CA1229305A - Neutralizing composition and method for hair waving and straightening - Google Patents
Neutralizing composition and method for hair waving and straighteningInfo
- Publication number
- CA1229305A CA1229305A CA000454949A CA454949A CA1229305A CA 1229305 A CA1229305 A CA 1229305A CA 000454949 A CA000454949 A CA 000454949A CA 454949 A CA454949 A CA 454949A CA 1229305 A CA1229305 A CA 1229305A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- hair
- neutralizing
- conditioning
- silicone polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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Classifications
-
- 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
- A61Q5/12—Preparations containing hair conditioners
-
- 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
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
Abstract
NEUTRALIZING COMPOSITION AND METHOD
FOR HAIR WAVING AND STRAIGHTENING
ABSTRACT OF THE DISCLOSURE
A neutralizing and conditioning composition for the hair includes an oxidizing agent such as hydrogen peroxide and an amino-functional polymeric silicone additive for imparting durable conditioning benefits to the hair. A method is provided for neutralizing and conditioning hair which has been subjected to a waving or straightening treatment with keratin reducing agent by applying the new composition to the treated hair.
FOR HAIR WAVING AND STRAIGHTENING
ABSTRACT OF THE DISCLOSURE
A neutralizing and conditioning composition for the hair includes an oxidizing agent such as hydrogen peroxide and an amino-functional polymeric silicone additive for imparting durable conditioning benefits to the hair. A method is provided for neutralizing and conditioning hair which has been subjected to a waving or straightening treatment with keratin reducing agent by applying the new composition to the treated hair.
Description
12293~S
NEUTRALIZING COMPOSITION AND METHOD
~--76 FOR HAIR WAVING AND STRAIGHTENING
BACKGROUND OF THE INVENTION
Field of the Invention This invention relates to a novel oxidant containing -neutralizing composition for use in conjunction with hair waving and straightening treatments and to a process for conditioning hair which has been subjected to such treatments.
More particularly, the present invention relates to a I neutralizing composition containing an oxidant and an amino-functional polymeric silicone additive for imparting durable conditioning benefits to hair which has been treatetl with a reducing agent to reduce the Courtney bonds in the hcLir as well as to the hair treating process using such opposition ' It Discussion of the Prior-Art Hair waving and hair straightening processes almost invariably include two sequential steps. In the first step, the hair is softened or relaxed with a reducing lotion which allows the hair to be molded to a desired shape. In the second, I a neutralizer is applied to the softened hair to harden and stabilize the newly imparted configuration.
The principal active ingredient of conventional neutralizers is an oxidizing agent, of which hydrogen peroxide is currently the most popular. The function of the oxidant is two-fold:
(i) to remove any residual excess of the reducing agent used in the softening step of the process; and (ii) to rebuild the disulfide cross-links in hair and, thus, to stabilize the new fiber shape and restore its strength and elasticity.
.
.. Z Z 9 3 is However, as presently practiced, not all of the disulfide _ bonds cleaved in the softening stage of the waving or straightening process can be rebuilt, and an increase in the fiber porosity and deterioration in tactile properties of hair are frequent side effects of such processes. In many cases, the neutralizing compositions contain conditioning agents such as qua ternary alkylammonium compounds, to assure smooth texture, easy combing and control of fly-away. However the conditioning effects obtained through such additives, IO although beneficial, are transient and are lost after a single shampooing.
An early example of a permanent "cold" hair waving process using mercaptan reducing agents is disclosed by Schwartz in US. Patent 2,540,494. Schwartz teaches that . the oxidizing agents in the neutralizing or setting solution used to restore the disulfide bonds can consist of any ox the typical oxidizing compounds which are non-harmful when applied to hair on the human head and are non-toxic and exemplifies such oxidizing agents with salts I of oxidizing acids, e.g. bromates and idiots ox sodium and potassium; hydrogen peroxide and its salts, such as ammonium-sulfate_p.eroxide~ urea peroxide and pyrophosphate peroxides, carbonate peroxides and perorates of sodium and potassium, as well as metal salt peroxides, salts of ~Z5 per sulfuric acid and organic peroxides and substituted peroxides. ---It--is--also known from-Schwarz thatch setting "neutralizing" solution can include at -least one acidifying reagent which may be provided by an acidic oxidizing agent such as potassium bromate or potassium idiot, or any acid . 93~5 capable of establishing a pi range in the neutralizing solution of from 2 to 4. This patent lists as exemplary _ acids moo- or poly-carboxylic organic acids such as Masonic, succinic, malefic, acetic, prop ionic, butyric and crotonic; organic acids with hydroxy groups, e.g. lactic, citric, tartaric, mafia and glycollic; inorganic acids such as sulfuric, hydrochloric and phosphoric; and acid salts including potassium or sodium, acid tart rate, citrate, or phthalate. It is further taught that a buffering salt can be employed to stabilize the phi for example, sodium acetate and acetic acid at a 2:1 ratio to provide a pi of about 3.
It is also known in the art to use various types of silicon containing polymers such as polysiloxanes for condo-toning hair in permanent waving processes. For instance, Stein Bach en at in US. Patent 3,248,~96 disclose various epoxy ~organosiloxanes to provide an elastic coating to protect hair which has been subjected Jo a sequential reducing treatment and oxidizing treatment from penetration by water without making the hairs stick to each other. In this case, the epoxy :organosiloxanes are applied after the neutralization step with hydrogen peroxide oxidizing agent.
Showier, et at in US. Patent 3,687,606, which is I described as an improvement of the aforementioned Steinbeck, et at patent, explains that the epoxy organosiloxanes function by having the epoxy groups react with the substance of the hair while the organcpolysiloxane moiety imparts water repellency. However, the prior compounds are noted to . ~293~i have the disadvantages of presenting an oily gloss to the hair and not being water soluble. Accordingly, Showier, _ et at provide epoxy sullenness as treating agents which are applied before the neutralizing treatment with the peroxide oxidizing agent but after the reducing treatment with, for example, a thioglycollic acid reducing agent.
In US. Patent 2,~44,94~ to Charles methylsilyl Marquette-acetates are used as permanent wave treating agents for single step use. These compounds dissociate into a Marquette reducing agent while generating polymers of silanols to protect the hair and facilitate combing. This patent does not talk about any subsequent treatment such as fixing by peroxides and it is not clear whether any such treatment would be required.
Other hot and cold waving and straightening hair treating compositions, which may or may not be used in conjunction with reducing and/or oxidizing agent, in which various types of selection polymers are used to fur protective film coatings on individual hairs are described in, for example, US.
Patents 2,643,375, ~,750,947, 2~782,796, 2,7~7,274, and I 2,840,087. US. Patent 3,143,476 to Grant discloses a cold wave neutralizing composition and process in which sodium and potassium bromates are used as the neutralizing agents in the presence~o~-~erruus,~~fer^ic and copper ions which junction as catalysts to increase the reaction rate of I the neutralizing agents.
There swill remains a need fox neutralizing compositions for use in-a cold permanent waving or straightening hair treating process which provides durable conditioning benefits, i.e. stable to repeated shampooings. There is additionally guy a need in the art for such neutralizing compositions which can be applied to either waved or straightened hair which significantly reduces drying time and which bring about a drastic decrease in the hair fiber porosity resulting from excessive destruction of the hair bonds while bringing about such additional beneficial results as smooth texture, easy combing and control of fly-away and which also reduces drying time.
SUMMERY OF THE INVENTION
It is an object of an aspect of the present inane-lion to provide a neutralizing composition for hair waving and straightening which provides durable conditioning benefits, namely stability to repeated shampooings.
It is an object of an aspect of the invention to provide a composition capable of neutralizing excess reducing agent and to rebuild the disulfide cross-links in hair resulting from a hair softening step which allows the hair to be dried in a reduced amount of time and which imparts improved texture, comb ability and reduced fly to the so-treated pair.
It its an object ox an aspect of toe present invent lion to provide a process for simultaneously neutralizing and conditioning hair on a human head which has been I subjected to exposure to a Courtney redwing agent such as thioglycollic acid These and other objects of the present invention which will become apparent from the hollowing detailed description of preferred embodiments are accomplished by a neutralizing and.condltioning composition four hair in the form ox an Allis solution of an oxidizing agent and I
~Z93~5 emulsified in the aqueous composition an amino-functional silicone polymer conditioning agent. The amino-functional silicone polymer is selected from the class of silicone polymers having amino functional group sand in particular, the silicone polymers include repeating structural units of the formula (It:
I Silo -R (I) C~3 NH
(R31 wherein R represents a hydrogen atom or trim ethyl-sill, lo Al represents.hydroxyl or methyl R2 represents an alkyd group of from l to 6 carbon atoms 7 R3 represents an alkyd group of from l to 4 carbon atoms, x is a positive number of at least I, y is a positive number of at least 2, and the sum ox x and y is such that the silicone polymer has a molecular weight of from about 5,000 to about Lowe, the composition having a pi in the range of from about 2.0 to 5.0 The present invention also provides a process for neutralizing and conditioning keratinic fibers such as human hair which has been subjected to a reducing treatment to reduce the disulfid~ bonds in the keratinic fibers by applying to the reduced fibers an aqueous solution of an oxidizing agent and emulsified in the solution an amino functional silicone polymer conditioning agent which includes the repeating structural units ox the Formula (I).
3 ~2~3~5 DETAILED DISCUSSION OF THE INVF,NTIOM
_ AND PREFERRED EMBODIMENTS_ .
The composition and process of the present invention are generally applicable to any of the conventional reducing agents and reducing compositions as well as to any of the conventional active neutralizing agents. The reducing agents and reducing agent compositions which are gerlerally based on ~hioglycollic acid or thioglycollic acid salts are well-known in the art and do not, per so, form any part of the lo present invention. In addition to the thioglycollic acid class of reducing agents other hair treating agents for imparting capability to hair, such as, for example, the "hair waving mercaptans" (see US. Patent 2,540,494); alkali relaxer co~Fositions, sulfite based systems, and the like can also be effectively neutralized by the neutralizing and conditioning composition of this invention.
In neutralizing and conditioning compositions of this invention, hydrogen peroxide is the preferred n~utral~zin~/oxidizing agent. However, other neutralizing agents including inorganic pa and organic peroxides and peroxide salts, perorates, bromates and the like, can also be used. In addition, neutralization can also be provided in the case of the alkali reducer compost-.. . .
toils by acidic neutralizing agents, including clowned other inorganic mineral acids in appropriate dilute concentrations.
US The amount of oxidizing agent can be within the ranges normally utilized for neutralizer compositions and will depend, for . ... . . ..
example, upon the type of oxidizing agent, the amount employed and the type of the reducing agent, etc. enroll, the amount of the oxidizing agent, will range from about 0.5% to I about 10% by weight preferably from about 1% to about 4% bar weight.
. - Z 2 3 ¦ . For optimum results, the neutralizing and conditioning ¦ compositions of the invention should have an acidic pi in the _ ¦ range of about 2 to 5, preferably about 2.5 to 4.5. Any Go l the acids conventionally used in hair neutralizing and oxidizing ¦ compositions such as those disclosed in the aforementioned Cheerios Patent 2,540,494 can be used in the present invention.
It is most preferred, however, to use a buffered acidified solution so that, for example, the generally present high natural alkalinity of hair will not substantially increase the pi of IO the invention compositions. Although optional, the use of the buffer is also preferred so that the amount of damage to the hair from harsh waving chemicals will be minimized. Any acid and buffer system capable of maintaining a pi in the desired pi range of 2 to 5 can be used in the composition of this invention.
Especially good results have been obtained using phosphoric acid as top acidifying agent and a citric acid/citrate ion buffer : siesta. however, other acids and buffer systems can also be used so long as the pi can be maintained in the range of 2 to 5.
Preferably, the buffering agent is provided separately from eye I remaining ingredients of the composition to avoid breaking the silicone emulsion in the, e.g. peroxide, neutralizing agent upon .
standing on the shelf for a prolonged time due to the high acid capacity generated my toe buffer,~and-is-combin~d with the-other- .
ingredients just prior to use.
The oxidizing agent, e.g. hydrogen peroxide, is the main active ingredient of the composition and functions to remove any residual excess of the reducing agent or alkali used in the -¦ softening step of the waving or straightening process wile additionally restoring the Courtney disulfide bonds cleaved in the previous reducing step.
it I ~Z293~5 .. , I
¦ The other critical component of the compositions of this . I invention is the silicone polymer conditioning agent. These ¦ are amino-functional silicone polymers which can be represented . ¦ by the following formula (I):
So - --O } -O R (I) i NH
wherein R represents a hydrogen atom or trimethylsilyl, Al represents hydroxyl or methyl, R2 represents a diva lent alkyd group of from 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms, which may be straight or lo branched;
R3 represents a diva lent alkyd group of from 1 to 4 carbon atoms, preferably 2 to 3 carbon atoms, which may be straight or branched;
. x is a positive number of at least 4; and y is a positive number of at least I.
One such suitable amino-functional silicone polymer has top common name amodimethicone which is a cat ionic polymer of the formula (1) wherein R is hydrogen, Al is -SHEA, R2 is SHEA and I is ~GH~2. Amodimethicone is commercially availably in the form of its aqueous emulsion from Dow Corning under the designations Dow Corning 929 Emulsion and Silicone 929 Cat ionic Emulsion.
The amount of the silicone polymer- is generally in the range of from about 0.1 to 10% by weight, preferably from about 1 to 2% by weight of the composition. At amounts below about ."~,,~,.
~293~
¦ 0.1%, the conditioning benefits are insufficient while at amounts above about 10%, no additional benefits are observed and stable emulsions are more difficult to prepare.
l Any emulsifying agents which can maintain a stable Emil-soon and which are compatible with the remaining ingredients can be used in the neutralizing and conditioning compositions of this invention. Preferably cat ionic type emulsifying agents will be used with the cat ionic silicone polymers RHO and non ionic type emulsifying agents will be used with the non ionic silicone polymers (R= trimethylsilyl). Generally, these amino-functional silicone polymers are commercially available in the form of emulsions and can be used as such in the compositions of this invention without separate addition of an emulsifying agent. For instance, Dow Corning Emulsion 929, which is an emulsion of the cat ionic silicone polymer, amodimethicone, includes a mixture of a cat ionic emulsifier (tallow trimonium chloride) and a non ionic emulsifier Jan ethoxylated phenol).
The Dow Corning Emulsion X2-7224, which, according to its manufacturer, is an emulsion containing about 35% by weight of a non ionic silicone polymer of formula I in which R is in-methylsilyl, Al is methyl, I is isobutyl ~CH2CHCH2~ and SHEA
R3 is ethyl ~C~2CH I, includes-a-mixture of non ionic emuls liens, namely about 3% by weight of an ethoxylated alcohol (Briton X405, a product of Room and Hays) and about 3X by weight of an ethics-fated phenol ~Tergitol TMN-6, a product of Union Carbide).
Generally, any of the conventional emulsifying agents typically used in hair treating compositions can be used in the compositions ox this invention. Representative non ionic ' . 3 5 ¦ emulsifiers include, for example, polyethoxylated or Polyp ¦ glycerolated alcohols, alkylphenols or fatty acids having a .
¦ linear chain of 8 to 18 carbon atoms, and generally 2 to 3q moles l of ethylene oxide, ethylene oxide/propylene oxide copolymers, ¦ fatty alcohols, condensates of ethylene or propylene oxide with fatty alcohols, polyethoxylated fatty asides, polyethoxylated fatty amine, ethanolamides, glycol esters of fatty acids, sorbitol esters of fatty acids and succors esters of fatty acids.
I . Representative cat ionic emulsifiers include, for example, qua ternary ammonium, morpholinIum, and purred em compounds.
3~5 The amount of the emulsifying agent or agents is not particularly critical so long as the silicone polymer is main- _ twined in the emulsified state aster blending with the oxidizing agent and other components of the compositions. enroll, amounts of thy emulsifier or emulsifiers in the range of from about 2 to about 20%, preferably from about 8 to about 18 %, by weight of the silicone polymer are satisfactory.
The silicone polymer, if it is not provided in an emulsi-fled state, is preferably emulsified with one or more emulsifying I agents before being mixed with the aqueous acidic solution of the oxidizing agent. The mixing of the emulsifying agents) with the silicone polymer, if necessary, and the blending of the emulsified silicone polymer with the aqueous acidic solution of the oxidizing agent can be simply performed by It mixing the ingredients in any conventional mixing or blending apparatus at room temperature or at slightly elevated tempera-Tory Of course, mixing speeds, shear rate, etc., should not be such as to cause breaking of the emulsion.
Other conventional additives, such as, for example, ZOO perfumes and other fragrances, thickening agents, surface active agents, other conditioning agents, germicides, beater .
iocides, and the like, can be added to the compositions in amounts which-do~-not`interfere with the activity of the oxidizing agent or silicone polymer and which do not interfere with the
NEUTRALIZING COMPOSITION AND METHOD
~--76 FOR HAIR WAVING AND STRAIGHTENING
BACKGROUND OF THE INVENTION
Field of the Invention This invention relates to a novel oxidant containing -neutralizing composition for use in conjunction with hair waving and straightening treatments and to a process for conditioning hair which has been subjected to such treatments.
More particularly, the present invention relates to a I neutralizing composition containing an oxidant and an amino-functional polymeric silicone additive for imparting durable conditioning benefits to hair which has been treatetl with a reducing agent to reduce the Courtney bonds in the hcLir as well as to the hair treating process using such opposition ' It Discussion of the Prior-Art Hair waving and hair straightening processes almost invariably include two sequential steps. In the first step, the hair is softened or relaxed with a reducing lotion which allows the hair to be molded to a desired shape. In the second, I a neutralizer is applied to the softened hair to harden and stabilize the newly imparted configuration.
The principal active ingredient of conventional neutralizers is an oxidizing agent, of which hydrogen peroxide is currently the most popular. The function of the oxidant is two-fold:
(i) to remove any residual excess of the reducing agent used in the softening step of the process; and (ii) to rebuild the disulfide cross-links in hair and, thus, to stabilize the new fiber shape and restore its strength and elasticity.
.
.. Z Z 9 3 is However, as presently practiced, not all of the disulfide _ bonds cleaved in the softening stage of the waving or straightening process can be rebuilt, and an increase in the fiber porosity and deterioration in tactile properties of hair are frequent side effects of such processes. In many cases, the neutralizing compositions contain conditioning agents such as qua ternary alkylammonium compounds, to assure smooth texture, easy combing and control of fly-away. However the conditioning effects obtained through such additives, IO although beneficial, are transient and are lost after a single shampooing.
An early example of a permanent "cold" hair waving process using mercaptan reducing agents is disclosed by Schwartz in US. Patent 2,540,494. Schwartz teaches that . the oxidizing agents in the neutralizing or setting solution used to restore the disulfide bonds can consist of any ox the typical oxidizing compounds which are non-harmful when applied to hair on the human head and are non-toxic and exemplifies such oxidizing agents with salts I of oxidizing acids, e.g. bromates and idiots ox sodium and potassium; hydrogen peroxide and its salts, such as ammonium-sulfate_p.eroxide~ urea peroxide and pyrophosphate peroxides, carbonate peroxides and perorates of sodium and potassium, as well as metal salt peroxides, salts of ~Z5 per sulfuric acid and organic peroxides and substituted peroxides. ---It--is--also known from-Schwarz thatch setting "neutralizing" solution can include at -least one acidifying reagent which may be provided by an acidic oxidizing agent such as potassium bromate or potassium idiot, or any acid . 93~5 capable of establishing a pi range in the neutralizing solution of from 2 to 4. This patent lists as exemplary _ acids moo- or poly-carboxylic organic acids such as Masonic, succinic, malefic, acetic, prop ionic, butyric and crotonic; organic acids with hydroxy groups, e.g. lactic, citric, tartaric, mafia and glycollic; inorganic acids such as sulfuric, hydrochloric and phosphoric; and acid salts including potassium or sodium, acid tart rate, citrate, or phthalate. It is further taught that a buffering salt can be employed to stabilize the phi for example, sodium acetate and acetic acid at a 2:1 ratio to provide a pi of about 3.
It is also known in the art to use various types of silicon containing polymers such as polysiloxanes for condo-toning hair in permanent waving processes. For instance, Stein Bach en at in US. Patent 3,248,~96 disclose various epoxy ~organosiloxanes to provide an elastic coating to protect hair which has been subjected Jo a sequential reducing treatment and oxidizing treatment from penetration by water without making the hairs stick to each other. In this case, the epoxy :organosiloxanes are applied after the neutralization step with hydrogen peroxide oxidizing agent.
Showier, et at in US. Patent 3,687,606, which is I described as an improvement of the aforementioned Steinbeck, et at patent, explains that the epoxy organosiloxanes function by having the epoxy groups react with the substance of the hair while the organcpolysiloxane moiety imparts water repellency. However, the prior compounds are noted to . ~293~i have the disadvantages of presenting an oily gloss to the hair and not being water soluble. Accordingly, Showier, _ et at provide epoxy sullenness as treating agents which are applied before the neutralizing treatment with the peroxide oxidizing agent but after the reducing treatment with, for example, a thioglycollic acid reducing agent.
In US. Patent 2,~44,94~ to Charles methylsilyl Marquette-acetates are used as permanent wave treating agents for single step use. These compounds dissociate into a Marquette reducing agent while generating polymers of silanols to protect the hair and facilitate combing. This patent does not talk about any subsequent treatment such as fixing by peroxides and it is not clear whether any such treatment would be required.
Other hot and cold waving and straightening hair treating compositions, which may or may not be used in conjunction with reducing and/or oxidizing agent, in which various types of selection polymers are used to fur protective film coatings on individual hairs are described in, for example, US.
Patents 2,643,375, ~,750,947, 2~782,796, 2,7~7,274, and I 2,840,087. US. Patent 3,143,476 to Grant discloses a cold wave neutralizing composition and process in which sodium and potassium bromates are used as the neutralizing agents in the presence~o~-~erruus,~~fer^ic and copper ions which junction as catalysts to increase the reaction rate of I the neutralizing agents.
There swill remains a need fox neutralizing compositions for use in-a cold permanent waving or straightening hair treating process which provides durable conditioning benefits, i.e. stable to repeated shampooings. There is additionally guy a need in the art for such neutralizing compositions which can be applied to either waved or straightened hair which significantly reduces drying time and which bring about a drastic decrease in the hair fiber porosity resulting from excessive destruction of the hair bonds while bringing about such additional beneficial results as smooth texture, easy combing and control of fly-away and which also reduces drying time.
SUMMERY OF THE INVENTION
It is an object of an aspect of the present inane-lion to provide a neutralizing composition for hair waving and straightening which provides durable conditioning benefits, namely stability to repeated shampooings.
It is an object of an aspect of the invention to provide a composition capable of neutralizing excess reducing agent and to rebuild the disulfide cross-links in hair resulting from a hair softening step which allows the hair to be dried in a reduced amount of time and which imparts improved texture, comb ability and reduced fly to the so-treated pair.
It its an object ox an aspect of toe present invent lion to provide a process for simultaneously neutralizing and conditioning hair on a human head which has been I subjected to exposure to a Courtney redwing agent such as thioglycollic acid These and other objects of the present invention which will become apparent from the hollowing detailed description of preferred embodiments are accomplished by a neutralizing and.condltioning composition four hair in the form ox an Allis solution of an oxidizing agent and I
~Z93~5 emulsified in the aqueous composition an amino-functional silicone polymer conditioning agent. The amino-functional silicone polymer is selected from the class of silicone polymers having amino functional group sand in particular, the silicone polymers include repeating structural units of the formula (It:
I Silo -R (I) C~3 NH
(R31 wherein R represents a hydrogen atom or trim ethyl-sill, lo Al represents.hydroxyl or methyl R2 represents an alkyd group of from l to 6 carbon atoms 7 R3 represents an alkyd group of from l to 4 carbon atoms, x is a positive number of at least I, y is a positive number of at least 2, and the sum ox x and y is such that the silicone polymer has a molecular weight of from about 5,000 to about Lowe, the composition having a pi in the range of from about 2.0 to 5.0 The present invention also provides a process for neutralizing and conditioning keratinic fibers such as human hair which has been subjected to a reducing treatment to reduce the disulfid~ bonds in the keratinic fibers by applying to the reduced fibers an aqueous solution of an oxidizing agent and emulsified in the solution an amino functional silicone polymer conditioning agent which includes the repeating structural units ox the Formula (I).
3 ~2~3~5 DETAILED DISCUSSION OF THE INVF,NTIOM
_ AND PREFERRED EMBODIMENTS_ .
The composition and process of the present invention are generally applicable to any of the conventional reducing agents and reducing compositions as well as to any of the conventional active neutralizing agents. The reducing agents and reducing agent compositions which are gerlerally based on ~hioglycollic acid or thioglycollic acid salts are well-known in the art and do not, per so, form any part of the lo present invention. In addition to the thioglycollic acid class of reducing agents other hair treating agents for imparting capability to hair, such as, for example, the "hair waving mercaptans" (see US. Patent 2,540,494); alkali relaxer co~Fositions, sulfite based systems, and the like can also be effectively neutralized by the neutralizing and conditioning composition of this invention.
In neutralizing and conditioning compositions of this invention, hydrogen peroxide is the preferred n~utral~zin~/oxidizing agent. However, other neutralizing agents including inorganic pa and organic peroxides and peroxide salts, perorates, bromates and the like, can also be used. In addition, neutralization can also be provided in the case of the alkali reducer compost-.. . .
toils by acidic neutralizing agents, including clowned other inorganic mineral acids in appropriate dilute concentrations.
US The amount of oxidizing agent can be within the ranges normally utilized for neutralizer compositions and will depend, for . ... . . ..
example, upon the type of oxidizing agent, the amount employed and the type of the reducing agent, etc. enroll, the amount of the oxidizing agent, will range from about 0.5% to I about 10% by weight preferably from about 1% to about 4% bar weight.
. - Z 2 3 ¦ . For optimum results, the neutralizing and conditioning ¦ compositions of the invention should have an acidic pi in the _ ¦ range of about 2 to 5, preferably about 2.5 to 4.5. Any Go l the acids conventionally used in hair neutralizing and oxidizing ¦ compositions such as those disclosed in the aforementioned Cheerios Patent 2,540,494 can be used in the present invention.
It is most preferred, however, to use a buffered acidified solution so that, for example, the generally present high natural alkalinity of hair will not substantially increase the pi of IO the invention compositions. Although optional, the use of the buffer is also preferred so that the amount of damage to the hair from harsh waving chemicals will be minimized. Any acid and buffer system capable of maintaining a pi in the desired pi range of 2 to 5 can be used in the composition of this invention.
Especially good results have been obtained using phosphoric acid as top acidifying agent and a citric acid/citrate ion buffer : siesta. however, other acids and buffer systems can also be used so long as the pi can be maintained in the range of 2 to 5.
Preferably, the buffering agent is provided separately from eye I remaining ingredients of the composition to avoid breaking the silicone emulsion in the, e.g. peroxide, neutralizing agent upon .
standing on the shelf for a prolonged time due to the high acid capacity generated my toe buffer,~and-is-combin~d with the-other- .
ingredients just prior to use.
The oxidizing agent, e.g. hydrogen peroxide, is the main active ingredient of the composition and functions to remove any residual excess of the reducing agent or alkali used in the -¦ softening step of the waving or straightening process wile additionally restoring the Courtney disulfide bonds cleaved in the previous reducing step.
it I ~Z293~5 .. , I
¦ The other critical component of the compositions of this . I invention is the silicone polymer conditioning agent. These ¦ are amino-functional silicone polymers which can be represented . ¦ by the following formula (I):
So - --O } -O R (I) i NH
wherein R represents a hydrogen atom or trimethylsilyl, Al represents hydroxyl or methyl, R2 represents a diva lent alkyd group of from 1 to 6 carbon atoms, preferably 2 to 4 carbon atoms, which may be straight or lo branched;
R3 represents a diva lent alkyd group of from 1 to 4 carbon atoms, preferably 2 to 3 carbon atoms, which may be straight or branched;
. x is a positive number of at least 4; and y is a positive number of at least I.
One such suitable amino-functional silicone polymer has top common name amodimethicone which is a cat ionic polymer of the formula (1) wherein R is hydrogen, Al is -SHEA, R2 is SHEA and I is ~GH~2. Amodimethicone is commercially availably in the form of its aqueous emulsion from Dow Corning under the designations Dow Corning 929 Emulsion and Silicone 929 Cat ionic Emulsion.
The amount of the silicone polymer- is generally in the range of from about 0.1 to 10% by weight, preferably from about 1 to 2% by weight of the composition. At amounts below about ."~,,~,.
~293~
¦ 0.1%, the conditioning benefits are insufficient while at amounts above about 10%, no additional benefits are observed and stable emulsions are more difficult to prepare.
l Any emulsifying agents which can maintain a stable Emil-soon and which are compatible with the remaining ingredients can be used in the neutralizing and conditioning compositions of this invention. Preferably cat ionic type emulsifying agents will be used with the cat ionic silicone polymers RHO and non ionic type emulsifying agents will be used with the non ionic silicone polymers (R= trimethylsilyl). Generally, these amino-functional silicone polymers are commercially available in the form of emulsions and can be used as such in the compositions of this invention without separate addition of an emulsifying agent. For instance, Dow Corning Emulsion 929, which is an emulsion of the cat ionic silicone polymer, amodimethicone, includes a mixture of a cat ionic emulsifier (tallow trimonium chloride) and a non ionic emulsifier Jan ethoxylated phenol).
The Dow Corning Emulsion X2-7224, which, according to its manufacturer, is an emulsion containing about 35% by weight of a non ionic silicone polymer of formula I in which R is in-methylsilyl, Al is methyl, I is isobutyl ~CH2CHCH2~ and SHEA
R3 is ethyl ~C~2CH I, includes-a-mixture of non ionic emuls liens, namely about 3% by weight of an ethoxylated alcohol (Briton X405, a product of Room and Hays) and about 3X by weight of an ethics-fated phenol ~Tergitol TMN-6, a product of Union Carbide).
Generally, any of the conventional emulsifying agents typically used in hair treating compositions can be used in the compositions ox this invention. Representative non ionic ' . 3 5 ¦ emulsifiers include, for example, polyethoxylated or Polyp ¦ glycerolated alcohols, alkylphenols or fatty acids having a .
¦ linear chain of 8 to 18 carbon atoms, and generally 2 to 3q moles l of ethylene oxide, ethylene oxide/propylene oxide copolymers, ¦ fatty alcohols, condensates of ethylene or propylene oxide with fatty alcohols, polyethoxylated fatty asides, polyethoxylated fatty amine, ethanolamides, glycol esters of fatty acids, sorbitol esters of fatty acids and succors esters of fatty acids.
I . Representative cat ionic emulsifiers include, for example, qua ternary ammonium, morpholinIum, and purred em compounds.
3~5 The amount of the emulsifying agent or agents is not particularly critical so long as the silicone polymer is main- _ twined in the emulsified state aster blending with the oxidizing agent and other components of the compositions. enroll, amounts of thy emulsifier or emulsifiers in the range of from about 2 to about 20%, preferably from about 8 to about 18 %, by weight of the silicone polymer are satisfactory.
The silicone polymer, if it is not provided in an emulsi-fled state, is preferably emulsified with one or more emulsifying I agents before being mixed with the aqueous acidic solution of the oxidizing agent. The mixing of the emulsifying agents) with the silicone polymer, if necessary, and the blending of the emulsified silicone polymer with the aqueous acidic solution of the oxidizing agent can be simply performed by It mixing the ingredients in any conventional mixing or blending apparatus at room temperature or at slightly elevated tempera-Tory Of course, mixing speeds, shear rate, etc., should not be such as to cause breaking of the emulsion.
Other conventional additives, such as, for example, ZOO perfumes and other fragrances, thickening agents, surface active agents, other conditioning agents, germicides, beater .
iocides, and the like, can be added to the compositions in amounts which-do~-not`interfere with the activity of the oxidizing agent or silicone polymer and which do not interfere with the
2-5 stability of the emulsion.
The buffering agent can be added to the composition sat any time, however, it issue lye preferred to package the buffering agent separately from the other components of the compositions with instructions to the user to mix the two packages just pa prior to use.
. . . .. . . . .. . .
lZ2~3~5 ¦ Although not wishing to be bound by any particular theory ¦ as to the mechanism by which the silicone polymers exhibit ¦ their beneficial properties, it is presumed that the silicone ¦ polymers form a stable, adherent, mechanically strong, and l abrasion resistant film on the individual hairs which eases ¦ comba~ility and facilitates drying ox the hair. The latter phenomenon may be due to the low surface tension properties of the silicone polymers which results in formation of thin water films which can be more easily evaporated from the treated hair.
As previously described, the neutralizing and conditioning compositions of this invention can be used with substantially any hair treating composition which accomplishes its waving or straightening function by reduction of the keratinic desulfide bonds. The following is representative of a typical relaxer composition:
Concentration Ingredient Lowe hi %) Petrolatum 24.00 Mineral Oil 16.00 Polawax (non ionic 8.00 emulsifying wax) Solulan 25 ~ethoxylated 3.00 lanolin alcohol) Propylene glycol 2.50 Sodium hydroxide 1~75 Seattle alcohol 1.25 Fragrance 0.50 Water us to 100.00 ' ~2293~S
A conventional thioglycolate waving composition is provided by the following lotion formulation:
Concentration Ingredient (Weight%) Ammonium thioglycolate 5.1 Monoethanolamine 2.5 Brim 35 (polyoxyethylene 1.2 laurel ether) Fragrance 1.0 Pacifier 1.0 Water us to 100.0 The invention will now be described by way of the following illustrative but non-limitative examples in which all "parts" and percentages are on a weight basis unless otherwise noted.
EXAMPLE I
Three brown Caucasian hair tresses, 2 g each, are wound on 1/2 inch rods and are saturated with a conventional thioglycolate lotion (0.6 M ammonium thioglycolate, pi 9.2).
After 20 minutes, the waving lotion is rinsed off and the tresses, while still on the rods, are treated in the following manner:
Tress #1 is saturated for 5 min. with 1.2% HOWE
adjusted to pi with phosphoric acid;
Tress #2 is saturated for 5 min. with 1.2% HOWE
containing 1.5% amodimethicone adjusted to pi 4 with phosphoric acid;
Tress #3 is saturated for 5 min. with 1.2% HOWE
containing 1.5% amodimethicone adjusted to pi 3 with phosphoric acid and buffered with citric acid (0.25 M).
,; Jo . , "
The buffering agent can be added to the composition sat any time, however, it issue lye preferred to package the buffering agent separately from the other components of the compositions with instructions to the user to mix the two packages just pa prior to use.
. . . .. . . . .. . .
lZ2~3~5 ¦ Although not wishing to be bound by any particular theory ¦ as to the mechanism by which the silicone polymers exhibit ¦ their beneficial properties, it is presumed that the silicone ¦ polymers form a stable, adherent, mechanically strong, and l abrasion resistant film on the individual hairs which eases ¦ comba~ility and facilitates drying ox the hair. The latter phenomenon may be due to the low surface tension properties of the silicone polymers which results in formation of thin water films which can be more easily evaporated from the treated hair.
As previously described, the neutralizing and conditioning compositions of this invention can be used with substantially any hair treating composition which accomplishes its waving or straightening function by reduction of the keratinic desulfide bonds. The following is representative of a typical relaxer composition:
Concentration Ingredient Lowe hi %) Petrolatum 24.00 Mineral Oil 16.00 Polawax (non ionic 8.00 emulsifying wax) Solulan 25 ~ethoxylated 3.00 lanolin alcohol) Propylene glycol 2.50 Sodium hydroxide 1~75 Seattle alcohol 1.25 Fragrance 0.50 Water us to 100.00 ' ~2293~S
A conventional thioglycolate waving composition is provided by the following lotion formulation:
Concentration Ingredient (Weight%) Ammonium thioglycolate 5.1 Monoethanolamine 2.5 Brim 35 (polyoxyethylene 1.2 laurel ether) Fragrance 1.0 Pacifier 1.0 Water us to 100.0 The invention will now be described by way of the following illustrative but non-limitative examples in which all "parts" and percentages are on a weight basis unless otherwise noted.
EXAMPLE I
Three brown Caucasian hair tresses, 2 g each, are wound on 1/2 inch rods and are saturated with a conventional thioglycolate lotion (0.6 M ammonium thioglycolate, pi 9.2).
After 20 minutes, the waving lotion is rinsed off and the tresses, while still on the rods, are treated in the following manner:
Tress #1 is saturated for 5 min. with 1.2% HOWE
adjusted to pi with phosphoric acid;
Tress #2 is saturated for 5 min. with 1.2% HOWE
containing 1.5% amodimethicone adjusted to pi 4 with phosphoric acid;
Tress #3 is saturated for 5 min. with 1.2% HOWE
containing 1.5% amodimethicone adjusted to pi 3 with phosphoric acid and buffered with citric acid (0.25 M).
,; Jo . , "
3~5 After 5 minutes, the rods are removed, the peroxide solutions are worked into loose hair coils, left for an additional 3 _ minutes and rinsed off under running tap water. The tresses are then wet combed using a strain gauge comb and the work of combing is recorded. The following results are obtained:
Tress # Work of Comb go (grow) Aster combing, the tresses are reimmersed in water, removed and freely hung to dry. Their weights are reworded immediately after removal from water and after drying. me water contents of tresses as calculated from the difference in dry end wet weights are as follows:
Tress Kit Water pickup 'glue of hair) Jo 1 2.5 2 1.5 3 1.6 The amount of water held by the hair after centrifuging (liquid retention of porosity index) is also measured, yielding the following results:
tress # Jo Liquid Retention (OWE) 1 42.5 2 41.3 Z5 3 it Finally, the tresses are shampooed twice and their wet combing is redetermined. the values of combing work are as follows:
. ~LZ~93~5 Tress T~Jork of Combing (Ram) 1 764 _ 2 1~0 EXAMPLE II
In order to demonstrate the faster rate of hair drying at the completion of the waving (or straightening) Procedure, the following experiment us carried out.
A group of four hair tresses (intact ~eMeo brown hair, It 2 g per tress) is waved for lo minutes at 35C using a con-~entional waving lotion. The hair is then rinsed and two tresses are neutralized with a conventional neutralizer (2.0%
H202) while the other two are neutralized with a combination of H202 (2.G%~ and amodimethicone I In Roth cases, the neutralization is carried out for 10 minutes, after which time the tresses are rinsed and each of them is attached to a stress gauge allowing for accurate weight determination. The weighing is continuously monitored for a period of 45 minutes. The data of Table I show the weight changes (mean average of 2) at I selected time interval. The lower the water content of hair .
the faster it dries.
TABLE I
__ _ Water content of hair 'g Hug of hair) following neutralization I Neutralization = - I 0 1 15( l I D 45 .51 1 lo I US I .84 '74 Lo 1 I
. .
. .
93~5 I EXAMPLE III
I
¦ A composition according to the invention is prepared by ¦ adding two thickening agents (Igepol C0 430 and Ige~ol (C0 630) l and an additional emulsifying agent, Seattle alcohol:
S Component Lotte Hydrogen peroxide 2.0 Seattle Alcohol 0.2 Igepol C0 430 4.0 Igepol C0 630 4.0 Phosphoric Acid 0.03 Dow Corning Emulsion 92~ ~.00 Water 85.77 A stable thickened composition is obtained.
.
I"
Tress # Work of Comb go (grow) Aster combing, the tresses are reimmersed in water, removed and freely hung to dry. Their weights are reworded immediately after removal from water and after drying. me water contents of tresses as calculated from the difference in dry end wet weights are as follows:
Tress Kit Water pickup 'glue of hair) Jo 1 2.5 2 1.5 3 1.6 The amount of water held by the hair after centrifuging (liquid retention of porosity index) is also measured, yielding the following results:
tress # Jo Liquid Retention (OWE) 1 42.5 2 41.3 Z5 3 it Finally, the tresses are shampooed twice and their wet combing is redetermined. the values of combing work are as follows:
. ~LZ~93~5 Tress T~Jork of Combing (Ram) 1 764 _ 2 1~0 EXAMPLE II
In order to demonstrate the faster rate of hair drying at the completion of the waving (or straightening) Procedure, the following experiment us carried out.
A group of four hair tresses (intact ~eMeo brown hair, It 2 g per tress) is waved for lo minutes at 35C using a con-~entional waving lotion. The hair is then rinsed and two tresses are neutralized with a conventional neutralizer (2.0%
H202) while the other two are neutralized with a combination of H202 (2.G%~ and amodimethicone I In Roth cases, the neutralization is carried out for 10 minutes, after which time the tresses are rinsed and each of them is attached to a stress gauge allowing for accurate weight determination. The weighing is continuously monitored for a period of 45 minutes. The data of Table I show the weight changes (mean average of 2) at I selected time interval. The lower the water content of hair .
the faster it dries.
TABLE I
__ _ Water content of hair 'g Hug of hair) following neutralization I Neutralization = - I 0 1 15( l I D 45 .51 1 lo I US I .84 '74 Lo 1 I
. .
. .
93~5 I EXAMPLE III
I
¦ A composition according to the invention is prepared by ¦ adding two thickening agents (Igepol C0 430 and Ige~ol (C0 630) l and an additional emulsifying agent, Seattle alcohol:
S Component Lotte Hydrogen peroxide 2.0 Seattle Alcohol 0.2 Igepol C0 430 4.0 Igepol C0 630 4.0 Phosphoric Acid 0.03 Dow Corning Emulsion 92~ ~.00 Water 85.77 A stable thickened composition is obtained.
.
I"
Claims (8)
1. A neutralizing and conditioning composition for hair comprising an aqueous emulsion of an aqueous solution of an oxidizing agent, and a silicone polymer of the formula wherein R represents hydrogen or trimethylsilyl, R1 represents hydroxyl or methl, R2 represents alkyl of from 1 to 6 carbon atoms, R3 represents alkyl of from 1 to 4 carbon atoms, x is a number of at least 4, y is a number of at least 2, and the sum of x + y is such that the silicone polymer has a molecular weight in the range of from about 5000 to about 100,000, said composition having a pH in the range of from about 2.0 to about 5Ø
2. The composition of claim 1 wherein the silicone polymer is present in an amount of from about 0.1 to about 10%
by weight based on the total composition.
by weight based on the total composition.
3. The composition of claim 2 where the amount of the silicone polymer is from about 1 to 2% by weight.
4. The composition of claim 1 wherein R is hydrogen, R1 represents,hydroxyl, R2 represents and R3 represent.
5. The composition of claim 1 which further comprises a buffering agent to maintain the pH of the composition in the range of from about 2.0 to 5Ø
6. The composition of claim 5 wherein the buffering agent is citric acid/citrate salt and wherein the composition is acidified to a pH of about 3,0 with phosphoric acid,
7. A method for neutralizing and conditioning hair which has been subjected to a waving or straightening treatment with a reducing agent capable of reducing keratinic disulfide bonds which comprises applying to the treated hair a composition containing an effective amount of neutralizing and conditioning composition of claim 1.
8. The method of claim 7 which further comprises mixing the neutralizing and conditioning composition, just prior to applying the composition to the treated hair, with a buffering agent capable of maintaining the pH of the neutralizing and conditioning composition within said pH range of 2.0 to 5.0 in the presence of any residual alkalinity in the treated hair.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50454183A | 1983-06-15 | 1983-06-15 | |
| US504,541 | 1983-06-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1229305A true CA1229305A (en) | 1987-11-17 |
Family
ID=24006715
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000454949A Expired CA1229305A (en) | 1983-06-15 | 1984-05-23 | Neutralizing composition and method for hair waving and straightening |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS608216A (en) |
| AU (1) | AU548452B2 (en) |
| CA (1) | CA1229305A (en) |
| DE (1) | DE3421358C2 (en) |
| FR (1) | FR2548020A1 (en) |
| GB (1) | GB2141454B (en) |
| GR (1) | GR82154B (en) |
| IT (1) | IT1181902B (en) |
| SE (1) | SE465204B (en) |
| ZA (1) | ZA844309B (en) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4915938A (en) * | 1987-11-13 | 1990-04-10 | Zawadzki Mary E | Hair treating composition |
| JP2579516B2 (en) * | 1988-02-09 | 1997-02-05 | 株式会社資生堂 | Hair cosmetics |
| US5068101A (en) * | 1988-03-25 | 1991-11-26 | Johnson Products Co., Inc. | Hair relaxer cream |
| US5077042A (en) * | 1988-03-25 | 1991-12-31 | Johnson Products Co., Inc. | Conditioning hair relaxer system with conditioning activator |
| US5171565A (en) * | 1988-03-25 | 1992-12-15 | Johnson Products Co., Inc. | Hair relaxer cream |
| US4950485A (en) * | 1988-03-25 | 1990-08-21 | Johnson Products Co., Inc. | Hair relaxer cream |
| US5270036A (en) * | 1992-10-13 | 1993-12-14 | Dow Corning Corporation | Permanent waving with silicones |
| US6274126B1 (en) | 1998-08-21 | 2001-08-14 | Helene Curtis, Inc. | Composition for lightening and highlighting hair |
| FR2823110B1 (en) * | 2001-04-06 | 2004-03-05 | Oreal | PROCESS FOR PERMANENT DEFORMATION OF HAIR USING AMINO SILICONES |
| US6723308B2 (en) | 2001-11-02 | 2004-04-20 | Kenra, Llc | Hair clarifying treatment |
| US6805136B2 (en) | 2001-11-02 | 2004-10-19 | Kenra, Llc | Hair relaxer |
| FR2831802B1 (en) * | 2001-11-08 | 2004-10-15 | Oreal | COSMETIC COMPOSITIONS CONTAINING AN AMINO SILICONE AND A THICKENING AGENT AND THEIR USES |
| FR2831801B1 (en) * | 2001-11-08 | 2003-12-19 | Oreal | COSMETIC COMPOSITIONS CONTAINING AN AMINO SILICONE AND A SOLUBLE CONDITIONING AGENT AND USES THEREOF |
| FR2831816B1 (en) * | 2001-11-08 | 2004-07-16 | Oreal | USE OF PARTICULAR AMINO SILICONE IN PRE- OR AFTER-TREATMENT OF KERATINIC FIBER DISCOLORATIONS |
| AU2002301803B2 (en) * | 2001-11-08 | 2004-09-09 | L'oreal | Cosmetic compositions containing an aminosilicone and a conditioner, and uses thereof |
| FR2831809B1 (en) * | 2001-11-08 | 2004-07-23 | Oreal | OXIDIZING COMPOSITION FOR THE TREATMENT OF KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE |
| FR2831800B1 (en) * | 2001-11-08 | 2004-09-17 | Oreal | COSMETIC COMPOSITIONS CONTAINING AN AMINO SILICONE AND AN INSOLUBLE CONDITIONING AGENT AND USES THEREOF |
| FR2831803B1 (en) * | 2001-11-08 | 2004-07-30 | Oreal | COSMETIC COMPOSITIONS CONTAINING AN AMINO SILICONE AND A THICKENING AGENT AND THEIR USES |
| FR2831813B1 (en) * | 2001-11-08 | 2004-10-01 | Oreal | USE OF PARTICULAR AMINO SILICONES IN PRE-TREATMENT OF DIRECT DYES OR OXIDATION OF KERATINIC FIBERS |
| FR2831811B1 (en) * | 2001-11-08 | 2004-07-23 | Oreal | USE OF PARTICULAR AMINO SILICONES AS A POST TREATMENT OF DIRECT DYES OR OF OXIDATION OF KERATIN FIBERS |
| FR2831805B1 (en) * | 2001-11-08 | 2004-08-06 | Oreal | PROCESS FOR PERMANENT DEFORMATION OF HAIR USING PARTICULAR AMINO SILICONES |
| FR2831808B1 (en) * | 2001-11-08 | 2003-12-19 | Oreal | DYE COMPOSITION FOR KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE |
| AU2002301801B2 (en) * | 2001-11-08 | 2004-09-30 | L'oreal | Cosmetic compositions containing an aminosilicone and a conditioner, and uses thereof |
| FR2831817B1 (en) * | 2001-11-08 | 2003-12-19 | Oreal | REDUCING COMPOSITION FOR THE TREATMENT OF KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE |
| FR2831818B1 (en) * | 2001-11-08 | 2004-07-16 | Oreal | OXIDIZING COMPOSITION FOR THE TREATMENT OF KERATINIC FIBERS COMPRISING A PARTICULAR AMINO SILICONE |
| FR2831804B1 (en) * | 2001-11-08 | 2004-07-30 | Oreal | PROCESS FOR PERMANENT DEFORMATION OF HAIR USING PARTICULAR AMINO SILICONES |
| GB0202631D0 (en) * | 2002-02-05 | 2002-03-20 | Dow Corning | Hair care compositions containing polysiloxanes |
| GB0209136D0 (en) * | 2002-04-22 | 2002-05-29 | Procter & Gamble | Durable hair treatment composition |
| WO2007085086A1 (en) * | 2006-01-30 | 2007-08-02 | Sanjeev Kaila | A composition including a silicone-based polymer and a method of treating skin disorders using the composition |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2840087A (en) * | 1952-12-19 | 1958-06-24 | Herman I Hersh | Hair setting composition and method for use of same |
| US3143476A (en) * | 1954-09-15 | 1964-08-04 | Curtis Helene Ind Inc | Cold wave neutralizing composition and process |
| BE630579A (en) * | 1962-04-06 | |||
| US3687606A (en) * | 1969-10-04 | 1972-08-29 | Bayer Ag | Permanent hair waving by artificially shaping with an epoxy-organo-silane |
| US4185087A (en) * | 1977-12-28 | 1980-01-22 | Union Carbide Corporation | Hair conditioning compositions containing dialkylamino hydroxy organosilicon compounds and their derivatives |
| FR2443476A1 (en) * | 1978-12-05 | 1980-07-04 | Oreal | NOVEL SURFACTANT POLYSILOXANES, PROCESS FOR PREPARING SAME AND COMPOSITIONS CONTAINING THE SAME |
| DE2912484A1 (en) * | 1979-03-29 | 1980-10-16 | Henkel Kgaa | NEW QUARTAERE POLYSILOXAN DERIVATIVES, THEIR USE IN HAIR COSMETICS, AND THEIR WASHING AND TREATMENT PRODUCTS CONTAINING THEM |
| DE2912485A1 (en) * | 1979-03-29 | 1980-10-09 | Henkel Kgaa | NEW QUARTAERE POLYSILOXAN DERIVATIVES, THEIR USE IN HAIR COSMETICS, AND THEIR WASHING AND TREATMENT PRODUCTS CONTAINING THEM |
| US4416297A (en) * | 1980-01-23 | 1983-11-22 | Clairol Incorporated | Hair waving or straightening process and product |
| LU83876A1 (en) * | 1982-01-15 | 1983-09-02 | Oreal | COSMETIC COMPOSITION FOR TREATMENT OF KERATINIC FIBERS AND METHOD FOR TREATING THE SAME |
| LU83949A1 (en) * | 1982-02-16 | 1983-09-02 | Oreal | COMPOSITION FOR THE TREATMENT OF KERATINIC MATERIALS CONTAINING AT LEAST ONE CATIONIC POLYMER AND AT LEAST ONE ANIONIC LATEX |
| LU84463A1 (en) * | 1982-11-10 | 1984-06-13 | Oreal | POLYQUATERNARY POLYSILOXANE POLYMERS |
| LU84894A1 (en) * | 1983-07-01 | 1985-04-17 | Oreal | HAIR COMPOSITION AND METHOD FOR TREATING HAIR |
| LU85303A1 (en) * | 1984-04-13 | 1985-11-27 | Oreal | HAIR COMPOSITION AND METHOD FOR TREATING HAIR |
-
1984
- 1984-05-23 CA CA000454949A patent/CA1229305A/en not_active Expired
- 1984-06-06 AU AU29140/84A patent/AU548452B2/en not_active Ceased
- 1984-06-07 ZA ZA844309A patent/ZA844309B/en unknown
- 1984-06-08 DE DE3421358A patent/DE3421358C2/en not_active Revoked
- 1984-06-13 JP JP59120066A patent/JPS608216A/en active Granted
- 1984-06-14 GR GR75012A patent/GR82154B/el unknown
- 1984-06-14 SE SE8403215A patent/SE465204B/en not_active IP Right Cessation
- 1984-06-14 IT IT21420/84A patent/IT1181902B/en active
- 1984-06-14 FR FR8409320A patent/FR2548020A1/en active Pending
- 1984-06-14 GB GB08415170A patent/GB2141454B/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1181902B (en) | 1987-09-30 |
| DE3421358A1 (en) | 1984-12-20 |
| GB2141454B (en) | 1987-07-22 |
| GR82154B (en) | 1984-12-13 |
| GB2141454A (en) | 1984-12-19 |
| JPS608216A (en) | 1985-01-17 |
| IT8421420A0 (en) | 1984-06-14 |
| SE8403215L (en) | 1984-12-16 |
| DE3421358C2 (en) | 1996-03-14 |
| FR2548020A1 (en) | 1985-01-04 |
| AU548452B2 (en) | 1985-12-12 |
| SE465204B (en) | 1991-08-12 |
| JPH0460447B2 (en) | 1992-09-28 |
| SE8403215D0 (en) | 1984-06-14 |
| GB8415170D0 (en) | 1984-07-18 |
| ZA844309B (en) | 1985-02-27 |
| AU2914084A (en) | 1984-12-20 |
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