US2304252A - Process of insolubilizing hydroxylcontaining sizes - Google Patents
Process of insolubilizing hydroxylcontaining sizes Download PDFInfo
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- US2304252A US2304252A US253996A US25399639A US2304252A US 2304252 A US2304252 A US 2304252A US 253996 A US253996 A US 253996A US 25399639 A US25399639 A US 25399639A US 2304252 A US2304252 A US 2304252A
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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
- D06M13/368—Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases
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- Patented Dec. 8, 1942 UNITED STATES ATENT OFFICE PROCESS OF INSOLUBILIZDN'G HYDROXYL- CONTAINING SIZES Onslow B. Hager, Glenside, and Louis H. Bock and Alva L. Honk, Philadelphia, Pa., assignors to Riihm & Haas Company, Philadelphia, Pa.
- R is an aliphatic hydrocarbon group
- X is a salt-forming anion
- R1, R2, and R3 are hydrogen or alkyl groups or R1 and R2 jointly form an aromatic ring.
- the high molecular weight, hydroxyl-containing substances which are water dispersible or water-soluble are useful for sizing or finishing fabric and paper; but they are readily redispersedby water. For many purposes it becomes desirable to provide a finish which is not readily removable by washing.
- the quaternary salts from heterocyclic amines are not entirely stable in aqueous solutions, a property which interferes with their practical application and with the compounding of prepared sizing compositions. When these compounds are heated to cause fix'ation of the starch, toxis fumes are evolved.
- the quaternary salts formed from trimetlrvlamine and the like are too stable for practical use and require excessive temperatures for their application. This results in injury to fabric as well as unsatisfactory finishes.
- size and of fixing agent is preferably performed in a single bath, but treatments with these substances in separate baths are also effective.
- Mildly acidic catalysts or alkaline catalysts seem to assist in the reaction between the sizing'materials and the fixing agent, but are not essential. For example, it is helpful to add ammonium chloride, sodium acetate, borax, sodium bicarbonate, sodium carbonate, and the like.
- the treated material may be dried in a separate operation before the final heating, but such drying is not essential as it may be performed as part of the heating procedure in which the size and agent are reacted. It is sometimes desirable to wash the sized fabric before the last finishing operation in order to remove salts, decomposition products, or excess, unfixed sizing material.
- Quaternary ammonium compounds of the above general type possess advantages over other quaternary compounds in having such a degree of stability that they may be incorporated in sizing preparations, whether in dry form or in paste form, yet they react under such conditions of moisture, temperature, and pH that fibers or fabrics are not unduly tendered. N0 noxious or toxic fumes are evolved. By proper choice of the individual compound different degrees of stiffness and qualities of finish may be produced. These compounds are useful with any of the sizing materials which contain a multiplicity of hydroxyl groups.
- Quaternary ammonium salts of the type found particularly effective may be prepared by reacting a tertiar amine carrying a flry-unsaturated hydrocarbon group, such as allyl dimethylamine or benzyl dimethylamine, with a halomethyl ether, such as caproxymethyl chloride.
- a tertiar amine carrying a flry-unsaturated hydrocarbon group such as allyl dimethylamine or benzyl dimethylamine
- a halomethyl ether such as caproxymethyl chloride.
- quaternary salts may also be prepared by steps involving (1) the synthesis of an alkoxymethyl tertiary amine, such as lauryloxymethyl dlmethyl amine, which is obtained by reacting a primary alcohol, formaldehyde, and a secondary amine, and (2) the reaction of the alkoxymethyl tertiary amine with a suitable unsaturated agent for alkylation, such as methallyl bromide, allyl chloride, benzyl-chloride, o'rthe like.
- a suitable unsaturated agent for alkylation such as methallyl bromide, allyl chloride, benzyl-chloride, o'rthe like.
- R-O-CHr-lL-R' c i on wherein R is a member of the class consisting of allyl, p-methallyl, crotyl and benzyl groups.
- the group R in the above formulae may be any aliphatic hydrocarbon radical. It may possess a straight chain or a branched chain; it may be saturated or unsaturated. We have observed that the maximum degree of fixation of starch occurs when the carbon atom content of R. is about about reaction of the sizing material and the four to eight, but fewer carbon atoms or more L.
- the water-soluble or water-dispersibie, polyhydroxy, high molecular weight compounds which" are useful for sizing or finishing include cellulose ethers, such as'the water-soluble forms of methyl and ethyl cellulose, hydroxyethyl cellulose and the like, polyvinyl alcohol, and the starches and starchy products, including com, rice, tapioca, sago, wheat, and potato starch, fiours containing starches, modified and treated starches, converted starches, etc.
- Other materials which are commonly applied with starch such as fillers, pigments, softeners, resins, etc., may also be incorporated in the finishing mixtures.
- the polyhydroxy sizing materials react at slightly elevated temperatures with thequaternary salts described above to form insoluble complexes which thus provide improved finishes.
- the sizing preparation is used to impregnate or coat fabric by any suitable means. such as padding. Then, the. fabric, with or without drying, is
- a size may be partially reacted with one of the quaternary ammonium compounds of the type described above by heating the size with the quaternary compound. The partially reacted size is then applied to fibers or fabric and completely insolubilized thereon by a final heating of the sized fibers or fabric.
- the temperature required to set the size is over C. In general a temperature of to 140 C. for fifteen minutes or more will render size permanently insoluble. In plant operations the heating step is accomplished on hot cans or in closed tenters, loop driers and the like.
- Example 1 Cotton yarn was treated with a preparation containing 2 parts of a 26% solution of cetyloxymethyl dimethyl benzyl ammonium chloride and 40 parts of a 4% aqueous solution of ethyl cellulose. The excess was squeezed off and 'the yarn dried at room temperature. It was then heated in the oven at C. for one-half hour. A stiff coating resulted, which softened when wet but regained its stifl'ness when dried. It was not removed by washing.
- Example 2 Cotton lawn was coated with an aqueous solution containing 1.2% of capryloxymethyl dimethyl benzyl ammonium chloride, 0.25% of sodium bicarbonate, and 4% of water-soluble ethyl cellulose. The excess was squeezed oil and the cloth dried at room temperature. It was heated at 125 C. for one-half hour, washed twice, and ironed. A stifl, full finish was obtained which was not removed by laundering.
- Example 3 Cotton lawn was coated with an aqueous solution containing 2.4% lauryloxymethyl dimethyl methallyl ammonium chloride and 4.5% hydroxyethyl cellulose. It-was squeezed and air-dried,
- Example 5 Woolen cloth was coated with an aqueous solution containing 4.5% of isobutyloxymethyl dimethyl benzyl ammonium chloride and 3.3% of water-soluble ethyl cellulose. The excess was pressed-on and the cloth air-dried, then heated at 125 C. for one-half hour. very stifl, retaining the stillness after washing.
- Example 6 A pure-silk fabric was coated with an aqueous solution containing 2.25% of capryloxymethyi di- The material was methyl benzyl ammonium chloride, 0.5% of disodium phosphate, and 7.25% of potato starch. The excess was squeezed oh and the cloth dried at room temperature. It was heated at 120 C. for one-half hour and washed. A still? finish resulted, permanent to washing.
- Example7 A viscose rayon fabric was coated with an aqueous solution containing 6.2% ethoxymethyldimethyl benzyl ammonium chloride and 3.0% of water-soluble ethyl cellulose. It was squeezed, dried, and heated one-half hour at 125 C. Good stiffening resulted, retained after washing and drying.
- Example 8 Cotton sheeting was coated with a solution containing 4.3% of methoxymethyl dimethyl benzyl ammonium chloride and 3.3% of water-soluble ethyl cellulose. The excess was squeezed oi, the cloth dried and heated at 125 C. for one-half hour. It was given two washes, retaining good stiffness.
- Example 9 Cotton sheeting was coated with an aqueous solution containing 3.7% of water-soluble ethyl cellulose and 2.7% of a compound obtained by the reaction of benzyl dimethylamine with a chloromethyl ether of an alcohol having an iodine number of 44 and a hydroxyl number of 228. The cloth was squeezed, dried, and heated one-half hour at 125 C. It gave a very stiff finish, permanent to washing, and exhibited some waterrepellency.
- Example 10 Cotton lawn was coated with a solution of 1 part of 26% cetyloxymethyl dimethyl benzyl ammonium chloride in 3 parts of 4% water-soluble ethyl cellulose. It was squeezed, dried, and heated at 120 C. for one-half hour. After washing, it was fairly stiff and very repellent to water. It had gained in weight 21%.
- Example 11 Cotton sheeting was coated with an aqueous solution of 3.7% tapioca starch and 6.5% cetyloxymethyl dimethyl benzyl ammonium chloride. The excess was squeezed out, the cloth dried. and heated one-half hour at 125 C. The cloth was fuller, with slight stiffening, and was waterrepellent.
- Ezample 12 A coating composition comprising 11.3%, of polyvinyl alcohol and 6.5% capryloxymethyl dimethyl benzyl ammonium chloride was adjusted to a pH of 5.8 with acetic acid, and applied to cotton sheeting, dried and heated one-half hour at 130 C. and washed. The cloth retained a stifi finish resistant to further washing.
- Example 13 An unmercerized, vat blue, x 80, 4-yd. percale was padded with moderate pressure through a solution containing 1.5% hydroxyethyl cellulose and 4% caproxymethyl dimethyl benzyl ammonium chloride. The cloth was dried at 37" in a closed tenter at 220-230 F. From the frame the fabric was baked for ten minutes at 290 F. in a loop drier with good circulation of air and calendered. The fabric was made full-bodied and given a slight degree of firmness and a wellfilled appearance. These properties were retained on laundering.
- This process of improving the fastness of waterdispersible sizes may be applied to yarn, fabric, thread or fibers of any material, which may be heated over C. without impairing the properties of the sized material. It may thus be applied to cotton, linen, paper, straw, jute, hemp, the various synthetic fibers, etc.
- a method for improving the wash-fastness on textile material of hydroxylecontaining size selected from the group consisting of watersoluble cellulose ethers, polyvinyl alcohol and starch sizes which comprises treating the textile material with said size and a quaternary ammonium salt of the formula-- wherein R represents an aliphatic hydrocarbon group, R represents a group selected from allyl, p-methallyl, crotyl, and benzyl radicals, and X represents a salt-forming anion, and subsequently heating the treated material to efiect reaction between the size and the quaternary ammonium salt.
- a method for improving the wash-fastness on textile material of a starch size which comprises treating the textile material with said size and a quaternary ammonium salt of the formulawherein R represents an aliphatic hydrocarbon group, R represents a group selected from allyl, p-methallyl, crotyl, and benzyl radicals, and X represents a salt-forming anion, and subsequently heating the treated material to eifect reaction between the size and the quaternary ammonium salt.
- a method for improving the wash-fastness on textile material of polyvinyl alcohol which comprises treating the textile material with said alcohol and a quaternary ammonium salt of the formulawherein R represents an aliphatic hydrocarbon group, R represents a group selected from allyl, p-methaliyl, crotyl, and benzyl radicals, and X represents 'a salt-forming anion, and subsequently heating the treated material to effect reaction between saidalcohol and the quaternary ammonium salt.
- a method for improving the wash-fastness on textile material of a water-soluble cellulose ether which comprises treating the textile material with said ether and a quaternary ammonium salt of the formulawherein R represents an aliphatic hydrocarbon group, R represents a group selected from allyl, p-methallyl, crotyl, and benzyl radicals, and X represents a salt-forming anion, and subsequently heating the treated material to effect reaction between said ether and said salt.
- a method for improving the wash-fastness on textile material of 'hydroxyl-containing size selected from the group consisting of watersoluble cellulose ethers, polyvinyl alcohol and starch sizes which comprises treating the textile material with said size and a quaternary ammonium salt ofthe formula i nocm-N-c CH1 CH1 wherein R represents an aliphatic hydrocarbon group and x represents a halogen, and subse I quently heating the treated material to efiect CH: CH:
- R represents an aliphatic hydrocarbon group and X represents a halogen
- a method for improving the wash-iastness V on textile material of polyvinyl alcohol which comprises treating the textile material with said alcohol and a quaternary ammonium salt of the formula- CH: CH;
- R represents an aliphatic hydrocarbon group and X represents a halogen
- a method for improving the wash-fastness on textile material 01' a water-soluble cellulose ether, which comprises treating the textile material with said ether and a quaternary ammonium salt of the formula methyl benzyl ammonium chloride, and subse-- quently heating the treated material to eifect reaction between the size and caproxymethyl dimethyl benzyl ammonium chloride.
- a method for improving the wash-fastness on textile material of starch size which comprises treating the textile material with said size and caproxymethyl dimethyl benzyl ammonium chloride, and subsequently heating the treated material to efiect reaction between the size and caproxymethyl dimethyl benzyl ammonium chloride.
- a method for improving the wash-iastness on textile material of hydroxyl-containing size from the group consisting of water-soluble cel lulose ethers, polyvinyl alcohol and starch sizes which comprises treating the textile material with said size and cetyloxymethyl dimethyl benzyl ammonium chloride, and subsequently heating the treated material to eiiect reaction between the size and cetyloxymethyl dimethyl benzyl ammonium chloride.
- a method for improving the wash-fastness on textile material of a water-soluble cellulose ether size which comprises treating the textile material with said size and cetyloxymethyl dimethyl benzyl ammonium chloride, and subsequently heating the treated material to attest reaction between the size and cetyloxymethyl-dimethyl benzyl ammonium chloride.
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Description
Patented Dec. 8, 1942 UNITED STATES ATENT OFFICE PROCESS OF INSOLUBILIZDN'G HYDROXYL- CONTAINING SIZES Onslow B. Hager, Glenside, and Louis H. Bock and Alva L. Honk, Philadelphia, Pa., assignors to Riihm & Haas Company, Philadelphia, Pa.
No Drawing. Application February 1, 1939, Serial No. 253,996
13 Claims.
wherein R is an aliphatic hydrocarbon group, X is a salt-forming anion and R1, R2, and R3 are hydrogen or alkyl groups or R1 and R2 jointly form an aromatic ring.
The high molecular weight, hydroxyl-containing substances which are water dispersible or water-soluble are useful for sizing or finishing fabric and paper; but they are readily redispersedby water. For many purposes it becomes desirable to provide a finish which is not readily removable by washing. No general method has heretofore been available for the treatment of sizing materials, although attempts have been made to fix starch. The setting of starch finishes by treating with quaternary organic compounds, built up from heterocyclic tertiary bases, such as pyridine, or from such tertiary amines as trimethylamine, triethylamine, triethanolamine, etc., presents various serious disadvantages. The quaternary salts from heterocyclic amines are not entirely stable in aqueous solutions, a property which interferes with their practical application and with the compounding of prepared sizing compositions. When these compounds are heated to cause fix'ation of the starch, toxis fumes are evolved. The quaternary salts formed from trimetlrvlamine and the like are too stable for practical use and require excessive temperatures for their application. This results in injury to fabric as well as unsatisfactory finishes.
It is an object of this invention to provide a general method of rendering water-soluble or water-dispersible, hydroxyl-containing, high molecular weight, sizing materials relatively insoluble. It is an object of this invention to provide a superior means for improving the fastness of water-dispersible, sizing materials on fabric without causing deterioration of fabric or finish and without evolving toxic fumes.
We have found that, when hydroxyl-containing, sizing materials are heated with a quaternary compound of the general formula given above, they become insolubilized. If. fabric, yarn, or fibers are treated with such a sizing material and with the said quaternary compound, and the sized fabric, yarn or fibers are then heated, the sizing and quaternary compound react and the sizing becomes fixed and fast to ordinary washing. Fabric sized by this method is permanently stiffened.
Application of size and of fixing agent is preferably performed in a single bath, but treatments with these substances in separate baths are also effective. Mildly acidic catalysts or alkaline catalysts seem to assist in the reaction between the sizing'materials and the fixing agent, but are not essential. For example, it is helpful to add ammonium chloride, sodium acetate, borax, sodium bicarbonate, sodium carbonate, and the like. After application of the sizing materials and the fixing agent to fabric, yarn, or fiber, the treated material may be dried in a separate operation before the final heating, but such drying is not essential as it may be performed as part of the heating procedure in which the size and agent are reacted. It is sometimes desirable to wash the sized fabric before the last finishing operation in order to remove salts, decomposition products, or excess, unfixed sizing material.
Quaternary ammonium compounds of the above general type possess advantages over other quaternary compounds in having such a degree of stability that they may be incorporated in sizing preparations, whether in dry form or in paste form, yet they react under such conditions of moisture, temperature, and pH that fibers or fabrics are not unduly tendered. N0 noxious or toxic fumes are evolved. By proper choice of the individual compound different degrees of stiffness and qualities of finish may be produced. These compounds are useful with any of the sizing materials which contain a multiplicity of hydroxyl groups.
Quaternary ammonium salts of the type found particularly effective may be prepared by reacting a tertiar amine carrying a flry-unsaturated hydrocarbon group, such as allyl dimethylamine or benzyl dimethylamine, with a halomethyl ether, such as caproxymethyl chloride.
or butyloxymethyl bromide. Certain suitable quaternary salts-may also be prepared by steps involving (1) the synthesis of an alkoxymethyl tertiary amine, such as lauryloxymethyl dlmethyl amine, which is obtained by reacting a primary alcohol, formaldehyde, and a secondary amine, and (2) the reaction of the alkoxymethyl tertiary amine with a suitable unsaturated agent for alkylation, such as methallyl bromide, allyl chloride, benzyl-chloride, o'rthe like.
The compounds which are most readily available may be conveniently grouped in the following general formula i R-O-CHr-lL-R' c i on, wherein R is a member of the class consisting of allyl, p-methallyl, crotyl and benzyl groups. The group R in the above formulae may be any aliphatic hydrocarbon radical. It may possess a straight chain or a branched chain; it may be saturated or unsaturated. We have observed that the maximum degree of fixation of starch occurs when the carbon atom content of R. is about about reaction of the sizing material and the four to eight, but fewer carbon atoms or more L. The water-soluble or water-dispersibie, polyhydroxy, high molecular weight compounds which" are useful for sizing or finishing include cellulose ethers, such as'the water-soluble forms of methyl and ethyl cellulose, hydroxyethyl cellulose and the like, polyvinyl alcohol, and the starches and starchy products, including com, rice, tapioca, sago, wheat, and potato starch, fiours containing starches, modified and treated starches, converted starches, etc. Other materials which are commonly applied with starch, such as fillers, pigments, softeners, resins, etc., may also be incorporated in the finishing mixtures.
The polyhydroxy sizing materials react at slightly elevated temperatures with thequaternary salts described above to form insoluble complexes which thus provide improved finishes. In carrying outsizing operations with fabric about two parts of the quaternary ammonium compound may be added to one to ten parts of a water-dispersible size in a treating bath. The sizing preparation is used to impregnate or coat fabric by any suitable means. such as padding. Then, the. fabric, with or without drying, is
heated to a temperature suiiiciently high to bring quaternary ammonium compound.
While a one-bath process is usually to be desired, the equivalent result is obtained from a two-bath process in which size is applied from one bath and the quaternary ammonium compound from a second bath. As yet another procedure, a size may be partially reacted with one of the quaternary ammonium compounds of the type described above by heating the size with the quaternary compound. The partially reacted size is then applied to fibers or fabric and completely insolubilized thereon by a final heating of the sized fibers or fabric.
The temperature required to set the size is over C. In general a temperature of to 140 C. for fifteen minutes or more will render size permanently insoluble. In plant operations the heating step is accomplished on hot cans or in closed tenters, loop driers and the like.
To illustrate the general process the following specific examples are given:
Example 1 Cotton yarn was treated with a preparation containing 2 parts of a 26% solution of cetyloxymethyl dimethyl benzyl ammonium chloride and 40 parts of a 4% aqueous solution of ethyl cellulose. The excess was squeezed off and 'the yarn dried at room temperature. It was then heated in the oven at C. for one-half hour. A stiff coating resulted, which softened when wet but regained its stifl'ness when dried. It was not removed by washing.
Example 2 Cotton lawn was coated with an aqueous solution containing 1.2% of capryloxymethyl dimethyl benzyl ammonium chloride, 0.25% of sodium bicarbonate, and 4% of water-soluble ethyl cellulose. The excess was squeezed oil and the cloth dried at room temperature. It was heated at 125 C. for one-half hour, washed twice, and ironed. A stifl, full finish was obtained which was not removed by laundering.
Example 3 Example 4 Cotton lawn was coated with an aqueous solution containing 2.4% lauryloxymethyl dimethyl methallyl ammonium chloride and 4.5% hydroxyethyl cellulose. It-was squeezed and air-dried,
then heated at 125 C. for one-half hour. The
material was very stiif even after washing.
Example 5 Woolen cloth was coated with an aqueous solution containing 4.5% of isobutyloxymethyl dimethyl benzyl ammonium chloride and 3.3% of water-soluble ethyl cellulose. The excess was pressed-on and the cloth air-dried, then heated at 125 C. for one-half hour. very stifl, retaining the stillness after washing.
Example 6 A pure-silk fabric was coated with an aqueous solution containing 2.25% of capryloxymethyi di- The material was methyl benzyl ammonium chloride, 0.5% of disodium phosphate, and 7.25% of potato starch. The excess was squeezed oh and the cloth dried at room temperature. It was heated at 120 C. for one-half hour and washed. A still? finish resulted, permanent to washing.
Example7 A viscose rayon fabric was coated with an aqueous solution containing 6.2% ethoxymethyldimethyl benzyl ammonium chloride and 3.0% of water-soluble ethyl cellulose. It was squeezed, dried, and heated one-half hour at 125 C. Good stiffening resulted, retained after washing and drying.
Example 8 Cotton sheeting was coated with a solution containing 4.3% of methoxymethyl dimethyl benzyl ammonium chloride and 3.3% of water-soluble ethyl cellulose. The excess was squeezed oi, the cloth dried and heated at 125 C. for one-half hour. It was given two washes, retaining good stiffness.
Example 9 Cotton sheeting was coated with an aqueous solution containing 3.7% of water-soluble ethyl cellulose and 2.7% of a compound obtained by the reaction of benzyl dimethylamine with a chloromethyl ether of an alcohol having an iodine number of 44 and a hydroxyl number of 228. The cloth was squeezed, dried, and heated one-half hour at 125 C. It gave a very stiff finish, permanent to washing, and exhibited some waterrepellency.
Example 10 Cotton lawn was coated with a solution of 1 part of 26% cetyloxymethyl dimethyl benzyl ammonium chloride in 3 parts of 4% water-soluble ethyl cellulose. It was squeezed, dried, and heated at 120 C. for one-half hour. After washing, it was fairly stiff and very repellent to water. It had gained in weight 21%.
Example 11 Cotton sheeting was coated with an aqueous solution of 3.7% tapioca starch and 6.5% cetyloxymethyl dimethyl benzyl ammonium chloride. The excess was squeezed out, the cloth dried. and heated one-half hour at 125 C. The cloth was fuller, with slight stiffening, and was waterrepellent.
Ezample 12 A coating composition comprising 11.3%, of polyvinyl alcohol and 6.5% capryloxymethyl dimethyl benzyl ammonium chloride was adjusted to a pH of 5.8 with acetic acid, and applied to cotton sheeting, dried and heated one-half hour at 130 C. and washed. The cloth retained a stifi finish resistant to further washing.
Example 13 Example 14 An unmercerized, vat blue, x 80, 4-yd. percale was padded with moderate pressure through a solution containing 1.5% hydroxyethyl cellulose and 4% caproxymethyl dimethyl benzyl ammonium chloride. The cloth was dried at 37" in a closed tenter at 220-230 F. From the frame the fabric was baked for ten minutes at 290 F. in a loop drier with good circulation of air and calendered. The fabric was made full-bodied and given a slight degree of firmness and a wellfilled appearance. These properties were retained on laundering.
This process of improving the fastness of waterdispersible sizes may be applied to yarn, fabric, thread or fibers of any material, which may be heated over C. without impairing the properties of the sized material. It may thus be applied to cotton, linen, paper, straw, jute, hemp, the various synthetic fibers, etc.
We claim:
1. A method for improving the wash-fastness on textile material of hydroxylecontaining size selected from the group consisting of watersoluble cellulose ethers, polyvinyl alcohol and starch sizes, which comprises treating the textile material with said size and a quaternary ammonium salt of the formula-- wherein R represents an aliphatic hydrocarbon group, R represents a group selected from allyl, p-methallyl, crotyl, and benzyl radicals, and X represents a salt-forming anion, and subsequently heating the treated material to efiect reaction between the size and the quaternary ammonium salt.
2. A method for improving the wash-fastness on textile material of a starch size, which comprises treating the textile material with said size and a quaternary ammonium salt of the formulawherein R represents an aliphatic hydrocarbon group, R represents a group selected from allyl, p-methallyl, crotyl, and benzyl radicals, and X represents a salt-forming anion, and subsequently heating the treated material to eifect reaction between the size and the quaternary ammonium salt.
3. A method for improving the wash-fastness on textile material of polyvinyl alcohol, which comprises treating the textile material with said alcohol and a quaternary ammonium salt of the formulawherein R represents an aliphatic hydrocarbon group, R represents a group selected from allyl, p-methaliyl, crotyl, and benzyl radicals, and X represents 'a salt-forming anion, and subsequently heating the treated material to effect reaction between saidalcohol and the quaternary ammonium salt.
4. A method for improving the wash-fastness on textile material of a water-soluble cellulose ether, which comprises treating the textile material with said ether and a quaternary ammonium salt of the formulawherein R represents an aliphatic hydrocarbon group, R represents a group selected from allyl, p-methallyl, crotyl, and benzyl radicals, and X represents a salt-forming anion, and subsequently heating the treated material to effect reaction between said ether and said salt.
5. A method for improving the wash-fastness on textile material of 'hydroxyl-containing size selected from the group consisting of watersoluble cellulose ethers, polyvinyl alcohol and starch sizes, which comprises treating the textile material with said size and a quaternary ammonium salt ofthe formula i nocm-N-c CH1 CH1 wherein R represents an aliphatic hydrocarbon group and x represents a halogen, and subse I quently heating the treated material to efiect CH: CH:
wherein R represents an aliphatic hydrocarbon group and X represents a halogen, and subsequently heating the treated material to eiiect reaction between the size and the quaternary ammonium salt.
'I. A method for improving the wash-iastness V on textile material of polyvinyl alcohol, which comprises treating the textile material with said alcohol and a quaternary ammonium salt of the formula- CH: CH;
wherein R represents an aliphatic hydrocarbon group and X represents a halogen, and subsequently heating the treated material to effect reaction between the size and the quaternary ammonium salt.
8. A method for improving the wash-fastness on textile material 01' a water-soluble cellulose ether, which comprises treating the textile material with said ether and a quaternary ammonium salt of the formula methyl benzyl ammonium chloride, and subse-- quently heating the treated material to eifect reaction between the size and caproxymethyl dimethyl benzyl ammonium chloride.
10. A method for improving the wash-fastness on textile material of starch size which comprises treating the textile material with said size and caproxymethyl dimethyl benzyl ammonium chloride, and subsequently heating the treated material to efiect reaction between the size and caproxymethyl dimethyl benzyl ammonium chloride. 1
. 11. A method for improving the wash-iastness on textile material of hydroxyl-containing size from the group consisting of water-soluble cel lulose ethers, polyvinyl alcohol and starch sizes, which comprises treating the textile material with said size and cetyloxymethyl dimethyl benzyl ammonium chloride, and subsequently heating the treated material to eiiect reaction between the size and cetyloxymethyl dimethyl benzyl ammonium chloride.
12. A method for improving the wash-fastness on textile material of a water-soluble cellulose ether size which comprises treating the textile material with said size and cetyloxymethyl dimethyl benzyl ammonium chloride, and subsequently heating the treated material to attest reaction between the size and cetyloxymethyl-dimethyl benzyl ammonium chloride.
13. The method of claim 12 in which the cellulose ether is a water-soluble ethyl cellulose.
ONSLOW B. HAGER. LOUIS H. BOCK. ALVA L. HOUK.
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Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
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US2445581A (en) * | 1943-12-09 | 1948-07-20 | Polaroid Corp | Treatment of polarizing polyvinyl alcohol-iodine sorption complex image with boric acid |
US2466404A (en) * | 1944-03-08 | 1949-04-05 | Eastman Kodak Co | Polyvinyl carbamates |
US2545070A (en) * | 1947-07-09 | 1951-03-13 | Du Pont | Cellulose ether solutions and method of spinning the same |
US2854441A (en) * | 1953-11-16 | 1958-09-30 | Ions Exchange & Chemical Corp | Water-soluble metal compounds and process for making same |
US2947594A (en) * | 1957-12-09 | 1960-08-02 | American Cyanamid Co | Animalization of cellulose |
US2989409A (en) * | 1955-09-02 | 1961-06-20 | Ohio Commw Eng Co | Dextran containing sizing composition |
US3076688A (en) * | 1954-10-05 | 1963-02-05 | Traitements Chimiques Des Text | Process of wet and dry creaseproofing cellulose fabrics with a pyridinium salt of a di-chloromethyl ether and rubber latex, bleaching the fabrics, and fabrics produced thereby |
US3147233A (en) * | 1960-04-18 | 1964-09-01 | Yarney Internat Corp | Polyvinyl compound and treatment involving same |
US3272640A (en) * | 1960-12-22 | 1966-09-13 | Hercules Powder Co Ltd | Water insolubilizing and insensitizing process |
US3314810A (en) * | 1963-06-19 | 1967-04-18 | Staley Mfg Co A E | Amylosic material plasticized with quaternary ammonium salt |
US3332794A (en) * | 1966-04-12 | 1967-07-25 | Oxford Paper Co | Carboxy-free polymeric composition containing ammonium zirconyl carbonate |
-
1939
- 1939-02-01 US US253996A patent/US2304252A/en not_active Expired - Lifetime
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2445581A (en) * | 1943-12-09 | 1948-07-20 | Polaroid Corp | Treatment of polarizing polyvinyl alcohol-iodine sorption complex image with boric acid |
US2466404A (en) * | 1944-03-08 | 1949-04-05 | Eastman Kodak Co | Polyvinyl carbamates |
US2545070A (en) * | 1947-07-09 | 1951-03-13 | Du Pont | Cellulose ether solutions and method of spinning the same |
US2854441A (en) * | 1953-11-16 | 1958-09-30 | Ions Exchange & Chemical Corp | Water-soluble metal compounds and process for making same |
US3076688A (en) * | 1954-10-05 | 1963-02-05 | Traitements Chimiques Des Text | Process of wet and dry creaseproofing cellulose fabrics with a pyridinium salt of a di-chloromethyl ether and rubber latex, bleaching the fabrics, and fabrics produced thereby |
US2989409A (en) * | 1955-09-02 | 1961-06-20 | Ohio Commw Eng Co | Dextran containing sizing composition |
US2947594A (en) * | 1957-12-09 | 1960-08-02 | American Cyanamid Co | Animalization of cellulose |
US3147233A (en) * | 1960-04-18 | 1964-09-01 | Yarney Internat Corp | Polyvinyl compound and treatment involving same |
US3272640A (en) * | 1960-12-22 | 1966-09-13 | Hercules Powder Co Ltd | Water insolubilizing and insensitizing process |
US3314810A (en) * | 1963-06-19 | 1967-04-18 | Staley Mfg Co A E | Amylosic material plasticized with quaternary ammonium salt |
US3332794A (en) * | 1966-04-12 | 1967-07-25 | Oxford Paper Co | Carboxy-free polymeric composition containing ammonium zirconyl carbonate |
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