CN112292382A - 作为稳定剂的3-苯基苯并呋喃-2-酮二磷酸酯衍生物 - Google Patents
作为稳定剂的3-苯基苯并呋喃-2-酮二磷酸酯衍生物 Download PDFInfo
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- CN112292382A CN112292382A CN201980041307.7A CN201980041307A CN112292382A CN 112292382 A CN112292382 A CN 112292382A CN 201980041307 A CN201980041307 A CN 201980041307A CN 112292382 A CN112292382 A CN 112292382A
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- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08K5/51—Phosphorus bound to oxygen
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/6574—Esters of oxyacids of phosphorus
- C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
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- C08K5/1345—Carboxylic esters of phenolcarboxylic acids
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- C08K5/524—Esters of phosphorous acids, e.g. of H3PO3
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- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
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- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/10—Homopolymers or copolymers of propene
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- C08L25/02—Homopolymers or copolymers of hydrocarbons
- C08L25/04—Homopolymers or copolymers of styrene
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- C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
- C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
- C09K15/32—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal
- C09K15/322—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing two or more of boron, silicon, phosphorus, selenium, tellurium or a metal containing only phosphorus
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- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
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- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
- C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
- C10M2223/04—Phosphate esters
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- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
- C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
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Abstract
本发明涉及一种包含易于氧化、热或光诱发降解的有机材料和式I‑P、I‑O或I‑M化合物的组合物。其他实施方案是式I‑P、I‑O或I‑M化合物,一种通过该化合物保护该有机材料的方法,该化合物防止该有机材料降解的用途,一种包含该化合物的添加剂组合物,制备该化合物的方法以及其中涉及的中间体。
Description
本发明涉及一种包含待稳定化有机材料和特定组的3-苯基苯并呋喃-2-酮二磷酸酯衍生物作为稳定剂的组合物。其他实施方案是一种由该特定组3-苯基苯并呋喃-2-酮二磷酸酯衍生物的保护该有机材料的方法,后者在稳定化中的用途,该特定组的3-苯基苯并呋喃-2-酮二磷酸酯衍生物,一种包含后者的添加剂组合物,制造后者的方法以及所涉及的中间体。
WO 80/01566 A公开了作为稳定剂的苯并呋喃-2-酮或吲哚啉-2-酮衍生物。
US 5428162尤其公开了作为稳定剂的3-苯基-3H-苯并呋喃-2-酮衍生物,其被膦酸二(C1-C6烷基)酯基团取代,例如下面所示的第120号化合物(=2-二乙氧基磷酰基乙酸2-[4-(5-甲基-2-氧代-3H-苯并呋喃-3-基)苯氧基]乙基酯):
WO 99/03915 A公开了具有3-苯基苯并呋喃-2-酮的基础结构的二亚磷酸酯和内酯的共混物作为聚合物的稳定剂。
WO 2016/020322 A公开了作为稳定剂的3-苯基苯并呋喃-2-酮二亚磷酸酯衍生物,特别是用于稳定聚合物。这些衍生物的实例是如下所示化合物(102):
尽管存在许多工业使用的稳定剂并且描述了显著更多化学类别的稳定剂,仍然需要其他稳定剂。在作为稳定剂防止待稳定化材料降解的性能之下,另一方面是稳定剂本身在作为稳定剂应用之前的稳定性,例如其储存稳定性和作为材料处理的容易性。关于磷基稳定剂,该稳定剂本身在其加入待稳定化材料中之前对潮湿条件的稳定性通常是个问题。例如,水解稳定性是聚合物生产设备的重要因素。在全球范围内(美国海湾沿岸;新加坡;中东等)聚合物生产设备相对常见的热和潮湿环境中,具有水解稳定的稳定剂不仅对于预期的稳定化活性是重要的,而且对于保持产物作为自由流动粉末或颗粒是重要的。在工业中众所周知的是水解亚磷酸酯非常难以处理并且它们中的一些甚至变成吸湿性材料。该水解材料还可能由于与亚磷酸酯水解相关的酸性副产物而对用于聚合物的熔体加工设备具有腐蚀性。对于一些亚磷酸酯稳定剂,工业上通常使用0.5-1重量%的水解抑制剂如三异丙醇胺。因此,在潮湿条件下对水解显示出相对稳定性的磷基稳定剂令人感兴趣。水解通常使得最初自由流动的材料变粘并且因此不利地影响在工业环境中将该稳定剂加入该待稳定化有机材料中的能力。独立于储存稳定性和作为材料处理的容易性,尽管暴露于潮湿条件,但保持其稳定化活性或者与相关磷基稳定剂相比至少不会以相同程度丧失其稳定化活性的磷基稳定剂也是令人感兴趣的。此外,由于该水解的稳定剂的酸性(磷基酸),水解的稳定剂可能不利地以黑斑影响待稳定化有机材料。
现已发现特定组的苯并呋喃-2-酮二磷酸酯衍生物适合稳定有机材料以防热、光和/或氧化降解。
本发明涉及一种组合物,包含:
a)一种易于氧化、热或光诱发降解的有机材料,和
b)式I-P、I-O或I-M的化合物:
其中
R1P表示子式II-P、II-O或II-M之一:
R1O表示子式II-O或II-M之一,或者
R1M表示子式II-M;
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RP2、RP3、RP5和RP6相互独立地为氢或C1-C8烷基,
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基,以及
RM1、RM3、RM5和RM6相互独立地为氢或C1-C8烷基。
式I-P、I-O或I-M化合物具有至少一个不对称碳原子,即在苯并呋喃-2-酮结构单元的3位上的碳原子。其他不对称碳原子可以存在于具有至少4个碳原子的烷基取代基中。被4个不同取代基取代的磷原子是不对称磷原子。本发明涉及所得对映体、所得非对映体或其混合物。
C1-C8烷基是线性或支化的且例如为甲基、乙基、正丙基、1-甲基乙基、正丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、正戊基、1-甲基丁基、3-甲基丁基、正己基、1-甲基戊基、2-甲基戊基、4-甲基戊基、2-乙基丁基、正庚基、1-甲基己基、正辛基、1-甲基庚基、2-乙基己基、5,5-二甲基己基或1,1,3,3-四甲基丁基。优选C1-C4烷基或C8烷基,特别是甲基、乙基、1-甲基乙基、1-甲基丙基、1,1-二甲基乙基或1,1,3,3-四甲基丁基。优选C1-C4烷基,特别是甲基、乙基、1-甲基乙基、1-甲基丙基、1,1-二甲基乙基,非常特别地是甲基、1-甲基丙基或1,1-二甲基乙基。
易于氧化、热或光诱发降解的有机材料例如是聚合物、低聚羟基化合物、蜡、脂肪或矿物油。
聚合物可以是天然、半合成或合成的。天然聚合物由天然源分离而没有进一步合成改性。合成聚合物不含由天然源分离的聚合物部分。半合成聚合物含有至少一种天然聚合物部分,其中该天然聚合物部分可以合成改性和/或与单体反应形成半合成聚合物。
聚合物可以是热塑性的,即它可以在升高的温度下,例如在135-350℃,尤其是150-340℃范围内的温度下成型为新的形式。
共聚物是其中至少两种不同单体共聚的聚合物。优选其中一种单体的重量含量基于所有单体的重量超过50%的共聚物。
优选聚合物是这样一种物质,其由特征在于一种或多种类型的单体单元序列的分子构成并且包含简单重量多数的含有至少三个共价键合于至少一个其他单体单元或其他反应物的单体单元的分子并且由少于简单重量多数的具有相同分子量的分子构成。该类分子必须分布在一定分子量范围上,其中分子量的不同主要可归因于单体单元数目的不同。就该定义而言,单体单元是指单体在聚合物中的已反应形式。
聚合物的实例为:
1.单烯烃和二烯烃的聚合物,例如聚丙烯、聚异丁烯、聚丁-1-烯、聚-4-甲基戊-1-烯、聚乙烯基环己烷、聚异戊二烯或聚丁二烯,以及环烯烃如环戊烯或降冰片烯的聚合物,聚乙烯(任选可交联),例如高密度聚乙烯(HDPE)、高密度和高分子量聚乙烯(HDPE-HMW)、高密度和超高分子量聚乙烯(HDPE-UHMW)、中密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、线性低密度聚乙烯(LLDPE)、(VLDPE)和(ULDPE)。
聚烯烃,即前段中所列举的单烯烃的聚合物,优选聚乙烯和聚丙烯,可以通过不同方法,尤其是下列方法制备:
a)游离基聚合(通常在高压和升高的温度下)。
b)使用通常含有一种或不止一种周期表第4、5、6(例如铬)或7族金属的催化剂的催化聚合。这些金属通常具有一种或不止一种配体,通常是氧化物、卤化物、醇盐、酯、醚、胺、烷基化物、链烯基化物和/或芳基化物,它们可以是π-或σ-配位的。这些金属配合物可以呈游离形式或固定在基材上,通常固定在活化氯化镁、氯化钛(III)、氧化铝或氧化硅上。这些催化剂可溶于或不溶于聚合介质中。催化剂本身可用于聚合中,或可使用其他活化剂,一般是金属烷基化物、金属氢化物、金属烷基卤化物、金属烷基氧化物或金属烷基氧丙环(alkyloxane),所述金属为周期表第1、2和/或3族元素。活化剂可方便地用其他酯、醚、胺或甲硅烷基醚基团改性。这些催化剂体系一般称为Phillips、Standard Oil Indiana、Ziegler(-Natta)、TNZ(DuPont)、金属茂或单中心催化剂(SSC)。
2.在1)下所提到聚合物的混合物,例如聚丙烯与聚异丁烯的混合物、聚丙烯与聚乙烯的混合物(例如PP/HDPE,PP/LDPE)以及不同类型聚乙烯的混合物(例如LDPE/HDPE)。
3.单烯烃和二烯烃彼此之间或与其他乙烯基单体的共聚物,例如乙烯/丙烯共聚物,线性低密度聚乙烯(LLDPE)及其与低密度聚乙烯(LDPE)的混合物,丙烯/丁-1-烯共聚物,丙烯/异丁烯共聚物,乙烯/丁-1-烯共聚物,乙烯/己烯共聚物,乙烯/甲基戊烯共聚物,乙烯/庚烯共聚物,乙烯/辛烯共聚物,乙烯/乙烯基环己烷共聚物,乙烯/环烯烃共聚物(例如乙烯/降冰片烯如COC),其中1-烯烃就地产生的乙烯/1-烯烃共聚物;丙烯/丁二烯共聚物,异丁烯/异戊二烯共聚物,乙烯/乙烯基环己烯共聚物,乙烯/丙烯酸烷基酯共聚物,乙烯/甲基丙烯酸烷基酯共聚物,乙烯/乙酸乙烯酯共聚物或乙烯/丙烯酸共聚物及其盐(离聚物)以及乙烯与丙烯和二烯如己二烯、二聚环戊二烯或亚乙基降冰片烯的三元共聚物;以及该类共聚物彼此之间和与上面1)中所提到聚合物的混合物,例如聚丙烯/乙烯-丙烯共聚物,LDPE/乙烯-乙酸乙烯酯共聚物(EVA),LDPE/乙烯-丙烯酸共聚物(EAA),LLDPE/EVA,LLDPE/EAA和交替或无规聚烯烃/一氧化碳共聚物及其与其他聚合物如聚酰胺的混合物。
两种单烯烃的特殊共聚物是管道级聚丙烯无规共聚物,其可以由大于90重量%的丙烯和小于10重量%,通常为2-6重量%的乙烯聚合而得到。
4.烃树脂(例如C5-C9),包括其氢化改性物(例如增粘剂)以及聚烯烃和淀粉的混合物。
来自1.)-4.)的均聚物和共聚物可具有立体结构,包括间规立构、等规立构、半等规立构或无规立构;其中优选等规立构聚合物。还包括立体嵌段聚合物。
5.聚苯乙烯、聚(对甲基苯乙烯),聚(α-甲基苯乙烯)。
6.衍生自乙烯基芳族单体的芳族均聚物和共聚物,所述单体包括苯乙烯,α-甲基苯乙烯,乙烯基甲苯的所有异构体,尤其是对乙烯基甲苯,乙基苯乙烯的所有异构体,丙基苯乙烯,乙烯基联苯,乙烯基萘,以及乙烯基蒽及其混合物。均聚物和共聚物可具有立体结构,包括间规立构、等规立构、半等规立构或无规立构;其中优选无规立构聚合物。还包括立体嵌段聚合物。
6a.包括上述乙烯基芳族单体和选自以下的共聚单体的共聚物:乙烯,丙烯,二烯,腈,酸,马来酸酐,马来酰亚胺,乙酸乙烯酯和氯乙烯或丙烯酸系衍生物及其混合物,例如苯乙烯/丁二烯,苯乙烯/丙烯腈,苯乙烯/乙烯(共聚物),苯乙烯/甲基丙烯酸烷基酯,苯乙烯/丁二烯/丙烯酸烷基酯,苯乙烯/丁二烯/甲基丙烯酸烷基酯,苯乙烯/马来酸酐,苯乙烯/丙烯腈/丙烯酸甲基酯;高抗冲强度的苯乙烯共聚物与其他聚合物例如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三元共聚物的混合物;以及苯乙烯的嵌段共聚物,例如苯乙烯/丁二烯/苯乙烯,苯乙烯/异戊二烯/苯乙烯,苯乙烯/乙烯/丁烯/苯乙烯或者苯乙烯/乙烯/丙烯/苯乙烯。
6b.由6.)下所提到聚合物的氢化衍生的氢化芳族聚合物,尤其包括通过氢化无规立构聚苯乙烯制备的聚环己基乙烯(PCHE),通常称为聚乙烯基环己烷(PVCH)。
6c.由6a.)下所提到聚合物的氢化衍生的氢化芳族聚合物。均聚物和共聚物可具有任何立体结构,包括间规立构、等规立构、半等规立构或无规立构;其中优选无规立构聚合物。还包括立体嵌段聚合物。
7.乙烯基芳族单体如苯乙烯或α-甲基苯乙烯的接枝共聚物,例如苯乙烯在聚丁二烯上的接枝共聚物,苯乙烯在聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物上的接枝共聚物;苯乙烯和丙烯腈(或甲基丙烯腈)在聚丁二烯上的接枝共聚物;苯乙烯、丙烯腈和甲基丙烯酸甲酯在聚丁二烯上的接枝共聚物;苯乙烯和马来酸酐在聚丁二烯上的接枝共聚物;苯乙烯、丙烯腈和马来酸酐或马来酰亚胺在聚丁二烯上的接枝共聚物;苯乙烯和马来酰亚胺在聚丁二烯上的接枝共聚物;苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯在聚丁二烯上的接枝共聚物;苯乙烯和丙烯腈在乙烯/丙烯/二烯三元共聚物上的接枝共聚物;苯乙烯和丙烯腈在聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上的接枝共聚物,苯乙烯和丙烯腈在丙烯酸酯/丁二烯共聚物上的接枝共聚物,及其与6)下所列共聚物的混合物,例如已知为ABS、MBS、ASA或AES聚合物的共聚物混合物。
8.含卤素的聚合物,如聚氯丁二烯,氯化橡胶,异丁烯-异戊二烯的氯化和溴化共聚物(卤代丁基橡胶),氯化或磺基氯化的聚乙烯,乙烯和氯化乙烯的共聚物,表氯醇均聚物和共聚物,尤其是含卤素的乙烯基化合物的聚合物,例如聚氯乙烯、聚偏二氯乙烯、聚氟乙烯、聚偏二氟乙烯,以及它们的共聚物,例如氯乙烯/偏二氯乙烯共聚物、氯乙烯/乙酸乙烯酯共聚物或偏二氯乙烯/乙酸乙烯酯共聚物。
9.衍生自α,β-不饱和酸及其衍生物的聚合物,例如聚丙烯酸酯和聚甲基丙烯酸酯;聚甲基丙烯酸甲酯,聚丙烯酰胺和聚丙烯腈,其用丙烯酸丁酯进行冲击改性。
10. 9)下所提到单体彼此之间或与其他不饱和单体的共聚物,例如丙烯腈/丁二烯共聚物,丙烯腈/丙烯酸烷基酯共聚物,丙烯腈/丙烯酸烷氧基烷基酯共聚物或丙烯腈/乙烯基卤共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
11.衍生自不饱和醇和胺或其酰基衍生物或缩醛的聚合物,例如聚乙烯醇、聚乙酸乙烯酯、聚硬脂酸乙烯基酯、聚苯甲酸乙烯基酯、聚马来酸乙烯基酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙酯或聚烯丙基蜜胺;以及它们与上面在1)中所提到烯烃的共聚物。
12.环醚的均聚物和共聚物,例如聚亚烷基二醇,聚氧化乙烯,聚氧化丙烯,或其与二缩水甘油醚的共聚物。
13.聚缩醛,例如聚甲醛以及含有氧化乙烯作为共聚单体的那些聚甲醛;用热塑性聚氨酯、丙烯酸酯或MBS改性的聚缩醛。
14.聚苯醚和聚苯硫醚,以及聚苯醚与苯乙烯聚合物或聚酰胺的混合物。
15.聚氨酯,例如由多元醇和脂族或芳族多异氰酸酯合成的聚氨酯,如一方面衍生自羟基封端的聚醚、聚酯或聚丁二烯且另一方面衍生自脂族或芳族多异氰酸酯及其前体的聚氨酯。
羟基封端的聚醚是已知的并且例如通过例如在BF3存在下聚合环氧化物如氧化乙烯、氧化丙烯、氧化丁烯、四氢呋喃、氧化苯乙烯或表氯醇自身或者通过使这些环氧化物与含有反应性氢原子的起始组分如水、醇、氨或胺,例如乙二醇、1,3-和1,2-丙二醇、三羟甲基丙烷、4,4'-二羟基二苯基丙烷、苯胺、乙醇胺或乙二胺单独或者作为混合物或者依次加成反应而制备。蔗糖聚醚按照本发明也适合。在许多情况下优选主要(至多90重量%,基于该聚醚中存在的所有OH基团)含有伯OH基团的那些聚醚。此外,例如通过在聚醚存在下聚合苯乙烯和丙烯腈而形成的由乙烯基聚合物改性的聚醚是合适的,正如含有OH基团的聚丁二烯一样。
具体而言,多元醇化合物具有400-10000,尤其是800-10000的分子量并且为含有大于一个OH基团,尤其是含有2-8个,尤其是2-4个OH基团的化合物。
合适的多异氰酸酯是脂族或芳族的,例如亚乙基二异氰酸酯、1,4-四亚甲基二异氰酸酯、1,6-六亚甲基二异氰酸酯、1,12-十二烷二异氰酸酯、环丁烷-1,3-二异氰酸酯、环己烷-1,3-和-1,4-二异氰酸酯以及还有这些异构体的任何所需混合物、1-异氰酸酯基-3,3,5-三甲基-5-异氰酸酯基甲基环己烷、2,4-和2,6-六氢甲苯二异氰酸酯以及还有这些异构体的任何所需混合物、六氢-1,3-和/或-1,4-苯二异氰酸酯、全氢-2,4'-和/或-4,4'-二苯基甲烷二异氰酸酯、1,3-和1,4-苯二异氰酸酯、2,4-和2,6-甲苯二异氰酸酯以及还有这些异构体的任何所需混合物、二苯基甲烷-2,4'-和/或-4,4'-二异氰酸酯、萘-1,5-二异氰酸酯、三苯基甲烷-4,4',4"-三异氰酸酯、通过苯胺-甲醛缩合以及随后光气化得到的多苯基多亚甲基多异氰酸酯、m-和p-异氰酸酯基苯基磺酰基异氰酸酯、全氯化芳基多异氰酸酯、含有碳二亚胺基团的多异氰酸酯、含有脲基甲酸酯基团的多异氰酸酯、含有异氰脲酸酯基团的多异氰酸酯、含有尿烷基团的多异氰酸酯、含有酰化脲基团的多异氰酸酯、含有缩二脲基团的多异氰酸酯、含有酯基的多异氰酸酯、上述异氰酸酯与缩醛的反应产物以及含有聚合脂肪酸基团的多异氰酸酯。
还可以使用含有异氰酸酯基团的蒸馏残余物,它们为一种或多种在异氰酸酯的工业制备过程中得到的上述多异氰酸酯或溶于其中。额外可以使用上述多异氰酸酯的任何所需混合物。
优选2,4-或2,6-甲苯二异氰酸酯和这些异构体的任何所需混合物(“TDI”),通过苯胺-甲醛缩合以及随后光气化得到的多苯基多亚甲基多异氰酸酯(“粗MDI”)或含有碳二亚胺、尿烷、脲基甲酸酯、异氰脲酸酯、脲或缩二脲基团的多异氰酸酯(“改性多异氰酸酯”)。
聚氨酯可以是均相聚氨酯或泡孔状的。
16.衍生自二胺和二羧酸和/或衍生自氨基羧酸或相应内酰胺的聚酰胺和共聚酰胺,例如聚酰胺4,聚酰胺6,聚酰胺6/6、6/10、6/9、6/12,4/6、12/12,聚酰胺11,聚酰胺12,由间二甲苯二胺和己二酸开始的芳族聚酰胺;在存在或不存在作为改性剂的弹性体下由六亚甲基二胺和间苯二甲酸或/和对苯二甲酸制备的聚酰胺,例如聚-2,4,4-三甲基六亚甲基对苯二甲酰胺或聚间亚苯基间苯二甲酰胺;以及还有上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学键合或接枝弹性体的嵌段共聚物;或与聚醚,例如聚乙二醇、聚丙二醇或聚四亚甲基二醇的嵌段共聚物;以及用EPDM或ABS改性的聚酰胺或共聚酰胺;以及在加工期间缩合的聚酰胺(RIM聚酰胺体系)。
17.聚脲、聚酰亚胺、聚酰胺-酰亚胺、聚醚酰亚胺、聚酯酰亚胺、聚乙内酰脲和聚苯并咪唑类。
18.衍生自二羧酸和二醇和/或衍生自羟基羧酸或相应内酯或交酯的聚酯,例如聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚1,4-二羟甲基环己烷对苯二甲酸酯、聚萘二甲酸亚烷基二醇酯和聚羟基苯甲酸酯,以及衍生自羟基封端聚醚的共聚醚酯,以及还有用聚碳酸酯或MBS改性的聚酯。共聚酯包括例如但不限于琥珀酸/对苯二甲酸聚丁二醇酯、聚己二酸/对苯二甲酸丁二醇酯、聚己二酸/对苯二甲酸四亚甲基二醇酯、聚琥珀酸/己二酸丁二醇酯、聚琥珀酸/碳酸丁二醇酯、聚-3-羟基丁酸酯/辛酸酯共聚物、聚-3-羟基丁酸酯/己酸酯/癸酸酯三元共聚物。
此外,脂族聚酯可以包括例如但不限于聚(羟基链烷酸酯)类别,特别是聚丙内酯、聚丁内酯、聚新戊内酯、聚戊内酯和聚己内酯,聚琥珀酸乙二醇酯、聚琥珀酸丙二醇酯、聚琥珀酸丁二醇酯、聚琥珀酸六亚甲基二醇酯、聚己二酸乙二醇酯、聚己二酸丙二醇酯、聚己二酸丁二醇酯、聚己二酸六亚甲基二醇酯、聚草酸乙二醇酯、聚草酸丙二醇酯、聚草酸丁二醇酯、聚草酸六亚甲基二醇酯、聚癸二酸乙二醇酯、聚癸二酸丙二醇酯、聚癸二酸丁二醇酯和聚乳酸(PLA)以及用聚碳酸酯或MBS改性的相应聚酯。术语“聚乳酸(PLA)”表示优选聚-L-丙交酯均聚物以及其与其他聚合物的任何共混物或合金;乳酸或丙交酯与其他单体,如羟基羧酸,例如羟基乙酸、3-羟基丁酸、4-羟基丁酸、4-羟基戊酸、5-羟基戊酸、6-羟基己酸及其环状形式的共聚物;术语“乳酸”或“丙交酯”包括L-乳酸、D-乳酸、其混合物和二聚体,即L-丙交酯、D-丙交酯、内消旋丙交酯及其任何混合物。
19.聚碳酸酯和聚酯碳酸酯。
20.聚酮。
21.聚砜、聚醚砜和聚醚酮。
22.一方面衍生于醛类并且另一方面衍生于酚类、脲类和蜜胺类的交联聚合物,如苯酚/甲醛树脂、脲/甲醛树脂和蜜胺/甲醛树脂。
23.干性和不干性醇酸树脂。
24.衍生于饱和和不饱和二羧酸与多元醇和作为交联剂的乙烯基化合物的共聚酯的不饱和聚酯树脂以及还有具有低可燃性的其含卤素改性物。
25.衍生于取代丙烯酸酯的可交联丙烯酸系树脂,例如环氧丙烯酸酯、尿烷丙烯酸酯或聚酯丙烯酸酯。
26.用蜜胺树脂、脲树脂、异氰酸酯、异氰脲酸酯、多异氰酸酯或环氧树脂交联的醇酸树脂、聚酯树脂和丙烯酸酯树脂。
27.衍生于脂族、脂环族、杂环或芳族缩水甘油基化合物的交联环氧树脂,例如双酚A和双酚F的二缩水甘油醚的产物,它们在有或没有促进剂下用常规硬化剂如酸酐或胺交联。
28.天然聚合物如纤维素、橡胶、明胶及其化学改性类似衍生物,例如纤维素乙酸酯、纤维素丙酸酯和纤维素丁酸酯,或纤维素醚如甲基纤维素;以及松香及其衍生物。
29.上述聚合物的共混物(聚合物共混物),例如PP/EPDM、聚酰胺/EPDM或ABS、PVC/EVA、PVC/ABS、PVC/MBS、PC/ABS、PBTP/ABS、PC/ASA、PC/PBT、PVC/CPE、PVC/丙烯酸酯、POM/热塑性PUR、PC/热塑性PUR、POM/丙烯酸酯、POM/MBS、PPO/HIPS、PPO/PA6.6和共聚物,PA/HDPE、PA/PP、PA/PPO、PBT/PC/ABS或PBT/PET/PC。
30.天然或合成橡胶的水乳液,例如羧化苯乙烯/丁二烯共聚物的天然胶乳。
低聚羟基化合物具有两个或更多个羟基,但不是根据the Organization forEconomic Co-operation and Development的聚合物定义的聚合物。低聚羟基化合物的实例是乙二醇、丙二醇、1,2-丁二醇、1,4-丁二醇、1,2-己二醇、1,6-己二醇、环己烷-1,2-二醇、甘油、季戊四醇、D-果糖、D-山梨糖醇、甘露糖醇或蔗糖。
蜡例如是蜡酸与醇的酯,例如用C15-C36一元醇、三萜烯醇或类固醇酯化的C22-C34单羧酸。该类酯例如含于巴西棕榈蜡、蜂蜡或霍霍巴油中。另一类蜡例如是基于C1化学的费托蜡。
脂肪是甘油和脂族饱和或不饱和羧酸的酯,例如单酰甘油、二酰甘油或三酰甘油。优选该羧酸是线性的。
矿物油是脂族液体饱和烃,其通过蒸馏由原油、煤焦油、沥青焦油、木材或泥炭得到。矿物油可以是液体、半固体或固体。在后一情形中,它被称为矿脂。矿物油的实例是粗汽油、柴油、燃料油、沥青或煤油。优选的矿物油是线性或支化的饱和C8-C22烃。尤其优选饱和C8-C14烃。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,其中该有机材料是聚合物、低聚羟基化合物、蜡、脂肪或矿物油,和
b)式I-P、I-O或I-M化合物。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,其中该有机材料是聚合物,特别是合成或半合成聚合物,非常特别是合成或半合成热塑性聚合物,和
b)式I-P、I-O或I-M化合物。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,其中该有机材料是聚合物,其为聚烯烃或其共聚物,聚苯乙烯或其共聚物,聚氨酯或其共聚物,可以通过环氧化物、氧杂环丁烷或四氢呋喃聚合而得到的聚醚或其共聚物,聚酯或其共聚物,聚碳酸酯或其共聚物,聚氯乙烯或其共聚物,聚偏二氯乙烯或其共聚物,聚砜或其共聚物,聚乙酸乙烯酯或其共聚物,聚乙烯醇或其共聚物,聚乙烯醇缩醛或其共聚物或者聚酰胺或其共聚物,和
b)式I-P、I-O或I-M化合物。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,其中该有机材料是聚烯烃或其共聚物、聚苯乙烯或其共聚物或者聚氨酯或其共聚物,特别是其中该有机材料是聚烯烃或其共聚物或者聚苯乙烯或其共聚物,和
b)式I-P、I-O或I-M化合物。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,其中该有机材料是聚烯烃或其共聚物,和
b)式I-P、I-O或I-M化合物。
上述组合物中式I-P、I-O或I-M化合物的优选情形如下:
优选如下式I-P、I-O或I-M的化合物,其中
R4和R6为氢,和
R5和R7相互独立地为氢或C1-C8烷基,特别是氢或C1-C4烷基。
优选如下式I-P、I-O或I-M的化合物,其中
R4、R6和R7为氢且R5为氢或C1-C8烷基,特别是氢或C1-C4烷基。
优选如下式I-P、I-O或I-M的化合物,其中
RP2和RP6相互独立地为氢或C1烷基,RP3和RP5相互独立地为氢或C1-C4烷基,
RO1和RO6相互独立地为氢或C1-C8烷基,RO2为氢或C1烷基且RO5为氢或C1-C4烷基,
RM1为氢或C1烷基,RM3和RM5相互独立地为氢或C1-C4烷基且RM6为氢或C1-C8烷基。
优选如下式I-P、I-O或I-M的化合物,其中
RP2和RP6为氢且RP3和RP5相互独立地为氢或C1-C4烷基,
RO1为氢或C1-C8烷基,RO2为氢,RO5和RO6相互独立地为氢或C1-C4烷基,
RM1和RM3为氢或C1烷基,RM5为氢或C1-C4烷基且RM6为氢或C1-C8烷基。
优选如下式I-P、I-O或I-M的化合物,其中
RP2和RP6为氢且RP3和RP5相互独立地为氢或C1-C4烷基,其中RP3和RP5之一不为C4烷基,
RO1为氢或C1-C8烷基,RO2为氢,RO5为氢或C1-C3烷基且RO6为氢或C1-C4烷基,和
RM1和RM3为氢或C1烷基,RM5为氢或C1-C3烷基且RM6为氢或C1-C8烷基。
优选如下式I-P、I-O或I-M的化合物,其中
RP2和RP6为氢且RP3和RP5之一为氢,而另一个为氢或C1-C4烷基,
RO1为氢或C1-C8烷基,RO2为氢,RO5为氢或C1烷基且RO6为氢或C1-C4烷基,和
RM1、RM3和RM5为氢且RM6为氢或C1-C8烷基。
优选如下式I-P、I-O或I-M的化合物,其中
R1P表示子式II-P,
R1O表示式II-O,和
R1M表示子式II-M。
优选式I-P、I-O或I-M的化合物,其具有式I-P或I-O,并且其中R1P或R1O不表示子式II-M。
优选式I-P、I-O或I-M的化合物,其具有式I-P或I-O,其中
R1P表示子式II-P或II-O之一,
R1O表示子式II-O。
优选式I-P、I-O或I-M的化合物,其具有式I-P,其中R1P表示子式II-P。
优选式I-P、I-O或I-M的化合物,其具有式I-O,其中R1O表示子式II-O。
式I-P、I-O或I-M化合物的上述优选情形单独涉及式I-P、I-O或I-M的三种结构单元。这些结构单元包含包括R4、R5、R6和R7的苯并呋喃-2-酮单元,包括RP2、RP3、RP5、RP6、RO1、RO2、RO5、RO6、RM1、RM3、RM5和RM6的亚苯基连接单元以及包括R1P、R1O和R1M的其他接近磷原子的单元。三种结构单元的上述优选情形可以组合。其实例提供如下。
优选如下式I-P、I-O或I-M的化合物,其中
R1P表示子式II-P、II-O或II-M之一,
R1O表示子式II-O或II-M之一,
R1M表示子式II-M,
R4和R6为氢,
R5和R7相互独立地为氢或C1-C8烷基,
RP2和RP6相互独立地为氢或C1烷基,
RP3和RP5相互独立地为氢或C1-C4烷基,
RO1和RO6相互独立地为氢或C1-C8烷基,
RO2为氢或C1烷基,
RO5为氢或C1-C4烷基,
RM1为氢或C1烷基,
RM3和RM5相互独立地为氢或C1-C4烷基,和
RM6为氢或C1-C8烷基。
优选如下式I-P、I-O或I-M的化合物,其中
R1P表示子式II-P,
R1O表示子式II-O,
R1M表示子式II-M,
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RP2、RP3、RP5和RP6相互独立地为氢或C1-C8烷基,
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基,和
RM1、RM3、RM5和RM6相互独立地为氢或C1-C8烷基,
优选式I-P、I-O或I-M的化合物,其具有式I-P或I-O,其中
R1P表示子式II-P或II-O之一,
R1O表示子式II-O,
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RP2、RP3、RP5和RP6相互独立地为氢或C1-C8烷基,和
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基。
优选式I-P、I-O或I-M的化合物,其具有式I-P或I-O,其中
R1P表示子式II-P或II-O之一,
R1O表示子式II-O,
R4和R6为氢,
R5和R7相互独立地为氢或C1-C8烷基,
RP2和RP6为氢,
RP3和RP5相互独立地为氢或C1-C4烷基,其中RP3和RP5之一不为C4烷基,
RO1为氢或C1-C8烷基,
RO2为氢,
RO5为氢或C1-C3烷基,和
RO6为氢或C1-C4烷基。
优选式I-P化合物,其为化合物(403),或式I-O化合物,其为化合物(402)。化合物(403)的结构示于合成实施例S-4a或S-4b中且化合物(402)的结构示于合成实施例S-3a、S-3b或S-3c中。
组分b),即式I-P、I-O或I-M化合物相对于组分a),即易于氧化、热或光诱发降解的有机材料的用量随着易于氧化、热或光诱发降解的特定有机材料和所需保护程度而变化。
优选如下组合物,包含易于氧化、热或光诱发降解的有机材料作为组分a)和式I-P、I-O或I-M化合物作为组分b),其中基于组分a)的重量以0.0005-10%,特别是0.001-2%,尤其是0.0025-1%,非常尤其是0.005-0.5%的量含有组分b)。
任选地,包含有机材料作为组分a)和式I-P、I-O或I-M化合物作为组分b)的组合物含有其他添加剂作为组分c)。
其他添加剂可以选自下面的列举:
1.抗氧化剂
1.1.不含亚磷酸酯基团或苯并呋喃-2-酮基团的烷基化单酚,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-正丁基苯酚,2,6-二叔丁基-4-异丁基苯酚,2,6-二环戊基-4-甲基苯酚,2-(α-甲基环己基)-4,6-二甲基苯酚,2,6-二-十八烷基-4-甲基苯酚,2,4,6-三环己基苯酚,2,6-二叔丁基-4-甲氧基甲基苯酚,侧链呈线性或支化的壬基酚类,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,2,4-二甲基-6-(1'-甲基-1'-十四烷基甲基)苯酚及其混合物。
1.2.烷硫基甲基酚类,例如2,4-二辛硫基甲基-6-叔丁基苯酚、2,4-二辛硫基甲基-6-甲基苯酚、2,4-二辛硫基甲基-6-乙基苯酚、2,6-二-十二烷硫基甲基-4-壬基苯酚。
1.3.氢醌类和烷基化氢醌类,例如2,6-二叔丁基-4-甲氧基苯酚、2,5-二叔丁基氢醌、2,5-二叔戊基氢醌、2,6-二苯基-4-十八烷氧基苯酚、2,6-二叔丁基氢醌、2,5-二叔丁基-4-羟基茴香醚、3,5-二叔丁基-4-羟基茴香醚、硬脂酸3,5-二叔丁基-4-羟基苯基酯、己二酸二(3,5-二叔丁基-4-羟基苯基)酯。
1.4.生育酚类,例如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)。
1.5.羟基化硫代二苯基醚类,例如2,2'-硫代二(6-叔丁基-4-甲基苯酚)、2,2'-硫代二(4-辛基苯酚)、4,4'-硫代二(6-叔丁基-3-甲基苯酚)、4,4'-硫代二(6-叔丁基-2-甲基苯酚)、4,4'-硫代二(3,6-二仲戊基苯酚)、4,4'-二(2,6-二甲基-4-羟基苯基)二硫化物。
1.6.亚烷基双酚类,例如2,2'-亚甲基二(6-叔丁基-4-甲基苯酚)、2,2'-亚甲基二(6-叔丁基-4-乙基苯酚)、2,2'-亚甲基二[4-甲基-6-(α-甲基环己基)苯酚]、2,2'-亚甲基二(4-甲基-6-环己基苯酚)、2,2'-亚甲基二(6-壬基-4-甲基苯酚)、2,2'-亚甲基二(4,6-二叔丁基苯酚)、2,2'-亚乙基二(4,6-二叔丁基苯酚)、2,2'-亚乙基二(6-叔丁基-4-异丁基苯酚)、2,2'-亚甲基二[6-(α-甲基苄基)-4-壬基苯酚]、2,2'-亚甲基二[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4'-亚甲基二(2,6-二叔丁基苯酚)、4,4'-亚甲基二(6-叔丁基-2-甲基苯酚)、1,1-二(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、1,1-二(5-叔丁基-4-羟基-2-甲基苯基)-3-正十二烷基巯基丁烷、乙二醇二[3,3-二(3'-叔丁基-4'-羟基苯基)丁酸酯]、二(3-叔丁基-4-羟基-5-甲基苯基)二聚环戊二烯、对苯二甲酸二[2-(3'-叔丁基-2'-羟基-5'-甲基苄基)-6-叔丁基-4-甲基苯基]酯、1,1-二-(3,5-二甲基-2-羟基苯基)丁烷、2,2-二(3,5-二叔丁基-4-羟基苯基)丙烷、2,2-二-(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基巯基丁烷、1,1,5,5-四(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
1.7.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、4-羟基-3,5-二甲基苄基巯基乙酸十八烷基酯、4-羟基-3,5-二叔丁基苄基巯基乙酸十三烷基酯、三(3,5-二叔丁基-4-羟基苄基)胺、二硫代对苯二甲酸二(4-叔丁基-3-羟基-2,6-二甲基苄基)酯、二(3,5-二叔丁基-4-羟基苄基)硫化物、3,5-二叔丁基-4-羟基苄基巯基乙酸异辛酯。
1.8.羟苄基化丙二酸酯类,例如2,2-二(3,5-二叔丁基-2-羟基苄基)丙二酸二-十八烷基酯、2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸二-十八烷基酯、2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸二-十二烷基巯基乙基酯、2,2-二(3,5-二叔丁基-4-羟基苄基)丙二酸酯二[4-(1,1,3,3-四甲基丁基)苯基]。
1.9.芳族羟苄基化合物,例如1,3,5-三(3,5-二叔丁基-4-羟基苄基)-2,4,6-三甲基苯、1,4-二(3,5-二叔丁基-4-羟基苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯酚。
1.10.三嗪化合物,例如2,4-二(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-4,6-二(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-二(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。
1.11.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-羟基苄基膦酸二-十八烷基酯、5-叔丁基-4-羟基-3-甲基苄基膦酸二-十八烷基酯、3,5-二叔丁基-4-羟基苄基膦酸单乙酯的钙盐。
1.12.酰氨基酚类,例如4-羟基月桂酰苯胺、4-羟基硬脂酰苯胺、N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.13.β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元醇或多元醇的酯,例如与甲醇、乙醇、正辛醇、叔辛醇、线性和支化C7-C9链烷醇的混合物、十八烷醇、线性和支化C13-C15链烷醇的混合物、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、异氰脲酸三(羟基乙基)酯、N,N'-二(羟基乙基)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]辛烷的酯。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇的酯,例如与甲醇、乙醇、正辛醇、叔辛醇、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、异氰脲酸三(羟基乙基)酯、N,N'-二(羟基乙基)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、3,9-二[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]十一烷的酯。
1.15.β-(3,5-二环己基-4-羟基苯基)丙酸与一元醇或多元醇的酯,例如与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟基乙基)酯、N,N'-二(羟基乙基)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]辛烷的酯。
1.16. 3,5-二叔丁基-4-羟基苯基乙酸与一元醇或多元醇的酯,例如与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫二甘醇、二甘醇、三甘醇、季戊四醇、异氰脲酸三(羟基乙基)酯、N,N'-二(羟基乙基)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]辛烷的酯。
1.17.β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺,例如N,N'-二(3,5-二叔丁基-4-羟基苯基丙酰基)六亚甲基二酰胺、N,N'-二(3,5-二叔丁基-4-羟基苯基丙酰基)三亚甲基二酰胺、N,N'-二(3,5-二叔丁基-4-羟基苯基丙酰基)肼、N,N'-二[2-(3-[3,5-二叔丁基-4-羟基苯基]丙酰氧基)乙基]草酰胺(Naugard XL-1(RTM),由Uniroyal供应)。
1.18.抗坏血酸(维生素C)
1.19.胺类抗氧化剂,例如N,N'-二异丙基对苯二胺、N,N'-二仲丁基对苯二胺、N,N'-二(1,4-二甲基戊基)对苯二胺、N,N'-二(1-乙基-3-甲基戊基)对苯二胺、N,N'-二(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'-二(2-萘基)对苯二胺、N-异丙基-N'-苯基对苯二胺、N-(1,3-二甲基丁基)-N'-苯基对苯二胺、N-(1-甲基庚基)-N'-苯基对苯二胺、N-环己基-N'-苯基对苯二胺、4-(对甲苯氨磺酰基)二苯基胺、N,N'-二甲基-N,N'-二仲丁基对苯二胺、二苯基胺、N-烯丙基二苯基胺、4-异丙氧基二苯基胺、N-苯基-1-萘基胺、N-(4-叔辛基苯基)-1-萘基胺、N-苯基-2-萘基胺,辛基化二苯基胺,例如p,p'-二叔辛基二苯基胺、4-正丁基氨基苯酚、4-丁酰氨基苯酚、4-壬酰氨基苯酚、4-十二烷酰氨基苯酚、4-十八烷酰氨基苯酚、二(4-甲氧基苯基)胺、2,6-二叔丁基-4-二甲氨基甲基苯酚、2,4'-二氨基二苯基甲烷、4,4'-二氨基二苯基甲烷、N,N,N',N'-四甲基-4,4'-二氨基二苯基甲烷、1,2-二[(2-甲基苯基)氨基]乙烷、1,2-二(苯基氨基)丙烷、邻甲苯基双胍、二[4-(1',3'-二甲基丁基)苯基]胺、叔辛基化N-苯基-1-萘基胺、单-和二烷基化叔丁基/叔辛基二苯基胺的混合物、单-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基胺的混合物、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基胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单-和二烷基化叔丁基/叔辛基吩噻嗪类的混合物、单-和二烷基化叔辛基吩噻嗪类的混合物、N-烯丙基吩噻嗪、N,N,N',N'-四苯基-1,4-二氨基丁-2-烯、N,N-二(2,2,6,6-四甲基哌啶-4-基)六亚甲基二胺、癸二酸二(2,2,6,6-四甲基哌啶-4-基)酯、2,2,6,6-四甲基哌啶-4-酮、2,2,6,6-四甲基哌啶-4-醇。
2.UV吸收剂和光稳定剂
2.1. 2-(2'-羟基苯基)苯并***类,例如2-(2'-羟基-5'-甲基苯基)苯并***、2-(3',5'-二叔丁基-2'-羟基苯基)苯并***、2-(5'-叔丁基-2'-羟基苯基)苯并***、2-(2'-羟基-5'-(1,1,3,3-四甲基丁基)苯基)苯并***、2-(3',5'-二叔丁基-2'-羟基苯基)-5-氯苯并***、2-(3'-叔丁基-2'-羟基-5'-甲基苯基)-5-氯苯并***、2-(3'-仲丁基-5'-叔丁基-2'-羟基苯基)苯并***、2-(2'-羟基-4'-辛氧基苯基)苯并***、2-(3',5'-二叔戊基-2'-羟基苯基)苯并***、2-(3',5'-二(α,α-二甲基苄基)-2'-羟基苯基)苯并***、2-(3'-叔丁基-2'-羟基-5'-(2-辛氧基羰基乙基)苯基)-5-氯苯并***、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***、2-(3'-叔丁基-2'-羟基-5'-(2-甲氧基羰基乙基苯基)-5-氯苯并***、2-(3'-叔丁基-2'-羟基-5'-(2-甲氧基羰基乙基)苯基)苯并***、2-(3'-叔丁基-2'-羟基-5'-(2-辛氧基羰基乙基)苯基)苯并***、2-(3'-叔丁基-5'-[2-(2-乙基己氧基)羰基乙基]-2'-羟基苯基)苯并***、2-(3'-十二烷基-2'-羟基-5'-甲基苯基)苯并***、2-(3'-叔丁基-2'-羟基-5'-(2-异辛氧基羰基乙基)苯基苯并***、2,2'-亚甲基二[4-(1,1,3,3-四甲基丁基)-6-苯并***-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***与聚乙二醇300的酯交换产物;其中R'=3'-叔丁基-4'-羟基-5'-2H-苯并***-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***;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***。
2.2. 2-羟基二苯甲酮类,例如4-羟基,4-甲氧基、4-辛氧基、4-癸氧基、4-十二烷氧基、4-苄氧基、4,2',4'-三羟基和2'-羟基-4,4'-二甲氧基衍生物。
2.3.取代和未被取代苯甲酸的酯,例如水杨酸4-叔丁基苯基酯、水杨酸苯基酯、水杨酸辛基苯基酯、二苯甲酰基间苯二酚、二(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯基酯、3,5-二叔丁基-4-羟基苯甲酸十六烷基酯、3,5-二叔丁基-4-羟基苯甲酸十八烷基酯、3,5-二叔丁基-4-羟基苯甲酸2-甲基-4,6-二叔丁基苯基酯。
2.4.丙烯酸酯类,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-甲酯基肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸甲酯、α-氰基-β-甲基-对甲氧基肉桂酸丁酯、α-甲酯基-对甲氧基肉桂酸甲酯、N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚和新戊基四(α-氰基-β,β-二苯基丙烯酸酯)。
2.5.镍化合物,例如2,2'-硫代二[4-(1,1,3,3-四甲基丁基)苯酚]的镍配合物,如1:1或1:2配合物,具有或不具有额外配体如正丁胺、三乙醇胺或N-环己基二乙醇胺,二丁基二硫代氨基甲酸镍,4-羟基-3,5-二叔丁基苄基膦酸的单烷基酯,例如甲基或乙基酯的镍盐,酮肟类如2-羟基-4-甲基苯基十一烷基酮肟的镍配合物,1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,具有或不具有额外配体。
2.6.位阻胺类,例如癸二酸二(2,2,6,6-四甲基-4-哌啶基)酯,琥珀酸二(2,2,6,6-四甲基-4-哌啶基)酯,癸二酸二(1,2,2,6,6-五甲基-4-哌啶基)酯,正丁基-3,5-二叔丁基-4-羟基苄基丙二酸二(1,2,2,6,6-五甲基-4-哌啶基)酯,1-(2-羟基乙基)-2,2,6,6-四甲基-4-羟基哌啶和琥珀酸的缩合物,N,N'-二(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物,次氮基三乙酸三(2,2,6,6-四甲基-4-哌啶基)酯,1,2,3,4-丁烷四甲酸四(2,2,6,6-四甲基-4-哌啶基)酯,1,1'-(1,2-亚乙基)-二(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,2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸二(1,2,2,6,6-五甲基哌啶基)酯,3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮,癸二酸二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)酯,琥珀酸二(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)酯,碳酸二[2,2,6,6-四甲基-1-十一烷氧基哌啶-4-基]酯,N,N'-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的线性或环状缩合物,2-氯-4,6-二(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物,2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙基氨基)乙烷的缩合物,8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮,3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮,3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮,4-十六烷氧基-和4-硬脂氧基-2,2,6,6-四甲基哌啶的混合物,N,N'-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合物,1,2-二(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪以及4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[136504-96-6]);1,6-己二胺和2,4,6-三氯-1,3,5-三嗪以及N,N-二丁基胺和4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[19226864-7]);N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀酰亚胺,N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀酰亚胺,2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷,7,7,9,9-四甲基-2-环十一烷基-1-氧杂-3,8-二氮杂-4-氧代螺[4,5]癸烷和表氯醇的反应产物,1,1-二(1,2,2,6,6-五甲基-4-哌啶基氧羰基)-2-(4-甲氧基苯基)乙烯,N,N'-二甲酰基-N,N'-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺,4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶的二酯,聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷,马来酸酐-α-烯烃共聚物与2,2,6,6-四甲基-4-氨基哌啶或1,2,2,6,6-五甲基-4-氨基哌啶的反应产物,为N,N’-二-(2,2,6,6-四甲基-1-丙氧基哌啶-4-基)-1,6-己二胺和2,4-二氯-6-{正丁基-(2,2,6,6-四甲基-1-丙氧基哌啶-4-基)氨基}-[1,3,5]三嗪的被2-氯-4,6-二-(二正丁基氨基)-[1,3,5]三嗪封端的形式缩合产物的齐聚化合物的混合物,为N,N'-二-(2,2,6,6-四甲基哌啶-4-基)-1,6-己二胺和2,4-二氯-6-{正丁基-(2,2,6,6-四甲基哌啶-4-基)氨基}-[1,3,5]三嗪的被2-氯-4,6-二(二正丁基氨基)-[1,3,5]三嗪封端的形式缩合产物的齐聚化合物的混合物,2,4-二[N-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)-N-丁基氨基]-6-(2-羟基乙基)氨基-1,3,5-三嗪,1-(2-羟基-2-甲基丙氧基)-4-十八烷酰氧基-2,2,6,6-四甲基哌啶,5-(2-乙基己酰基)氧甲基-3,3,5-三甲基-2-吗啉酮,Sanduvor(Clariant;CAS登记号106917-31-1],5-(2-乙基己酰基)氧甲基-3,3,5-三甲基-2-吗啉酮,2,4-二[(1-环己氧基-2,2,6,6-哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N'-二-(3-氨基丙基)乙二胺)的反应产物,1,3,5-三(N-环己基-N-(2,2,6,6-四甲基哌嗪-3-酮-4-基)氨基)-s-三嗪,1,3,5-三(N-环己基-N-(1,2,2,6,6-五甲基哌嗪-3-酮-4-基)氨基)-s-三嗪。
2.7.草酰胺类,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'-二十二烷氧基-5,5'-二叔丁基草酰苯胺、2-乙氧基-2'-乙基草酰苯胺、N,N'-二(3-二甲氨基丙基)草酰胺、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-和对-甲氧基二取代酰替苯胺的混合物以及邻-和对-乙氧基二取代酰替苯胺的混合物。
2.8. 2-(2-羟基苯基)-1,3,5-三嗪类,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)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2,4-二(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)-4,6-二(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷氧基苯基)-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷氧基苯基)-4,6-二(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]-4,6-二(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]-4,6-二(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]-4,6-二(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]-4,6-二(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}-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属钝化剂,例如N,N'-二苯基草酰胺、N-水杨醛-N'-水杨酰基肼、N,N'-二水杨酰基肼、N,N'-二(3,5-二叔丁基-4-羟基苯基丙酰基)肼、3-水杨酰氨基-1,2,4-***、二(亚苄基)草酸二酰肼、草酰苯胺、间苯二甲酸二酰肼、癸二酰二苯基酰肼、N,N'-二乙酰基己二酸二酰肼、N,N'-二水杨酰基草酸二酰肼、N,N'-二水杨酰基硫代丙酸二酰肼。
4.亚磷酸酯和亚膦酸酯,例如亚磷酸三苯酯,亚磷酸二苯基烷基酯,亚磷酸苯基二烷基酯,亚磷酸三(壬基苯基)酯,亚磷酸C12-C18烷基二[4-(1-甲基-1-苯基乙基)苯基]酯,亚磷酸C12-C18链烯基二[4-(1-甲基-1-苯基乙基)苯基]酯,亚磷酸二[4-(1-甲基-1-苯基乙基)苯基][(E)-十八碳-9-烯基]酯,亚磷酸癸基二[4-(1-甲基-1-苯基乙基)苯基]酯,亚磷酸二癸基[4-(1-甲基-1-苯基乙基)苯基]酯,亚磷酸[4-(1-甲基-1-苯基乙基)苯基]二[(E)-十八碳-9-烯基]酯,亚磷酸三月桂基酯,亚磷酸三-十八烷基酯,二亚磷酸二硬脂基季戊四醇酯,亚磷酸三(2,4-二叔丁基苯基)酯,二亚磷酸二异癸基季戊四醇二亚磷酸酯,二亚磷酸二(2,4-二叔丁基苯基)季戊四醇酯,二亚磷酸二(2,4-二枯基苯基)季戊四醇酯,二亚磷酸二(2,6-二叔丁基-4-甲基苯基)季戊四醇酯,二异癸氧基季戊四醇二亚磷酸酯,二亚磷酸二(2,4-二叔丁基-6-甲基苯基)季戊四醇酯,二亚磷酸二(2,4,6-三(叔丁基苯基)季戊四醇酯,亚磷酸[2-叔丁基-4-[1-[5-叔丁基-4-二(十三烷氧基)膦氧基-2-甲基苯基]丁基]-5-甲基苯基]二-十三烷基酯,三亚磷酸三硬脂基山梨糖醇酯,例如在US 7468410 B2中作为实施例1和2的产物提到的至少两种不同的亚磷酸三(单-C1-C8烷基)苯基酯的混合物,例如在US 8008383 B2中作为混合物14、15、16、17、18、19、20、21、22、23、24、25和26提到的包含至少两种不同的亚磷酸三(戊基苯基)酯的亚磷酸酯混合物,包含亚磷酸三[4-(1,1-二甲基丙基)苯基]酯、亚磷酸[2,4-二(1,1-二甲基丙基)苯基]二[4-(1,1-二甲基丙基)苯基]酯、亚磷酸二[2,4-二(1,1-二甲基丙基)苯基][4-(1,1-二甲基丙基)苯基]酯和亚磷酸三[2,4-二(1,1-二甲基丙基)苯基]酯的至少四种不同亚磷酸酯的混合物,例如在US 8008383 B2中作为混合物34、35、36、37、38、39和40提到的包含至少两种不同的亚磷酸三(丁基苯基)酯的亚磷酸酯混合物,例如在US 8304477 B2中作为实施例1、2、3、4、5、6、7、8、9、10、11、12、13、14、15、16和17的产物提到的可以通过使(i)三氯化膦与(ii)被一个或多个氧原子间隔的二羟基链烷烃和(iii)单羟基-C6芳烃在除去氯化氢下缩合而得到的氧亚烷基桥连的二亚磷酸二(二-C6芳基)酯或齐聚亚磷酸酯,例如在US 8563637 B2中作为实施例1、2、3、4、5、6、7、8、9、10和11的产物提到的可以通过使(i)亚磷酸三苯酯与(ii)任选被一个或多个氧原子间隔的二羟基链烷烃和/或二(羟基烷基)(烷基)胺和(iii)任选被一个或多个氧原子间隔的单羟基链烷烃在除去苯酚下酯交换而得到的聚合亚磷酸酯,4,4'-亚联苯基二亚膦酸四(2,4-二叔丁基苯基)酯,6-异辛氧基-2,4,8,10-四叔丁基-12H-二苯并[d,g]-1,3,2-二氧杂磷辛因,亚磷酸二(2,4-二叔丁基-6-甲基苯基)甲基酯,亚磷酸二(2,4-二叔丁基-6-甲基苯基)乙基酯,6-氟-2,4,8,10-四叔丁基-12-甲基-二苯并[d,g]-1,3,2-二氧杂磷辛因,1,3,7,9-四叔丁基-11-辛氧基-5H-苯并[d][1,3,2]苯并二氧杂磷辛因,2,2',2”-次氮基[亚磷酸三乙基三-(3,3',5,5'-四叔丁基-1,1'-联苯-2,2'-二基)酯],亚磷酸2-乙基己基-(3,3',5,5'-四叔丁基-1,1'-联苯-2,2'-二基)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丙烷,2-叔丁基-6-甲基-4-[3-(2,4,8,10-四叔丁基苯并[d][1,3,2]苯并二氧杂磷杂环庚烷-6-基)氧丙基]苯酚,式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯,例如化合物(102)和(103)[下文进一步作为制备式I-P、I-O或I-M化合物的方法的另一实施方案的原料所示的式PRE-I-P、PRE-I-O或PRE-I-M,所述化合物(102)和(103)在试验部分作为实施例S-1和S-2的产物示出]。
尤其优选下列亚磷酸酯:
亚磷酸三(2,4-二叔丁基苯基)酯(Irgafos 168,RTM BASF),亚磷酸三(壬基苯基)酯,
5.羟胺类和胺N-氧化物,例如N,N-二苄基羟胺、N,N-二乙基羟胺、N,N-二辛基羟胺、N,N-二月桂基羟胺、N,N-二-十四烷基羟胺、N,N-二-十六烷基羟胺、N,N-二-十八烷基羟胺、N-十六烷基-N-十八烷基羟胺、N-十七烷基-N-十八烷基羟胺、衍生于氢化牛脂胺的N,N-二烷基羟胺。
6.硝酮类,例如N-苄基-α-苯基硝酮、N-乙基-α-甲基硝酮、N-辛基-α-庚基硝酮、N-月桂基-α-十一烷基硝酮、N-十四烷基-α-十三烷基硝酮、N-十六烷基-α-十五烷基硝酮、N-十八烷基-α-十七烷基硝酮、N-十六烷基-α-十七烷基硝酮、N-十八烷基-α-十五烷基硝酮、N-十七烷基-α-十七烷基硝酮、N-十八烷基-α-十六烷基硝酮、衍生于N,N-二烷基羟胺衍生于氢化牛脂胺的硝酮。
7.胺N-氧化物,例如N,N-二-(氢化菜油烷基)-N-甲基胺N-氧化物、N-十六烷基-N-甲基-N-十八烷基-1-胺氧化物、N-十六烷基-N-甲基-N-十六烷基-1-胺氧化物、N-十八烷基-N-甲基-N-十八烷基-1-胺氧化物。
8.硫代增效剂,例如硫代二丙酸二月桂基酯、硫代二丙酸二肉豆蔻基酯、硫代二丙酸二硬脂基酯或季戊四醇四[3-正月桂基丙酸酯]。
9.过氧化物清除剂,例如α-硫代二丙酸的酯,例如月桂基、硬脂基、肉豆蔻基或十三烷基酯,巯基苯并咪唑或2-巯基苯并咪唑的锌盐,二丁基二硫代氨基甲酸锌,二-十八烷基二硫化物,季戊四醇四(β-十二烷基巯基)丙酸酯。
10.聚酰胺稳定剂,例如与碘化物和/或磷化合物和二价锰的盐组合的铜盐。
11.酸清除剂,例如蜜胺,聚乙烯基吡咯烷酮,双氰胺,氰脲酸三烯丙基酯,脲衍生物,肼衍生物,胺类,聚酰胺,聚氨酯,高级脂肪酸的碱金属盐和碱土金属盐,例如硬脂酸钙、硬脂酸锌、山萮酸镁、硬脂酸镁、蓖麻油酸钠和棕榈酸钾,邻苯二酚锑和邻苯二酚锌。
12.不同于式I-P、I-O和I-M化合物并且不同于式PRE-I-P、PRE-I-O和PRE-I-M化合物的苯并呋喃酮类和吲哚啉酮类,例如US-A-4,325,863;US A-4,338,244;US-A-5,175,312;US-A-5,216,052;US-A-5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839或EP-A-0591102中所公开的那些或3-[4-(2-乙酰氧基乙氧基)苯基]-5,7-二叔丁基苯并呋喃-2-酮,5,7-二叔丁基-3-[4-(2-硬脂酰氧基乙氧基)苯基]苯并呋喃-2-酮,3,3'-二[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-新戊酰氧基苯基)-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,3-(2-乙酰氧基-4-(1,1,3,3-四甲基丁基)苯基)-5-(1,1,3,3-四甲基丁基)苯并呋喃-2-酮,3,5-二叔丁基-4-羟基苯甲酸[5-叔丁基-2-(5-叔丁基-2-氧代-3H-苯并呋喃-3-基)苯基]酯,6-羟基己酸[6-[6-[2-[4-(5,7-二叔丁基-2-氧代-3H-苯并呋喃-3-基)苯氧基]乙氧基]-6-氧代己氧基]-6-氧代己基]酯。
13.成核剂,例如无机物质,如滑石,金属氧化物,如二氧化钛或氧化镁,优选碱土金属的磷酸盐、碳酸盐或硫酸盐;有机化合物,如单-或多羧酸及其盐,例如4-叔丁基苯甲酸、己二酸、二苯基乙酸、琥珀酸钠或苯甲酸钠;高分子化合物,如离子性共聚物(离聚物),Irgaclear XT 386(RTM BASF),1,3:2,4-二(3',4'-二甲基亚苄基)山梨糖醇,1,3:2,4-二(对甲基二亚苄基)山梨糖醇和1,3:2,4-二(亚苄基)山梨糖醇。
14.填料和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、玻璃珠、石棉、滑石、高岭土、膨润土、云母、水滑石、硫酸钡、金属氧化物和氢氧化物、炭黑、石墨、木粉以及其他天然产物的粉或纤维、合成纤维。
15.其他添加剂,例如增塑剂、润滑剂、流变添加剂、催化剂、流动控制剂、荧光增白剂、耐火剂、抗静电剂和发泡剂。
还惊人地发现许多式I-P、I-O或I-M化合物与其他添加剂组合对于稳定有机材料以防热、光和/或氧化降解非常有效,特别是与不同于式I-P、I-O或I-M化合物的酚类抗氧化剂或亚磷酸酯或亚膦酸酯作为其他添加剂组合。结果通常是式I-P、I-O或I-M化合物的存在允许降低其他添加剂的量超过基于其他添加剂重量的单纯1:1替代。
优选如下组合物,包含作为组分a)的易于氧化、热或光诱发降解的有机材料,作为组分b)的式I-P、I-O或I-M化合物和组分c)的其他添加剂。
优选如下组合物,其中组分b)与组分c)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10。
优选如下组合物,其中组分b)与组分c)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10并且其中组分b)和组分c)的总量小于组分a)的80重量%,尤其是50重量%。
优选如下组合物,其中组分b)与组分c)的重量比为4:1-1:20,特别是2:1-1:10并且组分b)和组分c)的总量基于组分a)的重量为0.005-50%,特别是0.005-10%,非常特别为0.005-1%。
优选如下组合物,包含作为组分c)的其他添加剂,其为抗氧化剂,UV吸收剂,受阻胺光稳定剂,镍化合物,金属钝化剂,不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯,羟胺或胺N-氧化物,硫代增效剂,过氧化物清除剂,成核剂,填料或增强剂。
优选如下组合物,包含作为组分c)的其他添加剂,其为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯,酸清除剂,酚类抗氧化剂或胺类抗氧化剂。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,
b)式I-P、I-O或I-M化合物,和
c)其他添加剂,其为酚类抗氧化剂或不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯。
优选包含作为组分c)的酚类抗氧化剂的组合物。
优选如下组合物,包含作为组分c)的酚类抗氧化剂,其为β-(3,5-二叔丁基-4-羟基苯基)丙酸的酯。
特别相关的酚类抗氧化剂是如下所示的化合物:
其中一种化学名是四[β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基]甲烷或四[3-(3,5-二叔丁基-4-羟基-苯基)丙酰氧基甲基]甲烷。它含于商品Irganox 1010(RTMBASF)中。
特别相关的另一种酚类抗氧化剂是如下所示的化合物:
其中一种化学名是β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯或3-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯。它含于商品Irganox 1076(RTM BASF)中。
优选如下组合物,包含作为组分c)的酚类抗氧化剂,其为四[β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基]甲烷或β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯。
优选如下组合物,包含作为组分c)的不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯。
特别相关的亚磷酸酯是如下所示的化合物:
其中一种化学名是亚磷酸三(2,4-二叔丁基苯基)酯。它含于商品Irgafos 168(RTM BASF)中。
优选如下组合物,包含作为组分c)的亚磷酸酯,其为亚磷酸三(2,4-二叔丁基苯基)酯。
特别相关的亚磷酸酯具有式PRE-I-P、PRE-I-O或PRE-I-M。
优选如下组合物,包含作为组分b)的式I-P、I-O或I-M化合物和作为组分c)的其他添加剂,其为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯。
优选如下组合物,包含作为组分b)的式I-P、I-O或I-M化合物和作为组分c)的其他添加剂,其为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯,其中
当组分b)具有式I-P时,该亚磷酸酯具有式PRE-I-P,
其中在式I-P和式PRE-I-P中的相应取代基相同,
当组分b)具有式I-O时,该亚磷酸酯具有式PRE-I-O,
其中在式I-O和式PRE-I-O中的相应取代基相同,
当组分b)具有式I-M时,该亚磷酸酯具有式PRE-I-M,
其中在式I-M和式PRE-I-M中的相应取代基相同。
上述组合物的实例是一种包含化合物(402)作为组分b)和化合物(102)作为组分c)的组合物或一种包含化合物(403)作为组分b)和化合物(103)作为组分c)的组合物。化合物(102)、(103)、(402)和(403)的结构示于相应实施例S-1、S-2、S-3a和S-4a中。
任选地,一种包含易于氧化、热或光诱发降解的有机材料作为组分a),式I-P、I-O或I-M化合物作为组分b)和其他添加剂作为组分c)的组合物含有第二种其他添加剂作为组分d)。
优选一种包含易于氧化、热或光诱发降解的有机材料作为组分a),式I-P、I-O或I-M化合物作为组分b),其他添加剂作为组分c)和第二种其他添加剂作为组分d)的组合物。
优选其中组分b)与组分d)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10的组合物。
优选其中组分b)与组分d)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10,并且其中组分b)、组分c)和组分d)的总量为组分a)的0.005-50重量%,特别是0.005-10重量%,非常特别0.005-1重量%的组合物。
优选包含组分a),组分b),作为组分c)的其他添加剂—选自不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯,酸清除剂,酚类抗氧化剂和胺类抗氧化剂—以及作为组分d)的第二种其他添加剂的组合物;条件是组分d)为不同于组分c)的化合物。
优选包含组分a)、组分b)、组分c)和组分d)的组合物,其中组分c)和组分d)相互独立地为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯,酸清除剂,酚类抗氧化剂或胺类抗氧化剂;条件是组分d)为不同于组分c)的化合物。
优选包含组分a)、组分b)、作为组分c)的酚类抗氧化剂和作为组分d)的胺类抗氧化剂的组合物。
优选包含组分a)、组分b)、作为组分c)的酚类抗氧化剂和作为组分d)的不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的组合物。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,以及
d)为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的第二种其他添加剂。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,所述酚类抗氧化剂为四[β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基]甲烷或β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯,以及
d)为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的第二种其他添加剂。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,以及
d)为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯的第二种其他添加剂,其中
当组分b)具有式I-P时,该亚磷酸酯具有式PRE-I-P,
其中在式I-P和式PRE-I-P中的相应取代基相同,
当组分b)具有式I-O时,该亚磷酸酯具有式PRE-I-O,
其中在式I-O和式PRE-I-O中的相应取代基相同,
当组分b)具有式I-M时,该亚磷酸酯具有式PRE-I-M,
其中在式I-M和式PRE-I-M中的相应取代基相同。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,以及
d)为亚磷酸酯的第二种其他添加剂,所述亚磷酸酯为亚磷酸三(2,4-二叔丁基苯基)酯。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,所述酚类抗氧化剂为四[β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基]甲烷或β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯,和
d)为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯的第二种其他添加剂,其中
当组分b)具有式I-P时,该亚磷酸酯具有式PRE-I-P,
其中在式I-P和式PRE-I-P中的相应取代基相同,
当组分b)具有式I-O时,该亚磷酸酯具有式PRE-I-O,
其中在式I-O和式PRE-I-O中的相应取代基相同,
当组分b)具有式I-M时,该亚磷酸酯具有式PRE-I-M,
其中在式I-M和式PRE-I-M中的相应取代基相同。
优选如下组合物,包含:
a)易于氧化、热或光诱发降解的有机材料,
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,所述酚类抗氧化剂为四[β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基]甲烷或β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯,以及
d)为亚磷酸酯的第二种其他添加剂,所述亚磷酸酯为亚磷酸三(2,4-二叔丁基苯基)酯。
与式PRE-I-P、PRE-I-O或PRE-I-M的相应前体化合物相比,式I-P、I-O或I-M化合物不太易水解,例如在潮湿条件下储存时。因此,该包含组分b)的组合物需要更少的水解抑制剂或者甚至不需要任何水解抑制剂。水解抑制剂例如是三异丙醇胺。
优选不含三异丙醇胺,更优选不含不为受阻胺光稳定剂的脂族仲或叔胺,最优选不含脂族仲或叔胺,非常优选不含脂族胺,尤其优选不含胺,非常尤其优选不含水解抑制剂的组合物。
对组合物描述作为组分a)的易于氧化、热或光诱发降解的有机材料和作为组分b)的式I-P、I-O或I-M化合物的上述优选情形。这些优选情形也适用于本发明的其他实施方案。在这些其他实施方案中,还包括其他添加剂作为组分c)的任选存在和第二种其他添加剂作为组分d)的任选存在。
本发明的另一实施方案涉及一种保护易于氧化、热或光诱发降解的有机材料,即组分a)的方法,包括下列步骤:
-提供该有机材料,即组分a),和
-将式I-P、I-O或I-M化合物,即组分b)掺入所提供的有机材料中或施用于其上。
组分b)的掺入或施用可以在优选可以密闭的加工设备,特别是装有搅拌机的可加热容器中进行。装有搅拌机的可加热容器例如是捏合机、挤出机、混合机或搅拌容器。其具体实例是单螺杆挤出机、反向旋转和同向旋转双螺杆挤出机、行星齿轮式挤出机、环形挤出机或共捏合机。还可以使用含有至少一个可以对其施加真空和/或可以将其设定在其中氧气含量低或者不存在氧气的气氛下,例如设定在氮气气氛下的除气室的加工设备。组分b)可以直接加入该加工设备中。
组分b)可以在组分a)的任何加工阶段掺入或施用。若组分a)为聚合物,则该阶段特别是在组分a)在该加工设备中的成型操作之前或其过程中。
组分b)可以以干粉形式、以粉末的压实形式如颗粒、以熔体形式、以包封形式如在蜡或辅助聚合物中的包封形式或者以湿混合物如例如在惰性溶剂、水或油中的溶液、分散体或悬浮液形式掺入或施用。在组分b)的湿混合物情况下可以存在分散或悬浮剂。
组分b)还可以通过喷雾于组分a)上而掺入或施用。
在组分a)为聚合物的情况下,将组分b)掺入或施用于组分a)中的另一可能性是在组分a)的相应原料,例如单体聚合之前、之中或者恰好之后加入。例如,在钝化聚合催化剂的过程中喷雾是特别有利的。若在组分a)的形成过程中发生交联,则优选在交联之前掺入或施用。
在组分a)为聚合物的情况下,该掺入或施用方法优选为模塑方法,特别是注塑、吹塑、压塑成型、旋转成型、搪塑或挤塑。
优选一种其中该易于氧化、热或光诱发降解的有机材料为聚合物并且包括下列步骤的方法:
-提供该易于氧化、热或光诱发降解的有机材料,和
-将式I-P、I-O或I-M化合物掺入所提供的有机材料中并且其中部分或全部掺入在135-350℃,优选150-340℃,特别是180-330℃,非常尤其是190-320℃范围内的温度下进行。
优选一种其中在为聚合物的组分a)加工过程中在挤出机中掺入或施用组分b)的方法。
在其他添加剂和任选地,第二种其他添加剂,即组分c)或组分c)和d)的情况下,组分b)和该其他添加剂或该第二种其他添加剂可以单独或者相互混合掺入组分a)中或施用于其上。需要的话,可以在掺入组分a)中之前例如通过干混、压实、熔融、用蜡或辅助聚合物包封或者作为例如在惰性溶剂、水或油中的溶液、分散体或悬浮液形式的湿混合物将各组分相互混合。
组分b)和其他添加剂以及任选地,第二种其他添加剂还可以以母料(‘浓缩物’)形式加入组分a)中,该含有组分b)、其他添加剂、任选第二种其他添加剂和作为辅助聚合物的母料聚合物。组分b)和其他添加剂以及任选地,第二种其他添加剂以例如为该母料的1-40重量%,优选2-20重量%的浓度掺入该母料中。该母料聚合物含量为到100重量%该母料的差值。该母料聚合物在组分a)为聚合物的情况下不必为与其相同的聚合物。
本发明的另一实施方案涉及一种由包含如下组分的组合物制成的制品:
a)易于氧化、热或光诱发降解的有机材料,和
b)式I-P、I-O或I-M化合物。
有利地由包含为聚合物的组分a)和组分b)的组合物制成的制品可以是成型制品。该类成型制品的实例是:
I-1)漂浮装置,海洋应用,浮筒,浮标,用于甲板、码头、船、皮艇、船桨和海滩增强材料的塑料木材。
I-2)汽车应用,特别是保险杠,仪表盘,电池,前后衬里,机罩下方的成型零件,帽架,后备箱衬里,内衬套,安全气囊罩,配件(灯光)用电子模件,仪表盘用板,前照灯玻璃,仪表板,外衬套,车内装饰,汽车灯,车前灯,停车灯,尾灯,停车灯,内饰和外饰;门嵌板;气罐;玻璃正面;后窗;座椅靠背,外壁板,导线绝缘,用于密封的型材挤出,镀层,立柱盖,底盘零部件,排气***,燃油滤清器/加油嘴,燃油泵,油箱,车侧饰条,折叠式车顶,车外后视镜,外饰,扣件/附件,前端模块,玻璃,铰链,门锁***,行李/车顶轨道,冲压零部件,密封垫,侧撞保护,减声器/隔音器和天窗。
I-3)道路交通设备,特别是信号岗,路标标杆,汽车配件,三角警示牌,医疗箱,头盔,轮胎。
I-4)用于飞机、铁路、汽车(小汽车、摩托车、卡车)的装置,包括器具。
I-5)空间应用设备,特别是火箭和卫星,例如再入防护罩。
I-6)建筑与设计设备,采矿应用,消声***,街道安全岛和避难所。
II-1)电器,通用和电气/电子设备(个人计算机、电话机、手机、打印机、电视机、音频和视频设备)中的箱和罩盖物,花盆、***天线罩和面板设备。
II-2)用于其他材料如钢或纺织品的外套。
II-3)电子工业用设备,特别是用于插头,尤其是计算机插头的绝缘材料,用于电气和电子零部件的外壳,印制板和电子数据存储材料如芯片、支票卡或***。
II-4)电气设备,特别是洗衣机、滚筒、烤炉(微波炉)、洗碗机、混合器和熨斗。
II-5)用于灯(例如路灯、灯罩)的罩。
II-6)在电线电缆中的应用(半导体、绝缘材料和电缆外套)。
II-7)用于冷凝器、冰箱、加热装置、空调机、电子器件封装、半导体、咖啡机和真空吸尘器的箔。
III-1)专业制品如齿轮、滑动街头、垫片、螺丝、螺栓、把手和旋钮。
III-2)旋转叶片、通风设备和风车轮叶、太阳能装置、游泳池、游泳池罩、池衬垫、塘衬垫、壁橱、衣橱、隔离墙、板条墙、折叠墙、屋顶、百叶窗(例如卷帘窗)、附件、管道之间的连接件、套筒和传送带。
III-3)卫生制品,特别是淋浴隔间、马桶座圈、罩和洗手池。
III-4)卫生用品,特别是尿布(婴儿、成人失禁)、女性卫生用品、浴帘、刷子、垫子、浴盆、移动厕所、牙刷和便盆。
III-5)水、废水和化学品用管(交联或未交联),电线电缆保护用管,气体、油和污水管道,排水槽,落水管和排水***。
III-6)具有任何几何形状的型材(窗玻璃)和壁板。
III-7)玻璃代用品,特别是挤出或共挤出板材,建筑物(整块料、双层或多层)、飞机、学校用玻璃,挤出板,建筑玻璃、火车、交通工具、卫生制品和温室用窗膜。
III-8)板材(壁、切菜板),挤出涂层(相纸、利乐包和管道涂层),筒仓,木材代用品,塑料木材,木材复合材料,壁,表面,家具,装饰铝箔,地板覆盖物(室内和室外应用),地板,木板道和瓦片。
III-9)进气和排气歧管。
III-10)水泥、混凝土、复合材料应用以及罩、壁板和镀层,栏杆,扶手,厨房工作台面,屋顶,屋顶板,瓷砖和油布。
IV-1)板材(壁和切菜板),托盘,人造草,体育馆环圈(体育运动)的合成(如AstroTurf(RTM))、人造罩,体育馆环圈(体育运动)的人造地面和胶带。
IV-2)长纤维和短纤维的纺织品(地毯/卫生用品/土工布/单丝;过滤器;抹布/帘(罩)/医疗应用),散纤维(诸如长袍/防护服的应用),网,绳,电缆,细绳,粗线,细线,安全带,衣服,内衣,手套;靴子;胶靴,贴身衣服,服装,游泳衣,运动服装,伞(阳伞、遮阳伞),降落伞,滑翔伞,帆,“气球绸”,野营用品,帐篷,充气床垫,日光浴床,集装袋和袋子。无纺布如医用织物和相关服装,工业服装,户外面料,屋内装饰和构筑织物。
IV-3)屋顶、隧道、堆放场、池塘、库房用膜、绝缘材料、罩和密封材料,墙面屋面膜,土工膜,游泳池,帘(罩)/遮阳板,雨篷,顶篷,壁纸,食品包装(软和硬),医药包装(软和硬),安全气囊/安全带,靠手和头枕,地毯,中控台,仪表板,驾驶舱,门,顶置中控模块,门饰板,头部衬垫,室内照明,内部后视镜,包裹架,后行李箱盖,座位,转向柱,方向盘,纺织品和行李箱衬垫。
V)薄膜(包装,堆放,层压,农业和园艺,温室,覆盖料,隧道,青贮饲料),捆包,游泳池,废物袋,壁纸,拉伸膜,拉菲草,脱盐膜,电池和连接件。
VI-1)食品包装(软和硬),瓶。
VI-2)储存***如盒(板条箱),行李箱,大木箱,家用盒子,运货板,搁板,轨道,螺丝盒,纸盒和罐。
VI-3)墨盒,注射器,医疗应用,任何运输用集装箱,废纸篓和垃圾桶,废物袋,箱,垃圾箱,垃圾箱衬袋,带轮垃圾箱,一般集装箱,水/用过的水/化学品/气体/油/汽油/柴油用罐;油箱衬板,盒,板条箱,电池盒,槽,医疗设备如活塞,眼科应用,诊断装置和药品泡罩包装。
VII-1)挤出涂层(相纸、利乐包和管道涂层),任何种类的家用制品(例如器具、暖水瓶/衣架),紧固***如衬套,电线电缆夹具,拉链,插栓,锁和搭扣。
VII-2)支撑装置,休闲用品如体育健身器材,体操垫,滑雪靴,直排轮,滑雪板,大脚板,运动场地(例如网球场);螺旋盖,瓶盖和瓶塞以及罐。
VII-3)一般家具,发泡制品(坐垫,缓冲器),泡沫,海绵,擦碗布,垫子,庭院椅,体育场座位,桌子,沙发,玩具,建筑套包(板/外形/球),游戏房,滑梯和玩耍车。
VII-4)光磁数据存储用材料。
VII-5)厨具(吃、喝、煮、存)。
VII-6)CD、盒式磁带和录像带用盒;DVD电子物品,任何种类的办公用品(圆珠笔,***和印泥,鼠标,搁板,轨道),任何体积和内容物的瓶子(饮料、洗涤剂、包括香水在内的化妆品)以及胶粘带。
VII-7)鞋类(鞋/鞋底),鞋垫,鞋罩,粘合剂,结构胶,食品盒(水果、蔬菜、肉、鱼),合成纸,瓶子标签,沙发,人工关节(人用),印制板(柔性),印刷电路板和显示技术。
VII-8)填充聚合物(滑石、白垩、瓷土(高岭土)、硅灰石、颜料、炭黑、TiO2、云母、纳米复合材料、白云石、硅酸盐、玻璃、石棉)的装置。
优选一种为成型制品的制品,所述成型制品为薄膜、关、型材、瓶、罐、容器或纤维。
优选一种模塑的成型制品。特别地,模塑通过注塑、吹塑、压塑成型、旋转成型、搪塑或挤塑进行。
本发明的另一实施方案涉及式I-P、I-O或I-M化合物,即组分b)在稳定易于氧化、热或光诱发降解的有机材料,即组分a),以防氧化、热或光降解中的用途。
优选组分b)在稳定泡沫形式的聚氨酯以防焦烧中的用途。
优选式I-P、I-O或I-M化合物与其他添加剂组合在稳定易于氧化、热或光诱发降解的有机材料以防氧化、热或光降解中的用途。
优选式I-P、I-O或I-M化合物与为酚类抗氧化剂或不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的其他添加剂组合在稳定易于氧化、热或光诱发降解的有机材料以防氧化、热或光降解中的用途。
优选式I-P、I-O或I-M化合物与为酚类抗氧化剂的其他添加剂以及为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的第二种其他添加剂组合在稳定易于氧化、热或光诱发降解的有机材料以防氧化、热或光降解中的用途。
优选式I-P、I-O或I-M化合物与为酚类抗氧化剂的其他添加剂以及为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的第二种其他添加剂组合在稳定为聚烯烃或其共聚物的易于氧化、热或光诱发降解的有机材料以防氧化、热或光降解中的用途。
加工组分a)的特征在于组分a)在组分a)的加工时间过程中短期暴露于热,例如在135-350℃,特别是150-340℃范围内的温度。加工时间与例如可能的使用时间相比要短,例如1小时以内对1周以上。使用通常在低于加工过程中的温度的温度下,例如0-50℃下进行。
优选组分b)在稳定组分a)以防在加工过程中氧化或热降解中的用途。
本发明的另一实施方案涉及式I-P、I-O或I-M化合物:
其中
R1P表示子式II-P、II-O或II-M之一:
R1O表示子式II-O或II-M之一,或
R1M表示子式II-M;
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RP2、RP3、RP5和RP6相互独立地为氢或C1-C8烷基,
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基,和
RM1、RM3、RM5和RM6相互独立地为氢或C1-C8烷基。
本发明的另一实施方案涉及一种添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,和
c)选自不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯,酸清除剂,酚类抗氧化剂和胺类抗氧化剂的其他添加剂。
优选如下组合物,其中组分b)与组分c)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10。
优选一种其中组分b)与组分c)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10的添加剂组合物。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,和
c)为酚类抗氧化剂或不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的其他添加剂。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,和
c)为酚类抗氧化剂的其他添加剂。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,和
c)为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的其他添加剂。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,和
c)为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯的其他添加剂。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,和
c)为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯的其他添加剂,其中当组分b)具有式I-P时,该亚磷酸酯具有式PRE-I-P,
其中在式I-P和式PRE-I-P中的相应取代基相同,
当组分b)具有式I-O时,该亚磷酸酯具有式PRE-I-O,
其中在式I-O和式PRE-I-O中的相应取代基相同,
当组分b)具有式I-M时,该亚磷酸酯具有式PRE-I-M,
其中在式I-M和式PRE-I-M中的相应取代基相同。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,和
c)为四[β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基]甲烷、β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯或亚磷酸三(2,4-二叔丁基苯基)酯的其他添加剂。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,和
c)为亚磷酸三(2,4-二叔丁基苯基)酯的其他添加剂。
优选包含第二种其他添加剂作为组分d)的添加剂组合物。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,
c)选自不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯,酸清除剂,酚类抗氧化剂和胺类抗氧化剂的其他添加剂,和
d)选自不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯,酸清除剂,酚类抗氧化剂和胺类抗氧化剂的第二种其他添加剂;条件是组分c)是不同于组分d)的化合物。
优选如下组合物,其中组分b)与组分c)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10,并且其中组分b)与组分d)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10。
优选如下添加剂组合物,其中组分b)与组分c)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10,并且其中组分b)与组分d)的重量比为10:1-1:30,特别是4:1-1:20,尤其是2:1-1:10。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,以及
d)为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的第二种其他添加剂。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,
c)为四[β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基]甲烷或β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯的其他添加剂,和
d)为不同于式I-P、I-O或I-M化合物的亚磷酸酯或亚膦酸酯的第二种其他添加剂。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,以及
d)为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯的第二种其他添加剂,其中
当组分b)具有式I-P时,该亚磷酸酯具有式PRE-I-P,
其中在式I-P和式PRE-I-P中的相应取代基相同,
当组分b)具有式I-O时,该亚磷酸酯具有式PRE-I-O,
其中在式I-O和式PRE-I-O中的相应取代基相同,
当组分b)具有式I-M时,该亚磷酸酯具有式PRE-I-M,
其中在式I-M和式PRE-I-M中的相应取代基相同。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,
c)为酚类抗氧化剂的其他添加剂,以及
d)为亚磷酸三(2,4-二叔丁基苯基)酯的第二种其他添加剂。
优选如下添加剂组合物,包含:
b)式I-P、I-O或I-M化合物,
c)为四[β-(3,5-二叔丁基-4-羟基苯基)丙酰氧基甲基]甲烷或β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯的其他添加剂,和
d)为亚磷酸三(2,4-二叔丁基苯基)酯的第二种其他添加剂。
本发明的另一实施方案涉及一种制备式I-P、I-O或I-M化合物的方法:
其中
R1P表示子式II-P、II-O或II-M之一:
R1O表示子式II-O或II-M之一,或
R1M表示子式II-M;
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RP2、RP3、RP5和RP6相互独立地为氢或C1-C8烷基,
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基,和
RM1、RM3、RM5和RM6相互独立地为氢或C1-C8烷基,
包括下列步骤:
-使在式I-P情况下的式PRE-I-P化合物、在式I-O情况下的式PRE-I-O化合物或在式I-M情况下的式PRE-I-M化合物与氧化剂反应:
其中在式I-P和式PRE-I-P中的相应取代基相同,在式I-O和式PRE-I-O中的相应取代基相同并且在式I-M和式PRE-I-M中的相应取代基相同。
式PRE-I-P和PRE-I-O化合物的实例如WO 2016/020322 A所述。
优选该氧化剂是一种包含氧-氧单键的化合物。具体而言,该氧化剂是过氧化合物。非常具体地,该氧化剂是过酸,尤其是过氧甲酸、过氧乙酸、过氧苯甲酸或间氯过苯甲酸(=3-氯过氧苯甲酸)。非常尤其地,该氧化剂是间氯过苯甲酸(=3-氯过氧苯甲酸)。
优选反应步骤在非质子溶剂如二氯甲烷、二氯乙烷或甲苯中进行。
若氧化剂在该制备方法中的量选择为不足化学计算量,则可以得到一种添加剂混合物。
在氧化剂在该方法中的量选择为不足化学计算量但接近化学计算量的情况下,该添加剂混合物包含:
b)式I-P、I-O或I-M化合物,和
c)为式MONO-I-P、MONO-I-O或MONO-I-M的亚磷酸酯的其他添加剂:
其中
R1P表示子式II-P、II-O或II-M之一:
R1O表示子式II-O或II-M之一,或
R1M表示子式II-M;
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RP2、RP3、RP5和RP6相互独立地为氢或C1-C8烷基,
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基,和
RM1、RM3、RM5和RM6相互独立地为氢或C1-C8烷基,
其中
当组分b)具有式I-P时,该亚磷酸酯具有式MONO-I-P,
其中在式I-P和式MONO-I-P中的相应取代基相同,
当组分b)具有式I-O时,该亚磷酸酯具有式MONO-I-O,
其中在式I-O和式MONO-I-O中的相应取代基相同,
当组分b)具有式I-M时,该亚磷酸酯具有式MONO-I-M,
其中在式I-M和式MONO-I-M中的相应取代基相同。
在氧化剂在制备式I-P、I-O或I-M化合物的方法中的量选择为不足化学计算量,准确地是在化学计算量和零之间的情况下,该添加剂混合物包含:
b)式I-P、I-O或I-M化合物,
c)为式MONO-I-P、MONO-I-O或MONO-I-M的亚磷酸酯的其他添加剂,和
d)为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯的第二种其他添加剂,
其中
当组分b)具有式I-P时,该其他添加剂是式MONO-I-P的亚磷酸酯并且该第二其他添加剂是式PRE-I-P的亚磷酸酯,其中在式I-P、式MONO-I-P和式PRE-I-P中的相应取代基相同,
当组分b)具有式I-O时,该其他添加剂是式MONO-I-O的亚磷酸酯并且该第二其他添加剂是式PRE-I-O的亚磷酸酯,其中在式I-O、式MONO-I-O和式PRE-I-O中的相应取代基相同,
当组分b)具有式I-M时,该其他添加剂是式MONO-I-M的亚磷酸酯并且该第二其他添加剂是式PRE-I-M的亚磷酸酯,其中在式I-M、式MONO-I-M和式PRE-I-M中的相应取代基相同。
因此,前一段落的添加剂混合物也是如下添加剂混合物的实例,其包含:
b)式I-P、I-O或I-M化合物,和
c)为式PRE-I-P、PRE-I-O或PRE-I-M的亚磷酸酯的其他添加剂,其中当组分b)具有式I-P时,该亚磷酸酯具有式PRE-I-P,
其中在式I-P和式PRE-I-P中的相应取代基相同,
当组分b)具有式I-O时,该亚磷酸酯具有式PRE-I-O,
其中在式I-O和式PRE-I-O中的相应取代基相同,
当组分b)具有式I-M时,该亚磷酸酯具有式PRE-I-M,
其中在式I-M和式PRE-I-M中的相应取代基相同。
氧化剂可以例如通过对于1mol式I-P、I-O或I-M化合物使用导致小于2mol氧化性氧当量的量的氧化剂而选择为不足化学计算量。这里的氧化性氧当量涉及将式PRE-I-P、PRE-I-O或PRE-I-M中的一个磷原子转化成相应式I-P、I-O或I-M中的相应P=O基团所需氧化剂量。例如,对于1mol式PRE-I-P、PRE-I-O或PRE-I-M化合物,将间氯过苯甲酸的量选择为1.0mol以获得添加剂混合物。该实例是其中将氧化剂在制备式I-P、I-O或I-M化合物的方法中的量选择为不足化学计算量,准确地是在化学计算量和0之间的情形。
本发明的另一实施方案涉及另一种制备式I-P、I-O或I-M化合物的方法。该制备的基本合成方法是使合适的卤素取代磷衍生物与相应羟基取代苯并呋喃-2-酮衍生物在碱和任选溶剂,尤其是非质子溶剂存在下反应。
卤素是氟原子、氯原子、溴原子或碘原子。优选氯或溴原子,尤其是氯原子。
优选另一种其中该碱为三乙胺、吡啶、碳酸钾或碳酸钠的方法。
非质子溶剂例如是乙腈、二氯乙烷或甲苯。
优选另一种制备式I-P化合物的方法:
其中
R1P表示子式II-P、II-O或II-M之一:
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RP2、RP3、RP5和RP6相互独立地为氢或C1-C8烷基,
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基,以及
RM1、RM3、RM5和RM6相互独立地为氢或C1-C8烷基,
包括下列步骤:
-使式S-IN-P化合物:
与式PS-IN-P化合物在碱和任选非质子溶剂存在下反应:
其中Z1P-IN和Z2P-IN相互独立地为卤素,
得到式IN-P化合物:
-使式IN-P化合物与式S1-IN-P化合物在碱和任选非质子溶剂存在下反应:
HO-R1P(S1-IN-P)
得到式I-P化合物,
其中所有式中的R1P、R4、R5、R6、R7、RP2、RP3、RP5、RP6、RO1、RO2、RO5、RO6、RM1、RM3、RM5、RM6、Z1P-IN和Z2P-IN为式I-P和PS-IN-P中的那些。
在该另一种制备式I-P化合物的方法中,使式S-IN-P化合物与式PS-IN-P化合物反应的步骤和使式IN-P化合物与式S1-IN-P化合物反应的步骤一旦形成一定量的化合物IN-P就可以平行进行。
优选另一种制备式I-O化合物的方法:
其中
R1O表示子式II-O或II-M之一:
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基,以及
RM1、RM3、RM5和RM6相互独立地为氢或C1-C8烷基,
包括下列步骤:
-使式S-IN-O化合物:
与式PS-IN-O化合物在碱和任选非质子溶剂存在下反应:
其中Z1O-IN和Z2O-IN相互独立地为卤素,
得到式IN-O化合物:
-使式IN-O化合物与式S1-IN-O化合物在碱和任选非质子溶剂存在下反应:
HO-R10(S1-IN-O)
得到式I-O化合物,
其中所有式中的R1O、R4、R5、R6、R7、RO1、RO2、RO5、RO6、RM1、RM3、RM5、RM6、Z1O-IN和Z2O-IN为式I-O和PS-IN-O的那些。
在该另一种制备式I-O化合物的方法中,使式S-IN-O化合物与式PS-IN-O化合物反应的步骤和使式IN-O化合物与式S1-IN-O化合物反应的步骤一旦形成一定量的化合物IN-O就可以平行进行。
优选另一种制备式I-M化合物的方法:
其中
R1M表示子式II-M:
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RM1、RM3、RM5和RM6相互独立地为氢或C1-C,
包括下列步骤:
-使式S-IN-M化合物:
与式PS-IN-M化合物在碱和任选非质子溶剂存在下反应:
Z1M-IN和Z2M-IN相互独立地为卤素,
得到式IN-M化合物:
-使式IN-M化合物与式S1-IN-M化合物在碱和任选非质子溶剂存在下反应:
HO-R1M(S1-IN-M)
得到式I-M化合物,
其中所有式中的R1M、R4、R5、R6、R7、RM1、RM3、RM5、RM6、Z1M-IN和Z2M-IN为式I-M和PS-IN-M的那些。
在制备式I-M化合物的方法中,使式S-IN-M化合物与式PS-IN-M化合物反应的步骤和使式IN-M化合物与式S1-IN-M化合物反应的步骤一旦形成一定量的化合物IN-M就可以平行进行。
式PS-IN-P、PS-IN-O和PS-IN-M涵盖相同化合物,但为清楚起见因式I-P、I-O或I-M化合物的反应方案而异。此外,式S1-IN-P在子式II-P的情况下对于R1P类似于式S-IN-P。式S1-IN-P在子式II-O的情况下对于R1P类似于式S-IN-O。式S1-IN-P在子式II-M的情况下对于R1P类似于式S-IN-M。式S1-IN-O在子式II-O的情况下对于R1O类似于式S-IN-O。式S1-IN-O在子式II-M的情况下对于R1O类似于式S-IN-M。式S1-IN-M在子式II-M的情况下对于R1M类似于式S-IN-M。
本发明的另一实施方案涉及式IN-P、IN-O或IN-M的中间体化合物:
其中
Z1P-IN、Z1O-IN和Z1M-IN相互独立地为卤素,
R4、R5、R6和R7相互独立地为氢或C1-C8烷基,
RP2、RP3、RP5和RP6相互独立地为氢或C1-C8烷基,
RO1、RO2、RO5和RO6相互独立地为氢或C1-C8烷基,以及
RM1、RM3、RM5和RM6相互独立地为氢或C1-C8烷基。
下列实施例进一步说明而不限制本发明。若无不同说明,则百分数值是重量百分数。
合成实施例
合成程序在氮气气氛下进行。
若无其他说明,则原料例如由Aldrich Corp市购。
实施例S-1:合成化合物(102)
在65℃下将5.0g(15mmol)化合物(202)(可以根据EP 2500341 A第8页实施例1通过使用相应4-叔辛基苯酚得到)溶于40mL无水二氯乙烷中。首先向该溶液中加入1.41g(18mmol)无水吡啶,然后在25分钟内加入1.96g(7mmol)化合物(301)(3,9-二氯-2,4,8,10-四氧杂-3,9-二磷杂螺[5.5]十一烷,可以根据Lucas等,Tetrahedron Lett.2005,46,3347得到)。将反应物料在回流下搅拌3小时,冷却至室温并过滤。在除去溶剂之后得到玻璃状残余物,将其在70℃和真空下进一步干燥。以无定形固体得到5.3g(理论值的69%)化合物(102)。
31P-NMR(甲苯-d8):116ppm
1H-NMR(甲苯-d8):4.3ppm(s,2H,内酯环中的CH)
MS(LC/MS,ACPI正模式):[M+1]+=1094
实施例S-2:合成化合物(103)
化合物(103)类似于实施例S-1由化合物(203)(可以根据EP 0648765 A第30页化合物115得到)制备并且作为无定形固体以理论值的81%的产率得到。
31P-NMR(甲苯-d8):122ppm
1H-NMR(甲苯-d8):4.3ppm(s,2H,内酯环中的CH)
MS(LC/MS,ACPI正模式):[M+1]+=926
实施例S-3a:用间氯过苯甲酸合成化合物(402)
将3.0g(3.0mmol)化合物(102)溶于40mL无水二氯甲烷中并将该溶液冷却至5℃。分两次加入1.0g(6mmol)间氯过苯甲酸。形成淡黄色沉淀,其再次缓慢溶解。将该溶液在5℃下搅拌3小时。在除去溶剂之后,固体残余物通过快速层析(SiO2,庚烷/乙酸乙酯9:1)提纯。以无色无定形固体得到2.7g(理论值的89%)化合物(402)。
31P-NMR(DCM-d2):-15.1ppm
1H-NMR(DCM-d2):4.75ppm(s,2H,内酯-H)
MS(LC/MS,ACPI正模式):[M+H]+=1125
实施例S-3b:用过氧化氢合成化合物(402)
将2.7g(2.5mmol)化合物(102)溶于25mL乙腈中,将该溶液冷却至5℃并在该温度下加入5mL 10%过氧化氢水溶液(15mmol)。在出现乳液状反应物料之后蜡状产物沉淀,在搅拌6小时之后将其滤出并再溶于80mL乙酸乙酯中。在用50mL 20%NaHSO3水溶液处理该溶液两次之后,将有机相用50mL盐水洗涤并在Na2SO4上干燥。在除去溶剂之后,以无色无定形固体得到2.2g(理论值的91%)纯净形式的化合物(402)。
分析数据如实施例S-3a所述。
实施例S-3c:通过与化合物(501)缩合合成化合物(402)
在室温下将7.8g(26mmol)如Polymer Degradation and Stability,2015,113,第86-94页所述通过使季戊四醇与磷酰氯(=POCl3)反应而制备的化合物(501)溶于100mL无水乙腈中。分三次加入24.5g(53mmol)化合物(202)。形成悬浮液。滴加8.0mL(57mmol)三乙胺。在回流下加热16小时之后,将反应物料冷却至室温。将沉淀的固体滤出并用250mL水洗涤。在最后用在0℃下用150mL乙腈洗涤之后,产物在60℃和真空下干燥。以无色无定形固体得到17.3g(理论值的59%)化合物(402)。
分析数据如实施例S-3a所述。
实施例S-4a:用间氯过苯甲酸合成化合物(403)
将5.02g(5mmol)化合物(103)溶于30mL无水二氯甲烷中并将该溶液冷却至5℃。分两次加入2.62g 70%间氯过苯甲酸(10mmol)。形成无色沉淀。将该悬浮液在5℃下搅拌3小时。将沉淀滤出并用额外100mL二氯甲烷洗涤。将合并的滤液蒸发至干并将固体残余物通过快速层析(SiO2,庚烷/乙酸乙酯9:1)提纯。以无色无定形固体得到1.4g(理论值的27%)化合物(403)。
31P-NMR(DCM-d2):-12.9ppm
1H-NMR(DCM-d2):4.82ppm(s,2H,内酯-H)
MS(LC/MS,正模式):[M+H]+=958
实施例S-4b:用过氧化氢合成化合物(403)
将6.8g(6.7mmol)化合物(103)溶于60mL乙腈中并在室温下加入15mL10%过氧化氢(45mmol)。将该混合物加热至40℃并在该温度下搅拌150分钟。在冷却至20℃之后将反应物料加入100mL 0℃的水中,将沉淀的产物滤出并溶于100mL乙酸乙酯中。在将该溶液用50mL 20%NaHSO3水溶液处理两次之后,将有机相用100mL盐水洗涤并在Na2SO4上干燥。在除去溶剂之后,将产物通过快速层析(SiO2,庚烷/乙酸乙酯9:1)提纯。以无色无定形固体得到5.0g(理论值的72%)化合物(403)。
分析数据如实施例S-4a。
应用实施例
除了本发明化合物外,部分使用下列已知稳定剂:
AO-1是Irganox 1010(RTM BASF),其含有季戊四醇四(3-(3,5-二叔丁基-4-羟基苯基)丙酸酯)。
AO-2是Irganox 1076(RTM BASF),其含有β-(3,5-二叔丁基-4-羟基苯基)丙酸硬脂基酯。
Phos-1是Irgafos 168(RTM BASF),其含有亚磷酸三(2,4-二叔丁基苯基)酯。
CaSt是市售硬脂酸钙,用作酸清除剂。
对于实施例A-1中的聚合物加工,根据相应表中所述配制剂的配方将呈颗粒形式的感兴趣聚合物与各种添加剂共混。共混使用Henschel、Turbula或Kitchen-Aid混合机进行。然后将彻底共混的配制剂在双螺杆挤出机中在更低温度(210℃[410°F])和氮气下熔体配混。这确保良好的熔体混合,由于氧化降解对该聚合物具有最小损害。得到零道次挤出物,其在实施例中表示为零道次挤出。
然后将在实施例A-1中所得零道次挤出物在装有Maddock混合段的单螺杆挤出机中在更高温度(260℃[500°F])和露天下多次挤出。在更高温度下挤出与氧气(空气)的存在结合提高了聚合物降解速率。这些侵略性挤出条件对该稳定化体系施加应变,这允许各种测试的分化。该多道挤出显示加工稳定性。收集零、一、三和五道次挤出物的造粒样品并在室温下在处于黑暗中的储存箱中储存于密封塑料袋中。
测试实施例A-1中样品的熔体流动速率以确定分子量的保留。这通过熔体流动速率保留(根据ASTM-1238)在Tinius-Olsen挤压式塑性计上测量。对于聚丙烯,测试条件为230℃和2.16kg。熔体流动速率以在10分钟内流出限定孔板的聚合物克数或分克/分钟测量。
测试实施例A-1中样品的烘箱老化以确定在该聚合物的熔点以下的氧化稳定性,这显示挤出后的长期热稳定性。在该聚合物的熔点以下加温促进了聚合物降解。烘箱老化通过将压塑板(1mm[40密耳])放入装有旋转木马的Blue M强制通风烘箱中以使对升高温度(130℃,150℃)的暴露在烘箱内均匀而进行。通过每3-4天弯曲该板直到该板由于氧化降解折断而以天数测量脆裂失败。时间按天测量。
测试实施例A-1中的氧化诱导时间(OIT)以确定在该聚合物的熔点以上的氧化稳定性,这显示挤出后的热稳定性。氧化诱导时间(OIT)是在高温(190℃)和氧化性环境(氧气)下测量该稳定剂在该聚合物熔体中的活性的手段。该试验在差示扫描量热仪(DSC)上运行。使用10℃/min的加热速率在氮气下从50℃到190℃收集扫描结果,然后切换到氧气并保持在等温条件下直到高温剧烈氧化。高温剧烈氧化(作为强放热观察到)开始的时间以分钟测量。该样品以厚度为0.25mm(10密耳)的薄膜形式测试。
测试实施例A-2中的黄度指数(YI)以确定颜色变化并且根据DIN 6167测量。
实施例A-1:聚丙烯均聚物的稳定化
如表A-1所述加工和评价来自本体/淤浆相聚合方法的熔体流动速率为12dg/min的市售模塑级Ziegler-Natta聚丙烯(zn-PP均聚物)—基本不含任何稳定化添加剂。
表A-1
脚注:
a)参照
b)本发明
c)基于Phos-1(4.8重量份P(III),基于100份亚磷酸三(2,4-二叔丁基苯基)酯;假定100%含量)提供的磷(III)[=P(III)]并且基于化合物(402)(5.5重量份P(V),基于100份化合物(402);假定100%含量)或化合物(403)(6.5重量份P(V),基于100份化合物(403);假定100%含量)无贡献计算表A-1的数据表明:
(i)在类似的总添加剂含量下以及甚至在明显降低的总添加剂含量下包含化合物(403)或化合物(402)的三组分混合物在加工过程中比没有化合物(403)或化合物(402)的双组分混合物保持熔体流动速率更稳定;
(ii)在类似的总添加剂含量下包括化合物(403)或化合物(402)的三组分混合物显示出与没有化合物(403)或化合物(402)的双组分混合物类似的烘箱老化值和氧化诱导时间值;
(iii)尽管据说因其与氧气反应成磷(V)而用作稳定化基团的磷(III)—例如来自亚磷酸酯或磷酸酯—含量降低,但得到(i)和(ii)的发现;特别是在烘箱老化中长期暴露于含氧空气中或者在氧化诱导时间中长期暴露于纯氧中得到(ii)的发现。
实施例A-2:线性低密度聚乙烯的稳定化
在高速混合机(Mixaco Lab CM2)中将呈聚合物粉末形式的市售线性低密度聚乙烯(来自BP Chemicals的LL 6130AP,线性LDPE)与表A-2中提供的稳定剂混合。将粉末形式的所得混合物在双螺杆挤出机(Collin25/42D)中在210℃和氮气保护下配混并造粒。这些粒料的加工稳定性用单螺杆挤出机在240℃下经由在空气下的多道挤出研究。将第一道次挤出、第三道次挤出和第五道次挤出之后的粒料压塑成2mm板并测量黄度指数。
结果示于表A-2中。
脚注:
a)参照
b)本发明
c)基于化合物(103)(6.7重量份P(III),基于100份化合物(103);假定100%含量)所提供的磷(III)[=P(III)]并且基于化合物(403)(6.5重量份P(V),基于100份化合物(403);假定100%含量)无贡献计算
表A-2的数据表明:
(i)化合物(403)提供了比化合物(103)更慢增加的黄度指数,即在配混之后更少的黄度指数变化或更少的初始色度变化;
(ii)化合物(403)与AO-2组合提供了比化合物(103)与AO-2组合更稳定的黄度指数,即在配混之后更少的黄度指数变化或更少的初始色度变化。
实施例H-1:化合物(402)和化合物(403)的水解稳定性
水解测试:使用具有适当调节以维持50℃(122°F)和80%相对湿度的强制通风湿度箱测试样品的水解稳定性。该测试方法包括将0.5克待测试材料放入适当标记的未加盖玻璃小瓶中。对于该测试,提供几组小瓶并将样品每过几天从该湿度箱中取出。然后通过高压液相色谱法(HPLC)测试暴露样品的水解程度,该色谱法测量完整原料的保留和转化化学。将水解产物存在的增加用作完整原料损失的标志。
通过观察化合物(202)的含量经由水解反应产生而测试化合物(402)和化合物(102)的水解。
通过观察化合物(203)的含量经由水解反应产生而测试化合物(403)和化合物(103)的水解。
样品H-1-I:
-呈白色粉末形式的化合物(402)
-61天后样品H-1-I仍为自由流动的白色材料
样品H-1-II:
-呈白色粉末形式的化合物(102)
-10天后样品H-1-II触碰起来呈蜡状并且自由流动性差
样品H-1-III:
-呈白色粉末形式的化合物(403)
-61天后样品H-1-III样品仍为自由流动的白色材料
样品H-1-IV:
-呈白色粉末形式的化合物(103)(由于水解具有5%已经释放的内酯结构部分,尽管之前在20℃下储存在干燥器中;该水解不稳定性要求某些类型的水解抑制剂如众所周知的三异丙醇胺)
-7天后样品H-1-IV触碰起来呈蜡状并且自由流动性差
表H-1-1
脚注:
a)参照
b)本发明
c)化合物(202)或化合物(203)的含量涉及由于水解反应而释放的内酯结构部分的百分数。评价该分析方法(HPLC),从而校正起始产物以及通过水解反应产生的产物各自的吸收系数。因此,100%水解涉及实际释放100%的可能释放的潜在内酯结构部分。
除化合物(103)外,所有测试样品起初是完整的,具有小于或约1%的化合物(202)或化合物(203)。在14天后化合物(102)失败并且在15天后化合物(103)基本失败。相比之下,化合物(402)或化合物(403)基本没有水解。优选的是水解降低并且测试样品保持为自由流动的白色材料。这表明式I-P、I-O或I-M化合物作为一类具有显著水解稳定性的强有力熔体加工稳定剂的优点。
Claims (20)
2.根据权利要求1的组合物,其中所述有机材料为一种聚合物、低聚羟基化合物、蜡、脂肪或矿物油。
3.根据权利要求2的组合物,其中所述有机材料是一种聚合物,其为聚烯烃或其共聚物,聚苯乙烯或其共聚物,聚氨酯或其共聚物,可以通过环氧化物、氧杂环丁烷或四氢呋喃聚合而得到的聚醚或其共聚物,聚酯或其共聚物,聚碳酸酯或其共聚物,聚氯乙烯或其共聚物,聚偏二氯乙烯或其共聚物,聚砜或其共聚物,聚乙酸乙烯酯或其共聚物,聚乙烯醇或其共聚物,聚乙烯醇缩醛或其共聚物或者聚酰胺或其共聚物。
4.根据权利要求1-3中任一项的组合物,其中
R4和R6为氢,
R5和R7相互独立地为氢或C1-C8烷基,
RP2和RP6相互独立地为氢或C1烷基,
RP3和RP5相互独立地为氢或C1-C4烷基,
RO1和RO6相互独立地为氢或C1-C8烷基,
RO2为氢或C1烷基,
RO5为氢或C1-C4烷基,
RM1为氢或C1烷基,
RM3和RM5相互独立地为氢或C1-C4烷基,和
RM6为氢或C1-C8烷基。
5.根据权利要求1-4中任一项的组合物,其中
所述化合物具有式I-P或I-O,
R1P表示子式II-P或II-O之一,和
R1O表示子式II-O。
6.根据权利要求1-5中任一项的组合物,包含:
a)一种聚合物,其为聚烯烃或其共聚物或者聚苯乙烯或其共聚物,和
b)具有式I-P或I-O的化合物,其中
R1P表示子式II-P,
R1O表示子式II-O,
R4和R6为氢,
R5和R7相互独立地为氢或C1-C8烷基,
RO1为氢或C1-C8烷基,
RO2、RO5和RO6为氢,
RP2和RP6为氢,和
RP3和RP5相互独立地为氢或C1-C4烷基。
7.根据权利要求1-6中任一项的组合物,其中基于组分a)的重量以0.0005-10%的量含有组分b)。
8.根据权利要求1-7中任一项的组合物,包含作为组分c)的其他添加剂。
9.根据权利要求8的组合物,包含作为组分c)的其他添加剂,其为不同于组分b)的亚磷酸酯或亚膦酸酯、酸清除剂、酚类抗氧化剂或胺类抗氧化剂。
10.根据权利要求9的组合物,包含作为组分c)的酚类抗氧化剂,其为β-(3,5-二叔丁基-4-羟基苯基)丙酸的酯。
11.根据权利要求8-10中任一项的组合物,包含作为组分d)的第二种其他添加剂,其为不同于组分b)的亚磷酸酯或亚膦酸酯、酸清除剂、酚类抗氧化剂或胺类抗氧化剂;条件是组分d)为不同于组分c)的化合物。
12.一种保护易于氧化、热或光诱发降解的有机材料的方法,包括下列步骤:
-提供所述有机材料,以及
-将如权利要求1所定义的式I-P、I-O或I-M化合物掺入所提供的有机材料中或施用于其上。
13.根据权利要求12的方法,其中所述有机材料为聚合物,其中进行的是掺入所述聚合物中并且部分或完全掺入在135-350℃的温度下进行。
14.如权利要求1所定义的式I-P、I-O或I-M化合物在稳定易于氧化、热或光诱发降解的有机材料以防氧化、热或光降解中的用途。
16.一种添加剂组合物,包含:
b)如权利要求1所定义的式I-P、I-O或I-M化合物,和
c)其他添加剂,其为不同于组分b)的亚磷酸酯或亚膦酸酯、酸清除剂、酚类抗氧化剂或胺类抗氧化剂。
17.根据权利要求16的添加剂组合物,包含作为组分c)的酚类抗氧化剂,其为β-(3,5-二叔丁基-4-羟基苯基)丙酸的酯。
18.根据权利要求16或17的添加剂组合物,包含作为组分d)的第二种其他添加剂,其为不同于组分b)的亚磷酸酯或亚膦酸酯、酸清除剂、酚类抗氧化剂或胺类抗氧化剂;条件是组分d)为不同于组分c)的化合物。
19.根据权利要求18的添加剂组合物,包含作为组分d)的第二其他添加剂,其为亚磷酸三(2,4-二叔丁基苯基)酯。
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