|Publication number||US3874870 A|
|Publication date||Apr 1, 1975|
|Filing date||Dec 18, 1973|
|Priority date||Dec 18, 1973|
|Publication number||US 3874870 A, US 3874870A, US-A-3874870, US3874870 A, US3874870A|
|Inventors||Green Harold A, Merianos John J, Petrocci Alfonso N|
|Original Assignee||Mill Master Onyx Corp|
|Export Citation||BiBTeX, EndNote, RefMan|
|Patent Citations (4), Referenced by (263), Classifications (28), Legal Events (10) |
|External Links: USPTO, USPTO Assignment, Espacenet|
Microbiocidal polymeric quarternary ammonium compounds
US 3874870 A
The use of polymeric quaternary ammonium compounds prepared by the condensation of 1,4-dihalo-2-butene and 1,4-bis-dimethylamino-2-butene as microbiocidal agents in aqueous systems.
United States Patent  3,874,870 Green et al. Apr. 1, 1975 MICROBIOCIDAL POLYMERIC  References Cited QUARTERNARY AMMONIUM UNITED STATES PATENTS COMPOUNDS 3,140,976 7/1964 Berenschot et a1. 424/329  Inventors; Harold A, Green, Havertown P3; 3,539,684 11/1970 Hoover 424/78 J Mel-ianos Jersey Ci 3,771,989 11/1973 Pera et al 424/329 Alfonso N. Petrocci, Glen Rock7 3,778,283 12/1973 Freyhold 106/84 both of FOREIGN PATENTS OR APPLICATIONS  Assignee: Mill Master Onyx Corporation, New 69-8949 7/1970 South rica York, N.Y.
Primary Examiner-Albert T. Meyers  Flled' 1973 Assistant Examiner-Douglas W. Robinson  App]. No.: 425,931 Attorney, Agent, or FirmArthur A. Jacobs, Esq.
52 U.S. Cl 71/67, 260/875 R, 424/78, ABSTRACT 424/329 The use of polymeric quaternary ammonium com- 1 AOIN AOlN A61K 0 pounds prepared by the condensation of 1,4-diha1o-2- A61K 17/00 butene and l,4-bis-dimethylamino-Z-butene as micro- Fleld of Search biocidal agents in aqueQuS Systems,
8 Claims, N0 Drawings MlCROBIOClDAL POLYMERIC QUARTERNARY AMMONIUM COMPOUNDS This invention relates to microbiocidal agents, and it particularly relates to microbiocidal agents comprising polymeric quaternary ammonium compounds.
It is known that many quaternary ammonium compounds have biocidal or inhibitory effects on microorganisms. However, few such compounds, or indeed few biocidal compounds of any type, have been found to have all the necessary characteristics required for the biocidal treatment of aqueous systems of the recirculated type such as industrial or process waters of the type used in paper manufacturing, cooling towers, air conditioners, humidifiers and the like. Even relatively standing waters such as swimming pools have been problems insofar as maintaining them substantially free of bacteria, fungi and algae,
The control of microorganisms in aqueous systems of the aforesaid type has long been recognized as a particularly burdensome problem since the environment of the aqueous medium itselfis often extremely conducive to rapid multiplication and growth of these undesirable organisms. Only through the rise of carefully tailored microbiocidal agents can this growth and reproduction be reliably controlled without detriment to the process in which the water is used. For example, many times a n X-CH biocidal compound is rendered completely inactive by the particular surrounding media containing the undesirable microorganisms. A particular problem in recirculated waters is that the recirculation causes many difficult problems, among which is the gradual build-up and accumulation of undesirable microorganisms in the aqueous fluid. Various bacteria, fungi and algae are favorably produced in such recirculated waters.
Another common feature of quaternary ammonium biocides is that their biocidal effectiveness is diminished in the presence of non-ionic emulsifiers, often to the point where they no longer function as acceptable biocides. This has significantly reduced their possible use in cosmetics and similar preparations that require the inclusion of non-ionic emulsifiers.
An additional problem in the use of most microbiocidal agents in aqueous systems is the formation of large amounts of foam. This foam is generally highly undesirable and the formation thereof by these agents often makes them useless for particular applications.
In accordance with the present invention, it has now been discovered that certain polymeric quaternary ammonium compounds and, particularly, the product made by the condensation of 1,4-dihalo-2-butene and l,4-bis-dimethylamino-2-butene is not only a highly effective microbiocidal agent in aqueous systems, including recirculating waters, industrial waters, cosmetics and other emulsions containing non-ionic emulsifiers, as well as in general usage, but also effects such purpose without causing undue foaming.
It is to be noted that a particular aspect of the present invention is that the quaternary ammonium moieties of -CH=CH-CH X n (CH the present compounds are part of a long chain rather than being on branches that are bonded to the long chain.
The aforesaid compounds are active against Pseudomonas aeruginosa at a concentration relative to the total composition as low as 25 ppm, although the preferred concentration is about 150 ppm. Against Aerohacter acrogenes, they are active at a concentration as low as ppm, although the preferred concentration is about 100 ppm. Against algae, such as Chlorella pyrenoidosa, they are active at a concentration at least as low as 1 ppm and probably even much below that concentration according to present indications.
Insofar as concerns upper limits, the concentration may apparently be increased indefinitely without deleteriously affecting the biocidal activity.
More specifically with regard to cosmetic compositions. the products of this invention are effective at a concentration at least as low as about 500 ppm relative to the total composition, and probably at even lower concentrations, according to present indications. The preferred range, however, is about I ,000 to 2,000 ppm.
There is no absolute certainty of the actual structure of the product of the condensation reaction because isomerizations are possible. However, ideally, the reaction would appear to be as follows:
wherein X is a halogen such as chlorine or bromine and n is an integer from about 2 to 30.
The following examples illustrate the present invention with no intent to be limited thereby, however, except as claimed:
EXAMPLE 1 14.2 grams of l,4-bis-dimethylamino-Z-butene (0.1 mole) was dissolved in grams of water, and to it was added 12.5 grams (0.] mole) of l,4-dicholoro-2- butene over a period of 15 to minutes while maintaining constant stirring. The reaction was exothermic so that the temperature rose to about 7()C. The reaction mixture was then warmed on a steam bath at a temperature of about C. for about 1 hour, after which the reaction was considered complete. Titration of ionized chlorine was used as a measure of the extent of the reaction and indicated between 98 and 10071 completeness. The reaction product was a viscous material containing about 50% active material.
It was found that when a significant excess of the dichlorobutene was used, a second phase separated out of the final reaction product. Analysis indicated this second phase to contain primarily unreacted dichlorobutene.
Quite surprisingly, the compounds of this invention may be obtained directly as crystalline-like solids when the reaction is carried out in certain organic solvents such isopropanol, acetone and inert halogenated solvents. This is illustrated as follows:
EXAMPLEZ 14.2 grams of l,4-bis-dimethylamino-2-butene were mixed with 25 grams of isopropanol, and to it was added, with stirring. 12.5 grams of 1.4-dichloro-2- butene over a period of about minutes (or at a rate which keeps the solvent gently refluxing). After the exothermic reaction subsided, the mixture was warmed on a ateam bath to reflux temperature and maintained at such temperature for about 1 hour. It was then cooled, to room temperature, whereby a precipitate was formed. The precipitate was then separated out by filtration as the final product. The precipitate weighed 18.7 grams. This product is substantially free from impurities caused by side reactions or due to absorption of unreactcd starting materials, thereby making it easier to purify for use in cosmetics or cosmetic emulsions.
Solid products of the above type have the commercial advantage over aqueous solutions or dispersions because they have less bulk on a pound for pound active ingredient basis.
EXAMPLE 3 The same reactants and procedures were used as in Example 2.except that instead of the isopropanol,
grams of acetone was used. It yielded 21.4 grams of a solid product.
The same procedures may be used except that 1,4- dibromo-2-butene is substituted for the 1,4-dichloro-2- butene, with equivalent mol ratios. The product is substantially similar in all essential characteristics.
EXAMPLE 4 142 grams of l,4'bis-dimethylamino-2-butcne were dissolved in 300 ml. of 1,1 ,l-trichloroethane and to it was added slowly, with constant stirring, 125 grams of l ,4-dichloro-2-butenc at a rate which kept the reaction mixture at a temperature between 45 and 60C., and stirring was continued at 45 to 60C. for 1 hour after an almost-white precipitate was first deposited. After cooling, the precipitate wascollected by filtration and dried in a vacuum desiccator. ltwcighed 245 grams.
Various changes in relative proportions were made to determine whether any significant variations occurred. These as illustrated as follows:
EXAMPLE 5 14.2 grams of l,4-bis-dimethylamino-2-butenc (0.1
mole) was dissolved in grams of water, and to it was added 25.0 grams of 1,4-dichloro-2-butene (0.2 moles) over a period of 15-30 minutes, maintaining constant stirring. The reaction was exothermic. After 1 hour analysis for ionic chloride showed that the reaction was about 98% complete.
EXAMPLE 6 The same reactants and procedures were used as in Example 5, but the solvent was 35 grams of isopropyl alcohol instead of water. After about 1 hour, the solid polymeric product was filtered off. It weighed about 18.7 grams. I
EXAMPLE 7 The same reactants and procedures as used in Example 5, but using 35 grams of acetone as a solvent instead of water, gave a solid product which weighed 21.4 grams after filtration.
EXAMPLE 8 14.2 grams of 1,4-bis-dimethylamino-2-butene (0. 1 mole) was dissolved in grams of water, and wit was added 37.5 grams of 1,4-dichloro-2-butene over a period of 1530 minutes, maintaining constant stirring.
The reaction was exothermic. After one hour, analysis for ionic chloride showed that the reaction was about 9894 complete.
EXAMPLE 9 EXAMPLE 10 The same reactants and procedures as used in Example 8, but using 45 grams of aceton'einstead of water gave a solid product which weighed 21.4 grams after filtration.
EXAMPLE 1 1 14.2 grams of bis-dimethylamino-Z-butene (0.1 mole) was dissolved in 20 grams of water and to it was added 6.3 grams of 1,4-dichloro-2-butene (0.05 mole) over a period of 15-30 minutes. The reaction was exothermic. After 1 hour, analysis for ionic chloride,
showed that the reaction was about 98% complete' EXAMPLE 12 The same reactants and procedures used in Example 1 1 were used with 20 grams of isopropyl alcohol as sol vent instead of water. After about 1 hour, the. solid f polymeric product was filtered off. It weighed. 9.4
EXAMPLE 13 The same reactants and procedures as used in Exam ple 1 1 were used, except that 20 grams of acetone replaced water as solvent. After about 1 hour, the product weighed about 10.7 grams.
EXAMPLE 14 21.3 grams of 1,4-bis-dimethylamino-2-butene was (0.15 moles) dissolved in 25 grams of water, and to it was added 6.3 grams of 1,4-dichloro-2-butene (0.05 moles) over a period of 15-30 minutes, maintaining constant stirring. After 1 hour, analysis for ionic ch1o-- ride showed about 9871 completion.
EXAMPLE 15 The same reactants used in Example l4,but with 25 grams of isopropyl alcohol replacing water as solvent,
produced 9.4 grams of solid polymeric product after filtration.
EXAMPLE 16 The same reactants used in Example 14, but with 25 1 grams of acetone replacing water as solvent, produced about 10.7 grams of solid polymeric product.
EXAMPLE '17 In order to determine the microbiocidal effectiveness of the present compound, the following test procedures were used:
Bactericidal Tests l. ml. volume of the product of Example 1 (here? inafter referred to as product A) was diluted in distilled water to the test concentration, and was added asceptically to previously sterilized cotton-stoppered 125 ml. Erlenmeyer flasks. For comparative purposes, the same test concentration was prepared using another known microbiocidal polymeric quaternary ammonium compound, namely a product produced by the reaction of bis(2-chlorocthyl) ether and tetramethyl ethylenediamine (hereinafter referred to as Product B").
2. One set of test flasks were each inoculated with 0.5 ml. of a 1/10 nutrient broth dilution of a 24-hour nutrient broth culture of Aerobactcr aerogenes and another set of test flasks were each inoculated with 0.5 ml. of a one-tenth nutrient broth dilution of a 24-hour nutri ent broth culture of Pseudomonas aeruginosa.
3. At 30 and 60, minutes following inoculation, a 1 ml. aliquot of each product was removed rrom each flask and added to 9 ml. of sterile azolectin/Tween 80" neutralizer from which additional fold serial dilutions were prepared in the sterile neutralizer solution.
4. Agar plate counts were prepared from 10 and 10 dilutions.
5. A control of sterile distilled water was similarly inoculated and aliquots were made at the same intervals and plates at 10*, 10", and 10 dilutions.
6. A comparison of the surviving organisms for various concentrations of test materials, at the different time periods was made. The results were as follows:
Table l AGAINST PSI-IUDUMONAS AEROGINOSA Cone. No. of Bacteria Surviving After Sample in ppm. 30 min. 60 min.
Product A 75 29,600 18,500
Product B" 150 26.000 6,800
-Untretlted 8,500,000 12,500,000
(Control) Table 2 AGAlNST AEROBACI'IJR AERUGl-INLZS Cone. No. of Bacteria Surviving After Sample in ppm. 30 min. 60 min.
Product A" 20 5,600 4,300 50 3,000 1 ,1 100 "Product 13" 100 30,000 30,000
Untreated (Control) 10,500,000 1 1,000,000
Table 3 The following 'l'ahlc comprises a comparison of Product A" and "Product B" at identical concentrations:
AGAINST AI-[ROIMCI'l-JR AEROGENl-IS' Algaestatie Tests 1. 24 ml. volumes of Product A and Product B were prepared in sterile Erlenmeyer flasks at various test concentrations.
2. 1 ml. of 5-7 days Allen's liquid medium growth of Chlorella pyrenoidosa (Wise. strain) was added to each flask (Allens liquid medium is a standard test composition comprising mg. NH,C1, 1000 mg. NaNo 250 mg. K HPO 3 mg. FcCl 513 mg. MgSO 50 mg. CaCl and 1000 mil. distilled water).
3. The inoculated flasks. plus untreated inoculated control flasks, were incubated at room temperature (about 25C.) under continuous artificial illumination.
4. Following 5 to 7 days incubation, observation was made for macroscopic growth to determine the minimum inhibitory level for each test material.
The results were as follows:
Table 4 Sample Minimum effective concentration in ppm.
Product A" 1.0 "Product 13" 1.5
A graduated blender cylinder is rinsed with distilled water. ml, of aqueous test solution is added downthe walls of the blender so as to cause no foam. the blender is turned to high speed for exactly 5 seconds, and upon turning the blades off, timing is started with a stop watch, and at the same time the foam height read in mm. from the 100 ml. mark. The foam half-life is defined as the time it takes for liquid to drain out of the foam and reach the 50 ml. mark.
A further test was made using the Cylinder Shake Test procedure which is as follows:
CYLINDER SHAKE TEST I ml. of test solution is gently poured down the walls of a 250 ml. graduated cylinder that has a glass stopper. The cylinder is stoppered and inverted times in 15 seconds, finally resting it in an upright position. The foam height is read in cc. from the base of the foam.
Table 6 Foam Height in cc. Sample ppm. Initial l min. 5 min.
B'I'C 77(1" 50 45 34 Product A" St) (I (l "BTC 2l25" 5U 50 (i 4 Another test used was .the standard Ross-Miles Test using the procedure reported in "ASTM Standards, Designation 1175-53, Part X, 1958, page 878," which is the ASTM test for foaming properties of surface active material. The results were as follows;
Table 7 Foam Height in cc. Sample ppm. Initial I min. 5 min.
BTC 776' 50 30 20 Product A" 50 0 t) I) BTC 2l25" 5O 35 I5 I() The above results clearly show not only that the product of this invention is highly biocidal but that it is non-foaming, whcreasother quaternary ammonium bi ocides cause a relatively large amount of foaming in aqueous composition.
The following examples illustrate various cosmetic compositions using the product of the present invention:
Example I8 Components 71 by Wt. I by by Wt. "/r by Wt.
Mineral oil (65/75 VisC.) 35.0 35.0 35.0 35.0
Lanolin (Cosmetic Grade) l.() 1.0 1.0 l.()
Celyl alcohol I.() l.() l.() 1.!)
'IWEEN 8t)" (Atlas Powder Co.) (non-ionic "SPAN Rt) (Atlas Powder Co.) (non-ionic emulsifier) "Product A Water (Distilled) 55.0
In the case of the first formulation, without Product A A, the mineral oil, lanolin, cetyl alcohol, Tween 80, and Span 80 were combined and heated to about (157()C. The water was heated to about 7()C. and added slowly to the hot non-aqucousphase while stirring the mixture until it emulsified completely. The emulsion was cooled to room temperatureusing con-. tinued agitation.
In each formulation when Product A was incorporated. the mineral oil, lanolin, cetyl alcohol,Twee n.8(), and Span were combined and heated to about 657()C. The water and Product A were combined and heated to about 6570C. Then the hot aqueous solution was added slowly to the hot non-aqueous phase while stirring, and agitation was maintained until emulsification was effected. Then the emulsion was cooled with continued stirring to room temperature. The resultant product was an oil-in-water emulsion.
These compositions are utilizable as hand creams and baby lotions.
These compositions were tested in thefollowing manner:
50 gm. samples from each composition were aseptieally transferred to sterile 8 02. wide mouth jars. Two replicate jars were prepared in everyinstance, includ; ing an untreated control. Each jar was inoculated with 2.5 ml. of a one-ten sterile nutrient heated dilution of pooled 24 hour broth cultures of Staphylococcus aureus. Pseudomonas aeruginosa, Escherichia coli, Enterobacteraerogenes, proteus species and Bacillus spe cies. In this manner a bacterial challenge load of l-l OX 1 O bacteria/nil. ofjar content was obtained. All. the inoculated jars were stored at 2527C. At weekly intervals following inoculation, 1 ml. aliquots of jar content were removed from each jar and tenfold serial dilutions were prepared therefrom in stcrile A zalectin/- Tween 80 neutralizer solution which wereplated into TGE a jar. In this manner the number of surviving viable bacteria in each jar was determined. In those instances where no viable surviving bacteria lO bac.teria) were observed at four weeks following inoculation,
the jar contents were reinoculated exactly as previously and IOXIO bacteria/ml. The. variation around the mean of the inoculum concentration is of little importance when a reduction to less than lO/ml. ofviable l bacteria is observed.
Table 8 INOCULATION at 6 X It) organisms/nth ol'jar content for each of the four formulations of Example 18.
From a statistical point of view, there is no significant difference between an initial inoculum load of IX I 0 Week Count Count Count Count I (19 X H)" l5.()(l() II) 10' 2 71 X [0" 74,000 H) l() 3 54 X It) 1.400 l(). [0 4 XI II) II) 10 In order to double'check the validity of this test showing less than 10 organisms/ml. after four weeks,
the samples were rcinoculat cd and the weekly counts Table 10 after reinoculation were:
INOCULATION at 3.8X10 organisms/ml. of jar content for each o1- the four formulations o1- Example 20:
Week Count Count Count Count 5 Count Count Count Count eek 5 10K X10" 10 10 10 6 169 X 10" 10 10 10 I [8x100 ISXIOIF RXXIUH 7 180x10" 10 10 10 2 23x1 :lxloli IZXIU ()IZXHW 8 209 X 10' 10 10 10 3 87x10 7 84x10" sfixloli 4 l()(t l0' 50x10" 70x10" 80x10" 10 5 109x10" 114x10" 50x10" 20x10" UZXIU 7'JXI1)" 45Xl0" 36 l0' The followmg example were prepared in the same 4X10 89x10" 67x10 750x10" manner as Example 18, but substnutmg other well- 8 fi mzxmfi xlxm" known, highly active biocidal quaternary ammonium compounds for Product A. They were then similarly evaluated.
Ex'tm 1e 19 p Example 21 I" F I/ I" Componuns h W1. 1 h Wt. by Wt. h Wt. Comlmmms (/1 by wt. by wt WL Mimml *1" Mineral 011 55.0 55.0 55.0 55.0 105/75 VISC.) 35.0 35.0 35.0 55.0 (65/75 visa) Lanolin Lanolin (Cosmetic Grade) 1.0 1.0 (Cosmetic Cetyl Alcohol 1.0 1.0 1.0 1 0 Grade) 1.0 1.0 1.0 1.0 TWEEN 150" 5.4 .1 5.4 Cetyl alcohol 1.0 1.0 1.0 1.0 SPAN 110 2.0 2.0 2.0 2.0 E 80' 5.4 .4 5.4 5.4 BTC snr SPAN 80 2.6 .0 2.6 2.6 (On\'x (711001.01) 0 0.1 0.2 04 HYAMINE 1633 Water (507') (131511110111 55.0 54.0 54.1: 54.0
Table 9 lNOCULATlON at 4.7 X 1()orgnnisn1s/ml. o1 jar content for each of the lour formulations of Example 19.
. Table 1 1 Count Count Count Count cck INOCULATION at 3.1"1 l0 organisms/ml. ot' jar content for each i 40 of the four formulations of Example 21: 1 10x10- 10x10" 10x10" 4x10" 3 98x10" 13x10" 1 1X10" 5X10" Count Count Count Count 1 07x10" 40x10 24x10 10x10" COR 4 142x10" lt)2 84x10" 01x10" 5 167Xl0" l19 l0 X4Xl0" (17 l0 l ZZXIU 19X 10 l7 l0"' l5 l0 6 180x10" l 14 10 32x11)" 44x11)" 2 P.4Xl0 21x11)" 19 l0 l -l l0 7 140x10" 95x10 82x10" 70x10" 3 80x10" 71x10" 94x10" 111x10" 8 4 0" 2 1 0 54 4 94x10 80x10 72Xl0 92X10" 5 106 l0 74 10" 67 l0 x10" 6 l loXlt) 91x10 84x10 X10 7 '-)Z l() 74 l0' 4ZX10 ZXXH)" 8 94X10" 82x10" 56 10' 43Xl0" 50 Example 20 Components "/1 by Wt. 71 hy Wt. 71 by Wt. by Wt.
Mineral oil gs (65/75 \-1se.) 35.0 35.0 35.0 35.0 Example 22 Lanolin (Cosmetic (irade) 1.0 1.0 1.0 1.0 Components "/1 by Wt. '/r by Wt. by Wt. 71 by Wt.
Cetyl alcohol 1.0 1.0 1.0 1.0 Mineral oil 0 (65/75 Vise.) 35.0 35.0 35.0 35.0 TWEEN 110" 5.4 5.4 5.4 0 5.4 Lwmlin (Cosmetic (irade) 1.0 1.0 1.0 1.0
. Z. 2. 2. 2X 51 AN 6 Cetyl 111001101 1.0 1.0 1.0 1.0 TWEEN 5.4 5.4 5.4 5.4 i 3135M "SPAN 2.0 2.0 2.0 2.0 HYAMINE 23110" (Onyx henLC o.) 0 0.1 0.2 0.4 1
(Robin & Haas) 0 0.1 0.2 0.4 Water Water (Distilled) 5540 54.) 54.1 5 (Distilled) 55.0 54.9 54.8 54.6
Table 12 INOCULATION at 4.l'l l() organisms/ml. of jar content for each of the four fornnilations of Example 22:
Although oil-in-water emulsions have been described above, it is within the scope of the present invention to use water-in-oil emulsions for the same purposes.
The invention claimed is:
l. A method of controlling the proliferation of deleterious microorganisms selected from the group consisting of bacteria and algae in an aqueous system, which comprises applying to said microorganisms a hacteriacidally or algaecidally effective amount of a condensation product formed'by mixing l,4-bisdimethylamino-Z-butene dissolved in a solvent with 1,4- dihalo-Z-butene at room temperature whereby an exothermic reaction is obtained causing the temperature of the mixture to rise, then maintaining the mixture at no higher than reflux temperature until the reaction is LII complete, wherein these reactants arepresent ina molar proportion of between about 1:3 and about 321 relative to each other.
2. The method of claim 1 wherein the dihalo is dichloro.
3. The method of claim 1 wherein the dihalo. is dibromo.
4. The method of claim 1 wherein the aqueousmedia is recirculated water.
5. An aqueous composition containing, as a biocidal agent, the condensation product formed by mixing] ,4- a
bis-dimethylamino-Z-butene dissolved in a solvent with l,4-dihalo-2-butene at room temperature whereby an .exothcrmicreaction is obtained causing the temperature of the mixture to rise, then maintaining the mixture at no higher than reflux temperature until the reaction is complete, wherein these reactants are in a molar proportion of between about about 1:3 and about 3:]
relative to each other, said agent being present in a bacteriacidally or algaecidally effective amount.
6. The composition of claim 5 wherein said aqueous media comprises recirculating water.
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|US5866016 *||Jul 1, 1997||Feb 2, 1999||Buckman Laboratories International, Inc.||Methods and compositions for controlling biofouling using combinations of an ionene polymer and a salt of dodecylamine|
|US5962555 *||Jun 25, 1997||Oct 5, 1999||Buckman Laboratories International, Inc.||Alkenyl succinic anhydride; paper sizing|
|US6008236 *||Apr 30, 1998||Dec 28, 1999||Buckman Laboratories International, Inc.||Microbiocide mixture for controlling the growth of microorganisms and prevent spoilage caused by microorganisms|
|US6051611 *||Feb 14, 1996||Apr 18, 2000||Alcon Laboratories, Inc.||Polymeric quaternary ammonium compounds and their use as ophthalmic antimicrobias|
|US6114484 *||Nov 16, 1998||Sep 5, 2000||Nalco Chemical Company||Polymers for chemical treatment and precipitation of soluble metal cyanide and oxoanion compounds from waste water|
|US6153570 *||Jun 6, 1997||Nov 28, 2000||L'oreal S.A.||Mixture of cationic polymer and amine-containing silicone|
|US6162423 *||Jul 21, 1997||Dec 19, 2000||L'oreal S.A.||A stabilizer for effectively maintaining insoluble silicones conditioning agents in suspension in shampoo compositions|
|US6177017 *||Apr 6, 2000||Jan 23, 2001||Nalco Chemical Company||Complexing with 1,4-diazabicyclo(2.2.2) octane polymers|
|US6203451||Jan 13, 1999||Mar 20, 2001||Acushnet Company||Zwitter-ion and ionene golf ball forming compositions and methods|
|US6260556||Jan 28, 2000||Jul 17, 2001||L'oreal||Anhydrous composition for bleaching keratin fibers|
|US6338842||Feb 3, 2000||Jan 15, 2002||L'oreal S.A.||Cosmetic composition comprising an anionic surfactant, an amphoteric surfactant, a polyolefin, a cationic polymer and a salt or an alcohol which is water-soluble, use and process|
|US6379401||Jan 28, 2000||Apr 30, 2002||L'oreal, S.A.||Alkaline agent, peroxygen salt and polymer thickeners and nonionic surfactant|
|US6410493||Nov 12, 1999||Jun 25, 2002||L'oreal S.A.||Cosmetics|
|US6423305||Dec 10, 1998||Jul 23, 2002||L'oreal S.A.||Amidoether acid derivatives as surfactants|
|US6436151||Jan 2, 2001||Aug 20, 2002||L'oreal S.A.||Compositions for oxidation dyeing keratin fibers comprising at least one oxidation dye, at least one thickening polymer comprising at least one fatty chain, and at least one fatty alcohol comprising more than twenty carbon atoms and uses thereof|
|US6444197||Dec 13, 2000||Sep 3, 2002||L'oreal S.A.||Bleaching composition for keratin fibers, comprising a combination of two polyurethane polyethers|
|US6451298||Oct 20, 2000||Sep 17, 2002||L'oreal, S.A.||One cationic polymer this combination can give cosmetic properties, such as at least one of smoothness, lightness, and softness, for hair|
|US6451747||Jun 6, 1997||Sep 17, 2002||L'oreal S.A.||Detergent cosmetic compositions for hair care and utilisation thereof|
|US6471953||Jun 28, 2000||Oct 29, 2002||L'oreal S.A.||Permanent-waving process comprising the preliminary application of a composition comprising at least one anionic polymer|
|US6482400||Jun 29, 2000||Nov 19, 2002||L'Oréal S.R.||Mascara containing film-forming polymers|
|US6506372||Jun 23, 2000||Jan 14, 2003||L'oreal S.A.||Cosmetic compositions containing an amphoteric polymer and a fixing/conditioner polymer, and their uses|
|US6514488||Feb 3, 2000||Feb 4, 2003||L'oreal S.A.||Shampoo; at least one cationic polymer and at least one anionic blockpolycondensate containing at least one polyurethane and/or polyurea|
|US6534047||Jun 29, 2000||Mar 18, 2003||L'oreal S.A.||Cosmetic for coating keratin fibers comprising cationic polymer, anionic polymer and aqueous dispersion of a polyalkyl methacrylate; coating, lengthening and curling eyelashes; durable|
|US6589519||Aug 24, 1998||Jul 8, 2003||L'oreal S.A.||Cosmetic compositions containing a polyoxyalkylenated aminosilicone block copolymer and a conditioner, and uses thereof|
|US6635262||Mar 14, 2001||Oct 21, 2003||L'oreal S.A.||Roll-on applicator comprising a hair composition|
|US6663902||Sep 19, 2000||Dec 16, 2003||Ecolab Inc.||And a source of chlorite ions; for cleaning, sanitizing, deodorizing, and disinfecting various surfaces|
|US6695887||Jan 2, 2001||Feb 24, 2004||L'oreal S.A.||Ready-to-use|
|US6800096||Nov 10, 2000||Oct 5, 2004||L'oreal S.A.||Viscosity; hair; amino resin-polyether copolymer as thickener|
|US6800098||Nov 10, 2000||Oct 5, 2004||L'oreal, S.A.||Oxidation dye composition for keratinic fibres containing a thickening polymer with an ether plastic skeleton|
|US6846333||Nov 8, 2002||Jan 25, 2005||L'oreal, S.A.||Mixture containing direct or oxidation dye|
|US6916344||Nov 10, 2000||Jul 12, 2005||L'oreal S.A.||A hair color mixtures comprising a thickener of amino resins-polyether copolymer, or an addition-condensation copolymer; two-compartment kits, in situ mixing|
|US6919073||May 16, 2002||Jul 19, 2005||L'oreal S.A.||Pulverulent composition for bleaching human keratin fibers|
|US6923835||Sep 9, 2003||Aug 2, 2005||L'oreal S.A.||Hair dyes comprising heterocyclic amines such as N,N'-bis[1-(4-aminophenyl)pyrrolidin-3-yl]-N,N,N',N'-tetramethylhexane-1,6-diaminium dichloride having colorfastness and chemical resistance|
|US6946005||Mar 27, 2003||Sep 20, 2005||L'oreal S.A.||Pyrrolidinyl-substituted para-phenylenediamine derivatives substituted with a cationic radical, and use of these derivatives for dyeing keratin fibers|
|US6955806||Jan 17, 2002||Oct 18, 2005||Genzyme Corporation||For therapy of microbial infection in mammal|
|US6984250||Nov 10, 2000||Jan 10, 2006||L'oreal||Composition, method, and kit for the bleaching or permanent reshaping of keratin fibers, comprising at least one thickening polymer with an aminoplast-ether skeleton|
|US6991707||Jun 4, 2002||Jan 31, 2006||Buckman Laboratories International, Inc.||Polymeric creping adhesives and creping methods using same|
|US7045673||Dec 8, 1999||May 16, 2006||Quick-Med Technologies, Inc.||improved antimicrobial dressing composition having a quaternary ammonium antimicrobial agent which can be maintained securely attached to a superabsorbent polymer upon exposure to acids and bases produced by infection and bacterial growth; wound dressing, sanitary napkins|
|US7066965||Nov 6, 2001||Jun 27, 2006||L'oreal S.A.||Hair dyes|
|US7077869||Nov 6, 2001||Jul 18, 2006||L'oreal S.A.||Composition for bleaching or permanent waving of keratinous fibers comprising a cationic associative polyurethane|
|US7101405||Nov 6, 2001||Sep 5, 2006||L'oreal S.A.||Oxidation dyeing composition for karatinous fibers comprising a cationic associative polyurethane|
|US7108726||Nov 6, 2001||Sep 19, 2006||L'oreal S.A.||Direct dyeing composition for keratinous fibres comprising a cationic associative polyurethane|
|US7128902||Nov 8, 2002||Oct 31, 2006||L'oreal, Sa||A dimethylsilanediol or alkoxydimethylsilanol end capped aminoethylamino/propylsilanetriol or alkoxysilanediol monomer containing polysiloxane and a reducing agent for the treatment of human hair|
|US7132534||Jul 7, 2003||Nov 7, 2006||L'oreal||Para-phenylenediamine derivatives containing a pyrrolidyl group, and use of these derivatives for coloring keratin fibers|
|US7135167||Nov 8, 2002||Nov 14, 2006||L'oreal, Sa||Oxidizing composition for treating keratin fibers, comprising a particular aminosilicone|
|US7138109||Nov 8, 2002||Nov 21, 2006||L'oreal, Sa||Using a polysiloxanes|
|US7147672||Oct 21, 2003||Dec 12, 2006||L'oreal S.A.||Dyeing human hair|
|US7147673||Apr 1, 2004||Dec 12, 2006||L'oreal S.A.||Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one insoluble polyorganosiloxane conditioning polymer, process therefor and use thereof|
|US7150764||Apr 1, 2004||Dec 19, 2006||L'oreal S.A.||compositions for dyeing with a lightening effect a human keratin material|
|US7153331||Dec 20, 2002||Dec 26, 2006||L'oreal S.A.||Dyeing composition for keratinous fibers comprising an oxyethylene rapeseed fatty acid amide|
|US7157413||Jul 8, 2003||Jan 2, 2007||L'oreal||Detergent cosmetic compositions comprising an anionic surfactant, an amphoteric, cationic, and/or nonionic surfactant, and a polysacchardie, and use thereof|
|US7179301||Mar 13, 2001||Feb 20, 2007||L'oreal S.A.||Hair dyes; variety of shades|
|US7186278||Apr 1, 2004||Mar 6, 2007||L'oreal S.A.||Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor|
|US7189266||Jun 10, 2002||Mar 13, 2007||L'oreal, S.A.||Dyeing composition for human keratinous fibres with direct dyes and dicationic compounds|
|US7192454||Apr 1, 2004||Mar 20, 2007||L'oreal S.A.||Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof|
|US7195650||Apr 1, 2004||Mar 27, 2007||L'oreal S.A.||Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye|
|US7195651||Apr 1, 2004||Mar 27, 2007||L'oreal S.A.||Reducing skin and/or hair color; lighter, uniform, homogeneous tones of natural appearance; kits|
|US7198650||Apr 1, 2004||Apr 3, 2007||L'oreal S.A.||Applying mixture to hair; development; rinsing|
|US7204860||Apr 1, 2004||Apr 17, 2007||L'oreal||Using aliphatic diol; dyeing hair|
|US7208018||Apr 1, 2004||Apr 24, 2007||L'oreal||Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof|
|US7211268||Nov 15, 2002||May 1, 2007||L'oreal S.A.||Preparation of polysaccharide betainate type compounds, compounds obtained, their use and compositions comprising them|
|US7217296||Sep 24, 2002||May 15, 2007||L'oreal S.A.||Dyeing composition with a lightening effect for human keratin materials comprising at least one fluorescent dye|
|US7217298||Jan 16, 2004||May 15, 2007||L'oreal S.A.||anhydrous bleaching paste and oxidizer; hydrogen peroxide in water in oil emulsion containing nonionic and, or anionic surfactant|
|US7220285||Apr 27, 2006||May 22, 2007||L'oreal S.A.||Pulverulent composition for bleaching human keratin fibers|
|US7220408||Nov 8, 2002||May 22, 2007||L'oreal, S.A.||Mixture of aminosilicone and thickener|
|US7223385||Nov 8, 2002||May 29, 2007||L'oreal S.A.||Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof|
|US7226486||Jan 15, 2004||Jun 5, 2007||L'oreal S.A||Ready-to-use bleaching compositions, preparation process and bleaching process|
|US7232561||Jun 2, 2003||Jun 19, 2007||L'oreal S.A.||Washing compositions comprising at least one amphiphilic block copolymer and at least one cationic or amphoteric polymer|
|US7250064||Apr 1, 2004||Jul 31, 2007||L'oreal S.A.||Using crosslinked acrylic polymer|
|US7258852||Sep 10, 2002||Aug 21, 2007||L'oreal S.A.||Cosmetic compositions containing a methacrylic acid copolymer and an oil, and uses thereof|
|US7261744||Dec 23, 2003||Aug 28, 2007||L'oreal S.A.||Method for dyeing or coloring human keratin materials with lightening effect using a composition comprising at least one fluorescent compound and at least one optical brightener|
|US7267696||Mar 25, 2004||Sep 11, 2007||L'oreal S.A.||Composition for dyeing keratinous fibers, comprising a hydroxycarboxylic acid or a salt, ready-to-use composition comprising it, implementation process and device|
|US7294152||Jan 7, 2005||Nov 13, 2007||L'oreal S.A.||Dyeing composition comprising at least one fluorindine compound for the dyeing of keratinic fibers, dyeing process comprising the composition and compound|
|US7303588||Mar 25, 2004||Dec 4, 2007||L'oreal S.A.||Composition for dyeing keratinous fibers, comprising at least one polycarboxylic acid or a salt, ready-to-use composition comprising it, implementation process and device|
|US7303589||Apr 1, 2004||Dec 4, 2007||L'oreal S.A.||Process for dyeing human keratin fibers, having a lightening effect, comprising at least one fluorescent compound and compositions of the same|
|US7323015||Oct 21, 2003||Jan 29, 2008||L'oreal S.A.||Dyeing human hair|
|US7326256||Dec 8, 2003||Feb 5, 2008||L'ORéAL S.A.||dyeing human hair; aqueous solution|
|US7329287||Dec 8, 2003||Feb 12, 2008||L'oreal S.A.||Oxidation dye composition for keratin fibers, comprising at least one oxidation dye, at least one associative polymer, at least one nonionic cellulose-based compound not comprising a C8-C30 fatty chain, and at least one cationic polymer with a charge density of greater than 1 meq/g and not comprising a C8-C30 fatty chain|
|US7348301||Feb 16, 2006||Mar 25, 2008||Buckman Laboratories International, Inc.||Lysozyme-based method and composition to control the growth of microorganisms in aqueous systems|
|US7364594||Nov 22, 2001||Apr 29, 2008||L'oreal S.A.||E.g., a quaternized polyetherurethane copolymer and an acrylamide/ dimethyldiallylammonium chloride/acrylic acid terpolymer.|
|US7429275||Dec 23, 2005||Sep 30, 2008||L'oreal S.A.||Use of at least one compound chosen from porphyrin compounds and phthalocyanin compounds for dyeing human keratin materials, compositions comprising them, a dyeing process, and compounds therefor|
|US7431740||Nov 22, 2001||Oct 7, 2008||L'oreal, S.A.||Oxidation dyeing composition for keratinous fibers comprising an associative polymer and a pearling agent|
|US7442214||Mar 31, 2006||Oct 28, 2008||L'oreal S.A.||Dye composition comprising at least one non-ionic associative polymer and process for dyeing keratin fibers using same|
|US7485289||Feb 15, 2007||Feb 3, 2009||L'oreal, S.A.||Cosmetic compositions containing a particular aminosilicone and a conditioner, and uses thereof|
|US7498022||Mar 28, 2003||Mar 3, 2009||L'oreal S.A.||One amphiphilic polymer chosen from branched block copolymers comprising at least one nonionic unit derived from at least one monomer chosen from C1-20 alkyl (meth)acrylates, N-mono-(C2-12 alkyl)- meth)acrylamides and N,N-di-(C2-12|
|US7504094||Feb 15, 2007||Mar 17, 2009||L'oreal, S.A.||Hair conditioners; alkoxy-capped copolymer with dimethylsiloxy units and 3-(2-aminoethyl)aminopropyl)methyl- (or alkoxy-)siloxy units; for improving the lightness, softness, sheen and/or disentangling, and/or facilitating styling of hair|
|US7510705||Sep 21, 2006||Mar 31, 2009||L'oreal, S.A.||Process for permanently reshaping the hair using particular aminosilicones|
|US7550015||Mar 31, 2006||Jun 23, 2009||L'oreal S.A.||hair dyes comprising oxidation dye precursors and direct dyes, nonionic surfactants or anionic surfactants, hydroxyethylcellulose, cationic polymer; and one fatty substance; fatty acid esters of polyethylene glycol; multi-compartment kit for store the dyes|
|US7569078||Mar 31, 2006||Aug 4, 2009||L'oreal S.A.||Dye composition comprising at least one cellulose and process for dyeing keratin fibers using the dye composition|
|US7575605||Mar 31, 2006||Aug 18, 2009||L'oreal S.A.||Dye composition comprising at least one glycerol ester and a process for dyeing keratin fibers using the composition|
|US7578854||Mar 31, 2006||Aug 25, 2009||L'oreal S.A.||Applying to wet or dry keratin fibers a formulation containing oxidation dye precursor such as phenolamines, a direct dye ( azo dye, methine dye etc.), a fatty alchol, a fatty alcohol ester of polyglycerol, a oxyalkylenated or glycerolated nonionic surfactant, a cationic polymer|
|US7608115||Apr 30, 2004||Oct 27, 2009||L'oreal S.A.||Via applying direct dye, oxidation base, coupler, and oxidizing agent, then heating; oxidation color dyes; hair conditioners; cosmetics|
|US7651533||Mar 31, 2006||Jan 26, 2010||Oreal||Dye composition with a reduced content of starting materials, process for dyeing keratin fibers using the same and device therefor|
|US7705112||Apr 17, 2007||Apr 27, 2010||Abbott Medical Optics Inc.||Mixing 1,4-bis(dimethylamino)-2-butene with triethanolamine, water and acid; then adding 1,4-dihalo-2-butene|
|US7708981||Mar 10, 2004||May 4, 2010||L'oreal S.A.||Cosmetic compositions comprising at least one crosslinked copolymer, at least one insoluble mineral particle and at least one polymer, and uses thereof|
|US7709694||Sep 28, 2001||May 4, 2010||Quick-Med Technologies, Inc.||Materials with covalently-bonded, nonleachable, polymeric antimicrobial surfaces|
|US7736631||Apr 1, 2004||Jun 15, 2010||L'oreal S.A.||Organic pigment colors and a modified polydimethylsiloxane homopolymer or copolymers for lightening hair or skin; multi-compartment kit for dyeing|
|US7771491||Dec 21, 2007||Aug 10, 2010||L'oreal S.A.||Hair dye; environmentally friendly, due to use of nonionic cellulose; good shampoo fastness|
|US7771492||Feb 23, 2009||Aug 10, 2010||L'oreal S.A.||Hair dyes; anionic thickener has hydrophilic olefinic unsaturated carboxylic acid and a C10-C30 alkyl unsaturated carboxylate; nonionic thickeners are celluloses modified by fatty chain or polyoxyethylenated polyurethanes; cationic thickener is quaternized cellulose with fatty acid chain; resists running|
|US7795374||Apr 23, 2009||Sep 14, 2010||Abbott Medical Optics Inc.||Mixing 1,4-bis(dimethylamino)-2-butene, water, a first portion of triethanolamine and acid; adding 1,4-dichloro-2-butene and heating the reaction mixture; adding a second portion of triethanolamine and acid, and isolating a quaternary ammonium polymer; antimicrobial for use with contact lenses|
|US7799093||Oct 25, 2007||Sep 21, 2010||L'ORéAL S.A.||Coloring composition of keratinous fibers comprising at least one polysiloxane/polyurea block copolymer|
|US7803899||Sep 27, 2006||Sep 28, 2010||Buckman Laboratories International, Inc.||combining water-soluble ionene polymer, polyaminoamide, or acrylamide/diallyldimethyl-ammonium halide copolymer in water with dry polar solvent (acetone) to form mixture that separates into layers, then separating layers and drying to obtain solid comprising water-soluble polymer; wet strength powders|
|US7867969||Oct 30, 2006||Jan 11, 2011||L'oreal S.A.||Composition for washing keratin materials comprising a magnesium salt anionic surfactant|
|US7914775||Nov 6, 2001||Mar 29, 2011||L'oreal S.A.||Treating keratinous fibres, in particular human keratinous fibres such as hair, comprising in a physiologically acceptable medium, at least a protecting or conditioning agent, and further at least a cationic associative|
|US7928087||Jan 11, 2002||Apr 19, 2011||L'oreal||provides a flow texture to cosmetic compositions and are easily rinsed; Hair treated with the composition has a soft feel free of residue; used for washing and/or conditioning keratinous matter such as hair or skin|
|US7976831||Apr 4, 2005||Jul 12, 2011||L'oreal S.A.||Method for treating hair fibers|
|US7998464||Sep 28, 2006||Aug 16, 2011||L'oreal S.A.||Process for the photoprotective treatment of artificially dyed keratin fibers by application of a liquid water/steam mixture|
|US7999063||Apr 23, 2009||Aug 16, 2011||Abbott Medical Optics Inc.||Polyquaternium-1 synthesis methods and associated formulations|
|US8106151||Jan 25, 2010||Jan 31, 2012||Abbot Medical Optics Inc.||Polyquaternium-1 synthesis methods|
|US8309679||Dec 21, 2011||Nov 13, 2012||Abbott Medical Optics Inc.||Polyquaternium-1 synthesis methods|
|US8586014||Oct 30, 2006||Nov 19, 2013||L'oreal||Composition for the care of keratin material and cosmetic treatment process using said composition|
|US8628586||Dec 7, 2011||Jan 14, 2014||L'oreal||Composition comprising an oxidation dye precursor, a polycondensate of ethylene oxide and propylene oxide and a cationic polymer with a charge density of greater than or equal to 4 meq./g|
|US8703109||Mar 28, 2008||Apr 22, 2014||L'oreal||Protection of keratinous fibers using ceramides and/or glycoceramides|
|US8784506||Oct 28, 2011||Jul 22, 2014||L'oreal||Dye composition having a low content of ammonia|
|US8790623||Jan 18, 2006||Jul 29, 2014||Il'Oreal||Composition for treating keratin fibers, comprising at least one aromatic alcohol, at least one aromatic carboxylic acid, and at least one protecting agent|
|US8802066||Dec 20, 2011||Aug 12, 2014||L'oreal||Cosmetic composition comprising a particular zinc salt and an amino silicone|
|DE19646726A1 *||Nov 13, 1996||May 14, 1998||Widulle Herbert Dipl Chem Dr||Topical composition containing polymeric quaternary ammonium salt|
|DE102007030642A1||Jul 2, 2007||Jan 8, 2009||Momentive Performance Materials Gmbh||Verfahren zur Herstellung von Polyorganosiloxanen mit (C6-C60)-Alkylmethylsiloxygruppen und Dimethylsiloxygruppen|
|DE102012012263A1 *||Jun 22, 2012||Dec 24, 2013||Alfred E. Tiefenbacher (Gmbh & Co. Kg)||Verfahren zur Herstellung von Polyquaternium-1|
|DE202013011676U1||Nov 8, 2013||Feb 14, 2014||L'oreal||Zusammensetzung, die eine Dicarbonylverbindung enthält|
|EP0382562A1 *||Feb 9, 1990||Aug 16, 1990||Buckman Laboratories International, Inc.||Polymeric quaternary ammonium trihalides useful as microbicides, sanitizers and disinfectants|
|EP0723772A1||Jan 10, 1996||Jul 31, 1996||L'oreal||Reducing composition bared on a basic amino acid and a cationic polymer|
|EP1634569A1||Aug 3, 2005||Mar 15, 2006||L'oreal||Cosmetic composition based on a cationic surfactant, a fatty alcohol, a cationic non-silicone polymer and a diol|
|EP1688127A1||Dec 12, 2005||Aug 9, 2006||L'oreal||Hair treatment composition containing an aromatic alcohol, an aromatic carboxylic acid a protecting agent|
|EP1698326A2||Jan 10, 2006||Sep 6, 2006||L'oreal||Cosmetic composition comprising a cationic surfactant, a cationic polymer, a solid compound and a starch, and cosmetic treatment process|
|EP1707181A1||Mar 28, 2006||Oct 4, 2006||L'oreal||Dye composition with a reduced content of starting materials, and process for dyeing keratin fibres using the same|
|EP1707182A1||Mar 28, 2006||Oct 4, 2006||L'oreal||Dye composition comprising a fatty acid ester and process for dyeing keratin fibres using the same|
|EP1707183A1||Mar 28, 2006||Oct 4, 2006||L'oreal||Dye composition comprising a non-ionic associative polymer, process for dyeing keratin fibres using same|
|EP1707184A1||Mar 28, 2006||Oct 4, 2006||L'oreal||Dye composition with a reduced content of starting materials, process for dyeing keratin fibres using the same and device therefor|
|EP1707190A1||Mar 28, 2006||Oct 4, 2006||L'oreal||Dye composition comprising a hydrophobically modified nonionic cellulose and method for dyeing keratin fibres using it|
|EP1716840A1||Mar 28, 2006||Nov 2, 2006||L'oreal||Hair-dye composition containing a glycerol ester and the corresponding hair-dyeing process|
|EP1716841A1||Nov 26, 2003||Nov 2, 2006||L'Oréal||Composition for the oxidative dyeing of keratinic fibers|
|EP1920755A1||Nov 9, 2007||May 14, 2008||L'Oréal||Method for permanently deforming keratinous fibres comprising a step of applying an intermediate rinsing component comprising a monovalent metal cation salt or an ammonia salt and an organic acid|
|EP1935396A1||Dec 20, 2007||Jun 25, 2008||L'Oreal||Method for permanently deforming keratinous fibres including a step of applying a reducing composition with a low concentration and an intermediate drying step|
|EP1944011A1||Jan 9, 2008||Jul 16, 2008||L'Oréal||Reductive composition designed to be used in a method for permanently deforming keratinous fibres containing cysteine and thiolactic acid or one of their salts|
|EP1997473A2||Apr 24, 2008||Dec 3, 2008||L'Oreal||Use of a multi-carbosite, multi-group coupling agent for protecting the colour of artificially dyed keratin fibres with respect to washing; dyeing processes|
|EP2011473A1||Jun 26, 2008||Jan 7, 2009||L'Oreal||Anhydrous composition in paste form for bleaching keratinous fibres.|
|EP2039344A2||Sep 12, 2008||Mar 25, 2009||L'Oréal||Cosmetic composition comprising a cationic copolymer and an anionic associative polymer and cosmetic treatment process|
|EP2039345A1||Sep 12, 2008||Mar 25, 2009||L'Oréal||Cosmetic compositions containing a cationic copolymer and a particular triglyceride and uses thereof|
|EP2039346A1||Sep 12, 2008||Mar 25, 2009||L'Oréal||Cosmetic composition comprising a cationic copolymer and a starch and cosmetic treatment process|
|EP2065023A2||Nov 28, 2008||Jun 3, 2009||L'Oreal||Hairstyling composition comprising at least one (meth)acrylic copolymer and at least one pearlescent agent|
|EP2065024A2||Nov 28, 2008||Jun 3, 2009||L'Oreal||Hairstyling composition comprising (meth)acrylic copolymers and at least one oil|
|EP2065028A2||Nov 28, 2008||Jun 3, 2009||L'Oreal||Repositionable hairstyling composition comprising at least one (meth)acrylic copolymer and at least one silicone.|
|EP2065074A2||Nov 7, 2008||Jun 3, 2009||L'Oréal||Composition for the oxidation dyeing of keratin fibres comprising a cellulose with hydrophobic substituent(s), an oxidation dye and a cationic polymer|
|EP2070511A2||Sep 12, 2008||Jun 17, 2009||L'Oreal||Cosmetic composition comprising at least one specific cationic polymer, at least one surface-active agent, at least one cationic or amphoteric polymer and at least one mineral particle, and cosmetic treatment method using said composition|
|EP2072033A2||Sep 12, 2008||Jun 24, 2009||L'Oreal||Cosmetic composition comprising at least one specific cationic polymer and at least one fatty acid ester in C8-C24 and oxyethylenated sorbitan comprising 2 to 10 oxyethylene patterns, and cosmetic treatment method using said composition|
|EP2072084A2||Sep 12, 2008||Jun 24, 2009||L'Oréal||Cosmetic compositions containing a cationic copolymer, an amino silicone and a cationic polymer, and uses thereof|
|EP2092933A1||Feb 20, 2009||Aug 26, 2009||L'Oréal||Use of particular cationic polymers in a dye composition and associated with a chelating agent as antioxidants or free-radical scavengers|
|EP2092961A1||Feb 20, 2009||Aug 26, 2009||L'Oréal||Use of particular cationic polymers as anti-oxidant or anti-radical agents|
|EP2111842A1||Mar 26, 2009||Oct 28, 2009||L'Oréal||Dyeing composition comprising ammonium chloride, method of colouring keratin fibres, and device|
|EP2113240A1||Apr 27, 2009||Nov 4, 2009||L'Oréal||Cosmetic composition comprising an emulsion obtained by a PIT method|
|EP2116220A1||Apr 16, 2009||Nov 11, 2009||L'Oreal||Cosmetic composition comprising an emulsion obtained by a PIT method|
|EP2181596A1||Feb 15, 2007||May 5, 2010||Buckman Laboratories International, Inc||Method of inhibiting the growth of microorganism in aqueous systems using a composition comprising lysozyme|
|EP2198837A1||Dec 17, 2009||Jun 23, 2010||L'oreal||Cosmetic composition containing four surfactants, a cationic polymer and a zinc salt|
|EP2198850A1||Dec 18, 2009||Jun 23, 2010||L'oreal||Cosmetic composition containing four types of surfactants and one non-silicone fatty derivative|
|EP2198929A1||Dec 18, 2009||Jun 23, 2010||L'oreal||Hair dye or lightening composition comprising a fatty substance and a cationic polymer, and use thereof|
|EP2236053A1||Apr 1, 2010||Oct 6, 2010||L'Oréal||Method for the steam treatment of hair|
|EP2246039A1||Apr 29, 2010||Nov 3, 2010||L'Oréal||Method for dyeing hair comprising the step of treating the hair with an organic silicon compound|
|EP2246040A2||Apr 12, 2010||Nov 3, 2010||L'Oréal||Method for the shaping of hair including a step of applying a reducing composition and a heating step|
|EP2266528A1||Apr 29, 2010||Dec 29, 2010||L'Oréal||Process for colouring and/or bleaching human hair using a composition comprising an amino trialkoxysilane or amino trialcenyloxysilane|
|EP2275082A1||Dec 4, 2003||Jan 19, 2011||L'Oréal||Composition for oxidation dyeing keratin fibers comprising a nonionic associative polymer, a specific cellulosic compound and a specific cationic polymer.|
|EP2301630A2||Dec 18, 2009||Mar 30, 2011||L'Oréal||Oxidizing composition for the treatment of keratin fibres comprising a cationic polymer, a fatty amide and an anti-oxygen agent|
|EP2338469A1||Dec 16, 2010||Jun 29, 2011||L'Oréal||Use of a cosmetic composition containing a linear volatile alcane and an associative non-ionic polymer for conditioning the hair|
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| || |
|U.S. Classification||504/158, 526/294, 424/78.35, 514/642|
|International Classification||A61K8/04, C08G73/00, C02F1/50, A61K8/30, A61K8/72, A61K8/06, A61K8/84, A61Q17/00, A61K8/40, C08G73/02|
|Cooperative Classification||C02F1/50, C08G73/0226, A61K8/06, A61K8/40, A61Q17/005, C08G73/0213, A61K8/84|
|European Classification||A61K8/40, C02F1/50, A61K8/84, A61Q17/00F, C08G73/02A9, C08G73/02A9C, A61K8/06|
|Jun 16, 1993||AS||Assignment|
Owner name: MILLMASTER ONYX GROUP, L.P.
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:MOG ACQUISITION CORPORATION;REEL/FRAME:006587/0526
Effective date: 19930122
Owner name: MOG ACQUISITION CORPORATION
Free format text: MERGER;ASSIGNOR:MILLMASTER ONYX GROUP, INC.;REEL/FRAME:006589/0218
Effective date: 19930121
|Jun 16, 1993||AS02||Assignment of assignor's interest|
Owner name: MILLMASTER ONYX GROUP, L.P. 500 POST ROAD EAST WES
Owner name: MOG ACQUISITION CORPORATION
Effective date: 19930122
|Jun 16, 1993||AS03||Merger|
Owner name: MILLMASTER ONYX GROUP, INC.
Owner name: MOG ACQUISITION CORPORATION 500 POST ROAD EAST WES
Effective date: 19930121
|Jan 21, 1993||AS||Assignment|
Owner name: MILLMASTER ONYX GROUP, INC., CONNECTICUT
Free format text: RELEASED BY SECURED PARTY;ASSIGNOR:BANKERS TRUST COMPANY;REEL/FRAME:006388/0575
Effective date: 19920630
|Jan 21, 1993||AS17||Release by secured party|
Owner name: BANKERS TRUST COMPANY
Owner name: MILLMASTER ONYX GROUP, INC. 500 POST ROAD EAST WES
Effective date: 19920630
|Nov 6, 1992||AS||Assignment|
Owner name: CIT GROUP/BUSINESS CREDIT, INC., NEW YORK
Free format text: SECURITY INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC.;REEL/FRAME:006319/0109
Effective date: 19920630
|Sep 30, 1992||AS||Assignment|
Owner name: MILLMASTER ONYX GROUP, INC.
Free format text: RE-ASSIGNMENT AND RELEASE.;ASSIGNOR:BANKERS TRUST COMPANY;REEL/FRAME:006273/0869
Effective date: 19920630
|Sep 30, 1992||AS99||Other assignments|
Free format text: MILLMASTER ONYX GROUP, INC. * BANKERS TRUST COMPANY : 19920630 OTHER CASES: NONE; RE-ASSIGNMENT ANDRELEASE.
|Oct 25, 1988||AS||Assignment|
Owner name: BANKERS TRUST COMPANY, A CORP. OF NY, NEW YORK
Free format text: SECURITY INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A CORP. OF DE;REEL/FRAME:005002/0735
Effective date: 19881019
|Jun 9, 1983||AS||Assignment|
Owner name: BARCLAYS AMERICAN, 1 BUSINESS CREDIT, INC. 111 FOU
Free format text: SECURITY INTEREST;ASSIGNOR:MILLMASTER ONYX GROUP, INC., A DE CORP.;REEL/FRAME:004139/0941
Effective date: 19821222
Owner name: MILLMASTER ONYX GROUP, INC., A DE CORP.
Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:KEWANEE INDUSTRIES, INC.;REEL/FRAME:004139/0909
Effective date: 19830407