CN1258587C - 含三氯苯脲的液体肥皂及其制备方法 - Google Patents
含三氯苯脲的液体肥皂及其制备方法 Download PDFInfo
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- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 1
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- 238000007669 thermal treatment Methods 0.000 description 1
- 229960001325 triclocarban Drugs 0.000 description 1
- 229960003500 triclosan Drugs 0.000 description 1
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- 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
- C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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Abstract
本发明涉及三氯苯脲(N-(4-氯苯基)-N′-(3，4-二氯苯基)脲，三氯对称二苯脲)作为抗细菌的有效成分，在液体肥皂中的应用。
Description
本发明涉及作为抗细菌的有效成分的三氯苯脲(triclocarban，(N-(4-氯苯基)-N′-(3，4-二氯苯基)脲)在液体肥皂中的应用。
三氯苯脲作为抗细菌的有效成分被成功地用于抗菌浴皂(固体肥皂)中，已有近40年的历史。人们仅能得到粉状的三氯苯脲，例如结晶(未磨碎的)或细微粒。和其它既能用于抗菌浴皂，又能用于液体肥皂的普通抗菌有效成分，如三克菌森(triclosan)、(chlorhexidine)或二甲氯酚(chloroxylenol)相反，三氯苯脲至今不能用于液体肥皂中。
其原因是三氯苯脲在液体肥皂和它们的主成分中的溶解度极低。例如，三氯苯脲在液体肥皂的主成分，水中的溶解度约为50-100ppb，实际上是零。三氯苯脲在普通的表面活性剂，例如月桂基聚氧乙烯醚硫酸钠或可可酰氨基丙基甜菜碱(cocamidopropylbetain)和普通溶剂，例如甘油或丙二醇中的溶解度也远低于1％。
因此，要把三氯苯脲混用于液体肥皂中，并能显示它的活性，具有像浴皂那样的使用浓度也就成了问题。
液体肥皂是用于手和身体的普通洗涤产品，即手和身体用液体肥皂，淋浴和/或盆浴液，混合的淋浴液和护肤产品，例如具有护肤功能的淋浴液等。
三氯苯脲在液体肥皂中的浓度优选为该产品的0.3～0.5％，虽然根据肥皂组合物和微生物试验，比较低一些(0.1～0.25％)或比较高一些(0.55～0.7％)的浓度也可以试用。
为此，打算将三氯苯脲以0.1或0.7％的浓度溶解于表1所列的市售液体肥皂中，并试验在冷冻温度、室温和40℃贮存几周，观察外观上的结晶或不希望出现的变化或化学有效成分的不稳定性(采用PreventolSB，≥97％三氟苯脲)。
表1
德国/欧洲市场上可买到的液皂/浴液
浴液 制造厂家，供应商
CD Elida Gibbs
Rexona Elida Gibbs
Satina Bayer AG
Azzurra paglieri Scholl
Fa(marine) Henkel
Lux(Wash & Lotion) Lever
Nivea(shower) Beiersdorf
Ellen Betrix(Sport+Beauty) Betrix
Cliff(ocean fresh) Procter & Gamble
dusch das Linger+Fischer
手用液皂 制造厂家
Seba MEVINACORd Sebapharma
Satina Bayer AG
Lux Lever
Kd Tag-Vertriebs GmbH
Dove(cream wash) Lever
Kur(cream soap) win cosmetic/Aldi
美国市场上可买到的液皂
液皂 生产厂家
Jergens liquid soap The Andrew Jergens Company
Lever 2000 liquid soap Lever Brothers Company
Clean & Smooth Benckiser Consumer Products Inc.
Softsoap liquid hand soap Colgate Palmolive
Ultra Palmolive handsoap Colgate Palmolive
(液体)
Dial liquid soap The Dial Corp.
粉状的三氯苯脲在所试验的22种液体肥皂中都不溶解，甚至在加热到约50℃时也不溶解。
在第2个试验系列中，将10％三氯苯脲的强预溶液(三氯苯脲溶解于PO/EO共聚物类型的加溶剂/乳化物中)混入到上述液体肥皂中，使三氯苯脲以0.7％的浓度存在。可是在20个产品中，仅几小时至最长的24小时之后，实际上所有的三氯苯脲都结晶析出了，余下的2个产品中，在几周之内，三氯苯脲也结晶析出。可是，液体肥皂必须有许多个月的货架寿命，也就是说，这些剂型都不适合于三氯苯脲。
相反，三克菌森可以0.7％的浓度混入所说的液体肥皂中。
所以，本发明的目的是开发以三氯苯脲为基础的，同时具有长货架寿命的，特殊的，化妆上需要的，生态与经济上可行的，以及具有微生物活性的液体肥皂。
现在已经惊奇地发现，尽管有高含量的水和表面活性剂，也已能制得化妆上高价值和稳定的液体肥皂。
本申请提供了液体肥皂的组成
a)0.1～0.7％重量计的三氯苯脲，和
b)11.2～14.7％重量计的月桂基聚氧乙烯醚硫酸钠，和
c)3～5％重量计的聚乙二醇-9可可甘油酯或聚乙二醇-7-甘油可可酯，和
d)2～10％重量计的聚乙二醇-400(聚乙二醇-8)或聚乙二醇-600(聚乙二醇-12)，和
e)0.2～0.4％重量计的香料，和
f)2.2～2.9％重量计的可可酰氨基丙基甜菜碱，和
至少一种或多种以下组分
g)1.0～2.5％重量计的月桂基聚氧乙烯(2)醚和/或月桂基聚氧乙烯(3)醚(laureth 2，laureth 3)
h)0.1～0.2％重量计的防腐剂
i)0.7～1.0％重量计的NaCl
k)14～21％重量计的山梨(糖)醇
l)0～2％重量计的聚山梨酸酯20
m)2.4％重量计的月桂基聚氧乙烯醚磺基琥珀酸二钠
用水补足至100％重量计的差额。
混入一般如下进行：通过三氯苯脲与液体肥皂的组分相混合，或优选以预溶液形式的三氯苯脲与一种或多种制备该液体肥皂的单个组分相混合，然后将所得的混合物与其它余下的组分相混合，或者将在一种溶剂中的三氯苯脲预溶液混入到已制成的液体肥皂中，这种溶剂是适宜溶解和/或分散三氯苯脲，并可用于液体肥皂的。
也可能将液体肥皂的单个组分或单个组分的混合物与三氯苯脲相混合，然后依次任意与其它液体肥皂的单个组分或单个组分的混合物或也含有三氯苯脲的溶剂相混合。
本申请还提出三氯苯脲可以微胶囊的形式混入到液体洗涤产品中。这可以提高溶液的性能和三氯苯脲对液体洗涤产品的稳定性。适当的微胶囊，例如基于明胶的微胶囊，其直径由几μm至＜1mm，它们仅在洗涤过程中，例如通过破裂而溶解。
三氯苯脲以溶解或分散的形式，任意与液体洗涤剂的其它组分或溶剂一起置于胶囊中。原则上，三氯苯脲可与三克菌森以任何比例混合用于液体洗涤产品(液体肥皂)，以实现液体洗涤产品的抗菌性或化妆品的特性。
以下配方是新的液体肥皂的实例。
实例
| 配方1 | ％(重量计) | 有效成分％ |
| 月桂基聚氧乙烯醚硫酸钠可可酰氨基丙基甜菜碱聚乙二醇-9可可甘油酯聚乙二醇-400(聚乙二醇8)三氯苯脲香料月桂基聚氧乙烯(2)醚(或月桂基聚氧乙烯(3)醚)月桂基聚糖/可可酰氨基丙基甜菜碱防腐剂NaCl水 | 5064100.1-0.5*0.2-0.41.060.1-0.20.7加至100 | 142.24100.1-0.51.02.60.7总水含量约65％ |
*浓度大于0.5％时，在室温存放几周会析出三氯苯脲结晶。
| 配方2 | ％(重量计) | 有效成分％ |
| 月桂基聚氧乙烯醚硫酸钠可可酰氨基丙基甜菜碱聚乙二醇-7甘油可可酯聚乙二醇600(聚乙二醇12)三氯苯脲香料月桂基聚氧乙烯(2)醚(或月桂基聚氧乙烯(3)醚)月桂基聚糖/可可酰氨基丙基甜菜碱防腐剂水 | 5064.06.00.3-0.5*0.2-0.41.060.1-0.2加至100 | 142.24.06.00.3-0.51.02.6总水含量约70％ |
*浓度大于0.5％时，在室温放置几周，会析出三氯苯脲结晶。
| 配方3 | ％(重量计) | 有效成分％ |
| 月桂基聚氧乙烯醚硫酸钠可可酰氨基丙基甜菜碱聚乙二醇-7甘油可可酯聚乙二醇400(聚乙二醇8)三氯苯脲香料防腐剂NaCl水 | 508.03.02.00.1-0.3*0.2-0.40.1-0.20.7加至100 | 142.93.02.00.1-0.30.7总水含量约76％ |
*浓度大于0.3％时，在室温存放几周，会析出三氯苯脲结晶。
| 配方4无防腐剂/自身防腐 | ％(重量计) | 有效成分％ |
| 月桂基聚氧乙烯醚硫酸钠可可酰氨基丙基甜菜碱聚乙二醇-9可可甘油酯聚乙二醇400(聚乙二醇8)三氯苯脲香料月桂基聚氧乙烯(2)醚(或月桂基聚氧乙烯(3)醚)山梨(糖)醇防腐剂水 | 52.57.54.26.30.3-0.5*0.2-0.41.620.0-30.0无加至100 | 14.72.74.26.30.3-0.51.614.0-21.0总水含量约49-56％ |
*浓度大于0.5％时，在室温放置几周，会析出三氯苯脲结晶。
| 配方5 | ％(重量计) | 有效成分％ |
| 月桂基聚氧乙烯醚硫酸钠可可酰氨基丙基甜菜碱月桂基聚氧乙烯醚磺基琥珀酸二钠聚乙二醇400(聚乙二醇8)聚乙二醇-9可可甘油酯聚山梨酸酯20三氯苯脲香料月桂基聚氧乙烯(2)醚(或月桂基聚氧乙烯(3)醚)防腐剂NaCl水 | 40.08.06.08.05.00-2.00.3-0.5*0.2-0.42.50.1-0.20.7-1.0加至100 | 11.22.92.48.05.00-2.00.3-0.52.50.7-1.0总水含量约62-64％ |
*浓度大于0.5％时，在室温存放几周会析出三氯苯脲结晶。
| 配方6 | ％(重量计) | 有效成分％ |
| 月桂基聚氧乙烯醚硫酸钠可可酰氨基丙基甜菜碱月桂基聚氧乙烯醚磺基琥珀酸二钠聚乙二醇400(聚乙二醇8)聚乙二醇-7甘油可可酯聚山梨酸酯20三氯苯脲香料月桂基聚氧乙烯(2)醚(或月桂基聚氧乙烯(3)醚)防腐剂NaCl水 | 40.08.06.08.05.0*0-2.00.3-0.7**0.2-0.42.50.1-0.20.7-1.0加至100 | 11.22.92.48.05.00-2.02.50.7-1.0总水含量约62-64％ |
*如果聚乙二醇-9可可甘油酯(见配方5)用聚乙二醇-7甘油可可酯代替，三氯苯脲也可以采用比较高的浓度，例如此处的0.7％。
**浓度大于0.7％时，在室温存放几周会析出三氯苯脲结晶。
| 配方7无防腐剂/自身防腐 | ％(重量计) | 有效成分％ |
| 月桂基聚氧乙烯醚硫酸钠可可酰氨基丙基甜菜碱聚乙二醇-7甘油可可酯聚乙二醇400(聚乙二醇8)三氯苯脲香料月桂基聚氧乙烯(2)醚(或月桂基聚氧乙烯(3)醚)山梨(糖)醇防腐剂水 | 52.57.54.2*6.30.3-0.7**0.2-0.41.626.56无加至100 | 14.72.74.2*6.30.3-0.71.618.6总水含量约51％ |
**浓度大于0.7％时，在室温存放几周会析出三氯苯脲结晶。
上述所有液体肥皂的配方都可产生带有令人愉快气味的清亮，无色的粘稠液体。pH约为6～6.5。如果需要，粘度可以调节至约4000mPas，在没有三氯苯脲稳定性的不利影响时，较低粘度或较高粘度的配方也是可能的。
而且在配方4和7中，一些水可用山梨(糖)醇代替。这样得到的液体肥皂具有如此的微生物稳定性，以至于不需要加防腐剂。这是很惊奇的，实际上不溶于山梨(糖)醇的三氯苯脲在液体肥皂中仍然保持稳定，没有结晶析出。
新颖的液体肥皂的稳定性或三氯苯脲的结晶行为以及氯苯胺的形成可调查如下：所有含0.1～0.7％三氯苯脲的配方的液体肥皂样品都在+6℃(冰箱)，室温和40℃(烘箱)，至少存放4周。在一定间隔检查确定三氯苯脲是否结晶析出。
在上述所有配方中，三氯苯脲都按给定的浓度保留在溶液中，没有结晶析出。高于给定浓度或配方作了明显改变，都会导致三氯苯脲结晶析出。
实施例A
对于在室温和40℃贮存的样品，采用HPLC来检测可能形成的氯苯胺，三氯苯脲被指定为Preventol SB(制造厂家：拜耳公司)，氯苯胺的最大含量为450ppm。从所采用的浓度，可以计算出理论的氯苯胺起始最大含量为3.15ppm。对于液体肥皂制备，由于采用冷技术，没有热处理，或由于pH也不太高，所以在制备过程中没有氯苯胺产生。HPLC分析法的测定限量为约10ppm。从表2可见，在室温贮存11或14周后，上述配方中的氯苯胺含量不是至关重要的，远低于FDA推荐的100ppm。在40℃贮存4或11周后(加速稳定性试验)，发现氯苯胺的含量也不高于100ppm。
表2
| 液体肥皂 | 贮存时间 | 氯苯胺总含量，ppm |
| 配方1配方2配方3配方4配方5配方6配方7 | 4周，40℃14周，室温4周，40℃14周，室温6周，40℃14周，室温4周，40℃11周，室温11周，40℃11周，室温11周，40℃11周，室温4周，40℃11周，室温 | 4416251815nd11nd3111321312nd |
nd＝≤10ppm的氯苯胺
实施例B
抗菌作用的微生物试验
所采用的试验方法是按照DGHM(德国卫生学和微生物学协会)试验推荐的一种改进的定量悬浮试验。试验中所采用的试验微生物是革兰氏阳性和革兰氏阴性细菌。微生物播种(微生物的起始数)是每毫升所用溶液8×106-1.1×107CFU(群落形成单位)，液体肥皂作为75％去离子水的稀释液被使用(模拟液体肥皂在湿手上的使用)。在接触1分钟后，测定与起始的微生物数相比，减少的微生物数。
结果：
接触1分钟后，在液体肥皂(75％)中微生物数比起始微生物数减少的百分率(％)。
| 液体肥皂 | 接触时间(分) | 试验微生物微生物减少％ | ||
| 配方2配方3配方5配方6 | 1111 | Staphylococcusaureus ATCC6538革兰氏阳性77-9591-979999 | Lactobacillusplantarum DSM20205革兰氏阳性97.3509691 | 假单胞菌aeruginosaDSM 1117革兰氏阴性63-67.5556392 |
概括地说，对于给定三氯苯脲浓度范围的配方1～7，是化妆品类型，高价值，对皮肤友好的液体肥皂/溶液，并对革兰氏阳性与革兰氏阴性细菌有高抗菌活性。这些配方在化学-物理上是稳定的，有效成分三氯苯脲不会结晶析出，各配方充分显示了抗菌特性，可能分解物，氯苯胺的含量保持低于FDA推荐的100ppm的限度。
Claims (9)
1.液体肥皂，包含如下组分：
a)0.1～0.7％重量计的 三氯苯脲和
b)11.2～14.7％重量计的 月桂基聚氧乙烯醚硫酸钠和
c)3～5％重量计的 聚乙二醇-9可可甘油酯或
聚乙二醇-7甘油可可酯和
d)2～10％重量计的 聚乙二醇-400或
聚乙二醇-600和
e)0.2～0.4％重量计的 香料和
f)2.2～2.9％重量计的 可可酰氨基丙基甜菜碱和
至少一种或多种以下组分
g)1.0～2.5％重量计的 月桂基聚氧乙烯(2)醚和/或月
桂基聚氧乙烯(3)醚
h)0.1～0.2％重量计的 防腐剂
i)0.7～1.0％重量计的 NaCl
k)14～21％重量计的 山梨(糖)醇
l)0～2％重量计的 聚山梨酸酯20
m)2.4％重量计的 月桂基聚氧乙烯醚磺基琥珀酸
二钠
用水补足至100％重量计的差额。
2.根据权利要求1的液体肥皂，包含如下组分，其中所有的量以重量百分比表示：
月桂基聚氧乙烯醚硫酸钠 14
可可酰氨基丙基甜菜碱 2.2
聚乙二醇-9可可甘油酯 4
聚乙二醇-400 10
三氯苯脲 0.3～0.5
香料 0.2～0.4
月桂基聚氧乙烯(2)醚
或月桂基聚氧乙烯(3)醚 1.0
月桂基聚糖 2.6
可可酰氨基丙基甜菜碱 2.2～2.9
防腐剂 0.1～0.2
NaCl 0.7
水 加至100，
用水补足至100％重量计的差额。
3.根据权利要求1的液体肥皂，包含如下组分，其中所有的量以重量百分比表示：
月桂基聚氧乙烯醚硫酸钠 14
可可酰氨基丙基甜菜碱 2.2
聚乙二醇-7甘油可可酯 4.0
聚乙二醇-600 6.0
三氯苯脲 0.3～0.5
香料 0.2～0.4
月桂基聚氧乙烯(2)醚或月桂基聚氧乙烯(3)醚 1.0
月桂基聚糖 2.6
可可酰氨基丙基甜菜碱 2.2～2.9
防腐剂 0.1～0.2
水 加至100，
用水补足至100％重量计的差额。
4.根据权利要求1的液体肥皂，包含如下组分，其中所有的量以重量百分比表示：
月桂基聚氧乙烯醚硫酸钠 14
可可酰氨基丙基甜菜碱 2.9
聚乙二醇-7甘油可可酯 3.0
聚乙二醇-400 2.0
三氯苯脲 0.1～0.3
香料 0.2～0.4
防腐剂 0.1～0.2
NaCl 0.7
水 加至100，
用水补足至100％重量计的差额。
5.根据权利要求1的液体肥皂，包含如下组分，其中所有的量以重量百分比表示：
月桂基聚氧乙烯醚硫酸钠 14.7
可可酰氨基丙基甜菜碱 2.7
聚乙二醇-9可可甘油酯 4.2
聚乙二醇-400 6.3
三氯苯脲 0.3～0.5
香料 0.2～0.4
月桂基聚氧乙烯(2)醚或月桂基聚氧乙烯(3)醚 1.6
山梨(糖)醇 14.0～21.0
水 加至100，
用水补足至100％重量计的差额。
6.根据权利要求1的液体肥皂，包含如下组分，其中所有的量以重量百分比表示：
月桂基聚氧乙烯醚硫酸钠 11.2
可可酰氨基丙基甜菜碱 2.9
月桂基聚氧乙烯醚磺基琥珀酸二钠 2.4
聚乙二醇-400 8.0
聚乙二醇-9可可甘油酯 5.0
聚山梨酸酯20 0～2.0
三氯苯脲 0.3～0.5
香料 0.2～0.4
月桂基聚氧乙烯(2)醚或月桂基聚氧乙烯(3)醚 2.5
防腐剂 0.1～0.2
NaCl 0.7～1.0
水 加至100，
用水补足至100％重量计的差额。
7.根据权利要求1的液体肥皂，包含如下组分，其中所有的量以重量百分比表示：
月桂基聚氧乙烯醚硫酸钠 11.2
可可酰氨基丙基甜菜碱 2.9
月桂基聚氧乙烯醚磺基琥珀酸二钠 2.4
聚乙二醇-400 8.0
聚乙二醇-7甘油可可酯 5.0
聚山梨酸酯 200～2.0
三氯苯脲 0.1～0.7
香料 0.2～0.4
月桂基聚氧乙烯(2)醚或月桂基聚氧乙烯(3)醚 2.5
防腐剂 0.1～0.2
NaCl 0.7～1.0
水 加至100，
用水补足至100％重量计的差额。
8.根据权利要求1的液体肥皂，包含如下组分，其中所有的量以重量百分比表示：
月桂基聚氧乙烯醚硫酸钠 14.7
可可酰氨基丙基甜菜碱 2.7
聚乙二醇-7甘油可可酯 4.2*
聚乙二醇-400 6.3
三氯苯脲 0.3～0.7
香料 0.2～0.4
月桂基聚氧乙烯(2)醚或月桂基聚氧乙烯(3)醚 1.6
山梨(糖)醇 18.6
水 加至100，
用水补足至100％重量计的差额。
9.制备如权利要求1～8所限定的液体肥皂的方法，其特征在于将三氯苯脲与液体肥皂的各个组分相混合，或任选一种预溶液形式的三氯苯脲与一种或多种制备液体肥皂的组分相混合，然后所得混合物再与其它剩余组分相混合。
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| FR2834448A1 (fr) * | 2002-01-04 | 2003-07-11 | Veyron Et Froment Lab | Composition demaquillante douce pour les yeux et le visage |
| US20040197845A1 (en) * | 2002-08-30 | 2004-10-07 | Arjang Hassibi | Methods and apparatus for pathogen detection, identification and/or quantification |
| DE10344956A1 (de) * | 2003-09-27 | 2005-07-21 | Beiersdorf Ag | Transparente Zwei-Phasen-Reinigungszubereitungen mit wechselnden Viskositäten |
| US7713617B2 (en) * | 2004-05-10 | 2010-05-11 | Hewlett-Packard Development Company, L.P. | Recording media for electrophotographic printing |
| WO2007092090A2 (en) * | 2005-12-30 | 2007-08-16 | The Dial Corporation | Liquid antibacterial compositions incorporating trichlorocarbanilide with reduced water activity |
| GB2449973B8 (en) * | 2007-05-31 | 2010-01-06 | Syntopix Group Plc | Antibacterial & anti-acne formulations containing dialkyl sulphosuccinates |
| WO2012162854A1 (en) * | 2011-05-27 | 2012-12-06 | Colgate-Palmolive Company | Liquid soaps with triclocarban |
| CN104768523B (zh) | 2012-10-29 | 2017-08-15 | 宝洁公司 | 10℃下具有0.30或更大损耗角正切值的个人护理组合物 |
| WO2018073616A1 (en) * | 2016-10-21 | 2018-04-26 | Greboval Elodie | Disinfecting composition |
| EP3366353A1 (en) * | 2017-02-28 | 2018-08-29 | Colgate-Palmolive Company | Personal care composition comprising a preservative system |
| EP3492068A1 (en) * | 2017-12-01 | 2019-06-05 | NCP NewCare Products GmbH | Composition for treating onychomycosis |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR7467M (zh) * | 1968-06-28 | 1969-11-24 | ||
| AU437869B2 (en) * | 1968-12-24 | 1973-07-11 | Malmstrom Chemical Corporation | Water-insoluble bacteriostats in soap and detergent solutions |
| ATE80794T1 (de) * | 1986-07-11 | 1992-10-15 | Procter & Gamble | Fluessige reinigungsmittelzusammensetzung. |
| FR2652741B1 (fr) * | 1989-10-10 | 1994-03-04 | Laboratoires Care System | Composition antimicrobienne pour application sur la peau, applications comme deodorant corporel et bactericide cutane. |
| AU671208B2 (en) * | 1993-06-30 | 1996-08-15 | Colgate-Palmolive Company, The | Anti-bacterial cleansing composition |
| EP0802786B1 (en) * | 1995-01-09 | 2000-12-13 | The Procter & Gamble Company | Three in one ultra mild lathering antibacterial liquid personal cleansing composition |
-
1997
- 1997-03-25 DE DE19712410A patent/DE19712410A1/de not_active Withdrawn
-
1998
- 1998-03-13 KR KR1019997007781A patent/KR20000075713A/ko not_active Application Discontinuation
- 1998-03-13 BR BRPI9807888-7A patent/BR9807888B1/pt not_active IP Right Cessation
- 1998-03-13 CN CNB988035448A patent/CN1258587C/zh not_active Expired - Fee Related
- 1998-03-13 IL IL13151498A patent/IL131514A0/xx unknown
- 1998-03-13 CA CA002284776A patent/CA2284776A1/en not_active Abandoned
- 1998-03-13 US US09/381,423 patent/US6121214A/en not_active Expired - Lifetime
- 1998-03-13 JP JP54482098A patent/JP2001521570A/ja active Pending
- 1998-03-13 AU AU70346/98A patent/AU733872B2/en not_active Ceased
- 1998-03-13 WO PCT/EP1998/001454 patent/WO1998042820A1/de not_active Application Discontinuation
- 1998-03-13 EP EP98916935A patent/EP0972010A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU7034698A (en) | 1998-10-20 |
| EP0972010A1 (de) | 2000-01-19 |
| WO1998042820A1 (de) | 1998-10-01 |
| US6121214A (en) | 2000-09-19 |
| AU733872B2 (en) | 2001-05-31 |
| DE19712410A1 (de) | 1998-10-01 |
| KR20000075713A (ko) | 2000-12-26 |
| BR9807888A (pt) | 2000-02-22 |
| CN1251129A (zh) | 2000-04-19 |
| JP2001521570A (ja) | 2001-11-06 |
| CA2284776A1 (en) | 1998-10-01 |
| BR9807888B1 (pt) | 2009-01-13 |
| IL131514A0 (en) | 2001-01-28 |
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