US3068151A - Hair control composition - Google Patents

Hair control composition Download PDF

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US3068151A
US3068151A US735924A US73592458A US3068151A US 3068151 A US3068151 A US 3068151A US 735924 A US735924 A US 735924A US 73592458 A US73592458 A US 73592458A US 3068151 A US3068151 A US 3068151A
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perfume
hair
pvp
resinous
weight
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Haefele John William
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Procter and Gamble Co
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Procter and Gamble Co
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35Ketones, e.g. benzophenone
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/817Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Compositions or derivatives of such polymers, e.g. vinylimidazol, vinylcaprolactame, allylamines (Polyquaternium 6)
    • A61K8/8182Copolymers of vinyl-pyrrolidones. Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/72Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toilet preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00Drug, bio-affecting and body treating compositions
    • Y10S424/01Aerosol hair preparation
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00Drug, bio-affecting and body treating compositions
    • Y10S424/02Resin hair settings

Description

Stats This invention relates to improved hair control compositionswhich tend to maintain the hair in a desired coiffure. The invention also relates to a method for treating human hair in such a manner as to impart to the hair improved maintenance of the desired configuration.

Polyvinylpyrrolidone (hereinafter referred to as PVP) and dimethyl hydantoin formaldehyde resin (hereinafter referred to as DHFR) have enjoyed widespread acceptance as resins to be applied to the hair for purposes of maintaining the hair in a desired configuration. They enjoy certain advantages over other resinous materials which have been employed for this purpose since they are water-soluble and are, therefore, easily removed from the hair. The stiffness imparted to the hair by PVP and DHFR is considerably less than that imparted by the resinous material which has traditionally been employed in commercial hair control preparations, i.e. shellac. In spite of this lesser stiffness, PVP and Dl-IFR are equal to shellac in hair control properties, e.g. resistance to the effect of humidity, and a large segment of the buying public considers this combination of lesser stiffness and outstanding hair control to be a substantial improvement.

The excellent hair control properties of PVP may be enhanced by copolymerizing the PVP with no more than an equal amount by weight of vinyl acetate (hereinafter referred to as VA). The copolymer (i.e. PVP/VA) obtained has the water-solubility of PVP and in addition holds curl better and is somewhat less sticky than PVP in moist atmosphere. Water-soluble polyacrylic resins (hereinafter referred to as polyacrylates) have also been found to be acceptable for use in hair compositions. Polyacrylates, PVP, DHFR and PVP/ VA copolymers are also soluble in alcohol, and the dual water-alcohol solubility makes it possible to apply the resins to hair through several different mechanisms. Whenever used herein, the designation PVP/VA is intended to refer to only those copolymers of PVP and VA which are water and alcohol soluble.

The simplest medium for application of polyacrylates, PVP, DHFR and PVP/VA to the hair is as a solution in Water or alcohol or a blend of the two solvents. However, in compounding a commercially acceptable cosmetic preparation of this type, it is usual, and often essential that certain additional ingredients be present. These ingredients include perfume (a commercially essential constituent) and hair-conditioners such as lanolin derivatives. These additional ingredients decrease the amount of curl control which the resin provides. This decrease in curl control is accompanied by an actual softening of the resinous film and a consequent reduction in the stiffness of the film. Therefore, there is an evident need for some inexpensive and commercially acceptable means to compensate for the loss in hair control afforded by and the reduction in the film stiffness of polyacrylate, PVP, DHFR and PVP/VA resins.

It is an object of the present invention to provide a composition having improved qualities as a means for maintaining a configuration in hair. Another object is to provide a number of chemical compounds which can be added to the conventional commercial polyacrylate, PVP, DHFR or PVP/ VA type of resinous hair control composition and which will effect a strengthening of the resinous film which results from the use of these compositions. It is another object to provide a composition suitable for aid- 3,%8,l51 Patented Dec. 11, 1962 ing the formation of a particular hair configuration, for example, by combing through the hair and allowing to dry. It is a further object to provide additives which minimize the resinous film softening effect of many of the ingredients which are normally present in commercial hair maintenance preparations, and which permit a substantial reduction in the amount of resin required to achieve a given level of hair control by the use of such preparations.

The present invention is based on the discovery that certain substituted diphenyl compounds, when employed in the conventional commercial polyacrylate, PVP, DHFR, or PVP/VA type of resinous hair control composition, will function through an apparent synergistic reinforcing mechanism to provide improved hair control and to strengthen the resinous films which result from the use of these compositions.

The particular substituted diphenyl compounds used in the practice of this invention may be expressed by the following general formula:

wherein each R and R in the formula is a radical selected from the group consisting of hydroxy and alkoxy of one to three carbons, x equals 0 to 2, and y equals 0 to 2, and wherein R is a radical selected from the group consisting of alkylene of one to three carbons, -CHNH Included within this class of substituted diphenyl compounds are the following:

Diphenylmethylamine lYTHr G -Q Diphenylrnethane Benzophenone Z-hydroxy-S-methoxybenzophenone 0H 0 3" C; O-

0 CH3 1,3 diphenylpropanone e 53 2,2',4,4'-tetrahydroxybenzophenone OH OH 3-propoxy-2-hydroxy-4'-methoxybenzophenone O CHzCHzCH; II

wherein each R and R is a radical selected from the group consisting of hydroxy and alkoxy of one to three carbon atoms, x equals one to two and y equals one to two.

The compositions of this invention will contain in solution a water-soluble resinous material consisting of polyacrylate, PVP, DHFR or PVP/VA, separately or in admixture, a perfume which has a softening effect upon the resinous films which result from the use of these compositions and from about 1% to about 50% based on the weight of the resinous material, of a substituted diphenyl compound which has a stiffening effect on films of the resinous material. Preferably the substituted diphenyl compound will be present in an amount from 5% to 20% by weight of the resinous material. Normally, the resinous material will constitute from /2 to by weight of the complete composition when dispensed from a pressurized container, the balance consisting essentially of substituted diphenyl compound, perfume, solvent and propellant. When applied to the hair in the form of a water solution, the resinous material can comprise from about 0.25% to about 10% by weight of the composition. In the preferred practice of the invention by either method, the resinous material constitutes from 0.5% to 5% by weight of the complete composition.

The resinous materials employed in the practice of this invention are available commercially in different degrees of polymerization. The degree of polymerization is usually expressed in terms of molecular weight. However, since the viscosity of a solution of a polymer is relatively easy to determine and is dependent on the molecular weight, the degree of polymerization is often expressed in terms of the viscosity of a dilute solution or as some numerical value based on this viscosity. Thus, the K value, discussed in Celluloschemie, 13, 58-64 and 71-74 (1932), is used by the manufacturer of PVP, General Aniline and Film Corporation, to express the degree of polymerization of PVP. The K value is a value calculated from relative viscosity which is the ratio of the viscosity of the solution to the viscosity of the solvent. The average molecular weight of PVP having a K value of 30 is 40,000. PVP resins having K values in the range of 26 to 36 and PVP/VA resins having K values of 30 to 50 have been found to be satisfactory in the practice of this invention, as have dimethyl hydantoin formaldehyde resins having a molecular weight of 240 to 300, and polyacrylate resins having a molecular weight of the order or 30,000.

The compositions of this invention can be applied to the hair from solution by manual means, such as, for example, by brushing or combing the solution through the hair. They may also be sprayed on the hair from a pressurized container equipped with a conventional spray nozzle. Low pressure aerosol bombs are well-known generally and are a preferred means for dispensing many industrial and household commodities, including many of the hair control preparations currently on the market.

Therefore, in one of its aspects this invention provides for the use of a hair control composition which comprises in combination, a resinous material such as polyacrylate, PVP, DHFR, PVP/ VA, or mixtures thereof, a substituted diphenyl compound which has a stiffening effect on filmsof the resinous material, perfume, a liquified normally gaseous propellant, and a solvent. Suitable propellants are CCl F and CCl F A suitable solvent for the resin, perfume, substituted diphenyl compound and propellant, such as ethyl alcohol or any other suitably volatile nontoxic organic solvent, is required. The container should be able to withstand pressures at 70 F. in the range of 25 to 70 pounds per square inch and can be made of any material which is compatible with the ingredients of the hair control composition, e.g. plastic coated glass bottles and tin and aluminum cans.

The compositions of this invention may be applied to hair tresses either before or after the tresses have been formed into the desired configuration, or they maybe applied in the process of forming the configuration.

The stiffening agents of this invention function in combination with commercial hair control preparations which contain perfume and resins such as polyacrylate, PVP, DHFR, PVP/VA or mixtures thereof, through an apparent synergistic mechanism to produce improved maintenance of a coiffure This improved maintenance results from an actual stiffening of the resinous film. Although many of these stiffening agents exhibit some slight stiffening effect on hair in the absence of the resin, i.e. they have an inherent stiffening power, the extent to whichthese agents toughen a resinous film is far more than could have been predicted from a knowledge of their inherent stiffening powers. Also, agents which have a low inherent stiffening power have been observed to have a much greater stiffening effect on the resinous films than do agents which have a pronounced inherent stiffening power.

The perfume which is present in the compositions of this invention can consist of one or more of the naturallyoccurring essential oils, one or more specific odorous synthetic organic compounds, or a blend of these essential oils and organic compounds. Essential oils are themselves a blend of a number of different odorous organic compounds. Lemon oil, citronella oil and bois de rose oil are representative of essential oils which are conventionally employed in perfume formulations. The following compounds are representative of the specific odorous organic materials which are also conventionally employed in the perfume formulations: citronellal, vetiverol acetate, methyl phenyl carbinyl acetate, phenyl ethyl acetate, hy' droxycitronellal and phenyl ethyl alcohol. It is the solvent action of these essential oils and odorous compounds which effects the undesirable softening of the watersoluble resinous films which are commonly employed in hair control preparations and which are a constituent of the compositions of this invention.

The effect which the stiffening agents of the invention have upon resinous films themselves can be accurately measured with an R. D. Stiffness Tester, Number 501854, manufactured by the W. & L. E. Gurley Co., of Troy, N.Y. The Gurley tester measures the force required to bend a standard sample a given distance. To test the stiffness of a film, a /2 inch sample is cut from a cast film, thethickness of the film is measured, and the film is placed in the tester. Following the test procedure recommended by the manufacturer, readings are made and a conversion table provided by the manufacturer is used to convert the readings to the stiffness in milligrams, of a standard sample one inch wide and three inches long. Care must be taken in handling the film samples so as not to touch them with moist fingers, since the slightest amount of moisture warps the film. Small tweezers should be used. where possible.

The efficacy of the hair control compositions of the invention to effect improved curl maintenance is determined by a test procedure which provides aquantitative;

expression of the extent of relaxation of a wound curl. In this procedure one-gram switches which are 17 mm. wide and 235 mm. long are water-wet, wound on a 16 mm. diameter test-tube, clamped and dried overnight at ambient temperature. The switches are then further dried for two hours in an oven at 50 C. The clamp and testtube are removed and the neatly formed coil is sprayed with the test preparation from a pressurized container. The spraying is conducted by mounting the coil on a motor-driven wheel in such a manner that as the curl passes the container, spray is directed upon it for 0.67 second. This is done twice to expose each curl to spray for 1.33 seconds. The rate of spraying is a function of the equipment used (i.e. valve) and propellant pressure, but for most commercial preparations is fairly constant at about 1 gram of liquid contents per second. When direct experimental comparisons are made the valve construction, propellant pressure, and container volume should be the same for all samples, and these conditions prevailed in the experiments reported in the examples which follow. After being sprayed, the curls are dried at ambient temperatures for 25 minutes and then suspended for a prescribed time from a fixed reference point in a controlled humidity jar. The length of uncurled hair below the reference point is 205 mm. The humidity employed for the relaxation test can range from about 30% to 100% at the test temperature and is attained in the jar through the conventional use of a saturated solution of a suitable salt.. For example, a saturated solution of ammonium chloride at room temperature (i.e. 70 F.) will provide a relative humidity of 80%.

The calculation of the extent of relaxation is made as follows. A sprayed curl, prepared as outlined above, is placed in the constant humidity jar. The distance from the reference point to the bottom of the sprayed curl is measured at the start of the test and this distance is designated :1 After the sprayed curl has been in the constant humidity jar for the selected testing time, the distance from the reference point to the bottom of this curl is measured, and the distance is designated d A standard fall for the completely relaxed switch is designated d This distance d represents the total possible fall of a water-set control switch under the particular test conditions which are employed. All measurements are made from photographs of the curls. The extent of relaxation can be expressed most usefully as that percent of the total possible fall which a resin treated switch fell under given conditions, and the following formula is used to derive this percent value at the selected testing time and test humidity:

- =percent of total possible fall With the above explanations, the results obtained with the compositions of the invention as set forth in the following examples, will be readily understood. It is to be understood, however, that the specific conditions given in the examples, wherein all parts shown are by weight, are merely illustrative of the broader aspects of the invention more fully covered in the appended claims.

EXAMPLE I The following viscous concentrates were prepared. The Uvinul 490 is a trade name for 2,2'-dihydroxy-4,4'-dimethoxybenzophenone and the Uvinul D50 is a trade name for 2,2',4,4 tetrahydroxybenzophenone. Perfumes A and B are typical of the perfumes commonly used in commercial cosmetic preparations and these two perfumes will be so designated throughout this specification. The composition of perfume A, which has a lilac scent and is composed entirely of synthetic organic compounds, is as follows:

Perfume "A The composition of perfume B, which is a cologne and is composed entirely of naturally occurring essential oils, is as follows:

Perfume B Ingredients: Parts by weight Bergamot 17.0 Lavender 10.0 Lemon (cold pressed) 33.0 Orange 33.0 Petitgrain 3.0 Rosemary 3.0 Thyme red 1.0

These concentrates were cast into films by pouring two cubic centimeters of the viscous concentrate on a 0.15 inch thick polyethylene film stretched over an eight by eight inch plate of double strength glass and held in place with Scotch tape on the reverse side of the plate. A Bird Film applicator which casts a wet-film of 0.004 inch thickness, was drawn slowly through the concentrate and across the plate. The films were then dried by storing the plates for from 1 to 2 hours in a room which had a 70 F. temperature and a 65% relative humidity. If the films become too dry they release from the polyethylene and are too brittle to out without cracking. If the films are not dry enough they stick to the templates which were used to cut one by two inch thick rectangular samples from each film strip for the stiffness testing which has been described hereinbefore. The Gurley stiffness is expressed in milligrams in Table I below.

TABLE I [Percent by weight of viscous concentrate] Perfume Stifiener Anhy- Gurley 127331 V IgVAE aifiousl stifilriiess,

v ue e arm 111 ll- UVllllll Uvinul A B 490 D50 grams It is readily apparent that the perfumes had a decided softening effect upon the PVP/VA films and that this film softening effect was definitely and dramatically reversed by the Uvinul 490 and the Uvinul D50.

EXAMPLE JI Compositions having the following formulation, expressed as parts by weight, were introduced into aerosol cans:

Wound curls were sprayed with these compositions and with a control composition which contained no stiffening agent. The test procedure followed was that described hereinbefore for providing a quantitative expression of the extent of relaxation of a wound curl. The curls re mained in the constant humidity jar at 75 F. for 30 minutes at a relative humidity of 90%. Measurements were converted into the percent of the total possible fall, and it is this percent which is expressed in the following table.

Percent of possible Stifiening agent fall in 30 minutes at 90% RH.

None 38 Diphenylmethlamine. 29

Diphenylmethane; 2

2-hydroxy-5-methylbenzophenonc. 18

1,3-diphenylpropanoue 16 1,3-diphenylpropancdionc-1,3. 14

2,2,4,4-tetrahydroxybenzophenone 11.

All of the designated substituted diphenyl compounds significantly decreased the extent to which the resinous film relaxed under humid conditions, and this decrease in relaxation bears a direct relationship to improved maintenance of a desired hair configuration.

EXAMPLE III The following three compositions expressed as parts by weight, were prepared and cast into films according to the procedure of Example I. The Silicone DC 555 is manufactured by The Dow Corning Corporation and sold under this trade name. It is a 50/50 methyl-phenyl substituted siloxane and is a common constituent in commercial hair control preparations.

PVP/VA-70/30-K value 40 4.00

Silicone/DC 555 0.375

Anhydrous ethanol 95.625

PVP/VA=.-70/30 .K value 40 4.00

Silicone DC 555 0.375

Perfume A 0.25

Anhydrous ethanol 95.375

PVP/VA70/30K value 40 4.00

Silicone DC 555 V 0.375

Perfume A 0.25

Uvinul 490 0.40

Anhydrous ethanol 94.975

The stiffness of the films was tested using the Gurley D.R. Stiffness Tester and the procedure described hereinbefore, andthe following results were obtained.

Film identification: Gurley stiffness, mg. No perfume or Uvinul (1) 17 Perfume but no Uvinul (2) 13 Perfume plus Uvinul (3) 33 Once again it is apparent that perfume has a softening effect on PVP/VA resinous films and that 2,2 dihydroxy 4,4 dimethoxy benzophenone effects a considerable strengthening of this resinous film, a strengthening which is reflected in improved hair control.

EXAMPLE IV A composition having the following formulation, expressed as parts by weight, was introduced into aerosol cans.

Perfume A,.

2,2,4,4'-tctrahydroxybenzophenone .09

PVP/VA-70/30-K value 35 .90

Anhydrous ethanol 28.91

8 CCl F/CC1 F -65%/35% 7000 When sprayed on wound tresses of human hair, this composition provided unusually good maintenance of the desired configuration. Similar results are obtained when a polyacrylate resin having a molecular weight of 30,000 is substituted for the PVP/ VA.

EXAMPLE V A composition having the following formulation, expressed as parts by weight, was introduced into aerosol cans.

Perfume .10 1,3-diphenylpropanedione-1,3 .15 PVP-K value 30 1.50 Anhydrous ethanol 28.25 CCl F/CCl F 65%/35% 70.00

The perfume (carnation) used in this formulation, a mixture of naturally-occurring essential oils and synthetic organic compounds, has the following composition:

When sprayed on wound tresses of human hair, the composition provides far better maintenance of the desired configuration than is provided by a control composition which contained no 1,3-diphenylpropanedione-l,3. Similar results are obtained with a corresponding composition containing a 50/50 mixture by weight of PVP and DHFR.

EXAMPLE VI Perfume B 0.9 2,2-dimethoxy-4,4-dihydroxybenzophenone 0.3 PVP/VA-50/50K value 45 1.5 Anhydrous ethanol 28.2 CCl F/CCl F 65 35 70.0

When sprayed on tresses of human hair, which were then wound to form the desired configuration, the above composition provides superior maintenance of the configuration than is provided by a control composition which contained no 2,2'-dimethoxy-4,4'-dihydroxybenzophenone.

EXAMPLE VII Compositions having the following formulation, expressed as parts by weight, were introduced into aerosol cans:

Dimethyl hydantoin formaldehyde resinmolecular weight 260 1.40 2,2',4,4-tetrahydroxybenzophenone 0.15 Perfume A 0.10 Anhydrous ethanol 28.35 CCl F/CCl F -65%/35% 70.00

Dimethyl hydantoin formaldehyde resinmolecular weight 260 1.40 Perfume A 0.10 Anhydrous ethanol 28.35 CCl F/CCl F 65%/35% 70.00

Wound curls were sprayed with these two compositions. The test procedure followed was that described hereinbefore for providing a quantitative expression of the extent of relaxation of a wound curl. The curls remained in the constant humidity jar at 75 F. for 25 minutes at 90% relative humidity. Measurements were converted into the percent of the total possible fall, and it is this percent which is expressed in the following table.

Percent of Formula: possible fall Did not contain 2,2',4,4 tetrahydroxybenzophenone 52 Contained 2,2,4,4'-tetrahydroxybenzophenone 23 It will thus be seen that the 2,2',4,4-tetrahydroxybenzophenone significantly decreased the extent to which the untreated resinous film would relax under humid conditions.

Having thus described my invention, what I claim and desire to secure by Letters Patent is:

1. A perfumed resinous hair control composition in alcoholic solvent solution, said solution having dissolved therein a stiffening agent to reduce the softening action of perfume on the resinous film resulting on drying and comprising (1) from about .25 to about 10% by weight of the total composition of a water soluble resin selected from the group consisting of polyacrylate, poly vinylpyrrolidone, dimethyl hydantoin formaldehyde, and copolymers of polyvinylpyrrolidone and vinyl acetate; (2) perfume; (3) as a resin stiffening agent, a substituted diphenyl compound having the following general formula:

wherein each R and R in the formula is a radical selected from the group consisting of hydroxy and alkoxy of one to three carbons, x equals to 2, and equals 0 to 2 and wherein R is a radical selected from the group consisting of alkylene of one to three carbons,

and (4) an alcoholic solvent for the resin, perfume, and stiffening agent, the said substituted diphenyl compound being present in an amount from about 1% to about 50% by weight of the resin.

2. A perfumed resinous hair control composition in alcoholic solvent solution, said solution having dissolved therein a stiffening agent to reduce the softening action of perfume on the resinous film resulting on drying and comprising (1) from about 0.5% to about by weight of the total composition of polyvinylpyrrolidone; (2) perfume; (3) as a resin stiffening agent, a substituted diphenyl compound having the following general formula:

wherein each R and R in the formula is a radical selected from the group consisting of hydroxy and alkoxy of one to three carbons, x equals one to two, and y equals one to two; and (4) an alcoholic solvent for the polyvinylpyrrolidone, perfume, and stiffening agent, the said substituted diphenyl compound being present in an amount from about 5% to about 20% by weight of the polyvinylpyrrolidone.

3. A perfumed resinous hair control composition in alcoholic solvent solution, said solution having dissolved therein a stiffening agent to reduce the softening action of perfume on the resinous film resulting on drying and comprising (1) from about 0.5 to about 5% by weight of the total composition of a water-soluble copolymer of polyvinylpyrrolidone and vinyl acetate; (2) perfume; (3) as a resin stiffening agent, a substituted diphenyl compound having the following general formula:

wherein each R and R in the formula is a radical selected from the group consisting of hydroxy and alkoxy of one to three carbons, x equals one to two, and y equals one to two; and (4) an alcoholic solvent for the copolymer of polyvinylpyrrolidone and vinyl acetate, perfume, and stiffening agent, said substituted diphenyl compound being present in an amount from about 5% to about 20% by weight of the copolymer of polyvinylpyrrolidone and vinyl acetate.

4. The composition of claim 3 wherein the substituted diphenyl compound is 2,2,4,4-tetrahydroxybenzophenone.

5. The composition of claim 3 wherein the substituted diphenyl compound is 2,2'-dimethoxy4,4-dihydroxy benzophenone.

6. A perfumed resinous hair control composition in alcoholic solvent solution, said solution having dissolved therein a stiffening agent to reduce the softening action of perfume on the resinous film resulting on drying and comprising (1) from about .5 to about 5% by weight of the total composition of polyacrylate; (2) perfume; (3) as a resin stiffening agent, a substituted diphenyl compound having the following general formula:

( 1) x (R2) y wherein each R and R in the formula is a radical selected from the group consisting of hydroxy and alkoxy of one to three carbons, 1: equals one to two, and y equals one to two; and (4) an alcoholic solvent for the polyacrylate, perfume, and stiffening agent, said substituted diphenyl compound being present in an amount from about 5% to about 20% by weight of the polyacrylate.

7. A perfumed resinous hair control composition in alcoholic solvent solution, said solution having dissolved therein a stiffening agent to reduce the softening action of perfume on the resinous film resulting on drying and comprising (1) from about .5 to about 5% by weight of the total composition of dimethyl hydantoin formaldehyde resin; (2) perfume; 3) as a resin stiffening agent, a substituted diphenyl compound having the following general formula:

1): 0 zly 6WD wherein each R and R in the formula is a radical selected from the group consisting of hydroxyand alkoxy of one to three carbons, as equals one to two, and y equals one to two; and (4) an alcoholic solvent for the dimethyl hydantoin formaldehyde resin, perfume, and stiffening agent, the said substituted diphenyl compound being present in an amount from about 5% to about 20% by weight of the dimethyl hydantoin formaldehyde resin.

8. The process of stiffening perfume-softened resinous film, formed on human hair treated with a solution of a hair control composition on drying, comprising the addition of a substituted diphenyl compound having the following general formula:

(Rat (Rm 6 6 1 1 to 2 and wherein R is a radical selected from the group consisting of alkylene of one to three carbons,

H ll 11 ll CHNH2, CH- CCH:, -CCHz-C-, and C as a resin stiffening agent to a composition comprising: (1) from about .25% to about 10% by weight of the total composition of a water soluble resin selected from the group consisting of polyacrylate, polyvinylpyrrolidone, dimethyl hydantoin formaldehyde, and copolymers of polyvinylpyrrolidone and vinyl acetate; (2) a perfume; and (3) an alcoholic solvent for the resin, perfume, and stiffening agent, the said substituted diphenyl compound being present in an amount from about 1% to about 50% by weight of the resin.

References Cited in the file of this patent UNITED STATES PATENTS 2,305,356 Luckenbach Dec. 15, 1942 FOREIGN PATENTS Great Britain Apr. 11,

OTHER REFERENCES Industrial and Engineering Chemistry, vol. 46, No. 7, page 150, July 1954.

46, pages 5577-9.

De Navarre: Arn. Perf. and Aromatics, vol. 69, No. 1, January 1957, page 31.

Di Giacomo: American Perfumer and Aromatics,

69:5, May 1957, pages -50, particularly page 47.

Chemicals, C & 'E News, Nov. 12, 1956, vol. 34, No.

Claims (1)

1. A PERFUMED RESINOUS HAIR CONTROL COMPOSITION IN ALCOHOLIC SOLVERT SOLUTION, SAID SOLUTION HAVING DISSOLVED THEREIN A STIFFENING AGENT TO REDUCE THE SOFTENING ACTION OF PERFUME ON THE RESINOUS FILM RESULTING ON DRYING AND COMPRISING (1) FROM ABOUT .25% TO ABOUT 10% BY WEIGHT OF THE TOTAL COMPOSITION OF A WATER SOLUBLE RESIN SELECTED FROM THE GROUP CONSISTING OF POLYACRYLATE, POLYVINYLPYRROLIDONE, DIMETHYL HYDANTOIN FORMALDEHYDE, AND COPOLYMERS OF POLYVINYLPYRROLIDONE AND VINYL ACETATE; (2) PERFUME; (3) AS A RESIN STIFFENING AGENT, A SUBSTITUTED DIPHENYL COMPOUND HAVING THE FOLLOWING GENERAL FORMULA:
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Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3231407A (en) * 1963-06-26 1966-01-25 Eagle Pencil Co Protection of charcoal and pastel crayon drawings with coatings composed of copolymers of n-vinyl-2-pyrrolidone and vinyl acetate
US3234285A (en) * 1962-04-04 1966-02-08 Dow Chemical Co Bis(cycloalkylphenols)
US3336156A (en) * 1963-05-20 1967-08-15 Gen Aniline & Film Corp Copolymer vinylpyrrolidone vinylacetate film former for coating or printing on water soluble films
US3337488A (en) * 1965-01-22 1967-08-22 Gulf Oil Corp Process for hydrolyzing ethylenealkyl acrylate copolymers with aqueous ammonia
US3346457A (en) * 1963-11-05 1967-10-10 Ciairol Inc Hair treating compositions containing a saturated hydrocarbon as a moisturebarrier material
US3395041A (en) * 1964-11-24 1968-07-30 Gillette Co Treatment of hair which has previously been treated with a resin composition
US3426137A (en) * 1965-12-23 1969-02-04 Olin Mathieson Hair growth inhibiting by aminobenzophenones
US3445566A (en) * 1966-03-18 1969-05-20 Nat Starch Chem Corp Hair spray compositions containing an ultraviolet absorbing film forming copolymer
US3512232A (en) * 1966-11-23 1970-05-19 Deering Milliken Res Corp Process for preparing twistless yarns
US3670074A (en) * 1971-01-22 1972-06-13 Cyril Doner Sunscreen formulation containing triethanolamine neutralized 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid
US3757804A (en) * 1968-07-18 1973-09-11 Fr Sa Product for treating hair
US3906091A (en) * 1969-12-24 1975-09-16 Oreal Hair-setting lotion containing a reducing agent
US3988110A (en) * 1969-12-24 1976-10-26 Societe Anonyme Dite: L'oreal Hair coloring and hair-setting lotion containing a direct dye, a reducing agent and a solar filter
US4015017A (en) * 1974-01-15 1977-03-29 Laboratoires Pharmascience Certain biphenyl derivatives used to treat disorders caused by increased capillary permeability
US4318906A (en) * 1979-06-25 1982-03-09 Establissement Rinrone Medicinal composition for external use for treating wounds
US4818523A (en) * 1987-06-17 1989-04-04 Colgate-Palmolive Company Hair rinse conditioner
US4886660A (en) * 1987-06-11 1989-12-12 Colgate-Palmolive Company Shine hair conditioner
US8877704B2 (en) * 2012-10-15 2014-11-04 Givaudan Sa Organic compounds

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2305356A (en) * 1940-04-04 1942-12-15 Rohm & Haas Dressing of hair
US2686812A (en) * 1951-09-07 1954-08-17 Gen Aniline & Film Corp 2, 2', 4-trihydroxy-4'-alkoxybenzophenones and the process of preparing the same
US2693492A (en) * 1954-11-02 - dihydroxy -
US2723248A (en) * 1954-10-01 1955-11-08 Gen Aniline & Film Corp Film-forming compositions
GB747806A (en) * 1953-03-27 1956-04-11 Gen Aniline & Film Corp Hair waving and setting composition
US2876210A (en) * 1954-02-10 1959-03-03 Gen Aniline & Film Corp 2,2'-dihydroxy-4, 4'-substituted benzophenones as ultraviolet absorbents for gr-a rubber
US2956927A (en) * 1956-06-01 1960-10-18 Curtis Helene Ind Inc 5, 5'-dialkylhydantoin-formaldehyde resin aerosol hair spray

Patent Citations (7)

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Publication number Priority date Publication date Assignee Title
US2693492A (en) * 1954-11-02 - dihydroxy -
US2305356A (en) * 1940-04-04 1942-12-15 Rohm & Haas Dressing of hair
US2686812A (en) * 1951-09-07 1954-08-17 Gen Aniline & Film Corp 2, 2', 4-trihydroxy-4'-alkoxybenzophenones and the process of preparing the same
GB747806A (en) * 1953-03-27 1956-04-11 Gen Aniline & Film Corp Hair waving and setting composition
US2876210A (en) * 1954-02-10 1959-03-03 Gen Aniline & Film Corp 2,2'-dihydroxy-4, 4'-substituted benzophenones as ultraviolet absorbents for gr-a rubber
US2723248A (en) * 1954-10-01 1955-11-08 Gen Aniline & Film Corp Film-forming compositions
US2956927A (en) * 1956-06-01 1960-10-18 Curtis Helene Ind Inc 5, 5'-dialkylhydantoin-formaldehyde resin aerosol hair spray

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3234285A (en) * 1962-04-04 1966-02-08 Dow Chemical Co Bis(cycloalkylphenols)
US3336156A (en) * 1963-05-20 1967-08-15 Gen Aniline & Film Corp Copolymer vinylpyrrolidone vinylacetate film former for coating or printing on water soluble films
US3231407A (en) * 1963-06-26 1966-01-25 Eagle Pencil Co Protection of charcoal and pastel crayon drawings with coatings composed of copolymers of n-vinyl-2-pyrrolidone and vinyl acetate
US3346457A (en) * 1963-11-05 1967-10-10 Ciairol Inc Hair treating compositions containing a saturated hydrocarbon as a moisturebarrier material
US3395041A (en) * 1964-11-24 1968-07-30 Gillette Co Treatment of hair which has previously been treated with a resin composition
US3337488A (en) * 1965-01-22 1967-08-22 Gulf Oil Corp Process for hydrolyzing ethylenealkyl acrylate copolymers with aqueous ammonia
US3426137A (en) * 1965-12-23 1969-02-04 Olin Mathieson Hair growth inhibiting by aminobenzophenones
US3445566A (en) * 1966-03-18 1969-05-20 Nat Starch Chem Corp Hair spray compositions containing an ultraviolet absorbing film forming copolymer
US3512232A (en) * 1966-11-23 1970-05-19 Deering Milliken Res Corp Process for preparing twistless yarns
US3757804A (en) * 1968-07-18 1973-09-11 Fr Sa Product for treating hair
US3988110A (en) * 1969-12-24 1976-10-26 Societe Anonyme Dite: L'oreal Hair coloring and hair-setting lotion containing a direct dye, a reducing agent and a solar filter
US3906091A (en) * 1969-12-24 1975-09-16 Oreal Hair-setting lotion containing a reducing agent
US3670074A (en) * 1971-01-22 1972-06-13 Cyril Doner Sunscreen formulation containing triethanolamine neutralized 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid
US4015017A (en) * 1974-01-15 1977-03-29 Laboratoires Pharmascience Certain biphenyl derivatives used to treat disorders caused by increased capillary permeability
US4318906A (en) * 1979-06-25 1982-03-09 Establissement Rinrone Medicinal composition for external use for treating wounds
US4886660A (en) * 1987-06-11 1989-12-12 Colgate-Palmolive Company Shine hair conditioner
US4818523A (en) * 1987-06-17 1989-04-04 Colgate-Palmolive Company Hair rinse conditioner
US8877704B2 (en) * 2012-10-15 2014-11-04 Givaudan Sa Organic compounds
CN105431510A (en) * 2012-10-15 2016-03-23 奇华顿股份有限公司 Organic compounds
WO2014060303A3 (en) * 2012-10-15 2016-04-07 Givaudan Sa Use of 2-hydroxyphenyl aryl ketones as fragrance or flavor components
JP2016518460A (en) * 2012-10-15 2016-06-23 ジボダン エス エー Organic compounds
CN105431510B (en) * 2012-10-15 2020-02-11 奇华顿股份有限公司 Organic compounds

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