CN101490148B - 有机材料防光的方法 - Google Patents
有机材料防光的方法 Download PDFInfo
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- CN101490148B CN101490148B CN200780025935.3A CN200780025935A CN101490148B CN 101490148 B CN101490148 B CN 101490148B CN 200780025935 A CN200780025935 A CN 200780025935A CN 101490148 B CN101490148 B CN 101490148B
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- Prior art keywords
- absorption agent
- pigment
- formula
- organic materials
- phenyl
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- 239000003795 chemical substances by application Substances 0.000 claims description 38
- 238000010521 absorption reaction Methods 0.000 claims description 37
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Classifications
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/205—Compounds containing groups, e.g. carbamates
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/22—Compounds containing nitrogen bound to another nitrogen atom
- C08K5/23—Azo-compounds
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Abstract
本发明涉及有机材料,尤其来自药品和食品领域的有机材料,防光的方法,在其中,在载体材料上施涂或掺进至少一种权利要求1中定义的式(1)、(2)、(3)、(4)、(5)、(6)及式(7)和(8)的颜料以及任选的UV吸收剂和任选的其它颜料和/或着色剂,并把如此处理过的载体材料放在光源和要受保护的有机材料之间。
Description
本发明涉及保护有机材料免受日光(“可见光”),尤其人造光,所能造成的损伤的方法。
有机材料,如药品或尤其来自例如蔬菜、水果和肉之类食品领域的有机材料,含有对光照,尤其在日光短波区(最高达500nm)和UV区内的光照敏感的有机物质。
日光和人造光的光谱是不同的。例如,在氖管的光谱中,250~400nm的UV的比例小于日光中的,但在400~500nm消光且在约480nm(蓝光区)为最大的光的比例远大于日光中的情况。
很多食品,如水果、肉、牛奶、啤酒和蘑菇,都含有已知对UV光和最高达500nm的日光很敏感的维生素B2。维生素B2,也称做核黄素,以高浓度特别存在于鸡蛋、牛奶、肝、奶酪和鱼中。
核黄素的光敏性也是为什么例如牛奶大多放在不透光菱角包或白色瓶内贮藏和销售的原因之一。
其它维生素,如维生素A、维生素C、维生素D和维生素E,也在更大或较小程度上显示高光敏性。
在食品工业中,使用少量着色剂和尤其UV吸收剂来避光本身是已知的。但已发现,商品UV吸收剂仅在约300~400nm的光谱区内起作用,而在400~500nm的同样关键的光谱区内不起作用。
因此,持续需要更好地保护有机材料免受整个关键光谱区内光的损伤作用。
已经意外地发现,按照本发明的方法基本达到了上述标准。
因此本发明涉及有机材料,尤其来自药品和食品领域的有机材料,防光的方法,在其中,在载体材料(carrier material)上施涂或在其中掺进至少一种式
或式
或式
或式
或式
的颜料或下列2式
的颜料的混合物及任选的UV吸收剂,并把如此处理过的载体材料放在光源与要受保护的有机材料之间。
优选在按照本发明的方法中使用式(1)的颜料和式(2)的颜料及任选UV吸收剂的组合。
优选在本发明的方法中使用至少一种式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料和UV吸收剂的组合。
在按照本发明的方法中,除了式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料以外,还可以存在其它颜料或着色剂。
在其中,与载体材料混合或施涂在载体材料上的所用颜料或所用组合的量能在宽阔范围内变化;已经证明,相对于载体材料为0.001wt%~5wt%,尤其0.01wt%~2wt%,更尤其0.03wt%~0.5wt%的用量一般是有利的。
作为适用于按照本发明方法的UV吸收剂,尤其可提到的有2-(2’-羟基苯基)苯并三唑、2-羟基二苯甲酮、取代或未取代的苯甲酸的酯、丙烯酸酯、草酰胺、2-(2-羟基苯基)-1,3,5-三嗪、间苯二酚单苯甲酸酯或甲脒和式
的25℃下特定分子量(specific weight)为1200~1400,优选1300~1350的聚酯UV吸收剂。
从2-(2’-羟基苯基)苯并三唑类,可提到的有例如2-(2’-羟基-5’-甲基苯基)苯并三唑、2-(3’,5’-二叔丁基-2’-羟基苯基)苯并三唑、2-(5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯苯并三唑、2-(3’-仲丁基-5’-叔丁基-2’-羟基苯基)苯并三唑、2-(2’-羟基-4’-辛氧基苯基)苯并三唑、2-(3’,5’-二叔戊基-2’-羟基苯基)苯并三唑、2-(3’,5’-二(α,α-二甲基苄基)-2’-羟基苯基)-苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)苯并三唑、2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧基羰基乙基)苯基-苯并三唑、2,2’-亚甲基-二[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物;(R-CH2CH2-COO-CH2CH2-)2-,在其中,R=3’-叔丁基-4’-羟基-5’-2H-苯并三唑-2-基-苯基;2-[2’-羟基-3’-(α,α-二甲基苄基)-5’-(1,1,3,3-四甲基丁基)苯基]苯并三唑;和2-[2’-羟基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)苯基]苯并三唑。
从2-羟基二苯甲酮类,可提到的有例如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。
从2-(2-羟基苯基)-1,3,5-三嗪类,可提到的有例如2,4,6-三(2-羟基-4-辛氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2,4-二(2-羟基-4-丙氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛氧基苯基)-4,6-二(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁氧基丙氧基)苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷氧基丙氧基)苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-己氧基)苯基-4,6-二苯基-1,3,5-三嗪、2-(2-羟基-4-甲氧基苯基)-4,6-二苯基-1,3,5-三嗪、2,4,6-三[2-羟基-4-(3-丁氧基-2-羟基丙氧基)苯基]-1,3,5-三嗪和2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪。
从草酰胺类,可以提到的有例如4,4’-二辛氧基-N,N’-草酰二苯胺、2,2’-二乙氧基-N,N’-草酰二苯胺、2,2’-二辛氧基-5,5’-二叔丁-N,N’-草酰二苯胺、2,2’-二(十二烷氧基)-5,5’-二叔丁-N,N’-草酰二苯胺、2-乙氧基-2’-乙基-N,N’-草酰二苯胺、N,N’-二(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙基-N,N’-草酰二苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁-N,N’-草酰二苯胺的混合物,以及邻-和对-甲氧基-二取代N,N’-草酰二苯胺的混合物,和邻-及对-乙氧基-二取代N,N’-草酰二苯胺的混合物。
作为取代或未取代苯甲酸的酯,可提到的有例如水杨酸4-叔丁基-苯酯、水杨酸苯酯、水杨酸辛基苯酯、二苯甲酰基间苯二酚、二(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2,4-二叔丁基苯酯、3,5-二叔丁基-4-羟基苯甲酸十六烷基酯、3,5-二叔丁基-4-羟基苯甲酸十八烷基酯和3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯酯。
从丙烯酸酯类,可提到的有例如α-氰基-β,β-二苯基丙烯酸乙酯、α-氰基-β,β-二苯基丙烯酸异辛酯、α-甲氧基羰基肉桂酸甲酯、α-氰基-β-甲基-对-甲氧基肉桂酸甲酯、α-氰基-β-甲基-对-甲氧基肉桂酸丁酯、α-甲氧基羰基-对-甲氧基肉桂酸甲酯和N-(β-甲氧基羰基-β-氰基乙烯基)-2-甲基二氢吲哚。
间苯二酚单苯甲酸酯是例如下式的化合物
甲脒是例如下式的化合物
作为UV吸收剂,也可以用包含活性次甲基化合物,如未取代或取代丙二酸酯的组合物,如US-A-6,207,740、WO-A-02/14418、EP-A-0350386、US-A-4,661,566、US-A-4,749,772和EP-A-0272692中所述。
适用的其它UV吸收剂是α-[4-(2-氰基-3-乙氧基-3-氧代-1-丙烯基)-2-甲氧基-苯基]-ω-羟基-聚(氧基-1,2-乙二基)和α-[4-(2-氰基-3-乙氧基-3-氧-1-丙烯基)-苯基]-ω-羟基-聚(氧基-1,2-乙二基),以及它们的混合物。
按照本发明所用的组合优选包含下式的UV吸收剂
其中
R1是氢或卤素,优选氯,
R2是C1~C12烷基,优选未取代或被苯基取代的C1~C6烷基,和
R3是C1~C12烷基,优选未取代或被苯基取代的C1~C6烷基。
作为R2或R3的C1~C12烷基和C1~C6烷基可以是线形的,或也可以是从C3支化的。
按照本发明所用的组合尤其包含一种或多种下式的UV吸收剂
UV吸收剂的用量可以在宽阔范围内变化,有利地使用基于载体材料的重量,0.01~1.0wt%,尤其0.02~0.6wt%,更尤其0.05~0.4wt%的UV吸收剂。
式(1)~(16)的化合物是已知的,而且能用本身已知的已知方法制备。
适用于按照本发明方法的载体材料一般由玻璃或任选地由高分子量有机材料制成的透明塑料薄膜、塑料片材、容纳固体或液体材料的塑料容器组成。
适用于生产塑料薄膜或片材的高分子量有机材料是很普通的聚合物,尤其如聚酯(PES、PET)、聚碳酸酯(PC)、聚苯乙烯(PS)、聚甲基丙烯酸甲酯(PMMA)、聚酰胺、聚乙烯和聚丙烯之类的聚烯烃、聚氯乙烯、丙烯酸乙酯丁酯(EBA)、聚乙烯醇缩丁醛(PVB)、苯乙烯/丙烯腈(SAN)或丙烯腈/丁二烯/苯乙烯(ABS)。
特别优选纯聚烯烃,如聚乙烯、聚丙烯和聚异丁烯,还有取代聚烯烃,如氯乙烯、乙酸乙烯酯、苯乙烯、丙烯腈、丙烯酸酯和/或甲基丙烯酸酯或丁二烯的聚合产物,还有上述单体的共聚产物,尤其ABS(丙烯腈/丁二烯/苯乙烯)或EVA(乙烯/乙酸乙烯酯)。
按照本发明的颜料制剂尤其适用于着色纯或取代聚烯烃。
按照本发明的颜料制剂尤其适用于着色聚氯乙烯和聚烯烃,如聚乙烯和尤其聚丙烯。按照本发明的颜料制剂能用来着色所有已知的聚烯烃类,如LDPE、LLDPE(低密度聚乙烯)和HDPE(高密度聚乙烯)、tPP(透明聚丙烯)、茂金属和透明聚丙烯。
按照本发明的颜料制剂也适用于着色聚烯烃塑料纤维,尤其聚丙烯纤维。
在诸如聚氯乙烯或聚烯烃的着色中,按照本发明的颜料制剂的特性是良好的综合颜料性,如良好的迁移稳定性、热稳定性、光稳定性和老化稳定性以及良好的覆盖能力和高的色牢度,但尤其是良好的分散性和特低的揉搓脱色性。
例如按照本发明的方法进行如下:使用挤出机、辊炼机或混合或研磨设备,把一种或多种式(1)~(8)的颜料和UV吸收剂混进拟生产塑料薄膜或片材的塑料材料或聚合物彩色颗粒内,使颜料和UV吸收剂溶解或细分散在高分子量材料内。按照本发明所用的组合中的颜料组分和UV吸收剂的加入可同时或相继进行,在后一情况下,加入顺序可按需要选择。
然后用本身已知的方法,把如此处理过的塑料材料或聚合物彩色颗粒加工成薄膜或片材或成形为模塑制品,例如,盛固体或液体物质的容器,如用于饮料、或药物制剂,如丸剂或滴剂的容器或瓶子。
颜料和任选UV吸收剂的混合也可以在实际加工步骤前一刻进行,例如通过把按照本发明所用组合中的颜料组分、粉状UV吸收剂和粒状或粉状高分子量有机材料以及任选的其它组分,如添加剂,连续地同时直接喂进挤出机的进料区,在此处进行混合后立即加工。但一般优选把按照本发明所用的颜料或按照本发明所用的组合预先混进高分子量有机材料。
为减少脆性,经常希望在高分子量有机材料中加入所谓的增塑剂后再生产薄膜。可用作增塑剂的有例如磷酸、邻苯二甲酸或癸二酸的酯。在按照本发明的方法中,增塑剂可以在加入按照本发明所用的颜料或按照本发明所用的组合之前或之后加进聚合物。为了实现不同的色调,在高分子量有机材料中,除了式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料以外,还能按任意所需量加入其它着色剂,任选地与其它添加剂,如填料或催干剂一起。
在按照本发明方法的另外的实施方案中,可以对玻璃或现有透明塑料薄膜进行处理,例如通过喷涂或施涂按照本发明所用的颜料或按照本发明所用的组合,或通过相互独立地喷涂或施涂按照本发明所用组合的颜料组分和UV吸收剂,喷涂或施涂以任何所需顺序进行。
用按照本发明的方法处理过的上述材料,尤其由聚烯烃制成的材料的特性是非常好的使用牢固性,尤其如良好的光牢度和高温光牢度。
本发明还涉及式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料或式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料和UV吸收剂的组合来保护有机材料,使其能防光的用途。
能以多种方法把已按照本发明用一种或多种式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料或用所述组合处理过的载体材料放在光源与要受保护的有机材料之间。
例如,可以把要保护的有机材料包裹在已按照本发明用一种或多种式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料或用所述组合处理过的塑料薄膜内。例如也可以用按照本发明生产的薄膜覆盖温室。
另一种可能性是把按照本发明的一种或多种式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料或组合直接施涂到例如玻璃窗、玻璃瓶、药物和药物制剂的容器或包装上,施涂到塑料窗或由玻璃或塑料制成的厨柜门上,或为玻璃或塑料窗或由玻璃或塑料制成的厨柜门提供已按照本发明用一种或多种式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料或用所述组合处理过的塑料薄膜。
也可以对直接光源,如氖管,处理如下:施涂按照本发明的一种或多种式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料或所述组合,或用胶粘剂粘结上已按照本发明用一种或多种式(1)、(2)、(3)、(4)、(5)、(6)及(7)和(8)的颜料或用所述组合处理过的塑料薄膜。
下列实施例用来举例说明本发明。除非另有说明,实施例中的份数都是重量份,百分数都是重量百分数。温度以摄氏度表示。重量份与体积份之间的关系与g和cm3之间的关系相同。
实施例1:
聚丙烯(tPP=透明聚丙烯)注塑成型:
在玻璃容器内称取进1500.0g获自Borealis的tPP型RD360MO和3.0g下式的颜料
并在转鼓混合器内在50rpm下混合10min。
用获自Labtech的单螺杆挤出机LE 25/30(I/D 30),以熔体形式均化该混合物。(温度范围:160℃~最高200℃,螺杆转速:200rpm)并对挤出条进行造粒。
注塑成型:Ferromatik-FM 40机,步-楔式模具1*b*d1,d2,d390*36*0.5,0.85,1.5mm。
最高塑化温度:250℃
模温冷却水:15~25℃。
实施例1a:
聚丙烯(tPP=透明聚丙烯)注塑成型:
在玻璃容器内称取进1500.0g获自Borealis的tPP型RD360MO和3.0g下式的颜料
和2.4g下式的UV吸收剂
并在转鼓混合器内在50rpm下混合10min。
用获自Labtech的单螺杆挤出机LE 25/30(I/D 30),以熔体形式均化该混合物。(温度范围:160℃~最高200℃,螺杆转速:200rpm)并对挤出条进行造粒。
注塑成型:Ferromatik-FM 40机,步-楔式模具1*b*d1,d2,d390*36*0.5,0.85,1.5mm。
最高塑化温度:250℃
模温冷却水:15~25℃。
实施例2~5:
类似实施例1和1a中所述的方法,也可以生产含式(1)、(2)、(3)、(5)、(6)的颜料及式(7)和(8)的颜料混合物的注塑品。
实施例6:
LDPE(低密度聚乙烯)吹塑薄膜
在玻璃容器内称取进获自DOW的1482.0g LDPE型300E、18.0g式(1)的颜料。类似实施例1进行粉末和熔体混合。
吹塑薄膜:Labtech“Scientific”机
最高塑化温度:220℃
挤出机速度:70~80rpm
环形喷嘴温度:230℃
调节熔体产率和负载空气压力,使管径为约0.075mm。
实施例6a
LDPE(低密度聚乙烯)吹塑薄膜
在玻璃容器内称取进获自DOW的1482.0g LDPE型300E、18.0g式(1)的颜料和2.2g式(13)的UV吸收剂。类似实施例1进行粉末和熔体混合。
吹塑薄膜:Labtech“Scientific”机
最高塑化温度:220℃
挤出机速度:70~80rpm
环形喷嘴温度:230℃
调节熔体产率和负载空气压力使管径为约0.075mm。
实施例7~10:
用类似于实施例6和6a中所述的方法,也可以生产含式(1)、(2)、(3)、(5)、(6)的颜料及式(7)和(8)的颜料混合物的吹塑薄膜。
Claims (12)
2.按照权利要求1的方法,其中在载体材料上施涂或在其中掺进式(1)的颜料及UV吸收剂和任选的其它颜料和/或着色剂的组合,并把如此处理过的载体材料放在光源和要被保护的有机材料之间。
4.按照权利要求3的方法,其中式(9)的聚酯UV吸收剂具有1300~1350的特定分子量。
5.按照权利要求3的方法,其中作为UV吸收剂,使用式
的UV吸收剂。
6.按照权利要求1的方法,其中有机材料是食品。
7.按照权利要求1的方法,其中有机材料是药品。
8.按照权利要求1的式(1)的颜料用于保护来自药品和食品领域的有机材料免受光的用途。
9.按照权利要求1的式(1)的颜料和UV吸收剂的组合用于保护来自药品和食品领域的有机材料免受光的用途。
11.按照权利要求10的用途,其中式(9)的聚酯UV吸收剂具有1300~1350的特定分子量。
12.按照权利要求10的用途,其中,作为UV吸收剂,使用式(13)、(14)、(15)或(16)的UV吸收剂。
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GB1076635A (en) * | 1965-01-26 | 1967-07-19 | Ciba Ltd | Processes for the manufacture of disazo pigments |
DE2739041A1 (de) * | 1976-09-02 | 1978-03-09 | Ciba Geigy Ag | Verfahren zum pigmentieren von hochmolekularem organischem material |
US20030091764A1 (en) * | 2001-04-27 | 2003-05-15 | Yasuhiko Fujii | Plastic film, and shopping bag and garbage bag produced from the same |
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JP2682818B2 (ja) * | 1995-08-04 | 1997-11-26 | 大成化工株式会社 | 害虫誘引阻止材 |
ATE353353T1 (de) * | 2000-02-01 | 2007-02-15 | Ciba Sc Holding Ag | Verfahren zum inhaltschutz mit dauerhaften uv- absorber |
US20050058846A1 (en) * | 2003-09-16 | 2005-03-17 | Ryosuke Matsui | Polyester film |
WO2005063592A1 (en) * | 2003-12-23 | 2005-07-14 | Ciba Specialty Chemicals Holding Inc. | Method of protecting organic material from light |
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GB1076635A (en) * | 1965-01-26 | 1967-07-19 | Ciba Ltd | Processes for the manufacture of disazo pigments |
DE2739041A1 (de) * | 1976-09-02 | 1978-03-09 | Ciba Geigy Ag | Verfahren zum pigmentieren von hochmolekularem organischem material |
US20030091764A1 (en) * | 2001-04-27 | 2003-05-15 | Yasuhiko Fujii | Plastic film, and shopping bag and garbage bag produced from the same |
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CN101490148A (zh) | 2009-07-22 |
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