US2060186A - Dyeing of acetate artificial silk - Google Patents
Dyeing of acetate artificial silk Download PDFInfo
- Publication number
- US2060186A US2060186A US731216A US73121634A US2060186A US 2060186 A US2060186 A US 2060186A US 731216 A US731216 A US 731216A US 73121634 A US73121634 A US 73121634A US 2060186 A US2060186 A US 2060186A
- Authority
- US
- United States
- Prior art keywords
- artificial silk
- dyeing
- acetate artificial
- dyestuffs
- 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 - Lifetime
Links
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
- 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
- C09B1/32—Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
- C09B1/325—Dyes with no other substituents than the amino groups
Definitions
- acetate artificial silk can be dyed by means of feebly basic, sparingly soluble or insoluble dyestuffs. While a large number of such dyestuffs dye acetate artificial silk only feeble or matt tints, the number of dyestuffs capable of dyeing such silk in deep full tints is comparatively small. The number cannot be increased directly by introducing substituents into the molecule of the dyestufi', since very frequently the enlargement of the molecule is associated with a strong diminution of the aflinity of the dyestufi for acetate artificial silk.
- the present invention relates to a composition of matter and to a process for dyeing acetate artificial silk in which the dyeing is conducted with a composition of matter consisting of a mixture of a feebly dyeing dyestufi with a similarly constituted dyestufi.
- the term similarly comprises the homologous, analogous and isomeric dyestuffs having a somewhat similar shade.
- Such a composition of matter' presents an increased aflinity for the fiber which is quite considerable and makes it possible to use products which hitherto have had no practical value.
- the dyestufi of low aflinity becomes more readily adsorbed when it is mixed with a dyestufl which in itself has a practically sufficient aflinity for acetate artificial silk.
- compositions of matter of the present invention may be made by adding to the components of a dyestuif during its manufacture a homologue, isomeride or analogue thereof, or by dissolving the finished dyestuffs in a common solvent and precipitating them together in a finely divided state, or by finely grinding together the finished dyestuffs, or by adding the previously finely subdivided dyestuffs to the same dye-bath.
- the process is applicable to all classes of dyestuffs usual in the acetate artificial silk dyehouse. It finds a special application in the case 'the temperature of the bath is raised within'% of dyestuif preparations from azo-dyestufls and in the present case from aminoanthraquinones.
- the preparation is to be made from an azo-dyestuff there may be added to the coupling component or to the diaZo-component or to both, 5 a homologue, isomeride or analogue thereof, and the mixture of dyestuffs may thus bemade directly, or the finished azo-dyestuffs may be mixed with each other by fine grinding or may be added to the same dye-bath.
- Example 1 6 parts of 1-amino-4anilidoanthraquinone and 4 parts of l-amino-4-para-toluidoanthraquinone are introduced into parts of sulfuric acid of 98 per cent. strength at 0-10 C. and the mass is stirred until dissolution is complete. The solution is poured upon ice, filtered and washed until neutral. If the dyestuff thus obtained is brought into a suitable form by grinding with a dispersing agent there is obtained a preparation which dyes acetate artificial silk intensely blue tints, whereas the dyeings obtained with the individual dyestuffs are less intense.
- the intimate mixture of 1-amino-4-paratoluidoanthraquinone and 1-monomethylamino-4-anilidoanthraquinone also dyes acetate artificial silk blue, as also the ternary mixture of 1-amino-4-anilidoanthra-, quinone, 1-amino-4 para-toluidoanthraquinone and 1-monomethylaminol-anilidoanthraquinone.
- Example 2 A greenish blue is obtained by the use of a 55 phenylaminoanthraquinone and 2.5 parts of 1- metholamino 4 (4'-hyd.roxy) -phenylaminoanthraquinone.
- a dyeing composition consisting of a mixture of at least two acetate artificial silk dyestufls, of which at least one has a poor afllnity for acetate artificial silk, selected from the group of the products of the general formula i H o N-R,
- R1 stands for a member of the group consisting of hydrogen and methyl
- R2 stands for a member of the group consisting of hydrogen, methyl, hydroxyl and amino
- R1 stands for a member of the group consisting of hydrogen and methyl
- R2 stands for a member of the group consisting of hydro- 20 gen, methyl, hydroxyl and amino.
Description
Fateznt eol New. MD, 1936 sates zerland, assignors to the firm Society of Chemical Industry in Basle, Basel, Switzerland No Drawing. Original application October 11,
1933, Serial No. 693,219. Divided and this application June 18, 1934, Serial No. 731,216.
Switzerland October 15, 1932 2 Claims.
This application is a division of our application for patent Serial No. 693,219, filed in the United States on October 11, 1933, and in Switzerland on October 15, 1932.
It is known that acetate artificial silk can be dyed by means of feebly basic, sparingly soluble or insoluble dyestuffs. While a large number of such dyestuffs dye acetate artificial silk only feeble or matt tints, the number of dyestuffs capable of dyeing such silk in deep full tints is comparatively small. The number cannot be increased directly by introducing substituents into the molecule of the dyestufi', since very frequently the enlargement of the molecule is associated with a strong diminution of the aflinity of the dyestufi for acetate artificial silk.
The present invention relates to a composition of matter and to a process for dyeing acetate artificial silk in which the dyeing is conducted with a composition of matter consisting of a mixture of a feebly dyeing dyestufi with a similarly constituted dyestufi. The term similarly comprises the homologous, analogous and isomeric dyestuffs having a somewhat similar shade. Such a composition of matter'presents an increased aflinity for the fiber which is quite considerable and makes it possible to use products which hitherto have had no practical value. The dyestufi of low aflinity becomes more readily adsorbed when it is mixed with a dyestufl which in itself has a practically sufficient aflinity for acetate artificial silk. In this manner the affinity of the already. useful acetate artificial silk dyestuff may be improved. Furthermore, it is possible by use of such a composition of matter to shift the color tint of the dyeing in a desired manner in one or the other direction without introduction of substituents into the dyestufi molecule of the dyestuff of good affinity, which introduction, as already stated, may affect the degree of afiinity of the dyestuff in an unfavourable manner.
The compositions of matter of the present invention may be made by adding to the components of a dyestuif during its manufacture a homologue, isomeride or analogue thereof, or by dissolving the finished dyestuffs in a common solvent and precipitating them together in a finely divided state, or by finely grinding together the finished dyestuffs, or by adding the previously finely subdivided dyestuffs to the same dye-bath.
The process is applicable to all classes of dyestuffs usual in the acetate artificial silk dyehouse. It finds a special application in the case 'the temperature of the bath is raised within'% of dyestuif preparations from azo-dyestufls and in the present case from aminoanthraquinones. When the preparation is to be made from an azo-dyestuff there may be added to the coupling component or to the diaZo-component or to both, 5 a homologue, isomeride or analogue thereof, and the mixture of dyestuffs may thus bemade directly, or the finished azo-dyestuffs may be mixed with each other by fine grinding or may be added to the same dye-bath. The procedureis similarin making dyestuff preparations from aminoanthraquinones; in this case a good intermixture may be achieved, among other methods, by dissolving the homologues, isomerides or other analogous dyestuffs in the same solvent and precipitating the mixture in finely divided form in some suitable manner.
The following examples illustrate the invention, the parts being by weight:
Example 1 6 parts of 1-amino-4anilidoanthraquinone and 4 parts of l-amino-4-para-toluidoanthraquinone are introduced into parts of sulfuric acid of 98 per cent. strength at 0-10 C. and the mass is stirred until dissolution is complete. The solution is poured upon ice, filtered and washed until neutral. If the dyestuff thus obtained is brought into a suitable form by grinding with a dispersing agent there is obtained a preparation which dyes acetate artificial silk intensely blue tints, whereas the dyeings obtained with the individual dyestuffs are less intense. The intimate mixture of 1-amino-4-paratoluidoanthraquinone and 1-monomethylamino-4-anilidoanthraquinone also dyes acetate artificial silk blue, as also the ternary mixture of 1-amino-4-anilidoanthra-, quinone, 1-amino-4 para-toluidoanthraquinone and 1-monomethylaminol-anilidoanthraquinone.
Example 2 A greenish blue is obtained by the use of a 55 phenylaminoanthraquinone and 2.5 parts of 1- metholamino 4 (4'-hyd.roxy) -phenylaminoanthraquinone.
What we claim is:
1. A dyeing composition consisting of a mixture of at least two acetate artificial silk dyestufls, of which at least one has a poor afllnity for acetate artificial silk, selected from the group of the products of the general formula i H o N-R,
H H R:
in which R1 stands for a member of the group consisting of hydrogen and methyl, and R2 stands for a member of the group consisting of hydrogen, methyl, hydroxyl and amino.
2. A process of dyeing acetate artificial silk mixture of 7.5 parts of 1-amino-4-(4'-amino)- H H R:
in which R1 stands for a member of the group consisting of hydrogen and methyl, and R2 stands for a member of the group consisting of hydro- 20 gen, methyl, hydroxyl and amino.
FRIEDRICH FELIX. MAX BOMMER.
WILHELM HUBER. 25
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB28090/33A GB428767A (en) | 1932-10-15 | 1933-10-11 | Improvements in the dyeing of cellulose acetate artificial silk |
US731216A US2060186A (en) | 1932-10-15 | 1934-06-18 | Dyeing of acetate artificial silk |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH428767X | 1932-10-15 | ||
US693219A US2058433A (en) | 1932-10-15 | 1933-10-11 | Dyeing of acetate artificial silk |
US731216A US2060186A (en) | 1932-10-15 | 1934-06-18 | Dyeing of acetate artificial silk |
Publications (1)
Publication Number | Publication Date |
---|---|
US2060186A true US2060186A (en) | 1936-11-10 |
Family
ID=31998311
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US731216A Expired - Lifetime US2060186A (en) | 1932-10-15 | 1934-06-18 | Dyeing of acetate artificial silk |
Country Status (2)
Country | Link |
---|---|
US (1) | US2060186A (en) |
GB (1) | GB428767A (en) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2506020A (en) * | 1947-11-26 | 1950-05-02 | Ciba Ltd | Mixture of insoluble aminoanthraquinone dyes |
US2610103A (en) * | 1949-02-11 | 1952-09-09 | Ciba Ltd | Dyeing processes for wool and preparations therefor |
US2768183A (en) * | 1954-08-04 | 1956-10-23 | Gen Aniline & Film Corp | Anthraquinone dyestuffs |
US2827356A (en) * | 1952-10-20 | 1958-03-18 | Celanese Corp | Anthraquinone dyestuffs |
US2888312A (en) * | 1952-08-28 | 1959-05-26 | Ciba Ltd | Vat dyestuff mixtures |
US2894800A (en) * | 1954-01-26 | 1959-07-14 | Saul & Co | Dyestuff mixtures |
US2967752A (en) * | 1958-05-30 | 1961-01-10 | Sandoz Ltd | Blue disperse dyestuffs of the anthraquinone series |
US2967754A (en) * | 1958-05-28 | 1961-01-10 | Sandoz Ag | Disperse dyestuffs of the anthraquinone series |
US2979066A (en) * | 1956-09-17 | 1961-04-11 | Proctor Silex Corp | Color control of liquids |
US3177049A (en) * | 1961-07-11 | 1965-04-06 | Bayer Ag | Anthraquinone dye mixture and wool dyeing therewith |
US3199941A (en) * | 1961-08-21 | 1965-08-10 | Kuhlmann Ets | N-(2-benzothiazoyl)-1, 4, 5, 8 diamino dihydroxy anthraquinones, mixtures and synthesis thereof |
US3220793A (en) * | 1963-07-25 | 1965-11-30 | Ici Ltd | Coloration process |
US3881865A (en) * | 1972-06-02 | 1975-05-06 | Ici Ltd | Anthraquinone dyestuff mixtures |
US3989449A (en) * | 1969-03-04 | 1976-11-02 | L. B. Holliday & Co. Limited | Dyestuff compositions |
-
1933
- 1933-10-11 GB GB28090/33A patent/GB428767A/en not_active Expired
-
1934
- 1934-06-18 US US731216A patent/US2060186A/en not_active Expired - Lifetime
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2506020A (en) * | 1947-11-26 | 1950-05-02 | Ciba Ltd | Mixture of insoluble aminoanthraquinone dyes |
US2610103A (en) * | 1949-02-11 | 1952-09-09 | Ciba Ltd | Dyeing processes for wool and preparations therefor |
US2888312A (en) * | 1952-08-28 | 1959-05-26 | Ciba Ltd | Vat dyestuff mixtures |
US2827356A (en) * | 1952-10-20 | 1958-03-18 | Celanese Corp | Anthraquinone dyestuffs |
US2894800A (en) * | 1954-01-26 | 1959-07-14 | Saul & Co | Dyestuff mixtures |
US2768183A (en) * | 1954-08-04 | 1956-10-23 | Gen Aniline & Film Corp | Anthraquinone dyestuffs |
US2979066A (en) * | 1956-09-17 | 1961-04-11 | Proctor Silex Corp | Color control of liquids |
US2967754A (en) * | 1958-05-28 | 1961-01-10 | Sandoz Ag | Disperse dyestuffs of the anthraquinone series |
US2967752A (en) * | 1958-05-30 | 1961-01-10 | Sandoz Ltd | Blue disperse dyestuffs of the anthraquinone series |
US3177049A (en) * | 1961-07-11 | 1965-04-06 | Bayer Ag | Anthraquinone dye mixture and wool dyeing therewith |
US3199941A (en) * | 1961-08-21 | 1965-08-10 | Kuhlmann Ets | N-(2-benzothiazoyl)-1, 4, 5, 8 diamino dihydroxy anthraquinones, mixtures and synthesis thereof |
US3220793A (en) * | 1963-07-25 | 1965-11-30 | Ici Ltd | Coloration process |
US3989449A (en) * | 1969-03-04 | 1976-11-02 | L. B. Holliday & Co. Limited | Dyestuff compositions |
US3881865A (en) * | 1972-06-02 | 1975-05-06 | Ici Ltd | Anthraquinone dyestuff mixtures |
Also Published As
Publication number | Publication date |
---|---|
GB428767A (en) | 1935-05-13 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2060186A (en) | Dyeing of acetate artificial silk | |
US3122410A (en) | Process for the dyeing, padding and printing of polyester fibers | |
US2342191A (en) | Dyeing and printing cellulose esters and ethers with amino-anthraquinone dyes | |
US3413075A (en) | Azo dyestuff mixtures and aromatic polyester fibers colored therewith | |
US2384734A (en) | Mixtures of azo dyestuffs | |
US2830043A (en) | Monoazo dyestuffs | |
US2819288A (en) | Polyhydroxy-beta-acylaminoanthraquinones | |
US2042757A (en) | Process of preparing acid wool dyestuffs of the anthraquinone series and the dyestuffs thus obtainable | |
US2058433A (en) | Dyeing of acetate artificial silk | |
US2830062A (en) | Method of preparing anthraquinone dyes | |
EP0098288A1 (en) | Mixtures of azo dyes from 2-amino-3-nitro-5-acyl thiophenes and certain aniline couplers | |
US3541182A (en) | Anthraquinone containing monoazo dyestuffs | |
US2312398A (en) | Dyestuff preparations | |
US2053818A (en) | Azo-dyestuffs and process of making same | |
US2585681A (en) | Antigas fading anthraqijinone dyes | |
US2407704A (en) | Anthraquinone acid dyestuff | |
US3023071A (en) | Process for the coloration of nylon type 11 fibres | |
US2053041A (en) | Dyestuff mixture | |
US2888312A (en) | Vat dyestuff mixtures | |
US1943170A (en) | Azo-dyestuffs and process of making same | |
US3434792A (en) | 1-amino- (and methylamino) 2-bromo-4-(p-(beta - hydroxyethyl) - anilino) - anthraquinone disperse dyes for nylon and polypropylene | |
US2053817A (en) | Azo-dyestuffs | |
US1509442A (en) | Azo dyes | |
US1762021A (en) | Condensation products of the naphthostyril series and process of preparing the same | |
US3350425A (en) | 1-alkylsulfonamido-4-anilino-anthraquinones |