CN100429259C - 用于聚烯烃的稳定剂混合物 - Google Patents
用于聚烯烃的稳定剂混合物 Download PDFInfo
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- CN100429259C CN100429259C CNB018054579A CN01805457A CN100429259C CN 100429259 C CN100429259 C CN 100429259C CN B018054579 A CNB018054579 A CN B018054579A CN 01805457 A CN01805457 A CN 01805457A CN 100429259 C CN100429259 C CN 100429259C
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen 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
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
-
- 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
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3462—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
Abstract
本发明涉及含有一种位阻胺化合物和一种含极性残基聚合物的一种稳定剂混合物,其中组分(A)∶(B)的重量比为20∶1到1∶20;前提是(1)组分(B)不同于组分(A),和组分(B)不含有式(I)或(II)的基团,其中G是氢或甲基,和G1和G2彼此独立地为氢、甲基或一起为取代基=O;和(2)组分(B)不同于具有酸性氢原子的聚合物。
Description
本发明涉及含有一种位阻胺化合物和一种含极性残基聚合物的一种稳定剂混合物;该混合物用于稳定聚烯烃防止因光、热或氧化诱导的降解中的应用,以及由此稳定的聚烯烃。
例如在EP-A-80431、EP-A-252877、EP-A-709426、EP-A-723990、EP-A-728806、GB-A-2301106、EP-A-741163和EP-A-754723中公开了含有两种位阻胺化合物的稳定剂混合物。
US-A-5643985涉及回收塑料的稳定方法。EP-A-220897、US-A-5475041和BE-A-775151公开了聚烯烃的稳定方法。
本发明尤其涉及一种稳定剂混合物,其含有
(A)一种位阻胺化合物,和
(B)一种含极性残基的聚合物;
组分(A)∶(B)的重量比为20∶1到1∶20;
前提是
(1)组分(B)不同于组分(A),并不含有式(I)或(II)的基团
其中G是氢或甲基,和
G1和G2彼此独立地为氢、甲基或一起为取代基=O;和
(2)组分(B)不同于具有酸性氢原子的聚合物。
具有酸性氢原子的聚合物是指具有诸如羧基、磺基和二氧磷基等官能团的聚合物。如EP-A-220897中所述,本发明的组分(B)不涵盖具有酸性氢原子的聚合物。
组分(A)∶(B)的重量比优选15∶1到1∶15;尤其是10∶1到1∶10,例如5∶1到1∶5、3∶1到1∶3、5∶1到1∶1、4∶1到1∶1、3∶1到1∶1或2∶1到1∶1。尤其优选1∶1的重量比。
位阻胺(组分(A))优选含有至少一种式(I)或(II)的基团的化合物
其中G是氢或甲基,和
G1和G2彼此独立地为氢、甲基或一起为取代基=O。
以下(a′)-(i′)组描述了位阻胺更详细的实例。
(a′)式(I a)的化合物
其中n1是从1到4的数,G和G1彼此独立地为氢或甲基,
G11是氢、O、羟基、C1-C18烷基、C3-C8链烯基、C3-C8炔基、C7-C12芳烷基、C1-C18烷氧基、C5-C8环烷氧基、C7-C9苯基烷氧基、C1-C8烷酰基、C3-C5链烯酰基、C1-C18烷酰氧基、缩水甘油基或式-CH2CH(OH)-Z的基团,其中Z是氢、甲基或苯基,G11优选H、C1-C4烷基、烯丙基、苄基、乙酰基或丙烯酰基,和若n1为1,则G12是氢、未被间隔或被一个或多个氧原子间隔的C1-C18烷基、氰乙基、苯甲酰基、缩水甘油基;脂族、脂环族、芳脂族、不饱和或芳族羧酸、氨基甲酸或含磷酸的一价基团,或者一价甲硅烷基基团,优选具有2-18个碳原子的脂族羧酸基团、具有7-15个碳原子的脂环族羧酸基团,或者具有3-5个碳原子的α,β-不饱和羧酸基团,或者具有7-15个碳原子的芳族羧酸基团,其中各羧酸可在脂族、脂环族或芳族部分被1-3个-COOZ12基团取代,其中Z12是H、C1-C20烷基、C3-C12链烯基、C5-C7环烷基、苯基或苄基;若n1为2,则G12是C2-C12亚烷基、C4-C12亚链烯基、亚二甲苯基;脂族、脂环族、芳脂族或芳族二羧酸、二氨基甲酸或含磷酸的二价基团,或者二价甲硅烷基基团,优选具有2-36个碳原子的脂族二羧酸或具有8-14个碳原子的脂环族或芳族二羧酸的基团,或者具有8-14个碳原子的脂族、脂环族或芳族二氨基甲酸的基团,其中各二羧酸可在脂族、脂环族或芳族部分被1或2个-COOZ12基团取代;若n1为3,则G12是脂族、脂环族或芳族三羧酸、芳族三氨基甲酸或含磷酸的三价基团,或者三价甲硅烷基基团,其中各羧酸可在脂族、脂环族或芳族部分被-COOZ12基团取代;若n1为4,则G12是脂族、脂环族或芳族四羧酸的四价基团。
在所有情况下,上述羧酸基团是指式(-CO)xR的基团,其中x如上述对n1的定义,和R的含义来于上述定义。
最多含20个碳原子的烷基例如是甲基、乙基、正丙基、正丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十六烷基或正十八烷基。
C3-C8链烯基G11可以是例如1-丙烯基、烯丙基、甲基烯丙基、2-丁烯基、2-戊烯基、2-己烯基、2-辛烯基或4-叔丁基-2-丁烯基。
C3-C8炔基G11优选炔丙基。
C7-C12芳烷基G11尤其是苯乙基,特别是苄基。
C1-C18烷氧基G11例如是甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、戊氧基、异戊氧基、己氧基、庚氧基、辛氧基、癸氧基、十二烷氧基、十四烷氧基、十六烷氧基和十八烷氧基。优选C6-C12烷氧基,尤其是庚氧基和辛氧基。
C5-C8环烷氧基G11例如是环戊氧基、环己氧基、环庚氧基、环辛氧基、环癸氧基和环十二烷氧基。优选C5-C8环烷氧基,尤其是环戊氧基和环己氧基。
C7-C9苯基烷氧基例如是苄氧基。
C1-C8烷酰基G11例如是甲酰基、丙酰基、丁酰基、辛酰基,但优选乙酰基,而C3-C5链烯酰基G11尤其是丙烯酰基。
C1-C18烷酰氧基G11例如是甲酰氧基、乙酰氧基、丙酰氧基、丁酰氧基、戊酰氧基、月桂酰氧基、棕榈酰氧基和硬脂酰氧基。
以下给出了一些G12基团的实例。
若G12是羧酸的一价基团,则它例如是乙酰基、己酰基、硬脂酰基、丙烯酰基、甲基丙烯酰基、苯甲酰基或β-(3,5-二叔丁基-4-羟苯基)丙酰基基团。
若G12是一价的甲硅烷基基团,则它例如是式-(CjH2j)-Si(Z′)2Z″的基团,其中j是介于2-5的整数,以及Z′和Z″彼此独立地为C1-C4烷基或C1-C4烷氧基。
若G12是二羧酸的二价基团,则它例如是丙二酰基、丁二酰基、戊二酰基、己二酰基、辛二酰基、癸二酰基、马来酰基、衣康酰基、邻苯三甲酰基、二丁基丙二酰基、二苄基丙二酰基、丁基(3,5-二叔丁基-4-羟苄基)丙二酰基或二环亚庚基二羰基基团或下式的基团
若G12是三羧酸的三价基团,则它例如是偏苯三酰基、柠檬酰基或次氮基三乙酰基基团。
若G12是四羧酸的四价基团,则它例如是丁烷-1,2,3,4-四羧酸的四价基团或均苯四酸的四价基团。
若G12是二氨基甲酸的二价基团,则它例如是六亚甲基二氨基甲酰基或2,4-亚甲苯甲酰基二氨基甲酰基基团。
优选其中G和G1是氢、G11是氢或甲基,n1是2,以及G12是具有4-12个碳原子的脂族二羧酸的二酰基基团的式(Ia)的化合物。
来源于该组的聚烷基哌啶化合物的实例是下述化合物:
1)4-羟基-2,2,6,6-四甲基哌啶
2)1-烯丙基-4-羟基-2,2,6,6-四甲基哌啶
3)1-苄基-4-羟基-2,2,6,6-四甲基哌啶
4)1-(4-叔丁基-2-丁烯基)-4-羟基-2,2,6,6-四甲基哌啶
5)4-硬脂酰氧基-2,2,6,6-四甲基哌啶
6)1-乙基-4-水杨酰氧基-2,2,6,6-四甲基哌啶
7)4-甲基丙烯酰氧基-1,2,2,6,6-五甲基哌啶
8)1,2,2,6,6-五甲基哌啶-4-基β-(3,5-二叔丁基-4-羟苯基)丙酸酯
9)二(1-苄基-2,2,6,6-四甲基哌啶-4-基)马来酸酯
10)二(2,2,6,6-四甲基哌啶-4-基)丁二酸酯
11)二(2,2,6,6-四甲基哌啶-4-基)戊二酸酯
12)二(2,2,6,6-四甲基哌啶-4-基)己二酸酯
13)二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯
14)二(1,2,2,6,6-五甲基哌啶-4-基)癸二酸酯
15)二(1,2,3,6-四甲基-2,6-二乙基-哌啶-4-基)癸二酸酯
16)二(1-烯丙基-2,2,6,6-四甲基哌啶-4-基)邻苯二甲酸酯
17)1-羟基-4-β-氰乙氧基-2,2,6,6-四甲基哌啶
18)1-乙酰基-2,2,6,6-四甲基哌啶-4-基乙酸酯
19)三(2,2,6,6-四甲基哌啶-4-基)偏苯三酸酯
20)1-丙烯酰基-4-苄氧基-2,2,6,6-四甲基哌啶
21)二(2,2,6,6-四甲基哌啶-4-基)二乙基丙二酸酯
22)二(1,2,2,6,6-五甲基哌啶-4-基)二丁基丙二酸酯
23)二(1,2,2,6,6-五甲基哌啶-4-基)丁基(3,5-二叔丁基-4-羟苄基)丙二酸酯
24)二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯
25)二(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯
26)己烷-1′,6′-双(4-氨基甲酰氧基1-正丁基-2,2,6,6-四甲基哌啶)
27)甲苯-2′,4′-双(4-氨基甲酰氧基1-正丙基-2,2,6,6-四甲基哌啶)
28)二甲基双(2,2,6,6-四甲基哌啶-4-氧基)硅烷
29)苯基三(2,2,6,6-四甲基哌啶-4-氧基)硅烷
30)三(1-丙基-2,2,6,6-四甲基哌啶-4-基)亚磷酸酯
30-a)三(1-甲基-2,2,6,6-四甲基哌啶-4-基)亚磷酸酯
31)三(1-丙基-2,2,6,6-四甲基哌啶-4-基)磷酸酯
32)苯基双(1,2,2,6,6-五甲基哌啶-4-基)膦酸酯
33)4-羟基-1,2,2,6,6-五甲基哌啶
34)4-羟基-N-羟乙基-2,2,6,6-四甲基哌啶
35)4-羟基-N-(2-羟丙基)-2,2,6,6-四甲基哌啶
36)1-缩水甘油基-4-羟基-2,2,6,6-四甲基哌啶
36-a-1)1,2,3,4-四[2,2,6,6-四甲基哌啶-4-基氧基羰基]丁烷
36-a-2)双[2,2,6,6-四甲基哌啶-4-基氧基羰基]-双[三癸氧基羰基]丁烷
36-b-1)1,2,3,4-四[1,2,2,6,6-五甲基哌啶-4-基氧基羰基]丁烷
36-b-2)双[1,2,2,6,6-五甲基哌啶-4-基氧基羰基]-双[三癸氧基羰基]丁烷
36-c)2,2,6,6-四甲基哌啶-4-基氧基羰基(C15-C17烷烃)
(b′)式(Ib)的化合物
其中n2是数1、2或3,G、G1和G11如(a′)中所定义,G13是氢、C1-C12烷基、C2-C5羟烷基、C5-C7环烷基、C7-C8芳烷基、C1-C18烷酰基、C3-C5链烯酰基、苯甲酰基或下述式的基团:
和若n2为1,则G14是氢、C1-C18烷基、C3-C8链烯基、C5-C7环烷基、被羟基、氰基、烷氧基羰基或脲基取代的C1-C4烷基、缩水甘油基、式-CH2-CH(OH)-Z或式-CONH-Z的基团,其中Z是氢、甲基或苯基;
和若n2为2,则G14是C2-C12亚烷基、C6-C12亚芳基、亚二甲苯基、-CH2-CH(OH)-CH2基团或-CH2-CH(OH)-CH2-O-D-O-基团,其中D是C2-C10亚烷基、C6-C15亚芳基、C6-C12亚环烷基,或者若G13不是烷酰基、链烯酰基或苯甲酰基,则G14可以是1-氧代-C2-C12亚烷基或脂族、脂环族或芳族二羧酸或二氨基甲酸的二价基团或-CO-基,
若n2为3,则G14是基团
或者若n2为1,则G13和G14一起可以为脂族、脂环族或芳族1,2-或1,3-二羧酸的二价基团。
以下给出了基团G13、G14和D的一些实例。
任何烷基取代基如(a′)中所定义。
任何C5-C7环烷基取代基尤其是环己基。
C7-C8芳烷基G13尤其是苯乙基,或特别是苄基。
C2-C5羟烷基G13尤其是2-羟乙基或2-羟丙基。
C1-C18烷酰基G13例如是甲酰基、乙酰基、丙酰基、丁酰基、辛酰基、十二烷酰基、十六烷酰基、十八烷酰基,但优选乙酰基,而C3-C5链烯酰基G13尤其是丙烯酰基。
C2-C8链烯基G14例如是烯丙基、甲基烯丙基、2-丁烯基、2-戊烯基、2-己烯基或2-辛烯基。
作为被羟基、氰基、烷氧基羰基或脲基取代的C1-C4烷基的G14可以是例如2-羟乙基、2-羟丙基、2-氰乙基、甲氧基羰基甲基、2-乙氧基羰基乙基/2-氨基羰基丙基或2-(二甲基氨基羰基)乙基。
任何C2-C12亚烷基基团例如是亚乙基、亚丙基、2,2-二甲基亚丙基、1,4-亚丁基、1,6-亚己基、1,8-亚辛基、1,10-亚癸基或1,12-亚十二烷基。
任何C6-C15亚芳基取代基例如是邻-、间-或对-亚苯基、1,4-亚萘基或4,4′-二亚苯基。
C6-C12亚环烷基尤其是亚环己基。
作为1-氧代-C2-C12亚烷基的G14优选下述基团;
优选的式(Ib)化合物中n2是1或2,G和G1是氢,G11是氢或甲基,G13是氢、C2-C12烷基或下述式的基团:
和在n=1的情况下,G14是氢或C1-C12烷基,和在n=2的情况下,G14是C2-C8亚烷基或1-氧代-C2-C8亚烷基。
来源于该组的聚烷基哌啶的实例是下述化合物:
37)N,N′-双(2,2,6,6-四甲基哌啶-4-基)六亚甲基-1,6-二胺
38)N,N′-双(2,2,6,6-四甲基哌啶-4-基)六亚甲基-1,6-二乙酰胺
39)双(2,2,6,6-四甲基哌啶-4-基)胺
40)4-苯甲酰基氨基-2,2,6,6-四甲基哌啶
41)N,N′-双(2,2,6,6-四甲基哌啶-4-基)-N,N′-二丁基己二酰胺
42)N,N′-双(2,2,6,6-四甲基哌啶-4-基)-N,N′-二环己基-2-羟基亚丙基-1,3-二胺
43)N,N′-双(2,2,6,6-四甲基哌啶-4-基)-对亚二甲苯基二胺
44)N,N′-双(2,2,6,6-四甲基哌啶-4-基)丁二酰胺
45)双(2,2,6,6-四甲基哌啶-4-基)N-(2,2,6,6-四甲基哌啶-4-基)-β-氨基二丙酸酯
46)下述式的化合物;
47)4-双(2-羟乙基氨基)-1,2,2,6,6-五甲基哌啶
48)4-(3-甲基-4-羟基-5-叔丁基-苯甲酰胺)-2,2,6,6-四甲基哌啶
49)4-甲基丙烯酰胺基-1,2,2,6,6-五甲基哌啶
49-b)N,N′,N″-三[2,2,6,6-四甲基哌啶-4-基氨基(2-羟基亚丙基)]异氰脲酸酯
49-c)2-(2,2,6,6-四甲基哌啶-4-基氨基)-2-(2,2,6,6-四甲基哌啶-4-基氨基羰基)丙烷
49-d)1,6-双[N-(2,2,6,6-四甲基哌啶-4-基)甲酰氨基]己烷
(c′)式(Ic)的化合物
其中n3是数1或2,G、G1和G11如(a′)中所定义,和若n3为1,则G15是C2-C8亚烷基、C2-C8羟基亚烷基或C4-C22酰氧基亚烷基;若n3为2,则G15是-(-CH2)2C(CH2-)2基团。
C2-C8亚烷基或C2-C8羟基亚烷基G15例如是亚乙基、1-甲基亚乙基、亚丙基、2-乙基亚丙基或2-乙基-2-羟甲基亚丙基。
C4-C22酰氧基亚烷基G15例如是2-乙基-2-乙酰氧基甲基亚丙基。
来源于该组的多烷基哌啶的实例是下述化合物:
50)9-氮杂-8,8,10,10-四甲基-1,5-二氧杂螺[5.5]十一烷
51)9-氮杂-8,8,10,10-四甲基-3-乙基-1,5-二氧杂螺[5.5]十一烷
52)8-氧杂-2,7,7,8,9,9-六甲基-1,4-二氧杂螺[4.5]十一烷
53)9-氮杂-3-羟甲基-3-乙基-8,8,9,10,10-五甲基-1,5-二氧杂螺[5.5]十一烷
54)9-氮杂-3-乙基-3-乙酰氧基甲基-9-乙酰基-8,8,10,10-四甲基-1,5-二氧杂螺[5.5]十一烷
55)2,2,6,6-四甲基哌啶-4-螺-2′-(1,3′-二噁烷)-5′-螺-5″-(1″,3″-二噁烷)-2″-螺-4″′-(2″′,2″′,6″′,6″′-四甲基哌啶)
(d′)式(Id-1)、(Id-2)或(Id-3)的化合物,
其中n4是数1或2,G、G1和G11如(a′)中所定义,G16是氢、C1-C12烷基、烯丙基、苄基、缩水甘油基或C2-C6烷氧烷基,和若n4是1,则G17是氢、C1-C12烷基、C3-C5链烯基、C7-C9芳烷基、C5-C7环烷基、C2-C4羟烷基、C2-C6烷氧烷基、C6-C10芳基、缩水甘油基或式-(CH2)p-COO-Q或-(CH2)p-O-CO-Q基团,其中p是1或2,和Q是C1-C4烷基或苯基,和若n4是2,则G17是C2-C12亚烷基、C4-C12亚链烯基、C6-C12亚芳基、式-(CH2)-CH(OH)-CH2-O-D′-O-CH2-CH(OH)-CH2-的基团,其中D′是C2-C10亚烷基、C6-C15亚芳基或C6-C12亚环烷基,或式-(CH2)CH(OD″)CH2-(OCH2-CH(OD″)-CH2)2-的基团,其中D″是氢、C1-C18烷基、烯丙基、苄基、C2-C12烷酰基或苯甲酰基,T1和T2彼此独立地为氢、C1-C18烷基或者未取代的或被卤素或C1-C4烷基取代的C6-C10芳基或C7-C9芳烷基,或者T1和T2一起与和它们键联的碳原子形成C5-C14环烷烃环。
优选式(Id-3)的化合物。
以下给出了式(Id-1)、(Id-2)和(Id-3)中一些变体的一些实例。
任何C1-C12烷基取代基例如是甲基、乙基、正丙基、正丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基或正十二烷基。
任何C1-C18烷基取代基可以是例如上述基团和另外,例如正十三烷基、正十四烷基、正十六烷基或正十八烷基。
任何C2-C6烷氧烷基取代基例如是甲氧基甲基、乙氧基甲基、丙氧基甲基、叔丁氧基甲基、乙氧基乙基、乙氧基丙基、正丁氧基乙基、叔丁氧基乙基、异丙氧基乙基或丙氧基丙基。
C3-C5链烯基G17例如是1-丙烯基、烯丙基、甲基烯丙基、2-丁烯基或2-戊烯基。
C7-C9芳烷基G17、T1和T2尤其是苯乙基,或特别是苄基。若T1和T2一起与碳原子键接,形成环烷烃环,则这可以是例如环戊烷、环己烷、环辛烷或环十二烷环。
C2-C4羟烷基G17例如是2-羟乙基、2-羟丙基、2-羟丁基或4-羟丁基。
C6-C10芳基G17、T1和T2尤其是未被取代或被卤素或C1-C4烷基取代的苯基或α-或β-萘基。
C2-C12亚烷基G17例如是亚乙基、亚丙基、2,2-二甲基亚丙基、1,4-亚丁基、1,6-亚己基、1,8-亚辛基、1,10亚癸基或1,12-亚十二烷基。
C4-C12亚链烯基G17尤其是2-亚丁烯基、2-亚戊烯基或3-亚己烯基。
C6-C12亚芳基G17例如是邻-、间-或对-亚苯基、1,4-亚萘基或4,4′-二亚苯基。
C2-C12烷酰基D″例如是丙酰基、丁酰基、辛酰基、十二烷酰基,但优选乙酰基。
C2-C10亚烷基、C6-C15亚芳基或C6-C12环亚烷基D′例如是(b′)中对D给出的定义之一。
来源于该组的多烷基哌啶的实例是下述化合物:
56)3-苄基-1,3,8-三氮杂-7,7,9,9-四甲基螺[4.5]癸烷-2,4-二酮
57)3-正辛基-1,3,8-三氮杂-7,7,9,9-四甲基螺[4.5]癸烷-2,4-二酮
58)3-烯丙基-1,3,8-三氮杂-1,7,7,9,9-五甲基螺[4.5]癸烷-2,4-二酮
59)3-缩水甘油基-1,3,8-三氮杂-7,7,8,9,9-五甲基螺[4.5]癸烷-2,4-二酮
60)1,3,7,7,8,9,9-七甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮
61)2-异丙基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代螺[4.5]癸烷
62)2,2-二丁基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代螺[4.5]癸烷
63)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
64)2-丁基-7,7,9,9-四甲基-1-氧杂-4,8-二氮杂-3-氧代螺[4.5]癸烷和优选地:
65)8-乙酰基-3-十二烷基-1,3,8-三氮杂-7,7,9,9-四甲基螺[4.5]癸烷-2,4-二酮
和下式的化合物:
(e′)式(Ie)的化合物
其中n5是数1或2,和G18是下式的基团:
其中G和G11如(a′)中所定义,以及G1和G2为氢、甲基或一起为取代基=O。
E是-O-或-ND″′-,
A是C2-C6亚烷基或-(CH2)3-O-和
x1是数0或1,
D″′是氢、C1-C12烷基、C2-C5羟烷基或C5-C7环烷基,
G19与G18相同,或是-N(G21)(G22)、-OG23、-N(H)(CH2OG23)或-N(CH2OG23)2中的基团之一;
若n5=1,则G20与G18或G19相同,和若n5=2,则G20是-E-DIV-E-基团,其中DIV是C2-C8亚烷基或被1个或2个-NG21-基团取代的C2-C8亚烷基,
G21是C1-C12烷基、环己基、苄基或C1-C4羟烷基或下式的基团:
G22是C1-C12烷基、环己基、苄基或C1-C4羟烷基,和
G23是氢、C1-C12烷基或苯基,或者G21和G22一起为C4-C5亚烷基或C4-C5氧杂亚烷基,例如-CH2CH2-O-CH2CH2-,或者式-CH2CH2-N(G11)-CH2CH2-的基团。
以下给出了式(Ie)中一些变体的一些实例。
任何C1-C12烷基取代基例如是甲基、乙基、正丙基、正丁基、仲丁基、叔丁基、正己基、正辛基、2-乙基己基、正壬基、正癸基、正十一烷基或正十二烷基。
任何羟烷基取代基例如是2-羟乙基、2-羟丙基、3-羟丙基、2-羟丁基或4-羟丁基。
任何C5-C7环烷基取代基例如是环戊基、环己基或环庚基。优选环己基。
C2-C6亚烷基A例如是亚乙基、异丙基、2,2-二甲基亚苯基、1,4-亚丁基或1,6-亚己基。
若G21和G22一起为C4-C5亚烷基或氧杂亚烷基,则它们是例如1,4-亚丁基、1,5-亚戊基或3-氧杂1,5-亚戊基。
来源于该组的多烷基哌啶的实例是下述化合物:
其中R具有与化合物74中相同的含义。
其中R′具有与化合物76中相同的含义。
(f′)式(If)的化合物
其中G11如(a′)中所定义。
这一类优选的实例是下述的化合物:
(g′)重复结构单元含有2,2,6,6-四烷基哌啶基团的低聚物或聚合化合物,尤其是聚酯、聚醚、聚酰胺、聚胺、聚氨酯、聚脲、聚氨基三嗪、聚(甲基)丙烯酸酯、聚(甲基)丙烯酰胺和含有这些基团的共聚物。
该组的2,2,6,6-聚烷基哌啶化合物的实例是下述式的化合物。m1-m14是2-约200的数,优选2-100,例如2-50,2-40,3-40或4-10。
使以下所列的低聚物或聚合化合物的自由价饱和的端基,其含义取决于制备所述化合物所使用的方法。也可在合成化合物之后另外改性端基。
在化合物82-a和82-b中,键合到-O-上的端基分别可以是例如氢或-CO-(CH2)2-COO-Y或-CO-(CH2)4-COO-Y基团,其中Y是氢或C1-C4烷基,以及键合到二酰基上的端基可以是例如-O-Y或下述基团:
在化合物83中,键合到氨基残基上的端基可以是例如基团和键合到二酰基残基上的端基可以是例如Cl。
在化合物84-1-a、84-1-b和84-2中,键合到三嗪残基上的端基可以是例如氯或下述基团:
以及键合到二氨基基团上的端基可以是例如氢或下述基团:
可方便地通过例如-OH或氨基来置换与三嗪连接的氯。合适的氨基典型地是吡咯烷-1-基、吗啉基、-NH2、-N(C1-C8烷基)2和-NY′(C1-C8烷基),其中Y′是氢或下述式的基团:
在化合物85中,键合到2,2,6,6-四甲基哌啶-4-基氨基残基上的端基可以是例如氢,和键合到2-羟基亚丙基残基上的端基可以是例如
在化合物89中,键合到-CH2-上的端基可以是例如氢,和键合到酯基残基上的端基可以是例如
在化合物90中,键合到-CH2-上的端基可以是例如氢,和键合到酯基残基上的端基可以是例如
在化合物91中,键合到-CH2-上的端基可以是例如氢,和键合到氨基残基上的端基可以是例如
其中m11 *如m11中的定义,基团R*彼此独立地为乙基或2,2,6,6-四甲基哌啶-4-基,前提是至少50%的基团R*是2,2,6,6-四甲基哌啶-4-基和其余基团R*是乙基。在化合物91-1)中,端基例如是氢。
可方便地通过例如-OH或氨基来置换与三嗪连接的氯。合适的氨基典型地是吡咯烷-1-基、吗啉基、-NH2、-N(C1-C8烷基)2和-NY′(C1-C8烷基),其中Y′是氢或下式的基团:
在化合物94中,键合到二氨基残基上的端基可以是例如氢,和键合到-CH2CH2-残基上的端基可以是例如
在化合物95-1中,键合到二氨基残基上的端基可以是例如氢,和键合到二酰基残基上的端基可以是例如Cl。
其中R″是下式的基团:
m′15和m″15各自为0-200的数,优选0-100,尤其是0-50,前提是m′15+m″15是2-200的数,优选2-100,尤其是2-50。在化合物95-1中,键合到二氨基残基上的端基可以是例如氢,和键合到-CH2CH2-基团上的端基可以是例如卤素,尤其是氯或溴。
式(96-I)或(96-II)的化合物
其中m16和m* 16是2-50的数,例如2-25。
在制备过程中,可一起以混合物的形式获得式(96-I)和(96-II)的化合物,从而也可如此使用该混合物。(96-I)∶(96-I I)的重量比例如是20∶1-1∶20或1∶10-10∶1。
在式(96-I)的化合物中,键合到氮上的端基可以是例如氢,和键合到2-羟基亚丙基残基上的端基可以是例如基团
在式(96-II)的化合物中,键合到二亚甲基残基上的端基可以是例如-OH,和键合到氧上的端基可以是例如氢。端基也可以是聚醚基团。
式(96-III)的化合物
其中Q1 *和Q2 *彼此独立地为氢或C1-C8烷基,或Q1 *和Q2 *一起为C5-C11亚烷基,变量m16 **彼此独立地为1-50的数。
聚合物化合物的进一步的实例是:
1)式(97)的化合物
其中G24、G25、G26、G27和G28彼此独立地为直接键或C1-C10亚烷基,G11如(a′)中所定义,和m17是1-50的数。
优选下述两种化合物:
其中m17是1-20的数。
2)式(98)的化合物
其中约1/3的RIV基团是-C2H5和其它是基团
和m18是介于2-200的数,优选2-100,尤其是2-50。
在化合物(98)中,键合到-CH2残基上的端基可以是例如氢,和键合到-CH(CO2RIV)-残基上的端基可以是例如-CH=CH-COORIV。
3)式(99)的化合物
其中G11如(a′)中所定义,G29和G32彼此独立地为直接键或-N(X1)-CO-X2-CO-N(X3)-基团,其中X1和X3彼此独立地为氢、C1-C8烷基、C5-C12环烷基、苯基、C7-C9苯烷基或式(99-1)的基团
和X2为直接键或C1-C4亚烷基,G30、G31、G34和G35彼此独立地为氢、C1-C30烷基、C5-C12环烷基或苯基,G33是氢、C1-C30烷基、C5-C12环烷基、C7-C9苯烷基、苯基或式(99-1)的基团,和m19是1-50的数。
在式(99)的化合物中,键合到2,5-二氧代吡咯烷环上的端基可以是例如氢,和键合到-C(G34)(G35)-基团上的端基可以是例如
式(99)的化合物的实例是:
其中G11是氢或甲基,和m19是1-25的数。
4)通过使式(100a)的多胺与氰尿酰氯反应而获得的中间产物与式(100b)的化合物反应而获得的产物。
其中m′20、m″20和m″′20彼此独立地为2-12的数,G36是氢、C1-C12烷基、C5-C12环烷基、苯基或C7-C9苯烷基,和G11如(a′)中所定义。优选的产物是Chemical Abstracts-CAS No.136 504-96-6(化合物100-A)。
一般地,可用式100-1、100-2或100-3的化合物表示上述反应产物。它们也可以是这三类化合物的混合物。
优选的式(100-1)是
优选的式(100-2)是
优选的式(100-3)是
在上述式100-1到100-3中,m20优选2-20,尤其是2-10。
5)式(101)的化合物
其中G11如(a′)中所定义,G37是C1-C10烷基、C5-C12环烷基、C1-C4烷基取代的C5-C12环烷基、苯基或C1-C10烷基取代的苯基,G38是C3-C10亚烷基,和m2是1-50的数。
在式(101)的化合物中,键合到硅原子上的端基可以是例如(G37)3Si-O-,和键合到氧上的端基可以是例如-Si(G37)3。
若m21是3-10的数,则式(101)的化合物也可呈环状化合物形式,即结构式中所示的自由价然后形成直接键。
式(101)的化合物的实例是
其中m21是1-20的数,例如2-20。
在以上所示的低聚物和聚合化合物中,烷基的实例是甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、正戊基、异戊基、1-甲基戊基、1,3-二甲基丁基、正己基、1-甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、2-乙基-己基、1,1,3-三甲基己基、1,1,3,3-四甲基戊基、壬基、癸基、十一烷基、1-甲基十一烷基、十二烷基、1,1,3,3,5,5-六甲基己基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基和二十二烷基;
环烷基的实例是环戊基、环己基、环庚基和环辛基;
C7-C9苯烷基的实例是苄基;和
亚烷基的实例是亚乙基、亚丙基、1,3-亚丙基、1,4-亚丁基、1,5-亚戊基、2,2-二甲基三亚甲基、1,6-亚己基、三甲基1,6-亚己基、1,8-亚辛基和1,10-亚癸基。
(h′)式(Ih)的化合物
其中n6是数1或2,G和G11如(a′)中所定义,和G14如(b′)中所定义,但G14不能是-CONH-Z和-CH2-CH(OH)-CH2-O-D-O-。
这些化合物的实例如下:
(i′)式(Ii)的化合物
其中基团G39彼此独立地为式(Ii-1)中的基团
其中G40是C1-C12烷基或C5-C12环烷基,G41是C2-C12亚烷基和G42是氢、C1-C8烷基、-O、-CH2CN、C3-C6链烯基、C7-C9苯烷基、在苯基上被C1-C4烷基取代的C7-C9苯烷基、或者C1-C8酰基。
烷基例如是C1-C4烷基,尤其是甲基、乙基、丙基或丁基。
环烷基优选环己基。
亚烷基例如是亚乙基、亚丙基、1,3-亚丙基、1,4-亚丁基、1,5-亚戊基、2,2-二甲基三亚甲基或1,6-亚己基。
链烯基优选烯丙基。
苯烷基优选苄基。
酰基优选乙酰基。
来自该组的化合物的实例是下式的化合物:
以上所列的位阻胺化合物是已知的,且若不是商购的话,则可根据已知的方法来制备。
一些优选的位阻胺是以下列商品名称商购的:
DASTIB 845(RTM),TINUVIN 770(RTM),TINUVIN 765(RTM),TINUVIN 144(RTM),TINUVIN 123(RTM),ADK STAB LA 57(RTM),ADK STAB LA 67(RTM),ADK STAB LA52(RTM),ADK STAB LA 62(RTM),SANDUVOR PR·31(RTM),CYASORB UV 3581(RTM),CYASORB UV 3604(RTM),SUMISORB TM 61(RTM),UVINUL 4050H(RTM),DIACETAM5(RTM),HOSTAVIN N 20(RTM),TINUVIN 440(RTM),SANDUVOR3050(RTM),HOSTAVIN N 24(RTM),CHIMASSORB 966(RTM),UVINUL 4049(RTM),GOODRITE UV3034(RTM),GOODRITE UV 3150(RTM),GOODRITE UV 3159(RTM),CHIMASSORB 119(RTM),TINUVIN 622(RTM),CHIMASSORB 944(RTM),CHIMASSORB 2020(RTM),DASTIB 1082(RTM),FERRO AM 806(RTM),CYASORB UV 3346(RTM),CYASORB UV3529(RTM),HOSTAVIN N 30(RTM),ADK STAB LA 68(RTM),ADK STAB LA 63(RTM),UVINUL 5050H(RTM),LICHTSCHUTZSTOFF UV 31(RTM),LUCHEM HA·B 18(RTM),UVASORB HA 88(RTM)and UVASIL 299(RTM).
根据令人关注的一个实施方案,组分(A)相应于化合物(5),(13),(14),(23),(24),(36-a-1),(36-a-2),(36-b-1),(36-b-2),(36-d),(49-a-1),(49-a-2),(49-c),(49-d),(49-e),(63),(65),(69-a),(81),(82),(102),(105)或(106),尤其是化合物(5),(13),(14),(24),(49-a-1),(49-a-2)或(49-d),特别是化合物(13)。
根据令人关注的另一实施方案,组分(A)相应于化合物(76),(82-a),(84-1-a),(84-1-b),(84-2),(91-1),(92),(93),(96-I),(96-II),(97-I),(97-I I),(99-I),(99-I I),(99-I I I),(100-A)或(101-I)。尤其是化合物(76),(84-1-a),(84-1-b),(92),(93),(99-I),(100-A)或(101-I),特别是化合物(76),(84-1-a),(84-1-b),(92)或(100-A)。
含有极性基团的聚合物(组分(B))优选:
(B-1)含卤素的聚合物,
(B-2)衍生于α,β-不饱和酸或其衍生物的聚合物
(B-3)丙烯腈/丁二烯共聚物、丙烯腈/丙烯酸烷基酯共聚物、乙烯/丙烯酸酯共聚物、丙烯腈/丙烯酸烷氧烷基酯或丙烯腈/卤代乙烯共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物,
(B-4)衍生于不饱和醇和胺或酰基衍生物或其缩醛的聚合物,
(B-5)环醚的均聚物或共聚物,
(B-6)聚缩醛,
(B-7)聚苯醚或聚苯醚与其它聚合物(例如聚酰胺)的混合物,
(B-8)聚氨酯,
(B-9)聚酰胺或共聚酰胺,
(B-10)聚脲、聚酰亚胺、聚酰胺-酰亚胺、聚醚酰亚胺、聚酯酰亚胺、聚海因(polyhydantoin)、聚苯并咪唑或聚乙烯基咪唑,
(B-11)聚酯,
(B-12)聚碳酸酯或聚酯碳酸酯(polyester carbonate),
(B-13)聚砜、聚醚砜或聚醚酮,
(B-14)一方面衍生于醛而另一方面衍生于酚、脲或蜜胺的聚合物,
(B-15)干燥或未干燥的醇酸树脂,
(B-16)不饱和的聚酯树脂,
(B-17)可交联的丙烯酸树脂,
(B-18)用蜜胺树脂、脲醛树脂、异氰酸酯、异氰脲酸酯、聚异氰酸酯或环氧树脂交联的醇酸树脂、聚酯树脂或丙烯酸酯树脂,
(B-19)环氧树脂,
(B-20)纤维素或其化学改性的同系衍生物,
(B-21)聚有机硅氧烷,
(B-22)聚乙烯醇缩甲醛(PVF),
(B-23)聚(芳基-醚-醚-酮)(PEEK),或
(B-24)乙烯基芳族单体的共聚物。
含卤素的聚合物(B-1)的实例是聚氯丁二烯、氯化橡胶、异丁烯-异戊二烯的氯化和溴化共聚物(卤丁橡胶)、氯化或氨磺化的聚乙烯、乙烯和氯化乙烯的共聚物、表氯醇的均聚物和共聚物,特别是含卤素的乙烯基化合物的聚合物,例如聚氯乙烯、聚偏氯乙烯、聚氟乙烯、聚偏氟乙烯、及其共聚物(如氯乙烯/偏氯乙烯、氯乙烯/醋酸乙烯酯或偏氯乙烯/醋酸乙烯酯的共聚物)。优选聚氟代烃和聚乙烯基缩甲醛。
衍生于α,β-不饱和酸或其衍生物的聚合物(B-2)的实例是聚丙烯酸酯和聚甲基丙烯酸酯;用丙烯酸丁酯抗冲改性的聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈。
衍生于不饱和醇和胺或酰基衍生物或其缩醛的聚合物(B-4)的实例是聚乙烯醇、聚醋酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙酯或聚烯丙基蜜胺及其与烯烃的共聚物。
环醚的均聚物或共聚物(B-5)的实例是聚亚烷基二醇、聚环氧乙烷、聚环氧丙烷或其与二缩水甘油基醚的共聚物。
聚缩醛(B-6)的实例是聚甲醛和含有环氧乙烷作为共聚单体的那些聚甲醛;用热塑性聚氨酯、丙烯酸酯或MBS改性的聚缩醛。
聚氨酯(B-8)的实例是一方面衍生于羟基封端的聚醚、甲酯或聚丁二烯和另一方面衍生于脂族或芳族聚异氰酸酯的那些及其母体。
聚酰胺或共聚酰胺(B-9)的实例是衍生于二胺和二羧酸和/或氨基羧酸或相应的内酰胺(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)、起始于间二甲苯二胺和己二酸的芳族聚酰胺、由六亚甲基二胺和间苯二酸或/和对苯二酸制备且有或无弹性体作为改性剂的聚酰胺(例如聚-2,4,4-三甲基六亚甲基对苯二胺或聚间苯二甲酰间苯二胺);以及前述聚酰胺与聚烯烃、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;或前述聚酰胺与聚醚(如与聚乙二醇、聚丙二醇或聚丁二醇)的嵌段共聚物;以及用EPDM或ABS改性的聚酰胺或共聚酰胺;和在加工过程中缩合的聚酰胺(RIM聚酰胺体系)。
聚酯(B-11)的实例是衍生于二羧酸和二醇的那些和/或衍生于羟基羧酸或相应的内酯(例如聚对苯二甲酸乙二酯、聚对苯二甲酸丁二酯、聚1,4-二羟甲基环己烷对苯二甲酸酯、聚萘二甲酸亚烷基二醇酯(PAN)和聚羟基苯甲酸酯)的那些,以及衍生于羟基封端的聚醚的嵌段共聚醚酯;以及用聚碳酸酯或MBS改性的聚酯。
一方面衍生于醛而另一方面衍生于酚、脲或蜜胺的聚合物(B-14)的实例是酚/甲醛树脂、脲/甲醛树脂和蜜胺/甲醛树脂。
不饱和聚酯树脂(B-16)的实例是衍生于饱和与不饱和二羧酸同作为交联剂的多元醇和乙烯基化合物的共聚酯的那些,以及可燃性低的含有卤素的改性物质。
可交联的丙烯酸树脂(B-17)的实例是衍生于取代的丙烯酸酯(环氧丙烯酸酯、氨基甲酸酯丙烯酸酯或聚酯丙烯酸酯)的那些。
环氧树脂(B-19)的实例是衍生于脂族、脂环族、杂环或芳族缩水甘油基化合物的那些,如双酚A和双酚F的二缩水甘油基醚产品,该产品在有或无促进剂情况下,可用常规的硬化剂如酸酐或胺交联。
纤维素或其化学改性的同系衍生物(B-20)的实例是乙酸纤维素、丙酸纤维素和丁酸纤维素或纤维素醚如甲基纤维素。
乙烯基芳族单体的共聚物(B-24)的实例是苯乙烯/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。
尤其优选丙烯酸酯/苯乙烯/丙烯腈共聚物(ASA)、苯乙烯/丙烯腈共聚物(SAN)和苯乙烯/马来酸酐共聚物(SMA)。
乙烯基芳族单体的实例是苯乙烯、α-甲基苯乙烯、乙烯基甲苯的所有异构体,特别是对乙烯基甲苯、乙基苯乙烯、丙基苯乙烯、乙烯基联苯、乙烯基萘和乙烯基蒽的所有异构体。这些乙烯基芳族单体的合适的共聚单体是例如腈、马来酸酐、马来酰亚胺、醋酸乙烯酯和氯乙烯或丙烯酸的衍生物。
组分(B)优选选自(B-2),(B-4),(B-6),(B-7),(B-8),(B-9),(B-11),(B-12)和(B-13)。
根据另一优选的实施方案,组分(B)是聚丙烯酸酯、聚甲基丙烯酸酯(PMA)、聚甲基丙烯酸甲酯(PMMA)、聚丙烯腈(PAN)、聚乙烯醇(PVA)、聚醋酸乙烯酯(PVAc)、聚甲醛(POM)、聚苯醚(PPE)、聚氨酯、聚酰胺3(PA 3)、聚酰胺6(PA 6)、聚酰胺11(PA 11)、聚酰胺12(PA 12)、聚酰胺66(PA 66)、聚对苯二甲酸乙二酯(PET)、聚对苯二甲酸丁二酯(PBT)、聚乳酸(PLA)、聚碳酸酯(PC)或聚醚砜(PES)或具有以下式的重复单元的芳族-脂族聚砜(PSP):
根据另一优选的实施方案,组分(B)是聚酰胺(PA),丙烯酸酯/苯乙烯/丙烯腈共聚物(ASA),苯乙烯/丙烯腈共聚物(SAN),苯乙烯/马来酸酐共聚物(SMA)或聚醚酰胺。
根据特别优选的实施方案,组分(B)是聚甲基丙烯酸酯(PMA)、聚甲基丙烯酸甲酯(PMMA)、聚酰胺(PA)、聚甲醛(POM)、丙烯酸酯/苯乙烯/丙烯腈共聚物(ASA)或聚醚酰胺。
优选的稳定剂混合物是其中组分(A)是化合物二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯,组分(B)是聚对苯二甲酸乙二酯(PET)、聚酰胺6(PA 6)、聚碳酸酯(PC)、聚甲基丙烯酸酯(PMA)或聚甲基丙烯酸甲酯(PMMA),尤其是聚甲基丙烯酸甲酯(PMMA)的那些混合物,和组分(A)∶(B)的重量比是5∶1-1∶5。
再一优选的稳定剂混合物是其中组分(A)是化合物二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯或下述式的化合物,
其中m4是2-40的数,
和组分(B)是聚酰胺(PA)、聚甲醛(POM)或聚醚酰胺的那些混合物。
本发明的又一优选实施方案涉及另外含有作为其它组分(XX)的有机Ca盐、无机Ca盐、Ca氧化物或Ca氢氧化物的组合物。
有机Ca盐的实例是硬脂酸钙、月桂酸钙、乳酸钙和硬脂酰月桂酸钙。
无机Ca盐的实例是碳酸钙、氯化钙、氟化钙、CaHPO4、Ca(PO3)2、Ca2P2O7、CaSO4和CaSiO3。
本发明另一优选的实施方案涉及另外含有作为其它组分(XXX)的有机Zn盐、无机Zn盐、Zn氧化物或Zn氢氧化物、有机Mg盐、无机Mg盐、Mg氧化物或Mg氢氧化物的组合物。
锌或镁的有机盐优选乙酰丙酮化物或例如具有1-24个碳原子的脂族单羧酸酯。醋酸镁、月桂酸镁和硬脂酸镁、甲酸锌、醋酸锌、庚酸锌和月桂酸锌以及乙酰丙酮化锌和乙酰丙酮化镁是特别优选的实例。
硬脂酸锌、硬脂酸镁、乙酰丙酮化锌、乙酰丙酮化镁、醋酸锌和醋酸镁是特别令人关注的。
无机锌盐或镁盐例如是
含有碳酸盐的化合物如
·Zn-氢氧化物-碳酸盐、Mg-氢氧化物-碳酸盐、白云石,如Ca/Mg碳酸盐如来源于Minerals(RTM)的Microdol Super(RTM);或
·天然或合成的水滑石。
认为天然合成的水滑石具有下述结构:Mg6Al2(OH)16CO3·4H2O。合成水滑石的典型的经验式是Al2Mg4.35OH11.36CO3(167)·xH2O。合成产品的实例包括:Mg0.7Al0.3(OH)2(CO3)0.15·0.54H2O、Mg4.5Al2(OH)13CO3·3.5H2O或Mg4.2Al2(OH)12.4CO3。
优选的合成水滑石是来源于REHEIS(RTM)的L-55R II(RTM)以及来源于Kyowa Chemical Industry Co(RTM)的ZHT-4A(RTM)和DHT-4A(RTM)。
本发明的稳定剂混合物用于稳定聚合物烯烃,防止因光、热或氧化诱导降解。合适的聚烯烃的实例如下所述。
1.单烯烃和二烯烃的聚合物,例如聚丙烯、聚异丁烯、聚丁-1-烯、聚-4-甲基戊-1-烯、聚异戊二烯或聚丁二烯,以及环烯烃的聚合物,例如环戊烯或降冰片烯、聚乙烯(可任选地被交联),例如高密度聚乙烯(HDPE)、高密度和高分子量聚乙烯(HDPE-HMW)、高密度和超高分子量聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、线形低密度聚乙烯(LLDPE)、(VLDPE)和(ULDPE)。
可通过不同的方法,特别是下述方法来制备聚乙烯,即前一段落例举的单烯烃的聚合物,优选聚乙烯和聚丙烯:
a)自由基聚合(通常在升高的温度和高压下进行),
b)使用通常含有一种或多种周期表中IVb、Vb、VIb或VIII族的金属。这些金属一般具有一种或多种可进行∏-或σ-配位的配体,典型地为氧化物、卤化物、醇化物、酯、醚、胺、烷基、链烯基和/或芳基。这些金属配合物可以呈游离形式或将其固定在基质上,典型地固定在活化的氯化镁、氯化钛(III)、氯化铝或二氧化硅上。这些催化剂在聚合介质中可以是可溶的或不可溶的。催化剂本身可用于聚合中或可进一步使用活化剂,典型地烷基金属、金属氢化物、烷基金属卤化物、烷基金属氧化物或金属烷氧烷,所述金属是周期表Ia、IIa和/或IIIa族的元素。可方便地进一步用酯、醚、胺或甲硅烷基醚基改性活化剂。这些催化剂体系通常称为Phillips,Standard OilIndiana,Ziegler(-Natta),TNZ(DuPont),茂金属或单一位点催化剂(SSC)。
2.1)中所涉及的聚合物混合物,例如聚丙烯与聚异丁烯的混合物、聚丙烯与聚乙烯(例如PP/HDPE,PP/LDPE)的混合物以及不同类型聚乙烯的混合物(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)及其与低密度聚乙烯(LDPE)的混合物、丙烯/丁-1-烯共聚物、丙烯/异丁烯共聚物、乙烯/丁-1-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/醋酸乙烯酯共聚物及其与一氧化碳的共聚物或乙烯/丙烯酸共聚物及其盐(离聚物)以及乙烯与丙烯和二烯烃(如己二烯、二环戊二烯或亚乙基-降冰片烯)的三元共聚物;和这些共聚物彼此间的混合物以及这些共聚物与以上1)中所涉及的聚合物(例如聚丙烯/乙烯-丙烯共聚物、LDPE/乙烯-醋酸乙烯酯共聚物(EVA)、LDPE/乙烯-丙烯酸共聚物(EAA)、LLDPE/EVA、LLDPE/EAA)的混合物和交替或无规聚亚烷基/一氧化碳共聚物及其与其它聚合物(例如聚酰胺)的混合物。
本发明因此还涉及含有聚烯烃和本文所述的稳定剂的组合物,以及涉及一种稳定聚烯烃,防止因光、热或氧化诱导降解的方法,该方法包括在聚烯烃中掺入本发明的稳定剂混合物。
优选以上1点中所列出的聚烯烃。尤其优选聚乙烯和聚丙烯以及聚乙烯共聚物或聚丙烯共聚物。
可向单独或彼此混合的待稳定的聚烯烃中加入新型的稳定剂混合物组分。稳定剂混合物(组分A和B)优选0.01-5%的存在量,尤其是0.05-1%,相对于聚烯烃的重量。
组分(B)的存在量例如为0.005-1.5%、0.005-1.0%、0.01-1%、0.05-1.0%、0.05-0.5%,尤其是0.05-0.2%或0.01-0.2%,相对于聚烯烃的重量。
Ca化合物(组分(XX))以例如0.005-1%,优选0.05-0.2%的用量任选地存在于待稳定的材料中。
组分(XXX)以例如0.005-1%,尤其是0.05-0.2%的用量任选地存在于待稳定的材料中,相对于所述材料的重量。
组分(A)∶(XX)的重量比例如是1∶10-100∶1,优选1∶5-5∶1,尤其是1∶2-2∶1。
组分(A)∶(XXX)的重量比例如是1∶10-20∶1,优选1∶5-5∶1,尤其是1∶2-2∶1。
例如在成型之前或成型之中,通过已知的方法,或通过向聚烯烃上涂敷溶解的或分散的化合物,视需要随后蒸发溶剂,可在聚烯烃中掺入新型的稳定剂混合物或其单独的组分。可向粉末、颗粒或母炼胶(masterbatch)形式的聚烯烃中加入新型的稳定剂混合物,其中它以例如2.5-25wt%的浓度含有混合物。
视需要,在掺入到聚烯烃中之前,可彼此熔融捏合新型的稳定剂混合物的各组分。
可在聚合之前或之中或者在交联之前加入新型稳定剂或其组分。
可以各种形式广泛应用以该方式稳定的材料,例如膜、纤维、胶带、模塑组合物、型材(profiles)或用作油漆、粘合剂或油灰中的粘合剂。
本发明稳定的聚烯烃可另外含有各种常规的添加剂,例如
1.抗氧剂
1.1烷基化一元酚,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-正丁基酚、2,6-二叔丁基-4-异丁基酚、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、2,4,6-三环己基酚、2,6-二叔丁基-4-甲氧基甲基苯酚、壬基酚,所述烷基化一元酚是线形的或侧链是支化的,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)酚、2,4-二甲基-6-(1′-甲基十七烷-1′-基)酚、2,4-二甲基-6-(1′-甲基十三烷-1′-基)酚及其混合物。
1.2烷基甲硫基酚,例如2,4-二辛基甲硫基-6-叔丁基酚、2,4-二辛基甲硫基-6-甲基苯酚、2,4-二辛基甲硫基-6-乙基苯酚、2,4-二(十二烷基)甲硫基-4-壬基酚。
1.3氢醌和烷基化氢醌,例如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、2,6-二叔丁基氢醌、3,5-二叔丁基-4-羟基茴香醚、3,5-二叔丁基-4-羟苯基硬脂酸酯、双(3,5-二叔丁基-4-羟苯基)己二酸酯。
1.4生育酚,例如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚及其混合物(维生素E)。
1.5羟基化硫代二苯基醚,例如,2,2′-硫代双(6-叔丁基-4-甲基苯酚)、2,2′-硫代双(4-辛基酚)、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)、4,4′-硫代双(3,6-二仲戊基酚)、4,4′-双(2,6-二甲基-4-羟苯基)二硫醚。
1.6亚烷基双酚,例如2,2′-亚甲基双(6-叔丁基-4-甲基苯酚)、2,2′-亚甲基双(6-叔丁基-4-乙基苯酚)、2,2′-亚甲基双[4-甲基-6-(α-甲基环己基)-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-甲基苯酚)、2,2′-亚甲基双(4,6-二叔丁基酚)、2,2′-亚乙基双(6-叔丁基-4-异丁基酚)、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]、4,4′-亚甲基双(2,6-二叔丁基酚)、4,4′-亚甲基双(6-叔丁基-2-甲基苯酚)、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基硫醇基丁烷、双[3,3-双(3′-叔丁基-4′-羟苯基)丁酸]乙二醇酯、双(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯、双[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-双-(3,5-二甲基-2-羟苯基)丁烷、2,2-双-(3,5-二甲基-4-羟苯基)丙烷、2,2-双(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基硫醇基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.70-,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-3,5-二甲基苄基硫醇基醋酸酯、十三烷基-4-羟基-3,5-二叔丁基苄基硫醇基醋酸酯、三(3,5-二叔丁基-4-羟苄基)胺、双(4-叔丁基-3-羟烷基-2,6-二甲基苄基)二硫代对苯二甲酸酯、双(3,5-二叔丁基-4-羟基-苄基)硫醚、异辛基-3,5-二叔丁基-4-羟基苄基硫醇基醋酸酯。
1.8羟苄基化的丙二酸酯,例如二(十八烷基)-2,2-双(3,5-二叔丁基-2-羟苄基)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)硫醇基乙基-2,2-双(3,5-二叔丁基-4-羟苄基)丙二酸酯、双[4-(1,1,3,3-四甲基丁基)苯基]-2,2-双(3,5-二叔丁基-4-羟苄基)丙二酸酯。
1.9芳族羟苄基化合物,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-双(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-羟苄基)酚。
1.10三嗪化合物,例如2,4-双(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-双(3,5-二叔丁基-4-羟苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(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、2,4,6-三(3,5二叔丁基-4-羟苯基乙基)-1,3,5-三嗪、1,3,5-三(3,5-二叔丁基-4-羟苯基丙酰基)-六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟苄基)异氰脲酸酯。
1.11苄膦酸酯,例如二甲基-2,5-二叔丁基-4-羟苄基膦酸酯、二乙基-3,5-二叔丁基-4-羟苄基膦酸酯、二(十八烷基)-3,5-二叔丁基-4-羟苄基膦酸酯、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-羟苄基膦酸的单乙酯的钙盐。
1.12酰氨基酚,例如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺、辛基N-(3,5-二叔丁基-4-羟苯基)氨基甲酸酯。
1.13β-(3,5-二叔丁基-4-羟苯基)丙酸的酯,它带有一元或多元醇,例如甲醇、乙醇、正辛醇、异辛醇、十八烷醇、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(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)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)丙酸的酯,它带有一元或多元醇,例如甲醇、乙醇、正辛醇、异辛醇、十八烷醇、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(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)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-羟甲基-1-磷杂-2,6,7-三氧杂二环[2.2.2]辛烷;3,9-双[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}-1,1-二甲基乙基]-2,4,8,10-四氧杂螺[5.5]-十一烷。
1.15β-(3,5-二环己基-4-羟苯基)丙酸的酯,它带有一元或多元醇,例如甲醇、乙醇、辛醇、十八烷醇、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(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)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-羟苯基)醋酸的酯,它带有一元或多元醇,例如甲醇、乙醇、辛醇、十八烷醇、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(羟乙基)异氰脲酸酯、N,N′-双(羟乙基)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-羟苯基)丙酸的酰胺,例如,N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)六亚甲基二酰胺、N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)三亚甲基二酰胺、N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)酰肼、N,N′-双[2-(3-[3,5-二叔丁基-4-羟苯基]丙酰氧基)草酰胺(Uni royal供应的NaugardXL-1)。
1.18抗坏血酸(维生素C)
1.19胺抗氧剂,例如N,N′-二异丙基-对苯二胺、N,N′-二仲丁基-对苯二胺、N,N′-双(1,4-二甲基戊基)-对苯二胺、N,N′-双(1-乙基-3-甲基戊基)-对苯二胺、N,N′-双(1-甲基戊基)-对苯二胺、N,N′-二环己基-对苯二胺、N,N′-二苯基-对苯二胺、N,N′-双(2-萘基)-对苯二胺、N-异丙基-N′-苯基-对苯二胺、N-(1,3-二甲基丁基)-N′-苯基-对苯二胺、N-(1-甲基庚基)-N′-苯基-对苯二胺、N-环己基-N′-苯基-对苯二胺、4-(对甲苯氨磺酰基)二苯胺、N,N′-二甲基-N,N′-二仲丁基-对苯二胺、二苯胺、N-烯丙基二苯胺、4-异丙氧基二苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺、辛基化二苯胺,例如p,p′-二叔辛基二苯胺、4-正丁基氨基苯酚、4-丁酰基氨基苯酚、4-壬酰基氨基苯酚、4-十二酰基氨基苯酚、4-十八酰基氨基苯酚、双(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-双[(2-甲基苯基)氨基]乙烷、1,2-双(苯氨基)丙烷、(邻甲苯基)双胍、双[4-(1′,3′-二甲基丁基)苯基]胺、叔辛基化N-苯基-1-萘胺;叔丁基/叔辛基二苯胺的一烷基化和二烷基化的混合物;壬基二苯胺的一烷基化和二烷基化的混合物;十二烷基二苯胺的一烷基化和二烷基化的混合物;异丙基/异己基二苯胺的一烷基化和二烷基化的混合物;叔丁基二苯胺、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪的一烷基化和二烷基化的混合物;叔丁基/叔辛基吩噻嗪的一烷基化和二烷基化的混合物;叔辛基吩噻嗪、N-烯丙基吩噻嗪、N,N,N′,N′-四苯基-1,4-二氨基丁-2-烯、N,N-双(2,2,6,6-四甲基哌啶-4-基)-六亚甲基二胺、双(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′-羟苯基)苯并三唑,例如2-(2′-羟基-5′-甲基苯基)苯并三唑、2-(3′,5′-二叔丁基-2′-羟苯基)苯并三唑、2-(5′-叔丁基-2′-羟苯基)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′-羟苯基)-5-氨-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′-羟苯基)苯并三唑、2-(3′,5′-双(α,α-二甲基苄基)-2′-羟苯基)苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-辛氧基羰基乙基)苯基)-5-氨-苯并三唑、2-(3′-叔丁基-5′-[2-(2-(2-乙基己氧基)羰基乙基]-2′-羟苯基)-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)-5-氯-苯并三唑、2-(3′-叔丁基-2′-羟基-5′-[2-(2-乙基己氧基)羰基乙基]-2′-羟苯基)苯并三唑、2-(3′-十二戊基-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′-亚甲基双[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′-羟苯基]-2H-苯并三唑与聚乙二醇300;[R-CH2CH2-COO-CH2CH2]2-(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、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)的酯交换产物。
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取代的和未被取代的苯甲酸酯,例如4-叔丁基苯基水杨酸酯、苯基水杨酸酯、辛苯基水杨酸酯、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、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、3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯基酯。
2.4丙烯酸酯,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,例如有或无另外的配体(如正丁胺、三乙醇胺或N-环己基二乙醇胺)的2,2′-硫代双[4-(1,1,3,3-四甲基丁基)苯酚]的镍配合物,如1∶1或1∶2的配合物,有或无另外的配体的二丁基二硫代氨基甲酸镍、单烷基酯的镍盐如4-氰基-3,5-二叔丁基苄基膦酸的甲酯或乙酯、酮肟的镍配合物如2-氰基-4-甲基苯基十一烷基酮肟的镍配合物、1-苯基-4-月桂酰基-5-氰基吡唑的镍配合物。
2.6草酰胺,例如4,4′-二辛氧基草酰二苯胺、2,2′-二乙氧基草酰二苯胺、2,2′-二辛氧基草酰二苯胺、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)草酰二苯胺、2-乙氧基-5-叔丁基-2′-乙基草酰二苯胺及其与2-乙氧基-2′-乙基-5,4′-二叔丁基草酰二苯胺、邻甲氧基和对甲氧基取代的草酰二苯胺的混合物以及邻乙氧基和对乙氧基取代的草酰二苯胺的混合物。
2.72-(2-羟苯基)-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-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(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-双(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-双(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-双(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-双(2,4-二甲基)-1,3,5-三嗪、2-[(2-羟基-4-(2-羟基-3-辛氧基丙氧基)苯基]-4,6-双(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-羟苯基]-4,6-双(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-双(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-双(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属去活化剂,例如N,N′-二苯基草酰胺、N-水杨醛-N′-水杨酰基肼、N,N′-双(水杨酰基)肼、N,N′-双(3,5-二叔丁基-4-羟苯基丙酰基)肼、3-水杨酰基氨基-1,2,4-三唑、双(亚苄基)草酰基二酰肼、草酰二苯胺、间苯二酰基二酰肼、癸二酰基二苯基酰肼、N,N′-二乙酰基己二酰基二酰肼、N,N′-双(水杨酰基)草酰基二酰肼、N,N′-双(水杨酰基)硫代丙酰基二酰肼。
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、三个(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、双(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯、双(2,4-二枯基苯基)季戊四醇二亚磷酸酯、双(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、双(2,4,6-三(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′-二亚苯基二亚磷酸酯、6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯[d,g]-1,3,2-二氧杂二亚磷酸酯(phosphocin)、双(2,4-二叔丁基-6-甲基苯基)甲基亚磷酸酯、双(2,4-二叔丁基-6-甲基苯基)乙基亚磷酸酯、6-氟-2,4,8,10-四叔丁基-12-甲基-二苯[d,g]-1,3,2-二氧杂二亚磷酸酯(phosphocin)、2,2′,2″-次氮基-[三乙基三(3,3′,5,5′-四叔丁基-1,1′-二苯基-2,2′-二基)亚磷酸酯]、2-乙基己基(3,3′,5,5′-四叔丁基-1,1′-二苯基-2,2′-二基)亚磷酸酯、5-丁基-5-乙基-2-(2,4,6-三叔丁基苯氧基)-1,3,2-二氧杂phosphirane。
特别优选下述亚磷酸酯:
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-十五烷基-N-十八烷基羟胺、衍生于氢化牛油脂肪胺的N,N-二烷基羟胺。
6.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-十四烷基硝酮、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、衍生于N,N-二烷基羟胺的硝酮,而N,N-二烷基羟胺衍生于氢化牛油脂肪胺。
7.硫代增效剂,例如硫代二丙酸二月桂基酯或硫代二丙酸二硬脂基酯。
8.过氧化物清除剂,例如β-硫代二丙酸酯,例如其月桂基酯、硬脂基酯、十四烷基酯或十三烷基酯、硫醇基苯并咪唑或2-硫醇基苯并咪唑的锌盐、二丁基二硫代氨基甲酸锌、二个(十八烷基)二硫化物、季戊四醇四(β-十二烷基硫醇基)丙酸酯。
9.聚酰胺稳定剂,例如与碘化物和/或含磷化合物结合的铜盐乙基二价镁盐。
10.碱性助稳定剂,例如蜜胺、聚乙烯吡咯烷酮、双氰胺、三烯丙基氰脲酸酯、脲的衍生物、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、二十二烷酸镁、硬脂酸镁、蓖麻酸钠和棕榈酸钾、儿茶酸锑或儿茶酸锌。
11.成核剂,例如无机物,如滑石、氧化物如二氧化钛或氧化镁,优选碱土金属的磷酸盐、碳酸盐或硫酸盐;有机化合物如一元或多元羧酸及其盐,如4-叔丁基苯甲酸、二苯基醋酸、琥珀酸钠、苯甲酸钠;聚合物化合物如离子共聚物(离聚物)。特别优选1,3:2,4-双(3′,4′-二甲基亚苄基)山梨醇、1,3:2,4-二(副甲基亚苄基)山梨醇和1,3:2,4-二(亚苄基)山梨醇。
12.填料和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、玻璃球、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、木粉乙基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、流变添加剂、催化剂、流动控制剂、光学增亮剂、阻燃剂、抗静电剂和发泡剂。
14.苯并呋喃酮和吲哚满酮,例如US4325863,US4338244,US5175312,US5216052,US5252643,DE-A-4316611,DE-A-4316622,DE-A-4316876,EP-A-0589839或EP-A-0591102中公开的那些,或者3-[4-(2-乙酰氧基乙氧基)-苯基]-5,7-二叔丁基苯并呋喃-2-酮、5,7-二叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮、3,3′-双[5,7-二叔丁基-3-(4-[2-羟基乙氧基]苯基)苯并呋喃-2-酮]、5,7-二叔丁基-3-(4-乙氧基苯基]苯并呋喃-2-酮、3-(4-乙酰氧基-3,5-二甲基苯基]-5,7-二叔丁基苯并呋喃-2-酮、3-(3,5-二甲基-4-新戊酰氧基苯基)-5,7-二叔丁基苯并呋喃-2-酮、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。
本发明的稳定剂混合物与常规添加剂的重量比可以是例如1∶0.1到1∶5。
下述实施例更详细地阐述本发明。所有百分数和分数均以重量为单位,除非特别说明。
下述实施例1-4中所使用的稳定剂和助添加剂
化合物(13):
化合物(14):
化合物(49-a-1):
化合物(5-1):
PVA:聚乙烯醇,
PA:聚酰胺,
PC:聚碳酸酯。
PET:聚对苯二甲酸乙二酯,
PBT:聚对苯二甲酸丁二酯,
PMMA:聚甲基丙烯酸甲酯,
POM:聚甲醛,
TPU:热塑性聚氨酯,
PPE:聚苯醚,
ASA:丙烯酸酯/苯乙烯/丙酰腈其聚物,
SAN:苯乙烯/丙酰腈共聚物,
SMA:苯乙烯/马来酸酐共聚物。
实施例1:聚丙烯均聚物膜的光稳定
在布雷本登塑性计中,在200℃下用0.05份四{3-(3,5-二叔丁基-4-羟苯基)丙酸}季戊四醇酯、0.05份三(2,4-二叔丁基苯基)亚磷酸酯、0.1份硬脂酸钙、0.25份二氧化钛(锐钛矿)和表1中所示的稳定剂混合物均化100份未被稳定的聚丙烯粉末(在230℃和2160g下的熔体流动指数:3.8g/10min)达10分钟。将由此获得的材料在260℃下在实验室压力机中在两块铝箔之间压模6分钟到0.5mm厚度的膜,将该膜在水冷压力机中迅速冷却到室温。从这些0.5mm厚的膜中切割出60mm×25mm的样品,并将其暴露在WEATHER-OMETER Ci 65(黑色面板的温度为63±2℃,没有喷水)中。
周期性地,将这些样品从暴露装置中除出,它们的羰基含量以红外分光光度计测量。暴露时间相应于形成0.1的羰基吸收,这是对于所述稳定剂混合物的有效性的量度。所获得的值总结于表1中。
表1;
稳定剂 *)T0.1(0.1羰基吸收的时间(小时))
0.05%化合物(13) 435
0.05%化合物(13)和 460
0.05%PET
0.05%化合物(13)和 770
0.10%PET
0.05%化合物(13)和 865
0.05%PA6
0.05%化合物(13)和 710
0.10%PA6
0.05%化合物(13)和 635
0.05%PC
0.05%化合物(13)和 685
0.10%PC
0.05%化合物(13)和 740
0.05%PMMA
0.05%化合物(13)和 960
0.10%PMMA
*)高的数值是所需的。
实施例2;聚丙烯均聚物膜的光稳定
在布雷本登塑性计中,在200℃下用0.05份四{3-(3,5-二叔丁基-4-羟苯基)丙酸}季戊四醇酯、0.05份三(2,4-二叔丁基苯基)亚磷酸酯、0.1份硬脂酸钙、0.25份二氧化钛(锐钛矿)和表2中所示用量的光稳定剂和极性聚合物来均化100份未被稳定的聚丙烯粉末(在230℃和2160g下的熔体流动指数:3.5g/10min)达10分钟。将由此获得的材料在260℃下在实验室压力机中在两块铝箔之间压模6分钟到0.5mm厚度的膜,将该膜在水冷压力机中迅速冷却到室温。从这些0.5mm厚的膜中切割出60mm×25mm的样品,并将其暴露在WEATHER-OMETER Ci65(黑色面板的温度为63±2℃,没有喷水)中。
周期性地将这些样品从暴露装置中移出,并用红外分光光度计测量其羰基含量。
相应于形成0.1的羰基吸收的暴露时间(T0.1)是稳定剂配方是否有效的量度。表2概括了所获得的值。
表2:
表2(续)
*)高的数值是所需的。
实施例3:聚丙烯均聚物膜的光稳定
在布雷本登塑性计中,在200℃下用0.05份四{3-(3,5-二叔丁基-4-羟苯基)丙酸}季戊四醇酯、0.05份三(2,4-二叔丁基苯基)亚磷酸酯、0.1份硬脂酸钙、0.25份二氧化钛(锐钛矿)和表3中所示用量的光稳定剂、极性聚合物和助添加剂来均化100份未被稳定的聚丙烯粉末(在230℃和2160g下的熔体流动指数:3.8g/10min)达10分钟。将由此获得的材料在260℃下在实验室压力机中在两块铝箔之间压模6分钟到0.5mm厚度的膜,将该膜在水冷压力机中迅速冷却到室温。从这些0.5mm厚的膜中切割出60mm×25mm的样品,并将其暴露在WEATHER-OMETER Ci 65(黑色面板的温度为63±2℃,没有喷水)中。
周期性地将这些样品从暴露装置中移出,并用红外分光光度计测量其羰基含量。
相应于形成0.1的羰基吸收的暴露时间(T0.1)是稳定剂配方是否有效的量度。表3概括了所获得的值。
表3:
*)高的数值是所需的。
实施例4:聚丙烯均聚物膜的光稳定
在布雷本登塑性计中,在200℃下用0.05份四{3-(3,5-二叔丁基-4-羟苯基)丙酸}季戊四醇酯、0.05份三(2,4-二叔丁基苯基)亚磷酸酯、0.1份硬脂酸钙、0.25份二氧化钛(锐钛矿)和表4中所示的光稳定剂和极性聚合物用量来均化100份未被稳定的聚丙烯粉末(在230℃和2160g下的熔体流动指数:3.5g/10min)达10分钟。将由此获得的材料在260℃下在实验室压力机中在两块铝箔之间压模6分钟到0.5mm厚度的膜,将该膜在水冷压力机中迅速冷却到室温。从这些0.5mm厚的膜中切割出60mm×25mm的样品,并将其暴露在WEATHER-OMETER Ci65(黑色面板的温度为63±2℃,没有喷水)中。
周期性地将这些样品从暴露装置中移出,并用红外分光光度计测量其羰基含量。
相应于形成0.1的羰基吸收的暴露时间(T0.1)是稳定剂配方是否有效的量度。表4概括了所获得的值。
表4:
*)高的数值是所需的。
Claims (19)
1.一种含有聚烯烃和稳定剂混合物的组合物,该混合物的含量相对聚烯烃的重量为0.01-5%,其中所述稳定剂混合物含有:
(A)一种位阻胺化合物,和
(B)一种含极性残基的聚合物,其含量相对于聚烯烃的重量为0.005-1.5%;组分(A)∶(B)的重量比为20∶1到1∶20;
其中组分(A)相应于如下所定义的化合物(5),(13),(14),(23),(24),(36-a-1),(36-a-2),(36-b-1),(36-b-2),(36-d),(49-a-1),(49-a-2),(49-c),(49-d),(49-e),(63),(65),(69-a),(81),(82),(102),(105)或(106),或
相应于如下所定义的化合物(76),(82-a),(84-1-a),(84-1-b),(84-2),(91-1),(92),(93),(96-I),(96-II),(97-I),(97-II),(99-I),(99-II),(99-III),(100-A)或(101-I):
5)4-硬脂酰氧基-2,2,6,6-四甲基哌啶
13)二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯
14)二(1,2,2,6,6-五甲基哌啶-4-基)癸二酸酯
23)二(1,2,2,6,6-五甲基哌啶-4-基)丁基(3,5-二叔丁基-4-羟苄基)丙二酸酯
24)二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯
36-a-1)1,2,3,4-四[2,2,6,6-四甲基哌啶-4-基氧基羰基]丁烷
36-a-2)双[2,2,6,6-四甲基哌啶-4-基氧基羰基]-双[三癸氧基羰基]丁烷
36-b-1)1,2,3,4-四[1,2,2,6,6-五甲基哌啶-4-基氧基羰基]丁烷
36-b-2)双[1,2,2,6,6-五甲基哌啶-4-基氧基羰基]-双[三癸氧基羰基]丁烷
49-c)2-(2,2,6,6-四甲基哌啶-4-基氨基)-2-(2,2,6,6-四甲基哌啶-4-基氨基羰基)丙烷
49-d)1,6-双[N-(2,2,6,6-四甲基哌啶-4-基)甲酰基氨基]己烷
63)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
65)8-乙酰基-3-十二烷基-1,3,8-三氮杂-7,7,9,9-四甲基螺[4.5]癸烷-2,4-二酮
其中m1是2-40的数,
其中m4是2-40的数,
其中m4是2-40的数,
其中m4是2-40的数,
其中m11 *是2-40的数,基团R*彼此独立地为乙基或2,2,6,6-四甲基哌啶-4-基,前提是至少50%的基团R*是2,2,6,6-四甲基哌啶-4-基和其余的基团R*是乙基,
其中m12是2-40的数,
其中m12是2-40的数,
其中m16是2-50的数,
其中m16 *是2-50的数,
其中m17是1-20的数,
其中m17是1-20的数,
其中G11是氢或甲基和m19是1-25的数,
其中G11是氢或甲基和m19是1-25的数,
其中G11是氢或甲基和m19是1-25的数,
100-A)通过使式(100a)的多胺与氰尿酰氯反应而获得的中间产物与式(100b)的化合物反应获得的产物,
H2N-(CH2)3-NH-(CH2)2-NH-(CH2)3-NH2 (100a)
其中m21是1-20的数;
其中组分(B)相应的化合物是:
(B-1)含卤素的聚合物,
(B-2)衍生于α,β-不饱和酸或其衍生物的聚合物
(B-3)丙烯腈/丁二烯共聚物、丙烯腈/丙烯酸烷基酯共聚物、乙烯/丙烯酸酯共聚物、丙烯腈/丙烯酸烷氧烷基酯或丙烯腈/卤代乙烯共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物,
(B-4)衍生于不饱和醇和胺或酰基衍生物或其缩醛的聚合物,
(B-5)环醚的均聚物或共聚物,
(B-6)聚缩醛,
(B-7)聚苯醚或聚苯醚与其它聚合物的混合物,
(B-8)聚氨酯,
(B-9)聚酰胺或共聚酰胺,
(B-10)聚脲、聚酰亚胺、聚酰胺-酰亚胺、聚醚酰亚胺、聚酯酰亚胺、聚海因、聚苯并咪唑或聚乙烯基咪唑,
(B-11)聚酯,
(B-12)聚碳酸酯或聚酯碳酸酯,
(B-13)聚砜、聚醚砜或聚醚酮,
(B-14)一方面衍生于醛而另一方面衍生于酚、脲或蜜胺的聚合物,
(B-15)干燥或未干燥的醇酸树脂,
(B-16)不饱和的聚酯树脂,
(B-17)可交联的丙烯酸树脂,
(B-18)用蜜胺树脂、脲醛树脂、异氰酸酯、异氰脲酸酯、聚异氰酸酯或环氧树脂交联的醇酸树脂、聚酯树脂或丙烯酸酯树脂,
(B-19)环氧树脂,
(B-20)纤维素或其化学改性的同系衍生物,
(B-21)聚有机硅氧烷,
(B-22)聚乙烯醇缩甲醛,
(B-23)聚(芳基-醚-醚-酮),或
(B-24)乙烯基芳族单体的共聚物。
2.权利要求1的组合物,其中组分(A)相应于化合物(5),(13),(14),(24),(49-a-1),(49-a-2)或(49-d)。
3.权利要求1的组合物,其中组分(A)相应于化合物(13)。
4.权利要求1的组合物,其中组分(A)相应于化合物(76),(84-1-a),(84-1-b),(92),(93),(99-I),(100-A)或(101-I)。
5.权利要求1的组合物,其中组分(A)相应于化合物(76),(84-1-a),(84-1-b),(92)或(100-A)。
6.权利要求1的组合物,其中组分(A)∶(B)的重量比为5∶1-1∶5。
7.权利要求1的组合物,其中含有极性残基的聚合物选自(B-2),(B-4),(B-6),(B-7),(B-8),(B-9),(B-11),(B-12)和(B-13)。
9.权利要求8的组合物,其中组分(B)是聚甲基丙烯酸甲酯。
10.权利要求1的组合物,其中组分(B)是聚酰胺、丙烯酸酯/苯乙烯/丙烯腈共聚物、苯乙烯/丙烯腈共聚物、苯乙烯/马来酸酐共聚物或聚醚酰胺。
11.权利要求1的组合物,其中组分(B)是聚丙烯酸甲酯、聚甲基丙烯酸甲酯、聚酰胺、聚甲醛、丙烯酸酯/苯乙烯/丙烯腈共聚物或聚醚酰胺。
12.权利要求1的组合物,其中组分(A)是化合物二(2,2,6,6-四甲基哌啶-4-基)癸二酸酯,组分(B)是聚对苯二甲酸乙二酯、聚酰胺6、聚碳酸酯、聚丙烯酸甲酯或聚甲基丙烯酸甲酯,以及组分(A)∶(B)的重量比为5∶1-1∶5。
13.权利要求12的组合物,其中组分(B)是聚甲基丙烯酸甲酯。
15.权利要求1的组合物,其中另外含有作为进一步的组分(XX)的有机Ca盐、无机Ca盐、Ca氧化物或Ca氢氧化物。
16.权利要求1的组合物,其中另外含有作为进一步的组分(XXX)的有机Zn盐、无机Zn盐、Zn氧化物、Zn氢氧化物、有机Mg盐、无机Mg盐、Mg氧化物或Mg氢氧化物。
17.权利要求1的组合物,其中聚烯烃是聚乙烯或聚丙烯或聚乙烯或聚丙烯的共聚物。
19.一种稳定聚烯烃防止因光、热或氧化诱导降解的方法,其中包括向聚烯烃中掺入权利要求1所定义的稳定剂混合物,该混合物的含量相对聚烯烃的重量为0.01-5%。
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EP00810149 | 2000-02-22 | ||
EP00810149.5 | 2000-02-22 |
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CN100429259C true CN100429259C (zh) | 2008-10-29 |
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US (1) | US6869992B2 (zh) |
EP (1) | EP1263855B1 (zh) |
JP (1) | JP4733898B2 (zh) |
KR (1) | KR100727524B1 (zh) |
CN (1) | CN100429259C (zh) |
AT (1) | ATE388988T1 (zh) |
AU (1) | AU2001233764A1 (zh) |
BR (1) | BR0108512B1 (zh) |
CA (1) | CA2400413C (zh) |
DE (1) | DE60133181T2 (zh) |
ES (1) | ES2301528T3 (zh) |
IN (1) | IN2002CH01489A (zh) |
MX (1) | MXPA02008161A (zh) |
PT (1) | PT1263855E (zh) |
RU (1) | RU2263688C2 (zh) |
WO (1) | WO2001062836A1 (zh) |
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US11767616B2 (en) | 2017-08-18 | 2023-09-26 | Glen Raven, Inc. | Acrylic compositions including a hindered amine light stabilizer and methods of making and using the same |
EP3578599A1 (en) * | 2018-06-08 | 2019-12-11 | Cytec Industries Inc. | Granular stabilizer compositions for use in polymer resins and methods of making same |
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CN116003680B (zh) * | 2022-12-26 | 2024-07-09 | 天集化工助剂(沧州)有限公司 | 一种聚合型抗光老型多功能添加剂及其制备方法和应用 |
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- 2001-02-15 KR KR1020027010787A patent/KR100727524B1/ko not_active IP Right Cessation
- 2001-02-15 ES ES01905773T patent/ES2301528T3/es not_active Expired - Lifetime
- 2001-02-15 AT AT01905773T patent/ATE388988T1/de active
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- 2001-02-15 EP EP01905773A patent/EP1263855B1/en not_active Expired - Lifetime
- 2001-02-15 US US10/182,073 patent/US6869992B2/en not_active Expired - Fee Related
- 2001-02-15 BR BRPI0108512-3A patent/BR0108512B1/pt not_active IP Right Cessation
- 2001-02-15 AU AU2001233764A patent/AU2001233764A1/en not_active Abandoned
- 2001-02-15 JP JP2001562615A patent/JP4733898B2/ja not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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IN2002CH01489A (en) | 2005-01-28 |
RU2263688C2 (ru) | 2005-11-10 |
US6869992B2 (en) | 2005-03-22 |
KR100727524B1 (ko) | 2007-06-14 |
AU2001233764A1 (en) | 2001-09-03 |
MX235505B (zh) | 2006-04-05 |
CN1404501A (zh) | 2003-03-19 |
DE60133181D1 (de) | 2008-04-24 |
CA2400413C (en) | 2010-01-12 |
PT1263855E (pt) | 2008-04-16 |
WO2001062836A1 (en) | 2001-08-30 |
ES2301528T3 (es) | 2008-07-01 |
EP1263855A1 (en) | 2002-12-11 |
EP1263855B1 (en) | 2008-03-12 |
IN205902B (zh) | 2007-06-29 |
RU2002123336A (ru) | 2004-01-20 |
DE60133181T2 (de) | 2009-03-12 |
JP2003524047A (ja) | 2003-08-12 |
BR0108512A (pt) | 2002-12-17 |
KR20020075922A (ko) | 2002-10-07 |
BR0108512B1 (pt) | 2012-07-24 |
JP4733898B2 (ja) | 2011-07-27 |
US20030069337A1 (en) | 2003-04-10 |
ATE388988T1 (de) | 2008-03-15 |
CA2400413A1 (en) | 2001-08-30 |
MXPA02008161A (es) | 2002-11-29 |
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