Organo-functional silicone crosslinker and durable finishing composition formed therefrom
Patent Information
- Authority / Receiving Office
- TW · TW
- Patent Type
- Patents
- Current Assignee / Owner
- ARCHROMA (SWITZERLAND) GMBH
- Filing Date
- 2024-09-19
- Publication Date
- 2026-08-01
AI Technical Summary
Existing textile softeners in the textile industry lose softening effect and hydrophilicity after several washing cycles, and formaldehyde-based additives pose environmental hazards.
Development of an organofunctional silicone emulsion formed by copolymerizing polysiloxane monomers, trialkoxysilane, and amine compounds to form an interpenetrating network structure with cellulose substrates, enhancing durability and hydrophilicity through covalent bonding.
The emulsion maintains soft handle and hydrophilic properties in textiles after multiple washings, improving durability and water absorption without environmental hazards.
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Abstract
Description
Organic Functional Polysiloxane Crosslinking Agent and Durable Processing Composition Formed Therefrom The present invention relates to the development of aqueous emulsions containing organofunctional polysiloxane copolymers having alkoxy / hydroxy end groups. Such flexible polymers act as binders to covalently crosslink with the free - OH groups of the substrate and enhance the durability of the coating film. The presence of a long - chain polysiloxane backbone in the polymer makes the polymer a flexible binder, which helps to control the cross - link density, thus not affecting the softness and flexibility of the polysiloxane film on the substrate. The present invention also relates to the development of compositions using such flexible binders and other polymers or additives, where the flexible binder covalently binds to other hydrophilic polysiloxane softeners and substrates with free - OH groups, such as cellulose fabrics, thereby forming an interpenetrating network structure. This gives the processed coating good durability and balanced handfeel and hydrophilic properties even after several washing cycles. Household softeners are widely used in daily life to soften clothes during washing. It is known that when washing woven fabrics or towels with such household softeners, the woven fabrics or towels will have good softness immediately after washing, but this softness will decline during use and will be completely lost after the washing operation. In the textile industry, softeners (also known as textile processing products) are used at the end of textile manufacturing to provide good softness to textiles. In contrast to household softeners, softeners used in the textile industry must have a lasting softening effect even after several washings when applied to textiles in the form of an emulsion. Thus, softeners used as textile processing products in the textile industry must exhibit high durability. In the textile industry, softeners, also known as textile processing products, are used at the end of textile manufacturing to provide good softness and maintain good absorbency of the textiles. Existing softeners in the textile industry exhibit such benefits, but they decline after several washing cycles. Therefore, there is a need for a softener processing product that must have a lasting softening effect even after several washings when applied to textiles in the form of an emulsion. Thus, softeners used as textile processing products in the textile industry must exhibit high durability. Various polysiloxane block copolymers and their emulsions have been studied as hydrophilic softeners for various types of fabrics. Amine - functional end - capping is beneficial for treating 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 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 together with urea, cyclic ureas, urethanes or with other amides as crosslinking agents, to impart smooth-dry and flame-retardant properties to synthetic cellulose blended fabrics. However, such durability solutions are limited due to the major problems associated with the continuous release of formaldehyde vapors. In the prior art, alkoxysilanes are well-known as adhesives to enhance the mechanical strength or durability of films coated on substrates and to provide hydrophobicity. The increase in the hardness and hydrophobicity of the coatings is mainly attributed to the extensive crosslinking of the di / trialkoxy groups of the molecular silyl groups. US8481668B2 discloses that functional alkoxysilanes have been advantageously used to improve the adhesion of sealants / adhesives / coatings. In US20090030148A1, an aqueous emulsion of a linear silicone copolymer containing linear polysiloxane and alkoxy organofunctional silane has been developed as a partial crosslinking system to enhance the surface smoothness and softness of various materials. Therefore, there is a need for a polymer suitable for textile end-products, which has good durability and at the same time exhibits an improved soft handle, and has an acceptable viscosity while maintaining acceptable hydrophilic properties, thus allowing manufacturers to operate more easily. In the past, aminosilicone has been known for its excellent handle and washing durability even after several washing cycles. However, it does not exhibit good water absorption. Therefore, to date, maintaining the softening agent properties of silicone polymers as well as water absorption after several washing cycles has been a key challenge for silicone softeners. One object of the present invention is to provide a polymer that overcomes all or part of the above disadvantages. To overcome this challenge, an organofunctional silicone emulsion has been developed as a flexible adhesive, which is capable of covalently bonding a hydrophilic silicone softener and a cellulose substrate to form an interpenetrating network structure. Thus, textiles treated with a composition containing the adhesive polymer according to the present invention exhibit a durable softness after several washing cycles. Another object of the present invention is to provide a composition for treating textiles, which comprises a flexible adhesive polymer according to the present invention, which exhibits excellent hydrophilic properties and improved soft handle properties simultaneously after several washing cycles. The term "consisting essentially of one or more features" means that in addition to the explicitly listed components or steps, the methods or materials of the present invention may also include components or steps that do not substantially affect the characteristics and features of the present invention. Unless otherwise expressly stated, the expression "comprised between X and Y" includes the boundaries. This expression means that the target range includes the X and Y values, and all values from X to Y. Throughout the description and claims of this specification, the phrases "comprise" and "contain" and variations thereof such as "comprising" and "comprises" mean "including but not limited to" and do not exclude other parts, additives, components, integers or steps. Further, unless otherwise required herein, the singular encompasses the plural: in particular, unless otherwise required herein, in the case of using an indefinite article, this specification should be understood to encompass both the plural and the singular. In the case of referring to upper and lower limits for a property, such as for the concentration of a component, the range of values defined by any combination of any upper limit and any lower limit may also be implied. The present invention relates to an organofunctional polysiloxane copolymer produced by copolymerizing: - at least one polysiloxane monomer containing at least 2 functional epoxy groups, - at least one trialkoxysilane monomer, and - at least one amine compound containing at least 2 functional amine groups. The present invention also relates to a method for preparing a copolymer according to any one of the preceding claims, the method comprising at least one polymerization step a) in which at least the following are brought into contact in a solvent: - at least one polysiloxane monomer containing at least 2 functional epoxy groups, - at least one trialkoxysilane having at least one functional epoxy group or amine group, and - at least one amine having at least 2 functional amine groups. The present invention further relates to an aqueous emulsion, solution or suspension comprising a) an organofunctional polysiloxane copolymer b) at least one nonionic surfactant, and c) at least one weak protonic acid. The present invention further relates to a composition comprising the aqueous emulsion, solution or suspension described above and at least one hydrophilic polymer. Furthermore, the present invention relates to the use of the aqueous emulsion, solution or suspension described above or the composition described above in treating textiles for simultaneously improving the soft handle and hydrophilicity after several washing cycles of the textiles. The present invention also relates to a textile treated with the aqueous emulsion, solution or suspension described above or with the composition described above. Finally, the present invention relates to a method for treating textiles, which comprises applying the aqueous emulsion, solution or suspension according to the present invention or the composition according to the present invention to the textiles. Organofunctional polysiloxane copolymer The present invention relates to an organofunctional polysiloxane copolymer produced by copolymerizing: - at least one polysiloxane monomer containing at least 2 functional epoxy groups, - at least one trialkoxysilane having at least one functional epoxy group or amino group, and - at least one amine having at least 2 functional amino groups. Specifically, the present invention relates to an organofunctional polysiloxane copolymer produced by reacting a polysiloxane monomer containing at least 2 functional epoxy groups with a diamine compound containing at least 2 functional amino groups to obtain a reaction product, and further reacting the reaction product with a trialkoxysilane having at least one functional epoxy group or amino group. When an organofunctional polysiloxane copolymer emulsion according to the present invention is applied to textiles, it is possible to obtain textiles that still have improved soft handle characteristics after 10 or more washing cycles. When an organofunctional polysiloxane copolymer emulsion according to the present invention is applied to textiles in the form of a composition with other hydrophilic additives or polymers, it is possible to obtain textiles that still have both improved handle and hydrophilic characteristics after 10 or more washing cycles. "Copolymer" means an oligomer or a linear or branched macromolecule having a sequence composed of several repeating units (or monomer units), wherein at least two units have different chemical structures. "Linear" means a polymer or copolymer composed of a single continuous chain of repeating units. Covalently bonded atoms form the main chain of the polymer, which may be optionally substituted by one or more alkyl groups containing less than 10 carbon atoms, preferably containing 1 to 8 carbon atoms, more preferably containing 1 to 4 carbon atoms. "Monomer unit" or "monomer" means a molecule that can be converted into an oligomer or macromolecule by combining with itself or with other molecules of the same type. A monomer represents the smallest building block, and its repetition produces an oligomer or macromolecule. "Random copolymer" means an oligomer or macromolecule in which the sequence distribution of monomer units follows known statistical laws. For example, a copolymer is called random when it is composed of monomer units, and the distribution of these monomer units is a Markov distribution. The distribution of monomer units in a polymer chain depends on the reactivity of the polymerizable functional groups of the monomers and the relative concentrations of the monomers. The organofunctional polysiloxane copolymer of the present invention is different from block copolymers and gradient copolymers. "Block" means a part of a copolymer containing several monomer units, the monomer units being the same or different and having at least one characteristic of a specific constitution or configuration, and can be distinguished from the part adjacent to this part by this at least one specific characteristic. A gradient copolymer means a copolymer having monomer units of at least two different structures, and its monomer composition gradually changes along the polymer chain, thus gradually transmitting from one end of the polymer chain rich in one monomer unit to the other end rich in another comonomer. According to the present invention, the terms "copolymer", "random linear copolymer" and "linear copolymer" all refer to the copolymers according to the present invention and can be used interchangeably. "Copolymerization" or "polymerization" means a method for converting a mixture of at least two monomer units of 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 interchangeable. In a specific example, the copolymer according to the present invention is applicable to textiles. More preferably, the copolymer according to the present invention is suitable for textile end products, such as softeners. As used herein, the terms "textile" and "textile material" must be interpreted broadly and can take a very wide range of manifestations, such as in the form of fibers, yarns, fabrics, clothing, knitted fabrics, towels, woven fabrics and non-woven fabrics. The copolymer according to the present invention is applicable to treating a wide variety of textile materials. The textiles according to the present invention can be natural (non-synthetic) cellulose-based textiles, such as cotton, silk, wool, linen and hemp, or synthetic textile materials, such as polyamides, polyurethanes, polyacrylics, polyesters, polyolefins, polylactides, or also blends of natural textile materials and synthetic textile materials, such as blends of cotton and polyester fibers or polyamide fibers. Advantageously, when applied to textiles, the copolymer of the present invention still provides excellent soft handle characteristics to the textiles after several washing cycles. Thereby providing durability of the processed polymer on the fabric. More advantageously, the copolymers according to the invention can be used with all types of textiles, meaning that the copolymers exhibit improved soft handfeel properties even after several washes when applied to different textiles, regardless of the type of textile to which the copolymer is applied. It is well known that cellulose-based textiles are hydrophilic in nature, and synthetic textile materials such as polyester textiles are hydrophobic in nature. Also as used herein, the terms "softener", "textile finishing product" and "textile end finishing product" have the same meaning and are used interchangeably. According to the invention, the terms "softener", "textile finishing product" and "textile end finishing product" refer to the copolymers according to the invention produced by the polymerization of polysiloxane monomers, trialkoxysilane monomers and amine compounds, and when applied to textiles, the textiles exhibit improved soft handfeel and hydrophilic properties. As used herein, the terms "soft handfeel" and "softeness" refer to the properties of textiles after being treated with the copolymers according to the invention. The soft handfeel of textiles treated with the copolymers according to the invention is a tactile evaluation or handfeel evaluation. The soft handfeel of the treated textiles according to the invention is obtained by a hand panel, and the tested textiles are rated from the softest to the roughest (1 being the softest). In a specific example, the organofunctional polysiloxane copolymer according to the invention has a molar percentage of polysiloxane monomers in the copolymer in the range of 35 to 55%, preferably 40 to 50%, more preferably in the range of 42 to 45%. In a preferred specific example, the organofunctional polysiloxane copolymer according to the invention has the following molar percentages: - the polysiloxane monomers in the copolymer are in the range of 35 to 55%, preferably 40 to 50%, more preferably in the range of 42 to 45%, - the amine compounds in the copolymer are in the range of 37 to 47%, preferably 37 to 45%, more preferably in the range of 37 to 40%, and - the trialkoxysilane in the copolymer is in the range of 10 to 30%, preferably 15 to 25%, more preferably in the range of 18 to 21%. The molar percentages of the monomers in the copolymer are a direct result of adjusting the amounts of the monomers used to synthesize the copolymer. Advantageously, the organofunctional polysiloxane copolymer according to the present invention has the following molar percentages: - the polysiloxane monomer in the copolymer is in the range of 42 to 45%, - the amine compound in the copolymer is in the range of 37 to 40%, and - the trialkoxysilane in the copolymer is in the range of 18 to 21%. In a specific example, the mass ratio between the polysiloxane monomer and the trialkoxysilane in the copolymer according to the present invention is in the range of 1:0.003 to 1:0.03 by weight, preferably 1:0.005 to 1:0.02, more preferably 1:0.008 to 1:0.009. In all aspects of the present disclosure, the mass ratio of the monomers can be adjusted as needed to manipulate the characteristics of the copolymer. For example, the monomers can be present in a mass ratio of polysiloxane 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 monomers can be present in a mass ratio of polysiloxane monomer to trialkoxysilane monomer of 99:1, 99.2:0.8, and 99.5:0.5. In a preferred specific example, the copolymer according to the present invention is produced by copolymerization of: - at least one polysiloxane monomer containing at least 2 functional epoxy groups, - at least one trialkoxysilane monomer containing 1 functional epoxy group, and - at least one amine compound containing at least 2 functional amine groups, wherein the equivalent ratio of epoxy groups to amines is 1:1 to 1:1.5 in equivalents. In a specific example, the organofunctional polysiloxane copolymer according to the present invention has a number average molecular weight in the range of 12,000 to 20,000 g / mol, preferably 14,000 to 18,000 g / mol. The term "number average molecular weight" used throughout the specification refers to the number average molecular weight obtained by measurement by size exclusion chromatography, specifically by using polystyrene calibration. The measurement method by size exclusion chromatography using polystyrene calibration is described, for example, in the work (Fontanille, M.; Gnanou, Y., Chimie et physico to Chimie des polymeres [Chemistry and physical chemistry of polymers]. 2nd edition; Dunod: 2010; p. 546). As used herein, unless otherwise specified, the term "average" refers to the number average. An advantage of the copolymer according to the invention is that it has an acceptable viscosity, which allows the manufacturer to easily operate without any stickiness problems, and the copolymer in the form of a solution, emulsion or dispersion can be easily and uniformly applied to textiles. In the context of the present invention, "acceptable viscosity" should be understood as a viscosity less than 3000 mPas, particularly in the range of 30 to 600 mPas, which allows the manufacturer to operate the copolymer without any stickiness problems. The copolymer with an acceptable viscosity according to the present invention also refers to a copolymer that is easy to handle, which means that the copolymer according to the present invention is easily soluble in an aqueous solution or dispersed in an emulsion or dispersion further applied to textiles. Therefore, the copolymer is uniformly applied to the textiles, which provides the whole treated textiles with a soft hand feeling and hydrophilic properties. The term "viscosity" refers to the Brookfield viscosity expressed in mPas. The viscosity is measured using a Brookfield viscometer in the 2000 + direction (heading). It is measured at 25 °C and a rotational speed of 200 revolutions per minute. The measured value is read after 30 seconds at 25 °C. Polysiloxane monomer The polysiloxane monomer according to the present invention has the structure M1D1 a M1 or M2D1 a D2 b M2, where M1 is R 1 R 2 R e SiO 1 / 2 D1 is R 3 R 4 SiO 1 / 2 M2 is R 5 R 6 R 7 SiO 1 / 2 D2 is R 8 R e SiO 1 / 2 , wherein R 1 、R 2 、R 3 、R 4 、R 5 、R 6 、R 7 are independently selected from C1 to C10 aliphatic or aromatic groups. R e has a composition of -A-Z; wherein A is selected from groups comprising an alkyl (C1 to C10) or a C3 to C10 polyester or a C2 to C10 polyether having ethylene oxide (EO) and propylene oxide (PO) groups; Z is an epoxy ring. 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 in the range of 2 to 4, more preferably 2 to 3, more preferably 2. In a specific example, the polysiloxane monomer according to the present invention has the general formula (Ia), (Ib), (Ic) or (Id): (Ia) wherein: m is an integer in the range of 1 to 10, more preferably 3 to 7, more preferably 3 to 4, a is an integer in the range of 200 to 400, more preferably 250 to 350, more preferably 280 to 330, and R 1 、R 2 、R 3 及R 4 are independently selected from C1 to C10 alkyl groups, preferably C1 to C4 alkyl groups, more preferably C1 to C2 alkyl groups, or C6 to C20 aromatic hydrocarbon groups, preferably C6 to C8 aromatic hydrocarbon groups. "Ci to Cj alkyl" means a saturated, straight-chain or branched-chain hydrocarbon chain containing i to j carbon atoms. An aromatic hydrocarbon group means an unsubstituted or substituted organic compound. (Ib) wherein: m is an integer in the range of 1 to 10, more preferably 3 to 7, even more preferably 3 to 4; n is an integer in the range of 1 to 10, more preferably 1 to 5, even more preferably 1 to 2; a is an integer in the range of 200 to 400, more preferably 250 to 350, even more preferably 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; and R 1 、R 2 、R 3 及R 4 are independently selected from C1 to C10 alkyl groups, preferably C1 to C4 alkyl groups, more preferably C1 to C2 alkyl groups, or C6 to C20 aromatic hydrocarbon groups, preferably C6 to C8 aromatic hydrocarbon groups. (Ic) wherein: m is an integer in the range of 1 to 10, more preferably 3 to 7, even more preferably 3 to 4; a is an integer in the range of 200 to 400, more preferably 250 to 350, even more preferably 280 to 330; b is an integer in the range of 2 to 4, more preferably 2 to 3, even more preferably 2; and R 3 、R 4 、R 5 、R 6 、R 7 及R 8 are independently selected from C1 to C10 alkyl groups, preferably C1 to C4 alkyl groups, more preferably C1 to C2 alkyl groups, or C6 to C20 aromatic hydrocarbon groups, preferably C6 to C8 aromatic hydrocarbon groups. (Id) wherein: m is an integer in the range of 1 to 10, more preferably 3 to 7, even more preferably 3 to 4; n is an integer in the range of 1 to 10, more preferably 1 to 5, even more preferably 1 to 2; a is an integer in the range of 200 to 400, more preferably 250 to 350, even more preferably 230 to 280; b is an integer in the range of 2 to 4, more preferably 2 to 3, even 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; and R 3 、R 4 、R 5 、R 6 、R 7 and R 8 independently selected from C1-C10 alkyl, preferably C1-C4 alkyl, more preferably C1-C2 alkyl, or C6-C20 aromatic hydrocarbon group, preferably C6-C8 aromatic hydrocarbon group. The polysiloxanes of formulas (Ia), (Ib), (Ic), and (Id) are known to those skilled in the art and are commercially available. Particularly suitable polysiloxane monomers are, for example, RH-NB-ES-12K from Runhe. According to a specific example, the polysiloxane monomer according to the present invention is at least one of the polysiloxane monomers of formulas (Ia), (Ib), (Ic), and (Id). According to another specific example, the polysiloxane monomer according to the present invention consists of a single polysiloxane monomer of one of formulas (Ia), (Ib), (Ic), and (Id). Trialkoxysilane monomer In a specific example, the trialkoxysilane monomer according to the present invention has the general formula (IIa) or (IIb): (IIa) (IIb) wherein: Y is a C1-C10 straight or branched carbon chain, preferably Me, Et, n-Pr, i-Pr, n-Bu, t-Bu, more preferably Me, Et. The trialkoxysilane monomers of formulas (IIa) or (IIb) are known to those skilled in the art and are commercially available. Particularly suitable trialkoxysilane monomers are, for example, (3-glycidyloxypropyl)trimethoxysilane from Sigma Aldrich. According to a specific example, the trialkoxysilane monomer according to the present invention is a mixture of at least two different trialkoxysilane monomers of formulas (IIa) or (IIb). Preferably, the trialkoxysilane monomer according to the present invention is a mixture of two different trialkoxysilane monomers of formulas (IIa) or (IIb). Preferably, the trialkoxysilane monomer according to the present invention consists of a single trialkoxysilane monomer of one of formulas (IIa) or (IIb). Amine compound In a specific example, the amine compound according to the present invention contains at least 2 functional amine groups. Preferably, the amine compound according to the present invention contains 2 functional amine groups. React the amino group of the amine compound according to the present invention with the epoxy group from the trialkoxysilane monomer (IIa) or from the polysiloxane monomers (Ia), (Ib), (Ic), (Id) to form the partially crosslinked organofunctional polysiloxane copolymer according to the present invention. Using an amine compound containing a functional amino group as a linking group between the monomers allows for the advantageous control of the structure of the copolymer during its polymerization and thus allows for obtaining a linear or branched copolymer according to the present invention. In a preferred embodiment, the amine compound according to the present invention is a cyclic or linear amine compound. Advantageously, the amine compound according to the present invention is a linear amine compound. In a preferred embodiment, the two functional amino groups of the amine compound according to the present invention are part of the main chain of the amine compound. Advantageously, the two functional amino groups of the amine compound according to the present invention are part of the cyclic main chain of the amine compound. In one embodiment, the amine compound according to the present invention has the general formula (IIIa), (IIIb) or (IIIc): (IIIa) (IIIb) wherein R is H or Me, y is an integer in the range of 2 to 39, more preferably 4 to 35, more preferably 10 to 30 or 7 to 11, and preferably, the sum of x and z is an average value in the range of 1.2 to 6, more preferably 1.8 to 4, more preferably 2 to 3 or 3 to 4, (IIIc) wherein u is an integer in the range of 2 to 68, more preferably 5 to 60, more preferably 10 to 50. The 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. According to one embodiment, the amine compound according to the present invention is a mixture of at least two different amine compounds of formula (IIIa), (IIIb) or (IIIc). Preferably, the trialkoxysilane monomer according to the present invention is a mixture of two different amine compounds of formula (IIIa), (IIIb) or (IIIc). According to another embodiment, the amine compound according to the present invention consists of a single amine compound monomer of formula (IIIa), (IIIb), (IIIc). In a preferred embodiment, in addition to the amine compound containing two functional amino groups according to the present invention, the composition further comprises piperidine. It should be understood that piperidine contains only one amino functional group, however, it can be added to a mixture containing an amine compound having two amino functional groups. According to another specific example, 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). According to another specific example, the amine compound according to the invention is a mixture of at least one amine compound of formula (IIIb) and piperidine. Method for preparing the copolymer according to the invention The invention also relates to a method for preparing the copolymer according to the invention, the method comprising at least one polymerization step a), in which at least the following are brought into contact in a solvent: - at least one polysiloxane 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. Preferably, in the first step, the polysiloxane 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 trialkoxysilane monomer. According to a preferred specific example, the solvent used in step a) has a boiling point of less than 150 °C, preferably less than 130 °C, more preferably comprising 65 °C to 130 °C. Preferably, the solvent used in step a) is isopropyl alcohol or diethylene glycol butyl ether. According to another preferred specific example, the polymerization step a) is carried out in an inert atmosphere such as a nitrogen atmosphere. In one specific example, the method further comprises adding a surfactant and water before the distillation step in order to avoid high viscosity and improve the handling and processing of the copolymer as well as its storage properties. Method for preparing an aqueous emulsion; solution or suspension of a copolymer The copolymer according to the invention is intended to be used as a softening agent for textiles. The invention also relates to an aqueous emulsion, solution or suspension comprising a) at least one copolymer according to the invention, b) at least one non-ionic surfactant, and c) at least one weak protonic acid. Preferably, the aqueous emulsion, solution or suspension is in the form of an aqueous emulsion. The aqueous emulsion, solution or suspension according to the invention comprises a non-ionic surfactant, wherein the non-ionic surfactant is an alkoxylated alcohol containing a C8 to C18 straight-chain or branched-chain carbon chain, and the alkoxy group is ethoxy and / or propoxy with 1 to 11 repeating units. The aqueous emulsion, solution or suspension according to the invention comprises at least one weak protonic acid, wherein at least one weak protonic acid has a pK of 0 to 10, more preferably 2 to 8, most preferably 3 to 7 a . Examples of weak protonic acids are acetic acid or formic acid. An aqueous emulsion, solution or suspension is applied to textiles to provide an improved soft handle even after several washing cycles of the textiles. In a preferred embodiment, based on the total weight of the composition, the copolymer is present in the aqueous emulsion, solution or suspension according to the invention at a concentration of 10 wt% to 60 wt%, preferably 10 wt% to 50 wt%, more preferably 15 wt% to 40 wt%, most preferably 20 wt% to 30 wt%. In a preferred embodiment, based on the total weight of the composition, the surfactant is present in the aqueous emulsion, solution or suspension according to the invention at a concentration of 3 wt% to 20 wt%, preferably 3 wt% to 15 wt%, more preferably 5 wt% to 10 wt%, most preferably 5 wt% to 8 wt%. The term "surfactant" refers to a substance that reduces the surface tension of a liquid. Typical examples applicable to be applied on textiles are anionic or nonionic surfactants such as fatty alcohol ethoxylates, fatty alcohol alkoxylates, etc., which act as wetting agents and rewetting agents. The nonionic surfactants mentioned in the present invention are straight-chain or branched-chain alkoxylated alcohols having a C8 to C18 carbon chain and an ethoxylation / propoxylation degree in the range of 1-12. The anionic surfactants are selected from sulfates, sulfonates, and phosphates of straight-chain or branched-chain alkyl chains with or without alkoxy groups. Advantageously, the aqueous emulsion, solution or suspension according to the invention comprises at least: - at least one copolymer according to the invention, at a concentration of 10 wt% to 60 wt%, preferably 10 wt% to 50 wt%, more preferably 15 wt% to 40 wt%, most preferably 20 wt% to 30 wt% based on the total weight of the aqueous emulsion, solution or suspension, and - a surfactant, at a concentration of 3 wt% to 20 wt%, preferably 3 wt% to 15 wt%, more preferably 5 wt% to 10 wt%, most preferably 5 wt% to 8 wt% based on the total weight of the aqueous emulsion, solution or suspension. Unless otherwise indicated, the "weight percentage" (expressed as % wt or wt%) of the copolymer or surfactant mixture in the aqueous emulsion, solution or suspension refers to the wt% of the compound used based on the total weight of the aqueous emulsion, solution or suspension. In a preferred embodiment, the aqueous emulsion, solution or suspension according to the invention may further comprise an organic solvent, preferably a monohydroxy alcohol or polyhydroxy alcohol having a hydroxyl functionality and selected from the group consisting of C2 to C10 monohydroxy alcohols or polyhydroxy alcohols having 1-3 hydroxyl groups and 0-4 ether bonds, such as butyl diglycol, polyethylene glycol / propylene glycol, diethylene glycol. In a specific example, the method further includes a distillation step of the solvent used in step a) to obtain the copolymer composition according to the present invention and as described above. This distillation step enables the obtaining of a copolymer composition that can be used without further purification. Preferably, the distillation step is carried out at 200 mbar. In a preferred specific example, the distillation step is carried out at the temperature of the boiling point of the solvent. Advantageously, preferably under a vacuum pressure, the temperature of the distillation step is lower than 100 °C, preferably lower than 70 °C, more preferably in the range of 30 °C to 50 °C. Compositions and uses The present invention also relates to a composition comprising at least one emulsion of an aqueous emulsion, solution or suspension according to the present invention and a hydrophilic polymer or at least one hydrophilic molecule. The term "hydrophilic polymer" or "hydrophilic molecule" refers to a substance that is essentially hydrophilic and enhances the water absorption property. Typical examples applicable to textiles are ionic and non-ionic polymers or hydrophilic molecules known in the prior art, where ionic polymers or molecules with carboxylate or sulfonate or phosphate or phosphonate groups and non-ionic polymers or molecules with polyether or acrylate or amide or hydroxyl groups, etc., act as hydrophilic agents. Preferably, the hydrophilic polymer is a polymerization product of: - at least one polysiloxane monomer containing at least 2 functional epoxy groups, - at least one amine compound containing at least 2 functional amine groups. More preferably, at least one hydrophilic polymer contains repeating units of the general formula (IV) well-known in the prior art: (IV) wherein: m is an integer in the range of 1 to 10, more preferably 3 to 7, even more preferably 3 to 4, a is an integer in the range of 200 to 400, more preferably 250 to 350, even more preferably 280 to 330, R 1 、R 2 、R 3 and R 4 are 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 X is an amine compound containing at least 2 functional amine groups. Preferably, the above definitions for at least one polysiloxane monomer and at least one amine compound to react with each other also apply to at least one polymer. 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 in a ratio of 50:50, more preferably 20:80, and most preferably 10:90. The hydrophilicity of textiles can be significantly improved by treating with the composition according to the invention without reducing the durability of the handfeel. Polymers containing the repeating unit of formula (IV) provide good hydrophilicity to textiles but do not have durability in terms of handfeel. Therefore, it is believed that the copolymer according to the invention interacts with the hydrophilic polymer in the composition according to the invention to form an interpenetrating network structure, which helps to retain the soft handfeel even after several washing cycles, thereby providing good durability and at the same time increasing hydrophilicity. The invention also relates to a method for treating textiles 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, wherein the composition or the aqueous emulsion, solution or suspension according to the invention or the copolymer according to the invention is applied to or incorporated into the textiles. The invention also relates to 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 for treating textiles to simultaneously improve the soft handfeel and hydrophilicity of the textiles after several washings. The invention also relates to a textile treated with the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention. Application process The invention also relates to a method for treating textiles, which comprises applying the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention to the textiles. The application of the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention can be carried out by various methods. Preferably, the application includes coating with an air knife or a rod coater, impregnation or immersion by padding or exhaustion methods, printing techniques, spraying, incorporating materials such as polyester, nylon or modified polyacrylonitrile fiber into the textile fibers during the textile process. Preferably, the composition according to the invention or the aqueous emulsion, solution or suspension according to the invention is applied to the 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. 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. More preferably, 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 present invention are suitable for treating a wide variety of substrates, including fibers, yarns, fabrics, knitted fabrics, towels, woven fabrics, non-woven fabrics, and garments. Textiles treated with the composition according to the present invention or with an aqueous emulsion, solution or suspension according to the present invention can be natural (non-synthetic) cellulose-based textiles such as cotton, silk, wool, linen and hemp, or synthetic textile materials such as polyamides, polyurethanes, polyacrylics, polyesters, polyolefins, polylactides, or also blends of natural and synthetic textile materials such as blends of cotton with polyester fibers or polyamide fibers. Examples Examples 1, 2 and 3 represent (AB)n polysiloxane polymers with crosslinker groups. Examples 4, 5 and 6 are comparative representatives of (AB)n polysiloxane polymers without crosslinker groups, which are known in the prior art and are typically used as hydrophilic softening agent coatings in textile processing. Examples 7, 8, 9, 10, 11, 12, 13, 14 and 15 represent coating compositions using polysiloxane crosslinker polymers, which can be used as softeners in textile processing to obtain a durable handfeel and hydrophilic performance. The following commercial products were used in the given examples - Surfactants: V51 (Imbentin-U / 050)-C11&5EO (non-ionic surfactant), Esteem-48-AK-C13&11EO (non-ionic surfactant) - Polysiloxane monomer: RH-NB-ES-12K (diepoxy-terminated PDMS) - Amine compounds: Piperazine (diamine), Jeffamine ED-600 (diamine polyether) - Solvents: water, isopropanol, butyl carbitol, glycerol. - Commercial product 1: Emulsion of a conventional ABn polysiloxane copolymer with hydrophilic groups - Antifoaming agent: Xiameter AFE050 (antifoam emulsion) - Preservative: Sodium benzoate or benzyl benzoate Examples of copolymer synthesis and emulsification according to the present invention Examples 1 200 g of RH-NB-ES-12K (dicycloepoxy polysiloxane, Mn = 12k) and 1.77 g of glycidyloxypropyltrimethoxysilane were added to a cylindrical reactor equipped with a reflux condenser, a thermometer pocket, and a nitrogen inlet. A mixture of 7 g of Jeffamine ED-600 and 0.25 g of piperidine in 200 g of isopropanol was added with continuous stirring. Subsequently, the solution was 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 an aqueous solution of 500 g of water and 50 g each of nonionic surfactants C13 / 11EO and C115EO surfactants at 25 °C - 60 °C and stirring for 30 minutes. The pH was maintained at 5 - 7 by neutralizing the solution with dilute acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the solid content of the observed emulsion was in the range of 27 - 30%. Example 1a 200 g of RH-NB-ES-12K (dicycloepoxy polysiloxane, Mn = 12k) and 1.77 g of glycidyloxypropyltrimethoxysilane were added to a cylindrical reactor equipped with a reflux condenser, a thermometer pocket, and a nitrogen inlet. A mixture of 7 g of Jeffamine ED-600 and 0.25 g of piperidine in 200 g of butyl carbitol was added with continuous stirring. Subsequently, the solution was 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 an aqueous solution of 500 g of water and 50 g each of nonionic surfactants C13 / 11EO and C115EO surfactants at 25 °C - 60 °C and stirring for 30 minutes. The pH was maintained at 5 - 7 by neutralizing the solution with dilute acetic acid (22%). The solid content of the emulsion was adjusted to be in the range of 27 - 30%. By using butyl carbitol as the solvent, the isopropanol stripping process was omitted. Example 2 200 g of RH-NB-ES-12K (dicycloepoxy polysiloxane, Mn = 12k) and 1.77 g of glycidyloxypropyltrimethoxysilane were added to a cylindrical reactor equipped with a reflux condenser, a thermometer pocket, and a nitrogen inlet. A mixture of 8.7 g of Jeffamine ED-600 in 250 g of isopropanol was added with continuous stirring. Subsequently, the solution was 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 an aqueous solution of 500 g of water and 50 g each of C13 / 11EO and C115EO surfactants at 25 °C - 60 °C and stirring for 30 minutes. The pH was maintained at 5 - 7 by neutralizing the solution with dilute acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the solid content of the observed emulsion was in the range of 27 - 30%. Example 3 200 g of RH-NB-ES-12K (dicycloepoxy polysiloxane, Mn = 12k) and 1.77 g of glycidyloxypropyltrimethoxysilane were added to a cylindrical reactor equipped with a reflux condenser, a thermometer pocket, and a nitrogen inlet. A mixture of 1.259 g of piperazine in 250 g of isopropanol was added with continuous stirring. Subsequently, the solution was 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 an aqueous solution of 500 g of water and 50 g each of C13 / 11EO and C115EO surfactants at 25 °C - 60 °C and stirring for 30 minutes. The pH was maintained at 5 - 7 by neutralizing the solution with dilute acetic acid (22%). The solid content of the observed emulsion was in the range of 27 - 30%. Comparative Example (Conventional Hydrophilic Softener without Crosslinking Agent) Example 4 150 g of RH-NB-ES-12K (dicycloepoxy polysiloxane, Mn = 12k) was added to a cylindrical reactor equipped with a reflux condenser, a thermometer pocket, and a nitrogen inlet. A mixture of 5.4 g of Jeffamine ED-600 and 0.2 g of piperidine in 150 g of isopropanol was added under continuous stirring. Subsequently, the solution was 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 each of C13 / 11EO and C115EO surfactants at 25 °C - 60 °C and stirring for 30 minutes. The pH was maintained at 5 - 7 by neutralizing the solution with dilute acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the observed solid content of the emulsion was in the range of 27 - 30%. Example 4a 150 g of RH-NB-ES-12K (dicycloepoxy polysiloxane, Mn = 12k) was added to a cylindrical reactor equipped with a reflux condenser, a thermometer pocket, and a nitrogen inlet. A mixture of 5.4 g of Jeffamine ED-600 and 0.2 g of piperidine in 75 g of butyl carbitol was added under continuous stirring. Subsequently, the solution was 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 an aqueous solution of 150 g of water and 50 g each of C13 / 11EO and C115EO surfactants at 25 °C - 60 °C and stirring for 30 minutes. The pH was maintained at 5 - 7 by neutralizing the solution with dilute acetic acid (22%). The solid content of the emulsion was adjusted to be in the range of 27 - 30%. The isopropanol was removed by a butyl carbitol solvent stripping process. Example 5 150 g of RH-NB-ES-12K (dicycloepoxy polysiloxane, Mn = 12k) was added to a cylindrical reactor equipped with a reflux condenser, a thermometer pocket, and a nitrogen inlet. A mixture of 6.6 g of Jeffamine ED-600 in 150 g of isopropanol was added under continuous stirring. Subsequently, the solution was 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 each of C13 / 11EO and C115EO surfactants at 25 °C - 60 °C and stirring for 30 minutes. The pH was maintained at 5 - 7 by neutralizing the solution with dilute acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the observed solid content of the emulsion was in the range of 27 - 30%. Example 6 150 g of RH-NB-ES-12K (dicycloepoxy polysiloxane, Mn = 12k) was added to a cylindrical reactor equipped with a reflux condenser, a thermometer pocket, and a nitrogen inlet. A mixture of 0.969 g of piperazine in 150 g of isopropanol was added with continuous stirring. Subsequently, the solution was 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 each of C13 / 11EO and C115EO surfactants at 25 °C - 60 °C and stirring for 30 minutes. The pH was maintained at 5 - 7 by neutralizing the solution with dilute acetic acid (22%). The solvent isopropanol was removed by vacuum distillation, and the solid content of the observed emulsion was in the range of 27 - 30%. Characteristics: The physical appearance and characteristics of the polymers and emulsions of Examples 1 - 6 are shown in Table 1. Table 1 Composition Example 7 using an organofunctional polysiloxane crosslinker copolymer emulsion Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Example 15 Fabric treatment and performance evaluation The test fabric (100% cotton knitted fabric) was treated by a continuous pad-dry process. Pad-dyeing was carried out by the wet-dry method, using a polysiloxane emulsion dosage of 30 g / l, a wet pickup of 65 - 75%, and drying at 130 °C for 2 min. Pad-dyeing was carried out by the wet-dry method, using a 30 g / l emulsion dosage, a wet pickup of 65 - 75%, and drying at 130 °C for 2 min. Washing was carried out using AATCC 135. Washing was carried out using AATCC 135. Before washing and up to 10 - 15 washing cycles, softness evaluation was carried out by a touch panel, and the tested fabrics were graded, where the lowest number in the grading is the best (1 > 3 > 5 > 7). Absorbency was tested by the drop test method AATCC 79 and the wicking test AATCC 197. The results are in Table 2 - 7. Performance data Softness evaluation and absorbency Comparative performance evaluation of polysiloxane softeners with and without cross - linker groups (Table 2 - 4) shows that due to the covalent cross - linking of the polymer with the fabric, after several washing cycles (10 - 15 HL), the polymer with cross - linker functional groups can remain on the fabric. However, due to the high cross - linking density that imparts a certain degree of water repellency on the fabric surface, low absorbency was observed. Hand - feel durability performance evaluation To understand the ability of cross - linker groups in the polymer and enhance hand - feel durability for several washing cycles, the emulsions in Examples 1, 2, 3, 4, 5, 6 were applied to cotton fabrics and hand - feel evaluation was carried out before and after washing. Pad - dyeing was carried out by the dry - wet method, using a 30 g / l emulsion dosage, a 65 - 75% wet pick - up rate, and drying at 130 °C for 2 min. Washing was carried out using AATCC 135. Before washing and up to 10 - 15 washing cycles, softness evaluation was carried out by a touch panel, and the tested fabrics were graded, where the lowest number in the grading is the best (1 > 3 > 5 > 7). A hand - feel comparison is provided in the following table for fabrics coated with polysiloxane softeners with cross - linkers (Examples 1, 1a, 2, 3), fabrics coated with polysiloxane softeners without cross - linkers (Examples 4, 4a, 5, 6), and blank (uncoated) fabrics. Table 2 Table 3 Table 4 Comparative performance evaluation of polysiloxane softeners with and without cross - linker groups (Table 2 - 4) shows that since the polysiloxane polymer remains even after several washings, the polymer with cross - linker functional groups shows the best grading in terms of hand - feel before washing and after several washing cycles (10 - 15 HL). Different from the conventional polysiloxane softeners that bind by ionic interactions, the retention of this polymer is mainly due to the covalent bonding between the cross - linker groups in the polymer and the fabric - OH groups. However, these polysiloxane softeners with crosslinking groups inhibit the water absorbency of fabrics. Therefore, in order to achieve balanced hydrophilicity and handle characteristics before washing and after several washes, compositions of the organofunctional polysiloxane copolymer emulsion according to the present invention are prepared using conventional hydrophilic polysiloxane softener emulsions, such as in Examples 7, 8, 9, 10, 11, 12, 13, 14, 15. The efficacy of the compositions is compared using Example 1 and conventional hydrophilic softeners known in the prior art (such as in Examples 4, 5, and 6). Efficacy benefits of compositions with balanced properties The following Tables 5 to 8 show the comparison of handle (before and after washing) and absorbency. The graphical representation of the results in Figures 1 to 4 indicates that the candidate with the highest durability and good absorbency should have the smallest handle rating (x-axis) and the smallest absorbency value (y-axis). Table 5 Table 6 Table 7 Table 8 Fabrics treated with the copolymer compositions of the present invention show comparable handle and absorbency efficacy to conventional hydrophilic polysiloxane softeners (comparative examples) before washing. However, after washing (up to 10 HL), they exhibit good handle retention as indicated by good ratings (the lowest rating is the best), indicating higher durability. Therefore, a good balance of handle, absorbency, and durability up to 10 HL can be achieved by using compositions prepared with the crosslinking agent copolymer and hydrophilic softener according to the present invention. In addition, enhancements in other properties are also obtained, such as wrinkle resistance, fabric strength, non-yellowing, color fastness of dyed fabrics, etc. Compatibility with different chemicals / additives optical brighteners, metal salts and stability to pH, shear, and agitation show additional benefits. Results: Comparative efficacy evaluation of fabrics coated with the compositions reveals good handle ratings before and after 10 HL washing compared to conventional hydrophilic softeners. The crosslinking agent copolymer crosslinks the hydrophilic softener polymer with the fabric, forming an interpenetrating network structure that ensures that the polymer is not removed from the fabric even after several wash cycles. Therefore, balanced hydrophilicity and handle durability are adequately obtained by using compositions with the crosslinking agent copolymer. None [Figure 1] Illustration of the results in Table 5. The hand feel grade is on the x-axis and the absorption value is on the y-axis. The double dots in the figure indicate the required performance. [Figure 2] Illustration of the results in Table 6. The hand feel grade is on the x-axis and the absorption value is on the y-axis. The double dots in the figure indicate the required performance. [Figure 3] Illustration of the results in Table 7. The hand feel grade is on the x-axis and the absorption value is on the y-axis. The double dots in the figure indicate the required performance. [Figure 4] Illustration of the results in Table 8. The hand feel grade is on the x-axis and the absorption value is on the y-axis. The double dots in the figure indicate the required performance.
Claims
1. An organofunctional polysiloxane copolymer produced by copolymerization of: at least one polysiloxane monomer comprising at least two functional epoxy groups, at least one trimekoxysilane monomer, and at least one amine compound comprising at least two functional amino groups, wherein the amine compound is a mixture of at least one amine compound of general formula (IIIa) and at least one amine compound of general formula (IIIb): (IIIa); and (IIIb); wherein R is H or Me, y is an integer in the range of 2 to 39, or, the sum of x and z is an average value in the range of 1.2 to 6.
2. The copolymer of claim 1, wherein the molar percentage of polysiloxane monomer in the copolymer is in the range of 35% to 55%.
3. The copolymer of claim 1 or 2, wherein the mass percentage of the trialkoxysilane monomer in the copolymer according to the invention is in the range of 0.5 to 1.5% by weight.
4. A copolymer of claim 1 or 2, wherein the polysiloxane monomer has the general formula (Ia), (Ib), (Ic), (Id): (Ia); or (Ib); or (Ic); or (Id) wherein: m is an integer in the range of 1 to 10, n is an integer in the range of 1 to 10, a is an integer in the range of 200 to 400, b is an integer in the range of 2 to 4, Z is a C2 to C10 polyester or polyether group, and R1, R2, R3, R4, R5, R6, R7 and R8 are independently selected from C1 to C10 alkyl or C6 to C20 aromatic hydrocarbon groups.
5. A copolymer of claim 1 or 2, wherein the trialkoxysilane monomer has the general formula (IIa) or (IIb): (IIa) (IIb) wherein: Y is a C1 to C10 straight-chain or branched carbon chain.
6. The copolymer of claim 1 or 2, wherein the amine compound is a cyclic or linear amine compound.
7. A method for preparing a copolymer as claimed in any one of claims 1 to 6, comprising at least one polymerization step a), wherein at least the following are contacted in a solvent: at least one polysiloxane monomer comprising at least two functional epoxy groups, at least one trimekoxysilane monomer, and at least one amine compound comprising at least two functional amino groups, wherein the amine compound is a mixture of at least one amine compound of general formula (IIIa) and at least one amine compound of general formula (IIIb): (IIIa); and (IIIb); wherein R is H or Me, y is an integer in the range of 2 to 39, or, the sum of x and z is an average value in the range of 1.2 to 6.
8. The method of claim 7, wherein the solvent used in step a) has a boiling point below 150°C.
9. The method of claim 7 or 8, which includes a distillation step of the solvent used in step a).
10. The method of claim 9, wherein the temperature of the distillation step is below 100°C.
11. An aqueous emulsion, solution or suspension comprising a) at least one copolymer of any one of claims 1 to 6, b) at least one nonionic surfactant, and c) at least one weak protic acid.
12. The aqueous emulsion, solution or suspension of claim 11, wherein the copolymer is present in the aqueous emulsion, solution or suspension at a concentration of 10 wt% to 60 wt% based on the total weight of the aqueous emulsion, solution or suspension.
13. The aqueous emulsion, solution or suspension of claim 11 or 12, wherein the surfactant is present in the aqueous emulsion, solution or suspension according to the invention at a concentration of 3 wt% to 20 wt% based on the total weight of the aqueous emulsion, solution or suspension.
14. A composition comprising an aqueous emulsion, solution or suspension as claimed in any one of claims 11 to 13, and an emulsion of at least one hydrophilic polymer or at least one hydrophilic molecule.
15. The composition of claim 14, wherein the ratio of the aqueous emulsion, solution or suspension of any one of claims 11 to 13 to the emulsion of at least one hydrophilic polymer is 50:
50.
16. Use of a composition as claimed in claim 14 or 15 or an aqueous emulsion, solution or suspension as claimed in any one of claims 11 to 13, for treating textiles to simultaneously improve the softness and hydrophilicity of the textiles after several washing cycles.
17. A textile product treated with a composition as claimed in claim 14 or 15 or an aqueous emulsion, solution or suspension as claimed in any one of claims 11 to 13.
18. A method for treating textiles, comprising applying to the textiles a composition as claimed in claim 14 or 15 or an aqueous emulsion, solution or suspension as claimed in any one of claims 11 to 13.
19. The method of claim 18, wherein the application includes coating with an air knife or bar coater, impregnation or immersion by pressure dyeing or dip dyeing methods, printing techniques, spraying, or incorporation into textile fibers during the textile process.
20. The method of claim 19, wherein the composition of claim 14 or 15 or the aqueous emulsion, solution or suspension of any one of claims 11 to 13 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.
21. The method of any one of claims 18 to 20, wherein the composition of claim 14 or 15 or the aqueous emulsion, solution or suspension of any one of claims 11 to 13 is dried or cured at a temperature of 80 to 180°C and / or for a duration of 10 seconds to 12 minutes.