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KR-20260065950-A - Organic functional silicone crosslinking agent and durable finishing composition formed therefrom

KR20260065950AKR 20260065950 AKR20260065950 AKR 20260065950AKR-20260065950-A

Abstract

The present invention relates to copolymers suitable for textiles, more particularly to copolymers suitable for textile final finishing products, such as softeners. More specifically, the present invention relates to an organic functional silicone copolymer, which is an organic functional silicone copolymer produced by the polymerization of a silicone monomer, a trialkoxysilane monomer, and an amine compound. Furthermore, the present invention relates to a composition of a hydrophilic polymer other than the copolymer and to the use of the copolymer and the composition thereof.

Inventors

  • 메라 메에날
  • 나라야난 사노오지
  • 파텔 차야 엠 타카르
  • 쿠마르 리시
  • 칼리아판 라자

Assignees

  • 아크로마 (스위처랜드) 게엠베하

Dates

Publication Date
20260511
Application Date
20240919
Priority Date
20231120

Claims (20)

  1. As an organic functional silicone copolymer, - At least one silicon monomer comprising at least two functional epoxy groups, - At least one trialkoxysilane monomer and - An organic functional silicone copolymer produced by copolymerizing at least one amine compound comprising at least two functional amine groups.
  2. An organic functional silicone copolymer according to claim 1, wherein the molar percentage of the silicone monomer in the organic functional silicone copolymer is 35 to 55%, preferably 40 to 50%, more preferably 42 to 45%.
  3. An organic functional silicone copolymer according to claim 1 or 2, wherein the mass% of the trialkoxysilane monomer in the organic functional silicone copolymer is 0.5 to 1.5 wt%, preferably 0.5 to 1.2 wt%, more preferably 0.8 to 1 wt%.
  4. An organic functional silicon copolymer according to any one of claims 1 to 3, wherein the silicon monomer has the chemical formula (Ia), (Ib), (Ic) or (Id). [Chemical Formula (Ia)] [Chemical formula (Ib)] [Chemical Formula (Ic)] [Chemical Formula (Id)] In the above chemical formulas (Ia), (Ib), (Ic) and (Id), m is an integer in the range of 1 to 10, more preferably 3 to 7, and more preferably 3 to 4, and n is an integer in the range of 1 to 10, more preferably 1 to 5, and more preferably 1 to 2, and a is an integer in the range of 200 to 400, more preferably 250 to 350, more preferably 280 to 330, and b is an integer from 2 to 4, more preferably an integer from 2 to 3, more preferably 2, and 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, and R1 , R2 , R3 , R4 , R5 , R6 , R7 , and R8 are selected from C1 to C10 alkyl groups, preferably C1 to C4 alkyl groups, more preferably C1 to C2 alkyl groups, C6 to C20 aromatic hydrocarbon groups, and preferably C6 to C8 aromatic hydrocarbon groups.
  5. An organic functional silicone copolymer according to any one of claims 1 to 4, wherein the trialkoxysilane monomer has the chemical formula (IIa) or (IIb). [Chemical Formula (IIa)] [Chemical Formula (IIb)] In the above chemical formulas (IIa) and (IIb), Y is a C1 to C10 linear or branched carbon chain, preferably Me, Et, n-Pr, i-Pr, n-Bu or t-Bu, and more preferably Me or Et.
  6. An organic functional silicone copolymer according to any one of claims 1 to 5, wherein the amine compound is a cyclic or linear amine compound.
  7. An organic functional silicone copolymer according to any one of claims 1 to 6, wherein the amine compound has the chemical formula (IIIa), (IIIb) or (IIIc). [Chemical Formula (IIIa)] [Chemical Formula (IIIb)] [Chemical Formula (IIIc)] In the above chemical formulas (IIIa), (IIIb), and (IIIc), R is H or Me, and y is an integer in the range of 2 to 39, more preferably 4 to 35, and more preferably 10 to 30, and u is an integer in the range of 2 to 68, more preferably 5 to 60, and more preferably 10 to 50, and Preferably, the sum of x and z has an average value in the range of 1.2 to 6, more preferably 1.8 to 4, and more preferably 2 to 3.
  8. An organic functional silicone copolymer according to any one of claims 1 to 7, wherein the amine compound is a mixture of at least one amine compound of formula (IIIa) and at least one amine compound of formula (IIIb). [Chemical Formula (IIIa)] [Chemical Formula (IIIb)] In the above chemical formulas (IIIa) and (IIIb), R is H or Me, and y is an integer in the range of 2 to 39, more preferably 4 to 35, and more preferably 10 to 30, and Preferably, the sum of x and z has an average value in the range of 1.2 to 6, more preferably 1.8 to 4, and more preferably 2 to 3.
  9. An organic functional silicone copolymer according to any one of claims 1 to 8, wherein the amine compound is a mixture of at least one amine compound of formula (IIIb) and piperidine. [Chemical Formula (IIIb)] In the above chemical formula (IIIb), y is an integer in the range of 2 to 39, more preferably 4 to 35, and more preferably 10 to 30, and Preferably, the sum of x and z has an average value in the range of 1.2 to 6, more preferably 1.8 to 4, and more preferably 2 to 3.
  10. A method for manufacturing a copolymer as described in any one of claims 1 to 9, comprising at least one polymerization step a), wherein in step a), at least, - At least one silicon monomer comprising at least two functional epoxy groups, - At least one trialkoxysilane monomer and - A method for preparing a copolymer in which at least one amine compound comprising at least two functional amine groups is contacted in a solvent.
  11. A method for preparing a copolymer according to claim 10, wherein the boiling point of the solvent used in step a) is less than 150°C, preferably less than 130°C, more preferably 65 to 130°C.
  12. A method for preparing a copolymer, comprising, in claim 10 or 11, a distillation step of the solvent used in step a).
  13. A method for producing a copolymer according to any one of claims 10 to 12, wherein the temperature of the distillation step is preferably less than 100°C, preferably less than 70°C, more preferably 30 to 50°C, under vacuum pressure.
  14. As an aqueous emulsion, solution, or suspension, a) at least one copolymer described in any one of claims 1 to 9, b) at least one nonionic surfactant and c) An aqueous emulsion, solution, or suspension comprising at least one protic weak acid.
  15. In claim 14, the aqueous emulsion, solution, or suspension in which the copolymer is present at a concentration of 10 to 60 wt%, preferably 10 to 50 wt%, more preferably 15 to 40 wt%, and most preferably 20 to 30 wt% based on the total weight of the aqueous emulsion, solution, or suspension.
  16. An aqueous emulsion, solution, or suspension according to claim 14 or 15, wherein the nonionic surfactant is present in the aqueous emulsion, solution, or suspension at a concentration of 3 to 20 wt%, preferably 3 to 15 wt%, more preferably 5 to 10 wt%, and most preferably 5 to 8 wt% based on the total weight of the aqueous emulsion, solution, or suspension.
  17. A composition comprising an aqueous emulsion, solution, or suspension described in any one of claims 14 to 16, and an emulsion of at least one hydrophilic polymer or at least one hydrophilic molecule.
  18. A composition according to claim 17, wherein the ratio of the aqueous emulsion, solution, or suspension described in any one of claims 14 to 16 to the emulsion of at least one hydrophilic polymer is 50:50, more preferably 20:80, and most preferably 10:90.
  19. The use of a composition described in claim 17 or 18 or an aqueous emulsion, solution, or suspension described in any one of claims 14 to 16 in a textile treatment for simultaneously improving the softness and hydrophilicity of a textile after multiple washing cycles.
  20. Textile treated with the composition described in paragraph 17 or 18 or the aqueous emulsion, solution, or suspension described in any one of paragraphs 14 to 16.

Description

Organic functional silicone crosslinking agent and durable finishing composition formed therefrom The present invention relates to the development of an aqueous emulsion containing an organic functional silicone copolymer having alkoxy/hydroxy terminal groups. This flexible polymer acts as a binder that improves the durability of a coating film by crosslinking with free -OH groups of the substrate through covalent bonding. Since long-chain silicone main chains are present in the polymer, the flexible binder can help control the crosslinking density, and thus does not affect the softness and flexibility of the silicone film on the substrate. In addition, the present invention relates to the development of a composition in which such a flexible binder is combined with other polymers or additives to form an interpenetrating network by covalently bonding with other hydrophilic silicone softeners and substrates having free -OH groups, such as cellulose fabrics. This provides excellent durability of the finishing coating while maintaining a balanced feel and hydrophilicity up to multiple washing cycles. Household fabric softeners are widely used in daily life to soften laundry during washing. When washing cloths or towels using these household fabric softeners, excellent softness is obtained immediately after washing, but this softness gradually disappears with use and is completely gone after washing. In the textile industry, softeners, also known as textile finishing products, are used in the final stage of textile manufacturing to impart excellent softness to textiles. Unlike household softeners, softeners used in the textile industry, when applied to textiles in the form of an emulsion, must maintain a long-lasting softness effect even after multiple washes. Therefore, softeners used as textile finishing products in the textile industry must exhibit high durability. In the textile industry, fabric softeners, also known as textile finishing products, are used at the end of textile manufacturing to provide excellent softness and maintain superior absorbency. While conventional fabric softeners in the textile industry exhibit these benefits, they gradually diminish after multiple wash cycles. Therefore, there is a need for a fabric softener finishing product that provides a long-lasting softness effect even after multiple washes when applied to textiles in emulsion form. Fabric softeners used as textile finishing products in the textile industry must exhibit high durability. Various silicone block copolymers and their emulsions have been studied as hydrophilic softeners for various types of fabrics. Amine-functional terminal blocking is advantageous for the treatment of textiles or fibers. However, because these softeners have weak ionic interactions, they do not remain on the substrate after multiple washes. WO 97/32917, US 8,013,097 B2; US 6,475,568 B1. To improve the durability of polymers on a fabric substrate, US 4,536,422 and US 4,618,512 disclose a method of imparting smooth dryness and flame retardancy to synthetic or cellulose blend fabrics by using formaldehyde-based additives, such as urea, cyclic urea, carbamate esters, or other amides, as crosslinking agents. However, such durability solutions have limitations due to the major problem associated with the continuous release of formaldehyde vapors. In the prior art, alkoxysilanes are widely known as binders that improve the mechanical strength or durability of films coated on a substrate and provide hydrophobicity. The increase in hardness and hydrophobicity of the coating is primarily attributed to the extensive cross-linking of the di/trialkoxy groups of the molecular silane groups. US8481668B2 discloses that functional alkoxysilanes can be advantageously used to improve the adhesion of sealants/adhesives/coatings. In US20090030148A1, an aqueous emulsion comprising a linear siloxane copolymer of a linear silicon and an alkoxy organic functional silane is developed as a partial crosslinking system to improve the surface smoothness and softness of various materials. Therefore, there is a need for a polymer that is suitable for textile final finishing products, exhibits excellent durability and an improved soft touch, maintains acceptable hydrophilicity, and has acceptable viscosity, making it easy for manufacturers to handle. In the past, aminosilicone was widely known to maintain excellent feel and wash durability up to multiple wash cycles. However, aminosilicone does not exhibit excellent moisture absorption. Therefore, maintaining moisture absorption along with the softening properties of the silicone polymer after multiple wash cycles has been a significant challenge for silicone softeners to date. The object of the present invention is to provide a polymer that overcomes all or part of the above disadvantages. To overcome these challenges, an organic functional silicone emulsion was developed as a flexible binder capable of forming an interpenet