CN104704038B - 脂环族多亚磷酸酯聚合物稳定剂 - Google Patents
脂环族多亚磷酸酯聚合物稳定剂 Download PDFInfo
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- CN104704038B CN104704038B CN201380044359.2A CN201380044359A CN104704038B CN 104704038 B CN104704038 B CN 104704038B CN 201380044359 A CN201380044359 A CN 201380044359A CN 104704038 B CN104704038 B CN 104704038B
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- Prior art keywords
- butyl
- polyphosphite
- alkyl
- phenyl
- double
- Prior art date
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- 229920000642 polymer Polymers 0.000 title claims description 42
- 239000003381 stabilizer Substances 0.000 title description 12
- 239000000203 mixture Substances 0.000 claims description 71
- 238000006116 polymerization reaction Methods 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 13
- 229920000098 polyolefin Polymers 0.000 claims description 6
- 230000003252 repetitive effect Effects 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 5
- 229920001059 synthetic polymer Polymers 0.000 claims description 4
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000006713 (C5-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- -1 CHDM Chemical class 0.000 abstract description 199
- 229920001577 copolymer Polymers 0.000 abstract description 44
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 abstract description 24
- 229910052698 phosphorus Inorganic materials 0.000 abstract description 15
- 239000011574 phosphorus Substances 0.000 abstract description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract description 12
- 239000011368 organic material Substances 0.000 abstract description 10
- 239000003963 antioxidant agent Substances 0.000 abstract description 7
- 230000008901 benefit Effects 0.000 abstract description 4
- 238000005516 engineering process Methods 0.000 abstract description 4
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 abstract description 3
- 230000015556 catabolic process Effects 0.000 abstract description 2
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 abstract 1
- 230000006641 stabilisation Effects 0.000 abstract 1
- 238000011105 stabilization Methods 0.000 abstract 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 69
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 67
- 229910052757 nitrogen Inorganic materials 0.000 description 66
- 239000002585 base Substances 0.000 description 64
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 52
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 49
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 40
- 150000008301 phosphite esters Chemical class 0.000 description 39
- 239000000376 reactant Substances 0.000 description 39
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 30
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 26
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 22
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- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 230000007423 decrease Effects 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000004821 distillation Methods 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- 239000000654 additive Substances 0.000 description 13
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 10
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
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- 150000001875 compounds Chemical class 0.000 description 9
- 229920000092 linear low density polyethylene Polymers 0.000 description 9
- 239000004707 linear low-density polyethylene Substances 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 238000004806 packaging method and process Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
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- 125000001931 aliphatic group Chemical group 0.000 description 8
- 150000001336 alkenes Chemical class 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 8
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 8
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 8
- 239000004700 high-density polyethylene Substances 0.000 description 8
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- 230000015572 biosynthetic process Effects 0.000 description 7
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- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 description 6
- 235000006708 antioxidants Nutrition 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
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- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 6
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
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Abstract
本文描述了聚合和共聚多亚磷酸酯,所述多亚磷酸酯在多亚磷酸酯主链中含有脂环族部分,优选环己烷二甲醇。本文描述的新型亚磷酸酯适用于使有机材料对氧化、热或光化降解稳定。该技术的至少一个优点在于认识到,基于脂环族二醇例如CHDM的亚磷酸酯具有高百分比的磷,因此为非常有效的抗氧化剂。
Description
技术领域
本文描述的发明一般属于改善的聚合物组合物,所述组合物含有至少一种在多亚磷酸酯中具有脂环族部分的多亚磷酸酯添加剂。
发明背景
有机亚磷酸酯因为其加入到聚合物或其它有机材料时的抗氧化剂特性而已知。与向聚合物树脂加入稳定剂有关的至少一个目的,是防止衍生于树脂的聚合物在高温加工期间变质,而且还允许制备内在质量提高的产品,该内在质量的提高至少部分归因于在其预定的应用期间对热和光降解的抗性增大。
有机亚磷酸酯可自各种醇、二醇、三醇和烷基酚合成。它们当中有商业上重要的亚磷酸酯、三(壬基苯基)亚磷酸酯(TNPP)和三(2,4-二叔丁基苯基)亚磷酸酯。在历史上,这两种亚磷酸酯一直为橡胶和塑料工业的低成本稳定剂。然而,近来,由于担忧它们是外源性雌激素和生物累积性的,自它们制备的烷基酚和亚磷酸酯已经受到密切注意。因此,期望这些物质的合适替代物。
已经确定许多有用的多亚磷酸酯可基于脂环族二醇例如环己烷二甲醇(“CHDM”)来合成,并且其为含有烷基酚的亚磷酸酯的合适替代。在性能、热稳定性和水解稳定性方面,至少部分自CHDM制备的亚磷酸酯优于许多市售亚磷酸酯。而且,可自具有多种特性的脂环族二醇(例如CHDM)产生各种各样的亚磷酸酯。
因此,公开的是至少部分自饱和脂环族反应物(例如脂环族二醇)、起链终止剂作用的单羟基封端的醇和三官能的含磷部分(例如三芳基亚磷酸酯)合成的固体和液体多亚磷酸酯,及其作为稳定剂的性能。
发明概述
本文描述的新型亚磷酸酯适用于使有机材料对氧化、热或光化降解稳定。该技术的至少一个优点在于认识到,基于脂环族二醇例如CHDM的亚磷酸酯具有高百分比的磷,因此为非常有效的抗氧化剂。特别是,CHDM也为多用途原料,其允许适用于许多应用的宽范围的产品合成。
例如,在某些聚烯烃,期望具有高分子量的固体或液体聚合或寡聚亚磷酸酯,使得自聚合物的迁移和起霜减至最少。高的热稳定性和水解稳定性由于高的加工温度也是非常重要的。本文描述的通用结构的中到高分子量的亚磷酸酯满足聚烯烃的所有这些要求。而且通过加入与CHDM组合的合适的醇,可以合成固体和液体多亚磷酸酯两者。具有大于16的碳链长度的醇倾向于产生固体多亚磷酸酯,而具有少于16的碳链长度的醇倾向于产生液体多亚磷酸酯。
具有高羟基数的多亚磷酸酯可适用于用作抗焦剂以及火焰层合添加剂的聚氨酯。本文描述的通用结构的CHDM亚磷酸酯可被合成具有合适的羟基数,以便成为聚氨酯中的有用添加剂。
本文描述的通用结构的低和高分子量多亚磷酸酯在PVC中显示出色的相容性和稳定性。这些通用结构的亚磷酸酯在PVC中赋予出色的颜色稳定性和增加热稳定性。
当根据详细描述和所附权利要求考虑,本发明的这些和其它目的将是显而易见的。
发明详述
为了说明在递交本发明的时候,申请人已知的最佳方式的目的,现描述实施本发明的最佳方式。实施例和附图仅为举例说明性的,并不意味着限制本发明,本发明由权利要求的范围和精神衡量。
当本文使用,并且除非另外指明,术语“烷基”意指直链和支链的饱和无环烃一价基团,所述烷基可进一步任选包括一个或多个独立选自以下的合适取代基:氨基、卤素、羟基、巯基、卤代烷基、烷氧基等。直链或支链烷基的具体非限制性实例为C1-20烷基,例如甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基、十二烷基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基和硬脂基。应认识到烷基可用氧、硫或氮中断,散置基团的非限制性实例包括:CH3-O-CH2CH2-、CH3-S-CH2CH2-、CH3-N(CH3)-CH2CH2-、CH3-O-CH2CH2-O-CH2CH2-、CH3-(O-CH2CH2-)2O-CH2CH2-、CH3-(O-CH2CH2-)3O-CH2CH2-或CH3-(O-CH2CH2-)4O-CH2CH2-。
当本文使用,并且除非另外指明,术语“烯基”意指直链和支链的不饱和无环烃一价基团,所述烯基可进一步任选包括一个或多个独立选自以下的合适取代基:氨基、卤素、羟基、巯基、卤代烷基、烷氧基等。直链或支链烯基的具体非限制性实例为具有2-30个碳原子的那些,其中双键的位置可以变化,例如丁烯基、戊烯基、己烯基、庚烯基、辛烯基、壬烯基、癸烯基、十一碳烯基、十二碳烯基、十三碳烯基、十四碳烯基、十五碳烯基、十六碳烯基、十七碳烯基和十八碳烯基。应再次认识到,烯基可用氧、硫或氮中断,散置基团的非限制性实例包括:-CH2-O-CH2-、-CH2-S-CH2-、-CH2-N(CH3)-CH2-、-CH2-O-CH2CH2-、-CH2CH2-O-CH2CH2-、-CH2CH2-O-CH2CH2-O-CH2CH2-、-CH2CH2-(O-CH2CH2-)2O-CH2CH2-、-CH2CH2-(O-CH2CH2-)3O-CH2CH2-、-CH2CH2-(O-CH2CH2-)4O-CH2CH2-、-CH2CH2-S-CH2CH2-或-CH2CH2-N(CH3)-CH2CH2-。
当本文使用,并且除非另外指明,术语“脂环族”指具有3-10个碳原子的单-或多环饱和烃一价基团,或者具有7-10个碳原子的C7-10多环饱和烃一价基团。可具有取代基的脂环族的或环状烷基的具体非限制性实例为具有5-7个碳原子的环烷基,例如环戊基、环己基和环庚基,和具有6-11个碳原子的烷基环烷基,其中烷基的位置可以变化,例如甲基环戊基、二甲基环戊基、甲基乙基环戊基、二甲基环戊基、甲基环己基、二甲基环己基、甲基乙基环己基、二乙基环己基、甲基环庚基、二甲基环庚基、甲基环庚基和二乙基环庚基。应再次认识到,脂环族基团可用氧和/或羰基(例如内酯)或者其它不干扰的原子中断。
当本文使用,并且除非另外指明,术语“烷氧基”指其中烷基通过单键连接于氧原子的取代基。
当本文使用,并且除非另外指明,术语“卤代”或“卤素”意指选自氟、氯、溴和碘的任何原子。
本发明至少部分涉及固体和液体亚磷酸酯,其至少部分由饱和的脂环族反应物(例如脂环族二醇,更优选的为环己烷二甲醇(“CHDM”))构成。
环己烷二甲醇为具有两个键合于环上任何位置的甲醇基团的环己烷环,如由通用结构(I)阐明的那样。
应该认识到,顺式或反式异构体的CHDM或其组合可用作反应物。尽管CHDM为本发明许多描述的焦点,但是本发明并不限于此,并且事实上包括其它“基于脂环族二醇的”衍生物,例如环戊烷二甲醇、环戊烷二乙醇、环戊烷二丙醇、环戊烷二丁醇、环戊烷二戊醇、环己烷二乙醇、环己烷二丙醇、环己烷二丁醇、环己烷二戊醇、环庚烷二甲醇、环庚烷二乙醇、环庚烷二丙醇、环庚烷二丁醇、环庚烷二戊醇、环辛烷二甲醇、环辛烷二乙醇、环辛烷二丙醇、环辛烷二丁醇和环辛烷二戊醇。
在更一般的意义上,基于脂环族二醇的组分为HO-[R7]a-R8-[R9]b-OH (结构II),其中R7、R8、R9、a和 b如以下定义。在本发明的一个优选方面,R7和R9为CH2基团,并且a和b为1。
其中
(i) R7和R9独立选自直链和支链C1-6亚烷基;
(ii) R8选自C5-10饱和碳环;和
(iii) a和b为0和1。
在一个方面,本发明提供一种聚合多亚磷酸酯,含有1-1000个下式的重复单元:
其中R2选自
(i) C1-20烷基或C2-22烯基,所述C1-20烷基或C2-22烯基任选用C5-10环烷基或环烯基中断或封端,
(ii) 任选用C1-4烷基封端的C2-22聚烷二醇链,和
(iii) 含有-CO-O-基团并任选用C1-20烷基取代的3-7元环;
R7和R9中的每一个独立表示C1-6亚烷基;
R8选自C5-10饱和碳环;和
a和b独立选自0和1;
和0-1000个下式的重复单元:
其中Y表示C2-22亚烷基,m为1-20;
邻近上式的-P(OR2)-基团,所述多亚磷酸酯用基团R1O-封端,并且在链的另一个末端用基团-P(OR3)(OR4)封端,其中可相同或不同的R1、R3和R4中的每一个,具有为R2给出的含义之一;并且
条件是当所述多亚磷酸酯含有多于1个但是少于12个式B的单元时,其必须含有2个或更多个式A的单元;和
进一步的条件是当所述多亚磷酸酯不含式B的单元时,其必须含有8个或更多个式A的单元。
在一个实施方案中,本发明提供一种聚合多亚磷酸酯,含有8-1000个下式的重复单元:
其中:
R2选自
(i)C1-20烷基或C2-22烯基,所述C1-20烷基或C2-22烯基任选用C5-10环烷基或环烯基中断或封端,
(ii) 任选用C1-4烷基封端的C2-22聚烷二醇链,和
(iii) 含有-CO-O-基团并任选用C1-20烷基取代的3-7元环;
R7和R9中的每一个独立表示C1-6亚烷基;
R8选自C5-10饱和碳环;和
a和b独立选自0和1;
邻近上式的-P(OR2)-基团,所述多亚磷酸酯用基团R1O-封端,并且在链的另一个末端用基团-P(OR3)(OR4)封端,其中可相同或不同的R1、R3和R4中的每一个,具有为R2给出的含义之一;
并且不含式B的单元。
在一个备选的实施方案中,本发明提供一种聚合多亚磷酸酯,含有1-1000个下式的重复单元:
和8-1000个下式的重复单元:
其中:
每一个R2独立选自
(i) C1-20烷基或C2-22烯基,所述C1-20烷基或C2-22烯基任选用C5-10环烷基或环烯基中断或封端,
(ii) 任选用C1-4烷基封端的C2-22聚烷二醇链,和
(iii) 含有-CO-O-基团并任选用C1-20烷基取代的3-7元环;
R7和R9中的每一个独立表示C1-6亚烷基;
R8选自C5-10饱和碳环;
a和b独立选自0和1;
Y表示C2-22亚烷基;和
m为1-20;
所述多亚磷酸酯邻近上式的-P(OR2)-基用基团R1O-封端,并且在链的另一个末端用基团-P(OR3)(OR4)封端,其中可相同或不同的R1、R3和R4中的每一个,具有为R2给出的含义之一。
如果单元B存在,那么Y优选表示-CH2CH2-或-CH(CH3)CH2-基团,并且m优选为5-20。
优选R2表示C10-20尤其是C12-C18烷基、C16-C18烯基或者用C1-4烷基封端的C2-10聚烷二醇链,例如用甲基封端的分子量350的聚乙二醇链或用丁基封端的二缩三丙二醇链。最优选R2表示C12-C18烷基。
优选R7和R9各自为亚乙基,或者尤其是亚甲基。优选a和b两者表示1。优选R8为C5-7亚环烷基,最优选为亚环己基。优选本发明的多亚磷酸酯含有10-1000个式A的单元。
一个优选组的本发明化合物为聚合多亚磷酸酯,其中R2表示C10-20尤其是C12-C18烷基、C16-C18烯基或者用C1-4烷基封端的C2-10聚烷二醇链,例如用甲基封端的分子量350的聚乙二醇链或用丁基封端的二缩三丙二醇链;R1、R3和R4中的每一个也具有这些含义之一,尤其是C12-C18烷基;R7和R9中的每一个独立表示亚乙基,或者尤其是亚甲基,并且a和b表示1;R8表示亚环己基;并且如果单元B存在,那么Y表示-CH2CH2-或-CH(CH3)CH2-基团,并且m为5-20。
在本发明的一个方面,作为结构(III)显示的说明性实例,聚合多亚磷酸酯至少部分采用CHDM合成。
其中
各R1、R2、R3和R4可相同或不同,并且独立选自C1-20烷基、C2-22烯基、C6-40环烷基、C7-40亚环烷基,或者R1、R2、R3和R4的Y-OH (用作封端部分);
Y选自C2-40亚烷基(例如亚乙基、亚丙基)、C2-40脂环族羧酸酯(例如辛内酯(caprylactone))和C3-40环烷基;
x在8-1000的范围内;进一步其中
所述聚合多亚磷酸酯为以下反应物的反应产物:
至少一种选自R1-OH、R2-OH、R3-OH和R4-OH的单羟基封端的反应物;和
至少一种二羟基封端的反应物(例如
);和
包含至少一个含磷部分的三官能反应物。
更一般地,结构(III)的聚合多亚磷酸酯可用结构(IIIa)说明。
其中
R1、R2、R3和R4可相同或不同,并且独立选自C1-20烷基、C2-22烯基、C6-40环烷基、C7-40亚环烷基,或者Y-OH (用作封端部分);
Y选自C2-40亚烷基(例如亚乙基、亚丙基)、C2-40脂环族羧酸酯(例如辛内酯)和C3-40环烷基;
x在8-1000的范围内;进一步其中
R7和R9独立选自直链和支链的C1-6亚烷基;和
R8选自C5-10饱和碳环;
a和b为独立选自0和1的整数值;并且其中
所述聚合多亚磷酸酯为以下反应物的反应产物:
至少一种选自R1-OH、R2-OH、R3-OH和R4-OH的单羟基封端的反应物;和
至少一种选自HO-[R7]a-R8-[R9]b-OH的二羟基封端的反应物;和
包含至少一个含磷部分的三官能反应物。
聚合多亚磷酸酯的共聚物至少部分采用CHDM合成,作为说明性实例用结构(IV)显示。
其中
每一个R1、R2、R3、R4、R5和R6可相同或不同,并且独立选自C1-20烷基、C2-22烯基、C6-40环烷基、C7-40亚环烷基,或者R1、R2、R3、R4、R5和R6的Y-OH (用作封端部分);
Y选自C2-40亚烷基(例如亚乙基、亚丙基)、C2-40脂环族羧酸酯(例如辛内酯)和C3-40环烷基;
x在1-1000的范围内;
z在0-1000的范围内,条件是当z大于1但是小于12,那么x在1-1000的范围内,并且进一步的条件是当z为0,那么x为8或者更大;
m在1-20的范围内;
w在1-1000的范围内;并且进一步其中
所述聚合多亚磷酸酯为以下反应物的反应产物:
至少一种选自R1-OH、R2-OH、R3-OH和R4-OH的单羟基封端的反应物;和
至少一种二羟基封端的反应物(例如
);和
包含至少一个含磷部分的三官能反应物。
更一般地,结构(IV)的二亚磷酸酯可用结构(IVa)说明。
其中
R1、R2、R3、R4、R5和R6可相同或不同,并且独立选自C1-20烷基、C2-22烯基、C6-40环烷基、C7-40亚环烷基,或者R1、R2、R3、R4、R5和R6的Y-OH (用作封端部分);
Y选自C2-40亚烷基(例如亚乙基、亚丙基)、C2-40脂环族羧酸酯(例如辛内酯)和C3-40环烷基;
x在1-1000的范围内;
z在0-1000的范围内,条件是当z大于1但是小于12,那么x在1-1000的范围内,并且进一步的条件是当z为0,那么x为8或者更大;
m在1-20的范围内;
w在1-1000的范围内;并且进一步其中
R7和R9独立选自直链和支链的C1-6亚烷基;和
R8选自C5-10饱和碳环;
a和b为独立选自0和1的整数值;并且其中
所述聚合多亚磷酸酯为以下反应物的反应产物:
至少一种选自R1-OH、R2-OH、R3-OH、R4-OH、R5-OH和R6-OH的单羟基封端的反应物;和
至少一种选自HO-[R7]a-R8-[R9]b-OH的二羟基封端的反应物;和
包含至少一个含磷部分的三官能反应物。
共聚多亚磷酸酯的聚烷二醇单元通常选自聚乙二醇和聚丙二醇。
优选,本发明的共聚亚磷酸酯的重均分子量为至少1200-100000,并且对于聚合亚磷酸酯,优选在6000-100000的范围内。
本发明的聚合多亚磷酸酯可表征为以下反应物的反应产物:(i) 至少一种醇R2OH;(ii) 至少一种二醇HO-[R7]a-R8-[R9]bOH;(iii) 包含至少一个含磷部分的三官能反应物;和(iv)如果单元B存在,则至少一种二醇H-[O-Y]mOH。适当地,所述三官能反应物为三芳基膦,尤其是三苯基膦。各种取代基的优选含义如以上给出。
本发明也提供用于制备本发明的聚合多亚磷酸酯的方法,所述方法包括以下反应物在碱的存在下一起反应:(i) 至少一种醇R2OH;(ii) 至少一种二醇HO-[R7]a-R8-[R9]bOH;(iii) 包含至少一个含磷部分的三官能反应物,尤其是三芳基膦,优选三苯基膦;并且如果单元B存在,那么(iv) 至少一种聚烷二醇H-[O-Y]mOH;其中R2选自:(i)C1-20烷基或C2-22烯基,所述C1-20烷基或C2-22烯基任选用C5-10环烷基或环烯基中断或封端,(ii) 任选用C1-4烷基封端的C2-22聚烷二醇链,和(iii) 含有-CO-O-基团并任选用C1-20烷基取代的3-7元环;R7和R9中的每一个独立表示C1-6亚烷基;R8选自C5-10饱和碳环;a和b独立选自0和1;Y表示C2-22亚烷基;和m为1-20。
成分的合成一般涉及酯交换,其中在20℃-250℃之间的温度下,并且更优选在50℃-185℃之间的温度下,用合适的碱催化剂,使三苯基亚磷酸酯(或者任何其它合适的烷基或芳基亚磷酸酯)与单烷基醇或单烯基醇或烷二醇醚(例如聚乙二醇醚或聚丙二醇醚)与至少一种二醇或聚合二醇H(OY)mOH反应,其中Y和m如下文定义。至少一种二羟基封端的反应物包含至少一个饱和碳环,例如环己烷二甲醇。单烷基醇或单烯基醇的非限制性实例包括癸醇、异癸醇、月桂醇、十三烷醇、异十三烷醇、肉豆蔻醇、十五烷醇、棕榈醇、硬脂醇、异硬脂醇、油醇、单羟基二醇醚等。
合适的碱催化剂包括氢氧化钠、甲醇钠、苯酚钠、氢氧化钾和碳酸钾。所使用的碱催化剂的量基于所加反应物的总量在0.01-10%重量的范围内。在一个优选的实施方案中,所述量在反应物的0.1-1.0%重量的范围内。
用于形成亚磷酸酯的烷基醇或二醇醚与二醇的摩尔比,对于亚磷酸三苯酯来说,为每摩尔亚磷酸三苯酯约0.9-2.2摩尔的醇或二醇醚和每摩尔亚磷酸三苯酯0.3-3.0摩尔的二醇。在一个优选的实施方案中,所述摩尔比为每摩尔亚磷酸三苯酯2.0-1.0的烷基或烯基醇或二醇醚,二醇与亚磷酸三苯酯的摩尔比为0.5-1.0。
亚磷酸酯的结构组成取决于反应条件例如温度、如何加入反应物的顺序、采用的烷基或烯基醇或二醇醚或者烷基或烯基醇或二醇醚的混合物或者一些或全部的组合、烷基或烯基醇或二醇醚与二醇的摩尔比和浓度以及选择的二醇的分子量。例如,亚磷酸酯的磷含量可通过所选择的二醇和烷基或烯基醇或二醇醚的分子量进行调整。
所采用的优选烷基醇为C12-C18。所采用的优选烯基醇为C16和C18。所采用的优选二醇醚为Carbowax 350 (聚乙二醇的单甲醚MW 350)和二缩三丙二醇单丁醚。
在用于共聚物的方法中采用的聚合物二醇为市售可得到的称为聚二醇的那些。优选的聚二醇为具有在200-3000范围内的分子量,并且在室温下作为液体存在的聚乙二醇或聚丙二醇。最优选的是具有300-400的分子量的聚乙二醇和具有300-1000的分子量的聚丙二醇。
向其中加入多亚磷酸酯和共聚多亚磷酸酯的有机材料,优选为合成聚合物。此类聚合物的非限制性的说明性实例包括以下聚合物:
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,以及环烯烃例如环戊烯或降冰片烯的聚合物;聚乙烯(其任选可为交联的),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)、以及以上描述的聚合物的掺混物,而不管制备方法。
以上聚合物的混合物,例如聚丙烯与聚异丁烯、聚丙烯与聚乙烯的混合物(例如PP/HDPE、PP/LDPE)和不同类型聚乙烯的混合物(例如LDPE/HDPE)。
单烯烃和二烯烃相互或与其它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/降冰片烯象COC)、乙烯/1-烯烃共聚物(其中1-烯烃原位产生)、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/醋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例如己二烯、二环戊二烯或乙叉-降冰片烯的三元共聚物,和此类共聚物相互和与先前提及的聚合物例如聚丙烯/乙烯-丙烯共聚物、LDPE/乙烯-醋酸乙烯酯共聚物(EVA)、LDPE/乙烯-丙烯酸共聚物(EAA)、LLDPE/EVA、LLDPE/EAA的混合物以及交替或无规的聚亚烷基/一氧化碳共聚物及其与其它聚合物例如聚酰胺的混合物。
烃树脂(例如C5-C9),包括其氢化修饰物(例如增粘剂)及聚亚烷基和淀粉的混合物。
来自以上并可具有任何立体结构的均聚物和共聚物,包括间同立构、全同立构、半全同立构或无规立构。立构规正嵌段聚合物也包括在内。
聚苯乙烯和聚(对-甲基苯乙烯)和聚(α-甲基苯乙烯)。
衍生于乙烯基芳族单体的芳族均聚物和共聚物,所述乙烯基芳族单体包括苯乙烯、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、丙基苯乙烯、乙烯基联苯、乙烯基萘和乙烯基蒽的所有异构体及其混合物。均聚物和共聚物可具有任何立体结构,包括间同立构、全同立构、半全同立构或无规立构。立构规正嵌段聚合物也包括在内。共聚物包括在内,例如选自以下的乙烯基芳族单体和共聚单体:乙烯、丙烯、二烯、腈、酸、马来酸酐、马来酰亚胺、醋酸乙烯酯和氯乙烯或者丙烯酸衍生物及其混合物,例如苯乙烯/丁二烯、苯乙烯/丙烯腈、苯乙烯/乙烯(互聚物)、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/丙烯酸甲酯;高冲击强度的苯乙烯共聚物和另一种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;和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/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。衍生于以上提及的聚合物的氢化作用的氢化芳族聚合物包括在内,尤其是包括通过氢化无规聚苯乙烯制备的、通常称为聚乙烯基环己烷(PVCH)的多环六方乙烯(polycyclohexylethylene)(PCHE)。还包括的是衍生于先前提及的聚合物的氢化作用的氢化芳族聚合物。均聚物和共聚物可具有任何立体结构,包括间同立构、全同立构、半全同立构或无规立构。立构规正嵌段聚合物也包括在内。
乙烯基芳族单体例如苯乙烯或α-甲基苯乙烯的接枝共聚物,例如聚丁二烯上的苯乙烯、聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物上的苯乙烯;聚丁二烯上的苯乙烯和丙烯腈(或甲基丙烯腈);聚丁二烯上的苯乙烯、丙烯腈和甲基丙烯酸甲酯;聚丁二烯上的苯乙烯和马来酸酐;聚丁二烯上的苯乙烯、丙烯腈和马来酸酐或马来酰亚胺;聚丁二烯上的苯乙烯和马来酰亚胺;聚丁二烯上的苯乙烯和丙烯酸或甲基丙烯酸烷基酯;乙烯/丙烯/二烯三元共聚物上的苯乙烯和丙烯腈;聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上的苯乙烯和丙烯腈、丙烯酸酯/丁二烯共聚物上的苯乙烯和丙烯腈、以及其与以上列出的共聚物的混合物,例如称为ABS、MBS、ASA或AES聚合物的共聚物混合物。
含有卤素的聚合物,例如聚氯丁二烯、氯化橡胶、异丁烯-异戊二烯的氯化和溴化共聚物(卤化丁基橡胶)、氯化或磺基-氯化聚乙烯、乙烯和氯化乙烯的共聚物;环氧氯丙烷均聚物和共聚物,尤其是含有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;及其共聚物例如氯乙烯/偏二氯乙烯、氯乙烯/醋酸乙烯酯或偏二氯乙烯/醋酸乙烯酯共聚物,例如聚丁二烯上的苯乙烯、丁二烯上的苯乙烯和丙烯酸或甲基丙烯酸烷基酯、乙烯/丙烯/二烯三元共聚物上的苯乙烯和丙烯腈、聚丙烯酸酯或聚甲基丙烯酸酯上的苯乙烯和丙烯腈、丙烯酸酯/丁二烯共聚物上的苯乙烯和丙烯腈,以及称为ABS、MBS和AES聚合物的共聚物掺混物。
衍生于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;用丙烯酸丁酯冲击改性的聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈。
在前述段落提及的单体相互或与其它不饱和单体的共聚物,例如丙烯腈/丁二烯共聚物、丙烯腈/丙烯酸烷基酯共聚物、丙烯腈/丙烯酸烷氧基烷基酯或丙烯腈/卤乙烯共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
衍生于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、聚醋酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚乙烯醇缩丁醛、聚邻苯二甲酸烯丙酯或聚烯丙基三聚氰胺,及其与以上提及的烯烃的共聚物。
环状醚的均聚物和共聚物,例如聚烷二醇、聚环氧乙烷、聚环氧丙烷或其与缩水甘油醚的共聚物。
聚缩醛,例如聚甲醛和含有环氧乙烷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。
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。
一方面衍生于羟基封端的聚醚、聚酯或聚丁二烯和另一方面衍生于脂族或芳族聚异氰酸酯及其前体的聚氨酯。
衍生于二胺和二羧酸和/或衍生于氨基羧酸或相应的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、自间二甲苯二胺和己二酸开始的芳族聚酰胺;自己二胺和间苯二甲酸或/和对苯二甲酸制备并且含有或不含弹性体作为改性剂的聚酰胺,例如聚对苯二甲酰2,4,4-三甲基己二胺或聚间苯二甲酰间苯二胺;以及以上提及的聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学键合的或接枝弹性体,或者与聚醚例如与聚乙二醇、聚丙二醇或聚丁二醇的嵌段共聚物;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 聚酰胺系统)。
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。
衍生于二羧酸和二醇和/或衍生于羟基羧酸或相应的内酯的聚酯,例如聚对苯二甲酸乙二醇酯、聚对苯二甲酸丁二醇酯、聚1,4-二甲醇环己烷对苯二甲酸酯、聚萘二甲酸亚烷基酯(PAN)和聚羟基苯甲酸酯,以及衍生于羟基封端的聚醚的嵌段共聚醚酯;还有用聚碳酸酯或MBS改性的聚酯。
聚碳酸酯和聚酯碳酸酯。
聚砜、聚醚砜和聚醚酮。
一方面衍生于醛的和另一方面衍生于苯酚、尿素和三聚氰胺的交联聚合物,例如苯酚/甲醛树脂、尿素/甲醛树脂和三聚氰胺/甲醛树脂。
干燥和非干燥的醇酸树脂。
不饱和聚酯树脂,其衍生于饱和和不饱和的二羧酸与多元醇和作为交联剂的乙烯基化合物的共聚酯,及其低可燃性的含有卤素的改性物。
衍生于取代的丙烯酸酯例如环氧丙烯酸酯、氨酯丙烯酸酯或聚酯丙烯酸酯的可交联丙烯酸树脂。
与三聚氰胺树脂、尿素树脂、异氰酸酯、异氰脲酸酯、聚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。
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,在含有或不含促进剂的情况下其与惯用的硬化剂例如酐或胺交联。
天然聚合物,例如纤维素、橡胶、明胶及其化学改性的同系衍生物,例如醋酸纤维素、丙酸纤维素和丁酸纤维素,或者纤维素醚例如甲基纤维素,以及松香及其衍生物。
以上提及的聚合物的掺混物和合金(聚合物共混物),例如PP/EPDM、聚酰胺/EPDM或ABS、PVC/EVA、PVC/ABS、PVC/MBS、PC/ABS、PC/聚酯、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。
其为纯的单体化合物或这种化合物的混合物的天然存在的和合成的有机材料,例如矿物油、动物和植物脂肪、油和蜡,或者基于合成酯(例如邻苯二甲酸酯、己二酸酯、磷酸酯或偏苯三酸酯)的油、脂肪和蜡,以及合成酯与矿物油以任何重量比率存在的混合物,一般地用作这种材料的纺纱组合物以及水性乳液的那些。
天然或合成橡胶的水性乳液,例如羧化苯乙烯/丁二烯共聚物的一种或多种天然胶乳。
通常以要稳定的有机材料的重量的约0.001 wt%-约5 wt%的量,把本发明的聚合二亚磷酸酯和聚合亚磷酸酯加入到要稳定的有机材料中。更优选的范围为约0.01%-2.0%。最优选的范围为0.025%-1%。
本发明的稳定剂可使用本领域已知的技术,在制备成型物品之前,于任何方便的阶段加入到有机材料中。
所稳定的本发明的聚合物组合物也可含有约0.001%-5%,优选0.01%-2%,和最优选0.025%-1%的其它常规稳定剂,以下提供非限制性的示例性列表。
受阻酚性抗氧化剂,例如2,6-二叔丁基-4-甲基苯酚、3,5-二叔丁基-4-羟基氢化肉桂酸十八烷基酯、四亚甲基(3,5-二叔丁基-4-羟基氢化肉桂酸酯)甲烷和三(3,5-二叔丁基-4-羟基苄基)异氰酸酯。
硫酯,非限制性的示例性列表包括硫代二丙酸二月桂醇酯和硫代二丙酸二硬脂醇酯。
芳族胺稳定剂,非限制性的示例性列表包括N,N’-二苯基-对-苯二胺。
受阻胺光稳定剂,称为HALS,非限制性的示例性列表包括双(2,2,6,6-四甲基哌啶基)癸二酸酯、N,N’-(2,2,6,6-四甲基哌啶基)-己二胺与4,4-辛基氨基-2,6-二氯-均三嗪的缩合产物及N,N’-(2,2,6,6-四甲基哌啶基)-己二胺与4-N-吗啉基-2,6-二氯-均三嗪的缩合产物。
紫外线吸收剂,非限制性的示例性列表包括2-羟基-4-正辛氧基二苯甲酮、2(2’-羟基-5’-甲基苯基)-苯并三唑和2(2’-羟基-5-叔辛基苯基)-苯并三唑。
亚磷酸酯,非限制性的示例性列表包括三(2,4-二叔丁基苯基)亚磷酸酯、二硬脂基季戊四醇二亚磷酸酯和2,4-二枯基苯基季戊四醇二亚磷酸酯。
酸中和剂,非限制性的示例性列表包括硬脂酸钙、硬脂酸锌、乳酸钙、硬脂酰乳酸钙、环氧化大豆油和水滑石(天然和合成的)。
其它添加剂,例如润滑剂、抗静电剂、抗粘连剂、滑爽剂、阻燃剂、成核剂、冲击改性剂、起泡剂、增塑剂、填充剂、染料和颜料可以合适的量和与所发明的聚合二亚磷酸酯组合使用,以改变聚合物例如链烷醇胺的所选择的性质,非限制性的示例性列表包括三乙醇胺和三异丙醇胺。
新型亚磷酸酯可特别地与酚类抗氧化剂、光稳定剂和/或加工稳定剂的组合一起使用。另外,亚磷酸酯组合物可进一步包含添加剂,例如以下的任何添加剂。
抗氧化剂:
烷基化一元酚类,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;其侧链为直链或支链的壬基苯酚, 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。
烷基硫甲基苯酚类,例如2,4-二辛基硫甲基-6-叔丁基苯酚、2,4-二辛基-硫甲基-6-甲基苯酚、2,4-二辛基硫甲基-6-乙基苯酚、2,6-双十二烷基硫甲基-4-壬基苯酚。
氢醌和烷基化氢醌类,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、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)。
羟基化二苯基硫醚类,例如2,2’-硫基双(6-叔丁基-4-甲基苯酚)、2,2’-硫基双(4-辛基苯酚)、4,4’-硫基双(6-叔丁基-3-甲基苯酚)、4,4’-硫基双(6-叔丁基-2-甲基苯酚)、4,4’-硫基双(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。
烷叉基双酚类,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’-乙叉双(4,6-二叔丁基苯酚)、2,2’-乙叉双(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、双[3,3-双(3’-叔丁基-4’-羟基苯基)丁酸]乙二醇酯、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-、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、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)硫化物、3,5-二叔丁基-4-羟基苄基巯基乙酸异辛基酯。
羟基苄基化丙二酸酯,例如2,2-双(3,5-二叔丁基-2-羟基苄基)丙二酸双十八烷基酯、2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸双十八烷基酯、2,2-双(3,5-二叔丁基-4-羟基苄基)丙二酸双十二烷基巯基乙基酯、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(辛巯基)-6-(3,5-二叔丁基-4-羟基-苯胺基)-1,3,5-三嗪、2-辛巯基-4,6-双(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛巯基-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。
苄基膦酸酯类,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烷基酯、5-叔丁基-4-羟基-3-甲基苄基膦酸双十八烷基酯、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。
β-(3,5-二叔丁基-4-羟基苯基)丙酸与单-或多元醇,例如与以下醇的酯: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、三乙二醇、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-羟基甲基-1-磷杂(phospha)-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)丙酸与单-或多元醇,例如与以下醇的酯: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、三乙二醇、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-羟基甲基-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)丙酸与单-或多元醇,例如与以下醇的酯: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、二乙二醇、三乙二醇、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-羟基甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
3,5-二叔丁基-4-羟基苯基乙酸与单-或多元醇,例如与以下醇的酯: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、二乙二醇、三乙二醇、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-羟基甲基-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)己二胺、N,N’-双(3,5-二叔丁基-4-羟基-苯基丙酰基)丙二胺、N,N’-双(3,5-二叔丁基-4-羟基苯基)丙酰肼、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)。
胺的抗氧化剂,例如N,N’-二异丙基-对-苯二胺、N,N’-二仲丁基-对-苯二胺、N,N’-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-甲苯氨磺酰基)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-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、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N-苯基-1-萘胺、单-和二烷基化叔丁基/叔辛基二苯胺的混合物、单-和二烷基化壬基二苯胺的混合物、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、N,N-双(2,2,6,6-四甲基哌啶-4-基-己二胺、双(2,2,6,6-四甲基哌啶-4-基)癸二酸酯、2,2,6,6-四甲基哌啶-4-酮、2,2,6,6-四甲基哌啶-4-醇。
紫外线吸收剂和光稳定剂。
2-(2’-羟基苯基)苯并三唑类,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’,5’-二-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。
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。
取代和未取代的苯甲酸的酯,例如4-叔丁基苯基水杨酸酯、水杨酸苯酯、辛基苯基水杨酸酯、二苯甲酰间苯二酚、双(4-叔丁基苯甲酰)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、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、2-甲基-4,6-二叔丁基苯基-3,5-二叔丁基-4-羟基苯甲酸酯。
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-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。
镍化合物,例如2,2’-硫基双[4-(1,1,3,3-四甲基-丁基)苯酚]的含有或不含另外的配体例如正丁胺、三乙醇胺或N-环己基二乙醇胺的镍络合物,例如1:1或1:2络合物;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酯或乙酯的镍盐;酮肟例如2-羟基-4-甲基苯基十一烷基酮肟的镍络合物;1-苯基-4-月桂酰-5-羟基吡唑的含有或不含另外配体的镍络合物。
空间位阻胺,例如双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、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-羟基苄基丙二酸酯;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’-双(2,2,6,6-四甲基-4-哌啶基)己二胺和以下物质的线性或环状缩合物:4-叔辛基氨基-2,6-二氯-1,3,5-三嗪、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-2,2,6,6-四甲基哌啶、4-硬脂酰氧基-2,2,6,6-四甲基-哌啶、双(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸酯、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、双(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、双(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯;N,N’-双(2,2,6,6-四甲基-4-哌啶基)己二胺和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-双(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-双(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)-1,3,5-三嗪和以下物质的缩合物:1,2-双(3-氨基丙基氨基)乙烷、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-硬脂酰氧基-2,2,6,6-四甲基哌啶的混合物;N,N’-双(2,2,6,6-四甲基-4-哌啶基)己二胺和4-环己基氨基-2,6-二氯-1,3,5-三嗪的缩合物;1,2-双(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;1,6-己二胺和2,4,6-三氯-1,3,5-三嗪以及N,N-二丁胺和4-丁基氨基-2,2,6,6-四甲基哌啶、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]癸烷的缩合物;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]癸烷和环氧氯丙烷、1,1-双(1,2,2,6,6-五甲基-4-哌啶基氧基羰基)-2-(4-甲氧基苯基)乙烯、N,N’-双-甲酰基-N,N’-双(2,2,6,6-四甲基-4-哌啶基)己二胺的反应产物;4-甲氧基亚甲基丙二酸与1,2,2,6,6-五甲基-4-羟基哌啶、聚[甲基丙基-3-氧基-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷的二酯;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。
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’-二叔丁氧基草酰苯胺、2,2’-双十二烷氧基-5,5’-二叔丁氧基草酰苯胺、2-乙氧基-2’-乙基草酰苯胺、N,N’-双(3-二甲基氨基丙基)草酰胺、2-乙氧基-5-叔丁基-2’-乙氧基草酰苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁氧基草酰苯胺的混合物、邻-和对-甲氧基-二取代的草酰苯胺的混合物以及邻-和对-乙氧基-二取代的草酰苯胺的混合物。
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-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-4-十三烷氧基苯基)-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、2-[2-羟基-4-(2-乙基乙氧基)苯基]-4,6-二苯基-1,3,5-三嗪。
金属减活剂,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-水杨酰氨基-1,2,4-三唑、双(苄叉)草酸二酰肼、草酰苯胺、间苯二甲酸二酰肼、癸二酸双苯基酰肼、N,N’-二乙酰基己二酸二酰肼、N,N’-双(水杨酰)草酸二酰肼、N,N’-双(水杨酰)硫代丙酸二酰肼。
亚磷酸酯和亚膦酸酯类,例如亚磷酸三苯酯、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、亚磷酸三月桂醇酯、亚磷酸三(十八烷基)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]-1,3,2-二氧杂磷杂八环(dioxaphosphocin)、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]-1,3,2-二氧杂磷杂八环、2,2’,2’’-次氮基-[三乙基三(3,3’,5,5’-四叔丁基-1,r-二[rho]henyl-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丙烷(dioxaphosphirane)。
膦类,例如1,3-双(二苯基膦基)-2,2-二甲基-丙烷。
羟胺类,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-双十四烷基羟胺、N,N-双十六烷基羟胺、N,N-双十八烷基羟胺、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。
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-二烷基羟胺的硝酮(这种羟胺衍生于氢化牛脂胺)。
硫代增效剂(Thiosynerqists),例如硫代二丙酸二月桂醇酯或硫代二丙酸二硬脂醇酯。
过氧化物清除剂,例如β-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、双(十八烷基)二硫化物、季戊四醇四(β-十二烷基巯基)丙酸酯。
聚酰胺稳定剂,例如与碘化物和/或磷化合物组合的铜盐和二价锰的盐。
碱性共稳定剂,例如三聚氰胺、聚乙烯吡咯烷酮、双氰胺、氰脲酸三烯丙酯、尿素衍生物、肼衍生物、胺、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、山嵛酸镁、硬脂酸镁、蓖麻油酸钠和棕榈酸钾、焦基茶酚锑或焦基茶酚锌。
成核剂,例如无机物质,例如滑石、金属氧化物例如二氧化钛或氧化镁,优选为碱土金属的磷酸盐、碳酸盐或硫酸盐;有机化合物,例如单-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;聚合化合物,例如离子共聚物(离聚物),例如1,3:2,4-双(3’,4’-二甲基苄叉)山梨醇、1,3:2,4-二(对甲基二苄叉)山梨醇和1,3:2,4-二(苄叉)山梨醇。
填充剂和增强剂,例如碳酸钙、硅酸盐、玻璃纤维、玻壳、石棉、滑石、高岭土、云母、硫酸钡、金属氧化物和氢氧化物、炭黑、石墨、木粉和其它天然产物的粉末或纤维、合成纤维。
其它添加剂,例如增塑剂、润滑剂、乳化剂、颜料、流变学添加剂、催化剂、流动控制剂、荧光增白剂、耐火剂、抗静电剂、起泡剂和红外(IR)吸收剂。优选的IR吸收剂为例如颜料、染料或有机金属化合物。
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-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-酮或3-(2-乙酰基-5-异辛基苯基)-5-异辛基苯并呋喃-2-酮。
以这种方式制备的合成聚合物可以广泛种类的形式使用,例如作为泡沫、薄膜、纤维、带、成型组件,作为型材或作为用于涂层材料尤其是粉末涂料的粘合剂、胶粘剂、腻子或者尤其是作为与萃取介质长期接触的厚层聚烯烃模制件,例如液体或气体的管道、薄膜、纤维、土工膜、带、型材或槽。
在一个非限制性的实施方案中,优选的厚层聚烯烃模制件具有1-50 mm,特别是1-30 mm,例如2-10 mm的层厚度。
本发明的组合物可有利地用于制备各种形状的制品。最终用途应用的示例性非限制性的列表包括但不限于:漂浮设备、海洋应用、浮舟、浮标、甲板塑性木材、码头、船、独木舟、桨和海滩加固;汽车应用,特别是保险杠、仪表板、电池、前后衬里、罩下成型部件、帽架、行李箱衬层、内部衬里、气囊盖、装配的电子模制件(光源)、仪表盘嵌板、头灯玻璃、仪表板、外部衬里、室内装饰品、汽车灯、车头灯、停车指示灯、尾灯、刹车灯、内部和外部装饰;门板、油箱、玻璃正面、后窗;座位支持、外板、绝缘导线、密封用型材挤出、覆层、支柱盖、底盘部件、排气系统、燃油滤器/填充剂、燃油泵、燃油箱、车身侧面模制件、摺合式敞蓬车顶、车外后视镜、外饰件、紧固件/附件、前端模块、玻璃、铰链、锁系统、行李/行李架、按压/冲压部件、密封、侧面碰撞保护、减声器/隔离物和天窗;道路交通设备,特别是标志帖、道路标记用帖、汽车配件、三角警示牌、医用箱、头盔、轮胎;飞机、铁路、汽车(小汽车、摩托车)的设备,包括陈设;空间应用,特别是火箭和卫星的设备,例如再入盾;建筑与设计用的设备、开采应用、声学隔音系统、街道安全带和避难所。
本发明还在以下方面具有适用性:一般的器具、容器和覆盖物及电气/电子设备(个人电脑、电话、便携式电话、打印机、电视机、音频和视频设备)、花盆、卫星电视碗和面板设备;用于其它材料例如钢铁或织物的护套;用于电子工业的设备,特别是绝缘插头,尤其是电脑插头、用于电气和电子部件的容器、印刷电路板、以及用于电子数据存储的材料,例如芯片、支票卡或信用卡;电器,特别是洗衣机、酒杯、烤箱(微波炉)、洗碗机、混合器和熨斗;灯罩(例如路灯、灯罩);在电线电缆方面的应用(半导体、绝缘和电缆护套)、以及用于电容器、冰箱、加热设备、空调设备、电子封装、半导体、咖啡机和真空吸尘器的箔。
本发明进一步在以下方面具有适用性:技术物品,例如齿轮(齿轮)、滑动装置、垫片、螺钉、螺栓、把手和旋钮;转子叶片、通风机和风车叶片、太阳能设备、游泳池、游泳池盖、池的衬垫、池塘衬垫、壁橱、衣柜、隔离墙、板条墙、折叠墙、屋顶、百叶窗(例如卷帘百页)、配件、在管道、套管和输送带之间的连接;清洁物品,特别是淋浴房、马桶座椅、盖和槽;卫生物品,特别是尿布(婴儿、成人失禁)、女性卫生用品、浴帘、刷、垫、浴缸、移动厕所、牙刷和便盆;用于水、废水和化学品的管道(交联的或不交联的)、用于电线电缆的保护管道、用于天然气、油和污水、排水系统、下水管和排水系统的管道;任何几何形状(窗玻璃)和旁轨的型材;玻璃替代品,特别是挤出或共挤出板、用于建筑(整体式、双壁或多个壁)、飞机、学校、挤出板的上釉、用于建筑玻璃、火车、运输、卫生用品和温室的窗膜;板(墙壁、砧板)、挤压涂层(相纸、利乐包和管道涂层)、筒仓、木材替代品、塑性木材、木复合材料、墙、表面、家具、装饰箔、地板蒙布(内部和外部的应用)、地板、沟槽板道和瓷砖;摄入和出口歧管;以及水泥-、混凝土-、复合材料-应用和覆盖物、旁轨和覆层、扶手、栏杆、厨房工作台面、屋顶、屋顶板材、瓷砖和防水帆布。
还进一步的应用包括:板(墙壁和砧板)、托盘、人造草、人工草皮、体育场环的人工覆盖物(体育运动)、体育场环人造地板(体育运动)和带子;连续和主要的织造织物、纤维(地毯/卫生用品/土工布/单纤丝、过滤器、湿巾/窗帘(罩)/医疗应用)、大体积纤维(应用例如罩袍/防护服)、网、绳、索、带、绳、线、座椅安全带、服装、内衣、手套;长靴;橡胶靴、贴身衣服、服装、泳装、运动服装、雨伞(太阳伞、遮阳伞)、降落伞、滑翔伞、帆、“气球绸”、露营用品、帐篷、充气床垫、阳床、散装袋和袋子;以及用于屋顶的膜、绝缘材料、覆盖物和密封、隧道、转储、池塘、转储、墙壁薄膜屋面、土工膜、游泳池、窗帘(罩)/遮阳板、遮篷、顶篷、墙纸、食品包装和包装(柔性和固态的)、医药包装(柔性和固态的)、安全气囊/安全带、扶手和头枕、地毯、中心控制台、仪表板、驾驶舱、门、头顶控制台模块、门饰板、顶篷、室内照明、室内镜、包裹架、后行李箱盖、座椅、转向柱、方向盘、织物和行李箱饰物。
另外的应用包括:薄膜(包装、转储、层压、农业和园艺、温室、覆盖物、隧道、青贮饲料)、捆包、游泳池、废物袋、壁纸、拉伸膜、酒椰纤维、海水淡化膜、电池和连接器;食品包装和包装(柔性和固态的)、瓶;存储系统例如盒(板条箱)、行李、箱子、家用盒、托盘、货架、轨道、螺丝盒、包和罐;以及弹药筒、注射器、医疗应用、任何运输容器、废纸篓和垃圾箱、废物袋、垃圾箱、尘埃箱、箱衬里、带轮箱、一般容器、用于水/使用水/化学/气/油/汽油/柴油的槽;槽衬、盒、板条箱、电池箱、槽、医疗器械,例如活塞、眼科应用、诊断设备和药品泡罩包装。
还另外的应用可包括:挤压涂层(相纸、利乐包、管道涂层)、任何种类的家居用品(例如器具、热水瓶/衣架)、紧固系统例如插头,电线和电缆夹、拉链、封闭,锁和按扣;支撑装置、休闲用品例如体育和健身设备、体操垫、滑雪靴、轮刀、滑雪板、大脚、运动表面(例如网球场地);螺旋盖、瓶顶和塞、以及罐;一般家具、泡沫物品(垫、减震器)、泡沫、海绵、洗碗布、垫、花园椅、体育场座椅、桌、沙发、玩具、建筑设备(板/图/球)、剧场、幻灯片和活动车辆;光学和磁性数据存储材料;厨房用具(吃、喝、烹饪、储存);CD盒、磁带和录像带;DVD电子物品、任何种类的办公用品(圆珠笔、印章和印台、鼠标、货架、轨道)、任何体积和容量的瓶子(饮料、洗涤剂、化妆品包括香料)以及胶带;鞋类(鞋/鞋底)、鞋垫、鞋罩、胶粘剂、结构胶粘剂、食品盒(水果、蔬菜、肉、鱼)、合成纸、瓶子标签、沙发、人工关节(人)、印刷板(柔性版)、印制电路板和显示技术;以及填充聚合物(滑石粉、粉笔、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)的设备。
还进一步的应用可包括:组合物,作为组分包含(a):用于非织造医用织物及相关衣服(手术袍、窗帘、绷带)的纤维和织物、结构织物(房子包装、屋顶、游泳池包装),和家具(地毯、桌布、浴帘)。
因此,本发明的再一个实施方案涉及成型物品,特别是膜、管、型材、瓶、罐或容器,如以上描述的含有纤维的组合物。
根据以上显而易见的是,要保护的有机材料优选为有机聚合物,特别是合成聚合物。热塑性材料,特别是聚烯烃,受到特别有利地保护。特别是,应该强调亚磷酸酯的聚合化合物作为加工稳定剂(热稳定剂)的优良有效性。为了这个目的,它们最好在其加工之前或期间加入到聚合物中。然而,其它聚合物(例如弹性体)或润滑剂或液压用液体也可对降解稳定,例如光诱导或热氧化降解。弹性体在以上可能的有机材料列表中给出。
本发明现在将通过一系列实施例进行描述。
实施例#1
向配备有磁力搅拌器、连接于接收器和真空系统的蒸馏柱的三颈5000 mL烧瓶中加入778克(5.4 mol)的环己烷二甲醇、亚磷酸三苯酯(1775 g, 5.7 mol)、硬脂醇(1806 g,6.67 mol)和0.3克氢氧化钾。把混合物很好混合,并在氮气下加热至约150℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为软的固体,熔点为约30℃。
实施例#2
采用实施例#1中的装置。加入100克(0.69 mol)的环己烷二甲醇、亚磷酸三苯酯(237 g, 0.76 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约280) (190 g, 0.95 mol)和0.4克氢氧化钾。把混合物很好混合,并在氮气下加热至约150℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为非粘性液体。
实施例#3
采用实施例#1中的装置。加入65克(0.45 mol)的环己烷二甲醇、亚磷酸三苯酯(189 g, 0.61 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约280) (166 g, 0.85 mol)、平均分子量为400的聚丙二醇(25 g, 0.063 mol)和0.4克氢氧化钾。把混合物很好混合,并在氮气下加热至约150℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为非粘性液体。
实施例#4
采用实施例#1中的装置。加入20克(0.14 mol)的环己烷二甲醇、7 g聚丙二醇400(0.02 m)、亚磷酸三苯酯(100 g, 0.32 mol)、硬脂醇(188 g, 0.70 mol)和0.4克氢氧化钾。把混合物很好混合,并在氮气下加热至约150℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为固体。
实施例#5
采用实施例#1中的装置。加入20克(0.14 mol)的环己烷二甲醇、7 g聚丙二醇400(0.02 m)、亚磷酸三苯酯(100 g, 0.32 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约280) (136 g, 0.69 mol)和0.4克氢氧化钾。把混合物很好混合,并在氮气下加热至约150℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为非粘性液体。
实施例#6
采用实施例#1中的装置。加入38克(0.26 mol)的环己烷二甲醇、亚磷酸三苯酯(200 g, 0.65 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约196) (183 g, 0.93 mol)、平均分子量为300的聚乙二醇(84 g, 0.28 mol)和0.4克氢氧化钾。把混合物很好混合,并加热至约160℃。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为粘性液体。
实施例#7
采用实施例#1中的装置。加入38克(0.29 mol)的环己烷二甲醇、亚磷酸三苯酯(200 g, 0.64 mol)、月桂醇和肉豆蔻醇的混合物(183 g, 0.93 mol)、聚丙二醇400 (110,0.28)和0.4克氢氧化钾。把混合物很好混合,并在氮气下加热至约150℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为非粘性液体。
比较实施例#8 (非CHDM多亚磷酸酯)
采用实施例#1中的装置。加入PPG 400 (95 g, 0.237 mol)、亚磷酸三苯酯(73 g,0.235 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约280) (47 g, 0.235 mol)和0.8克氢氧化钾。把混合物很好混合,并在氮气下加热至160-162℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至170-172℃。把反应内容物在真空下,于170-172℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至50℃。产物为澄明的、无色液体。
比较实施例#9 (非CHDM多亚磷酸酯)
采用实施例#1中的装置。加入PPG 400 (100 g, 0.25 mol)、亚磷酸三苯酯(155g, 0.5 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约280) (200 g, 1.0 mol)和0.8克氢氧化钾。把混合物很好混合,并在氮气下加热至160-162℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至170-172℃。把反应内容物在真空下,于170-172℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至50℃。产物为澄明的、无色液体。
各种所合成添加剂的性质至少部分特征可在于下表。
表1
本发明的固体亚磷酸酯可与较高熔点的材料掺混在一起,以增大亚磷酸酯的熔点。来自实施例#1的亚磷酸酯用于所有以下实施例。
表2
A | B | C | D | |
实施例#1亚磷酸酯 | 40% | 50% | 50% | 50% |
硬脂酸Ca | 30% | 25% | 20% | |
硬脂酸Zn | 30% | 25% | 20% | |
季戊四醇四硬脂酸酯 | 50% | |||
硬脂酸Mg | 10% | |||
MP(℃) | 98 | 62 | 88 | 81 |
实施例#10
在PVC中进行比较研究,测量CHDM亚磷酸酯相对于标准亚磷酸酯DOVERPHOS® 6(亚磷酸三异癸基酯)的性能。把所有制剂在双辊磨上,于180℃下混合3分钟。然后把得到的片材切成条,并置于180℃下的Mathis烘箱中。测量各条中PVC炭化所用的时间。与DOVERPHOS® 6相比,CHDM亚磷酸酯均赋予PVC更大的热稳定性。
表3
实施例#11
在含有脂环族二醇的亚磷酸酯与不含脂环族二醇的那些之间进行比较。测试以下制剂。
表4
OxyVinyls®240 | 100 | 100 | 100 |
DINP (邻苯二甲酸二异壬酯) | 55 | 55 | 55 |
ESO (环氧油) | 3 | 3 | 3 |
ZnSt (硬脂酸锌) | 0.25 | 0.25 | 0.25 |
BBP (邻苯二甲酸苄酯丁酯) | 5 | 5 | 5 |
实施例#5CHDM亚磷酸酯 | 3 | ||
比较实施例#8亚磷酸酯 | 3 | ||
比较实施例#9亚磷酸酯 | 3 | ||
炭化时间(分钟),180℃ | >120 | 85 | 95 |
如在表4中说明的那样,在通过聚氯乙烯中炭化的时间测量的静态温度稳定性方面,基于饱和脂族二醇的亚磷酸酯表现的更好。
实施例#12
在含有脂环族二醇的亚磷酸酯与不含脂环族二醇的那些之间进行进一步比较。测试以下制剂。
表5
如在表5中说明的那样,在通过聚丙烯中的熔体流动指数和泛黄指数测量的挤出稳定性方面,基于饱和脂族二醇的亚磷酸酯表现的更好。
在含有脂环族二醇的亚磷酸酯与不含脂环族二醇的那些之间进行还进一步的比较。测试以下制剂。
表6
如在表6中说明的那样,在通过聚丙烯中的熔体流动指数和泛黄指数测量的挤出稳定性方面,基于饱和脂族二醇的亚磷酸酯表现的更好,甚至在比非饱和脂族二醇亚磷酸酯低的浓度下。
在含有脂环族二醇的亚磷酸酯与不含脂环族二醇的那些之间进行还进一步的比较。测试以下制剂。
表7
如在表7中说明的那样,在通过线性低密度聚乙烯中的熔体流动指数和泛黄指数测量的挤出稳定性方面,基于饱和脂族二醇的亚磷酸酯表现的更好,甚至在比非饱和脂族二醇亚磷酸酯低的浓度下。
在含有脂环族二醇的亚磷酸酯与不含脂环族二醇的那些之间进行还进一步的比较。测试以下制剂。
表8
如在表8中说明的那样,与非饱和脂族二醇亚磷酸酯相比,基于饱和脂族二醇的亚磷酸酯,在通过线性低密度聚乙烯中的熔体流动指数和泛黄指数测量的挤出稳定性方面表现的更好。
实施例#13
采用实施例#1中的装置。加入45克(0.31 mol)的环己烷二甲醇、亚磷酸三乙酯(60g, 0.36 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约280) (87 g, 0.44 mol)、平均分子量为400的聚丙二醇(5 g, 0.013 mol)和0.5克甲醇钠。把混合物很好混合,并加热至约160℃。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为非粘性液体。
实施例#14
采用实施例#1中的装置。加入25克(0.17 mol)的环己烷二甲醇、亚磷酸三苯酯(114 g, 0.37 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约280) (92 g, 0.47 mol)、平均分子量为400的聚己内酯(68 g, 0.17 mol)和0.5克氢氧化钾。把混合物很好混合,并加热至约160℃。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为非粘性液体。
实施例#15
采用实施例#1中的装置。加入87克(0.75 mol)的环己二醇、亚磷酸三苯酯(284 g,0.92 mol)、98%月桂醇(236 g, 1.27 mol)、平均分子量为400的聚丙二醇(6 g, 0.015mol)和0.5克氢氧化钾。把混合物很好混合,并加热至约160℃。然后把压力逐渐减小至0.3mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为粘性液体。
实施例#16
采用实施例#1中的装置。加入60克(0.42 mol)的环己烷二甲醇、亚磷酸三苯酯(284 g, 0.92 mol)、硬脂醇(293 g, 0.85 mol)、1,6己二醇(49 g, 0.42 mol)和1.5克氢氧化钾。把混合物很好混合,并加热至约160℃。然后把压力逐渐减小至0.3 mm Hg,并经1小时过程使温度增加至180℃。把反应内容物在真空下,于180℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为粘性液体。
实施例#13-#16中各种所合成添加剂的性质至少部分特征可在于下表。
表9
实施例# | #13 | #14 | #15 | #16 |
MP ℃ | 液体 | 液体 | 液体 | 40℃ |
AV | 0.01 | 0.01 | 0.01 | 0.01 |
% P | 7.6 | 5.8 | 7.9 | 6.6 |
平均MWw | 18926 | 15179 | 4066 | 29032 |
比较实施例#17
实施例#1中的装置用于合成低分子量(~2700 M.W.,即n=5-6)多亚磷酸酯,具有CHDM和C12-14醇作为反应物。加入50克(0.345 mol)的环己烷二甲醇、亚磷酸三苯酯(126 g,0.40 mol)、月桂醇和肉豆蔻醇的混合物(羟基数为约280) (112 g, 0.57 mol)和0.4克氢氧化钾。把混合物很好混合,并在氮气下加热至约150℃,且在该温度下保持1小时。然后把压力逐渐减小至0.3 mm Hg,并使温度保持在150℃,经1小时的过程。把反应内容物在真空下,于150℃下保持2小时,此时不再有苯酚蒸馏出来。然后用氮气破除真空,并使粗产物冷却至环境温度。产物为非粘性液体。
实施例#18
实施例#1的装置用于合成具有CHDM的高分子量(~14000 M.W.)多亚磷酸酯,采用在以上实施例#2中的相同实验条件和反应物的量。
表10
如在表10中说明的那样,与现有技术相对较低分子量的CHDM多亚磷酸酯相比,加入较高分子量的CHDM多亚磷酸酯显示改善的性能。同样显著并且也许更引人注目地,与其较低分子量的类似物相比,较高分子量的CHDM多亚磷酸酯的水解稳定性得到改善,改善本身在24小时显现,当然到48小时会显现。
以上已经说明的是CHDM的加入改善了亚磷酸酯添加剂的水解稳定性,在亚磷酸酯添加剂中CHDM刚性结构由于其饱和环而不弯曲。另外,其基本上无“气味”。一个实施方案采用与按重量计90% CHDM组合的约10%重量的聚丙二醇(“PPG”)。PPG防止交联,并保持亚磷酸酯为液体。增大量的CHDM另外增加分子中磷的百分数,这提供了性能增强。
在合成期间,以使封端羟基的数目减至最少的摩尔比,采用单羟基和二羟基反应物的组合(其中至少一种要求为CHDM)和三亚磷酸酯反应物。不束缚于任何反应理论或操作机制,以下说明实施例#7的说明性的典型反应流程描述。
通过控制反应物的摩尔比,相应地控制羟基端的量。优选的比率为约1:1:1,而更优选的比率将具有二羟基封端的反应物作为限制性试剂,并且单官能链终止剂稍微摩尔过量。尽管图示描述为典型化的,并且相信为准确的描述,但是化学反应的不可预知性质阻止了任何绝对确定性的描述。然而,所说明的是,尽管在多亚磷酸酯中可能具有一些羟基端,即以上单官能羟基部分中的一些,但是其可用二羟基部分替代。然而,通过控制反应物的摩尔比,链末端的羟基的量优选限于在分子内不多于1-2个链,取决于过量链终止剂的量。
通过采用上文描述的方法和技术,可以控制具有最少末端羟基的不含烷基酚的多亚磷酸酯的分子量和羟基端,包括以下步骤:
使三亚磷酸酯与限定摩尔量的二羟基封端的反应物以及摩尔过量的单官能链终止剂反应;
加入碱;
加热所述三亚磷酸酯、二羟基封端的反应物(其中所述二羟基封端的反应物包含至少一个饱和碳环)和单官能链终止剂及碱;和
进一步其中所述聚合多亚磷酸酯为以下反应物的反应产物:
至少一种单羟基封端的反应物;
至少一种选自HO-[R7]a-R8-[R9]b-OH的二羟基封端的反应物,其中R7为直链或支链的C1-6亚烷基,R8为环中具有5-10个碳原子的饱和碳环,和R9为直链或支链的C1-6亚烷基,并且进一步其中a和b为在0-1范围内的整数值;和
包含至少一个含磷部分的三官能反应物;和
分离所述不含烷基酚的亚磷酸酯。
当形成共聚物时,所述方法进一步包括加入至少一种第二聚烷二醇二羟基封端的反应物的步骤,并且其中所述聚烷二醇选自聚乙二醇和聚丙二醇。
已经证实的是,可以设计满足所有所需的性能属性而不需使用烷基酚作为第二抗氧化剂的聚合多亚磷酸酯。高分子量减少过程期间的析出,并使后处理期间的挤出/起霜减至最少。较高分子量也导致减少挥发性和减少迁移与暴露。
使用本发明亚磷酸酯的附加益处包括增加与许多聚合物的相容性,导致挤出期间的析出和后处理期间的挤出/起霜减少。析出是由于熔融处理期间的不相容性,并且在铸塑薄膜产品期间,导致材料在设备例如压延磨或冷却鼓/筒滚上留下沉积物。挤出/起霜为物理性质,随着时间推移,不相容的亚磷酸酯可在其已被混合/处理之后,起霜于聚合物膜(例如LLDPE膜)的表面。这导致粉化/粉末或粘性表面。较高分子量的多亚磷酸酯减少了亚磷酸酯迁移,导致消费者包装益处。
本发明已参照优选和备选的实施方案进行了描述。很明显,在阅读和理解说明书后,将对其它实施方案进行修改和改变。在它们落入所附权利要求或其等同实施方案的范围内,打算包括所有这样的修改和改变。
Claims (9)
1.一种聚合多亚磷酸酯,所述聚合多亚磷酸酯含有1-1000个下式的重复单元:
其中
R2选自
(i)C1-20烷基或C2-22烯基,所述C1-20烷基或C2-22烯基任选用C5-10环烷基或环烯基中断或封端,
(ii)任选用C1-4烷基封端的C2-20聚烷二醇链,和
(iii)含有-CO-O-基团并任选用C1-20烷基取代的3-7元环;
R7和R9中每一个独立表示C1-6亚烷基;
R8为亚环己基;和
a和b为1;
和0-1000个下式的重复单元:
其中Y表示C2-22亚烷基和m为1-20;
所述多亚磷酸酯邻近上式的-P(OR2)-基团用基团R1O-封端,并且在链的另一个末端用基团-P(OR3)(OR4)封端,其中可相同或不同的R1、R3和R4中的每一个,具有为R2给出的含义之一;
条件是当所述多亚磷酸酯含有多于1个但是少于12个式B的单元时,其必须含有2个或更多个式A的单元;和
进一步的条件是当所述多亚磷酸酯不含式B的单元时,其必须含有8个或更多个式A的单元。
2.权利要求1的聚合亚磷酸酯,其中Y表示-CH2CH2-或-CH(CH3)CH2-基团。
3.权利要求1或权利要求2的聚合多亚磷酸酯,其中m为5-20。
4.权利要求1的聚合多亚磷酸酯,所述聚合多亚磷酸酯不含式B的单元。
5.前述权利要求1或2的聚合亚磷酸酯,其中R2表示C10-20烷基。
6.权利要求1或2的聚合亚磷酸酯,其中R7和R9为亚甲基。
7.权利要求1或2的聚合亚磷酸酯,所述聚合亚磷酸酯含有10-1000个式A的单元。
8.一种聚合物组合物,所述组合物包含合成聚合物和权利要求1-7中任一项要求的聚合多亚磷酸酯。
9.如权利要求8要求保护的聚合物组合物,其中所述合成聚合物为聚烯烃。
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