GB2033939A - Low ammonia bleach compositions - Google Patents
Low ammonia bleach compositions Download PDFInfo
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- GB2033939A GB2033939A GB7935350A GB7935350A GB2033939A GB 2033939 A GB2033939 A GB 2033939A GB 7935350 A GB7935350 A GB 7935350A GB 7935350 A GB7935350 A GB 7935350A GB 2033939 A GB2033939 A GB 2033939A
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- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/22—Peroxides; Oxygen; Ozone
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- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides thereof
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- 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
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
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- 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
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Abstract
A thickened hair bleaching composition which produces only trace amounts of ammonia gas when applied to the users hair, having a water phase accounting for 80 to 100% of the total weight of the composition and an ammonium ion concentration in the water phase which is less than about 0.55% of the total composition which comprises 2-20% of a per-compound, 1.5-7% of hydrogen peroxide, an amine or quaternary ammonium compound, 4-8% of at least one water-soluble surfactant thickener, a buffering agent for maintaining the composition at a pH of from about 9 to 12, and the balance is water. The composition can contain additional ingredients including a sequestering agent, a viscosity modifier and a water-insoluble surfactant thickener.
Description
SPECIFICATION
Low ammonia bleach compositions
This invention relates to hair bleaching compositions containing a high degree of water-soluble surfactants and water-soluble compounds, and reduced levels of ammonium ions in the water phase thereby providing substantially reduced ammonia gas production and a more aesthetically pleasing result.
Any process relating to the treatment of hair must take into account a large number of variables.
Bleaching is basically a process to remove natural color from hair. The hair color, i.e. the degree of hair lightening desired by a patron may vary from the mere highlighting of hair through to the palest blonde. Bleaching compositions must therefore be capable of producing mild lightening to high lightening and all degrees of lightening in between. In addition, an entire head of hair may be bleached or only portions thereof, i.e. new growth or "root areas".
Bleaching compositions for streaking, frosting, or tipping may be self applied or operator assisted to gain special blonding effects.
Bleaching compositions used on hair differ from those used with textiles, fabrics, hard surface cleansing and the like in that hair bleaching compositions, in addition to oxidizing and destroying the colored melanin of the hair, must be suitable for use in contact with the human skin and must not damage the hair excessively. Furthermore, since hair bleaches are a member of the class of materials known as cosmetics, it is desirable that they be aesthetically acceptable to the user. Finally, it is desirable that a hair bleaching composition remove the melanin coloration from the hair as efficiently as possible, both for the sake of convenience and to help prevent damage to the hair and irritation to the skin and scalp. Most bleaching systems required exposure to the hair for periods from a few minutes to as long as about 2 to 3 hours, depending upon the desired degree of bleaching.
Hair bleaches commonly consist of a peroxide oxidizing agent, bleach enhancing agents, and a variety of additional cosmetic and bleach stabilizing agents. Oxidizing agents such as the various hypochlorites and halogenated cyanuric acid compounds suitable for use on hard surfaces and in fabric bleaching are not suitable for use on hair since they are too damaging and too irritating to the skin.
Peroxide bleaches used on hair must be "activated", this being accomplished by the use of an "activating" agent to adjust the pH to a basic range. The most common material for adjusting the pH of peroxide hair bleaching compositions is an aqueous solution of ammonia, commonly referred to as ammonium hydroxide.
The prior art discloses that aqueous solutions of certain compounds, namely hydrogen peroxide and
hydrogen peroxide generating compounds such as
peroxy compounds, e.g. persulfates, perborates,
percarbonates, are effective in bleaching human hair
or keratinous materials. In an effort to increase the
rate of bleaching with these hydrogen peroxide pro
ducts, an activator is used in conjunction with the hydrogen peroxide, the activator generally being an ammonium, an alkali metal hydroxide or an alkali metal hydroxide producing compound.
Hair lightening lotions used in two and three com
ponent systems typically contain between 2 and 5.5% by weight ammonium hydroxide. Generally, at
least half this amount is unneutralized and is present in the lotion as NH3 H2O. Because of the high concentration of neutralized and unneutralized ammonium ion bleach systems currently in consumer use today have a characteristic ammonia odor. As a result, bleach mixtures are not as aesthetic to use as other cosmetic preparations.
However, if ammonia or ammonium hydroxide is replaced by a higher molecular weight less volatile amine, the resulting bleach mixture is more damaging (for the same degree of lightening) to the keratine hairfibers. For example, U. S. Patent 2,283,350 to Baum discloses the use of aliphatic amines and hydroxyaliphatic amines as substitutes for ammonium hydroxide in hair bleaching compositions. Moreover, U. S. Patent3,816,615toZeffren et al discloses hair bleaches containing guanidine compounds in place of ammonium hydroxide.
Furthermore, to be effective, a bleach composition must remain in place for the time required to effectively lighten the hair, retaining while in place, the proper alkalinity and moisture content needed to continue the bleaching action. The bleach composition must form a foam of limited height and of suffi cientviscosityto hold in contact with the hairthe bleaching constituents and the oxygen released. The conventional bleaching compositions known in the art accomplish this by incorporating significant quantities of various types of water-insoluble thickeners, oils and fillers. For example, U. S.Patent 3,651,209 to Cohen describes the use of calcium carbonate, magnesium carbonate, plaster of Paris and other inert fillers such as talc, kaolin and bentonite as suitable thickening agents for bleaching compositions. "White henna" (i.e. mixtures of magnesium carbonate and magnesium oxide, magnesium trisilicate or the like) and other insoluble adsorbent materials have also been described as useful aids to build viscosity in bleaching compositions.
Hair lightening lotions presently in use are additionally known to contain substantial quantities of water insoluble esters, alcohols, ethoxylates and/or propoxylates to create viscosity. The most common alcohol used is the C1a oleyl derivative. The water insoluble surfactants form gels when the lotion is
mixed with aqueous peroxide solutions. The water
insoluble gel helps keep the bleach mixture on the
hair fibers and prevent it from running or creeping
away from the hair shaft. The use of water insoluble
su rfacta nts, however, greatly affects the lightening
ability of the bleach mixture. To overcome reduced
bleaching activity, high levels of ammonia are
required. Studies have shown that as the surfactant
becomes more water insoluble, the lightening ability
of the bleach system decreases.The functional
grouping of the surfactant appears to have little
effect upon the efficiency of the. resultant bleach mix
ture as long as water solubility is maintained.
Accordingly, to provide an improved peroxygen bleaching composition producing very little unpleasant ammonia odor and having the proper consistency throughout the bleaching operation to provide good lightening results while holding the amount of hair damage incurred by bleaching to an acceptable minimum level, it has been surprisingly found that this can be attained by keeping both water insoluble ingredients and amine levels to a minimum. As a consequence, lightener lotion formulations should contain surfactants which form soluble gels when mixed with peroxides and/or persulfates. The above criteria for solubility/gel formation places practical restrictions on the type of surfactants that can be used.
Accordingly, one aspect of the invention to be disclosed herein is a thickened hair bleaching composition comprising:
(a) 2 to 20 weight percent of at least one percompound selected from the group consisting of an ammonium-, alkali metal- and alkaline earth metalperborate, persu Ifate, perca rbonate, and carbonate peroxide;
(b) 1.5 to 7 weight percent of hydrogen peroxide;
(c) an amine or quaternary ammonium compound selected from the group consisting of ammonium hydroxide, morpholine, mono-, di-, and trialkanolamine, and mono-, di-, and trialkylamine, wherein the alkyl or alkanol substituents have a carbon chain length of 1 to 4 carbon atoms;
(d) 4-8 weight percent of at least one water-soluble surfactant thickener;
(e) a buffering agent for maintaining the composition ata pH of from about9to 12; and
(f) the balance is water, wherein the ammonium ion concentration in the water phase is less than about 0.55 weight percent based on teetotal composition resulting in substantially only trace amounts of ammonia gas produced as a result of interaction of these ingredients with each other or with hair.
Additionally, the composition according to the invention can contain, respectively, up to about 0.5 weight percent of a sequestering agent, 1.5 weight percent of a viscosity modifier, and 20 weight percent of at least one additional water-insoluble ingredient selected from the group consisting of surfactants, perfumes, oils, opacifiers, and dyestuffs.
Preferably, the composition according-to the invention can contain, respectively, about 6-8 weight percent of the percompound, 3.2-3.7 weight percent of hydrogen peroxide, and include as the watersoluble surfactant thickener the 8.5 mole ethoxylate
of cocoyl fatty acid. Additionally, the pH of the result
ing composition is preferably about 9.7 to 10.3.
The water-soluble su rfactant thickener can be
selected from the group consisting of:
(a) an alkylene glycol or an alkylene glycol ether
alcohol of the formula: R5O(R60)nR70H wherein R8 is H or alkyl having 1 to 4 carbon atoms
and R6 and R7 are divalentalkylene radicals having 2 to 4 carbon atoms and n is a number from 0 to 150;
(b) a long chain fatty acid soap of the formula
(R8COO)aM
wherein R8 is the hydrocarbon moiety of a long chain fatty acid having 10 to 20 carbon atoms, M is a monovalent or polyvalent salt-forming group and "A" is the valence of group M;;
(c) a long chain polyoxyalkylated compound selected from the group consisting of a polyoxyalkylated long chain fatty alcohol, a polyoxyalkylated polyhydroxyalkyl ester of a long chain fatty acid; a polyoxyalkylated long chain amine; a polyoxyalkylated long chain fatty acid; a polyoxyalkylated long chain fatty acid amide; a polyoxyalkylated long chain alkylphenol and polyoxyalkylated laurate esters of sorbitol and its anhydrides containing about 8 to 300 oxyalkyl groups in the structure; and
(d) mixtures thereof.
The thickened hair bleaching compositions in accordance with the invention herein generally have a viscosity in the range of 5000 to 100,000 centipoises.
As was previously mentioned, it is commonly accepted practice to incorporate an amine or quaternary ammonium compound in a peroxygen bleaching system to provide activation in the bleaching process.
Bleaching studies have surprisingly indicated that very good lightening, resulting in minimal hair damage, can be obtained with lotions containing an ammonium ion concentration of 0.55 weight percent or less based on the total composition weight, while at the same time having a water phase that accounts for 80 to 100 weight percent of the total composition.
Studies have also indicated that hair lightening is not substantially affected by ammonia basicity, i.e. the ammonia may nominally be present as either free NH3 H2O or as the neutralized ammonium ion,
NH4+. From A cosmetic viewpoint, the ammonium ion is preferable to free ammonia.
Because ofthe equilibrium between NH3,
NH3 H2O, NH4OH, NH4+ and OH-, it is not possible to have just one species present in an aqueous medium. The relative proportion of ammonia to ammonium can be shifted by pH, ionic strength, pressure and any other chemical technique that affects the concentration of each specie in the equilibrium constant. However, merely reducing amine or quaternary ammonium content, without also maintaining the higher concentrations of water-soluble components, or vice versa, as taught herein does not provide satisfactory hair lightening results. Moreover, to try to compensate for the inferior lightening resulting from using lower amine or quaternary ammonium concentrations by either using high concentrations of peroxygen compounds, alkaline ingredients, longer time periods for bleaching the hair, or highertemperature during the bleaching process will result in unsatisfactory damage levels to the hair. It is the intent of this invention to adjust the formula in such a way so as to favorthe formation of ammonium ion and keep the concentration of free ammonia as close as practical to the value dictated by the equilibrium constant.
One of the essential ingredients present in the
bleach compositions according to the invention herein is at least one percompound in a useful con
centration range of about 2 to 20%, and preferably 6 to 8%. It is pointed out that% throughout the specifi
cation are weight percent based on the total weight of the composition, unless otherwise indicated. The
percompound provides an additional source of oxygen generation necessary for bleaching, other than hydrogen peroxide. Such percompounds are
not limited to but can be selected from the ammonium-, alkali metal- and alkaline earth metalperborates, persulfates, percarbonates, and carbonate peroxides. The term "alkali metal" and "alkaline earth metal" as used herein and throughout the specification are deemed to have their ordinary accepted meaning in the art.
It is also essential to have present hydrogen peroxide in a useful concentration range of about 1.5 to 7% to provide bleaching of the hair. Stabilizers for the hydrogen peroxide, such as phenacetin, may also be present in minor amounts. Preferably the hydrogen peroxide concentration is from about 3.2 to 3.7%.
A third essential ingredient is a water-soluble amine or quaternary ammonium compound for providing necessary activation of the peroxide for enhanced bleaching, and also serving additionally as a pH adjusting agent and aiding in thickening the composition by the formation of water-soluble soap gels with fatty acids. The amine or quaternary ammonium compound most often used, and that preferred, is ammonium hydroxide because of its ready availability and effectiveness as a peroxide activator. However, other less effective amines can be used, typically in larger quantities, such as an amine or quaternary ammonium compound selected from the group consisting of at least one of morpholine, mono-, di-, trialkanolamine, and mono-, di-, and trialkylamine, wherein the alkyl or alkanol substituents have a carbon chain length of 1 to 4 carbon atoms.
As previously noted, it is critical that the ammonium ion concentration in the water phase of the bleaching composition be less than about 0.55% to prevent the formation of more than trace amounts of ammonia gas by the composition during the hair bleaching process and thereby overcoming the problems associated with the prior art, producing cosmetically pleasing results. Therefore it is apparent that the resulting ammonium ion concentration comes about from many factors not the least of which is the amount of ammonium compounds including ammonium percompounds present in the composition which are capable of ionizing in water to form the ammonium ion. Also affecting the ammonium ion concentration is the amount of other compounds that react with (e.g. neutralize) the ammonium ion, such as fatty acid compounds.
Finally, there are factors associated with the equilibrium in solutions between the ammonium ion, ammonium hydroxide, and ammonia gas. Furthermore, it is observed that the use of amines in place of ammonium hydroxide will not result in the formation of ammonium ion, but requires greater amounts of the same because of lower efficiency compared to ammonium hydroxide.
It is essential to include from about 4 to 8% of at least one water-soluble surfactant thickener. These are well known to anyone skilled in the art. For example, such water-soluble surfactant thickeners are those described as "coupling agents" at column 5, line 29 to column 6, line 56 of U. S. Patent 3,811,830 to R.
DeMarco issued May 21, 1974, and incorporated by reference herein. Additionally, useful are ethoxylated laurate esters of sorbitol and its anhydrides such as with 80 moles ethylene oxide (Tween 80); acid ethoxylates such as di-stearic acid with 150 moles ethylene oxide (PEG 6000 Distearate); and biock copolymers of ethylene oxide and propylene oxide (Pluronics). A preferred surfactant is cocoyl fatty acid ethoxylated with 8.5 moles of ethylene oxide.
The useful pH range for using the bleaching compositions as herein disclosed is from about9to 12, although preferably it is about 9.7 to 10.3. Below the pH of 9, insufficient bleaching action occurs; whereas above 12 excessive hair damage occurs.
To maintain the proper pH range, a buffering agent or pH adjustment agent is found to be essential. In addition to the alkalinity provided by the amine or quaternary ammonium compounds, useful agents are the alkali metal metasilicates such as sodium metasilicate; alkali metal carbonate, ortho-, meta- and tripolyphosphates.
Finally, water is an essential ingredient in providing the proper medium for the bleaching process to occur as previously discussed, and makes up the balance of the composition except for waterinsoluble ingredients and other optional additives.
Among the optional additive ingredients are sequestering agents for complexing metal ion inpurities which would tend to affect the stability of the hydrogen peroxide. Such sequestrants which may be present in a concentration up to about 0.5% and include the unneutralized and/or the alkali metal salts of nitrilotriacetic acid and alkylenepolyamine polycarboxylic acids having the formula (HOOCCH2)2N[(CH2)xNCH2COOH] yCH2COOH wherein x and y may vary independently from 1 to 4.
Representative of such acids are ethylenediaminetetraacetic acid and ethylenediaminetriacetic acid.
Also present may be up to about 1.5% of a viscosity modifier which can include water-soluble straight chain aliphatic alcohols (e.g. ethanol and butanol), aldehydes (e.g. acetaldehyde and butyraldehyde), ketones (e.g. acetone and 2-hexanone), and glycols (e.g. ethylene glycol and butylene glycol).
Additionally, the compositions can optionally include up to about 20% of at least one additional water-insoluble ingredient which includes for example, surfactants, perfumes, oils, opacifiers and dyestuffs (including dyes and dispersible pigments).
Such dyestuffs include for example, D & C Green #6, FD & Yellow #3, and pigments like ultramine blue and disperse blue 1.
Typical opacifiers include abietic/lauric ether polyesters, and polystyrene.
Oils include non-volatile oils such as mineral oil, isopropyl myristate, diisopropyl adipate, and volatile or essential oils such as peppermint, clove oil, and eucalyptus oils.
Typical of the water-insoluble surfactants that can be used for thickening and emulsifying properties are those well known in the art such as those dis closed in U. S. Patent 3,811,830 to DeMarco at color umn 3, line 64 to column 5, line 6, which is incorporated by reference herein, called "oily materials."
Still other optional additives can include waterinsoluble fats and waxes derived from natural or synthetic sources (e.g. beeswax or spermaceti) and skin emmolients well known in the art.
It is again pointed out that the use of water-soluble surfactantthickeners are essential, optionally in combination with limited quantities of the aforementioned water-insoluble ingredients, to provide for a low ammonia bleach composition in accordance with the invention herein. It is pointed out that the use of natural gums (e.g. xanthum or guar gum) and cellulose-based thickening agents (e.g. carbox ymethylcellu lose derivatives) with or without solvents such as low molecular weight alcohols and ketones do not provide the necessary thickening properties for use herein. The gums and cellulosebased agents being too difficult to conveniently mix and requiring excessive time to hydrate in orderto build the necessary viscosity to maintain the bleaching composition on the hair.Solvents which generally couple oil-soluble materials and water-soluble su rfacta nts produce compositions with low viscosity and are unsuitable for bleaching keratin fibers.
In the examples that follow the test methods used for evaluating bleaching (i.e. hair lightening effectiveness) and alkaline solubility (i.e. hair damage) are described as follows.
Test Method for Evaluating Bleaching Effectiveness
Surfactants and their effect upon lightening and damage were evaluated as part of a three component system. The system contained a powdered activator, a lotion and a developer. The chemical composition of the activator and developer were kept constant with the lotion being the vehicle for the evaluation of the surfactant. The activator had the following composition: ACTIVATOR Ingredient Grams WIW /O (Na2Si2Os) 2.1 9.05
Sodium Lauryl Sulfate 0.5 2.15
Methocel 60 HG (Hydroxypropyl
methyl cellulose) 0.3 1.30
Cabosil M5 (fumed Silica Dioxide) 0.3 1.30
Potassium Persulfate 10.0 43.10
Sodium Persulfate 10.0 43.10
23.2 100.00
The lotion consisted of 0.5% monoethanolamine (i.e.MEA) and 99.5% of the surfactantto be evaluated.
Bleaching tests were done as follows: * < Twenty-three grams of activator were added to 4 oz. of a 6% aqueous hydrogen peroxide solution and
shaken. Sixty grams of the test lotion was then
added and shaken until thoroughly mixed. The pH
and viscosity of the mixture were then measured.
The mixture was spread over and through a swatch
or brown pigmented hair. The swatch consisted of a
blend of commercially available virgin hair approxi
mately nine inches long. The bleaching was accomp
lished in a glass dish placed atop a constant temper
ature bath set at 38"C. The bleaching time was one
hour with the swatch being turned over and the
bleach mixture "reworked" every fifteen minutes. At
the end of one hour, the bleach mixture was rinsed
from the hair and the swatch shampooed with a mild
shampoo. The swatch was then visually compared
to a standard. If the swatches were comparable in
lightening to the standard, the reflectance of each
swatch was accurately measured at 560 m on a
Beckman DU-2 Spectrophotometer.
Where the surfactant was supplied as powdered
solid material, the necessary MEA and solid surfac
tant are dissolved in the 6% hydrogen peroxide solu
tion. The activator is then added to the resulting
lotion/peroxide mixture and shaken until uniform.
The bleaching process is the same as previously
described.
Test Procedure --Alkaline Solubility Test
Bleach hair swatches at 38"C. for 1 hour in bleaching composition. Then dry 1 gram sample of bleached hairfor3 hours at 110"C. Weigh the dried hair sample. Then immerse hair for 1 hour in 100 ml.
of 0.1 N sodium hydroxide at 66 C. Remove hair from sodium hydroxide solution and rinse with distilled water. Follow with rinse of 1% acetic acid solution. Again rinse with distilled water. Dry hair swatch for 3 hours at 11 0"C. Weight sample and calculate weight loss. The greater the weight loss the greater the hair damage that has occurred during the bleaching process.
The standard used was a commercially avaiable
Clairol Naturally Blonde Quick Lightening Kit comprising a three component system; 60 g. of lotion; 120 g. of developer and 28 g. of activator (208 g.
total). Percent composition is as follows:
CHEMICAL NAME WEIGHT% Lotion
Ammonium Hydroxide (29% aqueous solution) 2.45
Disodium ethylenediamine tetraacetic acid 0.30
Isopropanol 3.75
Ethoxydiglycol' 1.01
Ethoxylated nonylphenyl (10 moles of ethylene oxide)2* 1.59
Oleic acid 10.10
Polyethylene glycol ether of tridecyl alcohol (6 moles
of ethylene oxide)3* 1.20
Ethylhydroxymethyl oleyl oxazolineo 3.17
Polyethylene glycol amine of Soya Acid (5 moles of
ethylene oxide)5* 3.17
Water 2.22
Fragrance 0.14
Developer
Ethoxylated Nonylphenyl (4.0 moles of ethylene oxide)6* 2.88
Ethoxylated Nonylphenyl (9.0 moles of ethylene oxide)7 2.88
Cetyl Alcohol* 0.14
Hydrogen Peroxide (50 /O aqueous solution) 7.96
Water 44.68
Activator
Silica3* 0.20
Sodium metasilicate 1.82
Sodium lauryl sulfate 0.16
Disodium ethylenediamine tetraacedic acid 0.16
Ammonium Persulfate 2.80
Potassium Persulfate 8.28
100.00
1. Trade Name: Carbitol PM 600
2. Trade Name: Igepal DM 530
3. Trade Name: Emulphogene BC-610
4. Trade Name: Alkaterge C
5. Trade Name: Varonic L 205
6. Trade Name: Igepal CO 430
7. Trade Name: Igepal CO 630
8. Trade Name: Cabosil M5 Note: All of the oleic acid was converted to the water-soluble salt form.
This composition had an alkaline solubility of 30.2% (i.e. 30.2 wt.% of 1 g. sample dissolved in alkaline solution). Ammonium ion concentration1.70 wt./; water-soluble phase - 87.65 wit.%. In the
Naturally Blonde composition and the examples that follow, the designation "*" indicates that the particular ingredient is not water-solubie or only slightly water-soluble. Also, the wt. % of the water-soluble phase is determined by subtracting from 100% the wt. % of insoluble ingredients.
Additionally, the maximum ammonium ion concentration in the composition is determined by assuming complete ionization of the ammonium percompound and ammonium hydroxide.
In accordance with the aforementioned Bleaching and Alkaline Solubility Test methods, bleaching compositions including the following water-soluble surfactant thickeners tested and gave comparable and satisfactory light reflectance and alkaline solubility levels as that for Naturally Blonde.
Chemical Class Trade Name
Ethoxylated primary fatty amine Ethomeen C/25
Ethoxylated fatty acids Ethofat 242/25
Ethoxylated dialkyl quaternary
ammonium salts Ethoquad 18/25
Ethoxylated fatty alcohols BrijR 35
Propoxylated fatty alcohols ProcetylR 50
Ethoxylated lanolin Solulan 75
Ethoxylated lanolin alcohols Solulan 25
Acetylated polyoxyethylene lanolin derivatives Solulan 97
Nonylphenoxypoly(ethyleneoxy) types Igepal CO-630 Polyethylene/propylene glycols Pluronics/Carbowaxes
Polyethylene glycol 1000 monostearate Collemol 510
In the Examples 1-14 that follow, the resulting bleaching compositions had a pH of 9.8-10 and were evaluated using the aforementioned test methods for bleaching and alkaline solubility, except where indicated otherwise, providing similar light reflectance and solubility levels to that for Naturally
Blonde.In Examples 8-14, the entire composition was water-soluble and the ammonium ion concentration was 0.514 wt. %.
EXAMPLE 1
Three component system; 66 g. of lotion; 120 g. of developer; 28 g of activator. (214 g. total) The activator was mixed with the lotion and the peroxide developer was added to the lotion/activator mixture.
Percent composition of the total mixture is as follows:
CHEMICAL NAME WEIGHT % Lotion
Polyethylene glycol ether of Oleyl Alcohol (10
moles of ethylene oxide 14.02
Oleic Acid 7.01
Ethanol 4.67
Monoethanolamine 2.80
Ethoxylated nonylphenyl (49 moles of ethylene oxide) 2.33
Developer
Hydrogen Peroxide (50% aqueous solution) 6.89
Water 49.18
Activator
Potassium Persulfate 2.95
Ammonium Persulfate 0.92
Sodium Persulfate 2.95 Disodiumethylenediaminetetraacetic acid 0.13
Sodium meta silicate 6.15
100.00
Water-soluble phase- 100%.
Ammonium ion concentration-0.15% 1. Trade Name: Brij 96 2. Trade Name: Igepal DM 880
Note: All of the oleic acid was converted to the water-soluble salt form.
Lightening was measured in accordance with the test method procedure except that a 15 g. bundle of commercially available pigmented virgin hair approximately 9 inches long was bleached for 1 hour. The bleaching was conducted in a glass tray placed atop a constant temperature bath maintained at 39 C.
EXAMPLE2
Three component system; 60 g. of lotion; 120 g. of developer; 28 g. of activator (208 g. total) was mixed
as described in Example 1. Percent composition is as follows:
CHEMICAL NAME WEIGHT% Lotion
Polyethylene glycol ether of Lauryl Alcohol
(23 moles of ethylene oxide)' 0.48
Polyethylene glycol ether of Oleyl Alcohol
(10 moles of ethylene oxide)2 24.40
Ethanol 3.84
Monoethanolamine 0.12
Developer
Hydrogen Peroxide (50% aqueous solution) 7.10
Water 50.60
Activator
Potassium Persulfate 3 03 Ammonium Persulfate 0.94
Sodium Persulfate 3.03
Disodiumethylenediamine tetraacetic acid 0.13
Sodium Metasilicate 6.33
100.00 Water-soluble phase 100%.
Ammonium ion concentration-0.15% 1. Trade Name: Brij 35 2. Trade Name: Brij 96
EXAMPLE 3
Three component system; 66 g. of lotion; 120 g. of developer and 28 g. of activator (214 g. total) were mixed as previously described. Percent composition is as follows:
CHEMICAL NAME WEIGHT% Lotion
Laurate esters of sorbitol and sorbitol anhydrides
condensed with 80 moles of ethylene oxide1 23.36
Polyethylene glycol ester of oleic acid (5 moles
of ethylene oxide)2* 4.67
Monoethanolamine 2.80
Developer
Hydrogen Peroxide (50 /O aqueous solution) 6.89
Water 49.18
Activator
Potassium Persulfate 2.95
Ammonium Persulfate 0.92
Sodium Persulfate 2.95
Disodium Ethylenediamine tetraacetic acid 0.13
Sodium Metasilicate 6.15 100.00 Water-soluble phase - 95.33%.
Ammonium ion concentration-0.15% 1. Trade Name: Tween 80
2. Trade Name: EmulphorVN-430
EXAMPLE4
Three component system; 60 g. of lotion; 120 g. of
developer and 28 g. of activator (208 g. total) were
mixed as previously described. Percent composition
is as follows:
CHEMICAL NAME WEIGHT% Lotion
Oleic Acid 6.34
Ethoxylated Cocoyl Fatty Acid (8.5 moles of
Ethylene oxide)1 9.23
Ethoxylated Nonylphenol (4.0 moles of ethylene oxide)2 3.10
Polyethylene glycol amine of Soya Acid (5.0 moles
of ethylene oxide)3* 2.88
Ethanol 1.55
Polypropylene glycol ether of cetyl alcohol (5.0
moles of ethylene oxide)4 5.77
Perfume 0.08
Ammonium Hydroxide (59% aquous solution) 0.29
Developer
Hydrogen Peroxide (50 /O aqueous solution) 7.10
Water 50.20
Activator
Potassium Persulfate 3.03
Ammonium Persulfate 0.94
Sodium Persulfate 3.03
Disodiumethylenediamine tetraacetic acid 0.13
Sodium Metasilicate 6.33
100.00
Water-soluble phase - 94.02% Ammonium ion concentration - 0.24% 1. Trade Name: Nu-Mole7A-CM 2. Trade Name: Igepal C0430 3. Trade Name: Ethomeen S-15 4. Trade Name: Procetyl 50
EXAMPLE 5
Two component system; 88 g. of activator is mixed with 120 g. of developer (208 g. total).Percent composition is as follows:
CHEMICAL NAME WEIGHT %
Activator
Ethoxylated nonylphenol (150 moles of ethylene oxide)1 12.79
Polyethylene glycol diester of stearic acid (15G moles
of ethylene oxide)2 0.78
Palmitic acid3 2.19
Disodiumethylenediamine tetraacetic acid 0.26
Sodium Metasilicate 11.75
Sodium Persulfate 5.88
Potassium Persulfate 5.88
Ammonium Persulfate 2.78
Developer
Ethoxylated nonylphenol (4.0 moles of ethylene oxide)4* 2.89
Ethoxylated nonylphenol (9.0 moles of ethylene oxide)5 2.89
Cetyl Alcohol* 0.14
Hydrogen Peroxide (50 /O aqueous solution) 7.09
Water 44.68
100.00
Water-soluble phase - 96.97%.
Ammonium ion concentration-0.440 /O.
1. Trade Name: Igepal DM-970 2. Trade Name: PEG 6000 Distearate 3. Trade Name: Neo-Fat 16 4. Trade Name: Igepal CO 430 5. Trade Name: Igepal CO 630
EXAMPLE 6
Three component system; 60 g. of lotion; 120 g. of developer and 29 g. of activator (208 g. total) were
mixed as previously described. Percent composition
is as follows: :
CHEMICAL NAME WEIGHT% Lotion
Oleic Acid 7.21
Ethoxylated Cocyl Fatty Acid (8.5 moles of ethylene
oxide)' 6.35
Ethoxylated nonylphenol (4.0 moles of ethylene oxide)2* 2.02
Ethylhydroxymethyl oleyl oxazoline3* 3.97
Polyethylene glycol amine of Soya Acid (5.0 moles of
ethylene oxide)4* 2.88
Ammonium hydroxide (59 /O aqueous solution) 0.29
Ethanol 1.15
Polypropylene glycol ether of cetyl alcohol (5.0 moles
of ethylene oxide)5 4.90
Fragrance 0.07
Developer
Hydrogen Peroxide (50 /O of aqueous solution) 7.10
Water 44.70
Cetyl Alcohol* 0.14
Ethoxylated nonylphenyl (4 moles of ethylene oxide)2* 2.88
Ethoxylated nonylphenyl (9 moles of ethylene oxide)6 2.88
Activator
Potassium Persulfate 3.03
Ammonium Persulfate 0.94
Sodium Persulfate 3.03
Disodiumethylenediamine tetraacetic acid 0.13
Sodium Metasilicate 6.33
100.00
Water-soluble phase -88.11% Ammonium ion concentration-0.24% Alkaline solubility-30.7% 1. Trade Name: Nu-MoleCM-7A
2. Trade Name: igepal CO-430 3. Trade Name: Alkaterge E
4. Trade Name: Ethomeen S-15
5. Trade Name: Procetyl 50
6. Trade Name: Igepal CO-630 EXAMPLES 8- 14 #8 #9 #10 #11 #12 #13 #14 NH4OH(29%) 1.0 1.0 1.0 1.0 1.0 1.0 1.0
Nu-Mole CM-7A 8.0 x 4.0 x 4.0 x
Laureth-40 x 8.0 4.0 x x x x
PPG-50 Cetyl Ether2 x x x 8.0 4.0 x x
Nonyl Nonoxynol-493 x x x x x 8.0 x
Peg 400 Monolaurate4 x x x x x x 8.0 K2S2Os x 4.0 4.0 2.0 4.0 4.0 4.0 Na2S208 4.0 x x 2.0 x x
H202 6.0 6.0 6.0 6.0 6.0 6.0 6.0
Sodium Metasilicate 6.2 6.2 6.2 6.2 6.2 6.2 6.2
Water 74.8 74.8 74.8 74.8 74.8 74.8 74.8 1. Polyethylene glycol ether of lauryl alcohol (40 moles ethylene oxide).
2. Polypropylene glycol ether of cetyl alcohol (50 moles of ethylene oxide).
3. Ethoxylated dinonylphenol (49 moles of ethylene oxide).
4. Polyethylene glycol ester of lauric acid (400 moles of ethylene oxide).
Claims (13)
1. Athickened hair bleaching composition comprising a water phase, accounting for from about 80 to 100 weight percent of the total composition, said water phase comprising based on the total composition:
(a) 2 to 20 weight percent of at least one percompound selected from the group consisting of an ammonium-, alkali metal- and alkaline earth metalperborate, persulfate, percarbonate, and carbonate peroxide;
(b) 1.5 to 7 weight percent of hydrogen peroxide;
(c) an amine or quaternary ammonium compound selected from the group consisting of ammonium hydroxide, morpholine, mono-, di-, and trialkanolamine, and mono-, di-, and trialkylamine, wherein the alkyl or alkanol substituents have a carbon chain length of 1 to 4 carbon atoms;
(d) 4-8 weight percent of at least one watersoluble surfactantthickener;; (e) a buffering agent for maintaining the composition ata pH of from about9to 12; and
(f) the balance is water, wherein the ammonium ion concentration in the water phase is less than about 0.55 weight percent based on the total composition resulting in substantially only trace amounts of ammonia gas produced as a result of interaction of these ingredients with each other or with hair.
2. The composition of Claim 1 additionally containing up to about 0.5 weight percent of a sequestering agent.
3. The composition of Claim 1 additionally containing up to about 1.5 weight percent of a viscosity modifer selected from the group consisting of a water-soluble straight chain aliphatic alcohol, aldehyde, ketone, glycol, and mixtures thereof, having a carbon chain length of 1 to 6 carbon atoms.
4. The composition of Claim 1 additionally containing up to about 20 weight percent of at least one additional water-soluble ingredient selected from the group consisting of surfactants, perfumes, cils, opacifiers, and dyestuffs.
5. The composition of Claim 1 wherein said water-soluble su rfactant thickener is selected from the group consisting of:
(a) an alkylene glycol or an alkylene glycol ether alcohol or the formula: R5O(R6O)nR7OH wherein R5 is H or alkyl having 1 to 4 carbon atoms and R6 and R7 are divalent alkylene radicals having 2 to 4 carbon atoms and n is a numberfrom 0 to 150;
(b) a long chain fatty acid soap of the formula (R8COO)aM wherein R8 is the hydrocarbon moiety of a long chain fatty acid having 10 to 20 carbon atoms, M is a monovalent or polyvalent salt-forming group and "a" is the valance of group M;;
(c) a long chain polyoxyalkylated compound selected from the group consisting of a polyoxyalkylated long chain fatty alcohol, a polyoxyalkylated polyhydroxyalkyl ester of a long chain fatty acid; a polyoxyalkylated long chain amine; a polyoxyalkylated long chain fatty acid; a polyoxyalkylated long chain fatty acid amide; a polyoxyalkylated long chain alkylphenol and polyoxyalkylated laurate esters of sorbitol and its anhydrides containing about 8to 300 oxyalkyl groups in the structure; and
(d) mixtures thereof.
6. The composition of Claim 5 wherein said percompound weight percent (a) is about 6 to 8.
7. The composition of Claim 6 wherein said hydrogen peroxide weight percent (b) is about 3.2 to 3.7.
8. The composition of Claim 7 wherein said pH is about 9.7 to 10.3.
9. The composition of Claim 8 wherein said water-soluble surfactant thickener (d) is cocoyl fatty acid ethoxylated with 8.5 moles of ethylene oxide.
10. A hair bleaching composition substantially as hereinbefore described in any one of the Examples.
11. A method of bleaching hair, comprising the step of applying to the hair a composition in accordance with any one of Claims 1 to 10.
12. The ingredients of the composition of Claim 1 when sold in a multi-part package comprising as the first part of the percompound, as the second part the amine or quaternary ammonium compound, with the surfactant and the buffering agent being incorporated in the first part or the second part or both, and with the hydrogen peroxide being supplied separately.
13. The ingredients of the composition of Claim 1 when sold in a multipart package comprising as the first partthe percompound, as the second part the amine, and as the third partthe hydrogen peroxide, with the surfactant and the buffering agent being incorporated in the first part or the second part or both.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US95092278A | 1978-10-12 | 1978-10-12 |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2033939A true GB2033939A (en) | 1980-05-29 |
GB2033939B GB2033939B (en) | 1983-01-19 |
Family
ID=25491031
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7935350A Expired GB2033939B (en) | 1978-10-12 | 1979-10-11 | Low ammonia bleach compositions |
Country Status (17)
Country | Link |
---|---|
BE (1) | BE879364A (en) |
CA (1) | CA1111349A (en) |
CH (1) | CH642534A5 (en) |
DE (1) | DE2941511A1 (en) |
DK (1) | DK425479A (en) |
FI (1) | FI76491C (en) |
FR (1) | FR2438477A1 (en) |
GB (1) | GB2033939B (en) |
GR (1) | GR74489B (en) |
IE (1) | IE48961B1 (en) |
IT (1) | IT1206994B (en) |
LU (1) | LU81777A1 (en) |
MX (1) | MX153887A (en) |
NL (1) | NL7907552A (en) |
NO (1) | NO155914C (en) |
SE (1) | SE7908473L (en) |
ZA (1) | ZA795463B (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5612022A (en) * | 1994-01-14 | 1997-03-18 | L'oreal | Pulverulent hair bleach of peroxygen oxidizer and polyoxyethylene/polyoxypropylene copolymer |
WO1999062469A1 (en) * | 1998-06-03 | 1999-12-09 | Henkel Kommanditgesellschaft Auf Aktien | Lightener |
WO2001043709A1 (en) * | 1999-12-17 | 2001-06-21 | Unilever Plc | Hair bleaching and colouring compositions having a ph greater than ph 10 comprising cholesterol |
WO2002078662A2 (en) | 2001-03-30 | 2002-10-10 | The Procter & Gamble Company | Hair bleach product |
EP1374842A1 (en) * | 2002-06-26 | 2004-01-02 | L'oreal | Composition for the oxidative dyeing of human keratin fibres |
WO2006060568A1 (en) * | 2004-12-02 | 2006-06-08 | The Procter & Gamble Company | Thickened hair colourant and bleaching compositions |
EP1669105A1 (en) * | 2004-12-02 | 2006-06-14 | The Procter and Gamble Company | Thickened hair colourant and bleaching compositions |
US7458993B2 (en) | 2002-06-26 | 2008-12-02 | L'oreal | Composition useful for the oxidation dyeing of human keratinous fibres |
EP1849499A3 (en) * | 2006-04-26 | 2010-01-20 | The Procter and Gamble Company | Amide surfactant thickening systems for hair colouring and bleaching compositons |
US7731944B2 (en) | 2000-09-21 | 2010-06-08 | Kao Corporation | Hair cosmetic compositions |
FR2994650A1 (en) * | 2012-08-23 | 2014-02-28 | Oreal | Composition in compressed form, useful for bleaching keratin fibers e.g. human hair, comprises persulfate including e.g. sodium persulfate, and fatty alcohol including e.g. cetylstearyl alcohol |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4847089A (en) * | 1986-07-16 | 1989-07-11 | David N. Kramer | Cleansing and distinfecting compositions, including bleaching agents, and sponges and other applicators incorporating the same |
DE3844956C2 (en) * | 1988-04-28 | 1996-03-21 | Schwarzkopf Gmbh Hans | Two component compsn. for making hair bleaching paste |
DE3814685A1 (en) * | 1988-04-30 | 1988-09-01 | Schwarzkopf Gmbh Hans | TWO-COMPONENT PREPARATION FOR THE PRODUCTION OF A POWDERED, APPLICABLE PREPARATION FOR THE TREATMENT OF HUMAN HAIR |
DE102005059647A1 (en) * | 2005-12-12 | 2007-06-14 | Henkel Kgaa | bleach |
FR2988588B1 (en) * | 2012-03-30 | 2014-08-29 | Oreal | PROCESS FOR DECOLORIZING KERATIN FIBERS |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2283350A (en) * | 1939-02-15 | 1942-05-19 | Mclaughlin & Wallenstein | Composition for bleaching hair |
GB1083007A (en) * | 1964-11-26 | 1967-09-13 | Rayette Faberge | Hair bleaching composition |
DE1617480B2 (en) * | 1967-08-01 | 1973-02-01 | Farbwerke Hoechst AG, vormals Mei ster Lucius & Brunmg, 6000 Frankfurt | GEL BASES |
FR2117760B1 (en) * | 1970-12-15 | 1974-03-01 | Gallia Sa Eugene | |
US3823231A (en) * | 1971-04-20 | 1974-07-09 | F Bucaria | Hair bleach containing a thiocyanate catalyst |
AU7076774A (en) * | 1974-07-04 | 1976-01-08 | Kintex Inc | Bleach |
-
1978
- 1978-12-04 CA CA317,279A patent/CA1111349A/en not_active Expired
-
1979
- 1979-10-01 GR GR60156A patent/GR74489B/el unknown
- 1979-10-09 FI FI793123A patent/FI76491C/en not_active IP Right Cessation
- 1979-10-09 DK DK425479A patent/DK425479A/en not_active Application Discontinuation
- 1979-10-09 NO NO793241A patent/NO155914C/en unknown
- 1979-10-11 IT IT7950539A patent/IT1206994B/en active
- 1979-10-11 IE IE1935/79A patent/IE48961B1/en unknown
- 1979-10-11 FR FR7925333A patent/FR2438477A1/en active Granted
- 1979-10-11 BE BE0/197609A patent/BE879364A/en not_active IP Right Cessation
- 1979-10-11 NL NL7907552A patent/NL7907552A/en not_active Application Discontinuation
- 1979-10-11 LU LU81777A patent/LU81777A1/en unknown
- 1979-10-11 GB GB7935350A patent/GB2033939B/en not_active Expired
- 1979-10-11 MX MX179622A patent/MX153887A/en unknown
- 1979-10-12 ZA ZA00795463A patent/ZA795463B/en unknown
- 1979-10-12 DE DE19792941511 patent/DE2941511A1/en not_active Ceased
- 1979-10-12 SE SE7908473A patent/SE7908473L/en not_active Application Discontinuation
- 1979-10-12 CH CH924379A patent/CH642534A5/en not_active IP Right Cessation
Cited By (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5612022A (en) * | 1994-01-14 | 1997-03-18 | L'oreal | Pulverulent hair bleach of peroxygen oxidizer and polyoxyethylene/polyoxypropylene copolymer |
US5622691A (en) * | 1994-01-14 | 1997-04-22 | L'oreal | Preparing pulverulent hair bleach of peroxygen oxidizer and polyoxyethylene/polyoxypropylene copolymer |
WO1999062469A1 (en) * | 1998-06-03 | 1999-12-09 | Henkel Kommanditgesellschaft Auf Aktien | Lightener |
WO2001043709A1 (en) * | 1999-12-17 | 2001-06-21 | Unilever Plc | Hair bleaching and colouring compositions having a ph greater than ph 10 comprising cholesterol |
US7731944B2 (en) | 2000-09-21 | 2010-06-08 | Kao Corporation | Hair cosmetic compositions |
EP1372588A4 (en) * | 2001-03-30 | 2005-01-19 | Procter & Gamble | Hair bleach product |
EP1372588A2 (en) * | 2001-03-30 | 2004-01-02 | The Procter & Gamble Company | Hair bleach product |
WO2002078662A2 (en) | 2001-03-30 | 2002-10-10 | The Procter & Gamble Company | Hair bleach product |
FR2844711A1 (en) * | 2002-06-26 | 2004-03-26 | Oreal | COMPOSITION FOR THE OXIDATION DYE OF HUMAN KERATIN FIBERS |
EP1374842A1 (en) * | 2002-06-26 | 2004-01-02 | L'oreal | Composition for the oxidative dyeing of human keratin fibres |
US7458993B2 (en) | 2002-06-26 | 2008-12-02 | L'oreal | Composition useful for the oxidation dyeing of human keratinous fibres |
WO2006060568A1 (en) * | 2004-12-02 | 2006-06-08 | The Procter & Gamble Company | Thickened hair colourant and bleaching compositions |
EP1669105A1 (en) * | 2004-12-02 | 2006-06-14 | The Procter and Gamble Company | Thickened hair colourant and bleaching compositions |
US7875269B2 (en) | 2004-12-02 | 2011-01-25 | The Procter & Gamble Company | Thickened hair colourant and bleaching compositions |
AU2005311859B2 (en) * | 2004-12-02 | 2011-12-08 | The Procter & Gamble Company | Thickened hair colourant and bleaching compositions |
AU2005311859B8 (en) * | 2004-12-02 | 2012-01-19 | The Procter & Gamble Company | Thickened hair colourant and bleaching compositions |
EP1849499A3 (en) * | 2006-04-26 | 2010-01-20 | The Procter and Gamble Company | Amide surfactant thickening systems for hair colouring and bleaching compositons |
FR2994650A1 (en) * | 2012-08-23 | 2014-02-28 | Oreal | Composition in compressed form, useful for bleaching keratin fibers e.g. human hair, comprises persulfate including e.g. sodium persulfate, and fatty alcohol including e.g. cetylstearyl alcohol |
Also Published As
Publication number | Publication date |
---|---|
MX153887A (en) | 1987-02-09 |
DK425479A (en) | 1980-04-13 |
FR2438477B1 (en) | 1983-04-08 |
GB2033939B (en) | 1983-01-19 |
DE2941511A1 (en) | 1980-04-30 |
FI76491C (en) | 1988-11-10 |
GR74489B (en) | 1984-06-28 |
IT1206994B (en) | 1989-05-17 |
SE7908473L (en) | 1980-04-13 |
FR2438477A1 (en) | 1980-05-09 |
NO793241L (en) | 1980-04-15 |
NO155914C (en) | 1987-06-24 |
NL7907552A (en) | 1980-04-15 |
LU81777A1 (en) | 1980-05-07 |
FI793123A (en) | 1980-04-13 |
FI76491B (en) | 1988-07-29 |
IE791935L (en) | 1980-04-12 |
BE879364A (en) | 1980-04-11 |
IE48961B1 (en) | 1985-06-26 |
IT7950539A0 (en) | 1979-10-11 |
CA1111349A (en) | 1981-10-27 |
CH642534A5 (en) | 1984-04-30 |
ZA795463B (en) | 1980-10-29 |
NO155914B (en) | 1987-03-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PCNP | Patent ceased through non-payment of renewal fee |