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WO2025061880A1 - Agent de réticulation à base de silicone organo-fonctionnel et composition de finition durable formée à partir de celui-ci - Google Patents

Agent de réticulation à base de silicone organo-fonctionnel et composition de finition durable formée à partir de celui-ci Download PDF

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Publication number
WO2025061880A1
WO2025061880A1 PCT/EP2024/076327 EP2024076327W WO2025061880A1 WO 2025061880 A1 WO2025061880 A1 WO 2025061880A1 EP 2024076327 W EP2024076327 W EP 2024076327W WO 2025061880 A1 WO2025061880 A1 WO 2025061880A1
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Prior art keywords
solution
copolymer
textile
aqueous emulsion
suspension
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PCT/EP2024/076327
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English (en)
Inventor
Meenal MEHRA
Sanooj NARAYANAN
Chaya M Thakkar PATEL
Rishi Kumar
Raja KALIAPPAN
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Archroma Switzerland GmbH
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Archroma Switzerland GmbH
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Publication of WO2025061880A1 publication Critical patent/WO2025061880A1/fr
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    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/04—Polysiloxanes
    • C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing 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
    • D06M15/6436—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
    • 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
    • C08G77/22—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
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/42—Block-or graft-polymers containing polysiloxane sequences
    • C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • the present invention relates to the development of an aqueous emulsion containing organo-functional silicone copolymer with alkoxy/hydroxy terminating groups.
  • Such flexible polymers act as a binder to covalently crosslink with free -OH groups of the substrate and enhance the durability of the coating film. Presence of long chain silicone backbone in the polymer makes it a flexible binder that helps to control over the crosslinking density thereby, not impacting the softness and flexibility of the silicone films on the substrate.
  • the present invention also relates to the development of compositions using this flexible binder in combination with other polymers or additives that covalently binds other hydrophilic silicone softeners and the substrates, bearing free -OH groups such as cellulosic fabric, forming interpenetrated network.
  • This provides good durability of the finishing coating with balanced handfeel and hydrophilic properties until several wash cycles.
  • BACKGROUND OF THE INVENTION Domestic softeners are widely used in everyday life to soften the laundry during washing. It is known that when a cloth or a towel are washed with such domestic softeners, it receives a good softness just after its washing, but this softness will fade as it used and will be totally lost after the washing operation.
  • softeners also called textile finishing products are used at the end of the manufacture of a textile to provide a good softness to the textile. Contrary to the domestic softeners, the softeners used in the textile industry when applied under the form of an emulsion on the textile, must have a long-lasting softness effect even after several washes. Softeners used as textile finishing products in the textile industry must then exhibit a high durability. Meissner Bolte 2 M/HTM-262-PC In the textile industry, softeners are called textile finishing products that are used at the end of the manufacture of a textile to provide a good softness as well as retain good absorbency to the textile. Existing softeners in the textile industry exhibit such benefits but they fade away after several wash cycles.
  • softener finishing products which when applied under the form of an emulsion on the textile, must have a long-lasting softness effect even after several washes.
  • Softeners used as textile finishing products in the textile industry must then exhibit high durability.
  • Various silicone block copolymers and their emulsions thereof, has been explored as hydrophilic softeners on various type of fabrics.
  • Amine functional end blocking has advantageous for the treatment of textiles or fibers. However, owing to weak ionic interactions these softeners are not retained on the substrates after several washing conditions.
  • Meissner Bolte 3 M/HTM-262-PC Therefore, there is a need for a polymer suitable for textile end finishing product, having a good durability and exhibiting simultaneously improved soft handfeel, and maintains acceptable hydrophilicity properties while having an acceptable viscosity, thereby allowing an easier handling by the manufacturer.
  • aminosilicones has been well known for very high handfeel and wash durability up to several wash cycles. However, they do not exhibit good water absorbency. Hence retaining softener properties of the silicone polymers after several wash cycles along with water absorbency has been a key challenge for silicone softeners till date.
  • An object of the present invention is to provide a polymer overcoming all or part of the aforementioned drawbacks.
  • organo-functional silicone emulsion has been developed as a flexible binder that enables covalent binding of hydrophilic silicone softeners and cellulosic substrates forming interpenetrated network.
  • textile treated with the composition comprising of the binder polymer according to the invention exhibit durable softness after several wash cycles.
  • Another object of the present invention is to provide a composition for treating a textile comprising of the flexible binder polymer according to the invention which exhibit simultaneously excellent hydrophilicity property and improved soft handfeel property after several wash cycles.
  • the term “consists essentially of” followed by one or more characteristics, means that may be included in the process or the material of the invention, besides explicitly listed components or steps, components or steps that do not materially affect the properties and characteristics of the invention.
  • the present invention concerns an organo-functional silicone copolymer resulting from the copolymerization of: - at least one silicone monomer comprising at least 2 functional epoxy groups, - at least one trialkoxy silane monomer, and - at least one amine compound comprising at least 2 functional amine groups.
  • the invention also concerns a method for preparing a copolymer according to any of foregoing claims comprising at least one polymerization step a) in which at least the following are brought into contact in a solvent: - at least one silicone monomer comprising at least 2 functional epoxy groups, - at least one trialkoxy silane with at least one functional epoxy or amino group, and - at least one amine with at least 2 functional amine groups.
  • the invention further concerns an aqueous emulsion, solution or suspension comprising a) the organo-functional silicone copolymer b) at least one nonionic surfactant, and c) at least one weak protic acid.
  • the invention further concerns a composition comprising the aqueous emulsion, solution or suspension as described above and at least one hydrophilic polymer. Moreover, the invention concerns the use of the aqueous emulsion, solution or suspension as described above or the composition as described above in treating textile for improving simultaneously the soft handfeel and the hydrophilicity after several wash cycles of said textile. The invention also concerns a textile treated with the aqueous emulsion, solution or suspension as described above or with the composition as describe above. Finally, the invention relates to a method for treating a textile comprising the application of the aqueous emulsion, solution or suspension according to the invention or the composition according to the invention to a textile.
  • Organo-functional silicone copolymer resulting from the copolymerization of: - at least one silicone monomer comprising at least 2 functional epoxy groups, - at least one trialkoxy silane with at least one functional epoxy or amino group, and - at least one amine with at least 2 functional amine groups.
  • the invention concerns organo-functional silicone copolymer resulting from the reaction of a silicone monomer comprising at least 2 functional epoxy groups with a diamine compound comprising at least 2 functional amine groups to obtain a reaction product and further reaction of said reaction product with a trialkoxy silane with at least one functional epoxy or amino group.
  • organo-functional silicone copolymer emulsion according to the invention when applied on textile, makes it possible to obtain a textile having improved soft handfeel properties until 10 or more wash cycles.
  • the organo-functional silicone copolymer emulsion according to the invention when applied on textile in form of a composition with other hydrophilic additives or polymers, makes it possible to obtain a textile having simultaneously improved handfeel and hydrophilic properties until 10 or more wash cycles.
  • copolymer is meant an oligomer or a linear or branched macromolecule having a sequence constituted by several repeating units (or monomer units) of which at least two units have a different chemical structure.
  • linear is meant a polymer or copolymer consists of a single continuous chain of repeating units.
  • the covalently bonded atoms form the backbone of the polymer, which can be optionally substituted by one or more alkyl groups comprising less than 10 carbon atoms, preferably comprising between 1 and 8 carbon atoms, more preferably comprising between 1 and 4 carbon atoms.
  • monomer unit or “monomer” is meant a molecule that can be converted to an oligomer or a macromolecule by combining with itself or with other molecules of the same type. A monomer denotes the smallest constituent unit the repetition of which leads to an oligomer or a macromolecule.
  • random copolymer an oligomer or a macromolecule in which the sequential distribution of the monomer units obeys known statistical laws.
  • a copolymer is said to be random when it is constituted by monomer units the distribution of which is a Markov distribution.
  • the distribution of the monomer units in the polymer chain depends on the reactivity of the polymerizable functions of the monomers and the relative concentration of the monomers.
  • the organo-functional silicone copolymers of the invention are different from block copolymers and gradient copolymers.
  • block is meant a part of a copolymer comprising several monomer units, identical or different and which have at least one particular feature of constitution Meissner Bolte 7 M/HTM-262-PC or of configuration by which it can be distinguished from the parts adjacent to it.
  • a gradient copolymer denotes a copolymer with at least two monomer units of different structures the monomer composition of which changes gradually along the polymer chain, thus passing progressively from one end of the polymer chain rich in one monomer unit, to the other end rich in the other comonomer.
  • the terms “copolymer”, “random linear copolymer” and “linear copolymer” refer all to the copolymer according to the invention and can be interchangeably used.
  • copolymerization or “polymerization” is meant a process for converting a mixture of at least two monomer units of different chemical structures into an oligomer or a copolymer. According to the invention, the terms “copolymerization” and “polymerization” have the same meaning and can be interchangeable.
  • the copolymer according to the invention is suitable for textile. More preferably, the copolymer according to the invention is suitable for textile end finishing product such as softeners.
  • the terms “textile” and “textile materials” have to be interpreted broad and can be in a very wide range of forms of presentations, for example, in the form of fibers, yarns, fabrics, garments, knits, towels, wovens and non-wovens.
  • the copolymers according to the invention are suitable for treating a wide variety of textile materials.
  • the textile according to the present invention can be a natural (non-synthetic) cellulose-based textiles such as cotton, silk, wool, linen and hemp, or a synthetic textile material such as polyamides, polyurethanes, polyacrylics, polyesters, polyolefines, polylactide, or also blends of natural textile material with synthetic textile material such as blends of cotton and polyester fibres or polyamide fibres.
  • the copolymers of the invention when applied on textile, provide an excellent soft handfeel property to the textile until several wash cycles. Thereby providing durability of the finishing polymer on the fabric.
  • the copolymers according to the invention can be used with all types of textiles, meaning that the copolymers when applied on different textiles, exhibit improved soft handfeel properties until several washes regardless the type of textile on which they are applied. It is well known that the cellulose-based textiles are by nature hydrophilic and that the synthetic textile material such as polyester textile are by nature hydrophobic. As also used herein, the terms “softeners”, “textile finishing products” and “textile end finishing products” have the same meaning and can be interchangeably used.
  • the terms “softeners”, “textile finishing products” and “textile end finishing products” refer to the copolymers according to the invention resulting from the polymerization of silicone monomers, trialkoxy silane monomers and amino compounds and when applied on a textile, the said textile exhibits improved soft handfeel and hydrophilicity properties.
  • the terms “soft handfeel” and “softeness” refer to a property of the textile after being treated with the copolymer according to the invention.
  • the soft handfeel of the textile treated with the copolymer according to the invention is a tactile assessment or a hand assessment.
  • the organo-functional silicone copolymer according to the invention has a molar percentage of silicone monomer in said copolymer ranging from 35 to 55 %, preferably 40 to 50 %, more preferably ranging from 42 to 45 %.
  • the organo-functional silicone copolymer according to the invention has a molar percentage of: - silicone monomer in said copolymer ranging from 35 to 55%, preferably 40 to 50%, more preferably ranging from 42 to 45%.
  • organo-functional silicone copolymer according to the invention has a molar percentage of: - silicone monomer in said copolymer ranging from 42 to 45%, - amine compound in said copolymer ranging from 37 to 40%, and - trialkoxy silane in said copolymer ranging from 18 to 21%.
  • the mass ratio between the silicone monomer and the trialkoxy silane in the copolymer according to the invention is ranging from 1:0.003 to 1:0.03 by weight, preferably from 1:0.005 to 1:0.02, more preferably from 1:0.008 to 1:0.009.
  • the mass ratio of monomers in all aspects of the disclosure can be adjusted to manipulate the characteristics of the copolymer as desired.
  • the monomers can be present in mass ratios of silicone monomer to trialkoxy silane monomer of 97:3, 98: 2, 99:1, 99.2:0.8, 99.5:0.5 and 99.7:0.3, by weight.
  • the monomers can be present in mass ratios of silicone monomer to trialkoxy silane monomer of 99:1, 99.2:0.8, and 99.5:0.5 by weight.
  • the copolymer according to the invention results from the copolymerization of: - at least one silicone monomer comprising at least 2 functional epoxy groups, - at least one trialkoxy silane monomer comprising 1 functional epoxy group, and - at least one amine compound comprising at least 2 functional amine groups, wherein the equivalent weight ratio of the epoxy to amine is from 1:1 to 1:1.5 by equivalent weight.
  • the organo-functional silicone copolymer according to the invention has a number-average molecular weight ranging from 12000 to 20000 g/mol, preferably from 14000 to 18000 g/mol.
  • number average molecular weight refers to the number-average molecular weight being obtained by measurement by size exclusion chromatography, in particular by using polystyrene calibration.
  • the method of measurement by size exclusion chromatography using polystyrene calibration is for example described in the work (Fontanille, M.; Gnanou, Y., Chimie et physico to Chimie des polymeres [Chemistry and physical chemistry of polymers]. 2nd ed.; Dunod: 2010; p 546).
  • the word “average” refers to number average unless indicated otherwise.
  • the copolymer according to the invention has the advantage of having an acceptable viscosity which allows the manufacturer to handle it easily without any tackiness issues and to apply the copolymer in the form of a solution, emulsion or dispersion easily and evenly on the textile.
  • acceptable viscosity is to be understood as a viscosity being less than 3000 mPas, notably ranging from 30 to 600 mPas that allows the manufacturer to handle the copolymer without any issues of tackiness.
  • a copolymer having an acceptable viscosity according to the invention also refers to a copolymer being easy, processable meaning that the copolymer according to the invention is easily dissolved into an aqueous solution, or dispersed in an emulsion or dispersion that are further applied on the textile. Therefore, the copolymer is evenly applied on the textile which provides to the whole treated textile the soft handfeel and the hydrophilicity properties.
  • the term “viscosity” refers to the Brookfield viscosity expressed in mPas. The viscosity is measured using a Brookfield viscometer at 2000 + heading. It is measured at 25°C and at a speed of 200 rev/min rotation. Reading of the measurement is carried out after 30 seconds at 25°C.
  • the silicone monomer according to the invention is of the structure M1D1aM1 or M2D1aD2bM2, where M1 is R1R2ReSiO 1/2 D1 is R3R4SiO1/2 M2 is R5R6R7SiO1/2 D2 is R8ReSiO 1/2 , wherein R1, R2, R3, R4, R5, R6, R7 are independently chosen from a C1 to C10 aliphatic or aromatic group.
  • Re has a composition as -A-Z; where A is chosen from a group comprising an alkyl (C1 to C10), or C3 to C10 polyester or C2 to C10 polyether with EO (ethylene oxide) and PO (propylene oxide) groups ; Z is an epoxy ring.
  • A is chosen from a group comprising an alkyl (C1 to C10), or C3 to C10 polyester or C2 to C10 polyether with EO (ethylene oxide) and PO (propylene oxide) groups ;
  • Z is an epoxy ring.
  • a is an integer ranging from 200 to 400, more preferably from 250 to 350, more preferably from 280 to 330
  • b is an integer ranging from 2 to 4, more preferably from 2 to 3, more preferably 2.
  • the silicone monomer according to the invention has general formula (Ia), (Ib), (Ic) or (Id): m is an integer ranging from 1 to 10more preferably from 3 to 7, more preferably from 3 to 4, a is an integer ranging from 200 to 400, more preferably from 250 to 350, more preferably from 280 to 330, and R1, R2, R3 and R4 are independently chosen from a C1 to C10 alkyl group, preferably a C1 to C4 alkyl group, more preferably a C1 to C2 alkyl group, or a C6 to C20 aromatic hydrocarbon group, preferably a C6 to C8 aromatic hydrocarbon group.
  • Meissner Bolte 12 M/HTM-262-PC By “Ci to Cj alkyl” is meant a saturated, linear or branched hydrocarbon to Containing chain, comprising from i to j carbon atoms. By aromatic hydrocarbon group is meant an unsubstituted or substituted organic chemical compound.
  • m is an integer ranging from 1 to 10 more preferably from 3 to 7, more preferably from 3 to 4
  • n is an integer ranging from 1 to 10, more preferably from 1 to 5, more preferably from 1 to 2
  • a is an integer ranging from 200 to 400, more preferably from 250 to 350, more preferably from 280 to 330
  • Z is a C2 to C10 polyester or polyether group, preferably a C2 to C5 polyester or polyether group, more preferably a C2 to C3 polyester or polyether group
  • R1, R2, R3 and R4 are independently chosen from a C1 to C10 alkyl group, preferably a C1 to C4 alkyl group, more preferably a C1 to C2 alkyl group, or a C6 to C20 aromatic hydrocarbon group, preferably a C6 to C8. aromatic hydrocarbon group.
  • Meissner Bolte 13 M/HTM-262-PC m is an integer ranging from 1 to 10, more preferably from 3 to 7, more preferably from 3 to 4, a is an integer ranging from 200 to 400, more preferably from 250 to 350, more preferably from 280 to 330, b is an integer ranging from 2 to 4, more preferably from 2 to 3, more preferably 2, and R3, R4, R5, R6, R7 and R8 are independently chosen from a C1 to C10 alkyl group, preferably a C1 to C4 alkyl group, more preferably a C1 to C2 alkyl group, or a C6 to C20 aromatic hydrocarbon group, preferably a C6 to C8 aromatic hydrocarbon group.
  • Meissner Bolte 14 M/HTM-262-PC m is an integer ranging from 1 to 10 more preferably from 3 to 7, more preferably from 3 to 4
  • n is an integer ranging from 1 to 10, more preferably from 1 to 5, more preferably from 1 to 2
  • a is an integer ranging from 200 to 400, more preferably from 250 to 350, more preferably from 230 to 280
  • b is an integer ranging from 2 to 4, more preferably from 2 to 3, more preferably 2
  • Z is a C2 to C10 polyester or polyether group, preferably a C2 to C5 polyester or polyether group, more preferably a C2 to C3 polyester or polyether group
  • R3, R4, R5, R6, R7 and R8 are independently chosen from a C1 to C10 alkyl group, preferably a C1 to C4 alkyl group, more preferably a C1 to C2 alkyl group, or a C6 to C20 aromatic hydrocarbon group, preferably a C6 to C8 aromatic hydro
  • Silicones of formula (Ia), (Ib), (Ic), (Id) are known to a person skilled in the art and are commercially available. Particularly suitable silicone monomer is for example RH-NB- ES-12K from Runhe. According to an embodiment, the silicone monomer according to the invention is at least one of the silicone monomers of formula (Ia), (Ib), (Ic), (Id). According to another embodiment, the silicone monomer according to the invention consists of one single silicone monomer of formula (Ia), (Ib), (Ic), (Id).
  • the trialkoxy silane monomer according to the invention is a mixture of at least two different trialkoxy silane monomers of formula (IIa) or (IIb).
  • the trialkoxy silane monomer according to the invention is a mixture of two different trialkoxy silane monomers of formula (IIa) or (IIb).
  • the trialkoxy silane monomer according to the invention consists of one single trialkoxy silane monomer of formula (IIa) or (IIb).
  • Amine compound In an embodiment, the amine compound according to the invention comprises at least 2 functional amine groups. Preferably, the amine compound according to the invention comprises 2 functional amine groups.
  • the amine groups of the amine compound according to the invention are reacted with the epoxy groups from the trialkoxy silane monomer (IIa) or from the silicone monomer (Ia), (Ib), (Ic), (Id) to form the partial crosslinked organo-functional silicone copolymer according to the invention.
  • the use of amine compound comprising functional amine groups as linker between the monomers allows advantageously to control the structure of the copolymer during its polymerization and thus allows to obtain linear or branched copolymer according to the invention.
  • Meissner Bolte 16 M/HTM-262-PC In a preferred embodiment, the amine compound according to the invention is a cyclic or linear amine compound.
  • the amine compound according to the invention is a linear amine compound.
  • the 2 functional amine groups of the amine compound according to the invention are part of the backbone of said amine compound.
  • the 2 functional amine groups of the amine compound according to the invention are part of the cyclic backbone of said amine compound.
  • the amine compound according to the invention has general formula (IIIa), (IIIb), or (IIIc) : in which R is H or Me, y is an integer ranging from 2 to 39, more preferably from 4 to 35, more preferably from 10 to 30 or from 7 to 11, and Preferably, the sum of x and z is an average value ranging from 1.2 to 6, more preferably from 1.8 to 4, more preferably from 2 to 3 or from 3 to 4, Meissner Bolte 17 M/HTM-262-PC in which u is an integer ranging from 2 to 68, more preferably from 5 to 60, more preferably from 10 to 50.
  • the composition further comprises piperidine in addition to the amine compound comprising 2 functional amine groups according to the invention. It is understood that piperidine comprises only one amino function, nevertheless it may be added to the mixture comprising an amine compound which comprises two amino functions.
  • the amine compound according to the invention is a mixture of at least one amine compound of formula (IIIa) and at least one amine compound of formula (IIIb).
  • the amine compound according to the invention is a mixture of at least one amine compound of formula (IIIb) and piperidine.
  • the invention also concerns a method for preparing a copolymer according to the invention comprising at least one polymerization step a) in which at least the following are brought into contact in a solvent: - at least one silicone monomer comprising at least 2 functional epoxy groups, - at least one trialkoxy silane monomer, and - at least one amine compound comprising at least 2 functional amine groups.
  • a first step the silicone monomer comprising at least 2 functional epoxy groups is reacted with the amine compound comprising at least 2 functional amine groups to obtain a first reaction product and then this first reaction product is reacted with the trialkoxy silane monomer.
  • the solvent used in step a) has a boiling point of less than 150°C, preferably less than 130°C, more preferably comprised from 65°C to 130°C.
  • the solvent used in step a) is isopropanol or diethylene glycol butyl ether.
  • the polymerization step a) is carried under inert atmosphere such as nitrogen atmosphere.
  • the method further comprises the addition of a surfactant and water before the distillation step in order to avoid high viscosity and to improve handling and processing of the copolymer and its storage properties.
  • the copolymer according to the invention are intended as softeners for textile.
  • the invention also concerns an aqueous emulsion, solution or suspension comprising a) the least one copolymer according to the invention, b) at least one nonionic surfactant, and c) at least one weak protic acid.
  • Meissner Bolte 19 M/HTM-262-PC Preferably, the aqueous emulsion, solution or suspension is under the form of an aqueous emulsion.
  • the aqueous emulsion, solution or suspension according to the invention comprise non- ionic surfactants, wherein non-ionic surfactants are alkoxylated alcohols containing C8 to C18 liner or branched carbon chain and alkoxy group is an ethoxy and/or propoxy from 1 to 11 repeat units.
  • the aqueous emulsion, solution or suspension according to the invention comprise at least one weak protic acid, wherein the at least one weak protic acid has a pKa of 0 to 10, more preferably from 2 to 8, most preferably from 3 to 7.
  • An example for a weak protic acid is acetic acid or formic acid.
  • the aqueous emulsion, solution or suspension is applied on the textile for providing improved soft handfeel until several wash cycles to the textile.
  • the copolymer is present in the aqueous emulsion, solution or suspension according to the invention in a concentration from 10 wt% to 60 wt%, preferably from 10 wt% to 50 wt%, more preferably from 15 wt% to 40 wt%, most preferably from 20 wt% to 30 wt% calculated on the total weight of the composition.
  • the surfactant is present in the aqueous emulsion, solution or suspension according to the invention in a concentration from 3 wt% to 20 wt%, preferably from 3 wt% to 15 wt%, more preferably from 5 wt% to 10 wt%, most preferably from 5 wt% to 8 wt% calculated on the total weight of the composition.
  • surfactant refers to a substance that reduces surface tension of a liquid. Typical examples that are useful for applying on textile are anionic or non-ionic surfactants such as fatty alcohol ethoxylates, fatty alcohol alkoxylates etc. which acts a wetting and rewetting agent.
  • the non-ionic surfactants referred to this invention are linear or branched alkoxyated alcohol with C8 to C18 carbon chain and degree of ethoxylation/propoxylation ranging from 1-12.
  • Anionic surfactants are selected from Meissner Bolte 20 M/HTM-262-PC sulfate, sulfonate, phosphates of linear or branched alkyl chain with or without alkoxy group.
  • the aqueous emulsion, solution or suspension according to the invention comprises at least: - at least one copolymer according to the invention in a concentration from 10 wt% to 60wt%, preferably from 10 wt% to 50 wt%, more preferably from 15 wt% to 40 wt%, most preferably from 20 wt% to 30 wt% calculated on the total weight of the aqueous emulsion, solution or suspension, and - a surfactant in a concentration from 3 wt% to 20 wt%, preferably from 3 wt% to 15 wt%, more preferably from 5 wt% to 10 wt%, most preferably from 5 wt% to 8 wt% calculated on the total weight of the aqueous emulsion, solution or suspension Unless otherwise expressed, the “weight percentage” (indicated as % wt or wt%) of a copolymer or a surfactant mixture in the aqueous emul
  • the aqueous emulsion, solution or suspension according to the invention may further comprise organic solvents, preferably with hydroxyl functionality and selected from a group of mono or poly hydroxy alcohols from C2 to C10 with 1-3 hydroxy groups and 0-4 ether linkages such as butyl diglycol, poly ethylene/ propylene glycols, Diethylene glycols.
  • the method further comprises a distillation step of the solvent used in step a) in order to obtain the copolymer composition according to the invention and as above-described. This distillation step allows to obtain the copolymer composition ready to be used without any need of further purification.
  • the distillation step is carried under 200mbar.
  • the distillation step is carried at a temperature of the boiling point of the solvent.
  • the temperature of the distillation step is less than 100°C, preferably less than 70°C, more preferably in the range of 30°C to 50°C, preferably under vacuum pressure.
  • COMPOSITION AND USE The present invention also concerns a composition comprising the aqueous emulsion, solution or suspension according to the invention, and at least one emulsion of one hydrophilic polymer or at least one hydrophilic molecule.
  • hydrophilic polymer or “hydrophilic molecule” refers to a substance that is water loving in nature and enhances water absorbing property.
  • Typical examples that are useful on textile are ionic and non-ionic polymers or hydrophilic molecules known in the prior art wherein ionic polymers or molecules bearing carboxylates or sulfonates or phosphates or phosphonates groups as well as non-ionic polymers or molecules bearing polyether or acrylate or amide or hydroxy groups etc. act as hydrophilic agents.
  • the hydrophilic polymer is the polymerization product of - at least one silicone monomer comprising at least 2 functional epoxy groups, - at least one amine compound comprising at least 2 functional amine groups.
  • the at least one hydrophilic polymer comprises a repeating unit of the general formula (IV), well known in state of art: m is an integer ranging from 1 to 10 more preferably from 3 to 7, more preferably from 3 to 4, a is an integer ranging from 200 to 400, more preferably from 250 to 350, more preferably from 280 to 330, Meissner Bolte 22 M/HTM-262-PC R1, R2, R3 and R4 are independently chosen from a C1 to C10 alkyl group, preferably a C1 to C4 alkyl group, more preferably a C1 to C2 alkyl group, or a C6 to C20 aromatic hydrocarbon group, preferably a C6 to C8 aromatic hydrocarbon group, and X is an amine compound comprising at least 2 functional amine groups.
  • m is an integer ranging from 1 to 10 more preferably from 3 to 7, more preferably from 3 to 4
  • a is an integer ranging from 200 to 400, more preferably from 250 to 350, more preferably from 280
  • the above definition for the at least one silicone monomer and the at least one amine compound to be reacted with each other also applies to the at least one polymer.
  • the aqueous emulsion, solution or suspension according to the invention and an emulsion of atleast one hydrophilic polymer are present in a ratio of 50:50, more preferably of 20:80, most preferably from 10:90 in the composition according to the invention.
  • the hydrophilicity of a textile could be significantly improved by treatment with the composition according to the invention without reducing the durability of the hand feel.
  • the polymers comprising a repeating unit of the general formula (IV) provide good hydrophilicity for a textile but are not durable in hand feel.
  • the copolymer according to the invention interacts with the hydrophilic polymer in the composition according to the invention forming an interpenetrated network that helps to retain the soft handfeel even after several wash cycles thereby giving good durability and simultaneously increasing the hydrophilicity.
  • the present invention also concerns a process for treating the textile with the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention or the copolymer according to the invention, in which the said composition or the aqueous emulsion, solution or suspension according to the invention or copolymer according to the invention is applied to the said textile or incorporated into it.
  • the present invention also concerns the use of the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention or the copolymer according to the invention in treating textile for improving Meissner Bolte 23 M/HTM-262-PC simultaneously the soft handfeel until several washes and the hydrophilicity of said textile.
  • the present invention also concerns a textile treated with the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention.
  • APPLICATION PROCESS The present invention also concerns a method for treating a textile comprising the application of the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention to a textile.
  • composition according to the invention or the aqueous emulsion, solution or suspension according to the invention of the can be carried out by various methods.
  • the application comprises coating with an air knife or rod coater, impregnation or immersion by padding or exhaust method, printing techniques, spray coating, inclusion into the textile fibers such as polyester, nylon or modacrylic fiber material, during the spinning process.
  • the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention is applied to the textile at a concentration in the range of 20 to 80 g/l or 2 % to 12% and/or has a pH in the range of 3 to 11.
  • the textile treated with composition according to the invention or the aqueous emulsion, solution or suspension according to the invention is dried or cured.
  • the drying or curing is carried out at a temperature of 80 to 180°C and/or for a time of 10 seconds to 12 minutes.
  • the copolymers according to the invention are suitable for treating a wide variety of substrates including fibers, yarns, fabrics, knits, towels, woven, non-woven and garments.
  • the textile treated with composition according to the invention or the aqueous emulsion, solution or suspension according to the invention can be a natural (non- synthetic) cellulose-based textiles such as cotton, silk, wool, linen and hemp or a synthetic textile material such as polyamides, polyurethanes, polyacrylics, polyesters, polyolefins, polylactide or also blends of natural textile material with synthetic textile material such as blends of cotton and polyester fibers or polyamide fibers.
  • a natural (non- synthetic) cellulose-based textiles such as cotton, silk, wool, linen and hemp
  • a synthetic textile material such as polyamides, polyurethanes, polyacrylics, polyesters, polyolefins, polylactide or also blends of natural textile material with synthetic textile material such as blends of cotton and polyester fibers or polyamide fibers.
  • Examples 1, 2 and 3 represents (AB)n silicone polymer with crosslinker groups.
  • Examples 4, 5 and 6 are comparative representations of (AB)n silicone polymer without crosslinker groups that are known in state of art and are typically used as hydrophilic softener coatings in textile finishing.
  • Examples 7, 8, 9, 10, 11, 12, 13, 14 and 15 representing coating composition using silicone crosslinker polymer that can be used in textile finishing as softeners for durable performance of handfeel and hydrophilicity.
  • Surfactant V51(Imbentin-U/050)-C11&5EO (non-ionic surfactant), Esteem- 48-AK- C13&11EO (non-ionic surfactant) - Silicone monomer: RH-NB-ES-12K (Diepoxy terminated PDMS) - Amine compound: Piperazine (Diamine), Jeffamine ED-600 (Diamine polyether) - Solvent : water, isopropanol, Butyl carbitol, Glycerol.
  • each polymer solution was emulsified by adding the 400g of polymer solution in aqueous solution of 500g water and 50 g each of non-ionic surfactants C13/11EO and C115EO surfactants at 25oC-60oC and stirring for 30 minutes. pH 5-7 was maintained by neutralizing the solution with dilute acetic acid (22%). Solvent Meissner Bolte 26 M/HTM-262-PC isopropanol was removed by vaccum distillation and observed solid content of the emulsions is in the range of 27-30%.
  • each polymer solution was emulsified by adding the 400g of polymer solution in aqueous solution of 500g water and 50 g each of non-ionic surfactants C13/11EO and C115EO surfactants at 25oC-60oC- and stirring for 30 minutes. pH 5-7 was maintained by neutralizing the solution with dilute acetic acid (22%). Adjust solid content of the emulsions is in the range of 27-30%. With the use of butyl carbitol as solvent, the isopropanol stripping process is eliminated.
  • each polymer solution was emulsified by adding the 400g of polymer solution in aqueous solution of Meissner Bolte 27 M/HTM-262-PC 500g water and 50 g each of C13/11EO and C115EO surfactants at 25 oC-60oC and stirring for 30 minutes. pH 5-7 was maintained by neutralizing the solution with dilute acetic acid (22%). Observed solid content of the emulsions is in the range of 27-30%. Comparative Examples (conventional hydrophilic softner without crosslinker)
  • Adjust solid content of the emulsions is in the range of 27-30%. With the use of butyl carbitol as solvent, the isopropanol stripping process is eliminated.
  • composition of organo-functional silicone copolymer emulsion according to the invention was made with conventional hydrophilic silicone softeners emulsions as in example 7, 8, 9, 10, 11, 12, 13, 14, 15. Comparison of performance of the composition was done with example 1 and conventional hydrophilic softeners that are known in state of art, as in example 4, 5 and 6.
  • Handfeel ranking Absorbency (before Before wash After 10 HL washing) (sec) Blank 7 7 0.0 ULTRATEX SI 3 5 6.0 ULTRATEX 7 0.3 STS-U 3 Example 1 1 3 6.0 Example 10 3 5 1.0 Example 11 1 3 2.5 Example 12 1 3 3.0 Example 13 1 3 4.0 Example 14 1 3 2.5 Example 15 1 3 3.0 Meissner Bolte 36 M/HTM-262-PC Fabrics treated with copolymer compositions of the current invention showed comparable handfeel and absorbency performance to conventional hydrophilic silicone softeners (comparative examples) before washing. However, after washing (up to 10 HL) it exhibited good retention of handfeel as shown by good ranking (lowest ranking is the best), indicative of higher durability.
  • Crosslinker copolymer enables crosslinking of the hydrophilic softener polymers with the fabric forming interpenetrated network that ensures that polymer is not removed off from the fabric even after several washing cycles. Hence balanced hydrophilicity along with handfeel durability is well attained by the composition that uses crosslinker copolymer.
  • Figure 1 Graphical representation of the results from Table5. On the x-axis is the handfeel ranking and on the y-axis the absorption value. The double circle point in the graph refers to the desired performance.
  • Figure 2 Graphical representation of the results from Table 6. On the x-axis is the handfeel ranking and on the y-axis the absorption value. The double circle point in the graph refers to the desired performance.
  • Figure 3 Graphical representation of the results from Table 7. On the x-axis is the handfeel ranking and on the y-axis the absorption value. The double circle point in the graph refers to the desired performance.
  • Figure 4 Graphical representation of the results from Table 8. On the x-axis is the handfeel ranking and on the y-axis the absorption value. The double circle point in the graph refers to the desired performance.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

La présente invention concerne le domaine des copolymères appropriés pour le textile, plus particulièrement des copolymères appropriés pour des produits de finition finale textile tels que des adoucissants. Plus particulièrement, la présente invention concerne un copolymère de silicone organo-fonctionnel qui résulte de la polymérisation de monomères de silicone, de monomères de trialcoxy silane et de composés d'amine. La présente invention concerne également une composition desdits copolymères avec d'autres polymères hydrophiles et des utilisations desdits copolymères, ainsi que leurs compositions.
PCT/EP2024/076327 2023-09-19 2024-09-19 Agent de réticulation à base de silicone organo-fonctionnel et composition de finition durable formée à partir de celui-ci Pending WO2025061880A1 (fr)

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WO1997032917A1 (fr) 1996-03-04 1997-09-12 Osi Specialities, Inc. Copolymeres blocs de silicone et d'aminopolyalkyleneoxyde
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