WO2008127519A1 - Silcone polyether block copolymers having organofunctional endblocking groups - Google Patents
Silcone polyether block copolymers having organofunctional endblocking groups Download PDFInfo
- Publication number
- WO2008127519A1 WO2008127519A1 PCT/US2008/002962 US2008002962W WO2008127519A1 WO 2008127519 A1 WO2008127519 A1 WO 2008127519A1 US 2008002962 W US2008002962 W US 2008002962W WO 2008127519 A1 WO2008127519 A1 WO 2008127519A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silicone polyether
- group
- amine
- copolymer
- silicone
- Prior art date
Links
Classifications
-
- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- 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
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- 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
-
- 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
-
- 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
- D06M2200/50—Modified hand or grip properties; Softening compositions
Definitions
- This disclosure relates to silicone polyether copolymers having an organofunctional endblocking group, methods of making them, and their use for treating textiles or fibers.
- Silicones have been used extensively for fiber or textile treatments.
- various amine functional silicones have been developed and sold commercially under various tradenames.
- Common problems associated with amine functional silicones as textile treatments are their yellowing of textiles from the oxidation of the amine groups and extensive hydrophobic nature of the polydimethylsiloxane chains.
- efforts over the years have focused on modifying amine functional silicones by adding hydrophilic groups to the siloxane polymers, while altering or reducing the amine content to reduce yellowing.
- JP09183854, and JP03269570 describe a copolymer prepared by first making a block copolymer from Si-H terminal polydimethylsiloxane and allyl or methallyl terminal polyether, and then equilibrating that copolymer with an aminosiloxane to incorporate the amine functionality.
- the silicone polyether block copolymers may be prepared by hydrosilylating an SiH terminal silicone polyether block copolymer with an epoxy functional olefin such as allyl glycidyl ether or vinyl cyclohexene oxide. Then, the epoxy groups are reacted with an amine to convert the epoxides into beta hydroxy amine groups. Alternately, the epoxy groups may be reacted with tertiary amine salts to convert the epoxides into beta hydroxy quaternary ammonium groups.
- the advantage of using the hydrosilylation chemistry in conjunction with the amine-epoxide chemistry is that most polymer chains will contain hydrophilic polyether blocks and two amine groups.
- amine groups are at the chain end, it is possible to use a minimal amount of amine to minimize yellowing of fabrics.
- the amine groups can be further converted to the salt form by addition of acid or converted to their quaternary ammonium forms via the use of common quaternizing agents such as alkyl halides, benzyl halides, alkyl sulfates, aryl sulfates, or chloroacetate esters.
- This invention relates to a silicone polyether copolymer having the average formula; E-B-[AB] n -E where E is an organofunctional endblocking group, B is a diorganopolysiloxane,
- A is a divalent organic group comprising at least one polyether group, and n is ⁇ 1.
- the silicone polyether copolymer has the average formula
- R 1 is a divalent hydrocarbon containing 2 to 30 carbons.
- E is an organofunctional endblocking group that may have the formula
- R A CH 2 CH(OH)CH 2 OR 2 - where R A is a monovalent amine functional group, R 2 is a divalent hydrocarbon linking group containing 2 to 6 carbon atoms.
- the present disclosure also provides a process for preparing silicone polyether block copolymers having an organofunctional endblocking group.
- the present disclosure yet further provides a method of using the silicone polyether copolymers for treatment of textiles or fibers.
- the present disclosure relates to a silicone polyether copolymer having the average formula
- E-B-[AB] n -E where E is an organofunctional endblocking group, B is a diorganopolysiloxane,
- A is a divalent organic group comprising at least one polyether group, and n is > 1.
- the silicone polyether copolymers of the present disclosure are -[AB],,- copolymers having repeating units of A, a divalent organic group containing at least one polyether group, and B, a diorganopolysiloxane.
- the subscript n represents on average the number repeating units of [AB] in the copolymer, and n is > 1, alternatively n ranges from 1 to 50.
- the silicone polyether copolymers of the present disclosure are characterized by having an organofunctional endblocking group, designated as E, and described in more detail below.
- the divalent organic group in the silicone polyether copolymers of the present disclosure comprises at least one polyether group.
- polyether designates a polyoxyalkylene group.
- the polyoxyalkylene group may be represented by, although not limited to, the formula (C m H 2m O) y wherein m is from 2 to 4 inclusive, and y is greater than 4, alternatively y may range from 5 to 60, or alternatively from 5 to 30.
- the polyoxyalkylene group may comprise oxyethylene units (C 2 H 4 O), oxypropylene units (C 3 H 6 O), oxybutylene units (C 4 H 8 O), or mixtures thereof.
- the polyoxyalkylene group comprises oxyethylene units (C 2 H 4 O) or mixtures of oxyethylene units and oxypropylene units.
- the "silicone” group in the silicone polyether copolymers of the present disclosure is a diorganopolysiloxane, designated as B.
- the diorganopolysiloxane may be a predominately linear siloxane polymer having the formula (R 2 SiO) x , wherein R is independently selected from a monovalent hydrocarbon group, x is > 1, alternatively x may range from 2 to 100, or from 2 to 50.
- the hydrocarbon groups represented by R in the siloxane polymer are free of aliphatic unsaturation.
- organic groups may be independently selected from monovalent hydrocarbon and monovalent halogenated hydrocarbon groups free of aliphatic unsaturation.
- These monovalent groups may have from 1 to 30 carbon atoms, alternatively 1 to 10 carbon atoms, and are exemplified by, but not limited to alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, undecyl, and octadecyl; cycloalkyl such as cyclohexyl; aryl such as phenyl, tolyl, xylyl, benzyl, and 2-phenylethyl; and halogenated hydrocarbon groups such as 3,3,3- trifluoropropyl, 3-chloropropyl, and dichlorophenyl.
- the diorganopolysiloxane is a predominately linear polydimethylsiloxane having the
- the silicone polyether copolymer may be represented by the average formula
- E is an organofunctional endblocking group
- x is >
- m is from 2 to 4 inclusive
- y is > 4
- n is > 1,
- R is independently a monovalent hydrocarbon group containing 1 to 30 carbons
- R 1 is a divalent hydrocarbon containing 2 to 30 carbons.
- At least one end of each polyether block A is linked to an organopolysiloxane block B by a divalent hydrocarbon group, designated R 1 . This linkage is determined by the reaction employed to prepare the (AB) n block silicone polyether copolymer.
- the divalent hydrocarbon group R 1 may be independently selected from divalent hydrocarbon groups containing 2 to 30 carbons. Representative, non-limiting examples of such divalent hydrocarbon groups include; ethylene, propylene, butylene, isobutylene, pentylene, hexylene, heptylene, octylene, and the like. Representative, non-limiting examples of such divalent organofunctional hydrocarbons groups include acrylate and methacrylate. Typically, R 1 is isobutylene (- CH 2 CH(CH 3 )CH 2 -).
- the organofunctional endblocking group E may have the formula R A CH 2 CH(OH)CH 2 OR 2 - where R A is a monovalent amine functional group and R 2 is a divalent hydrocarbon linking group containing 2 to 6 carbon atoms, such as a divalent alkylene like ethylene, propylene, butylene, isobutylene, pentylene, or hexylene. Typically, R 2 is propylene -CH 2 CH 2 CH 2 -.
- the monovalent amine functional group R A may be any amine functional organic group. The nitrogen atom of the amine functional group is bonded to the methylene group of the -CH 2 CH(OH)CH 2 OR 2 - endblocking group.
- the amine functional group may be any secondary, tertiary, or quaternary amine, but typically are tertiary amines.
- the amine functional group may be include other organic functional groups, such as amino, hydroxy, epoxy, ether, amido, and carboxyl groups.
- R A may have the formula (R 3 ) 2 N- , H(R 3 )N-, or (R 3 ) 3 N- , wherein R 3 is independently a monovalent organic containing 1 to 30 carbon atoms.
- R 3 is independently a monovalent hydrocarbon group containing 1 to 30 carbon atoms, such as alkyl groups containing 1 to 30 carbons like methyl, ethyl, propyl, butyl, and similar homologs.
- the amine functional group may include cyclic amines such as; pyrrolidine; piperidine; morpholine; 3-pyrrolidinol; 2,5- dimethylpyrrolidine; 1-methylpiperazine; 4-hydroxypiperidine; N-(2- hydroxyethyl)piperazine, 2,6-dimethylpiperidine; 1-ethylpiperazine; l-amine-4- methylpiperazine; and isoindoline.
- organofunctional endblocking group E may have the formula
- n and x are as defined above, y' is > 0, alternatively y' is 0 to 60, y" is > 0, alternatively y" is 0 to 60, with the proviso that y' + y" > 4
- Me is methyl
- Et is ethyl
- EO is CH 2 CH 2 O
- the organofunctional endblocking group E is an epoxide functional group having the formula,
- R 2 is a divalent hydrocarbon linking group containing 2 to 6 carbon atoms, as described above.
- the epoxide functional silicone polyether block copolymers are particularly useful to prepare the amine terminal silicone polyether block copolymers of the present disclosure.
- the present disclosure further provides a process to prepare an amine terminal silicone polyether block copolymer comprising: I) reacting;
- step I C) a hydrosilylation catalyst, D) an optional solvent, where the molar ratio of B/A is greater than one, II) further reacting the product of step I with;
- Step I) in the above process involves reacting ingredients A) a polyoxyalkylene having an unsaturated hydrocarbon group at each molecular terminal, B) a SiH terminated organopolysiloxane, C) a hydrosilylation catalyst, and D) an optional solvent, where the molar ratio of B/A is greater than one.
- the polyoxyalkylene useful in the process of the present invention can be any polyoxyalkylene group that is terminated at each molecular chain end (i.e. alpha and omega positions) with a unsaturated organic group.
- the polyoxyalkylene may result from the polymerization of ethylene oxide, propylene oxide, butylene oxide, 1,2-epoxyhexane, 1, 2- epoxyoctance, cyclic epoxides such as cyclohexene oxide or exo-2,3-epoxynorborane.
- the polyoxyalkylene may be represented by the formula (C m H 2m O) y , wherein m is from 2 to 4 inclusive, and y is greater than 4, alternatively y may range from 5 to 60, or alternatively from 5 to 30.
- the polyoxyalkylene group may comprise oxyethylene units (C 2 H 4 O), oxypropylene units (C 3 H O O), oxybutylene units (C 4 H 8 O), or mixtures thereof.
- the polyoxyalkylene group comprises oxyethylene units (C 2 H 4 O) or mixtures of oxyethylene units and oxypropylene units.
- the unsaturated organic group can be an unsaturated aliphatic hydrocarbon group such as alkenyl or alkynyl group. Representative, non- limiting examples of the alkenyl groups are shown by the following structures;
- alkynyl groups are shown by the following structures; HC ⁇ C-, HC ⁇ CCH 2 -, HC ⁇ CC(CH 3 ) - , HC ⁇ CC(CH 3 ) 2 - , and HC ⁇ CC(CH 3 ) 2 CH 2 - .
- the unsaturated organic group can be an organofunctional hydrocarbon such as an acrylate, methacrylate and the like.
- the polyoxyalkylene may be selected from those having the average formula
- R 4 is hydrogen or an alkyl group containing 1 to 20 carbon atoms, EO is -CH 2 CH 2 O-,
- PO is -CH 2 CH(Me)O- or -CH 2 CH 2 CH 2 O-.
- Polyoxyalkylenes having an unsaturated aliphatic hydrocarbon group at each molecular terminal are known in the art, and many are commercially available.
- EO is -CH 2 CH 2 O-
- PO is -CH 2 CH(Me)O- or -CH 2 CH 2 CH 2 O-.
- Polyoxyalkylenes having an unsaturated aliphatic hydrocarbon group at each molecular terminal are commercially available from NOF (Nippon Oil and Fat, Tokyo, Japan) and Clariant Corp. (Charlottesville, NC).
- the SiH terminated organopolysiloxanes useful in the process of the present invention can be represented by the formula MOM', where "M'” means a siloxane unit of formula R 2 HSiO 1/2 , “D” means a siloxane unit of formula R 2 SiO 2 Z 2 , where R is independently a monovalent hydrocarbon group as defined above.
- the SiH terminated organopolysiloxane is a dimethylhydrogensiloxy-terminated polydimethylsiloxane having the average formula Me 2 HSiO(Me 2 SiO) x SiHMe 2 , where x is > 1, alternatively x may range from 2 to 100, or from 2 to 50.
- SiH terminated organopolysiloxanes and methods for their preparation are well known in the art.
- the SiH terminated organopolysiloxane and polyoxyethylene having an unsaturated organic group at each molecular terminal are reacted in the presence of a hydrosilylation catalyst, which are known in the art.
- Hydrosilylations are well known in the art and involves the reaction between a polysiloxane containing ⁇ Si-H groups, and a material containing unsaturation, e.g., vinyl groups.
- the reaction typically uses a catalyst to effect the reaction between the ⁇ SiH containing polysiloxane and the material containing unsaturation.
- Suitable catalysts are Group VIII transition metals, i.e., the noble metals.
- Such noble metal catalysts are described in US Patent 3,923,705, incorporated herein by reference to show platinum catalysts.
- One preferred platinum catalyst is Karstedt's catalyst, which is described in Karstedt's US Patents 3,715,334 and 3,814,730, incorporated herein by reference.
- Karstedt's catalyst is a platinum divinyl tetramethyl disiloxane complex typically containing one weight percent of platinum in a solvent such as toluene.
- Another preferred platinum catalyst is a reaction product of chloroplatinic acid and an organosilicon compound containing terminal aliphatic unsaturation. It is described in US Patent 3,419,593, incorporated herein by reference.
- the catalyst is a neutralized complex of platirious chloride and divinyl tetramethyl disiloxane, for example as described in US Patent 5,175,325.
- the noble metal catalyst can be used in an amount of from 0.00001-0.5 parts per 100 weight parts of the ⁇ SiH containing polysiloxane. Alternatively, the catalyst should be used in an amount sufficient to provide 0.1-15 parts per million (ppm) Pt metal per total composition.
- the hydrosilylation reaction can be conducted neat or in the presence of D), a solvent.
- the solvent can be an alcohol such as methanol, ethanol, isopropanol, butanol, or n- propanol, a ketone such as acetone, methylethyl ketone, or methyl isobutyl ketone; an aromatic hydrocarbon such as benzene, toluene, or xylene; an aliphatic hydrocarbon such as heptane, hexane, or octane; a glycol ether such as propylene glycol methyl ether, dipropylene glycol methyl ether, propylene glycol n-butyl ether, propylene glycol n-propyl ether, or ethylene glycol n-butyl ether, a halogenated hydrocarbon such as dichloromethane, 1,1,1- trichloroethane or methylene chloride, chloroform
- the amount of solvent can be up to 70 weight percent, but is typically from 20 to 50 weight percent, said weight percent being based on the total weight of components in the hydrosilylation reaction.
- the solvent used during the hydrosilylation reaction can be subsequently removed from the resulting silicone polyether by various known methods.
- Step I) effects a hydrosilylation reaction, wherein the SiH units of ingredient B react with the unsaturated aliphatic hydrocarbon group of ingredient A to form an Si-C bond.
- the reaction may be conducted under those conditions known in the art for effecting hydrosilylations reactions.
- Additional components can be added to the hydrosilylation reaction which are known to enhance such reactions.
- step I provides a reaction product comprising a silicone polyether [AB] n copolymer having terminal SiH units. These SiH units are further reacted in step II.
- Step II) in the process of the present disclosure involves further reacting the product of step I with E) an epoxide having at least one aliphatic unsaturated hydrocarbon group to form an epoxide terminal silicone polyether block copolymer.
- the reaction in step II is another hydrosilylation reaction.
- the epoxide having at least one aliphatic unsaturated hydrocarbon group is simply added at the end of step I, and the second hydrosilylation reaction allowed to progress under the same conditions.
- additional amounts of the hydrosilylation catalyst C) may be added.
- epoxide having at least one aliphatic unsaturated group suitable for the reaction in step II include;
- Step II Allyloxy-3,4-epoxytricyclo(5.2.1.0 2,6)decane, CAS: 2279-19-8.
- the amount of the epoxide added in step II may vary, but is typically added in sufficient amount to consume the residual Si-H, that is a molar excess of epoxide to SiH is used. Lower amounts of the epoxide may be used if limiting free epoxide is desired, with the understanding that only partial endblocking will be achieved.
- Step I) and Step II) may be carried out sequentially or simultaneously; however typically the reactions are conducted sequentially to build molecular weight of the (AB) n before consuming the final quantities of Si-H with an excess of the epoxy endcapping group.
- Step III) in the process of the present disclosure involves reacting the epoxide terminal silicone polyether block copolymer formed in step II) with F) an amine compound to form the amine terminal silicone polyether block copolymer.
- Step III effects a ring opening reaction of the epoxide by the addition of an amine compound.
- the amine compound may be any amine compound, but typically are secondary amines.
- the amine compound may be selected from an amine compound containing an R A group, where R A is as defined above.
- R A may have the formula (R 3 ) 2 N- , H(R 3 )N-, or (R 3 ) 3 N- , wherein R 3 is independently a monovalent organic containing 1 to 30 carbon atoms.
- R 3 is independently a monovalent hydrocarbon group containing 1 to 30 carbon atoms, such as alkyl groups containing 1 to 30 carbons like methyl, ethyl, propyl, butyl, and similar homologs.
- the amine compound may include other organic functional groups, such as amino, hydroxy, epoxy, ether, amido, and carboxyl groups.
- organic functional groups such as amino, hydroxy, epoxy, ether, amido, and carboxyl groups.
- Representative, non limiting examples include; (CH 3 )NH 2 , (CH 3 ) 2 NH, (CH 3 CH 2 )NH 2 , (CH 3 CH 2 ) 2 NH, (CH 3 CH 2 ) 3 N, (HOCH 2 CH 2 ) 2 NH.
- the amine functional group may include cyclic amines.
- suitable cyclic amines include; l-(2-hydroxyethyl)piperazine Pyrrolidine, CAS: 123-75-1
- the amine terminal silicone polyether block copolymer of the present disclosure may be further reacted to form amine salts or quaternary ammonium salts.
- the amine terminal silicone polyether block copolymer may be reacted with alkyl halides or alkyl sulfates to form a quaternary ammonium salt.
- the reaction may occur under those conditions known in the art for effecting quaternization of amines. It is not necessary to convert all the amine groups present in the amine terminal silicone polyether block copolymer.
- those silicone polyether block copolymers having a mixture of amine and quaternary groups are considered to be within the compositions of the present invention.
- the amine or quat terminal silicone polyether block copolymers of the present disclosure may be an ingredient in an emulsion composition.
- emulsion is meant to encompass water continuous emulsions (for example an oil in water type emulsion, or a silicone in water emulsion), oil or silicone continuous emulsions (water in oil emulsions or water in silicone emulsions), or multiple emulsions (water/oil/water, oil/water/oil types, water/silicone/water, or silicone/water/silicone).
- the amine or quat terminal silicone polyether block copolymers of the present disclosure may be added to any type of emulsion by common mixing techniques.
- amine or quat terminal silicone polyether block copolymers may occur either during the preparation of the emulsion, or subsequently post added to a pre-formed emulsion.
- Mixing techniques can be simple stirring, homogenizing, sonalating, and other mixing techniques known in the art to effect the formation of emulsions.
- the mixing can be conducted in a batch, semi-continuous, or continuous process.
- the amount of amine or quat terminal silicone polyether block copolymers of the present disclosure added to the emulsion can vary and is not limited, however the amounts typically may range from a silicone polyether copolymer/emulsion weight ratio of 0.1/99 to 99/0.1, alternatively 1/99 to 99/1.
- the emulsions used may be w/o, w/s, or multiple phase emulsions using silicone emulsifiers.
- the water-in-silicone emulsifier in such formulation is non-ionic and is selected from polyoxyalkylene-substituted silicones, silicone alkanolamides, silicone esters and silicone glycosides.
- Silicone-based surfactants may be used to form such emulsions and are well known in the art, and have been described for example in US 4,122,029 (Gee et al.), US 5,387,417 (Rentsch), and US 5,811,487 (Schulz et al).
- the emulsion when it is an oil-in-water emulsion, it may include common ingredients generally used for preparing emulsions such as but not limited to non ionic surfactants well known in the art to prepare o/w emulsions .
- nonionic surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenol ethers, polyoxyethylene lauryl ethers, polyoxyethylene sorbitan monoleates, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, polyethylene glycol, polypropylene glycol, diethylene glycol, ethoxylated trimethylnonanols, and polyoxyalkylene glycol modified polysiloxane surfactants.
- the method of the present invention comprises applying to fibers or textiles the silicone block copolymer or emulsions thereof, either of which are also referred herein as the treatment composition.
- the amount applied is a "hand improving" effective amount of the treatment composition and is applied to the fiber and/or textile by any convenient method.
- Hand for purposes of the invention means the softness and smoothness of the fabric.
- the treatment composition can be applied by padding, dipping, spraying or exhausting.
- the solutions, dispersions, and emulsions can be applied simultaneously or sequentially to the textiles.
- After the treatment composition is applied to the fiber and/or fabric, it can be dried by heat.
- the fiber/textile treatment composition can be applied to the fiber and/or textile during making the fibers or textiles, or later such as during laundering textiles. After application, carriers (if any) can be removed from the treatment composition for example by drying the composition at ambient or elevated temperature.
- the amount of treatment composition applied to the fibers and textiles is typically sufficient to provide 0.1 to 15 weight percent of the composition on the fibers and textiles, based on their dry weight, preferably in an amount of 0.2 to 5 weight percent based on the dry weight of the fiber or textile.
- Fibers and textiles that can be treated with the treatment composition include natural fibers such as cotton, silk, linen, and wool; regenerated fibers such as rayon and acetate; synthetic fibers such as polyesters, polyamides, polyacrylonitriles, polyethylenes, and polypropylenes; combinations, and blends thereof.
- the form of the fibers can include threads, filaments, tows, yarns, woven fabrics, knitted materials, non-woven materials, paper, carpet, and leather.
- Textiles treated with the silicone block copolymer have a feel or hand comparable to conventional hydrophobic silicone, but do not significantly impact negatively on the hydrophilicity of the textile.
- MEA N-methylethanolamine (CAS: 109-89-7), JEFF: Jeffamine M-IOOO (CAS: 83713-01-3), OCT: Octadecylamine (CAS: 124-30-1), and HEP: l-(2-hydroxyethyI)piperazine (CAS: 103-76-4)
- Example 6 N-methylethanolamine (CAS: 109-89-7), JEFF: Jeffamine M-IOOO (CAS: 83713-01-3), OCT: Octadecylamine (CAS: 124-30-1), and HEP: l-(2-hydroxyethyI)piperazine (CAS: 103-76-4)
- An amine terminate silicone polyether block copolymer having the target composition EB(AB) n E, where n 2, A represents a 17 DP polyether block, B represents a 45 DP silicone block, and E arises from hydroxyethylpiperazine, was subjected to quaternization with dimethylsulfate, as described in this example.
- Theoretical nitrogen content was 0.44 wt. % N or 0.314 meq/g amine.
- the quaternization was targeted to convert 45% of the nitrogen groups to quaternary ammonium groups.
- An amine terminated silicone polyether block copolymer having the target composition EB(AB) n E, where n 2, A represents a 14.1 DP polyether block, B represents a 34.5 DP silicone block, and E arises from reaction with diethylamine was emulsified as follows.
- Samples of the amine terminal (AB )n materials were emulsified and applied on cotton knit fabric for evaluation. As summarized in Table 2, samples of the amine terminal silicone significantly improved the feel of the fabric as shown by panel testing. Control samples treated with water typically had very poor hand, and received a rating of 1. Samples treated with the (AB) n polymers of the current invention were rated above 4.5, indicative of a significant improvement. The hydrophilicity and yellowing characteristics of the fabric were not affected to a great extent.
- 13 C NMR confirms the presence of chain extending and terminal amine groups.
- a peak at 49.3 ppm in the 13 C NMR spectrum was assigned to a methylene group alpha to the terminal amine nitrogen, whereas a peak at 54.97 ppm was assigned to a methylene group alpha to a chain extending amine nitrogen. Residual epoxide was observed at lower amine/epoxy ratios, but the epoxide could be eliminated by adding excess amine near the end of the reaction.
- An epoxy terminal (AB) n silicone polyether copolymer was synthesized with POLYETHER 2, an Si-H terminal silicone (0.061 wt% H as SiH) and allyl glycidyl ether to give a copolymer having a viscosity of 1650 cP and an epoxide content of 0.214 meq/g.
- To a 250 mL 3-neck flask was added 75.1 g (16.0 meq epoxide) of the above polymer, 1.54 g (17.9 mmol) of piperazine (CAS: 110-85-0), and 32.9 g of i-PrOH. The reaction was heated at reflux for six hours. After cooling, the solvent was removed in vacuo.
- Viscosity measurements showed that the viscosities of the epoxy terminal polymer relative to that of the resulting polymer increased from 1650 cP to 7130 cP. NMR analysis confirms that the average molecular weight is twice that of the starting epoxy terminal polymer.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Silicon Polymers (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/594,649 US8013097B2 (en) | 2007-04-11 | 2008-03-05 | Silicone polyether block copolymers having organofunctional endblocking groups |
EP20080726484 EP2139941A1 (en) | 2007-04-11 | 2008-03-05 | Silcone polyether block copolymers having organofunctional endblocking groups |
CN2008800143385A CN101675095B (en) | 2007-04-11 | 2008-03-05 | Silcone polyether block copolymers having organofunctional endblocking groups |
JP2010503000A JP5501951B2 (en) | 2007-04-11 | 2008-03-05 | Silicone polyether block copolymers with organofunctional end-capping groups |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US92287907P | 2007-04-11 | 2007-04-11 | |
US60/922,879 | 2007-04-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2008127519A1 true WO2008127519A1 (en) | 2008-10-23 |
Family
ID=39629125
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2008/002962 WO2008127519A1 (en) | 2007-04-11 | 2008-03-05 | Silcone polyether block copolymers having organofunctional endblocking groups |
Country Status (6)
Country | Link |
---|---|
US (1) | US8013097B2 (en) |
EP (1) | EP2139941A1 (en) |
JP (1) | JP5501951B2 (en) |
KR (1) | KR20090127950A (en) |
CN (1) | CN101675095B (en) |
WO (1) | WO2008127519A1 (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010047993A2 (en) * | 2008-10-22 | 2010-04-29 | Dow Corning Corporation | Aminofunctional endblocked silicone polyether copolymers in personal care compositions |
CN101994256A (en) * | 2009-08-17 | 2011-03-30 | 河南瑞贝卡发制品股份有限公司 | Method for preparing artificial synthetic fiber after finishing auxiliary agent and impregnation process |
WO2011127108A1 (en) | 2010-04-06 | 2011-10-13 | Dow Corning Corporation | Reactive amine-functional silicone-polyether block copolymers |
WO2013148979A1 (en) | 2012-03-28 | 2013-10-03 | Dow Corning Corporation | Amphiphilic resin-linear organosiloxane block copolymers |
WO2014104257A1 (en) | 2012-12-28 | 2014-07-03 | 東レ・ダウコーニング株式会社 | Method for manufacturing high-purity organosilicon compound |
WO2014151587A2 (en) | 2013-03-15 | 2014-09-25 | Dow Corning Corporation | Amphiphilic resin linear copolymers for pharmaceutical drug delivery applications |
EP2789642A1 (en) * | 2013-04-09 | 2014-10-15 | Evonik Industries AG | Polysiloxane-Polyether copolymers with amino and/or quaternary ammonium groups linked to the polyether part, and process to prepare such copolymers |
WO2017182061A1 (en) | 2016-04-19 | 2017-10-26 | Wacker Chemie Ag | Amino-organopolysiloxane and preparation method thereof |
CN107814941A (en) * | 2017-11-13 | 2018-03-20 | 清远市宏图助剂有限公司 | A kind of microwave preparation of the quaternized block organosilicon polymer of smooth type |
CN112680973A (en) * | 2020-12-28 | 2021-04-20 | 绍兴海成化工有限公司 | In-cylinder silicone oil and preparation method thereof |
CN113501962A (en) * | 2021-08-07 | 2021-10-15 | 佛山市顺德区德美瓦克有机硅有限公司 | Low-yellowing hydrophilic block polyether amino silicone oil and preparation method thereof |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101475802B1 (en) * | 2007-05-01 | 2014-12-23 | 아크조노벨코팅스인터내셔널비.브이. | Antifouling coating composition based on curable polyorganosiloxane polyoxyalkylene copolymers |
GB0708347D0 (en) * | 2007-05-01 | 2007-06-06 | Dow Corning | Polymer compositions |
US8263543B2 (en) | 2009-04-17 | 2012-09-11 | The Procter & Gamble Company | Fabric care compositions comprising organosiloxane polymers |
US8742154B2 (en) | 2011-11-16 | 2014-06-03 | Momentive Performance Materials Inc. | Block ABA silicone polyalkyleneoxicie copolymers, methods of preparation, and applications for employing the same |
US9718087B1 (en) * | 2013-03-15 | 2017-08-01 | The Sherwin-Williams Company | Treated applicator to increase performance |
US10441527B2 (en) | 2015-04-08 | 2019-10-15 | Dow Silicones Corporation | Fluid compositions and personal care |
CN107809993B (en) * | 2015-06-30 | 2021-03-05 | 吉列有限责任公司 | Lubricating member for razor cartridge |
US10982052B2 (en) * | 2016-05-10 | 2021-04-20 | Dow Silicones Corporation | Silicone block copolymer having an aminofunctional endblocking group and method for its preparation and use |
JP7145967B2 (en) * | 2018-11-20 | 2022-10-03 | ワッカー ケミー アクチエンゲゼルシャフト | Block-modified polysiloxane and compositions composed thereof |
CN110106711A (en) * | 2019-05-28 | 2019-08-09 | 朱建余 | A kind of textile fabric finishing agent and preparation method thereof |
EP3990522A1 (en) * | 2019-06-27 | 2022-05-04 | Wacker Metroark Chemicals Pvt. Ltd. | Hydrophillic silicone made of olefinic unsaturated polyoxyalkylene glycidyl ether, its composition and preparation method thereof |
KR20230058509A (en) * | 2020-09-08 | 2023-05-03 | 와커 헤미 아게 | Silicone copolymers, their preparation and their use for the treatment of fibrous substrates |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5539013A (en) * | 1991-12-05 | 1996-07-23 | General Electric Company | UV-curable epoxysilicone-polyether block copolymers combined with UV-detectable dye-marker |
JPH09183854A (en) * | 1995-12-28 | 1997-07-15 | Nippon Unicar Co Ltd | Amino-modified polysiloxane-polyoxyalkylene block copolymer and aqueous composition containing the same |
WO2005103117A1 (en) * | 2004-04-20 | 2005-11-03 | Dow Corning Corporation | Silicone polyether block copolymers |
Family Cites Families (102)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3046250A (en) * | 1957-10-04 | 1962-07-24 | Dow Corning | Organosilicon hydroxyalkyl-amine polymers |
NL132432C (en) | 1963-03-26 | |||
BE666745A (en) * | 1964-07-14 | 1966-01-12 | ||
NL131800C (en) * | 1965-05-17 | |||
US3655420A (en) * | 1970-03-06 | 1972-04-11 | Du Pont | Synthetic organic textile fiber with improved, durable, soft, lubricated feel |
US3814730A (en) * | 1970-08-06 | 1974-06-04 | Gen Electric | Platinum complexes of unsaturated siloxanes and platinum containing organopolysiloxanes |
US3715334A (en) * | 1970-11-27 | 1973-02-06 | Gen Electric | Platinum-vinylsiloxanes |
JPS5319715B2 (en) | 1973-09-05 | 1978-06-22 | ||
US3923705A (en) * | 1974-10-30 | 1975-12-02 | Dow Corning | Method of preparing fire retardant siloxane foams and foams prepared therefrom |
JPS5296297A (en) | 1976-02-10 | 1977-08-12 | Mitsubishi Rayon Co | Treatment of polyester fiber |
JPS5817310B2 (en) | 1976-07-08 | 1983-04-06 | 竹本油脂株式会社 | A new softening agent for synthetic fibers. |
JPS5951630B2 (en) | 1977-01-18 | 1984-12-14 | 大和紡績株式会社 | Feather-like polyester fiber |
US4122029A (en) * | 1977-07-27 | 1978-10-24 | Dow Corning Corporation | Emulsion compositions comprising a siloxane-oxyalkylene copolymer and an organic surfactant |
US4185087A (en) * | 1977-12-28 | 1980-01-22 | Union Carbide Corporation | Hair conditioning compositions containing dialkylamino hydroxy organosilicon compounds and their derivatives |
US4184004A (en) * | 1978-04-21 | 1980-01-15 | Union Carbide Corporation | Treatment of textile fabrics with epoxy-polyoxyalkylene modified organosilicones |
DE3035824A1 (en) | 1980-09-23 | 1982-05-06 | Chemische Fabrik Pfersee Gmbh, 8900 Augsburg | METHOD FOR HYDROPHOBIZING FIBER MATERIAL |
JPS6036513B2 (en) | 1981-02-05 | 1985-08-21 | ト−レ・シリコ−ン株式会社 | Textile treatment agent |
JPS57171768A (en) | 1981-04-15 | 1982-10-22 | Shinetsu Chem Ind Co | Fiber treating agent |
DE3215936C2 (en) | 1982-04-29 | 1985-10-24 | Chemische Fabrik Pfersee Gmbh, 8900 Augsburg | Aqueous textile treatment liquor |
JPS59179884A (en) | 1983-03-31 | 1984-10-12 | 信越化学工業株式会社 | Fiber softener |
JPS61296184A (en) | 1985-06-20 | 1986-12-26 | 信越化学工業株式会社 | Fiber treatment agent |
JPH0647787B2 (en) | 1985-08-14 | 1994-06-22 | 日華化学株式会社 | Silicone fiber treatment agent |
EP0235526A3 (en) | 1986-01-29 | 1988-03-23 | Leipziger Arzneimittelwerk GmbH | Activated polymer solids and process for their manufacture |
JPS62276090A (en) | 1986-05-22 | 1987-11-30 | 信越化学工業株式会社 | Treatment agent for synthetic fiber |
JPS6375184A (en) | 1986-09-19 | 1988-04-05 | 信越化学工業株式会社 | Treatment agent for synthetic fiber |
DE3641314A1 (en) * | 1986-12-03 | 1988-06-09 | Henkel Kgaa | LAUNDRY TREATMENT AGENT BASED ON LAYERED SILICATE |
JPS63212304A (en) | 1987-02-27 | 1988-09-05 | 岸田 喜広 | Brush made of polyamide fiber |
US4935464A (en) | 1987-04-30 | 1990-06-19 | Toray Silicone Company Limited | Organopolysiloxane microemulsion, process for its production and application thereof |
US4847154A (en) * | 1987-05-29 | 1989-07-11 | Basf Corporation | Thermosetting resin systems containing secondary amine-terminated siloxane modifiers |
JPH01221580A (en) * | 1988-02-27 | 1989-09-05 | Shin Etsu Chem Co Ltd | Textile treating agent |
JPH0291083A (en) * | 1988-09-27 | 1990-03-30 | Shin Etsu Chem Co Ltd | Siloxane compound of one reactive terminal |
JPH0768671B2 (en) | 1988-10-31 | 1995-07-26 | 共栄社化学株式会社 | Method for modifying cellulosic fibers |
JPH02154076A (en) | 1988-12-06 | 1990-06-13 | Shin Etsu Chem Co Ltd | Textile treating agent |
JPH0655817B2 (en) | 1989-04-27 | 1994-07-27 | 信越化学工業株式会社 | Method for producing aminosilicone fine particle emulsion |
JPH02311581A (en) | 1989-05-25 | 1990-12-27 | Toyo Ink Mfg Co Ltd | Water-based organosilicon composition and water-based coating agent |
US5008349A (en) * | 1989-10-26 | 1991-04-16 | Dow Corning Corporation | Silicone primer compositions |
US4973643A (en) * | 1989-12-11 | 1990-11-27 | Siltech Inc. | Ether amine fuctional silicone polymers |
JPH03269570A (en) | 1990-03-20 | 1991-12-02 | Fujitsu Ltd | Display device |
JPH0411078A (en) | 1990-04-21 | 1992-01-16 | Nikka Chem Co Ltd | Silicone-based textile treating agent |
JPH0411079A (en) | 1990-04-21 | 1992-01-16 | Nikka Chem Co Ltd | Silicone-based textile treating agent |
JPH0411080A (en) | 1990-04-21 | 1992-01-16 | Nikka Chem Co Ltd | Silicone-based textile treating agent |
US5472686A (en) * | 1990-12-28 | 1995-12-05 | Nippon Unicar Company Limited | Cosmetic formulations |
JP2935874B2 (en) | 1990-06-27 | 1999-08-16 | 帝人株式会社 | Deep-colored polyester fiber fabric and method for producing the same |
US5164522A (en) * | 1990-06-29 | 1992-11-17 | Karlshamns Ab | Cationic silicones |
DE4024403A1 (en) | 1990-08-01 | 1992-02-06 | Pfersee Chem Fab | AQUEOUS DISPERSION BASED ON SILICONES, THEIR PRODUCTION AND USE |
DE69109017T2 (en) | 1990-08-10 | 1995-08-31 | Osi Specialties Inc | Silicone textile finishing agent. |
GB9103191D0 (en) * | 1991-02-14 | 1991-04-03 | Dow Corning | Platinum complexes and use thereof |
US5196499A (en) * | 1991-03-25 | 1993-03-23 | Siltech, Inc. | Terminal silicone ester quaternary compounds |
US5098979A (en) * | 1991-03-25 | 1992-03-24 | Siltech Inc. | Novel silicone quaternary compounds |
JP3043838B2 (en) | 1991-06-05 | 2000-05-22 | 日本ユニカー株式会社 | Silicone block copolymer and epoxy resin composition for molding |
GB9115592D0 (en) * | 1991-07-18 | 1991-09-04 | Dow Corning | Organosilicon crosslinking compounds having multiple functionality |
US5387417A (en) * | 1991-08-22 | 1995-02-07 | Dow Corning Corporation | Non-greasy petrolatum emulsion |
JP2588804B2 (en) | 1991-08-30 | 1997-03-12 | 東レ・ダウコーニング・シリコーン株式会社 | Polyester fiber treatment composition |
US5328685A (en) * | 1993-03-30 | 1994-07-12 | Helene Curtis, Inc. | Clear conditioning composition |
DE4344082C1 (en) | 1993-12-23 | 1994-12-22 | Goldschmidt Ag Th | Process for the preparation of organopolysiloxanes containing secondary aminoalkyl groups bonded to silicon via carbon |
FR2714402B1 (en) * | 1993-12-27 | 1996-02-02 | Rhone Poulenc Chimie | Non-yellowing textile softening process in which a composition comprising a polyorganosiloxane is used. |
JPH09111668A (en) | 1995-10-18 | 1997-04-28 | Nippon Unicar Co Ltd | Fiber treating agent containing reactive silicone-based block copolymer |
EP0824563B1 (en) * | 1996-03-04 | 2005-06-15 | General Electric Company | Silicone aminopolyalkyleneoxide block copolymers |
US5811487A (en) * | 1996-12-16 | 1998-09-22 | Dow Corning Corporation | Thickening silicones with elastomeric silicone polyethers |
DE19810803A1 (en) * | 1998-03-12 | 1999-09-16 | Wacker Chemie Gmbh | Process for the production of microencapsulated products with organopolysiloxane walls |
DE19817776A1 (en) | 1998-04-21 | 1999-10-28 | Wacker Chemie Gmbh | New linear amino-functional polydialkylsiloxane-polyether block copolymers |
DE19836260A1 (en) * | 1998-08-11 | 2000-02-24 | Wacker Chemie Gmbh | Linear polyether-polysiloxane copolymers useful as foam stabilisers or defoaming agents in aqueous emulsions and compositions |
JP3862873B2 (en) | 1998-10-21 | 2006-12-27 | 花王株式会社 | Textile treatment composition |
DE59905052D1 (en) * | 1998-11-14 | 2003-05-22 | Goldschmidt Ag Th | Polyetherquat functional polysiloxanes |
US6238684B1 (en) | 1998-12-10 | 2001-05-29 | Osi Specialties, Inc. | Terminally modified, amino, polyether siloxanes |
US6197876B1 (en) * | 1999-02-24 | 2001-03-06 | Ck Witco Corporation | Heterocyclic amine modified siloxanes |
US6255429B1 (en) * | 1999-09-02 | 2001-07-03 | Dow Corning Corporation | Amine-, polyol-, amide-functional siloxane copolymers and methods for their preparation |
US6171515B1 (en) * | 1999-09-02 | 2001-01-09 | Dow Corning Corporation | Fiber treatment composition containing amine-, polyol-, functional siloxanes |
DE60014812T2 (en) | 1999-09-02 | 2006-03-09 | Dow Corning Corp., Midland | Fiber treatment compositions containing siloxanes with amine, polyol and amide functionality |
JP4367873B2 (en) | 1999-11-18 | 2009-11-18 | 竹本油脂株式会社 | Synthetic fiber treatment agent and synthetic fiber treatment method |
JP2001172878A (en) | 1999-12-15 | 2001-06-26 | Matsumoto Yushi Seiyaku Co Ltd | Softening agent for imparting fur-like texture |
EP1116813A1 (en) | 2000-01-10 | 2001-07-18 | Dow Corning Corporation | Hydrophilic softener for textiles comprising epoxy glycol siloxane polymers and amine funtional materials |
DE10036522A1 (en) | 2000-07-27 | 2002-02-21 | Ge Bayer Silicones Gmbh & Co | Novel linear aminoacid modified polyquaternary polysiloxanes are useful in cosmetic formulations for skin and hair care, in polishes and as softeners |
DE10036532A1 (en) | 2000-07-27 | 2002-02-21 | Ge Bayer Silicones Gmbh & Co | Novel approximatelya,approximatelyc-aminofunctionalized polysiloxanes are useful in cosmetic formulations for skin and hair care, in polishes and as softeners. |
DE10036533B4 (en) | 2000-07-27 | 2005-02-03 | Ge Bayer Silicones Gmbh & Co. Kg | Use of polyquaternary polysiloxanes as washable hydrophilic plasticizers |
DE10036699A1 (en) | 2000-07-27 | 2002-02-07 | Wacker Chemie Gmbh | New amino-organosilicon compounds, useful as softener for polymer-based substrate, e.g. fibers, textile or hair, or water-proofing mineral surface, are prepared by reacting epoxy-substituted organosilicon compound with (poly)amine |
WO2002010257A1 (en) * | 2000-07-27 | 2002-02-07 | Ge Bayer Silicones Gmbh & Co. Kg | Polyammonium-polysiloxane compounds, methods for the production and use thereof |
DE10036678A1 (en) * | 2000-07-27 | 2002-02-14 | Wacker Chemie Gmbh | Organosilicon compounds containing ammonium groups |
FR2815049B1 (en) * | 2000-10-05 | 2002-12-20 | Rhodia Chimie Sa | PROCESS FOR SOFTENING, MAKING HYDROPHILIC AND NON-YELLOWING A TEXTILE MATERIAL, IN WHICH A COMPOSITION COMPRISING A POLYORGANOSILOXANE IS USED |
JP2002194675A (en) | 2000-12-19 | 2002-07-10 | Ge Toshiba Silicones Co Ltd | Fiber treating agent |
JP2002194677A (en) | 2000-12-19 | 2002-07-10 | Ge Toshiba Silicones Co Ltd | Fiber treating agent |
JP2002194676A (en) | 2000-12-19 | 2002-07-10 | Ge Toshiba Silicones Co Ltd | Fiber treating agent |
US6475568B1 (en) * | 2001-05-15 | 2002-11-05 | Crompton Corporation | Block, non-(AB)n silicone polyalkyleneoxide copolymers with tertiary amino links |
JP4862226B2 (en) | 2001-06-13 | 2012-01-25 | 東レ株式会社 | Precursor fiber for carbon fiber and method for producing carbon fiber |
DE10139963A1 (en) | 2001-08-14 | 2003-03-06 | Wacker Chemie Gmbh | Organopolysiloxanes containing quaternary ammonium groups and process for their preparation |
GB2378960A (en) | 2001-08-22 | 2003-02-26 | Unilever Plc | Fabric care composition |
JP2003119674A (en) | 2001-10-11 | 2003-04-23 | Teijin Ltd | Polyester fabric with improved feeling and method of producing the same |
US6482969B1 (en) * | 2001-10-24 | 2002-11-19 | Dow Corning Corporation | Silicon based quaternary ammonium functional compositions and methods for making them |
US6407274B1 (en) * | 2001-12-26 | 2002-06-18 | Siltech Corporation | Silicone amine oxides |
US20040053810A1 (en) | 2002-08-16 | 2004-03-18 | Tully Jo Anne | Liquid laundry compositions comprising silicone additives |
DE10247462A1 (en) * | 2002-10-11 | 2004-04-22 | Basf Ag | A polymer composition containing a hydrophobic polymer and polyisobutene terminally modified with polar groups useful in the hydrophilization of hydrophobic polymers |
GB0225292D0 (en) * | 2002-10-30 | 2002-12-11 | Unilever Plc | Fabric care composition |
JP2006505643A (en) | 2002-11-04 | 2006-02-16 | ジーイー・バイエル・シリコーンズ・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング・ウント・コンパニー・コマンジツトゲゼルシヤフト | Linear polyamino and / or polyammonium polysiloxane copolymer II |
AU2003301852A1 (en) | 2002-11-04 | 2004-06-07 | Ge Bayer Silicones Gmbh And Co. Kg | Linear polyamino and/or polyammonium polysiloxane copolymers i |
CA2504914A1 (en) * | 2002-11-04 | 2004-06-03 | Ge Bayer Silicones Gmbh & Co. Kg | Formulations used for the treatment of substrate surfaces |
DE10253152A1 (en) * | 2002-11-14 | 2004-06-03 | Rudolf Gmbh & Co. Kg Chemische Fabrik | Partially quaternized, amino-functional organopolysiloxanes and their use in aqueous systems |
DE10320631A1 (en) * | 2003-05-08 | 2004-12-09 | Wacker-Chemie Gmbh | Organosilicon compounds containing polyalkoxy radicals |
CN1938364A (en) | 2003-10-07 | 2007-03-28 | 克莱里安特财务(Bvi)有限公司 | Polysiloxanes with multiple quaternary ammonium group |
FR2865223B1 (en) | 2004-01-21 | 2007-11-16 | Rhodia Chimie Sa | USE OF A SILICONE FORMULATION FOR THE SUSTAINABLE FUNCTIONALIZATION OF TEXTILES FOR SPORTSWEAR |
DE102004006300A1 (en) | 2004-02-09 | 2005-09-08 | Schill + Seilacher "Struktol" Ag | Branched polyorganosiloxanes with quaternary ammonium groups |
US7304026B2 (en) | 2004-04-15 | 2007-12-04 | Colgate-Palmolive Company | Fabric care composition comprising polymer encapsulated fabric or skin beneficiating ingredient |
JP4630955B2 (en) | 2004-05-19 | 2011-02-09 | 大原パラヂウム化学株式会社 | Processing method of fiber fabric treated with hydrophilic / oil repellent finishing agent |
-
2008
- 2008-03-05 JP JP2010503000A patent/JP5501951B2/en not_active Expired - Fee Related
- 2008-03-05 KR KR1020097023332A patent/KR20090127950A/en active IP Right Grant
- 2008-03-05 CN CN2008800143385A patent/CN101675095B/en not_active Expired - Fee Related
- 2008-03-05 EP EP20080726484 patent/EP2139941A1/en not_active Withdrawn
- 2008-03-05 US US12/594,649 patent/US8013097B2/en not_active Expired - Fee Related
- 2008-03-05 WO PCT/US2008/002962 patent/WO2008127519A1/en active Application Filing
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5539013A (en) * | 1991-12-05 | 1996-07-23 | General Electric Company | UV-curable epoxysilicone-polyether block copolymers combined with UV-detectable dye-marker |
JPH09183854A (en) * | 1995-12-28 | 1997-07-15 | Nippon Unicar Co Ltd | Amino-modified polysiloxane-polyoxyalkylene block copolymer and aqueous composition containing the same |
WO2005103117A1 (en) * | 2004-04-20 | 2005-11-03 | Dow Corning Corporation | Silicone polyether block copolymers |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2010047993A3 (en) * | 2008-10-22 | 2010-09-16 | Dow Corning Corporation | Aminofunctional endblocked silicone polyether copolymers in personal care compositions |
US8734767B2 (en) | 2008-10-22 | 2014-05-27 | Dow Corning Corporation | Aminofunctional endblocked silicone polyether copolymers in personal care compositions |
WO2010047993A2 (en) * | 2008-10-22 | 2010-04-29 | Dow Corning Corporation | Aminofunctional endblocked silicone polyether copolymers in personal care compositions |
CN101994256A (en) * | 2009-08-17 | 2011-03-30 | 河南瑞贝卡发制品股份有限公司 | Method for preparing artificial synthetic fiber after finishing auxiliary agent and impregnation process |
WO2011127108A1 (en) | 2010-04-06 | 2011-10-13 | Dow Corning Corporation | Reactive amine-functional silicone-polyether block copolymers |
US20130030131A1 (en) * | 2010-04-06 | 2013-01-31 | Dow Corning Corporation | Reactive Amine-Functional Silicone-Polyether Block Copolymers |
US8664347B2 (en) * | 2010-04-06 | 2014-03-04 | Dow Corning Corporation | Reactive amine-functional silicone-polyether block copolymers |
WO2013148979A1 (en) | 2012-03-28 | 2013-10-03 | Dow Corning Corporation | Amphiphilic resin-linear organosiloxane block copolymers |
US10066060B2 (en) | 2012-12-28 | 2018-09-04 | Dow Corning Toray Co., Ltd. | Production method for high-purity organosilicon compound |
WO2014104257A1 (en) | 2012-12-28 | 2014-07-03 | 東レ・ダウコーニング株式会社 | Method for manufacturing high-purity organosilicon compound |
WO2014151587A2 (en) | 2013-03-15 | 2014-09-25 | Dow Corning Corporation | Amphiphilic resin linear copolymers for pharmaceutical drug delivery applications |
EP2789642A1 (en) * | 2013-04-09 | 2014-10-15 | Evonik Industries AG | Polysiloxane-Polyether copolymers with amino and/or quaternary ammonium groups linked to the polyether part, and process to prepare such copolymers |
US9346919B2 (en) | 2013-04-09 | 2016-05-24 | Evonik Degussa Gmbh | Polysiloxane-polyether copolymers with amino groups and/or quaternary ammonium groups in the polyether moiety and processes for the preparation thereof |
WO2017182061A1 (en) | 2016-04-19 | 2017-10-26 | Wacker Chemie Ag | Amino-organopolysiloxane and preparation method thereof |
US10954342B2 (en) | 2016-04-19 | 2021-03-23 | Wacker Chemie Ag | Amino-organopolysiloxanes and preparation method therefor |
CN107814941A (en) * | 2017-11-13 | 2018-03-20 | 清远市宏图助剂有限公司 | A kind of microwave preparation of the quaternized block organosilicon polymer of smooth type |
CN107814941B (en) * | 2017-11-13 | 2020-09-15 | 清远市宏图助剂有限公司 | Microwave preparation method of smooth quaternary ammonium block organic silicon polymer |
CN112680973A (en) * | 2020-12-28 | 2021-04-20 | 绍兴海成化工有限公司 | In-cylinder silicone oil and preparation method thereof |
CN112680973B (en) * | 2020-12-28 | 2022-06-17 | 绍兴海成化工有限公司 | In-cylinder silicone oil and preparation method thereof |
CN113501962A (en) * | 2021-08-07 | 2021-10-15 | 佛山市顺德区德美瓦克有机硅有限公司 | Low-yellowing hydrophilic block polyether amino silicone oil and preparation method thereof |
CN113501962B (en) * | 2021-08-07 | 2022-08-19 | 佛山市顺德区德美瓦克有机硅有限公司 | Low-yellowing hydrophilic block polyether amino silicone oil and preparation method thereof |
Also Published As
Publication number | Publication date |
---|---|
US8013097B2 (en) | 2011-09-06 |
KR20090127950A (en) | 2009-12-14 |
US20100048795A1 (en) | 2010-02-25 |
EP2139941A1 (en) | 2010-01-06 |
CN101675095A (en) | 2010-03-17 |
CN101675095B (en) | 2012-11-28 |
JP5501951B2 (en) | 2014-05-28 |
JP2010523790A (en) | 2010-07-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US8013097B2 (en) | Silicone polyether block copolymers having organofunctional endblocking groups | |
CN108884323B (en) | Amino-organopolysiloxanes and method for the production thereof | |
KR100890982B1 (en) | Block, non-abn silicone polyalkyleneoxide copolymers with tertiary amino links | |
JP3476214B2 (en) | Organosiloxanes with nitrogen-containing and ether-containing residues | |
US8742154B2 (en) | Block ABA silicone polyalkyleneoxicie copolymers, methods of preparation, and applications for employing the same | |
US7896929B2 (en) | Treating textiles with silicone polyether-amide block copolymers | |
EP0399706B1 (en) | Method of treating fibrous materials | |
EP2271713B1 (en) | Low viscosity, high molecular weight linear random-block silicone polyalkyleneoxide copolymers | |
KR101003798B1 (en) | Hydrophilic amino modified polysiloxane and method for preparing thereof | |
KR100777010B1 (en) | Amino oil having goods alkali resistance property | |
WO2013177531A1 (en) | Composition and method for treating textiles |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200880014338.5 Country of ref document: CN |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 08726484 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 12594649 Country of ref document: US |
|
ENP | Entry into the national phase |
Ref document number: 2010503000 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2008726484 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 20097023332 Country of ref document: KR Kind code of ref document: A |