CN1849349A - 防止甲基丙烯酸甲酯-丁二烯-苯乙烯接枝共聚物热氧化的稳定化 - Google Patents
防止甲基丙烯酸甲酯-丁二烯-苯乙烯接枝共聚物热氧化的稳定化 Download PDFInfo
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- CN1849349A CN1849349A CNA2004800258164A CN200480025816A CN1849349A CN 1849349 A CN1849349 A CN 1849349A CN A2004800258164 A CNA2004800258164 A CN A2004800258164A CN 200480025816 A CN200480025816 A CN 200480025816A CN 1849349 A CN1849349 A CN 1849349A
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- Prior art keywords
- graft copolymer
- butyl
- styrene
- mbs
- phenyl
- Prior art date
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- WWNGFHNQODFIEX-UHFFFAOYSA-N buta-1,3-diene;methyl 2-methylprop-2-enoate;styrene Chemical compound C=CC=C.COC(=O)C(C)=C.C=CC1=CC=CC=C1 WWNGFHNQODFIEX-UHFFFAOYSA-N 0.000 title claims abstract description 52
- 229920000578 graft copolymer Polymers 0.000 title claims abstract description 36
- 230000006641 stabilisation Effects 0.000 title abstract description 9
- 238000011105 stabilization Methods 0.000 title abstract description 9
- 230000003647 oxidation Effects 0.000 title description 5
- 238000007254 oxidation reaction Methods 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 150000003568 thioethers Chemical class 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 10
- -1 phosphorous acid ester Chemical class 0.000 claims description 106
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- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 45
- 229920000642 polymer Polymers 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 24
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 20
- 239000003963 antioxidant agent Substances 0.000 claims description 16
- 239000004816 latex Substances 0.000 claims description 16
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- 239000000843 powder Substances 0.000 claims description 14
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- 229910052751 metal Inorganic materials 0.000 claims description 10
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- 239000003795 chemical substances by application Substances 0.000 claims description 7
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 16
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- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 13
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 13
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 13
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 13
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- 239000004700 high-density polyethylene Substances 0.000 description 8
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- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- XYXJKPCGSGVSBO-UHFFFAOYSA-N 1,3,5-tris[(4-tert-butyl-3-hydroxy-2,6-dimethylphenyl)methyl]-1,3,5-triazinane-2,4,6-trione Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C)=C1CN1C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C(=O)N(CC=2C(=C(O)C(=CC=2C)C(C)(C)C)C)C1=O XYXJKPCGSGVSBO-UHFFFAOYSA-N 0.000 description 5
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 5
- PZBQVZFITSVHAW-UHFFFAOYSA-N 5-chloro-2h-benzotriazole Chemical compound C1=C(Cl)C=CC2=NNN=C21 PZBQVZFITSVHAW-UHFFFAOYSA-N 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
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- 239000000654 additive Substances 0.000 description 5
- 230000000996 additive effect Effects 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 239000012964 benzotriazole Substances 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 5
- 150000002429 hydrazines Chemical class 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 125000002347 octyl 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])[H] 0.000 description 5
- 229940059574 pentaerithrityl Drugs 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
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- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 description 4
- ICHKVCYUNCKCGL-UHFFFAOYSA-N CN(C)C.OCCCCCCO Chemical compound CN(C)C.OCCCCCCO ICHKVCYUNCKCGL-UHFFFAOYSA-N 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
- 239000003508 Dilauryl thiodipropionate Substances 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
- C08K5/372—Sulfides, e.g. R-(S)x-R'
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
- C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
- C08F279/06—Vinyl aromatic monomers and methacrylates as the only monomers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/13—Phenols; Phenolates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
- C08K5/3477—Six-membered rings
- C08K5/3492—Triazines
- C08K5/34924—Triazines containing cyanurate groups; Tautomers thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
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- C08K5/37—Thiols
- C08K5/375—Thiols containing six-membered aromatic rings
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L51/04—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to rubbers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
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Abstract
本发明涉及甲基丙烯酸甲酯-丁二烯-苯乙烯接枝共聚物与选择的空间位阻酚类抗氧剂和硫醚的稳定组合物。本发明的另一个主题是甲基丙烯酸甲酯-丁二烯-苯乙烯接枝共聚物的稳定化方法,以及选择的空间位阻酚类抗氧剂连同硫醚用于所述接枝共聚物的热稳定化的用途。
Description
本发明涉及甲基丙烯酸甲酯-丁二烯-苯乙烯接枝共聚物与选择的空间位阻酚类抗氧剂和硫醚的稳定组合物。本发明的另一个主题是甲基丙烯酸甲酯-丁二烯-苯乙烯接枝共聚物的稳定化方法,以及选择的空间位阻酚类抗氧剂连同硫醚用于所述接枝共聚物的热稳定化的用途。
具有接枝的聚丁二烯或者聚丁二烯-苯乙烯橡胶相的聚合物,例如ABS(丙烯腈-丁二烯-苯乙烯),或者MBS(甲基丙烯酸甲酯-丁二烯-苯乙烯),其橡胶相特别倾向于氧化降解,特别是在热和氧的影响下更是如此。在ABS-或者MBS-接枝-相粉末的空气-干燥期间尤其会有这样的问题。MBS甚至更倾向于氧化,因此是更难以稳定的,因为其通常具有与ABS相比较高的橡胶含量,并且具有较小的接枝-相粉末的颗粒尺寸(较高的表面面积)。MBS粉末的稳定性通常比ABS低得多。
现有技术在稳定MBS防止热氧化中使用了与硫醚结合的受阻酚抗氧剂的混合物。典型的受阻酚抗氧剂是BHT,Topanol CA,CIBAIrganox 1076,CIBAIrganox 245,CIBAIrganox 1141,等等。作为硫醚,通常使用DLTDP(二月桂基硫代二丙酸酯)或者DSTDP(二硬脂基硫代二丙酸酯)。为了在干燥步骤期间充分保护MBS,必须使用比在ABS中浓度大得多的这些稳定剂。然而,很高浓度的受阻酚抗氧剂和硫醚可能导致在加工和最终使用期间着色,因为受阻酚抗氧剂的过氧化以及随后形成高度着色的醌型结构。因此需要不要求这样高的剂量的更有效的MBS稳定剂包装。
令人惊奇地,已经发现,某些非常特殊的受阻酚抗氧剂,例如Wingstay L,CIBAIrganox 415或CIBAIrganox 3790,与上述的现有技术稳定剂相比,在MBS中具有特别良好的性能。虽然WingstayL和CIBAIrganox 415在ABS中具有优良的性能是众所周知的,但迄今为止尚未将Wingstay L、CIBAIrganox 415或CIBAIrganox3790用于稳定纯的MBS。
虽然MBS似乎是与ABS类似的聚合物,然而其在防止热氧化的稳定化方面的性状非常不同。此外,正如以上提到的,通常MBS与ABS相比具有低得多的热稳定性,因此下列差异是值得注意的。
ABS可以用单独的受阻酚抗氧剂稳定,或者用受阻酚抗氧剂和硫醚(DLTDP,DSTDP)的混合物稳定。另一方面,MBS不能用单独的受阻酚抗氧剂稳定。只有与硫醚的混合物才能提供足够的稳定性。
鉴于在MBS和ABS之间存在相当大的差异,因此Wingstay L、CIBAIrganox 415或者CIBAIrganox 3790和硫醚的混合物在MBS中显示最好的性能,这是令人惊讶的。
本发明的一个方面是稳定的聚合物组合物,其包含
a)聚合物,其是甲基丙烯酸甲酯和苯乙烯在聚丁二烯或者聚丁二烯-苯乙烯上的接枝共聚物(甲基丙烯酸甲酯-苯乙烯-丁二烯接枝共聚物MBS);
b)通式(I)、(II)或者(III)的空间位阻酚类抗氧剂或者它们的混合物:
其中,n为1-10;
和
c)不同于通式(II)的化合物的硫醚;
条件是,不存在不是在丁二烯上的接枝共聚物的其他苯乙烯聚合物或者共聚物。
MBS是商品接枝胶乳,其可以例如按照EP 0488550制备。
上述稳定的聚合物组合物可以是胶乳的形式,即包含水相的组合物。然而,优选所述稳定的聚合物组合物是固体状态。
例如,所述稳定的聚合物组合物是粉末或者颗粒的形式。
通式(I)、(II)和(III)的化合物是商品化合物。
通式(I)的化合物是双(3-叔丁基-4-羟基-5-甲基-苯基)双环戊二烯,由Eliokem以WingstayL出售或者由Raschig以RaloxLC出售。在商品化合物中,通式(I)中的n的平均值是大约1。
通式(II)的化合物是4,4’-硫代双(6-叔丁基-3-甲基苯酚),由CibaSpecialty Chemicals Inc.以CIBAIrganox 415出售。
通式(III)的化合物是1,3,5-三[4-(1,1-二甲基乙基)-3-羟基-2,6-二甲基苯基]甲基]-1,3,5-三嗪-2,4,6(1H,3H,5H)-三酮,或者1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯,其由Ciba SpecialtyChemicals Inc.以CIBAIrganox 3790出售。
通式(I)的化合物是最优选的。
在特殊的实施方案中,硫醚是通式(IV)或者(V)的化合物
其中,R1独立地是C8-C20烷基。
特殊的通式(IV)的化合物是二月桂基硫代二丙酸酯和二硬脂基硫代二丙酸酯,它们是Ciba Specialty Chemicals Inc.的商业产品,商品名为CIBA IrganoxPS 800和CIBA IrganoxPS 802。其中R1=C8烷基的通式(V)的化合物也是Ciba Specialty Chemicals Inc.的商业产品,并且以商品名CIBA Irganox1520销售。
例如,空间位阻酚类抗氧剂的存在量,基于干燥接枝共聚物、组分a)的重量为0.05到1%。
例如,硫醚的存在量基于干燥接枝共聚物、组分a)的重量为0.1到5%、优选0.1到3%。
优选空间位阻酚类抗氧剂与硫醚的比例为1∶1到1∶5、更优选1∶2到1∶4。
在特殊的实施方案中,所述稳定的聚合物组合物还包含不同于通式(I)、(II)或者(III)的那些的其他空间位阻酚类抗氧剂、亚磷酸酯加工稳定剂、紫外线吸收剂、空间位阻胺光稳定剂、金属减活剂、除酸剂、脂肪酸金属盐、荧光增白剂、杀生物剂或者表面活性剂。
附加组分的实例如下。
1.抗氧化剂
1.1.烷基化的一元酚,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,侧链为直链或支链的壬基酚如2,6-二壬基-4-甲基酚,2,4-二甲基-6-(1′-甲基十一烷基-1′-基)酚,2,4-二甲基-6-(1′-甲基十七烷-1′-基)酚,2,4-二甲基-6-(1′-甲基十三烷-1′-基)酚及它们的混合物。
1.2.烷硫基甲基苯酚,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-乙基苯酚,2,6-双十二烷基硫甲基-4-壬基苯酚。
1.3.氢醌和烷基化氢醌,例如,2,6-二叔丁基-4-甲氧基苯酚,2,5-二叔丁基氢醌,2,5-二叔戊基氢醌,2,6-二苯基-4-十八烷氧基苯酚,2,6-二叔丁基氢醌,2,5-二叔丁基-4-羟基苯甲醚,3,5-二叔丁基-4-羟基苯甲醚,3,5-二叔丁基-4-羟基苯基硬脂酸酯,二(3,5-二叔丁基-4-羟基苯基)己二酸酯。
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,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-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)二硫醚。
1.6.亚烷基双酚,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′-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[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,十八烷基-4-羟基-3,5-二甲基苄基巯基乙酸酯,十三烷基-4-羟基-3,5-二叔丁基苄基巯基乙酸酯,三(3,5-二叔丁基-4-羟基苄基)胺,二(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫代对苯二甲酸酯,二(3,5-二叔丁基-4-羟基苄基)硫醚,异辛基-3,5-二叔丁基-4-羟基苄基巯基乙酸酯。
1.8.羟苄基化的丙二酸酯,例如二(十八烷基)-2,2-二(3,5-二叔丁基-2-羟基苄基)丙二酸酯,二(十八烷基)-2-(3-叔丁基-4-羟基-5-甲基苄基)丙二酸酯,双十二烷基巯基乙基-2,2-二(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-羟基苄基)丙二酸酯。
1.9.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,1,4-二(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,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)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,二(十八烷基)-3,5-二叔丁基-4-羟基苄基膦酸酯,二(十八烷基)-5-叔丁基-4-羟基-3-甲基苄基膦酸酯,3,5-二叔丁基-4-羟基苄基膦酸的单乙酯的钙盐。
1.12.酰氨基苯酚,例如,4-羟基月桂酰苯胺,4-羟基硬脂酰苯胺,N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.13.β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元或多元醇的酯,例如,与下列各醇的酯: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′-二(羟乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元或多元醇的酯,例如与下列各醇的酯: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′-二(羟乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷;3,9-二[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。
1.15.β-(3,5-二环己基-4-羟基苯基)丙酸与一元或多元醇的酯,例如与下列各醇的酯: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′-二(羟乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.16. 3,5-二叔丁基-4-羟基苯基乙酸与一元或多元醇的酯,例如与以下各醇的酯: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′-二(羟乙基)草酰胺,3-硫杂十一烷醇,3-硫杂十五烷醇,三甲基己二醇,三羟甲基丙烷,4-羟甲基-1-磷杂-2,6,7-三氧杂双环[2.2.2]辛烷。
1.17.β-(3,5-二叔丁基-4-羟苯基)丙酸的酰胺,例如,N,N′-二(3,5-二叔丁基-4-羟苯基丙酰)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-羟苯基丙酰)肼,N,N′-二[2-(3-[3,5-二叔丁基-4-羟苯基]丙酰氧基)乙基]草酰胺(Uniroyal供应的NaugardXL-1)。
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)二苯胺,N,N′-二甲基-N,N′-二仲丁基对苯二胺,二苯胺,N-烯丙基二苯胺,4-异丙氧基二苯胺,N-苯基-1-萘胺,N-(4-叔辛基苯基)-1-萘胺,N-苯基-2-萘胺,辛基化的二苯胺(例如p,p′-二叔辛基二苯胺),4-正丁基氨基苯酚,4-丁酰氨基苯酚,4-壬酰基氨基苯酚,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-萘胺,一和二烷基化的叔丁基/叔辛基二苯胺的混合物,一和二烷基化的壬基二苯胺的混合物,一和二烷基化的十二烷基二苯胺的混合物,一和二烷基化的异丙基/异己基二苯胺的混合物,一和二烷基化的叔丁基二苯胺的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪,吩噻嗪,一和二烷基化的叔丁基/叔辛基吩噻嗪的混合物,一和二烷基化的叔辛基吩噻嗪的混合物,N-烯丙基吩噻嗪,N,N,N′,N′-四苯基-1,4-二氨基丁-2-烯,N,N-二(2,2,6,6-四甲基哌啶-4-基)六亚甲基二胺,二(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。
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。
2.2. 2-羟基二苯酮,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.取代和未取代的苯甲酸的酯,例如,4-叔丁基苯基水杨酸酯,苯基水杨酸酯,辛基苯基水杨酸酯,二苯甲酰间苯二酚,二(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,十六烷基3,5-二叔丁基-4-羟基苯甲酸酯,十八烷基3,5-二叔丁基-4-羟基苯甲酸酯,2-甲基-4,6-二叔丁基苯基3,5-二叔丁基-4-羟基苯甲酸酯。
2.4.丙烯酸酯,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-甲氧羰基肉桂酸甲酯,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-甲氧羰基对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′-硫代二[4-(1,1,3,3-四甲基丁基)苯酚]的镍络合物,如1∶1或1∶2络合物,可以有或没有另外的配体如正丁胺、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一烷基酯(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-羟基吡唑的镍络合物,有或没有另外的配体。
2.6.空间位阻胺,例如,二(2,2,6,6-四甲基-4-哌啶基)酸酯,二(2,2,6,6-四甲基-4-哌啶基)丁二酸酯,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,二(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-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶和丁二酸的缩合物,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-1,3,5-三嗪的线型或环状缩合物,三(2,2,6,6-四甲基-4-哌啶基)次氮基三乙酸酯,四(2,2,6,6-四甲基-4-哌啶基)-1,2,3,4-丁烷四羧酸酯,1,1’-(1,2-乙二基)-二(3,3,5,5-四甲基哌嗪酮),4-苯甲酰-2,2,6,6-四甲基哌啶,4-十八烷氧基-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)癸二酸酯,N,N’-二(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉基-2,6-二氯-1,3,5-三嗪的线型或环状缩合物,2-氯-4,6-二(4-正丁氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙氨基)乙烷的缩合物,2-氯-4,6-二(4-正丁氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-二(3-氨基丙氨基)乙烷的缩合物,8-乙酰-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-2,4-二酮,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4-十八烷氧基-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-氨基丙氨基)乙烷和2,4,6-三氯-1,3,5-三嗪以及4-丁氨基-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-1,3,5-三嗪及N,N-二丁胺和4-丁氨基-2,2,6,6-四甲基哌啶的缩合物(CAS登记号[192268-64-7]),N-(2,2,6,6-四甲基-4-哌啶基)正十二烷基丁二酰亚胺,N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基丁二酰亚胺,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-哌啶氧基羰基)-2-(4-甲氧基苯基)乙烯,N,N’-二甲酰-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。
2.7.草酰胺,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’-二叔丁基草酰二苯胺,2,2’-二(十二烷氧基)-5,5’-二叔丁基草酰二苯胺,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’-乙基草酰二苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁基草酰二苯胺的混合物,邻位和对位甲氧基双取代的草酰二苯胺的混合物及邻位和对位乙氧基双取代的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-羟基丙氧基]苯基}-4,6-二(2,4-二甲基苯基)-1,3,5-三嗪。
3.金属去活化剂,例如N,N’-二苯基草酰胺,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)草酰二肼,草酰二苯胺,间苯二甲酰二肼,癸二酰二苯基酰肼,N,N’-二乙酰己酰二肼,N,N’-二(水杨酰)草酰二肼,N,N’-二(水杨酰)硫代丙酰二肼。
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,亚磷酸三月桂酯,亚磷酸三(十八烷基)酯,二硬脂基季戊四醇二亚磷酸酯,亚磷酸三(2,4-二叔丁基苯基)酯,二异癸基季戊四醇二亚磷酸酯,二(2,4-二叔丁基苯基)季戊四醇二亚磷酸酯,二(2,4-二异丙苯基)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’-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]-1,3,2-二氧杂磷杂环辛烷,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]-1,3,2-二氧杂磷杂环辛烷,2,2’,2”-次氮基[三乙基三(3,3’,5,5’-四叔丁基-1,1’-联苯-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。
特别优选的是以下的亚磷酸酯:
三(2,4-二叔丁基苯基)亚磷酸酯(CIBAIrgafos 168,CibaSpecialty Chemicals),三(壬基苯基)亚磷酸酯,
5.羟胺,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,由氢化牛油胺衍生的N,N-二烷基羟胺。
6.硝酮,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-十二烷基-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,由氢化牛油胺衍生的N,N-二烷基羟胺衍生形成的硝酮。
7.过氧化物清除剂,例如,β-硫代二丙酸的酯,如,十二烷基酯、十八烷基酯、十四烷基酯或十三烷基酯;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)二硫醚,季戊四醇四(β-十二烷基巯基)丙酸酯。
8.碱性共稳定剂,例如蜜胺,聚乙烯吡咯烷酮,双氰胺,氰脲酸三烯丙酯,脲衍生物,肼衍生物,胺类,聚酰胺,聚氨基甲酸酯类、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,邻苯二酚锑或邻苯二酚锌。
9.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),碱土金属(优选)的磷酸盐、碳酸盐或硫酸盐;有机化合物,例如一元或多元酸及其盐,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;聚合物,例如离子型共聚物(离聚物)。特别优选的是1,3:2,4-二(3’,4’-二甲基亚苄基)山梨醇,1,3:2,4-二(对甲基二亚苄基)山梨醇,和1,3:2,4-二(亚苄基)山梨醇。
10.填料和增强剂,例如碳酸钙,硅酸盐,玻璃纤维,玻璃球,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或纤维,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.苯并呋喃酮和二氢吲哚酮,例如在US 4,325,863、US 4,338,244、US 5,175,312、US 5,216,052、US 5,252,643、DE-A-4316611、DE-A-4316622、DE-A-4316876、EP-A-0589839或EP-A-0591102中公开的那些,或者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。
13.除酸剂:有机酸清除剂,例如环氧化大豆油(ESBO),或者无机碱,例如NaOH、KOH、Ca(OH)2等等。
组合物的特殊的实例是:
MBS胶乳和
WingstayL,CIBA Irganox415或者CIBA Irganox3790,或者其混合物
二月桂基硫代二丙酸酯(CIBA IrganoxPS 800=DLTDP)或者二硬脂基硫代二丙酸酯(CIBA IrganoxPS 802=DSTDP)或者CIBAIrganox1520;
其他受阻酚抗氧剂,例如CIBA Irganox245、CIBA Irganox1076和其混合物;和
油酸钾或者油酸钠,硬脂酸钾或者硬脂酸钠。
MBS胶乳和
WingstayL,或者CIBA Irganox415,或者CIBA Irganox3790,或者其混合物
二月桂基硫代二丙酸酯(CIBA IrganoxPS 800=DLTDP)或者CIBA Irganox1520,和
油酸钾。
两种特殊的组合物是含水的胶乳形式。
两种特殊的组合物还可以是固体状态,例如是粉末或者颗粒。
本发明的另一个方面是甲基丙烯酸甲酯和苯乙烯在聚丁二烯或者聚丁二烯-苯乙烯上的接枝共聚物(甲基丙烯酸甲酯-苯乙烯-丁二烯接枝共聚物MBS)的稳定化方法,所述接枝共聚物中不存在不是丁二烯上的接枝共聚物的其他苯乙烯聚合物或者共聚物,该方法包括以下步骤:
a)向MBS胶乳中加入上述的通式(I)、(II)或者(III)的空间位阻酚类抗氧剂和硫醚;
b)将MBS胶乳凝聚,和
c)在升高的温度下将MBS胶乳干燥。
通式(I)、(II)或者(III)的空间位阻酚类抗氧剂和硫醚可以单独地加入或者一起加入。它们借助于传统方法混合到胶乳中,例如借助于搅拌器。稳定的胶乳的制备描述在例如US5,116,534中。
凝聚步骤是已知的工艺,其可以按照例如在EP 0488550中的描述进行。特别地,酸(例如盐酸或者硫酸)或者无机盐(例如硫酸镁或者氯化钙)可以用作凝聚剂。
通常,干燥步骤在40℃到150的温度下、优选在50℃到80℃的温度下进行。
在很多情况下,在降低的压力下、例如在10毫巴到500毫巴下实施干燥步骤可能是有用的。为了加速干燥步骤,可以施加附加的空气或者氮气。典型的干燥时间为1小时到24小时。
作为凝聚的替代方案,MBS接枝共聚物也可以通过冷冻或者喷雾干燥来分离。
本发明的又一个方面是通式(I)、(II)或者(III)的空间位阻酚类抗氧剂连同硫醚用于稳定甲基丙烯酸甲酯和苯乙烯在聚丁二烯或者聚丁二烯-苯乙烯上的接枝共聚物(甲基丙烯酸甲酯-苯乙烯-丁二烯接枝共聚物MBS)的用途,其中所述接枝共聚物中不存在不是丁二烯上的接枝共聚物的其他苯乙烯聚合物或者共聚物。
以上关于组合物给出的定义和优选特征也适合于本发明的其他方面。
胶乳形式或者干燥颗粒或者粉末形式的稳定的MBS可用作热塑性聚合物或者弹性体聚合物的冲击改性剂。
可以向其中引入干燥或者胶乳形式的稳定的MBS的聚合物实例如下。
1.单烯烃和双烯烃的聚合物,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,以及环烯烃的聚合物,例如环戊烯或降冰片烯,聚乙烯(可任选地交联),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,即前一段中列举的单烯烃的聚合物,优选聚乙烯和聚丙烯,可以用各种不同的方法、尤其是以下方法制备:
a)自由基聚合(通常在高压和高温下)。
b)利用通常含周期表IVb、Vb、VIb或VIII族中一种或多种金属的催化剂进行催化聚合。这些金属通常有一或多配体,一般是氧化物、卤化物、醇化物、酯、醚、胺、烷基、烯基和/或芳基,它们或是π配位或σ配位。这此金属络合物可以是游离形式或是固定在载体上,通常是在活化的氯化镁、氯化钛(III)、氧化铝或二氧化硅上。这些催化剂在聚合介质中可以溶解或不溶解。这些催化剂可以本身用于聚合反应,或是使用进一步的活化剂,一般是烷基金属、金属氢化物、金属烷基卤化物、金属烷基氧化物或金属烷基环氧化物,该金属是元素周期表的Ia、IIa、和/或IIIa族元素。活化剂可以方便地用酯、醚、胺或甲硅烷基醚基团改性。这些催化剂体系通常称为Phillips,standard OilIndiana,Ziegler(-Natta),TNZ(Dupont),金属茂或单中心催化剂(SSC)。
2. 1)中所述的聚合物的混合物,例如聚丙烯与聚异丁烯、聚丙烯与聚乙烯(例如PP/HDPE,PP/LDPE)的混合物和不同类型聚乙烯的混合物(例如LDPE/HDPE)。
3.单烯烃和双烯烃彼此间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,聚乙烯/丁-1-烯共聚物,聚乙烯/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),乙烯/1-烯烃共聚物(共中该1-烯烃原位生成),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,乙烯/丙烯酸共聚物及其盐(离聚物)以及乙烯与丙烯和一种二烯(例如己二烯、二环戊二烯或亚乙基降冰片烯)的三元共聚物;和这些共聚物相互间的混合物和与以上1)中所述聚合物的混合物,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以及交替或无规的聚烯烃/一氧化碳共聚物及其与其它聚合物如聚酰胺的混合物。
4.烃树脂(例如C5-C9),包括其氢化改性物(如增粘剂)和聚烯烃和淀粉的混合物。
1)至4)的均聚物和共聚物可以具有任何立体结构,包括间同、全同、半全同或无规立构结构,优选无规立构聚合物。立构规整嵌段聚合物也包括在内。
5.聚苯乙烯,聚(对甲基苯乙烯)、聚(α-甲基苯乙烯)。
6.自乙烯基芳族单体衍生的芳族均聚物和共聚物,这些单体包括苯乙烯,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,乙烯基萘和乙烯基蒽,以及它们的混合物。均聚物和共聚物可具有任何立体结构,包括间同、全同、半全同或无规立构结构,优选无规立构聚合物。立构规整嵌段聚合物也包括在内。
6a.包括上述乙烯基芳族单体和共聚单体的共聚物,该共聚单体选自乙烯、丙烯、二烯、腈类、酸、马来酸酐、马来酰亚胺、乙酸乙烯酯和氯乙烯或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(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/丙烯酸甲酯;高冲击强度苯乙烯共聚物和另一种聚合物,例如聚丙烯酸酯、一种二烯聚合物或一种乙烯/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/苯乙烯或苯乙烯/乙烯/丙烯/苯乙烯。
6b.由6)所述聚合物氢化衍生的氢化的芳族聚合物,特别包括由无规立构的聚苯乙烯氢化制得的聚环己基乙烯(PCHE),常称为聚乙烯基环己烷(PVCH)。
6c.由上述6a)中的聚合物氢化衍生的氢化的芳族聚合物。
均聚物和共聚物可以有任何立体结构,包括间同立构、全同立构、半全同立构或无规立构,其中优选无规立构聚合物。还包括立构规整嵌段聚合物。
7.含卤素聚合物,例如,聚氯丁二烯,氯化橡胶,氯化和溴化的异丁烯/异戊二烯共聚物(卤丁基橡胶),氯化或磺氯化的聚乙烯,乙烯和氯乙烯的共聚物,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1,1-二氯乙烯、聚氟乙烯、聚偏1,1-二氟乙烯、以及它们的共聚物,例如氯乙烯/1,1-二氯乙烯、氯乙烯/乙酸乙烯酯或1,1-二氯乙烯/乙酸乙烯酯共聚物。
8.由α,β-不饱和酸及其衍生物形成的聚合物,例如聚丙烯酸酯和聚甲基丙烯酸酯;用丙烯酸丁酯增韧的聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈类。
9.9)中所述单体彼此间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。
10.由不饱和醇和胺或其酰基衍生物或乙缩醛衍生的聚合物,例如聚乙烯醇、聚乙酸乙烯酯、聚硬脂酸乙烯酯、聚苯甲酸乙烯酯、聚马来酸乙烯酯、聚乙烯基缩丁醛、聚苯二甲酸烯丙酯或聚烯丙基蜜胺;及其与以上1)中所述烯烃的共聚物。
11.环醚的均聚物和共聚物,例如聚亚烷基二醇、聚环氧乙烷、聚环氧丙烷或它们与双缩水甘油醚的共聚物。
12.聚缩醛类,例如,聚甲醛和含环氧乙烷作为共聚单体的聚甲醛。
13.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。
14.以羟基结尾的聚醚、聚酯或聚丁二烯的一方,脂族或芳族聚异氰酸酯为另一方,衍生形成的聚氨酯,及其前体物。
15.由二胺和二羧酸和/或由氨基羧酸或相应的内酰胺衍生形成的聚酰胺和共聚酰胺,例如聚酰胺4、6、6/6、6/10、6/9、6/12、4/6、12/12、11、12;由间二甲苯二胺和己二酸起始的芳族聚酰胺;由六亚甲基二胺和间苯二甲酸和/或对苯二甲酸加或不加作为改性剂的弹性体制得的聚酰胺,例如聚-2,4,4-三甲基六亚甲基对苯二甲酰胺或聚间苯二甲酰间苯二胺;以及上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或者化学结合或接枝的弹性体的嵌段共聚物;或与聚醚,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;和在加工期间缩聚的聚酰胺(RIM聚酰胺体系)。
16.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。
17.由二羧酸和二醇以及/或由羟基羧酸或相应的内酯衍生的聚酯,例如聚对苯二甲酸乙二酯、聚对苯二甲酸丁二酯,聚-1,4-二羟甲基环己烷对苯二甲酸酯,聚亚烷基萘二甲酸酯(PAN)和聚羟基苯甲酸酯,以及由羟基终端的聚醚衍生的嵌段共聚醚酯;及用聚碳酸酯或MBS改性的聚酯。
18.聚碳酸酯和聚酯碳酸酯。
19.聚酮。
20.聚砜,聚醚砜和聚醚酮。
21.上述聚合物的共混物(高分子共混物),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/丙烯酸脂,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。
以下实施例举例说明本发明。
抗氧剂分散体按照US5,116,534中的描述制备,使用油酸和氢氧化钾作为表面活性剂。它们具有40%的活性物质含量。
实施例1-3和对比例2:MBS接枝胶乳的稳定化和凝聚
在环境温度下,在搅拌下,将计算量的相应的抗氧剂分散体加到MBS胶乳中。继续搅拌5分钟(磁力搅拌器,大约1000rpm)。在凝聚之前将稳定的MBS胶乳过滤。将210g去离子水与基于干燥的MBS为10.5%的盐酸(10%)混合,然后将混合物加热到55℃。在该温度和在700rpm的搅拌下,在1到2分钟内加入150g稳定的MBS接枝胶乳(37.7%总固体含量)。然后将温度提高到60℃(浴温73℃),在该水平下保持5分钟,然后提高到85℃(浴温103℃),并在该水平下保持5分钟。测定pH值。将混合物热过滤。将固体残余物取到在环境温度下的200克去离子水中,过滤,并且用去离子水洗涤。然后将MBS接枝粉末在60℃下、在大约150毫巴和空气流下干燥15h。
利用DSC设备,在氧气氛下测定所制备的MBS粉末的热稳定性。测定在180℃下放热反应达到极限时的时间。出现的放热反应是测定聚合物的降解的尺度。
制备的不同的MBS粉末的稳定化和其热稳定性示于表1中。
表1:稳定的MBS粉末的热稳定性
实施例 | 添加剂1 | 浓度* | 添加剂2 | 浓度* | 热稳定性** |
对比例1*** | Irganox 1076 | 0.2% | DLTDP | 0.6% | 35分钟 |
对比例2 | Irganox 245 | 0.3% | DLTDP | 0.9% | 283分钟 |
本发明1 | Irganox 3790 | 0.3% | DLTDP | 0.9% | 388分钟 |
本发明2 | Irganox 415 | 0.3% | DLTDP | 0.9% | 454分钟 |
本发明3 | Wingstay L | 0.3% | DLTDP | 0.9% | 350分钟 |
*添加剂浓度是基于干燥的MBS粉末的重量%。
**热稳定性DSC,180℃,氧气,铝杯:达到最大温升的分钟数。
***对比例1用基于干燥的MBS为1.21%的硫酸(6.8g 10%硫酸)凝聚的。
Claims (12)
2.权利要求1的稳定的聚合物组合物,其是固体状态。
3.权利要求2的稳定的聚合物组合物,其是粉末或者颗粒的形式。
5.权利要求1的稳定的聚合物组合物,其中所述空间位阻酚类抗氧剂的存在量基于干燥的接枝共聚物、组分a)的重量为0.05到1%。
6.权利要求1的稳定的聚合物组合物,其中所述硫醚的存在量基于干燥的接枝共聚物、组分a)的重量为0.1到5%。
7.权利要求1的稳定的聚合物组合物,其中空间位阻酚类抗氧剂与硫醚的比例为1∶1到1∶5。
8.权利要求1的稳定的聚合物组合物,其还包含不同于权利要求1中的那些的其他空间位阻酚类抗氧剂、亚磷酸酯加工稳定剂、紫外线吸收剂、空间位阻胺光稳定剂、金属减活剂、除酸剂、脂肪酸的金属盐、荧光增白剂、杀生物剂或者表面活性剂。
9.一种用于甲基丙烯酸甲酯和苯乙烯在聚丁二烯或者聚丁二烯-苯乙烯上的接枝共聚物(甲基丙烯酸甲酯-苯乙烯-丁二烯接枝共聚物MBS)的稳定化的方法,所述接枝共聚物中不存在不是丁二烯上的接枝共聚物的其他苯乙烯聚合物或者共聚物,该方法包括以下步骤:
a)向MBS胶乳中加入按照权利要求1的通式(I)、(II)或者(III)的空间位阻酚类抗氧剂和硫醚;
b)将MBS胶乳凝聚,和
c)在升高的温度下将MBS胶乳干燥。
10.权利要求9的方法,其中所述干燥步骤在40℃到150℃的温度下进行。
11.通式(I)、(II)或者(III)的空间位阻酚类抗氧剂连同硫醚用于稳定甲基丙烯酸甲酯和苯乙烯在聚丁二烯或者聚丁二烯-苯乙烯上的接枝共聚物(甲基丙烯酸甲酯-苯乙烯-丁二烯接枝共聚物MBS)的用途,其中所述接枝共聚物中不存在不是丁二烯上的接枝共聚物的其他苯乙烯聚合物或者共聚物。
12.按照权利要求9的稳定的MBS接枝共聚物作为聚合物的冲击改性剂的用途。
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US5451624A (en) * | 1994-02-15 | 1995-09-19 | Rohm And Haas Company | Stabilized modifier and impact modified thermoplastics |
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JP4781570B2 (ja) * | 2001-07-25 | 2011-09-28 | 日本エイアンドエル株式会社 | 安定剤の乳化・分散液を調合する方法 |
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