CN1184102A - 稳定的硝基氧与取代的乙烯的双加合物及稳定化组合物 - Google Patents
稳定的硝基氧与取代的乙烯的双加合物及稳定化组合物 Download PDFInfo
- Publication number
- CN1184102A CN1184102A CN97123041A CN97123041A CN1184102A CN 1184102 A CN1184102 A CN 1184102A CN 97123041 A CN97123041 A CN 97123041A CN 97123041 A CN97123041 A CN 97123041A CN 1184102 A CN1184102 A CN 1184102A
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- CN
- China
- Prior art keywords
- tetramethyl
- butyl
- compound
- acid
- diadduct
- 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.)
- Granted
Links
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- KMEUSKGEUADGET-UHFFFAOYSA-N 1-hydroxy-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)N1O KMEUSKGEUADGET-UHFFFAOYSA-N 0.000 claims description 2
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- HORBOHJHQGXXOR-UHFFFAOYSA-N n-octadecyloctadecan-1-imine oxide Chemical compound CCCCCCCCCCCCCCCCCC[N+]([O-])=CCCCCCCCCCCCCCCCCC HORBOHJHQGXXOR-UHFFFAOYSA-N 0.000 description 1
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- KISSZQOBOUCLMH-UHFFFAOYSA-N n-tetradecylhydroxylamine Chemical compound CCCCCCCCCCCCCCNO KISSZQOBOUCLMH-UHFFFAOYSA-N 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
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- JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/42—Use of additives, e.g. for stabilisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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Abstract
制备了稳定的受阻胺硝基氧化合物与取代的乙烯的1,2-双加合物,通过将等当量的硝酰基化合物与例如为苯乙烯或丙烯酸酯的烯不饱和化合物反应。这些加合物为十分有效的抑制剂以防止烯不饱和单体在蒸馏、加工或贮存时的早期聚合。
Description
本发明涉及稳定的受阻硝酰基化合物与取代的乙烯(如烯不饱和单体中的那些)的新型1,2-加合物。该化合物是防止乙烯基单体早期聚合的有效抑制剂。
许多在工业上重要的烯不饱和单体在热作用或杂质引发下十分容易产生不期望的自由基聚合。这些单体的实例包括苯乙烯、丙烯酸和甲基丙烯酸、丙烯酸酯和甲基丙烯酸酯,以及丙烯腈。早期聚合可以出现在单体的制备、纯化或贮存期间。许多这类单体是通过蒸馏纯化的。在这一操作中最容易出现早期聚合,因此是最麻烦的。因此十分需要防止或降低这种聚合的方法,因为防止或降低这种早期聚合提高了纯化的单体的产率,而且也防止在车间中的聚合失控,这种失控是危险的并且造成成本高。
本发明包括的稳定的受阻有机硝酰基化合物是在α碳原子上被完全取代的硝基氧。参见L.B.Volodarsky等人的“稳定的硝基氧的合成化学”,CRC出版社,Boca Raton,FL,1994。双(三氟甲基)硝基氧是稳定的硝基氧,并且它与乙烯的1,2-加合物是已知的。参见A.E.Tipping等人,J.Fluor,Chem.,69,163(1994);R.E.Banks等人,J.Chem.Soc.,C,901(1966);和R.E.Banks等人,J.Chem.Soc.,C,2777(1971)。
1-苯基-1,2-双(2,2,6,6-四甲基-哌啶-1-基氧)-乙烷是已知的双加合物。G.Moad等人在Polymer Bull.6,589(1982)中报道了这一物质是通过1-烃氧基-2,2,6,6-四甲基-哌啶与苯乙烯的反应而制备的。这一物质没有被给予化学文摘号(CAN),也没有描述过这类物质的任何用途。本发明的一个目的是提供新型的双加合物,它由稳定的受阻有机硝酰基化合物与烯不饱和单体的反应制备。
本发明的另一目的是展示这类双加合物在防止或降低烯不饱和单体在蒸馏和纯化过程中的早期聚合的能力。
本发明的再一目的是提供一种化合物,它对易受热或光诱导辐射影响的有机基质具有有效的稳定效应。
本发明涉及式I或II的新型1,2-双加合物,其中,R1和R2独立为C1-C4的烷基,或R1和R2一起为五亚甲基,优选R1和R2各为甲基;E为C6-C10的芳基;或被C1-C4烷基或被卤素取代的所述芳基,或E为-COOH或-COOR6,其中R6为C1-C18烷基或C2-C8羟基,或E为-CN,优选E为-COOH,-CN或-COOR6,其中R6为C1-C4烷基,最优选丁基;R3、R4和R5各自为C1-C4烷基,优选甲基;和T为完成5,6或7元环或1,1,3,3-四甲基异二氢吲哚部分所需的基团,所述T基团也可以被以下基团取代:羟基、氧代基(OXO)、乙酰胺基、-OR8,其中R8为C1-C18烷基、或-O-CO-R9,其中R9为C1-C17烷基或苯基,R9优选为C1-C11烷基或苯基,条件是式I化合物不为1-苯基-1,2-双(2,2,6,6-四甲基哌啶-1-基氧)-乙烷或1-苯基-1,2-双(1,1,3,3-四甲基-异二氢吲哚-2-基氧)乙烷。
化合物1-苯基-1,2-双(2,2,6,6-四甲基哌啶-1-基氧)-乙烷或1-苯基-1,2-双(1,1,3,3-四甲基-异二氢吲哚-2-基氧)乙烷是1-烃氧基-2,2,6,6-四甲基哌啶和苯乙烯的1,2-双加合物,以及2-烃氧基-1,1,3,3-四甲基-异二氢吲哚和苯乙烯的1,2-双加合物。
优选T为完成5,6或7元环或1,1,3,3-四甲基-异二氢吲哚部分所需的基团,其中所述T基是非取代的或被下列基团取代:羟基、氧代基、乙酰胺基或-O-CO-R9,其中R9为C1-C11烷基或苯基。
以下化合物是最优选的:(a)1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶和苯乙烯的1,2-双加合物;(b)1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶和4-氯-苯乙烯的1,2-双加合物;(c)1-烃氧基-2,2,6,6-四甲基-4-羟基哌啶和苯乙烯的1,2-双加合物;(d)1-烃氧基-2,2,6,6-四甲基-4-氧代哌啶和苯乙烯的1,2-双加合物;(e)1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶和丙烯酸丁酯的1,2-双加合物;(f)1-烃氧基-2,2,6,6-四甲基-4-羟基哌啶和丙烯酸丁酯的1,2-双加合物;或(g)1-烃氧基-2,2,6,6-四甲基-4-乙酰胺基哌啶和苯乙烯的1,2-双加合物;
式I代表环状的5,6或7元环稳定的硝基氧的加合物。式II代表丙烯酸系稳定的硝基氧的加合物。可以按照标准方法制备式I和II的化合物。本发明的另一方面是式I和II的双加合物作为有效抑制剂的应用,用于抑制烯不饱和单体的早期聚合。单体可以是任何的具有至少一个碳碳双键能进行自由基诱导聚合的单体。这些单体是市场上已知的,包括多种结构类型。这些单体典型的例子是乙烯基芳烃,如苯乙烯、α-甲基苯乙烯和二乙烯基苯;二烯,如丁二烯和异戊二烯;卤代单体,如氯乙烯、氯丁二烯、偏氯乙烯、偏氟乙烯和氟乙烯;不饱和酸,如丙烯酸、甲基丙烯酸和巴豆酸;不饱和酯,如丙烯酸酯和甲基丙烯酸酯,实例有丙烯酸丁酯、甲基丙烯酸甲酯、丙烯酸乙酯和丙烯酸甲酯;不饱和腈,如丙烯腈和甲基丙烯腈;不饱和醚,如甲基乙烯基醚;和各种乙烯基单体,如乙烯基吡啶、乙烯基磷酸二乙酯和苯乙烯磺酸钠。
本发明的另一方面是被稳定化以防止早期聚合的单体组合物,它包括:(a)烯不饱和单体,和(b)有效稳定量的上述式I或II的化合物。
烯不饱和单体优选:乙烯基芳族烃;二烯;卤化乙烯基单体;不饱和酸;不饱和酯;不饱和腈;不饱和醚;和各种乙烯基单体,如乙烯基吡啶、乙烯基膦酸二乙酯和苯乙烯磺酸钠。
更优选的组合物是,其中单体为α-甲基苯乙烯、二乙烯基苯、丁二烯、异戊二烯、氯乙烯、氯丁二烯、偏氯乙烯、偏氟乙烯、氟乙烯、丙烯酸、甲基丙烯酸、巴豆酸、丙烯酸丁酯、甲基丙烯酸甲酯、丙烯酸乙酯、丙烯酸甲酯、丙烯腈、甲基丙烯腈或甲基乙烯基醚。
尤其优选的组合物是,其中单体是丙烯酸、甲基丙烯酸、丙烯酸丁酯、丙烯酸乙酯或丙烯腈。
苯乙烯和乙烯基取代的芳族化合物(aromate)不在最优选的单体之列。
组分(b)的有效稳定量为基于组(a)单体重量的1至10000ppm(重)。优选组分(b)的量为基于组分(a)单体重量的10至1000ppm(重)。可通过任何常规方法将活化的聚合抑制剂混合物引入待稳定的单体中。可以用任何手段将它加入到所需应用点的上游。另外,该混合物可与单体加料一起分别加入蒸馏组中,或通过提供活化的抑制剂混合物有效分布的单独入口加入蒸馏组中。由于在操作过程中抑制剂逐渐消耗,通常需要在蒸馏过程中加入另外的抑制剂以维持蒸馏体系中活化抑制剂混合物的适当量。这种加入可以是连续的,或者间歇加入新的抑制剂,但抑制剂的浓度能够保持在所需最底限之上。
本发明的另一目的是使用式I和II的双加合物作为有效抑制剂防止烯不饱和单体的早期聚合。
式I和II的双加合物可以根据有机化学中的标准方法制备。起始原料,即N-氧基化合物,部分上是商购化合物或可由现有技术制得。
本发明也涉及稳定化的组合物,它包括:(a)易受热、氧或光化辐射不利影响的有机物质和(b)有效稳定量的上述式I或II化合物。
有机物质优选为聚合物,尤其是聚烯烃,如聚丙烯或聚乙烯,或其中至少一种聚合物或聚合物组分含有效烯不饱和位的聚合物、共聚物或聚合物共混物。后者的实例为选自下列的聚合物:ABS、HIPS、SBR乳液、PP/EPDM、PP/NBR、PP/NR、ABS/PC、ABS/尼龙、ABS/PVC、ABS/聚酯、ABS/SMA、ABS/聚砜、ASA/PC、缩醛/弹性体、聚酯/弹性体、尼龙/弹性体、PPO/NR、EPDM/NBR和EPDM/烯烃。
可被稳定的聚合物一般包括:
1.单烯烃和二烯烃的聚合物,例如聚乙烯(可以是交联的),聚丙烯,聚异丁烯,聚-1-丁烯,聚甲基-1-戊烯,聚异戊二烯或聚丁二烯,以及环烯烃的聚合物,例如,环戊烯或降冰片烯的聚合物。
2.1)项下提到过的聚合物的混合物,例如聚丙烯与聚异丁烯的混合物。
3.单烯烃和二烯烃彼此间的共聚物或与其他乙烯基单体的共聚物,例如,乙烯/丙烯共聚物,丙烯/1-丁烯共聚物,丙烯/异丁烯共聚物,乙烯/1-丁烯共聚物,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/醋酸乙烯酯共聚物或乙烯/丙烯酸共聚物和它们的盐(离聚物),还有乙烯与丙烯和另一种二烯如己二烯,双环戊二烯或乙叉-降水片烯的三元共聚物。
4.聚苯乙烯,聚(α-甲基苯乙烯)。
5.苯乙烯或甲基苯乙烯与二烯类或丙烯酸类衍生物的共聚物,例如,苯乙烯/丁二烯,苯乙烯/丙烯腈,苯乙烯/甲基丙烯酸乙酯,苯乙烯/丁二烯/丙烯酸乙酯,苯乙烯/丙烯腈/丙烯酸甲酯的共聚物;苯乙烯共聚物和另一种聚合物例如聚丙烯酸酯,二烯聚合物或乙烯/丙烯/二烯三元共聚物组成的高冲击强度的混合物;和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。
6.苯乙烯的接枝共聚物,例如,苯乙烯接在聚丁二烯上,苯乙烯和丙烯腈接在聚丁二烯上;苯乙烯和丙烯酸或甲基丙烯酸的烷基酯接在聚丁二烯上;苯乙烯和丙烯腈接在乙烯/丙烯/二烯烃的三元共聚物上;苯乙烯和丙烯腈接在聚丙烯酸酯或聚甲基丙烯酸酯上;苯乙烯和丙烯腈接在丙烯酸酯/丁二烯的共聚物上,以及它们与在5)项下列出的共聚物的混合物,例如,称为ABS,MBS,ASA或AES聚合物的这些共聚物混合物。
7.含卤素的聚合物,如聚氯丁橡胶,氯化橡胶,氯化或氯磺化的聚乙烯,表氯醇的均聚物和共聚物,含卤素的乙烯基化合物的聚合物,例如,聚氯乙烯,聚偏氯乙烯,聚氟乙烯,聚偏氟乙烯,以及它们的共聚物,如氯乙烯/偏氯乙烯,氯乙烯/醋酸乙烯酯,偏氯乙烯/醋酸乙烯酯或氟乙烯/乙烯基醚共聚物。
8.由α,β-不饱和酸及其衍生物得到的聚合物,如聚丙烯酸酯和聚甲基丙烯酸酯;聚丙烯酰胺和聚丙烯腈。
9.在8)项下提到过的单体彼此间的或与其他不饱和单体的共聚物,例如,丙烯腈/丁二烯共聚物,丙烯腈/丙烯酸烷基酯共聚物,丙烯腈/丙烯酸烷氧基烷基酯或丙烯腈/卤化乙烯基共聚物或丙烯腈/甲基丙烯酸烷基酯/丁二烯三元共聚物。
10.由不饱和醇和胺或它们的酰基衍生物或其缩醛得到的聚合物,例如,聚乙烯醇,聚醋酸乙烯酯,聚硬脂酸乙烯酯,聚苯甲酸乙烯酯,聚马来酸乙烯酯,聚乙烯醇缩丁醛,聚邻苯二甲酸烯丙基酯或聚烯丙基三聚氰胺。
11.环醚类的均聚物和共聚物,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.聚缩醛如聚甲醛和那些含环氧乙烷作为共聚单体的聚甲醛。
13.聚苯醚和聚苯硫醚,和聚苯醚与苯乙烯聚合物的混合物
14.由带末端羟基的聚醚,聚酯或聚丁二烯和脂肪或芳族的多异氰酸酯,以及它的前体(多异氰酸酯、多醇或预聚物)得来的聚氨酯。
15.同二胺和二羧酸和/或由氨基羧酸或相应的内酰胺制得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,聚酰胺11,聚酰胺12,聚-2,4,4-三甲基六亚甲基对苯二甲酰胺,聚对亚苯基对苯二甲酰胺或聚间亚苯基间苯二甲酰胺,或与聚醚,例如与聚乙二醇,聚丙二醇或聚丁二醇的共聚物。
16.聚脲类,聚酰亚胺类,聚酰胺-酰亚胺类。
17.从二羧酸和二醇和/或从羟基羧酸或相应的内酯得来的聚酯类,例如,聚对苯二甲酸乙二酯,聚对苯二甲酸丁二酯,聚对苯二甲酸1,4-二羟甲基环己烷酯,聚对苯二甲酸[2,2-(4-羟苯基)-丙烷]酯和聚羟基苯甲酸,以及由末端羟基的聚醚衍生的嵌段共聚醚酯。
18.聚碳酸酯。
19.聚砜类,聚醚砜类和聚醚酮类。
20.由醛和酚,尿素或三聚氰胺衍生的交联共聚物,如酚/甲醛树脂,尿素/甲醛树脂和三聚氰胺/甲醛树脂。
21.干性和非干性的醇酸树脂。
22.由共聚酯类衍生的不饱和聚酯,这些共聚酯是由饱和的和不饱和的二羧酸与多羟基醇并以乙烯基类化合物为交联剂制得。还有它们的含卤素的低可燃性改性体。
23.由取代丙烯酸酯,例如,环氧丙烯酸酯,尿烷丙烯酸酯或聚酯丙烯酸酯衍生的热固性丙烯酸类树脂。
24.用三聚氰胺树脂,尿素树脂,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。
25.由多环氧化物,如双缩水甘油基醚或环脂族二环氧化物衍生的交联环氧树脂类。
26.天然聚合物如纤维素,橡胶,明胶和由这些聚合物经化学改性的相应的衍生物类,例如乙酸纤维素,丙酸纤维素和丁酸纤维素,或纤维素醚类如甲基纤维素。
27.前面提到过的聚合物的共混物,例如,PP/EPDM,聚酰胺6/EPDM或ABS,PVC/EVA,PVC/ABS,PVC/MBS,PC/ABS,PBTP/ABS。
28,天然存在的和合成的有机材料,这些原料是纯的单体化合物或者是这些化合物的混合物,例如,矿物油,动物和植物脂肪,油和蜡,或以合成的酯类(例如,邻苯二甲酸酯,己二酸酯,磷酸酯或偏苯三酸酯)为基础的油,脂肪和蜡,还有合成的酯与矿物油按任意重量比的混合物,这些材料可用做聚合物增塑剂或用作纺丝油,以及这些材料的水乳液。
29.天然或合成橡胶的水乳液,例如,天然的胶乳或羧基化苯乙烯/丁二烯共聚物胶乳。
30.聚硅氧烷,如USP 4259467中描述的亲水性软聚硅氧烷;和如USP4355147中描述的硬聚有机基硅氧烷。
31.聚酮亚胺与不饱和丙烯酸类聚乙酰乙酸酯树脂或与不饱和丙烯酸类树脂的结合。不饱和丙烯酸类树脂包括尿烷丙烯酸酯、聚醚丙烯酸酯、具有不饱和侧基的乙烯基或丙烯酰基共聚物和丙烯酸化的蜜胺。聚酮亚胺是在酸催化剂存在下从多胺和酮制备的。
32.含烯不饱和单体或齐聚物和多不饱和脂族齐聚物的可辐射固化的组合物。
33.环氧蜜胺树脂,如通过环氧官能基的共醚化的高固含量蜜胺树脂交联的光稳定的环氧树脂如LSE-4103(Monsanto)。
通常,本发明化合物的使用量为稳定化组合物的约1至20%(重),尽管可以随具体基体物质和应用场合而改变。有利的范围是1~5%,优选1.5~2.5%。
本发明所得的稳定化组合物还可非必须地含有约0.01%至约5%,优选约0.025%至约2%,尤其约0.1%至约1%(重)的各种常规添加剂,如下列物质或其混合物。
特别有意义的其它组合物包括另外含如下UV吸收剂的那些:二苯酮、苯并***、氰基丙烯酸衍生物、羟基芳基-s-三嗪、有机镍化合物及N,N’-草酰二苯胺。
优选的UV吸收剂选自:2-[2-羟基-3,5-二(α,α-二甲基苄基)苯基]-2H-苯并***、2-[2-羟基-3-(α,α-二甲基苄基)-5-辛基-苯基]-2H-苯并***、2-[2-羟基-3,5-二叔戊基-苯基]-2H-苯并***、2-[2-羟基-3-叔丁基-5-(ω-羟基-八(亚乙基氧)羰基)乙基苯基]-2H-苯并***、2-[2-羟基-3-叔丁基-5-(2-辛氧基羰基-乙基)苯基]-2H-苯并***、4,4’-二辛氧基-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、2,6-双(2,4-二甲基-苯基)-4-(2-羟基-4-辛氧基-苯基)-s-三嗪、2,6-双(2,4-二甲基-苯基)-4-(2,4-二羟基-苯基)-s-三嗪、2,4-双(2,4-二甲基-苯基)-6-(4-氯苯基)-s-三嗪、2,6-双(2,4-二甲基-苯基)-4-[2-羟基-4-(2-羟基-3-十二烷氧丙氧)苯基]-s-三嗪和2,2’-二羟基-4,4’-二甲氧基-二苯酮。
有意义的其它组合物包括另外含有效稳定量的酚抗氧化剂的那些;另外含受阻胺衍生物的那些;或另外含亚磷酸酯或亚膦酸酯稳定剂的那些。
特别有意义的组合物还包括那些其中有机物质是用于工业精饰的高固含量瓷漆;用做线圈涂层;用做渗透性木材精饰剂或用做成膜木材精饰剂。
当本发明化合物还含有反应性官能基时,所述化合物可以通过缩合或自由基加成反应化学键接至聚合物基材上。着提供了非迁移的非升华的UV吸收剂稳定剂。这种反应性官能基包括羟基、氨基、酰胺基、羧基和烯不饱和部分。
用于本发明的各种有机物质以及各种共添加剂在以下的该应用场合中详细描述,其中共添加剂与本发明化合物共同使用通常十分有利。
本发明所得的稳定化的聚合物组合物可非必须地含约0.01至约5%,优选约0.025至约2%,尤其约0.1至约1%重量的各种常规添加剂,如以下所列物质或其混合物。
1.抗氧化剂
1.1.烷基化一元酚类,例如2,6-二叔丁基-4-甲基苯酚,2-叔丁基-4,6-二甲基苯酚,2,6-二-叔丁基-4-乙基苯酚,2,6-二叔丁基-4-正丁基苯酚,2,6-二-叔丁基-4-异丁基苯酚,2,6-二环戊基-4-甲基苯酚,2-(α-甲基环己基)-4,6-二甲基苯酚,2,6-二-十八烷基-4-甲基苯酚,2,4,6-三环己基苯酚,2,6-二-叔丁基-4-甲氧基甲基苯酚。
1.2.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。
1.3.羟基化二苯醚硫类,例如,2,2′-硫连双(6-叔丁基-4-甲基苯酚),2,2′-硫连双(4-辛基苯酚),4,4′-硫连二(6-叔丁基-3-甲基苯酚),4,4′-硫连双(6-叔丁基-2-甲基苯酚)。
1.4.烷叉双酚类,例如,2,2′-亚甲基双(6-叔丁基-4-甲苯酚),2,2′-亚甲基双(6-叔丁基-4-乙基苯酚),2,2′-亚甲基双[4-甲基-6-(α-甲基环己基)苯酚],2,2′-亚甲基双(4-甲基-6-环己基苯酚),2,2′-亚甲基双(6-壬基-4-甲基苯酚),2,2′-亚甲基双(4,6-二-叔丁基苯酚),2,2′-乙叉双(4,6-二-叔丁基苯酚),2,2′-乙叉双(6-叔丁基-4-异丁基苯酚),2,2′-亚甲基双[6-(α-甲基苄基)-4-壬基苯酚],2,2′-亚甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚],4,4′-亚甲基双(2,6-二叔丁基苯苯酚),4,4′-亚甲基双(6-叔丁基-2-甲基苯酚),1,1-双(5-叔丁基-4-羟基-2-甲苯基)丁烷,2,6-双(3-叔丁基-5-甲基-2-羟基苄基)-4-甲基苯酚,1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷,1,1-双(5-叔丁基-4-羟基-2-甲基-苯基)3-正十二烷硫基丁烷,双[3,3-双(3′-叔丁基-4′-羟基苯基)丁酸乙二醇酯,双(3-叔丁基-4-羟基-5-甲基苯基)二环戊二烯,对苯二甲酸双[2-(3′-叔丁基-2′-羟基-5′-甲基苄基)-6-叔丁基-4-甲基苯基]酯。1.5.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,二(3,5-二叔丁基-4-羟基苄基)-硫醚,3,5-二叔丁基-4-羟基苄基-硫基乙酸异辛酯,双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫醇对苯二甲酸酯,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,3,5-二叔丁基-4-羟基苄基磷酸二(十八烷基)酯,3,5-二叔丁基-4-羟基苄基磷酸单乙酯的钙盐。1.6.酰基氨基酚类,例如:4-羟基-月桂酰苯胺,4-羟基-硬脂酰苯胺,2,4-双(辛硫基)-6-(3,5-二叔丁基-4-羟基-苯胺基)-s-三嗪,N-(3,5-二叔丁基-4-羟基-苯基)氨基甲酸辛酯。1.7.β-(3,5-二叔丁基-4-羟基-苯基)丙酸与一元醇或多元醇的酯,例如:同甲醇、十八烷醇、1,6-己二醇、新戊醇、硫二甘醇、三乙醇胺、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、二(羟乙基)草酸二酰胺、三异丙醇胺。1.8.β-(5-叔丁基-4-羟基-3-甲基-苯基)丙酸与一元醇或多元醇的酯,例如:同甲醇、十八烷醇、1,6-己二醇、新戊醇、硫二甘醇、三乙醇胺、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、二(羟乙基)草酸二酰胺、三异丙醇胺。1.9.β-(3,5-二叔丁基-4-羟基-苯基)丙酸的酰胺,例如:N,N’-双(3,5-二叔丁基-4-羟基-苯丙酰基)六亚甲基二胺、N,N’-双(3,5-二叔丁基-4-羟基-苯丙酰基)三亚甲基二胺、N,N’-双(3,5-二叔丁基-4-羟基-苯丙酰基)肼。2.紫外吸收剂和光稳定剂2.1.2-(2’-羟基-苯基)苯并***类,例如:5’-甲基-、3’,5’-二叔丁基-、5’-叔丁基-、5’-(1,1,3,3-四甲基-丁基)-、5-氯-3’,5’-二叔丁基、5-氯-3’-叔丁基-5’-甲基-、3’-仲丁基-5’-叔丁基-、4’-辛氧基、3’,5’-二叔戊基、3’,5’-双(α,α-二甲基苄基)、3’-α-枯基-5’-叔辛基,3’-叔丁基-5’-(2-(σ-羟基-八(乙烯氧)羰基-乙基)-、3’-十二烷基-5’-甲基-和3’-叔丁基-5’-(2-辛氧基羰基)乙基-,和十二烷基化的5’-甲基衍生物。
2.2.2-羟基二苯酮类,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-苄氧基,4,2′,4′-三羟基和2′-羟基-4,4′-二甲氧基衍生物类。
2.3.取代和未取代的苯甲酸酯类,例如,水杨酸4-叔丁基苯基酯,水杨酸苯基酯,水杨酸辛基苯基酯,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-2,4-二叔丁基苯基酯,3,5-二叔丁基-4-羟基苯甲酸十六烷基酯。
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.镍化合物类,例如,2,2′-硫连双[4-(1,1,3,3-四甲基丁基)苯酚]的镍配合物,如1∶1或1∶2配合物,具有或不具有附加的配位体(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,一烷基酯类的镍盐,例如,4-羟基-3,5-二叔丁基苄基膦酸的甲基、乙基或丁基酯;酮肟的镍配合物,例如,2-羟基-4-甲基苯基·十一烷基酮肟的镍配合物;具有或不具有附加配位体的1-苯基-4-十二烷酰基-5-羟基吡唑的镍配合物。
2.6.空间位阻的胺类,例如,癸二酸双(2,2,6,6-四甲基哌啶基)酯,癸二酸双(1,2,2,6,6-五甲基哌啶基)酯,n-丁基-3,5-二叔丁基-4-羟基苄基丙二酸双(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-羟基哌啶和丁二酸的缩合物,N,N′-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和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)双(3,3,5,5-四甲基哌啶酮)。2.7.草酰胺,例如,4,4′-二辛氧基-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′-双(3-二甲氨基丙基)草酰胺,2-乙氧基-5-叔丁基-2′-乙基-N,N′-草酰二苯胺和它同2-乙氧基-2′-乙基-5,4′-二叔丁基-N,N′-草酰二苯胺的混合物,和邻和对甲氧基双取代的-N,N′-草酰二苯胺的混合物,邻和对-乙氧基双取代的-N,N′-草酰二苯胺的混合物。2.8.羟基苯基-s-三嗪,例如:2,6-双(2,4-二甲基苯基)-4-(2-羟基-4-辛氧基苯基)-s-三嗪;2,6-双(2,4-二甲基苯基)-4-(2,4-二羟基-苯基)-s-三嗪;2,4-双(2,4-二羟基苯基)-6-(4-氯-苯基)-s-三嗪;2,4-双[2-羟基-4-(2-羟基-乙氧基)-苯基]-6-(4-氯-苯基)-s-三嗪;2,4-双[2-羟基-4-(2-羟基-4-(2-羟基-乙氧基))-苯基]-6-(2,4-二甲基-苯基)-s-三嗪;2,4-双[2-羟基-4-(2-羟基-乙氧基)-苯基]-6-(4-溴-苯基)-s-三嗪;2,4-双[2-羟基-4-(2-乙酰氧乙氧基)-苯基]-6-(4-氯-苯基)-s-三嗪;2,4-双(2,4-二羟基-苯基)-6-(2,4-二甲基-苯基)-s-三嗪。
3.金属减活化剂,例如,N,N′-二苯基草酰胺,N-水杨醛-N′-水杨酰肼,N,N′-双(水杨酰基)肼,N,N′-双(3,5-二叔丁基-4-羟基苯丙酰基)肼,3-水杨酰氨基-1,2,4-***,双(亚苄基)草酰肼。
4.亚磷酸酯类和亚膦酸酯,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-三-十二烷基酯,亚磷酸-三-十八烷基酯,二亚磷酸二硬脂季戊四醇酯,亚磷酸三(2,4-叔丁基苯基)酯,二亚磷酸二异癸基季戊四醇酯,二亚磷酸双(2,4-二叔丁基苯基)季戊四醇酯,三亚磷酸三硬脂基山梨醇酯,4,4′-亚联苯基二亚膦酸-四(2,4-二叔丁基苯基)酯。
5.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)。
6.羟胺类,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。
7.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。
8.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。
9.碱性其稳定剂,例如密胺,聚乙烯基吡咯烷酮,二氰胺,氰脲酸三烯丙酯,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、硬脂酸镁、蓖麻酸钠和棕榈酸钾,邻苯二酚锑,或邻苯二酚锌。
10.成核剂,例如4-叔丁基苯甲酸、己二酸、二苯基乙酸。
11.填料和增强剂,例如碳酸钙,硅酸盐,玻璃纤维,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。
12.其它添加剂,例如增塑剂,润滑剂,乳化剂,颜料,光学增白剂,阻燃剂,抗静电剂,发泡剂以及硫增效剂,如硫连二丙酸二月桂酸酯或硫连二丙酸二(十八烷基)酯。
特别有意义的酚抗氧化剂选自:3,5-二叔丁基-4-羟基-氢化肉桂酸正十八烷酯,四(3,5-二叔丁基-4-羟基-氢化肉桂酸)新戊烷四酯,3,5-二叔丁基-4-羟基-苄基膦酸双正十八烷酯,1,3,5-三(3,5-二叔丁基-4-羟基-苄基)异氰脲酸酯,双(3,5-二叔丁基-4-羟基-氢化肉桂酸)硫二乙酯,1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基-苄基)苯,双(3-甲基-5-叔丁基-4-羟基氢化肉桂酸)(3,6-二氧杂八亚甲基)酯,2,6-二叔丁基-对甲酚,2,2’-乙叉-双(4,6-二叔丁基酚),1,3,5-三(2,6-二甲基-4-叔丁基-3-羟基-苄基)异氰脲酸酯,1,1,3-三(2-甲基-4-羟基-5-叔丁基苯基)丁烷,1,3,5-三[2-(3,5-二叔丁基-4-羟基-氢化肉桂酰氧)乙基]异氰脲酸酯,3,5-二(3,5-二叔丁基-4-羟基苄基)米酚,双(3,5-二叔丁基-4-羟基-氢化肉桂酸)六亚甲基酯,1-(3,5-二叔丁基-4-羟基-苯胺基)-3,5-二辛硫基-s-三嗪,N,N’-六亚甲基-双(3,5-二叔丁基-4-羟基-氢化肉桂酰胺),双(3,5-二叔丁基-4-羟基-苄基膦酸乙酯)钙,双[3,3-二(3-叔丁基-4-羟基苯基)丁酸二乙酯,3,5-二叔丁基-4-羟基-苄基硫基乙酸辛酯,双(3,5-二叔丁基-4-羟基-氢化肉桂酰)酰肼和N,N’-双[2-(3,5-二叔丁基-4-羟基-氢化肉桂酰氧)-乙基]-草酰胺。
最优选的酚抗氧化剂是四(3,5-二叔丁基-4-羟基-氢化肉桂酸)新戊烷四酯,3,5-二叔丁基-4-羟基-氢化肉桂酸正十八烷酯,1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基-苄基)苯,1,3,5-三(3,5-二叔丁基-4-羟基-苄基)异氰脲酸酯,2,6-二叔丁基-对甲酚,2,2’-乙叉-双(4,6-二叔丁基酚)。
特别有意义的受阻胺选自:癸二酸双(2,2,6,6-四甲基哌啶-4-基)酯,癸二酸双(1,2,2,6,6-五甲基哌啶-4-基)酯,(3,5-二叔丁基-4-羟基-苄基)丁基丙二酸双(1,2,2,6,6-五甲基哌啶-4-基)酯,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,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,次氮基三乙酸三(2,2,6,6-四甲基哌啶-4-基)酯,1,2-双(2,2,6,6-四甲基-3-氧哌啶-4-基)乙烷,2,2,4,4-四甲基-7-氧杂-3,20-二氮杂-21-氧二螺[5.1.11.2]二十一烷,2,4-二氯-6-叔辛氨基-s-三嗪和4,4’-六亚甲基双(氨基-2,2,6,6-四甲基-哌啶)的缩聚产物,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基-哌啶和丁二酸的缩聚产物,4,4’-六亚甲基双-(氨基-2,2,6,6-四甲基哌啶)和1,2-二溴乙烷的缩聚产物,1,2,3,4-丁四羧酸四(2,2,6,6-四甲基哌啶-4-基)酯,1,2,3,4-丁四羧酸四(1,2,2,6,6-五甲基哌啶-4-基)酯,2,4-二氯-6-吗啉代-s-三嗪和4,4’-六亚甲基双-(氨基-2,2,6,6-四甲基哌啶)的缩聚产物,N,N′,N″,N-四[(4,6-双(丁基-1,2,2,6,6-五甲基哌啶-4-基)-氨基-s-三嗪-2-基]-1,10-二氨基-4,7-二氮杂癸烷,混合的1,2,3,4-丁四羧酸[2,2,6,6-四甲基哌啶-4-基/β,β,β’,β’-四甲基-3,9-(2,4,8,10-四氧杂螺[5.5]-十一烷)二乙基]酯,混合的1,2,3,4-丁四羧酸[1,2,2,6,6-五甲基哌啶-4-基/β,β,β’,β’-四甲基-3,9-(2,4,8,10-四氧杂螺[5.5]-十一烷)二乙基]酯,双(2,2,6,6-四甲基哌啶-4-羧酸)八亚甲基酯,4,4’-乙撑双(2,2,6,6-四甲基哌嗪-3-酮),N-2,2,6,6-四甲基哌啶-4-基-正十二烷基丁二酸酰亚胺,N-1,2,2,6,6-五甲基哌啶-4-基-正十二烷基丁二酸酰亚胺,N-1-乙酰基-2,2,6,6-四甲基哌啶-4-基-正十二烷基-丁二酸酰亚胺,1-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,癸二酸双(1-辛氧基-2,2,6,6-四甲基哌啶-4-基)酯,丁二酸双(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)酯,1-辛氧基-2,2,6,6-四甲基-4-羟基-哌啶,聚{[6-叔辛氨基-s-三嗪-2,4-二基][2-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基-六亚甲基-[4-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基]},和2,4,6-三[N-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基]-s-三嗪。
最优选的受阻胺化合物是癸二酸双(2,2,6,6-四甲基哌啶-4-基)酯,癸二酸双(1,2,2,6,6-五甲基哌啶-4-基)酯,(3,5-二叔丁基-4-羟基-苄基)丁基丙二酸双(1,2,2,6,6-五甲基哌啶-4-基)酯,1-(2-羟乙基)-2,2,6,6-四甲基-4-羟基-哌啶和丁二酸的缩聚产物,2,4-二氯-6-叔辛氨基-s-三嗪和4,4’-六亚甲基双(氨基-2,2,6,6-四甲基-哌啶)的缩聚产物,N,N’,N″,N-四[(4,6-双(丁基-1,2,2,6,6-五甲基哌啶-4-基)-氨基)-s-三嗪-2-基]-1,10-二氨基-4,7-二氮杂癸烷,癸二酸双(1-辛氨基-2,2,6,6-四甲基哌啶-4-基)酯,丁二酸双(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)酯,1-辛氧基-2,2,6,6-四甲基-4-羟基-哌啶,聚{[6-叔辛氨基-s-三嗪-2,4-二基][2-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基-六亚甲基-[4-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)亚氨基]},和2,4,6-三[N-(1-环己氧基-2,2,6,6-四甲基哌啶-4-基)-正丁基氨基]-s-三嗪。
以下实施例用于说明本发明。实施例11-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶与苯乙烯的1,2-双加合物
将10g1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶在120m1苯乙烯中的脱氧溶液在100℃加热24小时。减压除去未反应的苯乙烯。用色谱将标题化合物从残留物中分离,并经己烷/乙酸乙酯结晶纯化得到5.3g加合产物,熔点175-176℃。实施例21-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶与4-氯苯乙烯的1,2-双加合物
按照实施例1中的方法,用等当量的4-氯苯乙烯代替苯乙烯,用色谱纯化后得到白色固状标题化合物,熔点76-78℃。实施例31-烃氧基-2,2,6,6-四甲基-4-羟基哌啶与苯乙烯的1,2-双加合物
按照实施例1中的方法,用等当量的1-烃氧基-2,2,6,6-四甲-4-羟基哌啶代替1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶,用色谱纯化后得到白色固状标题化合物,熔点104-108℃。实施例41-烃氧基-2,2,6,6-四甲基-哌啶与苯乙烯的1,2-双加合物
按照实施例1中的方法,用等当量的1-烃氧基-2,2,6,6-四甲基-哌啶代替1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶,用色谱纯化后得到无色油状的标题化合物。实施例51-烃氧基-2,2,6,6-四甲基-4-氧代基-哌啶与苯乙烯的1,2-双加合物
按照实施例1中的方法,用等当量的1-烃氧基-2,2,6,6-四甲基-4-氧代基哌啶代替1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶,用色谱纯化后得到无色蜡状固态标题化合物。实施例62-烃氧基-1,1,3,3-四甲基异二氢吲哚与苯乙烯的1,2-双加合物
按照实施例1中的方法,用等当量的2-烃氧基-1,1,3,3-四甲基异二氢吲哚代替1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶,用色谱纯化后得到白色固状标题化合物,熔点138-139℃。实施例71-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基-哌啶与丙烯酸丁酯的1,2-双加合物
将30g1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基-哌啶在50m1丙烯酸丁酯中的脱氧溶液在130℃加热22小时。减压除去未反应的丙烯酸丁酯。用色谱从残留物中分离出标题化合物,得到9.0g无色油状的加合物。实施例81-烃氧基-2,2,6,6-四甲基-4-羟基-哌啶与丙烯酸丁酯的1,2-双加合物
按照实施例7的方法,用等当量的1-烃氧基-2,2,6,6-四甲基-4-羟基-哌啶代替1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基-哌啶,用色谱纯化后得到白色固状标题化合物,熔点115~117℃。实施例9~15
通过用1N氢氧化钠水溶液清洗并随后减压蒸馏除去工业级苯乙烯中的叔丁基邻苯二酚贮存稳定剂。
向装有温度计、冷凝器、橡胶隔片和磁力搅拌棒的300ml三口烧瓶中加入100g如上纯化的无抑制剂(实施例9)的苯乙烯或在另外的实验中加入200mg本发明的各种测试化合物(实施例10~15)。通过五次连续抽空和反充氮气来建立无氧环境,随后用纯氮喷苯乙烯溶液15分钟。该容器浸入机械搅拌的控制在120℃的恒温油浴中。定时取出少份量样品并分析聚合物含量。然后用折射率方法测定形成的聚苯乙烯的量,用已知浓度的苯乙烯溶液中的真实聚苯乙烯校正。结果列于表1中。表1
实施例 | 以下实施例号的化合物 | 加热以下时间后形成的聚合物百分数 | ||
30分钟 | 60分钟 | 90分钟 | ||
9 | 无 | 3.7 | 8.4 | - |
10 | 1 | 0.0 | 0.5 | 2.8 |
11 | 2 | 0.0 | 0.8 | 3.8 |
12 | 3 | 0.0 | 0.2 | 1.6 |
13 | 4 | 0.0 | 0.0 | 1.0 |
14 | 5 | 0.1 | 0.1 | 1.9 |
15 | 6 | 0.0 | 0.2 | 1.3 |
从这些数据可以看到,与未受抑制的实施例9中苯乙烯样品相比,本发明的实施例10~15的每种加合物提供了优异的抑制效应以防止或降低苯乙烯单体的早期聚合。实施例161-烃氧基-2,2,6,6-四甲基-4-乙酰胺基-哌啶与苯乙烯的1,2-双加合物
按照实施例1中的方法,用等当量的1-烃氧基-2,2,6,6-四甲基-4-乙酰胺基哌啶代替1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶,用色谱纯化后得到标题化合物。实施例17ABS/聚碳酸酯共混物的光稳定化
通过在小型布拉本德挤出机中复合混合的树脂颗粒制备ABS(含受阻胺稳定剂式I化合物)和聚碳酸酯的50/50共混物。制备注塑而成的125密耳(3.2mm)Izod条用于评价光稳定性,通过进行标准的内部自动Xenon Arc Wea ther Ometer(氙弧老化仪)暴露和喷射Xenon Arc WeatherOmeter暴露测试来进行评价。
含有本发明式I化合物稳定剂的ABS/聚碳酸酯共混物与无受阻胺化合物的对比聚合物相比,体现增强的光稳定性。实施例18聚丙烯纤维的稳定化
当聚丙烯纤维含有式I化合物的稳定剂时,与未被稳定的聚丙烯纤维相比体现优异的光和热稳定性。
Claims (19)
1.式I或II的化合物 其中,R1和R2独立为C1-C4的烷基,或R1和R2一起为五亚甲基;E为C6-C10的芳基,或被C1-C4烷基或被卤素取代的所述芳基,或E为-COOH或-COOR6,其中R6为C1-C18烷基或C2-C8羟烷基,或E为-CN;R3、R4和R5各自为C1-C4烷基;和T为完成5,6或7元环或1,1,3,3-四甲基异二氢吲哚部分所需的基团,所述T基团也可以被以下基团取代:羟基、氧代基、乙酰胺基、-OR8,其中R8为C1-C18烷基、或-O-CO-R9,其中R9为C1-C17烷基或苯基,条件是式I化合物不为1-苯基-1,2-双(2,2,6,6-四甲基哌啶-1-基氧)-乙烷或1-苯基-1,2-双(1,1,3,3-四甲基-异二氢吲哚-2-基氧)乙烷。
2.根据权利要求1的化合物,其中R1和R2各为甲基。
3.根据权利要求1的化合物,其中E为-COOH、-CN或-COOR6,其中R6为C1-C4烷基。
4.根据权利要求3的化合物,其中R6为丁基。
5.根据权利要求1的化合物,其中R3、R4和R5各为甲基。
6.根据权利要求1的化合物,其中T为完成5、6或7元环或1,1,3,3-四甲基-异二氢吲哚部分所需的基团,其中所述T基团为未取代的或被羟基、氧代基、乙酰胺基或-O-CO-R9取代的基团,其中R9为C1-C11烷基或苯基。
7.根据权利要求1的化合物,它是(a)1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶和苯乙烯的1,2-双加合物;(b)1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶和4-氯-苯乙烯的1,2-双加合物;(c)1-烃氧基-2,2,6,6-四甲基-4-羟基哌啶和苯乙烯的1,2-双加合物;(d)1-烃氧基-2,2,6,6-四甲基-4-氧代哌啶和苯乙烯的1,2-双加合物;(e)1-烃氧基-2,2,6,6-四甲基-4-苯甲酰氧基哌啶和丙烯酸丁酯的1,2-双加合物;(f)1-烃氧基-2,2,6,6-四甲基-4-羟基哌啶和丙烯酸丁酯的1,2-双加合物;或(g)1-烃氧基-2,2,6,6-四甲基-4-乙酰胺基哌啶和苯乙烯的1,2-双加合物。
8.一种被稳定化以防止早期聚合的组合物,它包括
a.烯不饱和单体,和
b.有效稳定量的根据权利要求1的式I或II的化合物。
9.根据权利要求8的组合物,其中烯不饱和单体选自;乙烯基芳烃;二烯;卤化乙烯基单体;不饱和酸;不饱和酯;不饱和腈;不饱和醚;和各种乙烯基单体,它们为乙烯基吡啶、乙烯基膦酸二乙酯和苯乙烯磺酸钠。
10.根据权利要求9的组合物,其中单体是α-甲基苯乙烯、二乙烯基苯、丁二烯、异戊二烯、氯乙烯、氯丁二烯、偏氯乙烯、偏氟乙烯、氟乙烯、丙烯酸、甲基丙烯酸、巴豆酸、丙烯酸丁酯、甲基丙烯酸甲酯、丙烯酸乙酯、丙烯酸甲酯、丙烯腈、甲基丙烯腈或甲基乙烯基醚。
11.根据权利要求10的组合物,其中单体为丙烯酸、甲基丙烯酸、丙烯酸丁酯、丙烯酸乙酯或丙烯腈。
12.根据权利要求8的组合物,其中有效稳定量的组分(b)为基于组分(a)单体重量的1至10000ppm。
13.一种被稳定的组合物,它包括
a.易受热、氧或光化辐射不利影响的有机物质,和
b.有效稳定量的根据权利要求1的式I或II化合物。
14.根据权利要求13的组合物,其中组分(a)为聚合物。
15.根据权利要求14的组合物,其中聚合物为聚烯烃。
16.根据权利要求15的组合物,其中聚烯烃为聚丙烯或聚乙烯。
17.根据权利要求13的组合物,其中组分(a)为聚合物、共聚物或聚合物共混物,它在至少一种聚合物或聚合物组分中含有有效的烯不饱和位。
18.根据权利要求17的组合物,其中组分(a)聚合物选自:ABS、HIPS、SBR乳液、PP/EPDM、PP/NBR、PP/NR、ABS/PC、ABS/尼龙、ABS/PVC、ABS/聚酯、ABS/SMA、ABS/聚砜、ASA/PC、缩醛/弹性体、聚酯/弹性体、尼龙/弹性体、PPO/NR、EPDM/NBR和EPDM/烯烃。
19.根据权利要求1的式I和式II的双加合物的应用,用做有效的抑制剂防止烯不饱和单体的早期聚合。
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US755,882 | 1985-07-17 | ||
US08/755,882 US5844025A (en) | 1996-12-02 | 1996-12-02 | 1,2-Bis-adducts of stable nitroxides with substituted ethylenes and stabilized compositions |
US755882 | 1996-12-02 |
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US (2) | US5844025A (zh) |
EP (1) | EP0845458B1 (zh) |
JP (2) | JP4423485B2 (zh) |
KR (1) | KR100471949B1 (zh) |
CN (1) | CN1174968C (zh) |
BR (1) | BR9706064A (zh) |
CA (1) | CA2223112C (zh) |
DE (1) | DE69708028T2 (zh) |
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TW (1) | TW434287B (zh) |
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CN113166466A (zh) * | 2018-12-03 | 2021-07-23 | 盛禧奥欧洲有限责任公司 | 亚乙烯基芳族单体与具有酸基的不饱和化合物的共聚物的离聚物 |
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DE19725519A1 (de) * | 1997-06-17 | 1998-12-24 | Basf Ag | Stoffmischung, enthaltend vinylgruppenhaltige Verbindungen und Stabilisatoren |
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US6235819B1 (en) * | 1997-12-31 | 2001-05-22 | Bridgestone Corporation | Process to scavenge amines in polymeric compounds by treatment with triazine derivatives and compositions therefrom |
US6040488A (en) * | 1998-06-02 | 2000-03-21 | Ppg Industries Ohio, Inc. | Stabilization of vinylidene chloride |
US5910232A (en) * | 1998-06-10 | 1999-06-08 | Nalco/Exxon Energy Chemicals, L.P. | Method for inhibiting polymer formation in styrene processing |
KR20010079775A (ko) * | 1998-09-09 | 2001-08-22 | 칼 에이. 로월드 | 치환 디히드록시아렌 및 니트록시드를 이용한 스티렌모노머 중합반응 억제방법 |
KR20010079776A (ko) * | 1998-09-09 | 2001-08-22 | 칼 에이. 로월드 | 장애 히드록실아민을 이용한 비닐 모노머 중합반응 억제방법 |
US6271377B1 (en) | 1999-02-25 | 2001-08-07 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
US6376584B1 (en) | 1999-02-25 | 2002-04-23 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
GB0003326D0 (en) * | 1999-02-25 | 2000-04-05 | Ciba Sc Holding Ag | Hydroxy-Substituted N-Alkoxy hindered amines |
US6392041B1 (en) | 1999-02-25 | 2002-05-21 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
US6472486B2 (en) | 1999-03-09 | 2002-10-29 | Symyx Technologies, Inc. | Controlled stable free radical emulsion polymerization processes |
US6875831B1 (en) * | 1999-07-02 | 2005-04-05 | Ciba Specialty Chemicals Corp. | Mono and multifunctional alkoxyamines for the preparation of functionalized macromers |
US6716948B1 (en) | 1999-07-31 | 2004-04-06 | Symyx Technologies, Inc. | Controlled-architecture polymers and use thereof as separation media |
DE19938841A1 (de) * | 1999-08-17 | 2001-02-22 | Basf Ag | Inhibitorkomposition zur Stabilisierung von radikalisch polymerisierbaren Substanzen |
US6525146B1 (en) * | 2000-04-03 | 2003-02-25 | Baker Hughes Incorporated | Inhibition of popcorn polymer growth |
US20030041268A1 (en) * | 2000-10-18 | 2003-02-27 | Noriaki Hashimoto | Method and system for preventing unauthorized access to the internet |
DE10106543A1 (de) * | 2001-02-13 | 2002-08-22 | Basf Ag | Beschichtungsmittelzusammensetzungen |
US20040143051A1 (en) * | 2003-01-22 | 2004-07-22 | Jianfeng Lou | Unsaturated polyester resin compositions with improved processing and storage stability |
US7118689B2 (en) | 2003-08-27 | 2006-10-10 | Ppg Industries Ohio, Inc. | Stabilized polychloroethylenes |
US20100143580A1 (en) * | 2008-05-28 | 2010-06-10 | American Air Liquide, Inc. | Stabilization of Bicycloheptadiene |
KR101892623B1 (ko) * | 2011-04-29 | 2018-08-30 | 삼성디스플레이 주식회사 | 중성표면을 형성하기 위한 랜덤 공중합체 및 그 제조 및 사용 방법들 |
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US4547537A (en) * | 1984-08-02 | 1985-10-15 | Ciba-Geigy Corporation | N-Piperidyl tetrahydro-1,4-oxazin-2-one light stabilizers |
JPS62167734A (ja) * | 1986-01-18 | 1987-07-24 | Sumitomo Chem Co Ltd | 重合体副生成物の生成を防止する方法 |
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CN113166466A (zh) * | 2018-12-03 | 2021-07-23 | 盛禧奥欧洲有限责任公司 | 亚乙烯基芳族单体与具有酸基的不饱和化合物的共聚物的离聚物 |
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EP0845458B1 (en) | 2001-11-07 |
DE69708028T2 (de) | 2002-06-06 |
JPH10182605A (ja) | 1998-07-07 |
US5844025A (en) | 1998-12-01 |
RU2187502C2 (ru) | 2002-08-20 |
CA2223112A1 (en) | 1998-06-02 |
BR9706064A (pt) | 2000-03-14 |
US6218536B1 (en) | 2001-04-17 |
KR100471949B1 (ko) | 2006-04-28 |
ES2165015T3 (es) | 2002-03-01 |
DE69708028D1 (de) | 2001-12-13 |
CN1174968C (zh) | 2004-11-10 |
EP0845458A1 (en) | 1998-06-03 |
TW434287B (en) | 2001-05-16 |
MX9709369A (es) | 1998-07-31 |
KR19980063593A (ko) | 1998-10-07 |
JP4423485B2 (ja) | 2010-03-03 |
JP2009242802A (ja) | 2009-10-22 |
CA2223112C (en) | 2007-11-06 |
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