US3068150A - Method of rinsing hair with hydrazinium chlorides - Google Patents
Method of rinsing hair with hydrazinium chlorides Download PDFInfo
- Publication number
- US3068150A US3068150A US88669A US8866961A US3068150A US 3068150 A US3068150 A US 3068150A US 88669 A US88669 A US 88669A US 8866961 A US8866961 A US 8866961A US 3068150 A US3068150 A US 3068150A
- Authority
- US
- United States
- Prior art keywords
- hair
- hydrazinium
- chloride
- bis
- compounds
- 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 - Lifetime
Links
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical class Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 title description 6
- -1 HYDRAZINIUM COMPOUND Chemical class 0.000 claims description 13
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 8
- 239000003760 tallow Substances 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 6
- GIKDYMRZQQJQFB-UHFFFAOYSA-N Methylhydrazine hydrochloride Chemical compound Cl.CNN GIKDYMRZQQJQFB-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 7
- 150000001875 compounds Chemical group 0.000 description 7
- 238000009472 formulation Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 5
- 239000002304 perfume Substances 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 description 1
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004851 dishwashing Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-O hydrazinium(1+) Chemical compound [NH3+]N OAKJQQAXSVQMHS-UHFFFAOYSA-O 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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
- A61Q5/02—Preparations for cleaning the hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
Definitions
- This invention relates to improved hair rinse compositions and more particularly to a hair rinse containing certain hydrazinium compounds.
- the modern rinses are of an entirely different nature than the earlier acid type rinses. They may be defined as filmformers under proper conditions.
- the novel hydrazinium compounds of our composition fall within this type of composition. These compounds form what might be called monomolecular film on the hair. This type of film not only gives a pleasant sheen and appearance to the hair but also makes for easier combing and greater manageability.
- the hydrazinium compounds of our novel hair rinse composition form compounds with the ionic and non-ionic detergents. For this reason, the application of our novel compound is normally as a separate rinse after the shampooing of the hair has been completed. Alternately these materials may be applied with the shampoos. However, we prefer to use our formulations as a separate rinse.
- the hydrazinium compounds of our composition are represented by the general formula
- the R groups may be hydrogen, alkyl or substituted alkyl groups containing 1 to 45 carbon atoms.
- the X groups may be chlorine, bromine or iodine.
- the compounds have structures as shown and are named hydrazinium according to the International Union of Chemistry rules of nomenclature.
- R groups contains more than eight carbon atoms.
- suitable compounds include: N,N-bis (hydro tallow) N-methyl hydrazinium chloride, N,N-dimethyl- Ncoco hydrazinium chloride, N,N-dimethyl-N-octadecylhydrazinium chloride, N,N-dimethyl-N- (hydro tallow) hydrazinium chloride, N (Z-hydroxyethyl) N,N-bis (Z-stearoyloxyethyl) hydrazinium chloride, etc.
- the hydrazinium compounds are present as 2 to 15 percent, preferably 3 to 5 percent of the formulation.
- EXAMPLE VI The novel hydrazinium compounds of our invention were evaluated as hair conditioners using the compound N,N-bis(hydro tallow)N-methylhydrazinium chloride, hereafter referred to as CA-lOO.
- CA-lOO N,N-bis(hydro tallow)N-methylhydrazinium chloride
- the method of rinsing hair' whichcomprises treating said hair with a 145%- aqueoussolution of a hydrazinium compound selected from the group consisting 4 of N,N-bis -(hydro tallow) N-methyl-hydrazinium chlo ride; N,N-dimethyl-N-coco hydrazinium chloride; N,N- dimethyl-N-octadecyl hydrazinium chloride; and N(2-hydroxyethyl) N,N-bis (2-stearoyloxyethyl) hydrazinium 5 chloride.
- a hydrazinium compound selected from the group consisting 4 of N,N-bis -(hydro tallow) N-methyl-hydrazinium chlo ride; N,N-dimethyl-N-coco hydrazinium chloride; N,N- dimethyl-N-octadecyl hydrazinium chloride; and N(2-hydroxyethyl
- the method of rinsing hair which comprises treat ing said hair with a 3-5% aqueous solution of N,N-bis (hydro tallow) N-methyl-hydrazinium chloride.
- the method of rinsing hair which comprises treating said hair with a 3-5 aqueous solution of N,N-dimethyl-N-coco hydrazinium chloride.
- the method of rinsing hair which comprises treating said hair with a 3-5 aqueous solution of N,N-dimethyl-N-octadecyl hydrazinium chloride.
- the method of rinsing hair which comprises treating said. hair with a 35% aqueous solution of N(2-hydroxyethyl) N,N bis (2-stearoyloxyethyl) hydrazinium chloride.
Description
United States This invention relates to improved hair rinse compositions and more particularly to a hair rinse containing certain hydrazinium compounds.
Hair rinses have been used for several years. Both vinegar and lemon juice have been used to remove the lime soap after shampooing the hair. Even before the advent of the earlier detergents and the cold wave com-.
positions, improvements have been made to give added impetus to the field of hair rinses. Various types of solutions including polybasic hydroxy-acids are widely used. Solutions of citric and tartaric acid and later those of maleic acid were suggested as rinses. These materials were used as liquids but were generally sold as powders in which the customerdissolved the liquids or the correct amount of powder in water to make up th composition for use as a hair rinse.
The modern rinses, other than the color rinses, are of an entirely different nature than the earlier acid type rinses. They may be defined as filmformers under proper conditions. The novel hydrazinium compounds of our composition fall within this type of composition. These compounds form what might be called monomolecular film on the hair. This type of film not only gives a pleasant sheen and appearance to the hair but also makes for easier combing and greater manageability. The hydrazinium compounds of our novel hair rinse composition form compounds with the ionic and non-ionic detergents. For this reason, the application of our novel compound is normally as a separate rinse after the shampooing of the hair has been completed. Alternately these materials may be applied with the shampoos. However, we prefer to use our formulations as a separate rinse.
The hydrazinium compounds of our composition are represented by the general formula The R groups may be hydrogen, alkyl or substituted alkyl groups containing 1 to 45 carbon atoms. The X groups may be chlorine, bromine or iodine. The compounds have structures as shown and are named hydrazinium according to the International Union of Chemistry rules of nomenclature.
We prefer to use compounds wherein at least one of R groups contains more than eight carbon atoms. Examples of suitable compounds include: N,N-bis (hydro tallow) N-methyl hydrazinium chloride, N,N-dimethyl- Ncoco hydrazinium chloride, N,N-dimethyl-N-octadecylhydrazinium chloride, N,N-dimethyl-N- (hydro tallow) hydrazinium chloride, N (Z-hydroxyethyl) N,N-bis (Z-stearoyloxyethyl) hydrazinium chloride, etc.
The hydrazinium compounds are present as 2 to 15 percent, preferably 3 to 5 percent of the formulation.
aten t O "ice Although clear solutions of our novel hydrazinium compounds may be used, these formulations are normally This gives themade up as emulsions or dispersions. product a creamed appearance, and thus, the name creme rinse. Typical formulations of our novel hair rinse com.
position is as follows:
EXAMPLE I Acid stabilized, percent Hydrazinium compound [N,N-bis (hydro tallow-) N-methyl hydrazinium chloride] 3' Glyceryl monostearat 3 Distilled water 94 Water soluble perfum q.s. D and C Red No. 19 q.s.
EXAMPLE II Hydrazinium compound [N,N-bis(hydro tallow) N-methylhydrazinium chloride] 3 Glyceryl monopalmimte I 3 Distilled water 94 Water soluble perfume q.s.
EXAMPLE III Hydrazinium compound (N,N-dimethyl-N-soya" hydrazinium chloride) 3 Distilled water 94 Water soluble perfume q.s.
EXAMPLE 1V Hydrazinium compound (N,N-bis coco-N-methylhydrazinium chloride) 3 Glyceryl monostearate 3 Distilled water 94 Water soluble perfume q.s.
EXAMPLE V Hydrazinium compound [N,N-bis(hydro tallow) N-methylhydrazinium chloride] 15 Distilled water Water soluble perfume q.s.
EXAMPLE VI The novel hydrazinium compounds of our invention were evaluated as hair conditioners using the compound N,N-bis(hydro tallow)N-methylhydrazinium chloride, hereafter referred to as CA-lOO. In order to evaluate these compositions in the most severe conditions a series of swatches of hair were subjected to various conditions which would develop problem hair situations. The swatches were soaked for two or three hours in 6% hydrogen peroxide. After the bleach treatment, the hair Was washed with dishwashing detergent, soaked in vinegar, rinsed with water and then with the commercial creme rinses or our CA-lOO formulation. All the swatches were Wound up on permanent wave curlers and oven dried at a temperature of about 200 F. As a result of the bleaching and other preliminary treatment, the hair showed very definite evidences of damage. The hair was rough and tangled very badly to the point that several strands of the hair broke when combing was attempted. The damaged hair magnified the results of gall! rinse treatment. The results of this run are shown I e ow:
Table I Sample Treatment Wet combing (not Dry combing No. curled) (curled) 1 None Impossible Harsh stiff, nearly impossible.
2 Commercial Hair Rinse Combed Easily... Not much A. improve ment over 1. 3 Commercial Softening Hard to Comb.... Some improve- Agent. ment over 2. 4 CA-100 1% rinsed with Improved Comb- Best combing Hi0. ing. sample, least breaking. 5 (IA-100 1% not rinsed--- Nit as good as 6 Commercial hair rinseB- Combed easily-.-- Impossible.
The more these samples were handled and combed, the more hair broke out of each swatch. The worse the sample the more breakage occurred. The superiority of (4) (CA-1.00) formulation was demonstrable throughout.
Obviously many modifications and variations of the invention as here and above set forth may be made without departing from the essence and scope thereof and only such limitations should he applied as are indicated in the appended claims.
What is claimed is:
1. The method of rinsing hair'whichcomprises treating said hair with a 145%- aqueoussolution of a hydrazinium compound selected from the group consisting 4 of N,N-bis -(hydro tallow) N-methyl-hydrazinium chlo ride; N,N-dimethyl-N-coco hydrazinium chloride; N,N- dimethyl-N-octadecyl hydrazinium chloride; and N(2-hydroxyethyl) N,N-bis (2-stearoyloxyethyl) hydrazinium 5 chloride.
2. The method of rinsing hair which comprises treat ing said hair with a 3-5% aqueous solution of N,N-bis (hydro tallow) N-methyl-hydrazinium chloride.
3. The method of rinsing hair which comprises treating said hair with a 3-5 aqueous solution of N,N-dimethyl-N-coco hydrazinium chloride.
4. The method of rinsing hair which comprises treating said hair with a 3-5 aqueous solution of N,N-dimethyl-N-octadecyl hydrazinium chloride.
5. The method of rinsing hair which comprises treating said. hair with a 35% aqueous solution of N(2-hydroxyethyl) N,N bis (2-stearoyloxyethyl) hydrazinium chloride.
References Cited in the file of this patent UNITED STATES PATENTS Omietanski Oct. 4, 1960 OTHER REFERENCES
Claims (1)
1. THE MEHTOD OF RINSING HAIR WHICH COMPRISES TREATING SAID HAIR WITH A 1-15% AQUEOUS SOLUTION OF A HYDRAZINIUM COMPOUND SELECTED FROM THE GROUP CONSISTING OF N,N-BIS (HYDRO "TALLOW") N-METHYL-HYDRAZINIUM CHLORIDE; N,N-DIMETHYL-N-"COCO"HYDRAZINIUM CHLORIDE; N,NDIMETHYL-N-OCTADECYL HYDRAZINIUM CHLORIDE; AND N(2-HYDROCYETHYL) N,N-BIS (2-STEAROYLOXYETHYL) HYDRAZINIUM CHLORIDE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88669A US3068150A (en) | 1961-02-13 | 1961-02-13 | Method of rinsing hair with hydrazinium chlorides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88669A US3068150A (en) | 1961-02-13 | 1961-02-13 | Method of rinsing hair with hydrazinium chlorides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3068150A true US3068150A (en) | 1962-12-11 |
Family
ID=22212716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US88669A Expired - Lifetime US3068150A (en) | 1961-02-13 | 1961-02-13 | Method of rinsing hair with hydrazinium chlorides |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3068150A (en) |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2955108A (en) * | 1957-01-07 | 1960-10-04 | Univ Ohio State Res Found | Process for 1,1,1-trisubstituted hydrazinium chlorides |
-
1961
- 1961-02-13 US US88669A patent/US3068150A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2955108A (en) * | 1957-01-07 | 1960-10-04 | Univ Ohio State Res Found | Process for 1,1,1-trisubstituted hydrazinium chlorides |
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