GB917104A - Reactive sulfone-containing dyestuffs - Google Patents
Reactive sulfone-containing dyestuffsInfo
- Publication number
- GB917104A GB917104A GB4478260A GB4478260A GB917104A GB 917104 A GB917104 A GB 917104A GB 4478260 A GB4478260 A GB 4478260A GB 4478260 A GB4478260 A GB 4478260A GB 917104 A GB917104 A GB 917104A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- toluene
- dyestuff
- hydroxyethylsulphonylmethyl
- amino
- 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
- 150000003457 sulfones Chemical class 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 12
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 10
- -1 amine cation Chemical group 0.000 abstract 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 2
- 150000004056 anthraquinones Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 abstract 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 1
- ALNUOSXDMYFQNQ-UHFFFAOYSA-N 2-nitro-1,3-thiazole Chemical compound [O-][N+](=O)C1=NC=CS1 ALNUOSXDMYFQNQ-UHFFFAOYSA-N 0.000 abstract 1
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 abstract 1
- AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 abstract 1
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 229920003043 Cellulose fiber Polymers 0.000 abstract 1
- 235000000177 Indigofera tinctoria Nutrition 0.000 abstract 1
- 229930192627 Naphthoquinone Natural products 0.000 abstract 1
- 239000004677 Nylon Substances 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 229920002494 Zein Polymers 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical group 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 239000005018 casein Substances 0.000 abstract 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 abstract 1
- 235000021240 caseins Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- 150000005125 dioxazines Chemical class 0.000 abstract 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethyl mercaptane Natural products CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229940097275 indigo Drugs 0.000 abstract 1
- COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 abstract 1
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 abstract 1
- NYGZLYXAPMMJTE-UHFFFAOYSA-M metanil yellow Chemical group [Na+].[O-]S(=O)(=O)C1=CC=CC(N=NC=2C=CC(NC=3C=CC=CC=3)=CC=2)=C1 NYGZLYXAPMMJTE-UHFFFAOYSA-M 0.000 abstract 1
- 150000002791 naphthoquinones Chemical class 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229920001778 nylon Polymers 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 abstract 1
- 235000021286 stilbenes Nutrition 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical group OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 abstract 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 0.000 abstract 1
- 239000005019 zein Substances 0.000 abstract 1
- 229940093612 zein Drugs 0.000 abstract 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 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
- C09B49/00—Sulfur dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
4 - Amino-2:6-bis(b -sulphatoethylsulphonylmethyl)-toluene is made by sulphating 4-amino - 2:6 - bis(b - hydroxyethylsulphonylmethyl)-toluene obtained by reduction of the corresponding 4-nitro compound. The latter is obtained by oxidation of 4-nitro-2:6-bis(b -hydroxyethylmercaptomethyl)-toluene prepared by reacting 2:6 - bis(chloromethyl) - 4 - nitrotoluene with mercaptoethanol. 4-Hydrazino-2:6 - bis - (b - sulphatoethylsulphonylmethyl) toluene and 4-hydrazino-2:6-bis(b -hydroxyethylsulphonylmethyl)-toluene are made by diazotising and reducing the corresponding 4-amino compounds.ALSO:The invention comprises dyestuff mixtures of the formula:-<FORM:0917104/IV (b)/1> wherein A is a non-phthalocyanine dyestuff moiety, X is a bridging link containing up to 3 linking atoms selected from C, S, O and N and mixtures thereof, Y and Z are each hydrogen, lower alkyl, lower alkoxy or -CH2SO2CH2CH2OSO3M, M is hydrogen or an alkali metal, alkaline earth metal, ammonium or amine cation, n1 has an average value of 0 to 3 and n2 has an average value of 1 to 4. The residue A may be of the monoazo, disazo, polyazo, anthraquinone, nitro, thiazole, stilbene, azoic, di- or triphenylmethane, xanthene, acridine, azine, oxazine, thiazine, benzophenone, benzo- or naphthoquinone, indigo, thioindigo, sulphur dye or cyanine dye series. Examples illustrate dyes of the anthraquinone and dioxazine series. The bridging link X may be -SO2NR-NR, -O-, -NRSO2-, -SO2 NRNH-, -CH2-, -C2H4-, -CH2SO2-, -CH2NR-, -CH2S-, -CH2O-, -CO-, -S-, -CONH-, -NHCO- or -SCH2-. Dyes of the above formula may be made by reacting a compound of the formula shown in the right-hand bracketed portion above where X is amino or the corresponding hydroxyethylsulphonylmethyl compound with a dyestuff which contains 1 to 4 nuclear sulphochloride groups and 0 to 3 nuclear sulphonic acid groups or with a dyestuff which may or may not be sulphonated but which contains at least one halogen substituent and, if necessary, esterifying the hydroxy groups or sulphonating the radical A. Also a dyestuff may be chloromethylated and reacted with an aminobenzene containing at least one hydroxy- or sulphatoethyl-sulphonylmethyl group, or 4-hydrazino-2:6- bis(b - hydroxyethylsulphonylmethyl) toluene or its sulphate ester may be reacted with a chlorosulphonated dyestuff. The dyestuffs dye and print cellulose fibres by application to the fibre and curing at temperatures above about 220 DEG C. They also dye and print wool, silk, casein, zein, nylon and polyurethane fibres. Specification 733,471 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86276959A | 1959-12-30 | 1959-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB917104A true GB917104A (en) | 1963-01-30 |
Family
ID=25339290
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4478260A Expired GB917104A (en) | 1959-12-30 | 1960-12-30 | Reactive sulfone-containing dyestuffs |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB917104A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4395545A (en) * | 1979-02-02 | 1983-07-26 | Adam Jean Marie | Basic dioxazine compounds |
-
1960
- 1960-12-30 GB GB4478260A patent/GB917104A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4395545A (en) * | 1979-02-02 | 1983-07-26 | Adam Jean Marie | Basic dioxazine compounds |
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