CN116368185A - 去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物用于稳定有机材料的用途,经稳定的塑料组合物,稳定剂组合物和稳定有机材料的方法 - Google Patents
去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物用于稳定有机材料的用途,经稳定的塑料组合物,稳定剂组合物和稳定有机材料的方法 Download PDFInfo
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- CN116368185A CN116368185A CN202180063017.XA CN202180063017A CN116368185A CN 116368185 A CN116368185 A CN 116368185A CN 202180063017 A CN202180063017 A CN 202180063017A CN 116368185 A CN116368185 A CN 116368185A
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- Prior art keywords
- eugenol
- styrene
- tert
- copolymers
- antioxidants
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- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 title claims description 160
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Classifications
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- Organic Chemistry (AREA)
- Emergency Medicine (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
有机材料如塑料会受到老化过程的影响,最终导致所需性能,例如机械特性值的损失。这种被称为自氧化的过程导致聚合物链的变化,例如分子量的变化或新化学基团的形成,这些变化由通过机械化学过程或在氧气存在下通过UV辐射产生的自由基链裂解引起。因此,稳定剂被用来防止或至少延迟上述老化。稳定剂的重要代表是干扰自氧化过程中形成的自由基从而中断降解过程的抗氧化剂。主要抗氧化剂和次要抗氧化剂通常是有区别的,主要抗氧化剂可以直接与含氧自由基或C‑自由基发生反应,次要抗氧化剂则与中间形成的氢过氧化物发生反应(见C.
Description
有机材料,如塑料会受到老化过程的影响,最终导致所需性能,例如机械特性值的损失。这种被称为自氧化的过程导致聚合物链的变化,例如分子量的变化或新化学基团的形成,这些变化由通过机械化学过程或在氧气存在下通过UV辐射产生的自由基链裂解引起。因此,稳定剂被用来防止或至少延迟上述老化。稳定剂的重要代表是干扰自氧化过程中形成的自由基从而中断降解过程的抗氧化剂。主要抗氧化剂和次要抗氧化剂通常是有区别的,主要抗氧化剂可以直接与含氧自由基或C-自由基发生反应,次要抗氧化剂则与中间形成的氢过氧化物发生反应(见C.等人,Ullmann’s Encyclopedia of IndustrialChemistry中的Antioxidants,Wiley-VCH Verlag,Weinheim 2015)。主要抗氧化剂的典型代表是酚类抗氧化剂、胺类等,但也包括某些内酯类(苯并呋喃酮)。次要抗氧化剂的类别包括磷化合物,例如亚磷酸酯和亚膦酸酯,但也包括有机硫化合物,例如长链烷基衍生物形式的硫化物和二硫化物。典型地,主要抗氧化剂和次要抗氧化剂在实践中经常结合使用,这产生了协同效应。
由化石原料,如原油或天然气形成的塑料如今正越来越多地被基于可持续原料的塑料所补充或取代,相应的单体是通过生物化学过程产生的。因此,也有必要寻找同样基于可持续原料的添加剂。由于稳定剂,特别是抗氧化剂几乎用于所有的塑料,因此特别需要由可持续原料制成的高效稳定剂。
基本上,由可持续原料制成的主要抗氧化剂是已知的,其偶尔也用于塑料中。生育酚(维生素E)是典型的实例。生育酚,与传统的抗氧化剂类似,具有空间受阻酚结构,并可以单独使用或与次要抗氧化剂一起使用(例如S.Al-Malaika,Macromol.Symp.2001,176,107)。生育酚可以例如从小麦胚芽油、葵花籽油或橄榄油等天然产品中分离出来。在塑料中检验过的其他已知的由天然物质制成的酚类抗氧化剂包括,例如:
-槲皮素(B.Kirschweng等人,Melt stabilisation of PE with naturalantioxidants:Comparison of rutin and quercetin,ur.Pol.J.2018,103,228-237)
-二氢杨梅素(B.Kirschweng等人,Melt stabilization of polyethylene withdihydromyrecitin,a natural antioxidant,Pol.egr.tab.016,133,192-200)
-迷迭香酸的衍生物(K.Doudin等人,New genre of.antioxidants fromrenewable natural resources:Synthesis and characterisation of rosemary plant-derived antioxidants and their performance in polyolefins,Pol.Degr.Stab.2016,130,126-134,见附件)
-单宁(W.J.Grigsby等人,Esterification of condensed tannins and theirimpact on the properties of poly(lactic acid),Polymers·s(2013)344-360)
-姜黄素(D.Tatraaljai等人,Processing stabilisation of PE with anatural antioxidant,curcumin,European Polymer Journal 49(2013)1196-1203)和
-水飞蓟素和水飞蓟宾(B.Kirschweng等人,Melt stabilization ofpolyethylene with natural antioxidants:comparison of a natural extract andits main components.Journal of Thermal Analysis and Calorimetry https://doi.or g/10.1007/s10973-020-09709-5)
-来自茶叶和咖啡提取物的儿茶素(O.Olejnik,A.Masek,Bio-Based PackagingMaterials Containing Substances Derived from Coffee and Tea Plants,Materials2020,13,5719)
WO2020/083740描述了通过由多酚和糖醇或环多醇制成的协同组合物对天然酚用途的改进。
然而,一些已经作为塑料稳定剂检验过的天然酚类也有缺点,例如:不理想的密集着色(例如姜黄素),不同和变化的组合物的混合物(例如迷迭香和其他植物提取物,水飞蓟素),不充分的长期效果(例如生育酚)和/或挥发性。
去氢双丁香酚(低聚物、聚合物和共聚物)以前没有被用作热塑性塑料的稳定剂。文献WO2019/092359A1,或者Goswinus H.M.de Kruijff等人,Green Chem.,2019,21,481.5-4823中描述了去氢双丁香酚作为环氧树脂原料的用途。然而,在这种情况下,对作为抗氧化剂的效果至关重要的酚基要么被环氧化,要么在环氧树脂的交联反应中被反应性转化。
因此,人们仍在寻找基于可持续原材料且不存在这些缺点的有效稳定剂。
该问题通过去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物用于稳定有机材料、特别是抗氧化降解、热降解和/或光化降解的用途被解决。权利要求12涉及相应的经稳定的塑料组合物。权利要求14具体说明稳定剂组合物。权利要求16具体说明稳定有机材料的方法。从属权利要求涉及有利的实施方案。
低聚物或聚合物也可以理解为与其他合适单体的共低聚物或共聚物。对于作为抗氧化剂的效果至关重要的是:酚基在聚合物和低聚物或共聚物和共低聚物中作为活性成分被保留,和在聚合物合成中不在反应中失活,例如通过缩合和转化为酯基或醚基。用于聚碳酸酯进一步反应和合成聚硅氧烷共聚物的丁香酚端基,例如在WO2019/228783或WO2020/094553中描述的,由于这些聚合物不含游离酚基而不包括在本发明中。
用于制备去氢双丁香酚和丁香酚低聚物及丁香酚聚合物的天然原料丁香酚可以从丁香油中获得,但也可以通过生物技术工艺从生物质中获得,例如基于木材。
去氢双丁香酚是由丁香酚通过氧化偶联制备的,例如根据F.A.Marques等人,Tetrahedron Letters 1998,39,943-946,M.Ogata等人,Biol.Pharm.Bull.2005,28,1120-1 122;或通过电化学产生的(G.H.M.de Kruijff等人,Green Chem.2019,21,4815-4823);或通过漆酶酶促产生的(A.Llevot等人,Polym.Chem.2015,6.7693-7700)。
出人意料地,发现丁香酚或其衍生物对有机材料,特别是塑料具有稳定作用。
优选地,丁香酚共低聚物和/或丁香酚共聚物包含重复单元A和B或由其形成:
其中,重复单元A具有下式结构:
并且B是至少一个衍生自可自由基聚合、可阴离子聚合、可阳离子聚合或可配位聚合的单体的重复单元,特别是乙烯、丙烯、丁二烯、异戊二烯、苯乙烯或苯乙烯衍生物,如α-甲基苯乙烯、丙烯酸酯,如丙烯酸乙酯、丙烯酸丙酯、丙烯酸丁酯、丙烯酸月桂酯或丙烯酸硬脂酯、甲基丙烯酸酯,如甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸羟乙酯、甲基丙烯酸月桂酯或甲基丙烯酸硬脂酯、丙烯腈、及其混合物和组合。优选的可自由基聚合的单体B特别是苯乙烯、丙烯酸正丁酯和甲基丙烯酸甲酯。
得到的丁香酚低聚物或丁香酚聚合物中不存在共聚单体B。
特别地,根据本发明的共低聚物和共聚物的用途还具有以下特点:
重复单元A与所有重复单元总数的摩尔比为3%至99.99%,优选25%至99%,和/或
重复单元A的总数为3至100,重复单元B的总数为1至100。
这里,低聚物或共低聚物被理解为包含最多10个重复单元A或A和B的化合物;聚合物或共聚物被理解为包含多于10个重复单元A或A和B的化合物。
交联结构也可能存在于共聚物中,并通过向能够聚合的组合物中加入二官能、三官能或更高官能的单体,如二乙烯基苯或季戊四醇四丙烯酸酯,以及去氢双丁香酚来获得。
低聚物或共低聚物对于用途是优选的。去氢双丁香酚是更优选的。
这里,聚合物或低聚物可以通过丁香酚的烯丙基进行聚合反应而产生,因此酚基在低聚物或聚合物结构中基本保持不变。
例如,聚合的或低聚的丁香酚可以通过电化学方法由丁香酚合成。烯丙基化合物原则上可通过自由基聚合、受控自由基聚合、阴离子聚合、阳离子聚合或配位聚合进行聚合(参见例如A.Matsumoto,Polymerization of multiallyl monomers,Progress ofPolymer Science,2001,26,189-257)。聚合方法是本领域技术人员已知的,例如可以从相关著作中推断出来,如Ullmann’s Encyclopedia of Industrial Chemistry,Polymerisation Processes,Wiley 2015。对于自由基聚合、受控自由基聚合、阳离子聚合、阴离子聚合或配位聚合,首先需要通过已知的方法为酚基提供保护基团,例如提供乙酰基,在聚合或共聚后将其去除,对于乙酰基,例如通过水解。在用烯丙基进行自由基聚合的情况下,通常优选低聚结构。共聚物可以通过将带有保护基的丁香酚与另一种能够聚合的单体,例如苯乙烯、苯乙烯衍生物、丙烯酸酯或甲基丙烯酸酯,通过上述方法之一聚合而获得。
此外,低聚的和聚合的丁香酚可以通过氧化C-C偶联反应合成,例如铜催化或酶催化的。然后得到以下聚合结构,n=3至100、优选3至10。
自由基聚合、阳离子聚合或配位聚合也可用于获得具有下式的低聚的和聚合的丁香酚。
这里,n具有上述的含义。
这里,低聚物被理解为包含最多10个重复单元(n=3至10)的化合物;聚合物被理解为包含多于10个重复单元的化合物。
丁香酚低聚物或丁香酚聚合物也可以通过ZnO催化反应来制备(J.E.Weinberg等人,Journal of Dental Research(1972),51,1055-61),其中聚合也主要通过烯丙基进行,并且酚基基本保持。产生丁香酚(共)聚合物的另一种可能性是由丁香酚甲醛聚合物novolaks构成(M.Shibata等人,React.Funct.Polym.2013,73,1086)。
所有先前描述的制备丁香酚聚合物或去氢双丁香酚聚合物或共聚物的方法也可用于本发明的目的,因此也包括在本发明中。
由于除了酚基外,烯丙基也同样有助于稳定效果,因此非常特别地优选去氢双丁香酚。
优选的实施方案为塑料、涂料、润滑油、液压油、发动机油、涡轮机油、传动油、金属加工液、化学品或单体提供稳定作用。
稳定塑料的用途是非常特别优选的。
优选地,去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物在有机材料中的重量比为0.01重量%至10.00重量%、优选0.02重量%至5.00重量%、更优选0.05重量%至3.00重量%、特别优选0.10重量%至2.00重量%。
这里,优选的待稳定的塑料选自以下组:
a)烯烃或二烯烃的聚合物,例如聚乙烯(LDPE、LLDPE、VLDPE、ULDPE、MDPE、HDPE、UHMWPE)、茂金属-PE(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,例如天然橡胶(NR)、聚环辛烯、聚亚烷基-一氧化碳共聚物、以及无规结构或嵌段结构形式的共聚物,例如聚丙烯-聚乙烯(EP)、EPM或EPDM,其中例如5-亚乙基-2-降冰片烯作为共聚单体、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-(甲基)丙烯酸缩水甘油酯、接枝聚合物例如聚丙烯接枝马来酸酐、聚丙烯接枝丙烯酸、聚乙烯接枝丙烯酸、聚乙烯-聚丙烯酸丁酯-接枝-马来酸酐、以及共混物,例如LDPE/LLDPE或用α-烯烃作为共聚单体制备的长链支化聚丙烯共聚物,所述α-烯烃例如1-丁烯、1-己烯、1-辛烯或1-十八烯,
b)聚苯乙烯、聚甲基苯乙烯、聚α-甲基苯乙烯、聚乙烯基萘、聚乙烯基联苯、聚乙烯基甲苯、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(SAN)、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,包括对应的接枝共聚物,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构成的接枝共聚物(MABS)、以及氢化的聚苯乙烯衍生物,例如聚乙烯基环己烷,
c)含卤素的聚合物,例如聚氯乙烯(PVC)、聚氯丁二烯和聚偏二氯乙烯(PVDC)、氯乙烯和偏二氯乙烯的共聚物或氯乙烯和乙酸乙烯酯的共聚物、氯化的聚乙烯、聚偏二氟乙烯、环氧氯丙烷均聚物和共聚物,特别是与环氧乙烷的共聚物(ECO),
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)不饱和醇的聚合物和衍生物,例如聚乙烯醇、聚乙酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙酯、聚烯丙基三聚氰胺,
f)聚缩醛,例如聚甲醛(POM)或与例如丁醛的共聚物,聚苯醚以及与聚苯乙烯或聚酰胺的共混物,
g)环状醚的聚合物,例如聚乙二醇、聚丙二醇、聚环氧乙烷、聚环氧丙烷、聚四氢呋喃,
h)聚苯醚及其与聚苯乙烯和/或聚酰胺的共混物,
i)由羟基封端的聚醚或聚酯和芳香族或脂肪族异氰酸酯,例如2,4-甲苯二异氰酸酯或2,6-甲苯二异氰酸酯或亚甲基二苯基二异氰酸酯制成的聚氨酯,特别是线型聚氨酯(TPU)、聚脲,
j)聚酰胺,例如聚酰胺-6、聚酰胺-6.6、聚酰胺-6.10、聚酰胺-4.6、聚酰胺-4.10、聚酰胺-6.12、聚酰胺-10.10、聚酰胺-10.12、聚酰胺-12.12、聚酰胺11、聚酰胺12和(部分)芳香族聚酰胺,例如聚苯二甲酰胺,其例如由对苯二甲酸和/或间苯二甲酸以及脂肪族二胺例如六亚甲基二胺或间苯二甲基二胺制成,或由脂肪族二羧酸例如己二酸或癸二酸和芳香族二胺例如1,4-苯二胺或1,3-苯二胺制成,不同聚酰胺例如PA-6和PA 6.6的共混物或聚酰胺和聚烯烃的共混物,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)由脂肪族或芳香族二羧酸和二醇或由羟基羧酸制成的聚酯,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(PTT)、聚萘二甲酸乙二醇酯(PEN)、聚对苯二甲酸-1,4-环己烷二甲醇酯、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)、聚琥珀酸乙二醇酯、聚琥珀酸四亚甲酯、聚己内酯,
m)聚碳酸酯、聚酯碳酸酯和共混物,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、醋酸纤维素、丙酸纤维素、丁酸纤维素,
o)环氧树脂,其由双官能或多官能环氧化合物与例如基于胺、酸酐、双氰胺、硫醇、异氰酸酯的硬化剂或催化活性硬化剂结合组成,
p)酚醛树脂,例如苯酚甲醛树脂、脲甲醛树脂、三聚氰胺甲醛树脂,
q)由不饱和二羧酸和二醇与乙烯基化合物,例如苯乙烯制成的不饱和聚酯树脂、醇酸树脂,
r)硅酮,其例如基于二甲基硅氧烷、甲基-苯基-硅氧烷或二苯基硅氧烷,例如乙烯基封端的,
s)以及上述聚合物的一种或多于一种的混合物、组合或共混物。
如果a)至r)项下指定的聚合物是共聚物,它们可以以无规结构、嵌段结构或锥形结构的形式存在。
此外,所述聚合物可以以线型结构、支化结构、星形结构或超支化结构的形式存在。
如果a)至r)项下指定的聚合物是有规立构聚合物,它们可以以全同立构、立体定向的形式存在,但其也可以以无规立构形式或立体嵌段共聚物的形式存在。
此外,a)至r)项下指定的聚合物可以具有非晶形和(部分)结晶的形态。
任选地,a)项下提及的聚烯烃也可以是交联的,例如称为X-PE的交联聚乙烯。
此外,本发明的化合物还可用于稳定橡胶和弹性体。这可以是天然橡胶(NR)或合成橡胶材料,例如氯丁二烯(CR)、聚丁二烯(BR)、苯乙烯-丁二烯(SBR)、聚异戊二烯(IR)、丁基橡胶(IIR)、丁腈橡胶(NBR)、氢化丁腈橡胶(HNBR)、聚酯或聚醚氨酯橡胶或硅橡胶。
除了新商品,这些塑料可以是回收的塑料,例如,来自工业收集的塑料如生产废料,或来自家庭或可回收物收集的塑料。
此外,特别优选完全或部分由可持续原料,例如聚乳酸(PLA)、聚乳酸(PLA)、聚琥珀酸丁二酯(PBS)、聚琥珀酸丁二酯-co-己二酸酯(PBSA)、聚(己二酸丁二酯)(PBA)、聚(琥珀酸六亚甲酯)、聚对苯二甲酸乙二酯(PET)、聚对苯二甲酸丁二酯(PBT)、聚对苯二甲酸丙二酯(PPT)、聚呋喃酯(聚(2,5-呋喃二甲酸乙二酯))(PEF)、聚-3-羟基丁酸酯、聚-4-羟基丁酸酯、聚-3-羟基戊酸酯制备的聚合物。
此外,优选地,有机材料,特别是塑料,包含至少一种额外的添加剂,其选自主要抗氧化剂和/或次要抗氧化剂,特别地,主要抗氧化剂和/或次要抗氧化剂选自亚磷酸酯/盐、亚膦酸酯/盐、硫醇、酚类抗氧化剂、空间受阻胺、羟胺、及其混合物或组合,UV吸收剂、光稳定剂、基于羟胺的稳定剂、基于苯并呋喃酮的稳定剂、成核剂、抗冲改性剂、增塑剂、模具润滑剂、流变改性剂、扩链剂、加工助剂、颜料、染料、光学增白剂、抗微生物剂、抗静电剂、滑爽剂、防结块剂、偶联剂、分散剂、增容剂、氧清除剂、酸清除剂、共稳定剂、标记剂、防雾剂,特别地次要抗氧化剂在使用过程中被添加到塑料中,其中亚磷酸酯/盐、亚膦酸酯/盐、酸清除剂、受阻胺和/或其组合是特别优选的。
在上述实施方案中,如果至少一种添加剂的含量或添加量为基于去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物、有机材料和至少一种添加剂的总量的0.01重量%至9.99重量%、优选0.01重量%至4.98重量%、特别优选0.02重量%至2.00重量%。
本发明还涉及有机材料,特别是塑料组合物,其含有去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物作为稳定剂。
特别有利的是具有以下组成的有机材料,特别是塑料组合物:
0.01重量%至10.00重量%、优选0.02重量%至5.00重量%、更优选0.05重量%至3.00重量%、特别优选0.10重量%至2.00重量%的去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物,
99.99重量%至90.00重量%、优选99.89重量%至95.00重量%、更优选97.00重量%至99.95重量%、特别优选99.90重量%至98.00重量%的至少一种有机材料,优选地,其选自塑料、涂料、润滑剂、液压油、发动机油、涡轮机油、传动油、金属加工液、化学品或单体,和
0重量%至9.99重量%、优选0重量%至4.98重量%、特别优选0.02重量%至2.00重量%的至少一种添加剂,
其中各组分合计为100重量%。
塑料组合物可以以注塑件、箔或薄膜、泡沫、纤维、线缆和管道、型材、中空体、带状物、膜例如土工膜、或黏合剂的形式存在,其通过挤出、注塑、吹塑、压延、压制工艺、旋压工艺或滚塑制成,例如用于电气和电子工业、建筑业、运输业(汽车、飞机、船舶、铁路)、医疗应用、家用电器、车辆部件、消费产品、包装、家具、纺织品。其他应用领域是油漆、着色剂和涂料。
优选地,至少一种添加剂选自主要抗氧化剂和/或次要抗氧化剂,特别地,主要抗氧化剂和/或次要抗氧化剂选自亚磷酸酯/盐、亚膦酸酯/盐、硫醇、酚类抗氧化剂、空间受阻胺、羟胺、及其混合物或组合,UV吸收剂、光稳定剂、基于羟胺的稳定剂、基于苯并呋喃酮的稳定剂、成核剂、抗冲改性剂、增塑剂、模具润滑剂、流变改性剂、扩链剂、加工助剂、颜料、染料、光学增白剂、抗微生物剂、抗静电剂、滑爽剂、防结块剂、偶联剂、分散剂、增容剂、氧清除剂、酸清除剂、共稳定剂、标记剂、防雾剂,特别是次要抗氧化剂;
特别地,至少一种添加剂选自:选自亚磷酸酯/盐、亚膦酸酯/盐和硫醇的次要抗氧化剂,至少一种选自多元醇、酸清除剂和空间受阻胺的共稳定剂。
本发明还涉及稳定剂组合物,其包含以下组分或由以下组分组成:
去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物、及其混合物和组合,和
至少一种选自亚磷酸酯/盐、亚膦酸酯/盐或硫醇的次要抗氧化剂,和/或至少一种选自多元醇、酸清除剂或空间受阻胺的共稳定剂,及其混合物和组合。
因此,基于可持续原材料的新稳定剂组合物和稳定塑料的新方法成为可能,其具有高效,对环境友好,并具有有利的成本结构。
关于去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物的具体实施方案,请参考上述陈述。
优选地,在稳定剂组合物中去氢双丁香酚、低聚丁香酚或聚丁香酚和至少一种次要抗氧化剂和/或稳定剂以100:1至1:100、优选10:1至1:10、特别优选4:1至1:4的重量比存在。
本发明还涉及稳定有机材料,特别是抗氧化降解、热降解和/或光化降解的方法,其中将去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物并入有机材料中。
在优选的实施方案中,组合物含有次要抗氧化剂,特别是亚磷酸酯/亚膦酸酯或硫代化合物。
合适的亚磷酸酯是三苯基亚磷酸酯、二苯基烷基亚磷酸酯、苯基二烷基亚磷酸酯、三(壬基苯基)亚磷酸酯、三月桂基亚磷酸酯、三(十八烷基)亚磷酸酯、二硬脂基季戊四醇二亚磷酸酯、三(2,4-二叔丁基苯基)亚磷酸酯、二异癸基季戊四醇二亚磷酸酯、双(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯、双(2,4-二枯基苯基)季戊四醇二亚磷酸酯、双(2,6-二叔丁基-4-甲基苯基)季戊四醇二亚磷酸酯、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-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧磷杂环辛烷、双(2,4-二叔丁基-6-甲基苯基)甲基亚磷酸酯、双(2,4-二叔)-丁基-6-甲基苯基)乙基亚磷酸酯、6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧磷杂环辛烷、2,2’2”-次氮基[三乙基-三(3,3”,5,5’-四叔丁基-1,1’-联苯基-2,2’-二基)亚磷酸酯]、2-乙基己基(3,3’,5,5’-四叔丁基-1,1’-联苯基-2,2’-二基)亚磷酸酯、5-丁基-5-乙基-2-(2,4,6-三叔丁基苯氧基)-1,3,2-二氧磷杂环丙烷。
特别优选的亚磷酸酯/亚膦酸酯是:
其中n=3至100。
非常特别优选地,三(2,4-二叔丁基苯基)亚磷酸酯被用作次要抗氧化剂。
其中n=3至100。
非常特别优选地,三(2,4-二叔丁基苯基)亚磷酸酯被用作次要抗氧化剂。
此外,合适的次要抗氧化剂是有机硫化合物例如硫化物和二硫化物,例如二硬脂基硫代丙酸酯、二月桂基硫代丙酸酯;双十三烷基二硫代丙酸酯、双十四烷基硫代丙酸酯、3-(十二烷基硫代)-丙酸酯、1,1’-[2,2-双[[3-(十二烷基硫)-1-氧代丙氧基]甲基]-1,3-丙二基]丙酸酯。优选以下结构:
添加剂还可以选自:其他主要抗氧化剂、UV吸收剂、光稳定剂、金属减活剂、填料减活剂、抗臭氧剂、成核剂、抗成核剂、抗冲改性剂、增塑剂、模具润滑剂、流变改性剂、触变剂、扩链剂、加工助剂、脱模剂、阻燃剂、颜料、染料、光学增白剂、抗微生物剂、抗静电剂、滑爽剂、防结块剂、偶联剂、交联剂、抗交联剂、亲水剂、疏水剂、增附剂、分散剂、增容剂、氧清除剂、酸清除剂、发泡剂、降解助剂、消泡剂、气味清除剂、标记剂、防雾剂、填料和增强剂。
特别地,在优选的实施方案中,组合物含有酸清除剂。
合适的酸清除剂(“抗酸剂”)是一价、二价、三价或四价金属的盐,其中金属优选碱金属、碱土金属、铝或锌,特别是与脂肪酸形成的盐,例如硬脂酸钙、硬脂酸镁、硬脂酸锌、硬脂酸铝、月桂酸钙、山萮酸钙、乳酸钙、硬脂酰-2-乳酸钙。合适的酸清除剂的其他类别是水滑石,特别是基于铝、镁和锌的合成水滑石;水铝钙石;沸石,碱土金属氧化物,特别是氧化钙、氧化镁和氧化锌;碱土金属碳酸盐,特别是碳酸钙、碳酸镁、白云石;和氢氧化物,特别是水镁石(氢氧化镁)。
合适的其他主要抗氧化剂是酚类抗氧化剂、胺类和内酯类。
合适的酚类抗氧化剂是,例如:
烷基化的单酚,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-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-双十八烷基-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、直链或带支链的壬基苯酚如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、及其混合物;
烷基硫代甲基苯酚,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;
氢醌和烷基化的氢醌,例如2,6-二叔丁基-4-甲氧基苯基、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,如α-生育酚、β-生育酚、γ-生育酚、δ-生育酚、及其混合物(维生素E);
羟基化的硫代二苯基酯,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-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-双(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、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-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;
O-苄基、N-苄基和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、三癸基-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、双(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)硫醚、异辛基-3,5-二叔丁基-4-羟基苄基巯基乙酸酯;
羟基苄基化的丙二酸酯,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、双十二烷基巯基乙基-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;
芳香族羟基苄基化合物,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-羟基苯基乙基)-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-羟基苄基膦酸双十八酯、5-叔丁基-4-羟基-3-甲基苄基膦酸双十八酯、3,5-二叔丁基-4-羟基苄基膦酸单乙酯的钙盐;
酰胺基苯酚,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;
β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元醇或多元醇的酯,其中一元醇或多元醇例如甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、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)丙酸与一元醇或多元醇的酯,其中一元醇或多元醇例如甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二乙二醇、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]-2,4,8,10-四氧螺[5.5]十一烷;
β-(3,5-二环己基-4-羟基苯基)丙酸与一元醇或多元醇的酯,其中一元或多元醇例如甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、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)丙酸与一元或多元醇的酯,其中一元或多元醇例如甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二乙二醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、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;
抗坏血酸(维生素C)。
特别优选的酚类抗氧化剂具有以下结构:
特别优选的酚类抗氧化剂是3-(3,5-二叔丁基-4-羟基苯基)丙酸十八酯和季戊四醇四[3-(3,5-二叔丁基-4-羟基苯基)丙酸酯]。
其他特别优选的酚类抗氧化剂是基于可持续的原材料例如生育酚(维生素E)、生育三烯酚、生育单烯酚、类胡萝卜素、羟基苯乙醇、黄酮醇例如白杨素、槲皮素、橙皮苷、新橙皮苷、柚皮苷、桑色素、樟脑油、非瑟酮、花青素苷例如飞燕草素、锦葵色素、鼠尾草酸、鼠尾草酚、迷迭香酸、和白藜芦醇。
合适的胺类抗氧化剂是例如:
N,N’-二异丙基-对苯二胺、N,N’-二仲丁基-对苯二胺、N,N’-双(1,4-二甲基戊基)-对苯二胺、N,N’-双(1-乙基-3-甲基戊基)-对苯二胺、N,N’-双(1-甲基庚基)-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-(对甲苯磺酰胺基)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、辛基化的二苯胺,例如p,p’-二叔辛基二苯胺、4-正丁基氨基苯酚、4-丁酰基氨基苯酚、4-壬酰基氨基苯酚、4-十二烷酰基氨基苯酚、4-十八烷酰基氨基苯酚、双(4-甲氧基苯基)胺、2,6-二叔丁基-4-二甲基氨基甲基-苯酚、2,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基甲烷、N,N,N’,N’-四甲基-4,4’-二氨基二苯基甲烷、1,2-双[(2-甲基-苯基)氨基]乙烷、1,2-双(苯基氨基)丙烷、(邻甲苯基)双胍、双[4-(1’,3’-二甲基丁基)苯基]胺、叔辛基化的N-苯基-1-萘胺、单烷基化的叔丁基/叔辛基二苯胺和二烷基化的叔丁基/叔辛基二苯胺的混合物、单烷基化的壬基二苯胺和二烷基化的壬基二苯胺的混合物、单烷基化的十二烷基二苯胺和二烷基化的十二烷基二苯胺的混合物、单烷基化的异丙基/异己基二苯胺和二烷基化的异丙基/异己基二苯胺的混合物、单烷基化的叔丁基二苯胺和二烷基化的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、单烷基化的叔丁基/叔辛基苯基噻吩和二烷基化的叔丁基/叔辛基苯基噻吩嗪的混合物、单烷基化的叔辛基吩噻嗪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-2-烯、及其混合物或组合。
特别优选的胺类抗氧剂是: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。
特别优选的胺类抗氧化剂具有以下结构:
其他优选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(SI Group):
R1、R2=C14至C24烷基
合适的内酯是苯并呋喃酮和吲哚啉酮,例如3-[4-(2-乙酰氧基乙氧基)苯基]-5,7-二叔丁基-苯并呋喃-2-酮、5,7-二叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮、3,3’-双[5,7-二叔丁基-3-(4-(2-羟基乙氧基)苯基)苯并呋喃-2-酮)、5,7-二叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮、3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二叔丁基-苯并呋喃-2-酮、3-(3,5-二甲基-4-特戊酰氧基苯基)-5,7-二叔丁基-苯并呋喃-2-酮、3-(3,4-二甲基苯基)-5,7-二叔丁基-苯并呋喃-2-酮、3-(2,3-二甲基苯基)-5,7-二叔丁基-苯并呋喃-2-酮以及另外含有亚磷酸基团的内酯类例如:
另一组合适的抗氧化剂是异吲哚[2,1-A]喹唑啉,例如
此外,合适的共稳定剂是多元醇,特别是糖醇或环多醇。多元醇例如是季戊四醇、二季戊四醇、三季戊四醇、短链聚醚多元醇或短链聚酯多元醇、以及超支化聚合物/低聚物、或具有羟基的树枝状聚合物,例如:
优选地,至少一种糖醇选自苏糖醇、赤藓糖醇、半乳糖醇、甘露糖醇、核糖醇、山梨糖醇、木糖醇、阿糖醇、异麦芽糖醇、乳糖醇、麦芽糖醇、阿卓糖醇(塔罗糖醇)、艾杜糖醇、麦芽三糖醇、具有多元醇端基的氢化的寡糖和多糖及其混合物。特别优选地,至少一种优选的糖醇选自赤藓糖醇、甘露糖醇、异麦芽糖醇、麦芽糖醇及其混合物。
其他合适的糖醇的实例是庚糖醇和辛糖醇:内消旋-甘油型-阿洛型-庚糖醇,D-甘油型-D-阿卓型-庚糖醇,D-甘油型-D-甘露型-庚糖醇、内消旋-甘油型-古洛型-庚糖醇、D-甘油型-D-半乳糖型-庚糖醇(甘露庚糖醇)、D-甘油型-D-葡萄糖型-庚糖醇、L-甘油型-D-葡萄糖型-庚糖醇、D-赤型-L-半乳糖型-辛糖醇、D-苏型-L-半乳糖型-辛糖醇。
特别地,至少一种环多醇可以选自肌醇(肌肌醇(myo-inositol)、鲨肌醇(scyllo-inositol)、D-手性肌醇、L-手性肌醇、黏膜肌醇(muco-inositol)、新肌醇(neo-inositol)、异肌醇(allo-inositol)、表肌醇(epi-inositol)和顺肌醇)、1,2,3,4-四羟基环己烷、1,2,3,4,5-五羟基环己烷、栎醇、(1R,2S,3R,4S,5R,6S)-5,6-二甲氧基-1,2,3,4-环己烷四醇(viscumitol)、(1R,2R,3S,4S,5R,6S)-6-甲氧基-1,2,3,4,5-环己烷五醇(bornesitol)、牛弥菜醇、(1R,2S,3S,4S,5S,6S)-6-甲氧基-1,2,3,4,5-环己烷五醇(ononitol)、松醇、(1R,2R,3R,4S,5R,6S)-3,6-二甲氧基-1,2,4,5-环己烷四醇(pinpollitol)、白坚木醇、鹰嘴豆糖醇、奎宁酸、莽草酸和(1S,2S,3S,4R)-5-(羟甲基)-5-环己烯-1,2,3,4-四醇(valienol),这里优选肌肌醇(myo-inositol)。
合适的光稳定剂是例如基于2-(2’-羟基苯基)苯并三唑、2-羟基苯并苯酮、苯甲酸的酯、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)苯并三唑是例如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-氯代苯并三唑、2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯代苯并三唑、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’-二叔丁基-戊基-2’-羟基苯基)苯并三唑、2-(3’,5’-双(α,α-二甲基苯基)-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-氯代苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)-5-氯代苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯代苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-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’-月桂基-2’-羟基-5’-甲基苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧基羰基乙基)苯基苯并三唑、2,2’-亚甲基双[4-(1,1,3,3,-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟基苯基]-2H-苯并三唑与聚乙二醇300的酯交换产物;[R—CH2CH2—COO—CH2CH2-]-2,其中R=3’-叔丁基-4’-羟基-5’-2H-苯并三唑-2-基苯基、2-[2’-羟基-3’-(α,α-二甲基苄基)-5’-(1,1,3,3-四甲基丁基)苯基]苯并三唑、2-[-2’-羟基-3’-(1,1,3,3-四甲基丁基)-5’-(α,α-二甲基苄基)苯基]苯并三唑。
合适的2-羟基苯并苯酮是例如2-羟基苯并苯酮的4-羟基-、4-甲氧基-、4-辛氧基-、4-癸氧基-4-月桂氧基、4-苄氧基、4,2’,4-三羟基-和2’-羟基-4,4’-二甲氧基衍生物。
合适的丙烯酸酯是例如α-氰基-β,β-二苯基丙烯酸乙酯、α-氰基-β,β-二苯基丙烯酸异辛酯、α-羰基甲氧基肉桂酸甲酯、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-羰基甲氧基-对甲氧基肉桂酸甲酯和N-(β-羰基甲氧基-β-氰基乙烯基)-2-甲基吲哚啉。
合适的苯甲酸的酯是例如水杨酸-4-叔丁基苯酯、水杨酸苯酯、水杨酸辛基苯酯、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-2,4-二叔丁基苯酯、3,5-二叔丁基-4-羟基苯甲酸十六酯、3,5-二叔丁基-4-羟基苯甲酸十八酯、3,5-二-叔丁基-4-羟基苯甲酸-2-甲基-4,6-二叔丁基苯酯。
合适的草酰胺是例如4,4’-二辛氧基草酰苯胺、2,2’-二乙氧基草酰苯胺、2,2’-二辛氧基-5,5’-二叔丁基草酰苯胺、2,2’-双十二烷氧基-5,5’-二叔丁基草酰苯胺、2-乙氧基-2’-乙基草酰苯胺、N,N’-双(3-二甲基氨基丙基)草酰苯胺、2-乙氧基-5-叔丁基-2’-乙基草酰苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁基草酰苯胺的混合物、邻甲氧基-二取代的草酰苯胺和对甲氧基-二取代的草酰苯胺的混合物以及邻乙氧基-二取代的草酰苯胺和对乙氧基-二取代的草酰苯胺的混合物。
合适的2-(2-羟基苯基)-1,3,5-三嗪是例如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-4-三癸氧基苯基)-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/三癸氧基-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。
合适的金属减活剂是例如N,N’-二苯基草酰胺、N-水杨醛-N’-水杨酰肼、N,N’-双(水杨酰)肼、N,N’-双(3,5-二叔丁基-4-羟基苯基丙酰)肼、3-水杨酰基氨基-1,2,4-三唑、双(亚苄基)草酰二肼、草酰苯胺、间苯二甲酰二肼、癸二酰双苯肼、N,N’-二乙酰基己二酰二肼、N,N’-双(水杨酰基草酰二肼、N,N’-双(水杨酰基)硫代丙酰二肼、三[2-叔丁基-4-硫代(2’-甲基-4’-羟基-5’-叔丁基)-苯基-5-甲基]苯基亚磷酸酯。
特别优选的金属减活剂是:
合适的受阻胺是例如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、双(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)-正丁基-3,5-二叔丁基-4-羟基苯基丙二酸酯、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-1,3,5-三嗪的直链或环状缩合产物、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)六亚甲基二胺与4-吗啉基-2,6-二氯-1,3,5-三嗪的直链或环状缩合产物、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]癸烷和环氧氯丙烷的反应产物。
空间受阻的N-H、N-烷基如N-甲基或N-辛基、N-烷氧基衍生物如N-甲氧基或N-辛氧基、环烷基衍生物如N-环己氧基和N-(2-羟基-2-甲基丙氧基)类似物也各自包括在上述给出的结构中。
优选的受阻胺还具有以下结构:
优选的低聚和聚合的受阻胺具有以下结构:
在上述化合物中,n分别表示3至100。
另一种合适的光稳定剂是Hostanox NOW(制造商:Clariant SE),其一般结构如下:
合适的分散剂是例如:
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-乙烷二基双十八烷酰胺、脱水山梨醇酯例如脱水山梨醇单硬脂酯、钛酸酯和锆酸酯、具有官能团的反应性共聚物例如聚丙烯-co-丙烯酸、聚丙烯-co-马来酸酐、聚乙烯-co-甲基丙烯酸缩水甘油酯、聚苯乙烯-alt-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有羟基的树枝状聚合物。
合适的抗成核剂是吖嗪染料,例如苯胺黑。
特别地,合适的阻燃剂是:
无机阻燃剂例如Al(OH)3、Mg(OH)2、AIO(OH)、MgCO3、页硅酸盐例如蒙脱石或海泡石、未改性或有机改性的复盐例如Mg-Al-硅酸盐、POSS(多面体低聚倍半硅氧烷)化合物、碳酸钙镁石、水菱镁矿或埃洛石和Sb2O3、Sb2O5,MoO3、锡酸锌、羟基锡酸锌,
含氮的阻燃剂例如三聚氰胺、蜜勒胺、蜜白胺、聚[(8-氨基-1,3,4,6,7,9,9b-七氮杂非那烯-2,5-亚基)亚氨基]、三聚氰胺衍生物、三聚氰胺缩合产物或三聚氰胺盐、苯代三聚氰胺、聚异氰脲酸酯、尿囊素、磷腈,特别是三聚氰胺氰脲酸盐、磷酸三聚氰胺、磷酸二三聚氰胺、焦磷酸三聚氰胺、多磷酸三聚氰胺、三聚氰胺金属磷酸盐例如磷酸三聚氰胺铝、磷酸三聚氰胺锌、磷酸三聚氰胺镁以及相对应的焦磷酸盐和多磷酸盐、聚-[2,4-(哌嗪-1,4-基)-6-(吗啉-4-基)-1,3,5-三嗪]、多磷酸铵、硼酸三聚氰胺、氢溴酸三聚氰胺,
自由基形成剂例如烷氧基胺、羟胺酯、偶氮化合物、三嗪化合物、二硫化物、多硫化物、硫醇、硫化福美双、二硫代氨基甲酸酯、巯基苯并噻唑、亚磺酰胺、亚磺酰亚胺、二枯基或多枯基、羟基亚胺及其衍生物例如羟基亚胺酯或羟基亚胺醚,
含有磷的阻燃剂例如红磷、磷酸酯例如间苯二酚二磷酸酯、双酚A-二磷酸酯、及其低聚物、三苯基磷酸酯、乙二胺二磷酸酯、亚膦酸酯/盐例如次磷酸及其衍生物例如烷基亚膦酸盐,例如二乙基亚膦酸铝或二乙基亚膦酸锌或亚膦酸铝、亚磷酸铝、膦酸铝、膦酸酯、甲烷膦酸的低聚物和聚合物衍生物、9,10-二氢-9-氧杂-10-磷酰基菲-10-氧化物(DOPO)、及其经取代的化合物,
基于氯和溴的卤化阻燃剂,例如多溴联苯氧化物例如十溴二苯醚、三(3-溴-2,2-双(溴甲基)丙基-磷酸酯、三(三溴新戊基)磷酸酯、四溴邻苯二甲酸、1,2-双(三溴苯氧基)乙烷、六溴环十二烷、溴化的二苯基乙烷、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、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、溴化聚苯醚、溴化环氧树脂、聚五溴苄基丙烯酸酯、任选地与Sb2O3和/或Sb2O5结合,
硼酸盐,例如硼酸锌或硼酸钙,其任选地在载体材料例如二氧化硅上
含硫的化合物,例如元素硫、二硫化物和多硫化物、硫化福美双、二硫代氨基甲酸酯、巯基苯并噻唑和亚磺酰胺,
防滴剂,例如聚四氟乙烯,
含硅的化合物,如聚苯基硅氧烷,
碳改性物,例如碳纳米管(CNT)、剥落石墨或石墨烯、
及其组合或混合物。
以下是不含卤素的化合物,是非常特别优选的阻燃剂:
Al(OH)3,Mg(OH)2,
R=烷基、苯基
合适的增塑剂例如是邻苯二甲酸酯、己二酸酯、柠檬酸酯、1,2-环己烷二羧酸酯、偏苯三酸酯、异山梨醇酯、磷酸酯、环氧化物,如环氧化大豆油、或脂肪族聚酯。
合适的模具润滑剂和加工助剂是,例如聚乙烯蜡、聚丙烯蜡、脂肪酸的盐,例如硬脂酸钙、硬脂酸锌、或蒙脱石蜡的盐、酰胺蜡例如芥酸酰胺或油酸酰胺、含氟聚合物、硅酮、或新烷氧基钛酸酯/盐和锆酸酯/盐。
合适的颜料可以是无机的或有机的。无机颜料是例如二氧化钛、氧化锌、硫化锌、氧化铁、群青、炭黑;有机颜料是例如蒽醌、蒽缔蒽酮、苯并咪唑酮、喹吖啶酮、二酮基吡咯并吡咯、二嗪、靛蒽醌、异吲哚啉、偶氮化合物、二萘嵌苯、酞菁或吡喃酮。其他合适的颜料包括金属基底上的效果颜料或金属氧化物基底上的珠光颜料。
合适的填料减活剂是例如聚硅氧烷、聚丙烯酸酯,特别是嵌段共聚物例如聚甲基丙烯酸聚亚烷基氧化物或聚(甲基)丙烯酸缩水甘油酯、及其共聚物,例如与具有例如以下结构的苯乙烯和环氧化物:
合适的抗静电剂是例如乙氧基化的烷基胺、脂肪酸酯、烷基磺酸酯/盐、和聚合物例如聚醚酰胺。
合适的抗臭氧剂是上述的胺类,比如说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’-二环己基对苯二胺、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。
例如用于制备流变受控的聚丙烯(CR-PP)的合适的流变改性剂是例如过氧化物、烷氧基胺酯、氧胺磺酸酯,特别是以下结构:
合适的成核剂例如是单官能和多官能羧酸例如苯甲酸、琥珀酸、己二酸的滑石、碱金属或碱土金属盐,例如苯甲酸钠、甘油酸锌、羟基-双(4-叔丁基)苯甲酸铝、2,2’-亚甲基-双(4,6-二叔丁基苯基)磷酸盐、以及三酰胺和二酰胺例如均苯三甲酸三环己基胺、均苯三甲酸三(4-甲基环己基酰胺)、均苯三甲酸三(叔丁基酰胺)、N,N’,N”-1,3,5-苯甲三基三(2,2-二甲基丙酰胺)或2,6-萘二甲酸二环己基酰胺。
用于缩聚聚合物的直链分子量结构的合适的添加剂(扩链剂)是例如二环氧化物、双唑酮、双/>唑酮、双/>嗪、二异氰酸酯、二酐、双酰基内酰胺、双马来酰亚胺、二氰酸酯、碳化二亚胺。其它合适的扩链剂是聚合物化合物,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。
增加导电性的合适添加剂是例如上述抗静电剂、炭黑和碳化合物,如碳纳米管和石墨烯,金属粉末,如铜粉,以及导电聚合物,如聚吡咯、聚苯胺和聚噻吩。增加热导率的合适添加剂是例如氮化铝和氮化硼。
合适的红外活性添加剂是例如硅酸铝、氢氧化铝或染料,如酞菁或蒽醌。
合适的交联剂是例如过氧化物如二烷基过氧化物、烷基芳基过氧化物、过氧酯、过氧碳酸酯/盐、二酰基过氧化物、过氧缩酮,硅烷,例如乙烯基三甲氧基硅烷、乙烯基三乙氧基硅烷、乙烯基三乙酰氧基硅烷、乙烯基三(2-甲氧基乙氧基)硅烷、3-甲基丙烯酰氧基丙基三甲氧基硅烷、乙烯基二甲氧基甲基硅烷或乙烯-乙烯基硅烷共聚物。
合适的降解助剂是特别加速或控制聚合物在环境中的降解的添加剂。实例为过渡金属脂肪酸酯,例如锰或铁的,其可加速氧化和/或光氧化降解例如聚烯烃的,或诱导水解降解的酶,例如脂肪族聚酯。
合适的化学发泡剂是例如偶氮化合物如偶氮二羧酸二酰胺、磺酰半肼如对甲苯磺酰半肼、四氮唑如5-苯基四氮唑、酰肼如对甲苯磺酰肼、4,4’-氧代双(苯磺酰)肼、N-亚硝基化合物如N,N’-二硝基五亚甲基四胺、或碳酸盐如碳酸氢钠或碳酸锌。
合适的爽滑剂是例如酰胺蜡,如芥酸酰胺或油酸酰胺。
合适的防结块剂是例如二氧化硅、滑石或沸石。
合适的防雾剂是例如乙氧基化的脱水山梨醇酯、乙氧基化的脂肪酸醇或乙氧基化的烷基胺酯。
合适的杀菌剂是例如季铵盐或银盐、胶体银或银复合物或天然产品衍生物,例如甲壳素。
合适的醛清除剂是胺、羟胺、聚乙烯醇、沸石或环糊精,合适的甲醛清除剂是三聚氰胺衍生物,例如苯代三聚氰胺或尿素衍生物如尿囊素。
合适的气味结合或气味抑制物质是硅酸盐,如硅酸钙、沸石或羟基脂肪酸的盐类,例如赤霉酸锌。
合适的标记物是例如荧光染料或稀土。
增加塑料导热性的合适添加剂是例如无机填料如氮化硼、氮化铝、氧化铝、硅酸铝、碳化硅,但也包括碳纳米管(CNT)。
合适的抗冲击改性剂通常是针对特定的回收物而选择的,例如选自官能化或非官能化的聚烯烃,例如乙烯共聚物如EPDM或马来酸酐或苯乙烯-丙烯腈改性的EPDM、甲基丙烯酸缩水甘油酯改性的乙烯-丙烯酸酯共聚物或还有离子聚合物,例如基于MBS(甲基丙烯酸酯-丁二烯-苯乙烯共聚物)或丙烯酸酯-甲基丙烯酸甲酯的核壳聚合物、热塑性弹性体(TPE)例如基于苯乙烯嵌段共聚物(苯乙烯-丁二烯(SB)、苯乙烯-丁二烯-苯乙烯(SBS)、其任选地水合(SEBS)或由马来酸酐改性(SEBS-g-MAH),热塑性聚氨酯、共聚物或共聚酰胺。
合适的脱模剂是例如硅酮、肥皂和蜡,例如蒙旦蜡。
用于稳定的方法:
根据本发明的添加剂,即去氢双丁香酚、丁香酚低聚物和/或丁香酚聚合物可以以粉末、液体、油、压制的、在载体材料上、颗粒、溶液或片状的形式存在,优选与待稳定的聚合物混合;聚合物基体被融化,然后冷却。另外,也可以将添加剂引入熔融状态的聚合物熔体中。
如果在聚合物组合物中加入其他组分,这些组分可以以液体、粉末、颗粒或压制产品的形式单独加入聚合物中,或与上述根据本发明的添加剂组合物一起加入。
将上述添加剂组合物和任选地其他添加剂通过常规加工方法并入塑料材料中,其中聚合物被熔化并与根据本发明的添加剂组合物和任选地其他添加剂混合,优选通过搅拌机、捏和机、挤出机。挤出机例如单螺杆挤出机、双螺杆挤出机、行星辊挤出机、圆环挤出机、共捏合机是优选的,其优选装配有真空脱气装置。加工可以在空气或任选地惰性气体条件下进行。
此外,添加剂组合物可以以母料或浓缩物的形式制备和引入组合物中,例如包含10%至90%的根据本发明的组合物。
本发明将参照以下实施方案进行更详细的描述,而不将本发明限制在具体所示的实施例中。
实施方案:
为了测试根据本发明的稳定剂的效果,将商品聚丙烯(Moplen HP 500N,LyondellBasell Industries)与0.10%的去氢双丁香酚(试验1)、0.25%的去氢双丁香酚(试验2)和0.5%的去氢双丁香酚(试验3)均化为粉末-粉末混合物,在200℃和每分钟90转的双螺杆微挤出机(MC 5,制造商DSM)中旋转30分钟,并记录力的下降。力是衡量聚丙烯分子量的直接标准;减少量越小,稳定效果越好。
与不含添加剂的聚丙烯相比,随着去氢双丁香酚浓度的增加,实现了增加的加工稳定性,即产生了更大的剩余力。
类似地,通过将0.25%的去氢双丁香酚与0.25%的次要抗氧化剂(三(2,4-二叔丁基苯基)亚磷酸酯)相结合,进一步提高了加工稳定性。
类似地,通过将0.25%的去氢双丁香酚与0.25%的以甲硫氨酸形式存在的含硫次要抗氧化剂相结合,进一步提高了加工稳定性。
类似地,通过添加0.25%的去氢双丁香酚,提高了聚乙烯、聚苯乙烯、聚酰胺-6和聚丙烯-消费后回收物的加工稳定性。
为了测试改进后的长期稳定性,将含有0.25%的去氢双丁香酚的聚丙烯颗粒在135℃的循环空气炉中与经碱稳定的聚丙烯(含有0.05%的抗氧化剂)进行比较,通过测量MVR(熔融体积速率)的变化来确定聚合物开始降解的时间。与比较例相比,长期稳定性从100小时提高到300小时以上。
Claims (16)
1.去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物用于稳定有机材料,特别是抗氧化降解、热降解和/或光化降解的用途。
2.根据权利要求1所述的用途,其用于稳定塑料、涂料、润滑剂、液压油、发动机油、涡轮机油、传动油、金属加工液、化学品或单体。
6.根据前述权利要求所述的用途,其特征在于
重复单元A与所有重复单元总数的摩尔比为3%至99.99%,优选25%至99%,和/或
重复单元A的总数为3至100,且重复单元B的总数为1至100。
7.根据前述权利要求中任一项所述的用途,其特征在于去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物在有机材料中的重量比为0.01重量%至10.00重量%,优选0.02重量%至5.00重量%,更优选0.05重量%至3.00重量%,特别优选0.10重量%至2.00重量%。
8.根据前述权利要求中任一项所述的用途,其用于稳定塑料,其中塑料选自
a)烯烃或二烯烃的聚合物,例如聚乙烯(LDPE、LLDPE、VLDPE、ULDPE、MDPE、HDPE、UHMWPE)、茂金属-PE(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,例如天然橡胶(NR)、聚环辛烯、聚亚烷基-一氧化碳共聚物、以及无规结构或嵌段结构形式的共聚物,例如聚丙烯-聚乙烯(EP)、EPM或EPDM,其中例如5-亚乙基-2-降冰片烯作为共聚单体、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-(甲基)丙烯酸缩水甘油酯、接枝聚合物,例如聚丙烯接枝马来酸酐、聚丙烯接枝丙烯酸、聚乙烯接枝丙烯酸、聚乙烯-聚丙烯酸丁酯-接枝-马来酸酐、以及共混物,例如LDPE/LLDPE或用α-烯烃作为共聚单体制备的长链支化的聚丙烯共聚物,所述α-烯烃例如1-丁烯、1-己烯、1-辛烯或1-十八烯,
b)聚苯乙烯、聚甲基苯乙烯、聚α-甲基苯乙烯、聚乙烯基萘、聚乙烯基联苯、聚乙烯基甲苯、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(SAN)、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,包括对应的接枝共聚物,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构成的接枝共聚物(MABS)、以及氢化的聚苯乙烯衍生物,例如聚乙烯基环己烷,
c)含卤素的聚合物,例如聚氯乙烯(PVC)、聚氯丁二烯和聚偏二氯乙烯(PVDC)、氯乙烯和偏二氯乙烯的共聚物或氯乙烯和乙酸乙烯酯的共聚物、氯化的聚乙烯、聚偏二氟乙烯、环氧氯丙烷均聚物和共聚物,特别是与环氧乙烷的共聚物(ECO),
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、共聚物,例如聚丙烯腈-聚丙烯酸烷基酯,
e)不饱和醇的聚合物和衍生物,例如聚乙烯醇、聚乙酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙酯、聚烯丙基三聚氰胺,
f)聚缩醛,例如聚甲醛(POM)或与例如丁醛的共聚物,聚苯醚以及与聚苯乙烯或聚酰胺的共混物,
g)环状醚的聚合物,例如聚乙二醇、聚丙二醇、聚环氧乙烷、聚环氧丙烷、聚四氢呋喃,
h)聚苯醚及其与聚苯乙烯和/或聚酰胺的共混物,
i)由羟基封端的聚醚或聚酯和芳香族或脂肪族异氰酸酯,例如2,4-甲苯二异氰酸酯或2,6-甲苯二异氰酸酯或亚甲基二苯基二异氰酸酯制成的聚氨酯,特别是线型聚氨酯(TPU)、聚脲,
j)聚酰胺,例如聚酰胺-6、聚酰胺-6.6、聚酰胺-6.10、聚酰胺-4.6、聚酰胺-4.10、聚酰胺-6.12、聚酰胺-10.10、聚酰胺-10.12、聚酰胺-12.12、聚酰胺11、聚酰胺12和(部分)芳香族聚酰胺,例如聚苯二甲酰胺,其例如由对苯二甲酸和/或间苯二甲酸以及脂肪族二胺例如六亚甲基二胺或间苯二甲基二胺制成,或由脂肪族二羧酸例如己二酸或癸二酸和芳香族二胺例如1,4-苯二胺或1,3-苯二胺制成,不同聚酰胺例如PA-6和PA 6.6的共混物或聚酰胺和聚烯烃的共混物,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)由脂肪族或芳香族二羧酸和二醇或由羟基羧酸制成的聚酯,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(PTT)、聚萘二甲酸乙二醇酯(PEN)、聚对苯二甲酸-1,4-环己烷二甲醇酯、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)、聚琥珀酸乙二醇酯、聚琥珀酸四亚甲酯、聚己内酯,
m)聚碳酸酯、聚酯碳酸酯和共混物,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、醋酸纤维素、丙酸纤维素、丁酸纤维素,
o)环氧树脂,其由双官能或多官能环氧化合物与例如基于胺、酸酐、双氰胺、硫醇、异氰酸酯的硬化剂或催化活性硬化剂结合组成,
p)酚醛树脂,例如苯酚甲醛树脂、脲甲醛树脂、三聚氰胺甲醛树脂,
q)由不饱和二羧酸和二醇与乙烯基化合物,例如苯乙烯制成的不饱和聚酯树脂、醇酸树脂,
r)硅酮,其例如基于二甲基硅氧烷、甲基-苯基-硅氧烷或二苯基硅氧烷,例如乙烯基封端的,
s)以及上述聚合物的一种或多于一种的混合物、组合或共混物。
9.根据前述权利要求中任一项所述的用途,其特征在于塑料包含至少一种额外的添加剂,其选自主要抗氧化剂和/或次要抗氧化剂,特别地,主要抗氧化剂和/或次要抗氧化剂选自亚磷酸酯/盐、亚膦酸酯/盐、硫醇、酚类抗氧化剂、空间受阻胺、羟胺、及其混合物或组合,UV吸收剂、光稳定剂、基于羟胺的稳定剂、基于苯并呋喃酮的稳定剂、成核剂、抗冲改性剂、增塑剂、模具润滑剂、流变改性剂、扩链剂、加工助剂、颜料、染料、光学增白剂、抗微生物剂、抗静电剂、滑爽剂、防结块剂、偶联剂、分散剂、增容剂、氧清除剂、酸清除剂、共稳定剂、标记剂、防雾剂,特别地次要抗氧化剂在使用过程中被添加到塑料中,其中亚磷酸酯/盐、亚膦酸酯/盐、酸清除剂、受阻胺和/或其组合是特别优选的。
10.根据前述权利要求所述的用途,其特征在于至少一种添加剂的含量或添加量为基于去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物、有机材料和至少一种添加剂的总量的0.01重量%至9.99重量%、优选0.01重量%至4.98重量%、特别优选0.02重量%至2.00重量%。
11.一种包含去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物作为稳定剂的有机材料,特别是塑料组合物。
12.根据前述权利要求所述的有机材料,其具有以下组成
0.01重量%至10.00重量%、优选0.02重量%至5.00重量%、更优选0.05重量%至3.00重量%、特别优选0.10重量%至2.00重量%的去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物,
99.99重量%至90.00重量%、优选99.89重量%至95.00重量%、更优选97.00重量%至99.95重量%、特别优选99.90重量%至98.00重量%的至少一种有机材料,优选地,其选自塑料、涂料、润滑剂、液压油、发动机油、涡轮机油、传动油、金属加工液、化学品或单体,和
0重量%至9.99重量%、优选0重量%至4.98重量%、特别优选0.02重量%至2.00重量%的至少一种添加剂,
其中各组分合计为100重量%。
13.根据前述权利要求所述的有机材料,其特征在于至少一种添加剂选自主要抗氧化剂和/或次要抗氧化剂,特别地,主要抗氧化剂和/或次要抗氧化剂选自亚磷酸酯/盐、亚膦酸酯/盐、硫醇、酚类抗氧化剂、空间受阻胺、羟胺、及其混合物或组合,UV吸收剂、光稳定剂、基于羟胺的稳定剂、基于苯并呋喃酮的稳定剂、成核剂、抗冲改性剂、增塑剂、模具润滑剂、流变改性剂、扩链剂、加工助剂、颜料、染料、光学增白剂、抗微生物剂、抗静电剂、滑爽剂、防结块剂、偶联剂、分散剂、增容剂、氧清除剂、酸清除剂、共稳定剂、标记剂、防雾剂,特别是次要抗氧化剂;
特别地,至少一种添加剂选自:选自亚磷酸酯/盐、亚膦酸酯/盐和硫醇的次要抗氧化剂,至少一种选自多元醇、酸清除剂和空间受阻胺的共稳定剂。
14.一种稳定剂组合物,其包含以下组分或由以下组分组成:
去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物、及其混合物和组合,和
至少一种选自亚磷酸酯/盐、亚膦酸酯/盐或硫醇的次要抗氧化剂,和/或至少一种选自多元醇、酸清除剂或空间受阻胺的共稳定剂,及其混合物和组合。
15.根据前述权利要求所述的稳定剂组合物,其特征在于去氢双丁香酚、低聚丁香酚或聚丁香酚和至少一种次要抗氧化剂和/或共稳定剂以100:1至1:100、优选10:1至1:10、特别优选4:1至1:4的重量比存在。
16.一种用于稳定有机材料,特别是抗氧化降解、热降解和/或光化降解的方法,其中将去氢双丁香酚、丁香酚低聚物、丁香酚共低聚物、丁香酚聚合物和/或丁香酚共聚物并入有机材料中。
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BRPI0608631A2 (pt) * | 2005-03-18 | 2010-11-30 | Colgate Palmolive Co | composição oral antiplaca, pasta de dentes ou composição em gel, e, método para inibir crescimento bacteriano na cavidade oral de um animal |
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