GB2075040A - Organopolysiloxane Compositions - Google Patents
Organopolysiloxane Compositions Download PDFInfo
- Publication number
- GB2075040A GB2075040A GB8110640A GB8110640A GB2075040A GB 2075040 A GB2075040 A GB 2075040A GB 8110640 A GB8110640 A GB 8110640A GB 8110640 A GB8110640 A GB 8110640A GB 2075040 A GB2075040 A GB 2075040A
- Authority
- GB
- United Kingdom
- Prior art keywords
- composition
- organopolysiloxane
- emulsion
- aqueous
- carbon atoms
- 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
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
-
- 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
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/503—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms without bond between a carbon atom and a metal or a boron, silicon, selenium or tellurium atom
-
- 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
- D06M13/50—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with organometallic compounds; with organic compounds containing boron, silicon, selenium or tellurium atoms
- D06M13/51—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond
- D06M13/513—Compounds with at least one carbon-metal or carbon-boron, carbon-silicon, carbon-selenium, or carbon-tellurium bond with at least one carbon-silicon bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Inorganic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
An aqueous composition for the treatment of fibrous materials, particularly textile fibres such as cotton and synthetics, to impart properties such as soft handle and crease resistance consists of an aqueous emulsion of an organopolysiloxane together with an amino-substituted silane, zinc acetate and triethanolamine titanate.
Description
SPECIFICATION
Organopolysiloxane Compositions
This invention relates to aqueous compositions which are particularly adapted to the treatment of fibrous materials.
The treatment of fibrous materials with organopolysiloxane compositions has been carried out on a commercial scale for many years.
Among the desirable properties which can be obtained by such treatments are water repellency, lubricity, improved handle and dimensional stability. Usually, treatment of the fibrous material, for example a textile fabric or a sewing thread, has been carried out by passing the material through a solution or emulsion containing the organopolysiloxane and thereafter drying the treated fabric. Another method, which is better suited to the treatment of made up goods, involves immersing the goods in an emulsion of the organopolysiloxane for a time sufficient to allow the siloxane to become deposited on the fibres; see for example U.K.
Specification No. 802 540. Prior methods of carrying out this so-called 'substantive' or 'exhaust' treatment have not, however, been totally satisfactory. In some cases not all of the organopolysiloxane content of the treating emulsion is deposited on the fibres, that is the bath does not become completely exhausted. This results in a certain degree of wastage of organopolysiloxane. In other cases, even though substantially complete exhaustion may take place the treated fibres may not possess all of the potential desirable properties.
According to this invention there is provided an aqueous treating composition which comprises (i) an aqueous emulsion of one or more organopolysiloxanes (ii) a silane of the general formula
wherein R represents a hydrogen atom, an alkyl group having from 1 to 6 inclusive carbon atoms or a group composed of carbon, hydrogen and nitrogen which contains at least one -NH2 group, R' represents a divalent hydrocarbon radical having from 1 to 1 2 inclusive carbon atoms, X represents an alkyl, alkoxyalkyl or aminoalkyl group, said groups having from 1 to 6 inclusive carbon atoms, Y represents an alkyl group having from 1 to 4 inclusive carbon atoms and a has a value of 1, 2 or 3, (iii) zinc acetate and (iv) triethanolamine titanate.
The invention also includes a process for the treatment of fibrous materials which comprises contacting the said fibrous materials with the hereinabove-specified aqueous composition.
The organopolysiloxanes present in the aqueous composition of this invention may be any of those which find application in the treatment of fibrous materials to impart thereto such
properties as water repellency, lubricity, crease
resistance and soft handle. Such organopolysiloxanes are generally the polydiorganosiloxanes, that is organopolysiloxanes having on average about two organic groups per silicon atom. The organopolysiloxane may, however, comprise a poly(alkylhydrogen) siloxane either alone or in conjunction with, for example, a polydiorganosiloxane. As the organic substituents there may be present in the organopolysiloxane monovalent hydrocarbon groups such as alkyl e.g.
methyl, ethyl, butyl, and 2,4,4-trimethylpentyl, alkenyl e.g. vinyl and aryl e.g. phenyl, monovalent substituted hydrocarbon groups e.g. chlorophenyl, trifluoropropyl and carboxyalkyl. The generally preferred organopolysiloxanes are those in which at least about 80 per cent of the total siliconbonded substituents are methyl groups. Examples of organopolysiloxanes which may be present in the compositions of this invention are polydimethylsiloxanes, copolymers of dimethylsiloxane units and methylvinylsiloxane units and copolymers of dimethylsiloxane units and phenylmethylsiloxane units. The organopolysiloxanes may be chain-terminated with silanol groups or with organosiloxy groups, for example trimethylsiloxy groups, dimethyl(hydrogen)siloxy groups, methylphenylvinylsiloxy groups and methyl(dimethoxy)siloxy groups.Preferred as organopolysiloxanes for use according to this invention are the polydimethylsiloxanes, either employed alone or in conjunction with other siloxane polymers such as the poly( methylhydrogen)siloxanes.
The aqueous emulsion of the organopolysiloxane may be prepared employing any suitable techniques and emulsifying agents.
For example, the the emulsion may be obtained by mixing the organopolysiloxane, water and one or more emulsifying agents and passing the mixture through a homogeniser, e.g. a. colloid mill. More preferably the emulsion may be prepared by mixing the organopolysiloxane, emulsifying agent and some of the water and thereafter diluting the thick phase so obtained with the remainder of the water. Yet another method of preparing the organopolysiloxane emulsion is by emulsion polymerisation as described, for example, in U.K. Patents Nos.
1 024 024 and 1 039 460.
Suitable emulsifying agents for the preparation of aqueous organopolysiloxane emulsions are weli-known in the art. For most applications it is preferred to employ the non-ionic emulsifying agents but the cationic and anionic types may also be used. Specific examples of such emulsifying agents are esters of fatty acids and polyhydric alcohols e.g. glycerol monostearate, sorbitan monostearate, sorbitan sesquioleate, sorbitan tristearate and sorbitan monolaurate, monoesters of ethylene glycols and propylene glycols and fatty acids e.g. diethylene glycol monolaurate, tetraethyleneglycol monooleate, propylene glycol monostearate, propylene glycol monolaurate and ethoxylated fatty acids such as lauric acid, palmitic acid and stearic acid, ethoxylated fatty alcohols in which the alcohol is cetyl stearyl or olelyl alcohol and ethoxylated alkyl phenols e.g. the polyethoxyethers of octyl phenol and nonyl phenol, ethoxylated amines and their salts, the acetates of primary amines e.g.
octadecylamine acetate, the alkyl aryl sulphonates, alkyl sulphates e.g. sodium lauryl sulphate, and polyvinyl alcohol. In addition to the emulsifying agents the emulsions may also contain stabilisers for example methyl cellulose and carboxymethyl cellulose. The emulsifying agents can be employed in conventional proportions, generally from 1 to 15% by weight based on the weight of the organopolysiloxane.
In the general formula of the silanes which constitute component (ii) of the compositions of this inventions R may represent a hydrogen atom, a C16 alkyl group e.g. methyl, ethyl or amyl, or a group composed of carbon, hydrogen and nitrogen which contains at least one -NH2 group.Examples of the operative R groups therefore are -CH2CH2NH2, -CH2CH2NH CH2CH2NH2 and
The diva lent group R' may be for example -CH2-, -(CH2)4- or -(CH2)5-. The preferred silanes (ii), however, are those in which
R represents -CH2CH2NH2 and
R' represents -(CH2)3 or -CH2CH CH3CH2-. Preferably also a is 2 or 3 and X represents the methyl or ethyl groups but it
may if desired represent any other alkyl, alkoxyalkyl or aminoalkyl group having from 1 to
6 inclusive carbon atoms, for example butyl,
methoxyethyl or aminopropyl. The group Y, when present, may be methyl, ethyl, propyl or butyl.
Examples of the preferred silanes for use in the
compositions of this invention are H2NCH2CH2NH(CH2)3Si(OCH3)3 and
H2NCH2CH2NHCH2CH.(CH3) CH2Si (OCH3)3.
The proportion of the silane (ii) employed is not narrowly critical and may vary between about 0.2 parts and 10 parts by weight per 100 parts by weight of organopolysiloxane in the emulsion.
Components (iii) and (iv) of the compositions are each preferably employed in proportions of from about 0.2 parts to 1 5 parts by weight per
100 parts by weight of organopolysiloxane in the emulsion.
The aqueous compositions of this invention are
conveniently prepared by emulsifying the
organopolysiloxane and thereafter adding (ii), (iii)
and (iv) to the preformed emulsion. If desired the
silane, zinc acetate and triethanolamine titanate can be incorporated separately into the organopolysiloxane emulsion, either per se or as solutions in water or other suitable solvent. More conveniently, however, solutions of these three components can be mixed, employing a mutual solvent, if necessary, in the desired proportions prior to addition to the emulsion.In addition to the essential components (i)-(iv) the compositions of this invention may contain other,
ingredients for achieving certain effects or imparting certain properties to the treated fibres, for example waxes such as mineral and polyethylene waxes for improving lubricity, and siloxane curing catalysts, for example organic tin compounds such as dibutyltin dilaurate and dibutyltin dioctoate.
The aqueous compositions of this invention may be used for the treatment of a variety of fibrous materials by the exhaustion technique to impart to the materials desirable properties such as lubricity, water repellency and soft handle. The fibres may be for example of cotton, polyester, polyamide (nylon), wool, acrylic and acetate and mixtures thereof. They may be treated in any form, for example as filaments, sewing threads, piece goods, finished garments and as random fibres such as are employed as filling materials (fibrefill) for pillows and the like. When the organopolysiloxane comprises both a polydimethylsiloxane and a poly(alkylhydrogen)siloxane the aqueous compositions are particularly suitable for imparting to cotton and synthetic textile fibres an improved ability to recover from crushing and creasing.
The liquor to goods ratio employed to treat fibres according to this invention is not critical and may vary for example from 10:1 to 60:1.The concentration of organopolysiloxane present in the aqeuous treating composition will depend on the desired add-on of organopolysiloxane to the fibres and can readily be calculated by known procedures. For most applications the proportion of organopolysiloxane is adjusted to provide for an add-on of from about 0.5% to 7.5% by weight' based on the weight of the fibres. It is to be understood, however, that the treating process of this invention is not limited to the case in which all of the organopolysiloxane present in the treating composition is exhausted in a single treating operation.
Deposition of the organopolysiloxane on the fibres is indicated by clearing of the treating emulsion and can be followed if desired by light transmission measurements. The temperature of the treating composition is not critical but it is generally preferred to employ temperatures in the range from about 200C to about 700C.
Following immersion in the aqueous treating liquor the fibres are normally dried by exposure to normal ambient or elevated temperatures e.g.
from about 1 5 to 1 50 0C. Depending on the properties desired and the nature of the organopolysiloxane the treated fibres may be subjected to further treatment at normal or elevated temperatures to effect curing of the organopolysiloxane.
The following examples in which the parts are expressed by weight illustrate the invention.
Example 1
An aqueous emulsion containing 35% by weight of a trimethylsiloxy-terminated polydimethylsiloxane (viscosity=12,500 cS at 250C) was prepared by the emulsion polymerisation of low molecular weight methyl siloxanes. To this emulsion (100 parts) was then added with stirring H2NCH2CH2NH(CH2)3Si(OMe)3 (0.3 parts).
To a portion of the silane-containing emulsion
(3 parts) was added an aqueous solution (0.2
parts) containing both zinc acetate (11.2% by
weight) and triethanolamine titanate (50% by weight) and the resulting composition made up to 2000 parts by the addition of water. The temperature of the composition was then raised to 250C and pieces of woven nylon fabric (100
parts) immersed therein with periodic agitation.
After about 20 minutes the treating composition had become clear, indicating substantially complete deposition of the polydimethylsiloxane on to the fabric.
Similar results were obtained when the process was repeated using polyester fabric in place of nylon.
Example 2
The procedure of Example 1 was repeated except that the starting emulsion contained 18% by weight of the trimethylsiloxy-terminated polydimethylsiloxane (viscosity=12,500 cS at 25"C) and 10% by weight of a hydrocarbon wax, the emulsifying agent being an alkyl phenoi ethoxylate. The composition was employed to treat an equal weight of polyester sewing thread in place of the nylon fabric. The aqueous treating composition became clear in about 20 minutes indicating substantially complete deposition of the polydimethylsiloxane and wax on the thread.
Example 3
A 35% by weight aqueous emulsion of a hydroxy-terminated polydimethylsiloxane (viscosity 5000 cS at 250C) was prepared by a conventional technique employing a trimethylnonyl ether of polyethylene glycol (Tergitol TMN 6) as the emulsifying agent. This emulsion was used to prepare an aqueous treating composition as described for the starting emulsion in Example 1 except that the amount of the amino silane component was increased to 0.6 parts. The pH of the solution was adjusted to 5.5 using acetic acid and the temperature of the treating bath raised to 450C.
Pieces of scoured cotton fabric (100 parts) were immersed in the treating solution with periodic agitation. After about 20 minutes the composition had become clear indicating substantially complete deposition of the polydimethylsiloxane on to the fabric.
Similar results were obtained when the procedure was repeated with the cotton fabric replaced with an equal weight of cottonpolyester, polyester, or nylon fabric. Similar results were also obtained when the silane was replaced with an equal weight of H2NCH2CH2NH(CH2)3Si(CH3)(oCH3)2 Example 4
To a 35% by weight aqueous emulsion (100 parts) of a hydroxy-terminated polydimethylsiloxane (viscosity 5000 cS at 250C) prepared employing a trimethylnonyl ether of a polyethylene glycol (Tergitol TMN 6) as emulsifying agent was added with stirring
H2NCH2CH2NH(CH2)3Si(OCH3)3 (0.3 part). A portion (3 parts) of the resulting composition was then mixed with a 35% by weight aqueous emulsion (0.5 part) of polymethylhydrogen siloxane (M.Wt.
approximately 2400), a 20% by weight aqueous emulsion (0.2 part) of dibutyltin bis(laurylmercaptide), zinc acetate (0.22 part) and triethanolamine titanate (0.1 part). The resulting composition was then made up to 2,000 parts by the addition of water.
The temperature of the diluted treating composition prepared as above was raised to 250C and pieces of woven nylon fabric (100 parts) immersed therein with periodic agitation.
After about 20 minutes the treating composition had become clear. The fabric was removed and placed in an air circulating oven at 1 500C for 5 minutes to effect drying of the fabric and cure of the siloxane.
The crease recovery angle of the treated fabric was measured according to British Standard
Specification BS 3086. A value of 1520 was obtained compared with 1050 for the untreated fabric.
Example 5
The procedure described in Example 4 was repeated except that the aqueous emulsion of hydroxy-terminated polydimethylsiloxane had been prepared by emulsion polymerisation and the polydimethylsiloxane contained in the emulsion had a viscosity of about 150,000 cS at 250C.
The woven nylon fabric employed had a crease recovery angle of 1140 in the untreated state.
After treatment the crease recovery angle was
1600.
Similar results were obtained when the silane was replaced with an equal quantity of H2NCH2CH2NH(CH2)3Si(CH3)(0CH3)2.
Claims (10)
1. An aqueous treating composition which comprises (i) an aqueous emulsion of one or more organopolysiloxanes, (ii) a silane of the general formula
wherein R represents a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms or a group composed of carbon, hydrogen and nitrogen which contains at least one -NH2 group, R' represents a divalent hydrocarbon radical having from 1 to 12 inclusive carbon atoms, X represents an alkyl, alkoxyalkyl or aminoalkyl group, said groups having from 1 to 6 inclusive carbon atoms,
Y represents an alkyl group having from 1 to 4 inclusive carbon atoms and a has a value of 1,2 or 3, (iii) zinc acetate and (iv) triethanolamine titanate.
2. A composition as claimed in Claim 1 wherein the organopolysiloxane is a polydiorganosiloxane wherein at least 80 per cent of the total organic substituents are methyl groups.
3. A composition as claimed in Claim 1 wherein the organopolysiloxane comprises a polydimethylsiloxane, a poly(methyl hydrogen)siloran e or both.
4. A composition as claimed in any one of the preceding claims wherein the organopolysiloxane emulsion (i) is prepared employing one or more non-ionic emulsifying agents.
5. A composition as claimed in any one of the preceding claims wherein R' represents the -(CH2)3 or-CH2CH.CH3CH2- groups and R represents -CH2CH2NH2.
6. A composition as claimed in any one of the preceding claims wherein a is 2 or 3.
7. A composition as claimed in Claim 1 substantially as described with reference to the
Examples.
8. A process for the treatment of a fibrous material which comprises immersing said fibrous material in an aqueous composition as claimed in any one of the preceding claims and thereafter removing the fibrous material from the treating liquid and drying it.
9. A process as claimed in Claim 8 wherein the treated fibrous material is subjected to further treatment to effect cure of the organopolysiloxane deposited thereon.
10. Treated fibrous materials whenever obtained by the process claimed in Claim 8 or
Claim 9.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8110640A GB2075040B (en) | 1980-04-08 | 1981-04-06 | Organopolysiloxane compositions |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8011597 | 1980-04-08 | ||
| GB8110640A GB2075040B (en) | 1980-04-08 | 1981-04-06 | Organopolysiloxane compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2075040A true GB2075040A (en) | 1981-11-11 |
| GB2075040B GB2075040B (en) | 1983-11-23 |
Family
ID=26275100
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8110640A Expired GB2075040B (en) | 1980-04-08 | 1981-04-06 | Organopolysiloxane compositions |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB2075040B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039783A2 (en) * | 1980-04-16 | 1981-11-18 | Chemische Fabrik Pfersee GmbH | Process for the stabilisation of the dimensions of plane textile materials |
| EP0057937A2 (en) * | 1981-02-10 | 1982-08-18 | Wacker-Chemie GmbH | Process for impregnating organic fibers |
| FR2514014A1 (en) * | 1981-10-03 | 1983-04-08 | Dow Corning Ltd | PROCESS FOR THE PREPARATION OF ORGANOSILOXANES COMPRISING QUATERNARY AMMONIUM SUBSTITUENTS AND REACTIVE SILICON-RELATED SUBSTITUENTS |
| EP0143541A1 (en) * | 1983-10-31 | 1985-06-05 | Toray Silicone Company Limited | Method for producing silicone aqueous emulsion compositions |
| US4541936A (en) * | 1983-09-16 | 1985-09-17 | Toray Silicone Company, Ltd. | Method and siloxane composition for treating fibers |
| EP0201284A2 (en) * | 1985-05-02 | 1986-11-12 | Dow Corning Corporation | Silicone water-based caulking material |
| WO2003038023A1 (en) * | 2001-10-26 | 2003-05-08 | Unilever Plc | Care booster composition for supplementing the performance of laundry compositions |
| US20170121535A1 (en) * | 2014-10-15 | 2017-05-04 | Wacker Chemie Ag | Compositions of aminosiloxanes, alkoxysilicon compounds and metal carboxylates |
-
1981
- 1981-04-06 GB GB8110640A patent/GB2075040B/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039783A2 (en) * | 1980-04-16 | 1981-11-18 | Chemische Fabrik Pfersee GmbH | Process for the stabilisation of the dimensions of plane textile materials |
| EP0039783A3 (en) * | 1980-04-16 | 1982-08-11 | Chemische Fabrik Pfersee GmbH | Process for the stabilisation of the dimensions of plane textile materials |
| EP0057937A2 (en) * | 1981-02-10 | 1982-08-18 | Wacker-Chemie GmbH | Process for impregnating organic fibers |
| EP0057937A3 (en) * | 1981-02-10 | 1982-09-01 | Wacker-Chemie Gmbh | Process for impregnating organic fibers |
| FR2514014A1 (en) * | 1981-10-03 | 1983-04-08 | Dow Corning Ltd | PROCESS FOR THE PREPARATION OF ORGANOSILOXANES COMPRISING QUATERNARY AMMONIUM SUBSTITUENTS AND REACTIVE SILICON-RELATED SUBSTITUENTS |
| US4541936A (en) * | 1983-09-16 | 1985-09-17 | Toray Silicone Company, Ltd. | Method and siloxane composition for treating fibers |
| EP0143541A1 (en) * | 1983-10-31 | 1985-06-05 | Toray Silicone Company Limited | Method for producing silicone aqueous emulsion compositions |
| AU575868B2 (en) * | 1983-10-31 | 1988-08-11 | Toray Silicone Co. Ltd. | Method of producing a silicone emulsion |
| EP0201284A2 (en) * | 1985-05-02 | 1986-11-12 | Dow Corning Corporation | Silicone water-based caulking material |
| EP0201284A3 (en) * | 1985-05-02 | 1987-09-02 | Dow Corning Corporation | Silicone water-based caulking material |
| WO2003038023A1 (en) * | 2001-10-26 | 2003-05-08 | Unilever Plc | Care booster composition for supplementing the performance of laundry compositions |
| US20170121535A1 (en) * | 2014-10-15 | 2017-05-04 | Wacker Chemie Ag | Compositions of aminosiloxanes, alkoxysilicon compounds and metal carboxylates |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2075040B (en) | 1983-11-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |