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WO2025218529A1 - Composition de polyuréthane pouvant être teinte et procédé associé - Google Patents

Composition de polyuréthane pouvant être teinte et procédé associé

Info

Publication number
WO2025218529A1
WO2025218529A1 PCT/CN2025/087729 CN2025087729W WO2025218529A1 WO 2025218529 A1 WO2025218529 A1 WO 2025218529A1 CN 2025087729 W CN2025087729 W CN 2025087729W WO 2025218529 A1 WO2025218529 A1 WO 2025218529A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyurethane
radical
formula
guanidine compound
independently
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/CN2025/087729
Other languages
English (en)
Inventor
Liang Zhao
Jia Yue HUANG
Feng Chao HU
Hai Sheng Wu
Dong Liang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF China Co Ltd
BASF SE
Original Assignee
BASF China Co Ltd
BASF SE
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF China Co Ltd, BASF SE filed Critical BASF China Co Ltd
Publication of WO2025218529A1 publication Critical patent/WO2025218529A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3225—Polyamines
    • C08G18/3228—Polyamines acyclic
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    • C08G18/02—Polymeric products of isocyanates or isothiocyanates of isocyanates or isothiocyanates only
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
    • C08G18/0809—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups
    • C08G18/0814—Manufacture of polymers containing ionic or ionogenic groups containing cationic or cationogenic groups containing ammonium groups or groups forming them
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    • C08G18/08—Processes
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0847—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers
    • C08G18/0852—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of solvents for the polymers the solvents being organic
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    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
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    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1858—Catalysts containing secondary or tertiary amines or salts thereof having carbon-to-nitrogen double bonds
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    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/285—Nitrogen containing compounds
    • C08G18/2865—Compounds having only one primary or secondary amino group; Ammonia
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    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
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    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups
    • C08G18/7671—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl groups containing only one alkylene bisphenyl group
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    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
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    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
    • C08G18/808—Monoamines
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    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/02—Polyureas
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/08—Polyurethanes from polyethers
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    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/02—Polyureas
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    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/08—Polyurethanes from polyethers
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    • C08G2150/00—Compositions for coatings

Definitions

  • 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.
  • guanidine compound being a product of:
  • n is an integer no less than 1;
  • Q 1 and Q 2 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) :
  • R 1 and R 2 independently are monovalent hydrocarbon radicals
  • X 1 and X 2 independently are bivalent radicals represented by any of Formula (5) through Formula (13) :
  • Q 3 through Q 8 are independently a monovalent organic radical selected from:
  • a dyeable composition comprising:
  • a polymer selected from a polyester, a polyamide, and a polyurethane
  • a fabric made from the dyeable composition.
  • 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 CO 2 . 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.
  • the simplest guanidine is HNC (NH 2 ) 2 .
  • 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 -CH 3 , ethyl -C 2 H 5 , n-propyl -CH 2 CH 2 CH 3 , and isopropyl -CH (CH 3 ) 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.
  • 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 ⁇ CH 2 (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
  • 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
  • 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 -C 6 H 5 and naphthalenyl -C 10 H 7 .
  • 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 (-CH 2 -) , ethylene radical (-CH 2 CH 2 -) , and hexamethylene radical (-CH 2 CH 2 CH 2 CH 2 CH 2 -) .
  • 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
  • alkenylene radical refers to a bivalent hydrocarbon radical derived from an alkene by removal of two hydrogen atoms from the same.
  • 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
  • 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
  • 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 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.
  • 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.
  • 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.
  • the temperature refers to room temperature and the pressure refers to ambient pressure.
  • guanidine compound which is a product of an amine
  • n is an integer no less than 1;
  • Q 1 and Q 2 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) :
  • R 1 and R 2 independently are monovalent hydrocarbon radicals
  • X 1 and X 2 independently are bivalent radicals represented by any of Formula (5) through Formula (13) :
  • Q 3 through Q 8 are independently a monovalent organic radical selected from:
  • 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 (- (OCH 2 CH 2 ) n -) , a polyoxypropylene radical (- (OCH (CH 3 ) CH 2 ) n -) , or a polyoxytetramethylene radical (- (OCH 2 CH 2 CH 2 CH 2 ) n -) .
  • 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 trademark such as D 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 trademark such as FG polyethyleneimine.
  • the alkanolamine may include ethanolamine and propanolamine.
  • the amine is a mixture of two or more kinds of amine compounds.
  • the amine is a primary or secondary monoamine represented by HN (R 3 ) R 4 , and wherein at least one of R 3 and R 4 is a monovalent hydrocarbon radicals.
  • the amine is methylamine, ethylamine, n-propylamine, n-butylamine, n-hexylamine, dimethylamine, or diethylamine.
  • 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 trademark such as EC 301, EC 302, EC 303, EC 310, EC 311, or polyetheramine commercially available from Huntsman under the trademark such 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 CO 2 .
  • 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) .
  • the isocyanate may be an isocyanate-terminated prepolymer formed by reaction of a polyisocyanate and an active-hydrogen containing compound.
  • active-hydrogen containing compounds include without limitation to a bi-, tri-, or higher functional polyether polyol, polyester polyol, polycarbonate polyol, or polyetheramine.
  • Q 1 and Q 2 are independently a bivalent radical represented by any of Formula (14) through Formula (20) :
  • R 1 and R 2 are independently ethyl, isopropyl, n-butyl, cyclohexyl, benzyl, 2-ethoxyethyl, 2- (dimethylamino) ethyl, methoxy-terminated polyoxyethylene, or any combination thereof.
  • n is no less than 1 and no more than 5, preferably n is no less than 1 and no more than 3.
  • 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;
  • a compound consisting of an isocyanate-reactive functionality and a monovalent radical containing one or more oxygen, nitrogen, sulfur, phosphorus, or silicon atoms.
  • 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.
  • 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.
  • 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.
  • a monoalcohol for example,
  • end capping agent examples 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.
  • any skilled person may choose any other similar monofunctional isocyanate-reactive compound or any combination thereof as end capping agent.
  • a dyeable composition includes:
  • a polymer selected from a polyester, a polyamide, and a polyurethane
  • the polymer is a polyurethane.
  • the polyurethane may be a thermoplastic polyurethane, a crosslinked polyurethane, a polyurethane elastomer, or a polyurethane-urea.
  • the polyurethane is a polyurethane-urea obtained as a reaction product of an isocyanate-terminated prepolymer and a diamine or polyamine.
  • the isocyanate-terminated prepolymer is an adduct of a polyol and a polyisocyanate.
  • the polyurethane is a thermoplastic polyurethane.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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;
  • Antioxidant 245 from BASF;
  • UV absorber 1130 from BASF.
  • a polyurethane-urea solution “dope” for preparation of films was made according to the following steps:
  • 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°C 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 ⁇ m.
  • the dosage of a dye enhancer was calculated based on a weight of the polyurethane-urea to be dyed.
  • 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. %of Red 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°C in a speed of 2°C/min.
  • the dyeing bath was kept at 98°C for 1 hour and then cooled to 60°C in a speed of 3°C/min.
  • the film was rinsed thoroughly and dried to obtain a dry film.
  • 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 Na 2 CO 3 , the rest being water) under room temperature.
  • the washing system was heated to 60°C and then kept at the temperature for 40 minutes. After that it was cooled to 40°C. Finally, the film was thoroughly rinsed and dried.
  • 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 ⁇ 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.
  • 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.
  • 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.
  • 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.
  • the amount of guanidine was much lower than that of poly (N, N-diethyl-2-aminoethyl methacrylate) .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne un composé guanidine qui est un produit d'une amine et d'un carbodiimide ; une composition pouvant être teinte comprenant un polymère choisi parmi un polyester, un polyamide et un polyuréthane ; ainsi que le composé guanidine et un tissu.
PCT/CN2025/087729 2024-04-15 2025-04-08 Composition de polyuréthane pouvant être teinte et procédé associé Pending WO2025218529A1 (fr)

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CN2024087758 2024-04-15
CNPCT/CN2024/087758 2024-04-15

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WO2025218529A1 true WO2025218529A1 (fr) 2025-10-23

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3627735A (en) * 1969-11-12 1971-12-14 Louis E Trapasso Polyurethane elastomeric-shaped articles containing reactive sites
US6730807B1 (en) 1999-11-11 2004-05-04 Basf Aktiengesellschaft Carbodiimides with carboxyl or carboxylate groups
CN109295526A (zh) 2018-10-09 2019-02-01 浙江华峰氨纶股份有限公司 一种含嵌段胍类聚合物的抗菌型聚氨酯弹性纤维制备方法
US20200048189A1 (en) * 2017-03-24 2020-02-13 Sika Technology Ag Guanidine catalyst for curable compositions
CN116376013A (zh) 2023-06-05 2023-07-04 四川省纺织科学研究院有限公司 一种胍盐改性超支化聚酰胺-胺复合固色聚合物的制备方法及应用

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3627735A (en) * 1969-11-12 1971-12-14 Louis E Trapasso Polyurethane elastomeric-shaped articles containing reactive sites
US6730807B1 (en) 1999-11-11 2004-05-04 Basf Aktiengesellschaft Carbodiimides with carboxyl or carboxylate groups
US20200048189A1 (en) * 2017-03-24 2020-02-13 Sika Technology Ag Guanidine catalyst for curable compositions
CN109295526A (zh) 2018-10-09 2019-02-01 浙江华峰氨纶股份有限公司 一种含嵌段胍类聚合物的抗菌型聚氨酯弹性纤维制备方法
CN116376013A (zh) 2023-06-05 2023-07-04 四川省纺织科学研究院有限公司 一种胍盐改性超支化聚酰胺-胺复合固色聚合物的制备方法及应用

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