US2902472A - Production of dicyandiamide triethylene tetramine formaldehyde condensate - Google Patents
Production of dicyandiamide triethylene tetramine formaldehyde condensate Download PDFInfo
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- US2902472A US2902472A US493046A US49304655A US2902472A US 2902472 A US2902472 A US 2902472A US 493046 A US493046 A US 493046A US 49304655 A US49304655 A US 49304655A US 2902472 A US2902472 A US 2902472A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/28—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to cyano groups, e.g. cyanoguanidines, dicyandiamides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
- D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
- D06P1/56—Condensation products or precondensation products prepared with aldehydes
Definitions
- the present invention relates to products and processes for treatment of fabrics dyed with direct dyestuffs to increase the fastness of the dyestuffs to wet treatments including laundering.
- Another object is to provide novel textile assistant compositions which when utilized in a finishing bath will impart to dyed fabrics substantial resistance to alkaline treatments at a wide range of temperatures with a minimum of deleterious effect upon the fabric.
- polyethylene polyarnines which may be used are triethylene tetramine (preferred), diethylene triamine and ethylene diamine.
- This condensation product for the use of the invention is preferably formed in the presence of a Water soluble, low molecular weight aliphatic acid, such as propionic, lactic, acetic or formic, at a controlled pH of 4.5 to 6.0 at a controlled temperature range of 75 85 C.
- a Water soluble, low molecular weight aliphatic acid such as propionic, lactic, acetic or formic
- the organic acid should have 1 to 6 carbon atoms and the acid may contain from to 3 hydroXy groups and from 1 to 3 carboxy groups. Less preferred are citric, tartaric, maleic, succinic or fumaric acid.
- An important feature of the present invention resides in the fact that there is no formation of insoluble matter during the reaction carried out by our process, even after standing for several months at ordinary room temperatures (70 to 90 F.).
- the degree of polymerization is controlled so that a water soluble condensate of relatively low molecular weight is formed, without giving rise to side reactions which may yield products of relatively high molecular weight and low water solubility.
- the mixture was then cooled to 82 C., and maintained at 78 to 82 C. for about two hours.
- the mixture was then rapidly cooled to room temperature.
- Cloth was then rinsed thoroughly and dried.
- the aftertreated cloth is fast to bleeding in water.
- the aftertreated cloth was subjected to a 0.5% soap solution for 30 minutes at C. in a launderorneter with 10 steel balls.
- This last-mentioned treatment is hereafter referred to as a #2 AATCC test.
- the viscous, aqueous solution was cooled rapidly to room temperature.
- a cotton fabric dyed withDirect Red B (Color Index 419) was aftertreated at 30 to 1 bath ratio for 20 minutes at F. with 6.5% of this reaction product based on the weight of the fabric, and then rinsed with hot water and finally with cold water. The fabric was then sub jected to a #2 AATCC washing test.
- This treatment increased considerably the resistance of the dyeing to bleeding and washing at 120 F.
- Cotton cloth dyed with 1 /2% Direct Blue Green BL (Color Index 470) was aftertreated with 4.5% of the reaction product based on the weight of the fabric, plus 0.5% acetic acid-56% strength-for 20 minutes at 180 F. The cloth was then thoroughly rinsed and dried.
- This treatment made the dyeing resistant to #2 AATCC washing.
- the mixture was treated for 1% hours at 78 to 82 C.
- This treatment rendered the dyeing resistant to the #2 AATCC washing.
- Cotton cloth dyed with 2% Direct Brown BRL (Prototype 49) was aftertreated with 6.4% of the reaction product based on the weight of the fabric, using the same procedure as in Example No. 5.
- This treatment rendered the dyeing fast to bleeding in water and to #2 AATCC washing.
- Cotton cloth dyed with 2% Direct Brown BRL (Prototype 49) was aftertreated with 6.8% of the reaction product based on the weight of the fabric, according to the procedure used in Example No. 5.
- This treatment rendered dyeing fast to bleeding in water and to #2 AATCC washing.
- Cotton cloth dyed with 2% Direct Brown BRL (Prototype 47) was aftertreated for 20 minutes at 180 F. with 7.0% of the reaction product based upon the weight of the fabric. The cloth was then washed and dried.
- This treatment made the dyeing quite fast to bleeding in water and to #2 AATCC washing.
- the resultant treatment makes the dyeing more resistant to #2 AATCC washing.
- the product of this invention is chiefly recommended for use as an aftertreatment on fabrics dyed with direct dyestuffs to increase the fastness of hot alkaline treatments or launderings.
- the amount of the product used depends upon the depth of shade of the fabric in question, usually from 2% to 10% on the weight of the material together with a small amount of water soluble organic acid, if desired.
- compositions of this invention may be used as a pretreatment and in this way acts as a mordant for the dyestuffs.
- Such treatments are usually not as effective as aftertreatments in regard to resistance to bleeding and laundering.
- the products of this invention may also be used in connection with copper salts, such as copper chloride, and/or copper acetate, in dyeing procedures when dyes selected from a group suitable for use with copper salts are employed. As a result of such procedures, better wash-fastness is usually obtained as well as improved lightfastness.
- copper salts such as copper chloride, and/or copper acetate
- a nitrogenous base compound preferably dicyandiamide and less preferably urea, guanidine, acrylamide and l l 1 l l thiourea in amounts of V2 to 2 mols and preferably in amount of 1 mol.
- a polyalkylene polyamine such as tn'ethylene tetramine, diethylene triamine and ethylene diamine in amounts of A: to /2 mol and preferably 4 mol.
- a paraformaldehyde may be used in the presence of methyl alcohol, which functions as a methylating agent.
- the basic reaction that takes place is a combination in the fiber itself between the cationic condensation product of the two or three nitrogenous compounds above specified and the formaldehyde together with anionic dyestuff and this combination in the actual textile fiber is highly resistant to washing tests.
- the acid is used in aqueous condition, it is preferably added in water solution with cooling to the mixed nitrogenous bases.
- reaction mixture is heated.
- Process for the production of a condensation product suitable for the treatment of fabrics dyed with a direct dyestufi to increase the fastness properties of said dye stuff which comprises heating to a temperature of C. a mixture of about 3 mol of dicyandiamide, about mol of tn'ethylene tetramine and about 1% mols of formaldehyde 37%, the reaction mixture also containing water and acetic acid in an amount sufficient to maintain the pH of said reaction mixture within a range of about 4.5 to 6, and immediately after the initiation of the reaction maintaining the temperature of the reaction mixture for the balance of the course of the reaction at to C., the temperature at no time being allowed to exceed about C., the time of the reaction being from 1% to 5 hours.
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- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Coloring (AREA)
Description
gen:
2,902,472 Patented Sept. 1, 1959 PRODUCTION OF DICYANDIAMIDE TRIETHYL- ENE TETRAMINE FORMALDEHYDE CONDEN- SATE Alton A. Cook, Glen Ridge, and Ira Sapjers, Newark, N.J., assignors to Arkansas Company, Inc., Newark, NJ a corporation of New York No Drawing, Application March 8, 1955 Serial No. 493,046
1 Claim. (Cl. 260- 70) The present invention relates to products and processes for treatment of fabrics dyed with direct dyestuffs to increase the fastness of the dyestuffs to wet treatments including laundering.
It is among the objects of the present invention to provide pretreatments and aftertreatments and the assistants for such purposes for application to dyed fabrics which will render such dyed fabrics fast to hotalkaline treatments with little or no change in color value It is a further object of this invention to provide textile assistant compositions which are readily and practically employed in the treatment of textile fabrics both before and after dyeing.
Another object is to provide novel textile assistant compositions which when utilized in a finishing bath will impart to dyed fabrics substantial resistance to alkaline treatments at a wide range of temperatures with a minimum of deleterious effect upon the fabric.
Still further objects and advantages will appear in the more detailed description set forth below, it being understood, however, that this more detailed description is given by way of illustration and explanation only and not by Way of limitation, since various changes therein may be made by those skilled in the art without departing from the scope and spirit of the present invention.
In accomplishing the above objects it has been found highly satisfactory to treat the fabric, after it has been dyed, with a condensation product of a nitrogenous compound such as dicyandiamide, acrylamide, urea or guanidine on the one hand; low molecular polyethylene polyamines on the second hand; and formaldehyde on the third hand.
Some of the polyethylene polyarnines which may be used are triethylene tetramine (preferred), diethylene triamine and ethylene diamine.
This condensation product for the use of the invention is preferably formed in the presence of a Water soluble, low molecular weight aliphatic acid, such as propionic, lactic, acetic or formic, at a controlled pH of 4.5 to 6.0 at a controlled temperature range of 75 85 C.
The organic acid should have 1 to 6 carbon atoms and the acid may contain from to 3 hydroXy groups and from 1 to 3 carboxy groups. Less preferred are citric, tartaric, maleic, succinic or fumaric acid.
In the present invention particular care is used to control the pH of the reaction so as to keep it on the acid side at all times and the preferred pH range is 4.8 to 5.5
with a broader range of 4.5 to 6.5.
An important feature of the present invention resides in the fact that there is no formation of insoluble matter during the reaction carried out by our process, even after standing for several months at ordinary room temperatures (70 to 90 F.).
In the present invention the degree of polymerization is controlled so that a water soluble condensate of relatively low molecular weight is formed, without giving rise to side reactions which may yield products of relatively high molecular weight and low water solubility.
2 To give specific examples of this invention:
Example N0. 1
67.0 parts by weight dicyandiamide (about moi) 29.0 parts by Weight triethylene tetramine about mol) 110.0 parts by weight formaldehyde 37% (about 1 /3 mol) 30.0 parts by weight acetic acid (about /2 Incl) 40.0 parts by weight water A reactor was charged with dicyandiamide and triethylene tetramine. Acetic acid dissolved in water was then added, and finally the formaldehyde was added. The mixture was then heated slowly to 60 C.,. whereupon the temperature jumped automatically to 90 C.
The mixture was then cooled to 82 C., and maintained at 78 to 82 C. for about two hours.
The mixture was then rapidly cooled to room temperature.
A cotton muslin, dyed with 2% Direct Brown BRL (prototype 47), was aftertreated for 20 minutes at 160 F. at a 30 to 1 ratio bath with 6.5% of this reaction product based on the weight of the fabric.
Cloth was then rinsed thoroughly and dried.
The aftertreated cloth is fast to bleeding in water.
The aftertreated cloth was subjected to a 0.5% soap solution for 30 minutes at C. in a launderorneter with 10 steel balls.
This last-mentioned treatment is hereafter referred to as a #2 AATCC test.
There is no loss in color and the white cloth was only slightly stained. 1
Example N0. 2
84 parts by Weight dicyandiamide (about 1 mol) 15 parts by weight triethylene tetramine (about mol) 110 parts by Weight formaldehyde 37% (about 1% mol) 14 parts by Weight formic acid 90% (about /1 mol) 46 parts by Weight water A reactor was charged with the 'dicyandiamide; the triethylene tetramine and the formic acid. The Water was added and then the formaldehyde. The mixture raised slowly to 75 C. Then the heating was stopped and the temperature jumped automatically to 82? For about two hours the temperature was maintained at 78 to 82 C., with constant stirring.
The viscous, aqueous solution was cooled rapidly to room temperature.
A cotton fabric dyed withDirect Red B (Color Index 419) was aftertreated at 30 to 1 bath ratio for 20 minutes at F. with 6.5% of this reaction product based on the weight of the fabric, and then rinsed with hot water and finally with cold water. The fabric was then sub jected to a #2 AATCC washing test.
Compared with untreated cloth, it lost only little of the original color.
Example N0. 3
84 parts by weight dicyandiamide (about 1 mol) 34 parts by weight diethylene triamine (about /3 mol) 164 parts by weight lactic acid 44% (about 0.8 mol) 110partsby weight. formaldehyde 37% (about 1 /3 moi) type 49 was aftertreated with 6.5% of the reaction BRL (Protoproduct based on the weight of the fabric, according to procedure in Example No. 2.
This treatment increased considerably the resistance of the dyeing to bleeding and washing at 120 F.
Example N0. 4
84 parts by weight dicyandiamide (about 1 mol) 60 parts by weight acetic acid 100% (about 1 mol) 75 parts by weight triethylene tetramine (about /2 mol) 110 parts by weight formaldehyde 37% (about 1% mol) 60 parts by weight water The dicyandiamide was added to the acetic acid, which was diluted with water. The triethylene tetramine was then added and finally the formaldehyde. The mixture was then heated at 78 to 82 C. for about 3 hours and then cooled to room temperature.
Cotton cloth dyed with 1 /2% Direct Blue Green BL (Color Index 470) was aftertreated with 4.5% of the reaction product based on the weight of the fabric, plus 0.5% acetic acid-56% strength-for 20 minutes at 180 F. The cloth was then thoroughly rinsed and dried.
This treatment made the dyeing resistant to #2 AATCC washing.
Example N0. 5
84 parts by weight dicyandiamide (about 1 mol) parts by weight triethylene tetramine (about mol) 30 parts by weight acetic acid, glacial (about /2 mol) 163 parts by weight formaldehyde 37% (about 2 mol) 40 parts by weight water The acetic acid diluted in water was added to a mix ture of dicyandiamide and triethylene tetramine in a vessel, and then the formaldehyde was added.
The mixture was treated for 1% hours at 78 to 82 C.
Cotton cloth dyed with 2% Direct Blue FF (Color Index 518) was aftertreated for minutes at 160 F. with 8% of this product.
This treatment rendered the dyeing resistant to the #2 AATCC washing.
Example No. 6
67.0 parts by weight dicyandiamide (about /s mol) 14.0 parts by weight acrylamide (about /5 mol) 21 parts by weight diethylene triamine (about /5 mol) 40.0 parts by weight acetic acid, glacial (about mol) 123.0 parts by weight formaldehyde 37% (about 1% mol) 50.0 parts by weight water The reaction procedure was the same as in Example No. 5.
Cotton cloth dyed with 2% Direct Brown BRL (Prototype 49) was aftertreated with 6.4% of the reaction product based on the weight of the fabric, using the same procedure as in Example No. 5.
This treatment rendered the dyeing fast to bleeding in water and to #2 AATCC washing.
Example N 0. 7
67.0 parts by weight dicyandiamide (about mol) 38 parts by weight triethylene tetramine (about A mol) 12.0 parts by weight urea (about /5 mol) 110 parts by weight formaldehyde 37% (about 1% mol) 45 parts by weight acetic acid, glacial (about mol) 60.0 parts by weight water The reaction procedure was the same as in Example 5.
Cotton cloth dyed with 2% Direct Brown BRL (Prototype 49) was aftertreated with 6.8% of the reaction product based on the weight of the fabric, according to the procedure used in Example No. 5.
This treatment rendered dyeing fast to bleeding in water and to #2 AATCC washing.
Example N0. 8
63.0 parts by weight dicyandiamide (about mol) 47.0 parts by weight guanidine carbonate (about 4 mol) 20 parts by weight ethylene diamine 77% (about mol) 60.0 parts by weight acetic acid, glacial (about 1 mol) 122.0 parts by weight formaldehyde 37% (about 1% mol) 40.0 parts by weight water The acetic acid, dissolved in water, was slowly added to mixture of dicyandiamide, guanidine carbonate and ethylene diamine, and then formaldehyde was added. The temperature was slowly raised to 80 C. under constant stirring. The mixture was treated at 80 to C. for 1% hours.
Cotton cloth dyed with 2% Direct Brown BRL (Prototype 47) was aftertreated for 20 minutes at 180 F. with 7.0% of the reaction product based upon the weight of the fabric. The cloth was then washed and dried.
This treatment made the dyeing quite fast to bleeding in water and to #2 AATCC washing.
Erample N0. 9
84 parts by weight dicyandiamide 39 parts by weight ethylene diamine 77% (about /2 mol) 163 parts by weight formaldehyde 37% (about 2 mol) 51 parts by weight formic acid (about 1 mol) 60 parts by weight water Formic acid, diluted with water, was added to mixture of dicyandiamide and ethylene diamine with cooling and stirring. Then the formaldehyde was added under the same conditions. The temperature was slowly raised to 80 C. and maintained for 5 hours.
Cotton cloth, dyed with Direct Blue FF (Color Index 518) was aftertreated with 8% of the reaction product based on the weight of the fabric for 20 minutes at F.
The resultant treatment makes the dyeing more resistant to #2 AATCC washing.
Variations in the above formula are permissible but the proportion of formaldehyde should always be in the range of 1 to 2 mols to each mol of dicyandiamide or other nitrogenous component.
Variations are permissible in the type and amount of acid used with the restrictions that the acid must be a low molecular weight water soluble organic acid having 1 to 6 carbon atoms.
The product of this invention is chiefly recommended for use as an aftertreatment on fabrics dyed with direct dyestuffs to increase the fastness of hot alkaline treatments or launderings.
In this application the amount of the product used depends upon the depth of shade of the fabric in question, usually from 2% to 10% on the weight of the material together with a small amount of water soluble organic acid, if desired.
In some cases the compositions of this invention may be used as a pretreatment and in this way acts as a mordant for the dyestuffs. Such treatments are usually not as effective as aftertreatments in regard to resistance to bleeding and laundering.
The products of this invention may also be used in connection with copper salts, such as copper chloride, and/or copper acetate, in dyeing procedures when dyes selected from a group suitable for use with copper salts are employed. As a result of such procedures, better wash-fastness is usually obtained as well as improved lightfastness.
In general, in the above examples there was always one or more mols of formaldehyde for each mol of nitrogenous organic base and the molar proportion of dicyandiamide always exceeded the molar proportion of the polyamine.
In general the following ingredients were employed and condensed together:
(a) A nitrogenous base compound, preferably dicyandiamide and less preferably urea, guanidine, acrylamide and l l 1 l l thiourea in amounts of V2 to 2 mols and preferably in amount of 1 mol.
(b) A polyalkylene polyamine such as tn'ethylene tetramine, diethylene triamine and ethylene diamine in amounts of A: to /2 mol and preferably 4 mol.
(c) Formaldehyde in amount of /2 to 4 mols and preferably 1 to 2 mols.
Where it is desired to use anhydrous conditions, or a waterless system, a paraformaldehyde may be used in the presence of methyl alcohol, which functions as a methylating agent.
The molar proportions above are employed under these conditions except that the methyl alcohol is used in molar proportion ranging from /2 to 2 mols for each free NH, group.
The basic reaction that takes place is a combination in the fiber itself between the cationic condensation product of the two or three nitrogenous compounds above specified and the formaldehyde together with anionic dyestuff and this combination in the actual textile fiber is highly resistant to washing tests.
Where the acid is used in aqueous condition, it is preferably added in water solution with cooling to the mixed nitrogenous bases.
Following the addition of the acid, the formaldehyde in aqueous solution is also added slowly with cooling.
As a final operation, the reaction mixture is heated.
As many changes could be made in the above process for aftertreatment of dyed fabrics due to improve the wash fastness of dyes, and many widely different embodiments of this invention could be made without departing from th s p f t e laim, i is ia eus esl t at all ma ter antained in the above description shall be interpreted as illustrative and not in a limiting sense.
Having now particularly described and ascertained the nature of the invention, and in what manner the same is to be performed, what is claimed is:
Process for the production of a condensation product suitable for the treatment of fabrics dyed with a direct dyestufi to increase the fastness properties of said dye stuff, which comprises heating to a temperature of C. a mixture of about 3 mol of dicyandiamide, about mol of tn'ethylene tetramine and about 1% mols of formaldehyde 37%, the reaction mixture also containing water and acetic acid in an amount sufficient to maintain the pH of said reaction mixture within a range of about 4.5 to 6, and immediately after the initiation of the reaction maintaining the temperature of the reaction mixture for the balance of the course of the reaction at to C., the temperature at no time being allowed to exceed about C., the time of the reaction being from 1% to 5 hours.
References Cited in the file of this patent UNITED STATES PATENTS 2,214,067 Petersen Sept. 10, 1940 2,364,726 Landolt Dec. 12, 1944 2,366,129 Rust Dec. 26, 1944 2,405,863 Treboux Aug. 13, 1946 2,622,075 Hemmi Dec. 16, 1952 2,631,920 Albrecht Mar. 17, 1953 L647???
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US493046A US2902472A (en) | 1955-03-08 | 1955-03-08 | Production of dicyandiamide triethylene tetramine formaldehyde condensate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US493046A US2902472A (en) | 1955-03-08 | 1955-03-08 | Production of dicyandiamide triethylene tetramine formaldehyde condensate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2902472A true US2902472A (en) | 1959-09-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US493046A Expired - Lifetime US2902472A (en) | 1955-03-08 | 1955-03-08 | Production of dicyandiamide triethylene tetramine formaldehyde condensate |
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| Country | Link |
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| US (1) | US2902472A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2955050A (en) * | 1956-07-17 | 1960-10-04 | Geigy Ag J R | Water fastness of metal lakes of azo dyestuffs containing sulphonic acid groups |
| DE1292860B (en) * | 1965-06-26 | 1969-04-17 | Pfersee Chem Fab | Process for the production of water-soluble, nitrogen-containing condensation products |
| FR2513278A1 (en) * | 1981-06-15 | 1983-03-25 | Sandoz Sa | Treating dyed cellulosic fibrous substrates with precondensate - to improve wet fastness and crease resistance |
| FR2513279A1 (en) * | 1981-05-18 | 1983-03-25 | Sandoz Sa | Treating dyed cellulosic fibrous substrates with precondensate - to improve wet fastness and crease resistance |
| CH673195GA3 (en) * | 1981-05-14 | 1990-02-28 |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2214067A (en) * | 1937-07-03 | 1940-09-10 | Gen Aniline & Film Corp | Process for improving the fastness of dyeings |
| US2364726A (en) * | 1938-12-21 | 1944-12-12 | Firm Ciba Products Corp | Process for improving the dyeings and prings prepared with watersoluble dyestuffs |
| US2366129A (en) * | 1942-08-04 | 1944-12-26 | Montclair Res Corp | Water-soluble resinous products and process of making |
| US2405863A (en) * | 1942-06-22 | 1946-08-13 | Geigy Ag J R | Dicyanodiamide-ammonia condensation products and process for making same |
| US2622075A (en) * | 1946-12-03 | 1952-12-16 | Sandoz Ltd | Polyamine-cyanamide resins |
| US2631920A (en) * | 1948-11-24 | 1953-03-17 | Ciba Ltd | Compositions for the improvement of fastness properties of dyeings and printings of water-soluble dyestuffs |
| US2649354A (en) * | 1947-12-01 | 1953-08-18 | Sandoz Ltd | Process for improving fastiness properties of direct dyestuffs |
-
1955
- 1955-03-08 US US493046A patent/US2902472A/en not_active Expired - Lifetime
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2214067A (en) * | 1937-07-03 | 1940-09-10 | Gen Aniline & Film Corp | Process for improving the fastness of dyeings |
| US2364726A (en) * | 1938-12-21 | 1944-12-12 | Firm Ciba Products Corp | Process for improving the dyeings and prings prepared with watersoluble dyestuffs |
| US2405863A (en) * | 1942-06-22 | 1946-08-13 | Geigy Ag J R | Dicyanodiamide-ammonia condensation products and process for making same |
| US2366129A (en) * | 1942-08-04 | 1944-12-26 | Montclair Res Corp | Water-soluble resinous products and process of making |
| US2622075A (en) * | 1946-12-03 | 1952-12-16 | Sandoz Ltd | Polyamine-cyanamide resins |
| US2649354A (en) * | 1947-12-01 | 1953-08-18 | Sandoz Ltd | Process for improving fastiness properties of direct dyestuffs |
| US2631920A (en) * | 1948-11-24 | 1953-03-17 | Ciba Ltd | Compositions for the improvement of fastness properties of dyeings and printings of water-soluble dyestuffs |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2955050A (en) * | 1956-07-17 | 1960-10-04 | Geigy Ag J R | Water fastness of metal lakes of azo dyestuffs containing sulphonic acid groups |
| DE1292860B (en) * | 1965-06-26 | 1969-04-17 | Pfersee Chem Fab | Process for the production of water-soluble, nitrogen-containing condensation products |
| US3491064A (en) * | 1965-06-26 | 1970-01-20 | Pfersee Chem Fab | Process for producing water-soluble nitrogen-containing products by reacting a compound containing a group with formaldehyde and free amines |
| CH673195GA3 (en) * | 1981-05-14 | 1990-02-28 | ||
| FR2513279A1 (en) * | 1981-05-18 | 1983-03-25 | Sandoz Sa | Treating dyed cellulosic fibrous substrates with precondensate - to improve wet fastness and crease resistance |
| FR2513278A1 (en) * | 1981-06-15 | 1983-03-25 | Sandoz Sa | Treating dyed cellulosic fibrous substrates with precondensate - to improve wet fastness and crease resistance |
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