A fastness improving agent and preparation process thereof

Abstract

NOT VISIBLE DUE TO STATUS OF PATENT

Description

[0001] A FASTNESS IMPROVING AGENT AND PREPARATION PROCESS THEREOF

[0002] The present invention relates to a resin, obtained from the condensation of at least one sulfonated alkylated aromatic alcohol, at least one naphthalene diol and, optionally at least one phenolic diol, with at least one aliphatic carbonyl compound , to a method for forming such a resin, to the use of such a resin, to a dye fixing agent comprising such a resin, to a method for treating a fabric a dye fixing composition comprising such a resin.

[0003] Nylon fabrics compared to other commonly used fabrics are commonly applied in the fields of performance textiles and luxury fabric goods, due to showing increased tensile strength and being perceived as being light, haptically pleasant and comfortable when worn.

[0004] Nylon fabrics are commonly dyed with acid dyes to be more aesthetically pleasing. However, Nylon (Polyamide and its blends) problematically has a relatively low dye uptake, dyes unevenly and shows low colourfastness properties. To overcome the problems of dyeing Nylon, dye fixing agents are applied to dyed Nylon fabrics to improve their wet wash fastness and rubbing fastness properties.

[0005] However, dye fixing agents of the prior art are being prepared from petroleum based, highly hazardous synthetic chemical compounds, such as phenol or bisphenols. Since dye fixing agents of the prior art are also not ecologically friendly, they do not comply with common Eco certifications, standards or requirements, such as Bluesign®, OEKO-TEX ®, ZDHC, MRSL and PRSL.

[0006] Therefore, it is an objective to provide ecologically friendly, non-hazardous dye fixing agents, in particluar for polyamides, especially for polyamide and elastane blends of polyamide, which comply with common Eco certifications, standards or requirements, such as Bluesign®, OEKO-TEX ®, ZDHC, MRSL and PRSL. Furthermore, the ecologically friendly dye fixing agents would have to show similar, if not better, colourfastness properties, such as wet wash fastness and rubbing fastness properties, compared to the prior art dye fixing agents. Additionally, ecologically friendly dye fixing agents should be inexpensive.

[0007] It has now been surprisingly found that inexpensive, ecologically friendly, non- hazardous dye fixing agents could be formed, which comply with common Eco certifications, standards or requirements, such as Bluesign®, OEKO-TEX ®, ZDHC, MRSL and PRSL. The dye fixing agents show comparable wet wash fastness compared to the prior art dye fixing agents.

[0008] Hence, the instant invention relates to a resin, obtained from the condensation of at least one sulfonated alkylated aromatic alcohol, at least one naphthalene diol and, optionally at least one phenolic diol, with at least one aliphatic carbonyl compound, to a method for forming such a resin, to the use of such a resin, to a dye fixing agent comprising such a resin, to a method for treating a fabric a dye fixing composition comprising such a resin.

[0009] Said resin is inexpensive, ecologically friendly, non-hazardous, avoids the use of phenol and bisphenol, and complies with common Eco certifications, standards or requirements, such as Bluesign®, OEKO-TEX ®, ZDHC, MRSL and PRSL. The resin, when used within a dye fixing agent composition, shows wet wash fastness properties for all kinds of fabrics, including Nylon and its various compositions of elastane blends.

[0010] The expression "comprised between X and Y" includes boundaries, unless explicitly stated otherwise. This expression means that the target range includes the X and Y values, and all values from X to Y.

[0011] Throughout the description and claims of this specification, the words "comprise" and "contain" and variations of the words, for example "comprising" and "comprises", mean "including but not limited to", and do not exclude other moieties, additives, components, integers or steps. Moreover, the singular encompasses the plural unless the context otherwise requires: in particular, where the indefinite article is used, the specification is to be understood as contemplating plurality as well as singularity, unless the context requires otherwise.

[0012] Where upper and lower limits are quoted for a property, for example for the concentration of a component, then a range of values defined by a combination of any of the upper limits with any of the lower limits may also be implied.

[0013] The instant invention relates to a resin, obtained from the condensation of at least one sulfonated alkylated aromatic alcohol (A), at least one naphthalene diol (B) and, optionally at least one phenolic diol (C), with at least one aliphatic carbonyl compound.

[0014] The at least one sulfonated alkylated aromatic alcohol is according to formula (A)

[0015] The at least one naphthalene diol is according to formula (B)

[0016] The at least one phenolic diol is according to formula (C)

[0017] A sulfonated alkylated aromatic alcohol is commonly a structure with a sulfonated aromatic cycle, rather than a sulfonated alkyl substituent. The at least one sulfonated alkylated aromatic alcohol (A), which is used in the condensation to obtain the resin according to the invention, preferably is a sulfonated meta-alkylphenol, more preferably a para-sulfonated meta-alkylphenol.

[0018] A meta-alkylphenol refers to a phenol that is meta-substituted with an alkyl-group relative to the hydroxyl-moiety of the phenol. A para-sulfonated phenol refers to a phenol that is para-substituted with a sulfone-group relative to the hydroxyl -moiety of the phenol.

[0019] The at least one sulfonated alkylated aromatic alcohol (A) preferably is a sulfonated aromatic compound, according to formula (I),

[0020] (I), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na.

[0021] The at least one sulfonated alkylated aromatic alcohol (A) preferably is a parasulfonated aromatic compound, according to formula (I-para),

[0022] (I-para), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na.

[0023] The at least one sulfonated alkylated aromatic alcohol (A) more preferably is a parasulfonated cardanol compound, according to formula (I-cnol),

[0024] (I-cnol), wherein Y is hydrogen or an alkali metal, preferably Na.

[0025] Cardanol is a phenolic structure compound obtained from anacardic acid, and can be obtained via the vacuum distillation of roasted cashew nutshell liquid (CNSL), a byproduct of cashew nut processing obtained from the spongy mesocarp of cashew nut shells. Cardanol is a BioSource, non-edible source, and inexpensive organic renewable natural resource.

[0026] A sulfonated cardanol compound can be formed by sulfonation of cardanol with oleum.

[0027] The at least one naphthalene diol (B), which is used in the condensation to obtain the resin according to the invention, is preferably 1,5-dihydroxynaphthalene, 2,6- dihydroxynaphthalene and / or 2,7-dihydroxynaphthalene, more preferably 2,7- dihydroxynaphthalene.

[0028] The at least one phenolic diol (C), which is optionally used in the condensation to obtain the resin according to the invention, is preferably benzene-l,2-diol, benzene- 1,3-diol and / or benzene-l,4-diol, more preferably benzene-l,3-diol.

[0029] The at least one aliphatic carbonyl compound, which is used in the condensation to obtain the resin according to the invention, is preferably an aldehyde or ketone, more preferably a formaldehyde. The resin is preferably obtained from the condensation of a sulfonated aromatic compound, according to formula (I), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na, 2,7- dihydroxynaphthalene, benzene-l,3-diol, and formaldehyde.

[0030] The resin is more preferably obtained from the condensation of a para-sulfonated aromatic compound, according to formula (I-para), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na, 2,7-dihydroxynaphthalene, benzene-l,3-diol, and formaldehyde.

[0031] The resin is even more preferably obtained from the condensation of a parasulfonated aromatic compound, according to formula (I-para), wherein R = CisHsi-n, wherein n = 0 and wherein Y is Na, 2,7-dihydroxynaphthalene, benzene-l,3-diol, and formaldehyde.

[0032] The resin preferably contains the substructure according to formula (II), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0, wherein Y is hydrogen or an alkali metal, preferably Na, wherein V, W and X independently of each other stand for a natural number.

[0033] The resin more preferably contains the substructure according to formula (II -1),

[0034]

[0035] (IM), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0, wherein Y is hydrogen or an alkali metal, preferably Na, wherein V, W and X independently of each other stand for a natural number.

[0036] In one embodiment, the resin contains the substructure according to formula (II-2),

[0037] (H-2), wherein R = CisHsi-n, wherein n = 0, wherein V, W and X independently of each other stand for a natural number.

[0038] Preferably, V, W and X independently of each other stand for a natural number in the range of 1 to 20, more preferably of 1 to 10, even more preferably of 1 to 5.

[0039] In one embodiment V, W and X each stand for 1.

[0040] Preferably, the weight average molar mass of the resin is in the range of 400 to 2000 g / mol, more preferably of 600 to 1400 g / mol, especially preferably of 800 to 1300 g / mol, wherein the molar mass distribution of the resin is determined according to ISO 13885-3:2020.

[0041] Preferably, the resin, is obtained from the condensation of at least one sulfonated alkylated aromatic alcohol (A), at least one naphthalene diol (B) and, optionally at least one phenolic diol (C), with at least one aliphatic carbonyl compound, wherein the weight ratio of the at least one sulfonated alkylated aromatic alcohol (A) to the at least one naphthalene diol (B) is from 2: 1 to 8: 1, preferably 3: 1 to 6: 1, and / or wherein the weight ratio of the at least one sulfonated alkylated aromatic alcohol (A) to the at least one phenolic diol (C) is from 10: 1 to 30: 1, preferably 15: 1 to 22: 1, and / or wherein the weight ratio of the at least one naphthalene diol (B) to the at least one phenolic diol (C) is from 2: 1 to 8: 1, preferably 4: 1 to 6: 1, and / or wherein the weight ratio of the at least one sulfonated alkylated aromatic alcohol (A) to the at least one naphthalene diol (B) and the at least one phenolic diol (C) combined is from 2: 1 to 6: 1, preferably 3: 1 to 5: 1.

[0042] Preferably, the resin, is obtained from the condensation of at least one sulfonated alkylated aromatic alcohol (A), at least one naphthalene diol (B) and, optionally at least one phenolic diol (C), with at least one aliphatic carbonyl compound, wherein the weight ratio of the at least one sulfonated alkylated aromatic alcohol (A) to the at least one aliphatic carbonyl compound is from 6: 1 to 25: 1, preferably 10: 1 to 15: 1, and / or wherein the weight ratio of the at least one naphthalene diol (B) to the at least one aliphatic carbonyl compound is from 1: 1 to 4: 1, preferably 2: 1 to 3: 1, and / or wherein the weight ratio of the at least one phenolic diol (C) to the at least one aliphatic carbonyl compound is from 3: 1 to 1: 1, preferably 2: 1 to 2:3, and / or wherein the weight ratio of the at least one sulfonated alkylated aromatic alcohol (A), the at least one naphthalene diol (B) and the at least one phenolic diol (C) combined to the at least one aliphatic carbonyl compound is from 8: 1 to 20: 1, preferably 12: 1 to 18: 1.

[0043] The invention further relates to a dye fixing agent composition comprising a resin as defined above.

[0044] All definitions and preferred embodiments as set forth above apply analogously, to the dye fixing agent composition.

[0045] The invention further relates to a method for forming a resin comprising the following steps: i) providing at least one sulfonated alkylated aromatic alcohol (A), at least one naphthalene diol (B), optionally at least one phenolic diol (C), and at least one base or acid in a solvent, preferably a protic solvent, and ii) adding at least one aliphatic carbonyl compound to the mixture i) and heating the mixture from i) to a temperature of 50 °C to 140 °C over a period of 1 to 4 hours.

[0046] All definitions and preferred embodiments, as set forth above, apply analogously, to the method for forming a resin.

[0047] A protic solvent, preferably used in the method for forming a resin, may be water, an alcohol and / or diethylene glycol, preferably demineralized water and / or diethylene glycol.

[0048] Preferably, the method for forming a resin comprises the following steps: i) providing at least one sulfonated alkylated aromatic alcohol, according to formula (I), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na, at least one naphthalene diol (B), at least one phenolic diol (C), and at least one base in a protic solvent, and ii) adding at least one aliphatic carbonyl compound to the mixture i) and heating the mixture from i) to a temperature of 50 °C to 140 °C over a period of 1 to 4 hours. More preferably, the method for forming a resin comprises the following steps: i) providing at least one para-sulfonated aromatic compound, according to formula (I-para), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na, 2,7-dihydroxynaphthalene, benzene-l,3-diol, and at least one base in a protic solvent, and ii) adding formaldehyde to the mixture i) and heating the mixture from i) to a temperature of 50 °C to 140 °C over a period of 1 to 4 hours.

[0049] Even more preferably, the method for forming a resin comprises the following steps: i) providing at least one para-sulfonated aromatic compound, according to formula (I-para), wherein R = CisHsi-n, wherein n = 0 and wherein Y is Na, 2,7- dihydroxynaphthalene, benzene-l,3-diol, and sodium hydroxide in water, and ii) adding formaldehyde to the mixture i) and heating the mixture from i) to a temperature of 50 °C to 140 °C over a period of 1 to 4 hours.

[0050] Preferably, the method for forming a resin additionally comprises the following steps for providing the at least one sulfonated alkylated aromatic alcohol (A): ai) dissolving at least one alkylated aromatic alcohol in an organic acid, aii) cooling the mixture of ai) to a temperature of -20 °C to 20 °C, preferably to a temperature of 0 °C to 15 °C and adding oleum to the mixture of ai), and aiii) isolating the at least one sulfonated alkylated aromatic alcohol (A) from the mixture of aii) by distillation.

[0051] The organic acid, used in the method for forming the at least one sulfonated alkylated aromatic alcohol (A), may be a carboxylic acid, preferably acetic acid.

[0052] Such method for forming a resin has the advantage that the resin can be formed without further purification in moderate yields. More preferably, the method for forming a resin additionally comprises the following steps for providing the at least one sulfonated alkylated aromatic alcohol (A), which is a sulfonated aromatic compound, according to formula (I): ai) dissolving a meta-alkylphenol, wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na, in a carboxylic acid, aii) cooling the mixture of ai) to a temperature of -20 °C to 20 °C, preferably to a temperature of 0 °C to 15 °C and adding oleum to the mixture of ai), and aiii) isolating the sulfonated aromatic compound, according to formula (I) from the mixture of aii) by distillation.

[0053] Even more preferably, the method for forming a resin additionally comprises the following steps for providing the at least one sulfonated alkylated aromatic alcohol (A), which is a para-sulfonated aromatic compound, according to formula (I-para): ai) dissolving a meta-alkylphenol, wherein R = CisHsi-n, wherein n = 0 and wherein Y is Na, in a acetic acid, aii) cooling the mixture of ai) to a temperature of 0 °C to 15 °C and adding oleum to the mixture of ai), and aiii) isolating the sulfonated aromatic compound, according to formula (I-para) from the mixture of aii) by distillation.

[0054] Such method for forming the at least one sulfonated alkylated aromatic alcohol (A) has the advantage that the reaction proceeds with a degree of up to 99% sulfonation of the at least one alkylated aromatic alcohol, resulting in a higher yield and a cleaner reaction.

[0055] The invention further relates to a resin obtainable by the method for forming a resin as defined above.

[0056] All definitions and preferred embodiments as set forth above apply analogously, to the resin obtainable by the method for forming a resin. The invention further relates to the use of a resin as defined above as a dye fixing and / or reservation agent.

[0057] All definitions and preferred embodiments as set forth above apply analogously, to the use of a resin as defined above.

[0058] The dye fixing agent is preferably used for a fabric, preferably for a polyamide fabric, a polyamide-elastane blend fabric and / or wool, particularly a fabric containing polyamide, such as nylon and / or a nylon-elastane blend fabric.

[0059] The dye fixing agent may also be applied to other fabrics, such as fabrics containing cellulose acetate, cotton, polyester and / or polyacrylonitril .

[0060] Using the dye fixing agent for the aforementioned fabrics increases the dye fixing performance and the wash fastness performance for these fabrics.

[0061] The invention further relates to a method for treating a fabric with a dye fixing composition, comprising the following steps: bi) dyeing a fabric, preferably a fabric containing cellulose acetate, cotton, polyamide, polyester, polyacrylonitril and / or wool, more preferably a polyamide and its blends, with at least one dye, preferably at least one acid dye, and bii) treating the dyed fabric of bi) with the dye fixing composition as set forth above or with an aqueous solution comprising the dye fixing composition as set forth above, and biii) drying the dyed fixed fabric of bii) with dry heat or steam.

[0062] All definitions and preferred embodiments as set forth above apply analogously, to the method for treating a fabric with a dye fixing composition.

[0063] Preferably, the fabric according to bi) and / or the dyed fabric according to bii) are treated with the dye fixing composition or the aqueous solution comprising the dye fixing composition via application with an air knife or a road coater, impregnation or immersion via a padding or exhaust method, a printing technique, spray coating, or via spinning.

[0064] Preferably, the fabric according to bi) and / or the dyed fabric according to bii) is treated with the aqueous solution comprising the dye fixing composition, wherein the dye fixing composition is present in the aqueous solution at a mass concentration in the range of 1 to 20%.

[0065] Preferably, the fabric according to bi) and / or the dyed fabric according to bii) is treated with the aqueous solution comprising the dye fixing composition, wherein the pH of the aqueous solution is in the range of 3 to 9.

[0066] The following Examples serve to illustrate the invention. Unless otherwise indicated therein, parts are parts by weight and percentages are percentages by weight. Temperatures are given in degrees Celsius.

[0067] Examples

[0068] Sulfonation Results:

[0069] Example 1-1

[0070] 100 g of cardanol and 200 g of acetic acid as solvent are added in a dry round bottom reactor fitted with reflux condenser, thermometer pocket, nitrogen inlet and ice bath. Reaction mixture temperature reduced to below 10 °C with help of ice bath. Once temperature reduced to below 10 °C, 20 ml of Oleum dropwise added under continuous stirring. After sulfonation, Cardanol sulfonate solution taken out and purify product by distillation.

[0071] Example 1-2

[0072] 100 g of cardanol and 200 g of methanol as solvent are added in a dry round bottom reactor fitted with reflux condenser, thermometer pocket, nitrogen inlet and ice bath. Reaction mixture temperature reduced to below 10 °C with help of ice bath. Once temperature reduced to below 10 °C, 20 ml of Oleum dropwise added under continuous stirring. After sulfonation, Cardanol sulfonate solution taken out and purify product by distillation.

[0073] Example 1-3

[0074] 100 g of cardanol and 200 g of dimethyl sulfoxide as solvent are added in a dry round bottom reactor fitted with reflux condenser, thermometer pocket, nitrogen inlet and ice bath. Reaction mixture temperature reduced to below 10 °C with help of ice bath. Once temperature reduced to below 10 °C, 20 ml of Oleum dropwise added under continuous stirring. After sulfonation, Cardanol sulfonate solution taken out and purify product by distillation. Table 1:

[0075] Dve fixing agent Results:

[0076] Example 2-1

[0077] 20.48 g of sulfonated cardanol and 4.9 g of 2,7-dihydroxynapthanlene and 1.0 g of 1,3-dihydroxybenzene are added in a round bottom reactor fitted with reflux condenser, thermometer pocket and nitrogen inlet. Mixture of 6 g of Sodium hydroxide, 18 g of demineralized water was added under continuous stirring. Solution was then refluxed at 50-120 °C for 1-4 hours or more under nitrogen atmosphere with continuous formaldehyde dropwise addition until 1.85 g of formaldehyde were added (100% solution). After polymerization, resin solution taken out and used as dye fixing agent for polyamide fabric. Observed solid content of the resinous product is in the range of 30-50%.

[0078] Example 2-2

[0079] 20.48 g of sulfonated cardanol and 4.9 g of 2,7-dihydroxynapthanlene are added in a round bottom reactor fitted with reflux condenser, thermometer pocket and nitrogen inlet. Mixture of 6 g of Sodium hydroxide and 18 g of demineralized water was added under continuous stirring. Solution was then refluxed at 50-120 °C for 1- 4 hours or more under nitrogen atmosphere with continuous formaldehyde dropwise addition until 1.85 g of formaldehyde were added (100% solution). After polymerization, polymerized solution taken out and used as dye fixing agent for polyamide fabric. Observed solid content of the resinous product is in the range of 30-50%. Comparative Example 2-1

[0080] 20.48 g of sulfonated cardanol is added in a round bottom reactor fitted with reflux condenser, thermometer pocket and nitrogen inlet. Mixture of 6 g of Sodium hydroxide and 18 g of demineralized water was added under continuous stirring. Solution was then refluxed at 50-120 °C for 1-4 hours or more time under nitrogen atmosphere with continuous formaldehyde dropwise addition until 1.85 g of formaldehyde were added (100% solution). After polymerization, resin solution taken out and used as dye fixing agent for polyamide fabric. Observed solid content of the resinous product is in the range of 30-50%.

[0081] Table 2: Grey Scale wash fastness Rating for PA 66 fabric

[0082] Table 3: Grey Scale wash fastness Rating for PA / EL fabric 672:28) Blends

[0083] Samples of polyamide fabric and its blends with elastane were dyed with various acid dyes but not limited to colours, such as Red, Yellow, Black, and Blue. These dyed fabrics afterwards were treated with newly developed eco-friendly fixative and commercially available standard. They are then treated with dry heat or steam, and their wet fastness properties are determined. The fastness properties are assessed by comparison with the grey scale. Wash fastness tests were performed according to a method in which the fabrics were washed at 50 °C over 45 min according to ISO 105-C06-2010 at B1M (adjacent fabric - multifiber).

[0084] Polyamide PA 66 fabric was dyed with red dye in an exhaust dyeing process in which the dye solution is produced by dissolving the dye in the liquor according to a dye to liquor weight ratio of 1:20 (dye to liquor). Then the fabric is immersed into the dye solution and kept in the exhaust machine for one hour at 98 °C. This dyed fabric was further used for treatment process with the newly developed eco- friendly dye fixative and commercially available standard dye fixing agent. Results for Polyamide PA 66 fabric with red dye are summarized in Table 2, in which it can be sees that the development sample has better dye fixing performance than the blank sample and better or comparable performance with the standard product. Dyed fabric wash fastness performance was measured on adjacent fabric - multifiber (Cellulose acetate (CA), Cotton (CO), Polyamide (PA), Polyester (PES), Polyacrylonitril (PAN) and wool (WO) and its rating based on the grey scale are summariezed in Table 2. PA / EL Elastic swimwear PA / EL 72:28 was also dyed with Red Dye in an exhaust dyeing process in which the dye solution is produced by dissolving the dye in the liquor according to a dye to liquor weight ratio of 1:20 (dye to liquor). Then the fabric is immersed into the dye solution and kept in the exhaust machine for one hour at 98 °C. Then the dyed fabric was used for the treatment process with the newly developed eco-friendly dye fixative and commercially available standard dye fixing agent. Results for a PA / EL Elastic swimwear fabric dyed with red dye are summarized in the Table 3. Dyed fabric wash fastness performance was measured on the adjacent fabric - multifiber (Cellulose acetate (CA), Cotton (CO), Polyamide (PA), Polyester (PES), Polyacrylonitril (PAN) and wool (WO) and its rating based on the grey scale are summarized, in which it can be seen that the development samples have a better dye fixing performance than the blank sample and comparable performance with the standard products.

[0085] Overall results show the newly developed eco-friendly product is suitable for the commercial application as a dye fixing agent for polyamide and blend fabrics containing polyamide.

Claims

Claims1. A resin, obtained from the condensation of at least one sulfonated alkylated aromatic alcohol (A), at least one naphthalene diol (B) and, optionally at least one phenolic diol (C), with at least one aliphatic carbonyl compound.

2. Resin, according to claim 1, wherein the at least one sulfonated alkylated aromatic alcohol (A) is a sulfonated meta-alkylphenol, preferably a para-sulfonated meta-alkylphenol.

3. Resin, according to claims 1 or 2, wherein the at least one sulfonated alkylated aromatic alcohol (A) is a sulfonated aromatic compound, according to formula (I),(I), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na.

4. Resin, according to one of the claims 1 to 3, wherein the at least one naphthalene diol (B) is 1,5-dihydroxynaphthalene, 2,6-dihydroxynaphthalene and / or 2,7-dihydroxynaphthalene, preferably 2,7-dihydroxynaphthalene.

5. Resin, according to one of the claims 1 to 4, wherein the at least one phenolic diol (C) is benzene-l,2-diol, benzene-l,3-diol and / or benzene-l,4-diol, preferably benzene-l,3-diol.

6. Resin, according to one of the claims 1 to 5, wherein the at least one aliphatic carbonyl compound is formaldehyde.

7. Resin, according to one of the claims 1 to 6, wherein the, wherein the at least one sulfonated alkylated aromatic alcohol (A) is a sulfonated aromatic compound, according to formula (I), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0 and wherein Y is hydrogen or an alkali metal, preferably Na, wherein the at least one naphthalene diol (B) is 2,7-dihydroxynaphthalene, wherein the at least one phenolic diol (C) is benzene-l,3-diol, and wherein the at least one aliphatic carbonyl compound (D) is formaldehyde.

8. Resin, according to one of the claims 1 to 7, containing the substructure, according to formula (II)(II), wherein R = CisHsi-n, wherein n = 0, 2, 4 or 6, preferably n = 0, wherein Y is hydrogen or an alkali metal, preferably Na, wherein V, W and X independently of each other stand for a natural number.

9. A dye fixing agent composition comprising the resin according to one of the claims 1 to 8.

10. Method for forming a resin, comprising the following steps: i) providing at least one sulfonated alkylated aromatic alcohol (A), at least one naphthalene diol (B), optionally at least one phenolic diol (C), and at least one base or acid in a solvent, preferably a protic solvent, and ii) adding at least one aliphatic carbonyl compound to the mixture i) and heating the mixture from i) to a temperature of 50 °C to 140 °C over a period of 1 to 4 hours.

11. Method, according to claim 10, additionally comprising the following steps for providing the at least one sulfonated alkylated aromatic alcohol (A): ai) dissolving at least one alkylated aromatic alcohol in an organic acid, aii) cooling the mixture of ai) to a temperature of -20 °C to 20 °C, preferably to a temperature of 0 °C to 15 °C and adding oleum to the mixture of ai), and aiii) isolating the at least one sulfonated alkylated aromatic alcohol (A) from the mixture of aii) by distillation.

12. A resin obtainable by the process according to the claims 10 or 11.

13. Use of a resin according to one of the claims 1 to 8 or claim 12 as a dye fixing agent and / or as a reservation agent.

14. Use according to claim 13 for a fabric, preferably for a polyamide fabric, a polyamide-elastane blend fabric and I or wool, particularly a fabric containing polyamide, such as nylon and / or a nylon-elastane blend fabric.

15. Method for treating a fabric with a dye fixing composition, comprising the following steps: bi) dyeing a fabric, preferably a fabric containing cellulose acetate, cotton, polyamide, polyester, polyacrylonitril and / or wool, more preferably a polyamide and its blends, with at least one dye, preferably at least one acid dye, and bii) treating the dyed fabric of bi) with the dye fixing composition according to claim 9 or an aqueous solution containing the dye fixing composition, and biii) drying the dyed fixed fabric of bii) with dry heat or steam.

16. Method according to claim 15, wherein the dyed fabric according to bii) is treated with the aqueous solution comprising the dye fixing composition, wherein the dye fixing composition is present in the aqueous solution at a mass concentration in the range of 1 to 20%.

17. Method according to the claims 15 or 16, wherein the dye fixing composition is present in the aqueous solution at a mass concentration in the range of 1 to 20% and / or wherein the pH of the aqueous solution is in the range of 3 to 9.