CN1140168A - 新的2-(2-羟基-3-α-枯基-5-烷基苯基)-2H-苯并三唑 - Google Patents
新的2-(2-羟基-3-α-枯基-5-烷基苯基)-2H-苯并三唑 Download PDFInfo
- Publication number
- CN1140168A CN1140168A CN96105141A CN96105141A CN1140168A CN 1140168 A CN1140168 A CN 1140168A CN 96105141 A CN96105141 A CN 96105141A CN 96105141 A CN96105141 A CN 96105141A CN 1140168 A CN1140168 A CN 1140168A
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- China
- Prior art keywords
- benzotriazole
- cumyl
- hydroxy
- alpha
- phenyl
- Prior art date
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
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- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
- IJRHDFLHUATAOS-DPMBMXLASA-N sodium;(z,12r)-12-hydroxyoctadec-9-enoic acid Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IJRHDFLHUATAOS-DPMBMXLASA-N 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 230000003068 static effect Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
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- 150000003568 thioethers Chemical class 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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Abstract
苯并三唑紫外吸收剂,具有通式I其中R为叔辛基,壬基或十二烷基或-CHmCH2mCOOR4,其中R∴为烷基,且m为1-4,它能保护有机基质,提供优秀的光稳定性保护。
Description
本发明涉及新的2-(2-羟基-3-α-枯基-5-烷基苯基)-2H-苯并三唑,它对于稳定有机材料特别有效。
美国专利NO.4,278,589中描述了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No.4,278,589还描述了2-(2-羟基-3,5-二-α-枯基-苯基)-2H-苯并三唑的制备。这后面的化合物是非常有效的紫外吸收剂,但不利的是它是相对不溶的,它在二甲苯中的溶解度只有14%(重量比)。由于环境的关系这些香族溶剂是法律上禁用的,所以特别需要找到一种具有2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑的通常的光稳定效果,并能溶于环境允许的溶剂中的有效的苯并三唑。
日本公开75/158588中描述了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,它们可作为有效的紫外吸收剂。
美国专利No.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-2-(2-羟基-3,5-二-叔辛基苯基)-2H-苯并三唑的制备。美国专利NOS.4,587,346;4,675,352;4,973,701;5,095,062和5,240,975中描述了用高级烯烃和酸催化剂后烷基化上述苯并三唑制备液体苯并三唑混合物的方法。这些产物是不同的相关的苯并三唑的复杂液体混合物,并且它们可溶于环境上允许的溶剂。但是,尽管这些紫外吸收剂易溶于环境可接受的溶剂,但是它们不具有在3-位用α-枯基取代的苯并三唑化合物的热稳定性。
本发明的苯并三唑化合物是在3-位用α-枯基取代且5-位用烷基或羧烷基取代的烷基取代。这些物质比简单烷基官能化的三芳基-S-三嗪更易溶于常规涂层溶剂中。常规涂层溶剂包括二甲苯,甲基戊基酮,丁基溶纤剂,丁基卡必醇和甲基异丁基酮。
本发明的目的是提供新的可溶的2-(2-羟基-3-α-枯基-5-烷基苯基)-2H-苯并三唑。
本发明的另一目的是提供一种对光化光的有害影响稳定的有机组合物,它使用了在苯环的3-位用α-枯基取代的新的可溶性苯并三唑。
本发明还涉及2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑的新的可溶的晶体。
在美国专利US4,278,589的实施例18中公开了化合物2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑,它为灰白色粉末,熔点88~90℃。作为这样的的粉末产物在处理和表观密度方面存在很多缺点,显示出较差的流动性、可计量性和贮存稳定性。
现在发现可以获得以纯化的结晶颗粒的不同的晶体变体形式的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑,该结晶颗粒显示出合格的加工性、表观密度、流动性、可计量性和贮存稳定性。
该新的变体的特征在于为新的灰白色晶体,熔点范围为109-111℃;且在于Cu-Kα射线得到的X射线衍射图,所显示的衍射角(2Θ)如下:
峰No. | 2Θ | 峰No. | 2Θ | 峰No. | 2Θ | 峰No. | 2Θ |
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 | 234 | 24 | 24.6 |
25 | 26.0 | 26 | 28.0 | 27 | 29.0 | 28 | 30.4 |
29 | 31.0 |
本发明的化合物2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑也可以具有极好的溶解性的不定形的形式获得。
其中R为-CHmCH2mCOOR4,R4为含有1-18个碳原子的烷基,且m为1-4。
优选的上述通式化合物是那些R为壬基,十二烷基或-CHmCH2mCOOR4,R4为含有1-12个碳原子的烷基,且m为2。
具有1-18个碳原子的烷基的例子有甲基,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,及其相应的支链异构体。
本发明还涉及制备2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑的新的可溶性晶体的方法,它包括将所述化合物溶于芳香族溶剂,加入低级链烷醇将化合物沉淀出;或在单独使用的低级链烷醇或其与少量芳香族溶剂的混合物中结晶或重结晶该化合物。
优选地,此方法包括在具有1-4个碳原子的链烷醇中,或在其与少量芳香族溶剂的混合物中结晶或重结晶所述化合物。
上述方法中可使用的芳香族溶剂的例子有甲苯或二甲苯。当少量使用时,这个少量可以是,例如,不超过15%或,优选为5-15%(占所用溶剂总体积数的体积比)。
在本发明方法中可使用一些链烷醇,例如,甲醇,乙醇,正丙醇,异丙醇,1-丁醇,仲丁醇或异丁醇。优选的链烷醇是含有2,3或4个碳原子的链烷醇,特别优选异丙醇或1-丁醇。
本发明还涉及对光化诱导的降解稳定的组合物,它包括:
(a)预进行光化诱导的降解的有机材料,和
(b)如上所述的无定形或结晶形式的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑,2-(2-羟基3-α-枯基-5-十二烷基苯基)-2H-苯并三唑或具有以下通式的化合物:
其中R为-CHmH2mCOOR4,R4为具有1-18个碳原子的烷基,且m为1-4。
仿照本发明,苯并三唑的用量一般为被稳定组合物重量的0.01~20%。
在很长一段时间内苯并三唑紫外吸收剂,是本领域的主要依靠,2-〔2-羟基-3,5-二(α-枯基)苯基〕-2H-苯并三唑是多用途的并代表所能提供的苯并三唑紫外吸收剂。不幸地是,这些化合物在甲苯或二甲苯中只有有限的溶解度(约14%重量比),而在环境可接受的溶剂中极少溶解。这就成为一种严重的限制,因为环境的原因芳香族溶剂不能使用。
幸运地是,现已找到可溶的热稳定的苯并三唑紫外吸收剂,它主要是2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑的新的可溶的晶体,它具有与2-〔2-羟基-3,5-二(α-枯基)苯基〕-2H-苯并三唑所具有的同样的低挥发性和极好的光稳定性,而且它溶于环境上可接受的溶剂。
这些环境上可接受的溶剂是,例如,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,乙酸氧代己酯,乙酸氧代辛酯,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,丙二醇苯醚,丙二醇正丙醚,丙二醇叔丁醚,丙酸正戊酯,二异丁基酮,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,异十三烷醇,丁氧乙氧丙醇,异丁酸异丁酯,戊二酸二甲酯,3-甲氧基正丁基乙酸酯,丙酸正戊酯。
本发明的组合物还涉及其中附加含有光稳定剂三芳基-S-三嗪,受阻胺或苯并呋喃-2-酮或它们的混合物的组合物。
优选的这些组合物含有附加的有效量的稳定剂如2,4双(2,4-二甲基苯基)-6-(2-羟基-4-辛氧苯基)-S-三嗪;2,4-双-(2,4-二甲基苯基)-6-(2-羟基-4-〔3-(十五烷氧)-2-羟丙氧〕-S-三嗪;双-(1-辛氧-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。
依据本发明的优选实施方案,对光化光的有害影响稳定的组合物含有:
(a)预在光化光的有害影响下处理的有机物质,和
(b)苯并三唑紫外吸收剂,它是2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑或2-(2-羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑。
为了获得最大的光稳定性,同时使用其它常规光稳定剂更有利。这种稳定剂为紫外吸收剂如二苯酮,苯并三唑,氰基丙烯酸酯或N,N'-草酰二苯胺,或含金属的光稳定剂,例如有机镍化合物,或受阻胺类型的光稳定剂。
可被稳定的有机材料(聚合物)一般包括:
1.单烯属烃和二烯属烃聚合物,例如聚乙烯(可任意交联的),聚丙烯,聚异丁烯,聚丁烯-1-,聚甲基戊烯-1,聚异戊二烯或聚丁二烯,以及环烯烃,例如环戊烯或降冰片烯。
2.上述1)所述聚合物的混合物,例如聚丙烯和聚异丁烯的混合物。
3.单烯属烃和二烯属烃之间或它们与其它的乙烯基单体的共聚物,例如,乙烯/丙烯,丙烯/丁烯-1,丙烯/异丁烯,乙烯/丁烯-1,丙烯/丁二烯,异丁烯/异戊二烯,乙烯/丙烯酸烷基酯,乙烯/甲基丙烯酸烷基酯,乙烯/乙酸乙烯基酯或乙烯/丙烯酸共聚物及其盐(离聚物)和乙烯,丙烯和二烯的三元共聚物,其中二烯的例子如己二烯,二环戊二烯或亚乙基降冰片烯。
4.聚苯乙烯,聚(α-甲基苯乙烯)。
5.苯乙烯或甲基苯乙烯与二烯或丙烯酸衍生物的共聚物,例如,苯乙烯/丁二烯,苯乙烯/丙烯腈,苯乙烯/甲基丙烯酸乙酯,苯乙烯/丁二烯/丙烯酸乙酯,苯乙烯/丙烯腈/丙烯酸甲酯;由苯乙烯共聚物和其它聚合物形成的高冲击混合物,例如从聚丙烯酸酯,二烯聚合物或乙烯/丙烯/二烯三元共聚物得到的,和苯乙烯的嵌段共聚物,例如,苯乙烯/丁二烯/苯乙烯,/异戊二烯/苯乙烯,/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。
6.苯乙烯的接枝共聚物,如苯乙烯接枝在聚丁二烯上,苯乙烯和丙烯腈接枝在聚丁二烯上,苯乙烯和甲基丙烯酸烷基酯接枝在聚丁二烯上,苯乙烯和丙烯腈接枝在乙烯/丙烯/二烯三元共聚物上,苯乙烯和丙烯腈接枝在聚丙烯酸酯或聚甲基丙烯酸酯上,苯乙烯和丙烯腈接枝在丙烯酸酯/丁二烯共聚物上,以及它们和5)所列的共聚物的混合物,例如称作ABS-,MBS-,ASA-或AES-聚合物的共聚物混合物。
7.含卤素的聚合物,如聚氯丁二烯,氯化橡胶,氯化或氯磺化的聚乙烯,表氯醇均聚和共聚物,从含卤素的乙烯基化合物得到的聚合物,例如,聚氯乙烯,聚偏氯乙烯,聚氟乙烯,聚偏氟乙烯,以及它们的共聚物,例如氯乙烯/偏氯乙烯,乙烯基氯/乙酸乙烯基酯,偏氯乙烯/乙酸乙烯基酯共聚物,乙烯基氟/乙烯基醚共聚物。
8.由α,β-不饱和酸及其衍生物得到的聚合物,例如聚丙烯酸酯和聚甲基丙烯酸酯,聚丙烯酰胺和聚丙烯腈。
9.由上述8)所述的单体之间或其与其它不饱和单体形成的共聚物,例如,丙烯腈/丁二烯,丙烯腈/丙烯酸烷基酯,丙烯腈/丙烯酸烷氧烷基酯或丙烯腈/乙烯基卤化物共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
10.由不饱和醇和胺,或它们的酰基衍生物或它们的乙缩醛得到的聚合物,例如聚乙烯醇,聚乙酸乙烯基酯,聚硬脂酸乙烯基酯,聚苯甲酸乙烯基酯,聚顺丁烯二酸乙烯基酯,聚乙烯醇缩丁醛,聚邻苯二甲酸烯丙酯或聚烯丙基蜜胺。
11.环醚的均聚物和共聚物,例如聚亚烷基二醇,聚环氧乙烷,聚环氧丙烷或它们与双缩水甘油醚的共聚物。
12.聚缩醛,如聚甲醛和那些含有环氧乙烷作为共聚单体的聚甲醛。
13.聚苯氧和聚苯硫,和聚苯氧与聚苯乙烯的混合物。
14.聚氨酯,它是由聚醚,聚酯或聚丁二烯在一端以羟基结尾,而在另一端以脂肪族或芳香族聚异氰酸酯结尾而衍生来的,同样适用于它的前体(多异氰酸酯,多元醇或预聚物)。
15.由二胺和二羧酸和/或从氨基羧酸或相应的内酰胺得到的聚酰胺和共聚酰胺,例如聚酰胺4,聚酰胺6,聚酰胺6/6,聚酰胺6/10,聚酰胺11,聚酰胺12,聚-2,4,4-三甲基-六亚甲基对苯二酰胺,聚对苯基对苯二酰胺或聚间苯基间苯二酰胺,以及它们与聚醚的共聚物,例如与聚乙二醇,聚丙二醇,或聚亚丁基二醇。。
16.聚脲,聚酰亚胺和聚酰胺-酰亚胺。
17.由二羧酸和二醇和/或从羟基羧酸或相应的内酯得到的聚酯,例如聚对苯二甲酸乙二醇酯,聚对苯二甲酸丁二醇酯,聚对苯二甲酸-1,4-二甲基醇-环己烷酯,聚-〔2,2-(4-羟苯基)丙烷〕对苯二甲酸酯和聚羟基苯甲酸酯以及如由具有羟基末端基的聚醚得到的嵌段-共聚醚-酯。
18.聚碳酸酯
19.聚砜,聚醚砜和聚醚酮。
20.交联的聚合物,由在一面用醛而另一面用酚,脲和蜜胺处理得到,例如酚/甲醛树脂,脲/甲醛树脂和蜜胺/甲醛树脂。
21.干燥和非干燥的醇酸树脂。
22.不饱和聚酯树脂,它来自饱和和不饱和二羧酸和多元醇得到的共聚酯,并用乙烯基化合物作交联剂,且其含卤素的改性体具有低可燃性。
23.热固性丙烯酸树脂,由取代的丙烯酸树脂衍生而来,例如环氧丙烯酸酯,尿烷-丙烯酸酯或聚酯丙烯酸。
24.醇酸树脂,聚酯树脂或丙烯酸酯树脂与作为交联剂的蜜胺树脂,尿素树脂,聚异氰酸酯或环氧树脂混合物。
25.由聚环氧化物衍生来的交联的环氧树脂,例如来自双-缩水甘油醚或来自环脂肪族二环氧化物。
26.天然聚合物,例如纤维素,橡胶,明胶及其衍生物,它们都进行了同系物方式的化学改性,例如乙酸纤维素,丙酸纤维素和丁酸纤维素,或纤维素醚,例如甲基纤维素。
27.上述聚合物的混合物,例如PP/EPDM,聚酰胺6/EPDM或ABS,PVC/EVA,PVC/ABS,PVC/MBS,PC/ABS,PBTP/ABS。
28.天然获得的和合成的有机材料,它们是纯单体化合物或这些化合物的混合物,例如矿物油,动物和植物脂肪,油和蜡,或以合成酯为基础的油,脂肪和蜡(例如邻苯二甲酸酯,己二酸酯,磷酸酯或1,2,4-苯三酸酯)以及合成酯与矿物油按任意重量比的混合物,这些材料可用作聚合物的增塑剂或织物纺丝油,还包括这些材料的含水乳液。
29.天然或合成橡胶的水乳液,例如天然胶乳或羧化苯乙烯/丁二烯共聚物胶乳。
30.聚硅氧烷,如在美国专利No.4,259,467中描述的软性的,亲水的聚硅氧烷;和在美国专利No.4,355,147中描述的硬性聚有机硅、氧烷。
31.与不饱和的丙烯酸聚乙酰乙酸酯树脂或不饱和的丙烯酸树脂结合的聚酮亚胺。不饱和的丙烯酸树脂包括尿烷而烯酸酯,聚醚丙烯酸酯,具有不饱和侧基的乙烯基或丙烯酰基共聚物和丙烯酸化的蜜胺。聚酮亚胺是多胺和酮在酸催化剂存在下制备得到的。
32.辐射可固化的组合物,含有烯键的不饱和单体或齐聚物和聚不饱和脂肪族齐聚物。
33.环氧蜜胺树脂如用环氧官能共醚化高固体蜜胺树脂如LSE-4103(Monsanto)交联的光稳定的环氧树脂。
一般地,本发明化合物的用量为被稳定组分重量的0.01~20%,但可根据特定的基质和应用改变用量。优选的范围为0.1~5%,更优选1~5%。
依本发明所得的稳定的组合物还可任意含有0.01~10%,优选0.025~5%,更优选0.1~1%(重量比)的不同的常规添加剂,如下列材料或它们的混合物。
其它特别需要的组合物包括哪些附加含有选自下列的紫外吸收剂的化合物,该紫外吸收剂包括二苯酮类,苯并三唑类,氰基丙烯酸衍生物,羟基芳基-S-三嗪基,有机镍化合物和N,N′-草酰二苯胺类。
优选的紫外吸收剂选自下列化合物: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-(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-辛氧羰乙基)苯基〕-2H苯并三唑,4,4′-二辛氧-N,N′-草酰二苯胺、2,2′-双辛基氧-5,5′-二叔丁基-N,N′-草酰二苯胺,2,2′-双辛基氧-5,5′-二叔丁基-N,N′-草酰二苯胺,2,2′-双十二烷基氧-5,5′-二叔丁基-N,N′-草酰二苯胺,2-乙氧-2′-乙基-N,N′-草酰二苯胺,2,6-双(2,4-二甲基苯基)-4-(2-羟基-4-辛氧苯基-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)-,2,6-双(2,4-二甲基苯基)-4-〔2-羟基-4-(2-羟基-3十二烷基氧丙氧)苯基〕-S-三嗪和2,2′-二羟基-4,4′-二甲氧二苯酮。
其它需要的组合物包括那些附加含有有效的稳定剂量的酚类抗氧化剂的组合物;那些附加含有受阻胺衍生物的组分;或附加含有亚磷酸盐或亚膦酸盐稳定剂的组分。
特别需要的组合物还包括其中有机物质是高固含量的用作工业精饰的瓷漆,也可用作线圈涂层;也可用作渗透木材的涂料或用作膜形成木材涂料。
当本发明化合物含有反应功能基时,所述化合物可通过缩聚或自由基反应化学地键接在聚合物基质上。这样就提供了一种不迁移的,不可升华的紫外吸收剂稳定剂。这些反应基团包括羟基,羧基和不饱和的乙烯基部分。
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-4,6-二甲基苯酚,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)-4,6-二甲基苯酚,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-甲氧甲基苯酚。
1.2.烷基化的氢醌,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.羟基化的硫代二苯醚,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.亚烷基双苯酚,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-羟苄基)-4-甲基苯酚,1,1,3-三-(5-叔丁基-4-羟-2-甲基苯基)-,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,亚乙基二醇双-〔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)-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,例如:1,3,5-三-(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯,二-(3,5-二叔丁基-4-羟苄基)硫醚,3,5-二-叔丁基-4-羟基苄基-巯基-乙酸异辛酯,双-(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二酸酯,1,3,5-三-(3,5-二-叔丁基-4-羟苄基)异氰尿酸酯,1,3,5-三-(4-叔丁基-3-羟基-2,6-二甲基苄基)-异氰尿酸酯,3,5-二叔丁基-4-羟基苄基-磷酸二-十八烷基酯,3,5-二叔丁基-4-羟基苄基-磷酸单乙酯,钙盐。
1.6.酰氨基酚类,例如:
4-羟基-N-月桂酰苯胺,4-羟基-N-硬脂酰苯胺、2,4-双-辛巯基-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-羟苯基)-氨基甲酸酯。
1.7.β-(3,5-二叔丁基-4-羟基-3-羟基苯基)-丙酸与单羟基或多羟基醇形成的酯,例如:甲醇 二甘醇十八醇 三甘醇1,6-己二醇 季戊四醇新戊二醇 二-羟乙基异氰尿酸酯硫代二甘醇 二羟乙基草酸二酰胺
1.8.β-(5-叔丁基-4-羟基-3-甲基苯基)-丙酸与单羟基或多羟基醇形成的酯,例如:甲醇 二甘醇十八醇 三甘醇1,6-己二醇 季戊四醇新戊二醇 二-羟乙基异氰尿酸酯硫代二甘醇 二羟乙基草酸二酰胺
19.β-(3,5-二叔丁基-4-羟基苯基)-丙酸的酰胺,例如:
N,N′-二-(3,5-二叔丁基-4-羟苯基丙酰)六亚甲基二胺,
N,N′-二-(3,5-二叔丁基-4-羟苯基丙酰)三亚甲基二胺,
N,N′-二-(3,5-二叔丁基-4-羟苯基丙酰)-肼。
2.紫外吸收剂和光稳定剂
2.1.2-(2′-羟基苯基)-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,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)羰基-乙基)-,3′-十二烷基-5′-甲基-,和3′-叔丁基-5′-(2辛氧羰基)乙基-,以及十二烷基化的-5′-甲基衍生物。
2.2.2-羟基-二苯酮,例如:4-羟基-,4-甲氧基-,4-辛氧,4-癸氧-,4-十二烷氧,4-苄氧-,4,2′,4′-三羟基-和2′-羟基-4,4′-二甲氧基衍生物。
2.3.任意取代的苯甲酸的酯,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,苯甲酰间苯二酚,3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯酯,和3,5-二叔丁基-4-羟基苯甲酸十六烷基酯。
2.4.丙烯酸酯,例如:α-氰基-β,β-二苯基丙烯酸乙酯或异辛酯,α-甲酯基-肉桂酸甲酯,α-氰基-β-甲基-P-甲氧基-肉桂酸甲酯或丁酯,α-甲酯基-P-甲氧基-肉桂酸甲酯,N-(β-甲酯基-β-氰乙烯基)-2-甲基-二氢吲哚。
2.5.镍化合物,例如2,2′-硫代-双-〔4-(1,1,3,3-四甲基丁基)-苯酚〕的镍络合物,比如1∶1或1∶2的络合物,任意地附加配体如正丁胺,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的镍盐,如甲酯,乙酯或丁酯,酮肟的镍络合物,如2-羟基-4-甲基苯基十一烷基酮肟,1-苯基-4-月桂酰-5-羟基-吡唑的镍络合物,任意含有附加配体。
2.6.立体受阻胺,例如: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)-六亚甲基胺和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-丁烷四羧酸酯,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,例如:4,4′-二辛氧-N,N′-草酰二苯胺,2,2′-二辛氧-5,5′-二叔丁基-N,N′-草酰二苯胺,2,2′-二-十二烷氧-5,5′-二叔丁基-N,N′-草酰二苯胺,2-乙氧-2′-乙基-N,N′-草酰二苯胺,N,N′-双(3-二甲基氨基丙基)-草酰胺,2-乙氧-5-叔丁基-2′-乙氧-N,N′-草酰二苯胺和它与2-乙氧-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-,以及O-和P-乙氧二取代N,N′-草酰二苯胺的混合物。
2.8.羟苯基-S-三嗪,例如:2,6-双-(2,4-二甲基苯基)-4-(2-羟基-4-辛氧苯基)-S-三嗪;2,6-双-(2,4-二甲基苯基)-4-(2,4-二羟苯基)-;2,4-双(2,4-二羟苯基)-6-(4-氯苯基)-;2,4-双〔2-羟-4-(2-羟乙氧)苯基〕-6-(4-氯苯基)-S-三嗪;2,4-双〔2-羟基-4-(2-羟基-4-(2-羟乙氧)苯基〕-6-(2,4-二甲基苯基)-S-三嗪;2,4-双〔2-羟基-4-(2-羟乙氧)苯基〕-6-(4-溴苯基)-S-三嗪;2,4-双〔2-羟基-4-(2-乙酸基乙氧)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)-;2,4-双-(2,4-二甲基苯基)-6-{2-羟基-4-〔3-(2-乙基己氧)-2-羟丙氧〕苯基}-S-三嗪;2,4-双-(2,4-二甲基苯基)-6-{2-羟-4-〔3-(十五烷氧)-2-羟丙氧〕苯基}-S-三嗪。
3.金属钝化剂,例如: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.亚磷酸盐和亚膦酸盐,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-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,三硬酯酰-山梨醇三亚磷酸酯,四-(2,4-二叔丁基苯基)4,4′-二亚苯基二亚膦酸酯。
5.破坏过氧化物的化合物,例如:β-硫代二丙酸酯,例如月桂基,硬脂酰基,肉豆蔻基或十三烷基酯,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,二(十八烷基)二硫醚,季戊四醇四-(β-十二烷基巯基)-丙酸酯。
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-二(十四烷基)羟胺,N,N-二(十八烷基)羟胺,N,N-二(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,由氢化牛脂基胺衍生来的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-十五烷基硝酮,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,由氢化的牛脂基胺衍生来的N,N-二烷基羟胺衍生来的硝酮。
8.聚酰胺稳定剂,例如与碘化物和/或磷化合物结合的铜盐,和二价锰盐。
9.碱性共稳定剂,例如:蜜胺,聚乙烯吡咯烷酮,双氰胺,氰尿酸三烯丙基酯,尿素衍生物,肼的衍生物,胺,聚酰胺,聚氨酯,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,焦儿茶酚锑盐或焦儿茶酚锌盐。
10.亲核试剂,例如:4-叔丁基-苯甲酸,己二酸,二苯基乙酸。
11.填充剂和增强剂,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,阻燃剂,抗静电剂,发泡剂和硫代增效剂如二月桂基硫代二丙酸酯或二硬脂酰基硫代二丙酸酯。
特别需要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),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-羟苄基)异氰尿酸酯,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,3,6-二氧杂亚辛基双(3甲基-5-叔丁基-4-羟基氢化肉桂酸酯),2,6-二叔丁基-P-甲酚,2,2′-亚乙基-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)异氰尿酸酯,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)乙基〕异氰尿酸酯,3,5-二-(3,5-二叔丁基-4-羟苄基)2,4,6-三甲苯酚,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-羟基氢化肉桂酸酰胺),双(乙基3,5-二叔丁基-4-羟苄基膦酸钙,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酯,双(3,5-二叔丁基-4-羟基氢化肉桂酰基)酰肼,和N,N′-双〔2-(3,5-二叔丁基-4-羟基氢化肉桂酰氧)-乙基〕-草酰胺。
特别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-羟苄基)异氰尿酸酯,2,6-二叔丁基对甲酚或2,2′-亚乙基-双(4,6-二叔丁基苯酚)。
特别需要的受阻胺化合物选自: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-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,二(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〕二十一烷,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-羟基哌啶和琥珀酸的缩聚产物,4,4′-亚乙基双(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-2,2,6,6-四甲基-哌啶-4-基)-氨基-S-三嗪-2-基〕-1,10-二氨基-4,7-二氮杂癸烷,混合〔2,2,6,6-四甲基哌啶-4-基/β,β,β′,β′-四甲基-3,9-(2,4,8,10-四氧杂螺〔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-(2,4,8,10-四氧杂螺〔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-1,3,8-三氮杂螺〔4.5〕癸烷-2,4-二酮,二-(1-辛基氧-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯,1-辛基氧-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-2,2,6,6-四甲基哌啶-4-基)亚氨基-亚己基-〔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-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基〕-S-三嗪,2,4-双〔N-(1-环己基氧-2,2,6,6-四甲基哌啶-4-基)-正丁基氨〕-6-〔二-(2-羟乙基)氨基〕-S-三嗪,和2,4-双〔N-(1辛基氧-2,2,6,6-四甲基哌啶-4-基)-正丁基氨〕-6-〔二-(2-羟乙基)氨基〕-S-三嗪。
特别优选的受阻胺化合物是双(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-羟基哌啶和琥珀酸的缩聚产物,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-2,2,6,6-四甲基-哌啶-4-基)-氨基-S-三嗪-2-基〕-1,10-二氨基-4,7-二氮杂癸烷,二-(1-辛基氧-2,2,6,6-四甲基-哌啶-4-基)癸二酸酯,二-(1-环己基氧-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯,1-辛基氧-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-2,2,6,6-四甲基哌啶-4-基)亚氨基-亚己基-〔4-(1-环己基氧-2,2,6,6-四甲基哌啶-4-基)亚氨基〕,或2,4,6-三〔N-(1-环己基氧-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基〕-S-三嗪。
本发明的另一目的是提供稳定有机材料对抗光化诱导的降解的方法,它包括
在有机物质中混入或对其施用本发明的无定形或结晶形式的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑或具有下式结构的化合物
其中R为-CHmCH2mCOOR4,R4为具有1-18个碳原子的烷基,且m为1-4。
本发明的另一目的是提供一种方法,使有机材料在放入QUV试验仪中时,可对抗光化诱导的降解长于3000小时,(周期:8小时光照且70℃;4小时黑暗,50℃且相对湿度100%),其特征是
在有机材料中混合或对其施用本发明的无定形的或结晶形式的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5壬基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5-十二烷基苯基)2H-苯并三唑或具有下式的化合物
其中R为-CHmCH2mCOOR4,R4为具有1-18个碳原子的烷基,且m为1-4。
X-射线衍射图案在Philips Norelco X-射线衍射仪上记录,使用Cu-Kα射线,并用镍滤光片。所有样品都具有相同粒径,为40-75微米。
下列实施例只是为了举例说明本发明,并不以任何方式限制本发明的特性和范围。
实施例1:2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑
向5升装备有搅拌器,温度计,回流冷凝管和氮气入口的三颈瓶中放入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并丙醇和240ml水。导入氮气并加入160ml 50.1%的氢氧化钠水溶液。将含有158.2g(2.42克原子)锌的烧瓶接在反应烧瓶上,经90分钟将锌粉分批加入。在加入锌粉的过程中使内部温度保持在40和45℃之间,加完后再保持此温度1小时,然后将混合物在70℃下加热3小时。将混合物冷却至室温,用600ml浓盐酸酸化。过滤除去锌淤渣。产物含有有机层中,将其用4份340ml的稀盐酸洗涤,并用无水硫酸钠干燥。真空除去有机溶剂,得到粘稠的糖浆状粗产物。
将300g粗产物样品溶于300ml二甲苯。在搅拌下向此溶液中加入600ml乙醇,得到254g新的可溶性式I化合物的结晶,其熔点为109-111℃,在薄层色谱中只有一个点。
分析:
C29H35N3O的计算值:C,78,9;H,8.0;N,9.5
C,78.7; H,8.1;N,9.6
此产物使用Cu-Kα射线得到的X-射线衍射图形显示出的衍射角(2θ)列于下表:
峰No. | 2Θ | 峰No. | 2Θ | 峰No. | 2Θ | 峰No. | 2Θ |
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 |
实施例2:2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑(对比实施例)
按美国专利No.4,278,589中实施例18描述的方法制备标题化合物,得到灰白色结晶,熔点88-90℃。此化合物用Cu-Kα射线得到的X-射线衍射图形显示出的衍射角(2θ)列于下表:
峰No. | 2Θ | 峰No. | 2Θ | 峰No. | 2Θ | 峰No. | 2Θ |
1 | 5.2 | 2 | 6.2 | 3 | 6.8 | 4 | 9.2 |
5 | 9.7 | 6 | 11.0 | 7 | 12.0 | 8 | 12.2 |
9 | 13.0 | 10 | 13.6 | 11 | 14.6 | 12 | 15.4 |
13 | 15.6 | 14 | 16 4 | 15 | 17.8 | 16 | 18.8 |
17 | 19.4 | 18 | 19.8 | 19 | 20.4 | 20 | 21.0 |
21 | 22.4 | 22 | 22.8 | 23 | 23.4 | 24 | 24.2 |
25 | 25.0 | 26 | 25.4 | 27 | 26.0 | 28 | 27.6 |
29 | 29.4 | 30 | 30.8 | 31 | 31.2 | 32 | 32.4 |
本发明的实施例1的结晶的X-射线衍射图与现有技术的美国专利No.4,278,589中实施例18的化合物的X-射线衍射图的对比明显地表明这两种物质不一样。
实施例3:无定形的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑
将实施例1的化合物加热至熔化,然后使之再固化。这样获得的无定形物质的熔点为59-74°。薄层色谱显示出一个点,该点实施例1的产物获得的点相同。
X-射线衍射图显示出无特征图形,证明了此实施例中化合物的无定形特性。
实施例4:2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑
按实施例1的一般方法制备为琥珀色树脂状的标题化合物,但其中间体O-硝基偶氮苯的还原是使用催化氢化。
分析:
C30H37N3O的计算值:C,79.1;H,8.2;N,9.2
实测值:C,79.5;H,8.5;N,9.0
实施例5:2-(2-羟基-3-α-枯基-5-叔辛基苯基)2H-苯并三唑
将实施例1的O-硝基偶氮苯化合物催化氢化制备标题化合物,得到灰白色固体。将100g所述固体的样品在100ml异丙醇中重结晶,再在100ml 19∶1的异丙醇∶甲苯中重结晶,最后在100ml9∶1的异丙醇:甲苯中重结晶,得到78g标题化合物,熔点109-111℃。具有与实施例1化合物同样的晶形和X-射线衍射图。
实施例6:2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑
按实施例1的一般方法制备标题化合物,得到琥珀色树脂状产物。
实施例7:2-(2羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑
按实施例1的一般方法制备标题化合物,得到琥珀色树脂状产物
H-NMR数据,在CDCl3中〔ppm〕:0.8-0.9三峰;1.3-1.42单峰;1.9单峰;7.14-7.30多峰;7.44多峰;7.48-7.64不规则双峰;7.86多峰;8.20-8.34-不规则双峰;11.38-11.46单峰;这些与标题化合物一致。
实施例8:2-(2羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑
按实施例1的一般方法制备标题化合物,但其中中间体O-硝基偶氮苯的还原是使用催化氢化,得到琥珀色树脂状产物。
实施例9和10
实施例11:在有机溶剂中的溶解性
要将紫外吸收剂稳定剂掺入高固性热塑性丙烯酸树脂系统,紫外吸收剂必须溶于适当的有机溶剂。到目前为止溶剂如芳香烃,甲苯或二甲苯,对这些紫外吸收剂提供了足够的溶解能力,即使是微溶的2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑。
但是,由于环境的原因这种芳香烃溶剂有逐步淘汰的可能,现在的倾向是高固化涂层和汽车工业日益增长所需的汽车涂层,它最好能用10年,这就是说需要更易溶,非挥发性,且具有紫外吸收剂同样效果的物质。另外,这种紫外吸收剂必须溶于环境可接受的溶剂。
将苯并三唑紫外吸收剂溶于50-100ml五种不同的溶剂直至溶液达到过饱和来测定三种不同的苯并三唑紫外吸收剂在五种典型的有机溶剂中的相对溶解度。过饱和是通过观察苯并三唑开始沉积到测试瓶底判定的。保持过饱和溶液不被破坏过夜。然后倾析出上层溶液过滤。将含有苯并三唑溶于溶剂的滤液分三份按ASTM测试法D2369-81测定固体百分含量三次。高的固体含量表明苯并三唑易溶,所得结果列于下表。
溶解度(以g/100溶剂计* | ||||
溶剂 | A | B | C | D |
二甲苯 | 14 | 76 | >50 | >50 |
乙酸丁酯 | 6 | 33 | >50 | >50 |
甲基戊基酮 | 4 | 33 | >50 | >50 |
丙酮 | n.d. | n.d. | >50 | >50 |
E××ATE600 | 4 | 22 | >50 | >50 |
PM乙酸酯 | 3 | 14 | >50 | >50 |
PM溶剂 | n.d. | 4 | n.d. | n.d. |
*A为2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑(用于对比)
B为实施例5的化合物。
C为实施例4的化合物。
D为实施例8的化合物。
EXXATE600为从Exxon得来的乙酸乙酯。
PM乙酸酯为1-甲氧基-2-丙基乙酸酯。
PM溶剂为1-甲氧基-2-丙醇。
n.d.:未测量。
二甲苯为常用溶剂且已列入HAP′S溶剂(有害的空气污染物)。因此,二甲苯用于各类型的涂层溶剂将快被淘汰,强制使用适当的溶剂替代物将很快进行。
上表中所列的其它溶剂不是现在的调整或废除的目标的溶剂,它们将在涂层工业中更广泛地应用。
现代涂层工业趋向于高固体的涂层,它意味着用很少的溶剂溶解紫外吸收剂。所以,对更易溶,非挥发性的紫外吸收剂的需要变得特别明显。
上表的数据显示,紫外吸收剂A在各种溶剂中的溶解度明显低于紫外吸收剂B-D。事实上,从上表的对比可看出,紫外吸收剂A在除了二甲苯之外的其它溶剂中的溶解度很低,作为在新的长效汽车涂层中的实用性稳定剂已不考虑它。
紫外吸收剂B-D具有紫外吸收剂A显示的同样优秀的非挥发性。这些特性的结合使得紫外吸收剂B-D在长效汽车高固化涂层中作为首选。
实施例12:
在实施例3中制备的无定形的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑与实施例1或5中制备的新的结晶形式的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑相比,在实施例11中所列的不同溶剂中的溶解度基本相同,只是无定形的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑在非-HAPS溶剂中更易溶且溶解快。这在实际应用中,使用实施例3的无定形化合物具有明显的进步。
实施例13:
使用的化合物:
A.2-(2-羟基-3-α-枯基-5-叔辛基苯基)2H-苯并三唑实施例5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4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8的化合物;
D.2-(2-羟基-3,5-二-α-枯基苯基)-2H-苯并三唑,商业上可得的为由Ciba-Geigy Corporntion出品的TinuvinR900(用于对比);
将60份丙烯酸多羟基化合物与40份ResimeneR 747(六甲氧甲基蜜胺,Monsanto)和酸催化剂还有助流剂混合制备透明涂层。底层使用丙烯酸蜜胺。金属银丙烯酸蜜胺底层喷涂约0.6密耳厚。当底层还是湿的时候,向其上喷涂透明涂层,厚度约2密耳。
使用乙酸丁酯(非-HAPS溶剂)为溶剂将试验化合物A-D加到用作透明涂层的模式高固体热塑性丙烯酸尿烷树脂。
下表中图像差异值是将样品暴露于QUV(FD40 Bulbs)数小时得到的。
*I为未被稳定的空白对照;II含有0.24%(重量比)的化合物D;III含有1.2%(重量比)的化合物A;
图像差异 | ||||||||
样品* | 暴露小时数 | |||||||
0 | 896 | 1860 | 2169 | 2468 | 2739 | 2990 | 3300 | |
I | 93 | 23 | 8 | 6 | 3 | 4 | 3 | 3** |
II | 93 | 69 | 38 | 34 | 25 | 29 | 21 | 7** |
III | 94 | 95 | 90 | 88 | 81 | 82 | 68 | 55 |
IV | 91 | 90 | 85 | 85 | 81 | 81 | 80 | 72 |
V | 94 | 95 | 91 | 89 | 74 | 91 | 90 | 88 |
IV含有3%(重量比)的化合物C;且
V含有3%(重量比)的化合物B。
**涂层在此点开裂。
在此试验方法中,紫外吸收剂溶于非-HAPS溶剂乙酸丁酯中,并按一般工业方法加入到树脂系统中。由于化合物D在乙酸丁酯中的有限的溶解度,它只能在涂层中加入占树脂固体重量0.24%的量。化合物A在乙酸丁酯中较大的溶解度使它在涂层中可占到树脂固体重量的1.2%。化合物B和C在乙酸丁酯中的更大的溶解度,使得化合物B或化合物C在涂层中可占到树脂固体重量的3%。
在每种情况下,更易溶的化合物A、B或C与难溶的化合物D相比可提供较大的图像差异。
Claims (15)
1.结晶形式的2-(2-羟基3-α-枯基-5-叔辛基苯基)-2H-苯并三唑,其特征在于其熔点范围为109-111℃,且由Cu-Kα得到的X-射线衍射图的衍射角(2θ)如下:
峰No.
2Θ
峰No.
2Θ
峰No.
2Θ
峰No.
2Θ
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
2.无定形的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑化合物。
4.权利要求3的化合物,其中R为壬基,十二烷基或-CHmCH2COOR4,R4为具有1-12个碳原子的烷基,且m为2。
5.制备权利要求1所述的结晶形式的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑的方法,包括将所述化合物溶于芳香溶剂,并加入低级烷醇沉淀所述化合物,或者仅使用低级烷醇或与使用其与少量芳香溶剂结合来结晶或重结晶所述化合物。
6.权利要求5的方法,它包括单独用具有1-4个碳原子的烷醇或结合使用最多占溶剂总体积15%的芳香溶剂结晶或重结晶所述化合物。
7.权利要求5的方法,其中烷醇是具有2,3,或4个碳原子的烷醇。
8.一种对光化光的不良影响稳定的组合物,它包括:
(a)将受到光化光不良影响的有机材料,和
(b)如权利要求1和2分别描述的无定形的或结晶形式的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑或具有以下通式的化合物,其中R为-CHmCH2mCOOR4,R4为具有1-18个碳原子的烷基,且m为1-4。
9.权利要求8的组合物,其中有机材料为天然的,半合成的或合成的聚合物。
10.权利要求9的组合物,其中聚合物为热塑性聚合物。
11.权利要求9的组合物,其中聚合物为聚烯烃。
12.权利要求8的组合物,它还附加含有酚类抗氧化剂,光稳定剂,加工稳定剂或它们的混合物。
13.权利要求8的组合物,它还附加含有三-芳基-S-三嗪,受阻胺或苯并呋喃-2-酮光稳定剂或它们的混合物。
14.一种稳定有机材料使其能抗光化诱导降解的方法,它包括:
向其中掺入或对其施用如权利要求1和2分别描述的无定形或结晶形式的2-(2-羟基-3-α-枯基-5-叔辛基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5-壬基苯基)-2H-苯并三唑,2-(2-羟基-3-α-枯基-5-十二烷基苯基)-2H-苯并三唑或具有以下通式的化合物,
其中R为CHmCH2mCOOR4,R4为具有1-18个碳原子的烷基,且m为1-4。
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- 1996-04-10 EP EP96810220A patent/EP0738718A1/en not_active Withdrawn
- 1996-04-10 GB GB9607427A patent/GB2299957B/en not_active Expired - Lifetime
- 1996-04-16 DE DE19615000A patent/DE19615000A1/de not_active Ceased
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- 1996-04-19 JP JP8122465A patent/JPH08291151A/ja active Pending
- 1996-05-14 TW TW085105661A patent/TW419497B/zh not_active IP Right Cessation
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CN1996062B (zh) * | 2006-01-06 | 2010-09-01 | 住友化学株式会社 | 多层光漫射板 |
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