GB2160421A - Hair and fabric conditioning preparation - Google Patents
Hair and fabric conditioning preparation Download PDFInfo
- Publication number
- GB2160421A GB2160421A GB08514222A GB8514222A GB2160421A GB 2160421 A GB2160421 A GB 2160421A GB 08514222 A GB08514222 A GB 08514222A GB 8514222 A GB8514222 A GB 8514222A GB 2160421 A GB2160421 A GB 2160421A
- Authority
- GB
- United Kingdom
- Prior art keywords
- preparation according
- conditioning preparation
- amine
- conditioning
- quaternary ammonium
- 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.)
- Withdrawn
Links
Classifications
-
- 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
- A61K8/42—Amides
-
- 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
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
Abstract
A conditioning and softening preparation for treating fabrics and hair comprises a solution of fatty amide-amine quaternary compound which can be easily diluted with cold water. Typical quaternary compounds have the formula: <IMAGE> wherein R is a C17-35 alkyl group, and R<1>, R<2> and R<3> are optionally substituted alkyl, aryl or aralkyl groups. The compositions may constitute a hair shampoo together with a suitable detergent.
Description
SPECIFICATION
Conditioning Preparation
This invention concerns a conditioning, which is to say softening, preparation for application to the hair or skin or for domestic use on fabrics.
Generally, the active ingredient in known hair or skin conditioning preparations comprises a fatty amine quaternary compound. Such compounds are normally solid or paste-like at room temperatures and must be emulsified using an appropriate agent in hot water to form a product of sufficiently low viscosity for bottling in a form suitable for use in the salon or home.
The present invention is based on the discovery that the fatty amide-amine quaternary compounds have broadly comparable properties for the conditioning of human hair or skin and can be readily diluted in water if necessary with use of a suitable solvent such as iso-butyl alcohol.
Thus, according to the present invention, there is provided a conditioning preparation comprising a solution of fatty amide-amine quaternary compound which can be easily diluted with cold water.
The viscosity of preparation may be increased as desired by the addition of common salt-compared with the addition of a relatively costly thickening agent, such as carboxy methyl cellulose, to the conventional fatty amine quaternary compounds.
Generally the preparation will include colouring agents, a perfume and possibly an opacifier or pearlising agent such as ethylene glycol mono stearate, for example.
If desired a cleansing agent may be added to produce a "liquid soap or shampoo".
One cleansing agent may be an anionic compound such as an alkyl ether sulphate, an alkyl alcohol sulphate, or a sulpho-succinate derivative, for example.
Since the cationic quaternary compound and anionic compound may react to limitfoaminga customary desirable attribute of this kind of preparation-a foaming agent such as an amphoteric or amine oxide may be added.
Another cleansing agent may be an amide-amine betaine or sultaine, for example, which, being fully compatible with the quaternary compound, may be admixed in desired proportion to produce a preparation of desired characteristics.
The invention will be further apparent from the following description which concerns, by way of example only, a number of compounds which may be utilised in its practice.
The quaternary ammonium compound utilised in the present composition is of the type derived from amide-amines having the formula R-CO-N H-(CH2)3-N-(CH3)2 where R-CO is a fatty acid residue ranging from 10 to 18 carbon atoms. The resulting amide-amine quaternary ammonium compound has the following general formula
A preferred quaternary ammonium compound for use in the present invention is the stearamidopropyl dimethyl hydroxypropyl quaternary ammonium compound where R=C"H35, R1 is CH3 and R2 is 2-hydroxy propyl. A further preferred quaternary ammonium compound for use in accordance with the present invention is the stearamidopropyl dimethyl benzyl quaternary ammonium compound where R is C,7H3 > , R, is CH3 and R2 is a benzyl group.
Although these two quaternary ammonium compounds are preferred, many other possible amide-amine quaternary ammonium compounds may also be used in a conditioning preparation of the present invention. For example, R2 may include other groups such as lower alkyl groups having 1 to 4 carbons, hydroxy substituted alkyl groups, aralkyl groups other than benzyl such as tolyl and xylyl and also dihydroxy substituted alkyl groups.
Examples of preparation of suitable compounds follow.
Benzyl Quaternary Compound
1. To an aqueous suspension of 350 parts by weight of Stearamido-propyl Dimethylamine in 800 parts water, add slowly benzyl chloride to 125 parts, stirring at a temperature of 75 to 850C. After all the benzyl chloride is added, slowly raise the heat to 90"C continuing stirring until no further benzyl chloride odour is detectable (about 2 hours).
2. To test for unreacted benzyl chloride: take lcc of mixture and add 0.1 normal silver nitrate until precipitation of silver chloride ceases. Note the quantity of silver nitrate required.
3. To another cc of the mixture add Scc sodium hydroxide (0.1 normal) and heat for 30 minutes at 95"C. Cool and add nitric acid bringing ph to 7. Add 0.1 normal silver nitrate until precipitation of silver chloride ceases. This should require about the same quantity as in step 2. If more than 0.06cc of excess silver nitrate is required in step 3 as compared to step 2, there is excess unreacted benzyl chloride.
The Benzyl Quaternary solution should be 37% active.
Hydroxypropyl Quaternary Compound
1. To the same suspension as in step 1 above, bubble in 56 parts by weight propylene oxide gas using a closed vessel with air displaced by nitrogen.
Maintain temperature at 75"C for one hour.
2. Cool and add 57% active glycolic acid until ph 7 is reached. This should require 133 parts by weight.
The achievement of neutrality is an adequate control check. Hydroxypropyl Quaternary should be 36% active.
If Stearamidopropyl Dimethylamine is not available, it may be prepared as follows:- 1. By weight: 270 parts StearicAcid, 100 parts
DMPA (Dimethylamino propylamine).
2. Charge into reaction kettle fitted with heating elements (steam coil high pressure or otherwise).
Heat to 1400Cto 1500C and reactfor3 hours. This will expel most of the water along with some amine.
Then slowly allow the temperature to rise to 1 650C to 1700C and hold for one hour completing the reaction.
A reflux condenser or partial reflux condenser is helpful in producing high yields. In large quantities, the water mixture can be collected and worked up for amine.
3. Following completion of the reaction, it is desirable to cool the mixture to 1 200C and stir under a partial vacuum of 20mm to 50mm of mercury to evacuate any residual amine. Nitrogen purging or steam stripping in vacuo will also accomplish this.
4. To test for unreacted Stearic acid: In a 50% alcohol solution (20cc) with phenol phthalein as indicator, add sodium hydroxide until a faint pink colour is evident. Next, dissolve 0.5 grams of mixture (colour should disappear). No more than 1cc of 0.1 normal sodium hydroxide solution should bring back the pink colour or there is excess unreacted Stearic acid.
In one conditioning shampoo embodying the invention the quaternary compound is admixed with an amide-amine betaine derived from an amide-amine. It is of the type
where R-CO is a fatty acid residue ranging from 10 to 18 carbon atoms and where R, is a lower alkyl radical ranging from 1 to 3 carbon atoms.
Because of the compatibility of the amide-amine betaine and amide-amine quaternary ammonium compounds, the concentration of a quaternary ammonium compound can be varied from 1 to 30% by weight. In prior art shampoos, quaternary ammonium compound levels were necessarily kept low not only because of incompatibility of the detergent compounds, but also due to eye irritation and possible damage from high quaternary ammonium compounds concentrations. In the present invention, however, the amide-amine quaternary ammonium compounds are less irritating than prior quaternary ammonium compounds used in shampoo formulations, and their irritating effects are moderated by the amideamine betaine thereby allowing the use of higher concentrations without the dangers of possible eye irritation and damage.
The conditioning shampoo composition ofthe present invention is highly compatible with hard waters and will even foam quite well in sea water. In addition, any biocidal activity which the amideamine quaternary ammonium compounds have is not destroyed or otherwise compromised in the presence of the amide-amine betaine compounds.
Furthermore, the use of the amide-amine betaine, which is also well absorbed on most surfaces, regulates any build-up of overconditioning which
can take place if strong quaternary conditioners
alone are used separately either on hair or textile
fibres.
The preferred concentrations of amide-amine
betaine and amide-amine quaternary ammonium
compound is from between 1 to 30% of each
compound. These compounds are dissolved in
water to form an aqueous solution thereof. If
desired, standard shampoo additives may also be
included to enhance certain other shampoo
characteristics for example, to increase or decrease
viscosity, coconut diethanol amide may be added in
concentrations ranging from 1 to 5% by weight. In
addition fragrances may be added if desired without
deleteriously affecting the shampoo composition.
Exampies of shampoos or bath preparations
based on the amide-amine type of betaines and
quaternary are as follows:- Coco amido betaine 10 parts w/w
Amide-amine stearic
benzyl quaternary 6 parts w/w
Coconut diethanolamide 3 parts w/w
Perfume q.s.
Distilled or deionized
water 81 parts w/w
While the above formulation may be regarded as
suitable for average hair, a particularly dry hair
which is fine and long may be better served with the
following formulation affording greater
conditioning action:- Coco amido betaine 8 parts w/w
Amide-amine stearic
benzyl quaternary 10 partsw/w
Coconut diethanolamide 3 parts w/w
Perfume q.s.
Distilled or deionized
water 79 parts w/w
For maximum conditioning of very dry hair, the amount of quaternary ammonium compound can be increased to 30 parts by weight. Accordingly, for maximum cleaning, the betaine concentration may be increased to 30 parts by weight. For very oily hair, the amount of quaternary may be reduced to low levels or near 1 part by weight.
Another example in which sulfobetaine or sultaines are used with a different quaternary compound is as follows: Amide-amine coco
sultaine 10 parts w/w
Amide-amine palmitic
hydroxy-propyl
quaternary 5 parts w/w
Coconut diethanolamine 2 parts w/w
Deionized water 83 parts wiw Further examples of shampoos or bath preparations based on different types of amideamine betaines and quaternary compounds are as follows:
Amide-amine lauric
betaine 10 partsw/w
Amide-amine stearic
benzyl quaternary 6 parts w/w
Coconut diethanolamide 2 parts w/w
Perfume q.s.
Distilled or deionized
water 81 parts w/w
A formulation for particularly dry hair which is fine and long is:
Amide-amine myristic
betaine 8 parts w/w
Amide-amine stearic
hydroxy-propyl
quaternary 10 partsw/w
As is apparent, the relative amounts of detergent
(betaine) and conditioner (quaternary ammonium)
may be varied widely to achieve many different desirable characteristics. The two compounds are in all respects fully compatible. This is particulary advantageous for large scale production of hair shampoos, since a wide variety of shampoos for dry through oily hair may be formulated by simply varying the relative amounts of the betaine and
quaternary ammonium compounds. This foregoes the need for constant changing of equipment and chemicals to produce shampoos with different con
ditioning qualities. Although it is preferred that the
quaternary ammonium compound be an amide
amine derivative, this is not absolutely necessary
with possible conditioning shampoo compositions
including an amide-amine betaine in combination
with a quaternary compound.
It will be appreciated that it is not intended to limit the invention to the above example only, many variations, such as might readily occur to one skilled in the art, being possible, without departing from the scope thereof as defined by the appended
Claims (14)
1. A conditioning preparation comprising a solution of fatty amide-amine quaternary compound which can be easily diluted with cold water.
2. A conditioning preparation according to claim 1 wherein the quaternary ammonium compound utilised is of the type derived from amide-amines having the formula R-CO-NH-(CH2)3-N-(CH3)2 where R-CO is a fatty acid residue ranging from 10 to 18 carbon atoms.
3. A conditioning preparation according to claim 2 wherein the amide-amine quaternary ammonium compound has the following general formula
4. A conditioning preparation according to claim 3 wherein the quaternary ammonium compound is stearamidopropyl dimethyl hydroxypropyl quaternary ammonium compound where R=C17H3s, R1 is CH3 and R2 is 2-hydroxy propyl.
5. A conditioning preparation according to claim 3 wherein the quaternary ammonium compound is stearamidopropyl dimethyl benzyl quaternary ammonium compound where R is C17H3s, R1 is CH3 and R2 is a benzyl group.
6. A conditioning preparation according to any preceding claim wherein the viscosity of the preparation is increased by the addition of common salt.
7. A conditioning preparation according to any preceding claim including coiouring agents.
8. A conditioning preparation according to any preceding claim including a perfume.
9. A conditioning preparation according to any preceding claim including an opacifier or pearlising agent.
10. A conditioning preparation according to claim 9 wherein said opacifier is ethylene glycol mono stearate.
11. A conditioning preparation according to any preceding claim including a cleansing agent.
12. A conditioning preparation according to claim 11 wherein said cleansing agent is an anionic compound such as an alkyl ether sulphate, an alkyl alcohol sulphate, ora sulpho-succinate derivative.
13. A conditioning preparation according to claim 12 including a foaming agent such as an amphoteric or amine oxide.
14. A conditioning preparation according to claim 11 wherein said cleansing agent is an amide-amine betaine or sultaine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB848414701A GB8414701D0 (en) | 1984-06-08 | 1984-06-08 | Conditioning preparation |
Publications (2)
Publication Number | Publication Date |
---|---|
GB8514222D0 GB8514222D0 (en) | 1985-07-10 |
GB2160421A true GB2160421A (en) | 1985-12-24 |
Family
ID=10562148
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB848414701A Pending GB8414701D0 (en) | 1984-06-08 | 1984-06-08 | Conditioning preparation |
GB08514222A Withdrawn GB2160421A (en) | 1984-06-08 | 1985-06-05 | Hair and fabric conditioning preparation |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB848414701A Pending GB8414701D0 (en) | 1984-06-08 | 1984-06-08 | Conditioning preparation |
Country Status (1)
Country | Link |
---|---|
GB (2) | GB8414701D0 (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988003016A1 (en) * | 1986-10-23 | 1988-05-05 | Stevens Frank H | Particulate emulsifiable hair conditioning composition |
EP0435900A1 (en) * | 1988-09-26 | 1991-07-10 | Inolex Chemical Company | Hair and skin conditioning agents and methods. |
EP0472178A1 (en) * | 1990-08-22 | 1992-02-26 | Kao Corporation | Fabric softener composition |
US5282983A (en) * | 1990-08-22 | 1994-02-01 | Kao Corporation | Fabric softener composition and ammonium salt |
WO1998047860A1 (en) * | 1997-04-22 | 1998-10-29 | Akzo Nobel N.V. | Process for making carboxylic amides |
US5916863A (en) * | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
US6525034B2 (en) | 1999-05-12 | 2003-02-25 | Goldschmidt Chemical Corporation | Clear personal care formulations containing quaternary ammonium compounds and other nitrogen-containing compounds |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB773336A (en) * | 1953-08-11 | 1957-04-24 | Ciba Ltd | Manufacture and use of new amine condensation products |
GB818361A (en) * | 1954-07-20 | 1959-08-12 | Ciba Ltd | Detergent preparations for the hair |
GB818362A (en) * | 1954-07-20 | 1959-08-12 | Ciba Ltd | Detergent preparations for the hair |
GB815784A (en) * | 1954-08-11 | 1959-08-17 | Ciba Ltd | Cosmetic preparations for the hair |
GB842842A (en) * | 1958-01-20 | 1960-07-27 | Chemische Werke Witten Gmbh | Improvements in or relating to softeners for textile fibres |
GB874032A (en) * | 1957-01-14 | 1961-08-02 | Ciba Ltd | New di-quaternary ammonium compounds |
GB1029043A (en) * | 1963-05-03 | 1966-05-11 | Ciba Ltd | Gelatinous preparations containing quaternary ammonium salt derivatives |
-
1984
- 1984-06-08 GB GB848414701A patent/GB8414701D0/en active Pending
-
1985
- 1985-06-05 GB GB08514222A patent/GB2160421A/en not_active Withdrawn
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB773336A (en) * | 1953-08-11 | 1957-04-24 | Ciba Ltd | Manufacture and use of new amine condensation products |
GB818361A (en) * | 1954-07-20 | 1959-08-12 | Ciba Ltd | Detergent preparations for the hair |
GB818362A (en) * | 1954-07-20 | 1959-08-12 | Ciba Ltd | Detergent preparations for the hair |
GB815784A (en) * | 1954-08-11 | 1959-08-17 | Ciba Ltd | Cosmetic preparations for the hair |
GB874032A (en) * | 1957-01-14 | 1961-08-02 | Ciba Ltd | New di-quaternary ammonium compounds |
GB842842A (en) * | 1958-01-20 | 1960-07-27 | Chemische Werke Witten Gmbh | Improvements in or relating to softeners for textile fibres |
GB842829A (en) * | 1958-01-20 | 1960-07-27 | Chemische Werke Witten Gmbh | Quaternary amide-zinc pentachlorophenolate salts |
GB1029043A (en) * | 1963-05-03 | 1966-05-11 | Ciba Ltd | Gelatinous preparations containing quaternary ammonium salt derivatives |
Non-Patent Citations (1)
Title |
---|
AM SCHWARTZ J W PERRY + J BERCH }SURFACE ACTIVE AGENTS AND DETERGENTS}, 1958 INTERSCIENCE PUBLISHERS INC PAGES 266-267 * |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1988003016A1 (en) * | 1986-10-23 | 1988-05-05 | Stevens Frank H | Particulate emulsifiable hair conditioning composition |
US4891214A (en) * | 1986-10-23 | 1990-01-02 | Sherex Chemical Company, Inc. | Particulate emulsifiable hair conditioning composition |
EP0435900A1 (en) * | 1988-09-26 | 1991-07-10 | Inolex Chemical Company | Hair and skin conditioning agents and methods. |
EP0435900A4 (en) * | 1988-09-26 | 1992-04-08 | Inolex Chemical Company | Hair and skin conditioning agents and methods |
EP0472178A1 (en) * | 1990-08-22 | 1992-02-26 | Kao Corporation | Fabric softener composition |
US5282983A (en) * | 1990-08-22 | 1994-02-01 | Kao Corporation | Fabric softener composition and ammonium salt |
US6037315A (en) * | 1996-05-03 | 2000-03-14 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions |
US5916863A (en) * | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
US6004913A (en) * | 1996-05-03 | 1999-12-21 | Akzo Nobel N.V. | High di(alkyl fatty ester) quaternary ammonium compound in esteramine from triethanolamine |
US6323167B1 (en) | 1996-05-03 | 2001-11-27 | Akzo Nobel N.V. | High di(alkyl fatty ester) quaternary ammonium compounds in fabric softening and personal care compositions |
US6770608B2 (en) | 1996-05-03 | 2004-08-03 | Akzo Nobel N.V. | High di(alkyl fatty ester) amines and quaternary ammonium compounds derived therefrom |
WO1998047860A1 (en) * | 1997-04-22 | 1998-10-29 | Akzo Nobel N.V. | Process for making carboxylic amides |
US6107498A (en) * | 1997-04-22 | 2000-08-22 | Akzo Nobel N.V. | Process for making carboxylic amides |
US6525034B2 (en) | 1999-05-12 | 2003-02-25 | Goldschmidt Chemical Corporation | Clear personal care formulations containing quaternary ammonium compounds and other nitrogen-containing compounds |
Also Published As
Publication number | Publication date |
---|---|
GB8414701D0 (en) | 1984-07-11 |
GB8514222D0 (en) | 1985-07-10 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4069347A (en) | Compositions of quaternary ammonium derivatives of lanolin acids | |
US3155591A (en) | Hair rinse compostions of polyoxypropylene quaternary ammonium compounds | |
US5939059A (en) | Hair conditioner and 2 in 1 conditioning shampoo | |
US4818440A (en) | Novel polyether carboxylic acid derivatives, as well as their uses | |
US3578719A (en) | Surface active agents | |
US4012398A (en) | Quaternary halides of mink oil amides | |
US3322676A (en) | Shampoos | |
EP0980352B1 (en) | Softening active substance for textiles and textile-softening compositions containing it | |
JP3524223B2 (en) | Thickened detergent composition containing a mixture of polyoxypropylene fatty acid isopropanolamides | |
JPH08337560A (en) | Mixture of polyoxypropylene fatty acid alkanolamide compound, its production and chemical agent containing the same mixture | |
US4515775A (en) | Polyhydroxyl non-ionic surfactant, process for preparing the same and cosmetic composition containing the same | |
US6287547B1 (en) | Hair treatment composition | |
US4247425A (en) | Light duty non-irritating detergent compositions | |
GB2160421A (en) | Hair and fabric conditioning preparation | |
US3865542A (en) | Hair dyeing compositions containing polyhydroxylated polyether nonionic surfactants | |
JPH0115482B2 (en) | ||
EP0176151A1 (en) | Detergents containing amides as thickening agents | |
JPS5914518B2 (en) | Liquid shampoo composition | |
JP3088804B2 (en) | Skin cleanser | |
US3877955A (en) | Cosmetic compositions | |
JP3871730B2 (en) | Novel quaternary ammonium salt, process for producing the same and surfactant composition, and hair cosmetic containing the same | |
EP0279457B1 (en) | Detergent composition | |
US3290304A (en) | Quaternary ammonium compounds, their preparation and their use | |
JP4647808B2 (en) | Thickener for liquid detergent and liquid detergent composition containing the same | |
JPH1072331A (en) | Cosmetic and cleansing agent composition |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |