US2347024A - Impregnating composition for textile materials - Google Patents
Impregnating composition for textile materials Download PDFInfo
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- US2347024A US2347024A US484462A US48446243A US2347024A US 2347024 A US2347024 A US 2347024A US 484462 A US484462 A US 484462A US 48446243 A US48446243 A US 48446243A US 2347024 A US2347024 A US 2347024A
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- urea
- formaldehyde
- textile materials
- oxymethyl
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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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
- D06M13/477—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having six-membered heterocyclic rings
Definitions
- This invention relates to a method and means for treating textile materials and has particular relation to a process and a composition for reducing or eliminating the tendency of textile materials to shrink in laundering, and simultaneously improving the wearing qualities of said materials.
- the main object of my present invention consists in treating textil materials with acomposition adapted to yield shrlnkproof products of improved wearing quality.
- Another object of my invention is to reduce or eliminate the tendency of textile materials to shrink, by means of impregnating solutions of relatively low concentration.
- a further object of this invention consists in the use of impregnating solutions which reduce the tendency of textile materials to shrink withoutimpairlng other properties of said materials.
- 1 use an, aqueous solution containing about 2% by weight of the urea-formaldehyde type condensation prodnot and about (id-0.6% of octadecyboxymethyb pyridlnium chloride.
- aqueous solution containing about 2% by weight of the urea-formaldehyde type condensation prodnot and about (id-0.6% of octadecyboxymethyb pyridlnium chloride.
- a small amount of a salt of a strong inorganic base, such as sodium or potassium, and a weak organic acid such as formic, acetic or lactic acid or an acid of similar strength After passing through th impregnating solution, the textile material is squeezed out until it contains about 100% by weight of solution based on the weight of the dry starting material.
- the impregnated material is then dried at a relatively low temperature, f. e. at
- aldehyde type condensation products in mixture with octadecyl-oxymethyl-pyridinium chloride, with or without the addition of a catalyst, as specified in the following examples.
- the impregnating solution may preferably contain a catalyst.
- a catalyst consisting of about equal parts of hexamethylenetetramine and a suitable ammonium salt, such as ammonium sulfate, is. advantageous, particularly in the treatment of cellulosic materials.
- textile materials such as fabrics, spun goods, filaments, webs, etc. consisting of W001, natural or regenerated cellulose, cellulose derivatives, such as cellulose acetate, or mixtures of these materials may be successfully treated according to the present invention.
- W001 natural or regenerated cellulose
- cellulose derivatives such as cellulose acetate
- treated textile materials are shrinkproof and they show a substantial improvement with respect to their wearing qualities and particularly their re sistance to abrasion. In the case of woolen materials the tendency .to felt formation is also reduced.
- Example I.Woolen stockings are wetted and immersed in an aqueous liquid containing in solution 2% by weight of a water-soluble ureaformaldehyde condensation product and 0.6% of octadecyl-oxymethyl-pyridinium chloride.
- the stockings are then squeezed or subjected to centrifugal action until they contain by weight of liquid based on the dry weight of the starting material. They are then dried at about 60- 70 C. and finally heated for about 5 minutes at -130 C. in a chamber heated by means of hot air. If the product thus obtained is subjected to washing with an aqueous soap solution, it substantially retains its original shape and dimensions.
- the resistance to abrasion of the material treated shows a very substantial increase in comparison to that of the untreated material. While the latter is rubbed through at 1000 cycles in Taber's testing machine. the treated material requires 4000 cycles for obtaining the sam effect under otherwise equal conditions.
- Example II A fabric consisting of 50% wool and 50% of cotton is treated with an aqueous liquid containing in 1 liter of the solution Grams Urea thiourea formaldehyde condensation produc l8 Octadecyl-oxymethyl-pyridinium chloride '6 sodium formate" 1 The treatment of the fabric with liquid and.
- Example I The product obtained shows an improvement of the resistance to abrasion of 500 cycles on Taber's testing device in comparison to 350 cycles in the case of the untreated starting material
- Example IV A cotton fabric consisting of cotton yarn in warp and filling is impregnated at l8-20 C. with a solution of Grams Urea thiourea formaldehyde condensation product 20 Octadecyl-oxymethyl-pyridinium chloride-.. 4 sodium formate 0.6 Hexamethylenetetramine 0.4 Ammoniumsulfate 0.4
- Example V.-A fabric consisting of 50% of cotton and 50% of viscose rayon is treated in the manner described in Example I with the following solution:
- Example II Sodium lactate 1 dissolved in 1 liter of water. Drying and heatin of the impregnated fabric are also carried out in the manner described in Example I. . The finished product is rubbed through at 600 cycles in the Taber machine in comparison to 450 cycles in the case of the untreated starting material.
- the eifect obtained in carrying out my present invention is unobvious because the use of an urea-formaldehyde type resin by itself under otherwise similar conditions does not result in a shrink-proof product, and because it could not be expected that deterioration of the textile product by the urea-formaldehyde compounds can be prevented by the presence of the octadecyl-oxymethyl-pyridinium chloride. Moreover, the use of said resin by itself causes deterioration of properties of the starting material while the combined use of resin and pyridinium salt under the conditions of my present invention, results in an improvement of said properties.
- a rayon fabric which, in its original, untreated condition, is rubbed through in Tabers testing device at 400 cycles, requires only 250 cycles after being treated in the customary manner with urea-formaldehyde type condensation products. If, however, the same fabric is treated in accordance with the present invention with a mixture of urea-formaldehyde type condensation products and octadecyl-oxymethyl-pyridinium chloride, it will be rubbed through in Taber's testing device at 550 cycles,
- the urea condensation products used in carrying out my present invention are prepared in a manner known per se, f. e. by condensing one mol of urea or a mixture of urea and thiourea, with 2 mols of formaldehyde to a water-soluble condensation product which is recovered from the aqueous solution.
- the figures stated in the above examples relate to the solid, technically pure condensation products.
- compositions for textile materials containing in aque ous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about Lil-2.2% by weight of a thermosetting condensation product selected from the group consisting of urea-formaldehyde and urea-thioureaformaldehyde condensation products.
- thermosetting condensation product selected from the group,
- ' catalyst consistng of about equal parts of hen-- methylene tetramine and ammonium sulfate.
- compositions for textile materials containing in aqua ous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about 1.8-2.2% by weight of a thermo-setting ureathiourea-formaldehyde condensation product.
- compositions for textile materials said composition containing in aque-- materials, said composition containing in aqueous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about 1.8-2.2% by weight of a thermo-setting ureaformaldehyde condensation product.
- compositions for textile materials consisting of 3-6 parts by weight of octadecyl-oxymethyl-pyridinium chloride and about 18-22 parts by weight of a thermo-setting urea-formaldehyde condensation product dissolved in one liter of water.
- An impregnating composition for textile materials saidcomposition containing in aqueous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about 13.-2.2% by weight of a thermo-setting ureaformaldehyde condensation product and a catalyst consisting of about equal parts of hexamethylene tetramine and ammonium sulfate.
- compositions for textile materials said composition containing in aqueous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about 1.8-2.2% by weight of a thermo-setting condensation product selected from the group consisting of urea-formaldehyde and urea-thi'oureaformaldehyde condensation products, and an alkali salt of a weak organic acid.
- compositions for textile materials consisting of an aqueous solution containing about 2% by weight of a thermosetting condensation product selected from the group consisting of urea-formaldehyde and urea-thiourea-formaldehyde condensation products, and about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride.
- An impregnating composition for textile materials consisting of an aqueous solution containing about 2% by weight of athermosetting condensation product selected from the group consisting of urea-formaldehyde and urea' thiourea-formaldehyde condensation products, about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride. and about 0.05-0.l% by weight of an alkali salt of a weak organic acid.
- An impregnating composition for textile materials consisting of an aqueous solution containing about 2% by weight of a thermosetting condensation product selected from the group consisting of urea-formaldehyde and -urea-thiourea-formaldehyde condensation products, about 0.3-0.6% by weight of octadecyloxymethyl-pyridinium chloride, and about 0.05- 0.1% by weight of an alkali saltof a weak organic acid, and a catalyst consisting of about.
- a thermosetting condensation product selected from the group consisting of urea-formaldehyde and -urea-thiourea-formaldehyde condensation products, about 0.3-0.6% by weight of octadecyloxymethyl-pyridinium chloride, and about 0.05- 0.1% by weight of an alkali saltof a weak organic acid, and a catalyst consisting of about.
- a process for the treatment of textile materials consisting in impregnating the textile material with an aqueous solution containing about 2% by weight of a thermosetting condensation product selected from the group consisting of urea-formaldehyde and ureathiourea-formaldehyde condensation products and about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride, drying the impregnated material at a temperature below C.
- a thermosetting condensation product selected from the group consisting of urea-formaldehyde and ureathiourea-formaldehyde condensation products and about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride
- a process for the treatment of textile materials consisting in introducing into the textile material by weight of an aqueous solution containing about 2% by weight of a. thermosetting condensation product selected from the group consisting of urea-formaldehyde and urea-thiourea-i'ormaldehyde condensation products, about 0.3-0.6% by weight of octadecyloxymethyl-pyridinium chloride, about ODS-0.1% by weight of an alkali salt of a weak organic acid, and a catalyst consisting of about equal parts of hexamethylene tetramine and ammonium sulfate, drying the impregnated material at 60-70 C. and heating the dried material at -130 C. for 5-10 minutes.
- a thermosetting condensation product selected from the group consisting of urea-formaldehyde and urea-thiourea-i'ormaldehyde condensation products, about 0.3-0.6% by weight of octadecyloxymethyl-pyr
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Apr. 18, 1944 UNlTED RMPREGNATENG TEXTEE MATE Leo Beer, Padelpliia, Pa.
Ne Drawing. Application April 2 3, 1M3, Serial No. ceases (oi. zet -es) 13 Claims.
This invention relates to a method and means for treating textile materials and has particular relation to a process and a composition for reducing or eliminating the tendency of textile materials to shrink in laundering, and simultaneously improving the wearing qualities of said materials.
The main object of my present invention consists in treating textil materials with acomposition adapted to yield shrlnkproof products of improved wearing quality.
Another object of my invention is to reduce or eliminate the tendency of textile materials to shrink, by means of impregnating solutions of relatively low concentration.
A further object of this invention consists in the use of impregnating solutions which reduce the tendency of textile materials to shrink withoutimpairlng other properties of said materials.
Further objects and the advantages of the present invention will be apparent to those skilled in the art from the following specification and the appended claims.
It has been known in the art to produce shrinkproof textile materials by introducing thermosetting formaldehyde condensation products, particularly condensation products of the urea-formaldehyde type into the textil materials and converting said condensation products into resinous substances by heating. It has been found, however, that these condensation products must be used for the treatment of textiles in solutions of relatively high concentrations in order to obtain shrinkproof effects. Furthermore, incorporation of the condensation products in the textile fibers in the corresponding, relatively high amounts, results in deterioration of the wearing properties of the treated materials, particularly their resistance to abrasion. It has been suggested, therefore, to improve the wearin properties of fibers containing urea-formaldehyde resins by the application of rubber latex in mixture with said resins (U. S. Patent No. 2,299,786 of Oct. 27, 1942). g
I have now found that the necessity of using urea-formaldehyde type condensation products in relatively concentrated solutions, and the adherent disadvantage of adversely afiecting certain properties of the textile material treated, can be avoided by the use of solutions containing low amounts of heat-hardenable urea-form- In carrying out my present invention, the textile material to be treated is impregnated at ordlnary room temperature by causing'it to pass through aqueous liquid containing the above described mixture of urea-formaldehyde or ureathiourea=formaldehyde condensation product and octadecyloxymethyl-pyridinium chloride. In the preferred form of my invention, 1 use an, aqueous solution containing about 2% by weight of the urea-formaldehyde type condensation prodnot and about (id-0.6% of octadecyboxymethyb pyridlnium chloride. In the treatment of cellulosic materials it is advisable to add to the impregnatlng solution a small amount of a salt of a strong inorganic base, such as sodium or potassium, and a weak organic acid such as formic, acetic or lactic acid or an acid of similar strength. After passing through th impregnating solution, the textile material is squeezed out until it contains about 100% by weight of solution based on the weight of the dry starting material. The impregnated material is then dried at a relatively low temperature, f. e. at
aldehyde type condensation products in mixture with octadecyl-oxymethyl-pyridinium chloride, with or without the addition of a catalyst, as specified in the following examples.
about 4070 0., preferably at -70 C., and after drying heated for some minutes, f. e. 5-10 minutes, at l20-130 C. The impregnating solution may preferably contain a catalyst. I have found that the use of a catalyst consisting of about equal parts of hexamethylenetetramine and a suitable ammonium salt, such as ammonium sulfate, is. advantageous, particularly in the treatment of cellulosic materials.
It has been found that textile materials, such as fabrics, spun goods, filaments, webs, etc. consisting of W001, natural or regenerated cellulose, cellulose derivatives, such as cellulose acetate, or mixtures of these materials may be successfully treated according to the present invention. The
treated textile materials are shrinkproof and they show a substantial improvement with respect to their wearing qualities and particularly their re sistance to abrasion. In the case of woolen materials the tendency .to felt formation is also reduced.
Example I.Woolen stockings are wetted and immersed in an aqueous liquid containing in solution 2% by weight of a water-soluble ureaformaldehyde condensation product and 0.6% of octadecyl-oxymethyl-pyridinium chloride. The stockings are then squeezed or subjected to centrifugal action until they contain by weight of liquid based on the dry weight of the starting material. They are then dried at about 60- 70 C. and finally heated for about 5 minutes at -130 C. in a chamber heated by means of hot air. If the product thus obtained is subjected to washing with an aqueous soap solution, it substantially retains its original shape and dimensions. The resistance to abrasion of the material treated shows a very substantial increase in comparison to that of the untreated material. While the latter is rubbed through at 1000 cycles in Taber's testing machine. the treated material requires 4000 cycles for obtaining the sam effect under otherwise equal conditions.
Example II.A fabric consisting of 50% wool and 50% of cotton is treated with an aqueous liquid containing in 1 liter of the solution Grams Urea thiourea formaldehyde condensation produc l8 Octadecyl-oxymethyl-pyridinium chloride '6 sodium formate" 1 The treatment of the fabric with liquid and.
the subsequent drying and heating are carried out substantially in the manner described in Example I. The product obtained shows an improvement of the resistance to abrasion of 500 cycles on Taber's testing device in comparison to 350 cycles in the case of the untreated starting material,
Example IV.A cotton fabric consisting of cotton yarn in warp and filling is impregnated at l8-20 C. with a solution of Grams Urea thiourea formaldehyde condensation product 20 Octadecyl-oxymethyl-pyridinium chloride-.. 4 sodium formate 0.6 Hexamethylenetetramine 0.4 Ammoniumsulfate 0.4
in 1 liter of water. The treatment of the fabric is in all respects identical with that described in Example I. The product obtained is rubbed through at 850 cycles on the Taber machine in comparison to 600 cycles in the case of the untreated material.
Example V.-A fabric consisting of 50% of cotton and 50% of viscose rayon is treated in the manner described in Example I with the following solution:
Grams Urea-formaldehyde condensation product- 20 Octadecyl-oxymethyl-pyridinium chloride- 3 Hexamethylene tetramine 0.35 Aimnonium sulfate 0.4
Sodium lactate 1 dissolved in 1 liter of water. Drying and heatin of the impregnated fabric are also carried out in the manner described in Example I. .The finished product is rubbed through at 600 cycles in the Taber machine in comparison to 450 cycles in the case of the untreated starting material.
The eifect obtained in carrying out my present invention is unobvious because the use of an urea-formaldehyde type resin by itself under otherwise similar conditions does not result in a shrink-proof product, and because it could not be expected that deterioration of the textile product by the urea-formaldehyde compounds can be prevented by the presence of the octadecyl-oxymethyl-pyridinium chloride. Moreover, the use of said resin by itself causes deterioration of properties of the starting material while the combined use of resin and pyridinium salt under the conditions of my present invention, results in an improvement of said properties. For example, a rayon fabric, which, in its original, untreated condition, is rubbed through in Tabers testing device at 400 cycles, requires only 250 cycles after being treated in the customary manner with urea-formaldehyde type condensation products. If, however, the same fabric is treated in accordance with the present invention with a mixture of urea-formaldehyde type condensation products and octadecyl-oxymethyl-pyridinium chloride, it will be rubbed through in Taber's testing device at 550 cycles,
The urea condensation products used in carrying out my present invention are prepared in a manner known per se, f. e. by condensing one mol of urea or a mixture of urea and thiourea, with 2 mols of formaldehyde to a water-soluble condensation product which is recovered from the aqueous solution. The figures stated in the above examples relate to the solid, technically pure condensation products.
It will be understood that this invention is not limited to the specific embodiments set forth in the above examples, and the details set forth in these examples, such as the amount of the ingredients used or their relative proportions etc, may be varied without departing from the spirit of the invention as defined in the appended claims. a
I claim:
1. An impregnating composition for textile materials, said composition containing in aque ous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about Lil-2.2% by weight of a thermosetting condensation product selected from the group consisting of urea-formaldehyde and urea-thioureaformaldehyde condensation products.
2. An impregnating composition for textile materials, said composition containing in aqueous solution about 03-05% by weight of octadecyl-oxymethyl-pyridinium chloride and about 1.8-2.2% by weight of a thermosetting condensation product selected from the group,
' catalyst consistng of about equal parts of hen-- methylene tetramine and ammonium sulfate.
3. An impregnating composition for textile materials, said composition containing in aqua ous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about 1.8-2.2% by weight of a thermo-setting ureathiourea-formaldehyde condensation product.
4. An impregnating composition for textile materials, said composition containing in aque-- materials, said composition containing in aqueous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about 1.8-2.2% by weight of a thermo-setting ureaformaldehyde condensation product.
6. An impregnating composition for textile materials, said composition consisting of 3-6 parts by weight of octadecyl-oxymethyl-pyridinium chloride and about 18-22 parts by weight of a thermo-setting urea-formaldehyde condensation product dissolved in one liter of water.
7. An impregnating composition for textile materials, saidcomposition containing in aqueous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about 13.-2.2% by weight of a thermo-setting ureaformaldehyde condensation product and a catalyst consisting of about equal parts of hexamethylene tetramine and ammonium sulfate.
8. An impregnating composition for textile materials said composition containing in aqueous solution about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride and about 1.8-2.2% by weight of a thermo-setting condensation product selected from the group consisting of urea-formaldehyde and urea-thi'oureaformaldehyde condensation products, and an alkali salt of a weak organic acid.
9. An impregnating composition for textile materials, said composition consisting of an aqueous solution containing about 2% by weight of a thermosetting condensation product selected from the group consisting of urea-formaldehyde and urea-thiourea-formaldehyde condensation products, and about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride.
10. An impregnating composition for textile materials, said composition consisting of an aqueous solution containing about 2% by weight of athermosetting condensation product selected from the group consisting of urea-formaldehyde and urea' thiourea-formaldehyde condensation products, about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride. and about 0.05-0.l% by weight of an alkali salt of a weak organic acid.
11. An impregnating composition for textile materials, said composition consisting of an aqueous solution containing about 2% by weight of a thermosetting condensation product selected from the group consisting of urea-formaldehyde and -urea-thiourea-formaldehyde condensation products, about 0.3-0.6% by weight of octadecyloxymethyl-pyridinium chloride, and about 0.05- 0.1% by weight of an alkali saltof a weak organic acid, and a catalyst consisting of about.
equal parts of hexamethylene tetramine and ammonium sulfate.
12. A process for the treatment of textile materials, said process consisting in impregnating the textile material with an aqueous solution containing about 2% by weight of a thermosetting condensation product selected from the group consisting of urea-formaldehyde and ureathiourea-formaldehyde condensation products and about 0.3-0.6% by weight of octadecyl-oxymethyl-pyridinium chloride, drying the impregnated material at a temperature below C.
and heating the dried material at l20-130 C. 13. A process for the treatment of textile materials, said process consisting in introducing into the textile material by weight of an aqueous solution containing about 2% by weight of a. thermosetting condensation product selected from the group consisting of urea-formaldehyde and urea-thiourea-i'ormaldehyde condensation products, about 0.3-0.6% by weight of octadecyloxymethyl-pyridinium chloride, about ODS-0.1% by weight of an alkali salt of a weak organic acid, and a catalyst consisting of about equal parts of hexamethylene tetramine and ammonium sulfate, drying the impregnated material at 60-70 C. and heating the dried material at -130 C. for 5-10 minutes.
\ LEO BEER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US484462A US2347024A (en) | 1943-04-24 | 1943-04-24 | Impregnating composition for textile materials |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US484462A US2347024A (en) | 1943-04-24 | 1943-04-24 | Impregnating composition for textile materials |
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| US2347024A true US2347024A (en) | 1944-04-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US484462A Expired - Lifetime US2347024A (en) | 1943-04-24 | 1943-04-24 | Impregnating composition for textile materials |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2443368A (en) * | 1942-12-14 | 1948-06-15 | William Walker And Sons Ltd | Plasticized urea-formaldehyde resin |
| US2602018A (en) * | 1949-11-22 | 1952-07-01 | Beer Leo | Monomethylol dimethyl hydantoin and dimethylol urea to shrinkproof and creaseproof cellulose fabrics |
| US2622995A (en) * | 1948-02-21 | 1952-12-23 | Bancroft & Sons Co J | Process for resin impregnating cellulosic fabrics |
| US2644773A (en) * | 1949-03-17 | 1953-07-07 | Montclair Res Corp | Control of wool shrinkage by polyamides |
| US2696448A (en) * | 1949-03-17 | 1954-12-07 | Montclair Res Corp | Shrinkproofed wool and method for producing same |
| DE1043272B (en) * | 1952-05-10 | 1958-11-13 | Boehme Fettchemie Gmbh | Process for making textile materials crease-resistant |
-
1943
- 1943-04-24 US US484462A patent/US2347024A/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2443368A (en) * | 1942-12-14 | 1948-06-15 | William Walker And Sons Ltd | Plasticized urea-formaldehyde resin |
| US2622995A (en) * | 1948-02-21 | 1952-12-23 | Bancroft & Sons Co J | Process for resin impregnating cellulosic fabrics |
| US2644773A (en) * | 1949-03-17 | 1953-07-07 | Montclair Res Corp | Control of wool shrinkage by polyamides |
| US2696448A (en) * | 1949-03-17 | 1954-12-07 | Montclair Res Corp | Shrinkproofed wool and method for producing same |
| US2602018A (en) * | 1949-11-22 | 1952-07-01 | Beer Leo | Monomethylol dimethyl hydantoin and dimethylol urea to shrinkproof and creaseproof cellulose fabrics |
| DE1043272B (en) * | 1952-05-10 | 1958-11-13 | Boehme Fettchemie Gmbh | Process for making textile materials crease-resistant |
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