CN1245816A - 保护胶体稳定的聚合物组合物 - Google Patents
保护胶体稳定的聚合物组合物 Download PDFInfo
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- CN1245816A CN1245816A CN99111539A CN99111539A CN1245816A CN 1245816 A CN1245816 A CN 1245816A CN 99111539 A CN99111539 A CN 99111539A CN 99111539 A CN99111539 A CN 99111539A CN 1245816 A CN1245816 A CN 1245816A
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- protective colloid
- polymer
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- ester
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Classifications
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B40/00—Processes, in general, for influencing or modifying the properties of mortars, concrete or artificial stone compositions, e.g. their setting or hardening ability
- C04B40/0028—Aspects relating to the mixing step of the mortar preparation
- C04B40/0039—Premixtures of ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/16—Aqueous medium
- C08F2/22—Emulsion polymerisation
- C08F2/24—Emulsion polymerisation with the aid of emulsifying agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6888—Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0617—Polyalkenes
- C09K2200/062—Polyethylene
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0615—Macromolecular organic compounds, e.g. prepolymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C09K2200/0622—Polyvinylalcohols, polyvinylacetates
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2200/00—Chemical nature of materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K2200/06—Macromolecular organic compounds, e.g. prepolymers
- C09K2200/0645—Macromolecular organic compounds, e.g. prepolymers obtained otherwise than by reactions involving carbon-to-carbon unsaturated bonds
- C09K2200/0655—Polyesters
Abstract
本发明涉及一种呈聚合物水分散体形式或呈水可再分散聚合物粉末形式的保护胶体稳定的聚合物组合物,所述组合物包含:至少一种成膜原料聚合物和一种保护胶体,其中所述的保护胶体是磺化的缩合产物,所述缩合产物由不饱和的二—或多羧酸和至少一种选自二元醇、多元醇、二胺和多胺的化合物制得。
Description
本发明涉及呈聚合物水分散体或水可再分散聚合物粉末形式的保护胶体稳定的聚合物组合物,所述组合物包含:成膜的原料聚合物和保护胶体,另外,本发明还涉及所述组合物的制备方法及其用途。
尤其是呈水分散体或水可再分散聚合物粉末形式的保护胶体稳定的聚合物组合物,在广泛的用途中被用作例如在各种基材上的涂布剂或粘合剂。常用的保护胶体为聚乙烯醇(PVAL)。为产生一定的作用,这些保护胶体必须具有一定的分子量。通常使用郝普勒粘度至少为4mPas的聚乙烯醇(4%水溶液)。更低粘度以及相应分子量的聚乙烯醇不能得到没有结块并易于再分散的自由流动粉末。
这些保护胶体的缺点在于:它们具有相当高的分散体粘度,并且当制备粉末时,喷雾混合物的固含量必须保持得很低,这将大大地损害该处理过程的投资效率。就制备包含PVAL的粉末而言,能进行喷雾的固含量通常不高于45重量%,或者在例外情况下不高于48重量%。就喷雾而言,50重量%以上的固含量将不能进行加工(喷雾),这是因为粘度将随固含量而升高。通常对待喷雾分散体的固含量进行选择,以便使粘度小于500mPas(在20转和23℃时的Brookfield粘度),优选小于250mPas。此外,由包含PVAL的粉末得到的可再分散体的高粘度在许多应用中是不利的。
尽管在许多场合的稳定作用(不采用低分子量化合物,例如乳化剂、糖衍生物、低分子量糊精)得到了低粘度的分散体和可再分散体,但该稳定作用通常不足以得到其再分散性和抗粘着性足以与保护胶体稳定的粉末的再分散性和抗粘着性相比的粉末。此外,由于水泥的稳定性常常不够,因此,在水凝粘合剂的应用中使用乳化剂稳定的粉末将出现一些困难。
特别是,当聚合物以其再分散粉末的形式使用,以改善砂浆(即再分散粉末的一种主要应用领域)性能时,该配方必须能稳定一定的时间并且不会明显改变其加工稠度(粘度稳定性或水泥稳定性),这是因为,当经历短时期时,使用者不能预计制备一种新的混合物。在混凝土和砂浆工业中,机械性能如抗压强度、多孔性以及气孔含量也将起重要的作用。如果存在太多的气孔,那么,抗压强度将明显下降,如果在砂浆或混凝土中的气孔太少或没有气孔,那么,该结构材料将得不到足够的抗冻熔性。此外,通过添加分散粉末而改善的水凝体系的粘合力仍应好于没进行所述改善的体系的粘合力。
EP-A723975(CA-A2168157)披露了:由聚乙烯醇稳定的、基于乙酸乙烯酯—乙烯共聚物的、水可再分散的分散粉末。在喷雾干燥之前,所述的分散体必须稀释至40重量%的固含量。
EP-A770640(AU-A9670406)披露了含有任何所需原料树脂的、水可再分散的分散粉末。将保护胶体用作聚电解质,所述电解质带有与树脂电荷相反的电荷。在喷雾之前,将分散体稀释至35重量%的固含量。
EP-A725092(CA-A2168826)披露了基于苯乙烯-丙烯酸酯共聚物的、水可再分散的分散粉末。其稳定作用只是通过乳化剂和含磺酸的共聚单体起作用,不使用任何辅加的保护胶体。该分散体在喷雾干燥之前被稀释至30重量%的固含量。
EP-A723975(CA-A2168157)披露了:基于苯乙烯-丙烯酸酯共聚物的、水可再分散的、可交联的分散粉末。所述分散体在固含量55重量%时,具有高达8000mPas的高粘度,并且在喷雾干燥之前,必须稀释至低于50重量%的固含量。
EP-A629650(US-A5462978)描述了:烯属不饱和单体和带有磺化官能的单体,特别是丙烯酰氨基甲基丙烷磺酸的共聚物,作为喷雾助剂在聚合物水分散体喷雾干燥中的用途。
因此,根据本发明的目的是提供可再分散的粉末,以及用于制备所述粉末的分散体,所述粉末及分散体没有现有技术中的上述缺点。这意味着本发明可得到相当低粘度的分散体,如果需要还具有大于50重量%的固含量,根据本发明得到的粉末可得到低粘度可再分散体,与此同时还是易于再分散、自由流动和抗粘合的。特别是用于水凝粘合剂的应用时,所述产品应当具有十分令人满意的粘度/水泥稳定性并且应当不会阻碍水泥的固化。
本发明提供呈聚合物水分散体或水可再分散的聚合物粉末形式的、保护胶体稳定的聚合物组合物,该组合物包含:至少一种成膜原料聚合物和一种保护胶体,其中所述的保护胶体是磺化的缩合产物,所述缩合产物由不饱和的二-或多羧酸和至少一种选自二元醇、多元醇、二胺和多胺的化合物制得。
通过将亚硫酸加成至不饱和聚酯或聚酰胺的双键中而由其制备本发明的保护胶体。这类缩聚物的合成方法对于本领域熟练技术人员来说是已知的并且详细描述于下列文献中(H.G.Elias,高分子,Hüthig& Wepf,Basle,第四版,1981,第784页)。为此,根据所要得到的产物带有末端醇基、末端胺基还是末端羧基,所用的醇组分、胺组分或羧酸组分的用量通常超过1-20%。而且,末磺化原料的重均分子量(MW)从500至1,000,000,优选从1000至20,000(通过SEC以聚苯乙烯为准而测定)。
以现有技术中已知的方法,通过烯属不饱和二-或多羧酸与饱和二醇或多元醇的酯化作用而得到不饱和聚酯。合适的羧酸组分是:烯属不饱和脂族或芳族二羧酸或多羧酸,或其活性衍生物,如酸酐,通常带有4-10个碳原子和2-4个羧酸官能团或者由其衍生得到的羧酸酐基团。通常使用不饱和二羧酸。所述羧酸的例子有:马来酸,马来酸酐,富马酸,衣康酸,柠康酸,中康酸,邻苯二酸,邻苯二酸酐,间苯二酸和对苯二酸。优选的是:马来酸,马来酸酐,富马酸和衣康酸。特别优选的是马来酸酐。
合适的二元醇或多元醇组分是:环脂族多元醇或开链的脂族多元醇,所述多元醇含两个或多个OH基团,通常含两个或三个OH基团,并且优选含2-12个碳原子。优选的是二元醇,例如,1,2-乙二醇,1,2-丙二醇,1,3-丙二醇,1,3-丁二醇,1,4-丁二醇,1,5-戊二醇,1,6-已二醇,1,7-庚二醇,1,8-辛二醇,1,9-壬二醇,1,10-癸二醇,1,11-十一烷醇,1,12-十二烷醇;二甘醇,三甘醇,四甘醇和五甘醇;1,4-双(羟甲基)环已烷,1,4-环已二醇和2,2’-二甲基丙二醇(新戊二醇)。特别优选的是:1,2-乙二醇,1,2-丙二醇,1,3-丁二醇,1,4-丁二醇,1,4-环已二醇和2,2’-二甲基丙二醇。
以现有技术中已知的方法,通过使烯属不饱和二羧酸或多羧酸与饱和二胺反应而制得不饱和聚酰胺。使用上述的二羧酸或多羧酸。通常用来制备聚酰胺的二胺的例子是:1,6-已二胺,4,4’-二氨基二环已基甲烷和三甲基六亚甲基二胺。
通过不饱和聚酯和聚酰胺与焦亚硫酸(pyrosulfite)钠反应而得到磺化的聚酯和聚酰胺。就磺化而言,在回流条件下,将聚酯以及相应的聚酰胺在实际上与水混溶的溶剂中的溶液与磺化剂的水溶液混合;并在回流条件下保持若干小时;其中所述的与水混溶的溶剂例如为丙酮、THF、异丙醇、DMSO或氯仿;磺化剂例如为碱金属焦亚硫酸盐,如焦亚硫酸钠。通过每摩尔不饱和单体单元使用适量摩尔量的焦亚硫酸盐,通过所使用的磺化剂量,可以对聚酯的磺化度进行调节。以聚酯以及相应聚酰胺的双键计,通常将磺化度调至10-100摩尔%,优选50-100摩尔%。平均分子量(重均分子量MW)从500至1,000,000,优选从1000至20,000。
最优选的保护胶体是通过下列步骤而得到的磺化聚酯:首先使作为羧酸组分的选自马来酸、马来酸酐和富马酸或衣康酸之一或多种化合物与作为二醇组分的选自1,2-乙二醇、1,2-丙二醇、1,3-丁二醇、1,4-丁二醇和1,4-环己二醇或2,2’-二甲基丙二醇之一或多种的化合物进行缩聚;然后将亚硫酸加成至双键上。优选的是,磺化度从50-100摩尔%,重均分子量MW从1000-20,000。
在聚合物水分散体中或在水可再分散的聚合物粉末组合物中,保护胶体的比例,以成膜的原料聚合物计,通常从3-30重量%,优选从5-15重量%。
合适的原料聚合物是选自下列的一种或多种单体的聚合物,所述单体选自:含1-12碳原子的无支链或支链羧酸的乙烯基酯、丙烯酸和甲基丙烯酸与1-12碳原子的无支链或支链醇的酯、乙烯基芳香烃、乙烯基卤化物、烯烃或二烯烃。
优选的乙烯基酯是乙酸乙烯酯,丙酸乙烯酯,丁酸乙烯酯,2-乙基已酸乙烯酯,月桂酸乙烯酯,乙酸1-甲基乙烯酯,新戊酸乙烯酯以及9-11碳原子的α-支链单羧酸的乙烯酯,如VeoVa9R或VeoVa10R(Shell的商品名)。特别优选的是乙酸乙烯酯。
优选的甲基丙烯酸酯或丙烯酸酯是:丙烯酸甲酯,甲基丙烯酸甲酯,丙烯酸乙酯,甲基丙烯酸乙酯,丙烯酸丙酯,甲基丙烯酸丙酯,丙烯酸正丁酯,甲基丙烯酸正丁酯和丙烯酸2-乙基己酯。特别优选的是:丙烯酸甲酯,甲基丙烯酸甲酯,丙烯酸正丁酯和丙烯酸2-乙基已酯。
优选的乙烯基芳香烃是苯乙烯,甲基苯乙烯和乙烯基甲苯。优选的乙烯基卤化物是氯乙烯。优选的烯烃是乙烯和丙烯,优选的二烯烃是1,3-丁二烯和异戊二烯。
如果需要,还可以使以单体混合物总重量计从0.05-10重量%的共聚单体进行共聚合。共聚单体的例子是:烯属不饱和单羧酸和二羧酸,优选丙烯酸,甲基丙烯酸,富马酸,或马来酸;烯属不饱和羧酰胺和烯属不饱和腈,优选丙烯酰胺和丙烯腈;富马酸和马来酸的单酯和二酯,如二乙基酯和二异丙酯,以及马来酸酐,烯属不饱和磺酸及其盐,优选乙烯基磺酸和2-丙烯酰氨基-2-甲基丙磺酸。其它的例子是:预交联的共聚单体,如带有多于一个烯属不饱和度的共聚单体,例如,己二酸二乙烯酯,马来酸二烯丙酯,甲基丙烯酸烯丙酯以及氰尿酸三烯丙酯;后交联的共聚单体,如丙烯酰氨基乙醇酸(AGA),甲基丙烯酰氨基乙醇酸甲酯(MAGME),N-羟甲基丙烯酰胺(NMA),N-羟甲基甲基丙烯酰胺,N-羟甲基氨基甲酸烯丙酯,烷基醚,如异丁氧基醚,或N-羟甲基丙烯酰胺,N-羟甲基甲基丙烯酰胺以及N-羟甲基氨基甲酸烯丙酯的酯。环氧官能的共聚合单体,如甲基丙烯酸缩水甘油酯和丙烯酸缩水甘油酯也是合适的。其它的例子是:硅-官能的共聚单体,如丙烯酰氧丙基三(烷氧基)硅烷和甲基丙烯酰氧丙基三(烷氧基)硅烷,乙烯基三烷氧基硅烷和乙烯基甲基二烷氧基硅烷。可以存在的烷氧基的例子是乙氧基基团和乙氧基(丙二醇)醚基团。另外还可提及的是由单体和羟基或CO基团制得的物质,例如,甲基丙烯酸羟烷基酯和丙烯酸羟烷基酯,如羟乙基,羟丙基和羟丁基的丙烯酸酯和甲基丙烯酸酯,以及还有这样的化合物,如二丙酮丙烯酰胺和乙酰乙酰氧乙基的丙烯酸酯和甲基丙烯酸酯。
重量百分比数据的总量总是100重量%。对于在本发明中提及的成膜原料聚合物,这意味着对单体的选择或共聚单体重量比例的选择应这样进行,以便通常使玻璃化转变温度Tg从-50℃至+50℃,优选从-30℃至+40℃。所述聚合物的玻璃化转变温度Tg可利用差示扫描量热法(DSC)用已知的方法进行测定。另外,Tg还可以利用Fox方程式(Fox equation)进行估算。根据Fox T.G.,Bull.Am.Physics Soc.1,3,第123页(1956):1/Tg=X1/Tg1+X2/Tg2+…+Xn/Tgn,式中Xn为单体n的重量比例(重量%/100),Tgn为单体n的均聚物的绝对玻璃化转变温度。均聚物的Tg值列于聚合物手册第二版中(J.Wiley & Sons,NewYork,1975)。
特别优选的成膜原料聚合物是其中共聚单体的比例适当的如下聚合物:乙酸乙烯酯聚合物,乙酸乙烯酯-乙烯共聚物,乙烯基酯-乙烯-氯乙烯共聚物,乙烯基酯-丙烯酸酯共聚物,丙烯酸正丁酯或丙烯酸2-乙基己酯的聚合物,甲基丙烯酸甲酯与丙烯酸正丁酯和/或丙烯酸2-乙基己酯的共聚物,乙酸乙烯酯-氯乙烯-乙烯共聚物,氯乙烯-乙烯共聚物,氯乙烯-丙烯酸酯共聚物,苯乙烯-丁二烯共聚物和苯乙烯-丙烯酸酯共聚物。
通过使原料聚合物进行乳液聚合或悬浮聚合,然后如果需要使水分散体进行干燥,制得了保护胶体稳定的聚合物水分散体和相应的水可再分散的聚合物粉末。在聚合之前或聚合期间或聚合之后和/或在对以此方法得到的水分散体进行干燥之前,或在对水分散体干燥之后,将一些或所有磺化的聚酯和/或聚酰胺加至粉状原料聚合物中。
当通过乳液聚合或悬浮聚合制备原料聚合物时,聚合温度通常从40-100℃,优选从60-90℃。对于气相共聚单体如乙烯、1,3-丁二烯或氯乙烯的共聚,还可以使用通常从5-100巴的压力。
特别优选的是乳液聚合,并利用常用于乳液聚合的引发剂或氧化还原引发剂混合物引发聚合。合适的引发剂的例子是过氧化氢,如叔丁基过氧化氢、过新戊酸叔丁酯、异丙苯基过氧化氢和一氢过氧化异丙苯,或偶氮化合物,如偶氮二异丁腈。合适的无机引发剂是过硫酸的钠盐,钾盐和铵盐。所提及的引发剂其通常的用量,以单体总重量计从0.05-3重量%。
所使用的氧化还原引发剂是:所提及的引发剂与还原剂的混合物。合适的还原剂是碱金属或铵的亚硫酸盐和亚硫酸盐,例如,亚硫酸钠,次硫酸的衍生物,如甲醛次硫酸锌或碱金属甲醛次硫酸盐,如羟基甲亚磺酸钠,和抗坏血酸。以单体总重量计,还原剂的用量优选从0.01-5.0重量%。
为控制分子量,在聚合期间可以使用调节物质,以聚合单体计,所述物质的通常用量从0.01-5.0重量%,它们可以单独计量加入或与反应组分预先混合。这类调节物质的例子是:正十二烷硫醇,叔十二烷硫醇,巯基丙酸,巯基丙酸甲酯,异丙醇和乙醛。
利用乳化剂和/或保护胶体稳定聚合混合物。优选的是通过乳化剂来稳定,以便得到低粘度的分散体。以共聚单体总重量计,乳化剂的总量优选从0.1-5重量%,特别是从0.5-3重量%。合适的乳化剂是阴离子乳化剂或非离子乳化剂,如:
1)硫酸烷基酯,特别是链长从8-18碳原子的硫酸烷基酯,以及疏水基团中有8-18碳原子且有1-50个环氧乙烯单元的烷基醚硫酸酯和烷芳基醚硫酸酯。
2)磺酸酯,特别是带8-18碳原子的烷基磺酸酯,带8-18碳原子的烷芳基磺酸酯,以及磺基丁二酸与一元醇的酯,或者与烷基基团中带4-15碳原子的烷基苯酚的酯和一酯;如果需要,所述的这些醇或烷基苯酚还可以与1-40环氧乙烷单元进行乙氧基化。
3)磷酸部分酯,以及所述部分酯的碱金属盐和铵盐;特别是有机基团中有8-20碳原子的烷基磷酸酯和烷芳基磷酸酯,在烷基以及相应的烷芳基基团中有8-20碳原子且有1-50个EO单元的烷基醚磷酸酯和烷芳基醚磷酸酯。
4)烷基聚乙二醇醚,优选含有8-40个EO单元,并且烷基基团含有8-20碳原子。
5)烷芳基聚乙二醇醚,优选含有8-40个EO单元,并且在烷基和芳基基团中含有8-20个碳原子。
6)环氧乙烷-环氧丙烷(EO-EP)嵌段共聚物,优选含有8-40个EO以及相应的PO单元。
在聚合期间,如果需要,可以使用磺化聚酯或磺化聚酰胺,以便尽早地进行稳定。在本发明中所使用的保护胶体的用量以原料聚合物计从3-30重量%,优选从5-15重量%,并且所述保护胶体在聚合之前或聚合期间添加。如果需要,也可以在聚合期间使用磺化聚酯或磺化聚酰胺与其它保护胶体的混合物,例如与一种或多种选自下列保护胶体的混合物:部分水解的聚乙酸乙烯酯,聚乙烯吡咯烷酮,羧甲基纤维素,甲基纤维素,羟乙基纤维素或羟丙基纤维素,淀粉,蛋白质,聚(甲基)丙烯酸,聚(甲基)丙烯酰胺,聚乙烯磺酸,蜜胺甲醛磺酸酯,甲醛磺酸萘,苯乙烯-马来酸共聚物和乙烯基醚-马来酸共聚物。优选不添加其它保护胶体使用磺化的聚酯以及相应的聚酰胺。
所述单体可以全部在起始进料中加入或全部通过计量加入,或者一定比例在起始进料中加入,剩余部分在引发聚合之后计量加入。在优选的方法中,以单体总重量计,10-25重量%的单体在起始进料中加入,而剩余部分以计量加入。进料可以是独立的(在空间和时间上),或某些或所有待计量加入的组分可以是已预乳化的。
引发聚合的热引发剂可以全部在起始进料中加入,或一部分在起始进料中加入,一部分计量加入,或全部都计量加入。
利用已知方法的后聚合作用可以在聚合后进行,以便除去残余的单体,例如利用氧化还原催化引发的后聚合。另外还可以通过蒸馏除去挥发性残余单体,优选在降压下进行,并且如果需要,可将惰性载气如空气,氮气或水蒸汽穿过所述混合物或在混合物上方经过。
根据所述方法得到的水分散体其固含量从30-75重量%,优选从55-65重量%。
如果需要,在添加磺化聚酯以及相应的聚酰胺之后,对水分散体进行干燥,以便制备水可再分散的聚合物粉末,例如,利用流化床干燥,冷冻干燥或喷雾干燥。优选对分散体进行喷雾干燥。在本发明中,利用单流体喷嘴,双流体喷嘴或多流体喷嘴的雾化作用,或利用转盘,根据常规的喷雾干燥系统进行喷雾干燥。取决于所述系统、树脂的Tg以及所希望的干燥程度,出料温度通常从45-120℃,优选从60-90℃。
在干燥步骤之前,保护胶体的总量,以聚合物量计至少从3-30重量%。以聚合物量计,优选的用量从5-20重量%,并且该用量对于保护胶体是在聚合期间还是在聚合之后添加并不重要。如果需要的话,还可以将磺化聚酯或聚酰胺与其它希望的常规保护胶体混合。合适的其它保护胶体/喷雾助剂是上述的保护胶体。除磺化聚酯以及相应的聚酰胺以外,优选的是不将任何其它的保护胶体用作喷雾助剂。
业已证明,在喷雾干燥期间,在许多情况下,使用以原料聚合物计至多1.5重量%的消泡剂将是有用的。为通过改善抗粘性能而增加使用寿命,特别是在低玻璃化转变温度的粉末的情况下,所得到的粉末可以包含有抗粘剂,其用量以聚合组分总量计至多为30重量%。抗粘剂的例子是:粒径优选在10纳米至10微米的碳酸钙、碳酸镁、滑石、石膏、硅石、高岭土和硅酸盐。
通过固含量对待喷雾的分散体的粘度进行调节,以便使粘度值小于500mPas(在20转和23℃的Brookfield粘度),优选小于250mPas。固含量从50-65%,优选从55-65%。
为改善使用性能,在喷雾期间还可以使用其它的添加剂。存在于分散粉末组合物优选实施方案中的其它组分的例子是:颜料,填料,泡沫稳定剂以及疏水剂。
在通常用于下列产品的应用成份中,本发明的保护胶体稳定的聚合物组合物还可以以其聚合物水分散体的形式或以水可再分散的聚合物粉末的形式与水凝结合剂结合使用,所述产品例如:建筑化学产品,例如水泥(波特兰水泥,高铝水泥,火山灰水泥,炉渣水泥,镁氧胶结料或磷酸盐水泥)、烧石膏、水玻璃;以及用于生产建筑粘合剂,烧石膏和抹灰,高粘度组合物,地面填充组合物,密封浆,连接砂浆和涂料;另外,还可以用作涂料组合物的打底粘合剂(solebinder),或者用作纺织物或纸张的涂布组合物或粘合剂。
下面的实施例用来进一步描述本发明:实施例1制备聚酯PE1
在1升的三颈烧瓶中,将233.4克二甘醇加热至70℃,所述烧瓶装有带精确玻璃密封盖的搅拌器,以及内部温度计和回冷凝器。利用15分钟添加196.1克马来酸酐(MA)。在没有辅助加热的情况下,放热反应将混合物加热至120℃。一旦温度再降至80℃,利用5小时,将混合物加热至190℃。在此期间,蒸馏出反应中所形成的水份。在四小时之后,观察不到明显的蒸馏作用。为增加转换率,在190℃另外进行一小时的喷水抽吸作用。最终产物是:在室温高粘稠的浅棕色物质。实施例2聚酯PE2的制备
按照实施例1的步骤,所不同的是,使用247.8克1,4-丁二醇和245.1克马来酸酐。最终产物是乳白色的蜡状物。实施例3聚酯PE3的制备
按照实施例1的步骤,所不同的是,使用396.6克1,4-二羟甲基环己烷和245.1克马来酸酐。最终产物是,在室温为脆性的玻璃状透明无色的聚酯。实施例4聚酯PE4的制备
按照实施例1的步骤,所不同的是,使用325克1,6-己二醇和245.1克马来酸酐。最终产物是乳白色的蜡状物。实施例5聚酯PE5的制备
按照实施例1的步骤,所不同的是,使用195.5克1,2-乙二醇和294.1克马来酸酐。最终产物呈浅黄色。实施例6聚酯PE6的制备
按照实施例1的步骤,所不同的是,使用309.9克1,4-环己二醇和245.1克马来酸酐。最终产物在室温下是玻璃状透明的脆性物。实施例7聚酯PE7的制备
按照实施例1的步骤,所不同的是,使用267克2,2’-二甲基丙二醇和245.1克马来酸酐。最终产物是玻璃状透明物。实施例8聚酯PE8的制备
按照实施例1的步骤,所不同的是,使用991克1,4-丁二醇和1132克马来酸酐。最终产物是乳白色的蜡状物。实施例9聚酯PE9的制备
按照实施例1的步骤,所不同的是,使用1050克1,4-环己二醇和931.2克马来酸酐。最终产物是:乳白色的蜡状物。
未磺化聚酯的数据列于下表1中:
表1
磺化聚酯的制备:(实施例10-27)
Tg(℃) | Mw | %C计算值 | %C理论值 | %H计算值 | %H理论值 | |
PE 1 | - 22 | 6000 | 51.3 | 50.6 | 5.9 | 5.4 |
PE 2 | -15 | 3000 | 56.1 | 55.8 | 6.5 | 5.9 |
PE 3 | +9 | 64.0 | 63.9 | 7.6 | 7.5 | |
PE 4 | -45 | 7000 | 60.3 | 60.5 | 7.6 | 7.5 |
PE 5 | +8 | 50.4 | 49.5 | 4.9 | 4.5 | |
PE 6 | +48 | 3500 | 60.9 | 60.3 | 6.6 | 6.1 |
PE 7 | -5 | 4500 | 58.4 | 57.9 | 7.1 | 6.5 |
PE 8 | -14 | 5100 | 56.1 | 55.9 | 6.5 | 6.3 |
PE 9 | +48 | 2300 | 60.9 | 61 | 6.6 | 6.8 |
在所有情况下,均将表2中给出的不饱和聚酯溶于沸腾的异丙醇(20%浓度的溶液)中。在轻柔回流条件下,在3小时时间内计量加入Na2S2O5的水溶液,然后另外回流3小时。然后蒸发出异丙醇。通过所使用的亚硫酸盐的用量,控制磺化度:如果每摩尔双键使用一摩尔亚硫酸盐的话,得到了充分磺化的产物。然而,如果每摩尔双键仅使用0.5摩尔亚硫酸盐的话,所得到的产物的磺化度为50摩尔%。
磺化聚酯的数据列于表2中:
表2:
实施例28利用实施例15的磺化聚酯制备粉末
序号 聚酯 磺化度(摩尔%) 固含量(%) pH K值 表面张力(mN/M)4% 1% 0.2% 0.1%10 PE 1 100 43.3 5.29 22 64.5 68.3 70.6 72.111 PE 2 100 25.3 5.52 33 49.7 53.4 53.5 67.612 PE 3 100 30.6 6.91 9 51.9 57.5 66.8 67.013 PE 4 100 49.8 5.63 12 57.1 60.6 66.8 68.214 PE 5 100 35.6 5.35 16 55.5 66.9 71.0 72.615 PE 6 100 47.6 5.55 14 52.3 49.4 66.5 68.516 PE 7 100 45.4 5.90 13 46.5 52.3 57.5 61.317 PE 1 50 33.7 3.28 13 50.1 54.8 55.6 59.618 PE 2 50 25.8 5.07 60.1 61.6 65.2 66.519 PE 3 50 47.9 5.60 10 53.6 55.2 57.5 57.720 PE 4 50 57.6 5.11 11 49.5 51.8 53.0 53.821 PE 5 50 25.6 3.90 14 54.7 56.5 59.6 60.722 PE 6 50 36.5 4.68 55.1 56.3 58.1 59.123 PE 7 50 32.5 5.35 41.1 45.8 48.5 49.624 PE 8 100 22.6 11 52.0 54.4 56.1 57.825 PE 9 100 20.0 10 49.6 50.7 52.9 56.126 PE 8 50 20.6 11 53.2 54.2 55.2 55.797 PE 9 50 20.0 10 52.5 55.3 55.7 56.0 |
将3500克乳化剂稳定的乙酸乙烯-乙烯共聚物水分散体(通过常规乳液聚合法制得的VAc/E分散体)直接与540克得自实施例15的磺化聚酯(47.6重量%的水溶液)和300克水进行混合,所述共聚物水分散体的固含量为61.1%,粘度为174mPas,粒径DW为450纳米,Tg为0℃。喷雾混合物的固含量为55.2%,且粘度为80mPas。
利用双液喷嘴使分散体进行喷雾。对于喷雾来说,使用加压至4巴的空气,并且利用加热至125℃的空气对所形成的液滴进行顺流干燥。
将所得到的干粉与市售的抗粘剂(碳酸钙镁和硅酸氢镁的混合物)混合。实施例29利用得自实施例22的磺化聚酯制备粉末
将3500克乳化剂稳定的VAc/E分散体直接与585克得自实施例22的磺化聚酯(36.5重量%的水溶液)和100克水进行混合,所述共聚物分散体的固含量为61.1%,粘度为174mPas,粒径DW为450纳米,Tg为0℃。喷雾混合物的固含量为56.2%,且粘度为160mPas。按实施例28的方法进行干燥。实施例30利用得自实施例25的磺化聚酯制备粉末
将3500克乳化剂稳定的VAc/E分散体直接与1070克得自实施例25的磺化聚酯(20重量%的水溶液)进行混合,所述共聚物分散体的固含量为61.1%,粘度为174mPas,粒径DW为450纳米,Tg为0℃。喷雾混合物的固含量为51.5%,且粘度为60mPas。按实施例28的方法进行干燥。实施例31利用得自实施例15的磺化聚酯制备粉末
将3500克乳化剂稳定的VAc/E分散体直接与450克得自实施例15的磺化聚酯(47.6重量%的水溶液)和300克水进行混合,所述共聚物分散体的固含量为61.1%,粘度为174mPas,粒径DW为450纳米,Tg为0℃。喷雾混合物的固含量为55.3%,且粘度为110mPas。按实施例28的方法进行干燥。实施例32利用得自实施例27的磺化聚酯制备粉末
将3500克乳化剂稳定的VAc/E分散体直接与1070克得自实施例27的磺化聚酯(20重量%的水溶液)进行混合,所述共聚物分散体的固含量为61.1%,粘度为174mPas,粒径DW为450纳米,Tg为0℃。喷雾混合物的固含量为51.5%,且粘度为53mPas。按实施例28的方法进行干燥。实施例33利用得自实施例24的磺化聚酯制备粉末
将3500克乳化剂稳定的VAc/E分散体直接与950克得自实施例24的磺化聚酯(22.6重量%的水溶液)进行混合,所述共聚物分散体的固含量为61.1%,粘度为174mPas,粒径DW为450纳米,Tg为0℃。喷雾混合物的固含量为52.9%,且粘度为48mPas。按实施例28的方法进行干燥。实施例34利用得自实施例26的磺化聚酯制备粉末
将3500克乳化剂稳定的VAc/E分散体直接与1040克得自实施例26的磺化聚酯(20.6重量%的水溶液)进行混合,所述共聚物分散体的固含量为61.1%,粘度为174mPas,粒径DW为450纳米,Tg为0℃。喷雾混合物的固含量为51.8%,且粘度为42mPas。按实施例28的方法进行干燥。对比例1含聚乙烯醇的粉末的制备
将20,000克乳化剂稳定的VAc/E分散体直接与4760克聚乙烯醇21.1%浓度的水溶液(郝普勒粘度为4mPas,水解度为88摩尔%)和650克水混合,所述共聚物分散体的固含量为50.2%,粘度为53mPas,粒径为1100纳米,Tg为-1℃。喷雾混合物的固含量为43.4%,且粘度为124mPas。按实施例28的方法进行干燥。对比例2含淀粉粉末的制备
将3500克乳化剂稳定的VAc/E分散体直接与683克31.1%浓度的淀粉水溶液(分子量4500)和300克水混合,所述共聚物分散体的固含量为61.1%,粘度为174mPas,粒径为450纳米,Tg为1℃。喷雾混合物的固含量为52.3%,且粘度为53mPas。按实施例28方法进行干燥。聚合物薄膜的再分散性能:
在玻璃片上,将所述实施例中的分散体(喷雾干燥之前)用来制备厚度为0.2mm的薄膜,并在105℃对这些薄膜干燥15分钟。为检测薄膜的再分散性,用吸移管在室温下将一点水移至待测试的每个薄膜的均匀区域。在该区域暴露至水滴中60秒钟之后,用手指尖对其进行磨擦,直至该薄膜从玻璃片的该区域除去,或薄膜破碎成碎片,或保持完整无缺。
利用下列的评估尺度来评估聚合物薄膜的可再分散性:
1级:轻轻地磨擦立即使薄膜再分散,或者薄膜自发地再分散;
2级:磨擦将使薄膜再分散,但有些薄膜碎片难于分散;
3级:需要强烈磨擦来再分散薄膜,并形成薄膜碎片;
4级:甚至在长时间剧烈磨擦之后,除碎片以外,薄膜仍不能再分散。粉末沉降性能的测定(试管沉降):
为测定沉降性能,将每次50克的粉末再分散于50ml的水中,然后稀释至0.5%的固含量,并且对100ml倒入刻度管中的该再分散体测量沉淀固体的高度,沉降是在一小时之后进行测量的。抗粘性的测量:
为测量抗粘性,将分散粉末置于带螺纹的铁管中,然后使之经受来自金属撞锤的负荷。施加负荷是在干燥室中于50℃储存16小时之后进行的。在冷却至室温之后,从管中取出粉末,并通过粉碎粉末,定性地测量抗粘性。所述抗粘性按如下进行分类:
1=很好的抗粘性
2=良好的抗粘性
3=令人满意的抗粘性
4=没有抗粘性,在破碎之后粉末不再能自由流动。砂浆中空气含量的测定:
将DIN砂浆(DIN1164)与下列配方混合,其中水-水泥因子W/C为0.45,聚合物-水泥因子P/C为0.15:
PZ-35F波特兰水泥 900克
标准砂 2700克
S-860硅氧烷消泡剂(Wacker Chemie) 7.2克
分散粉末 135克
水 405克
利用DIN 18555第二部分测量空气含量。水泥稳定性的测量:
利用下列配方制备水泥混合物:
波特兰水泥 82.5克
方解石(CaCO310-40mm) 75克
石英砂(200-500mm) 142克
分散粉末 14.5克
水 85克
利用2小时的时间,观察水泥混合物的加工性能并定性地进行评估。对水凝薄层粘合剂(砖瓦粘合剂)的抗张结合强度的测量:
利用下列配方制备水泥混合物:
PZ35F波特兰水泥 300克
12号石英砂 150克
F32石英砂 465克
FL15002纤基乙酸钠 3克
分散粉末 48.3克
水 242克
将带有拖出夹的砖置于待测试的粘合剂中,并且在发生硬化之后,利用牵引活塞,根据预选的负荷增加速率将砖向外拉出。根据极限拉伸力以及在该测试中使用的撞捶的面积计算出合适的抗张结合强度。测试保持在下列条件下:
A)在标准温度和湿度条件(23℃和50%相对湿度)下28天
B)在标准温度和湿度条件下7天,再加上水中21天(20℃)
C)在标准温度和湿度条件下14天,加上干燥室(70℃)14天,再加上在标准温度和湿度条件下1天
D)在标准温度和湿度条件下7天,加上水中(20℃)21天,再加上交替的冻融(冷冻至少保持在-15℃,以及熔融保持在约12℃的水中)25天
测试结果列于表3和4中。
由于分散体的粘度相当低,因此,当使用磺化聚酯时,能进行喷雾的百分浓度将明显增高。由于含PVAL的体系其粘度高,因此,利用含PVAL的体系将不成功。尽管将淀粉用作保护胶体能得到低粘度的分散体,但所得到的粉末不能再分散或按所希望的进行分散,并且还易于粘合,而且对水泥还是不稳定的。相反,含磺化聚酯的组合物得到的粉末,能进行充分的再分散,并且是抗粘合的且对水泥是稳定的。抗张结合强度试验的结果(表4)表明:当与对比例1和2进行对比时,通过添加得自实施例28-34的新颖分散粉末,将明显增加抗张结合强度。
表3
实施例 | 固含量(%) | 粘度(mPas) | 薄膜再分散性 | 试管沉降1小时(cm) | 抗粘性 | 砂浆空气含量 | 水泥稳定性 |
实施例28 | 55.2 | 80 | Grade 1 | 0.1 | 2 | 5% | 2 h |
实施例29 | 56.2 | 160 | Grade 1 | 0.1 | 2 | 4% | 2 h |
实施例30 | 51.5 | 60 | Grade 1 | 0.2 | 2 | 5% | 2 h |
实施例31 | 55.3 | 110 | Grade 1 | 0.3 | 2 | 5% | 2 h |
实施例32 | 51.5 | 53 | Grade 1 | 0.1 | 2 | 4% | 2 h |
实施例33 | 52.9 | 48 | Grade 1 | 0.2 | 2 | 5% | 2 h |
实施例34 | 51.8 | 42 | Grade 1 | 0.1 | 2 | 5% | 2 h |
对比例1 | 43.4 | 124 | Grade 1 | 0.4 | 2 | 4% | 2 h |
对比例2 | 52.3 | 53 | Grade 2 | 1.1 | 4 | 9% | 15min |
表4: (在保持一段时间之后,于A-D之下的抗张结合强度,N/mm2)
实施例 | A | B | C | D |
实施例28 | 1.45±0.08 | 0.88±0.08 | 1.33±0.15 | 0.89±0.05 |
实施例29 | 1.32±0.05 | 0.63±0.02 | 1.2 6±0.09 | 0.73±0.05 |
实施例30 | 1.47±0.06 | 0.73±0.05 | 1.41±0.10 | 0.82±0.06 |
实施例31 | 1.32±0.09 | 0.81±0.08 | 1.31±0.14 | 0.89±0.03 |
实施例32 | 1.19±0.08 | 0.71±0.07 | 1.00±0.12 | 0.69±0.07 |
实施例33 | 1.45±0.07 | 0.90±0.08 | 1.29±0.08 | 0.90±0.05 |
实施例34 | 1.31±0.06 | 0.79±0.09 | 1.19±0.15 | 0.85±0.05 |
对比例1 | 1.08±0.10 | 0.60±0.06 | 0.78±0.06 | 0.56±0.05 |
对比例2 | 1.06±0.03 | 0.47±0.06 | 0.27±0.06 | 0.61±0.02 |
Claims (10)
1.一种呈聚合物水分散体形式或呈水可再分散聚合物粉末形式的保护胶体稳定的聚合物组合物,所述组合物包含:至少一种成膜原料聚合物和一种保护胶体,其中所述的保护胶体是磺化的缩合产物,所述缩合产物由不饱和的二-或多羧酸和至少一种选自二元醇、多元醇、二胺和多胺的化合物制得。
2.根据权利要求1所述的保护胶体稳定的聚合物组合物,其中保护胶体是:带4-10个碳原子和2-4个羧酸官能团的烯属不饱和脂族或芳族二羧酸或多羧酸、或所述羧酸衍生得到的羧酸酐,与带两个或三个羟基基团的环状或开链脂族多元醇的磺化的缩合产物。
3.根据权利要求1或2所述的保护胶体稳定的聚合物组合物,其中磺化度从10-100摩尔%,重均分子量MW从500-1,000,000。
4.根据权利要求1-3之一所述的保护胶体稳定的聚合物组合物,其中含有磺化聚酯,所述磺化聚酯是通过下列步骤得到:首先使作为羧酸组分的选自马来酸、马来酸酐和富马酸或衣康酸之一或多种化合物与作为二醇组分的选自1,2-乙二醇,1,2-丙二醇,1,3-丁二醇,1,4-丁二醇和1,4-环己二醇或2,2’-二甲基丙二醇之一或多种化合物进行缩聚;然后进行亚硫酸氢的加成,磺化度从50-100摩尔%,重均分子量MW从1000-20,000。
5.根据权利要求1-4之一所述的保护胶体稳定的聚合物组合物,其中所述的成膜原料聚合物是选自下列的一种或多种单体的聚合物,所述单体选自:含1-12碳原子的无支链或支链羧酸的乙烯基酯,丙烯酸和甲基丙烯酸与1-12碳原子的无支链或支链醇的酯,乙烯基芳香烃,乙烯基卤化物,烯烃或二烯烃。
6.根据权利要求1-4之一所述的保护胶体稳定的聚合物组合物,其中所存在的成膜原料聚合物是选自下列的聚合物:乙酸乙烯酯聚合物,乙酸乙烯酯-乙烯共聚物,乙烯基酯-乙烯-氯乙烯共聚物,乙烯基酯-丙烯酸酯共聚物,丙烯酸正丁酯或丙烯酸2-乙基已酯的聚合物,甲基丙烯酸甲酯与丙烯酸正丁酯和/或丙烯酸2-乙基已酯的共聚物,乙酸乙烯酯-氯乙烯-乙烯共聚物,氯乙烯-乙烯共聚物,氯乙烯-丙烯酸酯共聚物,苯乙烯-丁二烯共聚物和苯乙烯-丙烯酸酯共聚物。
7.一种权利要求1-6之一所述的保护胶体稳定的聚合物组合物的制备方法,该方法包括:使原料聚合物进行乳液聚合或悬浮聚合,然后如果需要使水分散体进行干燥,在聚合之前或聚合期间或聚合之后和/或在对以此方法得到的水分散体进行干燥之前,或在对水分散体干燥之后,将一些或所有磺化的聚酯和/或聚酰胺加至粉状原料聚合物中。
8.权利要求1-6之一所述的保护胶体稳定的聚合物组合物与水凝粘合剂结合作为建筑粘合剂、烧石膏和抹灰、高粘度组合物、地面填充组合物、密封浆、连接砂浆和涂料的配方成分的应用。
9.权利要求1-6之一所述的保护胶体稳定的聚合物组合物作为涂料组合物和粘合剂的打底粘合剂的应用。
10.权利要求1-6之一所述的保护胶体稳定的聚合物组合物作为纺织物或纸张的涂布组合物或粘合剂的应用。
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DE19837856A DE19837856A1 (de) | 1998-08-20 | 1998-08-20 | Schutzkolloidstabilisierte Polymer-Zusammensetzungen |
DE19837856.4 | 1998-08-20 |
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CN1245816A true CN1245816A (zh) | 2000-03-01 |
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CN99111539A Pending CN1245816A (zh) | 1998-08-20 | 1999-08-20 | 保护胶体稳定的聚合物组合物 |
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US (1) | US6262167B1 (zh) |
EP (1) | EP0982351B1 (zh) |
JP (1) | JP3073739B2 (zh) |
KR (1) | KR20000017014A (zh) |
CN (1) | CN1245816A (zh) |
AT (1) | ATE198213T1 (zh) |
CA (1) | CA2280552A1 (zh) |
DE (2) | DE19837856A1 (zh) |
PL (1) | PL334989A1 (zh) |
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CN106164112A (zh) * | 2014-03-27 | 2016-11-23 | 瓦克化学公司 | 纸张涂料组合物的粘合剂 |
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- 1998-08-20 DE DE19837856A patent/DE19837856A1/de not_active Ceased
-
1999
- 1999-07-29 AT AT99114290T patent/ATE198213T1/de not_active IP Right Cessation
- 1999-07-29 DE DE59900028T patent/DE59900028D1/de not_active Expired - Lifetime
- 1999-07-29 EP EP99114290A patent/EP0982351B1/de not_active Expired - Lifetime
- 1999-08-02 KR KR1019990031725A patent/KR20000017014A/ko not_active Application Discontinuation
- 1999-08-11 US US09/371,815 patent/US6262167B1/en not_active Expired - Fee Related
- 1999-08-16 JP JP11229933A patent/JP3073739B2/ja not_active Expired - Fee Related
- 1999-08-19 PL PL99334989A patent/PL334989A1/xx not_active Application Discontinuation
- 1999-08-20 CA CA002280552A patent/CA2280552A1/en not_active Abandoned
- 1999-08-20 CN CN99111539A patent/CN1245816A/zh active Pending
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CN106164112A (zh) * | 2014-03-27 | 2016-11-23 | 瓦克化学公司 | 纸张涂料组合物的粘合剂 |
CN106164112B (zh) * | 2014-03-27 | 2018-02-06 | 瓦克化学公司 | 纸张涂料组合物的粘合剂 |
CN103936975A (zh) * | 2014-05-07 | 2014-07-23 | 中国科学院化学研究所 | 磺酸根阴离子功能化的可生物降解聚酯及其制备方法 |
CN109503869A (zh) * | 2018-09-27 | 2019-03-22 | 武汉纺织大学 | 一种纺织品增强树脂复合材料的制备方法 |
CN111971829A (zh) * | 2019-10-31 | 2020-11-20 | 帝伯爱尔株式会社 | 粘合剂 |
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Publication number | Publication date |
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EP0982351B1 (de) | 2000-12-20 |
DE59900028D1 (de) | 2001-01-25 |
DE19837856A1 (de) | 2000-02-24 |
US6262167B1 (en) | 2001-07-17 |
ATE198213T1 (de) | 2001-01-15 |
KR20000017014A (ko) | 2000-03-25 |
JP2000109716A (ja) | 2000-04-18 |
PL334989A1 (en) | 2000-02-28 |
JP3073739B2 (ja) | 2000-08-07 |
CA2280552A1 (en) | 2000-02-20 |
EP0982351A1 (de) | 2000-03-01 |
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