US2160375A - Water-repellent textile material and process of manufacturing it - Google Patents

Water-repellent textile material and process of manufacturing it Download PDF

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US2160375A
US2160375A US11867836A US2160375A US 2160375 A US2160375 A US 2160375A US 11867836 A US11867836 A US 11867836A US 2160375 A US2160375 A US 2160375A
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mixed
water
impregnated
vinyl
textile materials
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Voss Arthur
Staerk Hermann
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IG Farbenindustrie AG
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IG Farbenindustrie 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • D06M15/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
    • 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
    • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2221—Coating or impregnation is specified as water proof

Definitions

  • This invention relates to water-repellent textile material and to a process of manuiacturing the material and is a continuation in part of our application Ser. No. 94,482, flied August 5, 1936 l and entitled Water-repellent material and a process of manufacturing the material.
  • textile materials can be made water-repellent in an advantageous manner by treating them with solutions or emulsions of 10.
  • mixed polymerlzates which are prepared from maleic anhydride the free acid ora functional derivative thereoi and vinyl-esters of higher fatty acids (having at least 12 carbon atoms), Ior instance, according to the process described in U. s. Patent 2,047,398 for manufacturing mixed polymerisation products from maleic acid anhydrides and vinyl esters (see Example 4 oi the U. 8. Patent 2,047,398).
  • These mixed polymerizates yield stable solutions or emulsions which,
  • the mixed polymerisate from maleic anhydride and the vinyl ether of an aliphatic alcohol 80 of high molecular weight with at least 12 carbon atoms in the molecule as tree acid or a functional derivative thereof.
  • These mixed polymerisates which as previously stated are obtainable according to the process described in U. 8. Patent 85 2,047,398 (see Example 6 for the manufacture of mixed polymers from maleic acid anhydride and vinyl others) or which may be obtained by mutual polymerisation of a functional derivative of maleic acid and 01 a vinyl ester or vinyl ether of high 40 molecular weight are composed of compounds of the formula:
  • R1 and R2 stand for a member or the group consisting of COOH, C00, alkyl, CN, CONHz.
  • X stands for R, OR or 0.0CR, R representing an aliphatic hydrocarbon radical with at least 12 carbon atoms.
  • the reaction upon the textile materials is executed in the following way:
  • the textile material is introduced into the solution or emulsion of the mixed polymerisate and, after drying in the air, dried for a short time at a higher temperature (at about 100 C.)
  • the above described process is distinguished by the fact that the fiber is not only made waterproof when treated in this manner but that it retains its waterprootness even after repeated washing to an extent which could hitherto not be attained by any process, that is to say, the mixed polymerizates above characterized are so intimately combined with the fiber that similar to fast-dyestuffs, they irreversibly adhere to the fiber.
  • a web of cotton or artificial silk is impregnated with a solution of 0.5 per cent strength of the mixed polymerisate from vinyl-octodecylether and maleic-acid-dimethylester in carbon tetrachloride or a mixture thereof with alcohol, and is dried at ordinary temperature.
  • the web thus treated has a very good water-repellent effect and does not lose this property even when repeatedly washed or boiled with water.
  • Loose wool is impregnated as indicated in Example 1 with a solution of the mixed polymerisate from vinyl-octodecyl-ether and maleic acid in a mixture consisting of methylene chloride and ethyl-alcohol. After drying, the wool thus treated shows an enhanced water-repelling effect which it does not lose by washing.
  • a web of cotton or artificial silk is impregnated with a solution in methylene chloride of the mixed polymerisate from vinyl-stearate and the semi-ester oi maieic acid with methyl alcohol, and is dried at ordinary temperature.
  • the fabric thus treated has a very good waterrepellent effect and does not lose this property even after repeated washing or boiling with water.
  • a web of viscose artificial silk is treated with a solution of 0.5% strength in alcohol and carbon tetrachloride of the mixed polymerisate from maleic acid and vinyloctodecyl-ether obtained by treating with steam the anhydride mixed polymerisate and dried for a short time.
  • the fabric thus treated has a very good waterrepellent effect and does not lose this property even by washing or boiling.
  • Loose spun rayon is impregnated with a solution of 2% strength in carbon tetrachloride of the mixed polymerisate from vinyl-stearate and maleic acid monomethyl ester, squeezed and dried.
  • the spun rayon thus treated is very hydrophobe and does not lose this property by subsequent fulling.
  • Piece goods consisting of a mixture of wool and spun rayon are impregnated with an aqueous solution of 1% strength of the pyridine salt of a mixed polymerisate from maleic acid and vinylhexadecyl ether and subjected for a short time to a heat treatment at 90 C.-l C.
  • the material thus treated has a very good water-repellent effect and does not lose this property even by washing.
  • a cotton fabric is impregnated by passage through a solution of a mixed polymerizate from viral stearate and maleic anhydride in methylene chloride, dried by exposure to air and heated for half-an-hour to about 100 C.
  • the fabric thus treated is highly repellent to water and does not lose the property even after repeated washing with water and soap.
  • a cotton or artificial silk fabric is impregnated with an aqueous emulsion of a mixed polymerizate from vinyl palmitate and maleic anhydride and worked up as indicated in Example 8. If desired the heat-treatment may be followed by a further treatment with aluminium formate, whereby the water-repelling effect is further increased. .This fabric also retains its water-repellent property after repeated washing.
  • Loose wool is immersed into a solution of per cent strength of a mixed polymerizate from vinyl stearate and maleic anhydride, pressed and dried at 90-100 C.
  • the material thus treated has an increased resistance to water.
  • a fabric of cotton or artificial silk is impregnated with a solution of a mixed polymerizate from vinyl octo-decyl ether and maleic anhydride in ethylene chloride, dried and then heated for a short time at about 100 0., whereby the mixed polymerizate is intimately combined with the fibre.
  • the fabric thus treated is highly repellent to water and does not lose this property even when washed with water and soap.
  • the mixed polymerizate from maleic anhydride and the vinyl ether of the alcohol mixture obtainable by reduction of the coconut oil fatty acid and which contaim chiefly carbon chains with 12 to 14 carbon atoms, maybe applied in a similar manner for rendering the textile fiber highly waterproof.
  • a cotton fabric is impregnated with a solution of 0.5% strength of a mixed polymerizate of maleic anhydride and vinyl dodecyl ether in carbon tetrachloride and dried subsequently, finally for a short time at a temperature of 100 C.
  • the fabric treated in this manner is highly repellent to water and does not lose this property even when washed with water and soap.
  • a fabric of viscose artificial silk is imof maleic anhydride and hexa-decylene in carbon.
  • the material thus treated shows after drying which is finally performed for a short time at a temperature of 100 C., an excellent water-repellent eifect and a great stability to water.
  • a process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of compounds of the formula:
  • R1 and R2 standing for a member of the group consisting of (2001-1, C00, alkyl, CN and CONI-Iz and R1 and R2 together stand for and compounds of the formula:
  • X stands for a member of the group consisting of R, OR. 0.0C.R, R. standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
  • a process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
  • X stands for a member of the group consisting of R, OR, 0.0C.R, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
  • a process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
  • a process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
  • R1 and R standing for a member of the group consisting of coon, coo, alkrl. on, and com and R1 and R2 together stand for and compounds of the formula:
  • X stands for a member of the group consisting of R, OR, 0.00.3, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
  • HzC CHX wherein X stands for a member 01' the group consisting of R, OR, 0.003., R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
  • X stands for a member of the group consisting of R, OR, 0.00.3, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
  • HzC CHX wherein X stands for a member 01' the group consisting of R, OR, 0.003., R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.

Description

Patented May 30, 1939 UNITED STATES WATER-REPEILENT PATENT OFFICE TEXTILE MATERIAL AND PROCESS OF MANUFACTURING Il.
No Drawing.
Serial No. 118,618.
10 Claim.
This invention relates to water-repellent textile material and to a process of manuiacturing the material and is a continuation in part of our application Ser. No. 94,482, flied August 5, 1936 l and entitled Water-repellent material and a process of manufacturing the material.
We have found that textile materials can be made water-repellent in an advantageous manner by treating them with solutions or emulsions of 10. mixed polymerlzates which are prepared from maleic anhydride the free acid ora functional derivative thereoi and vinyl-esters of higher fatty acids (having at least 12 carbon atoms), Ior instance, according to the process described in U. s. Patent 2,047,398 for manufacturing mixed polymerisation products from maleic acid anhydrides and vinyl esters (see Example 4 oi the U. 8. Patent 2,047,398). These mixed polymerizates yield stable solutions or emulsions which,
90 when applied to textile fibers, especially fibers of vegetable origin, such as, for instance, cotton. have a very good waterproofing action, the treated material being repellent to water to a very high extent. The material has this property directly 86 after the treatment and does not require an altertreatment, as is the case in most similar processes.
With the same good result there may also be used the mixed polymerisate from maleic anhydride and the vinyl ether of an aliphatic alcohol 80 of high molecular weight with at least 12 carbon atoms in the molecule, as tree acid or a functional derivative thereof. These mixed polymerisates which as previously stated are obtainable according to the process described in U. 8. Patent 85 2,047,398 (see Example 6 for the manufacture of mixed polymers from maleic acid anhydride and vinyl others) or which may be obtained by mutual polymerisation of a functional derivative of maleic acid and 01 a vinyl ester or vinyl ether of high 40 molecular weight are composed of compounds of the formula:
1 wherein R1 and R2 stand for a member or the group consisting of COOH, C00, alkyl, CN, CONHz. R1 and R2 together represent and compounds of the formula 55 mc=cnx Application December 31. 1936,
In Germany January 4,
wherein X stands for R, OR or 0.0CR, R representing an aliphatic hydrocarbon radical with at least 12 carbon atoms.
The reaction upon the textile materials is executed in the following way: The textile material is introduced into the solution or emulsion of the mixed polymerisate and, after drying in the air, dried for a short time at a higher temperature (at about 100 C.)
The above described process is distinguished by the fact that the fiber is not only made waterproof when treated in this manner but that it retains its waterprootness even after repeated washing to an extent which could hitherto not be attained by any process, that is to say, the mixed polymerizates above characterized are so intimately combined with the fiber that similar to fast-dyestuffs, they irreversibly adhere to the fiber.
The following examples serve to illustrate the invention but they are not intended to limit it thereto:
(1) A web of cotton or artificial silk is impregnated with a solution of 0.5 per cent strength of the mixed polymerisate from vinyl-octodecylether and maleic-acid-dimethylester in carbon tetrachloride or a mixture thereof with alcohol, and is dried at ordinary temperature. The web thus treated has a very good water-repellent effect and does not lose this property even when repeatedly washed or boiled with water.
(2) Loose wool is impregnated as indicated in Example 1 with a solution of the mixed polymerisate from vinyl-octodecyl-ether and maleic acid in a mixture consisting of methylene chloride and ethyl-alcohol. After drying, the wool thus treated shows an enhanced water-repelling effect which it does not lose by washing.
(3) A web of cotton or artificial silk is impregnated with a solution in methylene chloride of the mixed polymerisate from vinyl-stearate and the semi-ester oi maieic acid with methyl alcohol, and is dried at ordinary temperature. The fabric thus treated has a very good waterrepellent effect and does not lose this property even after repeated washing or boiling with water.
(4) A web of viscose artificial silk is treated with a solution of 0.5% strength in alcohol and carbon tetrachloride of the mixed polymerisate from maleic acid and vinyloctodecyl-ether obtained by treating with steam the anhydride mixed polymerisate and dried for a short time. The fabric thus treated has a very good waterrepellent effect and does not lose this property even by washing or boiling.
(5) Loose spun rayon is impregnated with a solution of 2% strength in carbon tetrachloride of the mixed polymerisate from vinyl-stearate and maleic acid monomethyl ester, squeezed and dried. The spun rayon thus treated is very hydrophobe and does not lose this property by subsequent fulling.
(6) Piece goods consisting of a mixture of wool and spun rayon are impregnated with an aqueous solution of 1% strength of the pyridine salt of a mixed polymerisate from maleic acid and vinylhexadecyl ether and subjected for a short time to a heat treatment at 90 C.-l C. The material thus treated has a very good water-repellent effect and does not lose this property even by washing.
('7) Loose cotton is impregnated with an aqueous solution of 0.8% strength of the amide-ammonium salt of the mixed polymerisate from maleic acid and vinyl stearate,obtainableby the treatment of the anhydride with dry ammonia, and dried. Cotton thus treated has the same properties as those of the material obtained according to Example 6.
(8) A cotton fabric is impregnated by passage through a solution of a mixed polymerizate from viral stearate and maleic anhydride in methylene chloride, dried by exposure to air and heated for half-an-hour to about 100 C. The fabric thus treated is highly repellent to water and does not lose the property even after repeated washing with water and soap.
(9) A cotton or artificial silk fabric is impregnated with an aqueous emulsion of a mixed polymerizate from vinyl palmitate and maleic anhydride and worked up as indicated in Example 8. If desired the heat-treatment may be followed by a further treatment with aluminium formate, whereby the water-repelling effect is further increased. .This fabric also retains its water-repellent property after repeated washing.
(10) Loose wool is immersed into a solution of per cent strength of a mixed polymerizate from vinyl stearate and maleic anhydride, pressed and dried at 90-100 C. The material thus treated has an increased resistance to water.
(11) A fabric of cotton or artificial silk is impregnated with a solution of a mixed polymerizate from vinyl octo-decyl ether and maleic anhydride in ethylene chloride, dried and then heated for a short time at about 100 0., whereby the mixed polymerizate is intimately combined with the fibre. The fabric thus treated is highly repellent to water and does not lose this property even when washed with water and soap.
Instead of the aforesaid mixed polymerizate from maleic anhydride and vinyloctodecyl ether, the mixed polymerizate from maleic anhydride and the vinyl ether of the alcohol mixture obtainable by reduction of the coconut oil fatty acid and which contaim chiefly carbon chains with 12 to 14 carbon atoms, maybe applied in a similar manner for rendering the textile fiber highly waterproof.
(12) A cotton fabric is impregnated with a solution of 0.5% strength of a mixed polymerizate of maleic anhydride and vinyl dodecyl ether in carbon tetrachloride and dried subsequently, finally for a short time at a temperature of 100 C. The fabric treated in this manner is highly repellent to water and does not lose this property even when washed with water and soap.
(13) A fabric of viscose artificial silk is imof maleic anhydride and hexa-decylene in carbon.
tetrachloride. The material thus treated shows after drying which is finally performed for a short time at a temperature of 100 C., an excellent water-repellent eifect and a great stability to water.
We claim:
1. A process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of compounds of the formula:
R1 and R2 standing for a member of the group consisting of (2001-1, C00, alkyl, CN and CONI-Iz and R1 and R2 together stand for and compounds of the formula:
wherein X stands for a member of the group consisting of R, OR. 0.0C.R, R. standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
2. A process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
'nccoon and compounds of the formula:
wherein X stands for a member of the group consisting of R, OR, 0.0C.R, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
3. A process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
HC.COOH
HCLCOOH and vinyloctodecylether.
4. A process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
HC.COOH
HC.COOH
and vinylhexadecylether.
5. Textile materials impregnated with mixed polymerisates being composed of compounds of the formula:
R1 and R: standing for a member of the group consisting of coon, coo, alkrl. on, and com and R1 and R2 together stand for and compounds of the formula:
1110:0153- wherein X stands for a member of the group consisting of R, OR, 0.00.3, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
6. Textile materials impregnated with mixed poiymerisates being composed of malelc acid of the iormula n .0001; and compounds of the formula:
HzC=CHX wherein X stands for a member 01' the group consisting of R, OR, 0.003., R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
'7. Textile materials impregnated with mixed polymerisates being composed of maleic acid of the formula:
11 .coon 5 and vinyloctodecyiether.
8. Textile materials impregnated with mixed poiymerisates being composed of maleic acid of CERTIFICATE OF CORRECTION Patent No. 2,160,575;
ARTHUR voss, ET AL.
- It is-hereby certified that error appears requiring correction as follows: Page 1, first of the above numbered patent column, line 1 .6, and page 5, first column, comma after "000" and insertinstead a period;
"CONH and insert instead a comma;
1 7, strike out the period after in the printed specification line '1, claim 5 strike out the page 1, first column, lino P589 2, second column, line 27, claim 1, strike out the comma after "000"; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.
Signed and sealed this 19th day ofseptember, A. D. 1959.
(Seal) Henry Van Arsdale, Acting Comissioner of Patents.
consisting of coon, coo, alkrl. on, and com and R1 and R2 together stand for and compounds of the formula:
1110:0153- wherein X stands for a member of the group consisting of R, OR, 0.00.3, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
6. Textile materials impregnated with mixed poiymerisates being composed of malelc acid of the iormula n .0001; and compounds of the formula:
HzC=CHX wherein X stands for a member 01' the group consisting of R, OR, 0.003., R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
'7. Textile materials impregnated with mixed polymerisates being composed of maleic acid of the formula:
11 .coon 5 and vinyloctodecyiether.
8. Textile materials impregnated with mixed poiymerisates being composed of maleic acid of CERTIFICATE OF CORRECTION Patent No. 2,160,575;
ARTHUR voss, ET AL.
- It is-hereby certified that error appears requiring correction as follows: Page 1, first of the above numbered patent column, line 1 .6, and page 5, first column, comma after "000" and insertinstead a period;
"CONH and insert instead a comma;
1 7, strike out the period after in the printed specification line '1, claim 5 strike out the page 1, first column, lino P589 2, second column, line 27, claim 1, strike out the comma after "000"; and that the said Letters Patent should be read with this correction therein that the same may conform to the record of the case in the Patent Office.
Signed and sealed this 19th day ofseptember, A. D. 1959.
(Seal) Henry Van Arsdale, Acting Comissioner of Patents.
US11867836 1936-01-04 1936-12-31 Water-repellent textile material and process of manufacturing it Expired - Lifetime US2160375A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2160375X 1936-01-04
GB464237A GB472613A (en) 1936-03-27 1936-03-27 Process for waterproofing textile materials

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BE (1) BE416900A (en)
FR (1) FR809289A (en)
GB (1) GB464860A (en)
NL (1) NL44643C (en)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2439081A (en) * 1944-05-05 1948-04-06 Eastman Kodak Co Polymers of cyanoacrylic acid derivatives
US2499653A (en) * 1946-10-17 1950-03-07 American Cyanamid Co Treatment of protein-containing textile materials and products thereof
US2524022A (en) * 1948-03-04 1950-09-26 Montclair Res Corp Water repellent fabrics and composition and process for making same
US2746837A (en) * 1951-12-28 1956-05-22 Gen Aniline & Film Corp Manufacture of leather using a modified vinyl ether-maleic anhydride copolymer, and resulting product
US2780567A (en) * 1954-03-22 1957-02-05 Rohm & Haas Stabilization of protein-containing textiles
US2876895A (en) * 1953-02-26 1959-03-10 William S Port Release agents for pressure-sensitive adhesives
US2998326A (en) * 1956-04-04 1961-08-29 Nat Starch Products Inc Cleaning and sizing of fabrics
US3410720A (en) * 1965-07-12 1968-11-12 Monsanto Co Modified textile material resistant to penetration by aqueous media

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2439081A (en) * 1944-05-05 1948-04-06 Eastman Kodak Co Polymers of cyanoacrylic acid derivatives
US2499653A (en) * 1946-10-17 1950-03-07 American Cyanamid Co Treatment of protein-containing textile materials and products thereof
US2524022A (en) * 1948-03-04 1950-09-26 Montclair Res Corp Water repellent fabrics and composition and process for making same
US2746837A (en) * 1951-12-28 1956-05-22 Gen Aniline & Film Corp Manufacture of leather using a modified vinyl ether-maleic anhydride copolymer, and resulting product
US2876895A (en) * 1953-02-26 1959-03-10 William S Port Release agents for pressure-sensitive adhesives
US2780567A (en) * 1954-03-22 1957-02-05 Rohm & Haas Stabilization of protein-containing textiles
US2998326A (en) * 1956-04-04 1961-08-29 Nat Starch Products Inc Cleaning and sizing of fabrics
US3410720A (en) * 1965-07-12 1968-11-12 Monsanto Co Modified textile material resistant to penetration by aqueous media

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GB464860A (en) 1937-04-19
FR809289A (en) 1937-02-27
BE416900A (en) 1900-01-01

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