Organofunctional silicone crosslinkers and durable finishing compositions formed therefrom

Abstract

The present invention relates to the field of copolymers suitable for textiles, and more particularly to copolymers suitable for textile end-finished products such as softeners. More specifically, the present invention relates to organofunctional silicone copolymers resulting from the polymerization of a silicone monomer, a trialkoxysilane monomer and an amine compound. The invention also relates to compositions of said copolymers with other hydrophilic polymers and to the use of said copolymers and their compositions.

Description

Technical Field

[0001] This invention relates to the development of aqueous emulsions containing organofunctional silicone copolymers with alkoxy / hydroxyl end groups. Such flexible polymers act as adhesives, covalently crosslinking with the free -OH groups of the substrate and enhancing the durability of the coated film. The presence of a long-chain silicone backbone in the polymer makes it a flexible adhesive (which helps control the crosslinking density) without affecting the softness and flexibility of the silicone film on the substrate.

[0002] The present invention also relates to the development of compositions using the flexible adhesive in combination with other polymers or additives, wherein the flexible adhesive covalently binds other hydrophilic silicone softeners and a substrate with free -OH groups, such as cellulose fabric, to form an interpenetrating network. This provides good durability of the finishing coating, as well as a balanced hand feel and hydrophilicity up to several wash cycles. Background Technology

[0003] Household fabric softeners are widely used in daily life to soften laundry during washing. It is known that when fabrics or towels are washed with such household fabric softeners, they acquire good softness immediately after washing, but this softness weakens with use and is completely lost after the washing process.

[0004] In the textile industry, softeners (also known as textile finishing products) are used at the end of textile manufacturing to provide textiles with good softness. In contrast to household softeners, when textile industry softeners are applied to textiles in emulsion form, they must maintain a long-lasting softening effect even after several washes. Softeners used as textile finishing products in the textile industry must then exhibit high durability.

[0005] In the textile industry, softeners, referred to as textile finishing products, are used at the final stage of textile manufacturing to provide good softness and maintain good absorbency. Existing softeners in the textile industry demonstrate these benefits, but they gradually diminish after several wash cycles. Therefore, there is a need for softening finishing products that, when applied to textiles in emulsion form, must maintain a long-lasting softening effect even after several washes. Furthermore, softeners used as textile finishing products in the textile industry must exhibit high durability.

[0006] Various silicone block copolymers and their emulsions have been explored as hydrophilic softeners for various types of fabrics. Amine-functionalized end-capping is beneficial for the treatment of textiles or fibers. However, due to weak ionic interactions, these softeners do not remain on the substrate after several washing conditions. (WO 97 / 32917, US 8,013,097 B2; US 6,475,568 B1)

[0007] To enhance the durability of polymers on fabric substrates, US 4,536,422 and US 4,618,512 disclose the use of formaldehyde-based additives, such as those with urea, cyclourea, urethane, or other amides, as crosslinking agents to impart smooth-dry and flame-retardant properties to synthetic cellulose blend fabrics. However, such durability solutions are limited by major concerns associated with the continuous release of formaldehyde vapor.

[0008] In the prior art, alkoxysilanes are known as adhesives to enhance the mechanical strength or durability of films coated onto a substrate and to provide hydrophobicity. The increase in coating hardness and hydrophobicity is mainly due to the extensive crosslinking of the di / trialkoxy groups of the silane groups in the molecule. US8481668B2 discloses the advantageous use of functionalized alkoxysilanes to improve the bonding of sealants / adhesives / coatings.

[0009] In US20090030148A1, in order to enhance the surface smoothness and flexibility of various materials, an aqueous emulsion of linear siloxane copolymers with linear organosilicon and alkoxy organofunctional silanes has been developed as a partially crosslinked system.

[0010] Therefore, there is a need for polymers suitable for textile finishing products that have good durability, while exhibiting an improved soft hand feel, maintaining acceptable hydrophilic properties, and having acceptable viscosity, making them easier for manufacturers to handle.

[0011] In the past, amino silicones were known for their very high hand feel and wash durability for up to several wash cycles. However, they did not exhibit good absorbency. Therefore, retaining the fabric softener properties of silicone polymers, along with absorbency, after several wash cycles has been a key challenge for silicone fabric softeners to date.

[0012] The object of this invention is to provide a polymer that overcomes all or part of the above-mentioned defects.

[0013] To overcome this challenge, organofunctional silicone emulsions have been developed as flexible adhesives capable of covalently bonding hydrophilic silicone softeners and cellulose substrates to form interpenetrating networks. Textiles treated with compositions containing the adhesive polymer according to the invention exhibit durable softness after several wash cycles.

[0014] Another object of the present invention is to provide a composition for treating textiles, the composition comprising a flexible adhesive polymer according to the invention, which simultaneously exhibits excellent hydrophilic properties and improved soft hand feel properties after several washing cycles.

[0015] The term “consistently composed of” is followed by one or more characteristics, meaning that it may be included in the methods or materials of the invention, including components or steps that do not substantially affect the nature and characteristics of the invention, in addition to those expressly listed.

[0016] The phrase "inclusive between X and Y" includes the boundary unless otherwise explicitly stated. This means that the target range includes X and Y values, and all values ​​from X to Y.

[0017] Throughout the specification and claims of this document, the words “comprising” and “containing” and variations thereof, such as “comprising” and “comprise”, mean “including, but not limited to”, and do not exclude other structural parts, additives, components, integers, or steps. Furthermore, unless the context requires otherwise, the singular encompasses the plural: specifically, when the indefinite article is used, the document should be understood to consider both the plural and the singular, unless the context requires otherwise.

[0018] When citing upper and lower limits for properties, such as the concentration of a component, one can also imply the range of values ​​defined by any combination of upper and lower limits. Summary of the Invention

[0019] This invention relates to organofunctional organosilicon copolymers produced by copolymerization of the following:

[0020] - At least one organosilicon monomer containing at least two functional epoxy groups,

[0021] - at least one trialkoxysilane monomer, and

[0022] - At least one amine compound containing at least two functional amine groups.

[0023] The present invention also relates to a method for preparing the copolymer according to any one of the preceding claims, comprising at least one polymerization step a), wherein at least the following are contacted in a solvent:

[0024] - At least one organosilicon monomer containing at least two functional epoxy groups,

[0025] - at least one trialkoxysilane having at least one functional epoxy or amino group, and

[0026] - At least one amine having at least two functional amine groups.

[0027] The present invention also relates to aqueous emulsions, solutions or suspensions comprising...

[0028] a) Organofunctional organosilicon copolymers

[0029] b) at least one nonionic surfactant, and

[0030] c) At least one weak protic acid.

[0031] The present invention also relates to compositions comprising an aqueous emulsion, solution or suspension as described above and at least one hydrophilic polymer.

[0032] Furthermore, the present invention relates to the use of aqueous emulsions, solutions or suspensions as described above, or compositions as described above, in treating textiles thereby simultaneously improving the softness and hydrophilicity of the textiles after several washing cycles.

[0033] The present invention also relates to textiles treated with the aqueous emulsions, solutions or suspensions as described above, or with the compositions as described above.

[0034] Finally, the present invention relates to a method for treating textiles, comprising applying an aqueous emulsion, solution or suspension according to the invention or a composition according to the invention to the textiles. Detailed Implementation

[0035] Organic functional organosilicon copolymers

[0036] This invention relates to organofunctional organosilicon copolymers produced by copolymerization of the following:

[0037] - At least one organosilicon monomer containing at least two functional epoxy groups,

[0038] - at least one trialkoxysilane having at least one functional epoxy or amino group, and

[0039] - At least one amine having at least two functional amine groups.

[0040] In particular, the present invention relates to organofunctional organosilicon copolymers, which are produced by reacting an organosilicon monomer containing at least two functional epoxy groups with a diamine compound containing at least two functional amine groups to obtain a reaction product and by further reaction of said reaction product with a trialkoxysilane having at least one functional epoxy or amino group.

[0041] When the organic functional silicone copolymer emulsion of the present invention is applied to textiles, it enables the production of textiles with improved soft hand feel properties after up to 10 or more wash cycles.

[0042] When the organic functional silicone copolymer emulsion of the present invention is applied to textiles in the form of a composition together with other hydrophilic additives or polymers, it makes it possible to obtain textiles with improved hand feel and hydrophilic properties for up to 10 or more wash cycles.

[0043] "Copolymer" means an oligomer or linear or branched macromolecule having a sequence of repeating units (or monomer units), wherein at least two units have different chemical structures.

[0044] "Linear" means a polymer or copolymer consisting of a single continuous chain of repeating units. Covalently bonded atoms form the backbone of the polymer, which may be optionally substituted with one or more alkyl groups containing less than 10 carbon atoms, preferably 1 to 8 carbon atoms, and more preferably 1 to 4 carbon atoms.

[0045] A "monomer unit" or "monomer" is a molecule that can be transformed into an oligomer or macromolecule by combining with itself or with other molecules of the same type. A monomer represents the smallest building block, which repeats to produce oligomers or macromolecules.

[0046] "Random copolymer" means oligomer or macromolecule in which the sequential distribution of monomer units follows known statistical laws. For example, a copolymer is called random when it is composed of monomer units distributed in a Markov distribution. The distribution of monomer units in the polymer chain depends on the reactivity of the polymerizable functional groups of the monomers and the relative concentration of the monomers. The organofunctional organosilicon copolymers of the present invention are different from block copolymers and gradient copolymers. "Block" means a portion of a copolymer containing several monomer units (identical or different, and having at least one specific structural or configurational feature that distinguishes it from its adjacent portions). Gradient copolymers refer to copolymers having at least two different structures of monomer units, whose monomer composition gradually changes along the polymer chain, thus gradually progressing from one end of the polymer chain rich in one monomer unit to the other end rich in another comonomer.

[0047] According to the present invention, the terms "polymer", "random linear copolymer" and "linear copolymer" all refer to copolymers according to the present invention and are used interchangeably.

[0048] "Copolymerization" or "polymerization" refers to the process of converting a mixture of at least two monomer units with different chemical structures into an oligomer or copolymer. According to the present invention, the terms "copolymerization" and "polymerization" have the same meaning and can be used interchangeably.

[0049] In embodiments, the copolymers according to the invention are suitable for textiles. More preferably, the copolymers according to the invention are suitable for textile finishing products such as softeners.

[0050] As used herein, the terms "textiles" and "textile materials" must be interpreted broadly and can refer to a very wide range of appearances, such as fibers, yarns, fabrics, garments, knitted fabrics, towels, woven fabrics, and nonwoven fabrics. The copolymers according to the invention are suitable for processing a wide variety of textile materials. Textiles according to the invention can be natural (non-synthetic) cellulose-based textiles such as cotton, silk, wool, flax, and hemp, or synthetic textile materials such as polyamides, polyurethanes, polyacrylic acids, polyesters, polyolefins, polylactic acid, and blends of natural and synthetic textile materials, such as blends of cotton and polyester or polyamide fibers.

[0051] Advantageously, the copolymers of the present invention, when applied to textiles, provide the textiles with excellent soft hand feel properties prior to several wash cycles. This, in turn, provides durability of the finishing polymer on the fabric.

[0052] More advantageously, the copolymer according to the invention can be used with all types of textiles, meaning that when the copolymer is applied to different textiles, regardless of the type of textile to which it is applied, the copolymer exhibits improved soft-feel properties before several washes.

[0053] It is known that cellulose-based textiles are inherently hydrophilic, while synthetic textile materials such as polyester textiles are inherently hydrophobic.

[0054] As used herein, the terms “softener,” “textile finishing product,” and “finished textile product” have the same meaning and are used interchangeably. According to the invention, the terms “softener,” “textile finishing product,” and “finished textile product” refer to copolymers according to the invention produced by the polymerization of organosilicon monomers, trialkoxysilane monomers, and amino compounds, which, when applied to textiles, impart an improved soft hand feel and hydrophilic properties to the textile.

[0055] As used herein, the terms "soft hand feel" and "softness" refer to the properties of textiles after treatment with the copolymers according to the invention. The soft hand feel of textiles treated with the copolymers according to the invention is assessed by tactile evaluation or manual evaluation. The soft hand feel of the treated textiles according to the invention is assessed by a hand panel, and the tested textiles are ranked from softest to stiffest (1 being the softest).

[0056] In an embodiment, the organofunctional organosilicon copolymer according to the invention has a molar percentage of organosilicon monomers in the copolymer ranging from 35-55%, preferably 40-50%, and more preferably 42-45%.

[0057] In a preferred embodiment, the organofunctional organosilicon copolymer according to the present invention has the following molar percentages:

[0058] -The copolymer contains 35-55%, preferably 40-50%, and more preferably 42-45% of organosilicon monomers.

[0059] - An amine compound comprising 37-47%, preferably 37-45%, more preferably 37-40% in the copolymer, and

[0060] - Trialkoxysilane in the copolymer in the range of 10-30%, preferably 15-25%, more preferably 18-21%.

[0061] The molar percentage of monomers in a copolymer is a direct result of adjusting the amount of monomers used in the synthesis of the copolymer.

[0062] Advantageously, the organofunctional organosilicon copolymer according to the invention has the following molar percentages:

[0063] -The copolymer contains 42-45% organosilicon monomers.

[0064] - An amine compound in the copolymer, ranging from 37-40%, and

[0065] - 18-21% of a trialkoxysilane in the copolymer.

[0066] In the embodiments, the mass ratio of organosilicon monomer to trialkoxysilane in the copolymer according to the present invention is in the range of 1:0.003-1:0.03 by weight, preferably 1:0.005-1:0.02, more preferably 1:0.008-1:0.009.

[0067] The mass ratio of monomers in all aspects of the disclosed content can be adjusted to control the characteristics of the copolymer as needed.

[0068] For example, the monomer can exist in a mass ratio of organosilicon monomer to trialkoxysilane monomer of 97:3, 98:2, 99:1, 99.2:0.8, 99.5:0.5, and 99.7:0.3 by weight. Notably, the monomer can also exist in a mass ratio of organosilicon monomer to trialkoxysilane monomer of 99:1, 99.2:0.8, and 99.5:0.5 by weight.

[0069] In a preferred embodiment, the copolymer according to the invention is produced by copolymerization of the following:

[0070] - At least one organosilicon monomer containing at least two functional epoxy groups,

[0071] - At least one trialkoxysilane monomer containing one functional epoxy group, and

[0072] - At least one amine compound containing at least two functional amine groups, wherein the equivalence weight ratio of the epoxy group to the amine is 1:1 to 1:1.5 by equivalence weight.

[0073] In embodiments, the organofunctional organosilicon copolymer according to the present invention has a number-average molecular weight in the range of 12,000-20,000 g / mol, preferably 14,000-18,000 g / mol.

[0074] As used throughout this specification, the term "number-average molecular weight" refers to the number-average molecular weight obtained by size exclusion chromatography, particularly by a measurement calibrated with polystyrene. The measurement method using size exclusion chromatography with polystyrene calibration is described, for example, in the work (Fontanille, M., Gnanou, Y., Chimie et physico to Chimiedes polymeres [Chemistry and physical chemistry of polymers]. 2nd ed.; Dunod: 2010; p. 546).

[0075] As used in this article, the term "average" refers to the exponential average, unless otherwise specified.

[0076] The copolymers according to the invention have the advantage of having an acceptable viscosity, which makes it easy for manufacturers to handle without any stickiness problems, and allows for easy and uniform application of the copolymers in solution, emulsion or dispersion form onto textiles.

[0077] In the context of this invention, "acceptable viscosity" should be understood as a viscosity less than 3000 mPas, notably in the range of 30-600 mPas, which allows manufacturers to handle it without any tackiness issues. Copolymers with acceptable viscosity according to the invention also refer to easily processable copolymers, meaning that copolymers according to the invention are readily soluble in aqueous solutions or dispersed in emulsions or dispersions further applied to textiles. Thus, the copolymer is uniformly applied to the textile, providing a soft hand feel and hydrophilic properties to the entire treated textile.

[0078] The term "viscosity" refers to Brookfield viscosity expressed in mPas. Viscosity is measured using a Brookfield viscometer at a reading of 2000+. Measurements are taken at 25°C and at a rotational speed of 200 rpm. Readings are taken after 30 seconds at 25°C.

[0079] Organosilicon monomers

[0080] The organosilicon monomer according to the present invention has the structure M1D1 a M1 or M2D1 a D2 b M2, of which

[0081] M1 is R 1 R 2 R e SiO 1 / 2

[0082] D1 is R 3 R 4 SiO 1 / 2

[0083] M2 is R 5 R 6 R 7 SiO 1 / 2

[0084] D2 is R 8 R e SiO 1 / 2 ,

[0085] Where R 1 R 2 R 3 R 4 R 5 R 6 R 7 It is independently selected from C1-C10 aliphatic or aromatic groups.

[0086] R e It has a composition of -AZ; wherein A is selected from the group consisting of alkyl (C1-C10), or C3-C10 polyester or C2-C10 polyether having EO (ethylene oxide) and PO (propylene oxide) groups; and Z is an epoxy ring.

[0087] a is an integer in the range of 200-400, more preferably 250-350, more preferably 280-330, and

[0088] b is an integer in the range of 2-4, more preferably 2-3, and even more preferably 2.

[0089] In embodiments, the organosilicon monomers according to the present invention have the general formula (Ia), (Ib), (Ic), or (Id):

[0090] (Ia)

[0091] in:

[0092] m is an integer in the range of 1-10, more preferably 3-7, and even more preferably 3-4.

[0093] a is an integer in the range of 200-400, more preferably 250-350, more preferably 280-330, and

[0094] R 1 R 2 R 3 and R 4 The group is independently selected from C1-C10 alkyl groups, preferably C1-C4 alkyl groups, more preferably C1-C2 alkyl groups, or C6-C20 aromatic hydrocarbon groups, preferably C6-C8 aromatic hydrocarbon groups.

[0095] "Ci-Cj alkyl" means saturated linear or branched hydrocarbons containing chains with ij carbon atoms.

[0096] Aromatic hydrocarbon groups refer to unsubstituted or substituted organic chemical compounds.

[0097] (Ib)

[0098] in:

[0099] m is an integer in the range of 1-10, more preferably 3-7, and even more preferably 3-4.

[0100] n is an integer in the range of 1-10, more preferably 1-5, and even more preferably 1-2.

[0101] a is an integer in the range of 200-400, more preferably 250-350, and even more preferably 280-330.

[0102] Z is a C2-C10 polyester or polyether group, preferably a C2-C5 polyester or polyether group, more preferably a C2-C3 polyester or polyether group, and

[0103] R 1 R 2 R 3 and R 4 The group is independently selected from C1-C10 alkyl groups, preferably C1-C4 alkyl groups, more preferably C1-C2 alkyl groups, or C6-C20 aromatic hydrocarbon groups, preferably C6-C8 aromatic hydrocarbon groups.

[0104] (Ic)

[0105] in:

[0106] m is an integer in the range of 1-10, more preferably 3-7, and even more preferably 3-4.

[0107] a is an integer in the range of 200-400, more preferably 250-350, and even more preferably 280-330.

[0108] b is an integer in the range of 2-4, more preferably 2-3, and more preferably 2.

[0109] R 3 R 4 R 5 R 6 R 7 and R 8 The group is independently selected from C1-C10 alkyl groups, preferably C1-C4 alkyl groups, more preferably C1-C2 alkyl groups, or C6-C20 aromatic hydrocarbon groups, preferably C6-C8 aromatic hydrocarbon groups.

[0110] (Id)

[0111] in:

[0112] m is an integer in the range of 1-10, more preferably 3-7, and even more preferably 3-4.

[0113] n is an integer in the range of 1-10, more preferably 1-5, and even more preferably 1-2.

[0114] a is an integer in the range of 200-400, more preferably 250-350, and even more preferably 230-280.

[0115] b is an integer in the range of 2-4, more preferably 2-3, and even more preferably 2.

[0116] Z is a C2-C10 polyester or polyether group, preferably a C2-C5 polyester or polyether group, more preferably a C2-C3 polyester or polyether group, and

[0117] R 3 R 4 R 5 R 6 R 7 and R 8 The group is independently selected from C1-C10 alkyl groups, preferably C1-C4 alkyl groups, more preferably C1-C2 alkyl groups, or C6-C20 aromatic hydrocarbon groups, preferably C6-C8 aromatic hydrocarbon groups.

[0118] The organosilicones of formulas (Ia), (Ib), (Ic), and (Id) are known to those skilled in the art and are commercially available. Particularly suitable organosilicon monomers are, for example, RH-NB-ES-12K from Runhe.

[0119] According to the embodiments, the organosilicon monomer according to the present invention is at least one of the organosilicon monomers of formula (Ia), (Ib), (Ic), and (Id).

[0120] According to another embodiment, the organosilicon monomer according to the present invention is composed of a single organosilicon monomer of the formula (Ia), (Ib), (Ic), (Id).

[0121] Trialkoxysilane monomer

[0122] In embodiments, the trialkoxysilane monomer according to the invention has the general formula (IIa) or (IIb):

[0123] (IIa)

[0124] (IIb)

[0125] in:

[0126] Y is a linear or branched carbon chain from C1 to C10, preferably Me, Et, n-Pr, i-Pr, n-Bu, or t-Bu, and more preferably Me or Et.

[0127] Trialkoxysilane monomers of formula (IIa) or (IIb) are known to those skilled in the art and are commercially available. Particularly suitable trialkoxysilane monomers are, for example, (3-glycydyloxypropyl)trimethoxysilane from Sigma Aldrich.

[0128] According to the embodiments, the trialkoxysilane monomer according to the invention is a mixture of at least two different trialkoxysilane monomers of formula (IIa) or (IIb).

[0129] Preferably, the trialkoxysilane monomer according to the invention is a mixture of two different trialkoxysilane monomers of formula (IIa) or (IIb).

[0130] Preferably, the trialkoxysilane monomer according to the present invention consists of a single trialkoxysilane monomer of formula (IIa) or (IIb).

[0131] amine compounds

[0132] In embodiments, the amine compound according to the invention comprises at least two functional amine groups. Preferably, the amine compound according to the invention comprises two functional amine groups.

[0133] The amine group of the amine compound according to the invention reacts with an epoxy group from a trialkoxysilane monomer (IIa) or from an organosilicon monomer (Ia), (Ib), (Ic), (Id) to form a partially crosslinked organofunctional organosilicon copolymer according to the invention. Using an amine compound containing a functional amine group as a linker between monomers advantageously allows control over the structure of the copolymer during its polymerization, and thus allows for obtaining linear or branched copolymers according to the invention.

[0134] In a preferred embodiment, the amine compound according to the invention is a cyclic or linear amine compound. Advantageously, the amine compound according to the invention is a linear amine compound.

[0135] In a preferred embodiment, the two functional amine groups of the amine compound according to the invention are part of the skeleton of the amine compound.

[0136] Advantageously, the two functional amine groups of the amine compound according to the invention are part of the cyclic skeleton of the amine compound.

[0137] In embodiments, the amine compounds according to the invention have the general formula (IIIa), (IIIb) or (IIIc):

[0138] (IIIa)

[0139] (IIIb)

[0140] in

[0141] R is H or Me.

[0142] y is an integer in the range of 2-39, more preferably 4-35, more preferably 10-30 or 7-11, and

[0143] Preferably, the sum of x and z is an average value in the range of 1.2-6, more preferably 1.8-4, even more preferably 2-3 or 3-4.

[0144] (IIIc)

[0145] in

[0146] u is an integer in the range of 2-68, more preferably 5-60, and even more preferably 10-50.

[0147] Amine compounds of formula (IIIa), (IIIb), or (IIIc) are known to those skilled in the art and are commercially available. Particularly suitable amine compounds are, for example, Jeffamine ED-600 from Huntsman.

[0148] According to the embodiments, the amine compound according to the invention is a mixture of at least two different amine compounds of formula (IIIa), (IIIb) or (IIIc).

[0149] Preferably, the trialkoxysilane monomer according to the invention is a mixture of two different amine compounds of formula (IIIa), (IIIb) or (IIIc).

[0150] According to another embodiment, the amine compound according to the invention consists of a single amine compound monomer of formula (IIIa), (IIIb), (IIIc).

[0151] In a preferred embodiment, the composition comprises piperidine in addition to the amine compound comprising two functional amine groups according to the invention. It should be understood that piperidine contains only one amino functional group; however, it can be added to a mixture comprising an amine compound containing two amino functional groups.

[0152] According to another embodiment, 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).

[0153] According to another embodiment, the amine compound according to the invention is a mixture of at least one amine compound of formula (IIIb) and piperidine.

[0154] Method for preparing copolymers according to the present invention

[0155] The present invention also relates to a method for preparing copolymers according to the invention, comprising at least one polymerization step a), wherein at least the following are contacted in a solvent:

[0156] - At least one organosilicon monomer containing at least two functional epoxy groups,

[0157] - at least one trialkoxysilane monomer, and

[0158] - At least one amine compound containing at least two functional amine groups.

[0159] Preferably, in the first step, an organosilicon monomer containing at least two functional epoxy groups is reacted with an amine compound containing at least two functional amine groups to obtain a first reaction product, and then the first reaction product is reacted with a trialkoxysilane monomer.

[0160] According to a preferred embodiment, the solvent used in step a) has a boiling point below 150°C, preferably below 130°C, and more preferably 65°C-130°C.

[0161] Preferably, the solvent used in step a) is isopropanol or diethylene glycol butyl ether.

[0162] According to another preferred embodiment, the polymerization step a) is carried out in an inert atmosphere, such as a nitrogen atmosphere.

[0163] In one embodiment, the method further includes adding a surfactant and water prior to the distillation step to avoid high viscosity and improve the handling and processing of the copolymer and its storage properties.

[0164] Methods for preparing aqueous emulsions, solutions or suspensions of copolymers

[0165] The copolymers according to the present invention are intended as softeners for textiles.

[0166] This invention also relates to aqueous emulsions, solutions, or suspensions, comprising...

[0167] a) at least one copolymer according to the invention,

[0168] b) at least one nonionic surfactant, and

[0169] c) At least one weak protic acid.

[0170] Preferably, the aqueous emulsion, solution, or suspension is in the form of an aqueous emulsion.

[0171] The aqueous emulsions, solutions, or suspensions according to the present invention contain a nonionic surfactant, wherein the nonionic surfactant is an alkoxylated alcohol containing a linear or branched carbon chain of C8-C18 and the alkoxy group is 1-11 repeating units of ethoxy and / or propoxy.

[0172] The aqueous emulsions, solutions, or suspensions according to the present invention contain at least one weak protic acid, wherein the at least one weak protic acid has a pK value of 0-10, more preferably 2-8, and most preferably 3-7. a Examples of weak protic acids are acetic acid or formic acid.

[0173] Applying an aqueous emulsion, solution, or suspension to textiles provides an improved soft hand feel for up to several wash cycles.

[0174] In a preferred embodiment, the copolymer is present in the aqueous emulsion, solution or suspension according to the invention at a concentration of 10%-60% by weight, preferably 10%-50% by weight, more preferably 15%-40% by weight, and most preferably 20%-30% by weight, calculated by the total weight of the composition.

[0175] In a preferred embodiment, the surfactant is present in the aqueous emulsion, solution or suspension according to the invention at a concentration of 3%-20% by weight, preferably 3%-15% by weight, more preferably 5%-10% by weight, and most preferably 5%-8% by weight, calculated by the total weight of the composition.

[0176] The term "surfactant" refers to a substance that reduces the surface tension of a liquid. Typical examples that can be applied to textiles are anionic or nonionic surfactants, such as fatty alcohol ethoxylates, fatty alcohol alkoxylates, etc., which act as wetting and rewetting agents. The nonionic surfactants mentioned in this invention are linear or branched alkoxylated alcohols having a C8-C18 carbon chain and an ethoxylation / propoxylation degree ranging from 1 to 12. Anionic surfactants are selected from sulfates / esters, sulfonates / esters, and phosphates / esters with or without alkoxy groups and linear or branched alkyl chains.

[0177] Advantageously, the aqueous emulsion, solution, or suspension according to the invention comprises at least:

[0178] - At least one copolymer according to the invention, with a concentration of 10%-60% by weight, preferably 10%-50% by weight, more preferably 15%-40% by weight, and most preferably 20%-30% by weight, calculated by the total weight of the aqueous emulsion, solution, or suspension, and

[0179] - A surfactant with a concentration of 3%-20% by weight, preferably 3%-15% by weight, more preferably 5%-10% by weight, and most preferably 5%-8% by weight, calculated based on the total weight of the aqueous emulsion, solution, or suspension.

[0180] Unless otherwise stated, the “weight percentage” (expressed as % weight or % by weight) of a mixture of copolymers or surfactants in an aqueous emulsion, solution or suspension refers to the weight of the compound used, calculated on the total weight of the aqueous emulsion, solution or suspension.

[0181] In a preferred embodiment, the aqueous emulsion, solution, or suspension according to the invention may further contain an organic solvent, preferably having hydroxyl functionality and selected from the group consisting of C2-C10 mono- or polyhydroxy alcohols having 1-3 hydroxyl groups and 0-4 ether linkages, such as butyl diethylene glycol, polyethylene glycol / propylene glycol, and diethylene glycol.

[0182] In one embodiment, the method further includes a distillation step of the solvent used in step a) to obtain the copolymer composition according to the invention and as described above. This distillation step allows for the obtaining of a copolymer composition ready for use without any further purification.

[0183] Preferably, the distillation step is carried out at 200 mbar.

[0184] In a preferred embodiment, the distillation step is carried out at the boiling point temperature of the solvent.

[0185] Advantageously, the temperature of the distillation step is below 100°C, preferably below 70°C, more preferably in the range of 30°C to 50°C, and preferably under vacuum pressure.

[0186] Composition and Use

[0187] The present invention also relates to compositions comprising an aqueous emulsion, solution or suspension according to the invention, and at least one emulsion of a hydrophilic polymer or at least one hydrophilic molecule.

[0188] The term "hydrophilic polymer" or "hydrophilic molecule" refers to a substance that is inherently hydrophilic and enhances water absorption properties. Typical examples available in textiles are ionic and nonionic polymers or hydrophilic molecules known in the art, wherein ionic polymers or molecules with carboxylate / ester, sulfonate / ester, phosphate / ester, or phosphonate / ester groups, and nonionic polymers or molecules with polyether, acrylate, amide, or hydroxyl groups, act as hydrophilic agents.

[0189] Preferably, the hydrophilic polymer is a polymer product of the following.

[0190] - At least one organosilicon monomer containing at least two functional epoxy groups,

[0191] - At least one amine compound containing at least two functional amine groups.

[0192] More preferably, at least one hydrophilic polymer comprises a repeating unit of the general formula (IV) known in the prior art:

[0193] (IV)

[0194] in:

[0195] m is an integer in the range of 1-10, more preferably 3-7, and even more preferably 3-4.

[0196] a is an integer in the range of 200-400, more preferably 250-350, and even more preferably 280-330.

[0197] R 1 R 2 R 3 and R 4 Independently selected from C1-C10 alkyl groups, preferably C1-C4 alkyl groups, more preferably C1-C2 alkyl groups, or C6-C20 aromatic hydrocarbon groups, preferably C6-C8 aromatic hydrocarbon groups, and

[0198] X is an amine compound containing at least two functional amine groups.

[0199] Preferably, the above definitions of at least one organosilicon monomer and at least one amine compound to react with each other also apply to at least one polymer.

[0200] In a preferred embodiment, the aqueous emulsion, solution or suspension according to the invention and the emulsion of at least one hydrophilic polymer are present in the composition according to the invention at a ratio of 50:50, more preferably 20:80, and most preferably 10:90.

[0201] The hydrophilicity of textiles can be significantly improved by treatment with the compositions according to the invention without reducing the durability of the hand feel. Polymers containing repeating units of general formula (IV) provide good hydrophilicity to textiles, but the hand feel is not durable. Therefore, it is believed that the copolymers according to the invention interact with the hydrophilic polymers in the compositions according to the invention to form an interpenetrating network that helps retain a soft hand feel even after several wash cycles, thereby imparting good durability while simultaneously improving hydrophilicity.

[0202] The present invention also relates to a method of treating textiles with a composition according to the invention, or an aqueous emulsion, solution, or suspension according to the invention, or a copolymer according to the invention, wherein the composition, or an aqueous emulsion, solution, or suspension according to the invention, or a copolymer according to the invention, is applied to or incorporated into the textiles.

[0203] The present invention also relates to the use of compositions according to the invention, or aqueous emulsions, solutions, or suspensions according to the invention, or copolymers according to the invention, in treating textiles thereby simultaneously improving the softness and hydrophilicity of the textiles prior to several washes.

[0204] The present invention also relates to textiles treated with compositions according to the invention or aqueous emulsions, solutions or suspensions according to the invention.

[0205] Application method

[0206] The present invention also relates to a method of treating textiles, comprising applying a composition according to the invention or an aqueous emulsion, solution or suspension according to the invention to the textiles.

[0207] The compositions according to the invention or the aqueous emulsions, solutions or suspensions according to the invention can be applied by various methods.

[0208] Preferably, the coating includes coating with an air knife or bar coater, impregnation or immersion by padding or exhaust methods, printing techniques, spraying, or inclusion into textile fibers such as polyester, nylon, or modified polyacrylonitrile fiber materials during the spinning process.

[0209] Preferably, the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention is applied to textiles 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.

[0210] Preferably, the textiles treated with the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention are dried or cured. Particularly preferably, the drying or curing is carried out at a temperature of 80 to 180°C and / or for 10 seconds to 12 minutes.

[0211] The copolymers according to the invention are suitable for processing a wide variety of substrates, including fibers, yarns, fabrics, knitted fabrics, towels, woven fabrics, nonwoven fabrics, and garments.

[0212] Textiles treated with the compositions according to the invention or with the aqueous emulsions, solutions or suspensions according to the invention may be natural (non-synthetic) cellulose-based textiles such as cotton, silk, wool, flax and hemp, or synthetic textile materials such as polyamide, polyurethane, polyacrylic acid, polyester, polyolefin, polylactic acid, or blends of natural and synthetic textile materials, such as blends of cotton and polyester or polyamide fibers.

[0213] Example

[0214] Examples 1, 2 and 3 represent (AB)n organosilicon polymers with crosslinking agent groups.

[0215] Examples 4, 5, and 6 are comparative representatives of (AB)n organosilicon polymers known in the art that do not have crosslinking agent groups and are commonly used as hydrophilic softener coatings in textile finishing.

[0216] Examples 7, 8, 9, 10, 11, 12, 13, 14 and 15 represent coating compositions using silicone crosslinking polymers, which can be used as softeners in textile finishing to achieve hand feel and durable hydrophilic properties.

[0217] The following commercially available products are used in the given embodiments.

[0218] - Surfactants: V51 (Imbentin-U / 050)-C11&5EO (nonionic surfactant), Esteem-48-AK-C13&11EO (nonionic surfactant)

[0219] - Organosilicon monomer: RH-NB-ES-12K (diepoxy-terminated PDMS)

[0220] -Amine compounds: piperazine (diamine), Jeffamine ED-600 (diamine polyether)

[0221] Solvents: water, isopropanol, butyl carbitol, glycerin.

[0222] -Product 1 (for commercial purchase): Emulsion of conventional ABn silicone copolymer with hydrophilic groups

[0223] - Defoamer: Xiameter AFE050 (Defoaming Emulsion)

[0224] - Preservatives: Sodium benzoate or benzyl benzoate

[0225] Examples of copolymer synthesis and emulsification according to the present invention

[0226] Example 1

[0227] 200 g of RH-NB-ES-12K (diepoxysilane, Mn=12k) and 1.77 g of glycidoxypropyltrimethoxysilane were added to a cylindrical reactor equipped with a reflux condenser, thermometer socket, and nitrogen inlet. A mixture of 7 g of Jeffamine ED-600 and 0.25 g of piperazine in 200 g of isopropanol was added with continuous stirring. The solution was then refluxed at 80-82 °C for 7 hours under a nitrogen atmosphere. After complete polymerization, each polymer solution was emulsified by adding 400 g of the polymer solution to 500 g of water and 50 g of each of the nonionic surfactants C13 / 11EO and C115EO in an aqueous solution at 25-60 °C and stirring for 30 minutes. The pH was maintained at 5-7 by neutralizing the solution with diluted acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the observed solids content of the emulsion was in the range of 27-30%.

[0228] Example 1a

[0229] 200 g of RH-NB-ES-12K (diepoxysilane, Mn=12k) and 1.77 g of glycidoxypropyltrimethoxysilane were added to a cylindrical reactor equipped with a reflux condenser, thermometer socket, and nitrogen inlet. A mixture of 7 g of Jeffamine ED-600 and 0.25 g of piperazine in 200 g of butylcarbidol was added with continuous stirring. The solution was then refluxed at 80-82 °C for 7 hours under a nitrogen atmosphere. After complete polymerization, each polymer solution was emulsified by adding 400 g of the polymer solution to 500 g of water and 50 g of each of the nonionic surfactants C13 / 11EO and C115EO in an aqueous solution at 25-60 °C and stirring for 30 minutes. The pH was maintained at 5-7 by neutralizing the solution with diluted acetic acid (22%). The solids content of the emulsion was adjusted to 27-30%. Butylcarbitol was used as a solvent to eliminate the isopropanol stripping process.

[0230] Example 2

[0231] 200 g of RH-NB-ES-12K (diepoxysilane, Mn=12k) and 1.77 g of glycidoxypropyltrimethoxysilane were added to a cylindrical reactor equipped with a reflux condenser, thermometer socket, and nitrogen inlet. A mixture of 8.7 g of Jeffamine ED-600 in 250 g of isopropanol was added with continuous stirring. The solution was then refluxed at 80-82 °C for 7 hours under a nitrogen atmosphere. After complete polymerization, each polymer solution was emulsified by adding 400 g of the polymer solution to 500 g of water and an aqueous solution of 50 g of each of the C13 / 11EO and C115EO surfactants at 25-60 °C and stirring for 30 minutes. The pH was maintained at 5-7 by neutralizing the solution with diluted acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the observed solids content of the emulsion was in the range of 27-30%.

[0232] Example 3

[0233] 200 g of RH-NB-ES-12K (diepoxysilane, Mn=12k) and 1.77 g of glycidoxypropyltrimethoxysilane were added to a cylindrical reactor equipped with a reflux condenser, thermometer socket, and nitrogen inlet. A mixture of 1.259 g of piperazine in 250 g of isopropanol was added with continuous stirring. The solution was then refluxed at 80–82 °C for 7 hours under a nitrogen atmosphere. After complete polymerization, each polymer solution was emulsified by adding 400 g of the polymer solution to 500 g of water and an aqueous solution of 50 g of each of the C13 / 11EO and C115EO surfactants at 25–60 °C and stirring for 30 minutes. The pH was maintained at 5–7 by neutralizing the solution with diluted acetic acid (22%). The observed solids content of the emulsion was in the range of 27–30%.

[0234] Comparative example (conventional hydrophilic softener without cross-linking agent)

[0235] Example 4

[0236] 150 g of RH-NB-ES-12K (diepoxysilane, Mn=12k) was added to a cylindrical reactor equipped with a reflux condenser, thermometer socket, and nitrogen inlet. A mixture of 5.4 g of Jeffamine ED-600 and 0.2 g of piperazine in 150 g of isopropanol was added with continuous stirring. The solution was then refluxed at 80-82 °C for 7 hours under a nitrogen atmosphere. After complete polymerization, each polymer solution was emulsified by adding 300 g of the polymer solution to 375 g of water and an aqueous solution of 37.5 g of each of the C13 / 11EO and C115EO surfactants at 25-60 °C and stirring for 30 minutes. The pH was maintained at 5-7 by neutralizing the solution with diluted acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the observed solids content of the emulsion was in the range of 27-30%.

[0237] Example 4a

[0238] 150 g of RH-NB-ES-12K (diepoxysilane, Mn=12k) was added to a cylindrical reactor equipped with a reflux condenser, thermometer socket, and nitrogen inlet. A mixture of 5.4 g of Jeffamine ED-600, 0.2 g of piperazine, and 75 g of butylcarbitol was added with continuous stirring. The solution was then heated at 80-82 °C for 7 hours under a nitrogen atmosphere. After complete polymerization, each polymer solution was emulsified by adding 230 g of the polymer solution to 150 g of water and an aqueous solution of 50 g each of C13 / 11EO and C115EO surfactants at 25-60 °C and stirring for 30 minutes. The pH was maintained at 5-7 by neutralizing the solution with diluted acetic acid (22%). The solids content of the emulsion was adjusted to 27-30%. Butylcarbitol was used as a solvent to eliminate the isopropanol stripping process.

[0239] Example 5

[0240] 150 g of RH-NB-ES-12K (diepoxysilane, Mn=12k) was added to a cylindrical reactor equipped with a reflux condenser, thermometer socket, and nitrogen inlet. A mixture of 6.6 g of Jeffamine ED-600 in 150 g of isopropanol was added with continuous stirring. The solution was then refluxed at 80-82 °C for 7 hours under a nitrogen atmosphere. After complete polymerization, each polymer solution was emulsified by adding 300 g of the polymer solution to an aqueous solution of 375 g of water and 37.5 g of each of the C13 / 11EO and C115EO surfactants at 25-60 °C and stirring for 30 minutes. The pH was maintained at 5-7 by neutralizing the solution with diluted acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the observed solids content of the emulsion was in the range of 27-30%.

[0241] Example 6

[0242] 150 g of RH-NB-ES-12K (diepoxysilane, Mn=12k) was added to a cylindrical reactor equipped with a reflux condenser, thermometer socket, and nitrogen inlet. A mixture of 0.969 g of piperazine in 150 g of isopropanol was added with continuous stirring. The solution was then refluxed at 80-82 °C for 7 hours under a nitrogen atmosphere. After complete polymerization, each polymer solution was emulsified by adding 300 g of the polymer solution to an aqueous solution of 375 g of water and 37.5 g of each of the C13 / 11EO and C115EO surfactants at 25-60 °C and stirring for 30 minutes. The pH was maintained at 5-7 by neutralizing the solution with diluted acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the observed solids content of the emulsion was in the range of 27-30%.

[0243] nature:

[0244] Table 1 shows the physical appearance and properties of the polymers and emulsions of Examples 1-6.

[0245] Table 1

[0246]

[0247] Compositions using organofunctional organosilicon crosslinking copolymer emulsions

[0248] Example 7

[0249]

[0250] Example 8

[0251]

[0252] Example 9

[0253]

[0254] Example 10

[0255]

[0256] Example 11

[0257]

[0258] Example 12

[0259]

[0260] Example 13

[0261]

[0262] Example 14

[0263]

[0264] Example 15

[0265]

[0266] Fabric treatment and performance evaluation

[0267] The test fabric (100% cotton knit) was treated using a continuous pad-dry process. Padding was performed using a dry-on-wet process with a silicone emulsion dosage of 30 g / L, a liquid absorption rate of 65-75%, and drying at 130°C for 2 min. Washing was performed using AATCC 135.

[0268] Use AATCC 135 for washing.

[0269] Before and after 10-15 wash cycles, the softness was evaluated by the hand feel evaluation team, and the tested fabrics were sorted in order, with the smallest number in the sort being the best (1>3>5>7).

[0270] Absorption is tested using the drop test method AATCC 79 and the wicking test AATCC 197.

[0271] The results are shown in Table 2-7.

[0272] Performance data

[0273] Softness evaluation and absorbency

[0274] A comparative performance evaluation of silicone fabric softeners with and without crosslinking agent groups (Tables 2-4) shows that polymers with crosslinking agent functional groups can remain on the fabric after several washing cycles (10-15 HL) due to the covalent crosslinking of the polymer with the fabric. However, low absorbency is observed due to the high crosslinking density that imparts a degree of hydrophobic behavior to the fabric surface.

[0275] Hand feel durability performance evaluation

[0276] To understand the ability of crosslinking groups in the polymer and to enhance hand feel durability up to several wash cycles, cotton fabrics were coated with the emulsions from Examples 1, 2, 3, 4, 5, and 6, and their hand feel was evaluated before and after washing.

[0277] Padding is performed via a wet-on-dry process using an emulsion dosage of 30 g / L, a liquid absorption rate of 65-75%, and drying at 130°C for 2 min. Washing is then performed using AATCC 135.

[0278] The softness was evaluated by a hand feel evaluation team before and after 10-15 wash cycles, and the tested fabrics were ranked in order such that the smallest number in the ranking was the best (1>3>5>7). The table below provides a comparison of the hand feel of fabrics coated with silicone softeners containing crosslinking agents (Examples 1, 1a, 2, 3), fabrics without crosslinking agents (Examples 4, 4a, 5, 6), and blank (uncoated) fabrics.

[0279] Table 2

[0280]

[0281] Table 3

[0282]

[0283] Table 4

[0284]

[0285] A comparative performance evaluation of silicone fabric softeners with and without crosslinking agent groups (Tables 2-4) shows that polymers with crosslinking agent functional groups exhibit the best hand feel before and after several wash cycles (10-15 HL) due to the retention of the silicone polymer even after several washes. This polymer retention is primarily attributed to the covalent bonding between the crosslinking agent groups in the polymer and the -OH groups on the fabric, which differs from conventional silicone fabric softeners that are bonded through ionic interactions.

[0286] However, such cross-linked silicone softeners suppress the absorbency of fabrics. Therefore, in order to achieve a balance of hydrophilicity and hand feel before and after washing, compositions of the organofunctional silicone copolymer emulsion according to the invention and conventional hydrophilic silicone softener emulsions were prepared, as in Examples 7, 8, 9, 10, 11, 12, 13, 14, and 15. The performance of the compositions was compared using Examples 1 and conventional hydrophilic softeners known in the art (such as those in Examples 4, 5, and 6).

[0287] The composition properties that balance the benefits of different properties

[0288] Tables 5 to 8 below show a comparison of feel (before and after washing) and absorbency. Figures 1 to 4 The graph of the results indicates that the candidate with the highest durability and good absorbency should have the lowest feel ranking (x-axis) and the lowest absorbency value (y-axis).

[0289] Table 5

[0290]

[0291] Table 6

[0292]

[0293] Table 7

[0294]

[0295] Table 8

[0296]

[0297] Fabrics treated with the copolymer compositions of the present invention exhibit hand feel and absorbency properties comparable to conventional hydrophilic silicone softeners (comparative examples) before washing. However, after washing (up to 10 HL), they show good hand feel retention, as indicated by good sorting (lowest sorting is best), demonstrating high durability. Thus, a good balance of hand feel, absorbency, and up to 10 HL durability can be achieved by preparing compositions using crosslinking copolymers and hydrophilic softeners according to the present invention.

[0298] In addition, other properties such as wrinkle resistance, fabric strength, non-yellowing, and colorfastness of dyed fabrics are enhanced. Compatibility with various chemicals / additives (optical brighteners, metal salts) and stability to pH, shear, and shaking offer additional benefits.

[0299] result :

[0300] Comparative performance evaluations of fabrics coated with the composition demonstrated a superior hand feel rating before and after 10 HL washing compared to conventional hydrophilic softeners. The crosslinking copolymer enables the hydrophilic softener polymer to crosslink with the fabric to form an interpenetrating network, ensuring that the polymer is not removed from the fabric even after several wash cycles. Therefore, the composition using the crosslinking copolymer achieves a good balance between hydrophilicity and hand feel durability. Attached Figure Description

[0301] Figure 1

[0302] The results from Table 5 are illustrated in the graph. The x-axis represents the feel ranking and the y-axis represents the absorption value. The double-circled dots in the graph indicate the desired performance.

[0303] Figure 2

[0304] The results from Table 6 are illustrated in the graph. The x-axis represents the feel ranking and the y-axis represents the absorption value. The double-circled dots in the graph indicate the desired performance.

[0305] Figure 3

[0306] The results from Table 7 are illustrated in the graph. The x-axis represents the feel ranking and the y-axis represents the absorption value. The double-circled dots in the graph indicate the desired performance.

[0307] Figure 4

[0308] The results from Table 8 are illustrated in the graph. The x-axis represents the feel ranking and the y-axis represents the absorption value. The double-circled dots in the graph indicate the desired performance.

Claims

1. Organofunctional silicone copolymer resulting from the copolymerization of: - at least one silicone monomer comprising at least 2 functional epoxy groups, - at least one trialkoxysilane monomer, and - at least one amine compound comprising at least 2 functional amine groups.

2. Copolymer according to any one of the preceding claims, in which the molar percentage of silicone monomer in the copolymer ranges from 35 to 55%, preferably from 40 to 50%, more preferentially from 42 to 45%.

3. Copolymer according to any one of the preceding claims, in which the mass% of trialkoxysilane monomer in the copolymer according to the application ranges from 0.5 to 1.5 by weight, preferably from 0.5 to 1.2, more preferentially from 0.8 to 1.

4. Copolymer according to any one of the preceding claims, in which the silicone monomer has general formula (la), (lb), (lc), (Id): (Ia); or (Ib); or (Ic); or (Id) in which: m is an integer ranging from 1 to 10, more preferentially from 3 to 7, more preferentially from 3 to 4, n is an integer ranging from 1 to 10, more preferentially from 1 to 5, more preferentially from 1 to 2, a is an integer ranging from 200 to 400, more preferentially from 250 to 350, more preferentially from 280 to 330, b is an integer ranging from 2 to 4, more preferentially from 2 to 3, more preferentially 2, Z is a C2-C10 polyester or polyether radical, preferably a C2-C5 polyester or polyether radical, more preferentially a C2-C3 polyester or polyether radical, and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently selected from a C1-C10 alkyl group, preferably a C1-C4 alkyl group, more preferably a C1-C2 alkyl group, or a C6-C20 aromatic hydrocarbon group, preferably a C6-C8 aromatic hydrocarbon group.

5. Copolymer according to any one of the preceding claims, in which the trialkoxysilane monomer has general formula (Ila) or (lib): (Ia) (Ib) and (IIb) in which: Y is a C1-C10 linear or branched carbon chain, preferably Me, Et, n-Pr, i-Pr, n-Bu, t-Bu, more preferentially Me, Et.

6. Copolymer according to any one of the preceding claims, in which the amine compound is a cyclic or linear amine compound.

7. Copolymer according to any one of the preceding claims, in which the amine compound has general formula (Ilia), (Illb) or (IIIc): (IIIa); (IIIb); or (IIIc) in which R is H or Me, y is an integer ranging from 2 to 39, more preferentially from 4 to 35, more preferentially from 10 to 30, u is an integer ranging from 2 to 68, more preferentially from 5 to 60, more preferentially from 10 to 50, preferably the sum of x and z is an average ranging from 1.2 to 6, more preferentially from 1.8 to 4, more preferentially from 2 to 3.

8. Copolymer according to any one of the preceding claims, in which the amine compound is a mixture of at least one amine compound having general formula (Ilia) and at least one amine compound having general formula (Illb): (IIIa); and (IIIb); or in which R is H or Me, y is an integer ranging from 2 to 39, more preferentially from 4 to 35, more preferentially from 10 to 30, preferably the sum of x and z is an average ranging from 1.2 to 6, more preferentially from 1.8 to 4, more preferentially from 2 to 3.

9. Copolymer according to any one of the preceding claims, in which the amine compound is a mixture of at least one amine compound having general formula (Illb) and piperidine (IIIb); in which y is an integer ranging from 2 to 39, more preferentially from 4 to 35, more preferentially from 10 to 30, 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.

10. Process for the preparation of the copolymer according to any one of the preceding claims, comprising at least one polymerization step a) wherein at least the following are contacted in a solvent: - at least one silicone monomer comprising at least 2 functional epoxy groups, - at least one trialkoxysilane monomer, and - at least one amine compound comprising at least 2 functional amine groups.

11. Process according to claim 10, wherein the solvent used in step a) has a boiling point lower than 150°C, preferably lower than 130°C, more preferably from 65°C to 130°C.

12. Process according to any one of the preceding claims 10 or 11, comprising a distillation step of the solvent used in step a).

13. Process according to any one of the preceding claims 10 to 12, wherein the temperature of the distillation step is lower than 100°C, preferably lower than 70°C, more preferably from 30°C to 50°C, preferably under vacuum pressure.

14. Aqueous emulsion, solution or suspension comprising a) at least one copolymer according to any one of claims 1 to 9, b) at least one non-ionic surfactant, and c) at least one weak protic acid.

15. Aqueous emulsion, solution or suspension according to claim 14, wherein the copolymer is present in the aqueous emulsion, solution or suspension in a concentration of 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 aqueous emulsion, solution or suspension.

16. Aqueous emulsion, solution or suspension according to claim 14 or 15, wherein the surfactant is present in the aqueous emulsion, solution or suspension according to the invention in a concentration of 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.

17. Composition comprising an aqueous emulsion, solution or suspension according to any one of claims 14 to 16, and at least one emulsion of a hydrophilic polymer or at least one emulsion of a hydrophilic molecule.

18. Composition according to claim 17, wherein the ratio of the aqueous emulsion, solution or suspension according to claims 14 to 16 to the emulsion of at least one hydrophilic polymer is a ratio of 50:50, more preferably 20:80, most preferably 10:

90.

19. Use of the composition according to claim 17 or 18 or of the aqueous emulsion, solution or suspension according to any one of claims 14 to 16 for the treatment of a textile, thereby simultaneously improving the soft hand feel and the hydrophilicity of said textile after several wash cycles.

20. Textile treated with the composition according to claim 17 or 18 or with the aqueous emulsion, solution or suspension according to any one of claims 14 to 16.

21. A method of treating a textile comprising applying the composition according to claim 17 or 18 or the aqueous emulsion, solution or suspension according to any one of claims 14 to 16 to a textile.

22. The method according to claim 21, wherein the applying comprises coating with an air knife or rod applicator, impregnating or soaking by a pad or dip method, printing techniques, spraying, inclusion into textile fibres during the spinning process.

23. The method according to claim 22, wherein the composition according to claim 17 or 18 or the aqueous emulsion, solution or suspension according to any one of claims 14 to 16 is applied to the textile at a concentration in the range of 20 to 80 g / l or 2-12% and / or has a pH in the range of 3 to 11.

24. The method according to any one of claims 21 to 23, wherein the composition according to claim 17 or 18 or the aqueous emulsion, solution or suspension according to any one of claims 14 to 16 is dried or cured at a temperature of 80 to 180 °C and / or for a time of 10 seconds to 12 minutes.

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