CN1054143C - 2,4-二甲基-6-仲烷基苯酚 - Google Patents
2,4-二甲基-6-仲烷基苯酚 Download PDFInfo
- Publication number
- CN1054143C CN1054143C CN90106526A CN90106526A CN1054143C CN 1054143 C CN1054143 C CN 1054143C CN 90106526 A CN90106526 A CN 90106526A CN 90106526 A CN90106526 A CN 90106526A CN 1054143 C CN1054143 C CN 1054143C
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- Prior art keywords
- compound
- mixture
- butyl
- acid
- methyl
- Prior art date
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- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 claims abstract description 38
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
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- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/06—Alkylated phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms using aldehydes or ketones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract
一种组合物,含a)聚苯乙烯、取代的聚苯乙烯、苯乙烯或取代的苯乙烯的共聚物或三元共聚物,聚碳酸酯、聚酯-碳酸酯、聚氨基甲酸乙酯、聚酰胺、共聚酰胺、聚缩醛或聚苯氧;b)至少一种结构Ⅰ的化合物:
式中R1是甲基或乙基,R2是C2-C30烷基。式中R2是C8-C30烷基的结构式Ⅰ的化合物是新的,并且适于对有机材料的热、氧化和光降解起稳定作用。
Description
本发明涉及一种组合物,它含有挑选出来的有机聚合物(例如:丙烯腈/丁二烯/苯乙烯三元共聚物)及2,4-二甲基-6-仲烷基苯酚;本发明还涉及新的2,4-二甲基-6-仲烷基苯酚,以及对热、氧化及光降解起稳定作用的有机材料。
许多三烷基苯酚,例如2,6-二叔丁基-4-甲基苯酚(Swanox BHT)及用它们来稳定有机材料都是已知的,例如:在“Atmospheric Oxidation and Antioxidants;Elsevier Publishing Company(1965),第120-125页”中,G.Scott描述了对于矿物油苯酚中的取代与稳定作用之间的联系,在US-A3,511,802中描述了借助烷基取代的苯酚使丙烯树脂稳定,在化学文献(CA)69:10,147S及72:11,860t中则描述了仲烷基苯酚的制备及光谱。
本发明涉及的是一类组合物,包含a)聚苯乙烯或取代的聚苯乙烯、苯乙烯的共聚物或三元共聚物、取代的苯乙烯共聚物或三元共聚物、聚碳酸酯、聚酯碳酸酯、聚氨基甲酸乙酯、聚酰胺、共聚酰胺、聚缩醛或聚苯氧,b)至少一种结构式I的化合物式中R1是甲基或乙基,R2是C2-C30的烷基。例如R2是乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十八烷基、十九烷基、二十烷基、二十一烷基、二十二烷基、二十三烷基、二十四烷基、二十五烷基、二十六烷基、二十七烷基、二十八烷基、二十九烷基或三十烷基。
R2优选C8-C30烷基,如C8-C13或C10-C50烷基,特别优选R2为C12-C18烷基。
当结构式I的化合物为如下时,所构成的组合物是有益的:
含Ia和Ib两种化合物的混合物的那些组合物也是有益的:式中R′2是-CmH2m+1,R2″是-Cm-1H2m-1,m是2-30的整数,并在基团R2′和R2″中是相同的。化合物(Ia)/(Ib)的重量比为:如1/99至99/1,优选99/1至70/30,特别优选95/5至80/20。
优选的本发明的组合物还是那些组合物,其组份a)是聚苯乙烯或取代的聚苯乙烯或苯乙烯的共聚物或三元共聚物或取代的苯乙烯的共聚物或三元共聚物。下面举例说明:
1)聚苯乙烯、聚-对甲基苯乙烯或聚-α-甲基苯乙烯。
2)苯乙烯或α-甲基苯乙烯与二烯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/马来酸酐或苯乙烯/丙烯腈/丙烯酸甲酯);苯乙烯共聚物和另一聚合物(如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三元共聚物)组成的高抗冲强度混合物;还有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)。
3)苯乙烯或α-甲基苯乙烯的接枝共聚物,例如在聚丁二烯上接苯乙烯;在聚丁二烯/苯乙烯共聚物或聚丁二烯/丙烯腈共聚物上接苯乙烯;在聚丁二烯上接苯乙烯和丙烯腈(或甲基丙烯腈);在聚丁二烯上接苯乙烯、丙烯腈和甲基丙烯酸甲酯;在聚丁二烯上接苯乙烯和马来酸酐;在聚丁二烯上接苯乙烯、丙烯腈和马来酸酐或马来酰亚胺;在聚丁二烯上接苯乙烯和马来酰亚胺;在聚丁二烯上接苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯;在乙烯/丙烯/二烯三元共聚物上接苯乙烯和丙烯腈;在聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上接苯乙烯和丙烯腈、苯乙烯和丙烯腈接枝在丙烯酸酯/丁二烯共聚物上以及其与在2)中所述的共聚物的混合物,这些都是已知的,例如:称之为ABS、MBS、ASA或AES的聚合物。
特别优选的组份a)是抗冲击的聚苯乙烯(IPS)、苯乙烯/丙烯腈共聚物(SAN)和丙烯腈/丁二烯/苯乙烯三元共聚物(ABS);特别是丙烯腈/丁二烯/苯乙烯三元共聚物和甲基丙烯酸甲酯/丁二烯/苯乙烯接枝共聚物(MBS)。
有益的组份a)还可以是聚碳酸酯、聚酯碳酸酯、聚氨基甲酸乙酯、聚酰胺、共聚酰胺、聚缩醛和聚苯氧。下面举例说明:
(I)一部分是由具有端羟基的聚醚、聚酯和聚丁二烯衍生物出来的、而另一部分是由脂肪族或芳香族聚异氰酸酯和其前体衍生出来的聚氨基甲酸乙酯。
(II)由二胺和二羧酸衍生出来的和/或由氨基羧酸或相应的内酰胺衍生出来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或4/6、聚酰胺11、聚酰胺12、起源于间二甲苯、二胺和己二酸的芳香聚酰胺;由己二胺和间苯二酸和/或对苯二酸制得的聚酰胺,以及(如果合适)用作改性剂的弹性体,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。上述聚酰胺和聚烯烃、烯烃共聚物、离子键聚合物或化学键连接的或接枝的弹性体的嵌段共聚物;或与聚醚如聚乙二醇、聚丙二醇或聚亚丁基二醇的嵌段共聚物。还包括用EPDM和ABS改进的聚酰胺或共聚酰胺;以及在生产(“RIM聚酰胺体系”)过程中已缩合的聚酰胺。
(III)聚缩醛类,例如聚甲醛和含共聚单体如环氧乙烷的聚甲醛,用热塑性聚氨基甲酸乙酯、丙烯酸酯或MBS改性的聚缩醛。
R1是甲基或乙基、R2是C8-C30的烷基的结构式I的化合物是新颖的,并构成本发明更进一步的主题。
R2的优选含义可由前面的叙述得出。
本发明还与含有机材料及至少一种结构式I的化合物的组合物有关,其中这种有机材料是对氧、热或光的降解敏感的,并且式I中R1是甲基或乙基,R2是C8-C30的烷基。
有机材料的例子是上述1)-3)和I)-III)中指出的那些;另外还有:
1.单烯烃以及二烯烃的聚合物,如聚丙烯、聚异丁烯、聚丁烯-1、聚甲基戊烯-1、聚异戊二烯或聚丁二烯;还有环烯,例如环戊烯或降冰片烯的聚合物;还有聚乙烯(如果合适可是交联的)例如高密度聚乙烯(HDPE)、低密度聚乙烯(LDPE)以及线性低密度聚乙烯(LLDPE);
2.在上述1)中提及的聚合物的混合物,例如聚丙烯和聚异丁烯的混合物,聚丙烯和聚乙烯(例如PP/HDPE或PP/LDPE)的混合物以及不同类型聚乙烯(例如LDPE/HDPE)的混合物;
3.单烯烃以及二烯烃相互或与其它乙烯基单体的共聚物,如乙烯/丙烯共聚物,线性低密度聚乙烯(LLDPE)以及其与低密度聚乙烯(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/辛基共聚物、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/甲基丙烯酸烷基酯的共聚物,乙烯/醋酸乙烯共聚物或乙烯/丙烯酸的共聚物以及它们的盐(离子聚合物);还有乙烯和丙烯以及二烯的三元共聚物,二烯如己二烯、二环戊二烯或亚乙基降水片烯,以及还有这些共聚物与另一共聚物或在1)中所述的聚合物的混合物,例如聚丙烯-乙烯/丙烯共聚物,LDPE-乙烯/醋酸乙烯共聚物,LDPE-乙烯/丙烯酸共聚物,LLDPE-乙烯/醋酸乙烯共聚物和LLDPE-乙烯/丙烯酸共聚物;
3a.包括其氢化改性(如粘合剂树脂)的烃树脂(例如C5-C9);
4.含卤素的聚合物,例如氯丁橡胶,氯化的橡胶,氯化或氯磺化聚乙烯,表氯醇均聚物和共聚物,特别是由含卤的乙烯基化合物形成的聚合物,例如聚氯乙烯、聚偏二氯乙烯、聚氟乙烯或聚偏氟乙烯;以及它们的共聚物,如氯乙烯/偏二氯乙烯、氯乙烯/醋酸乙烯或偏二氯乙烯/醋酸乙烯;
5.由α,β-不饱和酸以及其衍生物衍生出来的聚合物,如聚丙烯酸酯和聚甲基丙烯酸酯,聚丙烯酰胺和聚丙烯腈;
6.在5)中提及的单体相互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共聚物,丙烯腈/卤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;
7.由不饱和醇、胺和酰基衍生物或它们的缩醛衍生出来的聚合物,例如,聚乙烯醇、聚醋酸乙烯酯、聚硬脂酸乙烯酯,聚苯甲酸乙烯酯或聚马来酸乙烯酯,聚乙烯醇缩丁醛,聚邻苯二甲酸烯丙酯或聚烯丙基嘧胺;以及它们与1中提及的烯烃的共聚物。
8.环醚的均聚物和共聚物,如聚亚烷基二醇、聚环氧乙烷。聚环氧丙烷或它们与二缩水甘油醚的共聚物;
9.聚苯硫以及它们与苯乙烯聚合物或聚酰胺的混合物;
10.聚脲,聚酰亚胺,聚酰胺-酰亚胺和聚苯并咪唑;
11.由二羧酸和二醇衍生出来的,和/或由羟基羧酸或相应的内酰胺衍生出来的聚酯,如聚对苯二甲酸乙酯、聚对苯二甲酸丁酯、聚对苯二甲酸-1,4-二甲基环己酯和聚羟基苯甲酸酯,以及由含末端羟基的聚醚衍生出来的嵌段聚醚-酯;还有用聚碳酸酯或MBS改性的聚酯;
12.聚砜、聚醚砜和聚醚酮,
13.一部分由醛、另一部分由苯酚、脲或密胺衍生出来的交联聚合物,如酚醛树脂、脲醛树脂和密胺甲醛树脂;
14.干燥的和没干燥的醇酸树脂;
15.不饱和的聚酯树脂,它是由饱和的和不饱和的二羧酸与多元醇和作为交联剂的乙烯基化合物,以及还有它们的含卤的低可燃性改性体的共聚多酯衍生出来的;
16.由取代的丙烯酸酯衍生出来的可交联的丙烯酸树脂,例如,由环氧丙烯酸酯、氨基甲酸乙酯-丙烯酸酯或聚酯-丙烯酸酯衍生出来的可交联的丙烯酸树脂;
17.与密胺树脂、脲树脂、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。
18.由聚环氧化物,例如由二缩水甘油醚或由环脂族二环氧化物衍生出来的交联的环氧树脂;
19.天然聚合物,如纤维素、天然橡胶、明胶以及它们的同系聚合物化学改性的衍生物,如醋酸纤维素,丙酸纤维素和丁酸纤维素以及纤维素醚、如甲基纤维素;还有松脂及其衍生物;
20.上述聚合物的混合物(复合高聚物),例如:PP/EPDM、聚酰胺/EPDM或ABS,PVC/EVA,PVC/ABS,PVC/MBS,PC/ABS,PBTP/ABSPC/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以及共聚物,PA/HDPE、PA/PP和PA/PPO;
21.天然及合成有机材料,它们是纯的单体化合物或它们的混合物,例如矿物油、动物脂或植物油脂、动植物油和动植物蜡、或基于合成酯(例如对苯二甲酸酯、己二酸酯,磷酸酯或偏苯三酸酯)的油、蜡和脂肪,以及合成酯与矿物油以任何希望的重量比的混合物,这样被使用的有如纺丝油剂和它们的水乳液;
22.天然或合成橡胶的水乳液,例如羧基化苯乙烯/丁二烯共聚物的天然橡胶胶乳液或胶乳混合物。
根据本发明的组合物,相对于要被稳定的有机材料的总重量,它们含0.01%至10%、较好0.05%至5%,特别是0.1%至2%的至少一种结构式I的化合物。
除结构式I的化合物外,根据本发明的组合物另外还可含常用的添加剂,例如:
1.抗氧剂
1.1、烷基化的单苯酚例如:
2,6-二叔丁基-4-甲基苯酚,
2-叔丁基-4,6-二甲基苯酚,
2,6-二叔丁基-4-乙基苯酚,
2,6-二叔丁基-4-正丁基苯酚,
2,6-二叔丁基-4-异丁基苯酚,
2,6-二环戊基-4-甲基苯酚,
2-(α-甲基环己基)-4,6-二甲基苯酚,
2,6-二十八烷基-4-甲基苯酚,
2,4,6-三环己基苯酚,
2,6-二叔丁基-4-甲氧基甲基苯酚,
2,6-二壬基-4-甲基苯酚,
1.2、烷基化氢醌,例如
2,6-二叔丁基-4-甲氧基甲基苯酚,
2,5-二叔丁基氢醌,
2,5-二叔戊基氢醌
2,6-二苯基-4-十八烷氧基苯酚
1.3、羟基化的硫代二苯醚,例如:
2,2′-硫-双(6-叔丁基-4-甲基苯酚),
2,2′-硫-双(4-辛基苯酚),
4,4′-硫-双(6-叔丁基-3-甲基苯酚), 4,4′-硫-双(6-叔丁基-2-甲基苯酚)1.4、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-甲苄基)-4-壬基苯酚〕2,2′-亚甲基-双〔6-(α,α-二甲苄基)-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-甲苯基)-丁烷2,6-双(3-叔丁基-5-甲基-2-羟苄基)-4-甲基苯酚1,1,3-三(5-叔丁基-4-羟基-2-甲苯基)-丁烷1,1-双(5-叔丁基-4-羟基-2-甲苯基)-3-正十二烷基巯基丁烷 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-甲苯基)-二环戊二烯双〔2-(3′-叔丁基-2′-羟基-5′-甲苄基)-6-叔丁基-4-甲苯基〕对苯二甲酸酯。1.5苄基化合物,例如1,3,5-三(3,5-二叔丁基-4-羟苄基)-2,4,6-三甲苯双(3,5-二叔丁基-4-羟苄基)硫化物,异辛基-3,5-二叔丁基-4-羟苄基巯基乙酸酯双(4-叔丁基-3-羟基-2,6-二甲苄基)-二硫羟对苯二甲酸酯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-2,6-二甲苄基)异氰脲酸酯二-十八烷基-3,5-二叔丁基-4-羟苄基膦酸酯单乙基-3,5-二叔丁基-4-羟苄基膦酸酯和1,3,5-双(3,5-二环己基-4-羟苄基)异氰脲酸酯的钙盐。1.6.酰氨基苯酚,例如:4-羟基月桂N-酰苯胺,4-羟基硬脂N-酰苯胺,2,4-双(辛基巯基)-6-(3,5-二叔丁基-4-羟基苯胺基)-S-三嗪,辛基-N-(3,5-二叔丁基-4-羟苯基)-氨基甲酸酯。
1.7、β-(3,5-二叔丁基-4-羟苯基)-丙酸与一元或多元醇的酯,例如与甲醇、十八烷醇、1,6-己二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟乙基)异氰尿酸酯和N,N′-双(羟基)草氨酸乙酯。
1.8β-(5-叔丁基-4-羟基-3-甲苯基)-丙酸与一元或多元醇的酯,例如与甲醇、十八烷醇、1,6-己二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟基)乙基异氰尿酸酯和N,N′-双(羟乙基)草酰胺。
1.9、β-(3,5-二环己基-4-羟苯基)-丙酸与一元或多元醇的酯,例如与甲醇、十八烷醇、1,6-己二醇、新戊二醇、硫代二乙二醇、二乙二醇、三乙二醇、季戊四醇、三(羟基)乙基异氰尿酸酯和N,N′-双(羟乙基)草酰胺。
1.10、β-(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)-己二胺
N,N′-双(3,5-二叔丁基-4-羟苯基丙酰)-丙二胺
N,N′-双(3,5-二叔丁基-4-羟苯基丙酰)-肼。
2.紫外线吸收剂和光稳定剂
2.1、2-(2′-羟苯基)-苯并三唑类,例如:5′-甲基-,3′,5′-二叔丁基-,5′-叔丁基-,5′(1,1,3,3,-四甲基丁基)-,5-氯-3′,5′-二叔丁基-,5-氯-3′-叔丁基-5′-甲基-、3′-仲丁基-5′-叔丁基-,4′-辛氧基-,3′,5′-二叔戊基或3′,5′-双(α,α-二甲苄基)-的衍生物。
2.2、2-羟基二苯酮类,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-或2′-羟基-4,4′-二甲氧基-的衍生物。
2.3、取代的或非取代的苯甲酸的酯,例如水扬酸4-叔丁基苯基酯,水扬酸苯基酯,水扬酸辛基苯基酯,二苯甲酰间苯二酚,双(4-叔丁基苯甲酰)-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-羟基苯甲酸酯和3,5-二叔丁基-4-羟基苯甲酸十六烷基酯。
2.4、丙烯酸酯类,例如α-氰基-β,β-二苯基丙烯酸乙酯或异辛酯,α-甲酯基肉桂酸甲酯、α-氰基-β-甲基-对-甲氧基肉桂酸甲酯或丁酯、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)-苯酸的镍配合物,如1∶1的配合物或1∶2的配合物,如果合适的话,还可含另外的配位体,如正丁胺、三乙醇胺或N-环己基二乙醇胺,二丁基二硫氨基甲酸镍,4-羟基-3,5-二叔丁基苄基膦酸单烷基酯(如甲酯或乙酯)的镍盐,酮肟如2-羟基-4-甲苯基十一烷基酮肟的镍配合物,以及1-苯基-4-月桂酰-5-羟基吡唑的镍配合物,如果合适还可有另外的配位体。
2.6、空间位阻的胺,例如双(2,2,6,6-四甲基哌啶基)癸二酸胺双(1,2,2,6,6-五甲基哌啶基)癸二酸酯,双(1,2,2,6,6-五甲基哌啶基)-正丁基-3,5-二叔丁基-4-羟苄基丙二酸酯,由1-羟乙基-2,2,6,6-四甲基-4-羟基哌啶和丁二酸形成的缩合产物,由N,N′-双(2,2,6,6-四甲基-4-哌啶基)-己二胺和4-叔辛氨基-2,6-二氯-1,3,5-S-三嗪形成的缩合产物,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-丁烷四酸酯(bulanetetraoate)和1,1′-(1,2-乙二酰基)-双(3,3,5,5-四甲基哌嗪酮)。
2.7、草酰胺类,例如4,4′-二辛氧基-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′-草酰二苯胺和它们与2-乙氧基-2′-乙基-5,4′-二叔丁基-N,N′-草酰二苯胺的混合物或者邻甲氧基的和对甲氧基的双取代的N,N′-草酰二苯胺的混合物,以及邻乙氧基的和对乙氧基的双取代的N,N′-草酰二苯胺的混合物。
2.8.2-(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(2,4-二甲苯基)-1,3,5-三嗪,2-(2,4-二羟苯基)-4,6-双(2,4-二甲苯基)-1,3,5-三嗪,2,4-双(2-羟基-4-丙氧基苯基)-6-(2,4-二甲苯基)-1,3,5-三嗪,2-(2-羟基-4-辛氧基苯基)-4,6-双(4-甲苯基)-1,3,5-三嗪和2-(2-羟基-4-十二烷氧基苯基)-4,6-双(2,4-二甲苯基)-1,35-三嗪。
3.金属纯化剂,例如,N,N′-二苯基草酰胺,N-水扬醛-N′-水扬酰肼,N,N′-双(水扬酰)-肼,N,N′-双(3,5-二叔丁基-4-羟苯基丙酰)-肼,3-水扬酰氨基-1,2,4-三唑和双(亚苄基)-乙二酸酰肼,
4.亚磷酸酯和亚膦酸酯,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)酯、二硬脂基季戊四醇二亚磷酸酯,亚磷酸三(2,4-二叔丁基苯基)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、三硬脂基山梨糖醇三亚磷酸酯,四(2,4-二叔丁基苯基)-4,4′-二亚苯基二亚膦酸酯和3,9-双(2,4-二叔丁基苯氧基)-2,4,8,10-四-噁-3,9-二磷膦螺〔5,5〕十一烷。
5.驱除过氧化物的化合物,例如,β-硫代二丙酸的酯,如月桂酯、硬脂酯、十四烷基酯或十三烷基酯,巯基苯并咪唑、α-巯基苯并咪唑的锌盐,二丁基二硫氨基甲酸锌、二(十八烷基)二硫和季戊四醇四(β-十二烷基巯基)丙酸酯。
6.聚酰胺稳定剂,例如,与碘化合物和/或磷化合物结合的铜盐和二价锰盐。
7.碱性共稳定剂,例如密胺、聚乙烯吡咯烷酮、双氰胺、氰尿酸三烯丙酯、尿素衍生物,肼衍生物,胺、聚酰胺、聚氨基甲酸乙酯,高级脂肪酸的碱性和碱土金属盐,例如,硬脂酸钙、硬脂酸锌、硬脂酸镁、蓖麻醇酸钠和棕榈酸钾、邻苯二酸锑或邻苯二酸锡。
8.核化剂,例如4-叔丁基苯甲酸、己二酸或二苯基乙酸。
9.填料和增强剂,例如:CaCO3、硅酸盐、玻璃纤维、石棉、滑石、高岭土、云母、BaSO4、金属氧化物和氢氧化物、碳黑和石墨。
10.其它的添加剂,例如增塑剂、润滑剂、乳化剂、颜料、荧光增自剂、防火剂、抗静电剂和发泡剂。
将结构式I的化合物和(如果合适的话)其它添加剂掺入有机材料是借助已知的方法进行的,例如可在成型前或成型期间,或者借助将溶解的或分解的化合物添加至有机材料,如果合适的话,随后进行溶剂蒸发。结构式I的化合物也能以浓缩母粒的形式加至要被稳定的有机材料;浓缩母粒含例如2.5至25%重量的这些化合物。
结构式I的化合物还能在聚合前或在聚合期间或在交联前添加。
结构式I的化合物能以纯的或用蜡、油或聚合物包封的形式掺入要被稳定的有机材料。
以这种方式稳定的材料能以多种形式使用,例如,以薄膜、纤维、带材,模塑料或型材或用于漆、粘合剂或水泥的粘结剂。
结构式I的化合物也适用作1,3-二烯阴离子溶液聚合物的链终止剂。
结构式I的化合物可用类似于已知方法的方法进行制备,例如,借助于α-烯烃的2,4-二甲苯酚的催化烃化。R是烷基。其中R是例如C13-C17烷基,C17-C21烷基或C21-C27烷基时,还可使用α-烯烃混合物作为结构式(III)的化合物。
在催化剂存在下,于80~250℃最好是130~200℃适当地进行反应。下述为合适的催化剂:
a)无机或有机酸,例如,硫酸或对甲苯磺酸;
b)沸石,例如ZSM沸石;
c)酸土,例如Fulmont 234,Fulcat 14或Fulmont 700;
d)Friedel-Crafts催化剂,例如在下述文献中描述的,Kozlikovski Ya.B.et al.,Zh.Org Khim23,1918-24(1987);Laan J.A.M;Chem.Ind.1,34-35(1987)和Kurashev M.V.etal.;Izv.Akad,NauK.SSSR,Ser.Khim 8,1843-1846(1986);
e)活化的γ-氧化铝,例如,在DE-B1,142,873和US-A3,367,981中描述的。
作为催化剂,活化的γ-氧化铝是特别优选的。
如果在结构式I的化合物的制备过程中,生产出了化合物(Ia)和(Ib)的混合物,该混合物可用例如色谱方法,特别是气相色谱和高压液相色谱(HPLC)分离。
由于在制备过程中,能生产出混合物形式的结构式I的化合物,因此,本发明也与化合物(Ia)和(Ib)的混合物有关,式中R2′是-CmH2m+1,R2″是-Cm-1H2m-1,m是8至30的整数,并且在基团R2′和R2″中是相同的。
也优选下述化合物的混合物:
结构式I的化合物可在催化剂存在下,借助将2,4-二甲苯酚和α-C10-C30烯烃的反应得到。
下面的例子进一步说明本发明,在这些例子中,份数和百分比均以重量计,除非有任何相反的说明。
实施例1
2,4-二甲基-6-仲十八烷基苯酚的制备
将756g α-十八烯(纯度:85%)、366.5g 2,4-二甲苯酚和30g作为催化剂的活化的γ-氧化铝(如DE-B-1,142,873实施例1中所述的)装入高压釜(2000ml),将反应混合物加热至310℃,并在该温度下搅拌15小时,冷却后滤出催化剂,在200-225℃、1KPa下蒸馏该粗产物。得到的产物是无色的蜡,并且是比率为74/11的2,4-二甲基-6-(1-甲基十七烷基)苯酚和2,4-二甲基-6-(2-乙基十六烷基)苯酚的混合物。
如果希望的话,可借助色谱法(例如气相色谱或高压液相色谱)分离异构体的混合物。
得率:770g(等于67%的理论值)
熔点:~30℃元素分析:
计算值:C=83.35%;H=12.38%。
测量值:C=83.49%;H=12.32%。实施例2a
2,4-二甲基-6-仲十六烷基苯酚的制备
用与实施例1类似的方法进行制备。使用672gα-十六烯(纯度:92%)和366.5g 2,4-二甲苯酚作为反应物。最终产物是无色液体,并且是比率为81/7的2,4-二甲基-6-(1-甲基十五烷基)苯酚和2,4-二甲基-6-(2-乙基十四烷基)苯酚的混合物。
如果希望的话,可借助色谱法分离异构体的混合物。
得率:749g(等于72%的理论值)
沸点:1KPa时为170~200℃
实施例2b
2,4-二甲基-6-仲十六烷基苯酚的制备
先将220g(1mol)的线性α-十六烯(纯度:92%)、122g(1mol)2,4-二甲苯酚和10g作为催化剂的活化的ZSM-沸石置于0.75升的高压釜中。将反应混合物加热至220℃,并在该温度搅拌15小时。冷却后滤出催化剂,借助蒸馏除去未反应的原始材料(二甲苯酚:在10-1毫巴时沸点为40℃;α-十六烯:在8×10-2毫巴时沸点为60-70℃)。随后,在高真空度(10-2毫巴)下,于142-147℃蒸馏液体剩余物。产物是无色液体,并且是比率为56/11的2,4-二甲基-6-(1-甲基十五烷基)苯酚和2,4-二甲基-6-(2-乙基十四烷基)苯酚的混合物。
如果希望的话,可借助色谱法分离异构体的混合物。元素分析
计算值:C=83.17%;H=12.21%。
测量值:C=83.14%;H=12.08%。
实施例3a
2,4-二甲基-6-仲十二烷基苯酚的制备
用与实施例1相类似的方法进行制备,得到的产物是比率为53/25的2,4-二甲基-6-(1-甲基十一烷基)苯酚和2,4-二甲基-6-(1-乙基癸基)苯酚的混合物。如果希望的话,可借助色谱法分离异构体的混合物,沸点:4毫巴下为175℃。
实施例3b
2,4-二甲基-6-仲十二烷基苯酚的制备
用与实施例1相类似的方法进行制备,得到的产物是比率为73/15的2,4-二甲基-6-(1-甲基十一烷基)苯酚和2,4-二甲基-6-(1-乙基癸基)苯酚的混合物。如果希望的话,可借助色谱法分离异构体的混合物。沸点:在4毫巴下为180℃。
实施例4
2,4-二甲基-6-仲-(C20-C24烷基)苯酚的制备
用与实施例1相类似的方法进行制备,使用2,4-二甲苯酚和α烯烃混合物(H2C=CH-CH2-R,其中R=C17-C21烷基)作为反应物。得到的反应混合物含比率为45/35/3的2,4-二甲基-6-(1-甲基十九烷基)苯酚、2,4-二甲基-6-(1-甲基二十一烷基)苯酚和2,4-二甲基-6-(1-甲基二十三烷基)苯酚。产物呈粘性油状。如果希望的话,可借助色谱法分离混合物。元素分析:
计算值:C=83.88%;H=12.84%。
测量值:C=84.12%;H=13.22%。
实施例5
2,4-二甲基-6-仲(C24-C30烷基)苯酚混合物的制备
用与实施例1相类似的方法进行制备,使用2,4-二甲苯酚和α烯烃混合物(H2C=CH-CH2-R,其中R为C21-C27烷基)作为反应物,得到的反应混合物含比率为15/35/33/14的2,4-二甲基-6-(1-甲基二十三烷基)苯酚、2,4-二甲基-6-(1-甲基二十五烷基)苯酚、2,4-二甲基-6-(1-甲基二十七烷基)苯酚和2,4-二甲基-6-(1-甲基二十九烷基)苯酚,产物呈蜡状。如果希望的话,可借助色谱法分离混合物。沸点:50-60℃。
实施例6
对丙烯腈/丁二烯/苯乙烯三元共聚物(ABS)的稳定作用
将列于表1或表2的添加剂溶于40ml的己烷/异丙醇溶剂混合物中。剧烈搅拌的同时,将该溶液加至溶解在600g水中的100g ABS的分散液中,该溶液在很短的时间(约1分钟)内被ABS完全吸收。用真空过滤将ABS粉末滤出,并在40℃于真空下干燥40小时。将2%的TiO2(颜料)以及1%的亚乙基双硬脂酰胺(滑爽剂)加至于燥的粉末中。然后将该混合物在双辊混炼机上于180℃混合4分钟。
将辊压的片坯在170℃压成0.8毫米厚的片材,冲出45×17mm2的试样,在循环老化恒温箱中于180℃通过加热老化,测试加入的添加剂的效果。以45分钟测试时间后的颜色变化作为判断依据,颜色深度用如在ASTM D1925-70中说明的“黄色指数”进行测定。测试表明:通过添加本发明的化合物,有效地抑制了黄色。
表1
其中DLTDP为:硫代二丙酸二月桂酯
添加剂 | - | 0.5%的DLTDP | 0.25%的实施例2b的化合物及0.5%的LLTDP |
于180℃ 45分钟后的黄色指数 | 78 | 75 | 43 |
表2
DLTDP:硫代二丙酸二月桂酯
添加剂 | - | 0.5%的DLTDP | 0.25%实施例4的混合物及0.5%DLTDP | 0.25%实施例5的混合物及0.5%DLTDP |
于180℃45分钟后的黄色指数 | 58 | 66 | 34 | 36 |
实施例7
对甲基丙烯酸甲酯/丁二烯/苯乙烯接枝共聚物(MBS)的稳定作用添加乳液的制备:
将6.4份实施例2a的化合物、25.6份硫代二丙酸二月桂酯和3.4份硬脂酸加热熔化(约80℃)。剧烈搅拌该混合物,并添加0.4份固体NaOH和21.4份水的温溶液。随后,借助添加42.8份温水改变得到的乳液(在有机介质中的水滴)。接着,用温水稀释乳液至1/10,并在60℃轻轻地搅拌直至使用。共絮凝条件:
将适量的列于表3的添加剂乳液加至100ml冷却的MBS胶乳,将该混合物搅拌30分钟。随后将该混合物倾入200ml 70℃的HCl水溶液(0.1N)中,最终的温度约为60℃。接着,剧烈搅拌该混合物,并加入约20ml的NaOH水溶液(1N),以调节pH值至5.5~6。将悬浮液加热至95℃并在该温度下保持5分钟。最后过滤该悬浮液。固体MBS用水洗涤并在60℃真空下干燥48小时。MBS颗粒的直径约为3至10μm。将MBS粉末暴露于200℃的空气中进行热分析。出现的放热反应用于聚合物的降解测量。稳定作用的判断依据是放热反应开始时间(T0)或最大放热量的时间(Tm)。列于表3的结果表明了对聚合物的良好稳定作用。
表3
*)该值相当于在干燥MBS中为3%。
在MBS胶乳中添加剂乳液的浓度 | T0(分钟) | Tm(分钟) |
1%* | 9-11 | 14-16 |
Claims (9)
2.根据权利要求1的组合物,其中R2是C12至C18的烷基。
5.根据权利要求1的组合物,其中组份a)是抗冲击聚苯乙烯(IPS),苯乙烯/丙烯腈共聚物(SAN)或丙烯腈/丁二烯/苯乙烯三元共聚物(ABS)。
6.根据权利要求1的组合物,其中组份a)是丙烯腈/丁二烯/苯乙烯三元共聚物(ABS)或甲基丙烯酸甲酯/丁二烯/苯乙烯接枝共聚物(MBS)。
9.一种用于聚苯乙烯、取代的聚苯乙烯、苯乙烯共聚物或三元共聚物或取代的苯乙烯的共聚物或三元共聚物对热降解、氧化降解或光学降解起稳定作用的方法,它包括将至少一种在权利要求1中定义的结构式I的化合物掺入这些材料中。
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EP0565487B1 (de) * | 1992-04-08 | 1997-04-16 | Ciba SC Holding AG | Flüssige Antioxidantien als Stabilisatoren |
TW276260B (zh) * | 1992-07-15 | 1996-05-21 | Ciba Geigy Ag | |
DE4226288A1 (de) * | 1992-08-08 | 1994-02-10 | Hoechst Ag | Verfahren zur thermooxidativen Stabilisierung von Oxalkylenglykolalkylethern und thermooxidativ stabilisierte Mischungen von Oxalkylenglykolalkylethern |
FR2696471B1 (fr) * | 1992-10-02 | 1994-12-23 | Inst Textile De France | Utilisation de la vanilline et de ses dérivés comme agents de protection anti-UV. |
ES2220910T3 (es) * | 1992-11-24 | 2004-12-16 | Commonwealth Scientific And Industrial Research Organisation | Eliminadores de oxieno independientes de catalizadores de metales. |
EP0669367A1 (de) * | 1994-02-24 | 1995-08-30 | Ciba-Geigy Ag | Phenolische Stabilisatormischungen |
MY113152A (en) * | 1996-01-31 | 2001-11-30 | Ciba Holding Inc | Synergistic mixture consisting of a 2-4-dimethyl-6-s-alkylphenol and a sterically hindered phenol |
ES2137101B1 (es) * | 1997-01-30 | 2000-11-01 | Ciba Sc Holding Ag | Mezcla sinergistica que consiste en un 2,4-dimetil-6-s-alquilfenol y un fenol estericamente impedido. |
JP3802999B2 (ja) * | 1999-08-09 | 2006-08-02 | 信越化学工業株式会社 | 塩化ビニル系重合体の製造方法 |
US6538056B1 (en) | 2000-10-10 | 2003-03-25 | Clariant International Ltd. | Polyolefin articles with long-term elevated temperature stability |
CN104591970B (zh) * | 2014-12-23 | 2016-06-15 | 天津利安隆新材料股份有限公司 | 2,4-二甲基-6-(1-甲基-十五烷基)苯酚的制备方法 |
RU2732401C2 (ru) | 2016-01-21 | 2020-09-16 | Басф Се | Аддитивная смесь для стабилизации полиола и полиуретана |
CN107602353A (zh) * | 2017-11-14 | 2018-01-19 | 郑程 | 一种防老剂264的制备方法 |
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US2198349A (en) * | 1932-10-10 | 1940-04-23 | Sharp & Dohme Inc | Alkyl cresols |
US2073995A (en) * | 1934-06-22 | 1937-03-16 | Abbott Lab | Alkyl cresols |
US2205947A (en) * | 1935-09-25 | 1940-06-25 | Nat Aniline & Chem Co Inc | Nuclear alkyl derivatives of phenol compounds |
US2202877A (en) * | 1937-04-12 | 1940-06-04 | Gulf Oil Corp | Antioxidants and petroleum oils containing the same |
US2605251A (en) * | 1946-03-09 | 1952-07-29 | Firestone Tire & Rubber Co | Butadiene rubbery copolymer stabilized with 2, 4-dimethyl-6-octylphenol |
US3082258A (en) * | 1960-05-12 | 1963-03-19 | Eastman Kodak Co | Alkylation of phenols |
DE1142873B (de) * | 1961-01-25 | 1963-01-31 | Bayer Ag | Verfahren zur Herstellung von 2- und bzw. oder 6-Alkylphenolen |
US3367981A (en) * | 1963-05-10 | 1968-02-06 | Ethyl Corp | Phenol alkylation process |
US3347938A (en) * | 1964-04-23 | 1967-10-17 | Eastman Kodak Co | Antioxidant composition |
US3511802A (en) * | 1968-06-10 | 1970-05-12 | Eastman Kodak Co | Stabilized polypropylene resin composition |
US3929912A (en) * | 1970-05-25 | 1975-12-30 | Universal Oil Prod Co | Alkylation of hydroxy-substituted aromatic compounds |
US4086283A (en) * | 1975-06-25 | 1978-04-25 | Bayer Aktiengesellschaft | Process for preparing thymol |
US4405818A (en) * | 1981-09-30 | 1983-09-20 | Mobil Oil Corporation | Production of meta-isopropylphenolic products |
SU1182020A1 (ru) * | 1983-07-08 | 1985-09-30 | Отделение Нефтехимии Института Физико-Органической Химии И Углехимии Ан Усср | Способ получени 2-(1-метилалкил)-фенолов |
US4954663A (en) * | 1988-10-06 | 1990-09-04 | Mobil Oil Corp. | Process for preparing long chain alkyl phenols |
CA1326095C (en) * | 1987-05-18 | 1994-01-11 | Toshikazu Ijitsu | Styrene-based resin composition and moldings produced from said composition |
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CZ285993B6 (cs) | 1999-12-15 |
RU2067972C1 (ru) | 1996-10-20 |
CA2020051C (en) | 2001-11-20 |
RU2068424C1 (ru) | 1996-10-27 |
CA2020051A1 (en) | 1990-12-31 |
SK321090A3 (en) | 1999-01-11 |
EP0406169B1 (de) | 1997-06-04 |
DD298945A5 (de) | 1992-03-19 |
CN1229783A (zh) | 1999-09-29 |
CZ321090A3 (cs) | 1999-08-11 |
DE59010722D1 (de) | 1997-07-10 |
ES2103732T3 (es) | 1997-10-01 |
KR910000939A (ko) | 1991-01-30 |
EP0406169A1 (de) | 1991-01-02 |
CN1090167C (zh) | 2002-09-04 |
US5098945A (en) | 1992-03-24 |
CN1048865A (zh) | 1991-01-30 |
SK279627B6 (sk) | 1999-01-11 |
JP2923674B2 (ja) | 1999-07-26 |
BR9003097A (pt) | 1991-08-27 |
KR0168044B1 (ko) | 1999-03-20 |
JPH0350247A (ja) | 1991-03-04 |
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