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US3109695A - Treatment of cellulosic fabrics and the fabrics thereby obtained - Google Patents

Treatment of cellulosic fabrics and the fabrics thereby obtained Download PDF

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US3109695A
US3109695A US58639A US5863960A US3109695A US 3109695 A US3109695 A US 3109695A US 58639 A US58639 A US 58639A US 5863960 A US5863960 A US 5863960A US 3109695 A US3109695 A US 3109695A
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fabric
fabrics
dihydroxyacetone
treatment
cellulosic
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US58639A
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Gardon John Leslie
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Rohm and Haas Co
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Rohm and Haas Co
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    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10Treating 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 oxygen
    • D06M13/12Aldehydes; Ketones
    • D06M13/127Mono-aldehydes, e.g. formaldehyde; Monoketones

Definitions

  • This invention relates to the treatment of cellulosic fabrics, such as those of cotton and regenerated cellulose rayon, for the purpose of imparting to them increased resilience, improved recovery from creasing, wrinkling, and other deformations, and the characteristic of having reduced shrinkage on washing so that partial or complete dimensional stabilization may be effected.
  • the invention also embraces the treated fabrics obtained.
  • cellulosic fabrics, woven, knitted, or otherwise formed have reduced shrinkage on washing and acquire resistance to creasing and crushing when they are treated with dihydroxyacetone of the formula HOCH COCH OH.
  • the extent of modification by means of this compound may be controlled by variation in the proportion of the dihydroxyacetone and by variation in the amount of catalyst employed during the treatment therewith.
  • the treatment with dihydroxyacetone may be effected most advantageously by means of aqueous solutions thereof in which the dihydroxyacetone is dissolved at a concentration which may vary from 2 to 25% by weight.
  • concentration is from 5 to 15% to obtain the maximum benefits in crease proofing and the like.
  • the treatment with dihydroxyacetone may be carried out in the presence of a catalyst.
  • Suitable catalysts are acids or acidic salts, such as oxalic acid, potassium persulfate, potassium bisulfate, magnesium chloride, ammonium chloride, zinc nitrate, zinc fluoborate, zinc perchlorate, and amine salts, such as the hydrochloride or sulfate of triethylamine, pyridine, morpholine, and 2- methyl-Z-aminopropanol-l.
  • Oxalic acid is a preferred catalyst with relatively little tendency to cause discoloration requiring bleaching.
  • the amount of catalyst may vary from about 0.1 to 5% and is preferably in the range of 1.0 to 2% concentration in the aqueous solution of dihydroxy- 'acetone.
  • the catalyzed solution of dihydroxyacetone is compatible with solutions or dispersions of most of the common textile finishing agents, such as synthetic polymer latices and aminoplast resins or precondensates, so that they may be applied with the dihydroxyacetone to produce changes in the hand or other properties of the fabric.
  • common textile finishing agents such as synthetic polymer latices and aminoplast resins or precondensates
  • the aqueous solution containing dihydroxyacetone and 'catalyst may be applied to the fabric in any suitable manner such as spraying or impregnation.
  • any suitable manner such as spraying or impregnation.
  • impregnation it is preferable to use some method of impregnation. With piece goods, this is conveniently carried out with the various machines used for treating fabrics in open width, such as pads or jigs.
  • the impregnation may be carried out in open width, and the fabric may be handled in any form.
  • the impregnation may be carried out in a tumble wheel, laundry machine, or other suitable equipment.
  • the drying and curing operations are preferably done with the fabric open and flat, so that it will have a smooth and even appearance when finished.
  • the impregnated fabric, immediately after impregnation and without preliminary low-temperature drying is carried in open width by a tenter frame through a curing oven where it is subjected to temperatures of about C. to about 2.00 C.
  • the treated fabrics exhibit a high degree of crush resistance and crease recovery with little or no change in the hand or feel of the fabric.
  • the treated fabrics have the important advantage that they do not retain chlorine, so that the use of bleaching agents containing chlorine does not cause deterioration either by way of discoloration or loss in tensile strength even when the treated fabrics which have been bleached are subjected to ironing temperatures.
  • the treated fabrics are also resistant to shrinkage during laundering, and the treatment is very permanent towards laundering, dry-cleaning, and other procedures for cleaning textile fabrics.
  • the treatment of the present invention using dihydroxyacetone as the sole cross-linking or crease-proofing agent provides a finish that is more stable to hydrolysis in acids and alkalies than the usual nitrogenous or aminoplast finishes. Any color introduced by the treatment is readily removable by reducing agents, such as sodium borohydride and sodium formaldehyde sulfoxylate.
  • Example 1 A sample of cotton printcloth was saturated with an aqueous solution containing 16% dihydroxyacetone and 0.8% zinc perchlorate. It was then put into an oven at 150 C. and baked for 15 minutes. A control treated with water was similarly prepared. After being conditioned, the samples had the following crease-recovery values:
  • Example 3 A sample of cotton printcloth was saturated with a 16% aqueous solution of dihydroxyacetone containing 0.4% NH Cl as the catalyst. It was cured in an oven at 150 C. for 15 minutes. After being conditioned, the sample had a creasearecovery angle of 136.
  • Example 4 A sample of cotton printcloth was treated with a solution containing 10% of dihydroxyacetone, 1% of oxalic acid, and 4% of a partially condensed urea-formaldehyde resin. The treated fabric was cured for 15 minutes at 150 C. After being conditioned, it had a stiffer, firmer, more resilient hand and a crease-recovery of 137.
  • Example 5 A sample of cotton printcloth was treated with a solution containing a mixture of 5% dihydroxyacetone and 5% dimethylol'N,N'-ethyleneurea with 1% oxalic acid as a catalyst. The application was made on a textile pad and the impregnated fabric was baked for minutes (2. at 150 C. After the fabric was conditioned, its creaserecovery angle was 139.
  • the process comprising impregnating a cellulosic fabric with an aqueous solution of dihydroxyacetone and an acidic catalyst and heating the impregnated fabric at a temperature of about to 200 (3., whereby the crease resistance of the fabric is increased.
  • a process as defined in is rayon.
  • the process comprising impregnating a cellulosic fabric with an aqueous solution containing 2 to 25% by weight of dihydroxyacetone and 0.1 to 5% of an acidic catalyst and heating the impregnated fabric at a temperature of about 110 to 200 C.
  • the process comprising impregnating a oellulosic fabric with an aqueous solution containing 2 to 25% by weight of dihydroxyacetone and 0.1 to 5% of oxalic acid as a catalyst, and heating the impregnated fabric at a temperature of about 110 to 200 C.
  • a cellulosic fabric having improved crease resistance obtained by the process claim 1.
  • a cotton fabric having improved crease resistance obtained by the process of claim 8.
  • a regenerated cellulosic fabric having improved crease resistance obtained by the process of claim 9.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)

Description

United States Patent Ofi ice 3,109,695 Patented Nov. 5, 1963 3,109,695 TREATMENT OF CELLULOSIC FABRICS AND THE FABRICS THEREBY OBTAINED John Leslie Gardon, Levittown, Pa., assignor to Rohm & Haas Company, Philadelphia, Pa., a corporation of Delaware No Drawing. Filed Sept. 27, 1960, Ser. No. 58,639
12 Claims. (Cl. 8-116.4)
This invention relates to the treatment of cellulosic fabrics, such as those of cotton and regenerated cellulose rayon, for the purpose of imparting to them increased resilience, improved recovery from creasing, wrinkling, and other deformations, and the characteristic of having reduced shrinkage on washing so that partial or complete dimensional stabilization may be effected. The invention also embraces the treated fabrics obtained.
In accordance with the present invention, it has been found that cellulosic fabrics, woven, knitted, or otherwise formed, have reduced shrinkage on washing and acquire resistance to creasing and crushing when they are treated with dihydroxyacetone of the formula HOCH COCH OH. The extent of modification by means of this compound may be controlled by variation in the proportion of the dihydroxyacetone and by variation in the amount of catalyst employed during the treatment therewith.
The treatment with dihydroxyacetone may be effected most advantageously by means of aqueous solutions thereof in which the dihydroxyacetone is dissolved at a concentration which may vary from 2 to 25% by weight. Preferably, the concentration is from 5 to 15% to obtain the maximum benefits in crease proofing and the like.
The treatment with dihydroxyacetone may be carried out in the presence of a catalyst. Suitable catalysts are acids or acidic salts, such as oxalic acid, potassium persulfate, potassium bisulfate, magnesium chloride, ammonium chloride, zinc nitrate, zinc fluoborate, zinc perchlorate, and amine salts, such as the hydrochloride or sulfate of triethylamine, pyridine, morpholine, and 2- methyl-Z-aminopropanol-l. Oxalic acid is a preferred catalyst with relatively little tendency to cause discoloration requiring bleaching.
Conveniently, the amount of catalyst may vary from about 0.1 to 5% and is preferably in the range of 1.0 to 2% concentration in the aqueous solution of dihydroxy- 'acetone.
The catalyzed solution of dihydroxyacetone is compatible with solutions or dispersions of most of the common textile finishing agents, such as synthetic polymer latices and aminoplast resins or precondensates, so that they may be applied with the dihydroxyacetone to produce changes in the hand or other properties of the fabric.
The aqueous solution containing dihydroxyacetone and 'catalyst may be applied to the fabric in any suitable manner such as spraying or impregnation. In general, it is preferable to use some method of impregnation. With piece goods, this is conveniently carried out with the various machines used for treating fabrics in open width, such as pads or jigs. However, it is not required that the impregnation be carried out in open width, and the fabric may be handled in any form. in treating garments or other articles made from cellulosic fabrics, the impregnation may be carried out in a tumble wheel, laundry machine, or other suitable equipment. After application of the solution, it is desirable to remove the excess solution by squeezing the fabric between rollers, or by shaking or centrifuging it, in order to insure a more even treatment. The fabric treated with solution may be dried, such as by a=ir-drying at normal room temperature or by heating in a drying oven at temperatures of 60 C. and up. The drying and curing operations are preferably done with the fabric open and flat, so that it will have a smooth and even appearance when finished. In a preferred embodiment; the impregnated fabric, immediately after impregnation and without preliminary low-temperature drying, is carried in open width by a tenter frame through a curing oven where it is subjected to temperatures of about C. to about 2.00 C. or higher for a period of time ranging from about one-half minute to about one-half hour or more, the shorter period being employed at the higher temperature and vice versa. Entirely satisfactory results are obtained by heating for 3 to 5 minutes at about C. This curing operation not only dries the impregnated fabric but apparently causes a reaction between the dihydroxyacetone and the hydroxyl groups of the cellulose. The precise reaction is not known. It is theorized that the two hydroxyl groups of the dihydroxyacetone may ethen'fy hydroxyl groups of the same or different molecules of cellulose, but it is also thought that the carbonyl group may take part in the reaction so that a single molecular residue of dihydroxyacetone is connected at three points to from one to three cellulose molecules. It is not intended, however, that the present invention be limited to this theory of operation.
The treated fabrics exhibit a high degree of crush resistance and crease recovery with little or no change in the hand or feel of the fabric. In addition, the treated fabrics have the important advantage that they do not retain chlorine, so that the use of bleaching agents containing chlorine does not cause deterioration either by way of discoloration or loss in tensile strength even when the treated fabrics which have been bleached are subjected to ironing temperatures. The treated fabrics are also resistant to shrinkage during laundering, and the treatment is very permanent towards laundering, dry-cleaning, and other procedures for cleaning textile fabrics. The treatment of the present invention using dihydroxyacetone as the sole cross-linking or crease-proofing agent provides a finish that is more stable to hydrolysis in acids and alkalies than the usual nitrogenous or aminoplast finishes. Any color introduced by the treatment is readily removable by reducing agents, such as sodium borohydride and sodium formaldehyde sulfoxylate.
The following examples illustrate the present invention, and the parts and percentages therein are by weight unless otherwise noted. The crease-recovery values given below were determined by the Shirley Institute procedure (British Standards Handbook No. 11, 1949 ed., page 128), in the warp direction.
Example 1 A sample of cotton printcloth was saturated with an aqueous solution containing 16% dihydroxyacetone and 0.8% zinc perchlorate. It was then put into an oven at 150 C. and baked for 15 minutes. A control treated with water was similarly prepared. After being conditioned, the samples had the following crease-recovery values:
Crease-recovery angle, degrees Water control 71 Dihydroxyacetone 141 The dihydroxyacetone-treated fabric was insoluble in cuprammonium hydroxide while the control dissolved readily.
The durability of the treatment was shown by the following tests. Samples of the dihydroxyacetone-treated fabric were extracted (1) in boiling water for one hour, (2) in 0.1 N HCl at 80 C. for one hour, and (3) in 0.1 N NaOH for 24 hours at 20 C. The extracted samples were still insoluble in cuprammonium hydroxide and had good crease-recovery, as shown by the following data:
Degrees Water extr on 132 HCl extr on 125 NaOH extr on 123 Example 2 Example 3 A sample of cotton printcloth was saturated with a 16% aqueous solution of dihydroxyacetone containing 0.4% NH Cl as the catalyst. It was cured in an oven at 150 C. for 15 minutes. After being conditioned, the sample had a creasearecovery angle of 136.
Example 4 A sample of cotton printcloth was treated with a solution containing 10% of dihydroxyacetone, 1% of oxalic acid, and 4% of a partially condensed urea-formaldehyde resin. The treated fabric was cured for 15 minutes at 150 C. After being conditioned, it had a stiffer, firmer, more resilient hand and a crease-recovery of 137.
Example 5 A sample of cotton printcloth was treated with a solution containing a mixture of 5% dihydroxyacetone and 5% dimethylol'N,N'-ethyleneurea with 1% oxalic acid as a catalyst. The application was made on a textile pad and the impregnated fabric was baked for minutes (2. at 150 C. After the fabric was conditioned, its creaserecovery angle was 139.
I claim:
1. The process comprising impregnating a cellulosic fabric with an aqueous solution of dihydroxyacetone and an acidic catalyst and heating the impregnated fabric at a temperature of about to 200 (3., whereby the crease resistance of the fabric is increased.
2. A process as defined in claim 1 in which the fabric is cotton.
3. A process as defined in is rayon.
4. The process comprising impregnating a cellulosic fabric with an aqueous solution containing 2 to 25% by weight of dihydroxyacetone and 0.1 to 5% of an acidic catalyst and heating the impregnated fabric at a temperature of about 110 to 200 C.
5. A process as defined in claim 4 in which the fabric is cotton.
6. A process as defined in claim 4 in which the fabric is rayon.
7. The process comprising impregnating a oellulosic fabric with an aqueous solution containing 2 to 25% by weight of dihydroxyacetone and 0.1 to 5% of oxalic acid as a catalyst, and heating the impregnated fabric at a temperature of about 110 to 200 C.
8. A process according to claim 7 in which the fabric is cotton.
9. A process according to claim 7 in which the fabric is rayon.
10. A cellulosic fabric having improved crease resistance obtained by the process claim 1.
11. A cotton fabric having improved crease resistance obtained by the process of claim 8.
12. A regenerated cellulosic fabric having improved crease resistance obtained by the process of claim 9.
claim 1 in which the fabric References Cited in the file of this patent UNITED STATES PATENTS

Claims (1)

1. THE PROCESS COMPRISING IMPREGNATING A CELLULOSIC FABRIC WITH AN AQUEOUS SOLUTION OF DIHYDROXYACETONE AND AN ACIDIC CATALYST AND HEATING THE IMPREGNATED FABRIC AT A TEMPERATURE OF ABUT 110* TO 200*C., WHEREBY THE CREASE RESISTANCE OF THE FABRIC IS INCREASED.
US58639A 1960-09-27 1960-09-27 Treatment of cellulosic fabrics and the fabrics thereby obtained Expired - Lifetime US3109695A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3477802A (en) * 1963-03-19 1969-11-11 Stevens & Co Inc J P Modification of cellulose,polyvinyl alcohol and starch with compounds characterized by ethylene radicals having an electron attracting group which stabilizes carbanions on one carbon atom thereof and an alkoxy or hydroxy group on the other

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2486399A (en) * 1947-10-28 1949-11-01 Dan River Mills Inc Polymeric polyhydric alcohol condensation products and treatment of cellulosic textiles therewith

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2486399A (en) * 1947-10-28 1949-11-01 Dan River Mills Inc Polymeric polyhydric alcohol condensation products and treatment of cellulosic textiles therewith

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3477802A (en) * 1963-03-19 1969-11-11 Stevens & Co Inc J P Modification of cellulose,polyvinyl alcohol and starch with compounds characterized by ethylene radicals having an electron attracting group which stabilizes carbanions on one carbon atom thereof and an alkoxy or hydroxy group on the other

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