US2060186A - Dyeing of acetate artificial silk - Google Patents

Dyeing of acetate artificial silk Download PDF

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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
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United States
Prior art keywords
artificial silk
dyeing
acetate artificial
dyestuffs
amino
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Expired - Lifetime
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US731216A
Inventor
Felix Fredrich
Huber Wilhelm
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FIRM SOCIETY OF CHEMICAL INDUSTRY IN BASLE
SOC OF CHEMICAL IND
Original Assignee
SOC OF CHEMICAL IND
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Filing date
Publication date
Priority to GB28090/33A priority Critical patent/GB428767A/en
Priority claimed from US693219A external-priority patent/US2058433A/en
Application filed by SOC OF CHEMICAL IND filed Critical SOC OF CHEMICAL IND
Priority to US731216A priority patent/US2060186A/en
Application granted granted Critical
Publication of US2060186A publication Critical patent/US2060186A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09BORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B1/00Dyes with anthracene nucleus not condensed with any other ring
    • C09B1/16Amino-anthraquinones
    • C09B1/20Preparation from starting materials already containing the anthracene nucleus
    • C09B1/26Dyes with amino groups substituted by hydrocarbon radicals
    • C09B1/32Dyes with amino groups substituted by hydrocarbon radicals substituted by aryl groups
    • C09B1/325Dyes 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
US731216A 1932-10-15 1934-06-18 Dyeing of acetate artificial silk Expired - Lifetime US2060186A (en)

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

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Cited By (14)

* Cited by examiner, † Cited by third party
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

Cited By (14)

* Cited by examiner, † Cited by third party
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

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