CN1030333C - 含有悬浮过氧漂白剂的液体洗涤剂组合物 - Google Patents
含有悬浮过氧漂白剂的液体洗涤剂组合物 Download PDFInfo
- Publication number
- CN1030333C CN1030333C CN91111077.1A CN91111077A CN1030333C CN 1030333 C CN1030333 C CN 1030333C CN 91111077 A CN91111077 A CN 91111077A CN 1030333 C CN1030333 C CN 1030333C
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- Prior art keywords
- water
- composition
- perborate
- peralcohol
- liquid detergent
- 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.)
- Expired - Lifetime
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- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000002426 superphosphate Substances 0.000 description 1
- 230000009974 thixotropic effect Effects 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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
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- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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Abstract
公开了液体洗涤剂组合物,该组合物含有悬浮于液相(含有水和至少一种与水互溶的溶剂)中的固体过氧化合物和低含量的硅酸盐,硅酸盐提供了固体过氧化合物在液相中的合乎要求的悬浮。
Description
本发明涉及含有悬浮固体过氧化合物以及低含量硅酸盐的液体洗涤剂组合物。
为了满足含漂白剂的水溶液洗涤剂组合物长期存在的需要,欧洲专利申请293040和294904描述了pH值大于8,含有阴离子表面活性剂(常规量)和固体过氧漂白剂的水溶液洗涤剂组合物。该固体过氧漂白剂悬浮于特殊水/溶剂介质中,所述介质发现可为组合物提供需要的化学稳定性。
然而在这些组合物中,对液体介质中悬浮颗粒的物理稳定性须给予特殊的注意。
一种选择方案以(例如)未决英国专利申请No.8926620.9为代表,该申请描述了液体洗涤剂组合物,其中的固体颗粒、尤其是过氧化合物颗粒是籍助于结构表面活性剂相(表面活性剂“净相”)悬浮的。然而,这就需要悬浮体系,该悬浮体系涉及到与结构表面活性剂相相比较为更容易的操作。
虽然不是为了悬浮过氧漂白剂颗粒的目的,但结构表面活性剂相在不同的专利文献中得到了描述;尤其是EP-A-79646、EP-A-86614、EP-A-203660和EP-A-295021描述了含有悬浮助洗剂颗粒的液体洗涤剂组合物,其中一种或多种“盐析”电解质或“表面活性剂减溶”电解质用于构成含有表面活性剂物质的结构相。
这些电解质除包括许多其他物质外,还包括硅酸盐,并且须以一定的量(如大于5%)使用以提供其“盐析”效应。
公开了在悬浮类型的洗涤/洗涤剂组合物中使用硅酸盐的其他专利文献包括GB-A-2031455和GB-A-1342612,其中被悬浮的固体物质包括研磨剂和非水溶性磷酸盐助洗剂盐,但没有包括过氧漂白剂颗粒;实际上,提到过硼酸盐在悬浮类型液体组合物中用作可能的漂白组份的GB-A-2158453,特别提倡这些组合物必须不含硅酸盐,否则必须含有羧酸防胶凝剂。
硅酸盐也被广泛地描述为含水触变液体组合物的碱性助洗组份,该液体组合物用于例如自动餐具洗涤目的。该技术的一个代表例子是EP-315024,其公开的硅酸盐用量在25%-40%范围。
现在意外地发现,低含量的硅酸盐可在
EP-A-293040所描述的类型的液体洗涤剂组合物中有效地悬浮过氧漂白剂颗粒,并只是适度地增强组合物的粘度。本发明的悬浮体系不涉及任何特殊的操作困难,而且硅酸盐的存在还带来了提高碱度以及提高洗涤机混溶性的优点。
因此,本发明提供理想的相稳定水溶液液体洗涤剂组合物,该组合物含有固体过氧漂白剂化合物、由水和与水互溶的有机溶剂组成的液相以及用于在液相中悬浮过氧漂白剂颗粒的低含量硅酸盐。
本发明涉及稳定的液体洗涤剂组合物,该组合物具有至少为8并小于约11的pH值,其包括一种水溶性固体过氧化合物,该固体过氧化合物悬浮于含有水和至少一种与水互溶的有机溶剂的液相中,水溶性固体过氧化合物的存在量使得由所述过氧化合物提供的有效氧量为0.5%至3%,所述组合物含有0.5%至5%、优选1%至3%(重量)的硅酸盐。
水溶性过氧化合物
水溶性固体过氧化合物在本发明组合物中的存在量优选为5-50%(以组合物总重量计),较优选5-40%,更优选5-30%,最优选10-30%(重量)。
适宜的水溶性固体过氧化合物的例子包括过硼酸盐、过硫酸盐、过二硫酸盐、过磷酸盐以及通过过氧化氢与碳酸钠(形成过碳酸盐)或尿素反应形成的结晶过氧水合物。优选的过氧漂白化合物是过硼酸盐和过碳酸盐。
在本文中最优选的漂白剂是颗粒状过硼酸盐漂白剂,颗粒的重均平均粒径为0.5-20微米,优选3-15微米。
小的平均粒度最好通过就地结晶获得,尤其对过硼酸盐一水合物更是这样。
就地结晶包括的工序涉及溶解和重结晶,如过硼酸盐一水合物的溶解以及接着形成过硼酸盐四水合物。通过使过硼酸盐一水合物吸收结晶水也可产生重结晶,从而一水合物直接重结晶变成四水合物,省去了溶解步骤。
就地结晶还包括涉及化学反应的过程,如当化学计算量的过氧化氢与偏硼酸钠或硼砂反应形成过硼酸钠时。
与水互溶的有机溶剂
本文固体过氧组份的悬浮体系是包括水和与水互溶有机溶剂的液相。这就使得将大量的水溶性固体过氧化合物掺入本文的液体洗涤剂组合物成为可能,然而要维持溶液中有效氧量低于液相重量的0.5%,优选低于0.1%。过氧化合物溶解于液相的量低于其总量的十分之一;实际上溶液中有效氧的低含量决定了体系的稳定性。
标准碘量法(例如,Methodender Orgonischen Chemie,Houben Weyl,1953,第2卷,第562页所描述的)适合用于测量组合物中有效氧(AVO)含量。
为保证在液相和固相间完全达到平衡、混合后的组合物要在室温下放置三天再进行AVO滴定测试。为保证正确取样,测定前产物要进行彻底摇动。
为测定液相中有效氧(AVO)组合物样品以10,000rpm的转速离心分离10分钟。然后将液体与固本分离,对液体滴定以测定有效氧量。
有机溶剂没有必要与水完全互溶,只要在组合物中与水混合的足够有机溶剂能够以所述的方式影响过氧化合物的溶解性即可。与水完全混溶的溶剂在本文中优选使用。
当然,与水互溶的有机溶剂必须在所使用的pH值下与过氧漂白剂化合物相容。因此,当过氧漂白剂化合物是过硼酸盐时,带有相邻羟基的多醇(例如1,2-丙二醇和甘油)不宜使用。
适宜的水互溶有机溶剂的例子包括低级脂族一元醇;二甘醇和低级单脂族一元醇的醚;尤其是乙醇;正丙醇;异丙醇;丁醇;聚乙二醇(例如PEG150,200,300,400);二丙二醇;己二醇;甲氧基乙醇;乙氧基乙醇;丁氧基乙醇;乙基二甘醇醚;苄醇;丁氧基丙醇;丁氧基丙氧基丙醇;及其混合物。优选的溶剂包括乙醇;异丙醇;1-甲氧基-2-丙醇和丁基二甘醇醚。优选的溶剂体系是乙醇。乙醇优选以水∶乙醇从8∶1至1∶3的比例存在。
虽然其他组份的存在与否也起一定的作用,但溶液中的有效氧量在很大程度上取决于水与有机溶剂的比例。然而,没有必要使用多于维持溶液中有效氧量低于0.5%、优选低于0.1%所需要的溶剂。
实际上,对大多数体系,水∶有机溶剂的比例在5∶1至1∶3范围,优选在4∶1至1∶2范围。
硅酸盐
硅酸盐在本发明组合物中的存在量为0.5%至5%,优选1%至3%。加入如此少量的硅酸盐不能促进结构表面活性剂相的形成,但意外地提供了对过氧漂白剂颗粒的有效和稳定的悬浮,而仅使组合物的粘度有适度的增加。
本发明使用的硅酸盐物质可以是天然硅酸盐,其SiO2对Na2O的比例从1∶1至4∶1,优选1∶1(偏硅酸盐)、1.6∶1或2∶1。
优选硅酸钠,当然硅酸钾也可以使用。
本发明的含漂白剂的液体洗涤剂组合物呈现至少为8并小于约11的pH值(在蒸馏水中的1%溶液),优选至少为9,更优选至少为9.5。碱性pH值导致过氧化合物的优良漂白作用,尤其是当过氧化合物是过硼酸盐时更是这样。
表面活性剂
本发明的组合物优选含有非离子或阳离子表面活性剂、或两种表面活性剂的混合物,表面活性剂的总量从1%至20%,最优选3%至10%。
非离子表面活性剂一般通过在酸性或碱性催化剂存在下,环氧乙烷与带有活泼氢原子(例如羟基、羧基或酰氨基)的烃缩合而制备。该种表面活性剂包括具有通式RA(CH2CH2O)nH的化合物,其中R代表疏水部分,A代表带活泼氢原子的基团,以及n代表环氧乙烷部分的平均数。R一般含有约8-22个碳原子。非离子表面活性剂也可通过1,2-环氧丙烷与低分子量化合物的缩合制备。n通常在约2-约24之间变化。
非离子化合物的疏水部分优选伯或仲、直链或支链脂肪族醇,该脂肪族醇具有约8-约24,优选约12-约20个碳原子。对适宜的非离子表面活性剂的更全面的揭示见于美国专利4,111,855。非离子表面活性剂的混合物也是适宜的。
优选的一类非离子乙氧基化物以具有12-15个碳原子的脂肪醇与每摩尔脂肪醇约4-10摩尔环氧乙烷的缩合物为代表。
该类乙氧基化物的合适物质包括:C12-C15羰基合成醇与每摩尔醇7摩尔环氧乙烷的缩合物;窄馏分C14-C15羰基合成醇与每摩尔脂肪(羧基合成)醇7或9摩尔环氧乙烷的缩合物;窄馏分C12-C13脂肪(羧基合成)醇与每摩尔脂肪醇6.5摩尔环氧乙烷的缩合物;以及C10-C14椰子脂肪醇的缩合物,其乙氧基化程度(摩尔EO/摩尔脂肪醇)在5-8范围。主要是直链的脂肪羰基合成醇可具有一定的支化度,尤其是带有诸如甲基支链的短链,这取决于制备条件和烯烃原料。
市场上可买到的羰基合成醇经常具有15%-50%(重量%)范围的支化度。
优选的非离子乙氧基化成分还可表示为两种分别乙氧基化的非离子表面活性剂混合物,二者具有不同的乙氧基化程度。例如,非离子乙氧基化表面活性剂含有每摩尔疏水部分3-7摩尔环氧乙烷的第一种乙氧基化物和每摩尔疏水部分8-14摩尔环氧乙烷的第二种乙氧基化合物。优选的非离子乙氧基化混合物含有低级乙氧基化物,即C12-C15羰基合成醇(带至多50%重量的支链)与每摩尔、脂肪羰基合成醇约3-7摩尔环氧乙烷的缩合物,和高级乙氧基化物,即C16-C19羰基合成醇(带有大于50%重量的支链)与每摩尔支化羰基合成醇约8-14摩尔环氧乙烷的缩合物。
半极性非离子表面活性剂包括水溶性氧化胺,该氧化胺含有一个约8-约28个碳原子的烷基或羟烷基部分和两部分选自烷基或羟烷基的基团,这些烷基或羟烷基含有1-约3个碳原子,并可任意地连成环结构。
本发明的液体洗涤剂组合物任意地含有阳离子表面活性剂,优选0.1%-10%,更优选0.1%-5%,以组合物重量计。
适宜的阳离子表面活性剂的例子包括结构式为R1R2R3R4N+X-的季铵化合物,其中R1是C12-C20烷基或羟烷基;R2是C1-C4烷基或羟烷基或C12-C20烷基或羟烷基或C1-C4羟烷基;R3和R4各自是C1-C4烷基或羟烷基、或C6-C8芳基或烷基芳基;以及X-是卤素。优选单一长链季铵化合物(如上述结构式中R2是C1-C4烷基或羟烷基的化合物)。
可用于本发明组合物的两性离子表面活性剂包括脂族季铵、鏻和锍化合物的衍生物,其中脂族部分可以是直链或支链,并且其中的一个脂族取代基含约8-约24个碳原子,另一个取代基含至少一个阴离子水溶性基团。特别优选的两性离子物质是乙氧基化磺酸铵或硫酸铵,公开在美国专利
3,925,262(Laughlin等人,1975年12月9日颁发)和3,929,678(Laughlin等人,1975年12月30日颁发)中。
本文的组合物还可含有阴离子表面活性剂。阴离子洗涤剂在洗涤剂领域中是众所周知的,并已在商业洗涤剂中获得了广泛的应用。适宜的合成阴离子表面活性盐选自磺酸盐和硫酸盐。优选的合成阴离子水溶性磺酸盐或硫酸盐在其分子结构中具有含约8-约22个碳原子的烷基。
相应地,若使用阴离子表面活性剂,其存在的量多至40重量,优选1%-30%重量,更优选5%-20%重量。
合成的阴离子表面活性剂可以通式R1SO3M表示,其中R1代表选自含有约8-约24个碳原子的直链或支链烷基以及在烷基部分含有约9-约15个碳原子的烷基苯基的烃基;M是成盐阳离子,一般选自钠、钾、铵离子、或这些离子的组合。
优选的合成阴离子表面活性剂是烷基苯磺酸的水溶性盐,其烷基上含有9-15个碳原子。另一类优选的合成阴离子表面活性剂是烷基硫酸盐或烷基多乙氧基醚硫酸盐的水溶性盐,其中烷基含有约8-约24、优选约10-约20个碳原子,并且其中优选含有约1-约12个乙氧基。美国专利4,170,565(Flesher等人,1979年10月9日颁发)公开了其他适宜的阴离子表面活性剂。
这些优选阴离子表面活性剂盐的实例有:对从牛脂和椰子油衍生的C8-C18脂肪醇硫酸化得到的反应产物;其中烷基含约9-15个碳原子的烷基苯磺酸盐;烷基甘油醚磺酸钠;从牛脂和椰子油衍生的脂肪醇的醚硫酸盐;椰子脂肪酸单甘油酯硫酸盐和磺酸盐;以及在烷基链上含有约8-约22个碳原子的链烷磺酸盐的水溶性盐。也可以使用磺化的烯烃表面活性剂,这类表面活性剂在例如美国专利说明书3,332,880中有更全面的描述。用于阴离子合成磺酸盐和/或硫酸盐的中和阳离子就是普通的阳离子,比如钠和钾,它们广泛地应用于洗涤剂技术中。
这里特别优选的阴离子合成表面活性剂组分是烷基苯磺酸的水溶性盐,尤其是烷基上具有约10-13个碳原子的烷基苯磺酸钠。
助洗剂
本发明的组合物可以含有助洗剂,其含量优选不超过50%,更优选的含量占全部组合物的5%-40%。
如果使用,这些助洗剂可由现有技术中已经描述过的无机或有机类型组成。
本发明的液体洗涤剂组合物任意含有作为助洗剂的脂肪酸组分。然而,脂肪酸的含量优选少于10%,更优选少于4%(以组合物重量计)。
优选的饱和脂肪酸具有10-16个碳原子、更优选12-14个碳原子。优选的不饱和脂肪酸是油酸和棕榈油酸。
无机助洗剂的实例包括磷基助洗剂,例如三聚磷酸钠、焦磷酸钠和硅铝酸盐(沸石)。
有机助洗剂的代表实例是多元酸,如柠檬酸、次氮基三乙酸,以及酒石酸单琥珀酸盐与酒石酸二琥珀酸盐的混合物。这里优选使用的助洗剂是柠檬酸和烷(烯)基取代的琥珀酸化合物,其中烷(烯)基含有10-16个碳原子。该组化合物的一个例子是十二烯基琥珀酸。聚合羧酸盐助洗剂包括聚丙烯酸盐、多羟基丙烯酸盐和聚丙烯酸盐/聚马来酸盐共聚物也可以使用,并且最好与上述的优选助洗剂如柠檬酸和烷(烯)基取代的琥珀酸化合物结合使用。
其他组份/添加剂
本发明的组合物还可含有其他组份和/或添加剂,含量优选低于约5%。这些添加剂(更优选的使用量为0.05%-2%)的非限制性实例包括多氨基羧酸盐添加剂,如亚乙基二氨基四乙酸,二亚乙基三氨基-五乙酸、亚乙基二氨基二琥珀酸或其水溶性碱金属盐。以该用量使用的其他添加剂包括有机-膦酸;特别优选亚乙基二氨基四亚甲基膦酸、二亚乙基三氨基五亚甲基膦酸和氨基三亚甲基膦酸、羟基亚乙基二膦酸。漂白剂稳定剂如抗坏血酸、吡啶二羧酸、锡酸钠、8-羟基喹啉、羟基亚乙基二膦酸(HEDP)和二亚乙基三胺五(亚甲基膦酸)也可以按这些用量包括在所述组合物中,更优选的用量是0.01-1%。
本发明的组合物可含有一系列更任意的成分,这些成分大都以添加剂量使用,通常低于约5%。这类成分的实例包括:多元酸、酶和酶催化稳定剂、泡沫调节剂、遮光剂、提高洗涤机相容性(对于搪瓷涂覆的表面)试剂、杀菌剂、染料、香料、
增白剂、软化剂,等等。
如上所述,洗涤性酶可用于本发明的液体洗涤剂组合物中。事实上,本发明组合物的一个合乎需要的特点就是这些组合物可与洗涤性酶相配伍。适宜的酶包括洗涤蛋白酶、淀粉酶、脂肪酶和纤维素酶。用于液体洗涤剂的酶催化稳定剂是人们所熟知的。如果使用酶稳定剂,其用量优选在约0.5%-5%范围。这里使用的优选酶催化稳定剂是甲酸、乙酸及其盐,例如甲酸钠和乙酸钠。更优选的稳定剂是甲酸钠和乙酸。
组合物的应用
本发明的组合物主要是想用于洗涤机的洗涤循环中,然而也可设想其他应用,如严重污染织物的产物预处理或浸泡产物;其使用没必要仅限于洗涤机范围,而且本发明的组合物可以单独使用也可与相容的手洗用组合物结合使用。
本发明的一些典型液体洗涤剂组合物具有下列配方:(表见文后)
实施例
组分 组合物 重量%
Ⅰ Ⅱ Ⅲ Ⅳ Ⅴ Ⅵ
直链烷基苯磺酸盐 10 12 10 8 10 12
C13-C15醇乙氧基化物(EO3) 5 0 0 10 5 3
C13-C15醇乙氧基化物(EO7) 0 7 5 0 2 4
柠檬酸 2.5 3.5 4 1 2.5 3
十二烯基琥珀酸 8.5 7 6.5 10 8.5 8
聚合羧酸盐助洗剂 1.5 1.5 2 1.5 1.5 1
牛油脂肪酸 - 1.5 2 - - 1
二亚乙基三氨五(亚甲基膦酸) 0.5 0.5 0.4 0.5 0.5 0.4
羟亚乙基二膦酸 0.2 0.2 0.3 0.2 0.3 0.4
甲酸钠 1.5 1 1.5 1.5 1 2
乙酸 1.4 1.5 1.4 1.4 2 -
乙醇 8 10 12 10 14 14
一水过硼酸钠 14 - 14 - - 14
四水过硼酸钠 - 20 - 22 20 -
硅酸盐SiO2∶Na2O=1.6 1 3 - - - -
硅酸盐SiO2∶Na2O=2.0 - - 1.5 3 - -
氢氧化钠 ……大于PH9.5……
水+少量物质(香料、增白剂、酶…) ……平衡至100……
Claims (13)
1、一种pH值至少为8但小于11的稳定液体洗涤剂组合物,其特征在于该组合物包括悬浮于液相中的水溶性固体过氧化合物,所述液相含有水和与水互溶的有机溶剂,水溶性固体过氧化合物的含量使得由该过氧化合物提供的有效氧量为0.5%-3%,水与溶剂的比例足以维持溶液中的有效氧量低于0.5%,所述组合物含有0.5%-5%(重量)的硅酸盐,其中所述溶剂选自低级脂族醇、二甘醇和低级单脂族一元醇的醚、苄醇及其混合物。
2、根据权利要求1的洗涤剂组合物,其中硅酸盐的含量为1%-3%。
3、根据权利要求1和2的液体洗涤剂组合物,其中与水互溶的有机溶剂是低级脂族一元醇。
4、根据权利要求2的液体洗涤剂组合物,其中与水互溶的有机溶剂是乙醇,并且水∶乙醇比例为8∶1-1∶3。
5、根据权利要求4的液体洗涤剂组合物,其中水∶乙醇比例为5∶1-1∶2。
6、根据权利要求1或2的液体洗涤剂组合物,其中水溶性固体过氧化合物是四水过硼酸盐,其含量为组合物总重量的5%-30%。
7、根据权利要求3的液体洗涤剂组合物,其中水溶性固体过氧化合物是四水过硼酸盐,其含量为组合物总重量的5%-30%。
8、根据权利要求6的组合物,其中四水过硼酸盐漂白剂呈颗粒状,具有0.5微米-20微米的重均粒径。
9、根据权利要求7的组合物,其中四水过硼酸盐漂白剂呈颗粒状,具有0.5微米-20微米的重均粒径。
10、根据权利要求6的组合物,其中四水过硼酸盐颗粒通过一水过硼酸盐重结晶形成。
11、根据权利要求7的组合物,其中四水过硼酸盐颗粒通过一水过硼酸盐重结晶形成。
12、根据权利要求1或2的组合物,其中水溶性固体过氧化合物是过碳酸盐。
13、根据权利要求3的组合物,其中水溶性固体过氧化合物是过碳酸盐。
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GB898900496A GB8900496D0 (en) | 1989-01-10 | 1989-01-10 | Liquid detergent composition containing enzyme and enzyme stabilization system |
EP90870197A EP0482274A1 (en) | 1989-01-10 | 1990-10-22 | Liquid detergent compositions containing a suspended peroxygen bleach |
EP90870197.0 | 1990-10-22 | ||
EP90870197,0 | 1990-10-22 |
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CN1061996A CN1061996A (zh) | 1992-06-17 |
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CN90100768.4A Expired - Fee Related CN1027080C (zh) | 1989-01-10 | 1990-01-10 | 含酶和酶稳定系统的液体洗涤剂组合物 |
CN91111077.1A Expired - Lifetime CN1030333C (zh) | 1989-01-10 | 1991-10-22 | 含有悬浮过氧漂白剂的液体洗涤剂组合物 |
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-
1989
- 1989-01-10 GB GB898900496A patent/GB8900496D0/en active Pending
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1990
- 1990-01-05 AT AT90200026T patent/ATE109201T1/de not_active IP Right Cessation
- 1990-01-05 DE DE69010922T patent/DE69010922T2/de not_active Expired - Fee Related
- 1990-01-05 EP EP90200026A patent/EP0378261B1/en not_active Expired - Lifetime
- 1990-01-09 CA CA002007381A patent/CA2007381C/en not_active Expired - Fee Related
- 1990-01-09 TR TR90/0095A patent/TR25347A/xx unknown
- 1990-01-09 NZ NZ232055A patent/NZ232055A/xx unknown
- 1990-01-10 CN CN90100768.4A patent/CN1027080C/zh not_active Expired - Fee Related
- 1990-01-10 IE IE900097A patent/IE900097L/xx unknown
- 1990-01-10 AU AU47871/90A patent/AU638961B2/en not_active Ceased
- 1990-01-10 JP JP2003298A patent/JP2749416B2/ja not_active Expired - Fee Related
- 1990-01-10 PT PT92820A patent/PT92820A/pt not_active Application Discontinuation
- 1990-01-10 FI FI900130A patent/FI900130A/fi not_active Application Discontinuation
- 1990-01-10 MX MX019083A patent/MX172149B/es unknown
- 1990-10-22 EP EP90870197A patent/EP0482274A1/en not_active Withdrawn
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1991
- 1991-10-15 CA CA002094604A patent/CA2094604C/en not_active Expired - Fee Related
- 1991-10-15 AU AU89523/91A patent/AU662501B2/en not_active Ceased
- 1991-10-15 WO PCT/US1991/007606 patent/WO1992007055A1/en active Application Filing
- 1991-10-15 JP JP3518590A patent/JPH06502440A/ja active Pending
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