US2657151A - Coating of fabrics - Google Patents

Coating of fabrics Download PDF

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US2657151A
US2657151A US169522A US16952250A US2657151A US 2657151 A US2657151 A US 2657151A US 169522 A US169522 A US 169522A US 16952250 A US16952250 A US 16952250A US 2657151 A US2657151 A US 2657151A
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coating
textiles
fabric
per cent
coated
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Gensel Herbert
Windemuth Erwin
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Bayer AG
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Bayer AG
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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
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • 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
    • D06M13/395—Isocyanates

Definitions

  • the present invention relates to the coating of fabrics and more particularly to a process whereby the fabrics are coated with isocyanate modified polyesters or with mixtures of polyesters and diisocyanates.
  • A.- further object resides in the provision of ing the textiles to be coated with water or an aqueous solution of analipha-tic diamine or amino alcohol, then coating said textiles in the moist state with a solution or emulsion of polyesters and di-isocyanatesor of their conversion products,
  • the textile material should contain about -100 per cent of its weight of water, in order to prevent the coating solution from penetrating through the fabric. If instead, of water, an aqueous solution of aliphatic diamines, especially ethylene diamine or amino alcohols such as diethanolamine, is used, a moisture content of 5-10 per cent of the weight of the fabric is sufficient and up to about 50 per cent may conveniently be employed.
  • polyesters polyesters from adipic acid and diethylene glycol and other polyglycols are preferred. Furthermore, polyesters from adipic acid and 1,2-propylene glycol, thiodiglycol, quim'te and others may be used. As-acid components, other dicarboxylic acids than adipic acid such as sebacic acid, thiodibutyric acid, maleic acid'and phthalic acid may be employed. Hydroxycarboxylic acids may also be employed for the production of the polyester. It is advisable to employ an excess of glycol, which excess causes the end groups of the polyester to consist mainly of hydroxyl groups, while free carboxyl groups occur only to a small degree.
  • polyesters are reacted with organic diisocyanates and then contain as reactive groups mainly isocyanate groups.
  • diisocyanates are suitable such as tetramethylene diisocyanate, hexamethylene diisocyanate, dodecamethylene diisocyanate, cyclohexane diisocyanate, dicyclohexylmethane diisocyanate, thiodipropyl diisoc-yanate, toluylene diisocyanate and others.
  • polyesters with diisocyanates which have not yet or only partly reacted with each other
  • polyhydroxy compounds with three hydroxyl groups such as glycerol, hexanetriol, trimethylolpropane, etc. may be employed, besides the dihydroxyl compounds enumerated.
  • 'As solvents for the combination of polyesters and diisocyanates or for the isocyanate modified polyesters organic solvents free from hydroxyl groups such as benzene, methylglycolacetate, ethyl acetate and the like or mixtures of these compounds may be employed. Naturally, care should be taken that the organic solvent does not destroy the fiber, which would be possible if cellulose acetate were employed in the fabric.
  • Aqueous emulsions of isocyanate modified polyesters may also be used.
  • the liquid coating medium preferably contains at least 50 per cent of its weight of the isocyanate modified polyester.
  • the reaction between the isocyanate groups and water or amine may be substantially accelerated by adding about 0.1-2 per cent of tertiary amines like dimethylaminocyclohexane, dimethylpiperazine, perhydroethylcarbazole, methylor butylpyrrolidine or trialliylamines.
  • coated fabrics of this invention are suitable for all purposes for which rubber coated fabrics have hitherto been employed, for instance for rain coats, oil cloth, water resistant chintz and the like.
  • the process is also suitable for the production of multilayer fabrics such as are for instance employed for automobile tops.
  • pretreatment of the fabric as well as the aftertreatment necessary for cross-linking is carried out in such a manner, that the fabric is soaked in an aqueous solution of ethylenediamine, two lengths of fabric are coated on one sideonly, the layers united on the coated side, and subsequently dried in the heat.
  • the pretreatment with the solution of diamine the penetration of the coating solution to the uncoated side of the fabric is prevented, while drying in the heat results in cross-linking of the isocyanate modified polyesters by means or the ethylene diamine and water vapour.
  • the isocyanate modified polyester is thus solidified.
  • V the filament is surrounded without being impregnated. Filaments of this kind may be used as substitutes for violin strings, wicker work etc.
  • Example 1 Cotton poplin fabric is treated with water on the foulard, and dried on a calender until the residual moisture is about 80 per cent of the fabric weight.
  • the pretreated fabric is then coated with a coating mixture consisting of an 30 per cent solution of an adipic acid diethylene glycol polyester having a hydroxyl number of 65 and an acid number of about 0.1, and 15 per cent of the weight of the polyester of toluylene diisocyanate.
  • the fabric is subsequently led through a chamber saturated with ethylene diamine vapor. This process may be repeated until the coating has the desired thickness.
  • the fabric is washed on a jigger with a solution of about 10 com. of acetic acid in one liter of water and dried.
  • a watertight poplin suitable for the production of rain coats is obtained in this manner, which is coated on one side only.
  • Example 2 A fabric of viscose taffeta is treated on a foulard with a 10 per cent aqueous solution of ethylenediamine and subsequently dried to a residual water content of about 30 per cent of the fabric weight.
  • the fabric thus pretreated is coated on one side in a coating machine with a coating mix ture obtained from a '70 per cent solution in benzene of an adipic acid diethyleneglycol polyester having an hydroxyl number of 55 and an acid number of 1.5, and 11 per cent of the weight of the polyester of hexamethylenediisocyanate.
  • the fabric is further treated as indicated in Example 1 and finally impregnated with one of the known water repelling agents, for instance a parafiin emulsion of an aluminium salt. In this manner a viscose taffeta suitable as rain coat material, which is water tight and water repellent, is obtained.
  • Example 3 A taffeta fabric from acetate rayon is treated on a foulard with a 5 per cent aqueous solution of ethylene diamine and subsequently dried to a residual water content of about 10 per cent.
  • the mixture employed for coating is obtained by reacting 100 parts of an adipic acid diethylene glycol polyester having a hydroxyl number of 33.4 and an acid number of 1.1 with 10.6 parts of l,6-cyclohexanediisocyanate.
  • the coating mixture is employed as an per cent solution in benzene.
  • the fabric is first washed with water as indicated in Example 2 and then treated with an agent imparting water repellent properties. In this manner a rain coat material is obtained, which is water tight and water repellent.
  • Example 4 A cotton'poplin fabric is treated on a foulard with a solution containing per liter of water 20 grams of diethanolamine and 10 grams of hexahydrodimethylaniline as a catalyst. The fabric is dried to a residual moisture content of about 10 per cent of water. The fabric is then coated with the coating mixture as described in Example 2 and led for a short period through a chamber saturated with the vapor of ethylenediamine.
  • Example 5 A canvas consisting of cotton and warp linen is treated on a foulard with a ten per cent aqueous solution of ethylene diamine. Two widths are made of the fabric and each of the widths coated on a lining machine with an 80 per cent solution of a coating mixture of the same composition as in Example 2. The Widths are then united with their coated sides in suitable manner and dried hot under pressure. In this manner a solid adhesion of the two widths results.
  • Example 6 A taffeta fabric of cupramrnonia rayon is treated on a foulard with a ten per cent aqueous tion:
  • Example 7 A viscose rayon taffeta fabric is treated on a foulardwith a five per cent aqueous solution of ethylene diamine and then dried to a residual moisture content of about 5 per cent.
  • the pretreated fabric is coated three times with a coating of the following composition, each coating being dried at 140 C.:
  • polyester 100 parts from three mols of adipic acid, two mols of trimethylolpropane and two mols of butyleneglycol,
  • the fabric is then coated again and immediately afterwards led through a chamber saturated with ethylene diamine vapor. Finally the fabric is washed with a 3 per cent acetic acid solution, rinsed, and dried. A fabric coated on one side having a delustered appearance is obtained.
  • Example 8 6.5 parts of a condensation product from xylene and formaldehyde, said condensation product being hydroxyethylated by means of ethylene oxide, are dissolved in 12.5 parts of water, and 130 parts of the coating composition as described in Example 2 are emulsified in this solution by gradual addition with stirring.
  • the 50 per cent emulsion obtained in this manner is coated on a cotton taffeta fabric pretreated with a 5 per cent aqueous ethylene diamine solution, and finally aftertreated with ethylene diamine vapor. In this manner a fabric is obtained coated on one side and having a rubbery hand.
  • a process of coating textiles which comprises impregnating said textiles with an aqueous medium of the group consisting of water, an aqueous solution of an aliphatic diamine and an aqueous solution of an aliphatic amino-alcohol, coating the impregnated textiles with a liquid medium containing an isocyanate modified polyester that is still soluble in organic solvents and whose sole reactive groups are isocyanate groups, said aqueous impregnating medium being present in said textiles in an amount sufficient to prevent substantial penetration of said liquid coating medium therein, and effecting cross-linking of said isocyanate modified polyester by treating said coated textiles with a cross-linking agent.
  • impregnated textiles are dried to a moisture content of from about to about per cent before applying the liquid coating medium.
  • aqueous impregnating medium is an aqueous solution of an aliphatic diamine and the impregnated textiles are dried to a moisture content of from about 5 to about 50 per cent before applying the liquid coating medium.
  • aqueous impregnating medium is an aqueous solution of an aliphatic amino alcohol and the impregnated textiles are dried to a moisture content of from about 5 to about 50 per cent before applying the liquid coating medium.
  • a process of coating textiles which comprises impregnating said textiles With an aqueous medium of the group consisting of water, an aqueous solution of an aliphatic diamine and an aqueous solution of an aliphatic amino-alcohol, coating the impregnated textiles on one side only with a liquid medium containing at least 50 per cent of an isocyanate modified polyester that is still soluble in organic solvents and whose sole reactive groups are isocyanate groups, said aqueous impregnating medium being present in said textiles in an amount sufficient to prevent substantial penetration of said liquid coating medium therein, and treating said coated textiles with the vapor of a cross-linking agent of the group consisting of water and an aliphatic diamine to effect cross-linking of the isocyanate modified polyester.
  • liquid coating-medium is a solution of the iso cyanate modified polyester in an hydroxyl-free organic solvent.
  • liquid coating medium is an aqueous emulsion of the isocyanate modified polyester.
  • liquid coating medium contains from about 0.1 per cent to about 2 per cent of a tertiary amine calculated on the weight of the isocyanate modified polyester.
  • a process as claimed in claim 6 wherein the isocyanate modified polyester is obtained by mixing an adipic acid diethyleneglycol polyester having a low acid number with an organic diisocyanate.

Description

Patented Oct. 7 27, 1953 COATING OF FABRICS Herbert Gensel, .LeverkusemWiesdor-f, and Erwin Windemuth, Leverkusen-Bayerwerk, Germany, assignors to Farbenfabriken Bayer Aktiengesellschaft, Leverkusen, Germany, a corporation of Germany No Drawing.
Application June 21, 1950, Serial No. 169,522. In Germany September 23, 1949 10 Claims.
The present invention relates to the coating of fabrics and more particularly to a process whereby the fabrics are coated with isocyanate modified polyesters or with mixtures of polyesters and diisocyanates.
It is known to produce polymers by reacting polyesters with diisocyanates, which polymers are of more or less elastic character depending upon the kind of polyester used. as a starting material. It is furthermore known to apply mixtures of polyesters and diisocyanates to various surfaces, hard or soft or even rubber-elastic coatings being obtained depending upon the nature of starting material employed. It has also been proposed to employ such products for the impregnation of textile materials.
All attempts to utilize the excellent properties of these polymers for the coating of fabrics, for instance for the production of rain coats and the like, have had no practical result. This is due to the fact that the components, viz. the diisocyanate modified polyesters or the polyesters on the one hand and the diisocyanates on the other can only be distributed on the fabrics in the form of their solutions in organic solvents. These solutions penetrate the textiles so farthat they I are impregnated throughout and thus lose their textile character. It is therefore impossible to coat the textiles with the polymers only on one side, that is to retain the textile character thereof on one side, such as is necessary for many rubber impregnated articles.
It is therefore an object of the invention to provide a process by which fabrics and other textile materials may be coated on one side only with a synthetic elastomer.
A.- further object resides in the provision of ing the textiles to be coated with water or an aqueous solution of analipha-tic diamine or amino alcohol, then coating said textiles in the moist state with a solution or emulsion of polyesters and di-isocyanatesor of their conversion products,
or an aqueous gsolution of a diamine.
If the pretreatment of the fabric to be coated is carried out with water, the textile material should contain about -100 per cent of its weight of water, in order to prevent the coating solution from penetrating through the fabric. If instead, of water, an aqueous solution of aliphatic diamines, especially ethylene diamine or amino alcohols such as diethanolamine, is used, a moisture content of 5-10 per cent of the weight of the fabric is sufficient and up to about 50 per cent may conveniently be employed.
By this pretreatment the undesirably deep penetration of the polymer solution into the fabric is avoided, and a rapid condensation of the polymer brought about. It is then only necessary to remove the excess water and to complete the reaction of the diisocyanate with the polyester and of the soluble isocyanate modified polyester with water or amine.
As starting materials for the coating of fabrics, especially such 'isocyanate modified polyesters are suitable, which are still soluble in organic solvents. As polyesters, polyesters from adipic acid and diethylene glycol and other polyglycols are preferred. Furthermore, polyesters from adipic acid and 1,2-propylene glycol, thiodiglycol, quim'te and others may be used. As-acid components, other dicarboxylic acids than adipic acid such as sebacic acid, thiodibutyric acid, maleic acid'and phthalic acid may be employed. Hydroxycarboxylic acids may also be employed for the production of the polyester. It is advisable to employ an excess of glycol, which excess causes the end groups of the polyester to consist mainly of hydroxyl groups, while free carboxyl groups occur only to a small degree.
Such polyesters are reacted with organic diisocyanates and then contain as reactive groups mainly isocyanate groups. For this reaction diisocyanates are suitable such as tetramethylene diisocyanate, hexamethylene diisocyanate, dodecamethylene diisocyanate, cyclohexane diisocyanate, dicyclohexylmethane diisocyanate, thiodipropyl diisoc-yanate, toluylene diisocyanate and others.
If, instead of 'isocyanate modified polyesters combinations of polyesters with diisocyanates are employed, which have not yet or only partly reacted with each other, polyhydroxy compounds with three hydroxyl groups, such as glycerol, hexanetriol, trimethylolpropane, etc. may be employed, besides the dihydroxyl compounds enumerated. v
'As solvents for the combination of polyesters and diisocyanates or for the isocyanate modified polyesters, organic solvents free from hydroxyl groups such as benzene, methylglycolacetate, ethyl acetate and the like or mixtures of these compounds may be employed. Naturally, care should be taken that the organic solvent does not destroy the fiber, which would be possible if cellulose acetate were employed in the fabric. Aqueous emulsions of isocyanate modified polyesters may also be used. The liquid coating medium preferably contains at least 50 per cent of its weight of the isocyanate modified polyester.
The reaction between the isocyanate groups and water or amine may be substantially accelerated by adding about 0.1-2 per cent of tertiary amines like dimethylaminocyclohexane, dimethylpiperazine, perhydroethylcarbazole, methylor butylpyrrolidine or trialliylamines.
In many cases it is advisable to treat the coated fabric, after distributing the solution thereon, with the vapor of an aliphatic diamine especially ethylene diamine. Thus a rapid cross-linking of the polymer on the coated side of the fabric is brought about. This aftertreatment may also be employed in order to deluster the surface of the coating. If the aftertreatment is not carried out, in contrast thereto shiny coatings having the appearance of lacquers are obtained. Instead of using the diamine in vapor form, it is also possible to employ it in solution for the aftertreatmerit.
The coated fabrics of this invention are suitable for all purposes for which rubber coated fabrics have hitherto been employed, for instance for rain coats, oil cloth, water resistant chintz and the like. The process is also suitable for the production of multilayer fabrics such as are for instance employed for automobile tops. In this case pretreatment of the fabric as well as the aftertreatment necessary for cross-linking is carried out in such a manner, that the fabric is soaked in an aqueous solution of ethylenediamine, two lengths of fabric are coated on one sideonly, the layers united on the coated side, and subsequently dried in the heat. By the pretreatment with the solution of diamine the penetration of the coating solution to the uncoated side of the fabric is prevented, while drying in the heat results in cross-linking of the isocyanate modified polyesters by means or the ethylene diamine and water vapour. The isocyanate modified polyester is thus solidified.
The process also be employed for the coating of filaments. V In this case the filament is surrounded without being impregnated. Filaments of this kind may be used as substitutes for violin strings, wicker work etc.
The present invention is illustrated by the following examples without being restricted thereto:
Example 1 Cotton poplin fabric is treated with water on the foulard, and dried on a calender until the residual moisture is about 80 per cent of the fabric weight. The pretreated fabric is then coated with a coating mixture consisting of an 30 per cent solution of an adipic acid diethylene glycol polyester having a hydroxyl number of 65 and an acid number of about 0.1, and 15 per cent of the weight of the polyester of toluylene diisocyanate. The fabric is subsequently led through a chamber saturated with ethylene diamine vapor. This process may be repeated until the coating has the desired thickness. Finally the fabric is washed on a jigger with a solution of about 10 com. of acetic acid in one liter of water and dried. A watertight poplin suitable for the production of rain coats is obtained in this manner, which is coated on one side only.
Example 2 A fabric of viscose taffeta is treated on a foulard with a 10 per cent aqueous solution of ethylenediamine and subsequently dried to a residual water content of about 30 per cent of the fabric weight. The fabric thus pretreated is coated on one side in a coating machine with a coating mix ture obtained from a '70 per cent solution in benzene of an adipic acid diethyleneglycol polyester having an hydroxyl number of 55 and an acid number of 1.5, and 11 per cent of the weight of the polyester of hexamethylenediisocyanate. The fabric is further treated as indicated in Example 1 and finally impregnated with one of the known water repelling agents, for instance a parafiin emulsion of an aluminium salt. In this manner a viscose taffeta suitable as rain coat material, which is water tight and water repellent, is obtained.
Example 3 A taffeta fabric from acetate rayon is treated on a foulard with a 5 per cent aqueous solution of ethylene diamine and subsequently dried to a residual water content of about 10 per cent. The mixture employed for coating is obtained by reacting 100 parts of an adipic acid diethylene glycol polyester having a hydroxyl number of 33.4 and an acid number of 1.1 with 10.6 parts of l,6-cyclohexanediisocyanate. The coating mixture is employed as an per cent solution in benzene. After each coating the coated side of the fabric is treated with an aqueous solution of ethylenediamine and dried. The fabric is first washed with water as indicated in Example 2 and then treated with an agent imparting water repellent properties. In this manner a rain coat material is obtained, which is water tight and water repellent.
Example 4 A cotton'poplin fabric is treated on a foulard with a solution containing per liter of water 20 grams of diethanolamine and 10 grams of hexahydrodimethylaniline as a catalyst. The fabric is dried to a residual moisture content of about 10 per cent of water. The fabric is then coated with the coating mixture as described in Example 2 and led for a short period through a chamber saturated with the vapor of ethylenediamine.
Finally the fabric is finished as indicated in Example 2.
Example 5 A canvas consisting of cotton and warp linen is treated on a foulard with a ten per cent aqueous solution of ethylene diamine. Two widths are made of the fabric and each of the widths coated on a lining machine with an 80 per cent solution of a coating mixture of the same composition as in Example 2. The Widths are then united with their coated sides in suitable manner and dried hot under pressure. In this manner a solid adhesion of the two widths results.
Example 6 A taffeta fabric of cupramrnonia rayon is treated on a foulard with a ten per cent aqueous tion:
solution of hexamethylene diamine and subsequently dried to a residual moisture content of about per cent. The pretreated fabric is then coated four times, each coating being dried at 140 C. with a coating of the following composi- 100 parts of the polyester from three mols of adipic acid, one mol of hexane trio] and three mols of butylene glycol,
36 parts of toluylene diisocyanate, and
10 parts of butylacetate.
Finally the fabric is washed on a jigger with a 3 per cent acetic acid solution, rinsed, and dried. In this manner a fabric coated on one side only With a coating having a high luster is obtained.
Example 7 A viscose rayon taffeta fabric is treated on a foulardwith a five per cent aqueous solution of ethylene diamine and then dried to a residual moisture content of about 5 per cent. The pretreated fabric is coated three times with a coating of the following composition, each coating being dried at 140 C.:
100 parts of polyester from three mols of adipic acid, two mols of trimethylolpropane and two mols of butyleneglycol,
36 parts of hexanediisocyanate, and
10 parts of butylacetate.
The fabric is then coated again and immediately afterwards led through a chamber saturated with ethylene diamine vapor. Finally the fabric is washed with a 3 per cent acetic acid solution, rinsed, and dried. A fabric coated on one side having a delustered appearance is obtained.
Example 8 6.5 parts of a condensation product from xylene and formaldehyde, said condensation product being hydroxyethylated by means of ethylene oxide, are dissolved in 12.5 parts of water, and 130 parts of the coating composition as described in Example 2 are emulsified in this solution by gradual addition with stirring. The 50 per cent emulsion obtained in this manner is coated on a cotton taffeta fabric pretreated with a 5 per cent aqueous ethylene diamine solution, and finally aftertreated with ethylene diamine vapor. In this manner a fabric is obtained coated on one side and having a rubbery hand.
We claim:
1. A process of coating textiles which comprises impregnating said textiles with an aqueous medium of the group consisting of water, an aqueous solution of an aliphatic diamine and an aqueous solution of an aliphatic amino-alcohol, coating the impregnated textiles with a liquid medium containing an isocyanate modified polyester that is still soluble in organic solvents and whose sole reactive groups are isocyanate groups, said aqueous impregnating medium being present in said textiles in an amount sufficient to prevent substantial penetration of said liquid coating medium therein, and effecting cross-linking of said isocyanate modified polyester by treating said coated textiles with a cross-linking agent.
2. A process as claimed in claim 1 wherein the aqueous impregnating medium is water and. the
impregnated textiles are dried to a moisture content of from about to about per cent before applying the liquid coating medium.
3. A process as claimed in claim 1 wherein the aqueous impregnating medium is an aqueous solution of an aliphatic diamine and the impregnated textiles are dried to a moisture content of from about 5 to about 50 per cent before applying the liquid coating medium.
4. A process as claimed in claim 1 wherein the aqueous impregnating medium is an aqueous solution of an aliphatic amino alcohol and the impregnated textiles are dried to a moisture content of from about 5 to about 50 per cent before applying the liquid coating medium.
5. A process as claimed in claim 1 wherein the coated textiles are treated with the vapor of a cross-linking agent of the group consisting of water and an aliphatic diamine to effect crosslinking of the isocyanate modified polyester.
6. A process of coating textiles which comprises impregnating said textiles With an aqueous medium of the group consisting of water, an aqueous solution of an aliphatic diamine and an aqueous solution of an aliphatic amino-alcohol, coating the impregnated textiles on one side only with a liquid medium containing at least 50 per cent of an isocyanate modified polyester that is still soluble in organic solvents and whose sole reactive groups are isocyanate groups, said aqueous impregnating medium being present in said textiles in an amount sufficient to prevent substantial penetration of said liquid coating medium therein, and treating said coated textiles with the vapor of a cross-linking agent of the group consisting of water and an aliphatic diamine to effect cross-linking of the isocyanate modified polyester.
7. A process as claimed in claim 6 wherein the liquid coating-medium is a solution of the iso cyanate modified polyester in an hydroxyl-free organic solvent.
8. A process as claimed in claim 6 wherein the liquid coating medium is an aqueous emulsion of the isocyanate modified polyester.
9. A process as claimed in claim 6 wherein the liquid coating medium contains from about 0.1 per cent to about 2 per cent of a tertiary amine calculated on the weight of the isocyanate modified polyester.
10. A process as claimed in claim 6 wherein the isocyanate modified polyester is obtained by mixing an adipic acid diethyleneglycol polyester having a low acid number with an organic diisocyanate.
HERBERT GEN SEL. ERWIN WINDEMU TH References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 2,121,717 Sullivan June 21, 1938 2,333,639 Christ et a1. Nov. 9, 1943 2,468,713 ropa et al Apr. 26, 1949 OTHER REFERENCES Ser. No. 397,741, Schlack (A. P. 0.), published Apr. 20, 1943.

Claims (1)

1. A PROCESS OF COATING TEXTILES WHICH COMPRISES IMPREGNATING SAID TEXTILES WITH AN AQUEOUS MEDIUM OF THE GROUP CONSISTING OF WATER, AN AQUEOUS SOLUTION OF AN ALIPHATIC DIAMINE AND AN AQUEOUS SOLUTION OF AN ALIPHATIC AMINO-ALCOHOL, COATING THE IMPREGNATED TEXTILES WITH A LIQUID MEDIUM CONTAINING AN ISOCYANATE MODIFIED POLYESTER THAT IS STILL SOLUBLE IN ORGANIC SOLVENTS AND WHOSE SOLE REACTIVE GROUPS ARE ISOCYANATE GROUPS, SAID AQUEOUS IMPREGNATING MEDIUM BEING PRESENT IN SAID TEXTILES IN AN AMOUNT SUFFICIENT TO PREVENT SUBSTANTIAL PENETRATION OF SAID LIQUID COATING MEDIUM THEREIN, AND EFFECTING CROSS-LINKING OF SAID ISOCYANATE MODIFIED POLYESTER BY TREATING SAID COATED TEXTILES WITH A CROSS-LINKING AGENT.
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Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2721811A (en) * 1954-01-07 1955-10-25 Us Rubber Co Textile material and method of making same
US2753276A (en) * 1953-08-19 1956-07-03 Bayer Ag Process of coating a surface with a foamed polyurethane composition
US2779689A (en) * 1955-07-19 1957-01-29 Pittsburgh Plate Glass Co Forming foamed polyurethane resins
US2866722A (en) * 1955-05-20 1958-12-30 Bayer Ag Process for the production of foamed urethan coatings
US2880114A (en) * 1955-05-04 1959-03-31 Samcoe Holding Corp Method of resin treating tubular knitted fabric
US2888409A (en) * 1955-03-21 1959-05-26 Goodyear Tire & Rubber Production of flexible cellular polyurethane material
US2888408A (en) * 1955-03-21 1959-05-26 Goodyear Tire & Rubber Treatment of flexible cellular polyurethane material with ammonia
US2890137A (en) * 1955-10-28 1959-06-09 Canadian Hanson Sisal buff oil impregnation method
US2890136A (en) * 1955-10-28 1959-06-09 Canadian Hanson And Van Winkle Sisal buff resin impregnation method
US2903380A (en) * 1954-02-05 1959-09-08 Bayer Ag Process for producing composite structures comprising rigid polyurethane foams and covering layers
US2967117A (en) * 1949-01-25 1961-01-03 Bayer Ag Process for coating a substrate with a mixture of a polyhydroxy polyester and a polyisocyanate
US2973284A (en) * 1957-04-30 1961-02-28 Goodrich Co B F Leather-like material
US2993813A (en) * 1956-02-29 1961-07-25 Bayer Ag Process of coating a substrate with polyurethane foam
US3009764A (en) * 1959-02-13 1961-11-21 Us Rubber Co Method of making polyurethane thread and thread produced by such method
US3009765A (en) * 1959-02-20 1961-11-21 Us Rubber Co Method of making polyurethane filamentary material
US3027276A (en) * 1959-05-15 1962-03-27 Allied Kid Company Crock-proof suedes and methods of making same
US3088172A (en) * 1956-05-12 1963-05-07 Bayer Ag Process for the production of molded cellular polyurethane plastics
US3102835A (en) * 1960-04-25 1963-09-03 Allen Ind Fibrous materials and method for making the same
US3196035A (en) * 1960-07-16 1965-07-20 Fuji Tsushinki Seizo Kk Method of bonding an epoxy coating to a polyisocyanate treated polyester fiber base
US3297649A (en) * 1962-11-13 1967-01-10 Rohm & Haas Process for curing polyurethanes
US3298854A (en) * 1962-02-02 1967-01-17 Owens Corning Fiberglass Corp Method of coating yarn
US3318727A (en) * 1965-09-27 1967-05-09 Brunswick Corp Scratch and wear resistant cured polyester surfaces
US3360394A (en) * 1964-01-24 1967-12-26 Burlington Industries Inc Process for forming breathable polyurethane coating on a textile fabric and the resulting product
US3384506A (en) * 1964-05-18 1968-05-21 Thiokol Chemical Corp Hydrophilic urethane compositions and process for preparation of moisture containing breathable fabrics
US3385728A (en) * 1964-06-22 1968-05-28 Uniroyal Inc Method of coating a base with a carboxylated latex containing hydroxylamine hydrochloride
US3505096A (en) * 1966-05-16 1970-04-07 Inmont Corp Method of producing blush coated fabrics of superior adhesion
US3515573A (en) * 1969-03-28 1970-06-02 Goodrich Co B F Method for coating impregnated textile substrates with polymeric coatings free of pits,air bubbles,and blisters
US3518141A (en) * 1967-10-30 1970-06-30 Eastman Kodak Co Method of applying photographic coatings to a moving web with a spliced joint
US3524791A (en) * 1967-07-03 1970-08-18 Du Pont Man-made suede and method of making same
US3619257A (en) * 1967-08-08 1971-11-09 Toyo Tire & Rubber Co Preparation of plural layer synthetic leather and the like
US3874898A (en) * 1972-06-19 1975-04-01 Hatrick Chemicals Pty Drying process and resultant product
US4006052A (en) * 1968-12-04 1977-02-01 Tenneco Chemicals, Inc. Diffusion method for depositing microporous film
US4049632A (en) * 1976-07-14 1977-09-20 Armstrong Cork Company Chain extending polyurethanes with a large excess of water
US4343839A (en) * 1980-12-15 1982-08-10 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4343924A (en) * 1981-09-14 1982-08-10 Ashland Oil, Inc. Stabilized phenolic resins for use in vapor permeation curing
US4365039A (en) * 1980-12-15 1982-12-21 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4366193A (en) * 1981-04-10 1982-12-28 Ashland Oil, Inc. Catechol-based vapor permeation curable coating compositions
US4368222A (en) * 1981-06-05 1983-01-11 Ashland Oil, Inc. Vapor permeation curable coatings for surface-porous substrates
US4374167A (en) * 1980-12-15 1983-02-15 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4374181A (en) * 1981-09-14 1983-02-15 Ashland Oil, Inc. Vapor permeation curable coatings for reaction injection molded parts
US4396647A (en) * 1982-02-22 1983-08-02 Ashland Oil, Inc. Vapor permeation curable coating compositions containing 2,3',4-trihydroxydiphenyl
US5047495A (en) * 1989-08-28 1991-09-10 The G. F. Goodrich Company Polyurethane for flexible fuel containers
US20110064898A1 (en) * 2008-05-19 2011-03-17 Lubrizol Advanced Materials, Inc. Thermoplastic Polyurethanes With Good Fuel Resistance
US9597848B1 (en) 2012-05-25 2017-03-21 Robertson Fuel Systems Llc Method and system for forming a self-sealing volume
US9802476B1 (en) 2012-05-25 2017-10-31 Robertson Fuel Systems, Llc Method and system for forming a self-sealing volume using a breather system
US10994464B1 (en) 2014-08-07 2021-05-04 Robertson Fuel Systems, L.L.C. Method and system for forming a self-sealing volume with an aqueous polyurethane dispersion layer

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DE2023671C3 (en) * 1970-05-14 1979-08-09 Kufner Textilwerke Kg, 8000 Muenchen Process for the anti-felting finishing of animal fibers

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US2333639A (en) * 1940-07-02 1943-11-09 Du Pont Treatment of polyesters and product therefrom
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US2333639A (en) * 1940-07-02 1943-11-09 Du Pont Treatment of polyesters and product therefrom
US2468713A (en) * 1947-04-16 1949-04-26 American Cyanamid Co Isocyanates and products prepared therefrom and methods of making the same

Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2967117A (en) * 1949-01-25 1961-01-03 Bayer Ag Process for coating a substrate with a mixture of a polyhydroxy polyester and a polyisocyanate
US2753276A (en) * 1953-08-19 1956-07-03 Bayer Ag Process of coating a surface with a foamed polyurethane composition
US2721811A (en) * 1954-01-07 1955-10-25 Us Rubber Co Textile material and method of making same
US2903380A (en) * 1954-02-05 1959-09-08 Bayer Ag Process for producing composite structures comprising rigid polyurethane foams and covering layers
US2888409A (en) * 1955-03-21 1959-05-26 Goodyear Tire & Rubber Production of flexible cellular polyurethane material
US2888408A (en) * 1955-03-21 1959-05-26 Goodyear Tire & Rubber Treatment of flexible cellular polyurethane material with ammonia
US2880114A (en) * 1955-05-04 1959-03-31 Samcoe Holding Corp Method of resin treating tubular knitted fabric
US2866722A (en) * 1955-05-20 1958-12-30 Bayer Ag Process for the production of foamed urethan coatings
US2779689A (en) * 1955-07-19 1957-01-29 Pittsburgh Plate Glass Co Forming foamed polyurethane resins
US2890137A (en) * 1955-10-28 1959-06-09 Canadian Hanson Sisal buff oil impregnation method
US2890136A (en) * 1955-10-28 1959-06-09 Canadian Hanson And Van Winkle Sisal buff resin impregnation method
US2993813A (en) * 1956-02-29 1961-07-25 Bayer Ag Process of coating a substrate with polyurethane foam
US3088172A (en) * 1956-05-12 1963-05-07 Bayer Ag Process for the production of molded cellular polyurethane plastics
US2973284A (en) * 1957-04-30 1961-02-28 Goodrich Co B F Leather-like material
US3009764A (en) * 1959-02-13 1961-11-21 Us Rubber Co Method of making polyurethane thread and thread produced by such method
US3009765A (en) * 1959-02-20 1961-11-21 Us Rubber Co Method of making polyurethane filamentary material
US3027276A (en) * 1959-05-15 1962-03-27 Allied Kid Company Crock-proof suedes and methods of making same
US3102835A (en) * 1960-04-25 1963-09-03 Allen Ind Fibrous materials and method for making the same
US3196035A (en) * 1960-07-16 1965-07-20 Fuji Tsushinki Seizo Kk Method of bonding an epoxy coating to a polyisocyanate treated polyester fiber base
US3298854A (en) * 1962-02-02 1967-01-17 Owens Corning Fiberglass Corp Method of coating yarn
US3297649A (en) * 1962-11-13 1967-01-10 Rohm & Haas Process for curing polyurethanes
US3360394A (en) * 1964-01-24 1967-12-26 Burlington Industries Inc Process for forming breathable polyurethane coating on a textile fabric and the resulting product
US3384506A (en) * 1964-05-18 1968-05-21 Thiokol Chemical Corp Hydrophilic urethane compositions and process for preparation of moisture containing breathable fabrics
US3385728A (en) * 1964-06-22 1968-05-28 Uniroyal Inc Method of coating a base with a carboxylated latex containing hydroxylamine hydrochloride
US3318727A (en) * 1965-09-27 1967-05-09 Brunswick Corp Scratch and wear resistant cured polyester surfaces
US3505096A (en) * 1966-05-16 1970-04-07 Inmont Corp Method of producing blush coated fabrics of superior adhesion
US3524791A (en) * 1967-07-03 1970-08-18 Du Pont Man-made suede and method of making same
US3619257A (en) * 1967-08-08 1971-11-09 Toyo Tire & Rubber Co Preparation of plural layer synthetic leather and the like
US3518141A (en) * 1967-10-30 1970-06-30 Eastman Kodak Co Method of applying photographic coatings to a moving web with a spliced joint
US4006052A (en) * 1968-12-04 1977-02-01 Tenneco Chemicals, Inc. Diffusion method for depositing microporous film
US3515573A (en) * 1969-03-28 1970-06-02 Goodrich Co B F Method for coating impregnated textile substrates with polymeric coatings free of pits,air bubbles,and blisters
US3874898A (en) * 1972-06-19 1975-04-01 Hatrick Chemicals Pty Drying process and resultant product
US4049632A (en) * 1976-07-14 1977-09-20 Armstrong Cork Company Chain extending polyurethanes with a large excess of water
US4343839A (en) * 1980-12-15 1982-08-10 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4374167A (en) * 1980-12-15 1983-02-15 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4365039A (en) * 1980-12-15 1982-12-21 Ashland Oil, Inc. Vapor permeation curable polyester resin coating compositions for flexible substrates
US4366193A (en) * 1981-04-10 1982-12-28 Ashland Oil, Inc. Catechol-based vapor permeation curable coating compositions
US4368222A (en) * 1981-06-05 1983-01-11 Ashland Oil, Inc. Vapor permeation curable coatings for surface-porous substrates
US4343924A (en) * 1981-09-14 1982-08-10 Ashland Oil, Inc. Stabilized phenolic resins for use in vapor permeation curing
US4374181A (en) * 1981-09-14 1983-02-15 Ashland Oil, Inc. Vapor permeation curable coatings for reaction injection molded parts
US4396647A (en) * 1982-02-22 1983-08-02 Ashland Oil, Inc. Vapor permeation curable coating compositions containing 2,3',4-trihydroxydiphenyl
US5047495A (en) * 1989-08-28 1991-09-10 The G. F. Goodrich Company Polyurethane for flexible fuel containers
US20110064898A1 (en) * 2008-05-19 2011-03-17 Lubrizol Advanced Materials, Inc. Thermoplastic Polyurethanes With Good Fuel Resistance
US9597848B1 (en) 2012-05-25 2017-03-21 Robertson Fuel Systems Llc Method and system for forming a self-sealing volume
US9802476B1 (en) 2012-05-25 2017-10-31 Robertson Fuel Systems, Llc Method and system for forming a self-sealing volume using a breather system
US10549470B1 (en) 2012-05-25 2020-02-04 Robertson Fuel Systems, L.L.C. Method and system for forming a self-sealing volume
US11065953B1 (en) 2012-05-25 2021-07-20 Robertson Fuel Systems, L.L.C. Method and system for forming a self-sealing volume using a breather system
US10994464B1 (en) 2014-08-07 2021-05-04 Robertson Fuel Systems, L.L.C. Method and system for forming a self-sealing volume with an aqueous polyurethane dispersion layer

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