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
  • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • D06M15/356—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms
  • D06M15/3568—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of other unsaturated compounds containing nitrogen, sulfur, silicon or phosphorus atoms containing silicon
• • 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
  • C08G77/12—Polysiloxanes containing silicon bound to hydrogen
• • 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
  • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing 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
  • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
  • C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl 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
  • C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
  • C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy 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
  • C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
  • C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
  • C08L83/04—Polysiloxanes
  • C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L83/00—Compositions of 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; Compositions of derivatives of such polymers
  • C08L83/04—Polysiloxanes
  • C08L83/08—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
  • 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
  • D06M15/65—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing epoxy groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L2205/00—Polymer mixtures characterised by other features
  • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
• • 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
  • D06M2101/10—Animal fibres
  • D06M2101/12—Keratin fibres or silk
• • 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
  • D06M2200/35—Abrasion, pilling or fibrillation resistance
• • 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
  • D06M2200/45—Shrinking resistance, anti-felting properties
• • 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
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
  • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
  • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
  • Y10T442/2762—Coated or impregnated natural fiber fabric [e.g., cotton, wool, silk, linen, etc.]
  • Y10T442/277—Coated or impregnated cellulosic fiber fabric
  • Y10T442/2803—Polymeric coating or impregnation from a silane or siloxane not specified as lubricant or water repellent

Definitions

• the present invention relates to a composition and method for treating textiles to impart one or more desirable properties thereto such as shrink resistance, wrinkle resistance, durable press, anti-pilling (in the case of woolen fabrics and wool blends), smoothness and elastic hand feel.
• the present invention fulfills the need for a composition and method for imparting at least one textile property-enhancing characteristic thereto, e.g., shrink resistance, wrinkle resistance, durable press, anti-pilling (in the case of woolen fabrics and wool blends), smoothness and/or elastic desirable hand feel, unaccompanied by the emission of harsh chemical odors and/or excessive or accelerated loss of strength of the treated textiles.
• at least one textile property-enhancing characteristic e.g., shrink resistance, wrinkle resistance, durable press, anti-pilling (in the case of woolen fabrics and wool blends), smoothness and/or elastic desirable hand feel, unaccompanied by the emission of harsh chemical odors and/or excessive or accelerated loss of strength of the treated textiles.
• M A is (OR R y SiOi / ,
• D B is R 3 2 Si0 2 2 ;
• D c is R 4 R 5 Si0 2/2 ;
• T D is R 6 Si0 3 2 ;
• T E is R 7 Si0 3/2 ; in which
• R 1 each instance, is independently hydrogen or a monovalent hydrocarbon group of from 1 to 22 carbon atoms;
• R 2 , R 3 , R 4 and R 6 each instance, is independently a monovalent hydrocarbon or alkoxy group of from 1 to 22 carbon atoms;
• R and R each instance, is independently a monovalent hydrocarbon group of from 1 to 22 carbon atoms and substituted with at least one amino and/or oxirane group;
• At least one macromonomer (ii) which is an oligomer or polymer containing at least two silylhydride ( ⁇ C-SiH) functional groups per molecule;
• a method for treating a textile to impart at least one property-enhancing characteristic thereto comprising: a) applying to a textile an amount of curable composition which after undergoing curing provides at least one cured resin composition which is effective to impart at least one textile property enhancing characteristic thereto, the curable composition comprising:
• M A is (OR R y SiOia
• D B is R 3 2 Si0 2 2 ;
• D c is R 4 R 5 Si0 2/2 ;
• T D is R 6 Si0 3 2 ;
• T E is R 7 Si0 3 2 ; in which
• R 1 each instance, is independently hydrogen or a monovalent hydrocarbon group of from 1 to 22 carbon atoms;
• R 2 , R 3 , R 4 and R 6 each instance, is independently a monovalent hydrocarbon or alkoxy group of from 1 to 22 carbon atoms;
• R 5 and R 7 each instance, is independently a monovalent hydrocarbon group of from 1 to 22 carbon atoms and substituted with at least one amino and/or oxirane group; and, 1 ⁇ a ⁇ 19, 1 ⁇ b ⁇ 9999, 1 ⁇ c ⁇ 19, 0 ⁇ d ⁇ 9, 0 ⁇ e ⁇ 9 and 0 ⁇ y ⁇ 3;
• At least one macromonomer (ii) which is an oligomer or polymer containing at least two silylhydride ( ⁇ C-SiH) functional groups per molecule;
• textile as used herein shall be understood to include blended and non-blended textile fibers and strands, knitted, woven, non- woven or otherwise constructed fabrics, and finished and semi-finished textile articles and subunits thereof such as garments and garment sections, etc.
• the curing of macromonomers (i) and (ii) involves the reaction of hydroxyl and/or alkoxyl groups present in each M A moiety of macromonomer(s) (i) with silyl hydride ( ⁇ C-SiH) groups present in macromonomer(s) (ii).
• the curing reaction results in the condensation of macromonomers (i) and (ii) to form cured resin composition possessing -SiO- linkages accompanied by the release of hydrogen;
• the reactive groups in moieties M A are alkoxy (i.e., the case where each R 1 group is a monovalent hydrocarbon and each R 2 group, where present, is alkoxy)
• the curing reaction will also result in condensation of macromonomers (i) and (ii) to form cured resin composition possessing -SiO- linkages but with the splitting out of hydrocarbon R1H wherein R 1 is a monovalent hydrocarbon group as defined above.
• the present invention also includes the cured resin composition resulting from the curing reaction of macromonomers (i) and (ii) contained in the aforedescribed curable resin composition, textile treated with the curable resin composition and textile containing cured resin composition resulting from the curing reaction of macromonomers (i) and (ii).
• a textile containing the cured resin composition is not subject to the release of disagreeable odors as are textiles treated with known and conventional formaldehyde derivative-based textile treating agents such as those referred to above.
• Use of the textile-treating composition of the invention permits one to dispense with the use of such formaldehyde derivatives entirely or to reduce their presence to such a level that formaldehyde release is no longer a significant problem.
• the curable textile-treating composition of this invention and the resulting cured resin composition contain no, or at most 20 weight percent, formaldehyde derivative(s) as auxiliary anti-wrinkling additive(s).
• the curable composition herein, the resulting cured resin composition and textile treating method of this invention are particularly advantageous for providing shrink resistant and wrinkle resistant textiles and textiles exhibiting favorable strength retention and hand characteristics.
• the cured resin composition of the invention advantageously imparts an effective anti-pilling characteristic thereto.
• the curable composition of the present invention includes at least one macromonomer (i) which is a polysiloxane of general formula (I):
• M A is (OR R ySiOia;
• D B is R 3 2 Si0 2/2 ;
• D c is R 4 R 5 Si0 2 2 ;
• T D is R 6 Si0 3/2 ;
• T E is R 7 Si0 3 2 ; in which R , each instance, is independently hydrogen or a monovalent hydrocarbon group of from 1 to 22 carbon atoms;
• R 2 , R 3 , R 4 and R 6 each instance, is independently a monovalent hydrocarbon or alkoxy group of from 1 to 22 carbon atoms;
• R and R each instance, is independently a monovalent hydrocarbon group of from 1 to 22 carbon atoms and substituted with at least one amino and/or oxirane group;
• each R 1 independently is hydrogen or a monovalent hydrocarbon group preferably having from 1 to 6 carbon atoms and more preferably from 1 to 4 carbon atoms.
• Each R 2 , R 3 , R 4 and R 6 independently is preferably a monovalent hydrocarbon or alkoxy group of from 1 to 6 carbon atoms, e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy and isomers thereof, and more preferably, from 1 to 4 carbon atoms, e.g., methoxy, ethoxy, propoxy, butoxy, and isomers thereof.
• Each R 5 and R 7 group independently is preferably a monovalent linear or branched hydrocarbon group of from 2 to 20 carbon atoms, and more preferably, from 2 to 10 carbon atoms.
• the values are 2 ⁇ a ⁇ 9, 25 ⁇ b ⁇ 999, 1 ⁇ c ⁇ 9, 0 ⁇ d ⁇ 5, 0 ⁇ e ⁇ 5 and 0 ⁇ y ⁇ 2 and more preferably, 2 ⁇ a ⁇ 5, 100 ⁇ b ⁇ 999, l ⁇ c ⁇ 7, 0 ⁇ d ⁇ 3, 0 ⁇ e ⁇ 3 and 0 ⁇ y ⁇ 1.
• Monomer(s) (i) preferably have a number average molecular weight ranging from 100 to 200,000 and preferably from 1000 to 100,000.
• the macromonomer (i) component(s) of the curable composition can be obtained by combining at least one cyclic and/or linear siloxane, at least one alkoxy- terminated functional silane, optional catalyst, optional surfactant(s) and water to provide a reaction mixture and heating the mixture to a temperature and for a period of time sufficient to achieve substantially complete conversion of the siloxane and alkoxy silane reactants to monomer(s) (i).
• a reaction mixture can be prepared by combining at least one silanol group-containing cyclic siloxane such as hexamethylcyclotrisiloxane,
• octamethylcyclotetrasiloxane or decamethylcyctopentasiloxane (commonly referred to, respectively, as D 3 , D 4 and D 5 , available from Momentive Performance Materials Inc.) and/or at least one silanol-containing linear siloxane with at least one aminoalkoxysilane, e.g., gamma-aminopropyl trimethoxy silane, aminopropyl triisopropoxy silane, and the like
• optional catalyst(s) e.g., a strong base such as sodium hydroxide, potassium hydroxide, ammonium hydroxide, and the like
• optional surfactant(s) e.g., anionic surfactant(s) such as polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, and the like, anionic surfactant(s) such as sodium lauryl sulfate, sodium dodecybenzene sufonate, and
• the curable resin-forming composition of the invention also includes at least one macromonomer (ii) which is an oligomer or polymer containing at least two silylhydride ( ⁇ C-SiH) functional groups per molecule.
• macromonomer (ii) which is an oligomer or polymer containing at least two silylhydride ( ⁇ C-SiH) functional groups per molecule.
• silylhydride ( ⁇ C-SiH)-containing macromonomers (ii) can be selected from among those of general formula (II):
• M is R 8 R 9 R 10 SiO 1/2 ;
• M ⁇ is R n R 12 R 13 SiOi /2 ;
• D is R 14 R 15 Si ⁇ 3 ⁇ 4/ 2 ;
• D ⁇ is R 16 R 17 Si0 2 2 ;
• T is R 18 Si0 3/2 ;
• T is R 19 Si0 3 2 ;
• Q is Si0 4/2 ; in which
• R 8 , R 9 , R 10 , R 14 , R 15 and R 18 each instance, independently is alkyl, aryl or aralkyl of up to 22 carbon atoms;
• R 11 , R 16 and R 19 each is hydrogen
• R 12 , R 13 and R 17 each instance, independently is hydrogen or alkyl, aryl or aralkyl of up to 22 carbon atoms;
• f, g, h, i, j, k and 1 are each integers wherein:
• f, g, j, k and 1 are each greater than or equal to 0 and less than or equal to 50,
• R 8 , R 9 , R 10 , R 12 , R 14 , R 15 and R 18 each instance, independently is alkyl of from 1 to 6 carbon atoms, and still more preferably methyl or ethyl, R 13 is hydrogen and 4 ⁇ i ⁇ 30; 1 ⁇ n ⁇ 15 and h, j, k, 1 and m are each 0.
• silylhydride-containing macromonomer(s) (ii) include any of the linear, branched and/or crosslinked polymers having any two or more of a combination of M, D, T, and Q groups, as defined above, and having at least two silylhydride functional groups.
• macromonomer(s) (ii) of general formula (II) is an
• MD-type of polysiloxane having one or more M and/or M H groups in combination with one or more D and/or groups, wherein M represents Si(CH 3 ) 3 0— , represents
• Suitable MD-type polysiloxanes for monomer (ii) include the M D virginM , M H D H TrustM, M3 ⁇ 43 ⁇ 4,M, ⁇ ⁇ ⁇ ⁇ till ⁇ ⁇ , M H O H CommunityO m M H , MD ⁇ M, and ⁇ ,,, ⁇ classes of MD- type polysiloxanes, and combinations thereof, wherein m and n each represent an integer at least 1 to 500.
• the D ⁇ groups can also be randomly incorporated (i.e., not as a block) among the D groups.
• ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ / ⁇ ⁇ can represent a polymer wherein n represents 5-20 and m represents 50-1500, and wherein the 5-20 D ⁇ groups are randomly incorporated among the 50-1500 D groups.
• M and D groups can independently have a higher number of silylhydride functional groups such as, for example, H 2 Si(CH 3 )0— and H 3 SiO— groups for M H or— Si(H) 2 0— for D H .
• Macromonomer(s) (ii) preferably have a number average molecular weight of from 200 to 30,000 and preferably from 500 to 20,000.
• the macromonomer (ii) component(s) of the curable composition can be obtained by carrying out the cohydrolysis reaction of two or more different alkylhalosilanes, e.g., SiH(CH 3 )Cl 2 with one or more of Si(CH 3 ) 3 Cl, SiH(CH 3 ) 2 Cl, Si(CH 3 ) 2 Cl 2 and
• Si(CH 3 )Cl 3 in the presence of water at, e.g., from 5 to 30 °C for from 5 to 30 hours.
• TSF 484 and SS 4300C Two commercially available macromonomers (ii) are TSF 484 and SS 4300C, both from Momentive Performance Materials Inc.
• the curable textile-treating composition of the invention includes at least one catalyst (iii) effective for catalyzing the curing reaction of macromonomers (i) and (ii) therein, to produce cured resin composition in which the macromonomer units are linked together through -SiO- linkages.
• Catalyst (iii) may be selected from the metallic fatty acid salts, amines, quaternary ammonium hydroxides, Lewis acids, and the like.
• useful metallic fatty acid salts include dibutyltin diacetate, dibutyltin dioctoate, dibutyltin dilaurate, dibutyltin dioleate, dibutyltin distearate, tributyltin acetate, tributyltin octoate, tributyltin laurate, dioctyltin diacetate, dioctyltin dilaurate, diethyltin dioleate and monomethyltin dioleate which have hydrocarbon groups directly bonded to metallic atoms, and zinc octenoate, iron octenoate and tin octenoate which do not have hydrocarbon groups directly bonded to metallic atoms.
• useful amines include organic amines such as monomethylamine, dimethylamine, monoethylamine, diethylamine, ethylenediamine and hexamethylenetetramine, amino group-containing silane compounds such as a- aminopropyltriethoxysilane and their salts.
• useful quaternary ammonium hydroxides include tetramethylammonium hydroxide, dimethylbenzyl ammonium hydroxide and their salts.
• useful Lewis acids include FeCl 3 , A1C1 3 , ZnCl 2 , ZnBr 2 , as well as those Lewis acids having greater solubility in siloxane media disclosed in U.S. Patent No. 7,064,173, the entire contents of which are incorporated by reference herein.
• the curable composition of this invention is provided as two, or even three, isolated units, i.e., macromonomer(s) (i) as one unit, macromonomer(s) (ii) as the second unit with catalyst(s) (iii) and optional component(s) (iv) added to unit (i) and/or unit (ii) or, preferably, provided as its own separate third unit.
• predetermined amounts of each unit are combined employing known and conventional mixing equipment and procedures to provide the curable textile-treating composition of the invention.
• macromonomers (i) and (ii), and if maintained separately from the macromonomers, catalyst(s) (iii), are provided as aqueous emulsions employing suitable surfactant(s) as emulsifier(s).
• suitable surfactant(s) as emulsifier(s).
• the use of surfactant(s) therefore allows both the curable composition and the subsequently cured resin to be applied to the textile as a water-based system, one containing no or at most only a minor amount by weight, e.g., not exceeding 20 weight percent of the total curable composition, of one or a mixture of organic solvents.
• the curable textile-treating composition of the invention is substantially devoid of organic solvent(s) and thus can be regarded as an essentially organic solvent-free system.
• Useful surfactants for the emulsification of the textile-treating composition herein can be selected from known and conventional nonionic, cationic or anionic surfactants.
• Useful nonionic surfactants include those having hydrophilic lipophilic balance (HLB) between 5 and 25.
• Some useful nonionic surfactants of this category are polyoxyalkylene alkyl ethers, polyoxyalkylene sorbitan esters, polyoxyalkylene esters and polyoxyalkylene alkylphenyl ethers.
• Some specific examples of primary surfactant are Brij 35, Brig 35L, Brij 58, Brij 78, Brij 98, Brij 700, and Brij 721, all products of Croda.
• Cationic surfactants useful for emulsifying the components of the curable composition of this invention include compounds containing quaternary ammonium hydrophilic moieties in the molecule which are positively charged such as quaternary ammonium salts or bases represented by R ⁇ R ⁇ NF 1" X " where R 3 to R 6 are alkyl groups containing from 10 to 30 carbon atoms, or alkyl groups derived from tallow, coconut oil or soy and X is hydroxide or halogen, e.g., chlorine or bromine.
• Dialkyl dimethyl ammonium salts which can be used are represented byR 7 R 8 N + (CH 3 ) 2 X " where R 7 and R 8 are alkyl groups containing from 10 to 30 carbon atoms or alkyl groups derived from tallow, coconut oil or soy and X is hydroxide or halogen.
• Monoalkyl trimethyl ammonium salts which can be used herein are represented by R 9 N + (CH 3 ) 3 X " where R 9 is an alkyl group containing from 10 to 30 carbon atoms or an alkyl group derived from tallow, coconut oil or soy and X is halogen.
• quaternary ammonium salts and hydroxides are dodecyltrimethyl ammonium chloride/lauryltrimethyl ammonium chloride (LTAC), cetyltrimethyl ammonium chloride (CTAC), didodecyldimethyl ammonium bromide, dihexadecyldimethyl
• ammoniumchloride dihexadecyldimethyl ammonium bromide, dioctadecyldimethyl ammonium chloride, dieicosyldimethyl ammonium chloride, didocosyldimethyl ammonium chloride, dicoconutdimethyl ammonium chloride, ditallowdimethyl ammonium chloride, ditallowdimethylammonium bromide and cetyltrimethyl ammonium hydroxide.
• Adogen Adogen
• Arquad Tomah and Variquat.
• Anionic surfactants useful for emulsifying the components of the curable composition of this invention include sulfonic acids and their salt derivatives. Some representative examples of useful anionic surfactants are alkali metal sulfosuccinates;
• hydrocarbons such as sodium alpha-naphthalene monosulfonate; condensation products of naphthalene sulfonic acids with formaldehyde; sodium octahydro anthracene sulfonate; alkali metal alkylsulfates; ether sulfates having alkyl groups of eight or more carbon atoms such as sodium lauryl ether sulfate; and alkylaryl sulfonates having one or more alkyl groups of eight or more carbon atoms such as hexadecylbenzene sulfonic acid and C 20 alkylbenzene sulfonic acid.
• Additional optional components of the curable composition of the invention include minor amounts of one or more organic solvents such as monohydric and polyhydric alcohols (when aqueous emulsions of curable and cured compositions are employed as described above), pH buffering agents such as strong or weak acids, e.g., HC1, H 2 S0 4 , phosphoric, benzoic or citric acid (the pH of the compositions are preferably less than 5.0), rewetting agents, viscosity modifiers such as electrolytes, for example, calcium chloride, anti- gelling agents, fragrances, fragrance carriers, fluorescers, colorants, hydrotropes, antifoaming agents, anti-redeposition agents, enzymes, optical brightening agents, opacifiers, stabilizers such as guar gum and polyethylene glycol, anti-shrinking agents, fabric crisping agents, anti- spotting agents, soil-release agents, germicides, fungicides, biocides, anti-oxidants, anti- corrosion agents,
• These and other optional components can be incorporated in the copolymer-forming composition in known and conventional amounts.
• the optional components can be incorporated in one or more of the aforementioned individual reaction component units to be later combined to provide the copolymer-forming composition herein (with due attention to storage stability concerns) or they can be added individually, in various sub-combinations or all at once when several optional components are utilized during or after the combining and mixing operation resulting in the fully formulated copolymer-forming composition.
• the amount of water used in the preparation of aqueous emulsions of macromonomers (i) and (ii) should be adequate to provide either an oil-in-water emulsion or a water-in-oil emulsion of good stability.
• the amount of water can be in the range of from about 20 parts by weight (pbw) to about 2000 pbw, preferably from about 100 pbw to about 500 pbw, per 100 pbw of the total amount of monomers (i) and (ii).
• Fully formulated curable compositions of this invention can be prepared by merely mixing and agitating macromonomers (i) and (ii), catalyst(s) (iii) and optional additional component(s) (iv) with a stirrer, e.g., a homogenizer.
• the components of the copolymer-forming composition can be introduced together into a vessel in a specific amount or as a pre-mixture of macromonomers (i) and (ii), catalyst(s) (iii) and optional component(s) (iv) followed by the addition of water.
• aqueous emulsion of curable composition of the oil-in-water or water-in-oil type is readily and conveniently obtained to provide the cellulosic textile-treating composition herein.
• the length of time for agitation depends upon the balance of the interfacial properties between the components of the curable composition including any optional surfactant(s) (iv) and water.
• Table 1 below sets forth suitable broad and preferred ranges for each of monomers (i) and (ii), catalyst(s) (iii) and optional components such as surfactants (iv), water, etc., for the copolymer-forming composition of the invention.
• Table 1 Weight Ranges of Components of the Curable Textile-Treating Composition As a Percent of the Total Composition
• textiles for treatment herein include nylon (polyarnides), polyester, wool, cotton, flax, hemp, jute and ramie, and the like, including blends of any of the foregoing with one or more other natural or synthetic fibers.
• cotton and wool can be blended with fibers derived from polyesters, polyarnides (e.g., nylons), acrylics (e.g., polyacrylonitrile), polyolefins, polyvinyl chloride, and polyvinylidene chloride.
• the textiles based on blends of fibers include at least 35 to 40 percent by weight, and most preferably at least 50 to 60 percent by weight, of cotton or other cellulosic fiber.
• the curable cellulosic textile treating composition of the present invention advantageously containing one or more surfactants (iv) as described above, can be diluted with water to a desired active level and applied to a fiber or textile by any suitable means such as spraying, dipping, padding, kiss roll, and the like. Removal of any treating composition can be achieved by using a mangle, centrifugal separator, or the like, to control the amount of liquid absorbed by the textile. Drying can be effected with or without heat. Depending upon the particular textile being treated, when drying is performed by application of heat, the drying temperature can generally range from 70° to 130°C and its duration from 1 to 30 minutes. After removal of any excess emulsion, subsequent heating to complete curing is usually required.
• Effective curing temperatures generally range from 130°C to 200°C for periods of from 1 to 30 minutes.
• the cured resin(s) impart one or more advantageous properties to the treated textile, e.g., shrink resistance, wrinkle resistance and/or desirable hand feel characteristics.
• the amount of aqueous emulsion of curable composition that a treated textile absorbs will generally range from 0.1 to about 5 weight percent based on the total weight of macromonomers (i) and (ii). It may be desirable to prepare emulsified reaction component units having higher macromonomer contents in order to reduce shipping and/or handling costs and then to dilute the emulsions with water immediately prior to use.
• macromonomer contents of the curable composition herein can range from 10 to 80 weight percent, preferably from 20 to 40 weight percent, based on the total weight of the
• Examples 4 to 6 illustrate the preparation of three different macromonomers (ii) and Examples 7-9 illustrate the preparation of three different catalysts (iii). In these examples, all indicated percents and parts are by weight.
• octamethylcyclotetrasiloxane (D 4 ) was charged to the vessel and mixed for 50min under high agitation (600rpm). The pre-emulsion was homogenized with the first pressure 50kg and the second pressure 500kg to provide an emulsion. Thereafter catalyst (2.0% of an aqueous solution of 10% KOH in water) was charged into the vessel. The vessel was then slowly heated to 80°C for 5 hours, and then the temperature was decreased to 45°C and maintained for 12 hours. Thereafter, 0.2% of acetic acid was charged to neutralize the solution.
• 16 parts of a silanol terminated polysiloxane (viscosity: 40,000 cps) was mixed with 8 parts TERGITOL TMN-6 and then 76 parts water was added slowly at 800-1000 rpm to form a homogeneous mixture.
• catalyst (2.0% of an aqueous solution of 10% KOH in water) was charged into the vessel.
• the vessel was then slowly heated to 80°C for 5 hours, and then the temperature was decreased to 45°C and maintained for 12 hours. Thereafter, 0.2% of acetic acid was charged to neutralize the solution.

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• 2013
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