US3822312A - Creamy rinsing agent composition - Google Patents

Creamy rinsing agent composition Download PDF

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US3822312A
US3822312A US00301103A US30110372A US3822312A US 3822312 A US3822312 A US 3822312A US 00301103 A US00301103 A US 00301103A US 30110372 A US30110372 A US 30110372A US 3822312 A US3822312 A US 3822312A
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carbon atoms
creamy
rinsing agent
wig
iii
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O Kojima
T Hara
T Sato
M Katsumi
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Kao Corp
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Kao Corp
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    • 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
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • 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
    • A61K8/34Alcohols
    • 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
    • A61K8/34Alcohols
    • A61K8/345Alcohols containing more than one hydroxy group
    • 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
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives 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
    • A61K8/72Cosmetics 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/667Neutral esters, e.g. sorbitan esters
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/72Ethers of polyoxyalkylene glycols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/74Carboxylates or sulfonates esters of polyoxyalkylene glycols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • C11D1/94Mixtures with anionic, cationic or non-ionic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2006Monohydric alcohols
    • C11D3/201Monohydric alcohols linear
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2041Dihydric alcohols
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2065Polyhydric alcohols
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59Mixtures
    • A61K2800/596Mixtures of surface active compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • C11D1/90Betaines

Definitions

  • An aqueous creamy rinsing agent composition for wig and hair comprising as essential components (I) 1-7% of a quaternary ammonium salt having two long-chain alkyl groups having 16 to 22 carbon atoms; (II) 0.1- of an antistatic agent expressed by the following formula wherein R stands for an alkyl group having 16 to 22 carbon atoms, R and R designate independently an alkyl group having 1 to 3 carbon atoms, and m is a number of from 1 to 4: (III) 05-10% of at least one compound selected from the group consisting of alcohols having up to 3 carbon atoms, glycols having up to 3 carbon atoms, glycerol, sorbitol, non-ionic surfactants containing no ethylene oxide units in the molecule or containing up to moles of ethylene oxide units in the molecule, polyalkylene oxide compounds having a molecular weight of greater
  • This invention relates to a creamy rinsing agent composition having an excellent effect for finishing wigs made from synthetic fibers or human hairs, or hairs.
  • the creamy rinsing agent composition of this invention exhibits a very excellent finishing effect particularly when it is used for finishing treatment of wigs made from synthetic fibers.
  • the direct rinse can be easily applied to a wig.
  • An antistatic property can be imparted to a wig.
  • Wigs made from synthetic fibers are, in particular, readily statically charged.
  • fibers of the wig 3,822,312 Patented July 2, 1974 is statically charged, they are entangled or bristled, resulting in a great damage on the wig.
  • it is a great defect of a wig of synthetic fibers that it is readily statically charged in the winter season when the wig is used more frequently.
  • Wigs can be combed smoothly. In other words, it is desired that a good smoothness can be imparted to wig fibers.
  • the rinsing agent is in the form of a stable emulsion having a relatively high viscosity.
  • the rinsing agent having such property is called creamy rinsing agent for convenience.
  • the creamy rinsing agent to be used for treatment of wigs has the above properties (2), (3) and (4).
  • the creamy rinsing agent should give a suitable softness to wig fibers and decrease unnatural feeling in wigs.
  • the rinsing agent is stable at a relatively high viscosity.
  • an aqueous creamy rinsing agent composition for wig and hair which comprises the following four ingredients (I) to (IV):
  • the balance is water.
  • quaternary ammonium salt (I) there may be exemplified distearyl dimethyl ammonium chloride, dipalmityl dimethyl ammonium chloride, di-hydrogenatedbeef-tallow-alkyl dimethyl ammonium chloride, dibehenyl dihydroxyethyl ammonium chloride, dipalmityl propylethyl ammonium ethylsulfate, etc.
  • antistatic agent (II) there may be mentioned stearyl dimethyl betaine [C H -(CH N+CH COO-] (structural formulae will be omitted below), cetyl dimethyl propiobetaine, cetyl dimethyl betaine, behenyl dipropyl betaine, behenyl dimethyl betaine, behenyl dimethyl propiobetaine, palmityl dimethyl betaine, etc.
  • methanol, ethanol, propanol, ethylene glycol, propylene glycol, glycerol, sorbitol compounds expressed by the formula RO (C H O) H in which m is to 10, and R is an alkyl or alkenyl group of 12-22 carbon atoms, a lanolin alcohol alkyl residue or an alkylphenyl group having an alkyl group of 8 to 12 carbon atoms, monoglycerides of higher fatty acids, sorbitan esters of higher fatty acids, adducts of 1 to moles of ethylene oxides to sorbitan esters of higher fatty acids, OH(CH CH O) OH,
  • inorganic and organic salts (IV having an electrolytic property there may be mentioned salts of alkali metals, ammonium, halogens, sulfuric acid, boric acid, phosphoric acid and organic acids having up to 6 carbon atoms.
  • each of the above four ingredients is an essential and indispensable component
  • the creamy rinsing agent of this invention should comprise all of the above four ingredients. More specifically, a mere blend of the quaternary ammonium salt (I) and the antistatic agent (II) cannot exhibit a stable creamy state, and a blend of any three ingredients of the above four indispensable ingredients cannot possess a stable creamy state or a good combination of properties intended in this invention. In short, only the rinsing agent composition comprising the four indispensable ingredients specified in this invention can possess a stable cream state and a good combination of intended properties.
  • the creamy rinsing agent composition according to this invention is especially suitable for the treatment of wigs made from synthetic fibers which are readily statically charged, but it may of course be effectively used for the finishing treatment of wigs made from human hairs or human hairs per se. Furthermore, the creamy rinsing agent composition of this invention may further comprise small amounts of known additives such as perfumes, fungicides, pigments, etc.
  • Example 1 Viscosity, antistatic property and other properties required of a rinsing agent were measured with respect to each of the compositions illustrated below. In the following, the compositions tested are shown first, and then the results of the measurement and evaluation in those compositions are shown. In each of compositions, symbols (I) to (IV) are those used throughout the instant specification to clearly indicate the four ingredients.
  • Composition 1 Percent (I) Di-hydrogenated-beef-tallow-alkyl dimethyl ammonium chloride 4
  • Water Balance Composition 2 Percent (I) Di-hydrogenated beef-tallow-alkyl ammonium (I) Dibehenyl dihydroxyethyl ammonium bro- 6 mide 6 (II) C H -(CH 'N+CH COO- 3 (IV) Sodium acetate 0.5
  • Water Balance Composition 13 (example): Percent (I) Dipalmityl propyl ethyl ammonium ethylsulfate 6 C22H45' 2N+CH2COO 1 (III) C H COO(C H O) H 5 (IV) Sodium phosphate 0.2
  • the measurement was carried out according to Rtider method.
  • the fibers there were used Kanekalon wig fibers (fibers of a copolymer of acrylonitrile and vinyl chloride manufactured by Kanegafuchi Kagaku Kogyo K.K.).
  • the fibers were dipped for 3 minutes in an aqueos solution containing 5% of the rinsing agent composition and then squeezed so that the aqueous solution was contained in an amount of 50% based on the fibers.
  • the fibers were dried and allowed to stand at a temperature of 25 C. under a relative humidity of 45% for 48 hours.
  • the treated fibers were used as test samples.
  • the fiber running velocities adopted in the measurement according to Roder method were 2 cm./min. (static friction) or cm./min. (dynamic friction).
  • Rinsing agents of compositions 9 to can fully meet all the necessary requirements and have an excellent creamy appearance.
  • An aqueous creamy rinsing agent composition for wigs consisting essentially of (I) 1 to 7% by weight of a quaternary ammonium salt having two long-chain alkyl groups having 16 to 22 carbon atoms and two short chain alkyl or hydroxyalkyl groups having 1 to 3 carbon atoms;
  • an anion selected from the group consisting of halogens, sulfate, borate, phosphate, acetate and lactate;
  • composition according to claim 1 in which said two short chain alkyl or hydroxy alkyl groups are selected from the group consisting of dimethyl, dihydroxyethyl and propylethyl.
  • composition according to claim 1 in which said quaternary ammonium salt *(I) is selected from the group consisting of distearyl dimethyl ammonium chloride, dipalmityl dimethyl ammonium chloride, di-hydrogenatedbeef-tallow-alkyl dimethyl ammonium chloride, dibehenyl dihydroxyethyl ammonium chloride and dipalmityl propylethyl ammonium ethylsulfate.
  • composition according to claim 1 in which said antistatic agent (II) is selected from the group consisting of stearyl dimethyl betaine, cetyl dimethyl propiobetaine, cetyl dimethyl betaine, "behenyl dipropyl betaine, behenyl dimethyl betaine, behenyl dimethyl propiobetaine and palmityl dimethyl betaine.

Abstract

AN AQUEOUS CREAMY RISING AGENT COMPOSITION FOR WIG AND HAIR COMPRISING AS ESSENTIAL COMPONENTS (I) 1-7% OF A QUATERNARY AMMONIUM SALT HAVING TWO LONG-CHAIN ALKYL GROUPS HAVING 16 TO 22 CARBON TOMS, (II) 0.1-5% OF AN ANTISTATIC AGENT EXPRESSED BY THE FOLLOWING FORMULA

R1-N(+)(-R2)(-R3)-(CH2)M-CO-O (-)

WHEREIN R1 STANDS FOR AN ALKYL GROUP HAVING 16 TO 22 CARBON ATOMS, R2 AND R3 DESIGNATE INDEPENDENTLY AN ALKYL GROUP HAVING 1 TO 3 CARBON ATOMS, AND M IS A NUMBER OF FROM 1 TO 4: (III) 0.5-10% OF AT LEAST ONE COMPOUND SELECTED FROM THE GROUP CONSISTING OF ALCOHOLS HAVING UP TO 3 CARBON ATOMS, GLYCOLS HAVING UP TO 3 CARBON ATOMS, GLYCEROL, SORBITOL, NON-IONIC SURFACTANTS CONTAINING NO ETHYLENE OXIDE UNITS IN THE MOLECULE OR CONTAINING UP TO 10 OLES OF ETHYLENE OXIDE UNITS IN THE NOLECULE, POLYALKYLENE OXIDE COMPOUNDS HAVING A MOLECULAR WEIGHT OF GREATER THAN 4000, AND LOWER ALKYL ESTERS OF HIGHER FATTY ACIDS, AND (IV) 0.05-1% OF AN INORGANIC OR ORGANIC SALT HAVING ELECTROLYTIC PROPERTY.

Description

United States Patent Office US. Cl. 252--527 4 Claims ABSTRACT OF THE DISCLOSURE An aqueous creamy rinsing agent composition for wig and hair comprising as essential components (I) 1-7% of a quaternary ammonium salt having two long-chain alkyl groups having 16 to 22 carbon atoms; (II) 0.1- of an antistatic agent expressed by the following formula wherein R stands for an alkyl group having 16 to 22 carbon atoms, R and R designate independently an alkyl group having 1 to 3 carbon atoms, and m is a number of from 1 to 4: (III) 05-10% of at least one compound selected from the group consisting of alcohols having up to 3 carbon atoms, glycols having up to 3 carbon atoms, glycerol, sorbitol, non-ionic surfactants containing no ethylene oxide units in the molecule or containing up to moles of ethylene oxide units in the molecule, polyalkylene oxide compounds having a molecular weight of greater than 4000, and lower alkyl esters of higher fatty acids; and (IV) ODS-1% of an inorganic or organic salt having electrolytic property.
BACKGROUND OF THE INVENTION Field of the invention This invention relates to a creamy rinsing agent composition having an excellent effect for finishing wigs made from synthetic fibers or human hairs, or hairs. The creamy rinsing agent composition of this invention exhibits a very excellent finishing effect particularly when it is used for finishing treatment of wigs made from synthetic fibers.
DESCRIPTION OF THE PRIOR ART Recent development and propagation of wigs composed of synthetic fibers and human hairs are conspicuous. These wigs, like ordinary hairs, need to be subjected to such treatments as washing and finishing during the manufacture or during everyday usage by customers. However, although wigs are composed of materials similar to materials of clothes and the like, it is not preferred to treat them by dipping them in an aqueous solution of a chemical because wigs have a special form and undesired deformation is easily caused to occur. In other words, conventional rinsing agents and fiber-treating agents are not suitable for the treatment of wigs, because in principle they are used in the form of an aqueous solution into which a material to be treated is dipped. Mainly for the above reason, in the treatment of wigs, a method comprising applying a rinsing agent directly to a wig, namely a direct rinse method, is preferred.
Properties necessary or preferable for rising agents for wigs are as follows:
(1) The direct rinse can be easily applied to a wig.
(2) An antistatic property can be imparted to a wig. Wigs made from synthetic fibers are, in particular, readily statically charged. When the moisture content in air is lowered in winter or the like, or when a wig is treated with a comb or brush, violent static electrification is frequently caused to occur on a wig. When fibers of the wig 3,822,312 Patented July 2, 1974 is statically charged, they are entangled or bristled, resulting in a great damage on the wig. Particularly, it is a great defect of a wig of synthetic fibers that it is readily statically charged in the winter season when the wig is used more frequently.
(3) Too high a surface gloss (luster) is not imparted to wig fibers. Cosmetics commercially available as hair creams have a hair rinsing effect to some extent, but since most of them comprise an aliphatic compound and a mineral oil as base materials, when wigs are treated with such hair creams, a high surface gloss is given throughout the wigs to impart to a wig an undesirable heavy feeling and unnatural impression. Moreover, such hair creams fail to impart on wig fibers various effects which can be attained by the creamy rinsing agent of this invention.
(4) Wigs can be combed smoothly. In other words, it is desired that a good smoothness can be imparted to wig fibers.
In order for a rinsing agent to have the above property (1), it is desired that the rinsing agent is in the form of a stable emulsion having a relatively high viscosity. In this invention, the rinsing agent having such property is called creamy rinsing agent for convenience. It is also desired that the creamy rinsing agent to be used for treatment of wigs has the above properties (2), (3) and (4). Of course, it is naturally required that the creamy rinsing agent should give a suitable softness to wig fibers and decrease unnatural feeling in wigs.
Furthermore, the following matters should be taken into consideration in order that the actual use of a creamy rinsing agent can be facilitated:
(a) The rinsing agent is stable at a relatively high viscosity.
(b) The viscosity of the creamy rinsing agent at a temperature approximating body temperature is relatively low, and it is handled with ease.
(c) In order to make a dipping treatment easy for broader application, it can be dispersed easily in water.
((1) Even when the creamy rinsing agent is applied only to a part of a wig, an undesired phenomenon called flaking, namely a phenomenon that a white powdery substance appears on the surface of the fibre, is not caused to occur.
SUMMARY OF THE INVENTION We have made extensive research works with a view to developing a rinsing agent composition meeting all of the above-mentioned complicated and delicate requirements, and We have now arrived at this invention.
In accordance with this invention, there is provided an aqueous creamy rinsing agent composition for wig and hair which comprises the following four ingredients (I) to (IV):
(I) 17% of a quaternary ammonium salt having two long-chain alkyl groups having 16 to 22 carbon atoms;
(II) 0.l5% of an antistatic agent expressed by the following formula wherein R stands for an alkyl group having 16 to 22 carbon atoms, R and R designate independently an alkyl group having 1 to 3 carbon atoms, and m is a number of from 1 to 4;
(III) 0.540% of at least one compound selected from the group consisting of alcohols having up to 3 carbon atoms, glycols having up to 3 carbon atoms, glycerol, sorbitol, non-ionic surfactants containing no ethylene oxide units in the molecule or containing up to 10 moles of ethylene oxide uni-ts in the molecule, polyalkylene oxide compounds having molecular weighths of greater than 4000, and lower alkyl esters of higher fatty acids; and
(IV) 0.05-1% of an inorganic or organic salt having electrolytic property.
The balance is water.
Throughout the instant specification and claims, each percent value is on the weight basis.
Preferred examples of the above indispensable ingredients of the creamy rinsing agent composition of this invention will now be illustrated.
As the quaternary ammonium salt (I) there may be exemplified distearyl dimethyl ammonium chloride, dipalmityl dimethyl ammonium chloride, di-hydrogenatedbeef-tallow-alkyl dimethyl ammonium chloride, dibehenyl dihydroxyethyl ammonium chloride, dipalmityl propylethyl ammonium ethylsulfate, etc.
As the antistatic agent (II) there may be mentioned stearyl dimethyl betaine [C H -(CH N+CH COO-] (structural formulae will be omitted below), cetyl dimethyl propiobetaine, cetyl dimethyl betaine, behenyl dipropyl betaine, behenyl dimethyl betaine, behenyl dimethyl propiobetaine, palmityl dimethyl betaine, etc.
As the compound (III), there may be exemplified methanol, ethanol, propanol, ethylene glycol, propylene glycol, glycerol, sorbitol, compounds expressed by the formula RO (C H O) H in which m is to 10, and R is an alkyl or alkenyl group of 12-22 carbon atoms, a lanolin alcohol alkyl residue or an alkylphenyl group having an alkyl group of 8 to 12 carbon atoms, monoglycerides of higher fatty acids, sorbitan esters of higher fatty acids, adducts of 1 to moles of ethylene oxides to sorbitan esters of higher fatty acids, OH(CH CH O) OH,
C -C lower alkyl esters of higher fatty acids having 14 to 22 carbon atoms, etc.
As the inorganic and organic salts (IV having an electrolytic property, there may be mentioned salts of alkali metals, ammonium, halogens, sulfuric acid, boric acid, phosphoric acid and organic acids having up to 6 carbon atoms.
In this invention, each of the above four ingredients is an essential and indispensable component, and the creamy rinsing agent of this invention should comprise all of the above four ingredients. More specifically, a mere blend of the quaternary ammonium salt (I) and the antistatic agent (II) cannot exhibit a stable creamy state, and a blend of any three ingredients of the above four indispensable ingredients cannot possess a stable creamy state or a good combination of properties intended in this invention. In short, only the rinsing agent composition comprising the four indispensable ingredients specified in this invention can possess a stable cream state and a good combination of intended properties.
The creamy rinsing agent composition according to this invention is especially suitable for the treatment of wigs made from synthetic fibers which are readily statically charged, but it may of course be effectively used for the finishing treatment of wigs made from human hairs or human hairs per se. Furthermore, the creamy rinsing agent composition of this invention may further comprise small amounts of known additives such as perfumes, fungicides, pigments, etc.
This invention will now be illustrated in detail by reference to examples.
Example 1 Viscosity, antistatic property and other properties required of a rinsing agent were measured with respect to each of the compositions illustrated below. In the following, the compositions tested are shown first, and then the results of the measurement and evaluation in those compositions are shown. In each of compositions, symbols (I) to (IV) are those used throughout the instant specification to clearly indicate the four ingredients.
4 Composition 1 (comparison): Percent (I) Di-hydrogenated-beef-tallow-alkyl dimethyl ammonium chloride 4 Water Balance Composition 2 (comparison): Percent (I) Di-hydrogenated beef-tallow-alkyl ammonium (I) Dibehenyl dihydroxyethyl ammonium bro- 6 mide 6 (II) C H -(CH 'N+CH COO- 3 (IV) Sodium acetate 0.5 Water Balance Composition 7 (comparison): Percent (I) Di-hydrogenated-beef-tallow alkyl dimethyl ammonium chloride 4 C13H37'(CH3)2'N+CH2COO 1 (III) Ethanol 7 Water Balance Composition 8 (comparison): Percent (I) Dibehenyl dihydroxyethyl ammonium bromide 6 m as'( a)2' 2)2 3 (III) Propylene glycol 7 Water Balance Composition 9 (example): Percent (I) Di-hydrogenated-beef-tallow alkyl dimethyl ammonium chloride 4 C18H37'(CH3)2'N+CH2COO (III) Ethanol 7 (IV) Sodium chloride 0.15 Water Balance Composition 10 (example): Percent (I) Dipalmityl propyl ethyl ammonium ethylsulfate 5 C16H33' a)2 2)2 (III) Propylene glycol 3 (IV) Sodium sulfate 0.3 Water Balance Composition 11 (example): Percent (I) Dibehenyl dihydroxyethyl ammonium bromide 4 C22H45' (C3H7)2N+CH2COO 1 (III) Glycerine 10 (IV) Sodium acetate 0.25 Water Balance Composition 12 (example): Percent (I) Di-hydrogenated-beef-tallow alkyl dimethyl ammonium chloride 2 C H '(CH -N CH COO 3 1a 3'z 2 4' )s 4 (IV) Sodium bromide 0.05
Water Balance Composition 13 (example): Percent (I) Dipalmityl propyl ethyl ammonium ethylsulfate 6 C22H45' 2N+CH2COO 1 (III) C H COO(C H O) H 5 (IV) Sodium phosphate 0.2 Water Balance Composition 14 (example): Percent (I) Dibehenyl dihydroxyethyl ammonium bromide 2 C13H37'(CH3)2'N+CH2COO (III) Oleyl monoglyceride 3 (IV) Potassium chloride 0.5 Water Balance Composition 15 (example): Percent (I) Di-hydrogenated-beef-tallow alkyl dimethyl ammonium chloride (II) C H -(CH -N+CH COO- 1.5 (III) Adduct of 4 moles of ethylene oxide to sorbitan monostearate 5 (IV) Sodium lactate 0.7 Water Balance Composition 16 (example): Percent (I; Dipalmityl propyl ethyl ammonium ethylsulate 5 C1BH37(CH3)2N+CH2COO (III) HO(C H O) H 2 (IV) Sodium borate 0.1 Water Balance Composition 17 (example): Percent (I) Dibehenyl dihydroxyethyl ammonium bromide C16H33'(CH3)2'N+(CH2)2C0O '(III) Butyl stearate 2 (IV) Sodium acetate 0.15 Water Balance Composition 18 (example): Percent (I) Di-hydrog'enated-beef-tallow alkyl dimethyl ammonium chloride 4 (II) C18H37(CH3)2N+CH2COO 0.75 (1H) Ethanol 2 (III) Lanolin alcohol 1 (IV) Sodium chloride 0.25 Water Balance Composition 19 (example): Percent (I) Di-hydrogenated-beef-tallow alkyl dimethyl ammonium chloride 3 C H -(CH -N+CH COO 1.5 (III) Glycerine 7 (III) Oleyl monoglyceride 3 (IV) Sodium bromide 0.15 Water Balance Composition 20 (example): Percent (I) Di-hydrogenated-beef-tallow alkyl dimethyl ammonium chloride 4 (II) C H -(CH -N+(CH C0O 1.5 (III) Sorbitol 4 (HI) Butyl stearate 3 (IV) Ammonium acetate 1 Water Balance Methods of Evaluation and Measurement (1) Viscosity: The viscosity was measured with a viscometer of the Brookfield type, the value being expressed in the cps. unit.
(2) Smoothness: Static and dynamic friction coefficients between fibers were measured, and based on these values, the smoothness was evaluated.
The measurement was carried out according to Rtider method. As the fibers, there were used Kanekalon wig fibers (fibers of a copolymer of acrylonitrile and vinyl chloride manufactured by Kanegafuchi Kagaku Kogyo K.K.). The fibers were dipped for 3 minutes in an aqueos solution containing 5% of the rinsing agent composition and then squeezed so that the aqueous solution was contained in an amount of 50% based on the fibers. Then, the fibers were dried and allowed to stand at a temperature of 25 C. under a relative humidity of 45% for 48 hours. The treated fibers were used as test samples. The fiber running velocities adopted in the measurement according to Roder method were 2 cm./min. (static friction) or cm./min. (dynamic friction).
The smoothness was evaluated based on the friction coeificients according to the following standard:
Static Dynamic Evaluation irletion friction grade coefiieient coetficient A 0. 0. 10 B 0. 12-0. 14 0. 10-0. 12 C 0. 14 0. l2
Grade of Antistatic Insulation Property Resistance (ohm) A 1.0 -10 (4) Solubility: 400 ml. of water maintained at 30 C. was placed in a vessel, and 20 g. of the sample (rinsing agent) was thrown into water. The frequency of hand agitation required for dissolving the sample uniformly in water was counted. Since it is diflicult to otbain accurate results in this measurement, the solubility was approximately evaluated by reckoning 5 times of agitation frequency as one unit of the solubility.
(5) State of Rinsing Agent: The state of the rinsing agent composition was evaluated from the appearance.
(6) Flaking: 10 g. of the sample (rinsing agent) was carefully applied by hand to a wig of synthetic fibers (the total weight being 1'50 g.), followed by drying. Formation or appearance of powdery substance on the wig surface was checked by naked eye.
Results In each sample, formation or appearance of powdery substance was not observed.
(7) Surface Gloss (Luster): A wig treated in the same manner as described with respect to the flaking test was evaluated with respect to the surface gloss by employing as a standard sample a wig treated with a commercially available hair cream (incorporated with a mineral oil).
Results No difference was observed between a wig treated with a rinsing agent of the composition 1 and the standard sample, but in wigs treated with rinsing agents of other compositions the surface gloss was reduced as compared with the standard sample.
All-Round Evaluation Test results of each sample are shown in Table 1. Samples of compositions 1 to 8 are defective in any of the smoothness, the antistatic property and the solubility, and they are fatally defective in that the viscosity is low and they are in the solution form, or that when the viscosity is high, they take a jelly-like form. It is impossible to apply such rinsing agents uniformly to wigs by the direct rinse method.
Rinsing agents of compositions 9 to can fully meet all the necessary requirements and have an excellent creamy appearance.
8 (IV) 0.05 to 1% by weight of an electrolytic inorganic or organic salt having a cation selected from the group consisting of alkali metals and ammonium TABLE 1 Viscosity smoothness Solu- Compositrou Antistatic bility State of rinsing agent number C. C. Static Dynamic property (unit) composition 250 B A C 1 Semi-transparent dispersion. 3, 000 B A C 20 Transparent jelly.
70 C B B 1 Transparent solution. 50 C B B 1 Do. 35 A A A 1 Dispersion. 95 A A A 1 Do. 85 A A A 1 Semi-transparent dispersion. 110 A A A 1 Do. 2, 700 A A A 2 Milky white cream. 4, 700 A A A 2 Do. 3, 800 A A A 2 Do. 2, 700 A A A 2 Do. 4, 200 A A A 2 Do. 780 A A A 1 Do. 7, 600 A A A 2 Do. 1, 150 A A B 1 D0. 3,800 A A A 2 Do. 4,600 A A A 2 D0. 4, 950 A A A 1 Do. 9, 800 A A A 2 Do. Control 1 0. 14 0.12 1. 2X10" l Data of control are those obtained by conducting the measurement on untreated fibers.
The embodiments of the invention in which an exclusive property or privilege is claimed are defined as follows:
1. An aqueous creamy rinsing agent composition for wigs consisting essentially of (I) 1 to 7% by weight of a quaternary ammonium salt having two long-chain alkyl groups having 16 to 22 carbon atoms and two short chain alkyl or hydroxyalkyl groups having 1 to 3 carbon atoms;
(II) 0.1 to 5% by weight of an antistatic agent of the formula wherein R is alkyl having 16 to 22 carbon atoms, R and R is alkyl having 1 to 3 carbon atoms, and m is a number of from 1 to 4;
(III) 0.5 to 10% by weight of at least one compound selected from the group consisting of methanol; ethanol; propanol; ethylene glycol; propylene glycol; glycerol; sorbitol; a compound of the formula RO(C H O) H in which m is 0 to 10 and R is an alkyl or alkenyl group of 12-22 carbon atoms, lanolin alcohol alkyl radical or alkylphenyl having an alkyl group of 8 to 12 carbon atoms; monoglyccrides of higher fatty acids; sorbitan esters of higher fatty acids; adducts of '1 to 10 moles of ethylene oxide to sorbitan esters of higher fatty acids;
HO 150OH,
C4Hg0 CH2 45H:
and C -C lower alkyl esters of higher fatty acids having 14 to 22 carbon atoms;
an anion selected from the group consisting of halogens, sulfate, borate, phosphate, acetate and lactate;
and
(V) the balance being water.
2. A composition according to claim 1 in which said two short chain alkyl or hydroxy alkyl groups are selected from the group consisting of dimethyl, dihydroxyethyl and propylethyl.
3. A composition according to claim 1, in which said quaternary ammonium salt *(I) is selected from the group consisting of distearyl dimethyl ammonium chloride, dipalmityl dimethyl ammonium chloride, di-hydrogenatedbeef-tallow-alkyl dimethyl ammonium chloride, dibehenyl dihydroxyethyl ammonium chloride and dipalmityl propylethyl ammonium ethylsulfate.
4. A composition according to claim 1, in which said antistatic agent (II) is selected from the group consisting of stearyl dimethyl betaine, cetyl dimethyl propiobetaine, cetyl dimethyl betaine, "behenyl dipropyl betaine, behenyl dimethyl betaine, behenyl dimethyl propiobetaine and palmityl dimethyl betaine.
References Cited UNITED STATES PATENTS 3,697,452 10/1972 Olson et al. 252--545 3,155,591 11/1964 Hilfer 424 3,156,656 11/1964 Libby 424-70 3,533,955 IO/1970 Pader et al. 252-547 OTHER REFERENCES Surfactant as a Conditioning Agent Cream Hair Rinse, American Perfumer, p. 54, 1958.
MAYER WEINBLATI, Primary Examiner E. L. ROLLINS, Assistant Examiner U.S. Cl. X.R.
252139, 153, 528, 541, 546, 547, Dig. 13; 42470 UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent no, 3 822'312- Dated July 2, 1974 Toshio Sato, Mamoru Katsumi, Inventor(s) Osamu Kojima and Tadao Hara It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
Add to the Heading:
' ----Foreign Application Priority Data Nov. '2, 1971 Japan 46-87388 Signdlahd sealed this 19th 'day of November 1974.
(SEAL) Attest:
McCOY M. GIBSON JR. Attesting Officer C. MARSHALL DANN Commissioner of Patents 93 po'wso ($69) 1 uscoMM-oc 60376-P69 v v U.$. GOVERNMENT PRINTING OFFICE l9, 0-365'33.
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Cited By (34)

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US3975313A (en) * 1974-06-19 1976-08-17 Shelmire Jr Jesse Bedford Solid amphoteric skin cleanser
DE2704343A1 (en) * 1976-02-09 1977-08-18 Bristol Myers Co CHEMICAL COMPOSITION FOR CONDITIONING, LIGHTENING OR COLORING HUMAN HAIR
US4102825A (en) * 1976-10-01 1978-07-25 Kao Soap Co., Ltd. Liquid light-duty detergent composition
US4144326A (en) * 1975-05-19 1979-03-13 American Cyanamid Company Oil free, water-soluble, clear creme rinse for hair
US4148762A (en) * 1976-04-15 1979-04-10 Henkel Kommanditgesellschaft Auf Aktien Cosmetic cleaning agents containing betaines and process
US4149551A (en) * 1977-03-28 1979-04-17 The Procter & Gamble Company Method of conditioning hair using a flexible substrate
US4165369A (en) * 1975-09-11 1979-08-21 Kao Soap Co., Ltd. Liquid hair rinse containing quaternary ammonium salts and a synthetic secondary alcohol
US4166048A (en) * 1975-09-22 1979-08-28 Kao Soap Co., Ltd. High foaming detergent composition having low skin irritation properties
US4187289A (en) * 1976-12-03 1980-02-05 Ciba-Geigy Corporation Softening agents containing diester/amine adducts and quaternary ammonium salts, valuable for use as after-rinse softeners and after-shampoo hair conditioners
US4220168A (en) * 1978-06-05 1980-09-02 Helene Curtis Industries, Inc. Method of moisturizing and maintaining normal moisture level in hair having a normal moisture content
US4220166A (en) * 1978-06-05 1980-09-02 Helene Curtis Industries, Inc. Method of restoring normal moisture level to hair with severe moisture deficiency
US4220167A (en) * 1978-06-05 1980-09-02 Helene Curtis Industries, Inc. Method of restoring normal moisture level to hair with slight to moderate moisture deficiency
US4261869A (en) * 1977-07-01 1981-04-14 Lever Brothers Company Detergent compositions
US4374125A (en) * 1978-06-05 1983-02-15 Helene Curtis Industries, Inc. Hair moisturizing compositions
US4421740A (en) * 1976-07-09 1983-12-20 S. C. Johnson & Son, Inc. Hair conditioning composition and process for producing the same
US4464273A (en) * 1982-02-10 1984-08-07 Lever Brothers Company Fabric softening composition
US4464272A (en) * 1982-02-10 1984-08-07 Lever Brothers Company Fabric softening composition
US4532127A (en) * 1976-02-09 1985-07-30 Clairol Incorporated Composition for lightening or coloring hair containing an oxidizing agent and certain quaternary amines
US4534877A (en) * 1982-07-30 1985-08-13 The Procter & Gamble Company Shampoo compositions comprising specific betaine surfactants and a quaternary compound
US4537762A (en) * 1983-11-14 1985-08-27 Bernel Chemical Co. Hair compositions containing mixtures of quaternary ammonium compounds and tertiary amine salts of long-chain acids
US4548810A (en) * 1979-05-03 1985-10-22 Albert Zofchak Method of lubricating the skin
US4636329A (en) * 1983-06-22 1987-01-13 The Procter & Gamble Company Shampoo compositions comprising quaternary imidazolinium compound and alkylamido betaine having low pH range
US4749411A (en) * 1986-03-14 1988-06-07 M. D. Stetson Company Disinfecting and high-speed buffing composition comprising polyethylene glycol and quaternary ammonium germicide, and method of use
US4917842A (en) * 1988-02-12 1990-04-17 The Standard Oil Company Process of making ceramics
US4979993A (en) * 1989-03-27 1990-12-25 Loctite Corporation Trialkylammonium alkyl carboxylate primer for cyanoacrylate bonding of polymeric substrates
US4986983A (en) * 1989-04-03 1991-01-22 Revlon, Inc. Superfatted betaine and zwitterionic hair and skin conditioner compositions
US5034218A (en) * 1990-07-13 1991-07-23 Helene Curtis, Inc. Stable conditioning shampoo containing compatible anionic surfactant/cationic conditioning agent-non-volatile silicone emulsion
US5066743A (en) * 1989-03-27 1991-11-19 Loctite Corporation Two-part composition comprising a cyanoacrylate adhesive and a primer comprising a tertiary ammonium carboxylate compound
US5078990A (en) * 1990-07-13 1992-01-07 Helene Curtis, Inc. Shampoos and conditioning shampoos having increased capacity for incorporation of conditioning agents and removal of hair soil
WO1992005234A1 (en) * 1990-09-21 1992-04-02 The Procter & Gamble Company Cleansing compositions
US5334376A (en) * 1993-08-13 1994-08-02 Colgate-Palmolive Company Compositions for conditioning hair
US5733536A (en) * 1995-06-05 1998-03-31 Whitehill Oral Technologies, Inc. Ultramulsion based hair care compositions
US20030125212A1 (en) * 2000-04-10 2003-07-03 Katsuhiko Yamaguchi Wetting agent composition for agricultural chemicals
US8277788B2 (en) 2005-08-03 2012-10-02 Conopco, Inc. Quick dispersing hair conditioning composition

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JPS5129233A (en) * 1974-09-03 1976-03-12 Kao Corp Heaarinsuzai soseibutsu
JPS5272834A (en) * 1975-12-15 1977-06-17 Kao Corp Clear hair rinse
JPS559016A (en) * 1978-07-04 1980-01-22 Kao Corp Rinse
US4375421A (en) * 1981-10-19 1983-03-01 Lever Brothers Company Viscous compositions containing amido betaines and salts
JPS5885810A (en) * 1981-11-17 1983-05-23 Kao Corp Hair treatment composition and its preparation
US4526781A (en) * 1984-04-25 1985-07-02 Revlon, Inc. Hair care compositions
JP3431737B2 (en) * 1995-10-25 2003-07-28 サンスター株式会社 High molecular weight emulsified hair treatment agent

Cited By (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3975313A (en) * 1974-06-19 1976-08-17 Shelmire Jr Jesse Bedford Solid amphoteric skin cleanser
US4144326A (en) * 1975-05-19 1979-03-13 American Cyanamid Company Oil free, water-soluble, clear creme rinse for hair
US4165369A (en) * 1975-09-11 1979-08-21 Kao Soap Co., Ltd. Liquid hair rinse containing quaternary ammonium salts and a synthetic secondary alcohol
US4166048A (en) * 1975-09-22 1979-08-28 Kao Soap Co., Ltd. High foaming detergent composition having low skin irritation properties
US4119399A (en) * 1976-02-09 1978-10-10 Clairol Incorporated Composition for coloring hair containing an oxidizing agent and certain quaternary amines
US4532127A (en) * 1976-02-09 1985-07-30 Clairol Incorporated Composition for lightening or coloring hair containing an oxidizing agent and certain quaternary amines
US4096243A (en) * 1976-02-09 1978-06-20 Clairol Incorporated Composition for lightening hair containing an oxidizing agent and certain quaternary amines
DE2704343A1 (en) * 1976-02-09 1977-08-18 Bristol Myers Co CHEMICAL COMPOSITION FOR CONDITIONING, LIGHTENING OR COLORING HUMAN HAIR
US4148762A (en) * 1976-04-15 1979-04-10 Henkel Kommanditgesellschaft Auf Aktien Cosmetic cleaning agents containing betaines and process
US4421740A (en) * 1976-07-09 1983-12-20 S. C. Johnson & Son, Inc. Hair conditioning composition and process for producing the same
US4102825A (en) * 1976-10-01 1978-07-25 Kao Soap Co., Ltd. Liquid light-duty detergent composition
US4187289A (en) * 1976-12-03 1980-02-05 Ciba-Geigy Corporation Softening agents containing diester/amine adducts and quaternary ammonium salts, valuable for use as after-rinse softeners and after-shampoo hair conditioners
US4149551A (en) * 1977-03-28 1979-04-17 The Procter & Gamble Company Method of conditioning hair using a flexible substrate
US4261869A (en) * 1977-07-01 1981-04-14 Lever Brothers Company Detergent compositions
US4220167A (en) * 1978-06-05 1980-09-02 Helene Curtis Industries, Inc. Method of restoring normal moisture level to hair with slight to moderate moisture deficiency
US4374125A (en) * 1978-06-05 1983-02-15 Helene Curtis Industries, Inc. Hair moisturizing compositions
US4220166A (en) * 1978-06-05 1980-09-02 Helene Curtis Industries, Inc. Method of restoring normal moisture level to hair with severe moisture deficiency
US4220168A (en) * 1978-06-05 1980-09-02 Helene Curtis Industries, Inc. Method of moisturizing and maintaining normal moisture level in hair having a normal moisture content
US4548810A (en) * 1979-05-03 1985-10-22 Albert Zofchak Method of lubricating the skin
US4464272A (en) * 1982-02-10 1984-08-07 Lever Brothers Company Fabric softening composition
US4464273A (en) * 1982-02-10 1984-08-07 Lever Brothers Company Fabric softening composition
US4534877A (en) * 1982-07-30 1985-08-13 The Procter & Gamble Company Shampoo compositions comprising specific betaine surfactants and a quaternary compound
US4636329A (en) * 1983-06-22 1987-01-13 The Procter & Gamble Company Shampoo compositions comprising quaternary imidazolinium compound and alkylamido betaine having low pH range
US4537762A (en) * 1983-11-14 1985-08-27 Bernel Chemical Co. Hair compositions containing mixtures of quaternary ammonium compounds and tertiary amine salts of long-chain acids
US4749411A (en) * 1986-03-14 1988-06-07 M. D. Stetson Company Disinfecting and high-speed buffing composition comprising polyethylene glycol and quaternary ammonium germicide, and method of use
US4917842A (en) * 1988-02-12 1990-04-17 The Standard Oil Company Process of making ceramics
US5066743A (en) * 1989-03-27 1991-11-19 Loctite Corporation Two-part composition comprising a cyanoacrylate adhesive and a primer comprising a tertiary ammonium carboxylate compound
US4979993A (en) * 1989-03-27 1990-12-25 Loctite Corporation Trialkylammonium alkyl carboxylate primer for cyanoacrylate bonding of polymeric substrates
US4986983A (en) * 1989-04-03 1991-01-22 Revlon, Inc. Superfatted betaine and zwitterionic hair and skin conditioner compositions
US5034218A (en) * 1990-07-13 1991-07-23 Helene Curtis, Inc. Stable conditioning shampoo containing compatible anionic surfactant/cationic conditioning agent-non-volatile silicone emulsion
US5078990A (en) * 1990-07-13 1992-01-07 Helene Curtis, Inc. Shampoos and conditioning shampoos having increased capacity for incorporation of conditioning agents and removal of hair soil
WO1992005234A1 (en) * 1990-09-21 1992-04-02 The Procter & Gamble Company Cleansing compositions
US5334376A (en) * 1993-08-13 1994-08-02 Colgate-Palmolive Company Compositions for conditioning hair
US5733536A (en) * 1995-06-05 1998-03-31 Whitehill Oral Technologies, Inc. Ultramulsion based hair care compositions
US20030125212A1 (en) * 2000-04-10 2003-07-03 Katsuhiko Yamaguchi Wetting agent composition for agricultural chemicals
US8277788B2 (en) 2005-08-03 2012-10-02 Conopco, Inc. Quick dispersing hair conditioning composition

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GB1410789A (en) 1975-10-22
IT1001509B (en) 1976-04-30
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