WO2004108798A1 - Silicone based flame retardant systems for textiles - Google Patents
Silicone based flame retardant systems for textiles Download PDFInfo
- Publication number
- WO2004108798A1 WO2004108798A1 PCT/US2004/017233 US2004017233W WO2004108798A1 WO 2004108798 A1 WO2004108798 A1 WO 2004108798A1 US 2004017233 W US2004017233 W US 2004017233W WO 2004108798 A1 WO2004108798 A1 WO 2004108798A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- accordance
- formula
- cellulose
- polysiloxane
- cross
- Prior art date
Links
Classifications
-
- 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
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/207—Substituted carboxylic acids, e.g. by hydroxy or keto groups; Anhydrides, halides or salts thereof
-
- 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
- D06M2101/00—Chemical constitution of the fibres, threads, yarns, fabrics or fibrous goods made from such materials, to be treated
- D06M2101/02—Natural fibres, other than mineral fibres
- D06M2101/04—Vegetal fibres
- D06M2101/06—Vegetal fibres cellulosic
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/30—Flame or heat resistance, fire retardancy properties
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/01—Silicones
Definitions
- the present invention relates to compositions for textile applications. More particularly, the present invention relates to silicone compositions which adhere durably to textiles and provide flame retardancy.
- Textiles used in the clothing industry must adhere to certain standards before they can be sold. According to government regulations, clothing garments must exhibit a certain level of flame retardancy. Flame retardancy can be achieved by blending fabrics with flame retardant textiles. For example, in many cases cotton is blended with polyester to achieve required levels of flame retardancy. Unfortunately, blending fabrics with flame retardant textiles can have a negative effect on properties of the final textile such as softness. In cases where softness is an issue, flame retardancy can be imparted via treatment with a flame retardant material. For instance, treatment of textiles with phosphorus-based molecules or polycarboxylates that react durable with the fabric can result in flame retardancy of the fabrics. Unfortunately, these treatments often cause an unacceptable loss of fabric strength or require specialized processing equipment.
- the present invention provides a silicone composition
- a silicone composition comprising at least one polysiloxane or siloxane oligomer functionalized with at least one amino group and at least three functional groups capable of cross-linking wherein the polysiloxane or silicone oligomer imparts flame retardancy on a cellulose-containing substrate.
- the present invention provides a method of treating a cellulose-containing substrate comprising (a) wetting the cellulose-containing substrate with an aqueous solution, dispersion, or emulsion of a silicone composition comprising at least one polysiloxane or siloxane oligomer functionalized with an amino group and at least three functional groups capable of cross-linking; and
- the present invention provides a cellulose-containing substrate comprising at least one polysiloxane or siloxane oligomer functionalized with at least one amino group and at least three functional groups capable of cross- linking.
- the present invention includes a silicone composition which includes at least one polysiloxane or siloxane oligomer functionalized with an amine containing group (hereinafter also referred to as "amino group”) and at least three functional groups capable of functioning as cross-linking sites (hereinafter also referred to as "cross- linking precursor").
- the polysiloxane of the present invention imparts flame retardancy to natural fiber/cellulose substrates or substrates containing natural fibers/ cellulose.
- the present invention includes at least one polysiloxane or siloxane oligomer having the formula:
- M' has the formula: (X) h R 2 3-h SiO,/2,
- T has the formula:
- T' has the formula:
- each R 1 , R 2 , R 3 , R 4 , R 5 is independently at each occurrence a cross-linking precursor, hydrogen atom, C 1-30 alkyl, Cj -22 alkoxy, C2.22 alkenyl, C 6- ⁇ 4 aryl, and C 6-22 alkyl-substituted aryl, and C 6-22 aralkyl, any of which groups may be halogenated, for example, fluorinated to contain fluorocarbons such as C 1-22 fluoroalkyl, or may contain polyether units of the formula (CH 2 CHR 6 O) where R 6 is independently in each repeat unit CH 3 or H and "k" is in a range between about 4 and about 50; X, independently at each occurrence, represents an amino group or a cross- linking precursor with the proviso that the polysiloxane or siloxane oli
- the amino group typically is in the form of C ⁇ - 0 aminoalkyls.
- the amino group can contain primary nitrogen groups, secondary nitrogen groups, tertiary nitrogen groups, quaternary nitrogen groups, or any mixture thereof. It may or may not be part of an aliphatic ring structure. It may also consist of or be interrupted by aromatic rings.
- the amino group may contain any number of nitrogen atoms, preferably 1 or 2.
- Preferred amino groups are aminopropyl and aminoethylaminopropyl.
- alkyl as used in various embodiments of the present invention, is intended to designate both normal alkyl, branched alkyl, aralkyl, and cycloalkyl radicals.
- Normal and branched alkyl radicals are preferably those containing in a range between about 1 and about 30 carbon atoms, and include as illustrative non-limiting examples methyl, ethyl, propyl, isopropyl, butyl, tertiary-butyl, pentyl, neopentyl, hexyl, dodecyl, cetyl, and stearyl.
- Cycloalkyl radicals represented are preferably those containing between about 4 and about 12 ring carbon atoms.
- cycloalkyl radicals include cyclobutyl, cyclopentyl, cyclohexyl, methylcyclohexyl, and cycloheptyl.
- Preferred aralkyl radicals are those containing between about 7 and about 14 carbon atoms. These include, but are not limited to, benzyl, phenylbutyl, phenylpropyl, and phenylethyl.
- Aryl radicals used in the various embodiments of the present invention are preferably those containing between about 6 and about 20 ring carbon atoms and contain at least one monocyclic or polycyclic moiety wherein a polycyclic may comprise fused or linked rings.
- aryl radicals include phenyl, biphenyl, and naphthyl.
- An illustrative non-limiting example of a suitable halogenated moiety is trifluoropropyl.
- cross-linking precursor includes any moiety that is capable of providing cross-linking either directly (e.g. hydroxy groups) or indirectly (e.g. alkoxy groups) with other amino functionalized polysiloxanes or siloxane oligomers of the present invention or with added cross- linking compounds containing at least two cross-linking precursors.
- Typical cross- linking precursors include hydroxy groups, alkoxy groups, hydrogen, and electrophilic groups combined with nucleophilic groups. Most typically, the cross- linking precursor is a hydroxy group.
- the number of amino groups on the polysiloxane or siloxane oligomer in the present invention that is capable of imparting flame retardancy to cellulose-containing substrates is at least one, however, all the silicon atoms of the polysiloxane or siloxane oligomer may be substituted with amino groups.
- the average ratio of Si atoms substituted with amino groups to those that are not is in a range between about 1 and about 5.
- the polysiloxane or siloxane oligomer is water soluble or capable of being emulsified.
- the polysiloxanes or siloxane oligomers of the present invention are typically prepared by equilibration reactions containing silanes or oligosilanes substituted with amino groups and cross-linking precursors in the presence of a suitable catalyst, subject to the structural parameters described above.
- the catalyst is preferably a basic catalyst.
- a silicone composition includes a preponderance of specific linear, branched, cross-linked, or cyclic polysiloxanes.
- suitable compositions may comprise one or more polysiloxanes or siloxane oligomers which may contain adventitious amounts of other species at a level in a range between about 0.0001 wt % and about 5 wt % based on total silicon-containing species, for example, arising during the synthesis process for said polysiloxanes or siloxane oligomers.
- suitable compositions may contain adventitious amounts of D 4 , or species containing Si-H, Si-OH, Si-O-alkyl bonds, and mixtures thereof that do not contain amino groups.
- the silicone fabric treatment composition of the present invention may also optionally- include additives such as a catalyst or mixture of catalysts; cross-linking agents; organic compounds; inorganic compounds that contain species such as phosphorus, boron, aluminum, magnesium, or zinc; or combinations thereof with the proviso that the additive or group of additives do not have a negative effect on the flame retardant benefits of the silicone composition.
- the silicone composition may include at least one aluminum compound, such as aluminum lactate.
- the aluminum compound is present in a range between about 0.01% and about 10% by weight based on the silicone composition, and more preferably, in a range between about 0.5% and about 5% by weight based on the silicone composition.
- Catalysts that accelerate curing of the silicone composition on the fabric may also be present.
- the catalyst is present in a range between about 0.0001 weight % and about 10 weight % with respect to silicon in the composition, and preferably, in a range between about 0.001 weight % and about 5 weight % with respect to the total composition.
- cure catalysts include, but are not limited to, organic or inorganic acids and bases.
- Silicone compositions of the present invention that include at least one polysiloxane or siloxane oligomer functionalized with at least one amino group and at least three functional groups capable of cross-linking typically impart flame retardant benefits to materials such as textiles, including cellulose-containing surfaces such as natural fibers and regenerated fibers including blends.
- a particular advantage of the present invention is that the described functional groups enable the silicone composition to adhere durably to a cellulose-containing surface.
- the silicone composition can be applied to the substrate by any method known to those skilled in the art.
- padding processes are typical for textile treatment.
- the substrate is wetted with an aqueous solution, non-aqueous solution, dispersion, or emulsion of the silicone composition.
- the silicone composition can be delivered in a water mixture which can contain the silicone composition in a range between about 0.01% by weight and about 99% by weight based on the total mixture.
- the composition can be cured over a period in a range between about 5 minutes and about 2 hours, and preferably over a period in a range between about 5 minutes and 30 minutes.
- the cure temperature is in a range between about 125DC and about 220DC, preferably in a range between about 150°C and about 200°C.
- the substituted silicone or silicone resin can be applied to the substrate neat and cured in the same manner.
- a 2 inch x 6 inch piece of 100% cotton fleece was shaken with an aqueous solution containing 5% by weight a siloxane oligomer (aminoethylaminopropyl silsesquioxane oligomer, Gelest, Inc., referred to as "siloxane” in Table 1) and aluminum lactate (0.9% or 3.7% by weight based on the total weight of the fabric treatment composition) at room temperature.
- the fabric was removed and run through a hand- turned clothes wringer. The wet pick up was determined to be approximately 100%. This was repeated on a total of 14 fleece samples.
- the samples were heated in a convection oven at 150°C for 20 minutes and then allowed to cool to room temperature. Five samples were evaluated for flame retardancy performance after treatment/heating, and five others were washed prior to flame testing.
- a one gallon metal paint can was mixed 3.9 grams of 1993 AATCC laundry detergent and 1.5 kg of tap water. The can was placed on a stirrer/hot plate and fitted with an overhead mechanical stirrer with a 3-bladed impeller positioned just below the surface of the water. A metal thermocouple was inserted at a 45° angle to the water. Seven pieces of treated fabric (all from the same treatment) were added. With the stirrer set at 60-70%, the samples were washed for 12 min at 49°C. The fabric samples were then removed and placed in a beaker under a flow of cold tap water ( ⁇ 15°C) for 5 min to rinse. The excess water was removed, and the samples were dried horizontally on a rack overnight at room temperature.
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Textile Engineering (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Silicon Polymers (AREA)
Abstract
Description
Claims
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2004245525A AU2004245525A1 (en) | 2003-06-02 | 2004-05-28 | Silicone based flame retardant systems for textiles |
MXPA05013068A MXPA05013068A (en) | 2003-06-02 | 2004-05-28 | Silicone based flame retardant systems for textiles. |
BRPI0411273-3A BRPI0411273A (en) | 2003-06-02 | 2004-05-28 | silicone based flame retardant systems for fabrics |
JP2006515057A JP2006526697A (en) | 2003-06-02 | 2004-05-28 | Silicone flame retardant for textile materials |
EP04753953A EP1633803A1 (en) | 2003-06-02 | 2004-05-28 | Silicone based flame retardant systems for textiles |
CA002527928A CA2527928A1 (en) | 2003-06-02 | 2004-05-28 | Silicone based flame retardant systems for textiles |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/449,893 | 2003-06-02 | ||
US10/449,893 US7147671B2 (en) | 2003-06-02 | 2003-06-02 | Silicone based flame retardant systems for textiles |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004108798A1 true WO2004108798A1 (en) | 2004-12-16 |
Family
ID=33451889
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2004/017233 WO2004108798A1 (en) | 2003-06-02 | 2004-05-28 | Silicone based flame retardant systems for textiles |
Country Status (12)
Country | Link |
---|---|
US (1) | US7147671B2 (en) |
EP (1) | EP1633803A1 (en) |
JP (1) | JP2006526697A (en) |
KR (1) | KR20060025543A (en) |
CN (1) | CN1832980A (en) |
AU (1) | AU2004245525A1 (en) |
BR (1) | BRPI0411273A (en) |
CA (1) | CA2527928A1 (en) |
MX (1) | MXPA05013068A (en) |
RU (1) | RU2349610C2 (en) |
WO (1) | WO2004108798A1 (en) |
ZA (1) | ZA200510261B (en) |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN100334137C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening and anti-shrinking function |
CN100334132C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with relaxing and anti-shrinking function |
CN100334133C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing cation composite modified organic silicon emulsion with softening, slipping and elastic function |
CN100389144C (en) * | 2005-03-07 | 2008-05-21 | 华明扬 | Process for preparing cation composite modified organic silicon emulsion with softening and anti-shrinking function |
CN100389143C (en) * | 2005-03-07 | 2008-05-21 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening, anti-shrinking and elastic function |
CN100334136C (en) * | 2005-03-07 | 2007-08-29 | 华明扬 | Process for preparing anion composite modified organic silicon emulsion with softening, slipping and elastic function |
US7632881B2 (en) * | 2006-06-22 | 2009-12-15 | Sabic Innovative Plastics Ip B.V. | Polycarbonate compositions and articles formed therefrom |
US7897678B2 (en) * | 2007-07-26 | 2011-03-01 | 3M Innovative Properties Company | Fluorochemical urethane compounds having pendent silyl groups |
US8015970B2 (en) * | 2007-07-26 | 2011-09-13 | 3M Innovative Properties Company | Respirator, welding helmet, or face shield that has low surface energy hard-coat lens |
WO2009075191A1 (en) * | 2007-12-12 | 2009-06-18 | Dow Corning Toray Co., Ltd. | Thermoplastic flame-retardant resin composition, flame-retardant fiber made of the resin composition and method for producing the same, and silicone flame retardant for thermoplastic resin and method for producing the same |
ES2426140T3 (en) * | 2009-06-08 | 2013-10-21 | Huntsman International Llc | Thermoplastic flame retardant composition |
TW201527424A (en) * | 2013-10-29 | 2015-07-16 | Dow Corning | Flame retardant thermoplastic polymer compositions |
CN107724080B (en) * | 2017-10-17 | 2020-07-21 | 厦门大学 | Super-hydrophobic flame-retardant fabric with oil-water separation function and preparation method thereof |
EP3670738A1 (en) * | 2018-12-21 | 2020-06-24 | Nolax AG | Textile heat, fire and/or smoke protection material |
CN109930392B (en) * | 2019-02-28 | 2021-10-26 | 上海驰纺材料科技有限公司 | Preparation method of washable long-acting cool cotton-containing knitted fabric |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1215328A (en) * | 1965-01-21 | 1970-12-09 | Dow Corning | Colloidal silsesquioxanes and methods for making same |
US4705704A (en) * | 1985-10-01 | 1987-11-10 | General Electric Company | Novel aminofunctional polysiloxane emulsions for treating textiles |
EP0699717A2 (en) * | 1994-08-30 | 1996-03-06 | Dow Corning Corporation | Organosiloxane compositions yielding cured products exhibiting adhesion and reduced flammability |
EP0702106A1 (en) * | 1994-09-16 | 1996-03-20 | Takata Corporation | Base fabric for air bags and method for the preparation thereof |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
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FR810805A (en) * | 1935-12-19 | 1937-03-31 | Process and product for water repellency of fabrics | |
US3504998A (en) * | 1960-05-13 | 1970-04-07 | Dow Corning | Dyeing textile coated with an aminoethylaminopropyl trialkoxy silane |
US3512915A (en) * | 1960-05-13 | 1970-05-19 | Dow Corning | Dyeing textile with a dye solution containing a copolymer of an alkyl siloxane and a polyaminoalkylsiloxane having at least 3 carbons in the alkyl chain |
US3355424A (en) * | 1964-07-29 | 1967-11-28 | Dow Corning | Method for the preparation of aminoalkylsiloxane copolymers |
US4476188A (en) * | 1983-12-23 | 1984-10-09 | Dow Corning Corporation | Compositions producing aminofunctional silicone foams and coatings |
JPS61159427A (en) * | 1984-12-29 | 1986-07-19 | Toshiba Silicone Co Ltd | Polyorganosiloxane composition for surface treatment |
JPS6375184A (en) * | 1986-09-19 | 1988-04-05 | 信越化学工業株式会社 | Treatment agent for synthetic fiber |
JPS6445466A (en) * | 1987-08-14 | 1989-02-17 | Shinetsu Chemical Co | Textile treating composition |
US4888136A (en) * | 1988-05-02 | 1989-12-19 | Witco Corporation | New flame retardant compositions of matter and cellulosic products containing same |
DE68920775T2 (en) * | 1988-05-17 | 1995-06-08 | Dow Corning Ltd | Treatment of fibrous materials. |
JPH0723585B2 (en) * | 1989-11-06 | 1995-03-15 | 信越化学工業株式会社 | Wool treating agent |
JP3211656B2 (en) * | 1996-03-18 | 2001-09-25 | 信越化学工業株式会社 | Water-soluble fiber treating agent and method for producing the same |
JP4114227B2 (en) | 1998-02-17 | 2008-07-09 | コニカミノルタホールディングス株式会社 | Inkjet liquid composition, image forming ink set, and image forming method |
JP4231983B2 (en) * | 2000-12-22 | 2009-03-04 | 信越化学工業株式会社 | Water-soluble water and oil repellent treatment agent and method for producing the same |
-
2003
- 2003-06-02 US US10/449,893 patent/US7147671B2/en not_active Expired - Fee Related
-
2004
- 2004-05-28 MX MXPA05013068A patent/MXPA05013068A/en unknown
- 2004-05-28 RU RU2005141143/04A patent/RU2349610C2/en not_active IP Right Cessation
- 2004-05-28 WO PCT/US2004/017233 patent/WO2004108798A1/en active Application Filing
- 2004-05-28 KR KR1020057023034A patent/KR20060025543A/en not_active Application Discontinuation
- 2004-05-28 EP EP04753953A patent/EP1633803A1/en not_active Withdrawn
- 2004-05-28 CA CA002527928A patent/CA2527928A1/en not_active Abandoned
- 2004-05-28 AU AU2004245525A patent/AU2004245525A1/en not_active Abandoned
- 2004-05-28 BR BRPI0411273-3A patent/BRPI0411273A/en not_active IP Right Cessation
- 2004-05-28 JP JP2006515057A patent/JP2006526697A/en active Pending
- 2004-05-28 CN CNA2004800224454A patent/CN1832980A/en active Pending
-
2005
- 2005-12-15 ZA ZA200510261A patent/ZA200510261B/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1215328A (en) * | 1965-01-21 | 1970-12-09 | Dow Corning | Colloidal silsesquioxanes and methods for making same |
US4705704A (en) * | 1985-10-01 | 1987-11-10 | General Electric Company | Novel aminofunctional polysiloxane emulsions for treating textiles |
EP0699717A2 (en) * | 1994-08-30 | 1996-03-06 | Dow Corning Corporation | Organosiloxane compositions yielding cured products exhibiting adhesion and reduced flammability |
EP0702106A1 (en) * | 1994-09-16 | 1996-03-20 | Takata Corporation | Base fabric for air bags and method for the preparation thereof |
Non-Patent Citations (1)
Title |
---|
GELEST, INC.: "AMINOPRPYLSILSESQUIOXANE-METHYLSILSESQUIOXANE", 9 June 2002 (2002-06-09), XP002301985, Retrieved from the Internet <URL:http://www.gelest.com/msds.asp?WSA-7011> [retrieved on 20041019] * |
Also Published As
Publication number | Publication date |
---|---|
EP1633803A1 (en) | 2006-03-15 |
CA2527928A1 (en) | 2004-12-16 |
KR20060025543A (en) | 2006-03-21 |
RU2005141143A (en) | 2006-06-10 |
AU2004245525A1 (en) | 2004-12-16 |
ZA200510261B (en) | 2006-09-27 |
CN1832980A (en) | 2006-09-13 |
RU2349610C2 (en) | 2009-03-20 |
JP2006526697A (en) | 2006-11-24 |
BRPI0411273A (en) | 2006-08-01 |
US7147671B2 (en) | 2006-12-12 |
MXPA05013068A (en) | 2006-03-02 |
US20040242768A1 (en) | 2004-12-02 |
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