基)-5-叔丁基-4-羟基氢化肉桂酸异辛基酯;
(i)5-三氟甲基-2-[2-羟基-5-(3-羟丙基)苯基]-2H-苯并三唑;
(n)5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑;
(o)5-三氟甲基-2-(2-羟基-3-α-异丙苯基-5-壬基苯基)-2H-苯并三唑;
(p)5-三氟甲基-2-[2-羟基-3-α-异丙苯基-5-(2-羟乙基)苯基]-2H-苯并三唑;
(q)5-三氟甲基-2-[2-羟基-3-α-异丙苯基-5-(3-羟丙基)苯基]-2H-苯并三唑;
(r)5-三氟甲基-2-(2-羟基-3,5-二-叔戊基苯基)-2H-苯并三唑;
(s)5-三氟甲基-2-(2-羟基-3,5-二-叔丁基苯基)-2H-苯并三唑;
(t)5-三氟甲基-2-(2-羟基-3-十二烷基-5-甲基苯基)-2H-苯并三唑;
(u)5-三氟甲基-2-[2-羟基-3-叔丁基-5-(3-羟丙基)苯基]-2H-苯并三唑;
(v)5-三氟甲基-2-[2-羟基-3-叔丁基-5-(2-羟乙基)苯基]-2H-苯并三唑;
(w)5-三氟甲基-2-[2-羟基-5-(2-羟乙基)苯基]-2H-苯并三唑;
(x)5-三氟甲基-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑;
(y)5-氟-2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并三唑,
或
(b2)基于粘合剂组合物为0.1-20%重量的高溶解性的和光稳定的苯并三唑,它是2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并三唑或2-(2-羟基-3-α-异丙苯基-5-叔丁基苯基)-2H-苯并三唑;或
基于粘合剂组合物为0.1-20%重量的(b1)和(b2)的化合物的混合物,其中(b1)与(b2)的重量相对量为75∶25到25∶75。
2.根据权利要求1的组合物,其中该层压或多层结构体是选自以下这些:
(a)后向反射片材和标志牌和保形标记片材;
(b)各种构造的日照控制膜;
(c)耐腐蚀的银镜和太阳光反射器;
(d)反射型打印标签;
(e)UV吸收玻璃和玻璃涂料;
(f)电致变色装置;
(g)膜/玻璃窗;
(h)挡风玻璃和中间层;和
(i)光学膜。
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US09/303,582 | 1999-05-03 | ||
US09/303,583 | 1999-05-03 | ||
US09/303,583 US6187845B1 (en) | 1999-05-03 | 1999-05-03 | Stabilized adhesive compositions containing highly soluble, red-shifted, photostable benzotriazole UV absorbers and laminated articles derived therefrom |
US09/303,582 US6268415B1 (en) | 1999-05-03 | 1999-05-03 | Stabilized adhesive compositions containing highly soluble, photostable benzotriazole UV absorbers and laminated articles derived therefrom |
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JP (4) | JP4705249B2 (zh) |
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CN (1) | CN1186417C (zh) |
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CN107148447B (zh) * | 2014-10-29 | 2020-02-21 | 首诺公司 | 包含增容剂的聚合物夹层 |
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KR20020034076A (ko) | 2002-05-08 |
CZ20013935A3 (cs) | 2002-02-13 |
KR100642675B1 (ko) | 2006-11-10 |
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TWI249561B (en) | 2006-02-21 |
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