EP0255205A2 - Treating composition comprising organopolysiloxane containing polyoxyalkylene and alkoxysilylalkyl radicals - Google Patents
Treating composition comprising organopolysiloxane containing polyoxyalkylene and alkoxysilylalkyl radicals Download PDFInfo
- Publication number
- EP0255205A2 EP0255205A2 EP87304333A EP87304333A EP0255205A2 EP 0255205 A2 EP0255205 A2 EP 0255205A2 EP 87304333 A EP87304333 A EP 87304333A EP 87304333 A EP87304333 A EP 87304333A EP 0255205 A2 EP0255205 A2 EP 0255205A2
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- EP
- European Patent Office
- Prior art keywords
- radical
- value
- organopolysiloxane
- denotes
- composition
- 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.)
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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
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
Abstract
Description
- The present invention relates to an agent for treating solids. More specifically, the present invention relates to a treatment agent which imparts a durable hydrophilicity and antistaticity to solid materials.
- In order to impart hydrophilicity and antistaticity to solids such as, for example, moldings, sheet-form materials, foams, fibers, and powders, treatments have heretofore been carried out using various organic surfactants, for example, cationic types,, anionic types, and nonionic types, etc.
- Furthermore, organopolysiloxane-polyoxyalkylene copolymer, such as that disclosed in Japanese Patent Publication Number 44-6069 (6,069/69), and organosilyl-terminated polyoxyalkylene-modified and alkoxysilylalkyl-modified organopolysiloxane, such as that disclosed in Japanese Patent Application Laid Open Number 57-139123 (139,123/82), are known as silicone-type agents for the treatment of solids.
- However, treatment methods which employ organic surfactant and the treatment method using the organopolysiloxane-polyoxyalkylene copolymer as described in Japanese Patent Publication Number 44-6069 suffer from the problem of providing only a temporary hydrophilicity and antistaticity, and these effects are readily lost upon exposure to water or organic solvent.
- While the silicone-type surfactant described in Japanese Patent Application Laid Open Number 57-139123 has the alkoxysilyl alkyl group as a side chain, an agent for treating solids whose principal agent is organopolysiloxane having at least 1 polyoxyalkylene group as a side chain or molecular terminal and having the alkoxysilylalkyl group at least at one molecular terminal, is unknown.
- The object of the present invention is to eliminate the problems described above by providing a novel agent for treating solids which can impart a durable hydrophilicity and antistaticity to solids. It is a particular object of this invention to provide a method for conferring durable hydrophilicity and antistaticity properties to fibers and fiber-containing materials.
- These objects, and others which will become apparent upon consideration of the following disclosure and appended claims, are obtained by the method of this invention which, briefly stated, comprises treating a solid material with a composition which comprises, as its principal component, an organopolysiloxane compound which contains at least one siloxane chain-terminating siloxane unit bearing an alkoxysilylalkyl radical and at least one siloxane unit bearing a polyoxyalkylene radical. In a preferred embodiment of this invention both of the siloxane chain-terminating siloxane units bear alkoxysilylalkyl radical.
- The present invention relates to a composition for treating solids, said composition comprising an organopolysiloxane compound which has the formula
A(R₂SiO)x(RQSiO)y(RGSiO)zSiR₂A, wherein
Q denotes a radical having the formula
-R¹SiXaR(3-a),
G denotes a radical having the formula
-R¹O(C₂H₄O)b(C₃H₆O)cR²,
A denotes a radical selected from the group consisting of Q and G radicals, at least one A radical being a Q radical,
x has a value of from 5 to 500,
y has a value of from 0 to 100,
z has a value of from 0 to 100,
X denotes an alkoxy or alkoxyalkoxy radical having from 1 to 4 carbon atoms,
R denotes a monovalent hydrocarbon or halogenated hydrocarbon radical having from 1 to 10 carbon atoms,
R¹ denotes an alkylene radical having from 2 to 5 carbon atoms,
R² denotes a hydrogen atom or a monovalent organic radical having from 1 to 5 carbon atoms,
a has a value of 2 or 3,
b has a value of from 0 to 50,
c has a value of from 0 to 50, and
b plus c has a value of from 2 to 100;
there being present in said organopolysiloxane at least one G radical. - By way of explanation of the preceding, R in the above formulas is a monovalent hydrocarbon group having 1 to 10 carbon atoms, and it is exemplified by alkyl groups such as methyl, ethyl, propyl, and octyl; by substituted alkyl groups such as 3,3,3-trifluoropropyl, 2-phenylethyl and 2-phenylpropyl; by aryl groups such as phenyl and tolyl; and by substituted aryl groups. Alkyl groups, most preferably methyl, are preferred here. The groups R in a single molecule may be identical or different.
- A can be a Q or G group, delineated below, with the proviso that at least one A is a Q group. Preferably all A groups are Q groups.
- Q is a group having the formula -R¹SiXaR(3-a) and it functions to impart durability by tightly bonding the present organopolysiloxane to solids. R¹ is to be an alkylene group having 2 to 5 carbon atoms, and is exemplified by -CH₂CH₂-, -CH₂CH₂CH₂-, -CH(CH₃)CH₂-, -(CH₂)₄-, and -(CH₂)₅-. The groups R¹ within the molecule may be identical or different. X is an alkoxy group having 1 to 4 carbon atoms, and it is exemplified by methoxy, ethoxy, propoxy, and methoxyethoxy.
- The value of ª is to be 2 or 3.
- G is a group having the formula -R¹O(C₂H₄O)b(C₃H₆O)cR², and it functions to impart antistaticity and hydrophilicity to the solid. R² is to be the hydrogen atom or a monovalent organic group having 1 to 5 carbon atoms, and said monovalent hydrocarbon groups are exemplified by alkyl groups such as methyl, ethyl, and propyl, and by acyl groups such as acetyl and propionyl. In each G group b and c are both integers having values of 0 to 50 wherein the sum b + c is to have a value of 2 to 100.
- In the organopolysiloxane x is an integer having a value of 5 to 500, y is an integer having a value of 0 to 100, and z is an integer having a value of 0 to 100, with the condition that when A consists entirely of Q, z is then to be an integer having a value of 1 to 100. When x is 50, lubricity will also be imparted to the solid.
- The organopolysiloxane to be used in the present invention can be synthesized, for example, by addition reacting diorganohydrogensilyl-terminated diorganosiloxane-organohydrogensiloxane copolymer with alkoxysilyl group-containing alkene and alkenyl-substituted polyoxyalkylene compound, the latter two being used in the appropriate ratio, under the catalytic activity of a platinum-type catalyst such as chloroplatinic acid. Further synthesis details are disclosed in the examples below.
- With regard to the use of the present invention's agent for treating solids, the above-described organopolysiloxane can be used as is, or it may be dissolved in water as is, or it may be auto-emulsified in water. Alternatively, it may be emulsified using a suitable emulsifying agent such as, for example, the salts of sulfate esters of higher alcohols, alkylbenzenesulfonate salts, higher alcohol-polyoxyalkylene adducts, alkylphenol-polyoxyalkylene adducts, higher fatty acid sorbitan esters, etc.
- Alternatively, the solid treatment agent of the present invention may be used by dissolving the above-described organopolysiloxane in an organic solvent such as, for example, toluene, xylene, benzene, n-hexane, heptane, acetone, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, mineral terpene, perchloroethylene, trichloroethylene, etc.
- Solids may be treated with the treatment agent of the present invention by methods such as spraying, roll coating, brush coating, immersion, etc. While the quantity of adhesion will vary with the type of solid and so cannot be strictly specified, it will generally be 0.01 to 10.0 wt % based on the solid. After application, a durable hydrophilicity and antistaticity will be imparted to the solid, for example, upon standing at room temperature, or upon blowing on hot air, or upon a heat treatment.
- Furthermore, treatment may be conducted using the treatment agent of the present invention in combination with the metal salts of organic acids, for example, their zinc, tin, zirconium, etc., salts such as zinc stearate, zinc oleate, dibutyltin diacetate, dibutyltin dioleate, dibutyltin dilaurate; zirconium stearate; and/or amino-containing alkoxysilanes, epoxy-containing alkoxysilanes, organohydrogenpolysiloxanes, silanol-containing organopolysiloxanes; etc.
- Solids which may be treated with the treatment agent of the present invention are exemplified by various fibers and their fabrics; sheet-form materials such as paper, natural and synthetic leathers, cellophane and plastic films; foams such as synthetic resin foams; synthetic resin moldings; natural and synthetic rubber moldings; metal moldings; glass moldings; and powders such as inorganic powders and synthetic resin powders.
- The aforesaid fibers are exemplified in terms of species by natural fibers such as hair, wool, silk, flax, cotton and asbestos; by regenerated fibers such as rayon and acetate; by synthetic fibers such as polyester, polyamide, vinylon, polyacryl nitrile, polyethylene, polypropylene and spandex; and by glass fibers; carbon fibers; and silicon carbide fibers. They are exemplified in terms of form by the staple, filament, tow, and yarn. Their fabrics are exemplified by knits, nonwovens, resin-finished fabrics, and sewn articles thereof.
- The invention will be explained in the following using illustrative examples. In the examples and reference examples, parts = weight parts and % = weight %, and the viscosity is the value measured at 25°C.
- Vinyltrimethoxysilane, 148.2 g, is placed in a three-neck 500 ml flask equipped with a reflux condenser, the internal temperature is raised to 60°C by heating, 0.15 g 2% isopropanolic chloroplatinic acid solution is added, and 51.8 g tetramethyldisiloxane is dripped in. Organosiloxane I having the following formula is obtained by a reaction at 100°C for 2 hours and distillation in vacuo at 140°C/5 mmHg.
- (CH₃O)₃SiCH₂CH₂Si(CH₃)₂OSi(CH₃)₂CH₂CH₂(OCH₃)₃ Organosiloxane I, 61.4 g, methylhydrogensiloxane cyclic tetramer, 59.8 g, cyclic dimethylsiloxane tetramer, 368.9 g, and 15 g thoroughly dried activated clay as polymerization catalyst are placed in a three-neck 500 ml flask equipped with a reflux condenser, and polymerized at 75°C for 10 hours. After cooling, filtration is conducted using an assistant.
- Exactly 136.9 g of this organopolysiloxane product, 13.4 g vinyltrimethoxysilane, 149.7 g allyl-containing polyether having the following formula CH₂=CHCH₂O(CH₂CH₂O)₁₂CH₃ and 90 g toluene are placed in a 500 ml three-neck flask equipped with a reflux condenser, the internal temperature is raised to 60°C by heating, 0.38 g 2% isopropanolic chloroplatinic acid solution is added, and a reaction is then carried out at 120°C for 2 hours. After the completion of the reaction, the volatiles are stripped in vacuo. The product is identified by infrared absorption spectral analysis and nuclear magnetic resonance analysis as an organopolysiloxane (Organopolysiloxane A, viscosity = 305 cS) having the following formula:
- Siloxane II, 89.1 g, having the formula
H(Me₂SiO)₄₁(MeHSiO)₆SiMe₂H,
7.5 g vinyltrimethoxysilane, and 60 g toluene are placed in a 500 ml three-neck flask equipped with a reflux condenser, the internal temperature is raised to 80°C by heating, 0.1 g 2% isopropanolic chloroplatinic acid solution is added, and a reaction is conducted at 110°C for 30 minutes. After cooling to 80°C, 103.4 g allyl-containing polyether I having the formula CH₂=CHCH₂O(CH₂CH₂O)₁₂H is added, the temperature is raised to 90°C, 0.15 g 2% isopropanolic chloroplatinic acid solution is added, and a reaction is conducted at 120°C for 1 hour. After the end of the reaction, the volatiles are stripped in vacuo at 140°C/5 mmHg. Infrared absorption spectral analysis and nuclear magnetic resonance analysis confirm the product to be an organopolysiloxane (Organopolysiloxane B, viscosity = 1,100 cS) having the following formula: - A siloxane, 69.3 g, having the formula
H(Me₂SiO)₂₀(MeHSiO)₄SiMe₂H,
11.0 g methylvinyldimethoxysilane and 60 g toluene are placed in a 500 ml three-neck flask equipped with a reflux condenser, the internal temperature is raised to 80°C by heating, 0.1 g 2% isopropanolic chloroplatinic acid solution is added, and a reaction is carried out for 30 minutes at 105°C. After cooling to 80°C, 119.7 g allyl-containing polyether having the formula CH₂=CHCH₂O(C₂H₄O)₈(C₃H₆O)₄H is added, the temperature is raised to 90°C, 0.15 g 2% isopropanolic chloroplatinic acid solution is added, and a reaction is conducted at 120°C for 1 hour. After the end of the reaction, the volatiles are stripped in vacuo at 140°C/5 mmHg. Infrared absorption spectral analysis and nuclear magnetic resonance analysis confirm the product to be an organopolysiloxane (Organopolysiloxane C, viscosity = 500 cS) having the following formula: - Siloxane II, as used in Reference Example 2, 89.1 g vinyltrimethoxysilane, 7.5 g, allyl group-containing polyether I as used in Reference Example 2, 103.4 g, and 60 g toluene are placed in a three-neck 500 ml flask equipped with a reflux condenser, the internal temperature is raised to 80°C by heating, 0.25 g 2% isopropanolic chloroplatinic acid solution is added, and a reaction is conducted at 125°C for 1 hour. After the reaction, the volatiles are stripped in vacuo at 140°C/5 mmHg.
-
- One part of the Organopolysiloxane A synthesized according to Reference Example 1 and having the formula
- In the water absorptivity test, the organopolysiloxane-finished fabric (before and after washing) is laid out horizontally on spread out filter paper, a drop of water is delivered from a syringe, and the time required for its soaking in is then measured.
- To measure the residual organopolysiloxane, the % residual organopolysiloxane after washing is analyzed using an X-ray fluorescent analyzer from Rigaku Corp. based on the difference in silicon atom counts before and after washing the treated fabric. The results are reported in Table 1.
-
- Five parts of Organopolysiloxane B, synthesized according to Reference Example 2 and having the formula
- Both before and after washing, the organopolysiloxane-finished fabric is subjected to the water absorptivity test and testing of the % residual organopolysiloxane as described in Example 1. These results are reported in Table 2.
-
-
-
- Organopolysiloxane A as used in Example 1, 5 parts, is dissolved to homogeneity in 995 parts toluene. A 65% polyester/35% cotton broadcloth (40 x 20 cm), coated with a 3% add-on of the glyoxal-type resin, is then immersed in this solution for 30 seconds, adjusted to an expression ratio of 100% on a mangle, dried by standing at room temperature for 10 hours, and then heated in an oven for 5 minutes at 150°C. The obtained organopolysiloxane-finished fabric is then cut in half, and one sample of organopolysiloxane-finished fabric is washed once under the wash conditions of Example 1 and rinsed twice. Test samples are thus prepared of organopolysiloxane-finished fabric before and after washing.
- An antistaticity test is carried out as follows. The treated fabrics (before and after washing) are allowed to stand at 20°C/RH 65% for 1 week. Their triboelectrification voltages are then measured using a Kyodai Kaken rotary static tester (800 rpm for 60 seconds). Cotton fabric (unbleached muslin #3) is used as the friction fabric.
- A soiling resistance test is conducted as follows. An artificial soilant is prepared by thoroughly mixing and pulverizing 300 g ASTM No. 1 oil, 3 g coal tar, 5 g dried clay powder, 5 g portland cement and 5 g sodium dodecylbenzenesulfonate in a mortar. 5 ml of this artificial soilant, 100 ml of a 0.5% aqueous solution of Marseilles soap and 10 steel balls are placed in a 450 ml glass bottle. Washed and unwashed samples of organopolysiloxane-finished fabric and untreated fabric are respectively placed in the bottle, treated at 60°C for 30 minutes, and then gently rinsed with water and dried. These are then washed for 10 minutes on high in an automatic reversing rotary washing machine using a 0.5% aqueous solution of Marseilles soap. After then washing in water and drying, the reflectance of the test fabrics is measured at a wavelength of 550 millimicrons using a reflectometer. These test results are reported in Table 3.
-
- Organopolysiloxane A as synthesized in Reference Example 1, 10 parts, and 1 part zinc stearate are dissolved to homogeneity in 89 parts water to prepare a treatment solution. This is then applied at an organopolysiloxane add-on of 0.2 g/m² by spraying on one side of a plasma-processed polyethylene terephthalate film. After coating, the film is dried at room temperature overnight and then heated in an oven at 130°C for 10 minutes.
- In the comparison examples, 10% aqueous solutions are prepared using, respectively, Organopolysiloxane (ii) (used in Comparison Example 3) or nonionic surfactant (NS-210 from Nippon Oils and Fats Co., Ltd.), and each is then sprayed on one side of the plasma-processed polyethylene terephthalate film at an add-on of 0.2 g/m², followed by drying and heating.
- The obtained three treated films are immersed in running water for 6 hours. After this, the upper surface of a thermostatted water bath (set at 60°C ± 2°C) is covered and sealed with each film, wherein the treated surface is down. The status of the films is inspected after 3 hours. The film treated with Organopolysiloxane A, a treatment agent of the present invention, is hydrophilic, presents uniform wetting of the lower film surface, and is transparent. However, the lower surfaces of the other 2 films are not hydrophilic, and are adhered with water droplets and are opaque.
- A 0.5% aqueous solution of Organopolysiloxane D, 100 g, (synthesized in Reference Example 4) is prepared, 50 g carbon black powder is added, and this mixture is allowed to dry by standing. Heating at 100°C for 5 minutes then affords a carbon black powder having a 1% add-on of Organopolysiloxane D.
- In the comparison example, carbon black powder is similarly treated with Organopolysiloxane (ii) to afford a carbon black powder having a 1% add-on of Organopolysiloxane (ii).
- 50 g of each carbon black powder is separately placed in 1 l of water, followed by stirring for 3 hours, filtration and drying. 5 Parts of each of the obtained carbon black powders is then separately dispersed to homogeneity in an aqueous acrylic emulsion paint to produce a paint. The paint containing the Organopolysiloxane D-treated carbon black powder presented a uniform dispersion, and did not suffer from sedimentation. However, the Organopolysiloxane (ii)-treated carbon black powder underwent rapid sedimentation, and the dispersion was inhomogeneous. These observations indicate that the present invention's agent for treating solids has the capacity to impart a durable hydrophilicity.
- Because the present invention's agent for treating solids has as its principal agent an organopolysiloxane which has the alkoxysilylalkyl group at least at one molecular terminal and which also has at least 1 polyoxyalkylene group as a pendant group or at the molecular terminals, it can impart a durable hydrophilicity and antistaticity to solid materials. As a consequence, it is very useful industrially.
Claims (7)
Q denotes a radical having the formula
-R¹SiXaR(3-a),
G denotes a radical having the formula
-R¹O(C₂H₄O)b(C₃H₆O)cR²,
A denotes a radical selected from the group consisting of Q and G radicals, at least one A radical being a Q radical,
x has a value of from 5 to 500,
y has a value of from 0 to 100,
z has a value of from 0 to 100,
X denotes an alkoxy or alkoxyalkoxy radical having from 1 to 4 carbon atoms,
R denotes a monovalent hydrocarbon or halogenated hydrocarbon radical having from 1 to 10 carbon atoms,
R¹ denotes an alkylene radical having from 2 to 5 carbon atoms,
R² denotes a hydrogen atom or a monovalent organic radical having from 1 to 5 carbon atoms,
a has a value of 2 or 3,
b has a value of from 0 to 50,
c has a value of from 0 to 50, and
b plus c has a value of from 2 to 100;
there being present in said organopolysiloxane at least one G radical.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP112391/86 | 1986-05-16 | ||
JP11239186A JPS62267359A (en) | 1986-05-16 | 1986-05-16 | Solid material-treating agent |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0255205A2 true EP0255205A2 (en) | 1988-02-03 |
EP0255205A3 EP0255205A3 (en) | 1990-01-10 |
Family
ID=14585495
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP87304333A Withdrawn EP0255205A3 (en) | 1986-05-16 | 1987-05-15 | Treating composition comprising organopolysiloxane containing polyoxyalkylene and alkoxysilylalkyl radicals |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0255205A3 (en) |
JP (1) | JPS62267359A (en) |
CA (1) | CA1293976C (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0510631A1 (en) * | 1991-04-24 | 1992-10-28 | Dow Corning Toray Silicone Company, Limited | Siloxane modified polyester for fibre treatment |
WO1994028229A2 (en) * | 1993-05-27 | 1994-12-08 | Comfort Technologies, Inc. | Polymers having enhanced durable hydrophilicity and durable rewetting properties and process of producing the same |
US6733840B2 (en) | 2002-06-05 | 2004-05-11 | General Electric Company | Silicone compositions for textile applications |
US6863762B2 (en) * | 2000-11-09 | 2005-03-08 | Canon Kabushiki Kaisha | Method for manufacturing fiber aggregate, fiber aggregate, and liquid container using such fiber aggregate |
EP2151420B1 (en) * | 2008-08-05 | 2019-01-23 | Evonik Degussa GmbH | Water repellent treatment for building elements containing mineral fibres |
CN114031780A (en) * | 2021-11-05 | 2022-02-11 | 广州集泰化工股份有限公司 | Antistatic silica gel compound and preparation method and application thereof |
Families Citing this family (3)
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CA2327034C (en) * | 1999-12-01 | 2007-07-17 | Canon Kabushiki Kaisha | Method of reforming element surface, element with reformed surface, method of manufacturing element with reformed surface, surface treatment liquid for forming reformed surface, and method of manufacturing surface treatment liquid |
US6796645B2 (en) * | 1999-12-06 | 2004-09-28 | Canon Kabushiki Kaisha | Surface reformed fiber body, liquid container using fiber absorber, and method of producing fiber absorber for use in liquid ejection |
CN110997840B (en) * | 2017-06-26 | 2021-09-07 | 美国陶氏有机硅公司 | Silicone-polyether copolymers, isocyanate-functionalized silicone-polyether copolymers formed therewith, silicone-polyether-urethane copolymers, sealants including the same, and related methods |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3140198A (en) * | 1961-06-01 | 1964-07-07 | Ici Ltd | Treatment of textile materials |
US4302571A (en) * | 1979-03-16 | 1981-11-24 | Shin-Etsu Chemical Co., Ltd. | Room temperature-curable polyoxyalkylene polyether compositions |
EP0186492A2 (en) * | 1984-12-21 | 1986-07-02 | Toray Silicone Company Limited | Method for treating materials with organopolysiloxane compounds |
-
1986
- 1986-05-16 JP JP11239186A patent/JPS62267359A/en active Pending
-
1987
- 1987-05-15 EP EP87304333A patent/EP0255205A3/en not_active Withdrawn
- 1987-05-15 CA CA000537247A patent/CA1293976C/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3140198A (en) * | 1961-06-01 | 1964-07-07 | Ici Ltd | Treatment of textile materials |
US4302571A (en) * | 1979-03-16 | 1981-11-24 | Shin-Etsu Chemical Co., Ltd. | Room temperature-curable polyoxyalkylene polyether compositions |
EP0186492A2 (en) * | 1984-12-21 | 1986-07-02 | Toray Silicone Company Limited | Method for treating materials with organopolysiloxane compounds |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0510631A1 (en) * | 1991-04-24 | 1992-10-28 | Dow Corning Toray Silicone Company, Limited | Siloxane modified polyester for fibre treatment |
WO1994028229A2 (en) * | 1993-05-27 | 1994-12-08 | Comfort Technologies, Inc. | Polymers having enhanced durable hydrophilicity and durable rewetting properties and process of producing the same |
WO1994028229A3 (en) * | 1993-05-27 | 1995-01-26 | Comfort Tech Inc | Polymers having enhanced durable hydrophilicity and durable rewetting properties and process of producing the same |
US5408012A (en) * | 1993-05-27 | 1995-04-18 | Comfort Technologies, Inc. | Polymers having enhanced durable hydrophilicity and durable rewetting properties and process of producing the same |
US6863762B2 (en) * | 2000-11-09 | 2005-03-08 | Canon Kabushiki Kaisha | Method for manufacturing fiber aggregate, fiber aggregate, and liquid container using such fiber aggregate |
US6733840B2 (en) | 2002-06-05 | 2004-05-11 | General Electric Company | Silicone compositions for textile applications |
EP2151420B1 (en) * | 2008-08-05 | 2019-01-23 | Evonik Degussa GmbH | Water repellent treatment for building elements containing mineral fibres |
CN114031780A (en) * | 2021-11-05 | 2022-02-11 | 广州集泰化工股份有限公司 | Antistatic silica gel compound and preparation method and application thereof |
Also Published As
Publication number | Publication date |
---|---|
JPS62267359A (en) | 1987-11-20 |
CA1293976C (en) | 1992-01-07 |
EP0255205A3 (en) | 1990-01-10 |
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