CN1314739C - 对热、氧化或光致降解稳定的组合物、稳定混合物及其制备方法 - Google Patents
对热、氧化或光致降解稳定的组合物、稳定混合物及其制备方法 Download PDFInfo
- Publication number
- CN1314739C CN1314739C CNB981156037A CN98115603A CN1314739C CN 1314739 C CN1314739 C CN 1314739C CN B981156037 A CNB981156037 A CN B981156037A CN 98115603 A CN98115603 A CN 98115603A CN 1314739 C CN1314739 C CN 1314739C
- Authority
- CN
- China
- Prior art keywords
- butyl
- triazine
- phenyl
- tert
- hydroxyl
- 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
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- 238000006243 chemical reaction Methods 0.000 claims description 21
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims description 18
- 125000002347 octyl 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])[H] 0.000 claims description 16
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08K5/34—Heterocyclic compounds having nitrogen in the ring
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
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Abstract
在标题表明的化合物的混合物、其纯异构体和烷桥接的衍生物在稳定聚合物组合物、特别是聚烯烃组合物中特别有效。
Description
本发明涉及选择的N,N’,N-三-{2,4-二[(1-烃氧基-2,2,6,6-四-甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺、其纯异构体和桥接的衍生物以及用其稳定的聚合物组合物。
由于该化合物的低碱性,在聚合物组合物的稳定中有特殊的价值,在聚合物组合物中,碱性大的受阻胺稳定剂由于与聚合物基体的相互作用而使其活性显著降低。本发明化合物对其特别有效的聚烯烃组合物实例包括阻燃剂聚烯烃,其中来自卤化的阻燃剂分解的酸残余物使常规受阻胺稳定剂失去活性;温室薄膜和农用覆盖薄膜,其中来自农药的酸残余物干扰常规受阻胺稳定剂的活性;热塑性聚烯烃,其中与碱性受阻胺稳定剂的相互作用干扰了基体的着色。
通过式I表示、其中R1-R4都是E的N,N’,N”,N-四取代的受阻胺在美国专利5004770、5096950、5204473、5112890和5124378、欧洲专利申请309402A1中已经作为低碱性、与聚合物不相互作用的稳定剂获得专利,用于各种环境和热固性汽车涂料、聚烯烃和非聚烯烃应用中。特别地,Winter等人在美国专利5204473的实施例62和67中分别描述了N,N’,N”,N-四{2,4-二[(1-环己基氧基-2,2,6,6-四-甲基哌啶-4-基)丁基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺和其辛基氧基类似物。同一专利还在权利要求25中要求保护1-甲氧基类似物。上述专利中没有一份对这些四取代-s-三嗪受阻胺稳定剂在任何有机基体中的任何特性数据有所描述。
本发明与现有技术不同,本发明化合物在四胺骨架上有一个未取代的氮原子。另外,包括描述了低聚的N-烃氧基受阻胺稳定剂的美国专利5015682的现有技术中没有一个公开了下面式II和III描述的桥接结构。
本发明涉及混合物N,N’,N-三-{2,4-二[(1-烃氧-2,2,6,6-四-甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺;N,N’,N-三-{2,4-二[(1-烃氧基-2,2,6,6-四-甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺和桥接的衍生物如式I、II、IIA和III所示
R1NH-CH2CH2CH2NR2CH2CH2NR3CH2CH2CH2NHR4 (I)
T-E1-T1 (II)
T-E1 (IIA)
G-E1-G1-E1-G2 (III)
E是
E1是
其中在式I的四胺中,
R1和R2是s-三嗪部分E;R3和R4之一是s-三嗪部分E,同时R3和R4另一个是氢,
R是甲基、环己基或辛基,优选环己基或辛基,
R5是1-12个碳原子的烷基,优选正丁基;
其中式II或IIA的化合物当R是环己基或辛基时,T和T1分别是被如上为式I定义的R1-R4取代的四胺,其中
(1)每个四胺中s-三嗪部分E之一被基团E1代替,其在两个四胺T和T1之间形成一个桥,或
(2)基团E1可如在式IIA中一样在相同的四胺T中都有终端,其中四胺的两个E部分被一个E1基团代替,或
(3)四胺T的所有三个s-三嗪取代基可以是E1,从而一个E1连接T和T1,并且第二个E1在四胺T中有两个终端,
L是环己烷二基或辛烷二基;
其中在式III化合物中,
G、G1、和G2分别是被如上为式I定义的R1-R4取代的四胺,除了G和G2分别有一个s-三嗪部分E被基团E1代替,G1有两个三嗪部分E被基团E1代替,从而在G和G1之间形成一个桥,在G1和G2之间形成第二个桥。
假定在分子之间没有桥接,式I的化合物有两种可能的异构体。这两种异构体用下列表表示。
异构体 R1 R2 R3 R4
1 E E H E
2 E E E H
通过2-4当量的2,4-二[(1-烃氧基-2,2,6,6-哌啶-4-基)丁基氨基]-6-氯-s-三嗪与1当量的N,N’-二-(3-氨基丙基)亚乙基二胺反应,特别是通过2-4当量的2,4-二[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)烷基氨基]-6-氯-s-三嗪与1当量的N,N’-二-(3-氨基丙基)亚乙基二胺在有酸受体——诸如氢氧化钠水溶液,用于中和反应中生成的盐酸——的烃溶剂中反应,有益地制备本发明的化合物混合物。在美国专利5216156和5204473中描述了2,4-二[(1-烃氧基-2,2,6,6-四-甲基哌啶-4-基)烷基氨基]-6-氯-s-三嗪各种离析物的合成。
在一个优选的方法中,2.5-3当量的s-三嗪、特别是3当量的s-三嗪与1当量的胺反应。
在2,4-二[(1-烃氧基-2,2,6,6-四-甲基哌啶-4-基)烷基氨基]-6-氯-s-三嗪优选的合成方法中,如美国专利4921962所述,加热相应的受阻胺取代的6-氯-s-三嗪与四丁基过氧化氢、金属氧化物催化剂、适合的烃溶剂的混合物直到排出红色的硝酰基中间产物。在一些情况下,二硝酰基自由基将结合相同的溶剂分子。这是桥接的物质被上述式II和III消耗的原因。本发明的N-甲氧基化合物不含这些桥接结构,因为使用了不同的合成方法制备1-甲氧基取代的受阻胺。
美国专利5204473描述了在四取代的s-三嗪受阻胺起始物上引入1-环己氧基或1-辛氧基取代基。本发明的三取代的化合物不同于现有技术的四取代的化合物,因为它们通过下文所述的不同的路线制备。即使使用4当量氯-s-三嗪中间产物,产物混合物的大多数也是三取代的。使用少到2当量的氯-s-三嗪中间产物还是能得到一些三取代的产物。
这里的术语“烃氧基”主要指甲氧基、环己氧基或辛氧基。在式I-III化合物中和由本发明方法生成的产物中,R通常是环己基或辛基,在式I化合物中还表示甲基。
优选式I-III化合物的混合物,其中R是环己基或辛基,特别是如式I、II、IIA和III所示的N,N’,N-三-{2,4-二[(1-环己氧基-2,2,6,6-四-甲基哌啶-4-基)正丁基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺;N,N’,N”-三-{2,4-二[(1-环己氧基-2,2,6,6-四-甲基哌啶-4-基)正丁基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺和桥接的衍生物的混合物。
还涉及如式I、II、IIA和III所示的N,N’,N-三-{2,4-二[(1-辛氧基-2,2,6,6-四-甲基哌啶-4-基)正丁基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺;N,N’,N”-三-{2,4-二[(1-辛氧基-2,2,6,6-四-甲基哌啶-4-基)正丁基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺和桥接的衍生物的混合物。技术上还涉及如式I、II、IIA和III所示的N,N’,N-三-{2,4-二[(1-甲氧基-2,2,6,6-四-甲基哌啶-4-基)正丁基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺;N,N’,N”-三-{2,4-二[(1-甲氧基-2,2,6,6-四-甲基哌啶-4-基)正丁基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺和桥接的衍生物的混合物。
作为烷基的R5表示甲基、乙基、丙基——诸如正丙基或异丙基、丁基——诸如正丁基、异丁基、仲丁基和叔丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基;优选丁基,特别是正丁基。
式I-III的化合物特别适合作为稳定剂用于有机材料抗热、抗氧化或抗光致降解;它们还可作为阻燃剂。因此,本发明还涉及一种对热、氧化或光致降解稳定的组合物,其含有,
(a)易热、氧化或光致降解的有机材料,和
(b)有效稳定量的式I、II、IIA或III化合物。
优选有机材料是天然的、半合成的或合成的聚合物,特别是热塑性的聚合物。
最优选聚合物是聚烯烃、热塑性烯烃或聚碳酸酯。特别重要的是聚烯烃,尤其是聚乙烯或聚丙烯。
当存在于一种被稳定的组合物中时,本发明的化合物有较高的水解稳定性、处理和储存稳定性以及好的抗萃取性。
在现有技术中描述了制备本发明化合物的方法。制备该化合物的中间体大都可从市场获得。
一般可被稳定化的聚合物包括
1.单烯烃和二烯烃的聚合物,例如聚丙烯、聚异丁烯、聚-1-丁烯、聚-4-甲基-1-戊烯、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的聚合物,聚乙烯(可任意交联),例如高密度聚乙烯(HDPE)、低密度聚乙烯(LDPE)、线形低密度聚乙烯(LLDPE)、支化低密度聚乙烯(BLDPE)。
聚烯烃,即上述例举的单烯烃聚合物,优选聚乙烯和聚丙烯,可用不同的方法制备,特别是用下列方法制备:
a)自由基聚合(通常在高压高温下)。
b)催化聚合,使用一般含有一种或多于一种周期表IVb、Vb、VIb或VIII族的金属的催化剂。这些金属一般有一个或多于一个的配位体、一般氧化物、卤化物、醇化物、酯类、醚类、胺类、烷基化物、链烯基化物、环烯基化物、环戊二烯化物和/或芳基化物,其可π-或σ-配位。这些金属配合物可以是自由形式或载于基体上,一般载于活化的氯化镁、氯化钛(III)、氧化铝或二氧化硅上。这些催化剂在聚合介质中可以是可溶性的或不溶性的。催化剂可在聚合反应中单独使用或还使用其它活化剂,一般为金属烷基化物、金属氢化物、金属烷基卤化物、金属烷基氧化物或金属烷基烷,或提供非配位阴离子的化合物,诸如三(五氟苯基)硼,所述金属是元素周期表的Ia、IIa和/或IIIa族元素。该活化剂可进一步被酯、醚、胺或甲硅烷基团方便地改进。这些催化剂体系一般称为Phillips、Standard Oil Indiana、Ziegler(-Natta)、TNZ(DuPont)、可限形状催化剂工艺CGCT(Dow)、茂金属或单点催化剂(SSC)。
2.在1)中描述的聚合物的混合物,例如聚丙烯与聚异丁烯的混合物、聚丙烯与聚乙烯的混合物(例如PP/HDPE、PP/LDPE)和不同类型的聚乙烯的混合物(例如LDPE/HDPE)。
3.单烯烃和二烯烃彼此的共聚物或与其它乙烯基单体的共聚物,例如乙烯/丙烯共聚物、线形低密度聚乙烯(LLDPE)和其与低密度聚乙烯(LDPE)的混合物、丙烯/1-丁烯共聚物、丙烯/异丁烯共聚物、乙烯/1-丁烯共聚物、乙烯/己烯共聚物、乙烯/甲基戊烯共聚物、乙烯/庚烯共聚物、乙烯/辛烯共聚物、丙烯/丁二烯共聚物、异丁烯/异戊二烯共聚物、乙烯/丙烯酸烷基酯共聚物、乙烯/甲基丙烯酸烷基酯共聚物、乙烯/乙酸乙烯酯共聚物和它们与一氧化碳的共聚物或乙烯/丙烯酸共聚物及其盐(离聚物)以及乙烯与丙烯和一种二烯烃——诸如己二烯、二环戊二烯或亚乙基降冰片烯——的三元共聚物;和这类共聚物与彼此的混合物和其与在上述1)中描述的聚合物的混合物,例如聚丙烯/乙烯-丙烯共聚物、LDPE/乙烯-乙酸乙烯酯共聚物(EVA)、LDPE/乙烯-丙烯酸共聚物(EAA)、LLDPE/EVA、LLDPE/EAA和交替或无规聚链烯烃/一氧化碳共聚物和其与其它聚合物——例如聚酰胺——的混合物。
4.烃树脂(例如C5-C9)包括其氢化的变体(例如粘合剂)和聚链烯烃与淀粉的混合物。
5.聚苯乙烯、聚(对甲基苯乙烯)、聚(α-甲基苯乙烯)。
6.苯乙烯或α-甲基苯乙烯与二烯烃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/甲基丙烯酸烷基酯/苯乙烯/丁二烯/丙烯酸烷基酯、苯乙烯/丁二烯/甲基丙烯酸烷基酯、苯乙烯/马来酸酐、苯乙烯/丙烯腈/丙烯酸甲酯;高冲击强度的苯乙烯共聚物和另一种聚合物——例如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三元共聚物——的混合物;苯乙烯的嵌段共聚物,诸如苯乙烯/丁二烯/苯乙烯、苯乙烯/异戊二烯/苯乙烯、苯乙烯/乙烯/丁烯/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。
7.苯乙烯或α-甲基苯乙烯的接枝共聚物,例如苯乙烯在聚丁二烯上、苯乙烯在聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物上;苯乙烯和丙烯腈(或甲基丙烯腈)在聚丁二烯上;苯乙烯、丙烯腈和甲基丙烯酸甲酯在聚丁二烯上;苯乙烯和马来酸酐在聚丁二烯上;苯乙烯、丙烯腈和马来酸酐或马来酰亚胺在聚丁二烯上;苯乙烯和马来酰亚胺在聚丁二烯上;苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯在聚丁二烯上;苯乙烯和丙烯腈在乙烯/丙烯/二烯三元聚合物上;苯乙烯和丙烯腈在聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上、苯乙烯和丙烯腈在丙烯酸酯/丁二烯共聚物上,以及它们与6)中所列共聚物的混合物,例如已知为ABS、MBS、ASA或AES聚合物共聚物混合物。
8.含卤聚合物,诸如聚氯丁二烯、氯化橡胶、氯化或氯磺化的聚乙烯、乙烯和氯化乙烯的共聚物、表氯醇均聚物和共聚物。特别是含卤素乙烯基化合物的聚合物,例如聚氯乙烯、聚(1,2-二氯乙烯)、聚氟乙烯、聚(1,2-二氟乙烯)以及它们的共聚物,诸如氯乙烯/1,2-二氯乙烯、氯乙烯/乙酸乙烯酯或1,2-二氯乙烯/乙酸乙烯酯共聚物。
9.从α,β-不饱和酸和其衍生物衍生的聚合物,诸如聚丙烯酸酯和聚甲基丙烯酸酯;聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈,由丙烯酸丁酯冲击改性。
10.在9)描述的单体彼此或与其它不饱和单体的共聚物,例如丙烯腈/丁二烯共聚物、丙烯腈/丙烯酸烷基酯共聚物、丙烯腈/丙烯酸烷氧基烷基酯或丙烯腈/乙烯基卤共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元聚合物。
11.从不饱和醇和胺或酰基衍生物或其乙缩醛衍生的聚合物。例如聚乙烯基醇、聚乙酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙酯或聚烯丙基三聚氰胺;以及它们与上述1)中的烯烃的共聚物。
12.环醚的均聚物和共聚物,诸如聚亚烷基二醇、聚环氧乙烷、聚环氧丙烷或其与二缩水甘油基醚的共聚物。
13.聚缩醛,诸如聚甲醛和含环氧乙烷作为共聚单体的那些聚甲醛;被热塑性聚氨基甲酸酯、丙烯酸酯或MBS改性的聚缩醛。
14.聚苯醚、聚苯硫醚、聚苯醚与苯乙烯聚合物或聚酰胺的混合物。
15.一方面从羟基终端的聚醚、聚酯或聚丁二烯和另一方面从脂族或芳族聚异氰酸酯衍生的聚氨基甲酸酯以及其前体。
16.从二胺和二羧酸和/或从氨基羧酸或相应的内酰胺衍生的聚酰胺和共聚酰胺,例如聚酰胺4、聚酰胺6、聚酰胺6/6、6/10、6/9、6/12、4/6、12/12、聚酰胺11、聚酰胺12、从m-二甲苯二胺和己二酸生成的芳族聚酰胺;从六亚甲基二胺和间苯二酸或/和对苯二酸在有或没有一种弹性体作为改性剂条件下制备的聚酰胺,例如聚-2,4,4-三甲基六亚甲基对苯二酰胺或聚间亚苯基间苯二酰胺;还有上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学键合的或接枝的弹性体的嵌段共聚物;或与聚醚,例如与聚乙二醇、聚丙二醇或聚-1,4-丁二醇的嵌段共聚物;以及被EPDM或ABS改性的聚酰胺或共聚酰胺;在处理中缩合的聚酰胺(RIM聚酰胺体系)。
17.聚脲、聚酰亚胺、聚酰胺-酰亚胺和聚苯并咪唑。
18.从二羧酸和二醇和/或从羟基羧酸或相应的内酯衍生的聚酯,例如聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚-1,4-二羟甲基环己烷对苯二甲酸酯和聚羟基苯甲酸酯以及从羟基终端的聚醚衍生的嵌段共聚醚酯;还有被聚碳酸酯或MBS改性的聚酯。
19.聚碳酸酯和聚酯碳酸酯。
20.聚砜、聚醚砜和聚醚酮。
21.一方面从醛类和另一方面从酚类、脲和密胺衍生的交联聚合物,诸如苯酚/甲醛树脂、尿素/甲醛树脂和密胺/甲醛树脂。
22.干的或不干的醇酸树脂。
23.从饱和的和不饱和的二羧酸与多元醇在乙烯基化合物作为交联剂条件下衍生的不饱和聚酯树脂,还有其低可燃性的含卤改性体。
24.从取代的丙烯酸酯衍生的可交联的丙烯酸树脂,例如环氧化的丙烯酸酯、氨基甲酸酯丙烯酸酯或聚酯丙烯酸酯。
25.与密胺树脂、尿素树脂、聚异氰酸酯或环氧树脂交联的醇酸树脂、聚酯树脂和丙烯酸酯树脂。
26.从聚环氧化物衍生的交联的环氧树脂,例如从二缩水甘油醚或从环脂族双环氧化物衍生的。
27.天然聚合物,诸如纤维素、橡胶、明胶和其化学改性的同系物衍生物,例如乙酸纤维素酯、丙酸纤维素酯和丁酸纤维素酯,或纤维素醚,诸如甲基纤维素;以及松香和其衍生物。
28.上述聚合物的混合物(polyblend),例如PP/EPDM、聚酰胺/EPDM或ABS、PVC/EVA、PVC/ABS、PVC/MBS、PC/ABS、PBTP/ABS、PC/ASA、PC/PBT、PVC/CPE、PVC/丙烯酸酯、POM/热塑性PUR、PC/热塑性PUR、POM/丙烯酸酯、POM/MBS、PPO/HIPS、PPO/PA6.6和共聚物、PA/HDPE、PA/PP、PA/PPO。
29.天然的和合成的有机物质,是纯单体的化合物或这类化合物的混合物,例如矿物油、动物和蔬菜脂肪油和蜡、或基于合成酯(例如苯二甲酸酯、己二酸酯、磷酸酯或苯三酸酯)的油、脂肪和蜡还有合成酯与矿物油以任何重量比的混合物,一般用作纺丝组合物的那些,以及这类物质的含水乳状液。
30.天然的或合成的橡胶的含水乳状液,例如天然胶乳或羧化苯乙烯/丁二烯共聚物的胶乳。
31.聚硅氧烷,诸如在例如美国专利4259467中描述的柔软的亲水聚硅氧烷;例如在美国专利4355147中描述的硬聚有机硅氧烷。
32.与不饱和丙烯酸聚乙酰乙酸酯树脂或与不饱和丙烯酸树脂结合的聚酮亚胺。不饱和的丙烯酸树脂包括聚氨酯丙烯酸酯、聚醚丙烯酸酯、有不饱和侧基的乙烯基或丙烯酰基共聚物和丙烯酸化的密胺。在酸催化剂存在下由聚胺和酮制备聚酮亚胺。
33.可辐射固化的组合物,含烯键不饱和单体或低聚物和聚不饱和脂族低聚物。
34.环氧密胺树脂,诸如被环氧官能共醚化的高固体密胺树脂——诸如LSE-4103(Monsanto)——交联的光稳定性环氧树脂。
一般本发明的化合物以被稳定组合物重量的约0.005-5%使用,尽管用量会随特定的基体和应用而变化。有益的范围是约0.01-3%,特别是约0.05-2%;最优选的范围是0.05-1%。
本发明的稳定剂可容易地用常规技术、在制备成型之前以任何常规工艺与有机聚合物结合。例如,稳定剂可与聚合物以干燥粉末的形式混合,或可将稳定剂的悬浮液或乳状液与聚合物的溶液、悬浮液或乳状液混合。生成的本发明的被稳定的聚合物组合物可任意地含有重量百分比约0.005-5%、优选约0.01或0.025-2%、特别是约0.1-1%的各种常规添加剂,诸如下列材料或其混合物。
1.抗氧化剂
1.1烷基化的单酚类,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-甲氧基甲基苯酚、壬基苯酚,其在侧链为线形或支化的,例如2,6-二壬基-4-甲基苯酚、2,4-二甲基-6-(1’-甲基十一烷-1’-基)-苯酚、2,4-二甲基-6-(1’-甲基十七烷-1’-基)苯酚、2,4-二甲基-6-(1’-甲基十三烷-1’-基)-苯酚和其混合物。
1.2烷基硫代甲基苯酚,例如2,4-二辛基硫代甲基-6-叔丁基苯酚、2,4-二辛基硫代甲基-6-甲基苯酚、2,4-二辛基硫代甲基-6-乙基苯酚、2,6-二十二烷基硫代甲基-4-壬基苯酚。
1.3氢醌和烷基化的氢醌,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、2,6-二叔丁基氢醌、2,5-二叔丁基-4-羟基苯甲醚、3,5-二叔丁基-4-羟基苯甲醚、3,5-二叔丁基-4-羟基苯基硬脂酸酯、二-(3,5-二叔丁基-4-羟基苯基)己二酸酯。
1.4生育酚,例如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚和其混合物(维生素E)。
1.5羟基化的硫代二苯基醚,例如2,2’-硫代二(6-叔丁基-4-甲基苯酚)、2,2,-硫代二(4-辛基苯酚)、4,4’-硫代二(6-叔丁基-3-甲基苯酚)、4,4’-硫代二(6-叔丁基-2-甲基苯酚)、4,4’-硫代二(3,6-二仲戊基苯酚)、4,4’-二(2,6-二甲基-4-羟基苯基)二硫醚。
1.6亚烷基二苯酚,例如2,2’-亚甲基二(6-叔丁基-4-甲基苯酚)、2,2’-亚甲基二(6-叔丁基-4-乙基苯酚)、2,2’-亚甲基二[4-甲基-6-(α-甲基环己基)苯酚]、2,2’-亚甲基二(4-甲基-6-环己基苯酚)、2,2’-亚甲基二(6-壬基-4-甲基苯酚)、2,2’-亚甲基二(4,6-二叔丁基苯酚)、2,2’-亚乙基二(4,6-二叔丁基苯酚)、2,2’-亚乙基二(6-叔丁基-4-异丁基苯酚)、2,2’-亚甲基二[6-(α-甲基苄基)-4-壬基苯酚]、2,2’-亚甲基二[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4’-亚甲基二(2,6-二叔丁基苯酚)、4,4’-亚甲基二(6-叔丁基-2-甲基苯酚)、1,1-二(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、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、乙二醇二[3,3-二(3’-叔丁基-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]对苯二甲酸酯、1,1-二(3,5-二甲基-2-羟基苯基)丁烷、2,2-二(3,5-二叔丁基-4-羟基苯基)丙烷、2,2-二(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基巯基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.7O-、N-和S-苄基化合物,例如3,5,3’,5’-四叔丁基-4,4’-二羟基二苄基醚、十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯、三癸基-4-羟基-3,5-二叔丁基苄基巯基乙酸酯、三(3,5-二叔丁基-4-羟基苄基)胺、二(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二酸酯、二(3,5-二叔丁基-4-羟基苄基)硫醚、异辛基-3,5-二叔丁基-4-羟基苄基巯基乙酸酯。
1.8羟基苄基化的丙二酸酯,例如二(十八烷基)-2,2-二(3,5-二叔丁基-2-羟基苄基)-丙二酸酯、二(十八烷基)-2-(3-叔丁基-4-羟基-5-甲基苄基)-丙二酸酯、二(十二烷基巯基乙基-2,2-二(3,5-二叔丁基-4-羟基苄基)-丙二酸酯、二[4-(1,1,3,3-四甲基丁基)苯基]-2,2-二(3,5-二叔丁基-4-羟基苄基)-丙二酸酯。
1.9芳族羟基苄基化合物,例如1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯、1,4-二(3,5-二叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯酚。
1.10三嗪化合物,例如2,4-二(辛基巯基)-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-二(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-二(3,5-二叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二叔丁基-4-羟基苯氧基)-1,2,3-三嗪、1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯、2,4,6-三(3,5-二叔丁基-4-羟基苯基乙基)-1,3,5-三嗪、1,3,5-三(3,5-二叔丁基-4-羟基苯基丙酰基)-六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟基苄基)异氰脲酸酯。
1.11苄基膦酸酯,例如二甲基-2,5-二叔丁基-4-羟基苄基膦酸酯、二乙基-3,5-二叔丁基-4-羟基苄基膦酸酯、二(十八烷基)-3,5-二叔丁基-4-羟基苄基膦酸酯、二(十八烷基)-5-叔丁基-4-羟基-3-甲基苄基膦酸酯、3,5-二叔丁基-4-羟基苄基膦酸的单乙基酯的钙盐。
1.12酰氨基酚,例如4-羟基-N-月桂酰苯胺、4-羟基-N-硬脂酰苯胺、辛基-N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸酯。
1.13β-(3,5-二叔丁基-4-羟基苯基)丙酸与单醇或多元醇的酯,例如与甲醇、乙醇、正辛醇、异辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟基乙基)异氰脲酸酯、N,N’-二(羟基乙基)草酰胺、3-硫代十一醇、3-硫代十五醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷。
1.14β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与单醇或多元醇的酯,例如与甲醇、乙醇、正辛醇、异辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟基乙基)异氰脲酸酯、N,N’-二(羟基乙基)草酰胺、3-硫代十一醇、3-硫代十五醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷。
1.15β-(3,5-二环己基-4-羟基苯基)丙酸与单醇或多元醇的酯,例如与甲醇、乙醇、辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟基乙基)异氰脲酸酯、N,N’-二(羟基乙基)草酰胺、3-硫代十一醇、3-硫代十五醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷。
1.163,5-二叔丁基-4-羟基苯基乙酸与单醇或多元醇的酯,例如与甲醇、乙醇、辛醇、十八醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟基乙基)异氰脲酸酯、N,N’-二(羟基乙基)草酰胺、3-硫代十一醇、3-硫代十五醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷。
1.17β-(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-羟基苯基丙酰基)六亚甲基二酰胺、N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰基)三亚甲基二酰胺、N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰基)肼、N,N’-二[2-(3-[3,5-二叔丁基-4-羟基苯基]丙酰基氧基)乙基]草酰胺(NaugardXL-1,Uniroyal提供)。
1.18抗坏血酸(维生素C)
1.19胺抗氧化剂,例如N,N’-二异丙基对亚苯基二胺、N,N’-二仲丁基对亚苯基二胺、N,N’-二(1,4-二甲基戊基)对亚苯基二胺、N,N’-二(1-乙基-3-甲基戊基)对亚苯基二胺、N,N’-二(1-甲基庚基)对亚苯基二胺、N,N’-二环己基对亚苯基二胺、N,N’-二苯基对亚苯基二胺、N,N’-二(2-萘基)对亚苯基二胺、N-异丙基-N’-苯基对亚苯基二胺、N-(1,3-二甲基丁基)-N’-苯基对亚苯基二胺、N-(1-甲基庚基)-N’-苯基对亚苯基二胺、N-环己基-N’-苯基对亚苯基二胺、4-(对甲苯亚磺酰基)二苯基胺、N,N’-二甲基-N,N’-二仲丁基对亚苯基二胺、二苯基胺、N-烯丙基二苯基胺、4-异丙氧基二苯基胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺、辛基化的二苯胺,例如对,对’-二叔辛基二苯基胺、4-正丁基氨基苯酚、4-丁酰氨基苯酚、4-壬酰氨基苯酚、4-十二酰氨基苯酚、4-十八酰氨基苯酚、二(4-甲氧基苯基)胺、2,6-二叔丁基-4-二甲基氨基甲基苯酚、2,4’-二氨基二苯基甲烷、4,4′-二氨基二苯基甲烷,N,N,N′,N′-四甲基-4,4′-二氨基二苯基甲烷、1,2-二[(2-甲基苯基)氨基]乙烷、1,2-二(苯基氨基)丙烷、(邻甲苯基)双胍、二[4-(1’,3’-二甲基丁基)苯基]胺、叔辛基化的N-苯基-1-萘胺,单-和二烷基化的叔丁基/叔辛基二苯基胺的混合物、单-和二烷基化的壬基二苯基胺的混合物、单-和二烷基化的十二烷基二苯基胺的混合物、单-和二烷基化的异丙基/异己基二苯基胺的混合物、单-和二烷基化的叔丁基二苯基胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单-和二烷基化的叔丁基/叔辛基吩噻嗪的混合物、单-和二烷基化的叔辛基吩噻嗪的混合物、N-烯丙基吩噻嗪、N,N,N’,N’-四苯基-1,4-二氨基-2-丁烯、N,N-二(2,2,6,6-四甲基-哌啶-4-基)-六亚甲基二胺、二(2,2,6,6-四甲基-哌啶-4-基)-癸二酸酯、2,2,6,6-四甲基-哌啶-4-酮、2,2,6,6-四甲基-哌啶-4-醇。
2.UV吸收剂和光稳定剂
2.12-(2’-羟基苯基)苯并***,例如2-(2’-羟基-5’-甲基苯基)苯并***、2-(3’,5’-二叔丁基-2’-羟基苯基)苯并***、2-(5’-叔丁基-2’-羟基苯基)苯并***、2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并***、2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯苯并***、2-(3’-仲丁基-5’-叔丁基-2’-羟基苯基)苯并***、2-(2’-羟基-4’-辛氧基苯基)苯并***、2-(3’,5’-二叔戊基-2’-羟基苯基)苯并***、2-(3’,5’-二(α,α-二甲基苄基)-2’-羟基苯基)苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)苯基)-5-氯苯并***、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***、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)-苯基)-5-氯苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)-苯基)苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-辛氧基羰基乙基)-苯基)苯并***、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)苯并***、2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并***、2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧基羰基乙基)苯基苯并***、2,2’-亚甲基-二[4-(1,1,3,3,-四甲基丁基)-6-苯并***-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***与聚乙二醇300的酯基转移反应产物;[R-CH2CH2-COO-CH2CH2-]2-,其中R=3’-叔丁基-4’-羟基-5’-2H-苯并***-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***,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***。
2.22-羟基二苯酮,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取代的和未取代的苯甲酸的酯,例如4-叔丁基苯基水杨酸酯、苯基水杨酸酯、辛基苯基水杨酸酯、二苯甲酰间苯二酚、二(4-叔丁基苯甲酰基)间苯二酚、苯甲酰间苯二酚、2,4-二叔丁基苯基3,5-二叔丁基-4-羟基苯甲酸酯、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、2-甲基-4,6-二叔丁基苯基3,5-二叔丁基-4-羟基苯甲酸酯。
2.4丙烯酸酯,例如α-氰基-β,β-二苯基丙烯酸乙基酯、α-氰基-β,β-二苯基丙烯酸异辛酯、α-甲酯基肉桂酸甲酯、α-氰基-β-甲基对甲氧基肉桂酸甲酯、α-氰基-β-甲基对甲氧基肉桂酸丁酯、α-甲酯基对甲氧基肉桂酸甲酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5镍化合物,例如镍的2,2’-硫-二[4-(1,1,3,3-四甲基丁基)苯酚]配合物,诸如1∶1或1∶2配合,有或没有附加的诸如正丁基胺、三乙醇胺或N-环己基二乙醇胺的配体;镍的二丁基二硫氨基甲酸盐;单烷基酯的镍盐,例如4-羟基-3,5-二叔丁基苄基膦酸的甲基或乙基酯;酮肟的镍配合物。例如2-羟基-4-甲基苯基十一烷基酮肟的镍配合物;镍的1-苯基-4-月桂酰基-5-羟基吡唑的配合物,有或没有附加的配体。
2.6立体受阻胺,例如二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、二(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯、二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、二(1,2,2,6,6-五甲基-4-哌啶基)正丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯、1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶和癸二酸的缩合物、N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5三嗪的线形或环状缩合物、三(2,2,6,6-四甲基-4-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-乙二基)-二(3,3,5,5-四甲基哌嗪酮)、4-苯甲酰-2,2,6,6-四甲基哌啶、4-十八烷氧基-2,2,6,6-四甲基哌啶、二(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸-2,4-二酮、二(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、二(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯、N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5三嗪的线形或环状缩合物、2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物、2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物、8-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-2,4-二酮、3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮、3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮、4-十六烷氧基-2,2,6,6-四甲基哌啶和4-十八烷氧基-2,2,6,6-四甲基哌啶的混合物、N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5三嗪的缩合物、1,2-二(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5三嗪以及4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS Reg.No.[136504-96-6]);N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧-螺[4.5]癸烷、7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧螺[4.5]癸烷与表氯醇的反应产物、1,1-二(1,2,2,6,6-五甲基-4-哌啶基氧羰基)-2-(4-甲氧基苯基)乙烷、N,N’-二甲酰-N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺、4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯、聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-哌啶基)硅氧烷、马来酸酐-α-烯烃共聚物与2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物。
2.7草酰胺,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’-乙基草酰胺、N,N’-二(3-二甲基氨基苯基)草酰胺、2-乙氧基-5-叔丁基-2’-乙基草酰胺和其与2-乙氧基-2’-乙基-5,4’-二叔丁基草酰胺的混合物、邻-和对-甲氧基-二取代的草酰胺和混合物和邻-和对-乙氧基取代的草酰胺的混合物。
2.82-(2-羟基苯基)-1,3,5-三嗪,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]-,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)-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、2-(2-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪、2-{2-羟基-4-[3-(2-乙基己基-1-氧基)-2-羟基丙氧基]苯基}-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属减活化剂,例如N,N’-二苯基草酰胺、N-水杨醛-N’-水杨酰肼、N,N’-二(水杨酰基)肼、N,N’-二(3,5-二叔丁基-4-羟基苯基丙酰基)肼、3-水杨酰氨基-1,2,4-***、二(亚苄基)草酰二酰肼、N,N’-草酰二苯胺、间苯二酰二酰肼、癸二酰联苯基酰肼、N,N’-二乙酰己二酰二酰肼、N,N’-二(水杨酰)草酰二酰肼、N,N’-二(水杨酰)硫代丙酰二酰肼。
4.亚磷酸酯和亚膦酸酯,例如三苯基亚磷酸酯、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(十八烷基)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、二(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、二异癸氧基季戊四醇二亚磷酸酯、二(2,4-二叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯、二(2,4,6-三(叔丁基苯基)季戊四醇二亚磷酸酯、三(十八烷基)山梨醇三亚磷酸酯、四(2,4-二叔丁基苯基)4,4’-联亚苯基二亚膦酸酯、6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂膦辛英、6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂膦辛英、二(2,4-二叔丁基-6-甲基苯基)甲基亚磷酸酯、二(2,4-二叔丁基-6-甲基苯基)乙基亚磷酸酯、2,2’,2”-次氮基[三乙基三(3,3’,5,5’-四叔丁基-1,1’联苯基-2,2’-二基)亚磷酸酯]、2-乙基己基(3,3’,5,5’-四叔丁基-1,1’联苯基-2,2’-二基)亚磷酸酯。
特别优选的是下列亚磷酸酯:
三(2,4-二叔丁基苯基)亚磷酸酯(Irgafos168,Ciba-Geigy),三(壬基苯基)亚磷酸酯,
5.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(十六烷基)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、从氢化的牛脂胺衍生的N,N-二烷基羟胺。
6.硝酮(nitrones),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、氢化的牛脂胺衍生的N,N’-二烷基羟胺衍生的硝酮。
7.硫代增效剂,例如硫代二丙酸二月桂酯或硫代二丙酸二(十八烷基)酯。
8.过氧化物净化剂,例如β-硫代二丙酸的酯,例如月桂酯、十八烷基酯、十四烷基酯、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、四(β-十二烷基巯基)丙酸季戊四醇酯。
9.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。
10.碱性共稳定剂,例如密胺、聚乙烯基吡咯烷酮、双氰胺、氰脲酸三烯丙基酯、脲衍生物、肼衍生物、胺、聚酰胺、聚氨基甲酸酯、碱金属和碱土金属的高级脂肪酸的盐,例如硬脂酸钙、硬脂酸锌、山嵛酸镁、硬脂酸镁、蓖麻酸钠和软脂酸钾、儿茶酸锑或儿茶酸锌。
11.成核剂,例如无机物质,诸如滑石,金属氧化物,诸如二氧化钛或氧化镁,磷酸盐、碳酸盐或硫酸盐,优选碱土金属的这些酸盐;有机化合物,诸如单-或多元羧酸和其盐,例如4-叔丁基苯甲酸、己二酸、二苯基乙酸、琥珀酸钠或苯甲酸钠;聚合化合物,诸如离子共聚物(离聚物)。
12.填料和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、玻璃珠、石棉、滑石、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、碳黑、石墨、木粉和其它天然产物的粉末或纤维、合成纤维。
13.其它添加剂,例如增塑剂、润滑剂、乳化剂、颜料、流变学添加剂、催化剂、流动性控制剂、光学增亮剂、防火剂、抗静电剂和发泡剂。
14.苯并呋喃酮和二氢吲哚酮,例如在US4325863、US4338244、US5175312、US5216052、US5252643、DE-A-4316611、DE-A-4316622、DE-A-4316876、EP-A-0589839或EP-A-0591102所述的那些或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’-二[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-(3,5-二甲基-4-特戊酰氧基苯基)-5,7-二-叔丁基苯并呋喃-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-(3,4-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮、3-(2,3-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮。
更优选的组合物除了包括成分(a)和(b)还特别加入酚美抗氧化剂、光稳定剂或加工稳定剂。
特别优选的添加剂是酚抗氧化剂(明细表的项1)、UV吸收剂(明细表的项2.1和2.2)、立体受阻胺(明细表的项2.6)、亚磷酸酯和亚膦酸酯(明细表的项4)和羟胺(明细表的项6)。
还特别优选的添加剂(稳定剂)是苯并呋喃-2-酮,诸如在US-A-4325863、US-A-4338244或US-A-5175312中描述的。
与本发明的化合物联合使用的特别重要的是苯并***类的UV吸收剂,例如上述2.1所列的,特别用于稳定合成的有机聚合物,诸如聚乙烯或聚丙烯。
特别有益的UV吸收剂选自2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并***;2-(2-羟基-5-甲基苯基)-2H-苯并***;2-(2-羟基-3-叔丁基-5-甲基苯基)-5-氯苯并***;5-氯-2-(2-羟基-3,5-二叔丁基苯基)-2H-苯并***;2-(2-羟基-3,5-二叔戊基苯基)-2H-苯并***;2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并***;3,5-二叔丁基-4-羟基苯甲酸(2,4-二叔丁基苯基)酯;2-羟基-4-正辛氧基二苯酮;2,4-二(2,4-二甲基苯基)-6-(2-羟基-4-辛氧基苯基)-s-三嗪。特别优选诸如2-(2-羟基-3-叔丁基-5-甲基苯基)-5-氯苯并***;
2-(2-羟基-3,5-二叔丁基苯基)-5-氯苯并***(CAS Reg.No.3864-99-1)的苯并***。
特别有益的酚抗氧化剂选自3,5-二叔丁基-4-羟基氢化肉桂酸正十八烷基酯、四(3,5-二叔丁基-4-羟基氢化肉桂酸)新季戊四醇酯、3,5-二叔丁基-4-羟基苄基磷酸二正十八烷基酯、1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯、硫代二亚乙基二(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二(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-二(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)莱酚、二(3,5-二叔丁基-4-羟基氢化肉桂酸)六亚甲基酯、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’-六亚甲基-二(3,5-二叔丁基-4-羟基氢化肉桂酸酰胺)、二(乙基3,5-二叔丁基-4-羟基苄基膦酸)钙、亚乙基二[3,3-二(3-叔丁基-4-羟基苯基)丁酸酯]、3,5-二叔丁基-4-羟基苄基巯基乙酸辛酯、二(3,5-二叔丁基-4-羟基氢化肉桂酰基)肼和N,N’-二[2-(3,5-二叔丁基-4-羟基氢化肉桂酰氧基)乙基]草酰胺。
最优选的酚抗氧化剂是四(3,5-二叔丁基-4-羟基氢化肉桂酸)新季戊四醇酯、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或2,2’-亚乙基-二(4,6-二叔丁基苯酚)。
特别有益的受阻胺化合物选自二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、二(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-2,2,6,6-四甲基哌啶、4-十八烷氧基-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-2,4-二酮、三(2,2,6,6-四甲基哌啶-4-基)次氮基三乙酸酯、1,2-二(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’-六亚甲基二(氨基-2,2,6,6-四甲基哌啶)的缩聚产物、1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩聚产物、4,4’-六亚甲基二(氨基-2,2,6,6-四甲基哌啶)与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-三嗪与4,4’-六亚甲基二(氨基-2,2,6,6-四甲基哌啶)的缩聚产物、N,N’,N”,N-四[(4,6-二(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-4- 基/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、混合的[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、八亚甲基二(2,2,6,6-四甲基哌啶-4-羧酸酯)、4,4’-亚乙基二(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-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、聚{[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-六亚甲基-[4-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基]}和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。
最优选的受阻胺化合物是二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、二(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-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩聚产物、2,4-二氯-6-叔辛基氨基-s-三嗪与4,4’-六亚甲基二(氨基-2,2,6,6-四甲基哌啶)的缩聚产物、N,N’,N”,N-四[(4,6-二(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、聚{[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-六亚甲基-[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。
特别重要的是根据本发明稳定的组合物,其中成分(a)是热塑性烯烃,成分(b)还含有低分子NOR受阻胺。
特别有益的是根据本发明稳定的组合物,其中成分(a)是暴露在农药——例如含卤素或硫的农药——下的农用薄膜,这类组合物有益地含有硬脂酸金属盐和氧化锌作为添加剂成分。
还优选根据本发明稳定的组合物,其中成分(a)是聚烯烃薄膜、纤维、厚片或另外含有卤化的阻燃剂——诸如十溴二苯基氧、亚乙基二(四溴苯邻二甲酰亚胺)或亚乙基二(二溴-降冰片烷二羰基酰亚胺)——的热塑性烯烃制品。
根据本发明稳定的组合物中成分(a)还可以是可着色的热塑性烯烃(TPO)。
本发明还提供制备混合物N,N’,N-三-{2,4-二[(1-烃氧基-2,2,6,6-四-甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺;N,N’,N-三-{2,4-二[(1-烃氧基-2,2,6,6-四-甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺和在前定义的式I、II、IIA和III所述的桥接的衍生物的方法,其包括
2-4当量的2,4-二[(1-烃氧基-2,2,6,6-四-甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与1当量N,N’-二(3-氨基丙基)亚乙基二胺反应。
优选本方法包括2.5-3当量的该s-三嗪与1当量的胺反应;最优选3当量的该s-三嗪与1当量胺反应。
相对于现有技术的四取代化合物该三取代的化合物有许多优点。用于将1-环己氧基或1-辛氧基引入四取代的s-三嗪受阻胺的叔丁基氢过氧化物氧化偶合反应导致四胺部分显著的链断裂,造成低分子量的副产物。在制备本发明化合物中消除了这种链断裂,因为在不存在四胺骨架的条件下引入了1-烷氧基。
下列实施例仅用于详细说明本发明,在任何情况下不认为是对本发明范围的限定。
用于本发明式I、II、IIA和III受阻胺化合物的共添加剂如下:
抗氧化剂:
四(3,5-二叔丁基-4-羟基氢化肉桂酸)新季戊四醇酯(IRGANOX1010,Ciba Specialty Chemicals Corp.);
3,5-二叔丁基-4-羟基氢化肉桂酸十八烷基酯(IRGANOX1076,CibaSpecialty Chemicals Corp.);
1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯(IRGANOX1330,Ciba Specialty Chemicals Corp.);
1,2-二(3,5-二叔丁基-4-羟基氢化肉桂酰基)肼(IRGANOXMD 1024,Ciba Specialty Chemicals Corp.);
[二(单乙基3,5-二叔丁基-4-羟基苄基)膦酸]钙(IRGANOX1425,Ciba Specialty Chemicals Corp.);
1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯(IRGANOX3114,Ciba Specialty Chemicals Corp.);
1,3,5-三(3-羟基-4-叔丁基-2,6-二甲基苄基)异氰脲酸酯(CYANOX1790,Cytec)。
含磷化合物:
三(2,4-二叔丁基苯基)亚磷酸酯(IRGAFOS168,Ciba SpecialtyChemicals Corp.);
二(2,4-二叔丁基-6-甲基苯基)乙基亚磷酸酯(IRGAFOS38,CibaSpecialty Chemicals Corp.);
2,2’,2”-次氮基[三乙基三(3,3’,5,5’-四叔丁基-1,1’-联苯基-2,2’-二基)亚磷酸酯](IRGAFOS12,Ciba Specialty Chemicals Corp.);
四(2,4-二丁基苯基)4,4’-联亚苯基二亚膦酸酯(IRGAFOSP-EPQ,Ciba Specialty Chemicals Corp.);
三(壬基苯基)亚磷酸酯(TNPP,General Electric);
二(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯(ULTRANOX626,General Electric);
2,2’-亚乙基二(2,4-二叔丁基苯基)氟代亚磷酸酯(ETHANOX398,Ethyl Corp.);
2-丁基-2-乙基丙烷-1,3-二基2,4,6-三叔丁基苯基亚磷酸酯(ULTRANOX641,General Electric);
苯并呋喃-2-酮:
5,7-二叔丁基-3-(3,4-二甲基苯基)-2H-苯并呋喃-2-酮(HP-136,Ciba Specialty Chemicals Corp.)
羟胺:
从N,N-二(氢化的牛脂)胺直接氧化制备的N,N-二烷基羟胺(FS-042,Ciba Specialty Chemicals Corp.)
受阻胺:
二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯(TINUVIN770,CibaSpecialty Chemicals Corp.)
1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩聚产物(TINUVIN622,Ciba Specialty Chemicals Corp.);
N,N’,N”,N-四[(4,6-二(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(CHIMASSORB119,CibaSpecialty Chemicals Corp.);
4,4’-六亚甲基二(氨基-2,2,6,6-四甲基哌啶)与2,4-二氯-6-叔辛基氨基-s-三嗪的缩聚产物(CHIMASSORB944,Ciba Specialty ChemicalsCorp.);
4,4’-六亚甲基二(氨基-2,2,6,6-四甲基哌啶)与2,4-二氯-6-吗啉代-s-三嗪的缩聚产物(CYASORB3346,Cytec);
2,2,6,6-四甲基哌啶-4-基十八烷酸酯(CYASORB3853,Cytec);
3-十二烷基-1-(1-乙酰基-2,2,6,6-四甲基哌啶-4-基)吡咯烷-2,5-二酮(CYASORB3581,Cytec);
1,3,5-三{N-环己基-N-[2-(2,2,6,6-四甲基哌嗪-3-酮-4-基)乙基]氨基}-s-三嗪(GOODRITE3150,B.F.Goodrich);
聚[甲基3-(2,2,6,6-四甲基哌啶-4-基氧基)丙基]硅氧烷(UVASIL299,Enichem);
2,4-二氯-6-(2,2,6,6-四甲基哌啶-4-基)-丁基氨基)-s-三嗪与2,2’-亚乙基-二{[2,4-(2,2,6,6-四甲基哌啶-4-基)丁基氨基-s-三嗪-6-基]氨基三亚甲基氨基}的缩聚产物(HA 88)。
NOR受阻胺:
二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯(TINUVIN123,Ciba Specialty Chemicals Corp.);
二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)己二酸酯;
二(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)己二酸酯;
二(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯;
1-环己氧基-2,2,6,6-四甲基哌-4-基十八烷酸酯。
阻燃剂:
三(3-溴-2,2-二(溴甲基)丙基)磷酸酯(PB 370,FMC Corp.);
十溴二苯基氧(DBDPO);
亚乙基二(四溴苯邻二甲酰亚胺)(SAYTEXBT-93);
亚乙基二(二溴-降冰片烷二羰基酰亚胺)(SAYTEXBT-451)
UV吸收剂:
2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并***(TINUVIN234,Ciba Specialty Chemicals Corp.);
2-(2-羟基-5-甲基苯基)-2H-苯并***(TINUVINP,CibaSpecialty Chemicals Corp.);
5-氯-2-(2-羟基-3,5-二叔丁基苯基)-2H-苯并***(TINUVIN327,Ciba Specialty Chemicals Corp.);
2-(2-羟基-3,5-二叔戊基苯基)-2H-苯并***(TINUVIN328,CibaSpecialty Chemicals Corp.);
2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并***(TINUVIN928,Ciba Specialty Chemicals Corp.);
3,5-二叔丁基-4-羟基苯甲酸(2,4-二叔丁基苯基)酯(TINUVIN120,Ciba Specialty Chemicals Corp.);
2-羟基-4-正辛氧基二苯酮(CHIMASSORB81,Ciba SpecialtyChemicals Corp.);
2,4-二(2,4-二甲基苯基)-6-(2-羟基-4-辛氧基苯基)-s-三嗪(CYASORB1164,Cytec)。
实施例1:2-氯-4,6-二[N-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-s-三嗪
剧烈搅拌57.7克(0.448摩尔)70%含水叔丁基氢过氧化物、250毫升环己烷和100毫升饱和的氯化钠溶液的混合物,随后分离有机层并用无水硫酸镁干燥。过滤除去干燥剂。滤液,30.0克(0.056摩尔)2-氯-4,6-二[N-(2,2,6,6-四甲基哌啶-4-基)丁基氨基]-s-三嗪和1.0克三氧化钼置于压力瓶中并在130-140℃加热。反应混合物迅速变红,持续加热直至红色放出。冷却反应混合物,用过滤除去固体。滤液减压浓缩,得到的一种油用在硅胶上的闪蒸色谱纯化,获得30.3克(74%产率)标题化合物的白色玻璃状物。
尽管白色玻璃状物基本上是标题化合物,但还可存在微量的桥接物质。
实施例2:2-氯-4,6-二[N-(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-s-三嗪
剧烈搅拌57.7克(0.448摩尔)70%含水叔丁基氢过氧化物、340毫升辛烷和50毫升饱和的氯化钠溶液的混合物,随后分离有机层并用无水硫酸镁干燥。过滤除去干燥剂。一半叔丁基氢过氧化物/辛烷溶液与30.0克(0.056摩尔)2-氯-4,6-二[N-(2,2,6,6-四甲基哌啶-4-基)丁基氨基]-s-三嗪和1.0克三氧化钼混合,回流加热该混合物。在Dean-Stark阱中收集水。当反应混合物一变红,在3小时加入所剩的叔丁基氢过氧化物/辛烷溶液,并同时保持反应混合物回流。再加热混合物1小时使红色放出。冷却反应混合物至室温,用过滤除去固体。滤液减压浓缩,得到的一种琥珀色的油用在硅胶上的闪蒸色谱纯化(40∶1,庚烷/乙酸乙酯),获得32.7克(74%产率)标题化合物的无色淤浆。
尽管无色淤浆基本上是标题化合物,但还可存在微量的桥接物质。
实施例3:2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)亚乙基二胺的反应
6.4克(37毫摩尔)N,N’-二(3-氨基丙基)亚乙基二胺、在环己烷中107.6克(147毫摩尔,4.0当量)实施例1制备的2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪的70%的溶液和31.0克20%氢氧化钠水溶液在160℃加热4小时。冷却反应物,用60克环己烷稀释。除去水层,浓缩有机层,加入水沉淀粗产物。固体用水洗至中性,干燥,得到102克产物。
分析:尽管每1当量四胺使用4当量6-氯-s-三嗪,nmr分析表明平均只有3个三嗪基与胺骨架连接。
产物是包括桥接化合物的异构体混合物。用制备色谱可将该混合物分离成纯的组分,特别是所述的两种非桥接的异构体更容易。
实施例4:2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)亚乙基二胺的反应
重复实施例3的过程,除了使用3.0当量2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪和反应在120℃进行9小时以外。
该产物还是包括桥接化合物的异构体混合物。nmr分析表明平均有2.5-3个三嗪基与胺骨架连接。DSC测定的该产物的Tg为104-118℃。
实施例4a:比较实施例
通过有四个取代的s-三嗪基与3,3’-亚乙基二亚胺基二丙胺骨架结合的受阻胺前体(CHIMASSORB905,Ciba)与三氧化钼和环己烷反应形成相应的1-环己氧基化合物,制备US5204473实施例62的化合物。基于初始的CHIMASSORB905起始原料,该化合物按照推测是四取代的。但是,nmr和GPC分析表明在该反应条件下s-三嗪基适合地***并形成未知的有色副产物,只有2个s-三嗪基仍可与胺骨架键合。
为区分实施例4的“三取代”化合物和在此指定为实施例4a的现有技术US5204473实施例62的化合物,用DSC测定每个化合物的Tg,对每个化合物进行DSC和TGA分析。
化合物 Tg(℃)
实施例4a 88-93
实施例4 104-118
DSC分析* | |||
开始(℃) | 峰值(℃) | ||
实施例4a实施例4 | 放热放热放热放热 | 141220228269 | 173292228299 |
TGA分析**如下重量损失的温度(℃) | |||
2% | 10% | 50% | |
实施例4a实施例4 | 171254 | 260285 | 321385 |
*DSC扫描(10℃/分钟至350℃,100毫升/分钟N2,Al中间罐,~10毫克)
DSC-误差估计,焓±10%,温度±2℃。
**TGA扫描(10℃/分钟至500℃,100毫升/分钟N2,Al中间罐,~10毫克)
TGA-误差估计,温度±5℃;重量±0.5%绝对。
从这些数据可清楚地表明用一种与现有技术的US5204473实施例62的化合物不同的工艺制备的实施例4的化合物是根本不同的物质,实施例4的化合物比现有技术实施例62的化合物热稳定性更高。
实施例5:2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)亚乙基二胺的反应
重复实施例4的过程,除了使用2.5当量2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪以外。
该产物也是包括桥接化合物的异构体混合物。nmr分析表明平均有2.5-3个三嗪基与胺骨架连接。
DSC测定的该产物的Tg为109-116℃。
实施例6:2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)亚乙基二胺的反应
重复实施例4的过程,除了使用2.0当量2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪和反应在120℃进行5小时以外。
该产物是包括桥接化合物的异构体混合物。如预期的那样,nmr分析表明平均有2个三嗪基与胺骨架连接。
DSC测定的该产物的Tg为101-114℃。
实施例7:2,4-二[1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)亚乙基二胺的反应产物的纯化
实施例4得到的反应混合物的一部分溶于甲苯并经过PhenomenexTM(10微米)柱,以甲苯为洗脱液。用凝胶渗透色谱收集和分析级分。通过蒸发溶剂将分子量分布与三取代的产物一致的物质分离。
实施例8:纯2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)亚乙基二胺的反应
步骤1
向过量的1-氧基-2,2,6,6-四甲基哌啶-4-酮和环己基碘化物在氯苯中的溶液加入三丁基锡氢化物。混合物与庚烷/乙酸乙酯一起经过硅胶,得到1-环己氧基-2,2,6,6-四甲基哌啶-4-酮,不含任何二(4-氧基-2,2,6,6-四甲基哌啶-1-基氧基)环己烷桥接的物质。
步骤2
将上述步骤1制备的化合物、正丁基胺、甲醇和5%铂在碳上的催化剂的混合物氢化(50psi,25℃)。过滤除去催化剂,蒸发滤液,得到4-丁基氨基-1-环己氧基-2,2,6,6-四甲基哌啶。
步骤3
将2当量步骤2制备的化合物在40℃加入氰尿酰氯和二甲苯的混合物中。加入氢氧化钠,加热该混合物到65℃,直到反应完成。冷却反应混合物,加入水。用稀释的酸、水洗涤有机层,干燥,蒸发,得到2,4-二[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪。
用这种制备方法,该中间体显然不是诸如实施例1制备的中间体这类化合物的混合物。
步骤4
N,N’-二(3-氨基丙基)亚乙基二胺和3.0当量步骤3制备的化合物的混合物根据实施例4的工艺反应。
实施例9:2,4-二[(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)亚乙基二胺的反应
N,N’-二(3-氨基丙基)亚乙基二胺、3当量实施例2制备的2,4-二[(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪在辛烷中的溶液和20%氢氧化钠水溶液在120℃加热直至反应完成。冷却反应物,有机层用水洗至中性,蒸发溶剂,得到产物混合物。
nmr分析与本反应的预计产物一致。
实施例10:2,4-二[1-甲氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-二(3-氨基丙基)亚乙基二胺的反应
N,N’-二(3-氨基丙基)亚乙基二胺、3当量2,4-二[(1-甲氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-1,3,5-三嗪在环己烷中的溶液和20%氢氧化钠水溶液的混合物在120℃加热直至反应完成。冷却反应物,有机层用水洗至中性,蒸发溶剂,得到产物混合物。
实施例11:含0.05%重量硬脂酸钙和0.05%重量从N,N-二(氢化的牛脂)胺直接氧化制备的羟胺的纤维级的聚丙烯与试验添加剂干混,然后在234℃(450)熔融混合成丸状。制成丸状的完全配方的树脂随后在246℃(475)用Hills实验室型纤维挤出机纺成纤维。以1∶3.2的比拉伸41长丝的粗纺纤维,得到最终的615/41旦。
在Lawson-Hemphill Analysis针织机(Knitter)上用稳定的聚丙烯纤维编制软套,在使用89℃bpt、在340nm 0.55kW/cm2、不带喷雾循环的SAE J 1885车内条件(Interior Automotivecondition)的Atlas氙弧光天候老化仪(Xenon-Arc WeatherOmeter)中暴露试验。通过观察当用圆头玻璃棒划伤软套时的物理破坏确定为在该试验中的破坏。导致这种严重破坏发生所需的时间越长,该稳定剂体系越有效。
不含有本发明化合物的对照软套在暴露试验200小时后损坏,而含有0.25%重量实施例4的本发明化合物混合物或含有0.25%重量实施例3的化合物的软套在暴露700小时后损坏。含有0.5%重量实施例4的本发明化合物的软套在暴露1000小时后损坏;含有0.75%重量实施例4的化合物的软套在暴露1000小时后未损坏。
实施例12:将其它实施例11制备的聚丙烯纤维软套暴露在120℃的Blue M压力送风炉中。用实施例11设定的标准确定损伤。导致这种严重损坏发生所需的时间越长,该稳定体系越有效。
含有本发明化合物的软套表现出好的热稳定效果。
实施例13:将薄膜级的聚乙烯与约10%重量的试验添加剂干混,然后在200℃熔融混合成“母料”颗粒。该母料与聚乙烯树脂干混得到所需的最终稳定剂浓度。这种稳定的全配方树脂随后用DOLCI膜生产线在200℃吹成150微米厚的膜。
吹制的膜根据ASTM G26在63℃bpt、在340nm 0.35W/m2、不带喷雾循环的Atlas氙弧光天候老化仪(Xenon-Arc WeatherOmeter)中暴露。用Instron 112抗拉试验仪周期性地测量膜的延展率的任何变化。在该试验中的破坏通过观察膜的延展率的损失%确定。导致这种损失发生所需的时间越长,该稳定剂体系越有效。
含有本发明化合物混合物的膜表现出好的光稳定效果。
实施例14:将热塑性烯烃(TPO)颗粒注塑制备模制试验样品,该热塑性烯烃颗粒含有颜料、亚磷酸酯、酚类抗氧化剂或羟胺、硬脂酸金属盐、UV吸收剂或受阻胺稳定剂或式I、II、IIA和III的受阻胺化合物;或一种受阻胺和UV吸收剂的混合物。
由纯颜料或颜料浓缩物、稳定剂、共添加剂和可从市场获得的热塑性烯烃通过在Superior/MPM 1”单螺杆挤压机使用一般通用的螺杆(24∶1L/D)在400(200℃)混合组分,在水浴中冷却并造粒,制备着色的TPO颗粒。生成的配方的颗粒在BOY 30M注塑机中在约375(190℃)模制成60密耳(0.006英寸)厚2”×2”装饰片。
染色的TPO配方由与橡胶改性剂混合的聚丙烯组成,其中橡胶改性剂是就地反应的共聚物或含有丙烯和乙烯有或没有第三成分——诸如亚乙基降冰片烯——的共聚物的混合产物,该配方由基础稳定体系稳定,该稳定体系含有N,N-二烷基羟胺或受阻酚类抗氧化剂和有机磷化合物的混合物。
在最终配方中的所有添加剂和颜料以基于树脂的重量百分比表示。
试验配方含有热塑性烯烃颗粒和下列成分的一种或多种:
0.0-2.0% 颜料
0.0-50.0% 滑石
0.0-0.5% 亚磷酸酯
0.0-1.25% 酚类抗氧化剂
0.0-0.1% 羟胺
0.0-0.5% 硬脂酸钙
0.0-1.25% UV吸收剂
0.0-1.25% 受阻胺稳定剂
在挤压和模塑前在鼓式干燥机中干混组分。
试验装饰片在金属框中测定,根据Society of AutomotiveEngineers(SAE J 1960)试验过程在70℃黑板测温温度、在340nm0.55W/m2和50%相对湿度、使用间歇光/暗循环和水喷雾、在Atlas Ci65氙弧光天侯老化仪(Xenon Arc WeatherOmeter)中暴露试验。根据ASTMD 2244-79用反射型Applied Co1or Systems分光光度计以约625千焦间隔对样品进行颜色测量试验。收集的数据包括ΔE、L*、a*和b*值。在60℃根据ASTM D523在BYK-GARDNER雾度/光泽仪(Haze/GloosMeter)上测定光泽。
UV辐照试验-当用含苯并***UV吸收剂和式I、II、IIA和III的受阻胺化合物的光稳定剂稳定时,被UV射线辐照的试验片表现出特异的抗光致降解性。
与现有技术的稳定体系比较,稳定的样品特别表现出改进的光泽保持力。UV辐照下的抗变色性也提高了。当用本发明体系稳定时,含有不饱和三元成分的聚合物混合物——诸如EPDM混合物——特别表现出提高的性质。
在所有情况下,与未稳定的试样在上述UV辐照条件下迅速破坏相比,光稳定化的配方表现出更大的抗光致降解性。
配方** | ΔE小时 | ΔE小时 | 光泽*小时 | %光泽保持 | ||
小时 | 小时 | 小时 | ||||
0 | 1868 | 0 | 1868 | 0 | 1868 | |
HALS A(0.2%)+HALS B(0.2%)HALS C(0.2%)+ | 0.00.0 | 7.94.6 | 74.579.4 | 21.472.2 | 100100 | 28.790.9 |
实施例4的
HALS(0.2%)
*在60℃
**HALS A是二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯。
HALS B是4,4’-六亚甲基-二(氨基-2,2,6,6-四甲基哌啶)和2,4-二氯-6-叔辛基氨基-s-三嗪的缩聚产物。
HALS C是二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯。
最终的配方含有0.25%颜料红177、0.05%新季戊四醇四(3,5-二叔丁基-4-羟基氢化肉桂酸酯)、0.05%三(2,4-二叔丁基苯基)亚磷酸酯和0.2%2-(2-羟基-3,5-二叔戊基苯基)-2H-苯并***。样品是60密耳厚2”×2”注塑装饰片。根据SAE J 1960规范在车外条件下进行UV辐照。
实施例15a:薄膜级的聚乙烯与10%填充试验添加剂干混,然后在200℃熔融混合成母料颗粒。母料颗粒与聚乙烯树脂干混得到最终的稳定剂浓度。然后在200℃用DOLCI薄膜生产线将全配方树脂吹成150微米厚的薄膜。
生成的膜在镀锌铁支架上在温室上暴露。处理包括使用常规基准的农药(即,每6个月用N-甲基二硫氨基甲酸钠盐VAPAM和每个月用SESMETRIN)。通过监测延展性保留比例测量性能。达到原延展性损失50%的时间定义为破坏。
含有0.4%重量4,4’-六亚甲基-二(氨基-2,2,6,6-四甲基哌啶)和2,4-二氯-6-叔辛基氨基-s-三嗪的缩聚产物的对照膜在160KLYS温室暴露试验后破坏。含有0.4%重量实施例3的本发明化合物的膜则在300KLYS曝光试验后才破坏。这些结果表明了式I、II、IIA和III化合物的抗农药性。
实施例15b:如实施例15a所述制备的母料颗粒与聚乙烯树脂干混得到最终的稳定剂浓度。全配方树脂然后在200℃用DOLCI薄膜生产线吹成25微米厚的膜。
生成的膜暴露在土地上模拟农用覆盖膜条件。处理包括使用甲基溴以60g/m3的量熏蒸3天。通过监测物理脆化的时间测量性能。
含有1.2%重量4,4’-六亚甲基-二(氨基-2,2,6,6-四甲基哌啶)和2,4-二氯-6-叔辛基氨基-s-三嗪的缩聚产物的对照膜在70KLYS室外暴露后破坏。含有1.2%重量实施例3的本发明化合物的膜在110KLYS曝光仍然完整。这些结果表明了式I、II、IIA和III化合物对熏蒸的耐受性。
实施例16:如实施例15所述制备温室膜样品,除了本发明式I、II、IIA和III化合物外还含有硬脂酸金属盐或金属氧化物。典型的配方含有0.05-2%重量本发明的受阻胺、0.05-0.5%硬脂酸金属盐——诸如氧化钙——和0.05-0.5%金属氧化物,诸如氧化锌或氧化镁。
如实施例15所述监测效果。含本发明受阻胺化合物的膜表现出好的光稳定性。
实施例17:如实施例11所述制备聚丙烯纤维。除了本发明式I、II、IIA和III受阻胺化合物外,配方中还含有选择的卤化的阻燃剂。阻燃剂是三(3-溴-2,2-二(溴甲基)丙基)磷酸酯、十溴二苯基氧、亚乙基二(四溴邻苯二甲酰亚胺)或亚乙基二(二溴-降冰片烷二羧酰亚胺)。
使用实施例11所述光稳定性的判据,用含本发明受阻胺的聚丙烯纤维编织的软套表现出好的光稳定性。
实施例18:模塑级的聚丙烯与试验添加剂干混,然后熔融混合成丸。除了本发明式I、II、IIA和III受阻胺化合物外,还含有选择的阻燃剂。阻燃剂是三(3-溴-2,2-二(溴甲基)丙基)磷酸酯、十溴二苯基氧、亚乙基二(四溴邻苯二甲酰亚胺)或亚乙基二(二溴-降冰片烷二羧酰亚胺)。然后,成丸的全配方树脂用Boy 50M试验室型注塑机注塑成试验片。
试验片在金属框中测定,根据ASTM G26试验程序使用间歇光/暗循环和水喷雾、在Atlas Ci65氙弧光天侯老化仪(Xenon ArcWeatherOmeter)中暴露试验。以周期性间隔测定样片的拉伸性能的变化。通过观察拉伸性能的损失确定在该试验中的破坏。导致这种性能损失发生所需的时间越长,该稳定剂体系越有效。
含本发明受阻胺化合物的试验样品表现出好的光稳定性。
实施例19:如实施例14所述通过注塑热塑性烯烃(TPO)丸制备模制的试验片。除了本发明式I、II、IIA和III受阻胺化合物外,试验样品中还含有选择的阻燃剂。阻燃剂是三(3-溴-2,2-二(溴甲基)丙基)磷酸酯、十溴二苯基氧、亚乙基二(四溴邻苯二甲酰亚胺)或亚乙基二(二溴-降冰片烷二羧酰亚胺)。
含本发明受阻胺的样品表现出好的光稳定性。
实施例20:混合薄膜级的聚乙烯并如实施例13所述在200℃用DOLCI薄膜生产线吹成膜。除了本发明式I、II、IIA和III受阻胺化合物外,在配方中还含有选择的阻燃剂。阻燃剂是三(3-溴-2,2-二(溴甲基)丙基)磷酸酯、十溴二苯基氧、亚乙基二(四溴邻苯二甲酰亚胺)或亚乙基二(二溴-降冰片烷二羧酰亚胺)。然后,成丸的全配方树脂用Boy 50M试验室型注塑机注塑成试验片。
当如实施例13所述进行光稳定活性试验时,含本发明受阻胺的膜表现出好的光稳定性。
实施例21:如实施例14所述通过注塑含本发明式I、II、IIA和III受阻胺化合物、颜料和其它共添加剂的热塑性烯烃(TPO)颗粒制备模塑的试验片。
用单组分的着色***将试验片染色,测试TPO/颜料相互作用。着色前,先用异丙醇和空气鼓风擦洗试验片除去任何灰尘。闪光5分钟后,这些试验片被增粘剂涂敷,然后是基础涂层,然后是任意的透明涂层。这些不同涂层的一般膜厚度为增粘剂0.1-0.3密耳,基础涂层0.6-0.8密耳,透明涂层1.2-1.5密耳。着色后,样片在120℃的炉中固化30分钟。
测试样品评价TPO/颜料相互作用如下:在起始的粘合试验中,用透明玻璃纸粘性胶带在3mm交叉刻线的颜料表面上粘拉;或在湿度试验中,着色的片在98%相对湿度的气氛中在38℃暴露240小时。根据ASTM D 714目测测量起泡率。
如根据上述判据确定的那样,含有本发明受阻胺化合物的样品表现出好的TPO/颜料相互作用性能。
实施例22:包括聚丙烯、聚乙烯均聚物、聚烯烃共聚物或热塑性烯烃(TPO)的聚烯烃树脂与本发明式I、II、IIA和III受阻胺化合物干混,然后熔融混合造粒。成粒的全配方树脂随后被加工成应用制品,如挤成纤维;吹塑或铸塑挤成膜;吹塑成瓶子;注塑成模塑制品;热成型为模塑制品;挤压成电线和电缆外壳;或滚塑成中空制品。
含有本发明受阻胺化合物的材料表现出对UV光和热辐照有害影响具有稳定性。
实施例23:根据实施例22制备的制品,还含有选择的有机颜料以及本发明式I、II、IIA和III受阻胺化合物,也表现出对光合光和热辐照有害影响具有稳定性。
实施例24:根据实施例22制备的制品,还含有选自四(3,5-二叔丁基-4-羟基氢化肉桂酸)新季戊四醇酯、3,5-二叔丁基-4-羟基氢化肉桂酸十八烷基酯、1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯、1,2-二(3,5-二叔丁基-4-羟基氢化肉桂酰基)肼、[二(一乙基3,5-二叔丁基-4-羟基苄基)膦酸]钙、1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯和1,3,5-三(3-羟基-4-叔丁基-2,6-二甲基苄基)异氰脲酸酯的受阻酚类抗氧化剂以及本发明式I、II、IIA和III化合物,也表现出对光合光和热辐照有害影响具有稳定性。
实施例25:根据实施例22制备的制品,还含有选自三(2,4-二叔丁基苯基)亚磷酸酯、二(2,4-二叔丁基-6-甲基苯基)乙基亚磷酸酯、2,2’,2”-次氮基[三乙基-三(3,3’,5,5’-四叔丁基-1,1’-联苯基-2,2’-二基)亚磷酸酯]、四(2,4-二丁基苯基)-4,4’-联亚苯基二亚膦酸酯、三(壬基苯基)亚磷酸酯、二(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯、2,2’-亚乙基二(2,4-二叔丁基苯基)氟代亚磷酸酯和2-丁基-2-乙基丙烷-1,3-二基-2,4,6-三叔丁基苯基亚磷酸酯的有机磷稳定剂以及本发明式I、II、IIA和III化合物,也表现出对光合光和热辐照有害影响具有稳定性。
实施例26:根据实施例22制备的制品,还含有5,7-二叔丁基-3-(3,4-二甲基苯基)-2H-苯并呋喃-2-酮的苯并呋喃酮稳定剂以及本发明式I、II、IIA和III化合物,也表现出对UV光和热辐照有害影响具有稳定性。
实施例27:根据实施例22制备的制品,还含有从N,N-二(氢化的牛脂)胺直接氧化制备的N,N-二烷基羟胺的二烷基羟胺稳定剂以及本发明式I、II、IIA和III化合物,也表现出对光合光和热辐照有害影响具稳定性。
实施例28:根据实施例22制备的制品,还含有选自二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶与琥珀酸的缩聚产物、N,N’,N”,N-四[4,6-二(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、4,4’-六亚甲基二(氨基-2,2,6,6-四甲基哌啶)与2,4-二氯-6-叔辛基氨基-s-三嗪的缩聚产物、4,4’-六亚甲基二(氨基-2,2,6,6-四甲基哌啶)与2,4-二氯-6-吗啉代-s-三嗪的缩聚产物、2,2,6,6-四甲基哌啶-4-基十八烷酸酯,3-十二烷基-1-(1-乙酰基-2,2,6,6-四甲基哌啶-4-基)吡咯烷-2,5-二酮、1,3,5-三{N-环己基-N-[2-(2,2,6,6-四甲基哌嗪-3-酮-4-基)乙基]氨基}-s-三嗪、聚[甲基3-(2,2,6,6-四甲基哌啶-4-基氧基)丙基]硅氧烷、2,4-二氯-6-(2,2,6,6-四甲基哌啶-4-基)-丁基氨基)-s-三嗪与2,2’-亚乙基-二{[2,4-(2,2,6,6-四甲基哌啶-4-基)丁基氨基-s-三嗪-6-基]氨基三亚甲基氨基}的缩聚产物的其它受阻胺稳定剂以及本发明式I、II、IIA和III化合物,也表现出对光合光和热辐照有害影响具有稳定性。
实施例29:根据实施例22制备的制品,还含有选自二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯、二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)己二酸酯、二(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)己二酸酯、二(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)琥珀酸酯和1-环己氧基-2,2,6,6-四甲基哌啶-4-基十八烷酸酯的其它的N-烃氧基取代的受阻胺以及本发明式I、II、IIA和III化合物,也表现出对光合光和热辐照有害影响具有稳定性。
实施例30:根据实施例22制备的制品,还含有选自2-(2-羟基-3,5-二-α-异丙苯基苯基)-2H-苯并***、2-(2-羟基-5-甲基苯基)-2H-苯并***、5-氯-2-(2-羟基-3,5-二叔丁基苯基)-2H-苯并***、2-(2-羟基-3,5-二叔戊基苯基)-2H-苯并***、2-(2-羟基-3-α-异丙苯基-5-叔辛基苯基)-2H-苯并***、2,4-二叔丁基苯基-3,5-二叔丁基-4-羟基苯甲酸酯、2-羟基-4-正辛氧基二苯酮和2,4-二(2,4-二甲基苯基)-6-(2-羟基-4-辛氧基苯基)-s-三嗪的邻羟基苯基-2H-苯并***、羟基苯基二苯酮或邻羟基苯基-s-三嗪UV吸收剂自的受阻的酚类抗氧化剂以及本发明式I、II、IIA和III化合物,也表现出对UV光和热辐照有害影响具有稳定性。
说明书或权利要求书中无论在何处描述,式中以下
部分都表示残基2,2,6,6-四甲基哌啶基(在1和4位键合)。
Claims (6)
1.一种对热、氧化或光致降解稳定的组合物,其含有,
(a)合成聚合物,和
(b)混合物N,N’,N-三{2,4-二[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺;N,N’,N”-三{2,4-二[(1-烃氧基-2,2,6,6-四甲基哌啶-4-基)烷基氨基]-s-三嗪-6-基}-3,3’-亚乙基二亚氨基二丙基胺和如式I、II、IIA和III所示桥接的衍生物 R1NH-CH2CH2CH2NR2CH2CH2NR3CH2CH2CH2NHR4 (I)
T-E1-T1 (II)
T-E1 (IIA)
G-E1-G1-E1-G2 (III)
其中E是
其中在式I的四胺中,
R1和R2是s-三嗪部分E;R3和R4之一是s-三嗪部分E,同时R3和R4另一个是氢,
R是甲基、环己基或辛基,
R5是1-12个碳原子的烷基,
其中式II或IIA的化合物当R是环己基或辛基时,
T和T1分别是被如上为式I定义的R1-R4取代的四胺,其中
(1)每个四胺中s-三嗪部分E之一被基团E1代替,其在两个四胺T和T1之间形成一个桥,或
(2)基团E1可如在式IIA中一样具有在相同的四胺T中的两个终端,其中四胺的两个E部分被一个E1基团代替,或
(3)四胺T的所有三个s-三嗪取代基可以是E1,从而一个E1连接T和T1,并且第二个E1具有在四胺T中的两个终端,
L是环己烷二基或辛烷二基;
其中在式III化合物中,
G、G1、和G2分别是被如上为式I定义的R1-R4取代的四胺,除了G和G2分别有一个s-三嗪部分E被基团E1代替、G1有两个三嗪部分E被基团E1代替,从而在G和G1之间形成一个桥,在G1和G2之间形成第二个桥;
其中成分(b)的混合物可通过2-4当量的2,4-二[(1-烃氧基-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’-二-(3-氨基丙基)亚乙基二胺反应获得。
2.根据权利要求1的组合物,其中合成聚合物是聚烯烃。
3.根据权利要求1的组合物,其中在成分(b)的化合物的E和E1部分,R是环己基或辛基,R5是丁基。
4.根据权利要求1的组合物,其中成分(b)含量为稳定的组合物重量的0.005-5%。
5.根据权利要求1的组合物,其还含有有效稳定量的至少一种共添加剂稳定剂,其选自酚类抗氧化剂、2-(2’-羟苯基)苯并***、羟苯基-s-三嗪、硬脂酸金属盐、金属氧化物、有机磷化合物、呋喃酮抗氧化剂、羟胺、空间受阻胺和其混合物。
6.根据权利要求2的组合物,其中成分(a)是暴露在农药下或含有卤化的阻燃剂的聚烯烃。
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Also Published As
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TW512160B (en) | 2002-12-01 |
AR016289A1 (es) | 2001-07-04 |
MX9805329A (en) | 1999-09-01 |
DE69806696D1 (de) | 2002-08-29 |
EP0889085A2 (en) | 1999-01-07 |
JP4340985B2 (ja) | 2009-10-07 |
DE69806696T2 (de) | 2003-04-03 |
EP0889085A3 (en) | 2000-01-26 |
CA2241495A1 (en) | 1998-12-30 |
BR9803109A (pt) | 2000-03-14 |
CN1519268A (zh) | 2004-08-11 |
CN1211588A (zh) | 1999-03-24 |
EP0889085B1 (en) | 2002-07-24 |
RU2230758C2 (ru) | 2004-06-20 |
IN232869B (zh) | 2009-03-27 |
ES2180133T3 (es) | 2003-02-01 |
JPH1180569A (ja) | 1999-03-26 |
KR100536920B1 (ko) | 2006-07-19 |
KR19990007422A (ko) | 1999-01-25 |
CN100393789C (zh) | 2008-06-11 |
BR9803109B1 (pt) | 2010-03-09 |
IN253973B (zh) | 2012-09-14 |
US5844026A (en) | 1998-12-01 |
CA2241495C (en) | 2007-12-04 |
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