CN1890284A - 聚醚多元醇、聚酯多元醇和聚氨酯的稳定 - Google Patents
聚醚多元醇、聚酯多元醇和聚氨酯的稳定 Download PDFInfo
- Publication number
- CN1890284A CN1890284A CNA2004800359131A CN200480035913A CN1890284A CN 1890284 A CN1890284 A CN 1890284A CN A2004800359131 A CNA2004800359131 A CN A2004800359131A CN 200480035913 A CN200480035913 A CN 200480035913A CN 1890284 A CN1890284 A CN 1890284A
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- China
- Prior art keywords
- butyl
- phenyl
- composition
- methyl
- hydroxyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
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- 238000010992 reflux Methods 0.000 description 5
- 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 5
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- HTSVYUUXJSMGQC-UHFFFAOYSA-N 2-chloro-1,3,5-triazine Chemical class ClC1=NC=NC=N1 HTSVYUUXJSMGQC-UHFFFAOYSA-N 0.000 description 4
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- MCMMSXFAWOGWQE-UHFFFAOYSA-N n-octadecylhexadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCC MCMMSXFAWOGWQE-UHFFFAOYSA-N 0.000 description 1
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- RQVGZVZFVNMBGS-UHFFFAOYSA-N n-octyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(CCCCCCCC)C1=CC=CC=C1 RQVGZVZFVNMBGS-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- 229960004418 trolamine Drugs 0.000 description 1
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- 235000019154 vitamin C Nutrition 0.000 description 1
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- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
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- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 description 1
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Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
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- C08G18/4833—Polyethers containing oxyethylene units
- C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
- C08G18/4841—Polyethers containing oxyethylene units and other oxyalkylene units containing oxyethylene end groups
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
- C08K5/134—Phenols containing ester groups
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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
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
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Abstract
具有突出的氧化降解、热降解或光-诱导降解稳定性并且具有减少的来自所述聚合物的雾化的聚醚多元醇、聚酯多元醇或聚氨酯,包括至少一种式(I)的液体化合物,其中R1是C1-C4烷基,R2是支链C12-C25烷基,和X是C1-C8亚烷基或C1-C4烷基取代的C2-C8亚烷基。
Description
本发明涉及组合物,所述组合物包括容易氧化降解、热降解或光-诱导降解的聚醚多元醇、聚酯多元醇或聚氨酯以及作为稳定剂的特定类型的液体酚类抗氧化剂。
使用酚类抗氧化剂作为稳定剂用于聚醚多元醇、聚酯多元醇或聚氨酯是已知的,例如在H.Zweifel;Plastic Additives Handbook,5thEdition,Hanser Publishers,Munich,88-109页(2001)中就有描述。
已知的稳定剂并不能在每一个方面都满足稳定剂需要达到的高要求,特别是对于存储寿命、吸水性、水解敏感性、加工稳定性、颜色性质、挥发性、迁移行为、相容性和耐光保护的改进。此外,汽车工业强烈希望显著减少挥发性有机化合物(VOC)特别是气体排放物(FOG)的数量。所述气体排放物通常也与‘雾化’现象有关,其中蒸发的挥发性物质可以冷凝在汽车挡风玻璃中导致在窗户上的沉积。而且,衬垫、家具和地毯底布泡沫体的最终使用者也向柔软泡沫胶板的生产商施加压力。辅助添加剂例如催化剂、表面活性剂、阻燃剂、抗氧化剂导致产生聚氨酯泡沫体的排放物。VOC的主要来源是如有机硅表面活性剂和胺催化剂的添加剂。本领域对柔软胶板进行稳定的现状是基于受阻酚和仲芳香胺的组合。液体酚类抗氧化剂尤其导致产生气体排放物(FOG)。
本发明涉及具有极低雾化作用的特定类型的液体酚类抗氧化剂。
本发明因此提供组合物,包括
a)容易氧化降解、热降解或光-诱导降解的聚醚多元醇、聚酯多元醇或聚氨酯;和
b)至少一种下式I的液体化合物
其中
R1是C1-C4烷基,
R2是支链C12-C25烷基,和
X是C1-C8亚烷基或C1-C4烷基取代的C2-C8亚烷基。
具有至多4个碳原子的烷基是支链或直链基团,例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基或叔丁基。R1的优选定义之一是甲基或叔丁基。
具有12-25个碳原子的烷基是支链基团,例如2-丁基-1-辛醇、2-丁基-1-壬醇、2-丁基-1-癸醇、2-丁基-1-十一烷醇、2-丁基-1-十二烷醇、2-丁基-1-十八烷醇、2-戊基-1-辛醇、2-戊基-1-壬醇、2-戊基-1-癸醇、2-戊基-1-十一烷醇、2-戊基-1-十二烷醇、2-戊基-1-十八烷醇、2-己基-1-辛醇、2-己基-1-壬醇、2-己基-1-癸醇、2-己基-1-十一烷醇、2-己基-1-十二烷醇、2-己基-1-十八烷醇、2-庚基-1-辛醇、2-庚基-1-壬醇、2-庚基-1-癸醇、2-庚基-1-十一烷醇、2-庚基-1-十二烷醇、2-庚基-1-十八烷醇、2-辛基-1-辛醇、2-辛基-1-壬醇、2-辛基-1-癸醇、2-辛基-1-十一烷醇、2-辛基-1-十二烷醇或2-辛基-1-十八烷醇。R2的优选定义是2-己基-1-癸醇和2-辛基-1-十二烷醇。
C1-C8亚烷基是支链或直链基团,例如亚甲基、亚乙基、亚丙基、三亚甲基、四亚甲基、五亚甲基、六亚甲基、七亚甲基或八亚甲基。X的优选定义是C1-C4亚烷基,特别是亚乙基。
C1-C4烷基取代的C1-C8亚烷基是支链或直链基团,例如乙叉基、1-甲基亚乙基、2-甲基亚乙基、1-甲基亚丙基或2-甲基亚丙基。X的优选定义是1-甲基亚乙基或2-甲基亚乙基。
优选的式I化合物是其中R1是甲基或叔丁基,R2是支链C14-C25烷基以及X是C1-C4亚烷基或甲基取代的C2-C4亚烷基的那些化合物。
进一步优选的式I化合物是其中X是亚乙基的那些。
特别令人感兴趣的是其中R2是支链C15-C22烷基的式I化合物。
R3是C3-C18烷基,和
R4是C5-C20烷基;条件是R3和R4碳原子的和是10-23。
还令人感兴趣的是其中R1是甲基或叔丁基,R2是支链C16-C20烷基以及X是亚乙基的式I化合物。
式I化合物可以通过本身已知的方式制备,例如通过用醇酯化羧酸。
式I化合物适合作为聚醚多元醇、聚酯多元醇或聚氨酯抗氧化降解、热降解或光-诱导降解的稳定剂,以及作为所述聚合物造成的雾化(fogging contribution)的降低剂。
式I的化合物同样也用于聚氨酯制造,特别是用于制造柔软聚氨酯泡沫体。在本文中,所述新型组合物以及由其制造的产品受到有效的降解保护。特别是在泡沫体制造期间避免了早期固化(scorching)。优选地,亚磷酸酯(phosphites)例如二苯基异癸基亚磷酸酯(DPDP)或苯基二异癸基亚磷酸酯(PDDP)作为抗氧化剂或抗焦化体系在发泡之前以相对高的浓度(基于聚醚多元醇至多1.5wt%)在混合头位置,被后加入被碱稳定的聚醚多元醇中。
所述聚氨酯例如通过使含有端羟基的聚醚、聚酯和聚丁二烯与脂肪族或芳香族多异氰酸酯反应得到。
具有端羟基的聚醚和聚酯是已知的,并且通过例如如下方式制备:通过例如在BF3的存在下使环氧化物例如环氧乙烷、环氧丙烷、环氧丁烷、四氢呋喃、氧化苯乙烯或表氯醇与它们自身聚合,或者通过这些环氧化物单独或作为混合物或顺序与含有反应性氢原子的起始组分进行加成反应,所述含有反应性氢原子的起始组分例如是水、醇、氨或胺,例如乙二醇、1,3-丙二醇和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。根据本发明蔗糖聚醚也是合适的。在很多情况下优选主要含有伯羟基的那些聚醚(高达90wt%,基于聚醚中存在的所有羟基)。此外,被乙烯基聚合物改性的聚醚,如例如通过在聚醚的存在下聚合苯乙烯和丙烯腈形成,也是合适的,例如含有羟基的聚丁二烯。
这些化合物通常分子量是40并且是多羟基化合物,特别是含有2-8个羟基的化合物,特别是分子量为800-10000优选1000-6000的那些化合物,例如含有至少2个,通常为2-8个,但优选2-4个羟基的聚醚,如已知用于制备均相聚氨酯和多孔聚氨酯的那些。
当然可以使用含有至少两个异氰酸酯反应性氢原子、分子量特别是400-10000的上述化合物的混合物。
合适的多异氰酸酯是脂肪族、脂环族、芳脂族(araliphatic)、芳香族和杂环多异氰酸酯,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1,3-二异氰酸酯和环己烷1,4-二异氰酸酯以及这些异构体的任何期望的混合物、1-异氰酸根合(isocyanato)-3,3,5-三甲基-5-异氰酸根合甲基环己烷、2,4-和2,6-六氢亚苄基二异氰酸酯以及这些异构体的任何期望的混合物、六氢-1,3-和/或-1,4-亚苯基二异氰酸酯、全氢-2,4’-和/或-4,4’-二苯基甲烷二异氰酸酯、1,3-和1,4-亚苯基二异氰酸酯、2,4-和2,6-亚苄基二异氰酸酯以及这些异构体的任何期望的混合物、二苯基甲烷2,4’-二异氰酸酯和/或二苯基甲烷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、如通过苯胺-甲醛缩合然后进行光气化(phosgenization)得到的多苯基-多亚甲基多异氰酸酯、间-和对-异氰酸根合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、含有酯基团的多异氰酸酯、上述异氰酸酯与缩醛的反应产物,和含有聚合脂肪酸基的多异氰酸酯。
还可以原样使用在工业制备异氰酸酯过程中得到的含有异氰酸酯基团的蒸馏残余物,或在将其溶于一种或多种上述多异氰酸酯中后进行使用。还可以使用上述多异氰酸酯的任意期望的混合物。
通常特别优选的是工业上容易得到的多异氰酸酯,2,4-和2,6-亚苄基二异氰酸酯以及这些异构体的任何期望的混合物(“TDI”),如通过苯胺-甲醛缩合然后进行光气化制备的多苯基-多亚甲基多异氰酸酯(“粗MDI”),以及含有碳二亚胺基团、尿烷基团、脲基甲酸酯基团、异氰脲酸酯基团、脲基团或缩二脲基团的多异氰酸酯(“改性多异氰酸酯”)。
聚氨酯泡沫体优选由液体起始组分制备,或者在一步法中混合在一起的起始组分相互反应,或者首先制备由多元醇和过量多异氰酸酯形成的含有NCO基团的预加合物然后发泡,通常是与水进行反应。
在泡沫体的制备中,发泡通常在模具中进行。在这种情况下,将反应混合物放置于模具中。合适的模具材料是金属,通常是铝,或者是塑料,通常是环氧树脂。在模具中,可发泡的反应混合物发泡并形成模塑制品。所述泡沫模塑可以以如下方式进行:所述模塑产品具有多孔的表面结构,或者所述模塑产品具有致密表层和多孔的内核。就这方面而言,可以向模具中放入足够量的可发泡反应混合物以便得到的泡沫体恰好填满模具。但是,也可以向模具中加入比用泡沫体填满模具内部所需的量多的可发泡反应混合物。所以在后面这种情况下操作是在过量加入的情况下进行。
在泡沫模塑的情况下,通常伴随使用已知的外脱模剂,通常是硅油。但是,也可以使用所谓的内脱模剂,任选与外脱模剂混用。也可以使用冷熟化泡沫体。当然,可选择的,所述泡沫体可以通过间歇发泡(block foaming)或通过已知的双传送带工艺制备。这些工艺可以用于制备柔软的、半柔软的或硬的聚氨酯泡沫体。所述泡沫体可用于使用这些产品的用途中,例如作为家具和汽车工业中的衬垫和装饰物,以及用于制造配件,例如用于汽车工业中,最后还可作为隔音组合物以及作为热绝缘和低温绝缘组合物,例如在建筑领域或在制冷工业中,或者在纺织工业中,例如作为肩垫。
基于待稳定的聚合物的重量,式I化合物优选以0.01-10,特别是0.01-5%,例如0.01-2%的量加入到所述待稳定的聚合物中。
除了组分(a)和(b)以外,所述的新型组合物可以进一步包括辅助稳定剂(添加剂),例如下面的这些:
1.抗氧化剂
1.1烷基化单酚类,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-双十八烷基-4-甲基苯酚、2,4,6-三环己基苯酚、2,6-二叔丁基-4-甲氧基甲基苯酚,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,以及它们的混合物。
1.2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。
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-羟基苯甲醚,3,5-二叔丁基-4-羟基苯甲醚,硬脂酸3,5-二叔丁基-4-羟基苯酯,二(3,5-二叔丁基-4-羟基苯基)己二酸酯。
1.4.生育酚,例如α-生育酚,β-生育酚,γ-生育酚,δ-生育酚和其混合物(Vitamin E)。
1.5.羟基化二苯基硫醚,例如2,2′-硫二(6-叔丁基-4-甲基苯酚),2,2′-硫二(4-辛基苯酚),4,4′-硫二(6-叔丁基-3-甲基苯酚),4,4′-硫二(6-叔丁基-2-甲基苯酚),4,4′-硫二(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.亚烷基二苯酚,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′-乙叉基二(4,6-二叔丁基苯酚),2,2′-乙叉基二(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)二环戊二烯,二[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,1,1-二(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-3,5-二甲基苄巯基乙酸十八烷基酯,4-羟基-3,5-二叔丁基苄巯基乙酸十三烷基酯,三(3,5-二叔丁基-4-羟基苄基)胺,二(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯,二(3,5-二叔丁基-4-羟基苄基)硫化物,3,5-二叔丁基-4-羟基苄巯基乙酸异辛基酯。
1.8.羟苄基化丙二酸酯,例如双十八烷基2,2-二(3,5-二叔丁基-2-羟苄基)丙二酸酯,双十八烷基2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸酯,双十二烷巯基乙基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]2,2-二(3,5-二叔丁基-4-羟苄基)丙二酸酯。
1.9.芳香族羟苄基化合物,例如1,3,5-三(3,5-二叔丁基-4-羟苄基)-2,4,6-三甲基苯,1,4-二(3,5-二叔丁基-4-羟苄基)-2,3,5,6-四甲基苯,2,4,6-三(3,5-二叔丁基-4-羟苄基)苯酚。
1.10.三嗪化合物,例如2,4-二(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-4,6-二(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛巯基-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,例如二甲基2,5-二叔丁基-4-羟基苄基膦酸酯,二乙基3,5-二叔丁基-4-羟基苄基膦酸酯,双十八烷基3,5-二叔丁基-4-羟基苄基膦酸酯,双十八烷基5-叔丁基-4-羟基-3-甲基苄基-膦酸酯,3,5-二叔丁基-4-羟基苄基膦酸单乙酯的钙盐。
1.12.酰氨基苯酚,例如4-羟基月桂酰苯胺(4-hydroxylauranilide),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)丙酸与单-或多-元醇的酯,例如与甲醇,乙醇,正辛醇,异辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,乙二醇,1,2-丙二醇,新戊二醇,硫二甘醇,二甘醇,三甘醇,季戊四醇,三(羟乙基)异氰脲酸酯,N,N′-二(羟乙基)草酰胺,3-硫代十一烷醇,3-硫代十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟基甲基-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)丙酸与单-或多-元醇的酯,例如与甲醇,乙醇,正辛醇,异辛醇,十八烷醇,1,6-己二醇,1,9-壬二醇,乙二醇,1,2-丙二醇,新戊二醇,硫二甘醇,二甘醇,三甘醇,季戊四醇,三(羟乙基)异氰脲酸酯,N,N′-二(羟乙基)草酰胺,3-硫代十一烷醇,3-硫代十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟基甲基-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)丙酸与单-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,三(羟乙基)异氰脲酸酯,N,N′-二(羟乙基)草酰胺,3-硫代十一烷醇,3-硫代十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟基甲基-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-羟基苯基乙酸与单-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,三(羟乙基)异氰脲酸酯,N,N′-二(羟乙基)草酰胺,3-硫代十一烷醇,3-硫代十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟基甲基-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)六亚甲基二酰胺,N,N′-二(3,5-二-叔丁基-4-羟基苯基丙酰)三亚甲基二酰胺,N,N′-二(3,5-二叔丁基-4-羟基苯基丙酰)酰肼),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(来自Uniroyal的NaugardXL-1)。
1.18.抗坏血酸(Vitamin C)。
1.19.胺类型(aminic)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′-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-环已基-N′-苯基-对苯二胺,4-(对甲苯磺酰胺基)-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,辛基化的二苯基胺,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,1,2-二[(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,叔辛基化的N-苯基-1-萘基胺,单-和二-烷基化的叔丁基/叔辛基二苯基胺的混合物,单-和二-烷基化的壬基二苯基胺的混合物,单-和二-烷基化的十二烷基二苯基胺的混合物,单-和二-烷基化的异丙基/异己基二苯基胺的混合物,单-和二-烷基化的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,酚噻嗪,单-和二-烷基化的叔丁基/叔辛基酚噻嗪的混合物,单-和二-烷基化的叔辛基酚噻嗪的混合物,N-烯丙基酚噻嗪,二壬基吩噻嗪,单壬基吩噻嗪,单-和二-烷基化的壬基吩噻嗪的混合物,N,N,N′,N′-四苯基-1,4-二氨基丁-2-烯,上述公开的未被取代或取代的二苯基胺之一与上述公开的未被取代或取代的吩噻嗪之一的混合物。
2.UV吸收剂和光稳定剂
2.1.2-(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′-二(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-甲氧羰基乙基)苯基)-5-氯苯并三唑,2-(3′-叔丁基-2′-羟基-5′-(2-甲氧羰基乙基)苯基)-苯并三唑,2-(3′-叔丁基-2′-羟基-5′-(2-辛氧羰基乙基)苯基)苯并三唑,2-(3′-叔丁基-5′-[2-(2-乙基己氧基)羰基乙基]-2′-羟基苯基)苯并三唑,2-(3′-十二烷基-2′-羟基-5′-甲基苯基)苯并三唑,2-(3′-叔丁基-2′-羟基-5′-(2-异辛氧羰基乙基)苯基苯并三唑,2,2′-亚甲基二[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;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。
2.2.2-羟基二苯甲酮类和甲脒类,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′-二甲氧基二苯甲酮;N-烯丙基-N,N’-二芳基甲脒类,例如苯甲酸,4-[[(甲基苯基氨基)亚甲基]氨基]乙酯[Tinuvin 101(TRM),Ciba Specialty ChemicalsInc.];苯甲酸,4-[[(乙基苯基氨基)亚甲基]氨基]乙酯;2-丙烯酸,3-(4-甲氧基苯基)-,2-乙基己酯[Uvinul 3088(RTM),BASF];2-丙烯酸,2-氰基-3,3-二苯基-,乙酯[Uvinul 3035(RTM),BASF];或2-丙烯酸,2-氰基-3,3-二苯基-,2-乙基己酯[Uvinul 3039(RTM),BASF]。
2.3.未取代或取代苯甲酸的酯,例如水杨酸4-叔丁基苯酯,水杨酸苯酯,水杨酸辛基苯酯,二苯甲酰基间苯二酚,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-4,6-二叔丁基苯酯。
2.4.丙烯酸酯,例如α-氰基-β,β-二苯基丙烯酸乙酯,α-氧基-β,β-二苯基丙烯酸异辛酯,α-甲氧羰基肉桂酸甲酯,α-氰基-β-甲基-p-甲氧基肉桂酸甲酯,α-氰基-β-甲基-p-甲氧基肉桂酸丁酯,α-甲氧羰基-p-甲氧基肉桂酸甲酯和N-(β-甲氧羰基-β-氰基乙烯基)-2-甲基二氢吲哚。
2.5.镍化合物,例如2,2′-硫二[4-(1,1,3,3-四甲基丁基)苯酚]的镍络合物,例如1∶1或1∶2络合物,有或没有额外的配体例如正丁胺,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单烷基酯的镍盐,例如甲基或乙基酯的镍盐,酮肟的镍络合物,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-月桂酰基-5-羟基吡唑的镍络合物,有或没有额外的配体。
2.6.位阻胺,例如二(2,2,6,6-四甲基-4-哌啶基)癸二酸酯,二(2,2,6,6-四甲基-4-哌啶基)琥珀酸酯,二(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯,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产物,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-1,3,5-三嗪的线型或环状缩合产物,三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯,四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯,1,1′-(1,2-乙烷二基)-二(3,3,5,5-四甲基哌嗪酮(piperazinone)),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,二(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,二(1-辛氧基-2,2,6,6-四甲基哌啶基)癸二酸酯,二(1-辛氧基-2,2,6,6-四甲基哌啶基)琥珀酸酯,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-1,3,5-三嗪的线型或环状缩合产物,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)乙烷的缩合产物,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)乙烷的缩合产物,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-1,3,5-三嗪的缩合产物,1,2-二(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪和4-丁基氨基-2,2,6,6-四甲基哌啶(CAS Reg.No.[136504-96-6])的缩合产物;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(CAS Reg.No.[192268-64-7])的缩合产物;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-4-(2,2,6,6-四甲基-4-哌啶基)]硅氧烷,马来酸酐α-烯烃共聚物和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。
27.草酸二酰胺,例如4,4′-二辛氧基草酰二苯胺,2,2′-二乙氧基草酰二苯胺,2,2′-二辛氧基-5,5′-二叔丁氧基草酰二苯胺,2,2′-双十二烷氧基-5,5′-二叔丁氧基草酰二苯胺,2-乙氧基-2′-乙基草酰二苯胺,N,N′-二(3-二甲基氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2′-乙氧基草酰二苯胺和其与2-乙氧基-2′-乙基-5,4′-二叔丁氧基草酰二苯胺的混合物,邻和对甲氧基二取代草酰二苯胺的混合物以及邻和对乙氧基二取代草酰二苯胺的混合物。
2.8.2-(2-羟基苯基)-1,3,5-三嗪,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)-2-羟基丙基氧]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′-二苯基草酸二酰胺,N-水杨醛-N′-水杨酰肼,N,N′-二(水杨酰)肼,N,N′-二(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,二(亚苄基)草酸二酰肼,草酰二苯胺,间苯二甲酸二酰肼,癸二酸二苯基酰肼,N,N′-二乙酰基己二酸二酰肼,N,N′-二(水杨酰)草酸二酰肼,N,N′-二(水杨酰)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,二苯基烷基亚磷酸酯,苯基二烷基亚磷酸酯,三(壬基苯基)亚磷酸酯,三月桂基亚磷酸酯,三(十八烷基)亚磷酸酯,二硬脂基季戊四醇二亚磷酸酯,三(2,4-二叔丁基苯基)亚磷酸酯,二异癸基季戊四醇二亚磷酸酯,二(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯,二(2,4-二枯基苯基)季戊四醇二亚磷酸酯,二(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,二(2,4-二叔丁基-6-甲基苯基)季戊四醇二亚磷酸酯,二(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′-二亚苯基二亚膦酸酯,6-异辛氧基-2,4,8,10-四叔丁基-12H-苯并[d,g]-1,3,2-二氧杂phosphocin,二(2,4-二叔丁基-6-甲基苯基)甲基亚磷酸酯,二(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phosphocin,2,2′,2″-次氮基[三乙基三(3,3′,5,5′-四叔丁基-1,1′-二苯基-2,2′-二基)-亚磷酸酯],2-乙基己基(3,3′,5,5′-四叔丁基-1,1′-二苯基-2,2′-二基)亚磷酸酯,5-丁基-5-乙基-2-(2,4,6-三叔丁基苯氧基)-1,3,2-二氧杂phosphirane。
5.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,来自氢化牛油脂肪胺的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,衍生自由氢化牛油脂肪胺制备的N,N-二烷基羟胺的硝酮。
7.硫协同剂,例如硫代二丙酸二月桂酯或硫代二丙酸二硬脂酯。
8.过氧化物清除剂,例如β-硫代二丙酸的酯,例如月桂酯,硬脂酯,肉豆蔻酯或十三烷基酯,巯基苯并咪唑,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。
9.碱性辅助稳定剂,例如蜜胺,聚乙烯吡咯烷酮,双氰胺,三烯丙基氰脲酸酯,脲衍生物,肼衍生物,胺,聚酰胺,聚氨基甲酸酯,高级脂肪酸的碱金属和碱土金属盐,例如硬脂酸钙,硬脂酸锌,山萮酸镁,硬脂酸镁,蓖麻醇酸钠,棕榈酸钾,儿茶酸锑或儿茶酸锌。
10.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,云母,硫酸钡,金属氧化物和氢氧化物,碳黑,石墨,木粉和其它天然产物的粉末和纤维,合成纤维。
11.其它添加剂,例如增塑剂,润滑剂,乳化剂,颜料,流变添加剂,催化剂,流动控制剂,荧光增白剂,阻燃剂,抗静电剂和发泡剂。
12.苯并呋喃酮和吲哚酮(indolinone),例如U.S.4325863;U.S.4338244;U.S.5175312,U.S.5216052;U.S.5252643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839;EP-A-0591102或EP-A-1291384中所述,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-酮或3-(2-乙酰基-5-异辛基苯基)-5-异辛基苯并呋喃-2-酮。
相对于待稳定的所述合成聚合物的总重量,所述辅助稳定剂的加入浓度例如为0.01-10%.
优选的进一步的添加剂是光稳定剂、加工稳定剂和/或胺类型抗氧化剂。优选的胺类型抗氧化剂例如公开在上述第1.19项中。优选的加工稳定剂是苯并呋喃酮类(第12项)、亚磷酸酯或亚膦酸酯类(第4项)。
作为胺类型(aminic)抗氧化剂,优选使用未取代或取代二苯基胺和未取代或取代吩噻嗪的混合物。
本发明还涉及式Ia、Ib、Ic、Id和Ie的新化合物。
本发明还涉及稳定聚醚多元醇、聚酯多元醇或聚氨酯对抗氧化降解、热降解或光-诱导降解并且减少所述聚合物造成的雾化的方法,所述方法包括在其中加入或向其涂布至少一种式I的液体化合物。
因此本发明一个优选的目的是使用式I的液体化合物作为聚醚多元醇、聚酯多元醇或聚氨酯对抗氧化降解、热降解或光-诱导降解的稳定剂,以及作为所述聚合物造成的雾化的降低剂。
下面的实施例更加详细地说明了本发明。份数和百分数都是以重量计。
实施例1:制备式Ia的化合物101。
通过在渗滤氮气流中在装配有搅拌器、温度计和短回流冷凝器的三口烧瓶中加热,将58.48g(0.20mol)3-(3’,5’-二叔丁基-4’-羟基苯基)-丙酸甲酯(Ciba Specialty Chemicals Inc.)熔于50.59g(0.2087mol)2-己基-1-癸醇(Isofol 16,纯度:97%,来自Condea)中。然后在搅拌下加入催化量的0.80g(0.0032mol)氧化二丁锡(Fluka,purum)并将反应混合物加热到190℃的浴温。得到透明的淡黄色溶液,将该溶液在所述温度下继续搅拌16小时。释放出的甲醇被流动的氮气流吹走。然后,将反应物冷却到室温,将液体物质过滤通过少量硅胶60(Merck)以除去所述催化剂。残余物产出100.50g(理论产量的100%)式Ia的化合物101.C33H58O3分析:理论值:C78.83;H11.63%。实测值:C78.55;H11.48%。
实施例2:制备式Ib的化合物102。
通过在渗滤氮气流中在装配有搅拌器、温度计和短回流冷凝器的三口烧瓶中加热,将58.48g(0.20mol)3-(3’,5’-二叔丁基-4’-羟基苯基)-丙酸甲酯(Ciba Specialty Chemicals Inc.)熔于59.70g(0.209mol)2-辛基-1-十二烷醇(Isofol 20,来自Condea)中。然后在搅拌下加入催化量的0.80g(0.0032mol)氧化二丁锡(Fluka,purum)并将反应混合物加热到190℃的浴温。得到透明的淡黄色溶液,将该溶液在所述温度下继续搅拌16小时。释放出的甲醇被流动的氮气流吹走。然后,将反应物冷却到室温,将液体物质过滤通过少量硅胶60(Merck)以除去所述催化剂。残余物产出110.98g(理论产量的99%)式Ib的化合物102。C37H66O3分析:理论值:C79.51;H11.90%。实测值:C79.36;H11.96%。
实施例3:制备式Ic的化合物103。
通过在渗滤氮气流中在装配有搅拌器、温度计和短回流冷凝器的三口烧瓶中加热,将1.194kg(7.619mol)3-(3’,5’-二叔丁基-4’-羟基苯基)-丙酸甲酯(Ciba Specialty Chemicals Inc.)熔于1.441kg(7.75mol)2-丁基-1-辛醇(Isofol 12,来自Condea)中。然后在搅拌下加入催化量的22.52g(0.091mol)三丁醇铝(aluminum-tris-butanolate)(95%,Flukapract.)并将反应混合物加热到170℃的浴温。得到透明的淡黄色溶液,将该溶液在所述温度下继续搅拌16小时。释放出的甲醇被流动的氮气流吹走。然后,将反应物冷却到室温,将液体物质过滤通过少量硅胶60(Merck)以除去所述催化剂。残余物产出3.11kg式Ic的化合物103。TLC(Merck TLC-板,硅胶60F 254,溶剂:己烷/丙酮=6/1)。主点位于Rf=0.45。
实施例4:制备式Id的化合物104。
通过在氮气下在装配有搅拌器、温度计和回流冷凝器的三口烧瓶中加热,将500.68g(2mol)3-(3’-叔丁基-5’-甲基-4’-羟基苯基)-丙酸甲酯(Ciba Specialty Chemicals Inc.)熔于605.84g(2.033mol)2-辛基-1-十二烷醇(Isofol20,来自Condea)中,其中在所述回流冷凝器顶部带有冷却到-78℃的冷阱。然后向反应混合物中加入催化量的6.0g(0.024mol)三丁醇铝(95%,Fluka pract.)。向所述冷阱施加200hPa的部分真空。在60分钟内将温度升至180℃。三小时后,将部分真空变至35hPa.10小时后,蒸馏出总量60.90g(理论:64g)的甲醇并收集在所述冷却冷阱中。所述反应混合物是淡黄色,并从180℃冷却到80℃。然后加入350ml去离子水并继续搅拌。分离有机层并抽滤通过硅藻土(Hyflo)。用200ml己烷冲洗过滤器,将所述己烷与经过滤的有机部分合并。合并的有机层用350ml去离子水洗涤两次。小心分离所述水相,从而在最后一次洗涤操作中达到5-6的最终pH值。所述有机物质再次抽滤通过Hyflo。然后在80℃在200hPa的部分真空中蒸除己烷。所得到的液体在搅拌下在125℃/25-30hPa下进一步干燥1小时。得到1016.6g(理论产量的98%)式Id的化合物104。分析(C34H60O3):理论值:C79.01;H11.70%。实测值:C79.12;H11.62%。
实施例5:聚醚/聚氨酯软泡沫体的制备及其稳定
将根据表1的0.72g(0.45%,基于多元醇)溶于160g聚醚多元醇[Petol 46-3MB(RTM)(具有伯羟基的三官能聚醚多元醇;羟值48mgKOH/g,水含量小于0.1%,酸值小于0.1mg KOH/g)],加入由1.6gTecostab(RTM)BF 2370(Goldschmidt,Germany提供)、0.16g TegoaminZE1(Goldschmidt,Germany提供)和6.4g去离子水组成的8.16g溶液,将所述反应混合物在2600rpm剧烈搅拌10秒钟。然后加入0.67gKosmos EF(Goldschmidt,Germany提供),再将所述反应混合物在2600rpm剧烈搅拌18秒钟。然后伴随着在2600rpm连续搅拌5-7秒钟加入80.96g异氰酸酯[Lupranat T80(RTM),由BASF提供;甲苯2,4-二异氰酸酯和甲苯2,6-二异氰酸酯的混合物]。然后将混合物倾倒进20×20×20cm的盒中并在发泡成泡沫块期间测量放热温度。冷却泡沫块并在室温存储24小时。第二天将所述泡沫体切成细管(2cm厚,直径1.5cm)
使用泡沫体样品的动态热老化作为抗焦化性的量度(动态铝块测试)。通常在烘箱或铝块中加入所述泡沫体样品,通过测量颜色变化评估抗焦化性。在所述“动态”热老化测试中,温度以恒定速率增加并且作为温度的函数(在170-230℃的温度30分钟)测定颜色变化。以根据ASTM 1926-70 Yellowness Test在泡沫体样品上测定的YellownessIndex(YI)对泡沫体颜色质量进行报告。低YI值表示样品基本没怎么变色,高YI值表示样品严重变色。所述泡沫体越白,所述泡沫体被稳定的效果越好。
可从所述泡沫体释放的物质以根据方法PB VWL709(“Determination of gaseous(VOC)and by thermodesorption”,Daimler Chrysler Ltd制定)在所述泡沫体样品上测定的挥发性有机化合物(VOC)或气体排放物和可冷凝排放物(FOG)进行报告。为此目的,在惰性气流中加热一定量的材料,然后在气相色谱的低温注射器中冷冻由此释放的物质。在分离混合物后,通过质量选择性检测器尽可能的鉴别单独的物质。用所述材料样品的相同子部分进行VOC和FOG测量。气体排放物(VOC)的定量使用外甲苯标准进行,可冷凝排放物(FOG)的定量使用十六烷(C16-正烷烃)进行。所报告的是等效于甲苯或十六烷的作为总排放物的以ppm(mg/kg)为单位的浓度。低VOC值表示从泡沫体样品排出较少的气体排放物;高VOC值表示从泡沫体样品排出较多的气体排放物。低FOG值表示从泡沫体样品排出较少的可冷凝排放物;高FOG值表示从泡沫体样品排出较多的可冷凝排放物。VOC/FOG值越低,所述泡沫体关于可释放排放物的性能越好。所述结果总结于表1中。
表1:
实施例 | 稳定剂 | VOC(mg/kg) | FOG(mg/kg) |
3aa) | 0.35%IRGANO×1135c)0.05%IRGAFOS38d)0.05%PS-1e) | 25 | 360 |
3bb) | 0.35%化合物101f)0.05%IRGAFOS 38d)0.05%PS-1e) | 25 | 40 |
3cb) | 0.35%化合物102g)0.05%IRGAFO838d)0.05%PS-1e) | 25 | 35 |
a)对比实施例。
b)根据本发明的实施例。
c)Irganox 1135(RTM)(Ciba Specialty Chemicals Inc.)是式AO-1的酚类抗氧化剂。
d)Irgafors 38(RTM)是二(2,4-二叔丁基-6-甲基苯基)乙基亚磷酸酯。
e)PS-1是式B1的3-(2-乙酰基-5-异辛基苯基)-5-异辛基苯并呋喃-2-酮。
f)化合物101的制备公开于实施例1中。
g)化合物102的制备公开于实施例2中。
Claims (12)
1.一种组合物,包括
a)容易氧化降解、热降解或光-诱导降解的聚醚多元醇、聚酯多元醇或聚氨酯;和
b)至少一种下式I的液体化合物
其中
R1是C1-C4烷基,
R2是支链C12-C25烷基,和
X是C1-C8亚烷基或C1-C4烷基取代的C2-C8亚烷基。
2.权利要求1的组合物,其中
R1是甲基或叔丁基,
R2是支链C14-C25烷基,和
X是C1-C4亚烷基或甲基取代的C2-C4亚烷基。
3.权利要求1的组合物,其中X是亚乙基。
4.权利要求1的组合物,其中R2是支链C15-C22烷基。
5.权利要求1的组合物,其中
R1是甲基或叔丁基,
R2是支链C16-C20烷基,和
X是亚乙基。
6.权利要求1的组合物,其中基于组分(a)的重量,组分(b)的存在量是0.01-10%。
7.权利要求1的组合物,除了组分(a)和(b)以外,还包括其它添加剂。
8.权利要求7的组合物,作为其它添加剂包括光稳定剂、加工稳定剂和/或胺类型抗氧化剂。
9.权利要求8的组合物,作为加工稳定剂包括苯并呋喃酮类、亚磷酸酯、亚膦酸酯或吩噻嗪类化合物。
11.稳定聚醚多元醇、聚酯多元醇或聚氨酯抗氧化降解、热降解或光-诱导降解并且减少所述聚合物造成的雾化的方法,所述方法包括在其中加入或向其涂覆至少一种权利要求1的式I液体化合物。
12.权利要求1的式I液体化合物作为聚醚多元醇、聚酯多元醇或聚氨酯抗氧化降解、热降解或光-诱导降解的稳定剂,以及作为所述聚合物造成的雾化的降低剂的用途。
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DE59808425D1 (de) * | 1997-09-29 | 2003-06-26 | Ciba Sc Holding Ag | Staubfreie epoxidhaltige Stabilisatorgranulate und Verfahren zur Herstellung |
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JP2003292788A (ja) * | 2002-03-29 | 2003-10-15 | Api Corporation | 樹脂安定剤組成物及びその用途 |
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2004
- 2004-11-24 SG SG200808994-8A patent/SG148999A1/en unknown
- 2004-11-24 JP JP2006541939A patent/JP5042630B2/ja active Active
- 2004-11-24 WO PCT/EP2004/053068 patent/WO2005054328A1/en active Application Filing
- 2004-11-24 CN CNA2004800359131A patent/CN1890284A/zh active Pending
- 2004-11-24 EP EP04819689.3A patent/EP1689799B1/en active Active
- 2004-11-24 ES ES04819689.3T patent/ES2568653T3/es active Active
- 2004-11-24 BR BRPI0417261-2A patent/BRPI0417261B1/pt active IP Right Grant
- 2004-11-24 CA CA2545680A patent/CA2545680C/en active Active
- 2004-11-24 US US10/580,444 patent/US20070185250A1/en not_active Abandoned
- 2004-12-02 TW TW093137168A patent/TWI398457B/zh active
-
2006
- 2006-05-04 KR KR1020067008730A patent/KR101175639B1/ko active IP Right Grant
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102361843A (zh) * | 2009-03-26 | 2012-02-22 | 朗盛德国有限责任公司 | 多元醇的稳定化 |
CN107922730A (zh) * | 2015-09-03 | 2018-04-17 | 艾得文瑞士有限公司 | 组合物 |
CN106916432A (zh) * | 2016-09-01 | 2017-07-04 | 艾特国际有限公司 | 用来稳定聚氧化烯烃聚醚多元醇,防止其氧化降解的方法 |
CN112513119A (zh) * | 2018-07-27 | 2021-03-16 | 美利肯公司 | 高分子酚抗氧化剂 |
Also Published As
Publication number | Publication date |
---|---|
EP1689799A1 (en) | 2006-08-16 |
BRPI0417261B1 (pt) | 2021-01-26 |
BRPI0417261A (pt) | 2007-03-06 |
SG148999A1 (en) | 2009-01-29 |
WO2005054328A1 (en) | 2005-06-16 |
US20070185250A1 (en) | 2007-08-09 |
JP2007513232A (ja) | 2007-05-24 |
EP1689799B1 (en) | 2016-01-20 |
CA2545680A1 (en) | 2005-06-16 |
JP5042630B2 (ja) | 2012-10-03 |
TW200533689A (en) | 2005-10-16 |
CA2545680C (en) | 2013-07-30 |
TWI398457B (zh) | 2013-06-11 |
ES2568653T3 (es) | 2016-05-03 |
KR101175639B1 (ko) | 2012-08-22 |
KR20060117317A (ko) | 2006-11-16 |
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