US3836636A - Oxidative treatment of human hair with an acylated glycoluril and an oxidizer - Google Patents
Oxidative treatment of human hair with an acylated glycoluril and an oxidizer Download PDFInfo
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- US3836636A US3836636A US00141373A US14137371A US3836636A US 3836636 A US3836636 A US 3836636A US 00141373 A US00141373 A US 00141373A US 14137371 A US14137371 A US 14137371A US 3836636 A US3836636 A US 3836636A
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- glycoluril
- acid
- human hair
- acylated
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- 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
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
- C11D3/3917—Nitrogen-containing compounds
- C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/08—Preparations for bleaching the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/10—Preparations for permanently dyeing the hair
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0245—Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
- B01J31/0249—Ureas (R2N-C(=O)-NR2)
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S424/00—Drug, bio-affecting and body treating compositions
- Y10S424/03—Hair bleach
Definitions
- Activator Activator: tetraaeetyltetrapropionyl- Sample taken after 0: minutes glycoluril glycoluril From the above, it can be seen that the extent of activation is dependent upon the pH, the temperature, the amount of the activator used and upon the nature of the acyl radical present. Thus, with tetraacetylglycoluril already at the start of the experiment, high degrees of activation are obtained, with tetrapropionylglycoluril the degrees of activations are higher near the end of the experiment.
- the bleaching activation is less at the start of the treatment. It is thus easier to attain only a partial lightening of the color tone up to a definite, desired color tone.
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (AREA)
- Materials Engineering (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
THE MEHTOD OF OXIDATIVE TREATMENT OF HUMAN HAIR WHICH COMPRISES TREATING SAID HAIR WITH AN AQUEOUS SOLUTION OF (1) WATER-SOLUBLE PEROXYHYDRATES OR HYDROGEN PEROXIDE AND (2) AN ACTIVATOR ACYLATED GLYCOLURIL.
Description
United States Patent O 3,836,636 OXIDATIVE TREATMENT OF HUMAN HAIR WITH AN ACYLATED GLYCOLURIL AND AN OXIDIZER Dieter Kuhling, Monheim, Rhineland, Germany, assignor to Henkel & Cie G.m.b.H., Dusseldorf-Holthauseu,
- Germany No Drawing. Continuation-in-part of abandoned application Ser. No. 787,597, Dec. 27, 1968. This application May 7, 1971, Ser. No. 141,373 Claims priority, application Germany, Dec. 30, 1967, P 16 95 219.5 Int. Cl. A61k 7/12 U.S. Cl. 424-62 8 Claims ABSTRACT OF THE DISCLOSURE The method of oxidative treatment of human hair which comprises treating said hair with an aqueous solution of (1) water-soluble peroxyhydrates or hydrogen peroxide and (2) an activator acylated glycoluril.
REFERENCE TO PRIOR APPLICATIONS This application is a continuation-in-part of copending Ser. No. 787,597, filed Dec. 27, 1968, and now abandoned.
THE PRIOR ART Aqueous solutions of inorganic per-compounds, especially of hydrogen peroxide or perborates, have been used for a long time as oxidizing and bleaching agents for a large variety of materials. However, for practical purposes the active oxygen released by the per-compounds does not act with sufiicient speed. Therefore, these bleach ing agents cannot be adequately used with materials such as human hair which is sensitive to temperature, and which has to be bleached at relatively low temperatures, except on prolonged application times.
OBJECTS OF THE INVENTION An object of the present invention is the development of materials which will activate per-compounds, particularly at temperatures below 45 C.
Another object of the invention is the development of a method of oxidative treatment of human hair which consists essentially of contacting human hair, at a temperature of from 20 C. to 45 C., with an aqueous liquid containing an oxidizer selected from the group consisting of water-soluble peroxyhydrates and hydrogen peroxide in an amount sufficient to supply from 10 gm. to 200 gm. per liter of H equivalent and from 20 gm. to 500 gm. per liter of an activator acylated glycoluril having the formula wherein at least two of R R R and R are acyls of organic carboxylic acids having from 2 to 8 carbon atoms selected from the group consisting of alkanoic acids, nitriloacetic acid, haloalkanoic acids, benzoic acid, nitrobenzoic acid, halobenzoic acid, toluic acid, nitro-toluic acid, halotoluic acid, methoxybenzoic acid and nitrilo- 3,836,636 Patented Sept. 17, 1974 benzoic acid, and the remainder of R R R and R are members selected from the group consisting of alkyl having from 1 to 8 carbon atoms and said acyls of organic carboxylic acids having from 2 to 8 carbon atoms.
These and other objects of the invention will become more apparent as the description thereof proceeds.
DESCRIPTION OF THE INVENTION The invention relates to the use of certain organic substances as activators for per-compounds, which enable the minimum temperature needed for a practically effective bleaching and oxidative treatment of human hair to be reduced and/ or the oxidation process to be accelerated.
The substances to be used as activators for the percompounds according to the invention are acylated glycolurils of the following formula f e K /i\ it, t.
where at least two of R R R and R are acyls of acids selected from the group consisting of alkanoic acids having 2 to 4 carbon atoms, chloroalkanoic acids having 2 to 4 carbon atoms and benzoic acid and the remainder of R R R and R are members selected from the group consisting of alkyl having 1 to 8 carbon atoms and said acyls of said acids.
Suitable acyl residues of organic carboxylic acids having from 2 to 8 carbon atoms are, for example, alkanoyls, such as acetyl, propionyl, butyryl, etc.; haloalkanoyls, such as monobromoacetyl and preferably chloroalkanoyls such as monochloroacetyl, dichloroacetyl, trichloroacetyl, etc.; nitriloacetyl, benzoyl and toluyl which may be substituted with nitro groups or halogen atoms such as chlorobenzoyl nitrobenzoyl, chlorotoluyl and nitrotoluyl; methoxybenzoyls; and nitrilobenzoyls. Suitable alkyls having 1 to 8 carbon atoms are, for example, methyl, ethyl, etc. Tetraacetylglycoluril and its preparation are known. It is obtained by acetylating glycoluril with acetic acid anhydride. The other acylated glycolurils can be prepared in an analogous way be reacting the glycoluril with carboxylic acid anhydrides, carboxylic acid chlorides or carboxylic acid esters. Apart from tetraacetyl-glycoluril, the activators to be used according to the invention are new chemical substances.
3 Among the preferred acylated glycouril can be mentioned the following:
tetraacetyl-glycoluril (mp. 233240 C.), tetrapropionyl-glycoluril (mp. l44-l46 C.), tetrabutyryl-glycoluril, 1,3-dimethyl-4,-diacetyl-glycoluril, 1-methyl-3.4,6-triacetyl-glycoluril (m.p. l79-l8() C), diacetyl-dipropionyl-glycoluril (mp. 144-l46 C.), 1,3-dimethy1-4-acetyl-6-propionyl-glycoluril, diacetyl-dibenzoylglycoluril (mp. 244249 C).
The alkyl and aryl substituted glycolurils may be produced by condensation of glyoxal with the alkyl or aryl substituted ureas. Any of the above acylated glycolurils may be substituted for the tetraacetylglycoluril and tetrapropionylglycoluril utilized in the examples with comparable activation of the active oxygen, taking into account the fact that a larger amount of a diacylated or triacylated glycoluril must be utilized in replacement of a tetraacylated glycoluril.
The per-compounds to be activated can be any type of inorganic or organic per-compound which will release active oxygen in an aqueous solution. For economic reasons, the per-compounds preferably utilized are inorganic peroxides, inorganic per-acids, inorganic peroxyhydratcs and products of the addition of hydrogen peroxide with inorganic and organic compounds.
Of the peroxides to be activated, hydrogen peroxide is of the greatest practical importance. It may be used as such, but may also be used in the form of its mostly solid peroxyhydrates or products of addition with inorganic and organic compounds. The latter include, for example, the products of addition of hydrogen peroxide to urea or melamine, and examples of the peroxyhydrates are the perborates, perortho-, perpyro-, and perpoly-phosphates, percarbonates and persilicates. These peroxyhydrates are preferably soluble in water and are ordinarily utilized in the form of their alkali metal salts, such as their sodium salts. The activators according to the invention, however, may also be used together with true per-acids, such as for example, Caros acid (peroxymonosulfuric acid, H 50 or peroxydisulfuric acid (H S O or their salts.
If one works at temperatures up to 45 C. with a tetraacylated glycoluril, 2 of the 4 acyl groups which are present are available for activation of the active oxygen. Theoretically, therefore, one molecule or tetraacetylglycoluril is in a position to activate 2 oxygen atoms. In practice, however, satisfactory effects are attained in many cases even with substantially smaller amounts of activator, while on the other hand, the activator may also be used in relatively large excess. In general, the amount of activator used is chosen so that 0.5 to 6, preferably 2 to 4 acyl residues are present per active oxygen atom.
The acceleration of the bleaching and oxidizing processes on human hair is shown at low temperatures in the range from 20 C. to 45 C., and preferably from 20 C. to 37 C. and more, particularly from 20 C. to 30 C. Depending upon the problem to be solved, it is possible for the technician, when using the activators according to the invention, either to reduce the temperature of treatment and/ or to shorten the time of treatment, the temperature remaining the same.
The conditions to be maintained during operation with the activators according to the invention, such as for example, the concentration of the peroxide, temperature, pH value and time of treatment, depend substantially on the color of the hair to be oxidized and/or bleached and the brightness of the desired color tone if an oxidative dyestutf is employed. The usually aqueous oxidizing or bleaching liquids may contain gm. to 200 gm., preferably gm. to 100 gm, per liter of H 0 equivalent and have a pH value from 7 to 11, and especially from 8 to 10.5.
As previously stated, aqueous solutions of per-compounds and acylated glycoluril activators, optionally with 4 other ingredients as indicated below may be utilized. These aqueous solutions preferably contain suflicient per-compounds to give a concentration of from 20 mg. to 500 mg., preferably 50 mg. to 250 mg. per liter of active oxygen and sufiicient acylated glycoluril activators to provide from 0.5 to 6, preferably 2 to 4 acyl residues of the acylated glycoluril per active oxygen atoms and preferably from 20 gm. to 500 gm. per liter of the acylated glycoluril.
The activators, according to the invention, may be used wherever per-compounds, especially hydrogen peroxide or perborates, have previously been used as oxidizing and/or bleaching agents for the oxidative treatment of human hair, preferably living human hair.
The desired pH value is adjusted by addition of neutralor alkaline-reacting substances, possibly by buffer mixtures, and particularly by additives which have also been co-employed in a corresponding, formerly customary, treatment.
These frequently include the suface-active substances which serve to decrease the surface tension of the aqueous oxidizing or bleaching liquid, such as for example, soap or known synthetic detergents of anionic, non-ionic or amphoteric nature. When working in the alkaline range, alkaline substances may be added as well as inorganic or organic complex-forming compounds, especially complexforming compounds suitable for binding the so-called hardness-producing substances in water or heavy metals which may possibly be present.
The following examples are illustrative of the practice of the invention without, however, being limitative in any manner.
EXAMPLE 1 Preparation of 1,3,4,6-tetraacetyl-glycoluril A suspension of gm. of glycoluril in 1.5 liters of acetic acid anhydride was boiled under reflux with stirring, until the glycoluril had completely dissolved. After distilling off the excess acetic acid anhydride and the acetic acid formed in the reaction, the crude tetraacetylglycoluril remained. It may be used without further processing, but if desired it can be purified, for example, by recrystallization in the following way.
The crude tetraacetyl-glycoluril was taken up in a little methanol and the solvent was filtered off from the residue remaining undissolved. The residue was recrystallized from a mixture of 4 parts by volume of methanol and 1 part by volume of ethyl acetate. g. (52.8% of theory) of tetraacetyl-glycoluril having a melting point of 233 to 240 C. were obtained. According to the data in the literature, the melting point is 236 to 238 C.
As may be seen, the analysis data calculated for the fzomplosition C H N O agreed well with the figures oun Calculated: C=46.40%; H=4.52%; N=18.05% Found: C=46.36%; H=4.97%; N=18.12%
Moreover, infra-red and NMR spectra showed the characteristic bands for tetraacetyl-glycoluril.
EXAMPLE 2 In an analogous way, 82 g. of tetrapropionyl-glycoluril having a melting point of 144 to 146 C. were obtained by acylating 100 g. of glycoluril in 1.5 liters of propionic acid anhydride and recrystallizing the reaction product from isopropanol. This corresponded to a theoretical yield of 31.5%. The analysis data found agreed well with the figures calculated for the composition C H N O Calculated: C=52.50%; H=6.06%; N=15.32% Found: C=52.64%; H=6.19%; N=15.61%
Moreover, the molecular Weight of 358.7, found by osmosis in acetone agreed with that calculated (366.38). Infra-red and NMR spectra showed the characteristic bands to be expected for tetrapropionyl-glycoluril.
EXAMPLES 3 AND 4 The usefulness of the activators according to the invention was demonstrated by the following experiments: 1;..A. solution which contained 0.615 gm. of NaBO .H O .3H O (4 mMol) and 2.5 gm. of Na PgO .l0H O per liter, after addition of 4 mMol of activator, was heated to 45 and maintained at the said temperature with stirring during the whole experiment. At certain intervals of time, 100 ml. samples were removed by' pipette, immediately added to a mixture of 250 gm. of ice and ml. of glacial acetic acid, and then, after addition of about 0.35 gm. of potassium iodide, were titrated with 0.1 N sodium thiosulfate solution using starch as an indicator.
Under. the experimental conditions indicated, 8.0 ml. ofethiosulfate solution were consumed with a 100% activation of the peroxy-compound used. The thiosulfate consumed and the percentage amount of activated peroxycompound are given in the Tables I and II.
Table for Example 3:
TABLE I.ACTIVATION 0F PERBORATE WITH TE'IRA ACETYL-GLYCOLURIL Activation obtained at 45 C.
. M1. 0.1 N Percent 0 Sample taken after 1 minutes NazSzOa activated Table for Example 4:
TABLE -H.-AC'IIVATION OF PERBORATE WITH TETRA- As will be perceived, when tetraacetyl-glycoluril is used, the maximum degree of activation is reached after a time, according to the experiment, of only one minute, and this is maintained in practice over a certain period irrespective of the temperature chosen. The subsequent falling off of the values is due to the spontaneous decomposition of the peracetic acid first formed. In the case of tetrapropionylglycoluril, the amount of activated oxygen increases more slowly. The products therefore differ in the progress of the activation per unit time and it is possible to select an activator, the action of which is optimal for the bleaching or oxidizing process in question.
EXAMPLES 5 AND 6 Solutions which contained 620 mg./l. of a commercial sodium perborate tetrahydrate with about 94% by weight active oxygen (4 mg.-atom/l. active oxygen) and 2.5 gm./l. Na P O- JOH O, were after addition of 620 mg./l. tetraacetyl-glycoluril (2 mMol/L, corresponding to 2 aeetyl radicals per active oxygen) kept at C. under constant stirring. In definite time periods 100 ml. were pipetted off, immedately put on a mixture of 250 gm. ice and 15 ml. glacial acetic acid and subsequently, after addition of about 0.35 gm. potassium iodide, titrated with 0.1 N sodium thiosulfate solution and starch as indicator. The pH of this solution, measured immediately after addition of the tetraacetylglycoluril, was 10.35; in two parallel experiments solutions were processed whose pH-values TAB LE III Percent oxygen activated at 20 0.,
activator: tetraacetylglycolun'l Sample taken after 2: minutes pH=8.20 H=10.05 pH=10.35
In a second experimental series the activation of tetraacetylglycoluril and tetrapropionylglycoluril was determined; the working conditions deviated from the abovedescribed in the following points:
The activator amount was only 1 mMol/l., corresponding to 1 acyl radical per active oxygen atom. No further chemicals for reducing the pH were added; the experimental temperature was 30" C. The results obtained are found in the following Table IV.
TABLE IV Percent oxygen activated at 30 C.
Activator: Activator: tetraaeetyltetrapropionyl- Sample taken after 0: minutes glycoluril glycoluril From the above, it can be seen that the extent of activation is dependent upon the pH, the temperature, the amount of the activator used and upon the nature of the acyl radical present. Thus, with tetraacetylglycoluril already at the start of the experiment, high degrees of activation are obtained, with tetrapropionylglycoluril the degrees of activations are higher near the end of the experiment.
EXAMPLE 7 For the bleaching of human hair, the dyeing of hair by means of oxidation dyestuffs, and the oxidative treatment of hair after setting by the action of reducing thiocompounds (cold wave process), aqueous solutions containing 10 gm. to 200 gm. of H 0 per liter are normally used. When this treatment was carried out after addition of 20 gm. to 500 gm. per liter of tetraacetylglycoluril, a considerable intensifying of the oxidizing action of the H 0 was observed, so that, if desired, smaller concentrations of H 0 could also be used.
EXAMPLE 8 For the bleaching of living human hair, for the dyeing of hair with the aid of oxidation dyes and for the oxidative treatment of hair after setting by the action of reducing thio-compounds, an aqueous solution is used which is prepared in the following way:
6 gm. of (NH SO 15 ml. of a 25% aqueous NH 37 ml. of a 30% H 0 were dissolved in 30 m1. of water and sufficient water is added to give 100 ml.
When such a solution is used for the lightening of darkblond hair, at 20 to 30 C. within 30 to minutes a noticeable lightening is attained. If, however, 40 gm. of tetraacetylglycoluril are added, the hair is in the same time substantially lightened. In addition, the time of treatment can also be shortened.
If the equivalent amount of tetrapropionylglycoluril is used, the bleaching activation is less at the start of the treatment. It is thus easier to attain only a partial lightening of the color tone up to a definite, desired color tone.
The preceding specific embodiments are illustrative of the practice of the invention. It is obvious, however, that other expedients known to those skilled in the art may be employed without departing from the spirit of the invention.
I claim:
1. A method of oxidative treatment of human hair which consists essentially of contacting human hair, at a temperature of from 20 C. to 45 C., with an aqueous liquid containing an oxidizer selected from the group consisting of a water-soluble peroxyhydrate and hydrogen peroxide in an amount sufficient to supply from 10 gm. to 200 gm. per liter of H equivalent and from 20 gm. to 500 gm. per liter of an activator acylated glycoluril having the formula wherein at least two of R R R and R are acyls of an organic carboxylic acid having from 2 to 8 carbon atoms selected from the group consisting of an alkanoic acid, nitriloacetic acid, haloalkanoic acid, benzoic acid, nitrobenzoic acid, halobenzoic acid, toluic acid, nitrotoluic acid, halotoluic acid, methoxybenzoic acid and nitrolohenzoic acid, and the remainder of R R R and R are members selected from the group consisting of alkyl having from 1 to 8 carbon atoms and said acyls of an organic carboxylic acid having from 2 to 8 carbon atoms.
2. The method of claim 1 wherein said aqueous liquid hasapHoffrom7to11.
3. The method of claim 2 wherein said aqueous liquid has a pH of from 8 to 10.5.
4. The method of claim 1 wherein said temperature is from 20 C. to 30 C.
5. The method of claim 1 wherein said activator acylated glycoluril is tetraacetylglycoluril.
6. The method of claim 1 wherein said activator acylated glycoluril is tetrapropionylglycoluril.
7. The method of claim 1 wherein the amount of said acylated glycoluril in said aqueous liquid is sufficient such that from 0.5 to 6 acyls in said acylated glycoluril are present per active oxygen atom in said aqueous solution.
8. The method of claim 1 wherein said temperature is from 20 C. to 37 C., and said human hair is living human hair.
References Cited UNITED STATES PATENTS 2,708,940 5/1955 De Mytt et a1 42472 X 2,914,374 11/1959 Harris et al 42462 X 3,193,464 7/1965 Edman et al 42462 3,236,734 2/1966 Charle et a1 8-10.2 3,533,417 10/ 1970 Bartoszewicz et a1. 42472 X ALBERT T. MEYERS, Primary Examiner V. C. CLARKE, Assistant Examiner US. Cl. X.R.
810.2, 11, 111; 252l86; 260309.7; 424Dig. 3, 71,72
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US00141373A US3836636A (en) | 1967-12-30 | 1971-05-07 | Oxidative treatment of human hair with an acylated glycoluril and an oxidizer |
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DEH0064923 | 1967-12-30 | ||
US78759768A | 1968-12-27 | 1968-12-27 | |
US00141373A US3836636A (en) | 1967-12-30 | 1971-05-07 | Oxidative treatment of human hair with an acylated glycoluril and an oxidizer |
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Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4110242A (en) * | 1976-04-02 | 1978-08-29 | Henkel Kommanditgesellschaft Auf Aktien | Compositions and method for activating oxygen utilizing N-acylated uracils and benzouracils |
US4911860A (en) * | 1986-10-31 | 1990-03-27 | Lever Brothers Company | Solid detergent composition: polyalkylene-glycol-mono-ester carrier and synthetic surfactant for laundry pretreatment |
-
1971
- 1971-05-07 US US00141373A patent/US3836636A/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4110242A (en) * | 1976-04-02 | 1978-08-29 | Henkel Kommanditgesellschaft Auf Aktien | Compositions and method for activating oxygen utilizing N-acylated uracils and benzouracils |
US4911860A (en) * | 1986-10-31 | 1990-03-27 | Lever Brothers Company | Solid detergent composition: polyalkylene-glycol-mono-ester carrier and synthetic surfactant for laundry pretreatment |
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