CN106661270A - 羟基苯并三唑衍生物和/或羟基吲唑衍生物作为塑料材料的阻燃剂的用途以及阻燃塑料材料模塑料 - Google Patents
羟基苯并三唑衍生物和/或羟基吲唑衍生物作为塑料材料的阻燃剂的用途以及阻燃塑料材料模塑料 Download PDFInfo
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- CN106661270A CN106661270A CN201580031450.XA CN201580031450A CN106661270A CN 106661270 A CN106661270 A CN 106661270A CN 201580031450 A CN201580031450 A CN 201580031450A CN 106661270 A CN106661270 A CN 106661270A
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- LRGQZEKJTHEMOJ-UHFFFAOYSA-N propane-1,2,3-triol;zinc Chemical compound [Zn].OCC(O)CO LRGQZEKJTHEMOJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
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Abstract
本发明涉及N‑羟基苯并三唑衍生物,特别是N‑羟基苯并三唑盐和/或N‑羟基吲唑,特别是N‑羟基吲唑盐作为塑料材料的阻燃剂的用途。本发明还涉及阻燃塑料材料模塑料,其包含作为阻燃剂的N‑羟基苯并三唑衍生物和/或N‑羟基吲唑衍生物。
Description
本发明涉及N-羟基苯并三唑衍生物,特别是N-羟基苯并三唑盐和/或N-羟基吲唑,特别是N-羟基吲唑盐作为塑料材料的阻燃剂的用途。本发明还涉及阻燃塑料材料模塑料,其包含作为阻燃剂的N-羟基苯并三唑衍生物和/或N-羟基吲唑衍生物。
大多数塑料材料,例如基于聚烯烃、聚苯乙烯、聚酰胺、聚氨酯或聚酯的塑料材料是可燃的并且相对易于燃烧。为了在特定应用中防止或排除塑料材料的火灾危险,因此必需要降低可燃性并使用防火或阻燃塑料材料组合物。通常,为了达到防止在特定时间的着火或显著地延迟火势蔓延的目的,在塑料材料中加入阻燃剂。传统的阻燃剂是基于含氯化合物和含溴化合物(主要与三氧化锑组合),含磷化合物,含氮化合物和/或无机氢氧化物。近来,出于环境原因和/或毒理学观点,无卤素阻燃溶液已成为优选。
为了生产阻燃塑料材料,存在大量的阻燃剂,其通常被用作特定聚合物和相应于构成其基础的国家标准和国际标准的特定使用区域的特定基材。阻燃塑料材料例如被用在电气和电子应用中、运输/汽车领域中、纺织品中、软垫家具和建筑中。
在过去几年中开发了一类非常有效的基于氮的阻燃剂,优选是基于烷氧基胺的聚烯烃(WO 99/00450、WO 2008101845、WO 2011086114)。在着火的情况下通过分裂烷氧基胺键产生自由基介入聚合物的分解过程,从而实现阻燃效果(C.R.Wilen,R.Pfaendner,J.Appl.Pol.Sci.129(2013),925-944,R.Pfaendner,C.R.Chemistry 9(2006),1338-1344)。烷氧基胺也可有利地用于与其它阻燃剂的协同组合(WO 02/074847、WO 03/016388、WO 2010026230、WO 2009080554、WO 2011003773、WO 2011117266)。此外,甚至发现羟胺稳定剂可以实现协同提高含溴、含磷和无机阻燃剂的效果(WO 02/074847)。
然而,许多已知和提到的自由基生成剂不能满足有效阻燃剂的所有要求,例如,足够的热稳定性,即在常温下掺入塑料材料(复合),阻燃剂已经发生过早地、即不希望的分解。这种过早分解的结果是,在着火的情况下会使效果降低和/或由于随后的反应,而对待保护的塑料材料的性质具有负面影响。因此,希望可以用作阻燃剂或阻燃增效剂的自由基生成剂在塑料材料加工期间、即通常高于300℃具有足够高的温度稳定性,但由于其能够快速分解而随后在着火的情况下实现特别好的效果。
因此,本发明的目的是提供高度有效并具有非常好的热稳定性的新型阻燃剂和协同阻燃组分。
通过专利权利要求1的特征:关于特定的N-羟基苯并三唑和/或N-羟基吲哚作为塑料材料的阻燃剂的用途实现了该目的。此外,根据专利权利要求7,本发明涉及包含至少一种N-羟基苯并三唑和/或至少一种N-羟基吲唑作为阻燃剂的阻燃塑料材料模塑料。因此相应的从属专利权利要求体现了有利的进展。
羟基苯并三唑是工业上可获得的原料,例如用于肽合成(B.Bacsa et al.,J.Org.Chem.2008,73,7532-7542)。然而,羟基苯并三唑在干燥状态下具有爆炸性并且对冲击敏感,因此储存在水溶液或湿润条件中,所以通常不能用于塑料材料加工过程,特别是所需求的加工温度下。相反,羟基苯并三唑盐是热稳定很强的化合物,并且通常仅在300℃以上才分解。
苯并三唑衍生物通常是最好的已知种类的UV稳定剂之一,然而这些衍生物结构不同(无羟基苯并三唑和无盐(no hydroxybenzotriazoles and no salts),参见塑料添加剂手册,第五版,出版人:H.Zweifel(H.茨魏费尔),汉泽尔(Hanser),慕尼黑(Munich)2001),因此,不具有作为阻燃剂和/或阻燃增效剂的效果。
迄今还不知道羟基苯并三唑盐在塑料材料中,特别是作为阻燃剂的用途。
令人惊讶的是,现在发现了N-羟基苯并三唑衍生物和/或N-羟基吲唑衍生物非常适合作为塑料材料组合物的阻燃剂。
因此,本发明涉及根据通式I至IV的化合物或至少两种通式I至IV的化合物的混合物作为塑料材料的阻燃剂的用途,
其中,在各种情况中,各自彼此独立的,
R1选自由氢,具有1至18个碳原子的烷基,具有1至18个碳原子的部分或全氟烷基,具有至多1至18个碳原子的不饱和有机基团,两个邻位基团R1能够连接形成的环,-NO2,-F,-Cl和-Br组成的组,和
R2选自由一价、二价或三价无机阳离子,或一价、二价或三价有机阳离子和氢组成的组。
在上述根据通式I至IV的化合物的情况下,分别优选地,R1选自氢,R2选自1-或2-价无机阳离子,或1-或2-价有机阳离子。
在根据式I至IV的化合物中,特别优选根据式I的化合物。
根据优选实施例,一价、二价或三价无机阳离子选自由Li+、Na+、K+、1/2Mg2+、1/2Ca2 +、1/3Al3+、1/2Zn2+组成的组和/或有机阳离子选自由含氮有机阳离子和/或含磷有机阳离子,特别是铵,三聚氰铵和鏻组成的组。
上述使用的命名法中2-或3-价阳离子(例如1/2Mg2+等)表示阳离子相对于根据式I至IV的一价阴离子以正确的化学计量比存在。
特别有利的是,在各种情况中,R1是氢和/或R2是一价或二价无机阳离子,特别是K+。
对于可以使用上述根据式I至IV的化合物来赋予阻燃的待保护的塑料材料,本发明不受限制。因此,优选地,待保护的塑料材料选自由热塑性材料、弹性体材料或热固性材料组成的组,特别是:
a)由烯烃或二烯烃构成的聚合物,例如聚乙烯(低密度聚乙烯(LDPE)、线性低密度聚乙烯(LLDPE)、极低密度聚乙烯(VLDPE)、超低密度聚乙烯(ULDPE)、中密度聚乙烯(MDPE)、高密度聚乙烯HDPE、超高分子量聚乙烯(UHMWPE)),茂金属-聚乙烯(m-PE),聚丙烯,聚异丁烯,聚-4-甲基戊烯-1,聚丁二烯,聚异戊二烯,聚环辛烯,聚亚烷基-一氧化碳共聚物,以及具有统计或嵌段结构形式的共聚物,例如聚丙烯-聚乙烯(EP),二元乙丙橡胶(EPM)或三元乙丙橡胶(EPDM),乙烯-乙酸乙烯酯(EVA);乙烯-丙烯酸酯,例如乙烯-丙烯酸丁酯,乙烯-丙烯酸及其盐(离聚物),以及三元共聚物,例如乙烯-丙烯酸-缩水甘油基丙烯酸酯;接枝聚合物,例如聚丙烯-接枝-马来酸酐,聚乙烯-接枝-丙烯酸,聚乙烯-聚丙烯酸丁酯-接枝-马来酸酐,
b)聚苯乙烯,聚甲基苯乙烯,聚乙烯基萘,苯乙烯-丁二烯(SB),苯乙烯-丁二烯-苯乙烯(SBS),苯乙烯-乙烯-丁烯-苯乙烯(SEBS),苯乙烯-乙烯-丙烯-苯乙烯,苯乙烯-异戊二烯,苯乙烯-异戊二烯-苯乙烯(SIS),苯乙烯-丁二烯-丙烯腈(ABS),苯乙烯-丙烯腈-丙烯酸酯(ASA),苯乙烯-乙烯,苯乙烯-马来酸酐聚合物,包括相应的接枝共聚物,例如丁二烯接枝苯乙烯,SBS或SEBS接枝马来酸酐,以及由甲基丙烯酸甲酯,苯乙烯-丁二烯和ABS(MABS)构成的接枝共聚物,
c)含卤聚合物,例如聚氯乙烯(PVC),聚氯丁二烯和聚偏二氯乙烯(PVDC),由氯乙烯和偏二氯乙烯、或氯乙烯和乙酸乙烯酯构成的共聚物,氯化聚乙烯,聚偏二氟乙烯,
d)不饱和酯的聚合物,例如聚丙烯酸酯和聚甲基丙烯酸酯,例如聚甲基丙烯酸甲酯(PMMA),聚丙烯酸丁酯,聚丙烯酸月桂酯,丙烯酸聚硬脂酯,聚丙烯酸缩水甘油酯,聚甲基丙烯酸缩水甘油酯,聚丙烯腈,聚丙烯酰胺;共聚物例如聚丙烯腈-聚丙烯酸烷基酯,
e)由不饱和醇和衍生物构成的聚合物,例如聚乙烯醇,聚乙酸乙烯酯,聚乙烯醇缩丁醛,
f)聚缩醛,例如聚甲醛(POM),或例如与丁醛形成的共聚物,
g)聚苯醚和与聚苯乙烯或聚酰胺的共混物,
h)环醚的聚合物,例如聚乙二醇,聚丙二醇,聚环氧乙烷,聚环氧丙烷,
i)聚氨酯,由羟基封端的聚醚或聚酯和芳族或脂族异氰酸酯构成,特别是线性聚氨酯,聚脲,
j)聚酰胺,例如聚酰胺-6,6.6,6.10,4.6,4.10,6.12,12.12,聚酰胺11,聚酰胺12以及(部分)芳族聚酰胺,例如聚邻苯二甲酰胺,例如,由对苯二甲酸和/或间苯二甲酸和脂族二胺或由脂族二羧酸制备,例如,己二酸或癸二酸和芳族二胺,例如,1,4-或1,3-二氨基苯;不同聚酰胺的共混物,例如聚酰胺(PA)-6和PA 6.6或聚酰胺和聚烯烃的共混物,例如聚酰胺/聚丙烯(PA/PP),
k)聚酰亚胺,聚酰胺酰亚胺,聚醚酰亚胺,聚酯酰亚胺,聚(醚)酮,聚砜,聚醚砜,聚芳砜,聚苯硫醚,聚苯并咪唑,聚乙内酰脲,
l)由脂族或芳族二羧酸和二醇构成或由羟基羧酸构成的聚酯,例如聚对苯二甲酸乙二醇酯(PET),聚对苯二甲酸丁二醇酯(PBT),聚对苯二甲酸丙二醇酯,聚萘二甲酸乙二醇酯,聚-1,4-二甲基环己烷对苯二甲酸酯,聚羟基苯甲酸酯,聚羟基萘二甲酸酯,聚乳酸(PLA),聚羟基丁酸酯(PHB),聚羟基戊酸酯(PHV),
m)聚碳酸酯,聚酯碳酸酯,以及共混物,例如PC/ABS、PC/PBT、PC/PET/PBT、PC/PA,
n)纤维素衍生物,例如硝酸纤维素,乙酸纤维素,丙酸纤维素,丁酸纤维素,
o)非热塑性或热固性(duroplastic)塑料材料,
p)以及两种或多种前述聚合物的混合物、组合物或共混物。
根据通式I至IV的化合物或至少两种式I至IV的化合物的混合物的用途优选存在于与塑料材料混合的相应化合物中。因此有利的是,在所得混合物中根据通式I和II的化合物的总含量优选为0.01至50重量%,更优选为0.05至25重量%。
此外,本发明涉及阻燃塑料材料模塑料,包含至少一种塑料材料以及作为阻燃剂的至少一种根据通式I至IV的化合物或至少两种通式I至IV的化合物的混合物,其中在各种情况中各自彼此独立的,
R1选自由氢,具有1至18个碳原子的烷基,具有1至18个碳原子的部分或全氟烷基,至多1至18个碳原子的不饱和有机基团,2个邻位R1基团能够连接形成的环,-NO2,-F,-Cl和-Br组成的组,和
R2选自由一价、二价或三价无机阳离子,或一价、二价或三价有机阳离子和氢组成的组。
关于化合物I至IV的优选选择,与上文已经描述的相同解释一样适用。
根据优选实施例,在塑料材料模塑料中根据通式I至IV的至少一种化合物的总含量是0.01到50重量%,优选的0.05到25重量%。
因此,进一步有利的是,除了至少一种根据通式I至IV的化合物和至少一种塑料材料之外,相对于至少一种根据通式I和II的化合物和至少一种塑料材料的总量,塑料材料模塑料还包含至多70重量份、优选至多25重量份的至少一种另外的阻燃剂,所述另外的阻燃剂选自由含磷、含氮、无机、含硅、含硼、含卤素、含硫和/或自由基形成的阻燃剂组成的组。
假如如a)至o)所示的聚合物、或两种或更多种这些聚合物的混合物或共混物涉及共聚物,这些共聚物可以以统计(“无规”)、嵌段或“递变”结构的形式存在。
假如如a)至o)所示的聚合物或这些聚合物中的两种或更多种的混合物或共混物涉及有规立构聚合物,这些聚合物可以以全同立构、立体定向形式存在,但也可以以无规立构形式存在。
此外,如a)至o)所示的聚合物或这些聚合物中两种或更多种的混合物或共混物可以具有无定形和(部分)结晶形态。
因此,所提及的聚合物a)至o)不仅可以作为原生材料存在,而且可以以回收物形式存在,例如作为生产废物或从有用的材料收集中得到(“消费后”回收物)。
可能地,在a)中提及的聚烯烃也可以存在交联,例如之后被称为X-PE的交联聚乙烯。在a)中提及的聚烯烃可具有任意立体结构,即全同立构、间同立构或无规立构,或以立构嵌段结构存在。
极其特别优选地,根据本发明使用的有机氧酰亚胺(oxyimide)被用于聚烯烃,特别是用于a)中提及的聚烯烃。
此外,本阻燃剂可用于以下的热固性或弹性体、非热塑性塑料材料中:
q)环氧树脂,由二官能或多官能环氧化合物与例如基于胺、酸酐、二氰基二酰胺、硫醇、异氰酸酯的硬化剂或催化作用的硬化剂组合而成,
r)酚树脂,例如酚醛树脂,脲醛树脂,三聚氰胺-甲醛树脂,
s)由不饱和二羧酸和二醇构成的不饱和聚酯树脂,
t)硅酮,
u)作为二官能或多官能异氰酸酯和多元醇的聚氨酯、聚脲,
v)醇酸树脂、烯丙树脂。
同样可能的是前述塑料材料彼此之间的混合物、共混物和组合物,或者与前面a)至o)中提到的塑料材料的混合物和组合物。
极其特别优选地,根据本发明的阻燃剂用于聚烯烃,优选聚丙烯和/或聚乙烯及其共聚物和共混物的情况中。
特别优选的是,如果根据本发明使用的根据式I至IV的阻燃剂与至少一种另外的阻燃剂组合使用,则由此产生协同效果。因此,所述至少一种另外的阻燃剂优选自由以下组成的组:
a)无机阻燃剂,例如Al(OH)3,Mg(OH)2,AlO(OH),MgCO3,层硅酸盐,例如蒙脱石或海泡石,有机或未改性的复盐,例如Mg-Al硅酸盐,POSS-(多面体低聚倍半硅氧烷)化合物,碳酸钙镁石,水菱镁矿或多水高岭土以及Sb2O3,Sb2O5,MoO3,锡酸锌,羟基锡酸锌,
b)含氮阻燃剂,例如三聚氰胺,蜜勒胺,蜜白胺,氰脲酰胺(melon),三聚氰胺衍生物,三聚氰胺缩合产物或三聚氰胺盐,苯并胍胺,聚异氰脲酸酯,尿囊素,磷腈(phosphacene),特别是三聚氰胺氰尿酸盐,磷酸三聚氰胺,磷酸二蜜胺,焦磷酸三聚氰胺,多磷酸三聚氰胺,三聚氰胺甲烷膦酸盐,三聚氰胺-金属磷酸盐,例如三聚氰胺磷酸铝,三聚氰胺磷酸锌,三聚氰胺磷酸镁,以及相应的焦磷酸盐和多磷酸盐,乙二胺甲烷膦酸盐,聚-[2,4-(哌嗪-1,4-基)-6-(吗啉-4-基)-1,3,5-三嗪],多磷酸铵,三聚氰胺硼酸盐,三聚氰胺氢溴酸盐,
c)自由基形成剂,例如烷氧基胺,羟胺酯,偶氮化合物,二枯基或聚枯基,羟基酰亚胺或其衍生物,例如羟基酰胺酯或羟基酰胺醚,
d)含磷阻燃剂,例如红磷,磷酸盐,例如间苯二酚二磷酸酯,双酚A二磷酸酯及其低聚物,磷酸三苯酯,二磷酸乙二胺,膦酸盐例如次磷酸的盐及其衍生物,例如烷基次膦酸盐,例如二乙基次膦酸铝或二乙基次膦酸锌或次膦酸铝,亚磷酸铝,膦酸铝,磷酸铝,膦酸酯,甲烷膦酸的低聚和聚合衍生物,9,10-二氢-9-氧杂-10-磷酰基菲-10-氧化物(DOPO)及其取代化合物,
e)基于氯和溴的含卤阻燃剂,例如多溴二苯醚,例如十溴二苯醚,(3-溴-2,2-双(溴甲基)丙基磷酸酯,磷酸三(三溴新戊基)酯,四溴邻苯二甲酸,1,2-二(三溴苯氧基)乙烷,六溴环十二烷,溴二苯乙烷,三(2,3-二溴丙基)异氰脲酸酯,亚乙基-双(四溴邻苯二甲酰亚胺),四溴双酚A,四溴双酚-A-双(2,3-二溴丙基醚),溴化聚苯乙烯,溴化聚丁二烯或聚苯乙烯,溴化聚丁二烯共聚物,溴化环氧树脂,聚丙烯酸苄酯,溴化聚苯醚,可能与Sb2O3和/或Sb2O5组合,
f)硼酸盐,例如硼酸锌或硼酸钙,可能在载体材料如二氧化硅,
g)含硫化合物,例如元素硫,二硫化物和多硫化物,硫脲硫化物,二硫代氨基甲酸盐,巯基苯并噻唑和次磺酰胺,
h)防滴剂,例如聚四氟乙烯,
i)含硅化合物,例如聚苯基硅氧烷,
j)碳改性,例如碳纳米管(CNT)或石墨烯。
在e)中提到的含卤阻燃剂,通常涉及可购商业产品,例如从雅宝(Albemarle)、科聚亚(Chemtura)/大湖(Great Lakes)或ICL-IP公司中购买。
特别是在根据本发明使用的根据式I至IV的化合物与至少一种作为另外的阻燃剂的自由基形成剂的组合物中,产生协同效果。
本发明意义上的自由基形成剂是可以通过热和光诱导分裂产生自由基的化合物。本文应用中合适的自由基形成剂是对于塑料材料或涂层加工方法具有足够的热稳定性的那些自由基形成剂,即在加工过程中始终不产生或仅产生非常少量的自由基,而仅在着火的较高温度下自发产生自由基。用于涂层和塑料材料加工过程的各个加工过程和温度是本领域技术人员所公知的。然而,塑料材料加工过程和相关温度也可以从技术文献中推导出,例如H.Domininghaus,P.Elsner,P.Eyerer,T.Hirth,Plastic Materials,8th edition,Springer 2012。
因此,自由基形成剂优选选自由N-烷氧基胺,-C-C-自由基形成剂,具有偶氮基(-N=N-)的自由基形成剂,具有肼基(-NH-HN-)的自由基形成剂,具有腙基(>C=N-NH-)的自由基形成剂,具有吖嗪基团(>C=N-N=C<)的自由基形成剂,具有三氮烯基团(-N=N-N<)的自由基形成剂组成的组。
合适的偶氮化合物的制备例如如M.Aubert et al.Macromol.Sci.Eng.2007,292,707-714或WO 2008101845所述,腙和吖嗪的制备如M.Aubert et al.,Pol.Adv.Technol.2011,22,1529-1538所述,三氮烯的制备如W.Pawelec et al.,Pol.Degr.Stab.2012,97,948–954所述。
因此,自由基形成剂特别优选选自由以下组成的组:
a)根据如下结构式所示的N-烷氧基胺
其中
R3代表氢或可能取代的烷基-、环烷基、芳基-、杂芳基-或酰基,特别是C1-C4烷基,
R4代表烷氧基-、芳氧基-、环烷氧基-、芳烷氧基-或酰氧基,
Z代表氢或可能取代的烷基-、环烷基-、芳基-、杂芳基-或酰基,两个基团Z能够形成闭合环,其可以被酯-、醚-、胺、酰胺、羧基或氨基甲酸酯基团所取代,
b)根据如下结构式所示的偶氮化合物
R5-N=N-R5或者
其中
R5是指烷基-、环烷基-或芳基,
R6在各种情况中是相同或不同的,是指直链或支链烷基,
R7在各种情况中是相同或不同的,是指氢或直链或支链烷基,和
R8在各种情况中是相同或不同的,是指烷基、烷氧基-、芳氧基-、环烷氧基-、芳烷氧基或酰氧基,
c)根据如下结构式所示的二枯基
R7具有前述含义,优选为甲基,
d)和/或根据如下结构式所示的聚枯基
R7具有前述含义,优选为甲基,且2<n<100。
因此,如上所述结构的N-烷氧基胺的典型示例是:
1-环己氧基-2,2,6,6-四甲基-4-十八烷基氨基哌啶;双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)癸二酸酯;2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-(2-羟乙基氨基-S-三嗪;己二酸双(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)酯;2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-S-三嗪;1-(2-羟基-2-甲基丙氧基)-4-羟基-2,2,6,6-四甲基哌啶;1-(2-羟基-2-甲基丙氧基)-4-氧代-2,2,6,6-四甲基哌啶;1-(2-羟基-2-甲基丙氧基)-4-十八酰氧基-2,2,6,6-四甲基哌啶;双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)癸二酸酯;双(1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基)己二酸酯;2,4-双{N-[1-(2-羟基-2-甲基丙氧基)-2,2,6,6-四甲基哌啶-4-基]-N-丁基氨基}-6-(2-羟基乙基氨基)-S-三嗪);4-哌啶醇,2,2,6,6-四甲基-1-(十一烷氧基)-4,4'-碳酸酯;2,4-双[(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)丁基氨基]-6-氯-S-三嗪和N,N'-双(3-氨基丙基乙二胺)的反应产物;4,4'-六亚甲基-双(氨基-2,2,6,6-四甲基哌啶)和2,4-二氯-6-[(1-环己氧基-2,2,6,6-四甲基-4-基)丁基氨基]-S-三嗪经过缩合反应,用2-氯-4,6-双(二丁基氨基)-S-三嗪封端得到的低聚物;脂族羟胺,例如二硬脂基羟胺;以及下式的化合物
其中n=1-15。
上述化合物部分是可购商业产品,并且以以下商品名出售:巴斯夫公司(BASF SE)的FLAMESTAB NOR 116(RTM)、TINUVIN NOR 371(RTM)、IRGATEC CR 76(RTM),科莱恩公司(Clariant)的Hostavin NOW(RTM)或者艾迪科公司(Adeka)的ADK Stab LA 81(RTM)。二枯基和聚枯基是可以从例如优耐德引发剂公司(United Initiators)获得的商业产品。
含硫阻燃剂同样是具有二硫化物或多硫化物基团(-S-S-)或硫醇基团(-S-H)的自由基形成剂,以及硫脲硫化物,例如四甲基秋兰姆二硫化物,二硫代氨基甲酸盐,例如二乙基二硫代氨基甲酸锌或二甲基二硫代氨基甲酸钠,巯基苯并噻唑,例如2-巯基苯并噻唑和次磺酰胺,例如N,N-二环己基-2-苯并噻唑次磺酰胺。
多硫化物的示例是元素硫,例如如US 4218332所述的其它多硫化物。
二硫化物、多硫化物、硫醇、硫脲硫化物、二硫代氨基甲酸盐、巯基苯并噻唑和次磺酰胺可通过商购获得。
其它合适的自由基形成剂是羟基酰亚胺及其衍生物,例如羟基酰亚胺酯或羟基酰亚胺醚,例如WO 2014/154636所述。
根据本发明的羟基苯并三唑盐与另外的自由基形成剂的组合可以是特别有利的,因为这些自由基形成可以在不同的分解温度下进行或者可以根据需要进行调节。
所述至少一种另外的阻燃剂还可以特别是含磷阻燃剂。优选的含磷阻燃剂是具有以下结构的次膦酸盐:
其中R1和R2优选相同或不同,并且选自直链或支链C1-C6烷基和/或芳基;M是选自Mg,Ca,Al,Sb,Sn,Ge,Ti,Fe,Zr,Ce,Bi,Sr,Mn,Li,Na,K,Zn和/或质子化的氮基,优选钙离子,镁离子,铝离子和/或锌离子;和m=1-4,优选2或3;n=1-4,更优选1或3;x=1–4,优选1或2。在特别优选的实施例中,R1=烷基,R2=烷基且M=Al或Zn。
根据本发明特别优选的示例,次膦酸盐来自Clariant SE的可商购获得的产品Exolit OP(RTM)。
进一步优选的含磷阻燃剂是具有下式结构的次磷酸的金属盐
其中Met是选自元素周期表I,II,III和IV族的金属,n是1至4的自然数,其对应于相应的金属离子Met的电荷。Metn+例如是Na+,Ca2+,Mg2+,Zn2+,Ti4+或者Al3+,其中,特别优选地是Ca2+,Zn2+和A3+。
部分上述次磷酸的盐可商购获得,例如来自意特麦琪(ItalmatchChemicals)公司的Phoslite(RTM)。
另一组优选的含磷阻燃剂是根据下式结构的膦酸酯或膦酸二芳基酯:
R8和R10=H,烷基,优选地C1-C4烷基,R9=C1-C4烷基,u=1-5和v=1-5。
相应的结构也可以以膦酸酯低聚物、聚合物和共聚物的形式存在。直链或支链的膦酸酯低聚物和聚合物在现有技术中是已知的。对于支链膦酸酯低聚物和聚合物,参考美国专利US 2 716 101、US 3 326 852、US 4 328 174、US 4 331 614、US 4 374 971、US 4415 719、US 5 216 113、US 5 334 692、US 3 442 854、US 6 291 630 B1、US 6 861 499B2和US 7816486 B2。对于膦酸酯低聚物,参考美国专利申请US 2005/0020800 A1,US2007/0219295 A1和US 2008/0045673 A1。关于直链膦酸酯低聚物和聚合物,参考美国专利文献US 3 946 093、US 3 919 363、US 6 288 210 B1、US 2 682 522和US 2 891 915。
膦酸酯聚合物和低聚物可以例如是从FRX聚合物公司(FRX polymers)获得,商品名Nofia(RMT)。
另一组优选的含磷阻燃剂是基于氧杂膦氧化物及其衍生物的化合物,例如具有以下结构:
其中,M是选自元素周期表的第二、第三、第十二或第十三族的金属,x=2或3,n≥10,m=0-25,R=H、卤素、1-32个C原子的脂族或芳族基团,R1=H、C1-C6烷基。
基于氧杂磷氧化物的产品可以例如是从席尔-塞拉赫有限公司(Schill andSeilacher GmbH)商购获得,商品名为Ukanol(RTM)。其它化合物可以例如根据专利说明WO2013020696、WO 2010135398、WO 03070736、WO 2006084488、WO 2006084489、WO2011000019、WO 2013068437、WO 2013072295制备。
另外的起协同作用的含磷阻燃剂是根据下述结构的环状膦酸酯:
其中A1和A2彼此独立地为具有1至4个碳原子的取代或未取代的直链或支链烷基、取代或未取代的苄基、取代或未取代的苯基、取代或未取代的萘基,其中A3和A4彼此独立地为甲基或乙基,A5是具有1至4个碳原子的直链或支链烷基或可以分别具有至多3个甲基的苯基或苄基。
环状膦酸酯例如可商购自托尔有限公司(Thor GmbH),商品名为Aflammit(RTM)或可以根据EP 2450401制备得到。
另外的起协同作用的含磷阻燃剂是磷睛,特别是聚合磷睛。相应的产品可商购获得,例如商购自大冢化学公司(Otsuka Chemicals)的SPB-100。
所述至少一种另外的阻燃剂特别地也可以是含氮阻燃剂。优选的含氮阻燃剂是三聚氰胺多磷酸盐,三聚氰胺氰尿酸盐,三聚氰胺-金属磷酸盐,聚-[2,4-(哌嗪-1,4-基)-6-(吗啉-4-基)-1,3,5-三嗪]和聚磷酸铵。这些化合物是商业产品,可通过商品名Melapur(RTM)购自BASFSE公司,通过Budit(RTM)购自博德化工厂(Budenheim Chemical Factory),通过Exolit AP(RTM)购自Clariant,通过Safire(RTM)购自弗洛瑞迪公司(Floridienne)或通过MCA PPM triazine购自MCA技术有限公司(MCA Technologies GmbH)。
在将根据本发明使用的通式I至IV的化合物与至少一种另外的阻燃剂组合使用的情况下,优选地前述化合物以重量比(根据式I至IV的化合物的总和:阻燃剂)从99:1到1:99使用,优选地5:95到50:50,特别优选地10:90到30:70。
此外,添加剂可以选自UV吸收剂,光稳定剂,稳定剂,羟胺,苯并呋喃酮,金属钝化剂,填料钝化剂,成核剂,冲击强度增强剂,增塑剂,润滑剂,流变改性剂,加工助剂,颜料,着色剂,荧光增白剂,抗微生物活性物质,抗静电剂,增滑剂,防粘连剂,偶联剂,链增长剂,分散剂,相容剂,集氧剂,酸收集剂,标记剂或防雾剂。在优选的实施例中,组合物特别包含酸收集剂,例如基于长链酸的盐,例如硬脂酸钙,硬脂酸镁,硬脂酸锌,乳酸钙,硬脂酰-2-乳酸钙或水滑石和/或选自酚类抗氧化剂和亚磷酸酯/次膦酸酯的稳定剂和/或选自受阻胺(HALS)的光稳定剂和/或分散剂。
合适的光稳定剂是例如基于2-(2'-羟基苯基)苯并三唑、2-羟基二苯甲酮、苯甲酸酯、丙烯酸酯、草酰胺和2-(2-羟基苯基)-1,3,5-三嗪的化合物。
合适的2-(2'-羟基苯基)苯并三唑例如为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'-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,2-(3'-叔丁基-2'-羟基-5'-(2-异辛氧羰基乙基)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'-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯交换反应产物;R为=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。
合适的2-羟基二苯甲酮例如为2-羟基二苯甲酮的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'-二甲氧基的衍生物。
合适的丙烯酸酯例如为乙基-α-氰基-β,β-二苯基丙烯酸酯,α-氰基-β-甲基-对甲氧基肉桂酸甲酯,丁基-α-氰基-β-甲基-对甲氧基肉桂酸甲酯,甲基-α-氰基-β-甲氧基肉桂酸甲酯,甲基-α-氰基-β-甲氧基肉桂酸甲酯和N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚。
合适的苯甲酸酯例如为4-叔丁基苯基水杨酸酯,苯基水杨酸酯,辛基苯基水杨酸酯,二苯甲酰间苯二酚,双(4-叔丁基苯甲酰基)间苯二酚,苯甲酰间苯二酚,2,4-二叔丁基苯基-3,5-二叔丁基-4-羟基苯甲酸酯,十六烷基-3,5-二-叔丁基-4-羟基苯甲酸酯,十八烷基-3,5-二叔丁基-4-羟基苯甲酸酯,2-甲基-4,6-二叔丁基苯基-3,5-二叔丁基-4-羟基苯甲酸酯。
合适的草酰胺例如是4,4'-二辛氧基草酰苯胺,2,2'-二乙氧基草酰替苯胺,2,2'-二辛氧基-5,5'-二叔丁基草酰替苯胺,2,2'-双十二烷氧基-5,5'-二叔丁基草酰替苯胺,2-乙氧基-2'-乙基草酰苯胺,N,N'-双(3-二甲基氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2'-乙氧基苯胺及其与2-乙氧基-2'-乙基-5,4'-二叔丁氧基苯胺的混合物,邻-和对甲氧基-二取代的草酰替苯胺的混合物以及邻-和对乙氧基-二取代的草酰替苯胺的混合物。
合适的2-(2-羟基苯基)-1,3,5-三嗪例如是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,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。
合适的金属钝化剂例如是N,N'-二苯基草酰胺,N-水杨醛-N'-水杨酰肼,N,N'-双(水杨酰基)肼,N,N'-双(3,5-二叔丁基-4-羟基苯基丙酰基)肼,3-水杨酰氨基-1,2,4-三唑,双(亚苄基)草酰二肼,草酰替苯胺,间苯二甲酰二酰肼,癸二酰联苯酰肼,N,N'-二乙酰己二酰二酰肼,N,N'-二(水杨酰)草酰二酰肼,N,N'-双(水杨酰)硫代丙酰二酰肼。
以下结构特别适合作为金属钝化剂:
合适的酚类抗氧化剂例如是:
烷基化单酚,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-N-丁基苯酚,2,6-二-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;直链或支链壬基酚,例如2,6-二壬基-4-甲基苯酚,2,4-二甲基-6-(1'-甲基十一烷-1'-基)苯酚,2,4-二甲基-6-(1'-甲基十七烷-1'-基)苯酚,2,4-二甲基-6-(1'-甲基十三烷-1'-基)苯酚及其混合物;
烷基硫代甲基酚,例如2,4-二辛基硫代甲基-6-叔丁基苯酚,2,4-二辛基硫代甲基-6-甲基苯酚,2,4-二辛基硫代甲基-6-乙基苯酚,2,6-双十二烷基硫代甲基-4-壬基苯酚;
氢醌和烷基化氢醌,例如2,6-二叔丁基-4-甲氧基苯酚,2,5-二叔丁基氢醌,2,5-二叔戊基氢醌,2,6-二苯基-4-十八烷氧基苯酚,2,6-二叔丁基氢醌,2,5-二叔丁基-4-羟基苯甲醚,3,5-二叔丁基-4-羟基苯甲醚,3,5-二叔丁基-4-羟基苯基硬脂酸酯,双(3,5-二叔丁基-4-羟基苯基)己二酸酯;
生育酚,例如α-,β-,γ-,δ-生育酚和他们的混合物(维生素E);
羟基化硫代二苯醚,例如2,2'-硫代双(6-叔丁基-4-甲基苯酚),2,2'-硫代双(4-辛基苯酚),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-戊基苯酚),4,4'-双(2,6-二甲基-4-羟基苯基)二硫化物;
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,2,6-二(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚,1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷,1,1-双(5-叔丁基-4-羟基-2-甲基苯基)-3-N-十二烷基巯基丁烷,乙二醇-双[3,3-双(3'-叔丁基-4'-羟基苯基)丁酸酯],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-羟基苯基)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-N-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;
O-、N-和S-苄基化合物,例如3,5,3',5'-四叔丁基-4,4'-二羟基二苄基醚,十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯,十三烷基-4-羟基-3,5-二叔丁基苄基巯基乙酸酯,三(3,5-二叔丁基-4-羟基苄基)胺,二(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯,双(3,5-二叔丁基-4-羟基苄基)-硫化物,异辛基-3,5-二叔丁基-4-羟基苄基巯基乙酸酯;
羟基苄基化丙二酸酯,例如双十八烷基-2,2-双(3,5-二叔丁基-2-羟基苄基)丙二酸酯,双十八烷基-2-(3-叔丁基-4-羟基-5-甲基-苄基)丙二酸酯,十二烷基巯基乙基-2,2-双(3,5-二叔丁基-4-羟基苄基)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-羟基苄基)丙二酸酯;
芳族羟基苄基化合物,例如1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯,1,4-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;
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-羟基苯氧基)-1,3,5-三嗪,2,4,6-三(3,5-二叔丁基-4-羟基苯氧基)-1,2,3-三嗪,1,3,5-三(3,5-二叔丁基-4-羟基苄基)异氰脲酸酯,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-羟基苯乙基)-1,3,5-三嗪,1,3,5-三(3,5-二叔丁基-4-羟基苯基丙酰基)六氢-1,3,5-三嗪,1,3,5-三(3,5-二环己基-4-羟基苄基)异氰脲酸酯;
苄基膦酸酯,例如二甲基-2,5-二叔丁基-4-羟基苄基膦酸酯,二乙基-3,5-二叔丁基-4-羟基苄基膦酸酯,双十八烷基-3,5-二叔丁基-4-羟基苄基膦酸酯,双十八烷基-5-叔丁基-4-羟基-3-甲基苄基膦酸酯,3,5-二叔丁基-4-羟基苄基膦酸的单乙酯的钙盐;
酰基氨基酚,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-羟基苯基)氨基甲酸酯;
β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元或多元醇的酯,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;
β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元或多元醇的酯,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,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;
β-(3,5-二环己基-4-羟基苯基)丙酸与一元或多元醇的酯,例如甲醇,乙醇,辛醇,异辛醇,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)异氰脲酸酯,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;
3,5-二-叔丁基-4-羟基苯基乙酸与一元或多元醇的酯,例如甲醇,乙醇,辛醇,异辛醇,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)异氰脲酸酯,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;
β-(3,5-二叔丁基-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)六亚甲基二酰胺,N,N'-双(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二酰胺,N,N'-双(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二酰胺,N,N'-双(3,5-二叔丁基-4-羟基苯基丙酰基)酰肼,N,N'-双[2-(3-[3,5-二叔丁基-4-羟基苯基]丙酰氧基)乙基]草酰胺( XL-1,由Uniroyal销售);
抗坏血酸(维生素C)。
特别优选的酚类抗氧化剂是:
十八烷基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯,季戊四醇-四[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯,三(3,5-二叔丁基-4-羟基苯基)异氰脲酸酯,1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苯基)异氰脲酸酯,1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯,三甘醇-双[3-(3-叔丁基-4-羟基-5-甲基苯基)丙酸酯,N,N'-己烷-1,6-二基-双[3-(3,5-二叔丁基-4-羟基苯基)丙酰胺。
合适的亚磷酸酯/次膦酸酯例如:
亚磷酸三苯酯,亚磷酸二苯基烷基酯,亚磷酸苯基二烷基酯,三(壬基苯基)亚磷酸酯,三月桂基亚磷酸酯,三十八烷基亚磷酸酯,二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,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,二异癸氧基季戊四醇二亚磷酸酯,双(2,4-二叔丁基-6-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,三硬脂基山梨醇三亚磷酸酯,四(2,4-二叔丁基苯基)-4,4'-亚联苯基二亚膦酸酯,6-异辛基氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂磷酸,亚磷酸双(2,4-二叔丁基-6-甲基苯基)甲酯,亚磷酸双(2,4-二叔丁基-6-甲基苯基)乙酯,6-氟-2,4,8,10-四叔丁基-12-甲基二苯并[d,g]-1,3,2-二氧杂磷酸,2,2'2”-次氮基[三乙基三(3,3”,5,5'-四叔丁基-1,1'-联苯-2,2'-二基)亚磷酸酯],2-乙基己基(3,3',5,5'-四叔丁基-1,1'-联苯-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)-1,3,2-二氧杂磷杂环戊烷。
特别优选的亚磷酸酯/次膦酸酯是:
其它合适的稳定剂是胺类抗氧化剂。合适的胺类抗氧化剂例如是:
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-N-丁基氨基苯酚,4-丁酰基氨基苯酚,4-壬酰基氨基苯酚,4-十二烷酰基氨基苯酚,4-十八酰基氨基苯酚,(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,(苯基氨基)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,单和二烷基化叔丁基/叔辛基二苯基胺的混合物,单烷基和二烷基化壬基二苯基胺的混合物,单和二烷基化十二烷基二苯胺的混合物,单和二烷基化异丙基/异己基二苯基胺的混合物,单和二烷基化叔丁基二苯胺的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪,吩噻嗪,单和二烷基化叔丁基/叔辛基吩噻嗪的混合物,单和二烷基化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-2-烯及其混合物或组合物。
其它合适的胺类抗氧化剂是羟胺或N-氧化物(硝酮),例如N,N-二烷基羟胺,N,N-二苄基羟胺,N,N-二月桂基羟胺,N,N-二硬脂基羟胺,N-苄基-α-苯基硝酮,N-十八烷基-α-十六烷基硝酮,和根据下式的Genox EP(添加剂):
其它合适的稳定剂是硫代增效剂。合适的硫代增效剂例如是二硬脂基硫代二丙酸酯,二月桂基二丙酸酯或根据下式的化合物:
其它合适的稳定剂,特别是聚酰胺的稳定剂是铜盐,例如铜-(I)-碘化物,铜-(I)-溴化物或铜络合物,例如三苯基膦铜-(I)-络合物。
合适的受阻胺例如是琥珀酸1,1-双(2,2,6,6-四甲基-4-哌啶基)酯,双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯,双(1,2,2,6,6-五甲基-4-哌啶基)-N-丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合产物,N,N'-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的线性或环状缩合产物,(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯,四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯,1,1'-(1,2-乙二基)-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-硬脂氧基-2,2,6,6-四甲基哌啶,N,N'-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉基-2,6-二氯-1,3,5-三嗪的直链或环状缩合物,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。
合适的分散剂例如是:
聚丙烯酸酯,例如具有长链侧基的共聚物,聚丙烯酸酯嵌段共聚物,烷基酰胺:例如N,N'-1,2-乙二基双十八酰胺脱水山梨糖醇酯,例如单硬脂基山梨糖醇酯,钛酸盐和锆酸盐,与官能团反应的共聚物例如聚丙烯-共-丙烯酸,聚丙烯-共-马来酸酐,聚乙烯-共-甲基丙烯酸缩水甘油酯,聚苯乙烯-马来酸酐-聚硅氧烷:例如二甲基硅烷二醇-环氧乙烷共聚物,聚苯基硅氧烷共聚物,两亲共聚物,例如聚乙烯-嵌段-聚环氧乙烷,树枝状聚合物,例如含羟基的树枝状聚合物。
合适的成核剂例如是滑石,单和多官能羧酸的碱金属盐或碱土金属盐,例如苯甲酸,琥珀酸,己二酸,例如苯甲酸钠,甘油锌,羟基-双(4-叔丁基)苯甲酸铝,亚苄基山梨醇,例如1,3:2,4-双(亚苄基)山梨醇或1,3:2,4-双(4-甲基亚苄基)山梨醇,2,2'-亚甲基-双-(4,6-二叔丁基苯基)磷酸酯,以及三酰胺,例如根据以下结构:
合适的填充材料和增强材料例如是合成的或天然材料,例如碳酸钙,硅酸盐,玻璃纤维,玻璃球(固体或空心),滑石,云母,高岭土,硫酸钡,金属氧化物和金属氢氧化物,炭黑,石墨,碳纳米管,石墨烯,天然产物的锯屑或纤维,例如纤维素,合成纤维或金属纤维。其它合适的填充材料是水滑石或沸石或层状硅酸盐,例如蒙脱石,膨润土,贝得石,云母,锂蒙脱石,皂石,蛭石,锂辉石,麦羟硅钠石,伊利石,高岭石,硅灰石,绿坡缕石。
用于缩聚聚合物的线性分子量增长的合适的链增长剂,例如聚酯或聚酰胺,例如双环氧化物,双恶唑啉,双恶唑酮,双恶嗪,二异氰酸酯,二酐,双酰基内酰胺,双马来酰亚胺,二氰酸酯碳二亚胺。其它合适的链增长剂是聚合化合物,例如聚苯乙烯-聚丙烯酸酯-聚(甲基)丙烯酸缩水甘油酯共聚物,聚苯乙烯-马来酸酐共聚物和聚乙烯-马来酸酐共聚物。
合适的颜料可以是无机或有机性质。合适的无机颜料例如是二氧化钛,氧化锌,硫化锌,氧化铁,群青,炭黑。合适的有机颜料例如是蒽醌,蒽嵌蒽,苯并咪唑酮,喹吖啶酮,二酮吡咯并吡咯,二嗪,阴丹酮,异吲哚啉酮,偶氮化合物,苝,酞菁或皮蒽酮。其它合适的颜料是基于金属的效应颜料或基于金属氧化物的珠光颜料。
荧光增白剂例如是双苯并恶唑,苯基香豆素或双(苯乙烯基)联苯,特别是下式的荧光增白剂:
合适的填充材料钝化剂例如是环氧化物,例如双酚A二缩水甘油醚,聚硅氧烷,聚丙烯酸酯,特别是嵌段共聚物,例如聚甲基丙烯酸-聚环氧烷或聚苯乙烯-聚丙烯酸酯-聚缩水甘油。
合适的抗静电剂例如是乙氧基化的烷基胺,脂肪酸酯,烷基磺酸盐和聚合物,例如聚醚酰胺或包含丙烯酸盐的共聚物,例如聚乙烯-聚丙烯酸酯-Na共聚物。
此外,本发明涉及一种模塑料、模制品、油漆或涂料,可由前述阻燃塑料材料组合物制成,特别是注塑制件、箔或薄膜、涂料或油漆、泡沫、纤维、电缆和管、型材、条、膜、例如土工膜、粘合剂的形式,其通过挤出、注塑、吹塑、压延、压制工艺、纺丝工艺或刷涂工艺制备而成,例如用于电气和电子工业,建筑业,运输业(汽车、飞机、船舶、火车),用于医疗应用,用于家用和电器,车辆部件,消费品,家具,纺织品。其它应用领域是清漆,油漆和涂料。
例如,根据本发明的组合物可以用于海洋应用(浮筒、板、船),汽车应用(保险杠、电池、覆盖部件、汽油箱、电缆、管道等),飞机部件,铁路部件,自行车和摩托车部件,航天旅行应用,例如卫星部件,用于电器(例如计算机、电话、打印机、音频和视频系统)的外壳部件,插头,印刷电路,开关,灯罩,冰箱,咖啡机,真空吸尘器,用于能量产生的转子叶片,通风机,屋顶结构的箔,建筑箔,管,如废水管和煤气管,连接部件,排水系统,型材,例如窗户型材或电缆管道,木质复合材料,家具,地板,覆盖板,合成草坪,体育场座椅,地毯,网,绳索,家具部件,垫子,花园座椅,瓶箱,容器和桶。
本发明同样涉及一种根据本发明的前述塑料材料组合物的制备方法,其中至少一种根据式I至IV的化合物与所述至少一种另外的阻燃剂同时或在其掺入之前、之后,掺入到至少一种塑料材料,优选至少一种热塑性聚合物中。
塑料材料中上述阻燃剂和其它添加剂的掺入通过常规加工方法进行,将聚合物熔融并与阻燃剂和添加剂混合,优选通过混合器、捏合机和挤出机。挤出机被优选作为加工机器,例如单螺杆挤出机、双螺杆挤出机、行星式辊挤出机、环形挤出机、共捏合机,其优选配备有真空脱气机。因此,该处理可以在空气或可能在惰性气体条件下进行。因此,不同的阻燃剂和添加剂可以单独或作为混合物以液体、粉末、颗粒或压实产品的形式或同样以母料或浓缩物的形式加入,其包含根据本发明的例如50-80%含量的组合物。
本发明参考后续实施例描述,但不将本发明限制于特定实施例。
实施例
a)盐的生产
实施例1:1-羟基苯并三唑钾盐(K-btaO)的合成
类似于文献(L.A.Carpino et al.,Applied Chemistry Int.Ed.2002,41,442–445),将1-羟基苯并三唑(36g)在搅拌下加入到分散在16%甲醇水溶液(171ml)中的K2CO3(29.5g)中。在气体释放结束后,将混合物再搅拌1小时,随后过滤掉过量的K2CO3。将该溶液在旋转蒸发仪上浓缩,所得产物通过在甲醇中溶解两次并在乙醚中沉淀而重结晶。
热重分析(TGA):在40-380℃失重1.6%;在380-390℃失重73.4%;在390-600℃失重0.2%。
实施例2:1-羟基苯并三唑锌盐(Zn-btaO)的合成
类似于文献(A.D.Katsenis et al.,Inorganic Chemistry Communication2009,12,92-96),将室温下以固体储存的Zn(ClO4)2(9.5g)的水溶液(375ml)与2倍当量的K-btaO(8.5g)在DMF(500ml)中反应,获得所需产物。
热重分析(TGA):在40-360℃失重3.3%;在360-370℃失重92.2%;在370-600℃失重0.3%。
b)根据本发明的阻燃塑料材料混合物的制备和测试
聚丙烯样品(DOW C766-03)的挤出在190℃的温度和150rpm的螺杆转速下在11mm双螺杆挤出机(赛默飞科技(Thermo Scientific)的方法11)上进行。聚合物和添加剂的所需比例首先通过混合均化,并通过体积计量供给到挤出。
用于耐火测试的试样,在220℃的温度和2t的压力下使用10t液压机(沃纳&普弗勒德(Werner&Pfleiderer))经颗粒制备得到。为此目的,将颗粒填充到压模中,并将其转移到已经预热的压机中。在0.5t的压力下,首先将颗粒熔化60秒。在熔化时间结束后,将压力增加至2t,并保持恒定3分钟。在保持压缩压力的同时,将模具冷却至60℃,然后取出试样。试样具有以下尺寸:根据标准为127.5×12.5×1.5mm。
表1中包含了本发明的实施例和对比例,按照DIN EN 60695-11-10进行测试,并且根据标准得到燃烧时间和分级:
表1:聚丙烯的组分和耐火测试结果
二乙基次膦酸铝(Exolit OP 1230,制造商:Clariant SE):
膦酸酯(Aflammit PCO 900,制造商:Thor GmbH),对应于以下结构:
根据本发明的实施例在除去点火源之后是自熄的,并且令人惊讶地,相较对比例降低了燃烧时间,被给予分级V-2。
由于其热稳定性和其盐结构,新的阻燃剂和新的阻燃组合物被提出,以期望相对于当前产品有一些优点,例如低迁移行为、可靠的掺入、长期稳定性。
Claims (14)
1.一种根据通式I至IV的化合物或至少两种通式I至IV的化合物的混合物作为塑料材料的阻燃剂的用途:
其中,在各种情况中,各自彼此独立的,
R1选自由氢,具有1至18个碳原子的烷基,具有1至18个碳原子的部分氟化的烷基或全氟烷基,具有至多1至18个碳原子的不饱和有机基团,两个邻位基团R1还能够连接形成环,-NO2,-F,-Cl和-Br组成的组,和
R2选自由一价、二价或三价无机阳离子,或一价、二价或三价有机阳离子和氢组成的组。
2.根据权利要求1所述的用途,其特征在于,所述一价、二价或三价无机阳离子选自由Li+、Na+、K+、1/2Mg2+、1/2Ca2+、1/3Al3+、1/2Zn2+组成的组,和/或所述有机阳离子选自由含氮有机阳离子和/或含磷有机阳离子组成的组,特别是铵、三聚氰胺和/或鏻。
3.根据前述任一项权利要求所述的用途,其特征在于,在各种情况中,R1是氢和/或R2是一价或二价无机阳离子,特别是K+。
4.根据前述任一项权利要求所述的用途,其特征在于,所述塑料材料选自由热塑性、弹性体或热固性塑料材料组成的组,特别是
a)由烯烃或二烯烃构成的聚合物,例如聚乙烯(LDPE、LLDPE、VLDPE、ULDPE、MDPE、HDPE、UHMWPE),茂金属-聚乙烯(m-PE),聚丙烯,聚异丁烯,聚-4-甲基戊烯-1,聚丁二烯,聚异戊二烯,聚环辛烯,聚亚烷基-一氧化碳共聚物,以及具有统计或嵌段结构形式的共聚物,例如聚丙烯-聚乙烯(EP),EPM或EPDM,乙烯-乙酸乙烯酯(EVA);乙烯-丙烯酸酯,例如乙烯-丙烯酸丁酯,乙烯-丙烯酸及其盐(离聚物),以及三元共聚物,例如乙烯-丙烯酸-缩水甘油基丙烯酸酯;接枝聚合物,例如聚丙烯-接枝-马来酸酐,聚乙烯-接枝-丙烯酸,聚乙烯-聚丙烯酸丁酯-接枝-马来酸酐,
b)聚苯乙烯,聚甲基苯乙烯,聚乙烯基萘,苯乙烯-丁二烯(SB),苯乙烯-丁二烯-苯乙烯(SBS),苯乙烯-乙烯-丁烯-苯乙烯(SEBS),苯乙烯-乙烯-丙烯-苯乙烯,苯乙烯-异戊二烯,苯乙烯-异戊二烯-苯乙烯(SIS),苯乙烯-丁二烯-丙烯腈(ABS),苯乙烯-丙烯腈-丙烯酸酯(ASA),苯乙烯-乙烯,苯乙烯-马来酸酐聚合物,包括相应的接枝共聚物,例如丁二烯接枝苯乙烯,SBS或SEBS接枝马来酸酐,以及由甲基丙烯酸甲酯、苯乙烯-丁二烯和ABS(MABS)构成的接枝共聚物,
c)含卤聚合物,例如聚氯乙烯(PVC),聚氯丁烯和聚偏二氯乙烯(PVDC),由氯乙烯和偏二氯乙烯、或氯乙烯和乙酸乙烯酯构成的共聚物,氯化聚乙烯,聚偏二氟乙烯,
d)不饱和酯的聚合物,例如聚丙烯酸酯和聚甲基丙烯酸酯,例如聚甲基丙烯酸甲酯(PMMA),聚丙烯酸丁酯,聚丙烯酸月桂酯,聚丙烯酸硬脂酯,聚丙烯酸缩水甘油酯,聚甲基丙烯酸缩水甘油酯,聚丙烯腈,聚丙烯酰胺;例如聚丙烯腈-聚丙烯酸烷基酯的共聚物,
e)不饱和醇及衍生物的聚合物,例如聚乙烯醇,聚乙酸乙烯酯,聚乙烯醇缩丁醛,
f)聚缩醛,例如聚甲醛(POM),或与例如丁醛形成的共聚物,
g)聚苯醚和由聚苯乙烯或聚酰胺形成的共混物,
h)环醚的聚合物,例如聚乙二醇,聚丙二醇,聚环氧乙烷,聚环氧丙烷,
i)聚氨酯,由羟基封端的聚醚或聚酯和芳族或脂族异氰酸酯构成,特别是线性聚氨酯,聚脲,
j)聚酰胺,例如聚酰胺-6,6.6,6.10,4.6,4.10,6.12,12.12,聚酰胺11,聚酰胺12以及(部分)芳族聚酰胺,例如聚邻苯二甲酰胺,例如,由对苯二甲酸和/或间苯二甲酸和脂族二胺或由脂族二羧酸制备,例如,己二酸或癸二酸和芳族二胺,例如,1,4-或1,3-二氨基苯;不同聚酰胺的共混物,例如PA-6与PA 6.6或聚酰胺与聚烯烃的共混物,例如PA/PP,
k)聚酰亚胺,聚酰胺酰亚胺,聚醚酰亚胺,聚酯酰亚胺,聚(醚)酮,聚砜,聚醚砜,聚芳砜,聚苯硫醚,聚苯并咪唑,聚乙内酰脲,
l)由脂族或芳族二羧酸和二醇构成或由羟基羧酸构成的聚酯,例如聚对苯二甲酸乙二醇酯(PET),聚对苯二甲酸丁二醇酯(PBT),聚对苯二甲酸丙二醇酯,聚萘二甲酸乙二醇酯,聚-1,4-二甲基环己烷对苯二甲酸酯,聚羟基苯甲酸酯,聚羟基萘二甲酸酯,聚乳酸(PLA),聚羟基丁酸酯(PHB),聚羟基戊酸酯(PHV),
m)聚碳酸酯,聚酯碳酸酯,以及共混物,例如PC/ABS,PC/PBT,PC/PET/PBT,PC/PA,
n)纤维素衍生物,例如硝酸纤维素,乙酸纤维素,丙酸纤维素,丁酸纤维素,
o)非热塑性或热固性材料,
p)环氧树脂,由二官能或多官能环氧化合物与例如基于胺,酸酐,二氰基二酰胺,硫醇,异氰酸酯或催化作用的硬化剂,
q)酚树脂,例如酚醛树脂,脲醛树脂,三聚氰胺-甲醛树脂,
r)由不饱和二羧酸和二醇构成的不饱和聚酯树脂,
s)硅酮,
t)作为二官能或多官能异氰酸酯和多元醇的反应产物的聚氨酯,聚脲,
u)醇酸树脂,烯丙基树脂,
v)以及两种或多种前述聚合物的混合物、组合物或共混物。
5.根据前述任一项权利要求所述的用途,其特征在于,将根据通式I至IV的化合物和/或至少两种式I至IV的化合物的混合物与塑料材料混合,在所得混合物中根据通式I至IV的化合物的总含量优选地为0.01至50重量%,更优选为0.05至25重量%。
6.一种阻燃剂塑料材料模塑料,包含至少一种塑料材料以及作为阻燃剂的至少一种根据通式I至IV的化合物或至少两种通式I和/或II的化合物的混合物,
其中,在各种情况中,各自彼此独立的,
R1选自由氢,具有1至18个碳原子的烷基,具有1至18个碳原子的部分氟化的烷基或全氟烷基,至多1至18个碳原子的不饱和有机基团、2个邻位R1基团能够连接形成环,-NO2,-F,-Cl和-Br组成的组,和
R2选自由一价、二价或三价无机阳离子,或一价、二价或三价有机阳离子和氢组成的组。
7.根据前述权利要求所述的塑料材料模塑料,其特征在于,所述塑料材料模塑料中至少一种根据通式I至IV的化合物的总含量是0.01到50重量%,优选0.05到25重量%。
8.根据前述两项权利要求中任一项所述的塑料材料模塑料,其特征在于,除了至少一种根据通式I至IV的化合物和至少一种塑料材料之外,相对于至少一种根据通式I和II的化合物和至少一种塑料材料的总量,所述塑料材料模塑料还包含至多70重量份,优选至多25重量份的至少一种另外的阻燃剂,所述另外的阻燃剂选自由含磷,含氮,无机,含硅,含硼,含卤素,含硫和/或自由基形成的阻燃剂组成的组。
9.根据前述权利要求所述的塑料材料模塑料,其特征在于,所述至少一种另外的阻燃剂优选自由以下组成的组:
a)无机阻燃剂,例如Al(OH)3,Mg(OH)2,AlO(OH),MgCO3,层硅酸盐,例如蒙脱石或海泡石,有机或未改性的复盐,例如Mg-Al硅酸盐,POSS-(多面体低聚倍半硅氧烷)化合物,碳酸钙镁石,水菱镁矿或多水高岭土以及Sb2O3,Sb2O5,MoO3,锡酸锌,羟基锡酸锌,
b)含氮阻燃剂,例如三聚氰胺,蜜勒胺,蜜白胺,氰脲酰胺,三聚氰胺衍生物,三聚氰胺缩合产物或三聚氰胺盐,苯并胍胺,聚异氰脲酸酯,尿囊素,特别是三聚氰胺氰尿酸盐,磷酸三聚氰胺,磷酸二蜜胺,焦磷酸三聚氰胺,多磷酸三聚氰胺,三聚氰胺甲烷膦酸盐,三聚氰胺-金属磷酸盐,例如三聚氰胺磷酸铝,三聚氰胺磷酸锌,三聚氰胺磷酸镁,以及相应的焦磷酸盐和多磷酸盐,乙二胺甲烷膦酸盐,聚-[2,4-(哌嗪-1,4-基)-6-(吗啉-4-基)-1,3,5-三嗪],多磷酸铵,三聚氰胺硼酸盐,三聚氰胺氢溴酸盐,
c)含磷阻燃剂,例如红磷,磷酸盐,例如间苯二酚二磷酸酯,双酚A二磷酸酯及其低聚物,磷酸三苯酯,二磷酸乙二胺,膦酸盐例如次磷酸的盐及其衍生物,例如烷基次膦酸盐,例如二乙基次膦酸铝或二乙基次膦酸锌或次膦酸铝,亚磷酸铝,膦酸铝,磷酸铝,膦酸酯,甲烷膦酸的低聚衍生物和多聚衍生物,9,10-二氢-9-氧杂-10-磷酰基菲-10-氧化物(DOPO)及其取代化合物,优选地是多聚磷酸酯,
d)基于氯和溴的含卤阻燃剂,例如多溴二苯醚,例如十溴二苯醚,(3-溴-2,2-双(溴甲基)丙基磷酸酯,磷酸三(三溴新戊基)酯,四溴邻苯二甲酸,1,2-二(三溴苯氧基)乙烷,六溴环十二烷,溴化二苯乙烷,三-(2,3-二溴丙基)异氰脲酸酯,亚乙基-双(四溴邻苯二甲酰亚胺),四溴双酚A,四溴双酚-A-双(2,3-二溴丙基醚),溴化聚苯乙烯,溴化聚丁二烯或聚苯乙烯,溴化聚丁二烯共聚物,溴化环氧树脂,聚丙烯酸苄酯,溴化聚苯醚,可能与Sb2O3和/或Sb2O5组合,
e)硼酸盐,例如硼酸锌或硼酸钙,可能在载体材料如二氧化硅上,
f)含硫阻燃剂,例如元素硫,二硫化物和多硫化物,硫脲硫化物,二硫代氨基甲酸盐,巯基苯并噻唑和次磺酰胺,
g)防滴剂,例如聚四氟乙烯,
h)含硅化合物,例如聚苯基硅氧烷,和/或
i)自由基形成剂阻燃剂,例如烷氧基胺,羟胺酯,偶氮化合物,二枯基或聚枯基,羟基酰亚胺或其衍生物,例如羟基酰亚胺酯或羟基酰亚胺醚,
j)碳改性,例如碳纳米管(CNT)或石墨烯。
10.根据权利要求6至9中任一项所述的塑料材料模塑料,其特征在于,包含选自由以下组成的组的添加剂:UV吸收剂,光稳定剂,稳定剂,如苯并呋喃酮,成核剂,冲击强度增强剂,增塑剂,润滑剂,流变改性剂,加工助剂,颜料,着色剂,荧光增白剂,抗微生物活性物质,抗静电剂,增滑剂,抗粘连剂,偶联剂,分散剂,相容剂,集氧剂,标记剂,防雾剂或酸收集剂,优选基于长链酸的盐的酸收集剂,例如硬脂酸钙,硬脂酸镁,硬脂酸锌,硬脂酸铝,乳酸钙,硬脂酰-2-乳酸钙或水滑石。
11.根据权利要求6至10中任一项所述的塑料材料模塑料,其特征在于,除了至少一种根据通式I至IV的化合物和至少一种塑料材料之外,相对于至少一种根据通式I和II的化合物和至少一种塑性材料的总量,所述塑料材料模制料还包含0.01-10重量份,优选0.05-3重量份的至少一种稳定剂,所述稳定剂选自由酚类抗氧化剂,亚磷酸酯/次膦酸酯,胺类抗氧化剂,含硫抗氧化剂或羟胺组成的组。
12.根据前一权利要求所述的塑料材料模塑料,其特征在于,所述至少一种稳定剂选自由以下组成的组:
a)酚类抗氧化剂,优选十八烷基-3-(3,5-二叔丁基-4-羟基苯基)丙酸酯,季戊四醇-四[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯,三(3,5-二叔丁基-4-羟基苯基)异氰脲酸酯,1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苯基)异氰脲酸酯,1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯,三甘醇-双[3-(3-叔丁基-4-羟基-5-甲基苯基)丙酸酯,N,N'-己烷-1,6-二基-双[3-(3,5-二叔丁基-4-羟基苯基)丙酰胺,
b)亚磷酸酯/次膦酸酯,优选亚磷酸三(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,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,二异癸氧基季戊四醇二亚磷酸酯,双(2,4-二叔丁基-6-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,四(2,4-二叔丁基苯基)-4,4'-亚联苯基二次膦酸酯,
c)胺类抗氧化剂,优选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,
d)含硫抗氧化剂,特别是硫代二丙酸二硬脂基酯,二月桂基二丙酸酯,
e)羟胺,优选N,N-二烷基羟胺、N,N-二苄基羟胺、N,N-二月桂基羟胺、N,N-二硬脂基羟胺、N-苄基-α-苯基硝酮、N-十八烷基-α-十六烷基硝酮,
f)受阻胺,优选1,1-双(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯,、双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,(、(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(1,2,2,6,6-五甲基-4-哌啶基)-N-丁基-3,5-二叔丁基-4-羟基苄基丙二酸酯、1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和与琥珀酸的缩合产物、N,N'-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和与4-叔辛基氨基-2,6-二氯-1,3,5-三嗪的线性或环状缩合产物、四(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯、四钛(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯、1,1'-(1,2-乙二基)-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-硬脂氧基-2,2,6,6-四甲基哌啶,、N,N'-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和与4-吗啉基-2,6-二氯-1,3,5-三嗪的直链线性或环状缩合产物、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]癸烷与表氯醇的反应产物。
13.根据权利要求6至12中任一项所述的塑料材料模塑料,其特征在于,所述至少一种塑料材料选自由以下组成的组:
a)由烯烃或二烯烃构成的聚合物,例如聚乙烯(LDPE、LLDPE、VLDPE、MDPE、HDPE),聚丙烯,聚异丁烯,聚-4-甲基戊烯-1,聚丁二烯,聚异戊二烯,聚环辛烯,以及具有统计或嵌段结构形式的共聚物,例如聚丙烯-聚乙烯(EP),EPM或EPDM,乙烯-乙酸乙烯酯(EVA);乙烯-丙烯酸酯,
b)聚苯乙烯,聚甲基苯乙烯,苯乙烯-丁二烯-苯乙烯(SBS),苯乙烯-异戊二烯,苯乙烯-丁二烯-丙烯腈(ABS),苯乙烯-丙烯腈-丙烯酸酯(ASA),苯乙烯-马来酸酐聚合物,包括相应的接枝共聚物,例如苯乙烯接枝丁二烯或马来酸酐接枝SBS,
c)含卤素聚合物,例如聚氯乙烯和聚偏二氯乙烯,
d)不饱和酯的聚合物,例如聚丙烯酸酯和聚甲基丙烯酸酯,例如PMMA,聚丙烯腈,
e)不饱和醇和衍生物构成的聚合物,例如聚乙烯醇,聚乙酸乙烯酯,聚乙烯醇缩丁醛,
f)聚缩醛,例如聚甲醛,
g)聚苯醚和与聚苯乙烯的共混物,
h)聚氨酯,特别是线性聚氨酯,
i)聚酰胺,例如聚酰胺-6,6.6,6.10,4.6,4.10,6.12,12.12,聚酰胺11,聚酰胺12以及(部分)芳族聚酰胺,例如聚邻苯二甲酰胺,
j)聚酰亚胺,聚酰胺酰亚胺,聚醚酰亚胺,聚酮,聚砜,聚醚砜,聚苯硫醚,
k)聚酯如聚对苯二甲酸乙二醇酯和聚对苯二甲酸丁二醇酯,聚乳酸,
l)聚碳酸酯,
m)纤维素衍生物,例如硝酸纤维素,乙酸纤维素,丙酸纤维素,
n)以及两种或多种上述聚合物的混合物、组合物或共混物。
14.根据权利要求6至13中任一项所述的塑料材料模塑料,以注塑制件、箔或薄膜、涂料或油漆、泡沫、纤维、电缆、电缆管道和管、型材、中空体、条、膜、例如土工膜、或粘合剂的形式,其通过挤出、注射、吹塑、压延、压制工艺、纺丝工艺或刷涂工艺制备而成,例如用于电气和电子工业,建筑业,运输业,用于医疗应用,用于家用和电器,车辆部件,消费品,家具,纺织品。
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PCT/EP2015/061771 WO2015189034A1 (de) | 2014-06-12 | 2015-05-28 | Verwendung von hydroxybenzotriazol-derivaten und/oder hydroxy-indazol-derivaten als flammschutzmittel für kunststoffe sowie flammgeschützte kunststoffformmasse |
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- 2015-05-28 ES ES15727343.4T patent/ES2669500T3/es active Active
- 2015-05-28 US US15/317,899 patent/US10323136B2/en not_active Expired - Fee Related
- 2015-05-28 CN CN201580031450.XA patent/CN106661270B/zh not_active Expired - Fee Related
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- 2015-05-28 JP JP2016572474A patent/JP6325694B2/ja not_active Expired - Fee Related
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CN115362142A (zh) * | 2020-03-27 | 2022-11-18 | 弗劳恩霍夫应用研究促进协会 | 经取代的肉桂酸酯作为有机材料的稳定剂的用途、稳定的有机材料、稳定有机材料的方法和特定的肉桂酸酯 |
CN115362142B (zh) * | 2020-03-27 | 2024-08-20 | 弗劳恩霍夫应用研究促进协会 | 经取代的肉桂酸酯作为有机材料的稳定剂的用途、稳定的有机材料、稳定有机材料的方法和特定的肉桂酸酯 |
CN111875954A (zh) * | 2020-08-07 | 2020-11-03 | 宁波耀众模塑科技有限公司 | 一种高效环保的聚氨酯发泡产品用阻燃剂 |
CN113150385A (zh) * | 2021-04-13 | 2021-07-23 | 中联重科股份有限公司 | 处理碳纳米管的方法、聚氨酯组合物和聚氨酯活塞及其制备方法 |
Also Published As
Publication number | Publication date |
---|---|
US20170121499A1 (en) | 2017-05-04 |
KR20170018032A (ko) | 2017-02-15 |
EP3155041B1 (de) | 2018-03-21 |
EP3155041A1 (de) | 2017-04-19 |
CN106661270B (zh) | 2018-12-07 |
JP6325694B2 (ja) | 2018-05-16 |
US10323136B2 (en) | 2019-06-18 |
KR101984077B1 (ko) | 2019-05-30 |
WO2015189034A1 (de) | 2015-12-17 |
ES2669500T3 (es) | 2018-05-28 |
JP2017520646A (ja) | 2017-07-27 |
DE102014211276A1 (de) | 2015-12-17 |
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