US2506020A - Mixture of insoluble aminoanthraquinone dyes - Google Patents
Mixture of insoluble aminoanthraquinone dyes Download PDFInfo
- Publication number
- US2506020A US2506020A US49292A US4929248A US2506020A US 2506020 A US2506020 A US 2506020A US 49292 A US49292 A US 49292A US 4929248 A US4929248 A US 4929248A US 2506020 A US2506020 A US 2506020A
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- United States
- Prior art keywords
- mixture
- parts
- anthraquinone
- dyeing
- 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
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- 239000000203 mixture Substances 0.000 title claims description 22
- 239000000975 dye Substances 0.000 title claims description 9
- 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 title description 2
- 238000004043 dyeing Methods 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 12
- -1 ANTHRAQUINONE COMPOUNDS Chemical class 0.000 claims description 6
- 239000000470 constituent Substances 0.000 claims description 6
- 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 claims description 5
- TVBNRFCUTVWHQB-UHFFFAOYSA-N 1-anilino-4-(methylamino)anthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(NC)=CC=C1NC1=CC=CC=C1 TVBNRFCUTVWHQB-UHFFFAOYSA-N 0.000 claims description 4
- 229920000297 Rayon Polymers 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- XUDJOVURIXHNRW-UHFFFAOYSA-N 1-amino-4-anilinoanthracene-9,10-dione Chemical compound C1=2C(=O)C3=CC=CC=C3C(=O)C=2C(N)=CC=C1NC1=CC=CC=C1 XUDJOVURIXHNRW-UHFFFAOYSA-N 0.000 description 3
- 229920002955 Art silk Polymers 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 3
- 229920002301 cellulose acetate Polymers 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- XRIGHGYEGNDPEU-UHFFFAOYSA-N 1-anilinoanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C(=O)C2=C1NC1=CC=CC=C1 XRIGHGYEGNDPEU-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- DQEFEBPAPFSJLV-UHFFFAOYSA-N Cellulose propionate Chemical compound CCC(=O)OCC1OC(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C1OC1C(OC(=O)CC)C(OC(=O)CC)C(OC(=O)CC)C(COC(=O)CC)O1 DQEFEBPAPFSJLV-UHFFFAOYSA-N 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical group O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000001000 anthraquinone dye Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229920001727 cellulose butyrate Polymers 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 229920006218 cellulose propionate Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000005608 naphthenic acid group Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 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
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/92—Synthetic fiber dyeing
- Y10S8/921—Cellulose ester or ether
Definitions
- mixtures of dyestuffs are in some cases of advantage for dyeing cellulose esters, for example, artificial silk or staple fibers of lower fatty acids of cellulose, such as cellulose butyrate, cellulose propionate and especially cellulose acetate, and also the corresponding mixed esters.
- the use of mixtures of dyestuffs is indicated, inter alia, when the dyestuif mixture is required not for producing a desired shade of color but when each of the dyestuffs to be mixed yields dyeings of the same tint or very similar tints, owing to the fact that in many cases such a mixture yields a stronger tint than do the individual pure components of the mixture. This so-called mixture effect varies in strength in difierent instances.
- the present invention is based on the observation that unexpectedly good dyeings on cellulose esters are obtained by using mixtures of which the dyeing constituents consist mainly of l-(c-hydroxyethyl) amino 4 phenylamino anthraquinone and l methylamino 4 phenylamino- .anthraquinone in finely divided form.
- cellulose esters to be dyed by the process of this invention there may be used the known esters of cellulose with aliphatic acids of low molecular weight mentioned above.
- the fibers of some cellulose ethers and of superpolyamides, superpolyurethanes and superpolyesters are to be regarded as equivalents of fibers of cellulose esters, owing to their similar properties.
- the individual components of the mixture namely 1 (fl-hydroxyethyl) -amino 4 phenylamlno anthraquinone and 1 methylamino- 4-phenylamino-anthraquinone, are in themselves known and can be obtained in various ways. It is of advantage to use them in the present process in a pure or relatively pure state. They may be converted in known manner into a finely divided condition prior to the dyeing process, for example, by grinding with a dispersing agent such as sulfite cellulose waste liquor, advantagefuric acid.
- a dispersing agent such as sulfite cellulose waste liquor, advantagefuric acid.
- the two components may be mixed together before or during the preparation of the dyebath.
- the relative proportions of the components may vary within fairly wide limits, but it is of advantage to use not less than 20 per cent, preferably 25-50 per cent, of the component which is present in lower proportion.
- Dyeing may be carried out in the usual manner, for example, in aqueous dispersion with the addition of a wetting or dispersing agent such as a soap, an N-benzyl- -heptadecyl-benzimidazole sulfonic acid, a condensation product of taurine or methyl-taurine with a fatty acid, or the like.
- a wetting or dispersing agent such as a soap, an N-benzyl- -heptadecyl-benzimidazole sulfonic acid, a condensation product of taurine or methyl-taurine with a fatty acid, or the like.
- a dyestuff preparation which contains the two components mentioned above in the desired relative proportions and in a state of fine dispersion and also contains a wetting or dispersing agent such as sulfite cellulose waste liquor, salts of condensation products from formaldehyde and naphthalene sulfonic acids, naphthenic acid salts, if desired with the addition of wetting agents, such as are mentioned above.
- a wetting or dispersing agent such as sulfite cellulose waste liquor, salts of condensation products from formaldehyde and naphthalene sulfonic acids, naphthenic acid salts, if desired with the addition of wetting agents, such as are mentioned above.
- Example 1 4 parts of 1 ([3 hydroxyethyl) amino- 4 phenylamino-anthraquinone and 4 parts of 1 methylamino-4-phenylamino anthraquinone are dissolved in 50 parts of sulfuric acid of per cent. strength. The solution is introduced into a mixture of parts of ice, 240 parts of water and 55 parts of ammonia solution of 25 per cent. strength, stirred well and filtered. The filter residue is washed neutral and ground with about 12 parts of dried sulfite cellulose waste liquor and the necessary quantity of water to form a dyestuif paste containing about 10 per cent. of the dyestufi mixture.
- the paste so obtained produces on cellulose acetate artificial silk blue dyeings of great purity. It enables dark blue tints to be obtained which are darker than those obtainable with the individual components of the mixture or can be obtained therewith only by using a very much greater quantity of dyestuff and then not in the same degree of purity.
- Example 2 By using in the procedure of Example 1, 6 parts, instead of 4 parts, of l-(p-hydroxethyl)-amino- 4-phenylamino-anthraquinone and 2 parts, instead of 4 parts, of l-methylamino--phenylamino-anthraquinone, there are obtained similar 3 results which approach closely the good results obtained in Example 1.
- Example 3 10 parts of a paste of 10 per cent strength of finely dispersed l-(fl-hydroxyethyl) amino-ephenylaminoanthraquinone and 10 parts of a paste of 10 per cent. strength of l-methylamino- 4-phenylamino-anthraquinone are introduced into a solution of 6 parts of the sodium salt of N- benzyl,u-heptadecyl benzimidazole disulfonic acid in 200 parts of water at 30 0., and 3000 parts of water at 40 C. are added while stirring well. 100 parts of well wetted cellulose acetate artificial sill: are entered at 40 C., the temperature is raised to 80 C. in the course of hour, and dyeing is carried on at that temperature for one hour. The artificial silk is then rinsed and finished in the usual manner. A deep blue dyeingis obtained of great purity.
- Example 4 The procedure is the same as that described in Example 3, except that 20 parts of a dyestuii paste are used containing 10 per cent. of the dyestuii mixture and prepared as described in Example l or 2. Very similar results are ob tained.
- the amount of dispersing agent contained in the dyestuii preparations is not critical and may range from one tenth to many times the combined weight of the two dyestuffs.
- the dispersing agent may be omitted altogether if care is taken that, nevertheless, the dyebath prepared with the prepara tion contains the dyestuffs in finely dispersed condition.
- the dyestuff preparations may be aqueous pastes or thinly liquid dispersions or they may be dried, for example in an atomizer, especially if the amount of dispersing agent is not too low.
- acetate rayon dyes other than those specified above, may
- a dyestuff preparation in which the dyeing constituent consists mainly of a mixture or" 1-([3- hydroxyethyl) aminol-phenylamino anthraquinone and 1-methylamino-4-phenylaminoanthraquinone in a finely divided and dispersible condition and in relative proportions ranging from about 4:1 to 1:4, the said anthraquinone compounds being substantially free from impurities possessing afiinity for acetate rayon.
- a dyestuff preparation consisting of Water, a dispersing agent, and approximately equal quantities or l-(fi-hydrcxyethyl) -amino-4-phenylaminoanthraquinone and l-methyl amino-ephenylaminoanthraquinone in a finely divided and dispersible condition.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Coloring (AREA)
Description
Patented May 2, 1950 MIXTURE OF INSOLUBLE AMINO- ANTHRAQUINONE DYES Paul Grossmann, Binningen, and Walter Kern, Sissach, Switzerland, assignors to Ciba Limited,
a Swiss firm No Drawing. Application September 14, 1948, Se-
rial No. 49,292. In Switzerland November 26,
Claims.
It is known that mixtures of dyestuffs are in some cases of advantage for dyeing cellulose esters, for example, artificial silk or staple fibers of lower fatty acids of cellulose, such as cellulose butyrate, cellulose propionate and especially cellulose acetate, and also the corresponding mixed esters. The use of mixtures of dyestuffs is indicated, inter alia, when the dyestuif mixture is required not for producing a desired shade of color but when each of the dyestuffs to be mixed yields dyeings of the same tint or very similar tints, owing to the fact that in many cases such a mixture yields a stronger tint than do the individual pure components of the mixture. This so-called mixture effect varies in strength in difierent instances. It naturally also occurs when by-products are formed in the manufacture of a single dyestufi and the by-products remain in the final dyestuif. Especially pronounced mixture effects, that is to say those in which the resulting mixed dyeing is very considerably stronger than the dyeings obtainable with the stronger-dyeing component of the mixture, are rare. Moreover, a dyeing of enhanced purity is not to be expected by the use of mixtures, and in some cases, as would be expected, the mixed dyeing is more or less markedly dull.
The present invention is based on the observation that unexpectedly good dyeings on cellulose esters are obtained by using mixtures of which the dyeing constituents consist mainly of l-(c-hydroxyethyl) amino 4 phenylamino anthraquinone and l methylamino 4 phenylamino- .anthraquinone in finely divided form.
As cellulose esters to be dyed by the process of this invention there may be used the known esters of cellulose with aliphatic acids of low molecular weight mentioned above. The fibers of some cellulose ethers and of superpolyamides, superpolyurethanes and superpolyesters are to be regarded as equivalents of fibers of cellulose esters, owing to their similar properties.
The individual components of the mixture, namely 1 (fl-hydroxyethyl) -amino 4 phenylamlno anthraquinone and 1 methylamino- 4-phenylamino-anthraquinone, are in themselves known and can be obtained in various ways. It is of advantage to use them in the present process in a pure or relatively pure state. They may be converted in known manner into a finely divided condition prior to the dyeing process, for example, by grinding with a dispersing agent such as sulfite cellulose waste liquor, advantagefuric acid.
The two components may be mixed together before or during the preparation of the dyebath. The relative proportions of the components may vary within fairly wide limits, but it is of advantage to use not less than 20 per cent, preferably 25-50 per cent, of the component which is present in lower proportion.
Dyeing may be carried out in the usual manner, for example, in aqueous dispersion with the addition of a wetting or dispersing agent such as a soap, an N-benzyl- -heptadecyl-benzimidazole sulfonic acid, a condensation product of taurine or methyl-taurine with a fatty acid, or the like.
It is also of advantage to make a dyestuff preparation which contains the two components mentioned above in the desired relative proportions and in a state of fine dispersion and also contains a wetting or dispersing agent such as sulfite cellulose waste liquor, salts of condensation products from formaldehyde and naphthalene sulfonic acids, naphthenic acid salts, if desired with the addition of wetting agents, such as are mentioned above.
The following examples illustrate the invention, the parts being by weight:
Example 1 4 parts of 1 ([3 hydroxyethyl) amino- 4 phenylamino-anthraquinone and 4 parts of 1 methylamino-4-phenylamino anthraquinone are dissolved in 50 parts of sulfuric acid of per cent. strength. The solution is introduced into a mixture of parts of ice, 240 parts of water and 55 parts of ammonia solution of 25 per cent. strength, stirred well and filtered. The filter residue is washed neutral and ground with about 12 parts of dried sulfite cellulose waste liquor and the necessary quantity of water to form a dyestuif paste containing about 10 per cent. of the dyestufi mixture.
The paste so obtained produces on cellulose acetate artificial silk blue dyeings of great purity. It enables dark blue tints to be obtained which are darker than those obtainable with the individual components of the mixture or can be obtained therewith only by using a very much greater quantity of dyestuff and then not in the same degree of purity.
Example 2 By using in the procedure of Example 1, 6 parts, instead of 4 parts, of l-(p-hydroxethyl)-amino- 4-phenylamino-anthraquinone and 2 parts, instead of 4 parts, of l-methylamino--phenylamino-anthraquinone, there are obtained similar 3 results which approach closely the good results obtained in Example 1.
Similar results are obtained by using 2 parts of 1 -(,8-hydroxyethy1) amino-e-phenylaminoanthraquinone and 6 parts of l-methyiaminoiphenylamino-anthraquinone.
Example 3 10 parts of a paste of 10 per cent strength of finely dispersed l-(fl-hydroxyethyl) amino-ephenylaminoanthraquinone and 10 parts of a paste of 10 per cent. strength of l-methylamino- 4-phenylamino-anthraquinone are introduced into a solution of 6 parts of the sodium salt of N- benzyl,u-heptadecyl benzimidazole disulfonic acid in 200 parts of water at 30 0., and 3000 parts of water at 40 C. are added while stirring well. 100 parts of well wetted cellulose acetate artificial sill: are entered at 40 C., the temperature is raised to 80 C. in the course of hour, and dyeing is carried on at that temperature for one hour. The artificial silk is then rinsed and finished in the usual manner. A deep blue dyeingis obtained of great purity.
Example 4 The procedure is the same as that described in Example 3, except that 20 parts of a dyestuii paste are used containing 10 per cent. of the dyestuii mixture and prepared as described in Example l or 2. Very similar results are ob tained.
It is to be understood that the amount of dispersing agent contained in the dyestuii preparations is not critical and may range from one tenth to many times the combined weight of the two dyestuffs. The dispersing agent may be omitted altogether if care is taken that, nevertheless, the dyebath prepared with the prepara tion contains the dyestuffs in finely dispersed condition.
If desired, the dyestuff preparations may be aqueous pastes or thinly liquid dispersions or they may be dried, for example in an atomizer, especially if the amount of dispersing agent is not too low.
It is further to be understood that acetate rayon dyes, other than those specified above, may
be present as impurities or purposely added to the preparations in minor amounts, for example if not all of the beneficial effects of the present invention are required, or if the dyes added do not interfere therewith.
What we claim is:
1. A dyestuff preparation in which the dyeing constituent consists mainly of a mixture or" 1-([3- hydroxyethyl) aminol-phenylamino anthraquinone and 1-methylamino-4-phenylaminoanthraquinone in a finely divided and dispersible condition and in relative proportions ranging from about 4:1 to 1:4, the said anthraquinone compounds being substantially free from impurities possessing afiinity for acetate rayon.
2. A dyestuii preparation containing a dispersing agent in which the dyeing constituent consists mainly of a mixture of l-(B-hydroxyethyl) amino 4 phenylaminoanthraquinone and 1- methyl-amino-4-phenylaminoanthraqulnone in a finely divided and dispersible condition and in relative proportions ranging from about 4:1 to 1:4.
3. A dyestuif preparation containing a dispers- 3 ing agent in which the dyeing constituent consists of a mixture of lJB-hydroxyethyl) -aminophenylaminoanthraquinone and 1methyl-amino-' i-phenylaminoanthraquinone in a finely divided and dispersible condition and in approximately equal quantities.
A dyestuif preparation containing a dispersing agent in which the dyeing constituent consists of a mixture of l-(B-hydroxyethyl) -amino- 4 phenylaminoanthraquinone and l methylaminoA-phenylaminoanthraquinone in a finely divided and dispersible condition and in relative proportions ranging from about 4:1 to 1:4, the said anthraquinone compounds being substantial- 1y free from impurities possessing affinity for acetate rayon.
5. A dyestuff preparation consisting of Water, a dispersing agent, and approximately equal quantities or l-(fi-hydrcxyethyl) -amino-4-phenylaminoanthraquinone and l-methyl amino-ephenylaminoanthraquinone in a finely divided and dispersible condition.
PAUL GROSSMANN. WALTER KERN.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,967,772 Grossmann July 24, 1934 2,060,186 Felix Nov. 10, 1936 2,272,294 Finlayson Feb. 10, 1942 2,342,191 Grossmann Feb. 22, 1944
Claims (1)
1. A DYESTUFF PREPARATION IN WHICH THE DYEING CONSTITUENT CONSISTS MAINLY OF A MIXTURE OF 1-(BHYDROXYETHYL) - AMINO-4-PHENYLAMINO - ANTHRAQUINONE AND 1-METHYLAMINO-4-PHENYLAMINOANTHRAQUINONE IN A FINELY DIVIDED AND DISPERSIBLE CONDITION AND IN RELATIVE PROPORTIONS RANGING FROM ABOUT 4:1 TO 1:4, THE SAID ANTHRAQUINONE COMPOUNDS BEING SUBSTANTIALLY FREE FROM IMPURITIES POSSESSING AFFINITY FOR ACETATE RAYON.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2506020X | 1947-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2506020A true US2506020A (en) | 1950-05-02 |
Family
ID=4569719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US49292A Expired - Lifetime US2506020A (en) | 1947-11-26 | 1948-09-14 | Mixture of insoluble aminoanthraquinone dyes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2506020A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| US3210345A (en) * | 1961-07-03 | 1965-10-05 | Ici Ltd | Phthalocyanine dyestuffs |
| US3264052A (en) * | 1962-01-05 | 1966-08-02 | Ciba Ltd | Process for dyeing polyester fibers |
| US3520648A (en) * | 1966-12-22 | 1970-07-14 | Geigy Ag J R | Process for dyeing organic polyester fibers and composite anthraquinone preparations therefor |
| US3755201A (en) * | 1971-07-26 | 1973-08-28 | Colgate Palmolive Co | Laundry product containing mixed dye bluing agents |
| 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 |
| WO2018177652A1 (en) * | 2017-03-29 | 2018-10-04 | Huntsman Advanced Materials (Switzerland) Gmbh | Process for printing cellulose containing textile fibre material |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1967772A (en) * | 1932-09-20 | 1934-07-24 | Chem Ind Basel | 1-alkylamino-4-arylaminoanthraquinones and process of making such products |
| US2060186A (en) * | 1932-10-15 | 1936-11-10 | Soc Of Chemical Ind | Dyeing of acetate artificial silk |
| US2272294A (en) * | 1938-07-23 | 1942-02-10 | Celanese Corp | Laminated materials |
| US2342191A (en) * | 1939-06-10 | 1944-02-22 | Soc Of Chemical Ind | Dyeing and printing cellulose esters and ethers with amino-anthraquinone dyes |
-
1948
- 1948-09-14 US US49292A patent/US2506020A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1967772A (en) * | 1932-09-20 | 1934-07-24 | Chem Ind Basel | 1-alkylamino-4-arylaminoanthraquinones and process of making such products |
| US2060186A (en) * | 1932-10-15 | 1936-11-10 | Soc Of Chemical Ind | Dyeing of acetate artificial silk |
| US2272294A (en) * | 1938-07-23 | 1942-02-10 | Celanese Corp | Laminated materials |
| US2342191A (en) * | 1939-06-10 | 1944-02-22 | Soc Of Chemical Ind | Dyeing and printing cellulose esters and ethers with amino-anthraquinone dyes |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| US3210345A (en) * | 1961-07-03 | 1965-10-05 | Ici Ltd | Phthalocyanine dyestuffs |
| US3264052A (en) * | 1962-01-05 | 1966-08-02 | Ciba Ltd | Process for dyeing polyester fibers |
| US3520648A (en) * | 1966-12-22 | 1970-07-14 | Geigy Ag J R | Process for dyeing organic polyester fibers and composite anthraquinone preparations therefor |
| US3989449A (en) * | 1969-03-04 | 1976-11-02 | L. B. Holliday & Co. Limited | Dyestuff compositions |
| US3755201A (en) * | 1971-07-26 | 1973-08-28 | Colgate Palmolive Co | Laundry product containing mixed dye bluing agents |
| US3881865A (en) * | 1972-06-02 | 1975-05-06 | Ici Ltd | Anthraquinone dyestuff mixtures |
| WO2018177652A1 (en) * | 2017-03-29 | 2018-10-04 | Huntsman Advanced Materials (Switzerland) Gmbh | Process for printing cellulose containing textile fibre material |
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