GB807241A - Anthraquinone dyestuffs - Google Patents
Anthraquinone dyestuffsInfo
- Publication number
- GB807241A GB807241A GB2657556A GB2657556A GB807241A GB 807241 A GB807241 A GB 807241A GB 2657556 A GB2657556 A GB 2657556A GB 2657556 A GB2657556 A GB 2657556A GB 807241 A GB807241 A GB 807241A
- Authority
- GB
- United Kingdom
- Prior art keywords
- anthraquinone
- chloroanthraquinone
- amino
- alkyl
- polyacrylonitrile
- 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
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 title abstract 5
- 150000004056 anthraquinones Chemical class 0.000 title abstract 5
- 239000000975 dye Substances 0.000 abstract 6
- 229920002239 polyacrylonitrile Polymers 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- -1 aliphatic radical Chemical class 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 2
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 abstract 2
- 239000000463 material Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- AIECXCOELYPOFN-UHFFFAOYSA-N 1-(methylamino)-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(NC)=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O AIECXCOELYPOFN-UHFFFAOYSA-N 0.000 abstract 1
- KXOGXZAXERYOTC-UHFFFAOYSA-N 1-amino-4-methoxyanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2OC KXOGXZAXERYOTC-UHFFFAOYSA-N 0.000 abstract 1
- QAZNDGDSNIGKLU-UHFFFAOYSA-N 1-amino-5-chloro-4-hydroxyanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C(O)=CC=C2N QAZNDGDSNIGKLU-UHFFFAOYSA-N 0.000 abstract 1
- QIHMGEKACAOTPE-UHFFFAOYSA-N 1-amino-5-chloroanthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2N QIHMGEKACAOTPE-UHFFFAOYSA-N 0.000 abstract 1
- WIMJTAGMOPIYOA-UHFFFAOYSA-N 1-bromo-4-(cyclohexylamino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Br)=CC=C1NC1CCCCC1 WIMJTAGMOPIYOA-UHFFFAOYSA-N 0.000 abstract 1
- IIPRUQZTMZETSL-UHFFFAOYSA-N 1-bromo-4-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(Br)=CC=C2NC IIPRUQZTMZETSL-UHFFFAOYSA-N 0.000 abstract 1
- BPZGOVZINFLGSQ-UHFFFAOYSA-N 1-chloro-5-(methylamino)anthracene-9,10-dione Chemical compound O=C1C2=C(Cl)C=CC=C2C(=O)C2=C1C=CC=C2NC BPZGOVZINFLGSQ-UHFFFAOYSA-N 0.000 abstract 1
- YNCUXTUVGBIQBZ-UHFFFAOYSA-N 1-chloro-8-(ethylamino)anthracene-9,10-dione Chemical compound C(C)NC1=CC=CC=2C(C3=CC=CC(=C3C(C1=2)=O)Cl)=O YNCUXTUVGBIQBZ-UHFFFAOYSA-N 0.000 abstract 1
- BWOZYUXKRAILOH-UHFFFAOYSA-N 1-methoxy-4-(4-methylanilino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(OC)=CC=C1NC1=CC=C(C)C=C1 BWOZYUXKRAILOH-UHFFFAOYSA-N 0.000 abstract 1
- CAPCBAYULRXQAN-UHFFFAOYSA-N 1-n,1-n-diethylpentane-1,4-diamine Chemical compound CCN(CC)CCCC(C)N CAPCBAYULRXQAN-UHFFFAOYSA-N 0.000 abstract 1
- YCANAXVBJKNANM-UHFFFAOYSA-N 1-nitroanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2[N+](=O)[O-] YCANAXVBJKNANM-UHFFFAOYSA-N 0.000 abstract 1
- XBNVWXKPFORCRI-UHFFFAOYSA-N 2h-naphtho[2,3-f]quinolin-1-one Chemical compound C1=CC=CC2=CC3=C4C(=O)CC=NC4=CC=C3C=C21 XBNVWXKPFORCRI-UHFFFAOYSA-N 0.000 abstract 1
- HUKPVYBUJRAUAG-UHFFFAOYSA-N 7-benzo[a]phenalenone Chemical compound C1=CC(C(=O)C=2C3=CC=CC=2)=C2C3=CC=CC2=C1 HUKPVYBUJRAUAG-UHFFFAOYSA-N 0.000 abstract 1
- GDALETGZDYOOGB-UHFFFAOYSA-N Acridone Natural products C1=C(O)C=C2N(C)C3=CC=CC=C3C(=O)C2=C1O GDALETGZDYOOGB-UHFFFAOYSA-N 0.000 abstract 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- FZEYVTFCMJSGMP-UHFFFAOYSA-N acridone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3NC2=C1 FZEYVTFCMJSGMP-UHFFFAOYSA-N 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- RGCKGOZRHPZPFP-UHFFFAOYSA-N alizarin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC=C3C(=O)C2=C1 RGCKGOZRHPZPFP-UHFFFAOYSA-N 0.000 abstract 1
- 125000005250 alkyl acrylate group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229920001577 copolymer Polymers 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 abstract 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 abstract 1
- MNRGFUBMMILKAL-UHFFFAOYSA-N methyl phenylmethanesulfonate Chemical compound COS(=O)(=O)CC1=CC=CC=C1 MNRGFUBMMILKAL-UHFFFAOYSA-N 0.000 abstract 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 abstract 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 abstract 1
- FNCVZYRPXOZNSM-UHFFFAOYSA-N n-(4-chloro-9,10-dioxoanthracen-1-yl)benzamide Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(Cl)=CC=C1NC(=O)C1=CC=CC=C1 FNCVZYRPXOZNSM-UHFFFAOYSA-N 0.000 abstract 1
- YRGGSPFTFSUVLS-UHFFFAOYSA-N n-(4-methoxy-9,10-dioxoanthracen-1-yl)acetamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(NC(C)=O)=CC=C2OC YRGGSPFTFSUVLS-UHFFFAOYSA-N 0.000 abstract 1
- OBJNZHVOCNPSCS-UHFFFAOYSA-N naphtho[2,3-f]quinazoline Chemical compound C1=NC=C2C3=CC4=CC=CC=C4C=C3C=CC2=N1 OBJNZHVOCNPSCS-UHFFFAOYSA-N 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 abstract 1
- 229950006389 thiodiglycol Drugs 0.000 abstract 1
- HHIMNFJHTNVXBJ-UHFFFAOYSA-L zinc;dinitrite Chemical compound [Zn+2].[O-]N=O.[O-]N=O HHIMNFJHTNVXBJ-UHFFFAOYSA-L 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/002—Dyes with anthracene nucleus not condensed with any other ring containing onium groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/26—Dyes with amino groups substituted by hydrocarbon radicals
- C09B1/28—Dyes with amino groups substituted by hydrocarbon radicals substituted by alkyl, aralkyl or cyclo alkyl groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B1/00—Dyes with anthracene nucleus not condensed with any other ring
- C09B1/16—Amino-anthraquinones
- C09B1/20—Preparation from starting materials already containing the anthracene nucleus
- C09B1/36—Dyes with acylated amino groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B3/00—Dyes with an anthracene nucleus condensed with one or more carbocyclic rings
- C09B3/02—Benzathrones
- C09B3/06—Preparation from starting materials already containing the benzanthrone nucleus
- C09B3/10—Amino derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
Textile materials of polyacrylonitrile or copolymers thereof with a minor proportion of e.g. alkyl acrylate or vinyl acetate are dyed or printed with an anthraquinone dyestuff which contains, besides any other groups which may be present, an alkamino group of the formula <FORM:0807241/IV (c)/1> where X is a bivalent aliphatic radical of up to six carbon atoms, R1 is hydrogen or alkyl, R2 and R3 are alkyl or together form a heterocyclic ring with the tertiary nitrogen atom, or with an alkyl ammonium salt of said dyestuff. The dyes are made by reacting anthraquinone derivatives (including condensed systems such as benzanthrone, acridone, anthrapyridone or anthrapyrimidine) which contain substituents such as halogen, nitro, hydroxy, alkoxy or arylhydroxy, with amines of the formula <FORM:0807241/IV (c)/2> The anthraquinone molecule may contain other substituents such as amino, alkylamino, hydroxyalkylamino, acylamino, alkyl, hydroxy, alkoxy, mercapto, carboxamide or cyano. In examples: (1) 1-methylamino-4-bromo-anthraquinone is reacted with 1-dimethylamino-3-aminopropane, 1 - dimethylamino - 2 - aminoethane, 1 - diethylamino - 3 - aminopropane, 1-diethylamino - 4 - amino - n - pentane or N-(b -aminoethyl) piperidine and the products obtained or their quaternary ammonium salts obtained by reacting with dimethyl sulphate, diethyl sulphate, methyl toluene sulphonate or benzyl chloride, are used to dye polyacrylonitrile fibres; (2) 1-methylamino-5-chloroanthraquinone is reacted with 1-dimethylamino-3-aminopropane, and the product obtained or its salt with dimethyl sulphate is used to dye or print polyacrylonitrile fibres. Other anthraquinone starting materials listed are 1-nitroanthraquinone, 1 - amino - 4 - methoxyanthraquinone, 1 - b - hydroxyethylamino - 4 - bromoanthraquinone, 1 - hexahydroanilino - 4 - bromoanthraquinone, 1 - p - methylanilino - 4 - methoxy - anthraquinone, 1 - benzoylamino - 4-chloroanthraquinone, 1 - acetylamino - 4 - methoxyanthraquinone, 1 - amino - 5 - chloranthraquinone, 1 - methylamino - 5 - nitro - anthraquinone, 1 - b - hydroxyethylamino - 5 - chloroanthraquinone, 1 - ethylamino - 8 - chloroanthraquinone, 1.4 - diamino - 5 - nitro - anthraquinone, 1 - amino - 4 - hydroxy - 5 - chloroanthraquinone. Dyeing may be effected in an acid, alkaline or neutral bath at temperatures up to or above 100 DEG C. Example (7) describes the printing of a polyacrylonitrile material, the thickened paste containing in addition to the dyestuff, thiodiglycol, cyclohexanol, acetic acid, zinc nitrite, turkey red oil and petrol. Specification 459,594, [Group IV], is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF18299A DE1150652B (en) | 1955-08-30 | 1955-08-30 | Dyeing of polyacrylonitrile fibers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB807241A true GB807241A (en) | 1959-01-14 |
Family
ID=7088896
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2657556A Expired GB807241A (en) | 1955-08-30 | 1956-08-30 | Anthraquinone dyestuffs |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH351575A (en) |
| DE (1) | DE1150652B (en) |
| FR (1) | FR1158839A (en) |
| GB (1) | GB807241A (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3202682A (en) * | 1961-07-27 | 1965-08-24 | Allied Chem | Synthetic pigments of the anthraquinone type |
| US3232934A (en) * | 1959-06-25 | 1966-02-01 | Allied Chem | Omega-(1-amino-5 and 8-anthraquinonylamino)-1-ammonium alkanes of 2 to 3 carbon atoms |
| US3272792A (en) * | 1961-12-18 | 1966-09-13 | American Aniline Prod | Quaternary ammonium salts of amino halohydrin dyestuffs |
| US3281434A (en) * | 1963-06-19 | 1966-10-25 | Gen Aniline & Film Corp | 1, 4-dihydroxy-5-butylamino-8-(3-trimethylamino-propylamino)-anthraquinone methylsulfate |
| DE1267360B (en) * | 1963-04-23 | 1968-05-02 | Sandoz Ag | Process for the preparation of anthraquinone dyes |
| DE1270712B (en) * | 1960-01-08 | 1968-06-20 | Gen Aniline & Film Corp | Process for the preparation of anthraquinone dyes |
| US3401003A (en) * | 1963-09-04 | 1968-09-10 | Therachemic Chemisch Therapeut | Diaminoanthraquinones and their use as human hair dyes |
| DE1281078B (en) * | 1963-04-23 | 1968-10-24 | Sandoz Ag | Process for the preparation of dyes of the anthraquinone series |
| US3515733A (en) * | 1961-04-21 | 1970-06-02 | Sandoz Ag | Basic dyes |
| US3546258A (en) * | 1964-01-27 | 1970-12-08 | Oreal | 1,4-diamino - 5 - (p-amino phenyl) amino anthraquinones,the acid addition and quaternary ammonium salts thereof |
| US3844712A (en) * | 1968-06-15 | 1974-10-29 | Bayer Ag | Treatment of dyed polyamides |
| WO2007090799A2 (en) | 2006-02-09 | 2007-08-16 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Dyestuffs and hair dye compositions |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2533428A1 (en) * | 1975-07-25 | 1977-02-10 | Bayer Ag | CATIONIC COLORS |
| DE2906132A1 (en) | 1979-02-17 | 1980-08-28 | Bayer Ag | METHOD FOR PRODUCING CATIONIC ANTHRACHINONE DYES |
| EP0055222A3 (en) * | 1980-12-24 | 1983-06-15 | Ciba-Geigy Ag | Salts of cationic anthraquinone dyes, their preparation and their use |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE618006C (en) * | 1933-09-03 | 1935-08-30 | I G Farbenindustrie Akt Ges | Process for coloring plastic masses from water-insoluble polymerization products of unsaturated compounds with an olefinic double bond |
| DE714986C (en) * | 1938-07-15 | 1941-12-11 | Ig Farbenindustrie Ag | Process for the production of basic dyes of the anthraquinone series |
| CH259411A (en) * | 1945-12-27 | 1949-01-31 | Rhodiaceta | Stable dye bath for objects or articles based on polyvinyl derivatives. |
-
1955
- 1955-08-30 DE DEF18299A patent/DE1150652B/en active Pending
-
1956
- 1956-08-25 CH CH351575D patent/CH351575A/en unknown
- 1956-08-29 FR FR1158839D patent/FR1158839A/en not_active Expired
- 1956-08-30 GB GB2657556A patent/GB807241A/en not_active Expired
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3232934A (en) * | 1959-06-25 | 1966-02-01 | Allied Chem | Omega-(1-amino-5 and 8-anthraquinonylamino)-1-ammonium alkanes of 2 to 3 carbon atoms |
| DE1270712B (en) * | 1960-01-08 | 1968-06-20 | Gen Aniline & Film Corp | Process for the preparation of anthraquinone dyes |
| US3515733A (en) * | 1961-04-21 | 1970-06-02 | Sandoz Ag | Basic dyes |
| US3202682A (en) * | 1961-07-27 | 1965-08-24 | Allied Chem | Synthetic pigments of the anthraquinone type |
| US3272792A (en) * | 1961-12-18 | 1966-09-13 | American Aniline Prod | Quaternary ammonium salts of amino halohydrin dyestuffs |
| DE1267360B (en) * | 1963-04-23 | 1968-05-02 | Sandoz Ag | Process for the preparation of anthraquinone dyes |
| DE1281078B (en) * | 1963-04-23 | 1968-10-24 | Sandoz Ag | Process for the preparation of dyes of the anthraquinone series |
| US3281434A (en) * | 1963-06-19 | 1966-10-25 | Gen Aniline & Film Corp | 1, 4-dihydroxy-5-butylamino-8-(3-trimethylamino-propylamino)-anthraquinone methylsulfate |
| US3401003A (en) * | 1963-09-04 | 1968-09-10 | Therachemic Chemisch Therapeut | Diaminoanthraquinones and their use as human hair dyes |
| US3546258A (en) * | 1964-01-27 | 1970-12-08 | Oreal | 1,4-diamino - 5 - (p-amino phenyl) amino anthraquinones,the acid addition and quaternary ammonium salts thereof |
| US3844712A (en) * | 1968-06-15 | 1974-10-29 | Bayer Ag | Treatment of dyed polyamides |
| WO2007090799A2 (en) | 2006-02-09 | 2007-08-16 | Dystar Textilfarben Gmbh & Co Deutschland Kg | Dyestuffs and hair dye compositions |
| EP1820826A1 (en) * | 2006-02-09 | 2007-08-22 | DyStar Textilfarben GmbH & Co. Deutschland KG | Dyestuffs and Hair Dye Compositions |
| WO2007090800A3 (en) * | 2006-02-09 | 2007-12-21 | Dystar Textilfarben Gmbh & Co | Hair dye compositions |
| JP2009529582A (en) * | 2006-02-09 | 2009-08-20 | ダイスター テクスティルファルベン ゲゼルシャフト ミト ベシュレンクテル ハフツング ウント コンパニー ドイツランド コマンデイトゲゼルシャフト | Dye and hair dye composition |
| JP2009531285A (en) * | 2006-02-09 | 2009-09-03 | ダイスター テクスティルファルベン ゲゼルシャフト ミト ベシュレンクテル ハフツング ウント コンパニー ドイツランド コマンデイトゲゼルシャフト | Hair dye composition |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1158839A (en) | 1958-06-19 |
| DE1150652B (en) | 1963-06-27 |
| CH351575A (en) | 1961-01-31 |
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