CN1066181C - 用苯并三唑紫外线吸收剂稳定的涂层及记录材料 - Google Patents
用苯并三唑紫外线吸收剂稳定的涂层及记录材料 Download PDFInfo
- Publication number
- CN1066181C CN1066181C CN96105137A CN96105137A CN1066181C CN 1066181 C CN1066181 C CN 1066181C CN 96105137 A CN96105137 A CN 96105137A CN 96105137 A CN96105137 A CN 96105137A CN 1066181 C CN1066181 C CN 1066181C
- Authority
- CN
- China
- Prior art keywords
- coating
- butyl
- benzotriazole
- tert
- undercoat
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000006096 absorbing agent Substances 0.000 title claims abstract description 54
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 title claims abstract description 51
- 239000012964 benzotriazole Substances 0.000 title claims abstract description 46
- 238000000576 coating method Methods 0.000 title claims description 98
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- -1 alpha -cumyl Chemical group 0.000 claims abstract description 75
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
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- GCDJFNYVSDFWDB-UHFFFAOYSA-N n-hexadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC GCDJFNYVSDFWDB-UHFFFAOYSA-N 0.000 description 1
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- WLROSFKLCOYXID-UHFFFAOYSA-N n-octadecoxyheptadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCONCCCCCCCCCCCCCCCCC WLROSFKLCOYXID-UHFFFAOYSA-N 0.000 description 1
- NXYYNGHWSMAGLN-UHFFFAOYSA-N n-octadecoxyhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCONCCCCCCCCCCCCCCCC NXYYNGHWSMAGLN-UHFFFAOYSA-N 0.000 description 1
- ZXGDIORKSOYRMQ-UHFFFAOYSA-N n-octadecylheptadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCC ZXGDIORKSOYRMQ-UHFFFAOYSA-N 0.000 description 1
- MCMMSXFAWOGWQE-UHFFFAOYSA-N n-octadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC MCMMSXFAWOGWQE-UHFFFAOYSA-N 0.000 description 1
- HORBOHJHQGXXOR-UHFFFAOYSA-N n-octadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCCC HORBOHJHQGXXOR-UHFFFAOYSA-N 0.000 description 1
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- LFEDBDWFFNNYNT-UHFFFAOYSA-N o-hexadecylhydroxylamine Chemical compound CCCCCCCCCCCCCCCCON LFEDBDWFFNNYNT-UHFFFAOYSA-N 0.000 description 1
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- 239000011368 organic material Substances 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N oxalic acid Substances OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
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- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
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- 239000011574 phosphorus Substances 0.000 description 1
- 230000000176 photostabilization Effects 0.000 description 1
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- 239000001103 potassium chloride Substances 0.000 description 1
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- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
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- BOXSVZNGTQTENJ-UHFFFAOYSA-L zinc dibutyldithiocarbamate Chemical compound [Zn+2].CCCCN(C([S-])=S)CCCC.CCCCN(C([S-])=S)CCCC BOXSVZNGTQTENJ-UHFFFAOYSA-L 0.000 description 1
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
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- G03F7/031—Organic compounds not covered by group G03F7/029
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- B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
- B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
- B41M5/00—Duplicating or marking methods; Sheet materials for use therein
- B41M5/50—Recording sheets characterised by the coating used to improve ink, dye or pigment receptivity, e.g. for ink-jet or thermal dye transfer recording
- B41M5/52—Macromolecular coatings
- B41M5/5227—Macromolecular coatings characterised by organic non-macromolecular additives, e.g. UV-absorbers, plasticisers, surfactants
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles
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Abstract
一种用式1表示的可溶性苯并三唑紫外线吸收剂,
其中R1是氢或氯,R2是烷基或-CH2-CH2COOR4,其中R4是氢或烷基,R3是α-枯基,它赋予电泳涂层/底涂层/清漆涂层面漆体系以及记录材料优异的光稳定性能。
Description
本发明涉及聚合物膜涂层或记录组合物,因所选的苯并三唑紫外线吸收剂的存在使其免受灾难性破坏。
美国专利4,278,589公开了2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑和2-(2-羟基-3-叔-辛基-5-α-枯基苯基)-2H-苯并三唑的制备。美国专利4,278,589还公开了2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑的制备。后一种化合物是非常有效的紫外线吸收剂,遗憾的是它是相对不溶的,只能以约14%(重量)含量溶于二甲苯中。由于关系到环境,这种芳族溶剂有可能被禁止使用,因此需要努力研究一种有效的苯并三唑,它具有2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑的一般性光稳定效果,并且能溶于环境许可的溶剂中。
日本专利公开75/158588公开了作为有效紫外线吸收剂的2-(2-羟基-3-α-枯基-5-甲基苯基)-2H-苯并三唑和2-(2-羟基-3-甲基-5-α-枯基苯基)-2H-苯并三唑的制备。
美国专利4,283,327公开了2-(2-羟基-3,5-二-叔-辛基苯基)-2H-苯并三唑和5-氯代-2-(2-羟基-3,5-二-叔-辛基苯基)-2H-苯并三唑的制备。美国专利4,587,346、4,675,352、4,973,701、5,095,062和5,240,975公开了液态苯并三唑混合物的制备:将预先形成的苯并三唑用高级烯烃及一种酸催化剂进行后烷基化制成的。该产物是各种所述苯并三唑的复杂液态混合物,并可溶于环境许可的溶剂中。
然而尽管这些紫外线吸收剂极易溶于环境许可的溶剂中,但它没有3位上被一个α-枯基取代的苯并三唑化合物所具有的热稳定性。
本发明的苯并三唑化合物在3位上被一个α-枯基取代,5位上被烷基或被羧烷基取代的烷基取代。这种材料比简单烷基官能化的三-芳基-S-三嗪更易溶于普通涂料用溶剂中。普通涂料用溶剂包括二甲苯、甲基戊基酮、丁基溶纤剂、丁基卡必醇和甲基异丁基酮。这种官能度与化合物的高分子量结合在一起使本发明的化合物当掺入清漆涂层/底涂层体系的底涂层中时具有低色移性。
本发明的目的是提供一种防止电泳涂层/底涂层/清漆涂层体系与被涂物分离的方法,该方法是向体系中加入一种所选的可溶性苯并三唑,这种苯并三唑在其苯环的3位上被α-枯基部分取代。
本发明的另一目的是提供稳定的记录材料,后者通过一种精选的在其苯环的3位上被α-枯基取代的可溶性苯并三唑使记录材料不受光化性光的损害。
应当注意的是,近些年来,对汽车涂料的要求已经历了惊人的变化。随着对环境要求的提高,芳烃溶剂的使用已给工业上施加了很大压力,迫使工业上对一些极难的问题提出解决办法。
由于苯并三唑紫外线吸收剂能提供2-〔2-羟基-3,5-二(α-枯基)苯基〕-2H-苯并三唑这一重要事实,因而长期以来苯并三唑紫外线吸收剂一直是该领域的主要依靠。遣憾的是,这种化合物在甲苯或二甲苯中的溶解度是有限的(约14%重量),并且不溶于更有益于环境的溶剂中。这一点已成为一种严重的限制,因为由于关系到环境,芳族溶剂即将被淘汰。另外,这种化合物的溶解度甚至在芳族溶剂中也是相对较低的,使得加入涂层体系中的苯并三唑紫外线吸收剂的总浓度受到限制。由于汽车面漆要求有加倍长的有效期,于是这种苯并三唑的低溶解度就成为真正的障碍。
幸而存在着可溶的并且可热稳定的苯并三唑紫外线吸收剂,尤其是2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑的新结晶转变体,它具有与2-[2-羟基-3,5-二(α-枯基)苯基]-2H-苯并三唑同样的低挥发度和优秀的光稳定效果,但它可溶于对环境有益的溶剂中,并能以足够高的浓度加入汽车面漆中,以满足这种面漆要求的新的、延长的有效期。这点在实施例中有所说明。
这些有益于环境的溶剂如乙酸乙酯、乙酸异丙酯、乙酸丁酯、乙酸异丁酯、乙酸戊酯、乙酸丙酯、氧代乙酸己酯、氧代乙酸辛酯、丙二醇单甲醚、二丙二醇单甲醚、丙二醇单、甲醚乙酸酯、二丙二醇单甲醚乙酸酯、丙二醇苯基醚、丙二醇正丙醚、丙二醇叔丁醚、正丙酸戊酯、二异丁酮、环己酮、甲基异戊基酮、甲基戊基酮、二异戊基酮、甲基己基酮、乙醇、2-乙基己醇、双丙酮醇、乙基戊基醇、丙醇、异丁醇、异三癸醇、丁氧基乙氧基丙醇、异丁酸异丁酯、戊二酸二甲酯、乙酸3-甲氧基正丁酯、丙酸正戊酯。
本发明的组合物也涉及一种另外含有有效稳定量的三-芳基-S-三嗪、位阻胺或苯并呋喃-2-单光稳定剂或其混合物的组合物。
这种组合物最好另外含有有效稳定量的2,4-双-(2,4-二甲基苯基)-6-(2-羟基-4-辛氧基苯基)-S-三嗪、2,4-双-(2,4-二甲基苯基)-6-(2-羟基-4-〔3-(十五烷氧基)-2-羟基丙氧基〕-S-三嗪、双-(1-辛氧基-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、N-1,2,2,6,6-五甲基哌啶-4-基-正十二烷基琥珀酰亚胺或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。
这种涂层体系中经稳定化处理的有机材料是聚合物膜,如丙烯酸蜜胺树脂、聚酯蜜胺树脂、丙烯酸/聚氨酯树脂、聚酯/聚氨酯树脂、环氧/酸树脂或硅氧烷改性的丙烯酸树脂。
本发明涉及一种聚合物膜组合物,包含(a)附着于金属基底上的电泳底涂层,(b)附着于电泳涂层上的底涂层或彩色涂层,该涂层含有成膜粘合剂及有机或无机颜料或其混合物,(c)附着于底涂层上的清漆涂层,该涂层含有成膜粘合剂,以及(d)涂层中含有占成膜粘合剂重量1-20%的苯并三唑,它是至少一种式1的苯并三唑紫外线吸收剂,其中R1是氢或氯,
R2是具有4-28个碳原子的烷基或是CmH2mCOOR4,
其中m为1-4,R4为氢或具有1-18个碳原子的烷基,以及
R3是α-枯基,它可存在于底涂层中或清漆涂层中,或同时存在于底涂层和清漆涂层中,好是存在于清漆涂层中。
优选的情况是:R1是氢,R2为具有8-12个碳原子的烷基或CmH2mCOOR4,其中m为2,R4为具有1-12个碳原子的烷基,以及R3是α-枯基。
更优选的情况是:R1为氢,R2为叔-辛基、壬基或十二烷基,以及R3为α-枯基;特别优选的是:R1为氢,R2为叔-辛基,以及R3为α-枯基。
具有1-18个碳原子的烷基如甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十六烷基和十八烷基,以及相应的支化异构体。
上述聚合物膜组合物中,还可在电泳底涂层和底涂层或彩色涂层之间包含一附加层,该附加层包括(ⅰ)成膜粘合剂及有机或无机颜料或其混合物,以及(ⅱ)至少一种式1的可溶并可热稳定的苯并三唑紫外线吸收剂。此外,该附加层还可含有有效稳定量的位阻胺光稳定剂。
本发明中能被稳定而不受光和潮气影响的涂料的例子是特别适用于涂覆汽车(作为汽车面漆)的普通醇酸树脂烘干型漆,例如基于醇酸/蜜胺树脂和醇酸/丙烯酸/蜜胺树脂的漆(见H.Wagner和H.F.Sarx编写的“Lackkunstharze”(1977),99-123页)。另外交联剂包括甘脲树脂、封端异氰酸酯或环氧树脂。
本发明中被稳定的漆既适于作为金属光泽面漆,又适于作为非金属光泽面漆,尤其适于作为修饰性面漆,还可用作各种卷材涂料。本发明中被稳定的漆优选按两种常规方法涂布:单涂层法或二道涂层法。后一方法中,先涂覆含颜料的底涂层,再在其上涂覆清漆罩面涂层。
还应当注意的是,本发明的涂料有可能是非酸催化的热固性树脂,如环氧-聚酯树脂、乙烯基树脂、醇酸树脂、丙烯酸树脂和聚酯树脂,并可选择性地用硅氧烷、异氰酸酯或异氰脲酸酯改性。环氧树脂和环氧-聚酯树脂交联时可用常规交联剂,如酸、酸酐、胺及类似物。相应地,经改性后主链结构上存在活性基团的各种丙烯酸树脂体系或聚酯树脂体系也可用环氧化合物作为其交联剂。
当本发明的化合物用于二道涂层表面涂料时,可将其加入清漆涂层中,或同时加入清漆涂层和颜料底涂层中。
为获得最大的光稳定效果,同时使用其它常规光稳定剂是有益的。这种稳定剂如二苯酮类、苯并三唑类、腈基丙烯酸酯类或N,N'-草酰二苯胺类的紫外线吸收剂,或是含金属的光稳定剂如有机镍化合物,或是位阻胺光稳定剂。在二道涂层体系中,这些附加的光稳定剂可加入清漆层中,或同时加入清漆涂层和颜料底涂层中。
通常,本发明化合物的用量约占成膜粘合剂重量的1-20%。有益的范围是1-5%,优选1.5-5%。
所得的本发明的稳定组合物中还可选择性地含有约0.01-5%重量,优选约0.025-2%重量,更优选约0.1-1%重量的各种常规添加剂,如以下列出的材料或其混合物。
特别有价值的还有那些含有附加紫外线吸收剂的组合物,附加的紫外线吸收剂选自二苯酮、苯并三唑、腈基丙烯酸衍生物、羟基芳基-S-三嗪、有机镍化合物和草酰二苯胺。
优选的紫外线吸收剂选自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-3,5-二-叔-戊基苯基)-2H-苯并三唑、2-〔2-羟基-3-叔-丁基-5-(ω-羟基-八(乙烯氧基)羰基)乙基苯基〕-2H-苯并三唑、2-〔2-羟基-3-叔-丁基-5-(2-辛氧基羰基乙基)苯基〕-2H-苯并三唑、4,4'-二辛氧基-草酰二苯胺、2,2'-二辛氧基-5,5'-二-叔-丁基-草酰二苯胺、2,2'-双十二烷氧基-5,5'-二-叔-丁基-N,N'-草酰二苯胺、2-乙氧基-2'-乙基-草酰二苯胺、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-(2,4-二羟基苯基)-S-三嗪、2,6-双(2,4-二甲基苯基)-6-(4-氯苯基)-S-三嗪、2,6-双(2,4-二甲基苯基)-4-〔2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基〕-S-三嗪和2,2'-二羟基-4,4'-二甲氧基二苯酮。
有价值的还有那些另含有效稳定量苯酚抗氧剂的组合物,那些另含受阻胺衍生物的组合物,或那些另含亚磷酸酯或膦酸酯稳定剂的组合物。
特别有价值的还包括那些其有机材料为高固含量磁漆,用作工业用面漆的组合物,那些用作卷材涂料的组合物,那些用作渗透性木材面漆的组合物,或那些用作成膜木材面漆的组合物。
当本发明的化合物还含有反应性官能团时,该化合物就能通过缩合反应或自由基加成反应与聚合物基底化学键合。由此得到了非色移性、不可升华的紫外线吸收剂。这种反应性官能团包括羟基、羧基和烯属不饱合体部分。
所得的本发明的稳定聚合物组合物中还可选择性地含有约0.01-5%重量,优选约0.025-2%重量,更优选约0.1-1%重量的各种常规添加剂,如以下列出的材料或其混合物。1.抗氧剂1.1烷基化一元酚,如:2,6-二-叔-丁基-4-甲基酚、2-叔-丁基-4,6-二甲基酚、2,6-二-叔-丁基-4-乙基酚、2,6-二-叔-丁基-4-正丁基酚、2,6-二-叔-丁基-4-异丁基酚、2,6-二-环戊基-4-甲基酚、2-(α-甲基环己基)-4,6-二甲基酚、2,6-二-十八烷基-4-甲基酚、2,4,6-三-环己基酚、2,6-二-叔-丁基-4-甲氧基甲基酚。1.2烷基化氢醌,如:2,6-二-叔-丁基-4-甲氧基酚、2,5-二-叔-丁基-氢醌、2,5-二-叔-戊基氢醌、2,6-二苯基-4-十八烷氧基酚。1.3羟基化硫代二苯基醚,如:2,2'-硫代-双-(6-叔-丁基-4-甲基酚)、2,2'-硫代-双-(4-辛基酚)、4,4'-硫代-双-(6-叔-丁基-3-甲基酚)、4,4'-硫代-双-(6-叔-丁基-2-甲基酚)。1.4亚烷基化-双酚,如:2,2'-亚甲基-双-(6-叔-丁基-4-甲基酚)、2,2'-亚甲基-双-(6-叔-丁基-4-乙基酚)、2,2'-亚甲基-双-〔4-甲基-6-(α-甲基环己基)-酚〕、2,2'-亚甲基-双-(4-甲基-6-环己基酚)、2,2'-亚甲基-双-(6-壬基-4-甲基酚)、2,2'-亚甲基-双-〔6-(α-甲基苄基)-4-壬基酚〕、2,2'-亚甲基-双-〔6-(α,α-二甲基苄基)-4-壬基酚〕、2,2'-亚甲基-双-(4,6-二-叔-丁基酚)、2,2'-亚乙基-双-(4,6-二-叔-丁基酚)、2,2'-亚乙基-双-(6-叔-丁基-4-异丁基酚)、4,4'-亚甲基-双-(2,6-二-叔-丁基酚)、4,4'-亚甲基-双-(6-叔-丁基-2-甲基酚)、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-甲基酚、1,1,3-三-(5-叔-丁基-4-羟基-2-甲基酚)-、1,1-双-(5-叔-丁基-4-羟基-2-甲基酚)-3-正十二烷基巯基丁烷、乙二醇双-〔3,3-双(3'-叔-下基-4-羟基苯基)-丁酸酯〕、二-(3-叔-丁基-4-羟基-5-甲基苯基)-二环戊二烯、二-〔2-(3'-叔-丁基-2'-羟基-5'-甲基-苄基)-6-叔-丁基-4-甲基苯基〕对苯二酸酯。1.5苄基化合物,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)硫化物、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-2,6-二甲基苄基)二硫酚对苯二酸酯、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-2,6-二甲基苄基)-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-磷酸单乙酯、钙盐。1.6酰氨基酚,如:4-羟基-月桂酸-N-酰苯胺、4-羟基-硬脂酸-N-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、辛基-N-(3,5-二-叔-丁基-4-羟基苯基)-氨基甲酸酯。1.7β-(3,5-二-叔-丁基-4-羟基苯基)-丙酸与一元醇或多元醇的酯,这类醇如:甲醇 二乙二醇十八醇 三乙二醇1,6-己二醇 季戊四醇新戊二醇 三-羟乙基异氰脲酸酯硫代二乙二醇 二-羟乙基草酸二酰胺1.8β-(5-叔-丁基-4-羟基-3-甲基苯基)-丙酸与一元醇或多元醇的酯,这类醇如:甲醇 二乙二醇十八醇 三乙二醇1,6-己二醇 季戊四醇新戊二醇 三-羟乙基异氰脲酸酯硫代二乙二醇 二-羟乙基草酸二酰胺1.9β-(3,5-二-叔-丁基-4-羟基苯基)-丙酸的酰胺,如:N,N'-二-(3,5-二-叔-丁基-4-羟基苯基丙酰基)-亚己基二胺、N,N'-二-(3,5-二-叔-丁基-4-羟基苯基丙酰基)-亚丙基二胺、N,N'-二-(3,5-二-叔-丁基-4-羟基苯基丙酰基)-肼。2.紫外线吸收剂和光稳定剂2.1 2-(2'-羟基苯基)-苯并三唑,如带以下基团的2-(2'-羟基苯基)-苯并三唑: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-、3'-叔-丁基-5'-(2-辛氧基羰基)乙基-和十二烷基化-5'-甲基衍生物。2.2 2-羟基-二苯酮。如带以下基团的2-羟基-二苯酮: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可选择性地被取代的苯甲酸的酯,如苯基水杨酸酯、4-叔-丁基苯基水杨酸酯、辛基苯基水杨酸酯、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,如α-氰基-β,β-二苯基丙烯酸乙酯或异辛酯、α-羰甲氧基-肉桂酸甲酯、α-氰基-β-甲基-对-甲氧基-肉桂酸甲酯或丁酯、α-羰甲氧基-对-甲氧基-肉桂酸甲酯、N-(β-羰甲氧基-β-氰基乙烯基)-2-甲基-二氢吲哚。2.5镍化合物,如:镍与2,2'-硫代-双-〔4-(1,1,3,3-四甲基丁基)-酚〕络合,如络合比为1∶1或1∶2,可选择性地带有附加配位体如正丁胺、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-丁基苄基磷酸单烷基酯(如甲酯、乙酯或丁酯)的镍盐,又如镍与酮肟(如2-羟基-4-甲基苯基十一烷基酮肟)络合,再如镍与1-苯基-4-月桂酰-5-羟基-吡唑络合,可选择性地带有附加配位体。2.6位阻胺,如双-(2,2,6,6-四甲基哌啶基)癸二酸酯、双-(1,2,2,6,6-五甲基哌啶基)癸二酸酯、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-羟基哌啶与琥珀酸的缩合产物、N,N'-(2,2,6,6-四甲基哌啶基)-六亚甲基二胺与4-叔-辛基氨基-2,6-二氯-S-三嗪的缩合产物、三-(2,2,6,6-四甲基哌啶基)-次氮基三乙酸酯、四-(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四甲酸酯、1,1'(1,2-乙烷二基)-双-(3,3,5,5-四甲基哌嗪酮。2.7草酸二酰胺,如4,4'-二-辛氧基-草酰二苯胺、2,2'-二-辛氧基-5,5'-二-叔-丁基-草酰二苯胺、2,2'-二-十二烷氧基-5,5'-二-叔-丁基-草酰二苯胺、2-乙氧基-2'-乙基-草酰二苯胺、N,N'-双(3-二甲基氨基丙基)-草酰胺、2-乙氧基-5-叔-丁基-2'-乙基草酰二苯胺以及它与2-乙氧基-2'-乙基-5,4'-二-叔-丁基草酰二苯胺的混合物,以及邻位-草酰二苯胺、对位-甲氧基草酰二苯胺和邻、对位双取代的草酰二苯胺的混合物。2.8羟基苯基-S-三嗪,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-(2,4-二羟基苯基)-S-三嗪、2,4-双-(2,4-二-羟基苯基)-6-(4-氯苯基)-S-三嗪、2,4-双〔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-乙酸基乙氧基)苯基〕-6-(4-氯苯基)-S-三嗪、2,4-双-(2,4-二-羟基苯基)-6-(2,4-二甲基苯基)-S-三嗪、2,4-双-(2,4-二甲基苯基)-6-{2-羟基-4-〔3-(2-乙基己氧基)-2-羟基丙氧基〕苯基}-S-三嗪、2,4-双-(2,4-二甲基苯基)-6-{2-羟基-4-〔3-(十五烷氧基)-2-羟基丙氧基〕苯基}-S-三嗪。3.金属减活剂,如N,N'-二苯基草酸二酰胺、N-水杨醛-N'-水杨酰肼、N,N'-双-水杨酰肼、N,N'-双-(3,5-二-叔-丁基-4-羟基苯基丙酰基)-肼、3-水杨酰氨基-1,2,4-三唑、双-亚苄基-草酸二酰肼。4.亚磷酸酯或膦酸酯,如三苯基亚磷酸酯、二苯基烷基亚磷酸酯、苯基二烷基亚磷酸酯、三-(壬基苯基)亚磷酸酯、三月桂基亚磷酸酯、三-十八烷基亚磷酸酯、二-硬脂酰-季戊四醇二亚磷酸酯、三-(2,4-二-叔-丁基苯基)亚磷酸酯、二-异癸基季戊四醇二亚磷酸酯、二-(2,4-二-叔-丁基苯基)季戊四醇二亚磷酸酯、三硬脂酰-山梨醇三亚磷酸酯、四-(2,4-二-叔-丁基苯基)-4,4'-二亚苯基二膦酸酯。5.破坏过氧化物的化合物,如β-硫代二丙酸的酯,如它的月桂基酯、硬脂酰酯、肉豆寇酯或十三烷基酯,巯基-苯并咪唑或2-巯基-苯并咪唑的锌盐,二丁基-二硫代氨基甲酸锌、双十八烷基二硫化物,季戊四醇四-(β-十二巯基)-丙酸酯。6.羟基胺,如N,N-二苄基羟基胺、N,N-二乙基羟基胺、N,N-二辛基羟基胺、N,N-二月桂基羟基胺、N,N-双十四烷基羟基胺、N,N-双十六烷基羟基胺、N,N-双十八烷基羟基胺、N-十六烷基-N-十八烷基羟基胺、N-十七烷基-N-十八烷基羟基胺、由氢化脂胺衍生的N,N-双烷基羟基胺。7.硝酮,如N-苄基-α-苯基硝酮、N-乙基-α-甲基硝酮、N-辛基-α-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、由氢化脂胺衍生的N,N-双烷基羟基胺得到的硝酮。8.聚酰胺稳定剂,如铜盐配合有碘化物和/或磷化合物以及二价锰盐。9.碱性共稳定剂,如三聚氰胺、聚乙烯吡咯烷酮、二氰基二酰胺、三烯丙基氰尿酸酯、脲衍生物、肼衍生物、胺、聚酰胺、聚氨酯、高级脂肪酸的碱金属盐或碱土金属盐如硬脂酸钙、硬脂酸锌、硬脂酸镁、蓖麻酸钠和棕榈酸钾、邻苯二酚酸锑或邻苯二酚酸锌。10.成核剂,如4-叔-丁基-苯甲酸、己二酸、二苯基乙酸。11.填料及增强剂,如碳酸钙、硅酸盐、玻璃纤维、石棉、滑石、高岭土、云母、硫酸钡、金属氧化物及金属氢氧化物、碳黑、石墨。12.其它添加剂,如增塑剂、润滑剂、乳化剂、颜料、荧光增白剂、阻燃剂、抗静电剂、发泡剂以及硫代增效剂如二月桂基硫代二丙酸酯或二硬脂酰硫代二丙酸酯。
特别有价值的苯酚抗氧剂选自:正十八烷基-3,5-二-叔-丁基-4-羟基氢化肉桂酸酯、新戊烷四基四(3,5-二-叔-丁基-4-羟基氢化肉桂酸酯、二-正十八烷基-3,5-二-叔-丁基-4-羟基苄基膦酸酯、1,3,5-三(3,5-二-叔-丁基-4-羟基苄基)异氰脲酸酯、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、3,6-二噁亚辛基双(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'-亚乙基-双(4,6-二-叔-丁基酚)、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-叔-丁基-4-羟基苄基)酚、亚己基双(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(辛基硫代)-S-三嗪、N,N'-亚己基-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-羟基苯基)丁酸酯〕、辛基3,5-二-叔-丁基-4-羟基苄基巯基乙酸酯、双(3,5-二-叔-丁基-4-羟基氢化肉桂酰基)酰肼以及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。
更优选的苯酚抗氧剂是新戊烷四基四(3,5-二-叔-丁基-4-羟基氢化肉桂酸酯)、正十八烷基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、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-甲酚或2,2'-亚乙基-双(4,6-二-叔-丁基酚)。
特别有价值的位阻胺化合物选自: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、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-螺〔4.5〕癸烷-2,4-二酮、三(2,2,6,6-四甲基哌啶-4-基)次氮基三乙酸酯、1,2-双(2,2,6,6-四甲基-3-氧基哌嗪-4-基)乙烷、2,2,4,4-四甲基-7-噁-3,20-二氮-21-氧基二螺〔5.1.11.2〕二十一烷、2,4-二氯-6-叔-辛基氨基-S-三嗪与4,4'-亚己基双(氨基-2,2,6,6-四甲基哌啶)的缩合产物、1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩合产物、4,4'-亚己基双(氨基-2,2,6,6-四甲基哌啶)与1,2-二溴乙烷的缩合产物、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-三嗪与4,4'-亚己基双(氨基-2,2,6,6-四甲基哌啶)的缩合产物、N,N',N″,N-四〔(4,6-双(丁基-2,2,6,6-四甲基-哌啶-4-基)-氨基-S-三嗪-2-基〕-1,10-二氨基-4,7-二氮癸烷、混合〔2,2,6,6-四甲基哌啶-4-基/β,β,β',β'-四甲基-3,9-(2,4,8,10-四噁螺〔5.5〕-十一烷)二乙基〕1,2,3,4-丁烷四羧酸酯、混合〔1,2,2,6,6-五甲基哌啶-4-基/β,β,β',β'-四甲基-3,9-(2,4,8,10-四噁螺〔5.5〕-十一烷)二乙基〕1,2,3,4-丁烷四羧酸酯、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-1,3,8-三氮螺〔4.5〕癸烷-2,4-二酮、二-(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯、二-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯、1-辛氧基-2,2,6,6-四甲基-4-羟基-哌啶、多-{〔6-叔-辛基氨基-S-三嗪-2,4-二基〕〔2-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基-亚己基-〔4-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基〕、2,4,6-三〔N-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基〕-S-三嗪、2,4-双〔N-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基〕-6-〔二-(2-羟乙基)氨基〕-S-三嗪以及2,4-双〔N-(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基〕-6-〔二-(2-羟乙基)氨基〕-S-三嗪。
更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-羟基哌啶与琥珀酸的缩合产物、2,4-二氯-6-叔-辛基氨基-S-三嗪与4,4 一亚己基双(氨基-2,2,6,6-四甲基哌啶)的缩合产物、N,N',N″,N-四〔(4,6-双(丁基-(2,2,6,6-四甲基-哌啶-4-基)氨基)-S-三嗪-2-基〕-1,10-二氨基-4,7-二氮癸烷、二-(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯、二-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯、1-辛氧基-2,2,6,6-四甲基-4-羟基-哌啶、多-{〔6-叔-辛基氨基-S-三嗪-2,4-二基〕〔2-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基-亚己基-〔4-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基〕或2,4,6-三〔N-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基〕-S-三嗪。
本发明的苯并三唑可以按常规的并且公知的方法制备。制备例1-9中举出了这种方法的例子。特别优选的2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑结晶转变体的熔点为109-111℃,其X-射线衍射花样(由Cu-Ka-幅射得到)呈现出以下衍射角(2θ):
结晶转变体可以如此得到:将所述化合物溶于芳族溶剂中,再加入低级链烷醇使之沉淀;或者使这种化合物仅从低级链烷醇中、或从结合有少量芳族溶剂的低级链烷醇中结晶或再结晶。
峰编号 | 2 | 峰编号 | 2 | 峰编号 | 2 | 峰编号 | 2 |
1 | 9.6 | 2 | 10.2 | 3 | 10.4 | 4 | 10.8 |
5 | 12.8 | 6 | 13.8 | 7 | 14.2 | 8 | 14.8 |
9 | 15.0 | 10 | 16.4 | 11 | 16.8 | 12 | 17.8 |
13 | 18.0 | 14 | 18.6 | 15 | 19.0 | 16 | 19.4 |
17 | 19.8 | 18 | 20.2 | 19 | 20.6 | 20 | 21.2 |
21 | 21.4 | 22 | 23.0 | 23 | 23.4 | 24 | 24.6 |
25 | 26.0 | 26 | 28.0 | 27 | 29.0 | 28 | 30.4 |
29 | 31.0 |
优选的方法包括将所述化合物从具有1-4个碳原子的链烷醇中结晶或再结晶,或者从结合有少量芳族溶剂的这种链烷醇中结晶或再结晶。
可用于以上方法中的芳族溶剂如甲苯或二甲苯。微量使用时其用量最高可达所用溶剂总体积的15%,或最好为5-15%。
可用于该方法中的链烷醇如甲醇、乙醇、正丙醇、异丙醇、1-丁醇、仲-丁醇或异丁醇。优选的链烷醇是具有2,3或4个碳原子的链烷醇,更优选的是异丙醇或1-丁醇。
本发明的另一方面就是本发明中式1的化合物在记录材料上的应用。本发明的记录材料适用于压敏复制系统、使用微胶囊的照相复制系统、热敏复制系统、照相材料及喷墨印刷中。
本发明的记录材料的特点在于该材料的质量有出乎意料的提高,尤其是在耐光性方面的提高。
本发明记录材料的结构是用于特定用途时的已知结构。由一般的载体组成,如涂有一道或多道涂层的纸或塑料薄膜。根据材料的类型,这些涂层中含有适当的必要成分,就照像材料来说,可含有如卤化银乳液、染料偶联剂、染料及类似物。特别适于喷墨印刷的材料在一般载体上有一层对油墨吸收性特别强的涂层。未涂覆的纸也可用于喷墨印刷。这种情况下,纸既作为载体材料,又作为油墨吸收层。适用于喷墨印刷的材料如美国专利5,073,448中所述(引入此处供参考)。
记录材料也可以是透明的,如投影薄膜。
式1的化合物可以早在载体材料制备时就加入载体材料中,例如,在纸的制备过程中将其加入纸浆中。第二种用法是用式1化合物的水溶液喷涂载体材料,或将式1的化合物加入涂料组合物中。
适用于投影的透明记录材料所用的涂料组合物不能含有任何散射光的粒子,如颜料和填料。
染料-粘合涂料组合物可以含有一定量的其它添加剂,如抗氧剂、光稳定剂(也包含不属于本发明紫外线吸收剂的其它紫外线吸收剂)、粘度改进剂、荧光增白剂、生物杀伤剂和/或抗静电剂。
涂料组合物通常是如此制备的:将水溶性组分如粘合剂溶于水中,并一起搅拌。将固体组分如上述填料和其它添加剂分散于这种水性介质中。分散过程通过以下装置很好地进行,如超生波装置、叶轮搅拌器、均化器、胶体磨、珠磨机、砂磨机、高速搅拌器及类似物。式1化合物的一个特别的优点在于它能很容易地混入涂料组合物中。
本发明的记录材料中式1化合物的含量优选为1-5000mg/m2,特别优选的是50-1200mg/m2。
如前所述,本发明的记录材料包含了很宽的应用领域。式1的化合物可用于如压敏复制系统中。可将该化合物掺入纸中,以保护纸中微囊包封的染料前体不受光的损害,或将该化合物掺入显影剂层的粘合剂中,保护在该处成色的染料。
U.S.4,416,966、US4,483,912、US4,352,200、US4,535,050、US4,5365,463、US4,551,407、US4,562,137和US4,608,330中,以及EP-A139,479、EP-A162,664、EP-A164,931、EP-A237,024、EP-A237,025或EP-A260,129中公开了使用光敏微胶囊的照相复制系统,这种微胶囊受压后显影。在所有这些系统中,式1的化合物可以掺入染料接收层中。但也可将式1的化合物掺入供体层中,以保护成色剂不受光的损害。
可被稳定的照相材料是照相染料和含有这种染料或其前体的涂层,如相纸及照相软片。适用的材料如公开于美国专利5,364,749中的材料(引入此处供参考)。这里,式1的化合物起了过滤紫外线的作用,以防止静电闪光的损害。在彩色照相材料中,还能保护偶联剂和染料不被光化分解。
式1的化合物可用于所有种类的彩色照相材料中。如可用于彩色相纸、彩色反转相纸、直接正像彩色材料、彩色底片、彩色正片、彩色反转片等。尤其优选地用于含有反转基底或形成正像的彩色照相材料中。
彩色照相记录材料通常在载体上含有感受蓝光和/或绿光和/或红光的卤化银乳液层,如需要,还可含一层保护层,式1的化合物最好处于感绿光层中或感红光层中,或处于感绿光层与感红光层之间的一层中,或处于卤化银乳液层顶部的一层中。
式1的化合物可根据光聚合、光增塑或微胶囊破裂的原理用于记录材料中,或在使用了热敏和光敏重氮盐、带氧化剂的无色染料或带路易斯酸的染料内酯的情况下,将式1化合物用于记录材料中。
此外,式1的化合物还可用于染料扩散转移印刷、热蜡转移印刷和点阵印刷所用的记录材料中,并可用于静电印刷机、电记录印刷机、电泳印刷机、磁记录印刷机和激光电照相印刷机中。以上用途中,用于染料扩散转移印刷所用的记录材料中是优选的,如EP-A507,734中公开的。
式1的化合物也可用于油墨中,优选用于喷墨印刷的油墨中,如美国专利5,098,477所公开的(引入此处供参考)。因此,本发明的另一个主题是含有至少一种式1化合物作为其稳定剂的油墨。这种油墨中、特别是用于喷墨印刷的油墨中最好含有水。油墨中式1的稳定剂的浓度最好为0.01-20%重量份,特别优选的是0.5-10%重量份。
X射线衍射花样记录在Philips Norelco X射线衍射仪上,是用带有镍过滤器的Cu-Ka幅射得到的。所有样品都具有40-75微米的均匀粒径。这种粒径分布与实施例2中的已知化合物的粒径分布是相同的。以下实施例仅用于解释本发明,而不会以任何一种方式限定本发明的种类或范围。
制备实施例1-9:实施例1:2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑
向一个装有搅拌器、温度计、回流冷凝器及入氮气口的5升三颈烧瓶中加入380g(0.8mol)2-硝基-2'-羟基-3'-α,α-二甲基苄基-5'-叔-辛基偶氮苯和1200ml甲苯。向所得溶液中加入240ml异丙醇和240ml水。充入氮气并加入160ml 50.1%的氢氧化钠水溶液。将一个装有158.2g(2.42克原子)锌的烧瓶连接到反应烧瓶上,在90分钟内将锌粉分批加入反应混合物中。加锌过程中瓶内温度保持在40-45℃之间,加完后再保持1小时,然后将该混合物在70℃下加热3小时。将混合物冷却至室温并用600ml浓盐酸酸化。通过过滤将锌渣除去。产物存在于有机层中,将该有机层用4份340ml稀盐酸洗涤,再经无水硫酸钠干燥。在真空下除去有机溶液以得到一种粘浆状粗制品。
将300g粗制品样品溶于300ml二甲苯中。再在搅拌下向该溶液中加入600ml乙醇以产生254g式1化合物的可溶性新结晶转变体,其熔点为109-111℃,而且在薄层色谱法中仅显示一种色谱斑。分析:
C29H35N3O理论值:C,78.9 H,8.0 N,9.5
测得值:C,78.7 H,8.1 N,9.6
这种产物的X射线衍射花样(由Cu-Ka幅射得到)显示出以下的衍射角(2θ):
实施例2:非晶态2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑
峰编号 | 2 | 峰编号 | 2 | 峰编号 | 2 | 峰编号 | 2 |
1 | 9.6 | 2 | 10.2 | 3 | 10.4 | 4 | 10.8 |
5 | 12.8 | 6 | 13.8 | 7 | 14.2 | 8 | 14.8 |
9 | 15.0 | 10 | 16.4 | 11 | 16.8 | 12 | 17.8 |
13 | 18.0 | 14 | 18.6 | 15 | 19.0 | 16 | 19.4 |
17 | 19.8 | 18 | 20.2 | 19 | 20.6 | 20 | 21.2 |
21 | 21.4 | 22 | 23.0 | 23 | 23.4 | 24 | 24.6 |
25 | 26.0 | 26 | 28.0 | 27 | 29.0 | 28 | 30.4 |
29 | 31.0 |
将实施例1制备的化合物加热到熔点后再凝固。所得的非晶态材料的熔点为59-74℃。薄层色谱法中显示出一种与实施例1的制品相同的色谱斑。
X射线衍射显示出无特征的花样,证实了此实施例中得到的化合物是非晶性的。实施例3:2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑
标题中的化合物可按实施例1中的一般方法制成一种琥珀色树脂,但对相应的邻-硝基偶氮苯中间体的还原用的是催化氢化法。分析:
C30H37N3O理论值:C,79.1 H,8.2 N,9.2
测得值:C,79.5 H,8.5 N,9.0实施例4:2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑
标题中的化合物由用于实施例1中的邻-硝基偶氮苯化合物经催化氢化制成一种近白色固体。将100g上述固体样品从100ml异丙醇中再结晶,再从100ml异丙醇:甲苯为19∶1的混合液中再结晶,最后从100ml异丙醇:甲苯为9∶1的混合液中再结晶,以产生78g标题中的化合物,其溶点为109-111℃,与实施例1制备的化合物有同样的结晶转变体和同样的X射线衍射花样。实施例5:2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑
标题中的化合物可按实施例1中的一般方法制成一种琥珀色树脂。实施例6:2-(2-羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑
标题中的化合物可按实施例1中的一般方法制成一种琥珀色树脂。
在CDCl3中的H-NMR数据〔ppm〕:0.8-0.9三线组,1.3-1.42单线组,1.9单线组,7.14-7.30复线组,7.44复线组,7.48-7.64偏双线组,7.86复线组,8.20-8.34偏双线组,11.38-11.46单线组,此数据符合标题化合物。实施例7:2-(2-羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑
标题中的化合物可按实施例1中的一般方法制成一种琥珀色树脂,但对相应的邻-硝基偶氮苯化合物的还原用的是催化氢化法。
实施例8和9:
为了将紫外线吸收稳定剂混入高固含量的热固性丙烯酸树脂中,必须将紫外线吸收剂溶于适当的有机溶剂中。至今,这类溶剂如芳烃溶剂、甲苯或二甲苯,能够充分地溶解这种紫外线吸收剂,甚至是溶解性很低的2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑。
由于环境原因,这类芳烃溶剂有可能被淘汰,涂料趋向于高固含量化,而且汽车工业中对汽车漆的需求量也日益增加,且这种状况还将持续近10年,因此意味着需要一种易溶的、不挥发的、但同样有效的紫外线吸收剂。此外,这种紫外线吸收剂必须能溶于有益于环境的溶剂中。
按以下方法测定了五种不同的苯并三唑紫外线吸收剂在七种典型有机溶剂中的相对溶解度:将紫外线吸收剂溶于50-100ml的七种不同溶剂中,直至溶液达到过饱合。看到苯并三唑开始沉淀入实验瓶底时就达到了过饱合。将过饱合溶液在不受干扰的情况下保持一夜。然后,将顶层滗去并过滤。所得滤液中含有溶于有机溶剂中的苯并三唑,将该滤液分为三份,用ASTM测试法D2369-81测试其固体百分含量。测得的固体百分含量越高,就说明滤解的苯并三唑越多。结果见下列。*A是2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑(用于对比)
B是实施例4的化合物
C是实施例3的化合物
D是实施例7的化合物
EXXATE600是Exxon的醋酸己酯
PM乙酸酯是1-甲氧基-2-丙基乙酸酯
PM溶剂是1-甲氧基-2-丙醇
二甲苯目前是被调整的溶剂,并被列入HAP'S溶剂(危险的空气污染物)。因此,用二甲苯作为各类涂料的溶剂很快将被淘汰,用适当的溶剂取代它将成为不可避免的。
其它列于上表中的溶剂目前还不是调整和撤换的对象,并且在涂料工业中变得更加通用。
涂料工业的近期趋向是高固含量涂料,这意味着甚至以更少的溶剂溶解紫外线吸收剂。因而对更易溶、不挥发性紫外线吸收剂的需求就更明显了。
对表中数据的研究显示,紫外线吸收剂A在每一种溶剂中的溶解量都比紫外线吸收剂B-D的少。实际上,紫外线吸收剂A在除二甲苯外的所有溶剂中的溶解度基本上使它不能在新一时期的汽车漆中作为有用的稳定剂。
紫外线吸收剂B-D也具有紫外线吸收剂A显示的不挥发性。结合了这种性能,使紫外线吸收剂B-D首选用于长期发展的高固含量汽车涂料中。实施例11:
实施例2制备的2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑非晶形转变体,它在实施例10中出现的各种溶剂中的溶解度参数与实施例1-4中制备的2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑新结晶转变体的溶解度参数基本相同,只是非晶形的2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑能更容易且更快地溶于非HAPS溶剂中。这点是实施例2的非晶形化合物用于实际应用中时的明显优点。
实施例12:含有紫外线吸收剂的高固含量热固性丙烯酸清漆的保光性(该清漆直接涂覆于银白色金属底漆和电泳底漆之上)
涂覆样板是如此制备的:在4″×12″(10.16cm×30.48cm)的带有电泳底漆的UNIPRIMER样板(Advanced Coating Technology公司制造)上直接涂覆一层可商业购买的银白色金属底漆,再以湿碰湿的方法,在其上喷涂一层1.8-2.0密耳(0.072-0.102毫米)厚的涂膜,该涂膜是HAPS标准所允许的,含有2%重量份测试稳定剂的高固含量热固性丙烯酸密胺清漆。将涂覆的样板在250°F(121℃)下烘烤30分钟。然后将涂覆的样板按ASTM G26-90标准暴露于Ci-65老化试验机中(Atlas电装置)。每隔300小时测一次暴露样板的光泽度。光泽度越高,表示可溶的苯并三唑紫外线吸收剂对涂料的保护性越强。
式1的可溶性化合物赋予涂料良好的保光性。
实际上,由于可溶性苯并三唑能很方便地以更高的浓度混入涂料中,因此它赋予高固含量热固性丙烯酸涂料体系的保光性远远超过了由于受溶解度的限制而少量存在的苯并三唑所能达到的。
实施例13:含有紫外线吸收剂的高固含量热固性丙烯酸清漆的保光性(该清漆直接涂覆于银白色金属底漆和电泳底漆之上)
将实施例12制备的涂覆样板按ASTM G53标准暴露于QUV暴露装置中(Q Panel公司)。每隔300小时测量20°光泽度值,光泽度值越高说明对涂料的保护作用越强。
式1的可溶性化合物赋予涂料良好的保光性。
实际上,由于可溶性苯并三唑能很方便地以更高的浓度混入涂料中,因此它赋予高固含量热固性丙烯酸涂料体系的保光性远远超过了由于受溶解度的限制而少量存在的苯并三唑所能达到的。
实际上,用式1的可溶性苯并三唑紫外线吸收剂稳定的样板,处于QUV暴露装置内3000小时之后仍显示出至少50%的保光性。
实施例14:含有紫外线吸收剂的丙烯酸聚氨酯清漆的保光性(该清漆直接涂覆于银白色金属底漆和电泳底漆之上)
涂覆样板是如此制备的:在4″×12″(10.16cm×30.48cm)的带有电泳底漆的UNIPRIM样板(Advanced Coating Technology公司制造)上直接涂覆一层可商业购买的银白色金属底漆,再以湿碰湿的方法,在其上喷涂一层1.8-2.0密耳(0.036-0.051mm)厚的涂膜,该涂膜是HAPS标准所允许的,含有试验稳定剂的高固含量丙烯酸聚氨酯清漆。接着将涂覆的样板在250°F(121℃)下烘烤30分钟。然后将涂覆的样板按ASTM G26-90标准暴露于Ci-65老化试验机中(Atlas电装置)。每隔300小时测一次暴露样板的光泽度。光泽度越高,表示可溶性苯并三唑紫外线吸收剂对涂料的保护性越强。
式1的可溶性化合物赋予涂料良好的保光性。
实际上,由于可溶性苯并三唑能很方便地以更高的浓度混入涂料中,因此它赋予高固含量热固性丙烯酸涂料体系的保光性远远超过了由于受溶解度的限制而少量存在的苯并三唑所能达到的。
实施例15:含有紫外线吸收剂的丙烯酸聚氨酯清漆的保光性(该清漆直接涂覆于银白色金属底漆和电泳底漆之上)
将实施例14制备的涂覆样板按ASTM G53标准暴露于QUV暴露装置中(Q样板公司)。每隔300小时测量20°光泽度值,光泽度值越高说明对涂料的保护作用越强。
式1的可溶性化合物赋予涂料良好的保光性。
实际上,由于可溶性苯并三唑能很方便地以更高的浓度混入涂料中,因此它赋予高固含量热固性丙烯酸涂料体系的保光性远远超过了由于受溶解度的限制而少量存在的苯并三唑所能达到的。
实施例16:直接涂覆于石英载玻片上的高固含量热固性丙烯酸清漆的UVA保留值
涂覆的石英载玻片是如此制备的:向载玻片上喷涂一层0.9-1.0密耳(0.018-0.026mm)厚的涂膜,该涂膜是HAPS标准所允许的,含有试验紫外线吸收剂的高固含量热固性丙烯酸密胺清漆。然后将涂覆的石英载玻片在250°F(121℃)下烘烤30分钟。此后测得涂膜的光密度为345nm。
接着将涂覆的石英载玻片按ASTM G53标准暴露于QUV暴露装置中(Q Panel公司)。每隔1000小时再测量其光密度,光密度值越高说明对涂料的保护作用越强。
式1的可溶性化合物在每个间隔中都赋予涂料更高的光密度值。
实际上,由于可溶性苯并三唑能很方便地以更高的浓度混入涂料中,因此它赋予高固含量热固性丙烯酸涂料体系的UVA保留值远远超过了由于受溶解度的限制而少量存在的苯并三唑所能达到的。
实施例17:直接涂覆于石英载玻片上的高固含量热固性丙烯酸清漆的UVA保留值
涂覆的石英载玻片按实施例16中说明的方法制备。也按ASTM G-26-90标准将这些涂覆的石英载玻片暴露于Ci-65老化试验机中(Atlas电装置)。每隔1000小时测一次光密度,光密度值越高说明对涂料的保护作用越强。
式1的可溶性化合物在每个间隔中都赋予涂料更高的光密度值。
实际上,由于可溶性苯并三唑能很方便地以更高的浓度混入涂料中,因此它赋予高固含量热固性丙烯酸涂料体系的UVA保留值远远超过了由于受溶解度限制而少量存在的苯并三唑所能达到的。
实施例18:
将紫外线吸收剂(其用量列于下表中)溶于2ml乙酸乙酯中。将1ml该溶液与9ml水性凝胶溶液混合,该凝胶溶液含有27.6g/l的凝胶,以及6.8g/l作为湿润剂的8%的4,8-二异丁基萘-2-磺酸(钠盐)水溶液。将此混合物用超生波乳化3分钟。将7.5ml这种紫外线吸收剂乳液与4.5ml固化剂水溶液混合,固化剂水溶液中含有0.24%的2-羟基-4,6-二氯-S-三嗪,钾盐。将8ml这种乳液浇在聚酯基底上(13×18cm)。浇注件在室温下固化7天。此后用紫外线分光仪测得的最大密度值在330-380nm之间。然后将样品暴露于30、60、90和120KJ/cm2的Atlas暴露装置中,测量最大密度值,并计算出对应值之间的差值(△Din%)。△D值越小,紫外线吸收剂的稳定作用就越强。*A是2-(2-羟基-3-仲-丁基-5-叔-丁基苯基)-2H-苯并三唑(对比)B是2-(2-羟基-3-十二烷基-5-甲基苯基)-2H-苯并三唑(对比)C是2-(2-羟基-3,5-二-叔-戊基苯基)-2H-苯并三唑(对比)D是2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑(由实施例1制得)E是2-(2-羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑(由实施例7制得)
很明显,紫外线吸收剂A、B和C的光稳定性不如紫外线吸收剂D和E。
实施例19-21:使用以下化合物:A.2-(2-羟基-3-α-枯基-5-叔-辛基苯基)-2H-苯并三唑,实施例4的化合物B.2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑,实施例3的化合物C.2-(2-羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑,实施例7的化合物D.2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑,商业可购产品,如Ciba-Geigy公司的Tinuvin900(用作对比),以及E.双-(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯,商业可购产品,如Ciba-Geigy公司的Tinuvin123试验方法1:将60份丙烯酸多羟基化合与40份Resimene747(六甲氧基甲基三聚氰胺,Monsanto制造)以及酸催化剂和助流剂混合制成清漆。底漆是丙烯酸三聚氰胺,喷涂0.6密耳厚的这种黑色底漆。在该底漆还未干时就在其上喷涂上述清漆,以形成2密耳厚的清漆涂层。
底漆中不含紫外线吸收剂或位阻胺。清漆中加入了试验化合物紫外线吸收剂,使化合物D和化合物A的溶解度达到最大,该清漆中含有足够的醋酸丁酯溶剂,使清漆具有能进行喷涂的粘度。
为了对比的目的,还对未加稳定剂的配方以及含有3%或4%常规量化合物A、含或不含位阻胺的配方进行了试验。试验方法2:本试验使用了不含光稳定剂的银白色金属丙烯酸三聚氰胺底漆。
向使用醋酸丁酯溶剂(一种非HAPS溶剂)的标准高固含量热固性丙烯酸三聚氰胺树脂或丙烯酸聚氨酯树脂清漆中加入试验化合物A-D。19.标准高固含量热固性丙烯酸清漆/黑色底漆用试验方法1进行试验,接着将样品按下表中规定的时间暴露于QUV(FS40 bulbs)装置中,然后测量20°光泽保留值。*Ⅰ是未加稳定剂的空白试样Ⅱ含有4%重量份的化合物AⅢ含有3%重量份的化合物A加1%重量份的化合物EⅣ含有4%重量份的化合物A加1%重量份的化合物EⅤ含有2.27%重量份的化合物D,以及Ⅵ含有2.27%重量份的化合物D加1%重量份的化合物E**涂层在此点发生破裂a样品Ⅱ的值在3770小时之后仍为65
化合物A可溶于树脂的最大量为4%重量份,化合物D可溶于树脂的最大量为2.27%重量份。
从这些稳定剂单独使用或结合位阻胺稳定剂用于树脂体系时所得的20°光泽保留值数据来看,显然化合物A更易溶于树脂体系中,并且远远超过了在树脂体系中只有有限溶解度的已有技术的化合物D。
实际上,化合物A至少可对涂层提供3770小时的保护,而化合物D最多只能达到3162小时。化合物A达到约20°光泽保留值比化合物D的高20%。
化合物A与化合物D结合使用时,所达到的暴露4602小时后的光泽保留值也比化合物D与E结合所达到的高21%。20.将试验方法2用于标准高固含量热固性丙烯酸清漆涂层/黑色底涂层体系,将样品按下表规定的时间暴露于Xenon arc(CAM180)装置中,测量其60°和20°光泽保留值和成像差异。 *Ⅰ是未加稳定剂的空白样品Ⅱ含有0.24%重量份的化合物DⅢ含有1.2%重量份的化合物AⅣ含有3%重量份的化合物C,以及Ⅴ含有3%重量份的化合物B**涂层在此点发生破裂
该方法中,紫外线吸收剂溶解于非-HAPS溶剂的醋酸丁酯中,然后按涂料工业的常规做法将其加入树脂体系中。由于化合物D在醋酸丁酯中溶解度是有限的,因而涂料中化合物D的重量含量只占树脂固体量的0.24%。化合物A在醋酸丁酯中的溶解度较高,因而涂料中化合物A的重量含量占树脂固体量的1.2%。化合物B和C在醋酸丁酯中的溶解度更高,因而涂料中化合物B或C的重量含量占树脂固体量的3%。
每种情况中,较易溶解的化合物A、B或C达到的60°或20°光泽保留值和成像差异都远好于不易溶解的化合物D。21.将实验方法2用于标准的2K丙烯酸聚氨酯面漆中,将样品按下表规定的时间暴露于Xenon arc(CAM 180)装置中,然后测量其20°光泽保留值和成像差异。 *Ⅰ是未加稳定剂的空白样品Ⅱ含有0.24%重量份的化合物DⅢ含有1.2%重量份的化合物AⅣ含有3%重量份的化合物C,以及Ⅴ含有3%重量份的化合物B**涂层在此点发生破裂
该方法中,紫外线吸收剂溶解于非-HAPS溶剂的醋酸丁酯中,然后按涂料工业的常规做法将其加入树脂体系中。由于化合物D在醋酸丁酯中溶解度是有限的,因而涂料中化合物D的重量含量只占树脂固体量的0.24%。化合物A在醋酸丁酯中的溶解度较高,因而涂料中化合物A的重量含量占树脂固体量的1.2%。化合物B和C在醋酸丁酯中的溶解度更高,因而涂料中化合物B或C的含量占树脂固体量的3%。
每种情况中,较易溶解的化合物A、B或C达到的20°光泽保留值和成像差异都远好于不易溶解的化合物D。
Claims (9)
2.权利要求1的聚合物膜结构,它在电泳底涂层与底涂层或彩色涂层之间含有一层附加涂层,该附加涂层包含(ⅰ)成膜粘合剂以及有机或无机颜料或其混合物,以及(ⅱ)至少一种权利要求1中式Ⅰ的可溶并可热稳定的苯并三唑紫外线吸收剂。
3.权利要求2的聚合物膜结构,其中附加涂层还含有位阻胺光稳定剂。
4.权利要求1的聚合物膜结构,其中在组分(d)中,R1是氢,R2是叔辛基,壬基或十二烷基,且R3是α-枯基。
5.权利要求1的聚合物膜结构,其中组分(d)掺入清漆涂层中。
6.权利要求1的聚合物膜结构,其中成膜粘合剂是高固含量的热固性丙烯酸/蜜胺树脂或丙烯酸/聚氨酯树脂。
7.权利要求1的聚合物膜结构,它在底涂层中或在清漆涂层中,或同时在底涂层和清漆涂层中另含位阻胺光稳定剂。
8.一种稳定化的组合物,包含:
(a)一种适用于喷墨打印、照相材料或适用于染料扩散转印的记录材料,以及
(b)至少一种式1的苯并三唑紫外线吸收剂,以记录材料为基准,其数量为0.5-10%重量,其中R1是氢,
R2是辛基,壬基或-C2H4COOR4,其中R4是甲基或辛基,且
R3是α-枯基。
9.权利要求8的组合物,其中在组分(b)中,R1是氢,R2是叔辛基、壬基或十二烷基,R3是α-枯基。
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CN96105137A Expired - Lifetime CN1066181C (zh) | 1995-04-19 | 1996-04-18 | 用苯并三唑紫外线吸收剂稳定的涂层及记录材料 |
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US5095062A (en) * | 1988-04-11 | 1992-03-10 | Ciba-Geigy Corporation | Stabilized compositions containing liquid substituted 2H-benzotriazole mixtures |
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DE58907949D1 (de) * | 1988-12-14 | 1994-07-28 | Ciba Geigy Ag | Aufzeichnungsmaterial für Tintenstrahldruck. |
US5354794A (en) * | 1993-02-03 | 1994-10-11 | Ciba-Geigy Corporation | Electro coat/base coat/clear coat finishes stabilized with S-triazine UV absorbers |
DE4404081A1 (de) * | 1994-02-09 | 1995-08-10 | Basf Ag | UV-stabilisierte Polyoxymethylenformmassen |
EP0698637A3 (en) * | 1994-08-22 | 1996-07-10 | Ciba Geigy Ag | Polyurethanes stabilized with selected UV absorbers of 5-substituted benzotriazole |
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1995
- 1995-04-19 US US08/424,843 patent/US5574166A/en not_active Expired - Lifetime
- 1995-06-06 US US08/466,851 patent/US5554760A/en not_active Expired - Lifetime
- 1995-06-06 US US08/466,850 patent/US5563242A/en not_active Expired - Lifetime
-
1996
- 1996-04-05 US US08/628,433 patent/US5607987A/en not_active Expired - Lifetime
- 1996-04-10 EP EP96810220A patent/EP0738718A1/en not_active Withdrawn
- 1996-04-10 SE SE9601345A patent/SE509606C2/sv not_active IP Right Cessation
- 1996-04-10 GB GB9607427A patent/GB2299957B/en not_active Expired - Lifetime
- 1996-04-16 DE DE19615000A patent/DE19615000A1/de not_active Ceased
- 1996-04-17 BE BE9600333A patent/BE1010550A3/fr not_active IP Right Cessation
- 1996-04-17 CA CA002174412A patent/CA2174412A1/en not_active Abandoned
- 1996-04-17 CA CA002174411A patent/CA2174411C/en not_active Expired - Fee Related
- 1996-04-17 AU AU50731/96A patent/AU707202B2/en not_active Ceased
- 1996-04-17 KR KR1019960012131A patent/KR100426626B1/ko not_active IP Right Cessation
- 1996-04-18 CN CN96105141A patent/CN1059899C/zh not_active Expired - Lifetime
- 1996-04-18 ES ES009600874A patent/ES2130930B1/es not_active Expired - Fee Related
- 1996-04-18 CN CN96105137A patent/CN1066181C/zh not_active Expired - Lifetime
- 1996-04-18 IT IT96MI000751A patent/IT1283615B1/it active IP Right Grant
- 1996-04-18 AU AU50784/96A patent/AU706957B2/en not_active Ceased
- 1996-04-18 AT AT0070596A patent/AT405936B/de not_active IP Right Cessation
- 1996-04-18 FR FR9604847A patent/FR2733239B1/fr not_active Expired - Lifetime
- 1996-04-18 KR KR1019960012170A patent/KR100378233B1/ko not_active IP Right Cessation
- 1996-04-19 NL NL1002904A patent/NL1002904C2/nl not_active IP Right Cessation
- 1996-04-19 BR BR9601992A patent/BR9601992A/pt not_active IP Right Cessation
- 1996-04-19 JP JP8122465A patent/JPH08291151A/ja active Pending
- 1996-04-19 JP JP12246696A patent/JP3309153B2/ja not_active Expired - Lifetime
- 1996-04-19 BR BR9601991A patent/BR9601991A/pt not_active IP Right Cessation
- 1996-05-14 TW TW085105661A patent/TW419497B/zh not_active IP Right Cessation
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
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US5364749A (en) * | 1991-06-03 | 1994-11-15 | Ciba-Geigy Corporation | Photographic material containing UV absorber |
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