WO2025218529A1

WO2025218529A1 - Dyeable polyurethane composition and method thereof

Info

Publication number: WO2025218529A1
Application number: PCT/CN2025/087729
Authority: WO
Inventors: Liang Zhao; Jia Yue HUANG; Feng Chao HU; Hai Sheng Wu; Dong Liang
Original assignee: BASF China Co Ltd; BASF SE
Current assignee: BASF China Co Ltd; BASF SE
Priority date: 2024-04-15
Filing date: 2025-04-08
Publication date: 2025-10-23
Anticipated expiration: 2026-10-15

Abstract

Provided are a guanidine compound being a product of an amine; and a carbodiimide; a dyeable composition comprising a polymer selected from a polyester, a polyamide, and a polyurethane; and the guanidine compound, and a fabric.

Description

DYEABLE POLYURETHANE COMPOSITION AND METHOD THEREOF

BACKGROUND

Guanidines and its salts are known in the art.

CN109295526A disclosed a preparation method of antimicrobial polyurethane elastomeric fiber containing guanidine block polymer. According to the disclosure, the guanidine structures were incorporated into the backbone of polyurethane-polyurea.

CN116376013A disclosed a preparation method of guanidinium-modified hyperbranched polyamide-amine composite color fixing polymer and its application.

There is a need of dyeable polyurethane-polyurea compositions that are easy to be dyed and lead to dyed products with high colorfastness.
BRIEF SUMMARY

According to at least one embodiment of the present disclosure, provided is a guanidine compound being a product of:

an amine; and

a carbodiimide represented by

wherein,

n is an integer no less than 1;

Q₁ and Q₂ independently are bivalent hydrocarbon radicals or bivalent hydrocarbon radicals interrupted by one or more bivalent radicals represented by any of Formula (2) through Formula (7) :

--O-- Formula (2) ,

and

R₁ and R₂ independently are monovalent hydrocarbon radicals; and

X₁ and X₂ independently are bivalent radicals represented by any of Formula (5) through Formula (13) :

Q₃ through Q₈ are independently a monovalent organic radical selected from:

A) an unsubstituted or substituted monovalent hydrocarbon radical,

B) a monovalent radical containing one or more oxygen, nitrogen, sulfur, phosphorus, or silicon atoms, and

C) a monovalent radical containing one or more repeating units selected from ether, ester, thioether, amide, imide, siloxane, urethane, urea, allophanate, or any combination thereof.

According to at least one embodiment of the present disclosure, further provided is a dyeable composition comprising:

a polymer selected from a polyester, a polyamide, and a polyurethane; and

the guanidine compound.

According to at least one embodiment of the present disclosure, further provided is a fabric made from the dyeable composition.

DETAILED DESCRIPTION

Unless defined otherwise, all technical and scientific terms used herein have the meaning commonly understood by a person skilled in the art to which the present disclosure belongs. As used herein, the following terms have the meanings ascribed to them below, unless specified otherwise.

Unless otherwise identified, all percentages (%) are “percent by weight" .

A carbodiimide refers to an organic compound having at least one bivalent moiety represented by the formula -N═C═N-. A carbodiimide may be formed by a carbodiimidization of a polyisocyanate, in which two -N═C═O groups form one -N═C═N-moiety and release CO₂. After the carbodiimidization, there may be one or more residual -N═C═O groups that can be end-capped by an end-capping agent containing at least one active hydrogen atom.

An isocyanate refers to an organic compound having at least one -N═C═O group. A polyisocyanate refers to an organic compound having two or more -N═C═O groups and may be a diisocyanate, a triisocyanate, or a higher-functionality isocyanate.

Guanidines refer to a group of organic compounds sharing a common functional group with the general structure (R₁R₂N) (R₃R₄N) C=N-R₅, wherein R₁ through R₅ are independently monovalent radicals including without limitation to hydrogen atom, substituted or unsubstituted alkyl radicals, substituted or unsubstituted cycloalkyl radicals, and substituted or unsubstituted aryl radicals. The simplest guanidine is HNC (NH₂) ₂.

An alkyl radical refers to a monovalent hydrocarbon radical derived from an alkane by removal of one hydrogen atom from any carbon atom. Exemplary alkyl radicals include without limitation to methyl -CH₃, ethyl -C₂H₅, n-propyl -CH₂CH₂CH₃, and isopropyl -CH (CH₃) ₂.

A cycloalkyl radical refers to a monovalent hydrocarbon radical derived from a cycloalkane by removal of one hydrogen atom from a ring carbon atom. Exemplary cycloalkyl radicals include without limitation to cyclobutyl, cyclopentyl, and cyclohexyl.

An alkenyl radical refers to a monovalent hydrocarbon radical derived from an alkene by removal of one hydrogen atom from an unsaturated carbon atom. Exemplary alkenyl radicals include without limitation to ethenyl radical -CH═CH₂ (commonly known as vinyl) .

A cycloalkenyl radical refers to a monovalent hydrocarbon radical derived from a cycloalkene by removal of one hydrogen atom from an unsaturated carbon atom. Exemplary cycloalkenyl radicals include without limitation to 3-cyclohexenyl radical

An alkynyl radical refers to a monovalent radical derived from an alkyne by removal of one hydrogen atom from a triply bonded carbon atom. Exemplary alkynyl radicals include without limitation to ethynyl (commonly known as acetylenic radical) .

A cycloalkynyl radical refers to a monovalent radical derived from a cycloalkyne by removal of one hydrogen atom from a triply bonded carbon atom. Exemplary cycloalkynyl radicals include without limitation to 3-cyclooctynyl radical

An aryl radical refers to a monovalent radical derived from an arene by removal of one hydrogen atom from an aromatic carbon atom. Exemplary aryl radicals include without limitation to phenyl -C₆H₅ and naphthalenyl -C₁₀H₇.

An alkylene radical refers to a bivalent hydrocarbon radical derived from an alkane by removal of two hydrogen atoms from the same. Exemplary alkylene radicals include without limitation to methylene radical (-CH₂-) , ethylene radical (-CH₂CH₂-) , and hexamethylene radical (-CH₂CH₂CH₂CH₂CH₂CH₂-) .

A cycloalkylene radical refers to a bivalent hydrocarbon radical derived from a cycloalkane by removal of two hydrogen atoms from the same. Exemplary cycloalkylene radicals include without limitation to 1, 4-cyclohexylene radical

An alkenylene radical refers to a bivalent hydrocarbon radical derived from an alkene by removal of two hydrogen atoms from the same. Exemplary alkenylene radicals include without limitation to ethenylene radical (-CH═CH-) .

A cycloalkenylene radical refers to a bivalent hydrocarbon radical derived from a cycloalkene by removal of two hydrogen atoms from the same. Exemplary cycloalkenylene radicals include without limitation to 3, 6-cyclohexenylene radical

An alkynylene radical refers to a bivalent hydrocarbon radical derived from an alkyne by removal of two hydrogen atoms from the same. Exemplary alkynylene radicals include without limitation to ethynylene radical (-C≡C-) .

A cycloalkynylene radical refers to a bivalent hydrocarbon radical derived from a cycloalkyne by removal of two hydrogen atoms from the same. Exemplary cycloalkynylene radicals include without limitation to 3, 7-cyclooctynylene radical

An arylene radical refers to a bivalent hydrocarbon radical derived from an arene by removal of two hydrogen atoms from two carbon atoms. Exemplary arylene radicals include without limitation to 1, 4-phenylene radical

Polyurethane, shortened as “PU” , refers to a polymer that is an addition product of di-or polyisocyanate and one or more isocyanate-reactive compounds, which preferably is a compound with two or more isocyanate-reactive functionalities. The isocyanate-reactive compounds include for example, polyethers, polyesters, polycarbonates, polyamines, diols, triols, diamines, triamines, etc. Herein, polyurethane includes thermoplastic polyurethane formed by diisocyanate, polyol, and small molecular diols; polyurethane-urea, formed by di-or polyisocyanate, polyol, and small molecular diamine or triamine; and/or other addition product of di-or polyisocyanate and polyol or polyamine.

Polyurethane-urea, also termed poly (urethane-urea) , refers to a polymer that contains urethane (-O-C (═O) -NH-) and urea (-NH-C (═O) -NH-) linkages as repeating units. Polyurethane-urea may be an addition product of a di-or polyisocyanate, a polyol, and a diamine or triamine as chain extender.

The term “substituted” applied to the terms such as “alkylene” , “cycloalkylene” , and “arylene” means that those groups are substituted by one or more identical or different radicals. The substitution may be one or more halogen atom, an alkoxy radical, a dialkylamino radical, an alkylthio radical, a nitro radical, a nitroso radical, a nitrile radical, or the like. The substitution may occur once or more times.

Unless otherwise identified, the temperature refers to room temperature and the pressure refers to ambient pressure.

Guanidine

Provided is a guanidine compound, which is a product of an amine; and

a carbodiimide represented by

wherein,

n is an integer no less than 1;

--O-- Formula (2) ,

and

R₁ and R₂ independently are monovalent hydrocarbon radicals; and

Q₃ through Q₈ are independently a monovalent organic radical selected from:

A) an unsubstituted or substituted monovalent hydrocarbon radical,

It is to be understood that an exemplary bivalent hydrocarbon radicals interrupted by one or more bivalent radicals represented by any of Formula (2) through Formula (7) may be a bivalent hydrocarbon radicals interrupted by one or more bivalent radicals represented by Formula (2) , for example, a polyoxyethylene radical (- (OCH₂CH₂) _n-) , a polyoxypropylene radical (- (OCH (CH₃) CH₂) _n-) , or a polyoxytetramethylene radical (- (OCH₂CH₂CH₂CH₂) _n-) .

Preferably, to prepare the guanidine compound, the amine comprises a monoamine, a diamine, a triamine, a tetraamine, a polyetheramine, a linear polyethyleneimine, a branched polyethyleneimine, or an alkanolamine.

The monoamine may include methylamine, ethylamine, isopropylamine, laurylamine, dimethylamine, diethylamine, cyclohexylamine, monofunctional polyetheramine, and aniline.

The diamine may include ethylenediamine, 1, 2-diaminopropane, 1, 3-diamionpropane, diaminocyclohexane, N, N-dimethylethylenediamine, N, N-Diethylethylenediamine, and isomers of phenylenediamines.

The triamine may include diethylenetriamine, 1, 3, 5-triaminobenzene, or cyclohexane-1, 3, 5-triamine.

The tetraamine may include triethylenetetraamine or 1, 2, 4, 5-benzenetetramine.

The polyetheramine may include polyetheramine commercially available from Huntsman under the trademarksuch asD series polyetheramines.

The linear polyethyleneimine may include polyethyleneimine commercially available from BASF under the trademark

The branched polyethyleneimine may include low molecular weight branched polyethyleneimine commercially available from BASF under the trademarksuch asFG polyethyleneimine.

The alkanolamine may include ethanolamine and propanolamine.

In some embodiments, the amine is a mixture of two or more kinds of amine compounds.

Preferably, the amine is a primary or secondary monoamine represented by HN (R₃) R₄, and wherein at least one of R₃ and R₄ is a monovalent hydrocarbon radicals.

Preferably, the amine is methylamine, ethylamine, n-propylamine, n-butylamine, n-hexylamine, dimethylamine, or diethylamine.

Alternatively, the amine is a polyetheramine which is an amine-terminated poly (alkylene oxide) . The alkylene oxide may include at least one of ethylene oxide, propylene oxide, or tetramethylene oxide. The poly (alkylene oxide) may be a homopolymer or a copolymer.

Exemplary polyetheramines include: polyetheramine commercially available from BASF under the trademarksuch asEC 301, EC 302, EC 303, EC 310, EC 311, or polyetheramine commercially available from Huntsman under the trademarksuch as D-230, D-400, D-2000, D-4000, ED-600, ED-900, EDR-148, THF-100, T-403.

The carbodiimide used for preparing the guanidine compound may be obtained as a product of carbodiimidization reaction of one or more isocyanates. During the reaction, two isocyanate groups form a carbodiimide and release CO₂. The isocyanate may be a simple isocyanate such as a monoisocyanate (e.g., phenyl isocyanate) or a polyisocyanate (e.g., methylene diphenyl diisocyanate, toluene diisocyanate, hexamethylene diisocyanate) . Alternatively, the isocyanate may be an isocyanate-terminated prepolymer formed by reaction of a polyisocyanate and an active-hydrogen containing compound. Exemplary active-hydrogen containing compounds include without limitation to a bi-, tri-, or higher functional polyether polyol, polyester polyol, polycarbonate polyol, or polyetheramine.

Preferably, Q₁ and Q₂ are independently a bivalent radical represented by any of Formula (14) through Formula (20) :

- (CH₂) ₆- Formula (14) ,

Preferably, R₁ and R₂ are independently ethyl, isopropyl, n-butyl, cyclohexyl, benzyl, 2-ethoxyethyl, 2- (dimethylamino) ethyl, methoxy-terminated polyoxyethylene, or any combination thereof.

Preferably, n is no less than 1 and no more than 5, preferably n is no less than 1 and no more than 3.

The preparation of carbodiimide is well-known and taught in, for example, US 6,730,807 B1. The process often involves an isocyanate undergoing a carbodiimidization reaction and then being end capped by an end capping agent.

End capping agents are isocyanate-reactive compounds that are able to react with terminal isocyanate functionalities (for example, those within a carbodiimide) to form chemical bonding. Exemplary end capping agents include without limitation to primary amines, secondary amines, ureas, urethanes, isocyanate, thiocarbamates, alcohols, phenols, thiols, or thiophenols. The chemical bonding formed during end capping may be a bivalent linkage of urea, biuret, uretonimine, uretdione, substituted 2, 4-diamino-1, 3-diazetidine, allophanate, thioallophanate, urethane, or thiourethane.

End capping agent may comprise besides the isocyanate-reactive functionality and a monovalent radical that is inert to the isocyanate functionalities.

The end capping agent may be:

(A) . A compound consisting of an isocyanate-reactive functionality and an unsubstituted or substituted monovalent hydrocarbon radical.

The monovalent hydrocarbon radical may be an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, or aryl radical. The monovalent hydrocarbon radical may be linear or branched. The substitution may be one or more halogen atom, an alkoxy radical, a dialkylamino radical, an alkylthio radical, a nitro radical, a nitroso radical, a nitrile radical, or the like. Examples may be small molecular alcohols, amines, or thiols;

(B) . A compound consisting of an isocyanate-reactive functionality and a monovalent radical containing one or more oxygen, nitrogen, sulfur, phosphorus, or silicon atoms.

As a specific example, the end capping agent may be a poly (ethylene glycol) methyl ether, or as another specific example, the reaction product of a hydrosiloxane containing a Si-H bond with a monoalcohol or monoamine with a carbon-carbon double bond; or

(C) . A compound consisting of an isocyanate-reactive functionality and a monovalent radical containing one or more repeating units selected from ether, ester, thioether, amide, imide, siloxane, or any combination thereof.

For example, the compound may be a polyether monoalcohol or monoamine. The oligomeric/polymeric diol or diamine may be based on polyether, polyester, polythioether, polyamide, polyimide, polysiloxane, or other repeating units. Examples are monohydroxy terminated polypropylene, monohydroxy terminated polycaprolactone, monoamine terminated polyamide, or monohydroxy terminated polydimethylsiloxane.

Preferably, the end capping agent is a monoalcohol, a monoamine, a tertiary amino monoalcohol (for example, N, N-dimethylaminoethanol) , an alkoxy or aryloxy monoamine (for example, 3-methoxypropylamine) , a diol monoether (for example, ethylene glycol monomethyl ether) , a monohydroxy terminated polystyrene, a monohydroxy terminated polyether (for example, reaction product of ethylene oxide with a monoalcohol) , a monoamine terminated polyether (for example, monoamines commercially available as M series monoamines) , a monohydroxy terminated polyester (for example, ring opening polymerization product of caprolactone with a monoalcohol) , a monoamine terminated polyester (for example, ring opening polymerization product of caprolactone with a monoamine) , a monohydroxy terminated siloxane, or the like.

Specific examples of the end capping agent include without limitation to ethanol, isopropyl alcohol, n-butanol, 1-octanol, benzyl alcohol, 2-ethoxyethanol, 2- (dimethylamino) ethanol, methoxy polyethylene glycol, or any combination thereof. However, any skilled person may choose any other similar monofunctional isocyanate-reactive compound or any combination thereof as end capping agent.

Dyeable composition

According to the present disclosure, a dyeable composition includes:

a polymer selected from a polyester, a polyamide, and a polyurethane; and

the guanidine compound.

Preferably, the polymer is a polyurethane. The polyurethane may be a thermoplastic polyurethane, a crosslinked polyurethane, a polyurethane elastomer, or a polyurethane-urea.

Preferably, the polyurethane is a polyurethane-urea obtained as a reaction product of an isocyanate-terminated prepolymer and a diamine or polyamine.

Preferably, the isocyanate-terminated prepolymer is an adduct of a polyol and a polyisocyanate.

Preferably, the polyurethane is a thermoplastic polyurethane.

Preferably, the guanidine compound has a content of 0.1 wt. %to 12 wt. %, preferably 0.3 wt. %to 7 wt. %, more preferably 0.5 wt. %to 3.0 wt. %, relative to a weight of the polyurethane.

The dyeable composition preferably further includes a solvent, wherein the solvent comprises at least one of N, N-dimethylformamide, N, N-dimethylacetamide, tetrahydrofuran, dimethylsulfoxide, and N-methyl-2-pyrrolidone. The dyeable composition can be used in a dry spinning process to manufacture synthetic fibers.

According to the present disclosure, the guanidine compound may introduce into the dyeable composition anti-bacteria activity. The dyeable composition may show broad spectrum antibacterial activity towards various microorganisms including escherichia coli, staphylococcus aureus, and candida albicans.

Fabric

According to the present disclosure, a fabric is made from the dyeable composition.

The fabric may find applications in apparel, vehicle interiors, furniture. The fabric has a good dyeability that makes articles made of the fabric can has a good and lasting color.

The fabric provided in the present disclosure has a high antibacterial activity, which makes it suitable for healthcare or hygiene uses such as, medical underwear, surgery wear, medical uniforms, medical caps, face masks, towels, blankets, and gloves.

Examples

The following materials were used in the examples:

Dye enhancers:

CDE 001, from BASF, a toluene diisocyanate based carbodiimide with about 13.72wt%NCN content.

SAM, poly (N, N-diethyl-2-aminoethyl methacrylate) , commercially available as a 35 wt. %solution in N, N-dimethylacetamide from Penglai Spark Chemicals.

Raw materials for synthesis of polyurethane-urea:

Methylene diphenyl diisocyanate, from BASF;

Oligomeric polyol: 1800 with average molecular weight of 1, 800 g/mol from BASF;

Amine: n-hexylamine, ethylenediamine and diethyl amine, all from BASF;

Solvent: N, N-dimethylacetamide from BASF;

Auxiliaries:

Antioxidant: 245 from BASF;

UV absorber: 1130 from BASF; and

Yellow inhibitor: HN-150 from Tokyo Chemical Industry.

Preparation of guanidine

100 g of CDE 001 was reacted with 34.71 g of n-hexylamine under 50 ℃ for one hour and a product (denoted as GUA hereinafter) was obtained. The characteristic peak of carbodiimide was found to disappear in the infra-red testing.

A polyurethane-urea solution “dope” for preparation of films was made according to the following steps:

1) Reacting 100 g of polyether polyol1800 and 23.07 g of methylene diphenyl diisocyanate in a reactor in the presence of N₂ and forming an isocyanate-terminated prepolymer with an isocyanate content of 2.50 wt. %. Adding 150.41 g of N, N-dimethylacetamide as solvent into the prepolymer to form a prepolymer solution after the prepolymer was cooled to 40℃;

2) To the prepolymer solution, adding a solution of 2.08 g of ethylenediamine and 0.46 g of diethyl amine in 116.49 g of N, N-dimethylacetamide under high speed mixing. In the end, a homogeneous polyurethane-urea solution was obtained; and

3) To the polyurethane-urea solution, adding 1.25 g of antioxidant, 0.63 g of UV absorber, and 1.25 g of yellow inhibitor, then mixing the system thoroughly to form a dope. In the dope, the weight of the polyurethane-urea equaled to the total weight of polyether polyol1800, methylene diphenyl isocyanate, ethylenediamine, and diethyl amine.

Film preparation

Polyurethane-urea films were prepared by following steps. Firstly, mixing the dope and the dye enhancer together to form a mixture; then pouring the mixture into a precisely horizontally aligned glass plate to form a thin layer; placing the glass plate in an oven under 50℃ in a nitrogen atmosphere for 3 days to evaporate the solvent; finally, removing the film as obtained from the glass plate. The film had an average thickness of 40-60 μm. The dosage of a dye enhancer was calculated based on a weight of the polyurethane-urea to be dyed.

Dyeing process

Dyeing process was done in a Mathis Labomat beaker dyeing system. The polyurethane-urea film was put into a red dyeing bath and a blue dyeing bath (for red dye: 2 wt. %ofRed M-R01 acid dyestuff in 10 wt. %acetic acid buffer; for blue dye: 2 wt. %of fabric Nylanthrene Brill Blue C-DFS dyestuff from Yorkshire Chemicals Holdings Limited in 10 wt. %acetic acid buffer) under room temperature. The weight ratio of dyeing bath to the film was 10. The pH of dyeing bath was adjusted to 4-5. The dyeing bath with the film soaked inside was heated to 98℃ in a speed of 2℃/min. The dyeing bath was kept at 98℃ for 1 hour and then cooled to 60℃ in a speed of 3℃/min. Finally, the film was rinsed thoroughly and dried to obtain a dry film.

Washing process

The dyed film after rinsing were attached to a piece of multifiber. The combination was put into a soaping solution (5 g/L ISO soap according to the standard ISO 105-C10, 2 g/L Na₂CO₃, the rest being water) under room temperature. The washing system was heated to 60℃ and then kept at the temperature for 40 minutes. After that it was cooled to 40℃. Finally, the film was thoroughly rinsed and dried.

To evaluate color depth of dyed film before and after washing, K/S value at the wavelength of 520 nm was measured for each sample. K represents the color absorption coefficient. S represents the color scattering coefficient. The color depth values (K/S) were calculated using Kubelka-Munk theory (ISO 9416) . They indicate the color intensity at a specific wavelength λ compared to a blank sample. The blank sample was a respective fiber textile fabric not immersed in a dyeing bath. The higher the K/S value, the darker the color. A Datacolor SF600 colorimeter was used under a D65 light source and a 10° viewing angle. The measurement was repeated four times, and the average value was obtained. The difference between K/S values before and after washing was used to evaluate the wash colorfastness. The smaller the absolute value of the change of K/S value, the better the wash colorfastness of the film.

Color shade lightness "L" values of the dyed films before and after washing were tested using the same Datacolor SF600 colorimeter. Results were reported in CIELAB units under a D65 light source and a 10° viewing angle. This scale is based on the principles described in ASTM E 308 Standard Practice for Computing the Colors of Objects by Using the CIE System. The measurement was repeated four times, and the average value was obtained.

A lower "L" value indicates a deeper color. Usually the “L” value will decrease after washing. The difference between “L” values before and after washing was used to evaluate the wash colorfastness. The smaller the absolute value of the change of L value, the better the wash colorfastness of the film.

The polyurethane-urea films had their dyeing and mechanical performances tested in accordance with the standards listed in Table 1. The tensile test started measuring tensile modulus in the strain interval of 0.05 %to 0.25 %with a crosshead-speed of 1 mm/min. The cross-speed for the tensile test following was 200 mm/min. For hysteresis test, a polyurethane-urea film was consecutively stretched (load) and released (unload) up to 300 %strain for five times. Values of residual elongation of the film after the first and fifth cycles were measured and denoted by “E_res-1” and “E_res-5” , respectively.
Table 1 Testing standards for performances of the polyurethane-urea film

By using different dye enhancers and varying dosage of dye enhancers in the polyurethane-urea dyeable composition, a series of polyurethane-urea films PF1 through PF7 were made. For each of films PF1 through PF7, one sample was dyed by the red dyestuff. Additionally, for each of films PF1 through PF7, another sample was dyed by the blue dyestuff. The films dyed respectively by the red dyestuff and the blue dyestuff have their performances are shown in Table 2 and Table 3.
Table 2 Performances of the polyurethane-urea films dyed by red dyestuff

Table 3 Performances of the polyurethane-urea films dyed by blue dyestuff

From Tables 2 and 3, the guanidine, when used as a dye enhancer, was able to achieve a good color fastness and dyeability even at a very low dosage. The mechanical strengths were not impacted by usage of guanidine. To reach the same level of dyeability, the amount of guanidine was much lower than that of poly (N, N-diethyl-2-aminoethyl methacrylate) .

Claims

A guanidine compound being a product of:

an amine; and

a carbodiimide represented by

wherein,

n is an integer no less than 1;

Q₁ and Q₂ independently are bivalent hydrocarbon radicals or bivalent hydrocarbon radicals interrupted by one or more bivalent radicals represented by any of Formula (2) through Formula (7) :
——O—— Formula (2) ,

R₁ and R₂ independently are monovalent hydrocarbon radicals; and

X₁ and X₂ independently are bivalent radicals represented by any of Formula (5) through Formula (13) :

and

Q₃ through Q₈ are independently a monovalent organic radical selected from:

A) an unsubstituted or substituted monovalent hydrocarbon radical,

B) a monovalent radical containing one or more oxygen, nitrogen, sulfur, phosphorus, or silicon atoms, and

C) a monovalent radical containing one or more repeating units selected from ether, ester, thioether, amide, imide, siloxane, urethane, urea, allophanate, or any combination thereof.
The guanidine compound of claim 1, wherein the amine comprises a monoamine, a diamine, a triamine, a tetraamine, a polyetheramine, a linear polyethyleneimine, a branched polyethyleneimine, or an alkanolamine.
The guanidine compound of claim 2, wherein the amine is a primary or secondary monoamine represented by HN (R₃) R₄, and wherein at least one of R₃ and R₄ is a monovalent hydrocarbon radicals.
The guanidine compound of claim 3, wherein the amine is methylamine, ethylamine, n-propylamine, n-butylamine, n-hexylamine, dimethylamine, or diethylamine.
The guanidine compound of claim 1, wherein Q₁ and Q₂ are independently a bivalent radical represented by any of Formula (14) through Formula (20) :
- (CH₂) ₆- Formula (14) ,
The guanidine compound of claim 1, wherein R₁ and R₂ are independently ethyl, isopropyl, n-butyl, cyclohexyl, benzyl, 2-ethoxyethyl, 2- (dimethylamino) ethyl, methoxy-terminated polyoxyethylene, or any combination thereof.
The guanidine compound of claim 1, wherein n is no less than 1 and no more than 5, preferably n is no less than 1 and no more than 3.
A dyeable composition comprising:

a polymer selected from a polyester, a polyamide, and a polyurethane; and

a guanidine compound according to any of claims 1 through 7.
The dyeable composition of claim 8, wherein the polymer is a polyurethane.
The dyeable composition of claim 9, wherein the polyurethane is a polyurethane-urea obtained as a reaction product of an isocyanate-terminated prepolymer and a diamine or polyamine.
The dyeable composition of claim 10, wherein the isocyanate-terminated prepolymer is an adduct of a polyol and a polyisocyanate.
The dyeable composition of claim 9, wherein the polyurethane is a thermoplastic polyurethane.
The dyeable composition of claim 9, wherein the guanidine compound has a content of 0.1 wt. %to 12 wt. %, preferably 0.3 wt. %to 7 wt. %, more preferably 0.5 wt. %to 3.0 wt. %, relative to a weight of the polyurethane.
The dyeable composition of claim 8, further comprising a solvent, wherein the solvent comprises at least one of N, N-dimethylformamide, N, N-dimethylacetamide, tetrahydrofuran, dimethylsulfoxide, and N-methyl-2-pyrrolidone.
A fabric made from a dyeable composition of any of claims 8 through 14.