US2505259A - Production of water-repellent textiles - Google Patents
Production of water-repellent textiles Download PDFInfo
- Publication number
- US2505259A US2505259A US692384A US69238446A US2505259A US 2505259 A US2505259 A US 2505259A US 692384 A US692384 A US 692384A US 69238446 A US69238446 A US 69238446A US 2505259 A US2505259 A US 2505259A
- Authority
- US
- United States
- Prior art keywords
- water
- repellent
- textile
- fabric
- long
- 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
Links
- 239000004753 textile Substances 0.000 title claims description 26
- 239000005871 repellent Substances 0.000 title description 25
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000005846 sugar alcohols Polymers 0.000 claims description 7
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 150000003609 titanium compounds Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 150000002646 long chain fatty acid esters Chemical class 0.000 claims description 4
- 150000004668 long chain fatty acids Chemical class 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical class [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 24
- 239000004744 fabric Substances 0.000 description 22
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 16
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 12
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 12
- 229910000349 titanium oxysulfate Inorganic materials 0.000 description 10
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- -1 fatty acid ester Chemical class 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000004900 laundering Methods 0.000 description 5
- 238000009877 rendering Methods 0.000 description 5
- 150000003608 titanium Chemical class 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- ARIWANIATODDMH-UHFFFAOYSA-N Lauric acid monoglyceride Natural products CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- ARIWANIATODDMH-AWEZNQCLSA-N 1-lauroyl-sn-glycerol Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)CO ARIWANIATODDMH-AWEZNQCLSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 150000002314 glycerols Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- QDZRBIRIPNZRSG-UHFFFAOYSA-N titanium nitrate Chemical compound [O-][N+](=O)O[Ti](O[N+]([O-])=O)(O[N+]([O-])=O)O[N+]([O-])=O QDZRBIRIPNZRSG-UHFFFAOYSA-N 0.000 description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- INNSZZHSFSFSGS-UHFFFAOYSA-N acetic acid;titanium Chemical compound [Ti].CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O INNSZZHSFSFSGS-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- DCKVFVYPWDKYDN-UHFFFAOYSA-L oxygen(2-);titanium(4+);sulfate Chemical compound [O-2].[Ti+4].[O-]S([O-])(=O)=O DCKVFVYPWDKYDN-UHFFFAOYSA-L 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- HHDOORYZQSEMGM-UHFFFAOYSA-L potassium;oxalate;titanium(4+) Chemical compound [K+].[Ti+4].[O-]C(=O)C([O-])=O HHDOORYZQSEMGM-UHFFFAOYSA-L 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229910000348 titanium sulfate Inorganic materials 0.000 description 1
- UBZYKBZMAMTNKW-UHFFFAOYSA-J titanium tetrabromide Chemical compound Br[Ti](Br)(Br)Br UBZYKBZMAMTNKW-UHFFFAOYSA-J 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
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
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- 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
- This invention relates to the production of improved, water-repellent textiles or other fibrous materialsy and more particularly to novel methods for treating such materials to impart permanent water-repellent characteristics thereto.
- the invention comprises treating textile materials, such as cotton fabrics, at room or slightlyelevated temperatures, with a combination of a water-soluble titanium salt, such as titanyl sulfate, and a long chain monocarboxylic acid ester of glycerol, such as glycerol monostearate, and then neutralizing, drying and recovering the resulting. impregnated, water-repellent material.
- a water-soluble titanium salt such as titanyl sulfate
- glycerol such as glycerol monostearate
- the invention can also be applied to other woven materials, including those made of wool, rayon, nylon, etc., or to unwoven fibers, threads or filaments, to coat or impregnate the same.
- textile here and in the claims, is generic to all such materials.
- the process of coating the fabrics with the contemplated water-repellent agents is preferably carried out at temperatures ranging from about 25 C. to 50 C., and generally may range from 15-100 C., the higher order of temperature advantageously increasing the rate of processing of the fabrics.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Apr. 25,
PRODUCTION OF WATER-REPELLENT TEXTILES Frank Kerr Signaigo, Kenmore, N. Y., assignor to E. I. du Pont de Nemours & Company, Wilmington, Del., a corporation 01' Delaware No Drawing. Application August 22, 1946,
Serial No. 692,384
8 Claims. (01. 117-1355) This invention relates to the production of improved, water-repellent textiles or other fibrous materialsy and more particularly to novel methods for treating such materials to impart permanent water-repellent characteristics thereto.
The treatment of textile materials with emulsions of parafiins, waxes, resins, and the like, to render them water-repellent has already been proposed. However, on subsequent customary laundering, washing or cleaning of the textile with detergents, such as soaps or with solvents, these treating agents are, for the most part, removed and the desired water repellency becomes lost. A real need has thus existed for a waterrepellent type of finish or' impregnating agent which is useful in treating textile or fabric materials which advantageously will be capable of permanent retention on the fabric to impart permanent water-repellency characteristics thereto.
It is among the objects of this invention to overcome the above and other disadvantages characterizing prior attempts to obtain a waterrepellent textile material and to provide a novel type of treating agent and method of rendering textile materials substantially permanent-1y water-repellent. A particular object is to provide a permanent water-repellent finish on fabrics or other textiles which will remain substantially unaffected by the customary laundering or other cleaning treatments to which-the same may be subjected during use. Other objects and advantages of the invention will be apparent from the ensuing description of my invention.
These objects are accomplishedin this invention which broadly comprisestreating textiles or similar fibrous materials'with a soluble titaniumcompound and a long chain (containing from the invention:
12 to 20 carbon atoms) fatty acid ester or a poly- [hydric alcohol (said ester. having at least one alcoholic hydroxyl and said polyhydric alcohol being free from other reactive groups) in order to impregnate said textile orfibrous materials with the resulting reaction product or insoluble titanium compound.
In a more specific andipre ferred embodiment, the invention comprises treating textile materials, such as cotton fabrics, at room or slightlyelevated temperatures, with a combination of a water-soluble titanium salt, such as titanyl sulfate, and a long chain monocarboxylic acid ester of glycerol, such as glycerol monostearate, and then neutralizing, drying and recovering the resulting. impregnated, water-repellent material.
To a clearer understanding of the invention, the following specific examples are given. These are merely illustrative and are not to be construed as limiting the underlying principles of Example I Khaki-dyed poplin is rendered water-repellent by first impregnating it with glycerol monostearate by treatment in a hot aqueous dispersion of glycerol monostearate for about 10 minutes, followed by treating for one hour at room temperature in a 25% aqueous solution of titanyl sulfate saturated with glycerol monostearate. The treated fabric is then passed through a 2% ammonia solution, and washed thoroughly with water, and dried. The finished fabric, after subjection to a laundering test, exhibits high water-repellency characteristics upon being subjected to a standard spray test, in compartson with a treated control. Controls treated with glycerol monostearate alone, and glycerol monostearate plus sulfuric acid possess no water repellency after laundering. The water repellency of the titanium-treated fabric is retained after washing in alcohol or chloroform.
' Example II Cotton twill fabric is rendered water-repellent by treating for about 5 minutes in a saturated acetone solution of glycerol monostearate, followed after drying by treatment at room temperature for about 30 minutes, in a 17% solution of titanylsulfate'saturated' with glycerol monostearate. The treated fabric is then thoroughly washed in cold water to remove excess titanyl sulfate and free sulfuric acid. The finished material possesses excellent water-repellent properties after laundering'with soap and warm water. 1 i
Example III Example IV Example III is duplicated, except that a cotton fabric is treated with 12% aqueous solution of titanyl sulfate saturated with the monolauryl ether of glycerol. The treated fabric is found to exhibit substantially similar, improved waterrepellent properties.
As already stated, the foregoing examples i1lustrate in detail certain aspects of the invention, but it is to be understood that the invention is not limited thereto. Thus, in lieu of titanyl sulfate, other soluble inorganic or organic compounds or salts of titanium, as well as varying amounts of these compounds, can be employed herein. For example, titanium tetrachloride, titanium bromide, titanium sulfate, titanium nitrate, titanium potassium oxalate, and titanium acetate or lactate, etc., can be used. The TiOz concentration of such solutions can range from about 1% to 30%, but preferably ranges from 15-25%.
Although preferably glycerol monostearate is used in combination with a soluble titanium compound to form upon or impregnate a fabric with water-repellent finish, other long chain fatty acid esters of a polyhydric alcohol in which the ester contains at least one alcoholic hydroxyl and the polyhydric alcohol is free from other reactive groups can be employed. Long-chain (containing from 12-20 carbon atoms) monocarboxylic acid esters of glycerol, such as glycerol monostearate or laurate, are especially useful, as are products resulting from the esterification of glycerol with other acids, such as those of myristic, palmitic, stearic, oleic, etc. Again, while the glycerol esters mentioned are preferred for use herein, those obtained from the esterification of other polyhydric alcohols which are free from reactive groups other than the alcoholic hydroxyl groups, such as from ethylene glycol, propylene glycol, pentaerythritol and serbitol, etc., can also be utilized.
Similarly, while especially useful for applying a water-repellent finish to a textile article, such as cotton fabric, the invention can also be applied to other woven materials, including those made of wool, rayon, nylon, etc., or to unwoven fibers, threads or filaments, to coat or impregnate the same. The term textile, here and in the claims, is generic to all such materials.
The process of coating the fabrics with the contemplated water-repellent agents is preferably carried out at temperatures ranging from about 25 C. to 50 C., and generally may range from 15-100 C., the higher order of temperature advantageously increasing the rate of processing of the fabrics.
As solvents for the preparation of solutions of titanium salts and glycerol esters. water, acetone. alcohol, or other solvent systems determined by the solubility characteristics of the titanium salts and the long-chain organic compounds can be employed.
As noted in the examples, after titanatlon the textile is passed through an ammoniacal solution to effect neutralization thereof and remove excess residual acid and avoid tendering of the fabric. Such residual acid removal can be effected by extended washing treatment in water or by resorting to other neutralizing agents, such as alkali metal hydroxides or carbonates generally, including potassium or sodium hydroxide or carbonate, ammonium hydroxide, or related materials.
I claim as my invention:
1. A water-repellent textile containing the reaction product of a soluble titanium compound with a long-chain fatty acid ester of a monomeric polyhydric alcohol, said ester containing at least 1 alcoholic hydroxyl and its long-chain fatty acid component having from 12 to 20 carbon atoms.
2. A wateflrepellent textile containing the reaction product of a water-soluble titanium salt with a long-chain monocarboxylic acid ester of glycerol, said long-chain fatty acid component containing from 12 to 20 carbon atoms.
3. A water-repellent textile containing the reaction product of titanyl sulfate with glycerol monostearate.
4. A water-repellent textile containing the reaction product of titanyl sulfate with glycerol monolaurate.
5. A method for rendering a textile material water-repellent which comprises treating said material with solutions of a soluble titanium compound and a long-chain fatty acid ester of a monomeric polyhydric alcohol, said ester containing at least 1 alcoholic hydroxyl and the long-chain fatty acid component thereof having from 12 to 20 carbon atoms, and then neutralizing, drying and recovering the resulting water-repellent textile.
6. A method for rendering a textile material Water-repellent which comprises treating said material at temperatures ranging from 15 C. to C. with a combination of a water-soluble titanium salt and a long-chain monocarboxylic acid ester of glycerol, said long-chain component containing from 12 to 20 carbon atoms, and then neutralizing, washing, drying and recovering the resulting Water-repellent textile.
'7. A method for rendering a textile fabric water-repellent which comprises treating said fabric at substantially room temperature with a combination of a solution of titanyl sulfate and glycerol monostearate, and then neutralizing, washing and drying the resulting water-repellent fabric.
8. A method for rendering a textile fabric water-repellent which comprises treating said fabric at substantially room temperature with a combination of a solution of titanyl sulfate and glycerol monolaurate, and then neutralizing. washing and drying the resulting water-repellent fabric.
FRANK KERR SIGNAIGO.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,035,483 Kirk et a1 Mar. 31, 1936 2,035,504 Parkinson et al Mar. 31, 1936 2,356,161 Iler Aug. 22, 1944 2,402,857 VanMater June 25, 1946 FOREIGN PATENTS Number Country Date 391,772 Great Britain July 14, 1932
Claims (1)
1. A WATER-REPELLANT TEXTILE CONTAINING THE REACTION PRODUCT OF A SOLUBLE TITANIUM COMPOUND WITH A LONG-CHAIN FATTY ACID ESTER OF A MONOMERIC POLYHYDRIC ALCOHOL, SAID ESTER CONTAINING AT LEAST 1 ALCOHOLIC HYDROXYL AND ITS LONG-CHAIN FATTY ACID COMPONENT HAVING FROM 12 TO 20 CARBON ATOMS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US692384A US2505259A (en) | 1946-08-22 | 1946-08-22 | Production of water-repellent textiles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US692384A US2505259A (en) | 1946-08-22 | 1946-08-22 | Production of water-repellent textiles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2505259A true US2505259A (en) | 1950-04-25 |
Family
ID=24780355
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US692384A Expired - Lifetime US2505259A (en) | 1946-08-22 | 1946-08-22 | Production of water-repellent textiles |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2505259A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE954738C (en) * | 1951-06-08 | 1956-12-20 | Titan Gmbh | Process for the production of gelled masses to be used in particular in linoleum production |
| US2933411A (en) * | 1953-06-18 | 1960-04-19 | Ohio Commw Eng Co | Method of dry cleaning and rendering fabrics water repellent |
| US2966505A (en) * | 1956-08-24 | 1960-12-27 | Du Pont | Preparation of organic titanium compounds |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB391772A (en) * | 1931-10-14 | 1933-04-18 | British Celanese | Improvements in or relating to the treatment of textile materials |
| US2035504A (en) * | 1929-11-06 | 1936-03-31 | Celanese Corp | Treatment of artificial materials |
| US2035483A (en) * | 1931-10-15 | 1936-03-31 | Celanese Corp | Treatment of textile materials |
| US2356161A (en) * | 1941-07-18 | 1944-08-22 | Du Pont | Chemical process and products |
| US2402857A (en) * | 1941-03-05 | 1946-06-25 | Titanium Alloy Mfg Co | Composition for waterproofing textiles and method of preparation |
-
1946
- 1946-08-22 US US692384A patent/US2505259A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2035504A (en) * | 1929-11-06 | 1936-03-31 | Celanese Corp | Treatment of artificial materials |
| GB391772A (en) * | 1931-10-14 | 1933-04-18 | British Celanese | Improvements in or relating to the treatment of textile materials |
| US2035483A (en) * | 1931-10-15 | 1936-03-31 | Celanese Corp | Treatment of textile materials |
| US2402857A (en) * | 1941-03-05 | 1946-06-25 | Titanium Alloy Mfg Co | Composition for waterproofing textiles and method of preparation |
| US2356161A (en) * | 1941-07-18 | 1944-08-22 | Du Pont | Chemical process and products |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE954738C (en) * | 1951-06-08 | 1956-12-20 | Titan Gmbh | Process for the production of gelled masses to be used in particular in linoleum production |
| US2933411A (en) * | 1953-06-18 | 1960-04-19 | Ohio Commw Eng Co | Method of dry cleaning and rendering fabrics water repellent |
| US2966505A (en) * | 1956-08-24 | 1960-12-27 | Du Pont | Preparation of organic titanium compounds |
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