US3494788A - Antisoiling treatment of a fibrous material and the treated material - Google Patents
Antisoiling treatment of a fibrous material and the treated material Download PDFInfo
- Publication number
- US3494788A US3494788A US633716A US3494788DA US3494788A US 3494788 A US3494788 A US 3494788A US 633716 A US633716 A US 633716A US 3494788D A US3494788D A US 3494788DA US 3494788 A US3494788 A US 3494788A
- Authority
- US
- United States
- Prior art keywords
- siloxane
- fibrous
- emulsion
- units
- sio
- 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
- 239000002657 fibrous material Substances 0.000 title description 21
- 239000000463 material Substances 0.000 title description 18
- 238000011282 treatment Methods 0.000 title description 9
- -1 hydrocarbon radical Chemical class 0.000 description 25
- 239000000839 emulsion Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 17
- 229920001577 copolymer Polymers 0.000 description 13
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- 239000004215 Carbon black (E152) Substances 0.000 description 10
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 238000001035 drying Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 239000004753 textile Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 210000002268 wool Anatomy 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229910020169 SiOa Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 240000000491 Corchorus aestuans Species 0.000 description 1
- 235000011777 Corchorus aestuans Nutrition 0.000 description 1
- 235000010862 Corchorus capsularis Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 240000006240 Linum usitatissimum Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- 241001417527 Pempheridae Species 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 229910004738 SiO1 Inorganic materials 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920006397 acrylic thermoplastic Polymers 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000004188 dichlorophenyl group Chemical group 0.000 description 1
- JVQOASIPRRGMOS-UHFFFAOYSA-M dodecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCC[N+](C)(C)C JVQOASIPRRGMOS-UHFFFAOYSA-M 0.000 description 1
- KWKXNDCHNDYVRT-UHFFFAOYSA-N dodecylbenzene Chemical compound CCCCCCCCCCCCC1=CC=CC=C1 KWKXNDCHNDYVRT-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000006232 furnace black Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 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
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/23907—Pile or nap type surface or component
- Y10T428/23986—With coating, impregnation, or bond
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
-
- 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
- Y10T442/2279—Coating or impregnation improves soil repellency, soil release, or anti- soil redeposition qualities of fabric
Definitions
- This invention relates to a process for imparting antisoiling properties to fibrous materials.
- this invention relates to a process for the treatment of a fibrous material which comprises applying to the fibrous material an emulsion of a solid siloxane copolymer consisting of 50 to 95 by Weight of RSiO units and 5 to 50% by weight of R' SiO units and R" SiO units wherein each R, R and R" radical is selected from the group consisting of hydrocarbon and substituted hydrocarbon radicals containing from 1 to 7 carbon atoms, and then drying the fibrous material.
- the process of this invention can be used for the treatment of any fibrous material Whether it be of natural or synthetic origin. Like any of the currently available treatments, the process and various siloxane copolymers of this invention perform better on some fibrous materials than on others. None-the-less, the treatment made in accordance with the process of this invention imparts improved soiling resistant properties to all fibrous materials.
- the fibrous materials that can be treated employing the process of this invention include, for example, those made from wool, jute, flax, asbestos, cotton, rayon, nylon, acrylics, polyacrylonitrile, polyvinylidene chloride, polyesters, cellulose acetate, glass and mixtures or blends thereof.
- the fibrous material is treated with an emulsion of a solid siloxane copolymer consisting of 50 to 95 by weight RSiO units and 5 to 50% by weight of R SiO and/or R SiO units wherein each R, R and R" is a hydrocarbon or substituted hydrocarbon radical containing from 1 to 7 carbon atoms.
- a solid siloxane it is meant that the siloxane is neither gaseous or liquid upon evaporation of the water'from the emulsion although it can be in the latter state while in emulsion.
- the siloxane that is deposited should be a friable or brittle solid, the former being preferred.
- the amount of the RSiO units is in the range of 60 to 80% and the amount of the R' SiO and R" SiO units is in the range of 20 to 40%.
- the R, R and R" radicals of the siloxane units can be alkyl, alkenyl, alkynyl, cycloalkyl, aryl, alkaryl or aralkyl radicals, and these radicals can contain substituents such as halogen atoms or amino, mercapto, hydroxyl, epoxy, acrylato, cyano and carboxy su-bstituents so long as there are no more than seven carbon atoms in the radical.
- radicals are the methyl, ethyl, propyl, butyl, arnyl, hexyl, heptyl, vinyl, allyl, hexenyl, propargyl, cyclohexyl, phenyl, tolyl, benzyl,
- CH, , CHCOO( CH CH :C( CH COO (CH cyanopropyl, cyanoethyl, carboxyethyl and carboxyphenyl radicals.
- CH cyanopropyl, cyanoethyl, carboxyethyl and carboxyphenyl radicals.
- the methyl and mercaptopropyl are preferred.
- emulsions used in the process of this invention can be prepared by the emulsion polymerization of a mixture of the appropriate silanes and/or siloxanes employing the techniques set forth in detail in US. 'Patents 2,891,920 and 3,294,725, and French Patent 1,460,203, the disclosures of which are incorporated herein by reference.
- the emulsions can be applied to the fibrous materials in any desired manner.
- the fibers can 'be dipped in or passed through the emulsion, or the emulsion can be padded, brushed, sprinkled or sprayed onto the fibrous material.
- the preferred method of applying the emulsion is to spray it onto the material, for example from an aerosol.
- Another way in which the emulsion can be applied to the material is to incorporate it in a cleaning formulation.
- This is a particularly useful means, for example, for applying the emulsion to rugs or carpeting once they are in place in a home or business establishment since it allows one to both clean and impart soiling resistance to the material in one operation. Best results are usually obtained, however, by first cleaning the carpeting and then applying the siloxane.
- the emulsion can be applied to the material by the consumer.
- the emulsions can also be applied to cloth or carpeting, for example, at the place of manufacture. It is also possible to apply the emulsions to the yarn prior to its use in making the finished article. Other points of applications will be apparent to those skilled in the art.
- the siloxane be applied to the fibrous material so as to achieve a weight pick-up in the range of 0.1 to 2% siloxane solids based on the weight of the fibrous material. Best results can usually be obtained in the range of 0.4 to 0.8%. Although more than 2% siloxane can be applied, the additional advantage (if any) usually is not justified by the increased cost. With respect to carpets and the like materials, this means that it is preferred that the siloxane be applied to the material in a quantity in the range of 0.1 to 1.5 g. of siloxane solids per square foot of material. Optimum results can usually be obtained when the amount applied is in the range of 0.3 to 0.6 g. per square foot.
- the siloxane When the siloxane is employed in a cleaning formulation, a rug or carpet shampoo for example, it is preferred that at least 0.4 g. per square foot be applied.
- the concentration of the siloxane in the emulsion is not critical and is immaterial to the process.
- the fibrous material is dried. Drying can be accomplished by any suitable means. For example, the simplest rneans of drying involves exposing the treated fibrous material to the air and allowing the water to evaporate. Of course, the drying can be accelerated by blowing air or some other suitable gas (particularly a gas that has been heated) across the material. Drying can also be accomplished by passing the treated material through an oven. Other means of drying the material will be obvious to those skilled in the art.
- EXAMPLE 1 The synthetic dirt used in this example was prepared as follows. 748 g. of minus 30 mesh peat moss, 109 g. of calcium carbonate, 21 g. of silica, 21 g. of cement, 21 g. of kaolin clay, 5 g. of furnace black and 1 g. of red iron oxide were placed in a bucket and mixed by hand. The mixture was then put into two Pyrex dishes and dried in a 100 C. oven for two hours. The mixture was then placed in a ball mill for two hours, 11 g. of mineral oil having been added at the end of the first hour.
- a solid siloxane copolymer consisting of to 95% by Weight of RSiO units and 5 to 50% by weight of at least one unit selected from the group consisting of R' SiO units and R" SiO units wherein each R, R and R radical is selected from the group consisting of hydrocarbon and substituted hydrocarbon radicals containing from 1
- R is selected from the group consisting of the methyl, ethyl, vinyl, phenyl 3-chloropropyl, 3-mercaptopropyl and 3,3,3-trifluoropropyl radicals, and each R and R" is a methyl radical.
- siloxane copolymer consists of HSCH CH CH SiO and (CH SiO units.
- a fibrous textile material having anti-soiling properties containing on at least a portion of its surface a solid siloxane copolymer consisting of 50 to 95% by weight of RSiO units and 5 to 50% by weight of at least one unit selected from the group consisting of R SiO units and R Sio units wherein each R, R and R" radical is selected from the group consisting .of hydrocarbon and substituted hydrocarbon radicals containing from 1 to 7 carbon atoms.
- fibrous material of claim 8 which is in the form of carpeting and wherein R is selected from the group consisting of the methyl, ethyl, vinyl, phenyl, 3-
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63371667A | 1967-04-26 | 1967-04-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3494788A true US3494788A (en) | 1970-02-10 |
Family
ID=24540817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US633716A Expired - Lifetime US3494788A (en) | 1967-04-26 | 1967-04-26 | Antisoiling treatment of a fibrous material and the treated material |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3494788A (ru) |
| AT (1) | AT284781B (ru) |
| BE (1) | BE714228A (ru) |
| CH (1) | CH615968D (ru) |
| DE (1) | DE1769249A1 (ru) |
| FR (1) | FR1561732A (ru) |
| GB (1) | GB1200237A (ru) |
| NL (1) | NL6805943A (ru) |
| SE (1) | SE362908B (ru) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030228419A1 (en) * | 2002-06-05 | 2003-12-11 | Byrne Christopher Michael | Silicone compositions for textile applications |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE754509A (fr) * | 1969-08-08 | 1971-02-08 | Dow Corning | Composition anti-salissement a base d'amidon et d'un siloxane solide |
| JPS5319709B1 (ru) * | 1970-09-03 | 1978-06-22 | ||
| US4311760A (en) * | 1976-10-04 | 1982-01-19 | Dow Corning Corporation | Method for applying mercaptoalkyl-containing polydiorganosiloxanes to textile fibers |
| DE3060191D1 (en) * | 1979-03-23 | 1982-03-25 | Goldschmidt Ag Th | Preparation for making wool shrink-proof |
| DE3034380A1 (de) * | 1980-09-12 | 1982-03-25 | Th. Goldschmidt Ag, 4300 Essen | Zubereitung zum schrumpffestmachen von wolle |
| DE3304100A1 (de) * | 1983-02-08 | 1983-09-01 | Martin 7500 Karlsruhe Sackmann | Silikonisierte textilien |
| DE19949485A1 (de) * | 1999-10-14 | 2001-04-19 | Schaeffler Waelzlager Ohg | Klemmgesperre |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2588366A (en) * | 1950-03-09 | 1952-03-11 | Dow Corning | Method of rendering fabrics waterrepellent and composition therefor |
| US2588365A (en) * | 1949-11-10 | 1952-03-11 | Dow Corning | Method of rendering fabrics waterrepellent and product resulting therefrom |
| US2914836A (en) * | 1957-06-25 | 1959-12-01 | Dow Corning | Method of making synthetic pile fabrics |
-
0
- CH CH615968D patent/CH615968D/xx unknown
-
1967
- 1967-04-26 US US633716A patent/US3494788A/en not_active Expired - Lifetime
-
1968
- 1968-03-26 GB GB14485/68A patent/GB1200237A/en not_active Expired
- 1968-04-01 SE SE04317/68A patent/SE362908B/xx unknown
- 1968-04-24 FR FR1561732D patent/FR1561732A/fr not_active Expired
- 1968-04-25 DE DE19681769249 patent/DE1769249A1/de active Pending
- 1968-04-25 BE BE714228D patent/BE714228A/xx not_active IP Right Cessation
- 1968-04-26 AT AT408068A patent/AT284781B/de not_active IP Right Cessation
- 1968-04-26 NL NL6805943A patent/NL6805943A/xx unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2588365A (en) * | 1949-11-10 | 1952-03-11 | Dow Corning | Method of rendering fabrics waterrepellent and product resulting therefrom |
| US2588366A (en) * | 1950-03-09 | 1952-03-11 | Dow Corning | Method of rendering fabrics waterrepellent and composition therefor |
| US2914836A (en) * | 1957-06-25 | 1959-12-01 | Dow Corning | Method of making synthetic pile fabrics |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030228419A1 (en) * | 2002-06-05 | 2003-12-11 | Byrne Christopher Michael | Silicone compositions for textile applications |
| US6733840B2 (en) * | 2002-06-05 | 2004-05-11 | General Electric Company | Silicone compositions for textile applications |
Also Published As
| Publication number | Publication date |
|---|---|
| BE714228A (ru) | 1968-10-25 |
| FR1561732A (ru) | 1969-03-28 |
| DE1769249A1 (de) | 1970-10-29 |
| AT284781B (de) | 1970-09-25 |
| GB1200237A (en) | 1970-07-29 |
| SE362908B (ru) | 1973-12-27 |
| NL6805943A (ru) | 1968-10-28 |
| CH615968D (ru) | 1900-01-01 |
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