CN1061076C - 用作有机材料稳定剂的二羧酸多烷基哌啶-4-基酯混合物 - Google Patents
用作有机材料稳定剂的二羧酸多烷基哌啶-4-基酯混合物 Download PDFInfo
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- CN1061076C CN1061076C CN97113189A CN97113189A CN1061076C CN 1061076 C CN1061076 C CN 1061076C CN 97113189 A CN97113189 A CN 97113189A CN 97113189 A CN97113189 A CN 97113189A CN 1061076 C CN1061076 C CN 1061076C
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- stabilizer blend
- butyl
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- acid
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Classifications
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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
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3472—Five-membered rings
- C08K5/3475—Five-membered rings condensed with carbocyclic rings
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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
- C08K5/0008—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
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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
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
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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
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3435—Piperidines
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- Compositions Of Macromolecular Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Paints Or Removers (AREA)
Abstract
一种含有通式(Ⅰ)的两种不同化合物的稳定剂混合物,其中n为2至22的整数,R为氢、C1-C8烷基、-O、-OH、-NO、-CH2CN、C1-C18烷氧基、C5-C12环烷氧基、C3-C6链烯基、C3-C6链炔基、C1-C8酰基或未取代或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;两种化合物的重量比为1∶20至20∶1,该混合物可用作有机材料抗氧化、热或光诱导降解的稳定剂。
Description
本发明涉及含有两种不同二羧酸多烷基哌啶-4-基酯的混合物,涉及借助该混合物稳定的抗光诱导、热或氧化降解的有机材料,并涉及该混合物用于稳定有机材料的用途。
几种二羧酸多烷基哌啶-4-基酯以单一化合物或混合物用于稳定有机材料的用途(例如)公开于US-A-5 028 645、US-A-4 461 898和US-A-4419 472,EP-A-146 878和GB-A-2 202 853中。
本发明涉及含有通式(Ⅰ)的两种不同化合物的稳定剂混合物其中n为2至22的整数,R为氢、C1-C8烷基、-O、-OH、-NO、-CH2CN、C1-C18烷氧基、C5-C12环烷氧基、C3-C6链烯基、C3-C6链炔基、C1-C8酰基或未取代或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;两种化合物的重量比为1∶20至20∶1。
C1-C8烷基的例子是甲基、乙基、丙基、异丙基、丁基、2-丁基、异丁基、叔丁基、戊基、2-戊基、己基、庚基、辛基、2-乙基己基和叔辛基。
C1-C18烷氧基的例子是甲氧基、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。C1-C8烷氧基,特别是庚氧基和辛氧基是优选的。
C5-C12环烷氧基的例子是环戊氧基、环己氧基、环庚氧基、环辛氧基、环癸氧基和环十二烷氧基。C5-C8环烷氧基,特别是环戊氧基和环己氧基是优选的。
C3-C6链烯基的例子是烯丙基、2-甲基烯丙基、丁烯基和己烯基。与氮相连的碳原子优选为饱和的。
C3-C6链炔基的例子是2-丙炔基。
C1-C8酰基的例子是甲酰基、乙酰基、丙酰基、丁酰基、戊酰基、己酰基、庚酰基、辛酰基和苯甲酰基。C1-C8烷酰基和苯甲酰基是优选的。乙酰基是特别优选的。
未取代或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基的例子是苄基、甲基苄基、二甲基苄基、三甲基苄基、叔丁基苄基和2-苯基乙基。苄基是优选的。
变量n优选为2至10,特别是2至8的整数,例如2至4或4至8的整数。
存在于稳定剂混合物中的通式(Ⅰ)的两种不同化合物的重量比优选为1∶15至15∶1,例如1∶10至10∶1、1∶8至8∶1、1∶6至6∶1、1∶5至5∶1、1∶4至4∶1或1∶3至3∶1。
当稳定剂混合物还含有通式(Ⅰ)的第三种化合物时,所述化合物与通式(Ⅰ)的其它两种化合物的总量的重量比可为1∶20至20∶1,优选1∶15至15∶1,例如1∶10至10∶1、1∶8至8∶1、1∶6至6∶1、1∶5至5∶1、1∶4至4∶1或1∶3至3∶1。
本发明一个优选实施方案涉及其中通式(Ⅰ)的两种化合物仅变量n不同的稳定剂混合物。
本发明另一优选实施方案涉及其中通式(Ⅰ)的两种化合物变量n不同且两个n值之差为1、2、3、4或5的稳定剂混合物。
特别感兴趣的是下列稳定剂混合物:
-其中通式(Ⅰ)的一种化合物的变量n为3同时通式(Ⅰ)的另一种化合物的变量n为4或8的混合物。
-其中通式(Ⅰ)的一种化合物的变量n为4同时通式(Ⅰ)的另一种化合物的变量n为7或8的混合物。
-其中通式(Ⅰ)的一种化合物的变量n为7同时通式(Ⅰ)的另一种化合物的变量n为8的混合物。
其中通式(Ⅰ)的一种化合物的变量n为2同时通式(Ⅰ)的另一种化合物的变量n为3的稳定剂混合物也是优选的;所述混合物还含有通式(Ⅰ)中n为4的第三种化合物。
进一步感兴趣的是其中通式(Ⅰ)的两种化合物仅基团R的含义不同的稳定剂混合物。
R优选为氢、C1-C4烷基、-OH、C1-C8烷氧基、C5-C8环烷氧基、烯丙基、苄基、乙酰基或丙烯酰基,特别是氢或甲基。
通式(Ⅰ)的化合物可按类似于已知的酯化或酯基转移方法通过通式(Ⅱ)的哌啶醇与通式(Ⅲ)的有机二羧酸酯的混合物或其衍生物反应制备。合适的二羧酸衍生物的例子是酰氯或低级烷基酯如甲酯或乙酯。当在反应中将酰氯用作二羧酸酯的衍生物时,加入数量上相对于酰氯至少2当量的酸受体如吡啶或三乙胺对反应是有利的。
当反应按通式(Ⅱ)的哌啶醇与通式(Ⅲ)的二羧酸酯混合物的酯基转移反应进行时,通常将酯基转移催化剂加入反应混合物中,所述催化剂的例子是有机碱或无机碱如LiNH2、LiOMe、KOH、叔丁基锂、叔戊基盐(如叔戊基钠)等或路易斯酸如氧化二丁基锡、三[异丙基]铝、三[仲丁基]铝、四[异丙基]钛或四[仲丙基]钛。
所需的二羧酸混合物可通过混合市购二羧酸制得。
特别感兴趣的是使用市购的二羧酸混合物如“Dicarbonsauregemischdestilliert”(=蒸馏过的二羧酸混合物),购自BASF,或二羧酸酯混合物如DBE、DBE2和DBE3,购自Du Pont。
还可以首先制备通式(Ⅰ)的单个化合物,随后将这些化合物按所需比例混合。
本发明的稳定剂混合物对于改进有机材料的耐光、热和氧化性非常有效。这些材料可以是(例如)油、脂、石蜡、化妆品或杀微生物剂。特别感兴趣的是它们在聚合物材料如塑料、橡胶和涂料中的用途。
可被稳定的有机材料的具体例子是:
1.单烯烃和二烯烃的聚合物,例如聚丙烯、聚异丁烯、聚丁烯-1、聚-4-甲基戊烯-1、聚异戊二烯或聚丁二烯,以及环烯烃如环戊二烯或降冰片烯的聚合物,聚乙烯(可非必要地交联)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)、线型低密度聚乙烯(LLDPE)、支化低密度聚乙烯(BLDPE)。
聚烯烃,即前一自然段中列举的单烯烃的聚合物(优选聚乙烯和聚丙烯)可通过不同的方法,特别是通过下列方法制备:
a)游离基聚合(通常在高压和高温下)。
b)使用通常含有一种或多种周期表Ⅳb族、Ⅴb族、Ⅵb族或Ⅷ族金属的催化剂的催化聚合。这些金属通常具有一个或多个可进行π-或σ-配位的配体,一般为氧化物、卤化物、醇化物、酯、醚、胺、烷基、链烯基和/或芳基。这些金属配合物可为游离形式或固定于载体上,所述载体通常为活化的氯化镁、氯化钛(Ⅲ)、氧化铝或氧化硅。这些催化剂可溶于或不溶于聚合介质中。这些催化剂本身可用于聚合中或可使用另一些活化剂,所述活化剂通常为金属烷基化物、金属氢化物、烷基金属卤化物、烷基金属氧化物或烷基金属氧噁烷,所述金属为周期表Ⅰa、Ⅱa和/或Ⅲa族的金属元素。活化剂可方便地用另外的酯、醚、胺或甲硅烷基醚基团改性。这些催化剂通常称为Phillips、Standard Oil Indiana、Zieglar(-Natta)、TNZ(Du Pont)、金属茂或单点催化剂(SSC)。
2.1)中提及的聚合物的混合物,如聚丙烯与聚异丁烯、聚丙烯与聚乙烯的混合物(例如PP/HDPE、PP/LDPE)和不同类型聚乙烯(例如LDPE/HDPE)的混合物。
3.单烯烃和二烯烃相互之间或与其它乙烯基单体的共聚物,如乙烯/丙烯共聚、线型低密度聚乙烯(LLDPE)和其与低密度聚乙烯(LDPE)的混合物、丙烯/丁烯-1共聚物、丙烯/异丁烯共聚物、乙烯/丁烯-1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其与一氧化碳的共聚物或乙烯/丙烯酸共聚物和其盐(离聚物),以及乙烯与丙烯和二烯烃如己二烯、双环戊二烯或亚乙基-降冰片烯的三元共聚物;及这些共聚物与另一种共聚物和与1)中提及的聚合物的混合物,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(EEA)、LLDPE/EVA、LLDPE/EEA和交替或无规聚亚烷基/一氧化碳共聚物和其与其它聚合物如聚酰胺的混合物。
4.烃树脂(例如C5-C9),包括其氢化改性物(如增粘剂)和聚亚烷基与淀粉的混合物。
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,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;高抗冲苯乙烯共聚物与另一种聚合物如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯烃三元共聚物的混合物;苯乙烯的嵌段共聚物如苯乙烯/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,如苯乙烯接枝到聚丁二烯上、苯乙烯接枝到聚丁二烯-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)接枝到聚丁二烯上;苯乙烯、丙烯腈和甲基丙烯酸甲酯接枝到聚丁二烯上;苯乙烯和马来酸酐接枝到聚丁二烯上、苯乙烯、丙烯腈和马来酸酐或马来酰亚胺接枝到聚丁二烯上;苯乙烯和马来酰亚胺接枝到聚丁二烯上;苯乙烯和丙烯酸或甲基丙烯酸烷基酯接枝到聚丁二烯上;苯乙烯和丙烯腈接枝到乙烯/丙烯/二烯烃三元共聚物上;苯乙烯和丙烯腈接枝到聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上;苯乙烯和丙烯腈接枝到丙烯酸酯/丁二烯共聚物上,及其与6)中列举的共聚物的混合物,如称为ABS、MBS、ASA或AES聚合物的共聚物混合物。
8.含卤素的聚合物如聚氯丁二烯、氯化橡胶、异丁烯-异戊二烯的氯化和溴化共聚物(卤丁橡胶)、氯化或氯磺化聚乙烯、乙烯与氯化乙烯的共聚物、表氯醇均聚物和共聚物,特别是含卤乙烯基化合物的聚合物,如聚氯乙烯、聚偏二氯乙烯、聚氟乙烯、聚偏二氟乙烯,及其共聚物如氯乙烯/偏二氯乙烯、氯乙烯/乙酸乙烯酯或偏二氯乙烯/乙酸乙烯酯共聚物。
9.衍生自α,β-不饱和酸和其衍生物的聚合物,如聚丙烯酸酯和聚甲基丙烯酸酯;用丙烯酸丁酯进行冲击改性的聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈。
10.9)中所述单体相互之间或与其它不饱和单体的共聚物,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/丁二烯三元共聚物。
11.衍生自不饱和醇和胺或其酰基衍生物或缩醛的聚合物,如聚乙烯醇、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、聚对苯二甲酸烯丙酯或聚烯丙基密胺;以及它们与上述1)中所列烯烃的共聚物。
12.环醚的均聚物和共聚物,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醚的共聚物。
13.聚缩醛,如聚氧亚甲基或那些含有环氧乙烷作为共聚单体的聚氧亚甲基;用热塑性聚氨酯、丙烯酸酯或MBS改性的聚缩醛。
14.聚苯醚或硫醚,和聚苯醚与苯乙烯聚合物或聚酰胺的混合物。
15.衍生自端羟基聚醚、聚酯或聚丁二烯(一方面)和脂族或芳族多异氰酸酯(另一方面)及其前体的聚氨酯。
16.衍生自二胺和二酸和/或衍生自氨基酸或相应的内酰胺的聚酰胺和共聚酰胺,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、由间二甲苯二胺和己二酸起始的芳族聚酰胺;由己二胺和间苯二甲酸或/和对苯二甲酸和在有或无弹性体作为改性剂下制备的聚酰胺,如聚-2,4,4-三甲基六亚甲基对苯二甲酰胺或聚间亚苯基间苯二甲酰胺;以及上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学键合或接枝弹性体的嵌段共聚物;或与聚醚,如聚乙二醇、聚丙二醇或聚四亚甲基二醇的嵌段共聚物;以及用EPDM或ABS改性的聚酰胺或共聚酰胺;和在加工期间缩聚的聚酰胺(RIM聚酰胺体系)。
17.聚脲、聚酰亚胺、聚酰胺-酰亚胺、聚醚酰亚胺、聚酯酰亚胺、聚乙内酰脲和聚苯并咪唑。
18.衍生自二羧酸和二醇和/或衍生自羟基羧酸或相应内酯的聚酯,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1,4-二羟甲基环己烷酯和聚羟基苯甲酸酯,以及衍生自端羟基聚醚的嵌段共聚醚酯;和用聚碳酸酯或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.衍生自醛(一方面)和酚、脲和密胺(另一方面)的交联聚合物,如苯酚/甲醛树脂、脲/甲醛树脂和密胺/甲醛树脂。
22.干燥和未干燥的醇酸树脂。
23.衍生自饱和和不饱和二羧酸与多元醇的共聚酯和乙烯基化合物作为交联剂的不饱和聚酯,以及其低燃性含卤改性物。
24.衍生自取代丙烯酸酯如环氧丙烯酸酯、聚氨酯丙烯酸酯或聚酯丙烯酸酯的可交联丙烯酸树脂。
25.用密胺树脂、脲树脂、异氰酸酯、异氰脲酸酯、多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.衍生自脂族、环脂族、杂环或芳族缩水甘油基化合物的交联环氧树脂,如双酚A和双酚F的二缩水甘油醚产物,它们用常规硬化剂如酸酐或胺在有促进剂或无促进剂下交联。
27.天然聚合物,如纤维素、橡胶、明胶和其化学改性的类似衍生物,如乙酸纤维素、丙酸纤维素和丁酸纤维素,或纤维素醚如甲基纤维素;以及松香和其衍生物。
28.上述聚合物的共混物(掺混聚合物),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、PBT/PC/ABS或PBT/PET/PC。
29.天然存在和合成的有机材料,它们是纯单体化合物或这些化合物的混合物,如矿物油,动物和植物脂、油和蜡,或基于合成酯(如邻苯二甲酸酯、己二酸酯、磷酸酯或偏苯三酸酯)的油、脂和蜡,以及合成酯与矿物油以任何重量比的混合物,通常用作纺丝组合物的那些混合物,及这些材料的水乳液。
30.天然和合成橡胶的水乳液,如天然胶乳或羧酸化的苯乙烯/丁二烯共聚物胶乳。
本发明还涉及包括容易氧化、热或光诱导降解的有机材料和本发明稳定剂混合物的组合物。
要稳定的有机材料优选为合成聚合物,特别是选自上述各组的合成聚合物,聚烯烃是优选的,聚乙烯和聚丙烯是特别优选的。
优选的有机材料还为热塑性聚合物或用于涂料的粘合剂。
要使用的稳定剂混合物的量取决于要稳定的有机材料和稳定的有机材料的预定用途。通常使用(例如)总量为0.01至10 wt%,优选0.01至5wt%,特别优选0.05至1wt%的稳定剂混合物(按要稳定的材料重量计)。
稳定剂混合物可在(例如)所述材料聚合或交联之前、期间或之后加入聚合物材料中。同时,稳定剂混合物可以纯净形式或在石蜡、油或聚合物中的胶囊化形式加入聚合材料中。
通常,本发明的稳定剂混合物可通过各种方法,如以粉末形式干混,或以溶液形式或悬浮液形式湿混或以母料形式加入有机材料中;在这些操作中,聚合物可以粉末、颗粒、溶液、悬浮液或胶乳形式使用。
同样,可将本发明稳定剂混合物的单个组分加入到要稳定的材料中。
用本发明稳定剂混合物稳定的材料可用于生产模塑制品、薄膜、胶带、单丝、纤维、表面涂料等。
若需要,可将用于合成聚合物的常规添加剂如抗氧剂、UV吸收剂、镍稳定剂、颜料、填料、增塑剂、防腐剂和金属钝化剂加入含本发明稳定剂混合物的有机材料中。所述常规添加剂的具体例子是:1.抗氧剂
1.1.烷基化的一元酚,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,线型或在侧链中支化的壬基苯酚如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 烷硫基甲基苯酚,例如2,4-二辛硫基甲基-6-叔丁基苯酚、2,4-二辛硫基甲基-6-甲基苯酚、2,4-二辛硫基甲基-6-乙基苯酚、2,6-二-十二烷硫基甲基-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-羟基茴香醚、3,5-二叔丁基-4-羟基茴香醚、硬脂酸3,5-二叔丁基-4-羟基苯基酯、己二酸双(3,5-二叔丁基-4-羟基苯基)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 羟基化的硫连二苯基醚,例如2,2′-硫连双(6-叔丁基-4-甲基苯酚)、2,2′-硫双(4-辛基苯酚)、4,4′-硫连双(6-叔丁基-3-甲基苯酚)、4,4′-硫连双(6-叔丁基-2-甲基苯酚)、4,4′-硫连双(3,6-二仲戊基苯酚)、4,4′-双(2,6-二甲基-4-羟基苯基)二硫化物。
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)-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(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)、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]、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-双(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、1,1-5双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、双[3,3-双(3′-叔丁基-4′-羟基苯基)丁酸]乙二醇酯、双(3-叔丁基-4-羟基-5-甲基苯基)双环戊二烯、对苯二甲酸双[2-(3′-叔丁基-2′-羟基-5′-甲基苄基)-6-叔丁基-4-甲基苯基]酯、1,1-双(3,5-二甲基-2-羟苯基)丁烷、2,2-双(3,5-二叔丁基-4-羟基苯基)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、4-羟基-3,5-二甲基苄硫基乙酸十八烷基酯、4-羟基-3,5-二叔丁基苄硫基乙酸十三烷基酯、三(3,5-二叔丁基-4-羟基苄基)胺、二硫代对苯二甲酸双(4-叔丁基-3-羟基-2,6-二甲基苄基)酯、双(3,5-二叔丁基-4-羟苄基)硫化物、3,5-二叔丁基-4-羟基苄硫基乙酸异辛基酯。
1.8 羟基苄基化的丙二酸酯,例如2,2-双-(3,5-二叔丁基-2-羟苄基)丙二酸二-十八烷基酯、2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸二-十八烷基酯、2,2-双-(3,5-二叔丁基-2-羟基苄基)丙二酸二-十二烷硫基乙基酯、2,2-双-(3,5-二叔丁基-4-羟基苄基)丙二酸双[4-(1,1,3,3-四甲丁基)苯基]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-羟基苄基)苯酚。
1.10 三嗪化合物,例如2,4-双(辛巯基)-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛巯基-4,6-双(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛巯基-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、2,4,6-三(3,5-二叔丁基-4-羟基苯乙基)-1,3,5-三嗪、1,3,5-三(3,5-二叔丁基-4-羟基苯丙酰基)-六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟基苄基)异氰尿酸酯。
1.11 膦酸苄基酯,例如2,5-二叔丁基-4-羟基苄基膦酸二甲酯、3,5-二叔丁基-4-羟基苄基膦酸二乙酯、3,5-二叔丁基-4-羟基苄基膦酸二-十八烷基酯、5-叔丁基-4-羟基-3-甲基苄基膦酸二-十八烷基酯、3,5-二叔丁基-4-羟基苄基膦酸单甲酯的钙盐。
1.12 酰氨基苯酚,例如4-羟基月桂酰苯胺、 4-羟基硬脂酰苯胺、N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.13 β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元醇或多元醇的酯,所述醇的例子是: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、硫二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N′-双(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.14 β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇的酯,所述醇的例子是: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、硫二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N′-双(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.15 β-(3,5-二环己基-4-羟基苯基)丙酸与一元醇或多元醇的酯,所述醇的例子是: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、硫二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N′-双(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.16 3,5-二叔丁基-4-羟基苯基乙酸与一元醇或多元醇的酯,所述醇的例子是: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、硫二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰尿酸酯、N,N′-双(羟乙基)草酰胺、3-硫杂十一烷醇、3-硫杂十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.17 β-(3,S-二叔丁基-4-羟基苯基)丙酸的酰胺,例如:N,N′-双(3,5-二叔丁基-4-羟基苯基丙酰基)己二胺、N,N′-双(3,5-二叔丁基-4-羟基苯基丙酰基)三亚甲基二胺、N,N′-双(3,5-二叔丁基-4-羟基苯基丙酰基)肼。
1.18 抗坏血酸(维生素C)
1.19 胺类抗氧剂,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-甲基庚基)-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)二苯基胺、N,N′-二甲基-N,N′-二仲丁基-对苯二胺、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,辛基化的二苯基胺如p,p′-二叔辛基二苯基胺、4-正丁氨基苯酚、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、双(4-甲氧基苯基)胺、2,6-二叔丁基-4-二甲氨基甲基苯酚、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-1,4-二氨基丁烯-2、N,N-双(2,2,6,6-四甲基-哌啶-4-基-己二胺、癸二酸双(2,2,6,6-四甲基-哌啶-4-基)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
2.1.2-(2′-羟基苯基)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′-羟基苯基)苯并三唑、2-(5′-叔丁基-2′-羟基苯基)苯并三唑、2-(2′-羟基-5′-(1,1,3,3-四甲基丁基)苯基)苯并三唑、2-(3′,5′-二叔丁基-2′-羟基苯基)-5-氯-苯并三唑、2-(3′-叔丁基-2′-羟基-5′-甲基苯基)-5-氯-苯并三唑、2-(3′-仲丁基-5′-叔丁基-2′-羟基苯基)苯并三唑、2-(2′-羟基-4′-辛氧基苯基)苯并三唑、2-(3′,5′-二叔戊基-2′-羟基苯基)苯并三唑、2-(3′,5′-双-(α,α-二甲基苄基-2′-羟基苯基)苯并三唑,2-(3′-叔丁基-2′-羟基-5′-(2-辛氧基羰基乙基)苯基)-5-氯-苯并三唑、2-(3′-叔丁基-5′-[2-(2-乙基己氧基)-羰基乙基]-2′-羟基苯基)-5-氯-苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-甲氧基羰基乙基)苯基)-5-氯-苯并三唑、2-(3′-叔丁基-2′-羟基-5′-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3′-叔丁基-2′-羟基5′-(2-辛氧基羰基乙基)苯基)苯并三唑、2-(3′-叔丁基-5′-[2-(2-乙基己氧基)羰基乙基]-2′-羟基苯基)苯并三唑、2-(3′-十二烷基-2′-羟基-5′-甲基苯基)苯并三唑和2-(3′-叔丁基-2′-羟基-5′-(2-异辛氧基羰基乙基)苯基苯并三唑的混合物,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′-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯基转移产物;其中R=3′-叔丁基-4′-羟基-5′-2H-苯并三唑-2-基苯基。
2.2.2-羟基二苯(甲)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.取代和未取代苯甲酸的酯,例如水杨酸4-叔丁基苯基酯、水杨酸苯基酯、水杨酸辛基苯基酯、二苯甲酰基间苯二酚、双(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯基酯、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,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-氰乙烯基)-2-甲基二氢吲哚。
2.5.镍化合物,例如2,2′-硫双-[4-(1,1,3,3-四甲基丁基)苯酚]的镍配合物,如1∶1或1∶2配合物,该配合物有或无另一些配体(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-3,5-二叔丁基苄基膦酸的单烷基酯如甲酯或乙酯的镍盐,酮肟如2-羟基-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-羟基吡唑的镍配合物(有或无另外的配体)。
2.6.受阻胺,如正丁基-3,5-二叔丁基-4-羟基苄基丙二酸双(1,2,2,6,6-五甲基-4-哌啶基)酯、1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基吡啶与丁二酸的缩合物、N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺与4-叔辛氨基-2,6-二氯-1,3,5-三嗪的缩合物、次氮基三乙酸三(2,2,6,6-四甲基-4-哌啶基)酯、1,2,3,4-丁烷-四羧酸四(2,2,6,6-四甲基-4-哌啶基)-酯、1,1′-(1,2-亚乙基)双(3,3,5,5-四甲基-哌嗪酮)、4-苯甲酰基-2,2,6,6-四甲基哌啶、4-硬脂酰氧基-2,2,6,6-四甲基哌啶、2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸双(1,2,2,6,6-五甲基-4-哌啶基)酯、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、癸二酸双(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)酯、丁二酸双(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)酯、N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺与4-吗啉代-2,6-二氯-1,3,5-三嗪的缩合物、2-氯-4,6-双(4-正丁氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪与1,2-双(3-氨丙基氨基)乙烷的缩合物、2-氯-4,6-二-(4-正丁氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪与1,2-双(3-氨丙基氨基)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]癸烷-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-和4-硬脂酰氧基-2,2,6,6-四甲基哌啶的混合物、N,N′-双(2,2,6,6-四甲基-4-哌啶基)己二胺与4-环己氨基-2,6-二氯-1,3,5-三嗪的缩合物、1,2-双(3-氨丙基氨基)乙烷与2,4,6-三氯-1,3,5-三嗪的缩合产物以及4-丁氨基-2,2,6,6-四甲基哌啶(CAS登记号[136504-96-6];N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基丁二酰亚胺、N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基丁二酰亚胺、2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代-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-氧代-螺[4.5]癸烷和表氯醇的反应产物。
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N,N′-草酰二苯胺、N,N′-双(3-二甲氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2′-乙基N,N′-草酰二苯胺和其与2-乙氧基-2′-乙基-5,4′-二叔丁基N,N′-草酰二苯胺的混合物,以及邻-与对-甲氧基二取代N,N′-草酰二苯胺的混合物和邻-与对-乙氧基二取代N,N′-草酰二苯胺的混合物。
2.8.2-(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-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-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[4-(十二烷氧基/十三烷氧基-2-羟基丙氧基)-2-羟基-苯基]-4,6-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-羟基苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪。
3.金属钝化剂,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-水杨酰氨基-1,2,4-三唑、双(亚苄基)草酰二酰肼、N,N′-草酰二苯胺、间苯二甲酰二酰肼、癸二酰联苯基酰肼、N,N′-二乙酰基己二酰二酰肼、N,N′-双(水杨酰基)草酰二酰肼、N,N′-双(水杨酰基)硫代丙酰二酰肼、
4.亚磷酸和亚膦酸酯,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、亚磷酸三月桂酯、亚磷酸三-十八烷基酯、二亚磷酸二(十八烷基)季戊四醇酯、亚磷酸三(2,4-二叔丁基苯基)酯、二亚磷酸二异癸基季戊四醇酯、二亚磷酸双(2,4-二叔丁基苯基)季戊四醇酯、二亚磷酸双(2,6-二叔丁基-4-甲基苯基)季戊四醇酯、二亚磷酸二异癸氧基季戊四醇酯、二亚磷酸双(2,4-二叔丁基-6-甲基苯基)季戊四醇酯、二亚磷酸双(2,4,6-三(叔丁苯基)季戊四醇酯、三亚磷酸三(十八烷基)山(梨)醇酯、4,4′-亚联苯基二亚膦酸四(2,4-二叔丁基苯基)酯、6-异辛氧基-2,4,8,10-四叔丁基-1 2H-二苯并[d,g]-1,3,2-二氧杂磷辛、6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂磷辛、亚磷酸双(2,4-二叔丁基-6-甲基苯基)甲基酯、亚磷酸双(2,4-二叔丁基-6-甲基苯基)乙基酯。
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、衍生自氢化动物脂胺的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、衍生自N,N-二烷基羟胺的硝酮(所述N,N-二烷基羟胺衍生自氢化动物脂胺)。
7.硫增效剂,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-硫连二丙酸的酯,如月桂基、硬脂基、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、二-十八烷基二硫化物、四(β-十二烷基巯基)丙酸季戊四醇酯。
9.多胺稳定剂,例如铜盐与碘和/或磷化合物的混合物及二价锰盐。
10.碱性共稳定剂,例如密胺、聚乙烯基吡咯烷酮、双氰胺、氰尿酸三烯丙基酯、脲衍生物、肼衍生物、胺、多胺、聚氨酯、高级脂肪酸的碱金属盐和碱土金属盐如硬脂酸钙、硬脂酸锌、山萮酸镁、硬脂酸镁、蓖麻酸钠和棕榈酸钾、焦儿茶酚锑或焦儿茶酚锡。
11.成核剂,例如无机物质,如滑石,金属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;有机化合物如单或多羧酸及其盐,如4-叔丁基苯甲酸、己二酸、二苯基乙酸、丁二酸钠或苯甲酸钠;聚合物,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、陶土、云母、硫酸钡、金属氧化物和金属氢氧化物、炭黑、石墨、木粉或其它天然产物的粉或纤维、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、光学增量剂、阻燃剂、抗静电剂和发泡剂。
14.苯并呋喃酮和二氢吲哚酮,例如US-A-4325863、US-A-4338244、US-A-5175312、US-A-5216052、US-A-5252643、DE-A-4316611、DE-A-4316622、DE-A-4316876、EP-A-0589839或EP-A-0591102中公开的那些或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′-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-乙氧基-3,5-二甲苯基)-5,7-二叔丁基-苯并呋喃-2-酮、3-(3,5-二甲基-4-戊酰氧基苯基)-5,7-二叔丁基-苯并呋喃-2-酮。
本发明稳定剂混合物与常规添加剂的重量比可以为(例如)1∶0.5至1∶5。
特别感兴趣的是将本发明的稳定剂混合物用作涂料(如漆)的稳定剂。因此,本发明还涉及其中要稳定的物质为用于涂料的成膜基的组合物。
新涂料组合物按每100重量份基料(固体形式)计优选包括0.01-10重量份,更优选0.05-10重量份,特别优选0.1-5重量份的本发明稳定剂混合物。
多层体系也是可能的,其中本发明稳定剂混合物在外层中的浓度可以更高,例如按每100重量份基料(固体形式)计为1-15重量份,优选3-10重量份。
用本发明的稳定剂混合物作为在涂层中的稳定剂具有的另一优点是可防止脱层,即涂层从基材上剥离。在金属基材情况(包括金属基材上的多层体系情况)下,此优点特别重要。
基料(要稳定的物质)原则上可以为工业上常用的任何基料,例如Ullmann工业化学大全,第五版,Vol.A18,pp.368-426,(VCH,Weinheim,1991)中描述的那些基料。通常,这是基于热塑性或热固性树脂(主要基于热固性树脂)的成膜基料。其例子是醇酸、丙烯酸、聚酯、酚醛、密胺、环氧和聚氨酯树脂及其混合物。
要稳定的物质可以是可冷固化或热固化的基料;可有利地加入固化催化剂。促进基料固化的合适催化剂描述于(例如)Ullmann工业化学大全,Vol.Al8,p469,(VCH,Verlagsgesell schaftWeinheim,1991)中。
其中要稳定的物质是包括官能丙烯酸酯树脂和交联剂的基料的涂料组合物是优选的。
含特定基料的涂料组合物的例子是:
1.基于可冷或热交联的醇酸、丙烯酸酯、聚酯、环氧或密胺树脂或这些树脂的混合物的漆,若需要可加入固化催化剂;
2.基于含羟基的丙烯酸酯、聚酯或聚醚树脂和脂族或芳族异氰酸酯、异氰尿酸酯或多异氰酸酯的双组分聚氨酯漆;
3.基于封闭异氰酸酯、异氰尿酸酯或多异氰酸酯(它们在烘烤过程中除去封闭)的单组分聚氨酯漆;
4.基于(聚)酮亚胺和脂族或芳族异氰酸酯、异氰尿酸酯或多异氰酸酯的双组分漆;
5.基于(聚)酮亚胺和不饱和丙烯酸酯树脂或聚乙酰乙酸酯树脂或甲基丙烯酰氨基甘醇酸酯甲基酯的双组分漆;
6.基于含羧基或氨基的聚丙烯酸酯或聚环氧化物的双组分漆;
7.基于含酸酐的丙烯酸酯树脂和多羟基或多胺组分的双组分漆;
8.基于含丙烯酸酯的酸酐和聚环氧化物的双组分漆;
9.基于(聚)恶唑啉和含酸酐的丙烯酸酯树脂或不饱和丙烯酸酯树脂或脂族或芳族异氰酸酯、异氰尿酸酯或多异氰酸酯的双组分漆;
10.基于不饱和聚丙烯酸酯和聚丙二酸酯的双组分漆;
11.基于热塑性丙烯酸酯树脂或外交联丙烯酸酯树脂与醚化密胺树脂的热塑性聚丙烯酸酯树脂漆。
12.基于硅氧烷改性或氟改性丙烯酸酯树脂的漆体系。
除了要稳定的物质和本发明的稳定剂混合物外,新涂料组合物还可包括受阻胺类和/或2-羟基苯基-2H-苯并三唑和/或2-(2-羟基苯基)-1,3,5-三嗪(如上面2.1、2.6和2.8中提及的)光稳定剂作为辅助组分。
当基于羟基苯基苯并三唑和/或羟基二苯(甲)酮和/或N-草酰苯胺和/或羟苯基-s-三嗪(如上面2.1、2.2、2.7和2.8中提及的)的UV吸收剂作为辅助组分存在时,尤其可改进本发明稳定剂混合物的效果。
辅助组分的用量按每100重量份基料(固体形式)计优选为0.05至5重量份。
除了要稳定的物质和本发明的稳定剂混合物外,涂料组合物可包括另一些组分,如溶剂、颜料、染料、增塑剂、稳定剂、触变剂、干燥催化剂和/或流动控制剂。可能组分的例子是描述于Ullmann工业化学大全,第五版,Vol.A18,pp.429-471,(VCH,Weinheim,1991)中的那些。
可能的干燥催化剂或固化剂是(例如)有机金属化合物、胺、含氨基的树脂和/或膦。有机金属化合物的例子是金属羧酸盐,特别是金属Pb、Mn、Co、Zn、Zr和Cu的羧酸盐,或金属螯合物,特别是Al、Ti和Zr的螯合物,或有机金属化合物如有机锡化合物。
金属羧酸盐的例子是Pb、Mn和Zn的硬脂酸盐,Co、Zn和Cu的辛酸盐,Mn和Co的环烷酸盐及相应的亚油酸盐、树脂酸盐和tallate(树脂酸盐)。
金属螯合物的例子是乙酰丙酮、乙酰乙酸乙酯、水杨醛、水杨醛肟、邻羟基苯乙酮和三氟乙酰乙酸乙酯的铝、钛和锆螯合物,及这些金属的醇盐。
有机锡化合物的例子是氧化二丁基锡、二月桂酸二丁基锡和二辛酸二丁基锡。
胺的例子具体为叔胺,如三丁胺、三乙醇胺、N-甲基二乙醇胺、N-二甲基乙醇胺、N-乙基吗啉、N-甲基吗啉和二氮杂环辛烷(三亚乙基二胺)及其盐。另一些例子是季铵盐,如氯化三甲基苄基铵。
含氨基的树脂同时为基料和固化催化剂。它们的例子是含氨基的丙烯酸酯共聚物。
固化剂还可为膦,如三苯基膦。
新涂料组合物也可以是辐射固化的,在这种情况下,基料基本上包括含烯属不饱和键的单体或低聚物,这些物质在涂布后通过光化辐射固化,即转化为交联高分子形式。UV-固化体系通常还包括光引发剂。相应的体系描述于上述出版物Ullmann工业化学大全,第五版,Vol.A18,pp.451-453中。在辐射固化涂料组合物中,新稳定剂混合物还可在不加受阻胺下使用。
新涂料组合物可涂于任何所需的基材,如金属、木材、塑料或陶瓷材料上。它们在汽车涂漆中优选用作面漆。若面漆包括两层(其中里层有颜料,外层无颜料),则新涂料组合物可用作外层或里层或用作这两层,但优选用作外层。
新涂料组合物可通过常规方法,如刷涂、喷涂、淋涂、醮涂或电泳涂于基材上;还可参见Ullmann工业化学大全,第五版,Vol.A18,pp.491-500。
涂料的固化(取决于基料体系)可在室温下或通过加热进行。涂料优选在50至150℃下固化,粉末涂料还可在更高温度下固化。
根据本发明获得的涂料具有极好的耐光、氧气和热的有害影响;特别应提及的是涂料(如按此方式获得的漆)的良好耐光或天候老化性。
因此,本发明还涉及一种涂料,特别是漆,它通过一定量的本发明稳定剂混合物稳定耐光、氧气和热的有害影响。该漆优选为用于汽车的面漆。
涂料组合物可包括有机溶剂或溶剂混合物,基料在其中是可溶的。然而,该涂料组合物也可为水溶液或分散体。溶剂还可为有机溶剂与水的混合物。涂料组合物还可以是高固含量的漆或不含溶剂(漆粉)。
颜料可以为无机、有机或金属颜料。该新涂料组合物优选不含颜料并可用作清漆。
同样优选的是将该涂料组合物在汽车工业中用作涂布面漆,特别是用作有颜料或无颜料的罩面漆的面漆。然而,该涂料组合物也可用作底层。
通式(Ⅰ)的化合物还可用作照相复制和其它复制技术领域的几乎所有材料(如“研究公开(Research Disclosure)”1990,31429,p474至480)的稳定剂,特别是光稳定剂。
下面的实施例详细描述本发明。在这些实施例中,份数和百分数都按重量计;室温是指20至25℃范围内的温度。除非另有说明,这些限定适用于所有实施例。
本发明稳定剂混合物的实施例在下表1中给出。表1:
表1(续):
实施例1:制备混合物101
混合物N编号 | R | n[%GC(气相色谱)] | 分析计算值 测定值 | 熔点℃ |
101 | H | 2(25),3(39),4(27) | C% 67.28 66.41H% 10.31 10.12N% 6.82 6.5 2 | 65-109 |
102 | Me | 2(26),3(40),4(24) | C% 68.45 68.14H% 10.57 11.33 | - |
N% 6.39 6.39 | ||||
103 | H | 2(20),3(52),4(15) | C% 67.28 65.62H% 10.31 10.51N% 6.82 6.37 | 47-74 |
104 | Me | 2(21),3(55),4(15) | C% 68.45 66.55H% 10.57 10.86N% 6.39 6.86 | - |
105 | H | 3(79),4(20) | C% 66.95 67.1H% 10.75 10.93N% 6.79 6.61 | 67-77 |
106 | Me | 3(74),4(23) | C% 68.14 66.82H% 10.98 11.00N% 6.36 6.13 | - |
107 | H | 3(9),4(85) | C% 68.21 66.58H% 10.02 10.74N% 6.63 6.10 | 78-87 |
108 | Me | 3(9),4(82) | C% 68.18 68.02H% 10.10 10.92N% 6.24 5.85 | 78-87 |
109 | H | 7(47),8(48) | C% 69.73 69.48H% 10.85 10.80N% 5.91 5.26 | - |
110 | H | 4(42),7(49) | C% 68.72 68.63H% 10.63 10.91N% 6.29 6.07 | 75-80 |
111 | Me | 4(43),7(42) | C% 69.73 68.92H% 10.85 10.84N% 5.91 5.85 | - |
112 | H/Me | 8(100) | C% 70.40 70.20 | - |
(1∶1) | H% 11.00 11.43N% 5.66 5.63 | |||
113 | H/Me(3∶1) | 2(20),3(40),4(20) | C% 67.89 68.10H% 10.44 10.84N% 6.60 6.29 | - |
混合物编号 | R | n[%GC(气相色谱)] | 分析计算值 测定值 | 熔点℃ |
114 | Me | 3(70.3),4(22.4) | C% 68.14 68.10H% 10.98 10.84N% 6.36 6.29 | - |
115 | -O- | 2(20),3(52),4(15) | 41-42 | |
116 | OC8H17 | 2(20),3(52),4(15) |
a)在室温下将19.6 g(0.2 mol)浓硫酸滴加入26.4 g(0.2 mol)“二羧酸混合物”(购自BASF)在200甲醇中的溶液中。将此反应混合物加热回流3小时。将此混合物用27.6 g(0.2 mol)碳酸钾中和,倒入饱和NH4Cl溶液中并用乙酸乙酯萃取。将有机萃取物干燥(盐水,Na2SO4)并在真空下浓缩制得32g(100%)所需甲基酯混合物,为无色液体。GC(气相色谱)/MS(质谱)分析:MW(分子量)115 g/mol(28.3%),MW 129 g/mol(42.5%),MW 143g/mol(29.2%)。
b)将26.7 g(0.15 mol)实施例 1a)所述的甲基二酯、58 g(0.38 mol)2,2,6,6-四甲基哌啶-4-醇和1.5 g(6 mmol)氧化二丁基锡加热至150℃,同时通过蒸馏除去甲醇。2小时后对反应混合物施加中等真空(300毫巴)并在150℃下再搅拌10小时。将反应混合物冷却,用己烷稀释,过滤并在真空下浓缩。将过量哌啶醇通过蒸馏(球管:170℃/0.08毫巴)除去得到标题混合物,为无定形固体(熔程:40-65℃)。实施例2:制备混合物102
用16 g(0.1 mol)实施例1a)所述的二酯混合物、42.8 g(0.25 mol)1.2,2,6,6-五甲基哌啶-4-醇和1 g(4 mmol)氧化二丁基锡,按照实施例1的步骤制备此混合物。得到34 g(78%)混合物102,为粘稠油。实施例3:制备混合物103
用8 g(0.05 mol)DBE(市购的丁二酸、戊二酸和己二酸甲基酯按比例20∶59∶21的混合物,购自Du Pont)、20.44 g(0.13 mol)2,2,6,6-四甲基哌啶-4-醇和0.62 g(2.5 mmol)氧化二丁基锡,按照实施例1的步骤制备此混合物。得到16.5 g(81%)混合物103,为无定形固体(熔程:45-74℃)。实施例4:制备混合物104
用8g(0.05 mol)DBE(市购的丁二酸、戊二酸和己二酸甲基酯按比例20∶59∶21的混合物,购自DuPont)、19.7 g(0.115 mol)1,2,2,6,6-五甲基哌啶-4-醇和0.62 g(2.5 mmol)氧化二丁基锡,按照实施例1的步骤制备此混合物。得到19.3 g(88%)混合物104,为粘稠油。实施例5:制备混合物105
将11.4 g(0.07 mol)DBE2(市购的戊二酸和己二酸甲基酯按比例77∶23的混合物,购自Du Pont)和26.4 g(0.17 mol)2,2,6,6-四甲基哌啶-4-醇在30ml二甲苯中的悬浮液加热至80℃。将氨基锂(0.08 g,3.5mmol)加入所得溶液中,并将此混合物加热至145℃以蒸馏甲醇。将此混合物再搅拌15小时。冷却至80℃时后,加入乙酸(0.3 g,5 mmol),并将此反应混合物用热甲苯稀释,过滤,然后在真空下浓缩。蒸馏出过量哌啶醇后(球管:180℃/0.1毫巴,得到20 g(69%)混合物105,白色固体(熔程:67-77℃)。实施例6:制备混合物106
将11.4 g(0.07 mol)DBE2(购自Du Pont,见实施例5)和26.4g(0.15 mol)1,2,2,6,6-五甲基哌啶-4-醇通过加入10 ml甲苯干燥,然后在140℃在真空(200毫巴)下加热以除去水-甲苯共沸物。将反应器用氮气加压并加入0.7 g(3.5 mmol)异丙醇铝。将此混合物加热至160℃以蒸馏甲醇。1小时后,施加真空(300毫巴),将此混合物再搅拌15小时。冷却至80℃时后,加入乙酸(0.3 g,5 mmol),并将此反应混合物用甲苯稀释,过滤,然后在真空下浓缩。蒸馏出过量哌啶醇后(球管:180℃/0.1毫巴),得到26.3 g(85%)混合物106,为油状物。实施例7:制备混合物107
用12.1 g(0.07 mol)DBE3(市购的戊二酸和己二酸甲基酯按比例10∶90的混合物,购自Du Pont)、23.6 g(0.15 mol)2,2,6,6-四甲基哌啶-4-醇和0.7 g(2.8 mmol)氧化二丁基锡,按照实施例1的步骤制备此混合物。得到20 g(68%)混合物107,无定形固体(熔程:78-87℃)。实施例8:制备混合物108
用12.1 g(0.07 mol)DBE3(市购的戊二酸和己二酸甲基酯按比例10∶90的混合物,购自Du Pont)、26.4 g(0.15 mol)1,2,2,6,6-五甲基哌啶-4-醇和0.7 g(2.8 mmol)氧化二丁基锡,按照实施例1的步骤制备此混合物。得到28 g(89%)混合物108,无定形固体(熔程:78-87℃)。实施例9:制备混合物109
将6.5 g(0.041 mol)2,2,6,6-四甲基哌啶-4-醇和4.9 g(0.048 mmol)三乙胺在150 ml 1,2-二氯乙烷中的悬浮液冷却至约5℃。滴加入2.25g(0.01 mol)壬二酰二氯和2.39 g(0.01 mol)癸二酰氯的混合物并除去冷水浴。将所得粘稠白色悬浮液加热至60℃,加热5小时。冷却至室温后,将此反应混合物过滤并在真空下浓缩。将残余物在高真空(70℃/0.08毫巴)下干燥,得到9.32 g(98%)混合物109,为浅橙色油状物。实施例10:制备混合物110
用22.65 g(0.144 mol)2,2,6,6-四甲基哌啶-4-醇、5.2 3 g(0.03 mol)己二酸甲酯、6.49 g(0.03 mol)壬二酸甲酯和0.07 g(3 mmol)氨基锂,按照实施例5的步骤制备此混合物。得到20.5 g(77%)混合物110,白色固体(熔程:75-80℃)。实施例11:制备混合物111
用25.65 g(0.15 mol)1,2,2,6,6-五甲基哌啶-4-醇、5.23 g(0.03 mol)己二酸甲酯、6.49 g(0.03 mol)壬二酸甲酯和0.75 g(3mmol)氧化二丁基锡,按照实施例1的步骤制备此混合物。得到25.9 g(91%)混合物111,为橙色油状物。实施例12:制备混合物112
用10.22 g(0.065 mol)2,2,6,6-四甲基哌啶-4-醇、11.13 g(0.065mol)1,2,2,6,6-五甲基哌啶-4-醇、11.52 g(0.05 mol)癸二酸甲酯和58 mg“Fascat 9201”(聚合的基于锡的催化剂,购自Elf Atochem),按照实施例1的步骤制备此混合物。得到24.5 g(98%)混合物112,为棕色油状物。实施例13:制备混合物113
用15.7 g(0.1 mol)2,2,6,6-四甲基啶-4-醇、5.14 g(0.03 mol)1,2,2,6,6-五甲基哌啶-4-醇、8 g(0.05 mol)DBE(购自Du Pont,见实施例3)和58 mg“Fascat 9201”(聚合的基于锡的催化剂,购自Elf Atochem),按照实施例1的步骤制备此混合物。得到14 g(70%)混合物113,为棕色油状物。实施例14制备混合物114
将12 g(0.07 mol)1,2,2,6,6-五甲基哌啶-4-醇通过在真空(100毫巴)下在140℃下加热1小时30分钟进行干燥(除去水)。冷却至100℃后,将反应器用氮气加压并加入5.7 g(0.035 mol)DBE2(购自Du Pont,见实施例5),接着加入0.45 ml(1.75 mmol)仲丁基铝。将此混合物加热至165℃以蒸馏甲醇。30分钟后,施加真空(200毫巴),将此混合物再搅拌5小时。冷却至约80℃时后,加入甲酸(0.2 ml),将此反应混合物用甲苯稀释,倒入水中并用甲苯萃取。将有机萃取物干燥(盐水,Na2SO4)并在真空下浓缩制得14.6 g浅黄色油状物。除去未反应的哌啶醇(球管:1 50℃/0.1毫巴/2h),得到13.53 g(88%)混合物114,为浅黄色油状物。实施例15制备混合物115
49.8 gDBE(0.3116 mol)(DuPont,见实施例3)与111.6 g 2,2,6,6-四甲基-4-羟基吡啶硝酰(0.6294 mol)和TPT催化剂(3.22 g,0.011 mol)[TPT=钛酸四异丙酯]在350 g正庚烷中的酯基转移反应在7小时内完成(除去甲醇期间,釜温保持于97-99℃下同时塔顶溜出物温度范围为64-96℃)。将物料用30 g正庚烷稀释并用20 g去离子水在90℃下处理TPT催化剂,然后共沸干燥至100℃并过滤。将产品溶液用5×100 g MeOH:H2O(10%)在70℃下洗涤除去过量2,2,6,6-四甲基-4-羟基吡啶硝酰。然后共沸干燥至100℃。将物料慢慢冷却至结晶点41-42℃,再冷却至10℃。将物料过滤用冷正庚烷漂洗,然后干燥得到124.3 g(90.7%离析产率)红色固体。实施例16制备混合物116
通过51g二硝酰(0.1159 mol)、0.13 g MoO3(0.0009 mol)、228 g正辛烷(1.996 mol)与在95-110℃下在1.75小时内加入的36.5 g×70%叔丁基过氧化氢(0.4050 mol)反应使DBE二硝酰(115,实施例15)转化为相应的NO-辛基衍生物。通过用5阶段Oldershow柱除去H2O/正丁醇/正辛烷溜出物使反应温度升至118℃,并保持13小时。将反应物冷却至55℃并通过过滤除去MoO3。分离需要27.8的g的11%硫化钠与2.5 g的20%NaOH相结合在55℃下处理1小时。然后除去水层,将有机层通过加入20 g去离子水和乙酸中和。然后加入Darco KB44(5g)(1CI的TM,活性炭),将此溶液加热至70℃并保持1小时。接着过滤并在70℃下在高真空下汽提,得到浅黄色油,它在425 nm、450 nm和500 nm处的透射率分别为98.3%、98.7%和99.3%。实施例17:2-道涂料金属漆的稳定性
将要测试的光稳定剂溶于30 g Solvesso100中并在具有如下组成的清漆中测试:SynthacrylSC 3031 27.51 gSynthacrylSC 3702 23.34 gMaprenal6503 27.29 g乙酸丁酯/丁醇(37/8) 4.33 g异丁醇 4.87 gSolvesso1504 2.72 g晶体油K-305 8.74 g匀涂助剂BaysilonMA6 1.20 g100.00 g1丙烯酸酯树脂,Hoechst AG;在二甲苯/丁醇(26∶9)中的65%溶液2丙烯酸酯树脂,Hoechst AG;在Solvesso1004中的75%溶液3密胺树脂,Hoechst AG;在异丁醇中的55%溶液4芳烃混合物,沸程:182-203℃(Solvesso150)或161-178℃(Solvesso100);生产商:Esso5脂族烃混合物,沸程:145-200℃;生产商:Shell61%,在Solvesso150中;生产商:Bayer AG
为了对比,使用不含光稳定剂的清漆。
将清漆用Solvesso100稀释至喷涂粘度,并通过喷涂施于制备的铝板上(Uniprime Epoxy,金属银底涂层),将此板在130℃下烘烤30分钟得到厚度40-50μm的干燥薄膜。
然后将样品在包括70℃下UV辐射8小时和50℃下缩合4小时的一次循环的AtlasUVCON老化设备(UVB-313灯)中老化。
接着在规定间隔测定样品的表面光泽(按DIN 67530中定义的20°光泽)。结果在表2a-2d中给出:表2a:
光稳定剂 | 在UVCON(UVB-313)中按DIN67530定义的在0、1600和2000小时老化后的20°*光泽 | ||
0小时 | 1600小时 | 2000小时 | |
无 | 87 | ** | |
(A) | 87 | 28 | 13 |
(B) | 86 | 24 | *** |
(C) | 86 | 49 | 21 |
*:高值表示良好的稳定性
**:在800小时后收缩
***:在1600小时后收缩
使用的光稳定剂:光稳定剂(A):R=-CH3;n=4光稳定剂(B):R=-CH3;n=7光稳定剂(C):混合物111(R=-CH3;比例n=4(43%)/7(42%))表2b:
光稳定剂 | UVCON(UVB-313)中按DIN67530定义的在0和1600小时老化后的20°*光泽 | |
0小时 | 1600小时 | |
无 | 87 | ** |
(D) | 87 | 53 |
(E) | 87 | 28 |
(F) | 87 | 61 |
*:高值表示良好的稳定性
**:在800小时后收缩
使用的光稳定剂:光稳定剂(D):R=-CH3;n=3光稳定剂(E):R=-CH3;n=4光稳定剂(F):混合物108(R=-CH3;比例n=3(9%)/4(82%))表2c:
光稳定剂 | UVCON(UVB-313)中按DIN67530定义的在0、4000和4400小时老化后的20°*光泽 | ||
0小时 | 4000小时 | 4400小时 |
无 | 87 | ** | |
TINUVIN 384 | 86 | *** | |
(A)+TINUVIN384 | 87 | 85 | 41 |
(B)+TINUVIN384 | 87 | 75 | 25 |
(C)+TINUVIN384 | 87 | 87 | 63 |
*:高值表示良好的稳定性
**:在1200小时后破裂
***:在2000小时后破裂
使用的光稳定剂:TINUVIN 384 光稳定剂(A):R=-CH3;n=4光稳定剂(B):R=-CH3;n=7光稳定剂(C):混合物111(R=-CH3;比例n=4(43%)/7(42%))表2d:
光稳定剂 | UVCON(UVB-313)中按DIN67530定义的在0、4000、4400和4800小时老化后的20°*光泽 | |||
0小时 | 4000小时 | 4400小时 | 4800小时 | |
无 | 87 | ** | ||
TINUVIN 384 | 86 | *** | ||
(G)+TINUVIN384 | 87 | 75 | 25 | *** |
(H)+TINUVIN384 | 86 | 48 | 24 | *** |
(I)+TINUVIN384 | 87 | 88 | 64 | 33 |
*:高值表示良好的稳定性
**:在1200小时后破裂
***:在2000小时后破裂
****:在4400小时后破裂使用的光稳定剂:
表2a、2b、2c和2d中给出的结果证明用本发明稳定剂混合物稳定的样品与未稳定的样品或用稳定剂混合物的单一组分稳定的样品相比,具有更好的耐老化稳定性(光泽保持性好)。实施例18:聚丙烯板的稳定
将1 g表3中给出的各化合物、1 g亚磷酸三(2,4-二叔丁基苯基)酯、0.5 g四[3-(3,5-二叔丁基-4-羟基苯基)丙酸]季戊四醇酯、1g硬脂酸钙和1 gFilofin Blue G(购自Ciba-Geigy)在涡轮混合机与1000 g熔体指数=4 g/10分钟(在230℃和2.16 kg下测定)的聚丙烯粉末混合。将得到的混合物在200-230℃下挤出制得聚合物粒料,然后将此粒料在200-220℃下注塑成为2mm厚的板。将所得的板暴露于黑板温度为63℃的65型WrWeather-O-Meter(ASTM D2565-85)中至开始表面发脆(粉化)为止。为了对比,将在上述相同条件但不加本发明的化合物下制备的聚丙烯板进行暴露。在表3中给出了达到开始发脆所需的暴露时间(小时)。时间越长,稳定效果越好。表3:
使用的光稳定剂:光稳定剂(J):R=-CH3;n=3光稳定剂(K):R=-CH3;n=4光稳定剂(L):混合物105(R=-CH3;比例n=3(79%)/4(20%))
光稳定剂 | 粉化时间(小时) |
无 | 570 |
(J) | 4460 |
(K) | 4050 |
(L) | 5020 |
表3中给出的结果证明,用本发明稳定剂混合物稳定的样品与未稳定的样品或用稳定剂混合物的单一组分稳定的样品相比,具有更好的耐粉化稳定性。
Claims (18)
1.一种含有通式(Ⅰ)的两种不同化合物的稳定剂混合物其中n为2至22的整数,R为氢、C1-C8烷基、-O-、-OH、-NO、-CH2CN、C1-C18烷氧基、C5-C12环烷氧基、C3-C6链烯基、C3-C6链炔基、C1-C8酰基或未取代或在苯基上被1、2或3个C1-C4烷基取代的C7-C9苯基烷基;两种化合物的重量比为1∶20至20∶1。
2.根据权利要求1的稳定剂混合物,其中n为2至10的整数。
3.根据权利要求1的稳定剂混合物,其中通式(Ⅰ)的两种化合物仅变量n不同。
4.根据权利要求1的稳定剂混合物,其中通式(Ⅰ)的两种化合物仅变量n不同且两个n值的差值为1、2、3、4或5。
5.根据权利要求1的稳定剂混合物,其中通式(Ⅰ)的一种化合物的n值为3且通式(Ⅰ)的另一种化合物的n值为4。
6.根据权利要求1的稳定剂混合物,其中通式(Ⅰ)的一种化合物的n值为4且通式(Ⅰ)的另一种化合物的n值为7。
7.根据权利要求1的稳定剂混合物,其中通式(Ⅰ)的一种化合物的n值为7且通式(Ⅰ)的另一种化合物的n值为8。
8.根据权利要求1的稳定剂混合物,还含有通式(Ⅰ)的第三种化合物。
9.根据权利要求1的稳定剂混合物,其中通式(Ⅰ)的一种化合物的n值为2,通式(Ⅰ)的另一种化合物的n值为3;所述混合物还含有通式(Ⅰ)的n为4的第三种化合物。
10.根据权利要求1的稳定剂混合物,其中通式(Ⅰ)的两种化合物仅基团R不同。
11.根据权利要求1的稳定剂混合物,其中R为氢、C1-C4烷基、-OH、C1-C8烷氧基、C5-C8环烷氧基、烯丙基、苄基、乙酰基或丙烯酰基。
12.根据权利要求1的稳定剂混合物,其中R为氢或甲基。
13.根据权利要求1的稳定剂混合物,还含有基于羟基苯基苯并三唑和/或羟基二苯(甲)酮和/或N-草酰苯胺和/或羟基苯基-s-三嗪的UV吸收剂作为辅助组分。
14.一种组合物,含有容易氧化、热或光诱导降解的有机材料和根据权利要求1的稳定剂混合物。
15.根据权利要求14的组合物,其中有机材料为合成聚合物。
16.根据权利要求14的组合物,其中有机材料为热塑性聚合物或用于涂料的基料。
17.根据权利要求14的组合物,其中有机材料为聚烯烃。
18.一种稳定有机材料抗氧化、热或光诱导降解的方法,包括将权利要求1的稳定剂混合物加入所述有机材料中。
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US6181042B1 (en) | 1998-05-30 | 2001-01-30 | General Electric Co. | Method for preventing corona surface damage in end windings of air-cooled motors and generators |
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TW546311B (en) * | 1999-11-25 | 2003-08-11 | Ciba Sc Holding Ag | Composition and method for color improvement of nitroxyl containing polymers |
GB2361005B (en) * | 2000-04-04 | 2002-08-14 | Ciba Sc Holding Ag | Synergistic mixtures of uv-absorbers in polyolefins |
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DE10161864A1 (de) * | 2001-12-14 | 2003-07-03 | Basf Ag | Stabilisatorzusammensetzung III |
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US20070191516A1 (en) * | 2004-03-15 | 2007-08-16 | Markus Frey | Process for the synthesis of amine ethers |
CN101712772B (zh) * | 2009-10-10 | 2012-02-15 | 南通惠康国际企业有限公司 | 一种光稳定剂及其生产方法 |
EP2514800B2 (de) * | 2011-04-21 | 2018-03-07 | Merck Patent GmbH | Verbindungen und flüssigkristallines Medium |
US20140323734A1 (en) * | 2011-12-19 | 2014-10-30 | Rohm And Haas Company | Method for the Preparation of N-Oxyl Hindered Amine Inhibitors |
DE102013017173A1 (de) * | 2012-10-18 | 2014-04-24 | Merck Patent Gmbh | Flüssigkristallines Medium, Methode zu seiner Stabilisierung und Flüssigkristallanzeige |
DE102013017174A1 (de) * | 2012-10-18 | 2014-04-24 | Merck Patent Gmbh | Flüssigkristallines Medium, Methode zu seiner Stabilisierung und Flüssigkristallanzeige |
CN107721910A (zh) * | 2017-08-28 | 2018-02-23 | 新秀化学(烟台)有限公司 | 一种双(1‑烷氧基‑2,2,6,6‑四甲基‑4‑哌啶基)烷基二酸酯的生产工艺 |
CN110387064A (zh) * | 2019-07-12 | 2019-10-29 | 西安工业大学 | 一种混合型低碱性受阻胺光稳定剂及其制备方法 |
CN111944199B (zh) * | 2020-08-21 | 2021-12-31 | 宿迁市振兴化工有限公司 | 一种光稳定剂及制备方法 |
CN113861102B (zh) * | 2021-10-12 | 2024-03-08 | 安阳加成新材料科技有限公司 | 一种受阻胺光稳定剂的制备及应用 |
CN115505957B (zh) * | 2022-09-27 | 2024-06-21 | 四川轻化工大学 | 一种电催化合成过氧化氢的镍氮掺杂碳材料及其制备方法 |
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US3640928A (en) * | 1968-06-12 | 1972-02-08 | Sankyo Co | Stabilization of synthetic polymers |
NL154241C (zh) * | 1971-01-29 | 1900-01-01 | ||
JPS5848580B2 (ja) * | 1975-05-28 | 1983-10-29 | 三共株式会社 | ゴウセイコウブンシザイリヨウヨウアンテイザイ |
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US5439959A (en) * | 1994-05-24 | 1995-08-08 | 3V Inc. | Compositions for the stabilization of synthetic polymers |
-
1997
- 1997-04-15 TW TW086104824A patent/TW358110B/zh active
- 1997-05-21 SE SE9701891A patent/SE9701891L/ not_active Application Discontinuation
- 1997-05-21 AU AU23557/97A patent/AU724746B2/en not_active Ceased
- 1997-05-21 KR KR1019970019755A patent/KR970074845A/ko active IP Right Grant
- 1997-05-22 US US08/862,033 patent/US5817821A/en not_active Expired - Lifetime
- 1997-05-22 GB GB9710431A patent/GB2313598B/en not_active Expired - Fee Related
- 1997-05-23 BE BE9700455A patent/BE1012526A5/fr not_active IP Right Cessation
- 1997-05-26 DE DE19721966A patent/DE19721966A1/de not_active Withdrawn
- 1997-05-26 CA CA002206181A patent/CA2206181A1/en not_active Abandoned
- 1997-05-26 IT IT97MI001224A patent/IT1291995B1/it active IP Right Grant
- 1997-05-27 ES ES009701140A patent/ES2142228B1/es not_active Expired - Lifetime
- 1997-05-27 FR FR9706450A patent/FR2749319A1/fr not_active Withdrawn
- 1997-05-27 AT AT0090397A patent/AT407640B/de not_active IP Right Cessation
- 1997-05-27 CN CN97113189A patent/CN1061076C/zh not_active Expired - Fee Related
- 1997-05-27 NL NL1006140A patent/NL1006140C2/nl not_active IP Right Cessation
- 1997-05-27 ZA ZA9704605A patent/ZA974605B/xx unknown
- 1997-05-28 BR BR9703323A patent/BR9703323A/pt not_active Application Discontinuation
- 1997-05-28 JP JP9176282A patent/JPH1081877A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
ES2142228B1 (es) | 2000-12-16 |
FR2749319A1 (fr) | 1997-12-05 |
GB9710431D0 (en) | 1997-07-16 |
NL1006140A1 (nl) | 1997-12-03 |
ATA90397A (de) | 2000-09-15 |
BE1012526A5 (fr) | 2000-12-05 |
BR9703323A (pt) | 1998-09-15 |
AU2355797A (en) | 1997-12-04 |
IT1291995B1 (it) | 1999-01-25 |
TW358110B (en) | 1999-05-11 |
JPH1081877A (ja) | 1998-03-31 |
ITMI971224A1 (it) | 1998-11-26 |
CA2206181A1 (en) | 1997-11-28 |
SE9701891L (sv) | 1997-11-29 |
ZA974605B (en) | 1997-11-28 |
KR970074845A (ko) | 1997-12-10 |
CN1167805A (zh) | 1997-12-17 |
NL1006140C2 (nl) | 2000-07-07 |
US5817821A (en) | 1998-10-06 |
GB2313598A (en) | 1997-12-03 |
ITMI971224A0 (zh) | 1997-05-26 |
DE19721966A1 (de) | 1997-12-04 |
SE9701891D0 (sv) | 1997-05-21 |
AT407640B (de) | 2001-05-25 |
GB2313598B (en) | 2000-08-16 |
ES2142228A1 (es) | 2000-04-01 |
AU724746B2 (en) | 2000-09-28 |
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