CA1141505A - Dyeing composition for fibrous materials - Google Patents
Dyeing composition for fibrous materialsInfo
- Publication number
- CA1141505A CA1141505A CA000338092A CA338092A CA1141505A CA 1141505 A CA1141505 A CA 1141505A CA 000338092 A CA000338092 A CA 000338092A CA 338092 A CA338092 A CA 338092A CA 1141505 A CA1141505 A CA 1141505A
- Authority
- CA
- Canada
- Prior art keywords
- composition
- dye
- dyeing
- acetyl
- hair
- 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
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
- 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
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/23—Sulfur; Selenium; Tellurium; Compounds thereof
-
- 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
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
- A61Q5/065—Preparations for temporary colouring the hair, e.g. direct dyes
-
- 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
- A61Q5/10—Preparations for permanently dyeing the hair
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
- D06P1/642—Compounds containing nitrogen
- D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
- D06P1/6495—Compounds containing carbonamide -RCON= (R=H or hydrocarbons)
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
DYEING COMPOSITION FOR FIBROUS MATERIALS
ABSTRACT OF THE DISCLOSURE
An improvement in a composition for dyeing fibrous material comprising a dye system and a liquid dispersing vehicle for the system, in which the composition contains N-acetyl ethanola-mine to promote dyeing of the material.
ABSTRACT OF THE DISCLOSURE
An improvement in a composition for dyeing fibrous material comprising a dye system and a liquid dispersing vehicle for the system, in which the composition contains N-acetyl ethanola-mine to promote dyeing of the material.
Description
2 Applicant: COM~E INCORPORATED
3 Inventor: DR. HERsERT LAPIDUS
4 Title: DYEING COMPOSITION FOR FIRsROUS MATERIALS
BACKGROUND OF THE INVENTION
6 Numerous dye systems have been employed to impart desired 7 color to fibrous materials, including textiles. Such materials 8 include "Natural" fibers, _g., cellulose-based fibers such as cotton, keratin-based fibers such as wool, and fibroin-based fibers such as silk; and "man-made" fibers, e.g., derivatives of 11 natural fibers such as rayon, and "synthetic" fibers, such as 12 nylon, polyester and polyolefin fibers of non-natural derivation.
13 Different types of dyestuffs are useful with these various fibers, 14 including acid, basic, direct, sulfur, vat, leuco esters, azo, acetate, pigment, oxidation, natural and inorganic dyes.
16 In addition to the textile field, dye systems are used in 17 the cosmetic industry for coloring hair. In this field, there is 18 need to avoid toxicity or other adverse effects upon the subject's 19 skin or hair.
Drawbacks of known dye systems occur in the resistance of 21 the dyed materials to fading; in the resistance of the dyed 22 materials to erosion of color by rubbing and the like; in the 23 depth of color imparted to the materials incidental to dyeing;
24 and/or in the efficiency and ease with which dye is imparted to materials for their coloration.
26 Much effort has been expended in seeking to improve the 27 dyeing of fibrous materials. However, known means of facilitat-28 ing and improving such dyeing processes have had only occasional 29 and/or limited success. Such means have often proven expensive, successful only for alleviation of some of the foregoing drawbac~s 31 and/or useful only with certain types of dye systems, 32 /~
f~,' J'~
2 In accordance with the present invention, it has been dis-3 covered that the incorporation of N-acetyl ethanolamine into dyeing compositions provides enhanced and more durable coloration than has heretofore been obtained, accelerates the dyeing process 6 and/or provides dyed products of enhanced and more resistant 7 colors.
8 This invention has been found to be useful throughout the 9 breadth of different dyestuffs in this art. Of particular im-portance, it has wide applicability to different types of fibrous 11 materials. Thus, it may be utilized for the dyeing of textiles 12 such as cotton, wool, silk, rayon, acetate, nylon, and other 13 natural or man-made fibrous materials and for the treatment of 14 hùman hair.
N-acetyl ethanolamine has been recognized in the cosmetics 16 art as a highly efficient conditioner or grooming aid for hair, 17 wherein it i9 used in place of mineral oil derivatives in sham-18 poos, rinses, conditioners, and the like, to coat the hair so the 19 hair lies flat, is not flyaway and has a shiny appearance. It has not, however, heretofore been appreciated that N-acetyl 21 ethanolamine will also function to promote or enhance the dyeing 22 of hair. Neither has it been recognized that this effect occurs 23 not only with hair but also with other fibrous materials, and 24 not only with conventional hair dyeing compositions but also with other dye systems.
26 In addition to its newly discovered property or function as 27 a dyeing enhancer, N-acetyl ethanolamine continues to provide 28 those advantages for which it has been generally recognized in 29 the cosmetic art. Accordir~gly, its presence in a dyeing composi-tion continues to provide the grooming or conditioning functions 31 for which it is known. Therefore, the present dyeing composi-32 tions, in addition to providing improved coloration, are also l less harsh in their effects on the material being dyed.
2 Although it is not wished to be bound by any theory, it is 3 believed that at least one of the means by which N-acetyl ethan-olamine functions to enhance or promote dyeing is through its ability to cause fiber expansion in the material being treated.
6 Such expansion of the individual fibers of the material being 7 dyed could account for the improved and accelerated penetration 8 of a dye system into the material. Also, it could explain the 9 observed acceleration and ease in imparting coloration and/or enhanced resistance of the dyed material to fading or loss of 11 coloration.
12 As has already been indicated, the chemical composition and 13 mechanism of the dye system utilized in the present compositions 14 is relatively unimportant. Any of the well known systems of the prior art including, for example, oxidative dyestuffs, basic 16 dyes and heavy metal salt/sulfur-containing reducing compound 17 systems such as those deccribed below may be utilized.
18 These prior art dye systems normally amount to up to about 19 50~ and preferably from about 1~ to 25~ of the total weight of the dyeing composition. The exact proportions, however, vary 21 from system to system and with their intended use in a conven-22 tional manner. They also are not critical to the function of 23 the N-acetyl ethanolamine.
24 In the present dye compositions (as in the prior art), the dye system is provided in a liquid dispersing vehicle therefor-26 commonly water or an aqueous mixture. This is not required, as 27 non-aqueous systems including alcohol, mineral oil and the like 28 may be employed. Similarly mixed aqueous/water-immiscible 29 liquid emulsions are suitable vehicles for dye systems in the present compositions.
31 The N-acetyl ethanolamine may be employed in aimost any 32 amount; however, it normally comprises from about l to 25%, 114150~i ~
1 preferably 10 to 15~, of the total weight of the dye composition.
2 While these proportions yenerally provide maximum dye promotion, 3 still greater amounts of N-acetyl ethanolamine may be present for 4 the addi~ional purpose of providing conditioning for the treated ~fibrous material, or where the N-acetyl ethanolamine constitutes 6 a major part, or all, of the vehicle itself. Consequently, the 7 amount of N-acetyl ethanolamine utilized in any given dyeing 8 composition may vary widely.
9 While the present invention has been described largely in terms of pre-formed compositions to be applied to the material 11 being dyed, this need not be the case. The present compositions 12 may also be formed on the fibrous material itself, through se-13 quential applications of N-acetyl ethanolamine and of the dye 14 system. It is thus necessary only that all of the essential components of the dyeing composition be present on, or in, the 16 fibrous material being dyed at the same time, to achieve the 17 advantages described hereinabove~
18 Several examples of compositions of the present invention 19 are described below. It should be understood, however, that these examples are solely for illustration and are not intended to limit 21 the scope of the invention.
23 Aqueous dyeing compositions of two standard dyes, FD&C Blue 24 #1 (at ~.25% by weight) and D&C Yellow #10 (at 0.75% by weight), were employed in comparative dye tests for the effects of N-acetyl 26 ethanolamine. Paired samples of these two dyeing compositions--27 a control sample containing 0% and a sample containing 10% of 28 N-acetyl ethanolamine by weight--were used for the comparison.
29 Swatches of different fabrics were immersed in the four test sample dyeing compositions at 60C for 1 minute. After drying, 31 the swatches were visually compared for intensity of dye color.
32 The results showed several instances in which N--acetyl ethano-1 lamine unexpectedly effected dyeing (not all the fabirc ma~erials 2 are normally susceptible to these particular dye compositions), 3 as well as others in which dyeing was clearly enhanced over the 4 respective control samples. The fabrics which evidenced in-creases in color intensity due to the presence of the N-acetyl 6 ethanolamine ranged broadly in types of fibers, including wool B 7 and worsted wool, rayon (trade name AVRIL~, v.iscose rayon, silk 8 nylon, cotton, acetate, acrylonitrile (ACRILAN), triacetate 9 (ARNEL), acrylic (CRESLAN, ORLON and ZEFRAN~, polyester (DACRON~, FORTREL and KoDEL7, olefin (HERCULO~ and modacrylic fibers 11 ~VEREL and DYNE~ .
12 From visual inspection, swatches dyed in the presence of 13 N-acetyl ethanolamine were also found to be more homogeneous in 14 color and less susceptible to runs and streaking. Thus, the N-acetyl ethanolamine improved the fix or set of the dye on the 16 fabrics.
18 A hair dyeing composition was prepared having the following 19 formula:
Bismuth Citrate 0.50%
21 Triethanolamine 3.00~
22 Alcohol 10.00%
23 Sulfur, precipitated0.50%
24 Octoxynol-9 (TR~TON X-100) 0.10%
N-acetyl ethanolamine15.00~
26 Water 70.80%
27 Perfume 0.10%
28 The composition was formed in a conventional manner -29 the N-acetyl ethanolamine ~tradename ACETAMID~ MEA) being added after combination of the other ingredients. To test this com-31 position, swatches of bleached hair were dunked into the composi-32 tion, removed, shaken to remove excess composition,and then ~ ~r~e ~a,~
BACKGROUND OF THE INVENTION
6 Numerous dye systems have been employed to impart desired 7 color to fibrous materials, including textiles. Such materials 8 include "Natural" fibers, _g., cellulose-based fibers such as cotton, keratin-based fibers such as wool, and fibroin-based fibers such as silk; and "man-made" fibers, e.g., derivatives of 11 natural fibers such as rayon, and "synthetic" fibers, such as 12 nylon, polyester and polyolefin fibers of non-natural derivation.
13 Different types of dyestuffs are useful with these various fibers, 14 including acid, basic, direct, sulfur, vat, leuco esters, azo, acetate, pigment, oxidation, natural and inorganic dyes.
16 In addition to the textile field, dye systems are used in 17 the cosmetic industry for coloring hair. In this field, there is 18 need to avoid toxicity or other adverse effects upon the subject's 19 skin or hair.
Drawbacks of known dye systems occur in the resistance of 21 the dyed materials to fading; in the resistance of the dyed 22 materials to erosion of color by rubbing and the like; in the 23 depth of color imparted to the materials incidental to dyeing;
24 and/or in the efficiency and ease with which dye is imparted to materials for their coloration.
26 Much effort has been expended in seeking to improve the 27 dyeing of fibrous materials. However, known means of facilitat-28 ing and improving such dyeing processes have had only occasional 29 and/or limited success. Such means have often proven expensive, successful only for alleviation of some of the foregoing drawbac~s 31 and/or useful only with certain types of dye systems, 32 /~
f~,' J'~
2 In accordance with the present invention, it has been dis-3 covered that the incorporation of N-acetyl ethanolamine into dyeing compositions provides enhanced and more durable coloration than has heretofore been obtained, accelerates the dyeing process 6 and/or provides dyed products of enhanced and more resistant 7 colors.
8 This invention has been found to be useful throughout the 9 breadth of different dyestuffs in this art. Of particular im-portance, it has wide applicability to different types of fibrous 11 materials. Thus, it may be utilized for the dyeing of textiles 12 such as cotton, wool, silk, rayon, acetate, nylon, and other 13 natural or man-made fibrous materials and for the treatment of 14 hùman hair.
N-acetyl ethanolamine has been recognized in the cosmetics 16 art as a highly efficient conditioner or grooming aid for hair, 17 wherein it i9 used in place of mineral oil derivatives in sham-18 poos, rinses, conditioners, and the like, to coat the hair so the 19 hair lies flat, is not flyaway and has a shiny appearance. It has not, however, heretofore been appreciated that N-acetyl 21 ethanolamine will also function to promote or enhance the dyeing 22 of hair. Neither has it been recognized that this effect occurs 23 not only with hair but also with other fibrous materials, and 24 not only with conventional hair dyeing compositions but also with other dye systems.
26 In addition to its newly discovered property or function as 27 a dyeing enhancer, N-acetyl ethanolamine continues to provide 28 those advantages for which it has been generally recognized in 29 the cosmetic art. Accordir~gly, its presence in a dyeing composi-tion continues to provide the grooming or conditioning functions 31 for which it is known. Therefore, the present dyeing composi-32 tions, in addition to providing improved coloration, are also l less harsh in their effects on the material being dyed.
2 Although it is not wished to be bound by any theory, it is 3 believed that at least one of the means by which N-acetyl ethan-olamine functions to enhance or promote dyeing is through its ability to cause fiber expansion in the material being treated.
6 Such expansion of the individual fibers of the material being 7 dyed could account for the improved and accelerated penetration 8 of a dye system into the material. Also, it could explain the 9 observed acceleration and ease in imparting coloration and/or enhanced resistance of the dyed material to fading or loss of 11 coloration.
12 As has already been indicated, the chemical composition and 13 mechanism of the dye system utilized in the present compositions 14 is relatively unimportant. Any of the well known systems of the prior art including, for example, oxidative dyestuffs, basic 16 dyes and heavy metal salt/sulfur-containing reducing compound 17 systems such as those deccribed below may be utilized.
18 These prior art dye systems normally amount to up to about 19 50~ and preferably from about 1~ to 25~ of the total weight of the dyeing composition. The exact proportions, however, vary 21 from system to system and with their intended use in a conven-22 tional manner. They also are not critical to the function of 23 the N-acetyl ethanolamine.
24 In the present dye compositions (as in the prior art), the dye system is provided in a liquid dispersing vehicle therefor-26 commonly water or an aqueous mixture. This is not required, as 27 non-aqueous systems including alcohol, mineral oil and the like 28 may be employed. Similarly mixed aqueous/water-immiscible 29 liquid emulsions are suitable vehicles for dye systems in the present compositions.
31 The N-acetyl ethanolamine may be employed in aimost any 32 amount; however, it normally comprises from about l to 25%, 114150~i ~
1 preferably 10 to 15~, of the total weight of the dye composition.
2 While these proportions yenerally provide maximum dye promotion, 3 still greater amounts of N-acetyl ethanolamine may be present for 4 the addi~ional purpose of providing conditioning for the treated ~fibrous material, or where the N-acetyl ethanolamine constitutes 6 a major part, or all, of the vehicle itself. Consequently, the 7 amount of N-acetyl ethanolamine utilized in any given dyeing 8 composition may vary widely.
9 While the present invention has been described largely in terms of pre-formed compositions to be applied to the material 11 being dyed, this need not be the case. The present compositions 12 may also be formed on the fibrous material itself, through se-13 quential applications of N-acetyl ethanolamine and of the dye 14 system. It is thus necessary only that all of the essential components of the dyeing composition be present on, or in, the 16 fibrous material being dyed at the same time, to achieve the 17 advantages described hereinabove~
18 Several examples of compositions of the present invention 19 are described below. It should be understood, however, that these examples are solely for illustration and are not intended to limit 21 the scope of the invention.
23 Aqueous dyeing compositions of two standard dyes, FD&C Blue 24 #1 (at ~.25% by weight) and D&C Yellow #10 (at 0.75% by weight), were employed in comparative dye tests for the effects of N-acetyl 26 ethanolamine. Paired samples of these two dyeing compositions--27 a control sample containing 0% and a sample containing 10% of 28 N-acetyl ethanolamine by weight--were used for the comparison.
29 Swatches of different fabrics were immersed in the four test sample dyeing compositions at 60C for 1 minute. After drying, 31 the swatches were visually compared for intensity of dye color.
32 The results showed several instances in which N--acetyl ethano-1 lamine unexpectedly effected dyeing (not all the fabirc ma~erials 2 are normally susceptible to these particular dye compositions), 3 as well as others in which dyeing was clearly enhanced over the 4 respective control samples. The fabrics which evidenced in-creases in color intensity due to the presence of the N-acetyl 6 ethanolamine ranged broadly in types of fibers, including wool B 7 and worsted wool, rayon (trade name AVRIL~, v.iscose rayon, silk 8 nylon, cotton, acetate, acrylonitrile (ACRILAN), triacetate 9 (ARNEL), acrylic (CRESLAN, ORLON and ZEFRAN~, polyester (DACRON~, FORTREL and KoDEL7, olefin (HERCULO~ and modacrylic fibers 11 ~VEREL and DYNE~ .
12 From visual inspection, swatches dyed in the presence of 13 N-acetyl ethanolamine were also found to be more homogeneous in 14 color and less susceptible to runs and streaking. Thus, the N-acetyl ethanolamine improved the fix or set of the dye on the 16 fabrics.
18 A hair dyeing composition was prepared having the following 19 formula:
Bismuth Citrate 0.50%
21 Triethanolamine 3.00~
22 Alcohol 10.00%
23 Sulfur, precipitated0.50%
24 Octoxynol-9 (TR~TON X-100) 0.10%
N-acetyl ethanolamine15.00~
26 Water 70.80%
27 Perfume 0.10%
28 The composition was formed in a conventional manner -29 the N-acetyl ethanolamine ~tradename ACETAMID~ MEA) being added after combination of the other ingredients. To test this com-31 position, swatches of bleached hair were dunked into the composi-32 tion, removed, shaken to remove excess composition,and then ~ ~r~e ~a,~
- 5 -1 permitted to dry overnight at room temperature. After drying, 2 the hair was observed to have changed from its initial blondish color to a brown shade. Repeated daily treatments, over a one-4 week period, yielded an increasingly deeper or darkened brown S shade of high durability.
6 EXAMPLE III
7 A hair dyeing composition was prepared having the following
8 formula:
Paraphenylene diamine sulfate 5.00%
Resorcinol 1.00 11 Alcohol 1~.00 12 N-acetyl ethanolamine 10.00~
13 Oleic acid 0.40%
14 Ammonia (25~ soln.) 10.00%
Water 63.60%
16 The composition was prepared in a conventional manner and 17 employed with a peroxide developer. In testing on bleached 18 swatches of hair, it produced a dark black coloration.
19 EX~MPLE IV
A semi-permanent dye and shampoo was prepared having the 21 following formula:
22 Monoethanolamine Lauryl Sulfate 20.00~
23 Ethylene Glycol Mono Stearate 3.00%
24 P-Nitro-o-phenylenediamine 1.50%
Diethanolamine coconut fatty acids 3.00~
26 N-acetyl ethanolamine 7.00%
27 Water 65.50%
28 When used in shampooing hair, an enhanced coloration with 29 increased resistance to erosion of coloration by rubbing off was observed.
Paraphenylene diamine sulfate 5.00%
Resorcinol 1.00 11 Alcohol 1~.00 12 N-acetyl ethanolamine 10.00~
13 Oleic acid 0.40%
14 Ammonia (25~ soln.) 10.00%
Water 63.60%
16 The composition was prepared in a conventional manner and 17 employed with a peroxide developer. In testing on bleached 18 swatches of hair, it produced a dark black coloration.
19 EX~MPLE IV
A semi-permanent dye and shampoo was prepared having the 21 following formula:
22 Monoethanolamine Lauryl Sulfate 20.00~
23 Ethylene Glycol Mono Stearate 3.00%
24 P-Nitro-o-phenylenediamine 1.50%
Diethanolamine coconut fatty acids 3.00~
26 N-acetyl ethanolamine 7.00%
27 Water 65.50%
28 When used in shampooing hair, an enhanced coloration with 29 increased resistance to erosion of coloration by rubbing off was observed.
Claims (10)
1. In a composition for dyeing fibrous material comprising a dye system and a liquid dispersing vehicle therefor, the improvement wherein said compostion contains N-acetyl ethanolamine to promote dyeing of said material.
2. The composition in Claim 1, wherein the N-acetyl ethanolamine amounts to about 1 to 25% of the total weight of the dye composition.
3. The composition of Claim 1, wherein the N-acetyl ethanolamine amounts to about 10 to 15% of the total weight of the dye composition.
4. The composition of Claim 1, wherein the dye system comprises an oxidative dyestuff.
5. The composition of Claim 1, wherein the dye system comprises a basic dye.
6. The composition of Claim 1, wherein the dye system comprises a heavy metal salt with a sulfur-containing reducing compound.
7. The composition of Claim 6, wherein the salt comprises a complex of bismuth citrate and triethanolamine.
8. The composition of Claim 7, wherein the reducing compound is sulfur.
9. The composition of Claim 1, wherein the fibrous material is composed of textile fibers.
10. The composition of Claim 1, wherein the fibrous material is hair.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95199878A | 1978-10-20 | 1978-10-20 | |
| US951,998 | 1978-10-20 | ||
| US3754779A | 1979-05-11 | 1979-05-11 | |
| US37,547 | 1979-05-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1141505A true CA1141505A (en) | 1983-02-22 |
Family
ID=26714239
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000338092A Expired CA1141505A (en) | 1978-10-20 | 1979-10-22 | Dyeing composition for fibrous materials |
Country Status (20)
| Country | Link |
|---|---|
| AR (1) | AR226829A1 (en) |
| AT (1) | AT386834B (en) |
| AU (1) | AU528723B2 (en) |
| BR (1) | BR7906765A (en) |
| CA (1) | CA1141505A (en) |
| CH (1) | CH659359GA3 (en) |
| DE (1) | DE2942376C2 (en) |
| DK (1) | DK149582C (en) |
| FI (1) | FI67578C (en) |
| FR (1) | FR2439223A1 (en) |
| GB (1) | GB2036093B (en) |
| GR (1) | GR82354B (en) |
| IE (1) | IE49088B1 (en) |
| IT (1) | IT1124611B (en) |
| LU (1) | LU81791A1 (en) |
| NL (1) | NL180773C (en) |
| NO (1) | NO152176C (en) |
| NZ (1) | NZ191878A (en) |
| PT (1) | PT70321A (en) |
| SE (1) | SE446752B (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2499852A1 (en) * | 1981-02-19 | 1982-08-20 | Rocador Sa | N-HYDROXYETHYLACETAMIDE DRUG FOR THE TREATMENT OF SEBORRHEA DISEASES ON HUMAN SCALP LEATHER |
| US4583986A (en) * | 1981-07-20 | 1986-04-22 | Combe Incorporated | Catalyzed bismuth dye system for human hair |
| DE3929333A1 (en) * | 1989-09-04 | 1991-03-07 | Henkel Kgaa | EQUALIZING OXIDATION HAIR COLORING AGENTS |
| US6440175B1 (en) * | 2001-06-28 | 2002-08-27 | Stanley, Iii Virgil E. | Hair coloring kit |
-
1979
- 1979-10-09 GR GR60224A patent/GR82354B/el unknown
- 1979-10-12 FI FI793179A patent/FI67578C/en not_active IP Right Cessation
- 1979-10-15 LU LU81791A patent/LU81791A1/en unknown
- 1979-10-16 PT PT70321A patent/PT70321A/en unknown
- 1979-10-17 AU AU51860/79A patent/AU528723B2/en not_active Ceased
- 1979-10-17 NL NLAANVRAGE7907668,A patent/NL180773C/en not_active IP Right Cessation
- 1979-10-18 NZ NZ191878A patent/NZ191878A/en unknown
- 1979-10-18 IT IT26585/79A patent/IT1124611B/en active
- 1979-10-18 GB GB7936256A patent/GB2036093B/en not_active Expired
- 1979-10-19 CH CH943079A patent/CH659359GA3/fr unknown
- 1979-10-19 SE SE7908700A patent/SE446752B/en not_active IP Right Cessation
- 1979-10-19 DE DE2942376A patent/DE2942376C2/en not_active Expired
- 1979-10-19 NO NO793373A patent/NO152176C/en unknown
- 1979-10-19 AR AR278563A patent/AR226829A1/en active
- 1979-10-19 FR FR7926081A patent/FR2439223A1/en active Granted
- 1979-10-19 DK DK442879A patent/DK149582C/en active
- 1979-10-19 BR BR7906765A patent/BR7906765A/en not_active IP Right Cessation
- 1979-10-19 IE IE2004/79A patent/IE49088B1/en not_active IP Right Cessation
- 1979-10-19 AT AT0682179A patent/AT386834B/en not_active IP Right Cessation
- 1979-10-22 CA CA000338092A patent/CA1141505A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NZ191878A (en) | 1981-05-15 |
| NO152176C (en) | 1985-08-14 |
| AR226829A1 (en) | 1982-08-31 |
| PT70321A (en) | 1979-11-01 |
| DK442879A (en) | 1980-04-21 |
| NO152176B (en) | 1985-05-06 |
| DK149582C (en) | 1987-02-09 |
| AT386834B (en) | 1988-10-25 |
| IT7926585A0 (en) | 1979-10-18 |
| FR2439223A1 (en) | 1980-05-16 |
| FR2439223B1 (en) | 1984-06-29 |
| AU528723B2 (en) | 1983-05-12 |
| GB2036093A (en) | 1980-06-25 |
| AU5186079A (en) | 1980-04-24 |
| FI67578B (en) | 1984-12-31 |
| NO793373L (en) | 1980-04-22 |
| DE2942376A1 (en) | 1980-04-30 |
| SE7908700L (en) | 1980-04-21 |
| NL180773C (en) | 1987-04-16 |
| GR82354B (en) | 1984-12-13 |
| LU81791A1 (en) | 1980-01-24 |
| NL180773B (en) | 1986-11-17 |
| NL7907668A (en) | 1980-04-22 |
| IT1124611B (en) | 1986-05-07 |
| IE792004L (en) | 1980-11-11 |
| IE49088B1 (en) | 1985-07-24 |
| ATA682179A (en) | 1988-03-15 |
| DE2942376C2 (en) | 1983-02-03 |
| BR7906765A (en) | 1980-09-09 |
| FI67578C (en) | 1985-04-10 |
| CH659359GA3 (en) | 1987-01-30 |
| DK149582B (en) | 1986-08-04 |
| FI793179A (en) | 1980-04-21 |
| GB2036093B (en) | 1982-10-27 |
| SE446752B (en) | 1986-10-06 |
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