GB2185269A - Hair relaxing compositions - Google Patents

Hair relaxing compositions Download PDF

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Publication number
GB2185269A
GB2185269A GB08700315A GB8700315A GB2185269A GB 2185269 A GB2185269 A GB 2185269A GB 08700315 A GB08700315 A GB 08700315A GB 8700315 A GB8700315 A GB 8700315A GB 2185269 A GB2185269 A GB 2185269A
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composition according
hair
poe
composition
ether
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GB2185269B (en
GB8700315D0 (en
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Dwaipayan Chaudhuri
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Gillette Co LLC
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Gillette Co LLC
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/04Preparations for permanent waving or straightening the hair
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/26Aluminium; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39Derivatives containing from 2 to 10 oxyalkylene groups
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41Amines
    • A61K8/416Quaternary ammonium compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/86Polyethers

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • Cosmetics (AREA)

Abstract

A hair relaxing composition comprises, by weight (i) 1.0 to 13.0% of ammonium or alkali metal bisulphite, (ii) 5.0 to 11.0% of a mixture of polyoxyethylene (POE) 100-stearyl ether and one or more other non- ionic surfactants, the mixture having a calculated HLB of from 7 to 9, and (iii) 5.0 to 20.0% of one or more oils, the balance being water and the composition being in the form of a stable creme emulsion. 0

Description

SPECIFICATION Hair relaxing compositions and preparation and use thereof This invention is concerned with hair relaxing compositions, with a process for their preparation, and with their use in the treatment of hair.
Hair waving, hair straightening and hair relaxing are all based on the breaking, rearranging and reforming of keratin protein bonds which are responsible for hair configuration. Affecting natural hair shape by lysing the cystine disulphide linkages of keratin protein is referred to as softening or relaxing the hair. Hair softening chemicals are generally called hair waving agents, but they can equally be used to straighten hair as well. A useful discussion of the state of this art can be found, for example, in European Patent Application 75475A.
The tight curly configuration of negroid hair poses special problems. Until recently, the approach to styling this type of hair has been to straightening it using products based on sodium hydroxide or thioglycollates as the active materials and various hair straightening compositions based on one or other of these active materials are available in the U.S. and African markets.
These active materials are relatively harsh in their effect and such compositions, if not properly used, can lead to hair breakage, to loss of hair colour (black hair becoming brown), and to drying of the scalp. Their use involves multiple stages, all of which have to be carefully carried out, and they are therefore generally unsuitable for home use.
In addition, there has been a movement recently in the styling of negroid hair away from a relatively harsh straightening effect to a less drastic effect in which the natural tight curly configuration is loosened or relaxed.
In our Patent Specification 2144989A we have described bisulphite-based hair relaxing compositions which can be used for the relaxing of negroid hair (and, of course, for the waving of caucasian hair) and which are suitable for use in a one stage process, thus avoiding the multiple stage processing of conventional hair straightening compositions. Such compositions are, therefore, well suited to home use.
While bisulphite-containing hair treatment compositions are known, it is believed that the compositions described in the said specification were the first which are adapted for use in a one stage process which does not require any pre-treatment or post-treatment of the hair.
The hair relaxing composition described in the said specification comprises, by weight, (1) 1.0 to 13.0% of ammonium or alkali metal bisulphite, (ii) 5.0 to 11.0% of a mixture of polyoxyethylene 21-stearyl alcohol and one or more other polyoxyethylene non-ionic surfactants, the mixture providing at least 1.33% of POE 21-stearyl alcohol and having a calculated HLB of 7-9, and/or 0.5 to 1.5% of cetyl trimethylammonium bromide, and (iii) 5.0 to 20.0% of one or more oils, the balance being water, and the composition being in the form of a stable creme emulsion.
Whilst we previously considered that the use of POE 21-stearyl alcohol (which can equally be referred to as POE 21-stearyl ether) was criticai in the non-ionic surfactant formulations described, we have now surprisingly found that the same or essentially similar effects can be obtained by replacing the mixture of POE 21-stearyl ether and one or more other POE non-ionic surfactants by a mixture of POE 100-stearyl ether and one or more other non-ionic surfactants having a suitably low HLB so that the mixture has an overall calculated HLB of from 7 to 9.
Such a mixture of POE 100-stearyl ether and one or more other non-ionic surfactants may be used as a weight-for-weight replacement for the POE 21-stearyl ether and one or more other POE non-ionic surfactants referred to in the said specification.
According to the present invention, therefore, there is provided a hair relaxing composition, which comprises by weight: (i) 1.0 to 13.0% of ammonium or alkali metal bisulphite, (ii) 5.0 to 11.0% of a mixture of polyoxyethylene (POE) 100-stearly ether and one or more other non-ionic surfactants, the mixture having a calculated HLB of from 7 to 9, and (iii) 5.0 to 20.0% of one or more oils, the balance being water, and the composition being in the form of a stable creme emulsion.
The preferred other non-ionic surfactants for use in the non-ionic surfactant component (ii) of the composition are POE stearyl ethers (other than 100-stearyl ether), cetyl ethers, cetostearyl ethers, lauryl ethers, myristyl ethers, oleyl ethers, and tridecyl ethers. Specific preferred non-ionic surfactants are, for example:: CTFA name HLB POE 4-cetyl ether Ceteth 4 8 POE 3-cetostearyl ether Ceteareth 3 6.6 POE 4-cetostearyl ether Ceteareth 4 8.0 POE 2-lauryl ether Laureth 2 6.1 POE 3-lauryl ether Laureth 3 6.6 POE 5 lauryl ether Laureth 5 POE 4-myristyl ether Myreth 4 8.0 POE 2-oleyl ether Oleth 2 4.9 POE 3-oleyl ether Oleth 3 6.5 POE 4-oleyl ether Oleth 4 8.0 POE 4-stearyl ether Steareth 4 8.0 POE 2-stearyl ether Steareth 2 4.9 POE 3-tridecyl ether Trideceth 3 7.9 (CTFA=Cosmetic Toiletry and Fragrance Association, names used in Cosmetic Ingredient Dictionary;) These non-ionic surfactants are available from various manufacturers/suppliers under different trade marks, of which the following is a selection:: CTFA Name Trade Mark(s) Ceteth 4 Procol CA-4(1) Ceteareth 3 Procol CS-3(1); Hostacerin T-3 (2) Ceteareth 4 Procol CS-4(1); Lipocol SC-4 (3) Laureth 2 Procol LA-2(1); Carsonol L-2 (4) Laureth 3 Procol LA-3(1); Carsonol L-3 (4) Laureth 5 Procol LA-5(1) Myreth 4 Procol MA-4 (1) Oleth 2 Procol OA-2(1); Lipocol 0-2 (3) Oleth 3 Procoi OA-3 (1) Oleth 4 Procol OA-4 (1) Steareth 4 Procol SA-4 (1) Steareth 2 Procol SA-2(1); Brij 72 (5) Trideceth 3 Procol TDA-2(1); Hetoxol TD-3 (6).
(1)''Procol" is the Trade Mark of Protameen Chemical Inc., New Jersey, U.S.A., (2) "Hostacerin" is the Trade Mark of American Hoechst Corporation, Somerville, New Jersey, U.S.A., (3) "Lipocol" is the Trade Mark of Lipo Chemicals Inc., Paterson, New Jersey, U.S.A., (4) "Carsonol is the Trade Mark of Lonza, Fair Lawn, New Jersey, U.S.A., (5) "Brij" is the Trade Mark of Atlas Chemical Industries.
It is preferred that the composition according to the invention should contain at least 1.25% of POE 100-stearyl ether. Since the latter has an HLB of 18.8, it will be appreciated that of the other non-ionic surfactants mentioned above, it is preferred to use those which have the lowest HLBs (more particularly POE 2-stearyl ether, HLB 4.9 and POE 261eyl ether, HLB 4.9). Indeed, if another non-ionic surfactant is used which has an HLB of more than 5, then it is necessary for the non-ionic surfactant component to be at least ternary in composition, that is it should comprise POE 100-stearyl ether, a non-ionic surfactant having an HLB of more than 5, and a non-ionic surfactant having an HLB of less than 5.
It is particularly preferred to use POE 2-stearyl ether as the other component of the non-ionic surfactant mixture. This component is preferably provided by a mixture of EM 1207 available from Croda Chemicals, which is itself a mixture of POE 100-stearyl ether and POE 2-stearyl ether in a ratio of approximately 3:1, and sufficient additional POE 2-stearyl ether, available for example as Brij 72 from Atlas Chemical Industries or as Procol SA-2 from Protameen Chemical Inc., to obtain the desired HLB, that is the composition should contain about 4.3 times as much POE 2-stearyl ether as POE 100-stearyl ether.
Given that the preferred source of POE 100-stearyl ether, EM 1207, itself contains about 25% by weight of POE 2-stearyl ether, when using this material, it is preferred to use 1.25 to 2.25% of EM 1207 and 3.75 to 8.25% of additional POE 2-stearyl ether, for example Brij 72 or Procol SA-2.
In other respects, the composition according to the invention may be as described in the said specification and, in particular, the preferred materials for use as the various other components specified and the preferred proportions in which they are used, are as described in that specification.
Thus, as the active material, it is preferred to use ammonium bisulphite, but alkali metal bisulphites, preferably sodium bisulphite, can be used if desired. It is preferred that the composition should contain 7.0% of the active material.
Ammonium bisulphite is conveniently obtained and handled as a 40% aqueous dispersion having a pH of about 7 (adjusted with ammonium hydroxide); if such a dispersion is used as the source of the bisulphite, the composition may contain 2.5 to 32.5% of it, preferably 17.5%.
The purpose of the oil component of the composition is to facilitate removal of oily residues (whether of natural origin or previously applied) from the hair so as to permit good contact between the active material of the composition, the bisulphite, and the hair and to leave some oil on the hair after treatment to condition the hair. The oil used should, therefore, be suitable for these purposes. Suitable oils include, for example, mineral oils, that is liquid paraffins, isopropyl myristate, isopropyl palmitate, and natural oils; mixtures of two or more oils can, of course, be used. A preferred oil is the liquid paraffin available under the Trade Mark "Carnation 70".
The amount of oil used is, as stated above, from 5.0 to 20.0%; it is preferred to use about 10.09/0 The composition according to the invention may additionally contain a number of optional ingredients.
(i) Emulsion stabilisers A variety of emulsion stabilisers are known to those skilled in the art and any of them can, in principle, be used in the composition according to the invention given, of course, that they are medically approved for use in a hair care product and are chemically compatible with the other ingredients.
A preferred class of emulsion stabilisers is fatty alcohols containing from 14 to 20 carbon atoms, of which cetyl alcohol and stearyl alcohol are particularly preferred. Stearyl alcohol is the more preferred of these two with compositions containing higher levels, that is 7.0% or more, of bisulphite.
Another class of stabilisers which is suitable are the partial esters of glycerol with long chain fatty acids, such as glyceryl monostearate.
The amount of emulsion stabiliser used is suitably from 1.0 to 10.0%, more preferably about 5.0%.
(ii) Thickening agents It is preferred that the composition should be structured, that is thickened, by the inclusion of one or more thickening agents. These may be compatible with the oil phase or the aqueous phase of the emulsion.
A preferred class of oil-compatible thickening agents are cationically treated montmorillonite clays such as those available under the Trade Marks "Bentone 38" and "Bentone 27", of which the first is particularly preferred. Where such a modified clay is used, it is preferred that the composition should also contain a small proportion of a lower aliphatic alcohol or propylene carbonate, the amount of this additive preferably being about half that of the modified clay, for example 0.05 to 0.25%, more preferably 0.1%, of 95% aqueous ethanol or of propylene carbonate. The lower aliphatic alcohol or propylene carbonate serves to de-agglomerate the clay platelets and thus enhance the thickening effect of the modified clay.
Another thickening agent compatible with the oil phase that can be used is aluminium stearate.
Suitable thickening agents which are compatible with the aqueous phase include, for example, sodium carboxymethyl cellulose, hydroxyethyl cellulose, and guat gum.
The amount of thickening agent used is suitably from 0.1 to 1.0%, more preferably about 0.2%.
(iii) Hair swelling agents Hair swelling agents promote the action of the active material, the bisulphite, on the hair.
Suitable hair swelling agents are, for example, isopropyl alcohol and urea.
The amount of hair swelling agent used is suitably from 1.0 to 10.0%, more preferably about 5.0%.
(iv) Others The composition according to the invention may additionally contain one or more colourants which are non-substantive to hair, perfumes, bacteriostats, or anti-oxidants. Any such additive should, of course, be one that is medically approved for inclusion in a hair care product.
Suitable additives of these kinds and the amounts in which they are suitably used will be known to those skilled in the art.
The composition according to the invention may be prepared in any convenient way; it is normally preferred to mix the components under high shear conditions. It is preferred to mix and emulsify all the ingredients except the bisulphite at a relatively elevated temperature, for example 70"C, and then to cool the emulsion obtained to a temperature of 40"C or less before adding the bisulphite. If ammonium bisulphite is added at a temperature above 45"C, some decomposition occurs with liberation of ammonia.
A preferred procedure is as follows: 1. When an oil compatible thickener is used, it is dispersed in the oil with high shear mixing, and when such a thickener is a modified clay, a lower alcohol, such as 95% aqueous ethanol, is added after dispersion of the clay.
2. The surfactant(s) and emulsion stabiliser(s), if used, and any other oil-soluble or oil-compatible additive(s) are then added and the mixture is heated to 70"C.
3. When a water-compatible thickener is used, it is dispersed in the water with appropriate mixing and any water-soluble or water-compatible additive(s) is/are added to the dispersion. The aqueous mixture is heated to 70"C.
4. The oil phase, at 70"C, is added to the aqueous phase, at 70"C, using high shear mixing.
5. The resulting emulsion is cooled to 45"C, the bisulphite is added and the mixture is homogenised.
In use, the composition according to the invention is applied to the hair (with the latter dry, that is pre-shampooing or pre-wetting of the hair is neither required nor desirable) and rubbed in, the composition is gently combed through the hair with more composition being added to any areas which are not covered, the hair is patted flat, and the hair is left in this state for 30 to 90 minutes depending on the degree of relaxation required; this period is referred to as the "passive phase". The passive phase is preferably about 60 minutes. However a passive phase lasting longer than 90 minutes is unlikely to cause damage to the hair or scalp. The composition is then rinsed off. No post-treatment, such as neutralisation or reoxidation, is required.
It is found that tight curly hair is substantially relaxed by this treatment and is left in a soft and manageable condition.
The following examples of compositions according to the invention are given by way of illustration only.
Example 1-3 Creme emulsions of the following compositions (all percentage by weight) were prepared by the preferred procedure described above: Example 1 2 3 Brij 72 6.0 6.0 6.0 EM 1207 2.0 2.0 2.0 Cetyl alcohol 5.0 - 5.0 Stearyl alcohol - 3.0 Carnation 70 10.0 10.0 10.0 Bentone 38 0.2 0.2 0.2 95 aq. ethanol 0.1 0.1 0.1 Amm. bisulphite (40my aq. dis.) 12.5 17.5! 17.5 Isopropyl alcohol .- - 5.0 Water to 100 to 100 to 100 Brij 72=POE 2-stearyl ether.
EM 1207=POE 100-stearyl ether/POE 2-stearyl ether 3:1.
Carnation 70=liquid paraffin Bentone 38=thickening agent; a cationically treated montmorillonite clay.
Each of these emulsions was stable on storage both at room temperature and at 45"C for at least three months.
Each composition was used to treat hair in the manner described above and in each case, after rinsing off the composition, the hair was found to be substantially relaxed and in a soft and manageable condition.
Examples 4-9 Creme emulsions of the following compositions (all precentages by weight) were prepared by the preferred procedure described above:
Example 4 5 6 7 8 9 Brij 700 1.46 1.50 1.44 1.36 1 1.36 1.26 Brij 72 6.00 6.00 6.00 6.00 6.00 6.00 X 0.54 0.5 0.56 0.64 0.64 0.74 Stearyl alcohol 5.00 5.00 5.00 5.00 5.00 5.00 Bentone 38 0.20 0.20f 0.20 0.20 0.20 0.20 95% aq. EtOH 0.10 ; 0.10: 0.10 1 0.10 0.10 0.10 Carnation 70 10.00 10.00' 10.00 10.00 10.00 10.00 Amm. bisulphite i I (40% aq. dis.) 17.50; 17.50 17.50 117.50 . 17.50'17.50 Water to ' to i to ' to , to to 100 I 100 l 100 l 100 l 100 100 Brij 700=POE 100-stearyl ether.
Brij 72=POE 2-stearyl ether.
Example 4; X=POE 2-lauryl ether as Carsonol L-2.
5; X=POE 2-oleyl ether as Lipocol 0-2.
6; X=POE 3-lauryl ether as Carsonol L-3.
7; X=POE 4-cetostearyl ether as Lipocol SC-4.
8; X=POE 3-tridecyl ether as Hetoxol TD-3.
9; X=POE 4-lauryl ether as Hetoxol L-4.
Bentone 38=thickening agent; a cationically treated montmorillonite clay.
Carnation 70=liquid paraffin.
Each of these emulsions was stable on storage both at room temperature and at 45"C for at least three months.
Each composition was used to treat hair in the manner described above and in each case, after rinsing off the composition, the hair was found to be substantially relaxed and in a soft and manageable condition.

Claims (17)

1. A hair relaxing composition which comprises, by weight, (i) -1.0 to 13.0% of ammonium or alkali metal bisulphite, (ii) 5.0 to 11.0% of a mixture of polyoxyethylene (POE) 100-stearyl ether and one or more other non-ionic surfactants, the mixture having a calculated HLB of from 7 to 9, and (iii) 5.0 to 20.0% of one or more oils, the balance being water, and the composition being in the form of a stable creme emulsion.
2. A composition according to claim 1, which contains at least 1.25% of POE 100-stearyl ether.
3. A composition according to claim 1 or 2, in which the other non-ionic surfactant in component (ii) is a POE stearyl ether other than 100-stearyl ether, or a POE cetyl ehter, cetostearyl ether, lauryl ether, myristyl ether, oleyl ether, or tridecyl ether.
4. A composition according to any of claims 1 to 3, in which the other non-ionic surfactant in component (ii) is POE 2-stearyl ether.
5. A composition according to claim 4, in which the weight ratio of POE 2-stearyl ether to POE 100-stearyl ether is approximately 4.3.
6. A composition according to any of claimd 1 to 5, which comprises approximately 7.0% of the bisulphite.
7. A composition according to any of claims 1 to 6, in which the oil is a liquid paraffin.
8. A composition according to any of claims 1 to 7, which comprises approximately 10% of oil.
9. A composition according to any of claims 1 to 8, which additionally comprises from 1.0 to 10% of one or more emulsion stabilisers.
10. A composition according to claim 9, in which the emulsion stabiliser is a fatty alcohol have 14 to 20 carbon atoms.
11. A composition according to any of claims 1 to 10, which additionally comprises from 0.1 to 1.0% of one or more thickening agents.
12. A composition according to claim 11, in which the thickening agent is a cationically treated montmorillonite clay, aluminium stearate, sodium carboxymethylcellulose, hydroxyethyl cellulose, or guar gum.
13. A composition according to claim 12, in which the thickening agent is a cationically modified montmorillonite clay and the composition additionally comprises 0.05 to 0.25% of 95% aqueous ethanol or of propylene carbonate.
14. A composition according to any of claims 1 to 13, which additionally comprises from 1.0 to 10.0% of one or more hair swelling agents.
15. A composition according to claim 14, in which the hair swelling agent is isopropyl alcohol or urea.
16. A hair relaxing composition subtantially as herein described in any of Examples 1 to 9.
17. A method of relaxing hair, which comprises applying a composition according to any of claims 1 to 16 to the hair to be relaxed, maintaining the hair in a configuration appropriate to the desired relaxed effect and in contact with the composition for 30 to 90 minutes, and then rinsing the composition from the hair.
GB8700315A 1986-01-10 1987-01-08 Hair relaxing compositions and preparation and use thereof Expired GB2185269B (en)

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GB2185269A true GB2185269A (en) 1987-07-15
GB2185269B GB2185269B (en) 1989-10-25

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Cited By (14)

* Cited by examiner, † Cited by third party
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US5100657A (en) * 1990-05-01 1992-03-31 The Procter & Gamble Company Clean conditioning compositions for hair
US5100658A (en) * 1989-08-07 1992-03-31 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
US5104646A (en) * 1989-08-07 1992-04-14 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
US5106609A (en) * 1990-05-01 1992-04-21 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
EP0487105A1 (en) * 1990-11-22 1992-05-27 Yanagita Company Waving lotion and method for use thereof
US5277899A (en) * 1991-10-15 1994-01-11 The Procter & Gamble Company Hair setting composition with combination of cationic conditioners
US5807545A (en) * 1991-03-19 1998-09-15 The Procter & Gamble Co. Cosmetic compositions containing hydrophobically modified nonionic polymer and unsaturated quaternary ammonium surfactant
US5843418A (en) * 1991-03-19 1998-12-01 The Procter & Gamble Co. Cosmetic compositions containing hydrophobically modified nonionic polymer and unsaturated quaternary ammonium surfactant
EP0943315A2 (en) * 1998-03-05 1999-09-22 Bristol-Myers Squibb Company Alkaline hair conditioning compositions containing cationic guar
WO2005025526A1 (en) * 2003-09-15 2005-03-24 Unilever Plc Leave- on hair care composition
WO2015166942A1 (en) * 2014-04-28 2015-11-05 株式会社菊星 In-bath treatment composition
US9775908B2 (en) 2007-07-10 2017-10-03 Egis Gyogyszergyar Nyilvanosan Mukodo Reszvenytarsasag Pharmaceutical preparations containing highly volatile silicones
US10045935B2 (en) 2012-07-31 2018-08-14 Egis Pharmaceuticals Plc Transdermal formulation containing COX inhibitors
US11154535B2 (en) 2012-07-31 2021-10-26 Egis Pharmaceuticals Plc Transdermal formulation containing COX inhibitors

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5100658A (en) * 1989-08-07 1992-03-31 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
US5104646A (en) * 1989-08-07 1992-04-14 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
US5100657A (en) * 1990-05-01 1992-03-31 The Procter & Gamble Company Clean conditioning compositions for hair
US5106609A (en) * 1990-05-01 1992-04-21 The Procter & Gamble Company Vehicle systems for use in cosmetic compositions
EP0487105A1 (en) * 1990-11-22 1992-05-27 Yanagita Company Waving lotion and method for use thereof
US5843418A (en) * 1991-03-19 1998-12-01 The Procter & Gamble Co. Cosmetic compositions containing hydrophobically modified nonionic polymer and unsaturated quaternary ammonium surfactant
US5807545A (en) * 1991-03-19 1998-09-15 The Procter & Gamble Co. Cosmetic compositions containing hydrophobically modified nonionic polymer and unsaturated quaternary ammonium surfactant
US5855878A (en) * 1991-03-19 1999-01-05 The Procter & Gamble Company Cosmetic compositions containing hydrophobically modified nonionic polymer and unsaturated quaternary ammonium surfactant
US5277899A (en) * 1991-10-15 1994-01-11 The Procter & Gamble Company Hair setting composition with combination of cationic conditioners
US5807543A (en) * 1993-08-27 1998-09-15 The Procter & Gamble Co. Cosmetic compositions containing hydrophobically modified nonionic polymer and unsaturated quaternary ammonium surfactant
EP0943315A2 (en) * 1998-03-05 1999-09-22 Bristol-Myers Squibb Company Alkaline hair conditioning compositions containing cationic guar
EP0943315A3 (en) * 1998-03-05 2001-08-29 Bristol-Myers Squibb Company Alkaline hair conditioning compositions containing cationic guar
WO2005025526A1 (en) * 2003-09-15 2005-03-24 Unilever Plc Leave- on hair care composition
JP2007533615A (en) * 2003-09-15 2007-11-22 ユニリーバー・ナームローゼ・ベンノートシヤープ Leave on hair care composition
US9775908B2 (en) 2007-07-10 2017-10-03 Egis Gyogyszergyar Nyilvanosan Mukodo Reszvenytarsasag Pharmaceutical preparations containing highly volatile silicones
US10045935B2 (en) 2012-07-31 2018-08-14 Egis Pharmaceuticals Plc Transdermal formulation containing COX inhibitors
US11154535B2 (en) 2012-07-31 2021-10-26 Egis Pharmaceuticals Plc Transdermal formulation containing COX inhibitors
WO2015166942A1 (en) * 2014-04-28 2015-11-05 株式会社菊星 In-bath treatment composition

Also Published As

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ZA8749B (en) 1987-08-26
OA08458A (en) 1988-06-30
GB8600568D0 (en) 1986-02-19
GB2185269B (en) 1989-10-25
GB8700315D0 (en) 1987-02-11

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