[go: up one dir, main page]

EP2215304A2 - Textiles traités au moyen de copolymères de composés époxy et des amino silanes - Google Patents

Textiles traités au moyen de copolymères de composés époxy et des amino silanes

Info

Publication number
EP2215304A2
EP2215304A2 EP08848440A EP08848440A EP2215304A2 EP 2215304 A2 EP2215304 A2 EP 2215304A2 EP 08848440 A EP08848440 A EP 08848440A EP 08848440 A EP08848440 A EP 08848440A EP 2215304 A2 EP2215304 A2 EP 2215304A2
Authority
EP
European Patent Office
Prior art keywords
emulsion
subscript
composition
carbon atoms
zero
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP08848440A
Other languages
German (de)
English (en)
Inventor
Benjamin Falk
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Momentive Performance Materials Inc
Original Assignee
Momentive Performance Materials Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Momentive Performance Materials Inc filed Critical Momentive Performance Materials Inc
Priority to EP12007526.2A priority Critical patent/EP2617893A3/fr
Priority to EP12007512.2A priority patent/EP2617892B1/fr
Priority to EP12007511.4A priority patent/EP2617891A3/fr
Publication of EP2215304A2 publication Critical patent/EP2215304A2/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/65—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing epoxy groups
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/30—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests characterised by the surfactants
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/68—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water
    • C02F1/682—Treatment of water, waste water, or sewage by addition of specified substances, e.g. trace elements, for ameliorating potable water by addition of chemical compounds for dispersing an oily layer on water
    • 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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
    • C08G59/4085—Curing agents not provided for by the groups C08G59/42 - C08G59/66 silicon containing compounds
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • 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
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds 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
    • C08G77/38—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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • 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
    • D06M15/507—Polyesters
    • D06M15/513—Polycarbonates
    • 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
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
    • C02F2103/02—Non-contaminated water, e.g. for industrial water supply
    • C02F2103/023—Water in cooling circuits
    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F2305/00—Use of specific compounds during water treatment
    • C02F2305/04—Surfactants, used as part of a formulation or alone

Definitions

  • the present invention relates to novel copolymers formed as the reaction product of epoxy compounds and amino silanes.
  • US patent 4,062,999 A describes a process for treating textile fibers with a mixture of an amino functional silane and an epoxy functional silicone. The unreacted mixture is applied to the fiber then heat treated in an oven.
  • US patent 4,359,545 A describes the process of reacting an amino functional silicone and an epoxy functional silicone onto a textile surface. The blend is applied to a textile then heat-treated in an oven.
  • US patent 5,384,340 describes the use of a moisture and or photo curable coatings system. The process involves first reacting an epoxy or methacryl functional silane with an excess of an amino functional silicone. The remaining unreacted amino groups are then reacted with an epoxy or isocyano functional vinyl containing molecule. The resulting material contains both moisture curable alkoxy silane groups and free radical curable vinyl groups.
  • EP 1,116,813Al describes a textile treatment composition containing siloxanes having epoxy- and glycol- functionalities and either an aminosilane or a silicone quaternary ammonium compound. The composition is preferably formulated as an aqueous emulsion. The emulsion is applied to the textile surface followed by heat treatment to cure the mixture.
  • US patent 5,102,930 A describes a silicone-based fabric finishing agent that is suitable for finishing a fabric material containing keratinous fibers, e.g., wool.
  • the fabric finishing agent is an aqueous emulsion of a hydroxy- containing organopolysiloxane with an admixture of a mixture of colloidal silica and a reaction product of an amino-functional alkoxy silane or a hydrolysis product thereof with an acid anhydride, an epoxy-functional alkoxy silane compound and a curing catalyst.
  • US patent 6,475,568 Bl describes the synthesis of non- crosslinkable silicone polyether non-(AB)n materials that do not contain silane or reactive groups. Modified silicones can exhibit a variety of physical properties. The polymers can be modified to be hydrophilic, lipophilic and hydrophobic depending on the nature of the organic substituents. Recently, linear alternating copolymers and linear random copolymers have been made using alkyl or polyether, and polydimethylsiloxane units. These materials have shown utility in a variety of applications including personal care (hair conditioners, skin care and color cosmetics), textile treatments, hard surface modifiers, agricultural adjuncts, and the like. Unfortunately these materials are liquids and show limited durability when applied to a surface.
  • the present invention provides for a composition
  • a composition comprising the reaction product of a) an oxirane or oxetane compound comprising at least two oxirane or oxetane groups; and
  • R 1 is chosen from the group consisting of H or a monovalent hydrocarbon radical containing one to 20 carbon atoms;
  • R 2 is selected from a group consisting of a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;
  • R 4 is a hydrocarbon radical that contains 3 to 200 carbon atoms
  • R 5 is selected from a group consisting of oxygen or a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;
  • R 3 , R 6 , R 7 , and R 8 are each independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 200 carbon atoms;
  • the subscript b is zero or a positive number and has a value ranging from 0 to 3;
  • the subscripts d and e are zero or positive and have a value ranging from 0 to 3 subject to the limitation that (d + e) ⁇ 3.
  • the present invention provides for a composition
  • a composition comprising the reaction product of a) an oxirane or oxetane compound comprising at least two oxirane or oxetane groups; and
  • R 1 is chosen from the group consisting of H or a monovalent hydrocarbon radical containing one to 20 carbon atoms;
  • R 2 is selected from a group consisting of a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;
  • R 4 is a hydrocarbon radical that contains 3 to 200 carbon atoms
  • R 5 is selected from a group consisting of oxygen or a divalent linear or branched hydrocarbon radical consisting of 1-60 carbons;
  • R 3 , R 6 , R 7 , and R 8 are each independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 200 carbon atoms;
  • the subscript b is zero or a positive number and has a value ranging from 0 to 3;
  • the present invention further provides for such reaction product compositions where the oxirane or oxetane compound is selected from the group consisting of siloxanes, hydrocarbons and polyethers particularly where the oxirane or oxetane compound is a siloxane having the formula:
  • M PE R 12 R 13 (.CH2CH(R 14 )(R 15 ) t O(R 16 ) u (C2H 4 O)v(C3H 6 O)w(C4H8 ⁇ ) ⁇ R 17 )SiO 1 /2;
  • D PE R2 0 (. CH2CH ( R 14 )( R 15 ) t O(R 16 ) u (C 2 H4 ⁇ )v(C3H 6 O)w(C4H8 ⁇ ) ⁇ R 17 )SiO 2 / 2
  • D E R 20 R E SiO 2 /2.
  • T R 21 SiO 3 /2;
  • T H HSiO 3 / 2 ;
  • T PE (-CH 2 CH(R 14 )(R 15 ) t O(R 16 ) u (C 2 H4 ⁇ )v(C3H 6 O)w(C4H8 ⁇ ) ⁇ R 17 )Si ⁇ 3/2;
  • T E R E SiO 3 /2;
  • R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 are each independently selected from the group of monovalent hydrocarbon radicals having from 1 to 60 carbon atoms;
  • R 14 is H or a 1 to 6 carbon atom alkyl group
  • R 15 is a divalent alkyl radical of 1 to 6 carbons
  • R 16 is selected from the group of divalent radicals consisting of -C 2 H 4 O-, -C3H6O- , and -C 4 HsO-
  • R 17 is H, a monofunctional hydrocarbon radical of 1 to 6 carbons, or acetyl
  • R E is independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from one to sixty carbon atoms;
  • the subscript f may be zero or positive subject to the limitation that when the subscript f is zero, h must be positive;
  • the subscript h may be zero or positive subject to the limitations that when h is zero, the subscript f must be positive, and that the sum of the subscripts h, 1 and p is positive;
  • the subscript k is zero or positive and has a value ranging from about 0 to about 1,000;
  • the subscript 1 is zero or positive and has a value ranging from about 0 to about 400 subject to the limitation that the sum of the subscripts h, 1 and p is positive;
  • the subscript 0 is zero or positive and has a value ranging from 0 to about 50;
  • the subscript p is zero or positive and has a value ranging from 0 to about 30 subject to the limitation that the sum of the subscripts h, 1 and p is positive;
  • the subscript s is zero or positive and has a value ranging from 0 to about 20;
  • the subscript i is zero or positive and has a value ranging from 0 to about 20;
  • the subscript m is zero or positive and has a value ranging from 0 to about 200;
  • the subscript q is zero or positive and has a value ranging from 0 to about 30;
  • the subscript j is zero or positive and has a value ranging from 0 to about 2;
  • n is zero or positive and has a value ranging from 0 to about 20;
  • the subscript r is zero or positive and has a value ranging from 0 to about 30;
  • v is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v + w + x) > 0;
  • the subscript w is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v + w + x) > 0;
  • the subscript x is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that (v + w + x) > 0;
  • oxirane or oxetane compound is a hydrocarbon having the formula:
  • R 23 and R 24 are each selected from the group consisting of H or a linear or branched monovalent hydrocarbon radical of 1 to 200 carbons;
  • R 26 and R 28 are independently a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from 3 to 12 carbon atoms;
  • R 27 is selected from the group of divalent radicals consisting of - C 2 H 4 O-, -C 3 H 6 O- , and -C 4 H 8 O-;
  • the subscript ⁇ is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that ( ⁇ + ⁇ + ⁇ ) > 0;
  • the subscript ⁇ is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that ( ⁇ + ⁇ + ⁇ ) > 0;
  • the subscript ⁇ is zero or positive and has a value ranging from 0 to about 100 subject to the limitation that ( ⁇ + ⁇ + ⁇ ) > 0.
  • the present invention also provides for a reaction product of an epoxy compound and an amino silane further comprising the reaction product of a compound having the formula: R29(R30) K Si(OR31) 3 - ⁇ - ⁇ (R 32 ) ⁇ (OR 33 ) ⁇
  • R 29 is a monovalent hydrocarbon radical containing one or more oxirane or oxetane moieties having from 3 to 12 carbon atoms;
  • R 30 is a divalent hydrocarbon radical consisting of 1-60 carbons and the subscript K has a value of zero or 1;
  • R 31 and R 32 are independently selected from the group of monovalent linear or branched hydrocarbon radicals having from 1 to 60 carbon atoms;
  • the subscript ⁇ is zero or positive and has a value ranging from 0 to 3;
  • the subscript ⁇ is greater than 0 and less than or equal to 3, subject to the limitation that 3- ⁇ - ⁇ is greater than or equal to zero;
  • R 33 is a hydrocarbon radical that contains 3 to 200 carbon atoms.
  • hydrocarbon radical includes hydrocarbon radicals that may be optionally substituted with hetero-atoms particularly nitrogen, oxygen, and sulfur, and may optionally contain ring structures such as oxirane and oxetane groups.
  • the mole ratio of oxirane or epoxy groups to amino groups is preferably about 1 to about 4, more preferably greater than about 1.1 and less than about 3.9, and most preferably greater than about 1.2 and less than about 3.8.
  • R 1 is preferably a monovalent hydrocarbon radical of from 1 to about 10 carbon atoms or hydrogen, more preferably from 1 to about 5 carbon atoms or hydrogen, most preferably R 1 is H.
  • R 2 is preferably a monovalent hydrocarbon radical of from 1 to about 10 carbon atoms more preferably 2 to about 8 carbon atoms, and most preferably 3 to about 5 carbon atoms.
  • R 4 is preferably a monovalent hydrocarbon radical of from 3 to about 10 carbon atoms more preferable 3to about 8 carbon atoms most preferable 3 to about 5 carbon atoms.
  • R 3 , R 6 , R 7 , and R 8 are each preferably a monovalent hydrocarbon radical of from 1 to about 20 carbon atoms more preferably 1 to about 15 carbon atoms, most preferably 2 to about 8 carbon atoms.
  • Subscript a is in the range of from 0 to about 3, preferably from about 1 to about 3, more preferably from about 2 to about 3, most preferably from 0 to about 1.
  • Subscript b is in the range of 0 to about 25, more preferably 0 to about 15 and most preferably 3.
  • Subscript c is in the range 0 to about 3, more preferably 0 to about 2, most preferably 0 to about 1.
  • R 9 , R 10 , R 11 , R 12 , R 13 , R 18 , R 19 , R 20 , and R 21 are each preferably a monovalent hydrocarbon radical of from 1 to about 4 carbon atoms, more preferably 1 to about 3 carbon atoms, and most preferably 1 carbon atom.
  • the subscripts f, 1, m, n, o p , q, r, s are each in the range of 0 to about 200, more preferably 0 to about 100, and most preferably 0 to about 50.
  • the subscript k is in the range of 0 to about500, more preferably 5 to about 250, and most preferably 5 to about 150.
  • the subscripts v, w, and x are each in the range of 0 to about 50, more preferably 0 to about 35, and most preferably 0 to about 25.
  • R 23 and R 24 are each preferably a monovalent hydrocarbon radical of from 5 to aboutlOOO carbon atoms, more preferably 10 - to about500, and most preferably 10 to about 300.
  • the subscripts ⁇ , ⁇ , ⁇ are in the range of 0 to about 50 more preferably, 0 to about 30, and most preferably 0 to about 15.
  • R 31 and R 32 are each preferably a monovalent hydrocarbon radical of from 1 to about 10 carbon atoms, more preferably 1 to about 8 carbon atoms, and most preferably 1 to about 4 carbon atoms.
  • R 33 are each preferably a monovalent hydrocarbon radical of from 3 to aboutlOO carbon atoms, more preferably 3 to about 50 carbon atoms, most preferably 3 to about 10 carbon atoms.
  • a substance, component or ingredient identified as a reaction product, resulting mixture, or the like may gain an identity, property, or character through a chemical reaction or transformation during the course of contacting, in situ formation, blending, or mixing operation if conducted in accordance with this disclosure with the application of common sense and the ordinary skill of one in the relevant art (e.g., chemist).
  • the transformation of chemical reactants or starting materials to chemical products or final materials is a continually evolving process, independent of the speed at which it occurs. Accordingly, as such a transformative process is in progress there may be a mix of starting and final materials, as well as intermediate species that may be, depending on their kinetic lifetime, easy or difficult to detect with current analytical techniques known to those of ordinary skill in the art.
  • Reactants and components referred to by chemical name or formula in the specification or claims hereof, whether referred to in the singular or plural, may be identified as they exist prior to coming into contact with another substance referred to by chemical name or chemical type (e.g., another reactant or a solvent).
  • Preliminary and /or transitional chemical changes, transformations, or reactions, if any, that take place in the resulting mixture, solution, or reaction medium may be identified as intermediate species, master batches, and the like, and may have utility distinct from the utility of the reaction product or final material.
  • Other subsequent changes, transformations, or reactions may result from bringing the specified reactants and /or components together under the conditions called for pursuant to this disclosure.
  • reaction product may identify or indicate the reaction product or final material.
  • additional materials may be added to the initial mixture of synthetic precursors. These additional materials may be reactive or non- reactive.
  • the defining characteristic of the instant invention is that the reaction product is obtained from the reaction of at least the components listed as disclosed. Non-reactive components may be added to the reaction mixture as diluents or to impart additional properties unrelated to the properties of the composition prepared as a reaction product.
  • finely divided solids such as pigments may be dispersed into the reaction mixture, before during or after reaction to produce a reaction product composition that additionally comprises the non-reactive component, e.g. a pigment.
  • additional reactive components may also be added; such components may react with the initial reactants or they may react with the reaction product; the phrase "reaction product" is intended to include those possibilities as well as including the addition of non-reactive components.
  • reaction of component A with component B can be conducted in the presence of a primary or secondary amine that may or may not possess a reactive alkoxy silane moiety.
  • the result will be a reaction product of A, B, and the primary or secondary amine.
  • Examples of these primary amines are; methylamine, ethylamine, propylamine, ethanol amine, isopropylamine, butylamine, isobutylamine, hexylamine, dodecylamine, oleylamine, aniline aminopropyltrimethylsilane, aminopropyltriethylsilane, aminomorpholine, aminopropyldiethylamine benzylamine, napthylamine 3- amino-9-ethy lcarbazole, 1 -aminoheptaphlorohexane, 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-l-octanamine and the like.
  • secondary amines are; methylethylamine, methylhexylamine, methyloctadecylamine, diethanolamine, dibenzylamine, dihexylamine dicyclohexylamine, piperidine, pyrrolidine phthalimide, and the like. Polymeric amines may also be used such.
  • the product of the reaction of A, an oxirane or oxetane compound possessing two or more oxirane or oxetane groups per molecule and B, an aminosilane results in a polymer that contains alkoxy silane functional moieties covalently bond to the polymer chain.
  • alkoxy silane groups may be activated particularly by hydrolysis and undergo further reactions leading to a cross-linked network.
  • the cross-linking mechanism of silanes is usually a two-step process. The first step usually involves the hydrolysis of an alkoxy silane to form silanols. The second step usually involves the condensation of the silanol groups so produced with themselves or with other reactive organic groups.
  • silanol groups may also condense reversibly with organic moieties such as alcohols, carboxylic acids, amines, mercaptans, and ketones (other reactive groups).
  • organic moieties such as alcohols, carboxylic acids, amines, mercaptans, and ketones (other reactive groups).
  • the bonds that are formed are less stable than the siloxane bonds.
  • rate of the reverse reaction may be severely reduced or even stopped.
  • compositions of the present invention may be utilized as pure components, mixtures, or emulsions.
  • emulsions comprise at least two immiscible phases one of which is continuous and the other which is discontinuous.
  • Further emulsions may be liquids or gases with varying viscosities or solids. Additionally the particle size of the emulsions may render them microemulsions and when sufficiently small microemulsions may be transparent.
  • emulsions of emulsions and these are generally known as multiple emulsions. These emulsions may be: 1) aqueous emulsions where the discontinuous phase comprises water and the continuous phase comprises the composition of the present invention;
  • discontinuous phase comprises the composition of the present invention and the continuous phase comprises water
  • discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the composition of the present invention
  • non-aqueous emulsions where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the discontinuous phase comprises the composition of the present invention.
  • the resulting reaction product may be soluble in polar aqueous or hydroxylic solvents or it may be soluble in non-polar solvents such as oils, low molecular weight siloxanes and silicones and the like.
  • the hydrophilic lipophilic balance of the resulting reaction product will result in imparting different properties to articles of manufacture depending on the hydrophilic lipophilic balance of the reaction product.
  • a more hydrophilic reaction product may impart hydrophilic properties to one or more surfaces of an article of manufacture such as a textile.
  • a more hydrophobic reaction product may impart hydrophobic properties of one or more surfaces of an article of manufacture such as a textile.
  • reaction product coating the material will not migrate as determined by AATCC Test Method 79-1995 such that an adjacent untreated nonwoven textile exhibits a strike-through time greater than 300 seconds.
  • the resulting treated non-woven textile will exhibit a water height of less than 0.5 cm, more preferably less than 0.4 cm and most preferably less than 0.1 cm when Inda Standard Test 1ST 80.4 is performed.
  • the resulting treated material Upon application and curing a reaction product of the present invention to a nonwoven textile, the resulting treated material exhibits a strike through time of less than 100 seconds, more preferably less than 50 seconds, and most preferably less than 10 seconds when Edana Strike Through Time 150.3-96 is performed.
  • the treated textile Upon application and curing a reaction product of the present invention to a textile the treated textile exhibits a wet out time of less than 50 sec more preferable less than 30 sec most preferably less than 20 sec when AATCC Test Method 79-1992 is performed. [0026] Upon application and curing a reaction product of the present invention to a textile, the treated textile exhibits a wicking value of greater than 10 mm, more preferably greater than 12 mm, and most preferably greater than 15 mm when ASTM D-5237 test protocol is performed.
  • the coating Upon application and curing a reaction product of the present invention to a nonwoven textile, the coating will not migrate following as determined by the a greater than 300 second strike-thorough time of greater than 300 sec of an adjacent untreated nonwoven textile as described in AATCC Test Method 79-1995.
  • the non-woven material Upon application and curing a reaction product of the present invention to a nonwoven textile, the non-woven material will exhibit a water height greater than 1.0 cm, more preferably greater than 1.2 cm, and most preferably greater than 1.5 cm when Inda Standard Test 1ST 80.4 is performed.
  • the non-woven textile Upon application and curing a reaction product of the present invention to a nonwoven textile, the non-woven textile will exhibit a strike through time of greater than 300 seconds, more preferably greater than 350 seconds and most preferably greater than 400 seconds when Edana Strike Through Time 150.3-96 is performed.
  • the treated textile Upon application and curing a reaction product of the present invention to a textile, the treated textile exhibits a wet out time of greater than 50 seconds, more preferably greater than 100 seconds and most preferably greater than 200 seconds when AATCC Test Method 79-1992 is performed.
  • the treated textile Upon application and curing a reaction product of the present invention to a textile, the treated textile exhibits a wicking value of less than 10 mm, more preferably less than 5 mm, and most preferably less than 2 mm when ASTM D-5237 test protocol is performed.
  • the treated textile Upon application and a reaction product of the present invention to a textile, the treated textile exhibits a rating value greater than 50 after 5 detergent washes, more preferably a rating value greater than 50 after 10 washes and most preferably a rating value greater than 50 after 20 washes when AATCC test method 22-1989 is performed.
  • adjuvants are provided either as a tank-side additive or used as a component in pesticide formulations.
  • Typical uses for pesticides include agricultural, horticultural, turf, ornamental, home and garden, veterinary and forestry applications.
  • the pesticidal compositions of the present invention also include at least one pesticide, where the composition of the present invention is present at an amount sufficient to deliver between 0.005% and 2% to the final use concentration, either as a concentrate or diluted in a tank mix.
  • the pesticidal composition may include excipients, cosurfactants, solvents, foam control agents, deposition aids, drift retardants, biologicals, micronutrients, fertilizers and the like.
  • pesticide means any compound used to destroy pests, e.g., rodenticides, insecticides, miticides, fungicides, and herbicides.
  • pesticides that can be employed include, but are not limited to, growth regulators, photosynthesis inhibitors, pigment inhibitors, mitotic disrupters, lipid biosynthesis inhibitors, cell wall inhibitors, and cell membrane disrupters.
  • the amount of pesticide employed in compositions of the invention varies with the type of pesticide employed.
  • Fungicide compositions that can be used with the present invention include, but are not limited to, aldimorph, tridemorph, dodemorph, dimethomorph; flusilazol, azaconazole, cyproconazole, epoxiconazole, furconazole, propiconazole, tebuconazole and the like; imazalil, thiophanate, benomyl carbendazim, chlorothialonil, dicloran, trifloxystrobin, fluoxystrobin,dimoxystrobin, azoxystrobin, furcaranil, prochloraz, flusulfamide, famoxadone, captan, maneb, mancozeb, dodicin, dodine, and metalaxyl.
  • Insecticide, larvacide, miticide and ovacide compounds that can be used with the composition of the present invention, but not limited to, Bacillus thuringiensis, spinosad, abamectin, doramectin, lepimectin, pyrethrins, carbaryl, primicarb, aldicarb, methomyl, amitraz, boric acid, chlordimeform, novaluron, bistrifluron, triflumuron, diflubenzuron, imidacloprid, diazinon, acephate, endosulfan, kelevan, dimethoate, azinphos- ethyl, azinphos-methyl, izoxathion, chlorpyrifos, clofentezine, lambda- cyhalothrin, permethrin, bifenthrin, cypermethrin and the like.
  • Fertilizers and micronutrients include, but not limited to, zinc sulfate, ferrous sulfate, ammonium sulfate, urea, urea ammonium nitrogen, ammonium thiosulfate, potassium sulfate, monoammonium phosphate, urea phosphate, calcium nitrate, boric acid, potassium and sodium salts of boric acid, phosphoric acid, magnesium hydroxide, manganese carbonate, calcium polysulfide, copper sulfate, manganese sulfate, iron sulfate, calcium sulfate, sodium molybdate, calcium chloride,
  • the pesticide or fertilizer may be a liquid or a solid. If a solid, it is preferable that it is soluble in a solvent, or the organomodified disiloxanes of the present invention, prior to application, and the silicone may act as a solvent, or surfactant for such solubility or additional surfactants may perform this function.
  • Buffers, preservatives and other standard excipients known in the art also may be included in the composition.
  • Solvents may also be included in compositions of the present invention. These solvents are in a liquid state at room temperature. Examples include water, alcohols, aromatic solvents, oils (i.e. mineral oil, vegetable oil, silicone oil, and so forth), lower alkyl esters of vegetable oils, fatty acids, ketones, glycols, polyethylene glycols, diols, paraffinics, and so forth. Particular solvents would be 2, 2, 4-trimethyl, 1-3-pentane diol and alkoxylated (especially ethoxylated) versions thereof as illustrated in US Patent No. 5,674,832 herein incorporated by reference, or n-methyl- pyrrilidone.
  • Cosurfactants useful herein include nonionic, cationic, anionic, amphoteric, zwitterionic, polymeric surfactants, or any mixture thereof.
  • Surfactants are typically hydrocarbon based, silicone based or fluorocarbon based.
  • compositions described above are also useful as the alkyl chloride, alkyl iodide and alkyl bromide analogues, as well as the acid pairs with HCl, acetic acid, propionic acid, glycolic acid, gibberellic acid and the like.
  • quaternizernization increases solubility and as well as makes possible potential interactions with nonionic and anionic cosurfactants.
  • Useful surfactants include alkoxylates, especially ethoxylates, containing block copolymers including copolymers of ethylene oxide, propylene oxide, butylene oxide, and mixtures thereof; alkylarylalkoxylates, especially ethoxylates or propoxylates and their derivatives including alkyl phenol ethoxylate; arylarylalkoxylates, especially ethoxylates or propoxylates.
  • amine alkoxylates especially amine ethoxylates; fatty acid alkoxylates; fatty alcohol alkoxylates; alkyl sulfonates; alkyl benzene and alkyl naphthalene sulfonates; sulfated fatty alcohols, amines or acid amides; acid esters of sodium isethionate; esters of sodium sulfosuccinate; sulfated or sulfonated fatty acid esters; petroleum sulfonates; N-acyl sarcosinates; alkyl polyglycosides; alkyl ethoxylated amines; and so forth.
  • alkyl acetylenic diols (SURFONYL- Air Products), pyrrilodone based surfactants (e.g., SURFADONE - LP 100 - ISP), 2-ethyl hexyl sulfate, isodecyl alcohol ethoxylates (e.g., RHODASURF DA 530 - Rhodia), ethylene diamine alkoxylates (TETRONICS - BASF), ethylene oxide/propylene oxide copolymers (PLURONICS - BASF), Gemini type surfactants (Rhodia) and diphenyl ether Gemini type surfactants (e.g. DOWFAX - Dow Chemical).
  • pyrrilodone based surfactants e.g., SURFADONE - LP 100 - ISP
  • 2-ethyl hexyl sulfate e.g., isodecyl alcohol ethoxylates
  • Preferred surfactants include ethylene oxide/propylene oxide copolymers (EO/PO); amine ethoxylates; alkyl polyglycosides; oxo-tridecyl alcohol ethoxylates, and so forth.
  • EO/PO ethylene oxide/propylene oxide copolymers
  • amine ethoxylates alkyl polyglycosides
  • oxo-tridecyl alcohol ethoxylates and so forth.
  • the agrochemical composition of the present invention further comprises one or more agrochemical ingredients.
  • Suitable agrochemical ingredients include, but not limited to, herbicides, insecticides, growth regulators, fungicides, miticides, acaricides, fertilizers, biologicals, plant nutritionals, micronutrients, biocides, paraffinic mineral oil, methylated seed oils (i.e.
  • methylsoyate or methylcanolate examples include soybean oils (such as soybean oil and canola oil), water conditioning agents such as Choice ® (Loveland Industries, Greeley, CO) and Quest (Helena Chemical, Collierville, TN), modified clays such as Surround ® (Englehard Corp.,), foam control agents, surfactants, wetting agents, dispersants, emulsifiers, deposition aids, antidrift components, and water.
  • Choice ® Loveland Industries, Greeley, CO
  • Quest Helena Chemical, Collierville, TN
  • modified clays such as Surround ® (Englehard Corp.,)
  • foam control agents surfactants, wetting agents, dispersants, emulsifiers, deposition aids, antidrift components, and water.
  • Suitable agrochemical compositions are made by combining, in a manner known in the art, such as, by mixing one or more of the above components with the organomodified disiloxane of the present invention, either as a tank-mix, or as an "In-can" formulation.
  • tank-mix means the addition of at least one agrochemical to a spray medium, such as water or oil, at the point of use.
  • In-can refers to a formulation or concentrate containing at least one agrochemical component. The "In-can” formulation may then diluted to use concentration at the point of use, typically in a Tank-mix, or it may be used undiluted.
  • coatings formulations will require a wetting agent or surfactant for the purpose of emulsification, compatibilization of components, leveling, flow and reduction of surface defects. Additionally, these additives may provide improvements in the cured or dry film, such as improved abrasion resistance, antiblocking, hydrophilic, and hydrophobic properties. Coatings formulations may exists as, Solvent-borne coatings, water-borne coatings and powder coatings.
  • the coatings components may be employed as: architecture coatings; OEM product coatings such as automotive coatings and coil coatings; Special Purpose coatings such as industrial maintenance coatings and marine coatings;
  • Typical resin types include: Polyesters, alkyds, acrylics, epoxies
  • the epoxy amino silane copolymers of the present invention comprises, per 100 parts by weight ("pbw") of the personal care composition, from 0.1 to 99 pbw, more preferably from 0.5 pbw to 30 pbw and still more preferably from 1 to 15 pbw of the composition of the present invention and from 1 pbw to 99.9 pbw, more preferably from 70 pbw to 99.5 pbw, and still more preferably from 85 pbw to 99 pbw of the personal care composition.
  • pbw parts by weight
  • compositions of the present invention may be utilized in personal care emulsions, such as lotions, and creams.
  • emulsions comprise at least two immiscible phases one of which is continuous and the other which is discontinuous.
  • Further emulsions may be liquids with varying viscosities or solids. Additionally the particle size of the emulsions may render them microemulsions and, when sufficiently small, microemulsions may be transparent.
  • emulsions of emulsions and these are generally known as multiple emulsions. These emulsions may be:
  • aqueous emulsions where the discontinuous phase comprises water and the continuous phase comprises the epoxy amino silane copolymers of the present invention
  • discontinuous phase comprises the epoxy amino silane copolymers of the present invention and the continuous phase comprises water;
  • discontinuous phase comprises a non-aqueous hydroxylic solvent and the continuous phase comprises the epoxy amino silane copolymers of the present invention
  • non-aqueous emulsions where the continuous phase comprises a non-aqueous hydroxylic organic solvent and the discontinuous phase comprises the epoxy amino silane copolymers of the present invention.
  • Non-aqueous emulsions comprising a silicone phase are described in US patent 6,060,546 and US patent 6,271,295 the disclosures of which are herewith and hereby specifically incorporated by reference.
  • non-aqueous hydroxylic organic compound means hydroxyl containing organic compounds exemplified by alcohols, glycols, polyhydric alcohols and polymeric glycols and mixtures thereof that are liquid at room temperature, e.g. about 25 0 C, and about one atmosphere pressure.
  • the non-aqueous organic hydroxylic solvents are selected from the group consisting of hydroxyl containing organic compounds comprising alcohols, glycols, polyhydric alcohols and polymeric glycols and mixtures thereof that are liquid at room temperature, e.g. about 25 0 C, and about one atmosphere pressure.
  • the non-aqueous hydroxylic organic solvent is selected from the group consisting of ethylene glycol, ethanol, propyl alcohol, iso-propyl alcohol, propylene glycol, dipropylene glycol, tripropylene glycol, butylene glycol, iso-butylene glycol, methyl propane diol, glycerin, sorbitol, polyethylene glycol, polypropylene glycol mono alkyl ethers, polyoxyalkylene copolymers and mixtures thereof.
  • the resulting material is usually a cream or lotion with improved deposition properties and good feel characteristics. It is capable of being blended into formulations for hair care, skin care, antiperspirants, sunscreens, cosmetics, color cosmetics, insect repellants, vitamin and hormone carriers, fragrance carriers and the like.
  • the personal care applications where the epoxy amino silane copolymers of the present invention and the silicone compositions derived therefrom of the present invention may be employed include, but are not limited to, deodorants, antiperspirants, antiperspirant/deodorants, shaving products, skin lotions, moisturizers, toners, bath products, cleansing products, hair care products such as shampoos, conditioners, mousses, styling gels, hair sprays, hair dyes, hair color products, hair bleaches, waving products, hair straighteners, manicure products such as nail polish, nail polish remover, nails creams and lotions, cuticle softeners, protective creams such as sunscreen, insect repellent and anti-aging products, color cosmetics such as lipsticks, foundations, face powders, eye liners, eye shadows, blushes, makeup, mascaras and other personal care formulations where silicone components have been conventionally added, as well as drug delivery systems for topical application of medicinal compositions that are to be applied to the skin.
  • the personal care composition of the present invention further comprises one or more personal care ingredients.
  • suitable personal care ingredients include, for example, emollients, moisturizers, humectants, pigments, including pearlescent pigments such as, for example, bismuth oxychloride and titanium dioxide coated mica, colorants, fragrances, biocides, preservatives, antioxidants, anti-microbial agents, anti-fungal agents, antiperspirant agents, exfoliants, hormones, enzymes, medicinal compounds, vitamins, salts, electrolytes, alcohols, polyols, absorbing agents for ultraviolet radiation, botanical extracts, surfactants, silicone oils, organic oils, waxes, film formers, thickening agents such as, for example, fumed silica or hydrated silica, particulate fillers, such as for example, talc, kaolin, starch, modified starch, mica, nylon, clays, such as, for example, bentonite and organo-modified clays.
  • Suitable personal care compositions are made by combining, in a manner known in the art, such as, for example, by mixing, one or more of the above components with the compositions of the present invention.
  • Suitable personal care compositions may be in the form of a single phase or in the form of an emulsion, including oil-in-water, water-in-oil and anhydrous emulsions where the silicone phase may be either the discontinuous phase or the continuous phase, as well as multiple emulsions, such as, for example, oil- in water-in-oil emulsions and water-in-oil-in water-emulsions.
  • an antiperspirant composition comprises the epoxy amino silane copolymers of the present invention and one or more active antiperspirant agents.
  • Suitable antiperspirant agents include, for example, the Category I active antiperspirant ingredients listed in the U.S.
  • a skin care composition comprises the compositions of the present invention, and a vehicle, such as, for example, a silicone oil or an organic oil.
  • the skin care composition may, optionally, further include emollients, such as, for example, triglyceride esters, wax esters, alkyl or alkenyl esters of fatty acids or polyhydric alcohol esters and one or more the known components conventionally used in skin care compositions, such as, for example, pigments, vitamins, such as, for example, Vitamin A, Vitamin C and Vitamin E, sunscreen or sunblock compounds, such as, for example, titanium dioxide, zinc oxide, oxybenzone, octylmethoxy cinnamate, butylmethoxy dibenzoylm ethane, p-aminobenzoic acid and octyl dimethyl-p-aminobenzoic acid.
  • emollients such as, for example, triglyceride esters, wax esters, alkyl or alken
  • a color cosmetic composition such as, for example, a lipstick, a makeup or a mascara composition
  • a coloring agent such as a pigment, a water soluble dye or a liposoluble dye.
  • compositions of the present invention are utilized in conjunction with fragrant materials.
  • These fragrant materials may be fragrant compounds, encapsulated fragrant compounds, or fragrance releasing compounds that either the neat compounds or are encapsulated.
  • Particularly compatible with the compositions of the present invention are the fragrance releasing silicon containing compounds as disclosed in US patents 6,046,156; 6,054,547; 6,075,111; 6,077,923; 6,083,901; and 6,153,578; all of which are herein and herewith specifically incorporated by reference.
  • compositions of the present invention are not restricted to personal care compositions, other products such as waxes, polishes and textiles treated with the compositions of the present invention are also contemplated.
  • Home care applications include laundry detergent and fabric softener, dishwashing liquids, wood and furniture polish, floor polish, tub and tile cleaners, toilet bowl cleaners, hard surface cleaners, window cleaners, antifog agents, drain cleaners, auto-dish washing detergents and sheeting agents, carpet cleaners, prewash spotters, rust cleaners and scale removers.
  • compositions of the present organomodified silylated surfactant invention are useful in oil and gas applications, including demulsification.
  • compositions comprising organomodified silylated surfactant invention are useful for applications involving commercial and industrial open recirculating cooling water towers, closed cooling water systems, cooling water conduits, heat exchangers, condensers , once-through cooling systems, Pasteurizers, air washers, heat exchange systems, air conditioning / humidifiers / dehumidifiers, hydrostatic cookers, safety and /or fire water protection storage systems, water scrubbers, disposal wells, influent water systems, including filtration and clarifiers, wastewater treatment, wastewater treatment tanks, conduits, filtration beds, digesters, clarifiers, holding ponds, settling lagoons, canals, odor control, ion exchange resin beds, membrane filtration, reverse osmosis, micro- and ultra-filtration, assisting in the removal of biofilms in cooling tower applications, heat exchangers and process water systems, and the like.
  • compositions of the present organomodified silylated surfactant invention are useful in pulp and paper applications, such as paperboard defoamers, and wetting agents for the pulping process.
  • Aminopropyltriisopropoxy silane (51.72 g), an epoxy encapped polyether with the average structure CH 2 (O)CHCH 2 (OCH 2 CH 2 ) 73 OCH 2 CH(O)CH 2 (148.28 g) and isopropanol (60.00 g) was combined in a 500 mL flask. The material was brought to reflux and stirred with an overhead stirrer. The refluxing continued for 24 hr until all epoxy groups were consumed as determined by titration. The material was transferred to a rotary evaporator and stripped at 70 0 C and 4 torr for 2 hrs to remove the isopropanol.
  • Aminopropyltriisopropoxy silane (54.27 g), an epoxy encapped polysiloxane with the average structure CH 2 (O)CHCH 2 OCH 2 CH 2 CH 2 Si(CH3)2 ⁇ [Si(CH3) 2 O] 5 o- Si(CH 3 ) 2 CH 2 CH 2 CH 2 OCH(O)CH 2 (185.70 g) and an epoxy encapped polyether with the average structure
  • Example J Aminopropyltriisopropoxy silane (27.00 g), an epoxy encapped polysiloxane with the average structure CH 2 (O)CHCH2 ⁇ CH 2 CH 2 CH2Si(CH3)2 ⁇ [Si(CH3)2 ⁇ ]50- Si(CHa) 2 CH 2 CH 2 CH 2 OCH(O)CH 2 (92.70 g), an epoxy encapped polyether with the average structure CH 2 (O)CHCH 2 O(CH 2 CH 2 O) 7 CH 2 CH(O)CH 2 (27.69 g) and isopropanol (253.43 g) was combined in a 500 mL flask. The material was brought to reflux and stirred with an overhead stirrer. The refluxing continued for 16 hr until all epoxy groups were consumed as determined by titration. The material was transferred to a rotary evaporator and stripped at 70 0 C and 4 torr for 2 hrs to remove the isopropanol.
  • Aminopropyltriisopropoxy silane (40.34 g), an epoxy encapped polysiloxane with the average structure CH 2 (O)CHCH2OCH2CH 2 CH 2 Si(CH 3 ) 2 O[Si(CH 3 ) 2 O]5-
  • Example A, B, C or D (5 g) was added to 20 g of distilled water. The solution was mixed with a magnetic stir bar and neutralized to pH 7 with acetic acid. The resulting formulation a listed in the table below.
  • Example formulations numbered 1-4 were coated on cleaned and dried untreated steal plates. The coating was conducted using a 3 mil wire wound rod. 5 mL of each formulation was added to the substrate in front of the rod. The rod was pulled across the substrate at constant force and velocity. The coating was allowed to cure for 4 days at room temperature.
  • Synthetic Example C, J, L, & M were diluted to a 20% aqueous formulation and neutralized with acetic acid (pH 7).
  • the hard surfaces tested in this application were Terracotta and Marble (3" x 3").
  • Half of each tile was treated by adding 0.5 mL of the formulation to each tile.
  • the coating was then smoothed using an applicator in order to have a uniform coating on half of each tile.
  • the tiles were allowed to cure overnight at ambient temperature.
  • the control formula was a commercial hard surface sealer from HG international. The following day each tile was subjected to two drops of staining solution.
  • the stains are listed in the table below. The stains were allowed to sit at ambient temperature on the surface for 16 hr.
  • Run-Off experiments were performed following the standard Edana 152.0-99. Given in the table is the percent run-off of a 0.9% sodium chloride solution when applied to a piece of treated spun polypropylene held at a 25° angle. Two different sets of treatments were chosen. Example formulations 11 and 12 are hydrophobic treatment while examples 13 and 14 are hydrophilic. An untreated sheet of polypropylene was used for comparison. Table Percent run off of 4 treated spun polypropylene sheets
  • Run-Off experiments were performed following the standard Edana Strike Through Time 150.3-96. Given in the table is the percent run-off of a O.%9 sodium chloride solution when applied to a piece of treated spun polypropylene held at a 25° angle. Two different sets of treatments were chosen. Example formulations 11 and 12 are hydrophobic treatment while examples 13 and 14 are hydrophilic. An untreated sheet of polypropylene was used for comparison.
  • a Hydrodrostatic pressure test was performed on the treated polypropylene to test resistance to water penetration when a column of water was placed on the surface.
  • the treated polypropylene was sandwiched between two pieces of plastic with a 2" circular hole in both. The upper piece was attached to a graduated column. Water was introduced through in inlet just over the PP material at a rate that did not allow for a vortex to form.
  • a mirror was positioned below the apparatus and the water was added to the column. The height of the water was recorded once drops of water formed and released from the bottom of the apparatus. The data is shown in the table below. For formulations 13 and 14 no buildup occurred and the water immediately penetrated and began to flow through the polypropylene.
  • a 20% microemulsion of Magnasoft Derma NT was made by the addition of 25.0 grams of a commercial polysilicone quat (Momentive Performance Materials) into a disposable beaker to 10.5 grams of TDA-6 and 1.8 grams of TDA-12 (both surfactants made by Ethox). The mixture was stirred using a mechanical stirrer, at moderate speed ( ⁇ 600 rpm) for 5 minutes. Separately a solution of 62.0 grams of deionized water, 0.4 grams of acetic acid, and 0.3 grams of sodium acetate was combined in an addition funnel. The water, acetic acid, and sodium acetate solution was added dropwise over 30 minutes. After the final addition the emulsion was stirrer for an additional 10 minutes.
  • a commercial polysilicone quat Momentive Performance Materials
  • the swatches Prior to any physical evaluation of the treated and untreated fabrics, the swatches were placed in an environmental chamber set at 21 0 C and 65% RH for a minimum of 24 hours.
  • a wicking test was performed in order to evaluate how well the treatments enhance or deter the wicking of water through the fabric. This test was performed in accordance with the ASTM D-5237 test protocol.
  • a 2" X 7" strip of treated or untreated fabric was cut from different sample sheets. One end the fabric was marked with a pencil line ⁇ 15 mm from the edge. 2 standard metal paper clips were fastened between this line and the edge of the sample. The other end of the fabric was secured a stand with a large (# 100) binder clip. The fabric was immersed up to the pencil line in a beaker of colored water. After 6 minutes the fabric samples were removed from the water and the distance from the pencil line to the final position of the wicked water was measured with a ruler and recorded in millimeters. The procedure was repeated 4 times and the measurement were averaged and given in the table below.
  • a Spray Test was run according to AATCC test method 22-1989. Treated cotton knit fabric was washed in the same manner as described in the Durability section above for 1, 3, 5, 10 and 20 wash/dry cycles. The fabric was secured a 6" embroidery ring. Care was taken so that the fabric did not stretch but it was taut and free of folds or wrinkles. The assembly was placed on the spray test apparatus that consisted of stand holding a jig set at a 45° angle positioned below a large funnel and showerhead. 250 mL of deionized water was poured through the funnel and showerhead onto the test specimen. The specimen/ring was removed and visually rated 0-100 by comparing its appearance to the spray test rating standard. The control sample was an untreated piece of cotton knit. The results are shown in the table below. The high numbers of 121-113 indicate that the surface remains hydrophobic even after 20 washes.
  • a panel of 5 people was designated to determine the softness and bulkiness that the treatment imparts to cotton knit fabric.
  • the test panels were asked to rate the softness of the fabric from 1 to 10.
  • An untreated swatch of fabric was used to indicate a 1.
  • a high value indicates a very soft and pleasant feel. Most of the formulations tested performed well against the untreated control.
  • the word "comprises” and its grammatical variants logically also subtend and include phrases of varying and differing extent such as for example, but not limited thereto, “consisting essentially of” and “consisting of.” Where necessary, ranges have been supplied; those ranges are inclusive of all sub-ranges there between. Such ranges may be viewed as a Markush group or a collection of Markush groups consisting of differing pairwise numerical limitations which group or groups is or are fully delimited by its lower and upper bounds, increasing in a regular fashion numerically from lower bounds to upper bounds.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Textile Engineering (AREA)
  • Polymers & Plastics (AREA)
  • Wood Science & Technology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • General Health & Medical Sciences (AREA)
  • Hydrology & Water Resources (AREA)
  • Agronomy & Crop Science (AREA)
  • Toxicology (AREA)
  • Dentistry (AREA)
  • Pest Control & Pesticides (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Plant Pathology (AREA)
  • Water Supply & Treatment (AREA)
  • Environmental & Geological Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Silicon Polymers (AREA)
  • Paints Or Removers (AREA)
  • Epoxy Resins (AREA)

Abstract

L'invention concerne une composition pour traiter des textiles comprenant un produit de réaction constitué : a) d'un composé oxirane ou d'un composé oxétane comprenant au moins deux groupes oxirane ou oxétane; et b) un amino silane représenté par la formule : N(H)(R1)R2Si(OR3)3-a-b-c(OR4)a(R5Si(OR6)d(R7)e)b R8c dans laquelle R1 est sélectionné dans le groupe constitué par H ou un radical hydrocarboné monovalent contenant 1-20 atomes de carbone; R2 et R5 sont sélectionnés indépendamment dans le groupe constitué par oxygène ou un radical hydrocarboné linéaire ou ramifié divalent contenant 1-60 atomes de carbone; R4 représente un radical hydrocarboné contenant 3-200 atomes de carbone; R3, R6, R7 et R8 sont chacun sélectionnés indépendamment dans le groupe de radicaux hydrocarbonés linéaires ou ramifiés monovalents contenant 1-200 atomes de carbone; l'indice b est égal à zéro ou à un nombre positif et présente une valeur comprise entre 0 et 3; les indices a et c sont égaux à zéro ou positifs et présentent une valeur comprise entre 0 et 3 soumise à la restriction suivante : (a + b + c) ≤ 3; les indices d et e sont égaux à zéro ou positifs et présentent une valeur comprise entre 0 et 3 soumise à la restriction suivante (d + e) ≤ 3 afin de réagir de manière améliorée à l'eau.
EP08848440A 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et des amino silanes Withdrawn EP2215304A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP12007526.2A EP2617893A3 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes
EP12007512.2A EP2617892B1 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes
EP12007511.4A EP2617891A3 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US98475307P 2007-11-02 2007-11-02
US19736708A 2008-08-25 2008-08-25
PCT/US2008/012302 WO2009061362A2 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et des amino silanes

Related Child Applications (1)

Application Number Title Priority Date Filing Date
EP12007512.2A Division EP2617892B1 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes

Publications (1)

Publication Number Publication Date
EP2215304A2 true EP2215304A2 (fr) 2010-08-11

Family

ID=43548812

Family Applications (4)

Application Number Title Priority Date Filing Date
EP12007512.2A Active EP2617892B1 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes
EP12007526.2A Withdrawn EP2617893A3 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes
EP08848440A Withdrawn EP2215304A2 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et des amino silanes
EP12007511.4A Withdrawn EP2617891A3 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes

Family Applications Before (2)

Application Number Title Priority Date Filing Date
EP12007512.2A Active EP2617892B1 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes
EP12007526.2A Withdrawn EP2617893A3 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP12007511.4A Withdrawn EP2617891A3 (fr) 2007-11-02 2008-10-30 Textiles traités au moyen de copolymères de composés époxy et amino silanes

Country Status (5)

Country Link
EP (4) EP2617892B1 (fr)
JP (1) JP5346948B2 (fr)
KR (1) KR101595329B1 (fr)
CN (1) CN101970750B (fr)
WO (1) WO2009061362A2 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2007101182B4 (en) * 2007-11-02 2008-08-07 Ifinder Pty Ltd A locating device
WO2011065956A1 (fr) * 2009-11-30 2011-06-03 Momentive Performance Materials Inc. Produit de réaction non réticulée d'un composé époxy ou oxétane et un aminosiloxane
CN103333339B (zh) * 2013-06-04 2016-08-10 黄山市强力化工有限公司 一种羟基封端苯基氨基聚醚改性硅油
CN109153789A (zh) 2015-02-28 2019-01-04 赢创德固赛有限公司 Oem纺织品整理组合物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5786032A (en) * 1991-11-22 1998-07-28 Vision-Ease Lens, Inc. Coating composition and process for producing coated articles

Family Cites Families (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA866244A (en) * 1971-03-16 W. Sullivan Philip Use of water-soluble salts of epoxy-amine condensates to disperse epoxy resins
US3449281A (en) * 1964-04-16 1969-06-10 Owens Corning Fiberglass Corp Water dispersible epoxy compositions
ZA702021B (en) * 1969-04-03 1971-01-27 Du Pont Synthetic organic textile fibres
JPS5319715B2 (fr) * 1973-09-05 1978-06-22
US4062999A (en) 1974-02-12 1977-12-13 Teijin Limited Synthetic organic fibers coated with an amino silane and an epoxy siloxane containing treating agent
JPS5319716B2 (fr) * 1974-02-12 1978-06-22
JPS54129098A (en) * 1978-03-30 1979-10-06 Japan Atom Energy Res Inst Thermosetting resin composition
JPS6036513B2 (ja) 1981-02-05 1985-08-21 ト−レ・シリコ−ン株式会社 繊維用処理剤
JPS6241379A (ja) * 1985-08-14 1987-02-23 日華化学株式会社 シリコ−ン系繊維処理剤
KR900007765B1 (ko) * 1987-11-25 1990-10-19 고려화학 주식회사 고무가 피복된 저용력화제 제조방법 및 이를 함유한 조성물
JPH0284580A (ja) 1988-07-19 1990-03-26 Shin Etsu Chem Co Ltd 繊維処理剤および繊維製品
US5206285A (en) * 1990-12-21 1993-04-27 Northrop Corporation Aqueous coating of silane precursor from epoxy and amino trialkoxysilanes
US5063260A (en) * 1991-05-01 1991-11-05 Dow Corning Corporation Compositions and their use for treating fibers
JPH05214216A (ja) * 1992-02-04 1993-08-24 Matsushita Electric Works Ltd 封止用エポキシ樹脂成形材料
JP3261592B2 (ja) * 1992-04-20 2002-03-04 株式会社スリーボンド 湿気硬化及び光硬化しうるシリコーン組成物
US5558806A (en) 1992-07-23 1996-09-24 Osi Specialties, Inc. Surfactant blend of a polyalkleneoxide polysiloxane and an organic compound having a short chain hydrophobic moiety
JP2885390B2 (ja) * 1993-05-19 1999-04-19 信越化学工業株式会社 繊維処理用組成物
US5674832A (en) 1995-04-27 1997-10-07 Witco Corporation Cationic compositions containing diol and/or diol alkoxylate
US6060546A (en) 1996-09-05 2000-05-09 General Electric Company Non-aqueous silicone emulsions
US6271295B1 (en) 1996-09-05 2001-08-07 General Electric Company Emulsions of silicones with non-aqueous hydroxylic solvents
US6054547A (en) 1998-08-28 2000-04-25 General Electric Company Fragrance releasing non-volatile polymeric-siloxanes
US6075111A (en) 1998-08-28 2000-06-13 General Electric Company Fragrance releasing non-volatile polymeric siloxanes
US6083901A (en) 1998-08-28 2000-07-04 General Electric Company Emulsions of fragrance releasing silicon compounds
US6046156A (en) 1998-08-28 2000-04-04 General Electric Company Fragrance releasing olefinic silanes
DE19964309C2 (de) * 1999-11-15 2003-07-03 Degussa Triamino- und fluoralkylfunktionelle Organosiloxane oder deren Gemische
EP1116813A1 (fr) * 2000-01-10 2001-07-18 Dow Corning Corporation Adoussicant hydrophilie pour des textiles comprenant des polymères de epoxy glycol siloxane et des matériaux avec des fonctions amines
AU2001261690A1 (en) * 2000-05-19 2001-12-03 General Electric Company Organosiloxane containing modified groups in agricultural compositions
JP2002037021A (ja) * 2000-07-26 2002-02-06 Toyobo Co Ltd 収納性に優れたシートベルト
JP2002194675A (ja) * 2000-12-19 2002-07-10 Ge Toshiba Silicones Co Ltd 繊維処理剤
US6475568B1 (en) 2001-05-15 2002-11-05 Crompton Corporation Block, non-(AB)n silicone polyalkyleneoxide copolymers with tertiary amino links
GB0202631D0 (en) * 2002-02-05 2002-03-20 Dow Corning Hair care compositions containing polysiloxanes
US20030177590A1 (en) * 2002-02-21 2003-09-25 L'oreal Aqueous dispersion and method of use
CN100354340C (zh) * 2002-10-11 2007-12-12 通用电气公司 聚醚硅氧烷共聚物网络组合物
DE10316662A1 (de) * 2003-04-11 2004-11-11 Ge Bayer Silicones Gmbh & Co. Kg Reaktive Amino- und/oder Ammonium-Polysiloxanverbindungen
JP2005281528A (ja) * 2004-03-30 2005-10-13 Yokohama Rubber Co Ltd:The 光学材料用接着剤組成物
US7507775B2 (en) * 2005-10-13 2009-03-24 Momentive Performance Materials Inc. Hydrolysis resistant organomodified disiloxane surfactants
US20070112078A1 (en) * 2005-11-15 2007-05-17 Ian Procter Silicone antifoam composition
AU2007101182B4 (en) * 2007-11-02 2008-08-07 Ifinder Pty Ltd A locating device

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5786032A (en) * 1991-11-22 1998-07-28 Vision-Ease Lens, Inc. Coating composition and process for producing coated articles

Also Published As

Publication number Publication date
EP2617893A2 (fr) 2013-07-24
EP2617892B1 (fr) 2018-09-19
CN101970750A (zh) 2011-02-09
KR101595329B1 (ko) 2016-02-19
CN101970750B (zh) 2015-06-10
EP2617893A3 (fr) 2013-12-18
JP5346948B2 (ja) 2013-11-20
WO2009061362A3 (fr) 2009-08-06
JP2011503376A (ja) 2011-01-27
KR20100091174A (ko) 2010-08-18
WO2009061362A2 (fr) 2009-05-14
EP2617892A3 (fr) 2013-12-18
EP2617892A2 (fr) 2013-07-24
EP2617891A2 (fr) 2013-07-24
EP2617891A3 (fr) 2013-12-25

Similar Documents

Publication Publication Date Title
US8530601B2 (en) Copolymers of epoxy compounds and amino silanes
US20140235885A1 (en) Copolymers of epoxy compounds and amino silanes
AU2008343778A1 (en) Mixtures of hydrolysis resistant organomodified trisiloxane ionic surfactants
EP2124545A1 (fr) Tensioactifs ioniques silylés organomodifés résistants à l'hydrolyse
EP2237670A2 (fr) Tensioactifs ioniques de type trisiloxane organomodifié résistants à l'hydrolyse
US20110201505A1 (en) Mixtures comprising hydrolysis resistant organomodified disiloxane ionic surfactants
KR101595329B1 (ko) 에폭시 화합물들과 아미노 실란들의 코폴리머들로 처리된 텍스타일들
US8367740B2 (en) Hydrolysis resistant organomodified disiloxane ionic surfactants
US20080167269A1 (en) Hydrolysis resistant organomodified silylated ionic surfactants
AU2018321549B2 (en) Organomodified monosilyl compound, its preparation and applications thereof
US20120220791A1 (en) Copolymers of epoxy compounds and amino silanes

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 20100531

AK Designated contracting states

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MT NL NO PL PT RO SE SI SK TR

AX Request for extension of the european patent

Extension state: AL BA MK RS

17Q First examination report despatched

Effective date: 20101026

DAX Request for extension of the european patent (deleted)
STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN

18D Application deemed to be withdrawn

Effective date: 20131204