US2731364A - Process for improving cellulose textile materials and product thereof - Google Patents

Process for improving cellulose textile materials and product thereof Download PDF

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US2731364A
US2731364A US304842A US30484252A US2731364A US 2731364 A US2731364 A US 2731364A US 304842 A US304842 A US 304842A US 30484252 A US30484252 A US 30484252A US 2731364 A US2731364 A US 2731364A
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textiles
parts
compounds
dihydroxyimidazolidone
methylol
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US304842A
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Bruno V Reibnitz
Ruemens Wilhelm
Beideck Kurt
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BASF SE
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BASF SE
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
    • D06M15/423—Amino-aldehyde resins

Definitions

  • This invention relates to a process for improving cellulose textile materials by impregnating with methylol compounds of 4,5-dihydroxyimidazolidone and to cellulose textile materials thus treated.
  • creaseproof and waterproof impregnations can be prepared on textiles on the basis of natural or regenerated cellulose by treating the textiles with solutions of methylol compounds of 4,5-dihydroxyimidazolidone in the presence of acid-reacting hardening catalysts, as for example acids, acid-reacting salts or potentially acid compounds (i. e. compounds which react acid when heated or in the presence of methylol compounds, as for example ammonium salts).
  • acid-reacting hardening catalysts as for example acids, acid-reacting salts or potentially acid compounds (i. e. compounds which react acid when heated or in the presence of methylol compounds, as for example ammonium salts).
  • Suitable 4,5 dihydroxyimidazoline of which the methylol compounds may be employed according to this invention are for example the 4,5-dihydroxyimidazolidone of the following constitution:
  • KOCH-NH /C X KOCH-NH (in which X represents 0, S or NH) and also the 4,5- dihydroxyimidazolidones of diacetyl, benzil and the like, in general monoureins of a-fi-dicarbonyl compounds.
  • methylol compounds we mean the addition products of 1 or 2 mols of formaldehyde to 1 mol of a monourein, or the water-soluble initial condensation products of these substances, or mixtures of the addition products and the initial condensation products. Description of the methylol compounds is set forth in greater detail in the application of Von Reibnitz, et al., Serial No. 304,841, filed August 16, 1952.
  • the textile material is preferably impregnated with an aqueous solution of the methylol compounds and the hardening catalyst, dried, for example at 40 to 85 C., and then heated for a short time at a higher temperature, preferably at from 110 to 140 C.
  • the methylol compounds may be produced from the 4,5-dihydroxyimidazolidones and formaldehyde on the fibres and then hardened.
  • Methylol compounds of other lowmolecular substances which form aminoplasts, as for example of urea, urethanes or melamine, or the said aminoplast-forming substances and formaldehyde may be added during the impregnation. It is also possible to add during the impregnation polyfunctional compounds having reactive hydrogen atoms which are capable of reacting with the methylol-4,5-dihydroxyimidazolidones to form resinous condensation products. Such compounds are for example glycols, amino alcohols and diamines.
  • the treated textiles are characterized by good resistance to creasing, increased resistance to shrinkage and wet tearing and reduced swelling value. It is especially remarkable that they have a higherabrasion resistance than textiles treated with methylol compounds of urea.
  • waterproof coatings and waterproof embossed effects can be prepared on textiles.
  • the textiles are impregnated with a solution of the methylol compounds of 4,S-dihydroxyimidazolidones and dried, for example at 40 to C.
  • the textiles are then calendered or embossed, with or without friction, at about to 150 C. under high pressure whereby at the same time a glossy and embossed effect are obtained. They are then heated for 5 to 10 minutes at higher temperatures, preferably at to C.
  • the textiles become waterproof by the treatment and acquire a chintz finish.
  • methylol-4,S-dihydroxyimidazolidones at the same time finishing agents, as for example high-molecular polyglycol ethers, polyvinyl pyrrolidone, poly acrylic acid and derivatives thereof, polyvinyl imidazole, saponificaticn products of polyacrylonitrile or polyacrylic acid esters, polyvinyl alcohol, soluble starch, dextrine, or cellulose ethers or esters also animal glue and amides obtained by the reaction of long-chain aliphatic carboxylic acids and aminoalcohols.
  • finishing agents as for example high-molecular polyglycol ethers, polyvinyl pyrrolidone, poly acrylic acid and derivatives thereof, polyvinyl imidazole, saponificaticn products of polyacrylonitrile or polyacrylic acid esters, polyvinyl alcohol, soluble starch, dextrine, or cellulose ethers or esters also animal glue and amides obtained by the reaction of long-chain alipha
  • Example 1 120 to 140 parts of the dimethylol-4,5-dihydroxyimidazolidone are dissolved in 1000 parts of water and 20 to 25 parts of zinc chloride are added. A staple fibre fabric is impregnated with this liquor, squeezed out and dried at 70 C. The fabric is thenheated for 5 minutes at 120 C. After this treatment it has a very good creaseproof effect which is stable to Washing. The swelling value is reduced by about 45 per cent.
  • Example 2 4 parts of ammonium chloride are added to 1000 parts of an 8 per cent aqueous solution of an initial condensation product from the 4,S-dihydroxyimidazolidone and formaldehyde (molecular ratio 1:2). There is then added an emulsion of 30 parts of a paraifin wax mixture containing zirconium or aluminium hydroxide in 100 parts :of water. A cotton fabric is impregnated with thismix ture, squeezed out and dried at 70 C. The fabric is then gcalendered under pressure at 120 C. and then heated for minutes at 130 C.
  • the fabric acquires a chintz-like coating with a glossy effect which is stable to water.
  • Example 4 160 parts of dimethylol-4,5-dihydroxyimidazolidone and 56 parts of ethyleneglycol are dissolved together with 4 parts of diammonium phosphate in 1000 parts of water. A staple fibre fabric is impregnated with this liquor, squeezed out, dried at 70 C. and then heated for 5 minutes at 170 C. The fabric thus treated has a creaseproof efiect which is stable to water and has a reduced swelling value.
  • Example 6 120 parts of the dimethylol-4,S-dihydroxyimidazolidone and 42 parts of ethylene glycol are dissolved in 900 parts of water. parts of polyvinyl alcohol and 5 parts of ammonium nitrate and 0.5 part of sodium bicarbonate or acetate in 100 parts of water are added to the solution. A staple fibre fabric is impregnated with this liquor, squeezed out and dried. It is then calendered l to 3 times under high pressure at 120 C. and then heated for '5 minutes at 130 C. The fabric acquires a washable coating with a glossy effect which is stable to water.
  • a process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution .of a methylol compound of a 4,5- dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, drying and heating then the impregnated textiles to harden the impregnating agent em- 'ployed.
  • a process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, drying and heating then the impregnated textiles to harden the impregnating agent employed.
  • a process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-di hydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, calandering the impregnated textiles after drying and heating then the textiles to harden the impregnating agent.
  • a process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, calendering the impregnated fabric after drying to a temperature from C. to 150 C. and heating then the textiles to a temperature from C. to C. to harden the impregnating agent.
  • Cellulose textiles having an impregnation of a hardened methylol compound of 4,5-dihydroxyimidazolidone.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Description

United States Patent PROCESS FOR IMPROVING CELLULOSE TEXTILE MATERIALS AND PRODUCT THEREOF Bruno v. Reihnitz, Mannheim-Feudcnheim, and Wilhelm Ruemens and Kurt Eeideck, Ludwigshafen (Rhine), Germany, assiguors to Badische Anilin- & Soda-Fabrik Aktiengesellschaft, Ludwigshafen (Rhine), Germany No Drawing. Application August 16, 1952, Serial No. 304,842
Claims priority, application Germany August 18, 1951 12 Claims. (Cl. 117-64) This invention relates to a process for improving cellulose textile materials by impregnating with methylol compounds of 4,5-dihydroxyimidazolidone and to cellulose textile materials thus treated.
For improving cellulose fibres it is advantageous to use methylol compounds of low-molecular nitrogenous compounds having the following grouping:
or their initial materials.
These compounds, either on the surface of or within the interior of the fibres, are converted into resinous condensation products in the presence of acids or acid-react ing compounds, preferably at elevated temperatures.
We have now found that creaseproof and waterproof impregnations can be prepared on textiles on the basis of natural or regenerated cellulose by treating the textiles with solutions of methylol compounds of 4,5-dihydroxyimidazolidone in the presence of acid-reacting hardening catalysts, as for example acids, acid-reacting salts or potentially acid compounds (i. e. compounds which react acid when heated or in the presence of methylol compounds, as for example ammonium salts).
Suitable 4,5 dihydroxyimidazoline of which the methylol compounds may be employed according to this invention, are for example the 4,5-dihydroxyimidazolidone of the following constitution:
KOCH-NH /C=X KOCH-NH (in which X represents 0, S or NH) and also the 4,5- dihydroxyimidazolidones of diacetyl, benzil and the like, in general monoureins of a-fi-dicarbonyl compounds.
By methylol compounds we mean the addition products of 1 or 2 mols of formaldehyde to 1 mol of a monourein, or the water-soluble initial condensation products of these substances, or mixtures of the addition products and the initial condensation products. Description of the methylol compounds is set forth in greater detail in the application of Von Reibnitz, et al., Serial No. 304,841, filed August 16, 1952.
in order to carry out the process, the textile material is preferably impregnated with an aqueous solution of the methylol compounds and the hardening catalyst, dried, for example at 40 to 85 C., and then heated for a short time at a higher temperature, preferably at from 110 to 140 C.
According to another modification of the process, the methylol compounds may be produced from the 4,5-dihydroxyimidazolidones and formaldehyde on the fibres and then hardened. Methylol compounds of other lowmolecular substances which form aminoplasts, as for example of urea, urethanes or melamine, or the said aminoplast-forming substances and formaldehyde may be added during the impregnation. It is also possible to add during the impregnation polyfunctional compounds having reactive hydrogen atoms which are capable of reacting with the methylol-4,5-dihydroxyimidazolidones to form resinous condensation products. Such compounds are for example glycols, amino alcohols and diamines.
The treated textiles are characterized by good resistance to creasing, increased resistance to shrinkage and wet tearing and reduced swelling value. It is especially remarkable that they have a higherabrasion resistance than textiles treated with methylol compounds of urea.
There is no unpleasant odour during the carrying out of the process, and the treated goods are also unobjectionable from the point of view of odour. The bath stability is also very good even after the addition of the hardening catalyst.
According to a further modification of the process, waterproof coatings and waterproof embossed effects can be prepared on textiles. For this purpose the textiles are impregnated with a solution of the methylol compounds of 4,S-dihydroxyimidazolidones and dried, for example at 40 to C. The textiles are then calendered or embossed, with or without friction, at about to 150 C. under high pressure whereby at the same time a glossy and embossed effect are obtained. They are then heated for 5 to 10 minutes at higher temperatures, preferably at to C. The textiles become waterproof by the treatment and acquire a chintz finish.
In order to increase the waterproof glossy effect, in particular with staple fibre fabrics, there may be added to the solutions of the methylol-4,S-dihydroxyimidazolidones at the same time finishing agents, as for example high-molecular polyglycol ethers, polyvinyl pyrrolidone, poly acrylic acid and derivatives thereof, polyvinyl imidazole, saponificaticn products of polyacrylonitrile or polyacrylic acid esters, polyvinyl alcohol, soluble starch, dextrine, or cellulose ethers or esters also animal glue and amides obtained by the reaction of long-chain aliphatic carboxylic acids and aminoalcohols.
The following examples will further illustrate this invention but the invention is not restricted to these ex amples. The parts are by weight.
Example 1 120 to 140 parts of the dimethylol-4,5-dihydroxyimidazolidone are dissolved in 1000 parts of water and 20 to 25 parts of zinc chloride are added. A staple fibre fabric is impregnated with this liquor, squeezed out and dried at 70 C. The fabric is thenheated for 5 minutes at 120 C. After this treatment it has a very good creaseproof effect which is stable to Washing. The swelling value is reduced by about 45 per cent.
Example 2 4 parts of ammonium chloride are added to 1000 parts of an 8 per cent aqueous solution of an initial condensation product from the 4,S-dihydroxyimidazolidone and formaldehyde (molecular ratio 1:2). There is then added an emulsion of 30 parts of a paraifin wax mixture containing zirconium or aluminium hydroxide in 100 parts :of water. A cotton fabric is impregnated with thismix ture, squeezed out and dried at 70 C. The fabric is then gcalendered under pressure at 120 C. and then heated for minutes at 130 C.
The fabric acquires a chintz-like coating with a glossy effect which is stable to water.
Example 4 Example 5 160 parts of dimethylol-4,5-dihydroxyimidazolidone and 56 parts of ethyleneglycol are dissolved together with 4 parts of diammonium phosphate in 1000 parts of water. A staple fibre fabric is impregnated with this liquor, squeezed out, dried at 70 C. and then heated for 5 minutes at 170 C. The fabric thus treated has a creaseproof efiect which is stable to water and has a reduced swelling value.
Example 6 120 parts of the dimethylol-4,S-dihydroxyimidazolidone and 42 parts of ethylene glycol are dissolved in 900 parts of water. parts of polyvinyl alcohol and 5 parts of ammonium nitrate and 0.5 part of sodium bicarbonate or acetate in 100 parts of water are added to the solution. A staple fibre fabric is impregnated with this liquor, squeezed out and dried. It is then calendered l to 3 times under high pressure at 120 C. and then heated for '5 minutes at 130 C. The fabric acquires a washable coating with a glossy effect which is stable to water.
What we claim is:
1. A process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution .of a methylol compound of a 4,5- dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, drying and heating then the impregnated textiles to harden the impregnating agent em- 'ployed.
2. A process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, drying and heating then the impregnated textiles to harden the impregnating agent employed.
3. A process as claimed in claim 2 wherein dimethylol- 4,S-dihydroxyimidazolidone is used.
4. A process as claimed in claim 2 wherein monomethylol-4,S-dihydroxyimidazolidone is used. 7
5. A process as claimed in claim 2 wherein the methylol compounds of 4,S-dihydroxyimidazolidone are prepared in the textiles from glyoxal monourein and formaldehyde.
6. A process as claimed in claim 2 wherein methylol compounds of aminoplast-forming substances selected from the class consisting of urea, urethanes and melamine are also added.
7. A process as claimed in claim alcohols are also added.
8. A process as claimed in claim 2 wherein waterrepellent substances are also added.
9. A process as claimed in claim 2 wherein finishing agents are also added.
10. A process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-di hydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, calandering the impregnated textiles after drying and heating then the textiles to harden the impregnating agent.
11. A process for the production of impregnations on cellulose textiles which comprises impregnating the textiles with a solution of a methylol compound of 4,5-dihydroxyimidazolidone in the presence of an acid-reacting hardening catalyst, calendering the impregnated fabric after drying to a temperature from C. to 150 C. and heating then the textiles to a temperature from C. to C. to harden the impregnating agent.
12. Cellulose textiles having an impregnation of a hardened methylol compound of 4,5-dihydroxyimidazolidone.
2 wherein polyhydric References Cited in the file of this patent UNITED STATES PATENTS 2,504,857 MacIntyre Apr. 18, 1950 2 ,574,114 Lehmann Nov. 6, 1951 2,588,640 Lehmann Mar. 11, 1952

Claims (1)

1. A PROCESS FOR THE PRODUCTION OF IMPREGNATIONS ON CELLULOSE TEXTILES WHICH COMPRISES IMPREGNATING THE TEXTILES WITH A SOLUTION OF A METHYLOL COMPOUND OF A 4,5DIHYDROXYIMIDAZOLIDONE IN THE PRESENCE OF AN ACID REACTING HARDENING CATALYST, DRYING AND HEATING THEN THE IMPREGNATED TEXTILES TO HARDEN THE IMPREGNATING AGENT EMPLOYED.
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Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2887408A (en) * 1957-09-27 1959-05-19 American Cyanamid Co Method of treating textile materials
US2898238A (en) * 1956-08-20 1959-08-04 American Cyanamid Co Process for treating textiles with ethylene urea-formaldehyde reaction products
US2926062A (en) * 1956-03-05 1960-02-23 Gagliardi Res Corp Water repellent compositions, products and processes for making same
US2992138A (en) * 1958-04-17 1961-07-11 Du Pont Cellulosic textile treating composition and process
US3029164A (en) * 1959-03-12 1962-04-10 Sumitomo Chemical Co Production of crease resistance in cellulosic fabrics with the aid of 1, 3-dimethylol-4, 5-bis(alkoxy)-2-imidazolidinones
US3049446A (en) * 1960-02-05 1962-08-14 Sun Chemical Corp Process for the manufacture of urea, glyoxal and formaldehye reaction product useful for improving cellulosic textile materials
DE1134655B (en) * 1959-06-11 1962-08-16 Cassella Farbwerke Mainkur Ag Process for the production of a chlorine-resistant anti-crease finish
US3112156A (en) * 1960-10-07 1963-11-26 Sidney L Vail Treatment of cellulosic textile material with 1, 3-dimethyl-4, 5-dihydroxy-2-imidazolidinone
US3116967A (en) * 1958-01-09 1964-01-07 Sun Chemical Corp Creaseproofing compositions for textiles
US3181927A (en) * 1959-11-16 1965-05-04 American Cyanamid Co Process of wet and dry wrinkleproofing cellulose fabric with an aminoplast resin and zinc chloride
US3260565A (en) * 1961-02-03 1966-07-12 American Cyanamid Co Novel imidazolidinones and their use as textile finishing agents
US3322569A (en) * 1962-11-10 1967-05-30 Basf Ag Treatment of cellulosic textiles with a crease resisting finish and a copolymer of a n-methylolamide of an acrylic acid for the purpose of reducing wet soiling
US3355242A (en) * 1960-07-11 1967-11-28 Sun Chemical Corp Reactive dyes and methylolated-4, 5-dihydroxy-imidazolidone-2, in coloring cellulosic textiles
US3376101A (en) * 1963-10-22 1968-04-02 Agriculture Usa Process of modifying cellulosic textiles with glyoxal-biscarbamate reaction products
US3377249A (en) * 1966-08-04 1968-04-09 Deering Milliken Res Corp Soil release of polyester containing textiles through treatment with aminoplast resins in conjunction with acrylic emulsion polymers containing at least 20% acid calculated as acrylic acid
US3381310A (en) * 1964-08-11 1968-05-07 Stevens & Co Inc J P Permanently creased and pleated fabrics and process for producing same
US3420702A (en) * 1965-05-11 1969-01-07 Dan River Mills Inc Double bath treatment of cellulosic fabrics to impart crease resistance and high abrasion resistance thereto
US3442905A (en) * 1966-09-08 1969-05-06 American Cyanamid Co N-methylol-n'-substituted-4,5-dihydroxy-2-imidazolidinones
US3505097A (en) * 1967-04-20 1970-04-07 Hercules Inc Lustrous pile fabric based on polypropylene
US3632422A (en) * 1969-12-04 1972-01-04 Burlington Industries Inc Textile fabric having soil release finish and method of making same
US3639096A (en) * 1964-10-19 1972-02-01 Dan River Inc Process of treating direct dyed cellulosic textiles with a mixture of aminoplast creaseproofing agents and products resulting therefrom
US3658575A (en) * 1969-09-29 1972-04-25 Dow Chemical Co Method and compositions for treating flexible substrates
US3768969A (en) * 1971-12-21 1973-10-30 Us Agriculture Sensitized textiles with decreased formaldehyde odor
US3890095A (en) * 1967-04-05 1975-06-17 American Cyanamid Co Cellulosic textile finish with 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, zinc nitrate and a sequestering agent
US3911181A (en) * 1968-09-27 1975-10-07 American Cyanamid Co Permanent press textile finish
US3920881A (en) * 1973-07-02 1975-11-18 American Cyanamid Co Textile finish using a combination of an aminoplast resin and monomethyloldicyandiamide
US3930087A (en) * 1971-12-22 1975-12-30 Basf Ag Crease resistant cellulosic textile material
US20080246177A1 (en) * 2005-03-04 2008-10-09 Basf Aktiengesellschaft Production of Moulded Bodies From Lignocellulose-Based Fine Particle Materials

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2810624A (en) * 1954-04-08 1957-10-22 Rohm & Haas Cellulose plisse fabric and method of producing by applying 1, 3-bis(hydroxy-methyl)-2-imidazolidone and chemical shrinking agent

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US2504857A (en) * 1948-06-03 1950-04-18 Bancroft & Sons Co J Art of imparting crease resistance to cotton fabrics
US2574114A (en) * 1948-04-26 1951-11-06 Bozel Maletra Prod Chimiques Amide-glyoxal-formaldehyde reaction product and shrinkproofing cellulose textile fibers therewith
US2588640A (en) * 1948-04-26 1952-03-11 Bozel Maletra Prod Chimiques Hydrofugation of textile materials

Patent Citations (3)

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US2574114A (en) * 1948-04-26 1951-11-06 Bozel Maletra Prod Chimiques Amide-glyoxal-formaldehyde reaction product and shrinkproofing cellulose textile fibers therewith
US2588640A (en) * 1948-04-26 1952-03-11 Bozel Maletra Prod Chimiques Hydrofugation of textile materials
US2504857A (en) * 1948-06-03 1950-04-18 Bancroft & Sons Co J Art of imparting crease resistance to cotton fabrics

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2926062A (en) * 1956-03-05 1960-02-23 Gagliardi Res Corp Water repellent compositions, products and processes for making same
US2898238A (en) * 1956-08-20 1959-08-04 American Cyanamid Co Process for treating textiles with ethylene urea-formaldehyde reaction products
US2887408A (en) * 1957-09-27 1959-05-19 American Cyanamid Co Method of treating textile materials
US3116967A (en) * 1958-01-09 1964-01-07 Sun Chemical Corp Creaseproofing compositions for textiles
US2992138A (en) * 1958-04-17 1961-07-11 Du Pont Cellulosic textile treating composition and process
US3029164A (en) * 1959-03-12 1962-04-10 Sumitomo Chemical Co Production of crease resistance in cellulosic fabrics with the aid of 1, 3-dimethylol-4, 5-bis(alkoxy)-2-imidazolidinones
DE1134655B (en) * 1959-06-11 1962-08-16 Cassella Farbwerke Mainkur Ag Process for the production of a chlorine-resistant anti-crease finish
US3181927A (en) * 1959-11-16 1965-05-04 American Cyanamid Co Process of wet and dry wrinkleproofing cellulose fabric with an aminoplast resin and zinc chloride
US3049446A (en) * 1960-02-05 1962-08-14 Sun Chemical Corp Process for the manufacture of urea, glyoxal and formaldehye reaction product useful for improving cellulosic textile materials
US3355242A (en) * 1960-07-11 1967-11-28 Sun Chemical Corp Reactive dyes and methylolated-4, 5-dihydroxy-imidazolidone-2, in coloring cellulosic textiles
US3112156A (en) * 1960-10-07 1963-11-26 Sidney L Vail Treatment of cellulosic textile material with 1, 3-dimethyl-4, 5-dihydroxy-2-imidazolidinone
US3260565A (en) * 1961-02-03 1966-07-12 American Cyanamid Co Novel imidazolidinones and their use as textile finishing agents
US3322569A (en) * 1962-11-10 1967-05-30 Basf Ag Treatment of cellulosic textiles with a crease resisting finish and a copolymer of a n-methylolamide of an acrylic acid for the purpose of reducing wet soiling
US3376101A (en) * 1963-10-22 1968-04-02 Agriculture Usa Process of modifying cellulosic textiles with glyoxal-biscarbamate reaction products
US3381310A (en) * 1964-08-11 1968-05-07 Stevens & Co Inc J P Permanently creased and pleated fabrics and process for producing same
US3639096A (en) * 1964-10-19 1972-02-01 Dan River Inc Process of treating direct dyed cellulosic textiles with a mixture of aminoplast creaseproofing agents and products resulting therefrom
US3420702A (en) * 1965-05-11 1969-01-07 Dan River Mills Inc Double bath treatment of cellulosic fabrics to impart crease resistance and high abrasion resistance thereto
US3377249A (en) * 1966-08-04 1968-04-09 Deering Milliken Res Corp Soil release of polyester containing textiles through treatment with aminoplast resins in conjunction with acrylic emulsion polymers containing at least 20% acid calculated as acrylic acid
US3442905A (en) * 1966-09-08 1969-05-06 American Cyanamid Co N-methylol-n'-substituted-4,5-dihydroxy-2-imidazolidinones
US3890095A (en) * 1967-04-05 1975-06-17 American Cyanamid Co Cellulosic textile finish with 1,3-dimethylol-4,5-dihydroxy-2-imidazolidinone, zinc nitrate and a sequestering agent
US3505097A (en) * 1967-04-20 1970-04-07 Hercules Inc Lustrous pile fabric based on polypropylene
US3911181A (en) * 1968-09-27 1975-10-07 American Cyanamid Co Permanent press textile finish
US3658575A (en) * 1969-09-29 1972-04-25 Dow Chemical Co Method and compositions for treating flexible substrates
US3632422A (en) * 1969-12-04 1972-01-04 Burlington Industries Inc Textile fabric having soil release finish and method of making same
US3768969A (en) * 1971-12-21 1973-10-30 Us Agriculture Sensitized textiles with decreased formaldehyde odor
US3930087A (en) * 1971-12-22 1975-12-30 Basf Ag Crease resistant cellulosic textile material
US3920881A (en) * 1973-07-02 1975-11-18 American Cyanamid Co Textile finish using a combination of an aminoplast resin and monomethyloldicyandiamide
US20080246177A1 (en) * 2005-03-04 2008-10-09 Basf Aktiengesellschaft Production of Moulded Bodies From Lignocellulose-Based Fine Particle Materials

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GB720387A (en) 1954-12-15
CH310796A (en) 1955-11-15
FR1061311A (en) 1954-04-12

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