CN1079809C - 协同稳定剂混合物 - Google Patents
协同稳定剂混合物 Download PDFInfo
- Publication number
- CN1079809C CN1079809C CN96101386A CN96101386A CN1079809C CN 1079809 C CN1079809 C CN 1079809C CN 96101386 A CN96101386 A CN 96101386A CN 96101386 A CN96101386 A CN 96101386A CN 1079809 C CN1079809 C CN 1079809C
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- China
- Prior art keywords
- formula
- compound
- alkyl
- phenyl
- component
- 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.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 239000003381 stabilizer Substances 0.000 title claims abstract description 46
- 230000002195 synergetic effect Effects 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 88
- 239000001257 hydrogen Substances 0.000 claims abstract description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 36
- -1 polyethylene Polymers 0.000 claims description 144
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 239000011368 organic material Substances 0.000 claims description 17
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000005977 Ethylene Substances 0.000 claims description 12
- 239000000047 product Substances 0.000 claims description 12
- 239000004743 Polypropylene Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 229920000768 polyamine Polymers 0.000 claims description 9
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 claims description 8
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- 238000000034 method Methods 0.000 claims description 7
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- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
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- 125000005466 alkylenyl group Chemical group 0.000 claims description 2
- 238000007334 copolymerization reaction Methods 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
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- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 11
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- 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 8
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 6
- 239000012964 benzotriazole Substances 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 5
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 5
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 5
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 5
- 229920000092 linear low density polyethylene Polymers 0.000 description 5
- 239000004707 linear low-density polyethylene Substances 0.000 description 5
- 238000002156 mixing Methods 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
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 5
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 4
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 4
- 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
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
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- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 3
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- NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 3
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- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
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Abstract
一种协同稳定剂混合物,包括组分a)和例如组分b),其中组分a)是至少一种式Ⅰ化合物,式Ⅰ中R1是C1-C10烷基、C5-C20环烷基、C1-C4烷基取代的C5-C12环烷基、苯基或C1-C10烷基取代的苯基,R2是C3-C10烷撑,R3是氢、C1-C8烷基、O、-CH2CN、C3-C6链烯基、C7-C9苯基烷基、苯基被C1-C4烷基取代的C7-C9苯基烷基或C1-C8酰基,和n1是1到50的数;和组分b)是例如下式化合物,其中n2是2到20的数。
Description
本发明涉及一种包括两种特殊高分子量多烷基哌啶衍生物的稳定剂体系,该稳定剂体系在稳定有机材料中的用途和借助所述稳定剂体系抗热、氧化或光引发降解的有机材料。
US-A-4692486,US-A-4863981,US-A-4957953,WO-A-92/12201,EP-A-449685,EP-A-632092,GB-A-2267499和Research Disclosure 34549(1993年1月)描述含两个多烷基哌啶衍生物的稳定剂混合物。
本发明涉及一种稳定剂混合物,包括组分a)和组分b)、c)、d)、e)、f)或g),其中
R2是C3-C10烷撑,
R3是氢,C1-C8烷基,O;-CH2CN,C3-C6链烯基,C7-C9苯基烷基,苯基被C1-C4烷基取代的C7-C9苯基烷基;或C1-C8酰基和,
n1是1到50的数;
组分b)是至少一种式(II)化合物其中R4,R6,R7和R8彼此独立地为氢,C1-C12烷基,C5-C12环烷基,C1-C4烷基取代的C5-C12环烷基,苯基,被-OH和/或C1-C10烷基取代的C7-C9苯基烷基;或式III基团R5是C2-C18烷撑,C5-C7亚环烷基或C1-C4烷撑二(C5-C7亚环烷基),或R4,R5和R6一起与它们相连的氮原子形成5元到10元杂环,或R7和R8一起与它们相连的氮原子形成5元到10元杂环,R9定义同R3,n2是2到50的数,和R4,R6,R7和R8至少一个是式(III)基团;
组分c)是将式IVa的多胺与氰尿酰氯反应获得的产物与式IVb化合物反应获得的产物, 其中n3’,n3”和n3彼此独立地是2到12的数,R10是氢,C1-C12烷基,C5-C12环烷基,苯基或C7-C8苯基烷基,和R11定义同R3;
组分e)是至少一种式(VIa)和(VIb)的化合物其中n5和n5 *彼此独立地是2到50的数;
组分f)是至少一种式(VII)化合物其中R14和R18彼此独立地是一直键或-N(X1)-CO-X2-CO-N(X3)-基团,其中X1和X3彼此独立地是氢、C1-C8烷基、C5-C12环烷基、苯基、C7-C9苯基烷基或式III基团,X2是一直键或C1-C4烷撑,R15定义同R3,R16,R17,R20和R21彼此独立地是氢、C1-C30烷基、C5-C20环烷基或苯基,R19是氢、C1-C30烷基、C5-C12环烷基、C7-C9苯基烷基、苯基或式III基团,和n6是1到50的数;
有至多30个碳原子烷基的例子是甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、正戊基、异戊基、1-甲基戊基、1,3-二甲基丁基、正己基、1-甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、2-乙基己基、1,1,3-三甲基己基、1,1,3,3-四甲基戊基、壬基、癸基、十一烷基、1-甲基十一烷基、十二烷基、1,1,3,3,5,5-六甲基己基、十三烷基、十四烷基、十五烷基、十六烷基、十七烷基、十八烷基、二十烷基,二十二烷基和二十三烷基。R3,R9,R11,R15,R17,R21和R27优选的定义之一是C1-C4烷基,特别是甲基,R16和R20优选的定义之一是C1-C25烷基,特别是C15-C25烷基,例如十六烷基和C18-C22烷基。R19优选的定义之一是C1-C25烷基,特别是十八烷基。
C5-C12环烷基的例子是环戊基,环己基,环庚基,环辛基和环十二烷基。C5-C8环烷基,特别是环己基是优选的。
C1-C4烷基取代的C5-C12环烷基是,例如,甲基环己基或二甲基环己基。
被-OH和/或C1-C10烷基取代的苯基是,例如,甲基苯基,二甲基苯基,三甲基苯基,叔丁基苯基或3,5-二叔丁基-4-羟基苯基。
C7-C9苯基烷基的例子是苄基和苯基乙基。
苯基被-OH和/或有至多10个碳原子的烷基取代的C7-C9苯基烷基是,例如,甲基苄基,二甲基苄基,三甲基苄基,叔丁基苄基或3,5-二叔丁基-4-羟基苯基。
C3-C6链烯基的例子是烯丙基,2-甲基烯丙基,丁烯基,戊烯基和己烯基。烯丙基是优选的。
C1-C8酰基优选是C1-C8链烷酰基,C3-C8链烯酰基或苯甲酰基。例子是甲酰基,乙酰基,丙酰基,丁酰基,戊酰基,己酰基,辛酰基,苯甲酰基,丙烯酰基和巴豆酰基。
有至多18个碳原子的烷撑的例子是亚甲基,乙撑,丙撑,三亚甲基,四亚甲基,五亚甲基,2,2-二甲基三亚甲基,六亚甲基,三甲基六亚甲基,八亚甲基,十亚甲基。R5优选是六亚甲基,R13优选是乙撑,R22和R24优选是亚甲基,R25优选是2,2-二甲基乙撑,和R26优选是1,1-二甲基乙撑。C5-C7亚环烷基的一个例子是亚环己基。
C1-C4烷撑二(C5-C7亚环烷基)的一个例子是亚甲基二亚环己基。
如果R4,R5和R6一起与它们相连的氮原子形成5元到10元杂环,这可例如是6元杂环是优选的。
如果R7和R8一起与它们相连的氮原子形成5元到6元杂环,这可为例如,1-吡咯烷基,哌啶子基,吗啉代,1-哌嗪基,4-甲基-1-哌嗪基,1-六氢吖庚因基,5,5,7-三甲基-1-高哌嗪基或4,5,5,7-四甲基-1-高哌嗪基,吗啉代是特别优选的。
R16和R20优选的定义之一是苯基。
X2和R23是优选是一直键。
X1,X3,R3,R9,R11,R15和R27优选是氢。
n1优选是1-25,特别是2-20或2-10。
n2优选2-25。
n3’,n3”,n3”优选是2-4。
n4优选是2-25,特别是2-20或2-10。
n5和n5 *优选是2-25,特别是2-20或2-10。
n6优选是1-25,特别是1-20或1-10。
n7优选是1-25,特别是1-20或1-10。
组分a)到g)中所述的化合物基本上是已知的(在某些情况下是可商购的)且可用已知方法制备,例如描述在US-A-5051458,US-A-4086204,US-A-4331586,US-A-4233412,US-A-4340534,US-A-4857595,DD-A-262434(Derwent 89-122983/17,Chemical Abstracts 111:58964u),DE-A-4239437(Derwent 94-177274/22)和US-A-4529760,US-A-4477615和ChemicalAbstracts-CAS No.136504-96-6中。
组分c)可用类似于已知方法制备,例如通过式IVa多胺与氰尿酰氯;摩尔比为1∶2到1∶4,在无水碳酸锂,碳酸钠或碳酸钾存在下,于有机溶剂如1,2-二氯乙烷,甲苯,二甲苯,苯,二恶烷或叔戊醇,在温度从-20℃到+10℃下,优选从-10℃到+10℃,特别是从0℃到+10℃下反应2到8小时,随后所得产物与式IVb的2,2,6,6-四甲基-4-哌啶基胺反应。2,2,6,6-四甲基-4-哌啶基胺和式IVa的多胺的摩尔比例如为4∶1到8∶1。2,2,6,6-四甲基-4-哌啶基胺可一次加入或多于一次,间隔几小时加入。
式IVa多胺:氰尿酰氯:式IVb的2,2,6,6-四甲基-4-哌啶基胺比优选为1∶3∶5到1∶3∶6。
下列实施例表明制备优选的组分c)的一个方法。
实施例
将23.6g(0.128mol)氰尿酰氯,7.43g(0.0426mol)N,N’-双[3-氨基丙基]亚乙基二胺和18g(0.13mol)无水碳酸钾在5℃下于250ml 1,2-二氯乙烷中,搅拌下反应3小时。将该混合物在室温下再温热4小时。将27.2g(0.128mol)N-(2,2,6,6-四甲基-4-哌啶基)丁胺加入,所得混合物在60℃下温热2小时。再加入18g(0.13mol)无水碳酸钾,将混合物在60℃下再温热6小时。在轻微真空(200mbar)下蒸馏除去溶剂并用二甲苯置换。将18.2g(0.085mol)N-(2,2,6,6-四甲基-4-哌啶基)丁胺和5.2g(0.13mol)细粉碎氢氧化钠加入,将混合物回流2小时,再用12小时共沸精馏除去反应中形成的水。过滤混合物,用水洗涤溶液并用Na2SO4干燥。蒸发溶剂,真空(0.1mbar)下在120-130℃干燥残留物,组分c)作为无色树脂获得。
优选式IV-1是
组分a)优选是UVSAIL 299或UVASIL 125,组分b)优选是CHIMASSORB 944、CYASORB UV 3346或DASTAB 1082,组分c)优选是UVASORB HA88,组分d)优选TINUVIN622,组分e)优选是HOSTAVIN 30,组分f)优选是UVINUL 5050H、LICHTSCHUTZSTOFF UV 31或LUCHEM B18,和组分g)优选是MARK LA63或MARK LA68。
式VIa和VIb化合物可一起作为混合物且也作为组分e)用于新型稳定剂体系中。VIa∶VIb之比是,例如从20∶1到1∶20或从1∶10到10∶1。
饱和式I,II,IV-1,IV-2,IV-3,V,VIa,VIb,VII和VIII空键的端基的定义取决于用来制备它们的方法。这些端基也可在化合物制成后改性。
在式I化合物中,连到硅原子上的端基可以是,例如(R1)3Si-O-,和连到氧上的端基可以是,例如,-Si(R1)3。
式I化合物也可为环状化合物如果n3是3到10的数,即示在结构式中的空键形成一直键。
如果X是卤素,当反应结束时,最好用例如-OH或氨基代换该卤素。可提及的氨基的例子是1-吡咯烷基,吗啉代,-NH2,-N(C1-C8烷基)2和-NR(C1-C8烷基),其中R是氢或式III基团。
在式VI-1,IV-2和IV-3化合物中,连到三嗪基团上的端基是,例如,Cl或和连到氨基上的端基是,例如,氢或如果式I化合物是例如通过下式化合物其中R12是氢或甲基,与式Y-OOC-R13-COO-Y的二元羧酸二酯,其中Y是例如甲基,乙基或丙基,和R13定义同上反应来制备,则连到2,2,6,6-四甲基-4-氧基哌啶-1-基上的端基是氢或-CO-R13-COO-Y,和连到二酰基上的端基是-O-Y或
在式VIb化合物中,连到二亚甲基上的端基可以是例如-OH,连到氧上的端基可以是例如,氢。这些端基也可为多醚基。
在式VII中,连到2,5-二氧吡咯烷环上的端基,例如是氢,连到-C(R20)(R21)-上的端基是例如在式VIII化合物中,连到羰基上的端基是例如和连到氧基上的端基是例如优选的稳定剂混合物是其中R3,R9,R11,R15和R17是氢或甲基。
同样优选的稳定剂混合物是其中R1是C1-C4烷基、C5-C8环烷基或苯基,R2是C3-C6烷撑,和n1是1到25的数;R4,R6,R7和R8彼此独立地是氢、C1-C8烷基、C5-C8环烷基、苯基、C7-C9苯基烷基或式III基团,或R7和R8一起与它们相连的氮原子形成一6元杂环,R5是C2-G10烷撑,和n2是2到25的数;n’3,n”3和n3彼此独立是2到4的数,和R10是C1-C4烷基;R12是氢,R13是乙撑,和n4是2到25的数;n5和n5 *彼此独立是2到25的数;R14和R18是一直键或-N(X1)-CO-X2-CO-N(X3)-基,X1和X3彼此独立地是氢或C1-C4烷基,X2是一直键,R16和R20是C1-C25烷基或苯基,R17和R21是氢或C1-C4烷基,R19是C1-C25烷基或式III基团,和n6是1到25的数;R22,R24,R25和R26是C1-C4烷撑,n23是一直键,和n7是1到25的数。
特别优选的稳定剂混合物是其中组分a)是至少一种式I-A化合物其中n1是1到20的数;组分b)是至少一种式(Il-B-1)、(II-B-2)或(II-B-3)的化合物 其中n2是2到20的数;组分c)是可由下式多胺H2N-(CH2)3-NH-(CH2)2-NH-(CH2)3-NH2与氰尿酰氯的反应产物与下式化合物反应获得的产物:组分d)是至少一种式(V-D)化合物其中n4是2到20的数;组分e)中的n5和n5 *彼此独立地是2到20的数;组分f)是至少一种式(VII-F-1)、(VII-F-2)或(VII-F-3)的化合物 其中n6是1到20的数;组分g)是至少一种式(VIII-G)的化合物其中R27是氢或甲基,和R7是1到20的数。
下列的稳定剂混合物可作为例子提及
1包括组分a)和b)的稳定剂混合物,
2包括组分a)和c)的稳定剂混合物,
3包括组分a)和d)的稳定剂混合物,
4包括组分a)和e)的稳定剂混合物,
5包括组分a)和f)的稳定剂混合物,和
6包括组分a)和g)的稳定剂混合物,
特别优选的是下列稳定剂体系:
a)包括至少一种式(I-A)化合物和至少一种式(II-B-1)化合物,
b)包括至少一种式(I-A)化合物和至少一种式(II-B-3)化合物,
d)包括至少一种式(I-A)化合物和至少一种式(V-D)化合物的稳定剂混合物,和
e)包括至少一种式(1-A)化合物和至少一种式(VIa)和(VIb))化合物的稳定剂混合物。
在上述稳定剂体系中,两种组分优选重量比为1∶1。
新型稳定剂混合物是适合稳定有机材料以防热、氧化或者光引发降解。这类材料的例子如下:
1.单烯烃和二烯烃的聚合物,例如聚丙烯、聚异丁烯、聚(1-丁烯)、聚(4-甲基-1-戊烯)、聚异戊二烯或聚异丁二烯,以及环烯如环戊烯或降冰片烯的聚合物,聚乙烯(它可以是交联的)如高密度聚乙烯(HDPE)、高密度高分子量聚乙烯(HDPE-HMW)、高密度超高分子量聚乙烯(HDPE-UHMW)、中等密度聚乙烯(MDPE)、低密度聚乙烯(LDPE)、线型低密度聚乙烯(LLDPE)、支化低密度聚乙烯(BLDPE)。
聚烯烃、即上段所述的单烯烃聚合物、特别是聚乙烯和聚丙烯可用各种方法、特别是下述方法制备:
a)自由基聚合(通常在高压和升高的温度下进行)。
b)使用催化剂的催化聚合,该催化剂通常含有1种或多种元素周期表IVb、Vb、VIb或VIII族的金属。这些金属通常具有1个或多个配位体,通常为氧化物、卤化物、醇盐、酯、醚、胺、烷基、链烯基和/或芳基,它们可以是π-或σ-配位的。这些金属配位化合物可以直接使用或固定于载体上、通常在活化氯化镁、氯化钛(III)、氧化铝或二氧化硅上使用。这些催化剂可溶于或不溶于聚合反应介质中,这些催化剂在聚合反应中可单独使用,或者进一步用烷基金属、金属氢化物、烷基金属卤化物、烷基金属氧化物或烷基恶唑烷金属进一步活化,活化剂中的金属为元素周期表Ia、IIa和/或IIIa族的元素。这些活化剂可用其它酯、醚、胺或甲硅烷基醚基团改性。这些催化体系通常被称作Phillips、Standard Oil Indiana、Ziegler(-Natta)、TNZ(Dupont)、金属茂或单中心催化剂(SSC)。
2.1中所述聚合物的混合物,例如聚丙烯与聚异丁烯的混合物,聚丙烯与聚乙烯的混合物(如PP/HDPE、PP/LDPE)以及不同类型聚乙烯的混合物(如LDPE/HDPE)。
3.单烯烃与二烯烃或其它乙烯基单体的共聚物,例如:乙烯/丙烯共聚物,线型低密度聚乙烯(LLDPE)及其与低密度聚乙烯(LDPE)的混合物,丙烯/1-丁烯共聚物,丙烯/异丁烯共聚物、乙烯/1-丁烯共聚物,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,丙烯/丁二烯共聚物,异丁烯/异戊二烯共聚物,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/乙酸乙烯酯共聚物以及它们与一氧化碳的共聚物,或乙烯/丙烯酸共聚物及它们的盐(离子聚合物),以及乙烯、丙烯与如己二烯、二环戊二烯或乙叉降冰片烯的二烯烃的三元共聚物;这些共聚物的混合物或与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-乙酸乙烯酯共聚物(EVA)、LDPE/乙烯-丙烯酸共聚物(EAA)、LLDPIE/EVA、LLDPE/EAA,以及聚亚烷基/一氧化碳交替或无规共聚物,和它们与其它聚合物如聚酰胺的混合物。
4.烃树脂(如C5-C9)及其氢化改性产物(如粘合剂)以及聚亚烷基与淀粉的混合物。
5.聚苯乙烯,聚(对甲基苯乙烯),聚(α-甲基苯乙烯)。
6.苯乙烯或α-甲基苯乙烯与二烯烃或丙烯酸衍生物的共聚物,例如:苯乙烯/丁二烯、苯乙烯/丙烯腈、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/马来酐、苯乙烯/丙烯腈/丙烯酸甲酯的共聚物;高冲击强度苯乙烯共聚物与另一聚合物如聚丙烯酸酯、二烯烃聚合物或乙烯/丙烯/二烯烃三元共聚物的混合物;苯乙烯的嵌段共聚物,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/苯乙烯嵌段共聚物。
7.苯乙烯或α-甲基苯乙烯的接枝共聚物,如:苯乙烯接枝于聚丁二烯、苯乙烯接枝于聚(丁二烯-苯乙烯)或聚(丁二烯-丙烯腈)上的接枝共聚物;苯乙烯和丙烯腈(或甲基丙烯腈)接枝于聚丁二烯上的共聚物;苯乙烯、丙烯腈和甲基丙烯酸甲酯接枝于聚丁二烯上的共聚物;苯乙烯和马来酐接枝于聚丁二烯上的共聚物;苯乙烯、丙烯腈和马来酐或马来酰亚胺接枝于聚丁二烯上的共聚物;苯乙烯和马来酰亚胺接枝于聚丁二烯上的共聚物;苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯接枝于聚丁二烯上的共聚物;苯乙烯和丙烯腈接枝于乙烯/丙烯/二烯烃三元共聚物上的共聚物;苯乙烯和丙烯腈接枝于聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上的共聚物;苯乙烯和丙烯腈接枝于丙烯酸酯/丁二烯共聚物上的共聚物;以及它们与6中所列共聚物的混合物,例如称作ABS、MBS、ASA或AES聚合物的共聚物混合物。
8.含卤聚合物,如:聚氯丁二烯,氯化橡胶,氯化和溴化异丁烯/异戊二烯共聚物(卤丁橡胶),氯化或氯磺化聚乙烯,乙烯和氯代乙烯的共聚物,表氯醇均聚物和共聚物,特别是含氯乙烯基化合物的聚合物,如聚氯乙烯、聚偏二氯乙烯、聚氟乙烯、聚偏二氟乙烯,以及它们的共聚物,如氯乙烯/偏二氯乙烯、氯乙烯/乙酸乙烯酯或偏二氯乙烯/乙酸乙烯酯共聚物。
9.衍生于α,β-不饱和酸及其衍生物的聚合物,如聚丙烯酸酯和聚甲基丙烯酸酯;用丙烯酸丁酯改进了耐冲击性能的聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈。
10.在9中提到的单体的共聚物或与其它不饱和单体的共聚物,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/丙烯酸烷氧烷基酯或丙烯腈/乙烯基卤共聚物,或者丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
11.衍生于不饱和醇和胺或其酰化衍生物或其缩醛的聚合物,例如,聚乙烯基醇,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,聚乙烯醇缩丁醛,聚邻苯二甲酸烯丙酯或聚烯丙基密胺;以及它们与1中的烯烃的共聚物。
12.环醚的均聚物和共聚物,聚烷二醇、聚环氧乙烷、聚氧化丙烯,或它们与二缩水甘油基醚的共聚物。
13.聚醛,如聚甲醛;以及含有环氧乙烷共聚单体的聚甲醛,用热塑性聚氨酯、聚丙烯酸酯或MBS改性的聚醛。
14.聚苯醚和聚苯硫醚,聚苯醚与苯乙烯聚合物或聚酰胺的混合物。
15.衍生于羟基封端的聚醚、聚酯或聚丁二烯与脂肪或芳香多异氰酸酯及其前体的聚氨酯。
16.衍生于二元胺和二元羧酸和/或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;间苯二甲胺和己二酸制得的芳香聚酰胺;由己二胺与间苯二甲酸或/和对苯二甲酸制得的聚酰胺(如需要可加入弹性体改性剂),如聚(2,4,4-三甲基己二胺/对苯二甲酸)或聚(间苯二胺/间苯二甲酸);以及上述聚酰胺与聚烯烃、烯烃共聚物、离聚物或者化学键合或接枝的弹性体的嵌段共聚物,或与聚醚(如聚乙二醇、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;以及加工过程中缩聚的聚酰胺(RIM聚酰胺体系)。
17.聚脲,聚酰亚胺,聚酰胺-酰亚胺,聚醚酰亚胺,聚酯酰亚胺,聚海因和聚苯并咪唑。
18.衍生于二元羧酸和二元醇和/或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,聚对苯二甲酸1,4-二羟甲基环己烷酯和聚羟基苯甲酸,以及衍生于羟基封端的聚醚的嵌段共聚醚酯,以及由聚碳酸酯或MBS改性的聚酯。
19.聚碳酸酯和聚酯碳酸酯。
20.聚砜,聚醚砜和聚醚酮。
21.衍生于醛与酚、脲和密胺的交联聚合物,如苯酚/甲醛树脂、脲/甲醛树脂和密胺/甲醛树脂。
22.干燥的和未干燥的醇酸树脂。
23.衍生于饱和和不饱和二元酸与多元醇的共聚酯和乙烯基化合物作交联剂的不饱和聚酯树脂,及其低燃性含卤改性产物。
24.衍生于取代的丙烯酸酯如环氧丙烯酸酯、尿烷丙烯酸酯或聚酯丙烯酸酯的可交联丙烯酸酯树脂。
25.用密胺树脂、脲树脂、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。
26.衍生于脂肪、脂环、杂环或芳香缩水甘油基化合物的交联环氧树脂,例如双酚A和双酚F的二缩水甘油醚用传统固化剂如酸酐或胺(如需要,以及促进剂)交联的反应产物。
27.诸如纤维素、橡胶、明胶的天然聚合物及其化学改性的衍生物,如乙酸纤维素、丙酸纤维素和丁酸纤维素,或纤维素醚如甲基纤维素;以及松香及其衍生物。
28.上述聚合物的共混物,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/聚丙烯酸酯、POM/热塑性PUR、PC/热塑性PUR、POM/聚丙烯酸酯、POM/MBS、PPO/HIPS、PPO/PA6.6和共聚物、PA/HDPE、PA/PP、PA/PPO、PBT/PC/ABS或PBT/PET/PC。
29.为纯净单体化合物或这些化合物的混合物的天然或合成有机材料,例如,矿物油,动物和植物脂、油和蜡,或基于合成酯(如邻苯二甲酸酯、己二酸酯、磷酸酯或偏苯三酸酯)的油、脂和蜡,以及合成酯与矿物油任意重量比的混合物、特别是用作纺丝组合物的混合物,以及这些材料的水乳液。
30.天然或合成橡胶的水乳液,例如天然胶乳或羧化苯乙烯/丁二烯共聚物的胶乳。
本发明进一步涉及一种组合物,包括一种易于氧化、热或光引发降解的有机材料和一种新型稳定剂混合物。
有机材料优选是合成聚合物,特别是上述几种之一、聚烯烃是优选的,聚乙烯,聚丙烯和其共聚物是特别优选的。
新型稳定剂体系的组分既可单独也可彼此混合后加到欲稳定的材料中。组分彼此独立地以0.01到4.99%的量使用,条件是组分a)和组分b),c),d),e),f)或g)基于欲稳定的材料的总重量为0.02到5%。
基于欲稳定的材料的总重量,组分a)和组分b),c),d),e),f)或g)的总量优选为0.05到3%,特别是0.05到2%,或0.05到1%。
组分a)和组分b),c),d),e),f)或g)之间的重量比优选从20∶1到1∶20,特别是10∶1到1∶10,例如5∶1到1∶5。
新型稳定剂混合物或其各个组分可用已知方法掺入到有机材料中,例如在成型前或成型期间或将溶解或分散后的化合物涂到有机材料上,如果需要,随后蒸发溶剂。新型稳定剂混合物的各个组分能以粉末、颗粒或母炼胶的形式加到欲稳定的材料中,该母炼胶含这些组分,其浓度为2.5到25%(重量)。
如果需要,新型稳定剂体系的组分在并入有机材料中前可彼此融熔掺混。
新型稳定剂体系或它的组分可在聚合前或聚合期间或交联前加入。
用这种方法稳定的材料可以各种形状使用,例如薄膜、纤维,带,模制组合物,成型物或用作油漆、粘合剂或腻子的粘接剂。
本发明的稳定后的有机材料也可附加含各种常规添加剂,例如:
1.抗氧剂
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-甲氧甲基苯酚,侧链为直链或支链的壬基苯酚如2,6-二壬基-4-甲基苯酚、2,4-二甲基-6-(1’-甲基-十一烷-1’-基)苯酚、2,4-二甲基-6-(1’-甲基-十七烷-1’-基)苯酚、2,4-二甲基-6-(1’-甲基-十三烷-1’-基)苯酚,以及它们的混合物。
1.2.烷硫甲基苯酚,如2,4-二辛硫甲基-6-叔丁基苯酚,2,4-二辛硫甲基-6-甲基苯酚,2,4-二辛硫甲基-6-乙基苯酚,2,6-二(十二烷硫甲基)-4-壬基苯酚。
1.3.氢醌及烷基化氢醌,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-羟基苯酚硬脂酸酯,己二酸二(3,5-二叔丁基-4-羟基苯酯)。
1.4.生育酚,如α.-生育酚、β-生育酚、γ-生育酚、δ-生育酚及其混合物(维生素E)。
1.5.羟基化的二苯硫醚,如2,2’-硫连二(6-叔丁基-4-甲基苯酚)、2,2’-硫连二(4-辛基苯酚)、4,4’-硫连二(6-叔丁基-3-甲基苯酚)、4,4’-硫连二(6-叔丁基-2-甲基苯酚)、4,4’-硫连二(3,6-二仲戊基苯酚)、4,4’-二(2,6-二甲基-4-羟基苯基)二硫。
1.6.烷叉双酚,如2,2’-甲叉二(6-叔丁基-4-甲基苯酚),2,2’-甲叉二(6-叔丁基-4-乙基苯酚)、2,2’-甲叉二[4-甲基-6-(α-甲基环己基)苯酚],2,2’-甲叉二(4-甲基-6-环己基苯酚),2,2’-甲叉二(6-壬基-4-甲基苯酚),2,2’-甲叉二(4,6-二叔丁基苯酚),2,2’-乙叉二(4,6-二叔丁基苯酚),2,2’-乙叉二(6-叔丁基-4-异丁基苯酚),2,2’-甲叉二[6-(α-甲基苯甲基)-4-壬基苯酚],2,2’-甲叉二[6-(α,α-二甲基苯甲基)-4-壬基苯酚],4,4’-甲叉二(2,6-二叔丁基苯酚),4,4’-甲叉二(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-羟基苯甲基)-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-正十二烷硫基丁烷,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、对苯二甲酸二[2-(3’-叔丁基-2’-羟基-5’-甲基苯甲基)-6-叔丁基-4-甲基苯基酯],1,1-二(3,5-二甲基-2-羟基苯基)丁烷,2,2-二(3,5-二叔丁基-4-羟基苯基)丙烷,2,2-二(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷硫基丁烷,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-苯甲基化合物,如3,5,3’,5’-四叔丁基-4,4’-二羟基-二苯甲醚,4-羟基-3,5-二甲基苯甲硫基乙酸十八烷酯,4-羟基-3,5-二叔丁基苯甲硫基乙酸十三烷酯,三(3,5-二叔丁基-4-羟基苯甲基)胺,对苯二甲酸二(4-叔丁基-3-羟基-2,6-二甲基苯甲硫基酯),二(3,5-二叔丁基-4-羟基苯甲基)硫,3,5-二叔丁基-4-羟基苯甲硫基乙酸异辛酯。
1.8.羟苯甲基化的丙二酸酯,如2,2-二(3,5-二叔丁基-2-羟基苯甲基)丙二酸二(十八烷基酯),2-(3-叔丁基-4-羟基-5-甲基苯甲基)丙二酸二(十八烷基酯),2,2-二(3,5-二叔丁基-4-羟基苯甲基)丙二酸二(十八烷硫基乙酯),2,2-二(3,5-二叔丁基-4-羟基苯甲基)丙二酸二[4-(1,1,3,3-四甲基丁基)苯基酯]。
1.9.芳香羟苯甲基化合物,如1,3,5-三(3,5-二叔丁基-4-羟基苯甲基)-2,4,6-三甲基苯,1,4-二(3,5-二叔丁基-4-羟基苯甲基)-2,3,5,6-四甲基苯,2,4,6-三(3,5-二叔丁基-4-羟基苯甲基)苯酚。
1.10.三嗪化合物,如2,4-二辛硫基-6-(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛硫基-4,6-二(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪,2-辛硫基-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-羟基苯甲基)异氰脲酸酯,1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苯甲基)异氰脲酸酯,2,4,6-三(3,5-二叔丁基-4-羟基苯乙基)-1,3,5-三嗪,1,3,5-三(3,5-二叔丁基-4-羟基苯丙酰基)-六氢化-1,3,5-三嗪,1,3,5-三(3,5-二环己基-4-羟基苯甲基)异氰脲酸酯。
1.11.苯甲基膦酸酯,如2,5-二叔丁基-4-羟基苯甲基膦酸二甲酯,3,5-二叔丁基-4-羟基苯甲基膦酸二乙酯,3,5-二叔丁基-4-羟基苯甲基膦酸二(十八烷基酯),5-叔丁基-4-羟基-3-甲基苯甲基膦酸二(十八烷基酯),3,5-二叔丁基-4-羟基苯甲基膦酸单乙酯的钙盐。
1.12.酰氨基苯酚,如N-(4-羟基苯基)月桂酰胺,N-(4-羟基苯基)硬脂酰胺,N-(3,5-二叔丁基-4-羟基苯基)氨基甲酸辛酯。
1.13.β-(3,5-二叔丁基-4-羟基苯基)丙酸与一元醇或多元醇的酯,醇例如为甲醇、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、硫连二乙醇、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-2,6,7-三氧杂二环[2.2.2]辛烷。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与一元醇或多元醇的酯,醇例如为甲醇、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、硫连二乙醇、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-2,6,7-三氧杂二环[2.2.2]辛烷。
1.15.β-(3,5-二环己基-4-羟基苯基)丙酸与一元醇或多元醇的酯,醇例如为甲醇、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、硫连二乙醇、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-2,6,7-三氧杂二环[2.2.2]辛烷。
1.16.3,5-二叔丁基-4-羟基苯基乙酸与一元醇或多元醇的酯,醇例如为甲醇、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、硫连二乙醇、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-2,6,7-三氧杂二环[2.2.2]辛烷。
1.17.β-(3,5-二叔丁基-4-羟基苯基)丙酸的酰胺,如N,N’-二(3,5-二叔丁基-4-羟基苯丙酰基)-1,6-己二胺,N,N’-二(3,5-二叔丁基-4-羟基苯丙酰基)-1,3-丙二胺,N,N’-二(3,5-二叔丁基-4-羟基苯丙酰基)肼。
1.18.抗坏血酸(维生素C)
1.19.胺类抗氧剂,如N,N’-二异丙基对苯二胺,N,N’-二仲丁基对苯二胺,N,N’-二(1,4-二甲基戊基)对苯二胺,N,N’-二(1-乙基-3-甲基戊基)对苯二胺,N,N’-二(1-甲基庚基)对苯二胺,N,N’-二环己基对苯二胺,N,N’-二苯基对苯二胺,N,N’-二(2-萘基)对苯二胺,N-异丙基-N’-苯基对苯二胺,N-(1,3-二甲基丁基)-N’-苯基对苯二胺,N-(1-甲基庚基)-N’-苯基对苯二胺,N-环己基-N’-苯基对苯二胺,4-(对甲苯氨磺酰基)二苯胺,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,辛基化的二苯胺如p,p’-二叔辛基二苯胺,4-正丁氨基苯酚,4-丁酰氨基苯酚,4-壬酰氨基苯酚,4-十二碳酰氨基苯酚,4-十八碳酰氨基苯酚,二(4-甲氧基苯基)胺,2,6-二叔丁基-4-二甲氨甲基苯酚,2,4’-二氨基二苯甲烷,4,4’-二氨基二苯甲烷,N,N,N’,N’-四甲基-4,4’-二氨基二苯甲烷,1,2-二[(2-甲基苯基)氨基]乙烷,1,2-二(苯氨基)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,单和双烷基化的叔丁基/叔辛基二苯胺的混合物,单和双烷基化的壬基二苯胺的混合物,单和双烷基化的十二烷基二苯胺的混合物,单和双烷基化的异丙基/异己基二苯胺的混合物,单和双烷基化的叔丁基二苯胺的混合物,2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪,吩噻嗪,单和双烷基化的叔丁基/叔辛基吩噻嗪的混合物,单和双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-2-丁烯,N,N-二(2,2,6,6-四甲基-哌啶-4-基)-1,6-己二胺,癸二酸二(2,2,6,6-四甲基-4-哌啶基酯),2,2,6,6-四甲基哌啶-4-酮,2,2,6,6-四甲基哌啶-4-醇。
2.紫外线吸收剂和光稳定剂
2.1.2-(2’-羟基苯基)苯并***类化合物,如2-(2’-羟基-5’-甲基苯基)苯并***,2-(3’,5’-二叔丁基-2’-羟基苯基)苯并***,2-(5’-叔丁基-2’-羟基苯基)苯并***,2-(2’-羟基-5’-(1,1,3,3-四甲基丁基)苯基)苯并***,2-(3’,5’-二叔丁基-2’-羟基苯基)-5-氯-苯并***,2-(3’-叔丁基-2’-羟基-5’-甲基苯基)-5-氯-苯并***,2-(3’-仲丁基-5’-叔丁基-2’-羟基苯基)苯并***,2-(2’-羟基-4’-辛氧基苯基)苯并***,2-(3’,5’-二叔戊基-2’-羟基苯基)苯并***,2-(3’,5’-二(α,α-二甲基苯甲基)-2’-羟基苯基)苯并***,2-(3’-叔丁基-2’-羟基-5’-(2-辛氧羰基乙基)苯基)-5-氯-苯并***,2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)-5-氯-苯并***,2-(3’-叔丁基-2’-羟基-5’-(2-甲氧羰基乙基)苯基)-5-氯-苯并***,2-(3’-叔丁基-2’-羟基-5’-(2-甲氧羰基乙基)苯基)苯并***,2-(3’-叔丁基-2’-羟基-5’-(2-辛氧羰基乙基)苯基)苯并***,2-(3’-叔丁基-5’-[2-(2-乙基己氧基)羰基乙基]-2’-羟基苯基)苯并***,2-(3’-十二烷基-2’-羟基-5’-甲基苯基)苯并***,和2-(3’-叔丁基-2’-羟基-5’-(2-异辛氧羰基乙基)苯基)苯并***,2,2’-甲叉二[4-(1,1,3,3-四甲基丁基)-6-苯并***-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧羰基乙基)-2’-羟基苯基]-2H-苯并***与聚乙二醇300的酯交换产物;其中的R为3’-叔丁基-4,-羟基-5’-2H-苯并***-2-基苯基的
2.2.2-羟基二苯酮类化合物,例如它的4-羟基、4-甲氧基4-辛氧基、4-癸氧基、4-十二烷氧基、4-苯甲氧基、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酯,如水杨酸4-叔丁基苯酯,水杨酸苯酯,水杨酸辛基苯酯,间苯二酚二苯甲酸酯,间苯二酚二(4-叔丁基苯甲酸酯),间苯二酚苯甲酸酯,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-羟基苯甲酸十六烷酯,3,5-二叔丁基-4-羟基苯甲酸十八烷酯,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.丙烯酸酯类化合物,如α-氰-β,β-二苯基丙烯酸乙酯α-氰基-β,β-二苯基丙烯酸异辛酯,α-甲酯基肉桂酸甲酯,α-氰基-β-甲基对甲氧基肉桂酸甲酯,α-氰基-β-甲基对甲氧基肉桂酸丁酯,α-甲酯基对甲氧基肉桂酸甲酯,和N-(β-甲酯基-β-氰乙烯基)-2-甲基二氢吲哚。
2.5.镍化合物,例如:2,2’-硫连二[4-(1,1,3,3-四甲基丁基)苯酚]与镍的配合物,如1∶1或1∶2配合物,如需要还可以有如正丁胺、三乙醇胺或N-环己基二乙醇胺的其它配位体;二丁基二硫代氨基甲酸镍;4-羟基-3,5-二叔丁基苯甲基膦酸单烷基酯如甲酯或乙酯的镍盐;酮肟的镍配合物,如2-羟基-4甲基苯基·十一烷基酮肟的镍配合物;1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,如需要,还可以有其它配位体。
2.6.位阻胺,例如癸二酸二(2,2,6,6-四甲基-4-哌啶基酯),丁二酸二(2,2,6,6-四甲基-4-哌啶基酯),癸二酸二(1,2,2,6,6-五甲基-4-哌啶基酯),癸二酸二(1-辛氧基-2,2,6,6-四甲基-4-哌啶基酯),正丁基-3,5-二叔丁基-4-羟基苯甲基丙二酸二(1,2,2,6,6-五甲基-4-哌啶基酯),1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基哌啶与丁二酸的缩合物,N,N’-二(2,2,6,6-四甲基-4-哌啶基)-1,6-己二胺与4-叔辛氨基-2,6-二氯-1,3,5-三嗪的缩合物,次氮基三乙酸三(2,2,6,6-四甲基-4-哌啶基酯),1,2,3,4-丁四酸四(2,2,6,6-四甲基-4-哌啶基酯),1,1’-(1,2-亚乙基)二(3,3,5,5-四甲基哌嗪酮),4-苯甲酰基-2,2,6,6-四甲基哌啶,4-硬脂酰氧基-2,2,6,6-四甲基哌啶,2-正丁基-2-(2-羟基-3,5-二叔丁基苯甲基)丙二酸二(1,2,2,6,6-五甲基哌啶基酯),3-正辛基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮,癸二酸二(1-辛氧基-2,2,6,6-四甲基哌啶基酯),丁二酸二(1-辛氧基-2,2,6,6-四甲基哌啶基酯),N,N’-二(2,2,6,6-四甲基-4-哌啶基)-1,6-己二胺与4-吗啉代-2,6-二氯-1,3,5-三嗪的缩合物,2-氯-4,6-二(4-正丁氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪与1,2-二(3-氨丙基氨基)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)-1,3,5-三嗪与1,2-二(3-氨丙基氨基)乙烷的缩合物,8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮杂螺[4.5]癸烷-2,4-二酮,3-十二烷基-1-(2,2,6,6-四甲基-4-哌啶基)吡咯烷-2,5-二酮,3-十二烷基-1-(1,2,2,6,6-五甲基-4-哌啶基)吡咯烷-2,5-二酮,4-十六烷氧基-和4-硬脂酰氧基-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)-1,6-己二胺与4-环己氨基-2,6-二氯-1,3,5-三嗪的缩合产物,1,2-二(3-氨丙基氨基)乙烷与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产物(CA登录号136504-96-6);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。
2.7.草酰胺,如4,4’-二辛氧基-N,N’-草酰二苯胺,2,2’-二乙氧基-N,N’-草酰二苯胺,2,2’-二辛氧基-5,5’-二叔丁基-N,N’-草酰二苯胺,2,2’-二(十二烷氧基)-5,5’-二叔丁基-N,N’-草酰二苯胺,2-乙氧基-2’-乙基-N,N’-草酰二苯胺,N,N’-二(3-二甲氨基丙基)-N,N’-草酰二苯胺,2-乙氧基-5-叔丁基-2’-乙基-N,N’-草酰二苯胺及其与2-乙氧基-2’-乙基-5,4’-二叔丁基-N,N’-草酰二苯胺的混合物,以及邻-和对-甲氧基二取代的N,N’-草酰二苯胺的混合物,邻-和对-乙氧基二取代的N,N’-草酰二苯胺的混合物。
2.8.2-(2-羟基苯基)-1,3,5-三嗪类化合物,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(2,4-二甲基苯基)-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(2,4-二甲基苯基)-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。
3.金属减活化剂,例如N,N’-二苯基草酰胺,N-水杨醛-N’-水杨酰基肼,N,N’-二(水杨酰基)肼,N,N’-二(3,5-二叔丁基-4-羟基苯丙酰基)肼,3-水杨酰氨基-1,2,4-***,二(苯甲叉基)草酰肼,N,N’-草酰二苯胺,间苯二甲酰肼,癸二酰二苯基酰肼,N,N’-二乙酰基己二酰肼,N,N’-二(水杨酰基)草酰肼,N,N’-二(水杨酰基)硫代丙酰基肼。
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(壬苯酯),亚磷酸三月桂酯,亚磷酸三(十八烷酯),二(十八烷醇)·季戊四醇二亚磷酸酯,亚磷酸三(2,4-二叔丁基苯酯),二异癸醇·季戊四醇二亚磷酸酯,二(2,4-二叔丁基苯酚)·季戊四醇二亚磷酸酯,二(2,6-二叔丁基-4-甲基苯酚)·季戊四醇二亚磷酸酯,二(2,4-二叔丁基-6-甲基苯酚)·季戊四醇二亚磷酸酯,二(2,4,6,-三叔丁基苯酚)·季戊四醇二亚磷酸酯,三(十八烷醇)·山梨醇三亚磷酸酯,4,4’-联苯基二亚膦酸四(2,4-二叔丁基苯酯),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烯(dioxaphosphocin),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烯,亚磷酸二(2,4-二叔丁基-6-甲基苯基)·甲基酯,亚磷酸二(2,4-二叔丁基-6-甲基苯基)·乙基酯。
5.羟胺类化合物,例如,N,N-二苯甲基羟胺,N,N-二乙基羟胺,N,N-二辛基羟胺,N,N-二月桂基羟胺,N,N-二(十四烷基)羟胺,N,N-二(十六烷基)羟胺,N,N-二(十八烷基)羟胺,N-十六烷基-N-十八烷基羟胺,N-十七烷基-N-十八烷基羟胺,衍生于氢化动物脂胺的N,N-二烷基羟胺。
6.硝酮,例如N-苯甲基-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,衍生于由氢化动物脂胺制得的N,N-二烷基羟胺的硝酮。
7.硫增效剂,如硫连二丙酸二月桂酯或硫连二丙酸二(十八烷基酯)。
8.过氧化物清除剂,例如β-硫连二丙酸的酯如月桂酯、十八烷酯、十四烷酯或十三烷酯,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,季戊四醇四(β-十二烷硫基丙酸酯)。
9.聚酰胺稳定剂,例如铜盐与碘化物的组合物和/或磷化合物与二价锰盐。
10.碱性共稳定剂,例如密胺,聚乙烯基吡咯烷酮,二氰胺,氰尿酸三烯丙酯,脲衍生物,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,如硬脂酸钙、硬脂酸锌、山嵛酸镁、硬脂酸镁、蓖麻酸钠和棕榈酸钾,邻苯二酚锑,或邻苯二酚锡。
11.成核剂,例如:无机物如滑石,金属氧化物如二氧化钛或氧化镁,磷酸盐、碳酸盐或硫酸盐(优选碱土金属的盐);有机化合物如一元或多元羧酸及其盐,如4-叔丁基苯甲酸、己二酸、二苯基乙酸、丁二酸钠或苯甲酸钠;聚合物,如离子共聚物(“离聚物”)。
12.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,碳黑,石墨,木粉和其它自然物的粉或纤维,合成纤维。
13.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,光学增白剂,阻燃剂,抗静电剂以及发泡剂。
14.苯并呋喃酮类和二氢吲哚酮类化合物,例如公开于US-A-4325863、US-A-4338244、US-A-5175312、US-A-5216052、US-A-5252643、DE-A-4316611、DE-A-4316622、DE-A-4316876、EP-A-0589839或EP-A-0591102中的上述化合物,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-戊酰氧基苯基)-5,7-二叔丁基-苯并呋喃-2-酮。
新型稳定剂混合物和常规添加剂之间的重量比是例如1∶0.5到1∶5。
本发明进一步涉及新型稳定剂混合物在稳定有机材料以防氧化、热或光引发降解中的用途。
用新型稳定剂体系稳定的有机材料不仅大大改进了光稳定性,而且在某些情况下也改进了热稳定剂。
下列实施例详细说明本发明。除非另有说明,所有百分数是指重量百分数。用于实施例1-4中的光稳定剂化合物An1的平均值是5.8。化合物B-1:n2的平均值是4.5。化合物B-2:n2的平均值是3.5。化合物C是可由下式多胺H2N-(CH2)3-NH-(CH2)2-NH-(CH2)3-NH2与氰尿酰氯的反应产物与下式化合物反应获得的产物:化合物D:n4的平均值是5.1。化合物E:式(VIa)和(VIb)化合物的混合物和其中n5的平均值约为3.9,n8 *的平均值约为4.2和
(VIa)和(VIb)之比为约4∶1。化合物F-1:n6的平均值是3.2。化合物F-2:化合物G-1:n7的平均值是2.5。化合物G-2:n7的平均值是2.5。实施例1在聚丙烯嵌段共聚物膜中光稳定作用
100份聚丙烯嵌段共聚物粉末在200℃下于Brabender混合器中与0.05份四[3-(3,5-二叔丁基-4-羟基苯基)丙酸]季戊四醇酯,0.10份亚磷酸三(2,4-二叔丁基苯基)酯,0.1份硬脂酸钙和表1所示量的光稳定剂均化10分钟,所得组合物尽可能快地从混合器中取出并在肘杆式压力机中压成2-3mm厚的板。所得粗压片切成片并在两个高光泽度硬铝箔之间于260℃下用水力压力机压6分钟压成0.5mm厚的板,将其立即在水冷压力机中冷却。将该0.5mm厚的板切成60mm×25mm的片并在WEATHR-O-METERCi65(黑板温度为63±2℃,不曝露在雨水中)曝光。这些试验试样定期从曝光设备上除去并在IR分光仪中测定其羰基含量。在曝光期间羰基吸光度的增加是聚合物光氧化降解的度量且从与力学性能有关的经验来看是已知的,结果示出在表1中。
表1
光稳定剂 在WEATHER-O-METERCi65中
达0.2羰基吸光度的小时数
无 110
0.2%的化合物A 2560
0.2%的化合物B-1 1740
0.2%的化合物B-2 2280
0.2%的化合物C 2400
0.2%的化合物D 2040
0.2%的化合物E 1710
0.2%的化合物F-1 505
0.2%的化合物F-2 260
0.2%的化合物G-1 1410
0.2%的化合物G-2 1230
0.1%的化合物A和
0.1%的化合物B-1 2890
0.1%的化合物A和
0.1%的化合物B-2 2880
0.1%的化合物A和
0.1%的化合物C 2990
0.1%的化合物A和
0.1%的化合物D 2950
0.1%的化合物A和
0.1%的化合物E 2400
0.1%的化合物A和
0.1%的化合物F-1 1840
0.1%的化合物A和
0.1%的化合物F-2 1610
0.1%的化合物A和
0.1%的化合物G-1 2160
0.1%的化合物A和
0.1%的化合物G-2 2100实施例2在高密度聚乙烯膜中的光稳定作用
100份高密度聚乙烯粉末(密度=0.965g/cm3)在180℃下于Brabender塑性混合器中与0.033份四[3-(3,5-二叔丁基-4-羟基苯基)丙醇]季戊四醇酯,0.066份亚磷酸三(2,4-二叔丁基苯基)酯,0.1份硬脂酸钙和表2所示的光稳定剂均化10分钟。将所得组合物尽可能快地从混合器中取出并在肘杆式压力机中压成2-3mm厚的板。所得粗压片切成片并在两个高光泽度硬铝箔之间于210℃下用水力压力机压6分钟压成0.5mm厚的板,将其立即在水冷压力机中冷却。将该0.5mm厚的板切成60mm×25mm的片并在WEATHR-O-METER Ci65(黑板温度为63±2℃,不曝露在雨水中)曝光。这些试验试样定期从曝光设备上除去并在IR分光仪中测定其乙烯基含量。在曝光期间乙烯基吸光度(909cm-1)的增加是聚合物光氧化降解的度量且从与力学性能有关的经验来看是已知的,结果示出在表2中。 表 2
在WEATHER-O-METERCi65
光稳定剂 中7222小时后乙烯基吸光度
无 318小时后0.097
0.1的化合物A 0.039
0.1%的化合物B-1 0.052
0.1%的化合物B-2 0.043
0.1%的化合物C 0.054
0.1%的化合物D 0.039
0.1%的化合物E 0.046
0.1%的化合物F-1 0.058
0.1%的化合物F-2 5286小时后0.143
0.1%的化合物G-1 0.040
0.1%的化合物G-2 0.040
0.05%的化合物A和
0.05%的化合物B-1 0.038
0.05%的化合物A和
0.05%的化合物B-2 0.038
0.05%的化合物A和
0.05%的化合物C 0.040
0.05%的化合物A和
0.05%的化合物D 0.029
0.05%的化合物A和
0.05%的化合物E 0.039
0 05%的化合物A和
0.05%的化合物F-1 0.036
0.05%的化合物A和
0.05%的化合物F-2 0.045
0.05%的化合物A和
0.05%的化合物G-1 0.030
0.05%的化合物A和
0.05%的化合物G-2 0.035
Claims (14)
1.一种稳定剂混合物,包括组分a)和组分b)、c)、d)、e)、f)或g),其中
组分a)是至少一种式I化合物其中R1是C1-C10烷基,C5-C12环烷基,C1-C4烷基取代的C5-C12环烷基,苯基或C1-C10烷基取代的苯基,
R2是C3-C10烷撑,
R3是氢,C1-C8烷基,O,-CH2CN,C3-C6链烯基,C7-C9苯基烷基,苯基被C1-C4烷基取代的C7-C9苯基烷基;或C1-C8酰基和,
n1是1到50的数;
组分b)是至少一种式(II)化合物其中R4,R6,R7和R8彼此独立地为氢,C1-C12烷基,C5-C12环烷基,C1-C4烷基取代的C5-C12环烷基,苯基,被-OH和/或C1-C10烷基取代的C7-C9苯基烷基;或式III基团R5是C2-C18烷撑,C5-C7亚环烷基或C1-C4烷撑二(C5-C7亚环烷基),或R4,R5和R6一起与它们相连的氮原子形成5元到10元杂环,或R7和R8一起与它们相连的氮原子形成5元到10元杂环,R9定义同R3,n2是2到50的数,和R4,R6,R7和R8至少一个是式(III)基团;
组分c)是将式IVa的多胺与氰尿酰氯反应获得的产物与式IVb化合物反应获得的产物,其中n3’,n3”和n3彼此独立地是2到12的数,R10是氢,C1-C12烷基,C5-C12环烷基,苯基或C7-C9苯基烷基,和R11定义同R3;
组分f)是至少一种式(VII)化合物其中R14和R18彼此独立地是一直键或-N(X1)-CO-X2-CO-N(X3)-基团,其中X1和X3彼此独立地是氢、C1-C8烷基、C5-C12环烷基、苯基、C7-C9苯基烷基或式III基团,X2是一直键或C1-C4烷撑,R15定义同R3,R16,R17,R20和R21彼此独立地是氢、C1-C30烷基、C5-C20环烷基或苯基,R19是氢、C1-C30烷基、C5-C12环烷基、C7-C9苯基烷基、苯基或式III基团,和n6是1到50的数;
2.根据权利要求1的稳定剂混合物,其中R3,R9,R11,R15和R27是氢或甲基。
3.根据权利要求1的稳定剂混合物,其中R1是C1-C4烷基、C5-C8环烷基或苯基,R2是C3-C6烷撑,和n1是1到25的数;R4,R6,R7和R8彼此独立地是氢、C1-C8烷基、C5-C8环烷基、苯基、C7-C9苯基烷基或式III基团,或R7和R8一起与它们相连的氮原子形成一6元杂环,R5是C2-C10烷撑,和n2是2到25的数;n’3,n”3和n3彼此独立是2到4的数,和R10是C1-C4烷基;R12是氢,R13是乙撑,和n4是2到25的数;n5和n5 *彼此独立是2到25的数;R14和R18是一直键或-N(X1)-CO-X2-CO-N(X3)-基,X1和X3彼此独立地是氢或C1-C4烷基,X2是一直键,R16和R20是C1-C25烷基或苯基,R17和R21是氢或C1-C4烷基,R19是C1-C25烷基或式III基团,和n6是1到25的数;R22,R24,R25和R26是C1-C4烷撑,n23是一直键,和n7是1到25的数。
4.根据权利要求1的稳定剂混合物,其中组分a)是至少一种式I-A化合物其中n1是1到20的数;组分b)是至少一种式(II-B-1)、(II-B-2)或(II-B-3)的化合物 其中n2是2到20的数;组分c)是可由下式多胺
5.根据权利要求1的稳定剂混合物,它包括组分a)和b)。
6.根据权利要求1的稳定剂混合物,它包括组分a)和c)。
7.根据权利要求1的稳定剂混合物,它包括组分a)和d)。
8.根据权利要求1的稳定剂混合物,它包括组分a)和e)。
9.根据权利要求1的稳定剂混合物,它包括组分a)和f)。
10.根据权利要求1的稳定剂混合物,它包括组分a)和g)。
11.一种组合物,包括一种对氧化、热或光引发降解敏感的有机材料和一种根据权利要求1的稳定剂混合物。
12.根据权利要求11的组合物,其中有机材料是聚烯烃。
13.根据权利要求11的组合物,其中有机材料是聚乙烯、聚丙烯或聚乙烯或聚丙烯的共聚。
14.一种稳定对氧化、热或光引发降解敏感的有机材料的方法,它包括将根据权利要求1的一种稳定剂混合物掺入到所述有机材料。
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EP95810091.9 | 1995-02-10 | ||
EP95810091 | 1995-02-10 |
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CN1136048A CN1136048A (zh) | 1996-11-20 |
CN1079809C true CN1079809C (zh) | 2002-02-27 |
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US (2) | US6020406A (zh) |
EP (1) | EP0728806B2 (zh) |
JP (1) | JPH08245834A (zh) |
KR (1) | KR100378234B1 (zh) |
CN (1) | CN1079809C (zh) |
BR (1) | BR9600376A (zh) |
CA (1) | CA2169124A1 (zh) |
DE (1) | DE59600119D1 (zh) |
ES (1) | ES2115421T5 (zh) |
SK (1) | SK17796A3 (zh) |
TW (1) | TW401437B (zh) |
ZA (1) | ZA961053B (zh) |
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-
1996
- 1996-01-23 TW TW085100736A patent/TW401437B/zh active
- 1996-02-02 DE DE59600119T patent/DE59600119D1/de not_active Expired - Fee Related
- 1996-02-02 ES ES96810069T patent/ES2115421T5/es not_active Expired - Lifetime
- 1996-02-02 EP EP96810069A patent/EP0728806B2/de not_active Expired - Lifetime
- 1996-02-08 SK SK177-96A patent/SK17796A3/sk unknown
- 1996-02-08 KR KR1019960002969A patent/KR100378234B1/ko not_active IP Right Cessation
- 1996-02-08 CN CN96101386A patent/CN1079809C/zh not_active Expired - Fee Related
- 1996-02-08 CA CA002169124A patent/CA2169124A1/en not_active Abandoned
- 1996-02-09 BR BR9600376A patent/BR9600376A/pt not_active IP Right Cessation
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- 1996-02-09 JP JP8048142A patent/JPH08245834A/ja not_active Withdrawn
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ZA961053B (en) | 1996-08-12 |
US6020406A (en) | 2000-02-01 |
US6365651B1 (en) | 2002-04-02 |
CA2169124A1 (en) | 1996-08-11 |
KR100378234B1 (ko) | 2003-06-11 |
SK281600B6 (sk) | 2001-05-10 |
JPH08245834A (ja) | 1996-09-24 |
CN1136048A (zh) | 1996-11-20 |
KR960031572A (ko) | 1996-09-17 |
EP0728806B2 (de) | 2003-05-14 |
DE59600119D1 (de) | 1998-04-30 |
ES2115421T3 (es) | 1998-06-16 |
BR9600376A (pt) | 1998-03-03 |
ES2115421T5 (es) | 2004-02-01 |
SK17796A3 (en) | 2001-05-10 |
TW401437B (en) | 2000-08-11 |
EP0728806B1 (de) | 1998-03-25 |
EP0728806A1 (de) | 1996-08-28 |
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