CN101072802A - 疏水性改性的阳离子聚合物及其作为清洁助剂的使用 - Google Patents
疏水性改性的阳离子聚合物及其作为清洁助剂的使用 Download PDFInfo
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- CN101072802A CN101072802A CNA2005800419688A CN200580041968A CN101072802A CN 101072802 A CN101072802 A CN 101072802A CN A2005800419688 A CNA2005800419688 A CN A2005800419688A CN 200580041968 A CN200580041968 A CN 200580041968A CN 101072802 A CN101072802 A CN 101072802A
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- water
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- 230000007103 stamina Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000012747 synergistic agent Substances 0.000 description 1
- VXHFNALHLRWIIU-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)C VXHFNALHLRWIIU-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 108010050327 trypticase-soy broth Proteins 0.000 description 1
- 108010046845 tryptones Proteins 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
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Abstract
其用于硬质表面的清洁组合物,其含有聚合物,该聚合物包含从至少下列单体组分衍生的主链:(I)20-99.9重量%的至少一种根据通式(I)的阳离子单体,式中R1和R2,各自独立地是氢或C1-C4烷基;R3和R4,各自独立地是氢或烷基、羟烷基、羧基烷基、羧酰胺烷基或烷氧基烷基,所述烷基具有1-18个碳原子;并且Y-表示阴离子,以及(II)0.1-80重量%的疏水性不饱和非离子单体,其在引发剂存在下聚合;任选的至多60重量%的水溶性单体(III),其不同于单体(I)或单体(II);和任选的反应物(IV),0-10重量%量的交联剂。该组合物提供改进的去污性质、抗菌的和生物膜抑制性质,以及对再污染和沾污的抗性。
Description
本发明涉及含有阳离子基团的疏水性改性的聚合物的制备,具体是衍生自二烯丙基二甲基氯化铵(diallyldimethyl ammonium chloride,DADMAC)和相似部分的那些聚合物的制备,且本发明涉及在硬质表面清洁制剂中使用这种聚合物的方法,该制剂对用所述聚合物处理的表面提供改进的去污性质、对后续污染和沾污(staining)的抗性,以及细菌生长的抑制。
对于家中硬质表面去除顽渍有效的清洁产品存在强烈的消费者需求。尤其是,这些污垢可包括皂垢(soap scum)、硬水斑(hard water stain)、锈、油脂污垢(greasy soil)、泥、厨房污垢和卫生间沾污。
此外,对提供抗菌效益的产品存在强烈的需求,即呈现显著抗菌作用的物质,特别抵抗致病的革兰氏阳性和革兰氏阴性菌并且还抵抗酵母和霉菌的性质。能够使用所述抗菌剂,以赋予表面材料抗菌性能或在使用前对硬质表面消毒。
重要的是,在消费产品中使用的抗菌产品是毒理容许的(toxicologicallyacceptable)且对皮肤不引起刺激和敏感。它们还必须是环境友好的且在使用后易于生物降解。同样越来越多的意识到,用于杀灭或控制微生物生长的抗菌剂不应引起微生物对抗生素的抗性。
一直以来,产生更有效清洁物的方法之一是将聚合物加入产品中,其能够在清洁期间通过吸附到表面而改性基底(substrate)的表面。因为表面经改性的性质的原因,后来被沉积到经改性表面的污垢较易于去除。通常认为,提高去污的实际机理由以下产生:1)因为经改性的表面性质的原因,污垢黏附力被降低;2)牺牲膜型机理(sacrificial film type mechanism),其中污垢同膜一起被洗掉;或3)增加表面上的吸水性,其阻止污垢干燥并且使它们更易于去除。也可能存在其他机理。
欧洲专利申请467,472 A2公开了季铵化的烷基甲基丙烯酸聚合物(quaternized ammonium alkyl methacrylate polymer)和其共聚物的使用,以改性硬质表面来提供较易清洁的优越性。美国专利No.6,025,314描述了洗碟漂洗助剂组合物(dishwashing rinse aid composition),其包含烷基铵丙烯酰胺聚合物(ammonium alkyl acrylamide polymer)或共聚物,其赋予了改进的蛋白质去污性质。
美国专利6,664,218公开了硬质表面清洁组合物,其含有两性离子表面活性剂和二烯丙基二甲基氯化铵/丙烯酰胺/丙烯酸共聚物。
美国专利申请公开2003/0203825描述了在自动洗碟机中使用清洁或漂洗组合物减少或防止污垢再沉积的方法,该清洁或漂洗组合物也含有二烯丙基二甲基氯化铵/丙烯酰胺/丙烯酸共聚物。
WO 03/070866要求保护用于硬质表面的防污洗涤剂(antifoulingdetergent),其包含具有由各种阳离子材料(优选为二烯丙基二甲基氯化铵)组成的单体单元的聚合物。美国专利申请公开2003/0216281描述了一种用于硬质表面的液体清洁组合物,其包含共聚物,该共聚物既具有阳离子单体也具有阴离子疏水性基团或不带电的疏水性基团。
WO 04/056888描述了二丙烯基二甲基氯化铵与疏水性共聚单体的共聚物的合成,以及其作为洗衣添加剂的用途,以防止染料渗色和/或染料从织物转移。存在的推测是,所述共聚物也用于以下的制剂中该制剂用于处理家中或其它室内的硬质表面,以防止沾污,例如在洗碟应用中的碟子,但这并非穷举性的。
这些公开中没有一个描述了,如本文所述的二烯丙基二甲基铵与疏水性共聚单体的共聚物在硬质表面清洁应用中的用途。然而,已经发现这些材料具有结合到硬质表面并且改性硬质表面的独特能力,这是因为它们联合了阳离子电荷和疏水性质。当被加入其中时,这些性质为清洁制剂提供了独特的去污性质。
本发明的一个目的是提供硬质表面清洁制剂,其含有疏水性改性的聚合物(hydrophobically modified polymer),该聚合物含有阳离子基团,具体为DADMAC部分。另一个目的是提供在硬质表面清洁制剂中使用这种聚合物的方法,该制剂提供改进的去污性质,以及对污染和沾污的抗性。这种表面的实例包括瓷砖(ceramic tile)、石材、玻璃、水泥、混凝土、砖、石膏(例如,墙)、大理石和石砖建筑(masonry);石材、大理石或塑料的工作台面,和木材、层压材料(laminate)或由有机或无机材料制成的其他类型地板。
同时具有疏水和阳离子基团的聚合物被认为能够提高聚合物对基底的直接性(substantivity,持久力),由此改进表面改性性能和后续的去污性能。同时,这些聚合物拥有合理的水溶性/可分散性,因而能够容易地将它们加入液体硬质表面清洁制剂中。
本发明的另一个目的是提供清洁产品或物质,其能够有助于在人类感兴趣的基底上防止微生物的生长和繁殖和/或生物膜的形成,后者通常由不能利用普通抗菌物质得以控制的大量微生物的积累产生。可以想象的是,这样的抗生物膜可以是聚合材料,因而所述聚合物质能够通过在基底上生成生物膜而对所述基底提供理想的抗菌性质。这种效果的作用方式可能是产生对感兴趣的微生物的附着(attachment)、黏附(adhesion)、生长、积累和繁殖不友好的表面的结果,而不是常规所述的抑制、杀灭、消除,即由常规抗菌物质提供的抑菌(bacteristatic)或杀菌效果。聚合膜还能够在以下方面拥有最小限度的风险:对生物基底例如皮肤、指甲和毛发的生物渗透(bio-penetration),以及对环境的生态毒性(eco-toxicity),其常常是所述物质对水生环境中存在的微生物的不合需要的抗菌效力的结果。此外,能够想象的是,这样的聚合物质在它们对任何有害物质的有限释放方面可以是优异的。
因此这样的物质,本文描述为弱抗菌微生物控制剂(weak antimicrobialmicroorganism-controlling agent),对许多应用以及对环境友好的解决方案规定将是具有显著有利的。
本发明涉及硬质表面防护和清洁组合物(hard surface protectant andcleaning composition),其含有聚合物,该聚合物包含从至少下列单体组分衍生的主链:
(I)至少一种通式(I)的阳离子单体,其量为20-99.9重量%的,优选为50-99重量%,
其中
R1和R2,各自独立地是氢或C1-C4烷基;
R3和R4,各自独立地是氢或烷基、羟烷基、羧基烷基、羧酰胺烷基(carboxyamide alkyl)或烷氧基烷基,其中所述烷基具有1-18个碳原子;和
Y-表示阴离子,以及
(II)0.1-80重量%的疏水性不饱和非离子单体,其在引发剂存在下聚合;
(III)任选的水溶性单体,其量为至多60重量%且其不同于单体(I)或单体(II);和
(IV)任选的反应物,其为0-10重量%量的交联剂。
本发明还涉及使硬质表面免于后续沾污或细菌污染的硬质表面清洁和保护方法,其包含使表面与有效清洁量的硬质表面清洁制剂接触,所述制剂含有如上定义的根据通式(I)的聚合物。
在本发明中有用的聚合物同时具有疏水基团和阳离子基团,其能够在活化剂(activator)的存在下,从聚合混合物产生,该聚合混合物包含:
(I)至少一种根据通式(I)的阳离子单体,其量为20-99重量%,优选为50-99重量%,并且特别优选为80-96重量%
其中
R1和R2,各自独立地是氢或C1-C4烷基;
R3和R4,各自独立地是氢烷基、羟烷基、羧基烷基、羧酰胺烷基或烷氧基烷基,其中烷基具有1-18个碳原子;和
Y-表示阴离子,
(II)疏水性不饱和非离子单体,其在引发剂存在下聚合,该疏水性不饱和非离子单体的量为0.1-80重量%,优选为1-50重量%,并且特别优选为4-20重量%;
(III)任选的水溶性单体,其不同于单体(I)或单体(II),且其量为至多60重量%,优选为至多20重量%;和
(IV)任选的反应物,0-10重量%(优选0-2重量%)量的交联剂。某些这种化合物从WO 2004/056888 A2中获知。
疏水性单体(II)在室温和pH 7时的水溶性值优选为每100g水小于约50g疏水性单体(即,小于约50g/100g水),并且更加优选小于5g/100g水。
优选阳离子单体(I)的实例包括二烯丙基二甲基氯化铵(DADMAC)、二烯丙基二甲基溴化铵、二烯丙基二甲基硫酸铵、二烯丙基二甲基磷酸铵、二(甲代烯丙基)二甲基氯化铵(dimethallyl dimethyl ammonium chloride)、二(乙基烯丙基)二甲基氯化铵(diethylallyl dimethyl ammonium chloride)、二烯丙基二(β-羟乙基)氯化铵(diallyl di(beta-hydroxyethyl)ammonium chloride)和二烯丙基二(β-乙氧基乙基)氯化铵(diallyl di(beta-ethoxyethyl)ammonium chloride)。最优选阳离子单体是DADMAC。优选地,聚合混合物包含50-99重量%(特别优选80-98重量%)的至少一种通式(I)的阳离子单体。
疏水性单体(II)的实例包括,但不限于,选择的乙烯类化合物和(甲基)丙烯酯类化合物((meth)acrylate based compound),和其它不饱和化合物例如(甲基)丙烯腈和不饱和多官能酸的酯。
用于单体(II)的合适乙烯类化合物的实例包括,但不限于,苯乙烯;C2-C18羧酸的乙烯基酯,例如乙酸乙烯酯和丁酸乙烯酯;C2-C18羧酸的N-乙烯基酰胺,例如N-乙烯基乙酰胺等。
作为单体(II)的合适(甲基)丙烯酯类化合物包括,但不限于,(甲基)丙烯酸的酯和(甲基)丙烯酸的酰胺。
(甲基)丙烯酸的酯和(甲基)丙烯酸酯((meth)acrylate)包含:
长链和短链烷基(甲基)丙烯酸酯(alkyl(meth)acrylate),例如(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸戊酯(amyl(meth)acrylate)、(甲基)丙烯酸异丁酯、(甲基)丙烯酸叔丁酯、(甲基)丙烯酸戊酯(pentyl(meth)acrylate)、(甲基)丙烯酸异戊酯、(甲基)丙烯酸己酯、(甲基)丙烯酸庚酯、(甲基)丙烯酸辛酯、(甲基)丙烯酸异辛酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸异癸酯、(甲基)丙烯酸十一烷基酯、(甲基)丙烯酸十二烷基酯(dodecyl(meth)acrylate)、(甲基)丙烯酸月桂酯(lauryl(meth)acrylate)、(甲基)丙烯酸十八烷酯(octadecyl(meth)acrylate)和(甲基)丙烯酸十八烷醇酯(stearyl(meth)acrylate);(甲基)丙烯酸烷氧基烷基酯(alkoxyalkyl(meth)acrylate),特别(甲基)丙烯酸C1-C4烷氧基C1-C4烷基酯,例如丙烯酸丁氧乙酯(butoxyethylacrylate)和丙烯酸乙氧基乙氧基乙酯(ethoxyethoxyethyl acrylate);
(甲基)丙烯酸芳氧基烷基酯(aryloxyalkyl(meth)acrylates),特别(甲基)丙烯酸芳氧基C1-C4烷基酯,例如丙烯酸苯氧乙酯(phenoxyethyl acrylate)(例如,Ageflex,Ciba Specialty Chemicals Corp.);
单环和多环的芳族或非芳族的丙烯酸酯,例如丙烯酸环己酯(cyclohexylacrylate)、丙烯酸苄酯(benzyl acrylate)、二环戊二烯丙烯酸酯(dicyclopentadieneacrylate)、丙烯酸二环戊烯基酯(dicyclopentanyl acrylate)、三环癸基丙烯酸酯(tricyclodecanyl acrylate)、丙烯酸冰片酯(bornyl acrylate)、丙烯酸异冰片酯(isobornyl acrylate)(例如,AgeflexIBOA,Ciba Specialty Chemicals Corp.)、丙烯酸四氢糠酯(tetrahydrofurfuryl acrylate)(例如,SR285,Sartomer Company,Inc.)、丙烯酸己内酯(caprolactone acrylate)(例如SR495,Sartomer Company,Inc.)和丙烯酰吗啉(acryloylmorpholine);
醇基(甲基)丙烯酸酯(alcohol-based(meth)acrylate)例如聚乙二醇单丙烯酸酯(polyethylene glycol monoacrylate)、聚丙二醇单丙烯酸酯(polypropyleneglycol monoacrylate)、甲氧基乙二醇丙烯酸酯(methoxyethylene glycolacrylate)、甲氧基聚丙二醇丙烯酸酯(methoxypolypropylene glycol acrylate)、甲氧基聚乙二醇丙烯酸酯(methoxypolyethylene glycol acrylate)、乙氧基二甘醇丙烯酸酯(ethoxydiethylene glycol acrylate)和各种烷氧基化的烷基酚丙烯酸酯例如乙氧基化(4)壬基酚丙烯酸酯(例如,Photomer 4003,Henkel Corp.);
(甲基)丙烯酸的酰胺例如双丙酮丙烯酰胺(diacetone acrylamide)、异丁氧甲基丙烯酰胺(isobutoxymethyl acrylamide)和叔辛基丙烯酰胺(t-octylacrylamide);
和
多官能不饱和酸的酯,例如马来酸酯和富马酸酯。
关于上列的长链和短链烷基丙烯酸酯,短链烷基丙烯酸酯的烷基带有6个或少于6个碳,长链烷基丙烯酸酯的烷基带有7个或多于7个碳。大多数合适的单体是商业上可获得的或使用本领域已知的反应方案易于合成的。例如,大多数上列单体能够通过将合适的醇或酰胺与丙烯酸或烯丙酰氯反应。
作为单体(II)使用的优选化合物的具体实例由通式(B)例示
其中
R5是H或CH3,
R6是C1-C12烷基、C1-C12烷氧基、可被C1-C12烷基或C1-C12烷氧基取代一至三次的C1-C6烷基苯基、被氧间隔一次或多次的C1-C6烷基苯基,其中所述苯基可以被C1-C12烷基、C1-C12烷氧基或羟基C1-C6烷基取代一至三次。
X是选自-O-、-NH-和-NR-的二价基,和
R是C1-C6烷基。
特别优选化合物由以下例示:
和
其中R5和X如上定义,并且n是1-5的数,优选2或3。
所述聚合混合物任选地进一步包括水溶性单体(III),其是不同于单体(I)和单体(II)的可聚合单体。水溶性单体(III)在室温和pH 7时的水溶性值优选大于50g/100g水。
水溶性单体(III)可以是非离子的、阴离子的或阳离子的。单体(III)的实例包括乙烯胺、乙烯基甲酰胺、乙烯醇、乙烯基吡咯烷酮、乙烯基己内酰胺、二甲基硅氧烷的乙烯基衍生物(vinyl derivative ofdimethyl siloxance)、氨基硅氧烷的乙烯基衍生物和其它衍生物,各种乙烯基碳氟化合物(vinylfluorocarbon),丙烯酸羟烷基酯(hydroxyalkyl acrylates)例如丙烯酸-2-羟乙基酯(2-hydroxyethyl-acrylate)、丙烯酸-2-羟丙基酯(2-hydroxypropyl-acrylate)和丙烯酸-2-羟丁基酯(2-hydroxybutyl-acrylate);丙烯酸氨烷基酯(aminoalkyl acrylate)例如丙烯酸二甲氨基乙酯(dimethylaminoethyl acrylate)、丙烯酸二乙氨基乙酯(diethylaminoethyl acrylate)和7-氨基-3,7-二甲基辛基丙烯酸酯(7-amino-3,7-dimethyloctyl acrylate),和它们的盐,包括它们的烷基和苯甲基季铵化盐;(甲基)丙烯酸和它们的盐;和丙烯酰胺、甲基丙烯酰胺、N,N-二甲基丙烯酰胺、N,N-二乙基丙烯酰胺、N,N’-二甲氨基丙基丙烯酰胺(N,N’-dimethylaminopropyl acrylamide),和它们的盐。
所述聚合混合物进一步任选地含有反应物(IV),其是0-10%重量的交联剂。合适的交联剂的优选实例包括亚甲基双丙烯酰胺(methylenebisacrylamide)、季戊四醇二丙酸酯,季戊四醇三丙烯酸酯和季戊四醇四丙烯酸酯、二乙烯基苯、聚乙二醇二丙烯酸酯(polyethylene glycol diacrylate)和双酚A二丙烯酸酯(bisphenol A diacrylate)。
更加常见的是,合适的交联剂是多官能烯属不饱和单体(polyfunctionalethylenically unsaturated monomer)。这样的单体包括,但不限于,烷氧基化双酚A二丙烯酸酯,例如乙氧化度为2或以上的乙氧基化双酚A二丙烯酸酯,乙氧化度优选为2至约30(例如,可从Sartomer Company,Inc.(West Chester,Pa.)获得的SR349和SR601和可从Henkel Corp.,Ambler,Pa.获得的Photomer 4025和Photomer 4028),和丙氧化度为2或以上,优选为2至约30的丙氧基化双酚A二丙烯酸酯;
具有或不具有烷氧基化的三羟甲基丙烷聚丙烯酸酯(trimethylolpropanepolyacrylate),例如乙氧化度为3或以上,优选从3至约30的乙氧基化三羟甲基丙烷三丙烯酸酯(例如,Photomer 4149,Henkel Corp.和SR499,SartomerCompany,Inc.),丙氧化度为3或以上,优选为3-30的丙氧基化三羟甲基丙烷三丙烯酸酯(例如,Photomer 4072,Henkel Corp.和SR492,Sartomer),和二(三羟甲基丙烷)四丙烯酸酯(ditrimethylolpropane tetraacrylate)(例如,Photomer4355,Henkel Corp.);
烷氧基化的甘油三丙烯酸酯(alkoxylated glyceryl triacrylate),例如丙氧化度为3或以上的丙氧基化甘油三丙烯酸酯(例如,Photomer 4096,Henkel Corp.和SR9020,Sartomer);
具有或不具有烷氧基化的季戊四醇聚丙烯酸酯(pentaerythritolpolyacrylate),例如季戊四醇四丙烯酸酯(例如,SR295,可从Sartomer Company,Inc.(West Chester,Pa.)获得)、乙氧基化的季戊四醇四丙烯酸酯(例如,SR494,Sartomer Company,Inc.),和二季戊四醇五丙烯酸酯(例如,Photomer 4399,Henkel Corp.和SR399,Sartomer Company,Inc.);
由合适的功能性异氰尿酸盐(或酯)与丙烯酸或烯丙酰氯反应形成的异氰尿酸酯聚丙烯酸酯(isocyanurate polyacrylate),例如三(2-羟乙基)异氰尿酸酯三丙烯酸酯(例如,SR368,Sartomer Company,Inc.)和三(2-羟乙基)异氰尿酸酯二丙烯酸酯;具有或不具有烷氧基化的多元醇聚丙烯酸酯,例如三环癸基二甲醇二丙烯酸酯(tricyclodecane dimethanol diacrylate)(例如,CD406,SartomerCompany,Inc.)和
乙氧基化的聚乙二醇二丙烯酸酯(ethoxylated polyethylene glycoldiacrylate),其具有2或以上乙氧基化,优选约2-30;通过将丙烯酸酯加入双酚A二缩水甘油基醚等形成的羟基丙烯酸酯(例如,Photomer 3016,HenkelCorp.);以及单环和多环的环状芳族或非芳族的聚丙烯酸酯,例如二环戊二烯基二丙烯酸酯(dicyclopentadiene diacrylate)和二环戊烷二丙烯酸酯(dicyclopentane diacrylate)。
本发明聚合物的制备可以如下进行:使用各种聚合技术,例如溶解、乳化、微乳化、逆乳化(inverse emulsion)和/或本体聚合,以及其它为本领域技术人员所知的技术。显然,聚合可以在有或没有各种浓度的各种引发剂下进行。共聚物或三聚物也能够这样的方法制备,其中所述聚合物的构造是随机的、嵌段的(block)、交替的(alternating)、芯壳型的(core-shell),以及使用或不使用聚合调节剂例如硝酰基醚(nitroxyl ether)或其它类型的硝酰基自由基(nitroxyl radical)。
用于制造本发明聚合物的优选方法是通过使用水溶性引发剂的水相聚合。合适的引发剂的实例包括过硫酸盐例如过硫酸铵(APS);过氧化物例如过氧化氢、叔丁基氢过氧化物和过氧化叔戊酸叔丁酯,偶氮基引发剂例如2,2’-偶氮双(2-脒基丙烷)二氢氯化物(2,2’-azobis(2-amidinopropane)dihydrochloride)、4,4’-偶氮双(4-氰基戊酸)和2,2’-偶氮双异丁腈;和氧化还原引发剂***例如叔丁基氢过氧化物/Fe(II)和过硫酸铵/亚硫酸氢铵。
使用过硫酸铵(APS)的水溶液聚合是用于制备具有优选阳离子DADMAC单体的聚合物的优选方法。在聚合过程中使用的自由基引发剂的量取决于总单体浓度和所用的单体类型,并且为达到多于99%的总单体转化,可以是约0.2-约5.0重量%的单体总量(total monomer charge)。
疏水性单体(II)在水相溶解,至少部分溶解,并且与优选的阳离子单体DADMAC共聚以形成,具有阳离子和疏水性基团的聚合物。当将疏水性单体(II)以高于其水溶性的量添加到聚合***中时,如果提供充分的搅拌,则超过的量能够形成微细液滴(fine droplet)的第二相。不旨在限制于此聚合机理,单体(II)的液滴可以作为单体储库(reservoir)以向水相提供单体(II)。
当使用水溶性引发剂时,单体(I)和疏水性单体(II)的溶解部分之间的共聚在水相中被引发。由此形成的疏水性改性的聚合物可溶于水或不溶于水,这取决于其疏水性或水溶性以及所用单体(II)的浓度。所得的聚合物能够具有表面活性剂的性质,并且可以胶态(colloidal state)出现,呈现半透明的外观。
所需量的单体(II)可以全部在开始时加入,递增地,或通过连续进料到反应器加入。连续进料疏水性单体(II)到水相反应介质可以具有以下优点:生成的疏水性改性共聚物而较少形成均聚物或大均聚链段(large homopolymericsegment)的形成。
优选在没有氧气存在下进行聚合。能够通过以下方法从反应介质中去除氧气:施用真空伴随以搅拌,或用惰性气体例如氮气或氩气吹扫。随后聚合可以在所述惰性气体层下进行。
所制备聚合物的分子量可以为一千至几百万。例如用GPC测量,其具有1000-5百万道尔顿的平均分子量。
所述聚合物可以呈现为各种形式呈现,即溶液、分散体(dispersion)、悬浮液、颗粒(granule)、粉末、珠粒(bead)、块(block)等。当处于液体形式时,例如溶液、分散体、悬浮液等时,液相可以是水性的和/或非水性的,例如大豆油、酯和矿物油。
本发明中使用的聚合物可以掺入本领域技术人员公知的任何类型清洁制剂中。清洁制剂中存在的聚合物的量可以为0.01-20重量%,或优选为0.05-5重量%,并且更优选为0.1-2重量%。清洁制剂也可以含有水、表面活性剂、溶剂、增效剂(builder)、增稠剂、染料、香料、盐、水溶助剂(hydrotropes)、杀生物药剂、杀真菌剂等。清洁制剂也可以含有其它类型的去污聚合物(soilrelease polymer)、着色剂、防腐剂、抗菌剂、光学增亮剂、紫外光吸收剂、其它光线控制剂(light management agent)、电离剂(ionization agent)、防沫剂(antifoam agent)、酶、漂白剂、氧化催化剂、沸石和/或气味抑制剂(odorsuppressing agent),包括但不限于环糊精,以及它们的衍生物或它们的混合物。
表面清洁制剂中使用的表面活性剂通常是水溶的或水可分散的。表面活性剂在本领域是熟知的。
本发明中使用的表面活性剂可以选自一种或多种表面活性剂,其可以为阴离子表面活性剂、阳离子表面活性剂、两性表面活性剂或两性离子表面活性剂。本发明中最优选的表面活性剂是阳离子表面活性剂和非离子表面活性剂,这是因为聚合物的阳离子属性可能与某些阴离子表面活性剂不相容。
可用于本发明的非离子表面活性剂包括,但不限于,烷氧基化醇,包括乙氧基化醇和丙氧基化醇,以及乙氧基化烷基酚和丙氧基化烷基酚。其它类型包括脱水山梨糖醇脂肪酯(sorbitan fatty ester)和不饱和醇的脂肪酸。
其它类型的非离子表面活性剂包括美国专利4,565,647中公开的烷基多糖,其具有含约6-30个碳原子的疏水性基团,优选约10-16个碳原子的疏水性基团;以及多糖亲水基团,例如聚糖苷(polyglycoside)。
另一类型的合适的表面活性剂包括某些单长链烷基阳离子表面活性剂,其用于本发明的硬质表面清洁组合物中。此类阳离子表面活性剂包括通式为R10R20R30R40N+X-的季铵盐,其中R基团是长烃链或短烃链,通常是烷基、羟烷基或乙氧基化烷基,并且X是反离子(例如,化合物中R10是C8-C22烷基,优选C8-C10或C12-C14烷基,R20是甲基,并且R30和R40可相同或不同,且为甲基或羟乙基);和阳离子酯(例如,胆碱酯)。X优选卤素反离子,例如氯或溴。
清洁制剂可作为即用型喷雾剂、液体或膏直接施加至表面上,随后使用纸巾、海绵、布、拖把或其它合适的擦拭工具将其擦去。或者,可以首先将组合物施加至擦拭工具上,随后施加至表面上。还可以以可稀释的形式提供组合物,即固体或液体浓缩物,其可以用水稀释以获得最终清洁组合物。例如,其可以为下列形式:可稀释的粉末或颗粒制剂,或片剂、成袋状(pouch)或囊剂(sachet)。
可将组合物加至可重复使用的或一次性的擦布或垫中,随后通过擦拭将其用于处理表面。所述组合物被吸收至擦布或垫内或者吸附在其上,换句话说,使擦布或垫浸渍含水清洁组合物。这样的擦布可以由天然的或人造的纤维制造,例如纤维素、聚酯、聚烯烃、织造纤维或非织造纤维或任何其它材料,或本领于技术人员已知的适合于制造擦布的材料的组合。这种擦布通常由非织造型材料制成。例如,聚烯烃是聚丙烯或聚丙烯共聚物或共混物。纤维素是指纤维素类的。
在清洁制剂中含有聚合物的组成通常将显示出pH 3-12,优选4-11。
本发明进一步涉及清洁硬质表面的方法,其包含使表面与有效量的本发明清洁制剂接触。所述清洁硬质表面的方法提供改进的去污性质,以及对污染、沾污和细菌污染的抗性。
在一个这种方法中,将本发明的清洁制剂喷洒至污染的硬质表面上。随后使用纸巾或其它合适的涂抹工具,将湿润的表面擦拭干净。该初始的清洁过程将使得本发明的聚合物沉积在所述硬质表面上,形成无形的膜(invisiblefilm)。在随后表面被再污染之后,与在初始清洁步骤中没有使用本发明的清洁制剂的情况相比,污垢更容易被去除。所述表面与未处理的表面相比还可保持更清洁更长久,因为由本发明的清洁制剂所赋予的更容易清洁的性质通常将倾向于防止污垢黏附到所述表面上。相对于未经所述聚合物组合物处理的类似表面,这样处理过表面还能抵抗细菌的生长。
在可供选择的施用方法中,可以将本发明的清洁制剂施用于清洁的表面上作为预处理步骤,从而使得所述聚合物以无形膜的形式黏附到表面上。所述表面也将对污渍和细菌污染具有抗性,并且与未经本发明的清洁组合物处理过的类似表面相比,该表面在后续的步骤中更容易被清洁。因此,本发明进一步涉及处理硬质表面的方法,由此改进对污染的抗性和后续去污的容易性,该方法包含将所述硬质表面与有效量的本发明制剂接触。
下列实施例描述了本发明的一些实施方案,但本发明不限于此。应该理解的是,在不偏离本发明的精神或范围的情况下,可根据本发明公开的内容,对所公开的实施方案作出众多改变。因此,这些实施例并非意图限制本发明的范围。相反,本发明的范围将仅由所附的权利要求及其等价物确定。在这些实施例中,除非另有说明,给出的所有部分均以重量计。
下列实施例7和8中使用的生物膜抑制完整描述和抗黏附测试方法可参考Bechert T.等,Nature Medicine(2000),Vol.6,No.9,pages 1053-6。
实施例
实施例1
向装备有冷凝器、温度计、氮气进口和置顶搅拌器的1升反应器中,装入453.8g的66%单体DADMAC、15.8g甲基丙烯酸甲酯(MMA)、57.4.0g去离子水和0.15g的20%Na4EDTA溶液。将所述聚合混合物用氮气吹扫,并且搅拌加热至温度90℃。将含有5.1g过硫酸铵(APS)的水溶液缓慢地进料至反应器中,历时190分钟。使反应温度增加至100℃以上,然后在APS进料期间保持在回流温度(100-110℃)。在APS进料之后,将反应温度降低,并且在95℃保持约30分钟。然后加入含有5.6g焦亚硫酸钠(MBS)的水溶液,历时30分钟。将反应器内含物在95℃再保持30分钟,以完成聚合(99%以上的转化率)。用充足的水将聚合物溶液稀释至约35%固体,并且冷却至室温。测得总单体转化率高于99.5%。最终产物于25℃具有23,400cps的布氏粘度(Brookfield viscosity)(使用Brookfield LV4轴,速度为12 rpms)和33.7%聚合物固体。
实施例2
向装备有冷凝器、温度计、氮气进口口和置顶搅拌器的1升反应器中,装入453.8g的66%单体DADMAC、15.8g乙氧基化壬基酚丙烯酸酯(ENPA)、57.4.0g去离子水和0.15g的20%Na4EDTA溶液。将所述聚合混合物用氮气吹扫,并且搅拌加热至温度90℃。将含有5.1g过硫酸铵(APS)的水溶液缓慢地进料至反应器中,历时190分钟。使反应温度增加至100℃以上,然后在APS进料期间保持在回流温度(100-110℃)。在APS进料之后,将反应温度降低,并且在95℃保持约30分钟。然后加入含有5.6g焦亚硫酸钠(MBS)的水溶液,历时30分钟。将反应器内含物在95℃再保持30分钟,以完成聚合(99%以上的转化率)。用充足的水稀释将聚合物溶液至约35%固体,并且冷却至室温。测得总单体转化率高于99.5%。最终产物于25℃具有15,700cps的布氏粘度(使用Brookfield LV4轴,速度为12rpms)和33.7%聚合物固体。
实施例3
本实施例显示了通过连续进料加入疏水性单体II。聚合方法类似于实施例1的方法,不同的是:将15.8g量的甲基丙烯酸甲酯进料到反应器中,进料是从APS引发剂进料开始,历时约45分钟。用充足的水稀释将聚合物溶液至约35%固体,并且冷却至室温。测得总单体转化率高于99.5%。最终产物于25℃具有19,500cps的布氏粘度(使用Brookfield LV4轴,速度为12rpms)和35%聚合物固体。相比于实施例1的产物的乳液外观,最终产物是透明的。
除非另有注释,以下测试的所有聚合物均以类似于实施例1和2所述的制备方法制造。
实施例4:应用
对于下表中描述的每种聚合物,在去离子水中制备该聚合物的0.5%溶液(按重量计)。将2mL所述聚合物溶液加入折叠的纸巾;然后用处理过的纸巾擦拭8英寸×8英寸瓷砖一半的正面30秒,导致那部分的瓷砖表面完全湿润。对瓷砖的另一半未处理,作为对照。随后在流动的去离子水下冲洗该瓷砖30秒;然后使其风干。
随后将整个瓷砖用模拟的皂垢污渍污染,其通过使用Preval Sprayer相继喷涂两种溶液到所述瓷砖的正面制备。第一种溶液是2.5%的氯化钙去离子水溶液,以及第二种溶液是4%油酸钾、0.5%硬脂酸钠和0.1%亚甲基蓝在去离子水中的溶液。风干15分钟后,将喷涂过的瓷砖在85℃烘烤1小时。
随后使用装有两块海绵的Gardner Washability and Wear Tester(ModelD10V)清洁被污染的瓷砖,两块海绵用去离子水润湿并且挤干至刚好潮湿。以并行清洁(side-by-side cleaning)的方式清洁所述瓷砖,直到基本上从瓷砖的至少一侧去除污垢。肉眼评价去污,测量在瓷砖的对照侧和聚合物处理侧的残留污垢百分比。将聚合物处理侧的残留百分比从对照侧的百分比中减去,并且将该分数标准化为“0”至“+++++”的标度,其中0代表对照侧与处理侧在去污中无差别,+++++代表处理侧污垢完全去除而对照侧污垢没有去除。
本发明三种聚合物的结果示于下表1中:
表1
聚合物 | Gardner Stroke数 | 去污分数 |
DADMAC/甲基丙烯酸苄酯(95/5) | 1 | ++++ |
DADMAC/甲基丙烯酸丁酯(95/5) | 2 | ++ |
DADMAC/甲基丙烯酸甲酯(95/5) | 2 | +++ |
实施例5:应用
将每种聚合物的0.5%溶液加入典型的硬质表面清洁制剂中,该制剂含有非离子和阳离子表面活性剂、溶剂和鳌合剂,如下表2所述:
表2
成分 | 描述 | 含量(有效含量) |
BTC50 NF (Stepan) | 阳离子表面活性剂 | 0.2% |
Tomadol 23-65 (Tomah) | 非离子表面活性剂 | 1.5% |
Tomadol 91-8(Tomah) | 非离子表面活性剂 | 1.5% |
丙二醇甲基醚 | 溶剂 | 2.0% |
乙二胺四乙酸,四钠盐 | 鳌合剂 | 0.5% |
去离子水 | -- | 至100% |
去污聚合物 | 去污剂 | 0.5% |
氢氧化钠 | 碱度 | 至pH11 |
将瓷砖的一半用含有去污聚合物的硬质表面清洁溶液,以与实施例4所述的相同方法处理,除了将对照侧用未添加聚合物的硬质表面清洁制剂处理之外。
如实施例4所述在用模拟的皂垢污垢污染并且清洁之后,评估瓷砖的去污。下表3总结了结果,其对于三种聚合物重复三次。
表3
聚合物 | Gardner Stroke数 | 去污分数 |
DADMAC/甲基丙烯酸苄酯(95/5) | 6233 | +++++++++ |
DADMAC/甲基丙烯酸丁酯(95/5) | 222 | ++++++ |
1DADMAC/甲基丙烯酸甲酯(95/5) | 2244 | +++++ |
1.如实施例3制备。
实施例6:应用
将瓷砖的一半用如实施例5所述的含DADMAC/甲基丙烯酸丁酯(95/5)聚合物溶液的硬质表面清洁制剂处理。随后将所述瓷砖通过刷子涂刷用1.5g模拟油脂微粒污浆(greasy particulate soil slurry)处理,其由39.55g玉米油、2.5g油酸、0.04g油蓝N和7.9g高岭土(kaolin clay)制备。然后,将被污染的瓷砖在85℃烘烤大约24小时,直到蓝色污垢变成粉色。冷却之后,将瓷砖在带有海绵的Gardner Washability Tester上清洗,该海绵首先用去离子水润湿,然后用10mL不添加聚合物的实施例5中所述的清洁制剂润湿。以如实施例4和5的相同方式对测试评分。(参见下表4。)
表4
聚合物 | Gardner Stroke数 | 去污分数 |
DADMAC/甲基丙烯酸丁酯(95/5) | 2513 | +++++ |
实施例7
DADMAC共聚物的生物膜增殖抑制
以合适的测试溶液,提供DADMAC共聚物在离子水中的溶液作为储备溶液。
测试原理:
将由聚甲基丙烯酸甲酯(PMMA)制造的标准针(pin)(2mm×8-9mm的小圆柱)在DADMAC共聚物储备溶液中温育20分钟并干燥。使涂覆的针与测试生物的悬浮液接触,以使所述测试生物黏附到针的表面。随后将针转移到生长培养基,以使子细胞能够释放到生长培养基中。然后在合适的温育时间之后移除针。在子细胞的生长之后,以578nm的正常光度单位,用小平板读数器监测生长培养基的光学密度。
测试生物: 表皮葡萄球菌(Staphylococcus epidermidis)
测试浓度: 0.5%(聚合物的重量%)
涂覆时间: 20分钟
干燥时间: 30分钟
接触时间(细胞): 1小时
子细胞释放: 24小时
温育时间: 48小时
表5提供生物膜增殖抑制测试的结果。
结果以小时数表示,其中生物膜生物的生长被抑制。48小时的结果说明生物膜增殖在48小时被完全抑制。
表5:
聚合物 | 生长减少[小时] |
DADMAC/甲基丙烯酸甲酯(95/5) | 48 |
乙醇参比 | 1.0 |
实施例8
通过DADMAC共聚物抑制微生物细胞初始(primary)黏附和附着如下所示。
测试原理:
将由PMMA制造的标准针(2mm×8-9mm的小圆柱)在共聚物储备溶液中温育20分钟并干燥。使涂覆的针与测试生物的悬浮液接触1小时,以使该测试生物黏附到针的表面。在洗涤和转移到遮断溶液(blocking solution)之后,用表皮葡萄杆菌抗体对针处理过夜,并且在进一步的洗涤步骤之后,用带有酶附着的第二抗体处理针(碱性磷酸酯酶)1小时。在最后的洗涤步骤之后,将针转移到酶底物溶液,并且用小平板读数器在405nm观察颜色改变。
测试生物: 表皮葡萄球菌
测试浓度: 储备溶液中0.5%(聚合物的重量%)
涂覆时间: 20分钟
干燥时间: 15分钟
接触时间细胞: 1小时
接触时间第一抗体: 24小时
接触时间第二抗体: 1小时
表6显示实施例8中进行的黏附测试的结果。
结果表示为与未处理的针相比的细胞黏附百分数。
共聚物溶液表明细菌附着中的显著减少。
表6:
聚合物 | 黏附[%] |
DADMAC/甲基丙烯酸甲酯(95/5) | 17 |
无涂覆 | 100 |
实施例9
测定不同DADMAC共聚物的杀微生物活性
测试原理:
将具有合适浓度测试产品的1g储备溶液与8g水混合,并且随后用1ml所选测试生物接种。在给定的接触时间之后,取等分样品,使失活并且稀释。
每ml温育测定液的存活细菌数通过平板计数测定。
稀释剂: 用于微生物的胰蛋白胨水(0.1重量%胰蛋白胨(Oxoid)、
0.85%NaCl、去离子水)
用于DADMAC聚合物溶液的去离子水
用于存活微生物检测的失活培养基
培养基: 酪蛋白大豆蛋白胨琼脂
失活培养基: 专用胰蛋白酶大豆肉汤
(10%Tween 80、3%卵磷脂、0.1%L-组氨酸、
0.055%硫代硫酸钠)
测试生物: 金黄色葡萄球菌(S.aureus)ATCC 6538
大肠杆菌(E.coli)ATCC 10536
测试浓度: 100-120 ppm(DADMAC聚合物浓度)
接触时间: 22℃,5和30分钟
温育: 37℃,24小时
结果作为最初计数的对数减少示于表7。测试的所有DADMAC聚合物显示对大肠杆菌良好的杀微生物活性和对金黄色葡萄球菌一些活性。
表7
聚合物 | 金黄色葡萄球菌/5分钟 | 金黄色葡萄球菌/30分钟 | 大肠杆菌/5分钟 | 大肠杆菌/30分钟 |
DADMAC/甲基丙烯酸甲酯(95/5) | 2.9 | 3.6 | >5 | 5 |
1DADMAC/乙氧基化壬基酚甲基丙烯酸酯(95/5) | 2.1 | 3.7 | >5 | >5 |
DADMAC/甲基丙烯酸苄酯(95/5) | 1.9 | 3.2 | >5 | >5 |
DADMAC/苯乙烯(95/5) | 2.1 | 3.4 | >5 | >5 |
DADMAC/甲基丙烯酸甲酯/丙烯酸(90/5/5) | >5 | >5 |
1.如实施例2制备.
Claims (21)
2.根据权利要求1的组合物,其中至少一种阳离子单体(I)是选自:二烯丙基二甲基氯化铵、二烯丙基二甲基溴化铵、二烯丙基二甲基硫酸铵、二烯丙基二甲基磷酸铵、二(甲代烯丙基)二甲基氯化铵、二(乙基烯丙基)二甲基氯化铵、二烯丙基二(β-羟乙基)氯化铵和二烯丙基二(β-乙氧基乙基)氯化铵。
3.根据权利要求1的组合物,其中至少一种阳离子单体是二烯丙基二甲基氯化铵。
4.根据权利要求1的组合物,其中疏水性单体(II)在室温和pH7时的水溶性值小于约50g/100g水。
5.根据权利要求4的组合物,其中至少一种疏水性单体(II)选自:乙烯类化合物和(甲基)丙烯酯类化合物,和(甲基)丙烯腈和不饱和多官能酸的酯。
6.根据权利要求4的组合物,其中至少一种疏水性单体(II)选自:苯乙烯、C2-C18羧酸的乙烯基酯和C2-C18羧酸的N-乙烯基酰胺。
9.根据权利要求1的组合物,其中水溶性单体(III)在室温和pH7时的水溶性值大于50g/100g水。
10.根据权利要求1的组合物,其中水溶性单体(III)选自下组:乙烯胺、乙烯基甲酰胺、乙烯醇、乙烯基吡咯烷酮、乙烯基己内酰胺、二甲基硅氧烷的乙烯基衍生物、氨基硅氧烷的乙烯基衍生物、乙烯基碳氟化合物、丙烯酸羟烷基酯;丙烯酸氨烷基酯和它们的盐,包括它们的烷基和苯甲基季铵化盐;(甲基)丙烯酸和它们的盐;和丙烯酰胺、甲基丙烯酰胺、N,N-二甲基丙烯酰胺、N,N-二乙基丙烯酰胺、N,N-二(甲氨基丙基)丙烯酰胺,和它们的盐。
11.根据权利要求1的组合物,其中所述聚合物具有1000至5百万道尔顿的平均分子量。
12.根据权利要求1的用于硬质表面的表面防护和清洁组合物,额外地包含有效量的一种或多种表面活性剂。
13.根据权利要求12的组合物,其是以下列形式:即用型喷雾剂、液体或膏,或是固体或可以用水稀释以获得最终清洁组合物的液体浓缩物。
14.根据权利要求12的组合物,包含0.001%-50%的所述聚合物。
15.根据权利要求12的组合物,进一步包含至少一种额外的成分,其是香料、另一种类型的去污聚合物、着色剂、防腐剂、抗菌剂、荧光增白剂、紫外光吸收剂、光线控制剂、电离剂、防沫剂、酶、漂白剂、氧化催化剂、沸石或包括但不限于环糊精及其衍生物的气味抑制剂,或它们的混合物。
16.可重复使用的或一次性的擦布或垫,其用于清洁或处理表面,其中所述擦布或垫已在其内吸收或在其上吸附根据权利要求12的组合物。
17.硬质表面清洁的方法,其包含用有效清洁量的根据权利要求1的清洁组合物接触所述表面。
18.根据权利要求17的方法,其中所述表面是瓷砖、石材、玻璃、水泥、混凝土、砖、石膏、大理石;石材、大理石或塑料的工作台面;和木材、塑料、层压材料或由有机或无机材料制成的其它类型地板。
19.处理硬质表面由此改善耐污性、后续去污容易性以及赋予抗菌性质的方法,该方法包含用有效量根据权利要求12的组合物接触所述硬质表面。
20.对硬质表面进行抗菌处理的方法,其包含用抗菌有效量的权利要求1中定义的聚合物接触所述硬质表面。
21.在硬质表面上抑制生物膜形成的方法,其包含用有效量的权利要求1中定义的聚合物接触所述表面。
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BR112014010971A2 (pt) * | 2011-11-11 | 2017-06-06 | Basf Se | emulsão, processo para fabricar uma emulsão, uso de uma emulsão, e, polímero |
MX2015000782A (es) | 2012-07-19 | 2015-05-07 | Procter & Gamble | Composiciones limpiadoras. |
DE102012221196A1 (de) * | 2012-11-20 | 2014-05-22 | Henkel Ag & Co. Kgaa | Anti-adhäsive Polymere zur mikrobiell-repulsiven Textilausrüstung |
JP6535192B2 (ja) * | 2015-03-25 | 2019-06-26 | 株式会社日本触媒 | 抗菌剤 |
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EP3418363A1 (en) * | 2017-06-21 | 2018-12-26 | The Procter & Gamble Company | Polymer containing antimicrobial hard surface cleaning compositions |
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US2923701A (en) * | 1955-05-02 | 1960-02-02 | American Cyanamid Co | Composition comprising a linear copolymer of a quaternary ammonium compound and an ethylenically unsaturated copolymerizable compound |
US4305860A (en) * | 1980-08-21 | 1981-12-15 | National Starch And Chemical Corporation | Stable, pumpable, solvent-free colloidal polyampholyte latices, their preparation and use in paper |
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JP4890027B2 (ja) * | 2002-12-23 | 2012-03-07 | チバ ホールディング インコーポレーテッド | 洗濯添加剤としての疎水的に変性されたポリマー |
-
2005
- 2005-11-28 WO PCT/EP2005/056256 patent/WO2006061334A1/en active Application Filing
- 2005-11-28 AT AT05823845T patent/ATE496949T1/de not_active IP Right Cessation
- 2005-11-28 CN CNA2005800419688A patent/CN101072802A/zh active Pending
- 2005-11-28 JP JP2007544880A patent/JP2008523184A/ja not_active Ceased
- 2005-11-28 KR KR1020077012200A patent/KR20070089138A/ko not_active Application Discontinuation
- 2005-11-28 MX MX2007006617A patent/MX2007006617A/es active IP Right Grant
- 2005-11-28 BR BRPI0518886-5A patent/BRPI0518886A2/pt not_active IP Right Cessation
- 2005-11-28 EP EP05823845A patent/EP1828269B1/en not_active Not-in-force
- 2005-11-28 US US11/792,031 patent/US8287657B2/en not_active Expired - Fee Related
- 2005-11-28 DE DE602005026165T patent/DE602005026165D1/de active Active
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN104487465A (zh) * | 2012-07-19 | 2015-04-01 | 巴斯夫欧洲公司 | 疏水改性阳离子聚合物 |
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US8287657B2 (en) | 2012-10-16 |
DE602005026165D1 (de) | 2011-03-10 |
BRPI0518886A2 (pt) | 2008-12-16 |
US20090117071A1 (en) | 2009-05-07 |
ATE496949T1 (de) | 2011-02-15 |
EP1828269A1 (en) | 2007-09-05 |
KR20070089138A (ko) | 2007-08-30 |
MX2007006617A (es) | 2007-06-15 |
EP1828269B1 (en) | 2011-01-26 |
JP2008523184A (ja) | 2008-07-03 |
WO2006061334A1 (en) | 2006-06-15 |
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