CN101278038B - 生产粒状或粉状洗涤剂组合物的方法 - Google Patents
生产粒状或粉状洗涤剂组合物的方法 Download PDFInfo
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- CN101278038B CN101278038B CN2006800366736A CN200680036673A CN101278038B CN 101278038 B CN101278038 B CN 101278038B CN 2006800366736 A CN2006800366736 A CN 2006800366736A CN 200680036673 A CN200680036673 A CN 200680036673A CN 101278038 B CN101278038 B CN 101278038B
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- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- URLJMZWTXZTZRR-UHFFFAOYSA-N sodium myristyl sulfate Chemical compound CCCCCCCCCCCCCCOS(O)(=O)=O URLJMZWTXZTZRR-UHFFFAOYSA-N 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002512 suppressor factor Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D11/00—Special methods for preparing compositions containing mixtures of detergents
- C11D11/0082—Special methods for preparing compositions containing mixtures of detergents one or more of the detergent ingredients being in a liquefied state, e.g. slurry, paste or melt, and the process resulting in solid detergent particles such as granules, powders or beads
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3746—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/3757—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions
- C11D3/3761—(Co)polymerised carboxylic acids, -anhydrides, -esters in solid and liquid compositions in solid compositions
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Detergent Compositions (AREA)
Abstract
本发明涉及一种生产粒状或粉状洗涤剂组合物的方法，包括通过干燥含水洗涤剂料浆生产洗涤剂基粉。本发明特征在于向料浆中添加共聚物。该共聚物可通过自由基共聚以下组分获得：(A)20～80重量％的选自单烯属不饱和一元羧酸、二元羧酸和二元羧酸酸酐至少一种单体，以及(B)20～80重量％的选自脂族或芳族单烯烃的至少一种单体。
Description
本发明涉及一种生产粒状或粉状洗涤剂组合物的方法，包括通过干燥含水洗涤剂料浆生产洗涤剂基粉，并且还涉及包含可通过自由基共聚以下组分获得的共聚物的洗涤剂料浆和洗涤剂组合物：
(A)20～80重量％的选自单烯属不饱和一元羧酸、二元羧酸和二元羧酸酸酐的至少一种单体
以及
(B)20～80重量％的选自脂族或芳族单烯烃的至少一种单体。
在粉末洗涤剂或用于进一步加工成固态洗涤剂(例如添加其它组分以挤压得到颗粒)的基粉的生产中，多至30种液态或固态组分(它们中一些的量差别很大)必须通过在水中浆化达到非常充分和统一的均化。在此期间，不同的组分，例如表面活性剂和用作助洗剂的沸石导致高度粘性混合物。由于非常高度浓缩的料浆是随后的喷雾干燥所需要的，因此有必要使用降低料浆粘度的助剂。
WO-A-91/09932描述了一种生产粒状洗涤剂组合物的方法，其中在洗涤剂料浆中添加了具有亲水聚合物主链和疏水侧链的抗絮凝聚合物。该主链基于不饱和一元羧酸、二元羧酸和/或醇作为单体单元；可包含聚氧化烯结构单元的侧链经由酯、醚或酰胺官能团连接到主链上。在实施例中，使用了丙烯酸和马来酸十二烷基酯的共聚物。
平均分子量Mw约为12000g/mol的丙烯酸和乙氧基化烯丙基醚的共聚物在US-A-5595968、5618782和5733861中用于此目的。
最后，WO-A-96/17919描述了作为洗涤剂料浆用抗絮凝剂的丙烯酸和马来酸的共聚物，其包含十二烷基巯基作为端基。
本发明的目的是通过使用降低粘度的聚合物以有利的方式生产固态洗涤剂组合物。
因此，已经发现了一种生产粒状或粉状洗涤剂组合物的方法，包括通过干燥含水洗涤剂料浆生产洗涤剂基粉，该方法包括向料浆中添加可通过自由基共聚以下组分获得的共聚物：
(A)20～80重量％的选自单烯属不饱和一元羧酸、二元羧酸和二元羧酸酸酐的至少一种单体
以及
(B)20～80重量％的选自脂族或芳族单烯烃的至少一种单体。
还发现一种降低洗涤剂料浆粘度的方法，其包括向料浆中添加这些共聚物。
此外，已经发现了包含这些共聚物的洗涤剂料浆和洗涤剂组合物。
按照本发明使用的共聚物包含单烯属不饱和一元羧酸或二元羧酸或这些酸的混合物作为共聚的单体(A)。这些酸可以以它们的水溶性盐，尤其是碱金属盐，例如钾盐以及特别是钠盐的形式，或铵盐的形式使用；二元羧酸也可以完全或部分部分以酸酐的形式存在。应该理解的是使用酸的混合物也是可能的。
单体(A)优选包含3～10个碳原子。
合适的单体(A)的具体实例包括：丙烯酸、甲基丙烯酸、巴豆酸、乙烯基乙酸、马来酸、马来酸酐、富马酸、柠康酸、柠康酸酐和衣康酸。
特别优选的单体(A)是丙烯酸、甲基丙烯酸和马来酸/酸酐，非常特别优选的是马来酸/酸酐。
按照本发明使用的共聚物包含20～80重量％，特别是30～70重量％的单体(A)。
作为共聚单体(B)，按照本发明使用的共聚物包含至少一种脂族或芳族单烯烃。
合适的单体(B)的具体实例是：1-丁烯，异丁烯，1-戊烯，1-己烯，二异丁烯(2-甲基-4，4-二甲基-1-戊烯)，1-癸烯，1-十二碳烯，1-十四碳烯，1-十六碳烯，C18-C24-α-烯烃如1-十八碳烯、1-二十碳烯、1-二十二碳烯和1-二十四碳烯，C20-C24-α-烯烃混合物，1-二十六碳烯，具有平均12～100个碳原子的聚异丁烯以及苯乙烯。
按照本发明使用的共聚物优选包含，(B1)至少一种具有≤8个碳原子的单烯烃和(B2)至少一种具有≥10个碳原子的单烯烃的混合物作为组分(B)。
合适的单烯烃(B1)特别是异丁烯、二异丁烯和苯乙烯。特别合适的单烯烃(B2)是1-十二碳烯、C18-C24-α-烯烃、C20-C24-α-烯烃混合物以及具有平均12～100个碳原子的聚异丁烯。
按照本发明使用的共聚物包含20～80重量％，优选30～70重量％的单体(B)。
按照本发明使用的非常特别优选的共聚物可通过自由基共聚(A)30～70重量％的马来酸/酸酐、(B1)20～40重量％的异丁烯以及(B2)5～20重量％的C18-C24-α-烯烃来获得。
按照本发明使用的共聚物具有的平均分子量Mw为1000～200000g/mol，优选2000～50,000g/mol(在室温下用水性洗脱液通过凝胶渗透色谱法测定)。
它们的K值相应地是10～150，优选15～60(根据H.Fikentscher，Cellulose-Chemie，第13卷，第58-64和71-74页(1932)，在25℃pH 7下在1重量％水溶液中测定)。
按照本发明使用的共聚物可以通过已知方法制备。
典型地，它们尤其以聚合物水溶液或水分散体的形式获得，其具有的固体含量为10～70重量％，优选25～60重量％。
按照本发明使用的共聚物可有效地降低含水洗涤剂料浆的粘度，尤其是用于干燥以生产粒状或粉状洗涤剂组合物的料浆，所以即使处理高度浓缩的料浆也毫无问题。因此，基于无水洗涤剂组分，料浆浓度可以总是≥50重量％，优选≥60重量％。
按照本发明使用的共聚物还致使料浆稳定化和均质化，并且防止分离。
它们添加到料浆中的量基于整个混合物一般为0.01～10重量％，优选0.05～5重量％并且更优选0.1～5重量％。
它们可添加到整个混合物中或以任意比例混合到单独的洗涤剂组分中，例如混合到表面活性剂中或助洗剂预混合物中，这样可能已经增加了其固体含量。
包含按照本发明使用的聚合物的本发明固态洗涤剂配方有利地具有例如以下组成：
(a)0.01～10重量％的至少一种本发明共聚物，
(b)0.5～40重量％的至少一种非离子、阴离子和/或阳离子表面活性剂，
(c)0.5～80重量％的无机助洗剂，
(d)0～10重量％的有机第二助洗剂，以及
(e)0～60重量％的其它常规成分，如标准化试剂(standardizer)、酶、香料、配位剂、缓蚀剂、漂白剂、漂白活性剂、漂白催化剂、染料转移抑制剂、泛灰抑制剂、去污聚酯、纤维和染料保护添加剂、硅氧烷、染料、杀菌剂、溶解改进剂和/或崩解剂，
组分(a)～(e)之和为100重量％。
合适的非离子表面活性剂(b)特别是：
-烷氧基化C8-C22-醇，例如脂肪醇烷氧基化物、羰基合成醇烷氧基化物和格尔伯特醇乙氧基化物：烷氧基化可用C2-C20-氧化烯进行，优选氧化乙烯、氧化丙烯和/或氧化丁烯。可存在嵌段共聚物或无规共聚物。每摩尔醇，它们典型地含有2～50摩尔，优选3～20摩尔的至少一种氧化烯。优选氧化烯是氧化乙烯。所述醇优选具有10～18个碳原子。
-烷基酚烷氧基化物，特别烷基酚乙氧基化物，其含有C6-C14-烷基链和5～30摩尔氧化烯/摩尔。
-烷基聚葡糖苷，其含有C8-C22-，优选C10-C18-烷基链和一般1～20，优选1.1～5葡糖苷单元。
-N-烷基葡糖酰胺，脂肪酸酰胺烷氧基化物，脂肪酸链烷醇酰胺烷氧基化物，和氧化乙烯、氧化丙烯和/或氧化丁烯的嵌段共聚物。
合适的阴离子表面活性剂是，例如：
-具有8～22、优选10～18个碳原子的(脂肪)醇的硫酸酯，特别是硫酸C9-C11-醇酯，硫酸C12-C14-醇酯，硫酸C12-C18-醇酯，硫酸十二烷基酯，硫酸十六烷基酯，硫酸十四烷基酯，硫酸棕榈基酯，硫酸硬脂基酯和硫酸牛油脂肪醇酯。
-硫酸化烷氧基化C8-C22-醇(烷基醚硫酸酯)：这类化合物例如通过首先烷氧基化C8-C22-，优选C10-C18-醇，例如脂肪醇，然后硫酸化该烷氧基化产物而制备。对于烷氧基化，优选使用氧化乙烯。
-线性C8-C20-烷基苯磺酸盐(LAS)，优选线性C9-C13-烷基苯磺酸盐和C9-C13-烷基甲苯磺酸盐。
-链烷磺酸盐，特别是C8-C24-，优选C10-C18-链烷磺酸盐。
-皂，如C8-C24-羧酸的钠和钾盐。
阴离子表面活性剂优选以盐的形式添加到洗涤剂中。合适的盐是，例如，碱金属离子如钠、钾和锂，以及铵盐如羟乙基铵、二(羟乙基)铵和三(羟乙基)铵盐。
特别合适的阳离子表面活性剂包括：
-C7-C25-烷基胺；
-N，N-二甲基-N-(羟基-C7-C25-烷基)铵盐；
-用烷基化试剂季铵化的单-和二(C7-C25-烷基)二甲基铵化合物；
-酯季化物，特别是已用C8-C22-羧酸酯化的酯化单-、二-和三链烷醇季铵；
-咪唑啉季铵化合物，特别是式I或II的1-烷基咪唑啉
盐
其中变量定义如下：
R1是C1-C25-烷基或C2-C25-烯基；
R2是C1-C4-烷基或羟基-C1-C4-烷基；
R3是C1-C4-烷基、羟基-C1-C4-烷基或R1-(CO)-X-(CH2)p-基(X：-O-或-NH-；p：2或3)，
其中至少一个R1基是C7-C22-烷基。
合适的无机助洗剂特别是：
-具有离子交换性能的结晶和无定形硅铝酸盐，特别是沸石：各种类型的沸石是合适的，尤其是沸石A、X、B、P、MAP和HS，它们为钠形式或钠部分交换为诸如锂、钾、钙、镁或铵的其它阳离子的形式。
-结晶硅酸盐，尤其是焦硅酸盐和页硅酸盐，例如δ-和β-Na2Si2O5。硅酸盐可以以它们的碱金属、碱土金属或铵盐的形式使用，优选钠、锂和镁的硅酸盐。
-无定形硅酸盐，如偏硅酸钠和无定形焦硅酸钠。
-碳酸盐和碳酸氢盐：它们可以以其碱金属、碱土金属或铵盐的形式使用。优选钠、锂和镁的碳酸盐和碳酸氢盐，尤其是碳酸钠和/或碳酸氢钠。
-聚磷酸盐，如三聚磷酸钠。
合适的有机第二助洗剂特别是：
-小分子量羧酸，例如，柠檬酸，疏水改性柠檬酸，如松蕈酸，苹果酸，酒石酸，葡糖酸，戊二酸，琥珀酸，亚氨二琥珀酸，羟基二琥珀酸，氧联二琥珀酸，丙烷三甲酸，丁烷四甲酸，环戊烷四甲酸，烷基-和烯基琥珀酸，以及氨基多羧酸，如氮三乙酸、β-丙氨酸二乙酸、乙二胺四乙酸、二亚乙基三胺五乙酸、丝氨酸二乙酸、异丝氨酸二乙酸、谷氨酰胺二乙酸、N-(2-羟乙基)亚氨基二乙酸、乙二胺二琥珀酸以及甲基-和乙基甘氨酸二乙酸。-低聚和聚合羧酸，例如，丙烯酸和天冬氨酸的均聚物，低聚马来酸，马来酸和丙烯酸、甲基丙烯酸或C2-C22-烯烃(如异丁烯或长链α-烯烃、乙烯基C1-C8-烷基醚、乙酸乙烯基酯、丙酸乙烯基酯、C1-C8-醇的(甲基)丙烯酸酯和苯乙烯)的共聚物。优选丙烯酸的均聚物以及丙烯酸和马来酸的共聚物。该低聚和聚合羧酸以酸的形式或作为钠盐使用。
合适的漂白剂例如是过氧化氢和无机盐的加合物，如过硼酸钠一水合物、过硼酸钠四水合物和过氧化氢碳酸钠；以及过羧酸，如邻苯二(甲)酰亚氨基过己酸。
合适的漂白活性剂例如是N，N，N″，N′-四乙酰基乙二胺(TAED)、对壬酰氧基苯磺酸钠和N-甲基吗啉
乙腈硫酸甲酯盐。
洗涤剂中优选使用的酶为蛋白酶、脂酶、淀粉酶、纤维素酶、氧化酶和过氧化物酶。
合适的染料转移抑制剂例如是1-乙烯基吡咯烷酮、1-乙烯基咪唑和4-乙烯基吡啶N-氧化物的均聚物、共聚物和接枝聚合物。和氯乙酸反应的4-乙烯基吡啶的均聚物和共聚物也适合作为染料转移抑制剂。
或者洗涤剂成分是众所周知的。详细的说明可以在例如WO-A-99/06524和99/04313以及Liquid Detergents，编辑：Kuo-Yann Lai，Surfactant Sci.Ser.，第67卷，Marcel Dekker，New York，1997，第272-304页中找到。
实施例
在两种洗涤剂料浆中研究共聚物P降低粘度的作用。
共聚物P是马来酸酐、异丁烯和1-十八碳烯的65∶26∶9重量比的共聚物，其平均分子量Mw是3000g/mol，K值是24(在25℃，pH 7下，在1重量％水溶液中测定)。共聚物以40重量％水溶液的形式使用。
两种洗涤剂料浆制备如下：
在500毫升具有可加热夹套的不锈钢容器中，在搅拌下生产两种不同的洗涤剂料浆。为此，最初在50℃，搅拌下加热液态组分10分钟。使用的搅拌器具有扭矩记录器。在4分钟内，将预先混合的固态组分均匀地计量加入，在此期间继续以150rpm搅拌料浆。添加结束后，继续以恒定的转速搅拌料浆，同时测定扭矩。
扭矩表示以恒定转速搅拌料浆所需要的力。扭矩越小，洗涤剂料浆的粘度也越低。
表1列出了洗涤剂料浆的组成。报告的量涉及无水形式的给料，即没有水级分或结晶水，它们计在总的水含量中。
表2汇集了在每种情况下30分钟后获得的扭矩。为了比较，还列出了没有添加聚合物获得的结果。
结果nd是指料浆的粘度非常高并且扭矩不再可测。
表1：洗涤剂料浆的组成
| 给料 | 料浆1[重量％] | 料浆2[重量％] |
| 十二烷基苯磺酸盐，钠盐 | 14.1 | 17.2 |
| C13/15羰基合成醇·7EO | 7.6 | 6.2 |
| 沸石A | 21.7 | - |
| 碳酸钠 | 16.3 | 7.8 |
| 偏硅酸钠 | 10.9 | - |
| 三聚磷酸钠 | - | 15.6 |
| 硫酸钠 | - | 27.3 |
| 共聚物P | 1.1 | 1.8 |
| 总含水量 | 28.3 | 24.1 |
| 总固体含量 | 71.7 | 75.9 |
表2：扭矩的测定
Claims (6)
1.一种生产粒状或粉状洗涤剂组合物的方法，包括通过干燥含水洗涤剂料浆生产洗涤剂基粉，该方法包括向料浆中添加可通过自由基共聚以下组分获得的共聚物：
(A)20～80重量％的选自具有3-10个碳原子的单烯属不饱和一元羧酸、二元羧酸和二元羧酸酸酐至少一种单体
以及
(B)20～80重量％的至少一种选自具有≤8个碳原子的单烯烃的单体(B1)和至少一种选自1-十二碳烯、C18-C24-α-烯烃、C20-C24-α-烯烃混合物以及具有平均12～100个碳原子的聚异丁烯的单烯烃(B2)的混合物。
2.根据权利要求1的方法，其中使用的共聚物基于选自马来酸、马来酸酐和丙烯酸的至少一种单体(A)。
3.根据权利要求1或2的方法，其中使用的共聚物可通过自由基共聚(A)30～70重量％的马来酸或马来酸酐、(B1)20～40重量％的异丁烯以及(B2)5～20重量％的C18-C24-α-烯烃来获得。
4.降低含水洗涤剂料浆粘度的方法，其包括向料浆中添加根据权利要求1～3的共聚物。
5.包含根据权利要求1～3的共聚物的洗涤剂料浆。
6.包含根据权利要求1～3的共聚物的洗涤剂组合物。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005047833.6 | 2005-10-05 | ||
| DE102005047833A DE102005047833A1 (de) | 2005-10-05 | 2005-10-05 | Verfahren zur Herstellung von granulären oder pulverförmigen Waschmittelzusammensetzungen |
| PCT/EP2006/066868 WO2007039554A1 (de) | 2005-10-05 | 2006-09-29 | Verfahren zur herstellung von granulären oder pulverförmigen waschmittelzusammensetzungen |
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| Publication Number | Publication Date |
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| CN101278038A CN101278038A (zh) | 2008-10-01 |
| CN101278038B true CN101278038B (zh) | 2012-11-28 |
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| CN2006800366736A Expired - Fee Related CN101278038B (zh) | 2005-10-05 | 2006-09-29 | 生产粒状或粉状洗涤剂组合物的方法 |
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| Country | Link |
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| US (1) | US8486884B2 (zh) |
| EP (1) | EP1941016B1 (zh) |
| JP (1) | JP5080480B2 (zh) |
| CN (1) | CN101278038B (zh) |
| CA (1) | CA2624919C (zh) |
| DE (1) | DE102005047833A1 (zh) |
| ES (1) | ES2388701T3 (zh) |
| PL (1) | PL1941016T3 (zh) |
| WO (1) | WO2007039554A1 (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE102005041349A1 (de) * | 2005-08-31 | 2007-03-01 | Basf Ag | Reinigungsformulierungen für die maschinelle Geschirrreinigung enthaltend hydrophil modifizierte Polycarboxylate |
| JP5208906B2 (ja) * | 2009-11-13 | 2013-06-12 | 本田技研工業株式会社 | 倒立振子型車両 |
| JP2021522394A (ja) * | 2018-05-04 | 2021-08-30 | ビーエイエスエフ・ソシエタス・エウロパエアＢａｓｆ Ｓｅ | 顆粒又は粉末及びその製造方法 |
| CN109234070B (zh) * | 2018-09-18 | 2020-12-15 | 祥瑞博特生物科技（北京）有限责任公司 | 一种含苯乙烯-丙烯酸-马来酸酐共聚物的洗涤产品及其应用 |
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| US3793228A (en) * | 1969-10-08 | 1974-02-19 | Knapsack Ag | Detergent compositions containing maleic acid vinyl alcohol copolymers as builders |
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- 2006-09-29 CA CA2624919A patent/CA2624919C/en not_active Expired - Fee Related
- 2006-09-29 JP JP2008533982A patent/JP5080480B2/ja not_active Expired - Fee Related
- 2006-09-29 ES ES06793896T patent/ES2388701T3/es active Active
- 2006-09-29 US US12/088,891 patent/US8486884B2/en not_active Expired - Fee Related
- 2006-09-29 PL PL06793896T patent/PL1941016T3/pl unknown
- 2006-09-29 WO PCT/EP2006/066868 patent/WO2007039554A1/de active Application Filing
- 2006-09-29 CN CN2006800366736A patent/CN101278038B/zh not_active Expired - Fee Related
- 2006-09-29 EP EP06793896A patent/EP1941016B1/de not_active Not-in-force
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| US3793228A (en) * | 1969-10-08 | 1974-02-19 | Knapsack Ag | Detergent compositions containing maleic acid vinyl alcohol copolymers as builders |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1941016A1 (de) | 2008-07-09 |
| CA2624919C (en) | 2015-01-27 |
| US20080255022A1 (en) | 2008-10-16 |
| DE102005047833A1 (de) | 2007-04-19 |
| JP2009511651A (ja) | 2009-03-19 |
| JP5080480B2 (ja) | 2012-11-21 |
| WO2007039554A1 (de) | 2007-04-12 |
| ES2388701T3 (es) | 2012-10-17 |
| CA2624919A1 (en) | 2007-04-12 |
| EP1941016B1 (de) | 2012-07-04 |
| CN101278038A (zh) | 2008-10-01 |
| PL1941016T3 (pl) | 2012-10-31 |
| US8486884B2 (en) | 2013-07-16 |
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