US2191982A - Water repellent textile material - Google Patents

Water repellent textile material Download PDF

Info

Publication number
US2191982A
US2191982A US21880038A US2191982A US 2191982 A US2191982 A US 2191982A US 21880038 A US21880038 A US 21880038A US 2191982 A US2191982 A US 2191982A
Authority
US
United States
Prior art keywords
water
textile material
fabric
acid
zirconium
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
Inventor
Doser Arnold
Bayer Otto
Hintzmann Karl
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Application granted granted Critical
Publication of US2191982A publication Critical patent/US2191982A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • D06M13/10—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 oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/1845—Aromatic mono- or polycarboxylic acids
    • 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
    • Y10T442/2164—Coating or impregnation specified as water repellent

Definitions

  • the present invention relates to a process for rendering fibrous materials water-repellent, and to materials so treated.
  • organic compounds are especially useful for the purpose of our invention as contain, attached to an aromatic nucleus in o-position to each other, a hydroxy or mercapto group and a carboxylic acid group, i. e. compounds like salicylic acid, thiosalicylic acid and derivatives thereof.
  • the compounds to be used for our invention should, furthermore, preferably contain as a hydrophobe radical, an aliphatic radical of at least 10 carbon atoms directly connected with each other which may be attached to the salicylic acid grouping directly or by means of a hetero atom or a hetero atom group.
  • Compounds of this kind which may be employed for the purpose of our invention,
  • Stearoyl-p-aminosalicylic acid Isoheptoyl-p-aminosalicylic acid Lauroyl-p-aminosalicylic acid StearoyF-p-aminothiosalicylic acid 55 4-hydroxydiphenyl-3-carboxylic acid
  • the alkylation product of 2.3-hydroxynaphthoic acid with dodecylene The condensation product of isooctylphenol-ocarboxylic acid with formaldehyde Reaction products of polyethylene-diamines and/or -imines with chloromethylcresotic acid Reaction product of salicylic acid-disulfochloride with 2 mol dodecylamine 10
  • the soluble compounds of zirconium those are especially suitable which dissolve in water with strong acid reaction, like zirconium chloride, zirconium nitrate and the water-soluble hydrolysates obtainable therefrom.
  • Our present process is preferably performed by impregnating the fibrous material with a solution of the organic component and, either before or afterwards, with a solution of the metal compound.
  • a solution of the organic component In the case of artificial fibrous material go it is also possible to incorporate with spinning solutions thereof a difllcultly soluble organic compound, containing, for instance, the salicylic acid grouping, and to aftertreat the material so obtained with a solution of the metal compound.
  • Our new process may be combined with other textile treatment processes, for instance, with animalizing of artificial fibers or with the dyeing of wool with such dyestuffs which are chromed on the fiber (use of chromium compounds). It may be noted, however, that the best result so far has been obtained by using zirconium compounds.
  • Example 1 A staple fiber fabric from viscose is treated 35 for 1 minute at 90 C. with an aqueous solution of 10 g. /l. of a sodium salt of stearyl-p-aminosalicylic acid, hydroextracted and dried for a short time. Thereupon the material is immersed for 5 minutes at 90 C. in an aqueous solution of 2,5 g./l. zirconiumoxychloride and 1 g./l. crystallized sodium acetate again hydroextracted and dried at 95-100 C.for 20 minutes. The fabric is waterrepellent and does not lose this property by washing with soap even if it is boiled for 10 minutes with an aqueous solution of 5 g./l. Marsellle soap and 3 g./l. soda.
  • the sodium salt of stearyl-p-aminosalicylic acid there may be used with similar result, for instance, the sodium salts of lauroylor isoheptoyl-p-aminosalicylic acid or the urea derivative which is obtainable from p-aminosalicylic acid and octadecylisocyanate.
  • the above mentioned organic compounds may be used.
  • Example 2 A staple fiber fabric from viscose is treated for 2 minutes at 90 C. with an aqueous solution of 10 g./l. zirconiumoxychloride and 4 g./l. crystallized sodium acetate. After hydroextraction and a short drying the fabric is treated for 2 minutes at 90 C. with an aqueous solution of 10 g./l. of the sodium salt of stearylureido-salicyclic acid, again hydroextracted and dried. The fabric has become water-repellent arid does not appreciably lose this property after washing and drying.
  • Example 3 The process as described in Example 3 may be applied with similar results to staple fiber fabrics which have been dyed with substantive dyestuffs, or to mixed fabrics from 1 part staple fiber and 1 part cotton or wool, or to satin-twill, wool fiannels or animalized copper artificial silk.
  • Example 5 A staple fiber fabric from viscose is treated as described in Example 1 with a sodium salt of stearoyl-p-aminosalieylic acid rnd thereupon,
  • Example 6 A staple fiber fabric from viscose is treated with a hot aqueous solution of 10 g./l. of the sodium salt of stearoyl-p-aminosalicylic acid, squeezed and thereupon treated for some minutes at 90 C. with an aqueous solution of 5 g./l. crystallized zirconiumoxychloride (having a zirconium content corresponding to about 44% ZrOz) and 2 g./l. crystallized sodium acetate. The fabric is again squeezed and immersed for a short time into an aqueous solution of 10 g./l. crystallized sodium acetate. After hydroextracting and drying at 110 C. the fabric has become water-repellent and does not lose this property even on Washing and boiling.
  • Example 7 A staple fiber fabric from viscose is impregnated with an aqueous solution of 1C g./l. of the sodium salt of technical alkyl salicylic acid (alkyl denotingalkyl radicals of from 10-18 carbon atoms). Thereupon the fabric is treated for some minutes with an aqueous solution of zirconiumoxychloride and sodium acetate as described in the foregoing example. After squeezing the fabric is treated for a short time in an aqueous solution of crystallized sodium acetate,
  • the fabric is water-repellent and does not lose this property even on washing, boiling and fulling.
  • zirconiumoxychloride instead of the zirconiumoxychloride also 20 com. of the zirconiumhydroxide sol containing about I 9.4% ZlOz and being obtainable, for instance,
  • Example 4 of the German specification 582,682 may be employed.
  • Eaample 8 effect is fast to washing. It is practically not impaired by boiling with an aqueous solution of 5 g./l. Marseille soap and 3 g./l. soda, or by fulling in an aqueous bath containing 50 g./l. soap and 5 g./l. soda or by treating with benzine or boiling for some hours in carbon tetrachloride.
  • Example 9 instead of the zirconiumoxychloride of Example 1 6.5 g./l. zirconiumnitrate per liter water containing, besides, 2 g;/l. crystallized sodium acetate may be used. After the zirconiumnitrate treatment the fabric is hydroextracted, rinsed for a short time with cold water and dried at 100 C. The result is similar as obtained according to Example 1.
  • Example '10 A cellulose acetate artificial silk fabric is treated for 10 minutes at 70 C. with a 1% aqueous solution of the sodium salt of stearoylp-aminosalicylic acid, slightly squeezed and dried. Thereupon the fabric is immersed for 5 minutes into a 2% aqueous solution of zirconium acetate or zirconium formate. After squeezing again the fabric is dried at 90-100" C. The fabric is excellently water-repellent.
  • Example 11 A staple fiber fabric from viscose is impregnated at C., with a solution of the sodium salt of stearoyl-p-aminosalicylic acid, hydroextracted and dried. Thereupon it is treated for a short time with a cold solution of 24 g./l. zirconiumoxychloride (containing 46% ZIO2) and 16 g./l.
  • Process of rendering textile material waterrepellent which comprises treating the material with an aromatic orthohydroxy carboxylic acid compound containing a hydrophobe radical, and with a water soluble complex forming metal compound selected from the group consisting of chr0- mium compounds and zirconium compounds.
  • Process of rendering textile material waterrepellent which comprises treating the material with an aromatic orthohydroxy carboxylic acid compound containing an aliphatic hydrocarbon radical of at least 10 carbon atoms directly connected with each other, and with a water soluble zirconium compound.
  • Process of rendering textile material water-repellent which comprises treating the material with an aromatic orthohydroxy carboxylic acid compound containing an aliphatic hydrocarbon radical corresponding to the radicals of the naturalhigher fatty acids, and with a water soluble zirconium compound.
  • Process of rendering textile material waterrepellent which comprises treating the material with a salicylic acid compound containing an aliphatic radical corresponding to the hydrocarbon radicals of the natural higher fatty acids, and with a water soluble zirconium compound.
  • Process of rendering textile material waterrepellent which comprises treating the material with an aromatic orthohydroxy carboxylic acid compound containing an aliphatic hydrocarbon radical corresponding to the radicals of the natural higher fatty acids and with a zirconium compound being soluble with strong acid reaction-in water and being selected from the group consisting of zirconium chloride, zirconium nitrate and I the water soluble hydrolysates obtainable therefrom.
  • Process of rendering textile material waterrepellent which comprises treating the material with a salicylic acid compound containing an ali phatic hydrocarbon radical corresponding tothe radicals of the natural higher fatty acids and with a zirconium compound being soluble with strong acid reaction in water and being selected from the group consisting of zirconium chloride, zirconium nitrate and the water soluble hydrolysates obtainable therefrom.

Landscapes

  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented Feb. 27, 1940 UNITED STATES PATENT orl-"lcc I 2,191,982 WATER REPELLENT TEXTILE MATERIAL No Drawing. Application July 12, 1938, Serial No. 218,800. In Germany July 26, 1937 12 Claims.
The present invention relates to a process for rendering fibrous materials water-repellent, and to materials so treated.
The known processes for making fibrous materials, especially textiles, water-repellent or impervious to water have the disadvantage that the effects so obtained are not sufiiciently fast to wet treatments so that the materials lose their water-repellent properties, for instance, by dyeing, washing or like wet treatments. We have now found that water-repellent properties of very good fastness to wet treatments can be imparted to any kind of textile material by treating the materials with an organic compound containing a complex forming group and a hydrophobe radical and with a soluble complex forming metal compound selected from the group consisting of chromium compounds and zirconium compounds.
We have, furthermore, found that such organic compounds are especially useful for the purpose of our invention as contain, attached to an aromatic nucleus in o-position to each other, a hydroxy or mercapto group and a carboxylic acid group, i. e. compounds like salicylic acid, thiosalicylic acid and derivatives thereof. The compounds to be used for our invention should, furthermore, preferably contain as a hydrophobe radical, an aliphatic radical of at least 10 carbon atoms directly connected with each other which may be attached to the salicylic acid grouping directly or by means of a hetero atom or a hetero atom group. Compounds of this kind which may be employed for the purpose of our invention,
are, for instance, the following:
Stearoyl-p-aminosalicylic acid Isoheptoyl-p-aminosalicylic acid Lauroyl-p-aminosalicylic acid StearoyF-p-aminothiosalicylic acid 55 4-hydroxydiphenyl-3-carboxylic acid The alkylation product of 2.3-hydroxynaphthoic acid with dodecylene The condensation product of isooctylphenol-ocarboxylic acid with formaldehyde Reaction products of polyethylene-diamines and/or -imines with chloromethylcresotic acid Reaction product of salicylic acid-disulfochloride with 2 mol dodecylamine 10 Among the soluble compounds of zirconium those are especially suitable which dissolve in water with strong acid reaction, like zirconium chloride, zirconium nitrate and the water-soluble hydrolysates obtainable therefrom.
Our present process is preferably performed by impregnating the fibrous material with a solution of the organic component and, either before or afterwards, with a solution of the metal compound. In the case of artificial fibrous material go it is also possible to incorporate with spinning solutions thereof a difllcultly soluble organic compound, containing, for instance, the salicylic acid grouping, and to aftertreat the material so obtained with a solution of the metal compound. Our new process may be combined with other textile treatment processes, for instance, with animalizing of artificial fibers or with the dyeing of wool with such dyestuffs which are chromed on the fiber (use of chromium compounds). It may be noted, however, that the best result so far has been obtained by using zirconium compounds.
Example 1 A staple fiber fabric from viscose is treated 35 for 1 minute at 90 C. with an aqueous solution of 10 g. /l. of a sodium salt of stearyl-p-aminosalicylic acid, hydroextracted and dried for a short time. Thereupon the material is immersed for 5 minutes at 90 C. in an aqueous solution of 2,5 g./l. zirconiumoxychloride and 1 g./l. crystallized sodium acetate again hydroextracted and dried at 95-100 C.for 20 minutes. The fabric is waterrepellent and does not lose this property by washing with soap even if it is boiled for 10 minutes with an aqueous solution of 5 g./l. Marsellle soap and 3 g./l. soda.
Instead of the sodium salt of stearyl-p-aminosalicylic acid there may be used with similar result, for instance, the sodium salts of lauroylor isoheptoyl-p-aminosalicylic acid or the urea derivative which is obtainable from p-aminosalicylic acid and octadecylisocyanate. In a similar way the above mentioned organic compounds may be used. The materials treated in this man- 55 ner, besides being water-repellent, display an agreeable full handle.
Example 2 A staple fiber fabric from viscose is treated for 2 minutes at 90 C. with an aqueous solution of 10 g./l. zirconiumoxychloride and 4 g./l. crystallized sodium acetate. After hydroextraction and a short drying the fabric is treated for 2 minutes at 90 C. with an aqueous solution of 10 g./l. of the sodium salt of stearylureido-salicyclic acid, again hydroextracted and dried. The fabric has become water-repellent arid does not appreciably lose this property after washing and drying.
Example 3 Example 4 The process as described in Example 3 may be applied with similar results to staple fiber fabrics which have been dyed with substantive dyestuffs, or to mixed fabrics from 1 part staple fiber and 1 part cotton or wool, or to satin-twill, wool fiannels or animalized copper artificial silk.
Example 5 A staple fiber fabric from viscose is treated as described in Example 1 with a sodium salt of stearoyl-p-aminosalieylic acid rnd thereupon,
with an aqueous solution of 15 g./l. of a B. solution of chromium acetate for 1 minute at 90 C. The fabric is then hydroextracted and dried for 30 minutes at 30 C. The fabric has become water-repellent; the impregnation is fast to washing and boiling. Instead of the p-aminosalicylic acid compound the other above mentioned compounds may be used.
Example 6 A staple fiber fabric from viscose is treated with a hot aqueous solution of 10 g./l. of the sodium salt of stearoyl-p-aminosalicylic acid, squeezed and thereupon treated for some minutes at 90 C. with an aqueous solution of 5 g./l. crystallized zirconiumoxychloride (having a zirconium content corresponding to about 44% ZrOz) and 2 g./l. crystallized sodium acetate. The fabric is again squeezed and immersed for a short time into an aqueous solution of 10 g./l. crystallized sodium acetate. After hydroextracting and drying at 110 C. the fabric has become water-repellent and does not lose this property even on Washing and boiling.
Example 7 A staple fiber fabric from viscose is impregnated with an aqueous solution of 1C g./l. of the sodium salt of technical alkyl salicylic acid (alkyl denotingalkyl radicals of from 10-18 carbon atoms). Thereupon the fabric is treated for some minutes with an aqueous solution of zirconiumoxychloride and sodium acetate as described in the foregoing example. After squeezing the fabric is treated for a short time in an aqueous solution of crystallized sodium acetate,
hydroextracted and dried at 80-100 C. The fabric is water-repellent and does not lose this property even on washing, boiling and fulling. Instead of the zirconiumoxychloride also 20 com. of the zirconiumhydroxide sol containing about I 9.4% ZlOz and being obtainable, for instance,
corresponding to Example 4 of the German specification 582,682 may be employed.
Eaample 8 effect is fast to washing. It is practically not impaired by boiling with an aqueous solution of 5 g./l. Marseille soap and 3 g./l. soda, or by fulling in an aqueous bath containing 50 g./l. soap and 5 g./l. soda or by treating with benzine or boiling for some hours in carbon tetrachloride.
Example 9 Instead of the zirconiumoxychloride of Example 1 6.5 g./l. zirconiumnitrate per liter water containing, besides, 2 g;/l. crystallized sodium acetate may be used. After the zirconiumnitrate treatment the fabric is hydroextracted, rinsed for a short time with cold water and dried at 100 C. The result is similar as obtained according to Example 1.
Example '10 A cellulose acetate artificial silk fabric is treated for 10 minutes at 70 C. with a 1% aqueous solution of the sodium salt of stearoylp-aminosalicylic acid, slightly squeezed and dried. Thereupon the fabric is immersed for 5 minutes into a 2% aqueous solution of zirconium acetate or zirconium formate. After squeezing again the fabric is dried at 90-100" C. The fabric is excellently water-repellent.
Example 11 A staple fiber fabric from viscose is impregnated at C., with a solution of the sodium salt of stearoyl-p-aminosalicylic acid, hydroextracted and dried. Thereupon it is treated for a short time with a cold solution of 24 g./l. zirconiumoxychloride (containing 46% ZIO2) and 16 g./l.
crystallized sodium acetate or 12 g./l. sodium tetraborate. After squeeezing and drying for 40 minutes at 90-95 C. the fabric has become water-repellent and does not lose this property even on washing and boiling.
We claim:
1. Process of rendering textile material waterrepellent which comprises treating the material with an aromatic orthohydroxy carboxylic acid compound containing a hydrophobe radical, and with a water soluble complex forming metal compound selected from the group consisting of chr0- mium compounds and zirconium compounds.
2. Process of rendering textile material waterrepellent which comprises treating the material with an aromatic orthohydroxy carboxylic acid compound containing an aliphatic hydrocarbon radical of at least 10 carbon atoms directly connected with each other, and with a water soluble zirconium compound.
3. Process of rendering textile material water-repellent which comprises treating the material with an aromatic orthohydroxy carboxylic acid compound containing an aliphatic hydrocarbon radical corresponding to the radicals of the naturalhigher fatty acids, and with a water soluble zirconium compound.
4. Process of rendering textile material waterrepellent which comprises treating the material with a salicylic acid compound containing an aliphatic radical corresponding to the hydrocarbon radicals of the natural higher fatty acids, and with a water soluble zirconium compound.
5. Process of rendering textile material waterrepellent which comprises treating the material with an aromatic orthohydroxy carboxylic acid compound containing an aliphatic hydrocarbon radical corresponding to the radicals of the natural higher fatty acids and with a zirconium compound being soluble with strong acid reaction-in water and being selected from the group consisting of zirconium chloride, zirconium nitrate and I the water soluble hydrolysates obtainable therefrom. Y
6. Process of rendering textile material waterrepellent which comprises treating the material with a salicylic acid compound containing an ali phatic hydrocarbon radical corresponding tothe radicals of the natural higher fatty acids and with a zirconium compound being soluble with strong acid reaction in water and being selected from the group consisting of zirconium chloride, zirconium nitrate and the water soluble hydrolysates obtainable therefrom.
7. Textile material when treated according to the process of claim 1.
8. Textile material when treated according to the process of claim 2.
9. Textile material when treated according to the process of claim 3.
10. Textile material when treated according to the process of claim 4.
11. Textile material when treated according to the process of claim 5.
12. Textile material when treated according to the process of claim 6.
ARNOLD DOSER. o'rro BAYER. KARL muzumm.
US21880038 1937-07-26 1938-07-12 Water repellent textile material Expired - Lifetime US2191982A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE517337X 1937-07-26

Publications (1)

Publication Number Publication Date
US2191982A true US2191982A (en) 1940-02-27

Family

ID=6549524

Family Applications (1)

Application Number Title Priority Date Filing Date
US21880038 Expired - Lifetime US2191982A (en) 1937-07-26 1938-07-12 Water repellent textile material

Country Status (3)

Country Link
US (1) US2191982A (en)
FR (1) FR841087A (en)
GB (1) GB517337A (en)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2457853A (en) * 1944-09-20 1949-01-04 Nat Lead Co Treatment of textiles and composition therefor
US2997407A (en) * 1956-01-23 1961-08-22 American Cyanamid Co Textile finishing agents
US3031335A (en) * 1958-08-01 1962-04-24 Segal Leon Oil-and water-resistant fabrics and method for their production
US3163552A (en) * 1960-02-27 1964-12-29 Bohme Fettchemie Gmbh Process for making fibrous material hydrophobic

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1275504B (en) * 1960-06-30 1968-08-22 Bayer Ag Process for making textile materials water-repellent

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2457853A (en) * 1944-09-20 1949-01-04 Nat Lead Co Treatment of textiles and composition therefor
US2997407A (en) * 1956-01-23 1961-08-22 American Cyanamid Co Textile finishing agents
US3031335A (en) * 1958-08-01 1962-04-24 Segal Leon Oil-and water-resistant fabrics and method for their production
US3163552A (en) * 1960-02-27 1964-12-29 Bohme Fettchemie Gmbh Process for making fibrous material hydrophobic

Also Published As

Publication number Publication date
FR841087A (en) 1939-05-10
GB517337A (en) 1940-01-26

Similar Documents

Publication Publication Date Title
US2329622A (en) Treatment of woolen textile materials
US2323387A (en) Process of producing water repellent textile material
GB345207A (en) Sizing textile fibres
US2426770A (en) Textile finishing composition comprising a methoxymethyl melamine and an aliphatic alcohol having at least eight carbon atoms
US2284895A (en) Treatment of textiles to impart water-repellence
US2328431A (en) Process for rendering textile materials water repellent
US2191982A (en) Water repellent textile material
US1536254A (en) Water-repellent textile material and method of producing the same
DE1237527B (en) Process for reducing the water absorbency and for making cellulose-containing textiles crease-resistant
GB413328A (en) Process for the improvement of vegetable and regenerated cellulose textiles
US2316057A (en) Textile material
US2423261A (en) Germicidal product and method of producing same
DE843395C (en) Process for improving in particular the ironing resistance of fiber material
US3130001A (en) Process for the production of dyed cellulosic textile materials with wet and dry wrinkle resistance
US2565832A (en) Process for treating cellulose fibers and composition therefor
US2505259A (en) Production of water-repellent textiles
US2282701A (en) Process of waterproofing
JPS6233348B2 (en)
US2702228A (en) Method of modifying cellulose fibers with alkali solutions of copper or nickel biuret
US2455886A (en) Method of rendering textile material water repellent, and the product
DE719056C (en) Process for rendering fibrous materials water repellent
US2186739A (en) Treatment of fibrous materials to make them resistant to mildew
US2702258A (en) Hydrous oxide containing resinous compositions
US2708642A (en) Process for imparting water-repellancy to textiles
US3677798A (en) Polymeric chromium sulfatozirconate compositions,their preparation and use