CN101558119A - 含丙烯酸酯橡胶的聚酰胺 - Google Patents
含丙烯酸酯橡胶的聚酰胺 Download PDFInfo
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- CN101558119A CN101558119A CNA200780046008XA CN200780046008A CN101558119A CN 101558119 A CN101558119 A CN 101558119A CN A200780046008X A CNA200780046008X A CN A200780046008XA CN 200780046008 A CN200780046008 A CN 200780046008A CN 101558119 A CN101558119 A CN 101558119A
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- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L13/00—Compositions of rubbers containing carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/08—Homopolymers or copolymers of acrylic acid esters
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/02—Polyamides derived from omega-amino carboxylic acids or from lactams thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
- C08L25/08—Copolymers of styrene
- C08L25/12—Copolymers of styrene with unsaturated nitriles
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Abstract
热塑性模塑组合物,包含:A)10-95重量%的热塑性聚酰胺,B)5-90重量%的丙烯酸酯橡胶,可通过在至少一种分散剂和至少一种自由基引发剂的存在下使烯键式不饱和单体进行自由基引发水乳液聚合获得,其中乳液聚合使用:1-50重量%的具有5-12个碳原子的链烯[单体A],和50-99重量%的基于具有3-6个碳原子的单烯键式不饱和单-或二羧酸和具有1-12个碳原子的链烷醇的酯[单体B],以及合适的话至多10重量%的具有3-6个碳原子的单烯键式不饱和单-或二羧酸和/或其酰胺[单体C],和至多30重量%的不同于单体A-C的烯键式不饱和化合物[单体D],并且单体A-D一共为100重量%,C)0-40重量%的包含乙烯基芳族单体单元的共聚物,D)0-70重量%的其它添加剂,其中A)-D)的总重量百分数为100%。
Description
本发明涉及热塑性模塑组合物,包含:
A)10-95重量%的热塑性聚酰胺,
B)5-90重量%的丙烯酸酯橡胶,可通过在至少一种分散剂和至少一种自由基引发剂的存在下使烯键式不饱和单体进行自由基引发水乳液聚合获得,其中乳液聚合使用:
1-50重量%的具有5-12个碳原子的链烯[单体A],和
50-99重量%的基于具有3-6个碳原子的α,β-单烯键式不饱和单-或二羧酸和具有1-12个碳原子的链烷醇的酯[单体B],以及合适的话
至多10重量%的具有3-6个碳原子的α,β-单烯键式不饱和单-或二羧酸和/或其酰胺[单体C],及
至多30重量%的不同于单体A-C的α,β-烯键式不饱和化合物[单体D],并且单体A-D一共为100重量%,
C)0-40重量%的包含乙烯基芳族单体单元的共聚物和
D)0-70重量%的其它添加剂,
其中A)-D)的总重量百分数为100%。
本发明还涉及这些模塑组合物在生产模制品、纤维和箔中的用途以及可由此获得的任何类型的模制品。
聚酰胺的抗冲改性已是多年来许多研究的主题(S.Wu,Polym.Eng.Sci.,27,335,1987)。在市购产品中,所用抗冲改性剂主要为烯烃橡胶。为了与PA基体相容,通常使用官能化烯烃橡胶,实例为EPDM-g-MA、EPR-g-MA、SBS-g-MA(R.Gaymans,《聚合物共混物》,第2卷,177-224,2000,编辑D.R.Paul,C.B.Bucknall)。
迄今为止通常将芯-壳橡胶用于聚酰胺的抗冲改性(C.A.Cruz-Ramos,《聚合物共混物》,第2卷,137-175,2000,编辑D.R.Paul,C.B.Bucknall),因为特别是丙烯酸酯改性剂由于它们的玻璃化转变温度为约-40℃至约-30℃而失去活性。
迄今已知的抗冲改性PA模塑组合物对于很多应用不具有足够的抗紫外性。
DE-A 10 2005 046 692.3提出了一种制备基于丙烯酸酯单体的乳液聚合物的新方法。
因此本发明的目的是提供具有高韧性和改进的抗紫外性的基于聚酰胺的热塑性模塑组合物。
因此,找到了引言中定义的模塑组合物。
在从属权利要求中给出了优选的实施方案。
本发明模塑组合物包含10-95重量%,优选20-94重量%,特别是30-85重量%的至少一种聚酰胺作为组分A)。
本发明模塑组合物的聚酰胺的粘数通常为70-350ml/g,优选为70-170ml/g,其根据ISO 307在25℃下在96重量%浓度硫酸中以0.5重量%浓度溶液测定。
优选分子量(重均)至少为5000的半结晶或无定形树脂,实例为在美国专利2 071 250、2 071 251、2 130 523、2 130 948、2 241 322、2 312 966、2 512 606和3 393 210中描述的那些。
在这里实例为衍生自具有7-13元环的内酰胺的聚酰胺,例如聚己内酰胺、聚辛内酰胺和聚月桂内酰胺以及经过二羧酸与二胺反应获得的聚酰胺。
可以使用的二羧酸为具有6-12个,特别是6-10个碳原子的链烷二羧酸和芳族二羧酸。可在这里提及的一些酸仅为己二酸、壬二酸、癸二酸、十二烷二酸和对苯二甲酸和/或间苯二甲酸。
特别合适的二胺为具有6-12个,特别是6-8个碳原子的链烷二胺,以及间苯二甲胺、双(4-氨基苯基)甲烷、双(4-氨基环己基)甲烷、2,2-双(4-氨基苯基)丙烷、2,2-双(4-氨基环己基)丙烷或1,5-二氨基-2-甲基戊烷。
优选的聚酰胺为聚六亚甲基己二酰二胺、聚六亚甲基癸二酰二胺和聚己内酰胺以及尼龙-6/6,6共聚酰胺,其特别具有5-95重量%己内酰胺单元。
其它合适的聚酰胺可使ω-氨基烷基腈如氨基己腈(PA 6)和己二腈与六亚甲基二胺(PA 66)在水的存在下通过已知的直接聚合而获得,例如如DE-A 10313681、EP-A 1198491和EP 922065中所述。
还可以提及的是可例如通过1,4-二氨基丁烷与己二酸在高温下缩合获得的聚酰胺(尼龙-4,6)。所述结构的聚酰胺的制备方法例如如EP-A 38 094、EP-A 38 582和EP-A 39 524中所述。
其它合适的聚酰胺为可通过两种或更多种上述单体共聚获得的那些或者多种聚酰胺以任何所需混合比的混合物。
此外已证明半芳族共聚酰胺如PA 6/6T和PA 66/6T特别有利,它们的三胺含量小于0.5重量%,优选小于0.3重量%(见EP-A 299 444)。
EP-A 129 195和129 196中描述的方法可以用于制备优选的具有低三胺含量的半芳族共聚酰胺。
以下列表(并不全面)中包括所述聚酰胺A)和其它用于本发明的聚酰胺A),这些单体包括:
AB聚合物:
PA 4 吡咯烷酮
PA 6 ε-己内酰胺
PA 7 乙内酰胺
PA 8 辛内酰胺
PA 9 9-氨基壬酸
PA 11 11-氨基十一酸
PA 12 月桂内酰胺
AA/BB聚合物:
PA 46 四亚甲基二胺,己二酸
PA 66 六亚甲基二胺,己二酸
PA 69 六亚甲基二胺,壬二酸
PA 610 六亚甲基二胺,癸二酸
PA 612 六亚甲基二胺,十二烷二酸
PA 613 六亚甲基二胺,十三烷二酸
PA 1212 1,12-十二烷二胺,十二烷二酸
PA 1313 1,13-十三烷二胺,十三烷二酸
PA 6T 六亚甲基二胺,对苯二甲酸
PA 9T 壬二胺/对苯二甲酸
PA MXD6 间苯二甲胺,己二酸
PA 6I 六亚甲基二胺,间苯二甲酸
PA 6-3-T 三甲基六亚甲基二胺,对苯二甲酸
PA 6/6T (见PA 6和PA 6T)
PA 6/66 (见PA 6和PA 66)
PA 6/12 (见PA 6和PA 12)
PA 66/6/610 (见PA 66、PA 6和PA 610)
PA 6I/6T (见PA 6I和PA 6T)
PA PACM 12 二氨基二环己基甲烷,月桂内酰胺
PA 6I/6T/PACM 如PA 6I/6T+二氨基二环己基甲烷
PA 12/MACMI 月桂内酰胺,二甲基二氨基二环己基甲烷,间苯二甲酸
PA 12/MACMT 月桂内酰胺,二甲基二氨基二环己基甲烷,对苯二甲酸
PA PDA-T 苯二胺,对苯二甲酸
根据本发明,热塑性模塑组合物包含5-90重量%,优选5-40重量%,特别是10-30重量%的丙烯酸酯橡胶作为组分B),其可通过在至少一种分散剂和至少一种自由基引发剂的存在下使烯键式不饱和单体进行自由基引发水乳液聚合而获得,其中乳液聚合使用:
1-50重量%的具有5-12个碳原子的链烯[单体A],和
50-99重量%的基于具有3-6个碳原子的α,β-单烯键式不饱和单-或二羧酸和具有1-12个碳原子的链烷醇的酯[单体B],以及合适的话
至多10重量%的具有3-6个碳原子的α,β-单烯键式不饱和单-或二羧酸和/或其酰胺[单体C],及
至多30重量%的不同于单体A-C的α,β-烯键式不饱和化合物[单体D],并且单体A-D一共为100重量%。
烯键式不饱和单体在含水介质中进行自由基引发乳液聚合反应在先前已被广泛描述,因此是本领域熟练技术人员所熟知的[就此参见《乳液聚合》,Encyclopedia of Polymer Science and Engineering,第8卷,第659页及随后页(1987);D.C.Blackley,《高聚物胶乳》,第1卷,第35页及随后页(1966);H.Warson,《合成树脂乳液的应用》,第5章,第246页及随后页(1972);D.Diederich,Chemie in unserer Zeit 24,第135-142页(1990);《乳液聚合》,Inter-science Publishers,纽约(1965);DE-A 40 03422和Dispersionen synthetischer Hochpolymerer,F.Springer-Verlag,柏林(1969)]。自由基引发水乳液聚合反应的通常方法为使烯键式不饱和单体以单体液滴形式分散在含水介质中(伴随使用分散剂),并通过自由基聚合引发剂使之聚合。本发明方法不同于该程序的地方仅在于使用特定单体组合物。
所用单体A可以包括任何具有5-12个,优选5-10个,特别优选6-8个碳原子的线性或环状烯烃,其中它们能够自由基共聚并且除了碳和氢之外不包含其它元素。其中它们例如为线性烯烃:2-甲基-1-丁烯、3-甲基-1-丁烯、3,3-二甲基-2-异丙基-1-丁烯、2-甲基-2-丁烯、3-甲基-2-丁烯、1-戊烯、2-甲基-1-戊烯、3-甲基-1-戊烯、4-甲基-1-戊烯、2-戊烯、2-甲基-2-戊烯、3-甲基-2-戊烯、4-甲基-2-戊烯、2-乙基-1-戊烯、3-乙基-1-戊烯、4-乙基-1-戊烯、2-乙基-2-戊烯、3-乙基-2-戊烯、4-乙基-2-戊烯、2,4,4-三甲基-1-戊烯、2,4,4-三甲基-2-戊烯、3-乙基-2-甲基-1-戊烯、3,4,4-三甲基-2-戊烯、2-甲基-3-乙基-2-戊烯、1-己烯、2-甲基-1-己烯、3-甲基-1-己烯、4-甲基-1-己烯、5-甲基-1-己烯、2-己烯、2-甲基-2-己烯、3-甲基-2-己烯、4-甲基-2-己烯、5-甲基-2-己烯、3-己烯、2-甲基-3-己烯、3-甲基-3-己烯、4-甲基-3-己烯、5-甲基-3-己烯、2,2-二甲基-3-己烯、2,3-二甲基-2-己烯、2,5-二甲基-3-己烯、2,5-二甲基-2-己烯、3,4-二甲基-1-己烯、3,4-二甲基-3-己烯、5,5-二甲基-2-己烯、2,4-二甲基-1-己烯、1-庚烯、2-甲基-1-庚烯、3-甲基-1-庚烯、4-甲基-1-庚烯、5-甲基-1-庚烯、6-甲基-1-庚烯、2-庚烯、2-甲基-2-庚烯、3-甲基-2-庚烯、4-甲基-2-庚烯、5-甲基-2-庚烯、6-甲基-2-庚烯、3-庚烯、2-甲基-3-庚烯、3-甲基-3-庚烯、4-甲基-3-庚烯、5-甲基-3-庚烯、6-甲基-3-庚烯、6,6-二甲基-1-庚烯、3,3-二甲基-1-庚烯、3,6-二甲基-1-庚烯、2,6-二甲基-2-庚烯、2,3-二甲基-2-庚烯、3,5-二甲基-2-庚烯、4,5-二甲基-2-庚烯、4,6-二甲基-2-庚烯、4-乙基-3-庚烯、2,6-二甲基-3-庚烯、4,6-二甲基-3-庚烯、2,5-二甲基-4-庚烯、1-辛烯、2-甲基-1-辛烯、3-甲基-1-辛烯、4-甲基-1-辛烯、5-甲基-1-辛烯、6-甲基-1-辛烯、7-甲基-1-辛烯、2-辛烯、2-甲基-2-辛烯、3-甲基-2-辛烯、4-甲基-2-辛烯、5-甲基-2-辛烯、6-甲基-2-辛烯、7-甲基-2-辛烯、3-辛烯、2-甲基-3-辛烯、3-甲基-3-辛烯、4-甲基-3-辛烯、5-甲基-3-辛烯、6-甲基-3-辛烯、7-甲基-3-辛烯、4-辛烯、2-甲基-4-辛烯、3-甲基-4-辛烯、4-甲基-4-辛烯、5-甲基-4-辛烯、6-甲基-4-辛烯、7-甲基-4-辛烯、7,7-二甲基-1-辛烯、3,3-二甲基-1-辛烯、4,7-二甲基-1-辛烯、2,7-二甲基-2-辛烯、2,3-二甲基-2-辛烯、3,6-二甲基-2-辛烯、4,5-二甲基-2-辛烯、4,6-二甲基-2-辛烯、4,7-二甲基-2-辛烯、4-乙基-3-辛烯、2,7-二甲基-3-辛烯、4,7-二甲基-3-辛烯、2,5-二甲基-4-辛烯、1-壬烯、2-甲基-1-壬烯、3-甲基-1-壬烯、4-甲基-1-壬烯、5-甲基-1-壬烯、6-甲基-1-壬烯、7-甲基-1-壬烯、8-甲基-1-壬烯、2-壬烯、2-甲基-2-壬烯、3-甲基-2-壬烯、4-甲基-2-壬烯、5-甲基-2-壬烯、6-甲基-2-壬烯、7-甲基-2-壬烯、8-甲基-2-壬烯、3-壬烯、2-甲基-3-壬烯、3-甲基-3-壬烯、4-甲基-3-壬烯、5-甲基-3-壬烯、6-甲基-3-壬烯、7-甲基-3-壬烯、8-甲基-3-壬烯、4-壬烯、2-甲基-4-壬烯、3-甲基-4-壬烯、4-甲基-4-壬烯、5-甲基-4-壬烯、6-甲基-4-壬烯、7-甲基-4-壬烯、8-甲基-4-壬烯、4,8-二甲基-1-壬烯、4,8-二甲基-4-壬烯、2,8-二甲基-4-壬烯、1-癸烯、2-甲基-1-癸烯、3-甲基-1-癸烯、4-甲基-1-癸烯、5-甲基-1-癸烯、6-甲基-1-癸烯、7-甲基-1-癸烯、8-甲基-1-癸烯、9-甲基-1-癸烯、2-癸烯、2-甲基-2-癸烯、3-甲基-2-癸烯、4-甲基-2-癸烯、5-甲基-2-癸烯、6-甲基-2-癸烯、7-甲基-2-癸烯、8-甲基-2-癸烯、9-甲基-2-癸烯、3-癸烯、2-甲基-3-癸烯、3-甲基-3-癸烯、4-甲基-3-癸烯、5-甲基-3-癸烯、6-甲基-3-癸烯、7-甲基-3-癸烯、8-甲基-3-癸烯、9-甲基-3-癸烯、4-癸烯、2-甲基-4-癸烯、3-甲基-4-癸烯、4-甲基-4-癸烯、5-甲基-4-癸烯、6-甲基-4-癸烯、7-甲基-4-癸烯、8-甲基-4-癸烯、9-甲基-4-癸烯、5-癸烯、2-甲基-5-癸烯、3-甲基-5-癸烯、4-甲基-5-癸烯、5-甲基-5-癸烯、6-甲基-5-癸烯、7-甲基-5-癸烯、8-甲基-5-癸烯、9-甲基-5-癸烯、2,4-二甲基-1-癸烯、2,4-二甲基-2-癸烯、4,8-二甲基-1-癸烯、1-十一烯、2-甲基-1-十一烯、3-甲基-1-十一烯、4-甲基-1-十一烯、5-甲基-1-十一烯、6-甲基-1-十一烯、7-甲基-1-十一烯、8-甲基-1-十一烯、9-甲基-1-十一烯、10-甲基-1-十一烯、2-十一烯、2-甲基-2-十一烯、3-甲基-2-十一烯、4-甲基-2-十一烯、5-甲基-2-十一烯、6-甲基-2-十一烯、7-甲基-2-十一烯、8-甲基-2-十一烯、9-甲基-2-十一烯、10-甲基-2-十一烯、3-十一烯、2-甲基-3-十一烯、3-甲基-3-十一烯、4-甲基-3-十一烯、5-甲基-3-十一烯、6-甲基-3-十一烯、7-甲基-3-十一烯、8-甲基-3-十一烯、9-甲基-3-十一烯、10-甲基-3-十一烯、4-十一烯、2-甲基-4-十一烯、3-甲基-4-十一烯、4-甲基-4-十一烯、5-甲基-4-十一烯、6-甲基-4-十一烯、7-甲基-4-十一烯、8-甲基-4-十一烯、9-甲基-4-十一烯、10-甲基-4-十一烯、5-十一烯、2-甲基-5-十一烯、3-甲基-5-十一烯、4-甲基-5-十一烯、5-甲基-5-十一烯、6-甲基-5-十一烯、7-甲基-5-十一烯、8-甲基-5-十一烯、9-甲基-5-十一烯、10-甲基-5-十一烯、1-十二烯、2-十二烯、3-十二烯、4-十二烯、5-十二烯或6-十二烯以及环状烯烃:环戊烯、2-甲基-1-环戊烯、3-甲基-1-环戊烯、4-甲基-1-环戊烯、3-丁基-1-环戊烯、乙烯基环戊烷、环己烯、2-甲基-1-环己烯、3-甲基-1-环己烯、4-甲基-1-环己烯、1,4-二甲基-1-环己烯、3,3,5-三甲基-1-环己烯、4-环戊基-1-环己烯、乙烯基环己烷、环庚烯、1,2-二甲基-1-环庚烯、环辛烯、2-甲基-1-环辛烯、3-甲基-1-环辛烯、4-甲基-1-环辛烯、5-甲基-1-环辛烯、环壬烯、环癸烯、环十一烯、环十二烯、双环[2.2.1]-2-庚烯、5-乙基双环[2.2.1]-2-庚烯、2-甲基双环[2.2.2]-2-辛烯、双环[3.3.1]-2-壬烯或双环[3.2.2]-6-壬烯.
优选使用1-链烯如1-戊烯、1-己烯、1-庚烯、1-辛烯、1-壬烯、1-癸烯、1-十一烯、1-十二烯、2,4,4-三甲基-1-戊烯、2,4-二甲基-1-己烯、6,6-二甲基-1-庚烯或2-甲基-1-辛烯。有利地将具有6-8个碳原子的链烯用作单体A,优选具有6-8个碳原子的1-链烯。特别优选使用1-己烯、1-庚烯或1-辛烯。当然还可以使用上述单体A的混合物。
所用单体B包括基于具有3-6个,特别是3或4个碳原子的α,β-单烯键式不饱和单-或二羧酸和具有1-12个,优选1-8个,特别是1-4个碳原子的链烷醇的酯,其中α,β-单烯键式不饱和单-或二羧酸的具体实例为丙烯酸、甲基丙烯酸、马来酸、富马酸和衣康酸,链烷醇的具体实例为甲醇、乙醇、正丙醇、异丙醇、正丁醇、2-甲基-1-丙醇、叔丁醇、正戊醇、3-甲基-1-丁醇、正己醇、4-甲基-1-戊醇、正庚醇、5-甲基-1-己醇、正辛醇、6-甲基-1-庚醇、正壬醇、7-甲基-1-辛醇、正癸醇、8-甲基-1-壬醇、正十二烷醇、9-甲基-1-癸醇和2-乙基-1-己醇。优选使用丙烯酸或甲基丙烯酸的甲酯、乙酯、正丁酯、异丁酯、戊酯、己酯、庚酯、辛酯、壬酯、癸酯、2-乙基己酯或十二烷基酯,或者使用富马酸或马来酸的二甲酯或二正丁酯。当然还可以使用上述酯的混合物。
任选使用的单体C包括具有3-6个碳原子的α,β-单烯键式不饱和单-或二羧酸和/或其酰胺,具体实例为丙烯酸、甲基丙烯酸、马来酸、富马酸或衣康酸,或者丙烯酰胺或甲基丙烯酰胺。当然还可以使用上述单体C的混合物。
所用不同于单体A-C的单体D的实例为α,β-烯键式不饱和化合物如乙烯基芳族单体如苯乙烯、α-甲基苯乙烯、邻氯苯乙烯或乙烯基甲苯,乙烯基卤化物如氯乙烯或偏二氯乙烯,由乙烯基醇和具有1-18个碳原子的单羧酸组成的酯如乙酸乙烯酯、丙酸乙烯酯、正丁酸乙烯酯、月桂酸乙烯酯和硬脂酸乙烯酯,α,β-单-或二烯键式不饱和羧酸的腈如丙烯腈、甲基丙烯腈、富马腈、马来腈以及具有4-8个碳原子的共轭二烯如1,3-丁二烯和异戊二烯,以及乙烯基磺酸、2-丙烯酰胺基-2-甲基丙烷磺酸、苯乙烯磺酸及其水溶性盐,以及N-乙烯基吡咯烷酮、2-乙烯基吡啶、4-乙烯基吡啶、2-乙烯基咪唑、丙烯酸2-(N,N-二甲基氨基)乙酯、甲基丙烯酸2-(N,N-二甲基氨基)乙酯、丙烯酸2-(N,N-二乙基氨基)乙酯、甲基丙烯酸2-(N,N-二乙基氨基)乙酯、甲基丙烯酸2-(N-叔丁基氨基)乙酯、N-(3-N’,N’-二甲基氨基丙基)甲基丙烯酰胺或甲基丙烯酸2-(1-咪唑啉酮-2-基)乙酯。其它单体D具有至少一个环氧基、羟基、N-羟甲基或羰基,或者至少两个非共轭烯键式不饱和双键。这里实例为具有两个乙烯基的单体、具有两个亚乙烯基的单体以及具有两个链烯基的单体。这里特别有利的化合物为二元醇与α,β-单烯键式不饱和单羧酸(其中优选丙烯酸和甲基丙烯酸)的二酯。这些具有两个非共轭烯键式不饱和双键的单体的实例为亚烷基二醇二丙烯酸酯和亚烷基二醇二甲基丙烯酸酯,例如乙二醇二丙烯酸酯、1,2-丙二醇二丙烯酸酯、1,3-丙二醇二丙烯酸酯、1,3-丁二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯及乙二醇二甲基丙烯酸酯、1,2-丙二醇二甲基丙烯酸酯、1,3-丙二醇二甲基丙烯酸酯、1,3-丁二醇二甲基丙烯酸酯、1,4-丁二醇二甲基丙烯酸酯以及二乙烯基苯;甲基丙烯酸乙烯酯、丙烯酸乙烯酯、甲基丙烯酸烯丙酯、丙烯酸烯丙酯、马来酸二烯丙酯、富马酸二烯丙酯、亚甲基二丙烯酰胺、丙烯酸环戊二烯酯、氰尿酸三烯丙酯或异氰尿酸三烯丙酯。就此其它特别重要的化合物为甲基丙烯酸和丙烯酸的C1-C8羟烷基酯,实例为丙烯酸正羟乙酯、丙烯酸正羟丙酯或丙烯酸正羟丁酯和甲基丙烯酸正羟乙酯、甲基丙烯酸正羟丙酯或甲基丙烯酸正羟丁酯,以及化合物如丙烯酸缩水甘油酯或甲基丙烯酸缩水甘油酯、双丙酮丙烯酰胺和乙酰乙酰氧基乙基丙烯酸酯及相应的甲基丙烯酸酯。当然也可以使用单体D的混合物。
然而,对于自由基引发水乳液聚合反应,优选使用
1-49.99重量%的单体A,
50-98.99重量%的单体B,以及
0.01-10重量%的单体C。
所用的特定单体A是1-戊烯、1-己烯、1-庚烯、1-辛烯、3-甲基-1-己烯、3-甲基-1-庚烯和/或3-甲基-1-辛烯,用作单体B的特定化合物为丙烯酸正丁酯、丙烯酸甲酯、丙烯酸2-乙基己酯、甲基丙烯酸甲酯和/或丙烯酸叔丁酯,用作单体C的特定化合物为丙烯酸、甲基丙烯酸和/或衣康酸。
特别优选用于自由基引发水乳液聚合反应的化合物为
5-40重量%的1-戊烯、1-己烯和/或1-辛烯[单体A],和
56-94.9重量%的丙烯酸正丁酯、丙烯酸甲酯、丙烯酸2-乙基己酯、甲基丙烯酸甲酯和/或丙烯酸叔丁酯[单体B],以及
0.1-4重量%的丙烯酸和/或甲基丙烯酸[单体C]。
这里通常可以至少将一部分单体A-D用作含水反应介质中的初始进料并且可将任何剩余量在自由基聚合反应引发之后以一部分分批、以多部分分批或者以不变或改变的流速连续加入。然而,也可以至少将一部分自由基聚合引发剂用作含水反应介质中的初始进料并且可以加热所得含水反应介质至聚合温度,并在该温度下将单体A-D以一部分分批、以多部分分批或者以不变或改变的流速连续加入含水反应介质中。在特别有利的方法中,将单体A-D以混合物形式加入含水反应介质中。有利的是将单体A-D以单体水乳液形式加入。
根据本发明,在本发明方法中伴随使用分散剂,它们使单体液滴以及在分散体中形成的聚合物颗粒保持在含水介质中并确保所产生的聚合物水分散体具有稳定性。可以使用的分散剂不仅是通常用于进行自由基水乳液聚合反应的保护胶体而且是乳化剂。
合适的保护胶体的实例为聚乙烯醇,聚亚烷基二醇,聚丙烯酸和聚甲基丙烯酸的碱金属盐,明胶衍生物或包含丙烯酸、甲基丙烯酸、马来酸酐、2-丙烯酰胺基-2-甲基丙烷磺酸和/或4-苯乙烯磺酸的共聚物及这些共聚物的碱金属盐,以及包含N-乙烯基吡咯烷酮、N-乙烯基己内酰胺、N-乙烯基咔唑、1-乙烯基咪唑、2-乙烯基咪唑、2-乙烯基吡啶、4-乙烯基吡啶、丙烯酰胺、甲基丙烯酰胺、带胺基的丙烯酸酯、甲基丙烯酸酯、丙烯酰胺和/或甲基丙烯酰胺的均聚物和共聚物。Houben-Weyl,Methoden derorganischen Chemie[有机化学方法],第XIV/1卷,MakromolekulareStoffe[大分子物质],Georg-Thieme-Verlag,Stuttgart,1961,第411-420页给出了其它合适保护胶体的详细描述。
当然还可以使用由保护胶体和/或乳化剂组成的混合物。所用分散剂通常仅包含相对分子量通常低于1000(不同于保护胶体的相对分子量)的乳化剂。它们可以是阴离子、阳离子或非离子的。如果使用表面活性剂混合物,则各组分当然必须彼此相容,并且在有疑问的情况下可以使用一些初步实验来检验。阴离子乳化剂通常彼此相容并且与非离子乳化剂相容。阳离子乳化剂同样如此,而阴离子与阳离子乳化剂则基本上不能彼此相容。Houben-Weyl,Methoden der organischen Chemie[有机化学方法],第XIV/1卷,Makromolekulare Stoffe[大分子物质],Georg-Thieme-Verlag,Stuttgart,1961,第192-208页给出了合适乳化剂的概述。
然而,根据本发明,乳化剂特别用作分散剂。
常用的非离子乳化剂的实例为乙氧基化的单-、二-和三烷基苯酚(EO数:3-50,烷基:C4-C12)以及乙氧基化的脂肪醇(EO数:3-80,烷基:C8-C36)。它们的实例为来自BASF AG的A品级(乙氧基化C12-C14脂肪醇,EO数:3-8)、AO品级(乙氧基化C13-C15羰基合成醇,EO数:3-30)、AT品级(乙氧基化C16-C18脂肪醇,EO数:11-80)、ON品级(乙氧基化C10羰基合成醇,EO数:3-11)和TO品级(乙氧基化C13羰基合成醇,EO数:3-20)。
一般阴离子乳化剂的实例为烷基硫酸盐(烷基:C8-C12)、乙氧基化链烷醇的硫酸半酯(EO数:4-30,烷基:C12-C18)和乙氧基化烷基苯酚(EO数:3-50,烷基:C4-C12)、烷基磺酸(烷基:C12-C18)和烷基芳基磺酸(烷基:C9-C18)的碱金属盐和铵盐。
已证明合适的其它阴离子乳化剂为式(I)化合物:
其中R1和R2为H或C4-C24烷基,但是不同时为氢,M1和M2可以为碱金属离子和/或铵离子。在通式(I)中,R1和R2优选为具有6-18个,特别是6、12或16个碳原子的线性或支化烷基或者氢,但是R1和R2不同时为H。M1和M2优选为钠、钾或铵,特别优选为钠。特别有利的化合物(I)为其中M1和M2为钠、R1为具有12个碳原子的支化烷基且R2为H或R1的那些。通常使用具有50-90重量%单烷基化产物的工业混合物,例如2A1(Dow Chemical Company的商标)。化合物(I)是熟知的,例如由US-A 4269 749熟知,并可市购。
合适的阳离子乳化剂通常为带C6-C18烷基或带C6-C18芳烷基或带杂环基的伯、仲、叔或季铵盐,链烷醇铵盐,吡啶鎓盐,咪唑啉鎓盐,噁唑啉鎓盐,吗啉鎓盐,噻唑啉鎓盐或氧化胺的盐或者喹啉鎓盐,异喹啉鎓盐,鎓盐,锍盐或鏻盐。它们的实例为十二烷基乙酸铵和相应的硫酸盐、2-(N,N,N-三甲基铵)乙基石蜡酸酯的硫酸盐或乙酸盐、N-十六烷基吡啶鎓硫酸盐、N-月桂基硫酸吡啶鎓盐以及N-十六烷基-N,N,N-三甲基硫酸铵、N-十二烷基-N,N,N-三甲基硫酸铵、N-辛基-N,N,N-三甲基硫酸铵、N,N-二硬脂基-N,N-二甲基硫酸铵以及双子表面活性剂N,N’-(月桂基二甲基)乙二胺二硫酸盐、乙氧基化的牛油脂肪烷基-N-甲基硫酸铵和乙氧基化的油胺(例如来自BASF AG的AC,约12个氧化乙烯单元)。在H.Stache,Tensid-Taschenbuch,Carl-Hanser-Verlag,Munich,Vienna,1981和《McCutcheon乳化剂和清洁剂》,MC Publishing Company,GlenRock,1989中找到许多其它实例。有利的是抗衡阴离子基团具有最小的亲核性,实例为高氯酸根,硫酸根,磷酸根,硝酸根和羧酸根如乙酸根、三氟乙酸根、三氯乙酸根、丙酸根、草酸根、柠檬酸根、苯甲酸根以及有机磺酸的共轭阴离子如甲基磺酸根、三氟甲基磺酸根和对甲苯磺酸根以及四氟硼酸根、四苯基硼酸根、四(五氟苯基)硼酸根、四[双(3,5-三氟甲基)苯基]硼酸根、六氟磷酸根、六氟砷酸根或六氟锑酸根。
优选用作分散剂的乳化剂的总用量每种情况下基于单体总量有利地为≥0.005且≤10重量%,优选≥0.01且≤5重量%,特别是≥0.1且≤3重量%。
除了乳化剂或代替乳化剂,用作分散剂的保护胶体的总量每种情况下基于单体总量通常为≥0.1且≤10重量%,常常为≥0.2且≤7重量%。
然而,优选阴离子和/或非离子乳化剂,特别优选阴离子乳化剂用作分散剂。
自由基引发水乳液聚合借助自由基聚合引发剂(自由基引发剂)引发。原则上它们可以是过氧化物或偶氮化合物。当然也可以使用氧化还原引发剂体系。原则上可以使用的过氧化物为无机过氧化物,例如过氧化氢或过氧二硫酸盐如过氧二硫酸的单-或二碱金属盐或铵盐(例如它的单-和二钠盐、钾盐或铵盐),或者有机过氧化物,例如烷基氢过氧化物如氢过氧化叔丁基、氢过氧化对基或氢过氧化枯基以及二烷基或二芳基过氧化物如过氧化二叔丁基或过氧化二枯基。所用偶氮化合物主要包括2,2’-偶氮双(异丁腈)、2,2’-偶氮双(2,4-二甲基戊腈)和2,2’-偶氮双(脒基丙基)二盐酸盐(AIBA,对应于来自Wako Chemicals的V-50)。用于氧化还原引发剂体系的氧化剂主要为上述过氧化物。所用相应的还原剂可以包括具有低氧化态的硫化合物,例如碱金属亚硫酸盐如亚硫酸钾和/或亚硫酸钠,碱金属亚硫酸氢盐如亚硫酸氢钾和/或亚硫酸氢钠,碱金属偏亚硫酸氢盐如偏亚硫酸氢钾和/或偏亚硫酸氢钠,甲醛化次硫酸盐如甲醛化次硫酸钾和/或甲醛化次硫酸钠,脂族亚磺酸的碱金属盐,尤其是钾盐和/或钠盐,碱金属氢硫化物如硫化氢钾和/或硫化氢钠,多价金属盐如硫酸亚铁、硫酸亚铁铵、磷酸亚铁,烯二醇如二羟基马来酸、安息香和/或抗坏血酸,以及还原糖类如山梨糖、葡萄糖、果糖和/或二羟基丙酮。所用自由基引发剂的量基于单体总量通常为0.01-5重量%,优选为0.1-3重量%,特别优选为0.2-1.5重量%。
根据本发明,全部量的自由基引发剂可以用作含水反应介质中的初始进料。然而,合适的话还可以仅将一部分自由基引发剂用作含水反应介质中的初始进料,然后在本发明自由基乳液聚合过程中根据消耗需求连续或分批加入全部量或任何剩余量。
0-170℃的整个范围可以用作本发明自由基水乳液聚合的反应温度。这里所用温度一般为50-120℃,通常为60-110℃,常常为70-100℃。本发明自由基水乳液聚合可以在比1巴(绝对)小、相等或大的压力下进行,因此聚合温度可以超过100℃且可以至多为170℃。优选使用超计大气压来聚合挥发性单体如2-甲基-1-丁烯、3-甲基-1-丁烯、2-甲基-2-丁烯、丁二烯或氯乙烯。这里压力可以假定为值1.2、1.5、2、5、10、15巴或甚至更高值。如果乳液聚合在低于一大气压下进行,则压力设置为950毫巴,通常为900毫巴,常常为850毫巴(绝对)。本发明自由基水乳液聚合有利地在惰性气体如氮气或氩气下在1atm(1.01绝对巴)下进行。
原则上,含水反应介质也可以包括辅助量的水溶性有机溶剂如甲醇、乙醇、异丙醇、丁醇、戊醇或丙酮等。然而,本发明方法优选在没有这种溶剂的情况下进行。
为了降低或控制可经由聚合获得的聚合物的分子量,除了上述组分外,还可以且任选使用自由基链转移化合物。这里所用化合物主要为脂族和/或芳脂族卤代化合物如正丁基氯,正丁基溴,正丁基碘,二氯甲烷,1,2-二氯乙烷,氯仿,溴仿,一溴三氯甲烷,二溴二氯甲烷,四氯化碳,四溴化碳,苄基氯,苄基溴,有机硫化合物,例如脂族伯,仲或叔硫醇如乙硫醇,正丙硫醇,2-丙硫醇,正丁硫醇,2-丁硫醇,2-甲基-2-丙硫醇,正戊硫醇,2-戊硫醇,3-戊硫醇,2-甲基-2-丁硫醇,3-甲基-2-丁硫醇,正己硫醇,2-己硫醇,3-己硫醇,2-甲基-2-戊硫醇,3-甲基-2-戊硫醇,4-甲基-2-戊硫醇,2-甲基-3-戊硫醇,3-甲基-3-戊硫醇,2-乙基丁硫醇,2-乙基-2-丁硫醇,正庚硫醇及其异构体化合物,正辛硫醇及其异构体化合物,正壬硫醇及其异构体化合物,正癸硫醇及其异构体化合物,正十一烷硫醇及其异构体化合物,正十二烷硫醇及其异构体化合物,正十三烷硫醇及其异构体化合物,取代硫醇如2-羟基乙硫醇,芳族硫醇如苯硫醇,邻-、间-或对甲基苯硫醇以及在“聚合物手册”第3版,1989,J.Brandrup和E.H.Immergut,John Wiley & Sons,第II部分,第133-141页中所述的所有其它硫化合物,以及脂族和/或芳族醛如乙醛、丙醛和/或苯甲醛,不饱和脂肪酸如油酸,具有非共轭双键的二烯如二乙烯基甲烷或乙烯基环己烷,或者具有易夺取的氢原子的烃如甲苯。然而,还可以使用上述不互相干扰的自由基链转移化合物的混合物。
任选使用的自由基链转移化合物的全部量基于单体总量一般为≤5重量%,通常为≤3重量%,常常为≤1重量%。
有利的是将部分或全部量的任选使用的自由基链转移化合物在自由基聚合引发之前加入反应介质中。此外,部分或全部量的自由基链转移化合物可有利地在聚合过程中与单体A-D一起加入含水反应介质中。
可通过本发明方法获得的聚合物原则上可以具有-70℃至+150℃,常常-30℃至+100℃,通常-20℃至+50℃的玻璃化转变温度。通常选择单体A-D应使形成的聚合物的Tg值为≤+10℃、≤0℃、≤-10℃、≤-20℃、≤-30℃、≤-40℃或≤-50℃。然而,还可以制备玻璃化转变温度为-70℃至+10℃、-60℃至-10℃或-50℃至-20℃的聚合物。这里玻璃化转变温度为根据ASTM D3418-82经由差示扫描量热计(DSC)测定的中点温度[还参见Ullmann’s Encyclopedia of Industrial Chemistry,第169页,VerlagChemie,Weinheim,1992和Zosel in Farbe und Lack,82,第125-134页,1976]。
根据Fox(T.G.Fox,Bull.Am.Phys.Soc.1956[系列II]1,第123页,及根据Ullmann’sder technischen Chemie[Ullmann工业化学百科全书],第19卷,第18页,第4版,Verlag Chemie,Weinheim,1980),通过下式给出至多弱交联的共聚物玻璃化转变温度的极近似值:
1/Tg=x1/Tg 1+x2/Tg 2+....xn/Tg n,
其中x1、x2....xn为单体1、2....n的质量分数,Tg 1、Tg 2....Tg n分别为每种情况下仅由单体1、2....n之一组成的聚合物的玻璃化转变温度(单位为K)。大部分烯键式不饱和单体的这些均聚物的玻璃化转变温度是已知的(或可以本身已知的方式容易地实验测定)并且例如在J.Brandrup,E.H.Immergut,聚合物手册,第1版,J.Wiley,纽约,1966,第2版.J.Wiley,纽约,1975和第3版J.Wiley,纽约,1989以及在Ullmann’s Encyclopediaof Industrial Chemistry,第169页,Verlag Chemie,Weinheim,1992中列出。
自由基引发水乳液聚合也可以任选在聚合物种子的存在下进行,例如在每种情况下基于单体总量为0.01-3重量%,通常为0.02-2重量%,常常为0.04-1.5重量%的聚合物种子的存在下进行。
特别是当待借助自由基水乳液聚合制备的聚合物颗粒的尺寸以可控方式设置时而使用聚合物种子(就此参见例如US-A 2,520,959和US-A 3,397,165)。
所用特别的聚合物种子的聚合物种子颗粒具有窄粒度分布且重均直径Dw≤100nm,通常≥5nm且≤50nm,常常≥15nm且≤35nm。测定重均粒径的方法是本领域熟练技术人员已知的,例如使用分析超离心法。这里,重均粒径指的是通过分析超离心法测定的重均Dw50值(就此参见S.E.Harding等人,《生物化学和聚合物科学中的分析超离心》,Royal Societyof Chemistry,剑桥,大不列颠1992,第10章,使用八池AUC倍增器分析聚合物分散体:高分辨率粒度分布和密度梯度技术,W.第147-175页)。
对于本说明书,窄粒度分布指的是重均粒径Dw50与数均粒径DN50之比[Dw50/DN50]≤2.0,优选≤1.5,特别优选≤1.2或≤1.1,通过分析超离心法测定。
聚合物种子的使用形式通常为聚合物水分散体。在这种情况下,上述定量数据基于聚合物种子水分散体的聚合物固体含量;因此它们以聚合物种子固体基于单体总量的重量份陈述。
如果使用聚合物种子,有利的是使用外来聚合物种子。不像已知的原位聚合物种子(其在反应容器中开始实际乳液聚合之前制备,并且其单体组成与经由随后的自由基引发水乳液聚合制备的聚合物的单体组成相同),外来聚合物种子为在单独的反应步骤中已制备好并且其单体组成与经由自由基引发水乳液聚合制备的聚合物的单体组成不同的聚合物种子。这简单意味着制备外来聚合物种子和制备聚合物水分散体使用不同单体或具有不同组成的单体混合物。外来聚合物种子的制备是本领域熟练技术人员熟悉的,通常通过使用较少的单体和较多的乳化剂作为反应容器中初始进料并在反应温度下加入足量的聚合引发剂而进行。
根据本发明,优选使用玻璃化转变温度≥50℃,通常≥60℃或≥70℃,常常≥80℃或≥90℃的外来聚合物种子。特别优选聚苯乙烯聚合物种子或聚甲基丙烯酸甲酯聚合物种子。
全部量的外来聚合物种子可以在开始加入单体A-D之前用作反应容器中初始进料。然而,还可以仅将一部分外来聚合物种子在开始加入单体A-D之前用作反应容器中初始进料并在聚合过程中加入剩余量。然而,需要的话,也可以在聚合过程中加入全部量的聚合物种子。优选将全部量的外来聚合物种子在开始加入单体A-D之前用作反应容器中初始进料。
根据本发明获得的聚合物水分散体的通常聚合物固体含量在每种情况下基于聚合物水分散体一般为≥10且≤80重量%,通常≥20且≤70重量%,常常≥25且≤60重量%。通过准弹性光散射(ISO标准13321)测定的数均粒径(累积z-均)一般为10-2000nm,通常为20-1000nm,常常为100-700nm或100-400nm。
为了降低未反应单体和其它低沸点化合物的残余含量,通常将同样对本领域熟练技术人员已知的化学和/或物理方法用在所得聚合物水分散体上[参见例如EP-A 771328、DE-A 196 24 299、DE-A 196 21 027、DE-A 19741 184、DE-A 197 41 187、DE-A 198 05 122、DE-A 198 28 183、DE-A 19839 199、DE-A 198 40 586和198 47 115]。
然而,在与A)配混过程中还可以在没有溶剂的情况下掺入组分B),这意味着去除溶剂且掺入固体。
本发明模塑组合物包含基于模塑组合物总重为0-40重量%,优选1-30重量%,特别是1-15重量%的共聚物或由两种或更多种不同共聚物(它们包括乙烯基芳族单体)组成的混合物作为组分C。优选基于苯乙烯或未取代苯乙烯和不饱和腈的共聚物。
特别优选本发明模塑组合物包含基于模塑组合物总重为2-50重量%的组分C。
可以使用的共聚物不仅为无规共聚物而且为嵌段共聚物。合适共聚物的实例为苯乙烯-丙烯腈共聚物或基于苯乙烯、丙烯腈和N-苯基马来酰亚胺的三元共聚物或包含噁唑啉基团的共聚物。
共聚物C特别优选由以下组成:
c1)60-95重量%,优选65-85重量%的苯乙烯或通式I的取代苯乙烯或它们的混合物,和
c2)5-40重量%,优选15-35重量%的至少一种不饱和腈,优选丙烯腈或甲基丙烯腈或它们的混合物。
共聚物C与树脂类似,为热塑性的且不含橡胶。特别优选的共聚物C为由苯乙烯和丙烯腈、由α-甲基苯乙烯和丙烯腈或由苯乙烯、α-甲基苯乙烯和丙烯腈组成的那些。
这些共聚物通常在接枝聚合制备组分B过程中作为副产物产生,特别是当大量单体接枝在少量橡胶上时。
共聚物C是本身已知的,并且可以经由自由基聚合,特别是经由乳液、悬浮、溶液或本体聚合而制备。它们的粘数为40-160ml/g,优选为60-110ml/g(在23℃下在二甲基甲酰胺中以0.5重量%浓度溶液测量),其对应的平均(重均)分子量Mw为40 000-2 000 000。
在一个优选的实施方案中,共聚物C基于乙烯基芳族化合物(c1)并包含二羧酸酐(c21)或二羧酰亚胺(c22)或者由c21)和c22)组成的混合物作为单元(c2),和衍生自其它不包含与聚酰胺端基反应或仅更慢地反应的基团的单体的单元(c3)。
根据该实施方案,单元c1)的比例优选为50-85重量%,特别是60-80重量%。共聚物C)非常特别优选包含65-78重量%的衍生自芳族乙烯基化合物的单元。重量%数据总是基于c1)-c3)总重。
衍生自α,β-不饱和二羧酸酐的单元c21)的比例优选为0.3-25重量%。具有基本上小于0.3重量%单元c21)的共聚物C),例如具有小于0.1重量%这些单元的那些,通常反应性不够。具有基本上大于25重量%的那些因其交联活性太高而大部分变得难于处理。共聚物C)优选包含0.5-15重量%,特别是0.7-10重量%,非常特别优选0.8-5重量%,例如1-3重量%的c21)。这里重量%数据每种情况下基于单元c1)-c3)的总重。
代替单元c21),或者优选除了单元c21),共聚物C)可以包含衍生自α,β-不饱和二羧酰亚胺,特别是环状二羧酰亚胺的单元c22)。它们通常在共聚物C)中以0-49.7重量%存在。优选共聚物C)包含0-39.5重量%,特别是0-34.2重量%的c22),每种情况下重量%数据基于单元c1)-c3)的总重。
如果共聚物不包含c22),则共聚物C)另外还可以包含基于单元c1)-c3)的总重为14.7-40重量%,优选19.5-35重量%,特别是21.3-33重量%的衍生自其它能够自由基聚合的化合物的单元c3)。
可以使用的特别的芳族乙烯基化合物c1)为苯乙烯和苯乙烯衍生物。其中合适的苯乙烯衍生物为α-甲基苯乙烯和在芳环上取代的苯乙烯衍生物如乙烯基甲苯、叔丁基苯乙烯或氯苯乙烯。当然还可以使用不同芳族乙烯基化合物的混合物。非常特别优选使用苯乙烯。
其中优选的α,β-不饱和二羧酸酐c21)为环状化合物,尤其是具有2-20个碳原子的那些。双键可以在环外或环内。在这些化合物中,特别优选马来酐、甲基马来酐或衣康酐。还可以使用各种二羧酸酐的混合物。非常特别优选仅使用马来酐。
α,β-不饱和二羧酰亚胺c22)通常对应于上述二羧酸酐。氮上的取代基通常为C1-C20烷基、C4-C20环烷基、C1-C10烷基-C6-C18芳基或C6-C18芳基。
烷基可以是线性或支化的并可以被一个或多个氧原子间隔,没有氧原子与氮原子或另一个氧原子直接连接。其中这些烷基为甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正己基、正癸基和正十二烷基。环烷基可以为未取代或取代的。合适的取代基的实例为烷基如甲基或乙基。可以提及的环烷基的实例为环丁基、环戊基、环己基和对甲基环己基。烷基芳基的烷基可以是线性或支化的,并且烷基芳基也可以具有取代基。这些取代基的实例为烷基如甲基或乙基,或者卤素原子如氯或溴。可以使用的烷基芳基的实例为苄基、乙基苯基或对氯苄基。芳基也可以为取代或未取代的,合适取代基的实例为烷基如甲基或乙基,或者卤素原子如氯或溴。其中优选的芳基为苯基和萘基。非常特别优选的基团为环己基或苯基。
作为单元c3)的实例,这里可以提及的是丙烯酸和丙烯酸衍生物,例如甲基丙烯酸、丙烯酸烷基酯如丙烯酸乙酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯或甲基丙烯酸环己酯,或者不饱和腈如丙烯腈、甲基丙烯腈。这些单体的混合物也同样可以使用。非常特别优选仅使用丙烯腈。
作为该实施方案优选的共聚物C)的实例,可以提及的是具有以下组成的那些:
包含以下组分的共聚物
c1)50-85重量%,优选60-81重量%的苯乙烯,
c2)0.5-10重量%,优选1-5重量%的马来酐,和
c3)14.5-40重量%,优选18-35重量%的丙烯腈,
其中c1)-c3)的比例一共为100重量%。
该实施方案的共聚物C)优选包含随机分布的单元c1)-c3)。共聚物C)的摩尔质量MW(重均)通常为30 000-500 000g/mol,优选为50 000-250000g/mol,特别是70 000-200 000g/mol,借助GPC使用四氢呋喃(THF)作为洗脱剂和聚苯乙烯校准测定。
该实施方案的共聚物C)可以例如通过相应单体的自由基聚合而制备。该反应可以悬浮或乳液聚合进行,或以溶液或本体聚合进行,优选后者。一般可以使用通常的方法如光或优选使用自由基引发剂如过氧化物如过氧化苯甲酰引发自由基反应。也可以热引发聚合。
制备该实施方案共聚物C)的另一个方法为首先使组分c1)、c21)和合适的话c3)彼此以自由基反应进行反应,然后使用合适的伯胺或氨将反应产物中存在的一些酸酐基团转化成二酰亚胺基团,由此产生单元c22)。该反应通常在叔胺作为催化剂的情况下在80-350℃的温度下进行。
在另一个优选的实施方案中,代替单元c21)或c22)或其混合物,共聚物C)包含衍生自含环氧基的不饱和单体的单元(c23)。单元c23)也可以基于两种或更多种这类不同单体的混合物。单体可以具有一个或者两个或更多个环氧基。特别优选仅使用甲基丙烯酸缩水甘油酯。
其中该实施方案优选的共聚物C)为包含以下组分的共聚物:
c1)65-85重量%,优选70-80重量%的苯乙烯,
c23)0.5-10重量%,优选1-5重量%的甲基丙烯酸缩水甘油酯,和
c3)14.5-34.5重量%,优选19-29重量%的丙烯腈,
其中c1)-c3)的比例一共为100重量%。
该实施方案的共聚物C)例如可以通过在过氧化引发剂的存在下在聚乙烯醇中悬浮聚合而制备。
该实施方案的共聚物C)的摩尔质量(重均Mw)通常为50 000-1 000000g/mol,优选为70 000-500 000g/mol,通过GPC使用THF作为洗脱剂,以聚苯乙烯为标准测定。
本发明模塑组合物可以包含0-70重量%,优选至多40重量%的其它添加剂作为组分D)。
本发明模塑组合物可以包含0-3重量%,优选0.05-3重量%,优选0.1-1.5重量%,特别是0.1-1重量%的润滑剂作为组分D)。
优选Al、碱金属或碱土金属盐,或者具有10-44个,优选14-44个碳原子的脂肪酸的酯或酰胺。
金属离子优选为碱土金属和Al,特别优选为Ca或Mg。
优选金属盐为硬脂酸钙和褐煤酸钙以及硬脂酸铝。
还可以使用各种盐以任何所需混合比的混合物。
羧酸可以是一元或二元酸。可以提及的实例为壬酸、棕榈酸、月桂酸、十七烷酸、十二烷二酸、山萮酸,特别优选硬脂酸、癸酸以及褐煤酸(具有30-40个碳原子的脂肪酸的混合物)。
脂族醇可以是一元至四元醇。醇的实例为正丁醇、正辛醇、硬脂醇、乙二醇、丙二醇、新戊二醇、季戊四醇,优选甘油和季戊四醇。
脂族胺可以是一元至三元胺。它们的实例为硬脂胺、乙二胺、丙二胺、六亚甲基二胺、双(6-氨基己基)胺,特别优选乙二胺和六亚甲基二胺。优选的酯或酰胺为相应的甘油二硬脂酸酯、甘油三硬脂酸酯、乙二胺二硬脂酸酯、甘油单棕榈酸酯、甘油三月桂酸酯、甘油单山萮酸酯和季戊四醇四硬脂酸酯。
还可使用各种酯或酰胺或者酯与酰胺以任何所需混合比组合的混合物。
本发明模塑组合物可以包含选自铜化合物、位阻酚、位阻脂族胺和/或芳族胺的热稳定剂或抗氧化剂或它们的混合物作为其它组分D)。
本发明模塑组合物包含0.05-3重量%,优选0.1-1.5重量%,特别是0.1-1重量%的铜化合物(其优选呈Cu(I)卤化物形式,特别是呈与碱金属卤化物(优选KI)特别是1∶4比例的混合物形式)或位阻酚或胺稳定剂或它们的混合物。
优选所用一价铜盐为乙酸亚铜、氯化亚铜、溴化亚铜和碘化亚铜。所述材料包含基于聚酰胺为5-500ppm,优选10-250ppm的铜。
如果铜在聚酰胺中以分子分布存在,则特别获得了有利性能。这可以在将呈固体均相溶液形式的包含聚酰胺和一价铜盐及碱金属卤化物的提浓物加入模塑组合物中时而实现。例如,典型的提浓物由79-95重量%的聚酰胺和21-5重量%的由碘化铜或溴化铜和碘化钾组成的混合物组成。铜在固体均相溶液中的浓度基于该溶液总重优选为0.3-3重量%,特别是0.5-2重量%,并且碘化亚铜与碘化钾的摩尔比为1-11.5,优选为1-5。
对于该提浓物,合适的聚酰胺为均聚酰胺和共聚酰胺,特别是尼龙-6和尼龙-6,6。
合适的位阻酚原则上为任何具有酚结构并在酚环上具有至少一个大基团的化合物。
例如可以优选使用下式化合物:
其中R1和R2为烷基、取代烷基或取代三唑基,其中基团R1和R2可以相同或不同,R3为烷基、取代烷基、烷氧基或取代氨基。
所述类型的抗氧化剂描述于例如DE-A 27 02 661(US-A 4 360 617)中。另一组优选的位阻酚为衍生自取代苯羧酸,特别是取代苯丙酸的那些。特别优选的该类化合物为下式化合物:
其中R4、R5、R7和R8彼此独立地为自身可以具有取代基(它们中的至少一个为大基团)的C1-C8烷基,R6为具有1-10个碳原子且其主链也可具有C-O键的二价脂族基团。
优选的化合物对应于以下这些式:
所有下列物质应当作为位阻酚的实例提及:2,2’-亚甲基双(4-甲基-6-叔丁基苯酚)、1,6-己二醇双[3-(3,5-二叔丁基-4-羟苯基)丙酸酯]、季戊四醇基四[3-(3,5-二叔丁基-4-羟苯基)丙酸酯]、二硬脂基3,5-二叔丁基-4-羟基苄基膦酸酯、2,6,7-三氧杂-1-磷杂双环[2.2.2]辛-4-基甲基3,5-二叔丁基-4-羟基氢化肉桂酸酯、3,5-二叔丁基-4-羟苯基-3,5-二硬脂基硫代三唑基胺、2-(2’-羟基-3’-羟基-3’,5’-二叔丁基苯基)-5-氯苯并三唑、2,6-二叔丁基-4-羟基甲基苯酚、1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯、4,4’-亚甲基双(2,6-二叔丁基苯酚)、3,5-二叔丁基-4-羟基苄基二甲基胺。
已证明特别有效且因此优选使用的化合物为2,2’-亚甲基双(4-甲基-6-叔丁基苯酚)、1,6-己二醇双(3,5-二叔丁基-4-羟苯基]丙酸酯(259)、季戊四醇基四[3-(3,5-二叔丁基-4-羟苯基)丙酸酯]以及N,N’-六亚甲基-双-3,5-二叔丁基-4-羟基氢化肉桂酰胺(1098),并且上述来自CibaGeigy的产品245具有特别好的适用性。
所述材料包含基于模塑组成A)-D)总重为0.05-3重量%,优选0.1-1.5重量%,特别是0.1-1重量%的酚类抗氧化剂,其可以单独使用或以混合物形式使用。
在某些情况下,已证明在酚羟基邻位具有不超过一个位阻基团的位阻酚是特别有利的,特别是当在漫射光中存储长时间后评价颜色坚牢度时。
本发明模塑组合物可以包含0-3重量%,优选0.01-2重量%,优选0.05-1.5重量%的胺稳定剂。位阻胺化合物具有优选的适用性。可以使用的化合物的实例为下式那些:
其中R为相同或不同的烷基,
R’为氢或烷基,及
A为任选取代的2-或3节亚烷基链。
优选组分为2,2,6,6-四甲基哌啶的衍生物,例如:4-乙酰氧基-2,2,6,6-四甲基哌啶、4-硬脂酰氧基-2,2,6,6-四甲基哌啶、4-芳酰氧基-2,2,6,6-四甲基哌啶、4-甲氧基-2,2,6,6-四甲基哌啶、4-苯甲酰氧基-2,2,6,6-四甲基哌啶、4-环己氧基-2,2,6,6-四甲基哌啶、4-苯氧基-2,2,6,6-四甲基哌啶、4-苯甲酰氧基-2,2,6,6-四甲基哌啶、4-(苯氨基甲酰氧基)-2,2,6,6-四甲基哌啶。
其它合适的化合物为双(2,2,6,6-四甲基-4-哌啶基)草酸酯、双(2,2,6,6-四甲基-4-哌啶基)丙二酸酯、双(2,2,6,6-四甲基-4-哌啶基)己二酸酯、双(1,2,2,6,6-五甲基哌啶基)癸二酸酯、双(2,2,6,6-四甲基-4-哌啶基)对苯二甲酸酯、1,2-双(2,2,6,6-四甲基-4-哌啶基氧基)乙烷、双(2,2,6,6-四甲基-4-哌啶基)六亚甲基1,6-二氨基甲酸酯、双(1-甲基-2,2,6,6-四甲基-4-二哌啶基)己二酸酯和三(2,2,6,6-四甲基-4-哌啶基)苯-1,3,5-三甲酸酯。
此外其它具有适用性的化合物为较高分子量哌啶衍生物,例如具有4-羟基-2,2,6,6-四甲基-7-哌啶基乙醇的琥珀酸二甲酯聚合物或聚6-(1,1,3,3-四甲基丁基)氨基-1,3,5-三嗪-2,4-二基(2,2,6,6-四甲基-4-哌啶基)亚氨基-1,6-己烷二基(2,2,6,6-四甲基-14-哌啶基)亚氨基,它们具有特别好的适用性,以及还有双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯。
根据本发明可以使用的其它特别优选的稳定剂的实例为基于芳族仲胺的那些,例如由苯二胺与丙酮产生的加合物(A)、由苯二胺与亚油精产生的加合物445(II)、N,N’-二萘基对苯二胺(III)、N-苯基-N’-环己基对苯二胺(IV)或者这些中两种或更多种的混合物。
可以提及的纤维或颗粒状填料D)为碳纤维、玻璃纤维、玻璃珠、无定形硅石、硅酸钙、偏硅酸钙、碳酸镁、高岭土、白垩、石英粉、云母、硫酸钡和长石,它们的用量为至多40重量%,特别是1-15重量%。
可以提及的优选的纤维填料为碳纤维、芳族聚酰胺纤维和钛酸钾纤维,这里特别优选E玻璃形式的玻璃纤维。它们可以可市购形式的粗纱或短切玻璃形式使用。
纤维填料可以用硅烷化合物进行表面预处理以改进与热塑性塑料的相容性。
合适的硅烷化合物为以下通式的那些:
(X-(CH2)n)k-Si-(O-CmH2m+1)4-k
其中取代基为:
n为2-10,优选3-4的整数
m为1-5,优选1-2的整数
k为1-3的整数,优选为1。
优选的硅烷化合物为氨基丙基三甲氧基硅烷、氨基丁基三甲氧基硅烷、氨基丙基三乙氧基硅烷、氨基丁基三乙氧基硅烷以及相应的包含缩水甘油基作为取代基X的硅烷。
用于表面涂布的硅烷化合物的用量一般为0.01-2重量%,优选为0.025-1.0重量%,特别是0.05-0.5重量%(基于纤维填料)。
针状矿物填料也合适。
对于本发明,针状矿物填料为具有非常显著针状特征的矿物填料。可以提及的实例为针状硅灰石。该矿物的L/D(长度/直径)比优选为8∶1-35∶1,优选为8∶1-11∶1。合适的话,该矿物填料可以用上述硅烷化合物预处理;然而,该预处理不重要。
其它可以提及的填料为高岭土、煅烧高岭土、硅灰石、滑石和白垩以及层状或针状纳米填料,它们的量优选为0.1-10%。优选用于此目的的那些为勃姆石、膨润土、蒙脱石、蛭石、锂蒙脱石和锂皂石。现有技术的层状纳米填料为有机改性的以获得层状纳米填料与有机胶粘剂的好的相容性。将层状或针状纳米填料加入本发明纳米复合物中导致机械强度的进一步增加。
所用滑石特别为组成为Mg3[(OH)2/Si4O10]或3MgO·4 SiO2·H2O的水合硅酸镁。这些“三层叶硅酸盐”具有三斜、单斜或正交晶体结构和层状晶形。其它可以存在的痕量元素为Mn、Ti、Cr、Ni、Na和K,并且羟基可以某种程度上被氟离子取代。
特别优选使用包含99.5%的尺寸<20μm的颗粒的滑石。粒度分布通常经由沉降分析法测定并优选为:
<20μm 99.5重量%
<10μm 99重量%
<5μm 85重量%
<3μm 60重量%
<2μm 43重量%。
这类产品可以Micro-Talc I.T.extra(Omya)市购。
本发明热塑性模塑组合物可以包含常规加工助剂如稳定剂、氧化抑制剂、其它抗热分解或紫外光分解的试剂、润滑剂、脱模剂、着色剂如染料和颜料、成核剂、增塑剂、阻燃剂等。
可以提及的氧化抑制剂和热稳定剂的实例为亚磷酸盐和其它胺(如TAD)、氢醌、这些基团的各种取代物及其混合物,浓度基于该热塑性模塑组合物的重量为至多1重量%。
可以提及的紫外稳定剂(它们的用量基于该模塑组合物通常为至多2重量%)为各种取代的间苯二酚、水杨酸盐、苯并三唑类和二苯甲酮类。
可以添加的着色剂为无机颜料如二氧化钛、群青蓝、氧化铁和炭黑和/或石墨以及有机颜料如酞菁、喹吖啶酮、苝以及染料如苯胺黑和蒽醌。
还可以使用阻燃剂如红磷。
可以使用的成核剂为苯基次膦酸钠、氧化铝、二氧化硅,优选滑石。
本发明热塑性模塑组合物可以通过本身已知的方法通过在常规混合设备如螺旋挤出机、布雷本登混合机或班伯里混合机混合起始组分并将它们挤出而制备。可以冷却并粉碎挤出物。还可以预混各组分,然后单独添加剩余原料和/或同样混合。混合温度通常为230-320℃。
在另一个优选的程序中,组分B)-C)以及合适的话D)可以与预聚物混合、配混和造粒。然后在惰性气体下将所得粒料在低于组分A)熔点的温度下连续或分批固相冷凝,直到达到所需粘度。优选将含有固体的分散体形式的乳液聚合物B)掺入熔体A)中。
本发明热塑性模塑组合物的特征在于良好的韧性(特别是好的断裂能)与良好的抗紫外性和耐热性。
这些材料适于生产纤维、箔和任何类型的模制品。下面将提及一些优选的实例:家居用品、电子元件、医疗设备、汽车组件。
实施例
使用以下组分:
组分A:
组分B1:
如下制备组分B1:
将800g去离子水、39.70g含水聚苯乙烯种子(固体含量33重量%,数均粒径32nm)、198.4g 1-辛烯、3.28g 50重量%浓度的乳化剂水溶液、19.65g 20重量%浓度的Lutensol TO 20乳化剂水溶液和19.65g 7重量%浓度的过二硫酸钠水溶液用作初始进料在20-25℃(室温)下在氮气下加入4l配置有锚式搅拌器、回流冷凝器和两个进料装置的四颈烧瓶中并搅拌加热至90℃。在90℃下开始,由600g去离子水、3.28g 40重量%浓度的乳化剂水溶液、19.65g 20重量%浓度的Lutensol TO 20乳化剂水溶液、8.38g 25重量%浓度的氢氧化钠水溶液、1076.82g丙烯酸正丁酯、26.20g丙烯酸和10.48g甲基丙烯酸烯丙酯组成的单体进料和由111.35g 7重量%浓度的过二硫酸钠水溶液组成的引发剂进料同时开始,并且单体进料在3小时内连续供入[以2步,0.5小时内500g(1000g/小时),2.5小时内1245g(498g/小时)],引发剂进料在3.5小时内连续供入。然后使所得聚合物水分散体在90℃下继续反应另外2小时。然后将聚合物水分散体冷却至室温并混入65.5g 10重量%浓度的氢氧化钠水溶液。聚合物水分散体的固体含量基于该水分散体总重为44重量%。聚合物的玻璃化转变温度为-42℃。聚合物粒径为105nm。通过在真空中排出水使固体含量增加至49%。
组分Bcomp 1:
乙烯丙烯酸正丁酯-丙烯酸共聚物如来自BASF AG的KR1270。
组分Bcomp 2:
组分C:
基于苯乙烯/丙烯腈/马来酐(75/24.1/0.9)的三元聚合物,粘数根据DIN53728为80ml/g(在25℃下在0.5%浓度DMF溶液中测量)。
组分D:
滑石如来自Omya的IT-Extra滑石。
模塑组合物的制备和测试:
根据DIN 53 727在96重量%硫酸中以0.5重量%浓度溶液测定聚酰胺的粘数。
通过在干燥箱中在140℃下将规定量的聚合物水分散体(约5g)干燥至恒重而测定固体含量。分别测量两次。实施例中所述值为这两次测量结果的平均值。
根据DIN 53 765借助来自Mettler-Toledo的TA 8000 DSC 820系列设备测定玻璃化转变温度。
借助维卡软化点根据标准小样品测定样品的耐热性。根据DIN 53 460使用49.05N的力和每小时50K的温度增加测定维卡软化点。
根据ISO 6603在瓷花金属板(60×60×3mm)上测定断裂能。根据Volkswagen AG PV 1303进行紫外老化。
根据ISO 1133使用240℃和5kg负载测定流动性。
在双螺杆挤出机中在240-260℃的熔融温度下混合各组分。此时将组分B1的乳液供入组分A熔体中。通过两个真空通气口除去水。将熔体通过水浴并造粒。
测试结果列在表1中。
表1
模塑组合物 | 组分1 | 组分2 | 3 | 组分4 | 5 | 组分6 | 7 |
A | 80 | 80 | 80 | 75 | 75 | 70 | 70 |
B1 | - | - | 20 | - | 20 | - | 20 |
Bcomp1 | 20 | - | - | 20 | - | 20 | - |
Bcomp2 | - | 20 | - | - | - | - | - |
C | - | - | - | 5 | 5 | - | - |
D | - | - | - | - | - | 10 | 10 |
维卡B[℃] | 156 | 157 | 162 | 154 | 163 | 153 | 161 |
MVI[ml/10’] | 16.5 | 16.4 | 11.7 | 11.2 | 9.1 | 14.3 | 10.5 |
Ws,RT,0h[Nm] | 80 | 43 | 84 | 71 | 73 | 67 | 78 |
Ws,500h[Nm] | 34 | 34 | 76 | 29 | 65 | 23 | 71 |
Ws,1000h[Nm] | 27 | 23 | 73 | 17 | 61 | 15 | 67 |
Ws,-30℃[Nm] | 67 | 11 | 79 | 56 | 60 | 45 | 55 |
Claims (7)
1.一种热塑性模塑组合物,包含
A)10-95重量%的热塑性聚酰胺,
B)5-90重量%的丙烯酸酯橡胶,通过在至少一种分散剂和至少一种自由基引发剂的存在下使烯键式不饱和单体进行自由基引发水乳液聚合获得,其中乳液聚合使用:
1-50重量%的具有5-12个碳原子的链烯[单体A],和
50-99重量%的基于具有3-6个碳原子的α,β-单烯键式不饱和单-或二羧酸和具有1-12个碳原子的链烷醇的酯[单体B],以及合适的话
至多10重量%的具有3-6个碳原子的α,β-单烯键式不饱和单-或二羧酸和/或其酰胺[单体C],和
至多30重量%的不同于单体A-C的α,β-烯键式不饱和化合物[单体D],并且单体A-D一共为100重量%,
C)0-40重量%的包含乙烯基芳族单体单元的共聚物和
D)0-70重量%的其它添加剂,
其中A)-D)的总重量百分数为100%。
2.根据权利要求1的热塑性模塑组合物,其中经由以下组分的乳液聚合获得丙烯酸酯橡胶B:
1-49.99重量%的单体A,
50-98.99重量%的单体B,以及
0.01-10重量%的单体C。
3.根据权利要求1或2的热塑性模塑组合物,其中将1-链烯用作丙烯酸酯橡胶B)的单体A。
4.根据权利要求1-3中任一项的热塑性模塑组合物,其中将基于具有3或4个碳原子的α,β-单烯键式不饱和单-或二羧酸和基于具有1-8个碳原子的链烷醇的酯用作单体B。
5.根据权利要求1-4中任一项的热塑性模塑组合物,包含
A)20-94重量%
B)5-40重量%
C)1-30重量%
D)0-40重量%。
6.权利要求1-5中任一项的热塑性模塑组合物在生产纤维、箔和模制品中的用途。
7.由根据权利要求1-5中任一项的热塑性模塑组合物获得的模制品。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP06125991 | 2006-12-13 | ||
EP06125991.7 | 2006-12-13 |
Publications (1)
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CN101558119A true CN101558119A (zh) | 2009-10-14 |
Family
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CNA200780046008XA Pending CN101558119A (zh) | 2006-12-13 | 2007-12-05 | 含丙烯酸酯橡胶的聚酰胺 |
Country Status (9)
Country | Link |
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US (1) | US7960477B2 (zh) |
EP (1) | EP2099866B1 (zh) |
JP (1) | JP5431168B2 (zh) |
KR (1) | KR101368128B1 (zh) |
CN (1) | CN101558119A (zh) |
BR (1) | BRPI0720299A2 (zh) |
ES (1) | ES2555519T3 (zh) |
MY (1) | MY146531A (zh) |
WO (1) | WO2008071603A2 (zh) |
Cited By (2)
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CN106543707A (zh) * | 2016-10-28 | 2017-03-29 | 上海耐特复合材料制品有限公司 | 耐低温超韧性尼龙复合材料及其制备方法 |
CN107400323A (zh) * | 2017-08-29 | 2017-11-28 | 常熟市中联光电新材料有限责任公司 | 一种聚酰胺组合物/丙烯酸酯橡胶动态硫化胶及其制备方法 |
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CN101955767B (zh) * | 2010-08-16 | 2013-01-09 | 大庆高新区华龙祥化工有限公司 | 一种用于三次采油化学驱油剂的双子表面活性剂及其制备方法 |
EP2723811B1 (en) | 2011-06-21 | 2015-08-26 | E. I. du Pont de Nemours and Company | Heat-stabilised polyamide-filled acrylate copolymer and process for its production |
EP2580285B8 (en) * | 2011-06-21 | 2014-02-19 | E. I. Du Pont de Nemours and Company | Process for production of a heat-stabilised polyamide-filled acrylate polymer |
PL2719726T3 (pl) * | 2012-10-10 | 2017-09-29 | Lanxess Deutschland Gmbh | Kompozycje do formowania |
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- 2007-12-05 US US12/519,030 patent/US7960477B2/en not_active Expired - Fee Related
- 2007-12-05 KR KR1020097014452A patent/KR101368128B1/ko not_active IP Right Cessation
- 2007-12-05 ES ES07857254.2T patent/ES2555519T3/es active Active
- 2007-12-05 JP JP2009540718A patent/JP5431168B2/ja not_active Expired - Fee Related
- 2007-12-05 BR BRPI0720299-7A patent/BRPI0720299A2/pt not_active IP Right Cessation
- 2007-12-05 EP EP07857254.2A patent/EP2099866B1/de not_active Not-in-force
- 2007-12-05 MY MYPI20092437A patent/MY146531A/en unknown
- 2007-12-05 WO PCT/EP2007/063329 patent/WO2008071603A2/de active Application Filing
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN106543707A (zh) * | 2016-10-28 | 2017-03-29 | 上海耐特复合材料制品有限公司 | 耐低温超韧性尼龙复合材料及其制备方法 |
CN106543707B (zh) * | 2016-10-28 | 2018-02-02 | 上海耐特复合材料制品有限公司 | 耐低温超韧性尼龙复合材料及其制备方法 |
CN107400323A (zh) * | 2017-08-29 | 2017-11-28 | 常熟市中联光电新材料有限责任公司 | 一种聚酰胺组合物/丙烯酸酯橡胶动态硫化胶及其制备方法 |
Also Published As
Publication number | Publication date |
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JP5431168B2 (ja) | 2014-03-05 |
US20100048821A1 (en) | 2010-02-25 |
US7960477B2 (en) | 2011-06-14 |
WO2008071603A3 (de) | 2008-11-20 |
ES2555519T3 (es) | 2016-01-04 |
EP2099866A2 (de) | 2009-09-16 |
KR101368128B1 (ko) | 2014-02-27 |
WO2008071603A2 (de) | 2008-06-19 |
EP2099866B1 (de) | 2015-09-23 |
KR20090087510A (ko) | 2009-08-17 |
JP2010513580A (ja) | 2010-04-30 |
BRPI0720299A2 (pt) | 2014-02-04 |
MY146531A (en) | 2012-08-15 |
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