ES265702A1 - New anthraquinone vat dyestuffs and process for their manufacture - Google Patents
New anthraquinone vat dyestuffs and process for their manufactureInfo
- Publication number
- ES265702A1 ES265702A1 ES0265702A ES265702A ES265702A1 ES 265702 A1 ES265702 A1 ES 265702A1 ES 0265702 A ES0265702 A ES 0265702A ES 265702 A ES265702 A ES 265702A ES 265702 A1 ES265702 A1 ES 265702A1
- Authority
- ES
- Spain
- Prior art keywords
- condensing
- dyes
- bis
- triazine
- 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
- 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 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 title 1
- 239000000975 dye Substances 0.000 abstract 11
- -1 anthraquinone radicals Chemical class 0.000 abstract 6
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical group C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- KHUFHLFHOQVFGB-UHFFFAOYSA-N 1-aminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2N KHUFHLFHOQVFGB-UHFFFAOYSA-N 0.000 abstract 2
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 abstract 2
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229940124530 sulfonamide Drugs 0.000 abstract 2
- 125000000565 sulfonamide group Chemical group 0.000 abstract 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 2
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 abstract 1
- IMRJHBSKCBVMDZ-UHFFFAOYSA-N 1-[[4-chloro-6-[(9,10-dioxoanthracen-1-yl)amino]triazin-5-yl]amino]anthracene-9,10-dione Chemical compound C1(=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O)NC1=C(C(=NN=N1)Cl)NC1=CC=CC=2C(C3=CC=CC=C3C(C12)=O)=O IMRJHBSKCBVMDZ-UHFFFAOYSA-N 0.000 abstract 1
- PHZPGLMKVOOUGI-UHFFFAOYSA-N 1-amino-5-nitroanthracene-9,10-dione Chemical compound O=C1C=2C(N)=CC=CC=2C(=O)C2=C1C=CC=C2[N+]([O-])=O PHZPGLMKVOOUGI-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
- HWAQOZGATRIYQG-UHFFFAOYSA-N 4-sulfobenzoic acid Chemical compound OC(=O)C1=CC=C(S(O)(=O)=O)C=C1 HWAQOZGATRIYQG-UHFFFAOYSA-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
- RXUAOGNTKWCWAG-UHFFFAOYSA-N [4-(N-carboxyanilino)-6-chlorotriazin-5-yl]-phenylcarbamic acid Chemical compound C(=O)(O)N(C1=CC=CC=C1)C1=C(C(=NN=N1)Cl)N(C(=O)O)C1=CC=CC=C1 RXUAOGNTKWCWAG-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000003368 amide group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 abstract 1
- 239000000835 fiber Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- HKTBRYQNVRPBCF-UHFFFAOYSA-N nitrobenzene;sulfurochloridic acid Chemical compound OS(Cl)(=O)=O.[O-][N+](=O)C1=CC=CC=C1 HKTBRYQNVRPBCF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 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
- 239000004627 regenerated cellulose Substances 0.000 abstract 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- 239000000984 vat dye Substances 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
- C09B6/00—Anthracene dyes not provided for above
-
- 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
- C09B1/363—Dyes with acylated amino groups the acyl groups being residues of a dicarboxylic compound forming a bridge between two anthraquinones
-
- 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
- C09B1/46—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound
- C09B1/467—Dyes with acylated amino groups the acyl groups being residues of cyanuric acid or an analogous heterocyclic compound attached to two or more anthraquinone 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/002—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the linkage of the reactive group being alternatively specified
- C09B62/004—Anthracene dyes
-
- 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
- C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
- C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
- C09B62/443—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being alternatively specified
- C09B62/445—Anthracene dyes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Abstract
3-aminobenzene-sulphonic acid-N:g -(N1:N1-bis-hydroxyethyl)-aminopropylamide is made by reducing 3-nitrobenzene-sulphonic acid-N:g -[N1:N1-bis-(hydroxyethyl)] - aminopropylamide which is obtained by condensing m-nitro-benzene-sulphochloride with N:N-bis-(hydroxyethyl)-propylene-diamine-(1:3). Specification 902,364 is referred to.ALSO:The invention comprises vat dyes which contain a 1:3:5-triazine residue linked through amino groups either directly or via benzoylamino groups to the nuclei of two identical or different anthraquinone radicals and at least one sulphonic acid -N-(sulphatoalkyl)-amide group having at least 3 carbon atoms between the sulphate group and the amide nitrogen atom the alkyl chain being uninterrupted or interrupted by an oxygen, sulphur or nitrogen atom. The sulphonamide group or groups may be attached directly to the anthraquinone nucleus or to a phenyl group attached directly or via an amino group to the triazine ring. Anthraquinone radicals specified are the unsubstituted radical or those substituted by acyl, acylamino or amino and the acedianthrone radical. Dyes preferred are those of the formula <FORM:0927713/IV(a)/1> in which m, n and p are each 1 or 2, A1 and A2 are anthraquinone radicals and R is an alkylene chain of 4 or 5 carbon atoms, and examples of these are given. Other dyes specified fall within the above formula but R has 3 carbon atoms or is interrupted by an amino, methylamino or b -sulphato ethylamino group and/or the sulphonamide nitrogen is substituted by methyl. Further dyes specified are of the formulae <FORM:0927713/IV(a)/2> The dyes are made by sulphating the corresponding dyes containing sulphonic acid -N-(hydroxyalkyl)amide groups. The dyes dye and print textile materials of natural or regenerated cellulose and it is stated that in the dyebath or on the fibre under the influence of alkali the sulphate radical is probably split off with the formation of a heterocyclic ring with the sulphonamide nitrogen atom and an insoluble compound is formed. The hydroxy compounds corresponding to dyes of Formula I above where m=n=1 and p=1 are made by condensing a hydroxyalkylamine with the appropriate dyestuff sulphochloride which may be made for example by treating a 2-phenyl-4:6-dichloro-triazine sulphochloride with 2 mols. of an aminoanthraquinone. Hydroxy compounds where m=n=1 and p=2 are made by condensing a bis-(anthraquinonylamino)-chloro-triazine with an aminobenzenesulphon-N-(hydroxyalkyl)-amide. Hydroxy compounds where m=n=2 and p=2 are made by condensing a di-acid halide of a bis(carboxyphenylamino)-chloro-triazine with 2 mols. of an aminoanthraquinone and then with an amino-benzene-sulphon-N-(hydroxyalkyl)amide. The hydroxy compound corresponding to the dye of Formula II above is made by condensing the bis-acid chloride of 2:4-bis-(41-carboxyphenylamino)-6-chloro-1:3:5-triazine with 2 mols. of 1-amino-5-nitro-anthraquinone and then with aniline, reducing the nitro groups, condensing with the dichloride of p-sulphobenzoic acid and reacting the product with 4-aminobutanol. The hydroxy compound corresponding to the dye of Formula III is made by condensing 1 - nitro - anthraquinone - 6- sulpho - chloride with 4-amino-butanol, reducing the nitro group and condensing 2 mols. of the product with 2-phenyl-4:6-dichloro-1:3:5-triazine. Specification 902,364 is referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH230660A CH389806A (en) | 1960-03-01 | 1960-03-01 | Process for the preparation of anthraquinone vat dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES265702A1 true ES265702A1 (en) | 1961-10-16 |
Family
ID=4230701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0265702A Expired ES265702A1 (en) | 1960-03-01 | 1961-02-28 | New anthraquinone vat dyestuffs and process for their manufacture |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH389806A (en) |
| DE (1) | DE1202418B (en) |
| ES (1) | ES265702A1 (en) |
| GB (1) | GB927713A (en) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069564B (en) * | 1959-11-26 | Badische Anilin- i£x Soda-Fabrik Aktiengesellschaft, Ludwigshafen/Rhein | Process for dyeing and printing structures made of cellulose |
-
1960
- 1960-03-01 CH CH230660A patent/CH389806A/en unknown
-
1961
- 1961-02-28 DE DEC23518A patent/DE1202418B/en active Pending
- 1961-02-28 ES ES0265702A patent/ES265702A1/en not_active Expired
- 1961-03-01 GB GB754261A patent/GB927713A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH389806A (en) | 1965-03-31 |
| DE1202418B (en) | 1965-10-07 |
| GB927713A (en) | 1963-06-06 |
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