US1940757A - Process for dyeing furs, hairs, and feathers - Google Patents
Process for dyeing furs, hairs, and feathers Download PDFInfo
- Publication number
- US1940757A US1940757A US675144A US67514433A US1940757A US 1940757 A US1940757 A US 1940757A US 675144 A US675144 A US 675144A US 67514433 A US67514433 A US 67514433A US 1940757 A US1940757 A US 1940757A
- Authority
- US
- United States
- Prior art keywords
- dyeing
- hairs
- feathers
- parts
- furs
- 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
- 238000004043 dyeing Methods 0.000 title description 22
- 210000003746 feather Anatomy 0.000 title description 11
- 210000004209 hair Anatomy 0.000 title description 11
- 238000000034 method Methods 0.000 title description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- 239000001257 hydrogen Substances 0.000 description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 150000004985 diamines Chemical class 0.000 description 12
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 11
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- -1 4 Chemical compound 0.000 description 7
- 239000000975 dye Substances 0.000 description 7
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 150000003568 thioethers Chemical class 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 description 4
- 125000005037 alkyl phenyl group Chemical group 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- NYWVNRRGNPHTLI-UHFFFAOYSA-N 1,2-dichloro-3,4-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(Cl)=C1[N+]([O-])=O NYWVNRRGNPHTLI-UHFFFAOYSA-N 0.000 description 1
- WHODQVWERNSQEO-UHFFFAOYSA-N 4-Amino-2-nitrophenol Chemical compound NC1=CC=C(O)C([N+]([O-])=O)=C1 WHODQVWERNSQEO-UHFFFAOYSA-N 0.000 description 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- MGLBJPXSLJNFAG-UHFFFAOYSA-N [1-chloro-2-(2-chloro-2-phenylethyl)sulfanylethyl]benzene Chemical compound C=1C=CC=CC=1C(Cl)CSCC(Cl)C1=CC=CC=C1 MGLBJPXSLJNFAG-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001844 chromium Chemical class 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- ZTQDYDIRBKMMQB-UHFFFAOYSA-N n-(4-aminophenyl)nitramide Chemical compound NC1=CC=C(N[N+]([O-])=O)C=C1 ZTQDYDIRBKMMQB-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/02—Material containing basic nitrogen
- D06P3/04—Material containing basic nitrogen containing amide groups
- D06P3/30—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts
- D06P3/305—Material containing basic nitrogen containing amide groups furs feathers, dead hair, furskins, pelts with oxidation dyes
Definitions
- Our invention relates to a new process for dyeing furs, hairs and feathers.
- R means phenyl or a substituted phenyl, such as halogenophenyl,.alkylphenyl, hydroxy phenyl, alkoxyphenyl, X means alkyl or hydroxyalkyl, z and a stand for hydrogen, alkyl or hydroxyalkyl and n for l or 2.
- substituted diamines of the benzene series may be used either alone-especially in the case of paradiamines-or together with other well known dyes for pelts and new shades are obtainable in this manner which could be obtained until yet, if at all, only by complicated dyeing processes.
- the manufacture'of the sulfides in question may be carried out, for instance, according to well known processes by treating diamines or the corresponding nitro compounds containing a radicle capable of exchange with mercaptans followed, if necessary, by reduction of the nitro group or groups.
- 2.4-dinitrochlorobenzcne may be treated with ethylmercaptan.
- a reducing agent 2.4- diaminophenylethylsulfide (1) is obtainable which, together with paraphenylenediamine, dyes furs bright black shades of greenish tinge which are not obtainable with other dyes,
- Example 1 -3 parts of a mixture of 80 parts of paraphenylenediamine and 20 parts of 2.4-diaminophenylethylsulfide (l) are dissolved in the form of their salts with hydrochloric acid in 1000 parts of water. Ammonia is added for binding w the hydrochloric acid and 30 parts of hydrogen
- Example 2. --White rabbit skinmordanted with a chromium or copper salt is treated with an aqueous solution, 1000 parts of which contain 3 parts of a mixture consisting of 80 parts of paraphenylenediamine and parts of 2.4-diaminobenzenehydroxyethylsulfide (l) of the formula and parts of a 3% hydrogen superoxide solution. After 3 hours the skin is dyed a clear, somewhat greenish black.
- Example 3 The skin is treated with an aqueous solution, 1000 parts of which contain 2 parts of 2.5-diamino-l-methoxyphenylethylsulfide (4) and 20 parts of a 3% hydrogen superoxide solution.
- a skin mordanted with chromium salts is dyed a dull bluish red brown; skin mordanted with copper salts a greyish brown, skin mordanted with iron salts a dark grey.
- Example 4 White rabbit skin mordanted with a copper salt is treated with an aqueous solution 1000 parts of which contain 3 parts of 5- amino-2-dihydroxypropylamino-l-chlorophenylethylsulfide (4) of the formula and 30 parts of a 3% hydrogen superoxide solution. The skin is dyed a clear yellowish brown.
- Diamines containing twice the thioether radicle are likewise suitable for dyeing furs, hairs and feathers and we enumerate, for instance,
- the dyeing of the furs may be carried out in a neutral, an acid or an alkaline dyeing bath.
- the thioethers of the diamines in question may contain in the benzene nucleus other substituents than those indicated in the examples. As such substituents we enumerate the hydroxy group and the alkyl group.
- One of the amino groups may be substituted by alkyl or hydroxyalkyl radicles to form a secondary or tertiary amine.
- ethyl or hydroxyethyl there may be bound with the sulfur another alkyl or monoor polyhydroxyalkyl radicle.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
Patented Declf26, 1933 PATENT OFF-ICE PROCESS FOR- :DYEING FURS, HAIRS, AND vFEATHERS Erich 'Lehmann, Bitterfeld, and Hans Wassenegger; Dessau in 1 rAnhalt, Germany, as-
1 signors to General Aniline Works, Inc., New York, N. a corporation of Delaware No Drawing. Application June 9, 1933, Serial No.675,144,-' and in Germany May 6, 1932 9 Claims.
Application has been filed in Germany, May
Our invention relates to a new process for dyeing furs, hairs and feathers.
We have found that for dyeing furs, hairs and feathers in the presence of an oxidizing agent,
in which R means phenyl or a substituted phenyl, such as halogenophenyl,.alkylphenyl, hydroxy phenyl, alkoxyphenyl, X means alkyl or hydroxyalkyl, z and a stand for hydrogen, alkyl or hydroxyalkyl and n for l or 2.
These substituted diamines of the benzene series may be used either alone-especially in the case of paradiamines-or together with other well known dyes for pelts and new shades are obtainable in this manner which could be obtained until yet, if at all, only by complicated dyeing processes.
The manufacture'of the sulfides in question may be carried out, for instance, according to well known processes by treating diamines or the corresponding nitro compounds containing a radicle capable of exchange with mercaptans followed, if necessary, by reduction of the nitro group or groups.
Thus, for instance, 2.4-dinitrochlorobenzcne may be treated with ethylmercaptan. By treating the reaction product'with a reducing agent 2.4- diaminophenylethylsulfide (1) is obtainable which, together with paraphenylenediamine, dyes furs bright black shades of greenish tinge which are not obtainable with other dyes,
The following examples serve to illustrate our invention, the parts being by weight:-
Example 1.-3 parts of a mixture of 80 parts of paraphenylenediamine and 20 parts of 2.4-diaminophenylethylsulfide (l) are dissolved in the form of their salts with hydrochloric acid in 1000 parts of water. Ammonia is added for binding w the hydrochloric acid and 30 parts of hydrogen Example 2.--White rabbit skinmordanted with a chromium or copper salt is treated with an aqueous solution, 1000 parts of which contain 3 parts of a mixture consisting of 80 parts of paraphenylenediamine and parts of 2.4-diaminobenzenehydroxyethylsulfide (l) of the formula and parts of a 3% hydrogen superoxide solution. After 3 hours the skin is dyed a clear, somewhat greenish black.
Example 3.The skin is treated with an aqueous solution, 1000 parts of which contain 2 parts of 2.5-diamino-l-methoxyphenylethylsulfide (4) and 20 parts of a 3% hydrogen superoxide solution. A skin mordanted with chromium salts is dyed a dull bluish red brown; skin mordanted with copper salts a greyish brown, skin mordanted with iron salts a dark grey.
2.5 diamino 1 chlorophenylethylsulfide (4) yields similar tints having a somewhat yellowish tinge.
Example 4.-White rabbit skin mordanted with a copper salt is treated with an aqueous solution 1000 parts of which contain 3 parts of 5- amino-2-dihydroxypropylamino-l-chlorophenylethylsulfide (4) of the formula and 30 parts of a 3% hydrogen superoxide solution. The skin is dyed a clear yellowish brown.
Diamines containing twice the thioether radicle are likewise suitable for dyeing furs, hairs and feathers and we enumerate, for instance,
1.3-diaminophenyldi(ethylsulflde) (4.6) and 1.3- diaminophem'ldflhydroxyethylsulflde) (4.6) of the formula HO-CHa-GH which are obtainable by treating dinitrodichlorobenzene with ethylmercaptan or hydroxyethylmercaptan and by reducing the nitro groups.
It is obvious that our invention is not limited to the foregoing examples or to the specific details given therein. Thus, the dyeing of the furs may be carried out in a neutral, an acid or an alkaline dyeing bath. The thioethers of the diamines in question may contain in the benzene nucleus other substituents than those indicated in the examples. As such substituents we enumerate the hydroxy group and the alkyl group. One of the amino groups may be substituted by alkyl or hydroxyalkyl radicles to form a secondary or tertiary amine. On the other hand, instead of ethyl or hydroxyethyl there may be bound with the sulfur another alkyl or monoor polyhydroxyalkyl radicle.
As may be seen from Examples 1 and 2, we
prefer to us the thioethers of metadiamines together with other dyes for furs and we have exemplified this possibility by mentioning paraphenylenediamine. As other dyes which may be used in combination with the thioethers in question, we enumerate chloroor nitroparaphenylenediamine, 4-amino-1-dimethylaminobenzene, 4-amino-1-hydroxybenzene, 2-nitro-4-amino-1- hydroxybenzene, 4-chlor'o-2-amino-l-hydroxybenzene, 4.4'-diaminodiphenylamine, 4-dimethylaminodiphenylamine and similar compounds well known in the art.
What we claim is:
1. The process for dyeing furs, hairs or feathers which comprises treating the said material in a dyeing bath containing hydrogen superoxide and a diamine of thegeneral formula HIN in which It means phenyl, halogenophenyl, hydroxyphenyl, alkoxyphenyl or alkylphenyl, and X means alkyl or hydroxyalkyl, z and z stand for hydrogen, alkyl or hydroxyalkyl and n for 1 or 2.
2. The process for dyeing furs, hairs or feathers which comprises treating the said material in a dyeing bath containing hydrogen superoxide and a diamine of the general formula in which R means phenyl, halogenophenyl, hydroxyphenyl, alkoxyphenyl or alkylphenyl, and X means alkyl or hydroxyalkyl, z and a stand for hydrogen, alkyl or hydroxyalkyl and n for 1 or 2, and a further dye for pelts of the group consisting of paradiamines and parahydroxyamino compounds of the benzene series.
3. The process for dyeing furs, hairs or feathers which comprises treating the said material in a dyeing bath containing hydrogen superoxide and a diamine of the general formula in which R means phenyl, halogenophenyl, hydroxyphenyl, alkoxyphenyl or alkylphenyl and X means alkyl or hydroxyalkyl.
4. The process for dyeing furs, hairs or feathers which comprises treating the said material in a. dyeing bath containing hydrogen superoxide and a diamine of the general formula N Hz alkyl-S- f in which 3 means hydrogen, halogen, alkoxy, alkyl or alkoxy and a further dye for pelts of the-1 group consisting of paradiamines and parahydroxyamino compounds of the benzene series.
6. The process for dyeing furs, hairs or feathers which comprises treating the said material in a dyeing bath containing hydrogen superoxide and a diamine of the general formula elkyllac in which 1/ means hydrogen, halogen, alkoxy, alkyl or alkoxy and paraphenylenediamine. 13!
7. The process for dyeing furs, hairs or feathers which comprises treating the said material in a dyeing bath containing hydrogen superoxide and the diamine of the formula 0 HtCrand paraphenylenediamine.
8. The process for dyeing furs, hairs or feathers which comprises treating the said material 150 in a dyeing bath containing hydrogen superoxide and the diamine 01. the formula are which comprises treating the said material in a dyeing bath containing hydrogen superoxide and the diamine of the formula ERICH LEI-MANN. HANS WASS ENEGGER.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1940757X | 1932-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1940757A true US1940757A (en) | 1933-12-26 |
Family
ID=7750456
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US675144A Expired - Lifetime US1940757A (en) | 1932-05-06 | 1933-06-09 | Process for dyeing furs, hairs, and feathers |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1940757A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3111541A (en) * | 1960-02-01 | 1963-11-19 | American Cyanamid Co | Novel aromatic sulfides and method of preparing same |
| US4594453A (en) * | 1984-06-11 | 1986-06-10 | Ethyl Corporation | Process for preparing (hydrocarbylthio)aromatic amines |
| US4760188A (en) * | 1984-06-11 | 1988-07-26 | Ethyl Corporation | Substituted diaminotoluene |
| US4799934A (en) * | 1987-10-30 | 1989-01-24 | Clairol Incorporated | Sulfur-containing nitroaminobenzene dyes, process and hair dye compositions |
| US5202487A (en) * | 1988-09-13 | 1993-04-13 | L'oreal | 2-substituted para-aminophenols and their use for dyeing keratinous fibres |
| EP0688767A1 (en) | 1994-06-24 | 1995-12-27 | Bristol-Myers Squibb Company | 5-mercapto-2-nitro paraphenylenediamine compounds and hair dye compositions containing same |
| US5505741A (en) * | 1992-03-25 | 1996-04-09 | L'oreal | Processes for dyeing of keratinous fibers with compositions which contain 2-sulfurated metaphenylenediamines in combination with oxidation dye precursors |
| US5534036A (en) * | 1992-10-02 | 1996-07-09 | L'oreal | Keratinous fiber dyeing methods and compositions which contain sulfated methaphenylenediamine couplers in combination with oxidation dye precursors |
| US5534037A (en) * | 1992-02-14 | 1996-07-09 | L'oreal | Dye composition for keratinic fibres containing sulfured metaphenylenediamines, dyeing process and new sulfured metaphenylenediamines and preparation method thereof |
| US5542952A (en) * | 1993-12-01 | 1996-08-06 | L'oreal | Dye composition containing sulphur-containing p-phenylenediamines and corresponding dyeing processes, novel sulphur-containing p-phenylenediamines and process for the preparation thereof |
| US6207838B1 (en) | 1999-04-30 | 2001-03-27 | The University Of Arizona | Electrochemically generated organothiating reagents and their use |
| US6432294B1 (en) | 2000-12-14 | 2002-08-13 | The University Of Arizona | Electrochemical activation of organic disulfides for electrophilic substitution |
| US6509434B1 (en) | 2000-03-20 | 2003-01-21 | Albemarle Corporation | Aromatic amine curatives and their use |
-
1933
- 1933-06-09 US US675144A patent/US1940757A/en not_active Expired - Lifetime
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3111541A (en) * | 1960-02-01 | 1963-11-19 | American Cyanamid Co | Novel aromatic sulfides and method of preparing same |
| US4594453A (en) * | 1984-06-11 | 1986-06-10 | Ethyl Corporation | Process for preparing (hydrocarbylthio)aromatic amines |
| US4760188A (en) * | 1984-06-11 | 1988-07-26 | Ethyl Corporation | Substituted diaminotoluene |
| US4799934A (en) * | 1987-10-30 | 1989-01-24 | Clairol Incorporated | Sulfur-containing nitroaminobenzene dyes, process and hair dye compositions |
| US5202487A (en) * | 1988-09-13 | 1993-04-13 | L'oreal | 2-substituted para-aminophenols and their use for dyeing keratinous fibres |
| US5534037A (en) * | 1992-02-14 | 1996-07-09 | L'oreal | Dye composition for keratinic fibres containing sulfured metaphenylenediamines, dyeing process and new sulfured metaphenylenediamines and preparation method thereof |
| US5672759A (en) * | 1992-02-14 | 1997-09-30 | L'oreal | Dye composition for keratinic fibres containing sulfured metaphenylenediamines, dyeing process and new sulfured metaphenylenediamines and preparation method thereof |
| US5505741A (en) * | 1992-03-25 | 1996-04-09 | L'oreal | Processes for dyeing of keratinous fibers with compositions which contain 2-sulfurated metaphenylenediamines in combination with oxidation dye precursors |
| US5710311A (en) * | 1992-03-25 | 1998-01-20 | L'oreal | 2-sulphured metaphenylenediamines for dyeing hair |
| US5534036A (en) * | 1992-10-02 | 1996-07-09 | L'oreal | Keratinous fiber dyeing methods and compositions which contain sulfated methaphenylenediamine couplers in combination with oxidation dye precursors |
| US5542952A (en) * | 1993-12-01 | 1996-08-06 | L'oreal | Dye composition containing sulphur-containing p-phenylenediamines and corresponding dyeing processes, novel sulphur-containing p-phenylenediamines and process for the preparation thereof |
| EP0688767A1 (en) | 1994-06-24 | 1995-12-27 | Bristol-Myers Squibb Company | 5-mercapto-2-nitro paraphenylenediamine compounds and hair dye compositions containing same |
| US6207838B1 (en) | 1999-04-30 | 2001-03-27 | The University Of Arizona | Electrochemically generated organothiating reagents and their use |
| US6509434B1 (en) | 2000-03-20 | 2003-01-21 | Albemarle Corporation | Aromatic amine curatives and their use |
| US6432294B1 (en) | 2000-12-14 | 2002-08-13 | The University Of Arizona | Electrochemical activation of organic disulfides for electrophilic substitution |
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