CN101111467A - 作为表面改性剂的全氟化醇或胺的功能化酯、酰胺或聚氨酯 - Google Patents
作为表面改性剂的全氟化醇或胺的功能化酯、酰胺或聚氨酯 Download PDFInfo
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- CN101111467A CN101111467A CNA2006800036543A CN200680003654A CN101111467A CN 101111467 A CN101111467 A CN 101111467A CN A2006800036543 A CNA2006800036543 A CN A2006800036543A CN 200680003654 A CN200680003654 A CN 200680003654A CN 101111467 A CN101111467 A CN 101111467A
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- Prior art keywords
- alkyl
- hydrogen
- phenyl
- butyl
- composition
- 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.)
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
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- MQOCIYICOGDBSG-UHFFFAOYSA-M potassium;hexadecanoate Chemical compound [K+].CCCCCCCCCCCCCCCC([O-])=O MQOCIYICOGDBSG-UHFFFAOYSA-M 0.000 description 1
- 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
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
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- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004460 silage Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
- 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
- IJRHDFLHUATAOS-DPMBMXLASA-N sodium;(z,12r)-12-hydroxyoctadec-9-enoic acid Chemical compound [Na+].CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O IJRHDFLHUATAOS-DPMBMXLASA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- 229920005613 synthetic organic polymer Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005382 thermal cycling Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- 229910000048 titanium hydride Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000005591 trimellitate group Chemical group 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
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Abstract
本发明描述包含下列组分的组合物:a)易受氧化、热或光诱导降解的有机材料,和b)至少一种通式I的化合物的熔体添加剂其中所有符号R1、R2、R3和X都如权利要求1中定义。通式I的化合物适用于作为有机材料的表面能降低剂,例如,用来提高有机材料的斥油和斥水性。
Description
本发明涉及包含易受氧化、热或光诱导降解的有机材料,优选是合成聚合物,的组合物以及涉及作为这类材料的表面能降低剂,如作为有机材料的斥油和斥水剂的全氟化醇的酯、酰胺或聚氨酯。
在纤维或纤维底基,如织物、地毯、纸、皮革和非织造纤网上用各种氟化学组合物来改善斥油和斥水性是已知的,如U.S.6,127,485中所述。该参考文献公开了包含合成有机聚合物的疏水和疏油纤维、薄膜和模塑制品,其中氟化学化合物被分散在纤维、薄膜或模塑制品内并存在于纤维、织物或模塑制品的表面。
已知的氟化合物在各方面都不满足高要求:为满足作为有机材料的表面能降低剂,例如,用来增加有机材料的斥油和斥水性,需要熔体添加剂。
现已发现,全氟化醇的酯、酰胺或聚氨酯适用于各种技术应用,例如,用来提高合成聚合物之类有机材料的斥油和斥水性。
因此本发明提供包含下列组分的组合物:
a)易受氧化、热或光诱导降解的有机材料,和
b)至少一种通式I的化合物
其中
R3是含氟基,
R4是C1~C25烷基、C3~C25链烯基、未取代或C1~C4烷基取代的苯基;
R6是氢、C1~C8烷基或苄基,
R7是C1~C25烷基、C2~C25链烯基、未取代或被C1~C4烷基或C1~C4烷酰基氨基取代的苯基;未取代或C1~C4烷基取代的苯基氨基,
R8是-NO2,-N=CH-R4或
R9是氢或-Y-R7,
R10是氢、C1~C8烷基或苄基,
R11是氢、C1~C8烷基或苄基,
Z是C1~C25亚烷基、1,2-亚苯基、1,3-亚苯基、1,4-亚苯基或
R12和R13彼此独立地是氢、C1~C12烷基或苯基,或R11和R12连同键接的碳原子一起形成未取代或被1~3个C1~C4烷基所取代的C5~C8亚环烷基环。
含氟基团是含至少一个氟原子的支化或未支化基团,例如,C1~C25氟代烷基,C1~C25氟代烷基是,例如,氟甲基、2-氟乙基、3-氟丙基、4-氟丁基、5-氟戊基、6-氟己基、7-氟庚基、二氟甲基、三氟甲基、五氟乙烯、五氟丁基或全氟烷基,如-CH2CH2(CF2)7CF3或-CH2CH2(CF2)3CF3。
含最多25个碳原子的烷基是支化或未支化基团,例如,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-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、二十烷基或二十二烷基。
含3~25个碳原子的链烯基是支化或未支化基团,例如,丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正-2,4-戊二烯基、3-甲基-2-丁烯基、正-2-辛烯基、正-2-十二碳烯基、异十二碳烯基、油基、正-2-十八碳烯基或正-4-十八碳烯基。优选含3~18个碳原子,尤其3~12个碳原子,例如,3~6个碳原子,尤其3~4个碳原子的链烯基。
优选含1~3个,尤其1或2个烷基或烷酰基氨基的C1~C4烷基取代的或C1~C4烷酰基氨基取代的苯基是,例如,邻-、间-或对-甲基苯基、2,3-二甲基苯基、2,4-二甲基苯基、2,5-二甲基苯基、2,6-二甲基苯基、3,4-二甲基苯基、3,5-二甲基苯基、2-甲基-6-乙基苯基、4-叔丁基苯基、4-叔新戊酰基氨基苯基、2-乙基苯基或2,6-二乙基苯基。
优选含1~3个,尤其1或2个烷基的C1~C4烷基取代的苯基氨基是,例如,邻-、间-或对-甲基苯基氨基、2,3-二甲基苯基氨基、2,4-二甲基苯基氨基、2,5-二甲基苯基氨基、2,6-二甲基苯基氨基、3,4-二甲基苯基氨基、3,5-二甲基苯基氨基、2-甲基-6-乙基苯基氨基、4-叔丁基苯基氨基、2-乙基苯基氨基或2,6-二乙基苯基氨基。
含最多4个碳原子的烷酰氨基是支化或未支化基团,例如,甲酰氨基、乙酰氨基、丙酰氨基、丁酰氨基或新戊酰氨基。
优选含1~3个,尤其1或2个支化或未支化烷基团的被C1~C4烷基取代的C5~C8亚环烷基环是,例如,亚环戊基、甲基亚环戊基、二甲基亚环戊基、亚环己基、甲基亚环己基、二甲基亚环己基、三甲基亚环己基、叔丁基亚环己基、亚环庚基或亚环辛基。优选亚环己基和叔丁基亚环己基。
重要的组合物包含至少一种通式I的化合物为组分(b),其中
R2是-X-R3,
R3是C1~C25氟代烷基,
R11是氢或C1~C4烷基。
优选的组合物包含至少一种通式I,其中R3是C1~C25氟代烷基,的化合物作为组分(b)。
还优选组合物包含至少一种通式I,其中R6和R10是氢,的化合物作为组分(b)。
尤其优选组合物包含至少一种通式I,其中R7是C1~C18烷基、C2~C18链烯基、未取代或被C1~C4烷基或C1~C4烷酰氨基取代的苯基;未取代或C1~C4烷基取代的苯基氨基,的化合物作为组分(b)。
重要的组合物包含至少一种通式I,其中R12和R13彼此独立地各是氢或C1~C4烷基,或R12和R13连同键合的碳原子一起形成亚环己基环,的化合物作为组分(b)。
也重要的组合物包含至少一种通式I的化合物作为组分(b),其中,
R1是-NO2,-N=CH-R4或
R3是-CH2CH2(CF2)7CF3或-CH2CH2(CF2)3CF3,
R4是C4~C12烷基、C4~C12链烯基、未取代或C1~C4烷基取代的苯基;
R5是氢、-Y-R7,
R6是氢,
R7是C1~C8烷基、C2~C8链烯基、苯基或苯基氨基,
R10是氢,
R11是氢,
Z是C4~C12亚烷基、1,3-亚苯基、1,4-亚苯基或
R12和R13是氢。
通式I的化合物可按本质上已知的方法,如通过羧酸与醇或酰胺的酯化或酰胺化而制成。聚氨酯优选由异氰酸酯与醇的反应而制成。
通式I的化合物适用于作有机材料的斥油和斥水剂。可存在于本发明组合物中的有机材料的实例如下:
1.单烯烃和二烯烃聚合物,例如,聚丙烯、聚异丁烯、聚丁烯-1、聚-4-甲基戊烯-1、聚乙烯基环己烷、聚异戊二烯或聚丁二烯,以及环烯烃聚合物,例如,环戊烯或降冰片烯,聚乙烯(任选地能被交联),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)、线形低密度聚乙烯(LLDPE)、(VLDPE)和(ULDPE)。
聚烯烃,即上一段所列举的单烯烃的聚合物,优选聚乙烯和聚丙烯,能用不同的,尤其下列方法制成:
a)自由基聚合(一般在高压和高温下)。
b)用通常含周期表内IVb、Vb、VIb或VIII族中一种或多种金属的催化剂的催化聚合。这些金属通常都有一个或一个以上的配位体,典型的是氧化物、卤化物、醇化物、酯、醚、胺、烷基、链烯基和/或可以是π-或σ-共轭的芳基。这些金属配合物可以呈游离形式或固定在基体上,典型地,在活性氯化镁、氯化钛(III)、氧化铝或氧化硅上。这些催化剂可以是可溶于或不溶于聚合介质的。在聚合中可以用催化剂本身或还可以用其它活化剂,一般是烷基金属、金属卤化物、烷基金属卤化物、烷基金属氧化物或烷氧烷金属,所述金属是周期表内Ia、IIa和/或IIIa族中的元素。传统上,活化剂可以用其它酯、醚、胺或甲硅烷基进行改性。这些催化剂体系通常称做Phillip、美孚Indiana、Ziegler(-Natta)、TNZ(杜邦)、茂金属或单点催化剂(SSC)。
2.在1)中提到的聚合物的混合物,例如,聚丙烯和聚异丁烯、聚丙烯和聚乙烯的混合物(例如,PP/HDPE、PP/LDPE),以及不同类型聚乙烯的混合物(例如,LDPE/HDPE)。
3.单烯烃和二烯烃相互之间或与其它乙烯基单体的共聚物,例如,乙烯/丙烯共聚物、线形低密度聚乙烯(LLDPE)及其混合物和低密度聚乙烯(LDPE)、聚丙烯/丁烯-1共聚物、丙烯/异丁烯共聚物、乙烯/丁烯-1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,其中1-烯烃是原位产生的;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/乙酸乙烯酯共聚物或乙烯/丙烯酸共聚物和它们的盐(离聚物),以及乙烯与丙烯和二烯的三元共聚物,所述二烯如己二烯、二环戊二烯或亚乙基-降冰片烯;以及这类共聚物相互之间和与以上1)中提到的聚合物的混合物,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)、LLDPE/EVA、LLDPE/EAA和交替或无规聚亚烃/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(如C5~C9),包括其氢化改性物(如增粘剂)和聚亚烃和淀粉的混合物在内。
1.)~4.)的均聚物和共聚物可具有任何空间立构,包括间同立构、全同立构、半全同立构或无规立构在内;优选无规立构聚合物。也包括空间立构嵌段聚合物在内。
5.聚苯乙烯、聚(对甲基苯乙烯)、聚(α-甲基苯乙烯)。
6.衍生自乙烯基芳族单体的均聚物和共聚物,所述乙烯芳族单体包括苯乙烯,α-甲基苯乙烯,乙烯基甲苯的所有异构体,尤其对-乙烯基甲苯,乙基苯乙烯、丙基苯乙烯、乙烯基联苯、乙烯基萘和乙烯基蒽的所有异构体,以及它们的混合物。均聚物和共聚物可具有任何空间立构结构,包括间同立构、全同立构、半全同立构或无规立构在内;优选无规立构聚合物。也包括空间立构嵌段聚合物在内。
6a.包括前述乙烯基芳族和选自下列共聚单体的共聚物:乙烯、丙烯、二烯、腈、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以及它们的混合物,例如,苯乙烯/丁二烯、苯乙烯/丙烯腈、苯乙烯/乙烯(共聚体)、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;高抗冲苯乙烯共聚物和另一种聚合物,如聚丙烯酸酯、二烯聚合物或乙烯/丙烯/二烯三元共聚物的混合物;以及苯乙烯的嵌段共聚物,如苯乙烯/丁二烯/苯乙烯、苯乙类/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.衍生自氢化6)中提到的聚合物的氢化芳族聚合物,尤其包括由氢化无规立构聚苯乙烯制成的聚环己基乙烯(PCHE)在内,常称之为聚乙烯基环己烷(PVCH)。
6c.衍生自氢化6a.)中提到的聚合物的氢化芳族聚合物。
均聚物和共聚物可具有任何空间立构,包括间同立构、全同立构、半全同立构或无规立构在内;优选无规立构聚合物。也包括空间立构嵌段聚合物在内。
7.乙烯基芳族单体如苯乙烯或α-甲基苯乙烯的接枝共聚物,例如,苯乙烯在聚丁二烯上、苯乙烯在聚丁二烯-苯乙烯或聚丁二烯-丙烯腈共聚物上;苯乙烯和丙烯腈(或甲基丙烯腈)在聚丁二烯上;苯乙烯、丙烯腈和甲基丙烯酸甲酯在聚丁二烯上;苯乙烯和马来酸酐在聚丁二烯上;苯乙烯、丙烯腈和马来酸酐或马来酰亚胺在聚丁二烯上;苯乙烯和马来酰亚胺在聚丁二烯上;苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯在聚丁二烯上;苯乙烯和丙烯腈在乙烯/丙烯/二烯三元共聚物上;苯乙烯和丙烯腈在聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上;苯乙烯和丙烯腈在丙烯酸酯/丁二烯共聚物上,以及它们和6)中所列共聚物的混合物,例如,以ABS、MBS、ASA或AES聚合物著称的共聚物混合物。
8.含卤聚合物,如氯丁橡胶、氯化橡胶、异丁烯-异戊二烯的氯化和溴化共聚物(卤代丁基橡胶)、氯化或氯磺化聚乙烯、乙烯和氯化乙烯的共聚物、表氯醇均聚物和共聚物,尤其含卤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/乙酸乙烯酯或偏氯乙烯/乙酸乙烯酯共聚物。
9.衍生自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;经丙烯酸丁酯冲击改性的聚甲基丙烯酸甲酯、聚丙烯酰胺和聚丙烯腈。
10.在9)中提到的单体相互之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/卤代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。
11.衍生自不饱和醇和胺或酰基衍生物或其缩醛的聚合物,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、聚乙烯基丁醛、聚对苯二甲酸烯丙酯或聚烯丙基密胺;以及它们与以上1)中提到的烯烃的共聚物。
12.环醚的均聚物和共聚物,如聚亚烷基二醇、聚环氧乙烷、聚环氧丙烷或它们与二缩水甘油醚的共聚物。
13.聚缩醛,如聚甲醛和含环氧乙烷为共聚单体的那些聚甲醛;用热塑性聚氨酯、丙烯酸酯或MBS改性的聚缩醛。
14.聚苯醚和聚苯硫醚,以及聚苯醚和苯乙烯聚合物或聚酰胺的混合物。
15.衍生自,一方面,羟端基聚醚、聚酯或聚丁二烯,另一方面,脂族或芳族多异氰酸酯的聚氨酯及其预聚体。
16.衍生自二胺和二羧酸和/或氨基酸或相应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,始自间二甲苯二胺和己二酸的芳族聚酰胺;从六亚甲基二胺和间苯二甲酸或/和对苯二甲酸制成的聚酰胺,不论有无弹性体改性剂,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;还有前述聚酰胺与聚烯烃、烯烃共聚物、离聚物或化学键合或接枝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1,4-丁二醇的嵌段共聚物,以及用EPDM或ABS改性的聚酰胺或共聚酰胺;以及在加工期间缩合的聚酰胺(RIM聚酰胺体系)。
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.衍生自二羧酸和二醇和/或衍生自羟基羧酸或相应内酯的聚酯,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1,4-二甲基环己酯、聚萘二羧酸亚烃酯(PAN)和聚羟基苯甲酸酯,以及衍生自羟端基聚醚的嵌段共聚醚酯;还有用聚碳酸酯或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.衍生自,一方面,醛和另一方面,苯酚、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.干燥和未干燥的醇酸树脂。
23.由饱和及不饱和二羧酸与多元醇的共聚酯并以乙烯基化合物为交联剂所生成的不饱和聚酯树脂,及其具有低阻燃性的含卤化合物改性物。
24.衍生自取代丙烯酸酯的可交联丙烯酸树脂,例如,环氧丙烯酸酯、聚氨酯丙烯酸酯或聚酯丙烯酸酯。
25.用密胺树脂、脲树脂、异氰酸酯、异氰脲酸酯、多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.衍生自脂族、环脂族、杂环或芳族缩水甘油基化合物的交联环氧树脂,例如,用常用硬化剂如酸酐或胺,不论有无促进剂,交联的双酚A和双酚F的缩水甘油醚产物。
27.天然聚合物,如纤维素、橡胶、明胶和衍生自它们的化学改性同类物,例如,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.前述聚合物的共混物(聚合物共混物),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/丙烯酸酯、POM/热塑性PUR、PC/热塑性PUR、POM/丙烯酸酯、POM/MBS、PPO/HIPS、PPO/PA 6.6和共聚物、PA/HDPE、PA/PP、PA/PPO、PBT/PC/ABS或PBT/PET/PC。
29.天然存在或合成的有机材料,它们是纯单体化合物或这类化合物的混合物,例如,矿物油、动物和植物脂肪、油和蜡、或基于合成酯(如对苯二甲酸酯、己二酸酯、磷酸酯或偏苯三酸酯)的油、脂肪和蜡以及合成酯与矿物油以任意比例的混合物,典型的是用作纺丝组合物的那些,以及这类材料的水乳浊液。
30.天然或合成橡胶的水乳浊液,例如,天然胶乳或羧酸酯化苯乙烯/丁二烯共聚物的胶乳。
优选的有机材料是天然、半合成或,优选地,合成聚合物。
尤其要提到的有机材料是合成聚合物,最优选热塑性聚合物。尤其优选的有机材料是聚缩醛,聚烯烃,如聚丙烯或聚乙烯,聚醚/聚氨酯,聚对苯二甲酸丁二酯、聚碳酸酯之类的聚酯或聚酰胺。
特别要提出的是通式I的化合物[组分(b)]作为有机材料表面能降低剂的效率。表面能低的有机材料固有地具有更好的如下性能:斥水和斥油性、疏水性、阻隔性、易清洁、自清洁、防乱涂或耐溶剂。
通式I的化合物在有机材料中的加入浓度,优选是所述材料重量的0.01~10%,优选0.01~2%,典型值为0.1~2%。
除组分(a)和(b)以外,本发明的组合物还可包含如下其它添加剂:
1.抗氧剂
1.1.烷基化单酚,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,侧链为线形或支化的壬基苯酚,例如,2,6-二壬基-4-甲基苯酚、2,4-二甲基-6-(1’-甲基十一烷-1’基)苯酚、2,4-二甲基-6-(1’-甲基十七烷-1’基)苯酚、2,4-二甲基-6-(1’-甲基十三烷-1’基)苯酚及它们的混合物。
1.2.烷基硫甲基苯酚,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-甲基苯酚、2,4-二辛基硫甲基-6-乙基苯酚、2,4-二-十二烷基硫甲基-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-4-十八烷基氧基苯酚、2,6-二叔丁基氢醌、2,5-二叔丁基-4-羟基苯甲醚、3,5-二叔丁基-4-羟基苯甲醚、硬脂酸3,5-二叔丁基-4-羟基苯基酯、己二酸双(3,5-二叔丁基-4-羟基苯基)酯。
1.4.维生素E,例如,α-维生素E、β-维生素E、γ-维生素E、δ-维生素E和它们的混合物(维他命E)。
1.5.羟基化硫二苯基醚,例如,2,2’-硫双(6-叔丁基-4-甲基苯酚)、2,2’-硫双(4-辛基苯酚)、4,4’-硫双(6-叔丁基-3-甲基苯酚)、4,4’-硫双(6-叔丁基-2-甲基苯酚)、4,4’-硫双(3,6-二仲戊基苯酚)、4,4’-双(2,6-二甲基-2-羟苯基)二硫化物。
1.6.亚烷基双酚,例如,2,2’-亚甲基双(6-叔丁基-4-甲基苯酚)、2,2’-亚甲基双(6-叔丁基-4-乙基苯酚)、2,2’-亚甲基双[4-甲基-6-(α-甲基环己基)苯酚]、2,2’-亚甲基双(4-甲基-6-环己基苯酚)、2,2’-亚甲基双(6-壬基-4-甲基苯酚)、2,2’-亚甲基双(4,6-二叔丁基苯酚)、2,2’-亚乙基双(4,6-二叔丁基苯酚)、2,2’-亚乙基双(6-叔丁基-4-异丁基苯酚)、2,2’-亚甲基双[6-(α-甲基苄基)-4-壬基苯酚]、2,2’-亚甲基双[6-(α,α-二甲基苄基)-4-壬基苯酚]、4,4’-亚甲基双(2,6-二叔丁基苯酚)、4,4’-亚甲基双(6-叔丁基-2-甲基苯酚)、1,1-双(5-叔丁基-4-羟基-2-甲基苯基)丁烷、2,6-双(3-叔丁基-5-甲基-2-羟苄基)-4-甲基苯酚、1,1,3-三(5-叔丁基-4-羟基-2-甲基苯基)丁烷、1,1-双(5-叔丁基-4-羟基-2-甲基-苯基)-3-正十二烷基巯基丁烷、乙二醇双[3,3-双(3’-叔丁基-4’-羟苯基)丁酸酯]、双(3-叔丁基-4-羟基-5-甲基-苯基)二环戊二烯、双[2-(3’-叔丁基-2’-羟基-5’-甲基苄基)-6-叔丁基-4-甲基苯基]对苯二甲酸酯、1,1-双-(3,5-二甲基-2-羟苯基)丁烷、2,2-双(3,5-二叔丁基-4-羟苯基)丙烷、2,2-双(5-叔丁基-4-羟基-2-甲基苯基)-4-正十二烷基巯基丁烷、1,1,5,5-四-(5-叔丁基-4-羟基-2-甲基苯基)戊烷。
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-羟苄基)胺、双(4-叔丁基-3-羟基-2,6-二甲基苄基)二硫对苯二甲酸酯、双(3,5-二叔丁基-4-羟苄基)硫化物、异辛基-3,5-二叔丁基-4-羟苄基巯基乙酸酯。
1.8.羟苄基化丙二酸酯,例如,二-十八烷基-2,2-双(3,5-二叔丁基-2-羟苄基)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、二-十二烷基巯基乙基-2,2-双(3,5-二叔丁基-4-羟苄基)丙二酸酯、双[4-(1,1,3,3-四甲基丁基)苯基]-2,2-双(3,5-二叔丁基-4-羟苄基)丙二酸酯。
1.9.芳族羟苄基化合物,例如,1,3,5-三(3,5-二叔丁基-4-羟苄基)-2,4,6-三甲基苯、1,4-双(3,5-二叔丁基-4-羟苄基)-2,3,5,6-四甲基苯、2,4,6-三(3,5-二叔丁基-4-羟苄基)苯酚。
1.10.三嗪化合物,例如,2,4-双(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-双(3,5-二叔丁基-4-羟基苯胺基)-1,3,5-三嗪、2-辛基巯基-4,6-双(3,5-二叔丁基-4-羟基苯氧基)-1,3,5-三嗪、2,4,6-三(3,5-二叔丁基-4-羟基苯氧基)-1,2,3-三嗪、1,3,5-三(3,5-二叔丁基-4-羟苄基)异氰脲酸酯、1,3,5-三(4-叔丁基-3-羟基-2,6-二甲基苄基)异氰脲酸酯、2,4,6-三(3,5-二叔丁基-4-羟苯基乙基)-1,3,5-三嗪、1,3,5-三(3,5-二叔丁基-4-羟基-苯基丙酰基)-六氢-1,3,5-三嗪、1,3,5-三(3,5-二环己基-4-羟苄基)异氰脲酸酯。
1.11.苄基膦酸酯,例如,二甲基-2,5-二叔丁基-4-羟苄基膦酸酯、二乙基-2,5-二叔丁基-4-羟苄基膦酸酯、二-十八烷基-3,5-二叔丁基-4-羟苄基膦酸酯、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-羟苄基膦酸的单乙基酯的钙盐。
1.12.酰氨基苯酚,例如,4-羟基月桂苯胺、4-羟基硬脂苯胺、N-(3,5-二叔丁基-4-羟苯基)氨基甲酸辛基酯。
1.13.β-(3,5-二叔丁基-4-羟苯基)丙酸与单-或多元醇形成的酯,例如,与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十-烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三二环[2.2.2]辛烷形成的酯。
1.14.β-(5-叔丁基-4-羟基-3-甲基苯基)丙酸与单-或多元醇形成的酯,例如,与甲醇、乙醇、正辛醇、异辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三二环[2.2.2]辛烷;3,9-双[2-{3-(3-叔丁基-4-羟基-5-甲基苯基)丙酰氧基}-1,1-二甲基乙基]-2,4,8,10-四螺[5.5]-十一烷形成的酯。
1.15β-(3,5-二环己基-4-羟苯基)丙酸与单-或多元醇形成的酯,例如,与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三二环[2.2.2]辛烷形成的酯。
1.16.3,5-二叔丁基-4-羟苯基乙酸与单-或多元醇形成的酯,例如,与甲醇、乙醇、辛醇、十八烷醇、1,6-己二醇、1,9-壬二醇、乙二醇、1,2-丙二醇、新戊二醇、硫代二甘醇、二甘醇、三甘醇、季戊四醇、三(羟乙基)异氰脲酸酯、N,N’-双(羟乙基)草酰胺、3-硫代十一烷醇、3-硫代十五烷醇、三甲基己二醇、三羟甲基丙烷、4-羟基甲基-1-磷杂-2,6,7-三二环[2.2.2]辛烷形成的酯。
1.17.β-(3,5-二叔丁基-4-羟苯基)丙酸的酰胺,例如,N,N’-双(3,5-二叔丁基-4-羟苯基丙酰基)六亚甲基二胺、N,N’-双(3,5-二叔丁基-4-羟苯基丙酰基)三亚甲基二胺、N,N’-双(3,5-二叔丁基-4-羟苯基丙酰基)肼、N,N’-双[2-(3-[3,5-二叔丁基-4-羟苯基]丙酰氧基)乙基]草酰胺(NaugardXL-1,Uniroyal供应)。
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’-双(1,4-二甲基戊基)-对苯二胺、N,N’-双(1-乙基-3-甲基戊基)-对苯二胺、N,N’-双(1-甲基庚基)-对苯二胺、N,N’-二环己基-对苯二胺、N,N’-二苯基-对苯二胺、N,N’-双(2-萘基)-对苯二胺、N-异丙基-N’-苯基-对苯二胺、N-(1,3-二甲基丁基)-N’-苯基-对苯二胺、N-(1-甲基庚基)-N’-苯基-对苯二胺、N-环己基-N’-苯基-对苯二胺、4-(对甲苯氨磺酰基)二苯胺、N,N’-二甲基-N,N’-二仲丁基对苯二胺、二苯胺、N-烯丙基二苯胺、4-异丙氧基苯胺、N-苯基-1-萘胺、N-(4-叔辛基苯基)-1-萘胺、N-苯基-2-萘胺,辛基化二苯胺,例如,p,p’-二叔辛基二苯胺、4-正丁基-氨基苯酚、4-丁酰基氨基苯酚、4-壬酰基氨基苯酚、4-十二烷酰基氨基苯酚、4-十八烷酰基氨基苯酚、双(4-甲氧基苯基)胺、2,6-二叔丁基-4-二甲基氨基-甲基苯酚、2,4’-二氨基二苯基甲烷、4,4’-二氨基二苯基甲烷、N,N,N’,N’-四甲基-4,4’-二氨基二苯基甲烷、1,2-双[(2-甲基苯基)氨基]乙烷、1,2-双(苯基氨基)丙烷、(邻-甲苯基)双胍、双[4-(1’,3’-二甲基丁基)苯基]胺、叔辛基化N-苯基-1-萘胺、单-和二烷基化叔丁基/叔辛基二苯胺的混合物、单-和二烷基化壬基二苯胺的混合物、单-和二烷基化十二烷基二苯胺的混合物、单-和二烷基化异丙基/异己基二苯胺的混合物、单-和二烷基化叔丁基二苯胺的混合物、2,3-二氢-3,3-二甲基-4H-1,4-苯并噻嗪、吩噻嗪、单-和二烷基化叔丁基/叔辛基吩噻嗪的混合物、单-和二烷基化叔辛基-吩噻嗪的混合物、N-烯丙基吩噻嗪、N,N,N’,N’-四苯基-1,4-二氨基-丁-2-烯。
2.UV吸收剂和光稳定剂
2.1.2-(2’-羟苯基)苯并三唑,例如,2-(2’-羟基-5’-甲基苯基)-苯并三唑、2-(3’,5’-二叔丁基-2’-羟苯基)苯并三唑、2-(5’-叔丁基-2’-羟苯基)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’-羟苯基)苯并三唑、2-(2’-羟基-4’-辛基氧基苯基)苯并三唑、2-(3’,5’-二叔戊基-2’-羟苯基)苯并三唑、2-(3’,5’-双-(α,α-二甲基苄基)-2’-羟苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛基氧基羰基乙基)苯基)-5-氯-苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己基氧基)-羰基乙基]-2’-羟苯基)-5-氯-苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)-5-氯-苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-甲氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-2’-羟基-5’-(2-辛基氧基羰基乙基)苯基)苯并三唑、2-(3’-叔丁基-5’-[2-(2-乙基己基氧基)羰基乙基]-2’-羟苯基)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-异辛基氧基羰基乙基)苯基苯并三唑、2,2’-亚甲基-双[4-(1,1,3,3-四甲基丁基)-6-苯并三唑-2-基苯酚];2-[3’-叔丁基-5’-(2-甲氧基羰基乙基)-2’-羟苯基]-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.羟基苯酮,例如,4-羟基、4-甲氧基、4-辛基氧基、4-癸基氧基、4-十二烷基氧基、4-苄基氧基、4,2’,4’-三羟基和2’-羟基-4,4’-二甲氧基的衍生物。
2.3.取代和未取代苯甲酸的酯,例如,水杨酸4-叔丁基-苯酯、水杨酸苯酯、水杨酸辛基苯酯、二苯甲酰基间苯二酚、双(4-叔丁基苯甲酰基)间苯二酚、苯甲酰基间苯二酚、3,5-二叔丁基-4-羟基苯甲酸2,4-二叔丁基苯酯、3,5-二叔丁基-4-羟基苯甲酸十六烷酯、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,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、N-(β-甲酯基-β-氰基乙烯基)-2-甲基二氢吲哚、四(α-氰基-β,β-二苯基)丙烯酸新戊酯。
2.5.镍化合物,例如,2,2’-硫-双[4-(1,1,3,3-四甲基-丁基)苯酚]的镍配合物,如1∶1或1∶2的配合物,不论有无其它配位体,如正丁胺、三乙醇胺或N-环己基二乙醇胺,二丁基二硫氨基甲酸镍,4-羟基-3,5-二叔丁基苄基膦酸的单烷基酯,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,1-苯基-4-月桂酰基-5-羟基吡唑的镍配合物,不论有无其它配位体。
2.6.空间受阻胺,例如,双(2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(2,2,6,6-四甲基-4-哌啶基)丁二酸酯、双(1,2,2,6,6-五甲基-4-哌啶基)癸二酸酯、双(1-辛基氧基-2,2,6,6-四甲基-4-哌啶基)癸二酸酯、双(1,2,2,6,6-五甲基-4-哌啶基)-正丁基-3,5-二叔丁基-4羟苄基丙二酸酯、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’-双(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-1,3,5-三嗪的线形或环状缩合物、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-乙烷二基)-双(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-硬脂基氧基-2,2,6,6-四甲基哌啶、双(1,2,2,6,6-五甲基哌啶基)-2-正丁基-2-(2-羟基-3,5-二叔丁基苄基)丙二酸酯、3-正辛基-7,7,9,9-四甲基-1,3,8-三氮螺[4.5]癸-2,4-二酮、双(1-辛基-氧基-2,2,6,6-四甲基哌啶基)癸二酸酯、双(1-辛基氧基-2,2,6,6-四甲基哌啶基)丁二酸酯、N,N’-双(2,2,6,6-四甲基-4-哌啶基)六亚甲基二胺和4-吗啉代-2,6-二氯-1,3,5-三嗪的线形或环状缩合物,2-氯-4,6-双(4-正丁基氨基-2,2,6,6-四甲基哌啶基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)-乙烷的缩合物、2-氯-4,6-二(4-正丁基氨基-1,2,2,6,6-五甲基哌啶基)-1,3,5-三嗪和1,2-双(3-氨基丙基氨基)乙烷的缩合物、8-乙酰基-3-十二烷基-7,7,9,9-四甲基-1,3,8-三氮螺[4.5]癸-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、4-十六烷基氧基-和4-硬脂基氧基-2,2,6,6-四甲基哌啶的混合物、N,N’-双(2,2,6,6-四甲基-4-哌啶基)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-双(3-氨基丙基氨基)乙烷和2,4,6-三氯-1,3,5-三嗪以及4-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS Reg.No.[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-丁基氨基-2,2,6,6-四甲基哌啶的缩合物(CAS Reg.No.[192268-64-7]);N-(2,2,6,6-四甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、N-(1,2,2,6,6-五甲基-4-哌啶基)-正十二烷基琥珀酰亚胺、2-十一烷基-7,7,9,9-四甲基-1-氧杂-3,8-二氮-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-4-氧代螺-[4.5]癸烷和表氯醇的反应产物,1,1-双(1,2,2,6,6-五甲基-4-哌啶基氧基羰基)-2-(4-甲氧基苯基)乙烷、N,N’-双-甲酰基-N,N’-双(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-氧基-4-(2,26,6-四甲基-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,2,4-双[N-(1-环己基氧基-2,2,6,6-四甲基哌啶-4-基)-N-丁基氨基]-6-(2-羟基乙基)氨基-1,3,5-三嗪、1-(2-羟基-2-甲基丙氧基)-4-十八烷酰基氧基-2,2,6,6-四甲基哌啶、5-(2-乙基己酰基)-氧基甲基-3,3,5-三甲基-2-吗啉酮,Sanduvor(Clariant;CAS Reg.No.[106917-31-1]),5-(2-乙基己酰基)-氧基甲基-3,3,5-三甲基-2-吗啉酮,2,4-双-[(1-环己基氧基-2,2,6,6-哌啶-4-基)丁基氨基]-6-氯-s-三嗪与N,N’-双(3-氨丙基)亚乙基二胺)的反应产物,1,3,5-三(N-环己基-N-(2,2,6,6-四甲基哌嗪-3-酮-4-基)氨基-s-三嗪,1,3,5-三(N-环己基-N-(1,2,6,6-五基哌嗪-3-酮-4-基)氨基-s-三嗪。
2.7.草酰胺,例如,4,4’-二辛基氧基N,N’-草酰二苯胺、2,2’-二乙氧基N,N’-草酰二苯胺、2,2’-二辛基氧基-5,5’-二N-叔丁氧酰苯胺、2,2’-二-十二烷基氧基-5,5’-二N-叔丁氧酰苯胺、2-乙氧基-2’-乙基N,N’-草酰二苯胺、N,N’-双(3-二甲基氨基丙基)N,N’-草酰胺、2-乙氧基-5-叔丁基-2-N-乙氧酰苯胺和它与2-乙氧基-2’-乙基-5,4’-二N-叔丁氧酰苯胺的混合物、邻-和对-甲氧基-二取代N,N’-草酰二苯胺的混合物和邻-和对-乙氧基-二取代N,N’-草酰二苯胺的混合物。
2.8.2-(2-羟苯基)-1,3,5-三嗪,例如,2,4,6-三(2-羟基-4-辛基氧基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛基氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2,4-二羟基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(2-羟基-4-丙基氧基苯基)-6-(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-辛基氧基苯基)-4,6-双(4-甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十二烷基氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-十三烷基氧基苯基)-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-丁基氧基丙氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-辛基氧基丙基氧基)苯基]-4,6-双(2,4-二甲基)-1,3,5-三嗪、2-[4-(十二烷基氧基/十三烷基氧基-2-羟基丙氧基)-2-羟苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-[2-羟基-4-(2-羟基-3-十二烷基氧基丙氧基)苯基]-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2-(2-羟基-4-己基氧基)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-羟苯基)-4-(4-甲氧基苯基)-6-苯基-1,3,5-三嗪、2-{2-羟基-4-[3-(2-乙基己基-1-氧基)-2-羟基丙基氧基]苯基}-4,6-双(2,4-二甲基苯基)-1,3,5-三嗪、2,4-双(4-[2-乙基己基氧基]-2-羟苯基)-6-(4-甲氧基苯基)-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’-水杨酰基肼、N,N’-双(水杨酰基)肼、N,N’-双(3,5-二叔丁基-4-羟苯基丙酰基)肼、3-水杨酰基氨基-1,2,4-三唑、双(亚苄基)草酰基二肼、N,N’-草酰二苯胺、间苯二甲酰基二肼、癸酰基二苯基肼、N,N’-二乙酰基己二酰基二肼、N,N’-双(水杨酰基)草酰基二肼、N,N’-双(水杨酰基)硫丙酰基二肼。
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、亚磷酸月桂基酯、亚磷酸三-十八烷基酯、二亚磷酸二硬脂基季戊四醇酯、亚磷酸三(2,4-二叔丁基苯基)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、二亚磷酸双(2,4-二枯基苯基)季戊四醇酯、二亚磷酸双(2,6-二叔丁基-4-甲基苯基)季戊四醇酯、二亚磷酸二异癸基氧基季戊四醇酯、二亚磷酸双(2,4-二叔丁基-6-甲基苯基)季戊四醇酯、二亚磷酸双(2,4,6-三(叔丁基苯基)季戊四醇酯、三亚磷酸三硬脂基山梨醇酯、二亚膦酸四(2,4-二叔丁基苯基)4,4’-亚联苯酯、6-异辛基氧基-2,4,8,10-四叔丁基-12H-二苯[d,g]-1,3,2-dioxaphosphocin、亚磷酸双(2,4-二叔丁基-6-甲基苯基)甲酯、亚磷酸双(2,4-二叔丁基-6-甲基苯基)乙酯、6-氟-2,4,8,10-四叔丁基-12-甲基-二苯[d,g]-1,3,2-dioxaphosphocin、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-dioxa-phosphirane。
5.羟基胺,例如,N,N-二苄基羟基胺、N,N-二乙基羟基胺、N,N-二辛基羟基胺、N,N-二月桂基羟基胺、N,N-二-十四烷基羟基胺、N,N-二-十六烷基羟基胺、N,N-二-十八烷基羟基胺、N-十六烷基-N-十八烷基羟基胺、N-十七烷基-N-十八烷基羟基胺、衍生自氢化牛脂胺的N,N-二烷基羟基胺。
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-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、从衍生自氢化牛脂胺的N,N-二烷基羟基胺衍生的硝酮。
7.硫代增效剂,例如,硫代二丙酸二月桂基酯、硫代二丙酸二dimistryl酯、硫代二丙酸二硬脂基酯或二硬脂基二硫化物。
8.过氧化物清除剂,例如,β-硫代二丙酸的酯,例如,月桂基酯、硬脂基酯、肉豆蔻基酯或十三烷基酯,巯基苯并咪唑或2-巯基苯并咪唑的锌盐,二丁基二硫氨基甲酸锌,二-十八烷基二硫化物,四(β-十二烷基巯基)丙酸季戊四醇酯。
9.聚酰胺稳定剂,例如,铜盐与碘化物和/或磷化合物的组合和二价锰的盐。
10.碱性助稳定剂,例如,密胺、聚乙烯基吡咯烷酮、双氰胺、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、山萮酸镁、硬脂酸镁、蓖麻醇酸钠和棕榈酸钾、焦儿茶酚锑或焦儿茶酚锌。
11.成核剂,例如,无机物质,如滑石粉,金属氢化物,如氢化钛或氧化镁,磷酸盐、碳酸盐或硫酸盐,优选碱土金属的;有机化合物,如单-或多元羧酸及其盐,例如,4-叔丁基苯甲酸、己二酸、二苯基乙酸、丁二酸钠或苯甲酸钠;聚合化合物,如离子共聚物(离聚物)。特别优选1,3:2,4-双(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。
12.填料和增强剂,例如,碳酸钙、硅酸盐、玻璃纤维、玻璃珠、石棉、滑石粉、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。
13.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。
14.苯并呋喃酮(?)和吲哚满酮,例如,U.S.4,325,863;U.S.4,338,244;U.S.5,175,312;U.S.5,216,052;U.S.5,252,643;DE-A-4316611;DE-A-4316622;DE-A-4316876;EP-A-0589839,EP-A-0591102;EP-A-1291384所公开的那些或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-硬脂酰基氧基乙氧基)苯基]苯并呋喃-2-酮、3,3’-双[5,7-二叔丁基-3-(4-[2-羟基乙氧基]苯基)苯并呋喃-2-酮]、5,7-二叔丁基-3-(4-乙氧基苯基)苯并呋喃-2-酮、3-(4-乙酰氧基-3,5-二甲基苯基)-5,7-二叔丁基苯并呋喃-2-酮、3-(3,5-二甲基-4-新戊酰基氧基苯基)-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、3-(2-乙酰基-5-异辛基苯基)-5-异辛基-苯并呋喃-2-酮。
其它添加剂一般以浓度为拟处理材料总重量的0.01~10%使用。
本发明的优选组合物包含酚醛抗氧剂、光稳定剂和/或加工稳定剂作为其它添加剂。
在合成聚合物中加入组分(b)和,如果希望,其它添加剂用已知方法进行,例如,在模塑之前或期间,或把溶解或分散的化合物涂布到合成聚合物上,如果合适,接着慢慢蒸发掉溶剂。
本发明还涉及组分(a)的含量为5~90重量%和组分(b)的含量为5~80重量%的母粒或浓缩物形式的组合物。
组分(b)和,如果希望,其它添加剂也可以在聚合前或聚合期间或交联前加入。
组分(b),不论有无其它添加剂,可以纯形式或包封在蜡、油或聚合物内的形式加进合成聚合物。
组分(b),不论有无其它添加剂,也可以喷涂到合成聚合物上。它能稀释其它添加剂(例如,以上所示的传统添加剂)或它们的熔体,从而它们也能与这类添加剂一起被喷涂到聚合物上。在聚合催化剂的去活化期间用喷涂法加入特别有利,这能用,例如,去活化所用的蒸气来进行喷涂。
在球状聚合的聚烯烃的情况下,优选用喷涂法涂布组分(b),不论有无其它添加剂。
以这种方法制成的合成聚合物能以多种形式使用,例如,泡沫、薄膜、纤维、带、模塑组合物、作为异型材或作为涂料尤其粉末涂料的粘结剂、胶粘剂、腻子,或尤其作为要长期接触萃取介质的厚层聚烯烃模塑制品,例如,用于液体或气体的管道、薄膜、纤维、地膜(geomembranes)、带、异型材或罐等。
优选的厚层聚烯烃模塑制品的层厚为1~50mm,特别1~30mm,例如,2~10mm。
按照本发明的组合物优选用来制造各种形状的制品,实例如下:
I-1)漂浮设备、潜水应用、浮桥、浮标;用于甲板、防波堤、船只、独木舟、桨和海滩增强剂的塑料成材。
I-2)汽车应用,特别在保险杠、仪表板、蓄电池、后和前衬、发动机罩下的模塑件、帽架、后备箱衬里、车内衬里、安全气囊盖、安装用电子模塑件(灯)、仪表板的板材、顶灯玻璃、仪器面板、车外衬里、内饰件、车灯、顶灯、停车灯、后灯、制动灯、内饰件和外饰件;门板;气罐;罩光前侧板、后窗;座椅靠背、外板、电线绝缘、密封用异型挤塑件,复合板、柱罩、底盘零件、排气系统、燃油过滤器/填料、燃油泵、燃油罐、车体侧面模塑件、活动轿车篷顶、外视镜、外饰件、紧固件、前端模块、玻璃、绞链、车锁系统、格栅式行李架/车顶行李架、压制/冲压零件、密封、侧面防冲件、消音器/绝缘器和遮阳板。
I-3)道路交通设备,尤其信号柱、路标牌、汽车附件、警示三角标志、医药箱、头盔、轮胎。
I-4)飞机、铁路、机动车(汽车、摩托车)用设备,包括陈设在内。
I-5)航天应用设备,特别是火箭和卫星用器件,如再入大气层防热瓦。
I-6)建筑和设计、采矿应用、消声系统、街道安全岛和避护用设备。
II-1)各类器具、箱盒和覆盖物及电气/电子设备(个人计算机、电话、移动电话、打印机、电视机、音响和视频设备)、花盆、卫星天线盘和面板设备。
II-2)用于钢或织物之类其它材料的外套。
II-3)电子工业用设备,尤其插座特别计算机插座的绝缘、电气和电子零件盒、印刷电路板和电子数据贮存材料,如芯片、校验卡或信用卡。
II-4)家用电器,尤其洗衣机、干衣机、炉(微波炉)、洗碗机、搅拌器和熨斗。
II-5)灯用遮盖物(例如,街灯、灯罩)。
II-6)电线和电缆中的应用(半导体、绝缘和电缆套)。
II-7)冷凝器、冰箱、加热设备、空调、电子器件封装、半导体、咖啡机和吸尘器用箔。
III-1)技术制品,如齿轮、滑动装配件、垫片、螺钉、螺栓、手柄和圆形把手。
III-2)旋转叶片、通风器和风车叶轮、太阳能设备、游泳池、游泳池盖、池衬、壁橱、衣柜、分隔墙、板条墙、折叠墙、屋顶、窗板(如卷轴窗板)、固定件、管道之间的接头、套筒和输送带。
III-3)保健用品,尤其淋浴室、卫生间座椅、遮盖物和洗涤槽。
III-4)卫生用品,尤其尿布(婴儿,成人失禁用)、妇女卫生用品,淋浴帘、刷子、垫子、桶、移动厕所、牙刷和bed pans。
III-5)水、废水和化学药品管道(交联或未交联)、电线和电缆防护管道、煤气、油和污水管道、沟槽、泄水管和下水道系统。
III-6)任意几何形状的异型材(窗框)和侧轨。
III-7)玻璃替代品,尤其挤出板,大厦、飞机、校舍用玻璃(整块、配对或有多层外皮的)、挤出片材、结构罩光面、火车、运输工具、卫生设备和温室用窗膜。
III-8)板(墙、隔板)、挤涂(照相纸、tetrapack和管道涂层)、饲料仓、木材代用品,塑料成材、木质复合材料、墙、表面、家具、装饰箔、地板表层(内部和外部应用)、地板、铺在泥泞地上的木板道和瓦。
III-9)输入和输出歧管。
III-10)水泥、混凝土、复合材料应用和遮盖物、侧轨和包覆,扶手、栏杆、厨房工作台面、屋顶、屋顶片材、瓦和焦油帆布。
IV-1)板(墙和隔板)、盘、人造草地、人造草皮、圆形看台(体育运动场)遮盖物、圆形看台(体育运动场)的人造地板和卷带。
IV-2)连续或短切纤维织物(地毯/卫生用品/铺地织物/单丝;过滤器;拭布/帘子(遮阳)/医疗应用、膨松纤维(外衣/防护服等应用)、网、粗绳、电缆、细绳、弦、线、安全椅带、衣服、内衣、手套、靴、胶靴、贴身内衣、外衣、游泳衣、运动衫、伞(阳伞、遮阳伞)、降落伞、滑翔机降落伞、帆篷、“气球布”、露营用品,帐篷、空气垫、日光床、大口袋、小口袋。
IV-3)膜、绝缘,屋顶、地道、垃圾场、池塘遮盖物和密封、屋顶盖膜、地膜、游泳池、窗帘(遮阳)/遮阳罩、遮阳篷、天篷、墙纸、食品包装(柔软而结实)、医药包装(柔软而结实)、气囊/安全带、扶手和头枕、地毯、中央控制柜、仪表板、驾驶舱、门、顶置控制台模块、门饰件、车顶内衬、车内灯、内视镜、小件行李搁板、后行李箱盖、座椅、转向管杆、方向盘、织物和行李舱饰件。
V)薄膜(包装、垃圾、层合、农业和园艺、温室、护根、地道、青贮饲料)、打包带、游泳池、废品袋、墙纸、拉伸薄膜、拉菲亚(raffia)包扎带、脱盐薄膜、电池和接头。
VI-1)食品包装和包裹(柔软而结实)、瓶子。
VI-2)贮藏系统,如盒(篓筐)、行李包、箱柜、家务盒、低台、货架、导轨、螺旋盒、包和罐。
VI-3)筒、注射器、医疗应用、任何运输容器、废纸篓和废品箱、废品袋、贮物箱、垃圾箱、箱衬、带轮箱、各类容器、水/已用水/化学品/煤气/油/汽油/柴油罐;罐衬、盒子、篓筐、电池盒,水槽、医疗设备,如活塞、眼科应用、诊断设备和药物泡。
VII-1)挤出涂层(照相纸、纸饮料罐、管道涂层)、各类家务用品(如家用器具、暖瓶/衣架)、固定系统如塞子、电线和电缆夹、拉锁、闭塞物、锁和卡锁。
VII-2)支撑器件,休闲用品,如运动和舒适器件,体操垫、滑雪靴、一字型溜冰鞋、big foot、运动表面(如网球场);螺旋盖、瓶盖和瓶塞和罐头(cans)。
VII-3)各类家具,发泡制品(枕头、防冲件)、泡沫、海绵、洗碗布、毡垫、花园椅、看台座椅、桌子、长沙发、玩具、建筑工具箱(板/图形/球)、游戏室、滑梯和游戏车。
VII-4)光学和磁数据贮存材料。
VII-5)厨房用具(吃、喝、烹煮、贮存)。
VII-6)CD、录音带和录象带盒;DVD电子制品,各类办公用品(圆珠笔、图章和印泥台、上下窗户的坠子、书架、导轨)、任意体积和容积的瓶子(饮料、清洁剂、包括香水在内的化装品)和胶带。
VII-7)足穿物(鞋子/鞋底)、鞋垫、鞋罩、胶粘剂、结构胶粘剂、食品盒(水果、蔬菜、肉、鱼)、合成纸、瓶子标签、长沙发、人造关节(人类)、印刷板(苯胺印刷)、印刷电路板和显示技术。
VII-8)填充聚合物(滑石粉、白垩、陶土(高岭土)、硅灰石、颜料、炭黑、TiO2、云母、纳米复合材料、白云石、硅酸盐、玻璃、石棉)器件。
其中特别重要的是包含纤维和非织造织物为组分(a)的组合物。
因此,本发明的另一个实施方案涉及成型制品,尤其含上述组合物的薄膜、管道、异型材、瓶子、罐或容器、纤维。
本发明的另一个实施方案涉及含上述组合物的模塑制品。模塑尤其用注塑、吹塑、压缩模塑、旋转模塑或搪塑或挤出法进行。
本发明还涉及减小有机材料表面能的方法,包含在有机材料中掺入至少一种通式I的化合物[组分(b)]。
在减小有机材料表面能(例如,提高斥油和斥水性)的方法中,通式I或组分(b)的优选化合物和任选地其它添加剂与对组合物所述的那些相同。
本发明的一个优选实施方案也是用通式I的化合物[组分(b)]作为有机材料的表面能降低剂[例如作为斥油和斥水剂]。
在用作有机材料表面能减小剂[例如,提高斥油和斥水性]中,通式I或组分(b)的优选化合物和任选的其它添加剂与对组合物所述的那些相同。
本发明还提供通式I的新型化合物
其中,
R2是-X-R3,
R3是含氟基团,
R4是C1~C25烷基、C3~C25链烯基、未取代或C1~C4烷基取代的苯基,
R6是氢、C1~C8烷基或苄基,
R7是C1~C25烷基、C2~C25链烯基、未取代或被C1~C4烷基或C1~C4烷酰基氨基取代的苯基;未取代或C1~C4烷基取代的苯基氨基,
R10是氢、C1~C8烷基或苄基,
R11是氢、C1~C8烷基或苄基,
Z是C1~C25亚烷基、1,2-亚苯基、1,3-亚苯基、1,4-亚苯基或
R12和R13彼此独立地各是氢、C1~C12烷基或苯基,或R11和R12连同键接的碳原子一起形成未取代或被1~3个C1~C4烷基取代的C5~C8亚环烷基环。
其中特别重要的是通式为I且其中各基团如下的化合物:
R1是-NO2,-N=CH-R4或
R2是-X-R3,
R3是-CH2CH2(CF3)7CF3或-CH2CH2(CF3)3CF3,
R4是C4~C12烷基、C4~C12链烯基、未取代或C1~C4烷基取代的苯基,
R6是氢,
R7是C1~C8烷基、C2~C8链烯基、苯基或苯基氨基,
R10是氢,
R11是氢,
Z是C4~C12烷基、1,3-亚苯基、1,4-亚苯基或
R12和R13是氢。
在通式I的新型化合物中所有符号的优选意义与有关本发明组合物中所列所有符号的优选意义相同。
以下实施例进一步说明本发明。份数和百分数都指重量。
实施例1:制备式101的化合物。
在50ml四氢呋喃中溶解17.8g(40.0mmol)氟化醇(Zonyl BA-L)和4.45g(44.0mmol)三乙胺。在10ml四氢呋喃中溶解4.96g(20.0mmo1)5-硝基间苯二甲酰氯并在氮气氛下逐滴慢慢加进0~10℃的反应混合物。形成大量白色固体,而且随反应变得难以搅拌,加入90ml四氢呋喃。在室温下搅拌该反应混合物12h。加入二乙基醚(200ml)并用1N NH4Cl和水反复洗涤有机相直到pH值呈中性。有机相经硫酸镁干燥、过滤和用真空旋转蒸发器浓缩,产生16.5g黄色固体。用在四氢呋喃/二乙基醚中重结晶的方法纯化粗固体,得到13.1g化合物101,即白色固体,熔点为108~110℃。1H NMR:(300MHz,CDCl3):δ=9.07(s,ArH,2H);9.00(s,ArH,1H);4.76(t,J=6.3Hz,OCH2CH2CF2,4H);2.80~2.55(m,OCH2CH2CF2,4H)。
实施例2:制备式102的化合物。
在热压釜(100ml Glass-Camile)内,在惰性气氛下,把8.50g(8.00mmol)式101的化合物[按照实施例1制成]和0.50g催化剂(Pd/C,10重量%)溶解在50ml四氢呋喃中。然后通进H2直到容器内的压力达到5巴。在75℃下搅拌该反应混合物12h。冷却反应混合物到室温,然后滤去催化剂并用真空旋转蒸发器蒸去溶剂,产生6.85g式102化合物,即灰黄色固体,熔点为132~133℃。1H NMR:(300MHz,丙酮-d6):δ=7.95~7.90(m,ArH,1H);7.60~7.55(m,ArH,1H);5.31(brs,NH2,2H);4.68(t,J=6.0Hz,OCH2CH2CF2,4H);3.00~2.55(m,OCH2CH2CF2,4H)。
实施例3:制备式103的化合物。
在30ml四氢呋喃中溶解1.21g(1.20mmol)式102的化合物[按照实施例2制成]和0.14g(1.40mmol)三乙胺。在室温和氮气氛下,把0.14g(1.20mmol)新戊酰氯加进反应混合物。在室温下搅拌该反应混合物6h。加入二乙基醚(80ml)并用水反复洗涤有机相直到pH值呈中性。有机相经硫酸镁干燥、过滤和用真空旋转蒸发器浓缩,产生1.20g灰棕色蜡。用闪蒸色谱法(己烷/乙酸乙酯:2∶1)纯化粗固体,得到1.10g式103的化合物,即灰黄蜡。1H NMR:(300MHz,丙酮-d6):δ=9.09(br,s,NH,1H);8.70~8.65(m,ArH,2H);8.40~8.30(m,ArH,1H);4.74(t,J=6.0Hz,OCH2CH2CF2,4H);3.00~2.75(m,OCH2CH2CF2,4H);1.34(s,叔丁基,9H)。
实施例4:制备式104的化合物。
在40ml四氢呋喃中溶解1.51g(1.50mmol)式102的化合物[按照实施例2制成]和0.18g(1.80mmol)三乙胺。在室温和氮气氛下,把0.15g(0.70mmol)对苯二甲酰氯加进反应混合物。在室温下搅拌该反应混合物12h。加入乙酸乙酯(100ml)和四氢呋喃(50ml)并用水和盐水反复洗涤有机相直到pH值呈中性。废弃水相并滤去有机相内的悬浮材料,产生0.95g式104的化合物,即白色固体,熔点为160~268℃。1H NMR:(300MHz,四氢呋喃-d8):δ=9.95(s,NH,2H);8.80~8.70(m,ArH,4H);8.50~8.40(m,ArH,2H);8.20~8.10(m,ArH,4H);4.71(t,J=6.0Hz,OCH2CH2CF2,8H);2.95~2.70(m,OCH2CH2CF2,8H)。
实施例5:制备式105的化合物。
在40ml四氢呋喃中溶解1.80g(1.70mmol)式102的化合物[按照实施例2制成]和0.21g(2.10mmol)三乙胺。在室温和氮气氛下,把0.21g(1.70mmol)苯基异氰酸酯加进反应混合物。在室温下搅拌该反应混合物24h。加入二乙基醚(100ml)并用1N NH4Cl、水和盐水反复洗涤有机相直到pH值呈中性。有机相经硫酸镁干燥、过滤和用真空旋转蒸发器的浓缩,产生2.00g灰黄色固体。用在乙酸乙酯内重结晶的方法纯化粗产物,得到0.67g式105的化合物,即白色固体,熔点为164~166℃。1H NMR:(300MHz,丙酮-d6):δ=8.58(br s,NH,1H);8.55~8.45(m,ArH,2H);8.35~8.25(m,1H);8.25~8.15(m,1H);7.65~7.50(m,ArH,2H);7.35~7.20(m,ArH,2H);7.10~6.95(m,ArH,1H);4.74(t,J=6.0Hz,OCH2CH2CF2,4H);3.00~2.70(m,OCH2CH2CF2,4H)。
实施例6:制备式106的化合物。
在50ml四氢呋喃中溶解2.25g(2.18mmol)式102的化合物[按照实施例2制成]和0.27g(2.62mmol)三乙胺。在室温和氮气氛下,把0.17g(1.09mmol)1,4-亚苯基二异氰酸酯加进反应混合物。在室温下搅拌该反应混合物24h。加入水(50ml)并搅拌该反应混合物15min,然后滤出固体并在烘箱内烘干,得到式106的化合物,即白色固体,熔点>200℃。
实施例7:制备式107的化合物。
在40ml四氢呋喃中溶解6.92g(15.6mmol)氟化醇(Zonyl BA-L)和2.37g(23.4mmol)三乙胺。在氮气氛下,把3.60g(15.6mmol)3,5-二硝基苯甲酰氯加进0~10℃的反应混合物。在室温下搅拌该反应混合物12h。加入二乙基醚(100ml)并用1N NH4Cl和水反复洗涤有机相直到pH值呈中性。有机相经硫酸镁干燥、过滤和用真空旋转蒸发器浓缩,产生9.40g黄色固体。用闪蒸色谱法(己烷/乙酸乙酯:4∶1)纯化粗产物,得到7.50g式107的化合物,即白色固体,熔点为111~113℃。1HNMR:(300MHz,CDCl3):δ=9.30~9.25(m,ArH,1H);9.20~9.15(m,ArH,2H);4.80(t,J=6.3Hz,OCH2CH2CF2,2H);2.85~2.60(m,OCH2CH2CF2,2H)。
实施例8:制备式108的化合物。
在120ml干燥甲苯中溶解18.8g(71.1mmol)氟化醇(FluorochemLimited)和8.63g(85.3mmol)三乙胺。在氮气氛下,把8.82g(35.6mmol)5-硝基间苯二甲酰氯逐份慢慢加进0~10℃的反应混合物。形成大量白色固体且随反应变得难以搅拌,加入280ml干燥甲苯。在室温下搅拌该反应混合物12h。然后加入水(300ml),搅拌该悬浮体1h并滤出固体,用水反复洗涤并在烘箱内烘干,产生14.9g式108的化合物,即白色固体,熔点为91~92℃。1H NMR:(300MHz,丙酮-d6):δ=9.00(brs,ArH,2H);8.95(br s,ArH,1H);4.83(t,J=6.0Hz,OCH2CH2CF2,4H);3.05~2.80(m,OCH2CH2CF2,4H)。
实施例9:制备式109的化合物。
在热压釜(100ml Glass-Camile)内,在惰性气氛下,把9.80g(13.9mmol)式108的化合物[按照实施例8制成]和0.80g催化剂(Pd/C,10重量%)溶解在50ml四氢呋喃中。然后通进H2直到容器内的压力达到5巴。在75℃下搅拌该反应混合物20h。冷却反应混合物到室温,然后滤去催化剂并用真空旋转蒸发器蒸去溶剂,得到8.00g式109的化合物,即白色固体,熔点为131~133℃。1H NMR:(300MHz,四氢呋喃-d8):δ=8.05(br s,ArH,1H);7.53(br s,ArH,2H);4.65(t,J=6.3Hz,OCH2CH2CF2,4H);4.00(br s,NH2,2H);2.75~2.50(m,OCH2CH2CF2,4H)。
实施例10:制备式110的化合物。
在25ml四氢呋喃中溶解1.78g(2.64mmol)式109的化合物[按照实施例9制成]和0.38g(3.70mmol)三乙胺。在室温和氮气氛下,把0.32g(2.64mmol)新戊酰氯加进反应混合物。在室温下搅拌该反应混合物1h。加入二乙基醚(80ml)并用水反复洗涤有机相直到pH值呈中性。有机相经硫酸镁干燥、过滤和用真空旋转蒸发器浓缩,产生式110的化合物,即灰黄色固体,熔点为71~73℃。1H NMR:(300MHz,CDCl3):δ=8.50~8.40(m,ArH,1H);8.45~8.35(m,ArH,1H);7.56(br s,NH,1H);4.67(t,J=6.3Hz,OCH2CH2CF2,4H);2.75~2.55(m,OCH2CH2CF2,4H);1.36(s,叔丁基,9H)。
实施例11:制备式111的化合物
在70ml四氢呋喃中溶解1.82g(2.70mmol)式109的化合物[按照实施例9制成]和0.33g(3.24mmol)三乙胺。在室温和氮气氛下,把0.27g(1.35mmol)对苯二甲酰氯加进反应混合物。在室温下搅拌该反应混合物2h。加入乙酸乙酯(200ml)并用水和盐水反复洗涤有机相直到pH值呈中性。有机相经硫酸镁干燥、过滤和用真空旋转蒸发器浓缩,产生1.90g灰黄色固体。用闪蒸色谱法(己烷/乙酸乙酯:2∶1)纯化粗固体,得到1.70g式111的化合物,即白色固体,熔点为187~223℃。1H NMR:(300MHz,丙酮-d6):δ=10.12(s,NH,2H);8.85~8.80(m,ArH,4H);8.45~8.40(m,ArH,2H);8.23(s,ArH,4H);4.77(t,J=6.0Hz,OCH2CH2CF2,8H);3.00~2.80(m,OCH2CH2CF2,8H)。
实施例12:制备式112的化合物。
在130ml四氢呋喃中溶解3.40g(5.05mmol)式109的化合物[按照实施例9制成]和0.62g(6.07mmol)三乙胺。在室温和氮气氛下,把0.67g(2.53mmol)5-硝基间对苯二甲酰氯加进反应混合物。在室温下搅拌该反应混合物10h。加入乙酸乙酯(300ml)并用水和盐水反复洗涤有机相直到pH值呈中性。有机相经硫酸镁干燥、过滤和用真空旋转蒸发器浓缩,形成3.80g黄色固体。用闪蒸色谱法(己烷/乙酸乙酯:3∶1)纯化粗固体,得到0.90g式112的化合物,即黄色固体,熔点为175~184℃。1H NMR:(300MHz,丙酮-d6):δ=10.50(s,NH,2H);9.10(s,ArH,3H);8.85~8.80(m,ArH,4H);8.50~8.40(m,ArH,2H);4.78(t,J=6.0Hz,OCH2CH2CF2,8H);3.00~2.80(m,OCH2CH2CF2,8H)。
实施例13:制备式113的化合物。
在50ml四氢呋喃中溶解1.50g(2.23mmol)式109的化合物[按照实施例9制成]和0.25g(2.46mmol)三乙胺。在室温和氮气氛下,把0.28g(1.12mmol)4,4’-亚甲基-双-苯基异氰酸酯加进反应混合物。在室温下搅拌该反应混合物24h。加入四氢呋喃(50ml)并搅拌该反应混合物15min,然后滤出固体。用乙酸乙酯稀释透明无色混合物,用水洗涤,在硫酸镁上干燥,过滤并浓缩。用在乙腈中重结晶的方法纯化粗材料,形成式113的化合物,即白色固体,熔点为189~191℃。1HNMR:(300MHz,丙酮-d6):δ=8.56(br s,NH,2H);8.52~8.42(m,ArH,4H);8.30~8.20(m,2H);8.19(br s,NH,2H);7.55~7.40(m,ArH,4H);7.22~7.10(m,ArH,4H);4.73(t,J=6.0Hz,OCH2CH2CF2,8H);3.92(s,ArCH2Ar,2H);3.00~2.70(m,OCH2CH2CF2,8H)。
实施例14:制备式114的化合物。
在热压釜(100ml Glass-Camile)内,在惰性气氛下,把2.30g(1.51mmol)式112的化合物[按照实施例12制成]和0.25g催化剂(Pd/C,10重量%)溶解在40ml四氢呋喃中。然后通进H2直到容器内的压力达到5巴。在75℃下搅拌该反应混合物6h。冷却反应混合物到室温,然后滤去催化剂并用真空旋转蒸发器蒸去溶剂,产生2.10g式114的化合物,即灰黄色固体。1H NMR:(300MHz,丙酮-d6):δ=10.00(s,NH,2H);8.85~8.70(m,ArH,4H);8.45~8.35(m,ArH,2H);7.82(br s,ArH,1H);7.55~7.45(m,ArH,2H);5.26(br s,NH2,2H);4.76(t,J=6.0Hz,OCH2CH2CF2,8H);3.00~2.75(m,OCH2CH2CF2,8H)。
实施例15:制备式115的化合物。
在30ml四氢呋喃中溶解1.95g(1.31mmol)式114的化合物[按照实施例14制成]和0.16g(1.56mmol)三乙胺。在室温和氮气氛下,把0.13g(0.65mmol)对苯二甲酰氯加进反应混合物。在室温下搅拌该反应混合物5h。加入水(30ml)并搅拌该反应混合物15min,然后滤出固体并在烘箱内烘干,产生式115的化合物,即白色固体,熔点为337~347℃。1H NMR:(300MHz,四氢呋喃-d8):δ=10.19(s,NH,4H);10.06(s,NH,2H);8.82~8.75(m,ArH,8H);8.72~8.65(m,ArH,4H);8.50~8.45(m,ArH,4H);8.45~8.35(m,ArH,2H);8.22~8.18(m,ArH,4H);4.72(t,J=6.0Hz,OCH2CH2CF2,16H);2.95~2.70(m,OCH2CH2CF2,16H)。
实施例16:在聚丙烯中的斥水和斥油性。
为了确定式I化合物的排斥性,按照下述步骤对它们进行试验。样品制备要组合聚丙烯非织造织物和添加剂并进行热处理(例如,130℃,10min),这能使添加剂迁移到表面并使化学基团作合适的表面重排。需要另外的热循环来熔化式I的化合物,以获得在基材表面上均匀的再分布。把织物重为40g/m2的聚丙烯非织造织物工业样品浸在试验化合物在异丙醇中浓度为1%的溶液内,同时供给超声能量1min。然后,样品在室温下干燥过夜,然后在90℃烘箱内烘2h。然后在130℃退火处理部分样品10min。
以类似于INDA试验方法80.8(99)的斥水性试验评价处理过的非织造样品。用一系列水/异丙醇混合物试验非织造织物的湿润行为。把观察到的湿润行为分成0(水浸润,无斥水性)~10(最佳斥水性)档。结果概括在表1中。
表1:
实施例 | 化合物 | 斥水性干燥后 | 斥水性退火后 |
16aa) | - | 2 | 2 |
16bb) | 101 | 9 | 10 |
16cb) | 102 | 8 | 9 |
16db) | 103 | 9 | 9 |
16eb) | 104 | 6 | 9 |
16fb) | 105 | 10 | 10 |
16gb) | 106 | 7 | 9 |
16hb) | 107 | 7 | 8 |
16ib) | 111 | 7 | 7 |
16jb) | 113 | 5 | 5 |
16kb) | 114 | 6 | 6 |
16lb) | 115 | 5 | 6 |
a)对比实施例。
b)按照本发明的实施例。
以类似于AATCC试验方法118-1997/ISO 14419的斥油性试验评价已处理非织造样品。该试验遵循已述斥水性试验方法的相同概念,但用一系列烃作为溶剂。把观察的湿润行为分为0(无斥油性)~8(最佳斥油性)档。结果概括在表2中。
表2:
实施例 | 化合物 | 斥油性干燥后 | 斥油性退火后 |
16ma) | - | 0 | 0 |
16nb) | 101 | 6 | 5 |
16ob) | 103 | 8 | 8 |
16pb) | 105 | 8 | 8 |
a)对比实施例。
b)按照本发明的实施例。
实施例17:聚丙烯非织造纤维
配混:在70℃烘箱内加热式101的化合物[按照实施例1制成]直到它完全呈液态。用Leistritz MIC 27/GL-32D双螺杆挤出机,把该液体以10~20ml/min经由加热量筒加进聚丙烯粒料的双螺杆挤出中。挤出区为150~195℃,主螺杆转速为500RPM,PP喂料器转速为200~250RPM。熔融聚合物和添加剂经由2孔圆口模排出。熔融材料立即在冷水槽内被冷却并凝固。把凝固条喂进Conair/Jetro 304造粒机。纺粘加工中所用的聚丙烯是获自ExxonMobil的PP 3155(熔体流率为36g/10min)和获自ExxonMobil的PP 3546(熔体流率为1200g/10min)用于熔喷加工。
或者,还由技术人员把式101的化合物制成母粒。然后把所需量的母粒与适量的聚丙烯进行翻滚混合,以制造纺粘和熔喷非织造织物。
转鼓混合:把浓缩颗粒加进另外的聚丙烯颗粒并用Marion SPS1224混合机进行混合,得到所期望的添加剂重量浓度。
纺粘工艺:从以上制成的经转鼓混合的添加剂颗粒,用1m宽的Reicofil II纺粘试验生产线在下列条件下制成纺粘非织造聚丙烯纤维:挤出机温度:200~220℃。过滤网更换器温度为205℃。纺丝泵速度为9rpm。4000孔喷丝板的温度梯度为223~240℃。粘结压力为260~300PLI,粘结温度为130~140℃。冷空气速度为1700rpm,空气抽吸速度为1500rpm,收丝速度调节到形成特定基础重量的非织造织物。
熔喷工艺:熔喷聚丙烯纤维也从以上制成的翻滚混合添加剂颗粒,用24-英寸Reifenhauser熔喷试验生产线,以双组分技术,在下列条件下制成:A、B挤出机的挤出机温度都为160~240℃,过滤网更换器温度为240℃。A、B挤出机的纺丝泵速度都为16rpm。口模温度梯度为240℃。产率为29.7kg/h。抽吸机的速度为2000rpm,纺丝带速度调节到形成特定基础重量的非织造织物。
或者:熔喷聚丙烯纤维也从以上制成的翻滚混合添加剂颗粒,用定制6英寸熔喷试验生产线,在下列条件下制成:挤出机温度为175~265℃。口模温度为265℃。产率为0.49g/h/m(4.44kg/h)。纺丝鼓速度调节到形成特定基础重量的非织造织物。
以类似于INDA标准(国际非织造织物和一次性制品协会)对所得非织造样品评价其斥水/斥油性。结果概括在表3中。
表3:
实施例 | 化合物 | 斥水性 |
17aa) | - | 2 |
17bb) | 1%化合物101c) | 7 |
17cb) | 2%化合物101c) | 9 |
a)对比实施例。
b)按照本发明的实施例。
Claims (17)
1.包含下列组分的组合物:
a)易受氧化、热或光诱导降解的有机材料,和
b)至少一种通式I的化合物
其中
R3是含氟基团,
R4是C1~C25烷基、C3~C25链烯基、未取代或C1~C4烷基取代的苯基,
R5是氢、-Y-R7,
R6是氢、C1~C8烷基或苄基,
R7是C1~C25烷基、C2~C25链烯基、未取代或被C1~C4烷基或C1~C4烷酰基氨基取代的苯基;未取代或C1~C4烷基取代的苯基氨基,
R10是氢、C1~C8烷基或苄基,
R11是氢、C1~C8烷基或苄基,
R12和R13各自独立地是氢、C1~C12烷基或苯基,或R11和R12连同键接的碳原子一起形成未取代或被1~3个C1~C4烷基取代的C5~C8亚环烷基环。
3.按照权利要求1的组合物,其中R3是C1~C25氟代烷基。
4.按照权利要求1的组合物,其中R6和R10是氢。
5.按照权利要求1的组合物,其中R7是C1~C18烷基、C2~C18链烯基、未取代或被C1~C4烷基或C1~C4烷酰基氨基取代的苯基;未取代或C1~C4烷基取代的苯基氨基。
6.按照权利要求1的组合物,其中R12和R13彼此独立地各是氢或C1~C4烷基,或R12和R13连同键接的碳原子一起形成亚环己基环。
8.按照权利要求1的组合物,其中组分(a)是天然、半合成或合成聚合物。
9.按照权利要求1的组合物,其中组分(a)是合成聚合物。
10.按照权利要求1的组合物,其中组分(b)是纤维或非织造织物。
11.按照权利要求1的组合物,其中组分(b)的存在量是组分(a)重量的0.01~10%
12.按照权利要求1的组合物,除包含组分(a)和(b)以外,还包含其它添加剂。
13.按照权利要求12的组合物,包含酚醛抗氧剂、光稳定剂和/或加工稳定剂作为其它添加剂。
14.通式I的化合物
其中
R2是-X-R3,
R3是含氟基团,
R4是C1~C25烷基、C3~C25链烯基、未取代或C1~C4烷基取代的苯基,
R6是氢、C1~C8烷基或苄基,
R7是C1~C25烷基、C2~C25链烯基、未取代或被C1~C4烷基或C1~C4烷酰基氨基取代的苯基;未取代或C1~C4烷基取代的苯基氨基,
R10是氢、C1~C8烷基或苄基,
R11是氢、C1~C8烷基或苄基,
R12和R13彼此独立地各是氢、C1~C12烷基或苯基,或R11和R12连同键接的碳原子一起形成未取代或被1~3个C1~C4烷基取代的C5~C8亚环烷基环。
16.减小有机材料表面能的方法,该方法包含在有机材料中掺入至少一个按照权利要求1的组分(b)。
17.按照权利要求1的组分(b)作为有机材料表面能降低剂的用途。
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JP3579912B2 (ja) | 1994-02-09 | 2004-10-20 | 三菱化学株式会社 | ベンゼン誘導体および液晶組成物 |
JPH08208836A (ja) * | 1995-02-02 | 1996-08-13 | Chisso Corp | 含フッ素ポリイミド |
US6127485A (en) * | 1997-07-28 | 2000-10-03 | 3M Innovative Properties Company | High temperature-stable fluorochemicals as hydrophobic and oleophobic additives to synthetic organic polymers |
WO2003006553A1 (fr) * | 2001-07-09 | 2003-01-23 | Kaneka Corporation | Composition de resine |
WO2004072168A2 (en) * | 2003-02-14 | 2004-08-26 | Ciba Specialty Chemicals Holding Inc. | Resin compositions |
-
2006
- 2006-01-06 MY MYPI20060061A patent/MY145424A/en unknown
- 2006-01-30 CA CA002595981A patent/CA2595981A1/en not_active Abandoned
- 2006-01-30 DE DE602006019550T patent/DE602006019550D1/de active Active
- 2006-01-30 JP JP2007553591A patent/JP5091683B2/ja not_active Expired - Fee Related
- 2006-01-30 CN CNA2006800036543A patent/CN101111467A/zh active Pending
- 2006-01-30 US US11/883,009 patent/US7560502B2/en not_active Expired - Fee Related
- 2006-01-30 EP EP06707887A patent/EP1846356B1/en not_active Not-in-force
- 2006-01-30 WO PCT/EP2006/050508 patent/WO2006082166A1/en active Application Filing
- 2006-01-30 AT AT06707887T patent/ATE495145T1/de not_active IP Right Cessation
- 2006-02-06 TW TW095103851A patent/TWI370829B/zh not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN104350188A (zh) * | 2012-05-04 | 2015-02-11 | 朗盛德国有限责任公司 | 具有降低的表面张力的热塑性塑料纤维 |
Also Published As
Publication number | Publication date |
---|---|
TW200640833A (en) | 2006-12-01 |
EP1846356A1 (en) | 2007-10-24 |
US7560502B2 (en) | 2009-07-14 |
TWI370829B (en) | 2012-08-21 |
ATE495145T1 (de) | 2011-01-15 |
DE602006019550D1 (de) | 2011-02-24 |
JP2008530260A (ja) | 2008-08-07 |
EP1846356B1 (en) | 2011-01-12 |
MY145424A (en) | 2012-02-15 |
US20080146742A1 (en) | 2008-06-19 |
JP5091683B2 (ja) | 2012-12-05 |
CA2595981A1 (en) | 2006-08-10 |
WO2006082166A1 (en) | 2006-08-10 |
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