US2930670A - Molten urea dyeing process - Google Patents

Molten urea dyeing process Download PDF

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US2930670A
US2930670A US2930670DA US2930670A US 2930670 A US2930670 A US 2930670A US 2930670D A US2930670D A US 2930670DA US 2930670 A US2930670 A US 2930670A
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urea
melting point
substance
mixture
dyeing
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    • 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
    • D06P1/64—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 low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6491—(Thio)urea or (cyclic) derivatives

Definitions

  • textiles are treated with an aqueous solution or dispersion of a dyestuff at a temperature depending on the nature of the material being dyed and the materials are left in the dyebath for a considerable period and are then rinsed and dried.
  • the dyebath may also contain one or more dyeing assistants, for example common salt or Glaubers salt or other compounds which assist the material in taking up the dye.
  • the ob ject of the present invention is to modify the process of (1.8. Serial No. 428,375 and its continuation-in-part Serial No. 668,043, filed June 26, 1957, to enable lower temperatures to be used.
  • textile materials are treated with a dyestuif in the presence of urea and one or more other substances soluble in urea and capable of lowering the melting point of the urea and are maintained at a temperature between the melting point of the mixture and 160 C.
  • the amount by which the melting point is lowered will depend on the nature and quantity of the-substance or substances added. Any suitable substance (hereinafter referred to as a melting point depressant or depressant) soluble in molten urea and capable of lowering its melting point may be used. These depressants may be used in amounts up to of the weight of the urea, or up to their maximum solubility in urea if this is less than /s.
  • the following table gives examples of suitable substances together with their maximum solubility in urea 2,930,670 Eaten-ted ,Mar. 29-, 1960 of the urea, also have a beneficial effect in reducing the tendency of the urea to decompose at elevated temperatures.
  • the melting point depressants may also be decomposition products formed in situ by heating urea above its melting point and allowing it to resolidify. If heated for a sufiicient time (for example from A to 2 hours) at a sufliciently high temperature (for example from to C.)-the resolidified urea has a lower melting point than the pure urea and can be used in the process of the present invention.
  • the following table shows the reduction in melting point obtained with different temperatures and'times of heating.
  • the method of carrying out the present invention may be similar to that described in US. Serial No. 428,375 and its continuation-in-part Serial No. 668,043, filed June 26, 1957; thus thetextile materials may be impregnated with an aqueous solution or dispersion of the urea and the melting point depressant and an aqueous solution or dispersion of the dyestufi? or a single aqueous solution or dispersion ofthe dyestufi, the urea and the melting point depressant, dried, baked to effect the dyeing, washed to remove the urea and dried.
  • the urea and the melting point depressant are preferably applied simultaneously from the same bath in an amount sufficient to give a take up of urea of 40 to 55 percent by weight of the dry textile materiaL.
  • the impregnation is preferably effected at room temperature. on the temperature used; in practice times varying from 1 /2 to 15 minutes have been found adequate.
  • the process of the present invention is suitable for dyeing with dyestuffs which are soluble in molten ureafor example direct cotton dyestuffs, dispersed acetatedyestufis, soluble acetate dyestulfs, leuco esters of vat dyestuffs, aggregated acid dyestuffs and metal complex dyestuffs. itis particularly suitable for dyeing withv direct cotton dyestuffs.
  • the process of the present invention is suitable for-dyeing those textiles which are not deleteriously affected by the baking, for example textile materials of cotton, wool, regenerated cellulose, artificial protein fibres, cellulose esters, synthetic polyamides and synthetic polyesters and materials made from mixtures of two or moreof these fibres. If the process is used for dyeing textiles from thermoplasticrfibres having a comparatively low melting point for example certain vinyl resin fibres the baking should be carried out at the lowest temperature and for the shortest time permissible.
  • the textile materials may be dyed according to the ample, the process may be applied to woven or knitted fabrics or to threads, yarns or fibres.
  • the impregnated material may be dried and baked in an oven.
  • the apparatus-normally used for carrying out a The time for the baking step will depend creaseeresisttreatment with a urea-formaldehyde resin on textile materials, can be. used without substantial alters, tron.
  • the urea melts and acts. as a dye transfer medium.
  • the process of the, present invention provides a simple and convenient alternative to the established practice of dyeing from aqueous dyebaths.
  • the process is simple, quick, easy to. control and eliminates many of thev difiiculties encountered in dyeing with aqueous dyebaths.
  • the process is particularly suitable for dyeing blends of two or more different fibres especially where one of the fibres shows a preferential absorption for the dyestulf from an aqueous dyebath, for examples blends of viscose rayon fibres and regenerated protein fibres can be dyed in an even shade with a direct cotton dyestufi by the process of the present invention whereas the blends would be diiferentially dyed from an aqueous dyebath.
  • Example 1 A fabric woven from 100 percent viscose rayon staple yarn was padded at 100 percent expression through a solution at room temperature prepared as follows:
  • Example 2 A fabric woven from 100 percent viscose rayon staple yarn was padded at 100 percent expression through a solution at room temperature prepared as follows:
  • Example 3 A fabric woven from continuous filament cellulose acetate yarn was padded at 65 percent expression through the, following solution at room temperature: 1
  • a fabric woven from 100 percent continuous filament nylon yarn was padded through this solution at 60 percent expression and then dried at C.
  • the sample was then split into two equal parts, one only of which was then baked for 10 minutes at 130 C., washed in cold water and dried at 80 C.
  • Example 5 A ab c woven f m Pe c n re en a e pr in ap e van; a p e at 0 p r xpr sion hro h a solution prepared as follows:
  • Example 6 Some urea was heated at C. until the melting point had fallen to 124 C. The melt of cooked urea was allowed to resolidify and then ground to a powder.
  • a process for dyeing organic textile materials which comprises impregnating the textile material with a solution of a mixture of urea and at least one another substance which is soluble in molten urea and capable of lowering the melting point of urea, the amount of said substance in the mixture being sufiicient to lower the melting point of the urea by at least 10 C., and with an aqueous solution or dispersion of at least one dyestull which is soluble in molten urea and is substantive to the textile materiahdrying the textile material at a temperature below the melting point of the mixture of urea and said substance, heating the dried material, in the absence of steam to a temperature between the melting point of the mixture of urea and said substance and 160 C.
  • the urea in the mixture serves as a solvent for the dyestutf, from which solution trans for of the dyestuif to the material takes place, washing the dyed material to remove the urea and said substance and again drying the material.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

2,930,670 MOLTEN UREA DYEING PROCESS Samuel Nelson Bradshaw, oyentry, and Harry B. Mann, Braintree, England, a'ssignors to Courtauids Limited; London, England, a British company No Drawing. Application July 24, 1956 Serial No. 607,252 Claims priority, application Great Britain July 29,1955 Claims. (Cl. 8-85) This invention relates to the dyeing of textile materials.
In the normal dyeing procedure textiles are treated with an aqueous solution or dispersion of a dyestuff at a temperature depending on the nature of the material being dyed and the materials are left in the dyebath for a considerable period and are then rinsed and dried. The dyebath may also contain one or more dyeing assistants, for example common salt or Glaubers salt or other compounds which assist the material in taking up the dye.
and give a uniform penetration of the material by the dye. In the normal dyeing process therefore, water is the usual medium in which the dye is transferred'to the textile materials but in the specification of co-pending application U.S. Serial No. 428,375, filed May 7, 1954, and its continuation-impart Serial No. 668,043, filed June 26, 1957, there is described a method of dyeing in which molten urea replaces water as the dyestuff transfer medium. In this method textile materials are treated with a dyestutf in the presence of urea and are maintained at a temperature between the melting point of urea and 160 C. Thus textile materials may be impregnated with an aqueous solution or dispersion of the dyestuif and the urea, the impregnated material is dried and then baked at a temperature above the melting point of the urea.
In any dyeing process, it is generally desirable for economic or other reasons to carry out the process at the lowest practicable temperature and accordingly, the ob ject of the present invention is to modify the process of (1.8. Serial No. 428,375 and its continuation-in-part Serial No. 668,043, filed June 26, 1957, to enable lower temperatures to be used.
According to the present invention textile materials are treated with a dyestuif in the presence of urea and one or more other substances soluble in urea and capable of lowering the melting point of the urea and are maintained at a temperature between the melting point of the mixture and 160 C.
The amount by which the melting point is lowered will depend on the nature and quantity of the-substance or substances added. Any suitable substance (hereinafter referred to as a melting point depressant or depressant) soluble in molten urea and capable of lowering its melting point may be used. These depressants may be used in amounts up to of the weight of the urea, or up to their maximum solubility in urea if this is less than /s. The following table gives examples of suitable substances together with their maximum solubility in urea 2,930,670 Eaten-ted ,Mar. 29-, 1960 of the urea, also have a beneficial effect in reducing the tendency of the urea to decompose at elevated temperatures. Examples of such substances are the ammonium salts of strong acids such as ammonium chloride and ammonium sulphate. The melting point depressants may also be decomposition products formed in situ by heating urea above its melting point and allowing it to resolidify. If heated for a sufiicient time (for example from A to 2 hours) at a sufliciently high temperature (for example from to C.)-the resolidified urea has a lower melting point than the pure urea and can be used in the process of the present invention. The following table shows the reduction in melting point obtained with different temperatures and'times of heating.
The method of carrying out the present invention may be similar to that described in US. Serial No. 428,375 and its continuation-in-part Serial No. 668,043, filed June 26, 1957; thus thetextile materials may be impregnated with an aqueous solution or dispersion of the urea and the melting point depressant and an aqueous solution or dispersion of the dyestufi? or a single aqueous solution or dispersion ofthe dyestufi, the urea and the melting point depressant, dried, baked to effect the dyeing, washed to remove the urea and dried. The urea and the melting point depressant are preferably applied simultaneously from the same bath in an amount sufficient to give a take up of urea of 40 to 55 percent by weight of the dry textile materiaL. The impregnation is preferably effected at room temperature. on the temperature used; in practice times varying from 1 /2 to 15 minutes have been found adequate.
The process of the present invention is suitable for dyeing with dyestuffs which are soluble in molten ureafor example direct cotton dyestuffs, dispersed acetatedyestufis, soluble acetate dyestulfs, leuco esters of vat dyestuffs, aggregated acid dyestuffs and metal complex dyestuffs. itis particularly suitable for dyeing withv direct cotton dyestuffs.
The process of the present invention is suitable for-dyeing those textiles which are not deleteriously affected by the baking, for example textile materials of cotton, wool, regenerated cellulose, artificial protein fibres, cellulose esters, synthetic polyamides and synthetic polyesters and materials made from mixtures of two or moreof these fibres. If the process is used for dyeing textiles from thermoplasticrfibres having a comparatively low melting point for example certain vinyl resin fibres the baking should be carried out at the lowest temperature and for the shortest time permissible.
The textile materials may be dyed according to the ample, the process may be applied to woven or knitted fabrics or to threads, yarns or fibres.
the impregnated material may be dried and baked in an oven. 'The apparatus-normally used for carrying out a The time for the baking step will depend creaseeresisttreatment with a urea-formaldehyde resin on textile materials, can be. used without substantial alters, tron.
In the baking step in the process of the present invention the urea melts and acts. as a dye transfer medium. The process of the, present invention provides a simple and convenient alternative to the established practice of dyeing from aqueous dyebaths. The process is simple, quick, easy to. control and eliminates many of thev difiiculties encountered in dyeing with aqueous dyebaths.
The process is particularly suitable for dyeing blends of two or more different fibres especially where one of the fibres shows a preferential absorption for the dyestulf from an aqueous dyebath, for examples blends of viscose rayon fibres and regenerated protein fibres can be dyed in an even shade with a direct cotton dyestufi by the process of the present invention whereas the blends would be diiferentially dyed from an aqueous dyebath.
The invention is illustrated by the following examples in which the parts are by weight.
Example 1 A fabric woven from 100 percent viscose rayon staple yarn was padded at 100 percent expression through a solution at room temperature prepared as follows:
1 part of Durazol Yellow 3115 (LC-II) 40 parts of urea I pa of th urea were made up to 100 parts with water. The fabric was dried at 80C. and then baked for 15 minutes at 130 C The dye mpl as heu w shed for m nu es in l water and dried at 80 C.
1 subje t ng the dyed abric to h ash ng t as described in the Second Report of the Fastness Tests Committee of the Society of Dyers and Colourists (Journal of the Society of Dyers and Colourists, 1948, volume 64, pages 136-.137, Test No. 1) it was found that the fabric dyed by the process of the present invention was of comparable fastness to a fabric dyed from a conventional aqueous dyebath.
Example 2 A fabric woven from 100 percent viscose rayon staple yarn was padded at 100 percent expression through a solution at room temperature prepared as follows:
1 part Durazol Rubine BS ('I.C.I.) Color Index 28-160 40 parts of urea 5 parts of boric acid were made up to 100 parts with water. The fabric was dried at 80 C. and then baked for minutes at 130 C. The sample was then washed, dried, and the dye fastness assessed according to the test described in Example 1.
Very little dye-was removed by this test.
Example 3 A fabric woven from continuous filament cellulose acetate yarn was padded at 65 percent expression through the, following solution at room temperature: 1
3 parts of Duranol Violet 2R 300 (I.C.I.) Color Index 40 par of urea 5 P rts of ly rol p r o D per a (LC-L) Example 4 A solution was prepared as follows:
1 part of Coomassie Violet 2R (I.C.I.) Color index 45190 40 parts urea 5 parts sodium chloride were. made up to 100 parts with water.
A fabric woven from 100 percent continuous filament nylon yarn was padded through this solution at 60 percent expression and then dried at C. The sample was then split into two equal parts, one only of which was then baked for 10 minutes at 130 C., washed in cold water and dried at 80 C.
Both samples were subjected to the washing test described in Example 1. The sample which had been baked showed satisfactory dye retention but much of the dye on the unbaked sample was removed during the washing test.
Example 5 A ab c woven f m Pe c n re en a e pr in ap e van; a p e at 0 p r xpr sion hro h a solution prepared as follows:
1 p rt Ca b la B u RS (I-S-D-Q 9 ,1 8 Co r Ind x 52 0 P rt me 5 parts ammon um hlo de 2 parts Calsolene Oil were made up to parts with water. The padded fabric was dried at 80 C. and then baked for 10 minutes at C. The dyed fabric was finally washed in cold water and dried at 80 C. A sample subjected to the washing test described in Example 1 showed good dye retention, very little staining of the undyed fabric being noted.
Example 6 Some urea was heated at C. until the melting point had fallen to 124 C. The melt of cooked urea was allowed to resolidify and then ground to a powder.
A solution was prepared as follows:
1 part of Durazol Yellow 3R8 45 parts of cooked urea wer made up o 100 pa ts ith ate A fabric woven from 100 percent viscose rayon staple yarn was p dd d th o h th s l n a 0 pe n expression and dried at 80 C. The fabric was then a d f 5 m n s a 30 (13., washed a r u e Onsubjectingthe dyed fabric to the wash test detailed n Example 1 here was very l ed n t e dy nto he ndyed fab ic n e h we c im s:
1. A process for dyeing organic textile materials which comprises impregnating the textile material with a solution of a mixture of urea and at least one another substance which is soluble in molten urea and capable of lowering the melting point of urea, the amount of said substance in the mixture being sufiicient to lower the melting point of the urea by at least 10 C., and with an aqueous solution or dispersion of at least one dyestull which is soluble in molten urea and is substantive to the textile materiahdrying the textile material at a temperature below the melting point of the mixture of urea and said substance, heating the dried material, in the absence of steam to a temperature between the melting point of the mixture of urea and said substance and 160 C. to melt the mixture whereby the urea in the mixture serves as a solvent for the dyestutf, from which solution trans for of the dyestuif to the material takes place, washing the dyed material to remove the urea and said substance and again drying the material.
24, A process. as. claimed. in claim 1 wherein they textile material is impregnated with a single solution of urea and the said substance in which the dyestufi is dissolved or dispersed.
3. A process as claimed in claim 1 wherein the textile material is impregnated with an aqueous solution of urea and the said substance.
4. A process as claimed in claim 1 wherein the substance used is thiourea.
5. A process as claimed in claim 1 wherein the substance used is boric acid.
6. A process as claimed in claim 1 wherein the substance used is glycerol.
7. A process as claimed in claim 1 wherein the substance used is sodium chloride.
8. A process as claimed in claim 1 wherein the substance used is ammonium chloride.
9. A process as claimed in claim 1 wherein the textile material is impregnated with urea in an amount suflicient to give a take-up of urea of to percent by weight of the dry textilematerial.
10. A process as claimed in claim 9 wherein the amount of depressant is from about 8 to about 33 percent of the weight of the urea.
References Cited in the file of this patent UNITED STATES PATENTS OTHER REFERENCES Am. Dyestutr Report, p. 802, November 1950.

Claims (1)

1. A PROCESS FOR DYEING ORGANIC TEXTILE MATERIALS WHICH COMPRISES IMPREGNATING THE TEXTILE MATERIAL WITH A SOLUTION OF A MIXTURE OF UREA AND AT LEAST ONE ANOTHER SUBSTANCE WHICH IS SOLUBLE IN MOLTEN UREA AND CAPABLE OF LOWERING THE MELTING POINT OF UREA, THE AMOUNT OF SAID SUBSTANCE IN THE MIXTURE BEING SUFFICIENT TO LOWER THE MELTING POINT OF THE UREA BY AT LEAST 10*C., AND WITH AN AQUEOUS SOLUTION OR DISPERSION OF AT LEAST ONE DYESTUFF WHICH IS SOLUBLE IN MOLTEN UREA AND IS SUBSTANTIVE TO THE TEXTILE MATERIAL, DRYING THE TEXTILE MATERIAL AT A TEMPERATURE BELOW THE MELTING POINT OF THE MIXTURE OF UREA AND SAID, SUBSTANCE, HEATING THE DRIED MATERIAL, IN THE ABSENCE OF STEAM TO A TEMPERATURE BETWEEN THE MELTING POINT OF THE MIXTURE OF UREA AND SAID SUBSTANCE AND 160*C. TO MELT THE MIXTURE WHEREBY THE UREA IN THE MIXTURE SERVES AS A SOLVENT FOR THE DYESTUFF, FROM WHICH SOLUTION TRANSFER OF THE DYESTUFF TO THE MATERIAL TAKES PLACE, WASHING THE DYED MATERIAL TO REMOVE THE UREA AND SAID SUBSTANCE AND AGAIN DRYING THE MATERIAL.
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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3052510A (en) * 1962-09-04 Art of dyeing synthetic polymeric
US3097042A (en) * 1959-08-04 1963-07-09 Ici Ltd Textile colouration process
US3206511A (en) * 1959-07-08 1965-09-14 Geigy Chem Corp Non-ionogenic polyamine ether capillary active compounds
US3418063A (en) * 1964-07-14 1968-12-24 Ciba Ltd Process for dyeing and printing cellulose fibres
US3493316A (en) * 1966-05-09 1970-02-03 Allied Chem Dyed fiber products
US3632289A (en) * 1969-04-01 1972-01-04 Du Pont Stable solutions of 4,4{40 -bis(diethylamino)-benzophenonimine hydrochloride

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1963975A (en) * 1928-08-07 1934-06-26 Celanese Corp Production of waterproof materials
US2080254A (en) * 1934-09-13 1937-05-11 Celanese Corp Dyed material of organic derivatives of cellulose
CH230891A (en) * 1941-08-28 1944-02-15 Rhodiaceta Dye bath for superpolyamide articles.
US2564225A (en) * 1946-08-07 1951-08-14 Chadeloid Corp Dyestuff purification
FR996335A (en) * 1949-09-28 1951-12-18 T E Marchington & Co Ltd Improvements to the coloring of threads or fabrics made entirely or partially of cellulose acetate

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1963975A (en) * 1928-08-07 1934-06-26 Celanese Corp Production of waterproof materials
US2080254A (en) * 1934-09-13 1937-05-11 Celanese Corp Dyed material of organic derivatives of cellulose
CH230891A (en) * 1941-08-28 1944-02-15 Rhodiaceta Dye bath for superpolyamide articles.
US2564225A (en) * 1946-08-07 1951-08-14 Chadeloid Corp Dyestuff purification
FR996335A (en) * 1949-09-28 1951-12-18 T E Marchington & Co Ltd Improvements to the coloring of threads or fabrics made entirely or partially of cellulose acetate

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3052510A (en) * 1962-09-04 Art of dyeing synthetic polymeric
US3206511A (en) * 1959-07-08 1965-09-14 Geigy Chem Corp Non-ionogenic polyamine ether capillary active compounds
US3097042A (en) * 1959-08-04 1963-07-09 Ici Ltd Textile colouration process
US3418063A (en) * 1964-07-14 1968-12-24 Ciba Ltd Process for dyeing and printing cellulose fibres
US3493316A (en) * 1966-05-09 1970-02-03 Allied Chem Dyed fiber products
US3632289A (en) * 1969-04-01 1972-01-04 Du Pont Stable solutions of 4,4{40 -bis(diethylamino)-benzophenonimine hydrochloride

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