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Publication numberUS2983651 A
Publication typeGrant
Publication dateMay 9, 1961
Filing dateDec 10, 1956
Priority dateDec 10, 1955
Publication numberUS 2983651 A, US 2983651A, US-A-2983651, US2983651 A, US2983651A
InventorsSeemuller John Robert
Original AssigneeOreal
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Dyeing of animal fibres
US 2983651 A
Abstract  available in
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Claims  available in
Description  (OCR text may contain errors)

United States Patent DYEING OF ANIMAL FIBRES John Robert Seemuller, Maisons-Lalfitte, France, assignor to Societe Monsavon-lOreal, Paris, France, a corporation of France No Drawing. Filed Dec. 10, 1956, Ser. No. 627,110

Claims priority, application France Dec. 10, 1955 3 Claims. c1; 167-'-88) .tate or other similar solvent and to, prepare an aqueous suspension from this solution with the aid of thickeners and/ or wetting agents.

Generally speaking, these processes only afford a slight improvement in the dyeing and fixation of the dyes when considered in relation to the already appreciable aflinity of the dyes for keratinic fibres at moderate temperature. Moreover, these methods considerably limit the range of dyestuffs which can be employed in hair dyeing. The

present invention obviates these disadvantages and in addition makes it possible to dye live or dead hair by means of dyestuffs "which have hithertobeen regarded as substantially unusable for that purpose. 1 r

It is an object of the present invention to provide a dyeing process in which an increased range of dyes can be employed, more particularly for dyeing hair, which promotesand accelerates the development of the shade and fixing of the dye, and which may be effected at the ambient temperature or at a moderately lowltemperature (e.g.

lower than 50 C) It is a further object of the invention to provide a dyeing process for hair which enables dyeing to be carried out very satisfactorily, from the viewpoint of rapidity and intensity, by means of dyes normallyhaving only very low afiinity, or even no afiinity, for hair under the aforesaid temperature conditions.

According to the present invention a composition for dyeing animalfibres comprises a solution of a direct dye in an aqueous organic solvent which is chemically indifierent with respect tothe dye and to the product to be dyed,

.the said solvent being completely miscible with water in the proportion in which it is present and having the general formula: R--(( -CH CH -OH in which Rrepresents a monovalent aliphatic hydrocarbon group having a straight or branched chain containing 4 to 5 carbonatoms and n is 1.

In the foregoing group R, thebranching may be either of the iso type (as for example inisoamyl alcohol).

Solvents of the aforesaid general formula include, for

example, the products sold under the trademark, Carbitol, and also condensation products of lower aliphatic alcohols with ethylene oxide. Preferred solvents are Z-butoxyethanol (,Butyl Cellosolve?) and the product of condensation of isoamyl alcohol with ethylene oxide in 'the proportion of 1 mole of isoamyl alcohol to .1 to 4, and J preferably 1.2 moles of ethylene oxide.

d ice 'I he above defined organic solvent is preferably used in the proportion of 5-20% by weight of the dyeing solution. However, larger or smaller proportions of solvent may be present depending upon the desired effect and provided that the solvent is wholly miscible with water. The inclusion of the solvent serves two purposes: on the one hand, it ensures, or increases the solubility of the dyestulf in the aqueous solution, and on the other hand, although the reason is not fully understood, the solvent appears to displace in favour of the fibre, the equilibrium which is established between the'dyestuff, the water in which it is dissolved and the fibre.

The expression direct dye is used herein to mean a dyestufi capable of,being directly applied to the fibre to give the final shade without involving the need of any chemical transformation such, for example, as oxidation, coupling or mo'rdanting of the fibre.

The direct dyes thus defined are divided into the following classes in accordance with the various preferred embodiments of the invention:

(A) Nitro dyes, such for example-as methyl-isoicramic acid and 1 hydroxy-2-amino-S-nitrobenzene;

(B) Azo dyes, such for example as those sold under the trade names:

Chrysoidine hydrochlori Edition, 1924) Supracide (Compagnie Frangaise des Matieres Colorantes) Supramine (Bayer) Kiton (Ciba) Cibacet (Ciba) and y Solacet (Imperial Chemical Industries Ltd.)

the last two to the extent to which they are actually azo dyes.

(C) Anthraquinone dyes, such for under the trade names:

Solway (Imperial Chemic Celliton (B.A.S.F.) Acetoquinone ,S (Compagnie tiresColorantes) Cibacet? (Ciba) Solacet (Imperial Chemical Industries Ltd.) Cellit (B.A.S.F.) and -Fenacet (General Dyestuff Corp. NY.)

de (No. 2 Color Index, 1st

example as those sold allndustries Ltd.) a

Frangaise des Ma- Artisil (Sandoz) and also Cibacet" to the extent to which it is applied to soluble pigment dyes. (E) Basic dyes, such as Janus dyes (Bayer),

(F) Complex metalliferous dyes, e.g. those marketed under the trademarks:

Irgalane (JIR. Geigy A.G.)

"Lanasyne (Sandoz S.A.)

Carbolan (Imperial Chemical Industries Cibalane (Ciba) "(G) Dyes of the Nigrosine type (H) Dyes of the Induline" type perature and the hair then rinsed with water.

EXAMPLES (A) Examples of dyeing by means nitro dyes EXAMPLE I Thefollowing solution is prepared:

p Percent Methyl isopicramic acid A Butyl Cellosolve (Z-bu'toxyethanoD 20 Triethanolamine 3 Water to make 100%.

Applied to live hair, 50-60% of which is naturally white, a beautiful violet shade is obtained.

EXAMPLE II The following solution is prepared:

. I Percent l-hydroxy-Z-amino-S-nitrobenzene 0.5 Butyl Cellosolve (Z-butoxyethanol) 20 Triethanolamine 3 Water to make 100%.

By means of this solution a beautiful golden hlonde shade is obtained onlive, white hair.

(B) Examples of dyeing by means of azodyes Water tomake 100%.

By means of this solution hair of a natural light brown shade is dyed a beautiful coppery shade comparable to that obtained with natural henna.

(C) Example of dyeing by means of anthraquinone dyes EXAMPLE IV The following solution is prepared:

. Percent Solway Blue 'RNS (No. 1076, Colour Index, 1st

Edition, 1924) 1 Condensate of isoamyl alcohol and ethylene oxide in molecular proportions of 1:152

Lactic acid 3 Water to make 100%.

By means of this solution an intense blue shade is obtained on naturally white live hair.

EXAMPLE V.DYEING BY MEANS OF CIBACET ANTHRAQUINONE DYES The following solution is prepared:

Percent Cibacet dye is one ofthe types mentioned below 3 Butyl Cellosolve (Z-butoxyethanol) 10 Lactic acid 3 Water to make 100%.

5 Violet Cibacet 2R Mauve.

o NH;

Blue Cibacet F3R Light blue.

( NH-GH;

( NH-oHioHioH Sapphire blue Cibacet 4G (is the colorant amino oxy anthraquinonique referred to as Disperse blue 16 Colour Index, 2nd Edition, 1956, p. 1720) Turquoise blue.

EXAMPLE VI The following solution is prepared:

' Percent Alizaiin Fast blue 'BE (referred Acid Blue 129,"

Colour Index, 2nd Edition, 1956,'p. 1287) 0:8 Butyl Cellosolve (Z-butoxyethanol) Lactic acid '3 40 Watertomake100%. By means of this solution an intense blue shade is obtained on naturally white live hair.

' EXAMPLE VII The following solution is prepared: 1 Percent Erio Fast Brown 5RL (referred Acid "Brown '11,

Colour Index, 2nd Edition, 1956, p. 1333) 5 'Butyl "Cellosolve (2-butoxyethanol) '10 Lactic acid 3 Water to make 100%.

A,. ,airly viscous solution is obtained which dyes white hair dark chestnut.

EXAMPLE VIII The following solution is prepared:

Percent Orange Nyloquinone 2R-(referred"Disperse Orange III, Colour'lndex, 2nd Edition, 1956, p. --1676)-- "1 ButylCellosolve (Z-butoxyethanol) 10 Lactic-acid and water to make 100% at pH 7.

By means of this solution a bright orange shade is obtained on naturally white live hair. (D) Examples 0') dyeing by means of waterinsoluble pigment dyes, known under the name "Orasol dyesf EXAMPLE IX The following solution is prepared:

1 Percent Orasol dye .1 Butyl Cellosolve (Z-butoxyethanol) -10 Water tomake 100%.

Depending upon the dye employed, there is obtained on naturally white live hair by means of this solution a shade as follows: i

aesaesi iibrasol-sBlue' BLW? (referred Solvent Blue 10, Colour Index, 2nd Edition, 1

blue.

1956,? p. 2876)-; Intense Oraso1=Blue'2GW Blue-grey.

-H on SOr-NH;

503E l Orasol Navy Blue RB (referred Solvent Blue 1, Colour Index, 2nd Edition, 1956, p. 2873) Slate blue. (E) Example of dyeing my means of basic dyes 1 EXAMPLE X I l i 1 a Percent Janus Black R 2 Butyl ,Cellosolve" (2 butoxyethanol) 10 Lactic acid to make pH 3. a Water to make 100%.

By means of this solution, a very intense grey having a mauve tinge is obtained on naturally white live hair.

EXAMPLE XI The following solution is prepared:

Percent Janus yellow R (No. 236, Colour Index, 1st Edition,

1924) Butyl Cellosolve 10 Water and ammonia to make 100% at pH 7.

By means of this solution a bright golden blonde shade is obtained on naturally white live hair.

EXAMPLE XII The following solution is prepared:

Percent Astracyanine B (referred Basic Blue 18, Colour Index, 2nd Edition, 1956, p. 1644) 2 Butyl Cellosolve (2-butoxyethanol) 10 Water and ammonia to make 100% at pH 8.

By means of this solution naturally white live hair is dyed a very deep blue shade and black hair is dyed a blue-black shade.

, EXAMPLE XIII The following solution is prepared:

' .7 Percent Chrysoidine hydrochloride (No. 20, Colour Index,

1st Edition, 1924) 0.1 Butyl Cellosolve (Z-butoxyethanol) 10 Water to make 100%.

By means of this solution a reddish-blonde shade is obtained on naturally white live hair.

EXAMPLE XIV The following solution is prepared:

Percent Methyl violet (No. 680, Colour Index, 1st Edition,

1924) 0.05 Butyl Cellosolve (2-butoxyethanol) 5 Water to make 100%.

1348) 1.5 Butyl Cellosolve (2-butoxyethanol) 10 Lactic acid 4 Water to make By means of this solution a light brown shade is obtained on naturallywhite live EXAMPLE XVI The following solution is prepared:

I Percent Violet fonce Lanasyne (referred Acid Violet 66,

Colour Index, 2nd Edition, 1916, p. 1221) 2.5 Butyl Cellosolve (2-butoxyethanol) 10 Lactic. acid l 4 Water to make 100%.

By means of this solution a very deep smoke-grey shade .is obtained on naturally white live hair.

EXAMPLE XVII The following solution is prepared:

Percent Cibalane Brown B.L. (referred Acid Brown 19,

Colour Index, 2nd Edition, 1956, p. 1336) 2.5 Butyl Cellosolve (Z-bntoxyethanol) i 10 Lactic acid *3 Water to make 100%.

By means of this solution a blonde shade is obtained on naturally white live hair. (G) Example of dyeing by means of dyes of the "Nigro sine EXAMPLE XVIII The following solution is prepared:

Percent Nigrosine CBRS (No. 865, Colour Index, 1st Edition, 1924) 0.5 Butyl Cellosolve (2-butoxyethanol) 15 Lactic acid 2.5

Water to make 100%.

By means of this solution, a beautiful grey shade having a mauve tinge is obtained on White hair.

(H) Example of dyeing by means of dyes of the "lndu line type A EXAMPLE XIX The following solution is prepared:

Percent Induline R.A.L. (No. 861, Colour Index, 1st Edition,

1924) 1 Butyl Cellosolve (2-butoxyethanol) 10 Lactic acid 3 Water to make 100%.

By means of this solution a beautiful grey-blue shade is obtained on white hair.

The invention is in no way limited to the use of a single solvent and it is possible without disadvantage, and sometimes even advantageously, to use two or more solvents of the foregoing general formula in combination, as in Example V.

The dyeing solutions may contain any of the usual adjuvants such as foaming agents, softeners and any other products intended to brighten or improve in any other manner the texture or appearance of the hair. It

no tut stherpf die hy n is also possible to: incorporatein. such solutions; a creambase of usual type soiasi to produce a cream dye which is tribution of the dye over the hair to be dyed; while preventing the contact of the dye with the scalp. The fol- I lowing is an example of suchja cream dye:

., "EXAMPLEXX' The following solution is prepared:

t er Nigrosine 3 (No. 865 in the color index, lstedition) 3 lycol or 2-[ (p-butoxy) oxyrl-ethanolj-s -.-r---t- Lactic acid 7 p 8 Water to make 100%.

The solution is brought to: about 50 C. on a waterbath, and the following incorporated:

Percent Lanette wax SX -Oxyethylenated alkylphenol 8 The cream thus obtained is allowed to cool. I

cream is applied at ambient temperature to naturally white live hair. It is left in contact therewith for 15 to minutes, and the hair is then-rinsed with tepid water. A beaut fiul clear grey shade isob'tained.

I claim: r

1. A method of dyeing live human hair which comprises applying thereto at room temperature a preformed dyestufl selected from the group consisting of acid dyes, ,basic dyes, dispersed dyes', direct dyes and solvent dyes in th e f orrn of a solution in a homogeneous aqueous mix- .ture essentially consisting of water and 5%, to 20% by weight of the dye solution of an organic water miscible solvent selected from the group consisting of2-butoxy- 8 ethanol and a condensation product of 1 moleofiisoamyl alcohol with 1.2 moles of ethylene oxide.

:2; Amethod. oi. dyeing livev thumani hai -11f which; eomprises: applying thereto. at room temperaturea preformed dyestutf selected from the group consisting of acid dyes, basic dyes, dispersed dyes, direct dyes and solvent dyes in the form of a solution in a homogeneous aqueous mixture essentially consisting of water and 5% to 20% by weight of the dye solution of Z-butoxyethanoLas an organic water miscible solvent. 7

3. A method of dyeing live human hair which comprises applying thereto at room temperature a preformed dyestutf selected from the group consisting of acid dyes, basic dyes, dispersed dyes, direct dyes and solvent dyes in the form of a solution in ahomogeneousaqueous mixture essentially consisting of water and to 20% by weight of the dye solution of a condensation produet of 1 mole. of isoamyl alcohol with, 1.2 moles of, ethylene, oxide as an organic water miscible solvent.

References Cited in the file of thispatent UNITED STATES PATENTs' OTHER REFERENCES Synthetic Organic Chemicals, 12th Ed.,,Union Carbide and Carbon Chemical, July 1, 1'945', ppl. 3'5' and

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2095221 *Jul 21, 1934Oct 5, 1937Smith Ida MDyeing method and bath
US2116521 *May 7, 1934May 10, 1938Rit Products CorpHair dyeing method and composition
US2118432 *Sep 10, 1937May 24, 1938Interchem CorpColoring medium
US2776668 *Jun 28, 1951Jan 8, 1957Rubinstein Inc HMethod and preparations for the permanent dyeing of keratinous material
CA509522A *Jan 25, 1955Raymond Lab IncHair treating composition
DE582521C *Jun 30, 1931Aug 16, 1933Eugen BaschMittel zum Faerben von lebendem Haar
GB669192A * Title not available
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3071427 *Apr 23, 1959Jan 1, 1963Ciba LtdProcess for dyeing nitrogenous fibers and preparations for carrying out the process
US3112983 *Feb 6, 1961Dec 3, 1963Daniel P CollinsProcess of low temperature dyeing of wool
US3168441 *Jul 31, 1961Feb 2, 1965Clairol IncBlue anthraquinone dye
US3192117 *Feb 20, 1962Jun 29, 1965Therachemie Chem TherapeutHair dye comprising substituted anthraquinones in shampoo base
US3317271 *Dec 26, 1963May 2, 1967American Cyanamid CoCompositions containing a neutraldyeing premetalized dye and process of dyeing polyamides therewith
US3346322 *Mar 25, 1963Oct 10, 1967Basf AgStable highly concentrated solutions of basic dyes
US3385652 *Aug 21, 1963May 28, 1968Union Carbide CorpDyeing polyolefin articles with soluble dye and a short chain polyethylene glycol ether
US3480377 *Apr 28, 1965Nov 25, 1969Lever Brothers LtdSolvent dyeing of living human hair
US3619102 *Jun 7, 1968Nov 9, 1971OrealDyeing keratinic fibers with aqueous solutions of direct dyes and organic solvents
US3632290 *Jan 26, 1968Jan 4, 1972Lowenstein Dyes & Cosmetics InDyeing of human hair using ethylene glycol ethers
US4168144 *Jul 14, 1975Sep 18, 1979Lever Brothers CompanyKeratinous fibers colorant compositions containing basic dyes and an anionic-cationic detergent complex
US4873079 *Dec 14, 1987Oct 10, 1989Clairol IncorporatedHair coloring composition and its method of use
US6371994 *May 28, 1999Apr 16, 2002L'oreal S.A.Dye composition for keratin fibers, with a cationic direct dye and a polyol or polyol ether
US6436153 *May 28, 1999Aug 20, 2002L'ORéAL S.A.Composition for the direct dyeing of keratin fibres with a cationic direct dye and a polyol and/or a polyol ether
US6440175 *Jun 28, 2001Aug 27, 2002Stanley, Iii Virgil E.Hair coloring kit
US20050204484 *Jan 7, 2005Sep 22, 2005Clariant GmbhHair colorants
DE3814685A1 *Apr 30, 1988Sep 1, 1988Schwarzkopf Gmbh HansZweikomponenten-zubereitung zur anfertigung einer breiartigen, auftragefaehigen zubereitung zur behandlung von humanhaar
EP0460879A1 *May 31, 1991Dec 11, 1991Bristol-Myers Squibb CompanyHair colorants
Classifications
U.S. Classification8/406, 8/426, 8/609, 8/425, 8/907
International ClassificationC09B67/00, D06P1/613, D06P3/14, D06P1/651, D06P1/92, D06P3/30
Cooperative ClassificationA61K8/39, D06P1/6133, A61K2800/432, Y10S8/907, A61K8/34, D06P3/30, A61Q5/065, D06P1/928, D06P1/65131
European ClassificationD06P3/30, D06P1/651B8, D06P1/92D, D06P1/613B2, A61Q5/06D, A61K8/34, A61K8/39