WO2022203649A1 - Composition de revêtement textile - Google Patents

Composition de revêtement textile Download PDF

Info

Publication number
WO2022203649A1
WO2022203649A1 PCT/US2021/023460 US2021023460W WO2022203649A1 WO 2022203649 A1 WO2022203649 A1 WO 2022203649A1 US 2021023460 W US2021023460 W US 2021023460W WO 2022203649 A1 WO2022203649 A1 WO 2022203649A1
Authority
WO
WIPO (PCT)
Prior art keywords
coating composition
textile coating
textile
heterocyclic compound
active
Prior art date
Application number
PCT/US2021/023460
Other languages
English (en)
Inventor
Zhang-Lin Zhou
Xiaoqi Zhou
Original Assignee
Hewlett-Packard Development Company, L.P.
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 Hewlett-Packard Development Company, L.P. filed Critical Hewlett-Packard Development Company, L.P.
Priority to PCT/US2021/023460 priority Critical patent/WO2022203649A1/fr
Publication of WO2022203649A1 publication Critical patent/WO2022203649A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0823—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing carboxylate salt groups or groups forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
    • C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • 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
    • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
    • C08G18/0866—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being an aqueous medium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/3231—Hydrazine or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/3234—Polyamines cycloaliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/34—Carboxylic acids; Esters thereof with monohydroxyl compounds
    • C08G18/348—Hydroxycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
    • C08G18/3857—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur having nitrogen in addition to sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
    • C08G18/44—Polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6648—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6651—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3225 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3225 or polyamines of C08G18/38
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6659—Compounds of group C08G18/42 with compounds of group C08G18/34
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/757—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing at least two isocyanate or isothiocyanate groups linked to the cycloaliphatic ring by means of an aliphatic group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/282—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing phosphorus
    • D06M13/288—Phosphonic or phosphonous acids or derivatives thereof
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/35—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
    • D06P1/5285—Polyurethanes; Polyurea; Polyguanides
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/54—Substances with reactive groups together with crosslinking agents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
    • D06P1/56—Condensation products or precondensation products prepared with aldehydes
    • D06P1/58—Condensation products or precondensation products prepared with aldehydes together with other synthetic macromolecular substances
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/667—Organo-phosphorus compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/002—Locally enhancing dye affinity of a textile material by chemical means
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/22—Effecting variation of dye affinity on textile material by chemical means that react with the fibre
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
    • D06P5/30—Ink jet printing

Definitions

  • Textile printing methods often include rotary and/or flat-screen printing.
  • Traditional analog printing typically involves the creation of a plate or a screen, i.e. , an actual physical image from which ink is transferred to the textile.
  • Both rotary and flat screen printing have great volume throughput capacity, but also have limitations on the maximum image size that can be printed. For large images, pattern repeats are used.
  • digital inkjet printing enables greater flexibility in the printing process, where images of any desirable size can be printed immediately from an electronic image without pattern repeats.
  • Inkjet printers are gaining acceptance for digital textile printing.
  • Inkjet printing is a non-impact printing method that utilizes electronic signals to control and direct droplets or a stream of ink to be deposited on media.
  • FIG. 1 is a schematic illustration of a portion of a polyurethane polymer of the self-crossl inked polyurethane binder particles disclosed herein;
  • FIG. 2 illustrates an example of a chemical structure for the portion shown in Fig. 1;
  • Fig. 3 is a flow diagram depicting an example of a method for making an example of a textile coating composition
  • FIG. 4 is schematic cross-sectional view of an example of the coated textile.
  • Fig. 5 is a flow diagram depicting an example of a method for making coated textile.
  • Untreated textile fibers do not include an ink receiving layer and are not treated with pre-treatment fluids and/or fixer fluids that render them suitable for receiving a digital inkjet ink.
  • pre-treatment fluids and/or fixer fluids that render them suitable for receiving a digital inkjet ink.
  • digital inkjet inks printed on untreated textiles may lead to prints with poor image quality and/or durability.
  • a textile coating composition that can be used to generate an image receiving layer at the surface(s) of a fabric substrate.
  • This image receiving layer improves the fabric substrate’s ability to create a durable printed image with improved image quality.
  • the textile coating composition imparts flame retardancy to the fabric substrate without the incorporation of organic bromides or other harsh flame retardants.
  • the textile coating composition incorporates a sulfonated polyurethane (which is anionic) with a phosphate salt (which is cationic) into the same formulation without initiating gelling, viscosity increase, or dispersion crashing.
  • a sulfonated polyurethane which is anionic
  • a phosphate salt which is cationic
  • the textile coating composition is applied to a fabric substrate and is dried. Drying initiates the formation of a crosslinked polymer network including a crosslinked heterocyclic compound.
  • the crosslinked heterocyclic compound is the product of a reaction between or an interaction between a heterocycle (e.g., epoxide) of the heterocyclic compound and a crosslinking agent (e.g., amine groups) in the textile coating composition.
  • the heterocycle of the heterocyclic compound may also react with functional groups (e.g., sulfonate, etc.) of the sulfonated polyurethane to generate additional crosslinks.
  • This crosslinked polymer network improves the durability of the coated textile.
  • wt% active refers to the loading percentage of an active component, without taking into account the weight of an aqueous solvent (e.g., water), that may be present with the active component.
  • a aqueous solvent e.g., water
  • the wt% active refers to the dry weight.
  • the term “wt%,” without the term active, refers to the loading percentage (in the particular fluid) that accounts for all of the components in a fluid.
  • the textile coating composition disclosed herein includes a self-crosslinked polyurethane binder particle including a polyurethane polymer with a polymerized sulfonated diamine; a heterocyclic compound that includes at least one ring with at least 3 members; a crosslinking agent to react or interact with the heterocyclic compound; a phosphate salt; and an aqueous vehicle.
  • the textile coating composition consists of these components.
  • the textile coating composition may include additives, such as a filler, a surfactant, and combinations thereof.
  • the textile coating composition includes a self-crosslinked polyurethane binder particle, which includes a polyurethane polymer with a polymerized sulfonated diamine.
  • Fig. 1 depicts a portion of the polyurethane polymer 10 that can be present as part of the polyurethane particles described herein. Fig. 1 does not show crosslinking, but rather shows the types of groups or moieties that can be present along the polyurethane polymer 10, some of which are available for internal crosslinking.
  • the polyurethane polymer structure 10 in Fig. 1 includes several chemical moieties, such as urethane linkage groups 12 (formed by the reaction of isocyanate groups 14 with any of a number of polymeric diols 16 that may be present).
  • a carbon atom of an isocyanate group 14 reacts with an oxygen atom of a hydroxyl of the polymeric diol 16 to form the urethane linkage group 12.
  • the polymeric diol 16 and the isocyanate groups 14 are shown schematically after polymerization.
  • the isocyanate groups 14 are shown along the polyurethane backbone, and are schematically represented by a circle with isocyanate groups on either side thereof.
  • urea group 18 formed by the reaction of isocyanate groups 14 with any of a number of diamines that may be present
  • a non-ionic diamine 20 formed by the reaction of isocyanate groups 14 with any of a number of diamines that may be present
  • a non-ionic diamine 20 formed by the reaction of isocyanate groups 14 with any of a number of diamines that may be present
  • a non-ionic diamine 20 and sulfonated diamine 22 are present along the polymer backbone, and the sulfonate group of the sulfonated diamine 22 is included in a side chain (e.g., -(CH2) X S03H) off the polymer backbone and/or as an end group.
  • a side chain e.g., -(CH2) X S03H
  • the polyurethane polymer structure 10 shown in Fig. 1 is not intended to depict a specific polymer, but rather show an example of the sulfonated side chain and the polyurethane backbone. It is contemplated that the polyurethane polymer structure 10 may include additional polymerized isocyanates 14, polymerized polymeric diols 16, polymerized non-ionic diamines 20, polymerized sulfonated diamine 22, urethane linkage groups 12, urea linkage groups 18, etc. Additionally, the diamines 20, 22 may be in different positions along the polymer backbone depending on the respective reactions with the isocyanates.
  • Fig. 2 depicts a portion of an example polyurethane polymer 10 formed with isophorone diisocyanate, polyester polyol, tetramethylethylenediamine (non-ionic diamine), and amine functionalized sulfonic acid (e.g., A-95 from Evonik Industries).
  • polymerized polymeric diols polymerized isocyanates
  • polymerized non-ionic diamines polymerized sulfonated diamines
  • the self-cross-linked polyurethane binder particles may be synthesized by reacting the diisocyanate with the polymeric diol in the presence of a catalyst in a solvent under reflux to create a pre-polymer; and reacting the pre-polymer with the non-ionic diamine and the sulfonated diamine.
  • the resulting polyurethane polymer 10 consists of the polymerized sulfonated diamine, the polymerized diisocyanate, the polymerized polymeric diol, and the polymerized non ionic diamine.
  • the resulting polyurethane polymer 10 consists of the polymerized sulfonated diamine, the polymerized diisocyanate, and the polymerized polymeric diol.
  • making the self-crossl inked polyurethane binder particles involves first reacting the diisocyanate with the polymeric diol. This reaction may occur in the presence of a catalyst (e.g., dibutyl tin dilaurate, bismuth octanoate, and 1 ,4-diazabicyclo[2.2.2]octane) and in an organic solvent (e.g., methyl ethyl ketone (MEK), tetrahydrofuran (THF), ethyl acetate, acetone, or combinations thereof) under reflux. This reaction forms a pre-polymer having urethane linkages. The pre-polymer is dissolved in the organic solvent.
  • a catalyst e.g., dibutyl tin dilaurate, bismuth octanoate, and 1 ,4-diazabicyclo[2.2.2]octane
  • organic solvent e.g., methyl
  • Some example diisocyanates include hexamethylene-1 ,6-diisocyanate (HDI), 2,2,4-trimethyl-hexamethylene-diisocyanate (TDMI), 1 ,12-dodecane diisocyanate, 2,4,4-trimethyl-hexamethylene diisocyanate, 2-methyl-1 ,5- pentamethylene diisocyanate, isophorone diisocyanate (IPDI), methylene diphenyl diisocyanate (MDI), 1 -lsocyanato-4-[(4-isocyanatocyclohexyl)methyl]cyclohexan (H12MDI, i.e., 4,4’-Methylenedicyclohexyl diisocyanate), and combinations thereof).
  • HDI hexamethylene-1 ,6-diisocyanate
  • TDMI 2,2,4-trimethyl-hexamethylene-diisocyanate
  • IPDI isophorone diiso
  • Suitable polymeric diols include a polyester diol, a polycarbonate diol, a polyether diol, or combinations thereof.
  • An example of a suitable commercially available polyester diol is STEPANPOL® PC-1015-55 (a solvent-free saturated polyester resin available from Stepan Co.).
  • An example of a suitable commercially available polycarbonate polyol is ETERNACOLL® UH200 (a solvent-free solid aliphatic polycarbonate diol from UBE Industries, Ltd.).
  • the diisocyanate is used in excess so that additional NCO groups are available for subsequent cross-linking.
  • the pre-polymer is then cross-linked.
  • Cross-linking may be accomplished by adding water and the diamines to the pre-polymer solution.
  • diamines that can be used in forming the polyurethane polymer and particles as described herein
  • polymerized sulfonated-diamines as well as non-ionic diamines can be used.
  • Polymerized sulfonated-diamines can be prepared from diamines by adding sulfonate groups thereto.
  • Non-ionic diamines can be diamines that include aliphatic groups that are not charged, such as alkyl groups, alicyclic groups, etc.
  • Example diamines can include various dihydrazides, alkyldihydrazides, sebacic dihydrazides, alkyldioic dihydrazides, aryl dihydrazides, e.g., terephthalic dihydrazide, organic acid dihydrazide, e.g., succinic dihydrazides, adipic acid dihydrazides, etc, oxalyl dihydrazides, azelaic dihydrazides, carbohydrazide, etc.
  • Example diamine structures are shown below. More specific examples of diamines include 4,4’-methylenebis(2-methylcyclohexyl-amine) (DMDC), 4-methyl-1 ,3’- cyclohexanediamine (HTDA), 4,4’-Methylenebis(cyclohexylamine) (PACM), isphorone diamine (IPDA), tetramethylethylenediamine (TMDA), ethylene diamine (DEA), 1,4- cyclohexane diamine, 1,6-hexane diamine, hydrazine, adipic acid dihydrazide (AAD), carbohydrazide (CHD), and/or diethylene triamine (DETA), notably, DETA includes three amines, and thus, is a triamine.
  • DMDC 4,4’-methylenebis(2-methylcyclohexyl-amine)
  • HTDA 4-methyl-1 ,3’- cyclohexanediamine
  • PAM 4,4’-Methylenebis(cyclohexy
  • diamine since it also includes 2 amines, it is considered to fall within the definition herein of “diamine,” meaning it includes two amines. Many of the diamine structures shown below can be used as the non-ionic diamine, such as the uncharged aliphatic diamines shown below.
  • alkyl diamines other than 1 ,6-hexane diamine
  • alkyl diamines other than 1 ,6-hexane diamine
  • sulfonated diamine is an alkylamine-alkylamine-sulfonate (shown as a sulfonic acid in Formula I below, but as a sulfonate, would include a positive counterion associated with an SC group). While one example is shown in Formula I below, it is to be understood that other diamines may be used to generate a sulfonated diamine, including those based on structures shown above.
  • the sulfonated diamine provides the polyurethane polymer with a polar stabilizing functional group, which is able to couple with polar aqueous groups (e.g., water) to form a stable dispersion that does not precipitate out, even in the presence of the phosphate salt.
  • the polyurethane polymer is formed with the sulfonated diamine and without the non-ionic diamine.
  • any solvent is then removed, e.g., by vacuum distillation to afford the final polyurethane dispersion (i.e. , self-cross-linked polyurethane binder particles (with a polymerized sulfonated diamine) dispersed in water). More specifically, the polyurethane solution may be slowly added to water including a base with vigorous agitation, or vice versa. The mixture may be stirred and the organic solvent may be removed by distillation to form the polyurethane binder particles in dispersion.
  • the polyurethane polymer 10 has an acid number of less than 30 and a weight average molecular weight ranging from about 10,000 to about 1,000,000.
  • the acid number of the polyurethane polymer 10 is 30 mg KOH/g solid resin or less, or 10 mg KOH/g solid resin or less.
  • the self polyurethane polymer 10 may have an acid number ranging from greater than 0 mg KOH/g to 30 mg KOH/g, or from greater than 0 mg KOH/g to about 20 mg KOH/g, or from greater than 0 mg KOH/g to about 19 mg KOH/g, or from greater than 0 mg KOH/g to about 15 mg KOH/g, or from greater than 0 mg KOH/g to about 10 mg KOH/g, etc.
  • the term “acid number” refers to the mass of potassium hydroxide (KOH) in milligrams that is used to neutralize one (1) gram of a particular substance (e.g., the polyurethane polymer 10).
  • the test for determining the acid number of a particular substance may vary, depending on the substance.
  • a known amount of a sample of the polyurethane polymer 10 e.g., in the form of the binder particles
  • the aqueous dispersion may be titrated with a polyelectrolyte titrant of a known concentration.
  • a current detector for colloidal charge measurement may be used.
  • the current detector measures colloidal substances in an aqueous sample by detecting the streaming potential as the sample is titrated with the polyelectrolyte titrant to the point of zero charge.
  • An example of a suitable polyelectrolyte titrant is poly(diallyldimethylammonium chloride) (i.e., PolyDADMAC). It is to be understood that any suitable test for a particular component may be used.
  • the average particle size (volume-weighted mean diameter) of the self- cross-linked polyurethane binder particles may range from about 20 nm to about 500 nm. In one example, this range refers to the D50 particle size of a particle distribution. In an example, the self-cross-linked polyurethane binder particles may have a D50 particle size ranging from about 50 nm to about 200 nm.
  • the self-cross-linked polyurethane binder particles may be incorporated into the textile coating composition as a polyurethane dispersion, and any liquid components of the dispersion become part of the composition’s aqueous vehicle.
  • the polyurethane dispersion is added in a suitable amount so that the desired solids content of self-cross-linked polyurethane binder particles is achieved in the textile coating composition.
  • the self-cross-linked polyurethane binder particles (which does not account for other dispersion components) are present in an amount ranging from about 1 wt% active to about 40 wt% active, based on a total dry weight of the textile coating composition.
  • the self-cross-linked polyurethane binder particles are present in an amount ranging from about 2 wt% active to about 30 wt% active, or from about 10 wt% active to about 25 wt% active, or from about 20 wt% active to about 35 wt% active, based on the total dry weight of the textile coating composition.
  • the textile coating composition that is applied to the fabric substrate may be further diluted to form the final textile coating composition, which has a total solids content ranging from about 1% to about 10%.
  • the self-cross-linked polyurethane binder particles may be formed from any of the example isocyanates, polyols, diamines, and sulfonated diamines set forth herein.
  • Table A illustrates some examples of the components used to make different examples of the sulfonated polyurethane.
  • IPDA Isophorone diisocyanate
  • TMDI trimethylhexamethylene diisocyanate
  • H6XDI 1,4- bis(isocyanatomethyl)cyclohexane
  • PCP polycarbonate polyol
  • PEP polyester polyol
  • DMPA 2,2-bis(hydroxymethyl)propionic acid
  • IPDA isophorone diamine
  • AAD adipic acid dihydrazide
  • PACM 4,4-methylenebis(cyclohexylamine)
  • TMDA 2, 4, 4-trimethylhexane-1 ,6-diamine
  • SAAS sodium aminoalklysulphonate.
  • Table A Components of Sulfonated Polyurethane Dispersion Examples [0040] Table B illustrates some example properties of the sulfonated polyurethanes described in Table A.
  • the textile coating composition further includes a heterocyclic compound that includes at least one ring including at least 3 members (i.e. , atoms) and a crosslinking agent to react or interact with the heterocyclic compound.
  • heterocyclic compound includes at least one ring (with 3 or more members) as a functional group, where at least one of the atoms in the ring is oxygen.
  • the 3 or more membered ring (or heterocycle) is a functional group of a larger macromolecule.
  • the heterocycle may be a glycidyl ether functional group.
  • the heterocyclic compound is selected from the group consisting of a glycidyl ether of a novolac resin, a glycidyl ether of an aromatic compound, a glycidyl ether of an aliphatic polyol, a glycidyl amine, a glycidyl triazine, a silicone glycidyl resin, a glycidyl (meth)acrylate resin, and a glycidyl fluorine resin.
  • glycidyl ether of an aliphatic polyol examples include ethylene glycol diglycidyl ether, neopentyl glycol diglycidyl ether, 1 ,6-hexanediol diglycidyl ether, glycerol diglycidyl ether, pentaerythritol diglycidyl ether, diglycerol diglycidyl ether, sorbitol diglycidyl ether, polyethylene glycol diglycidyl ether, glycerol triglycidyl ether, trimethylolpropane triglycidyl ether, diglycerol triglycidyl ether, polyglycerol triglycidyl ether, sorbitol triglycidyl ether, and combinations thereof.
  • glycidyl ether of an aromatic compound examples include resorcinol diglycidyl ether, diglycidyl terephthalate, diglycidyl o-phthalate, tetraphenylolethane glycidyl ether, diglycidyl ether of bisphenol A (i.e. , bisphenol A diglycidyl ether), and combinations thereof.
  • glycidyl (meth)acrylate resins include poly(glycidyl methacrylate), poly(ethylene-co-glycidyl methacrylate), poly(tert-butyl methacrylate-co- glycidyl methacrylate), poly(pentabromobenzyl methacrylate-co-glycidyl methacrylate, and combinations thereof.
  • Some examples of a commercially available heterocycle are EPI-REZTM Resin WD-510, EPI-REZTM Resin WD-512, EPI-REZTM Resin 3510-W-60, EPI-REZTM Resin 7510-W-60, EPI-REZTM Resin 3540-WY-55, EPI-REZTM Resin 3522-W-60, all from HEXION Inc.
  • Other examples of a commercially available heterocycle are Q- RITTM 1051, Q-RITTM 1061, Q-RITTM 1075; Q-RITTM 1072, all from QR Polymers.
  • Still other examples of a commercially available heterocycle include D.E.R.TM 913,
  • D.E.R.TM 915 and D.E.R.TM 900 all from Olin Corporation.
  • the heterocycle is ANCAREZTM AR555 (a waterborne epoxy resin available from Evonik Industries).
  • the crosslinking agent included in the textile coating composition is capable of reacting with or interacting with the ring of the heterocyclic compound.
  • the reaction or interaction that takes place will depend upon the crosslinking agent that is used, as well as the at least 3 membered ring present on the heterocyclic compound.
  • the crosslinking agent includes at least one functional group that reacts with the at least 3 membered ring to form a crosslinked polymer.
  • Amines, acids, acid anhydrides, phenols, alcohols, and thiols are examples of functional groups that may crosslink with the at least 3 membered ring(s) of the heterocyclic compound.
  • the crosslinking agent is a catalyst that initiates self-crosslinking of the at least 3 membered ring(s) of the heterocyclic compound.
  • the crosslinking agent acts as catalyst to initiate opening of the ring of the heterocyclic compound, and then react with other opened rings, thus self-crosslinking.
  • the crosslinking agent is selected from the group consisting of an aliphatic amine, a cycloaliphatic amine, an amine adduct, polyamines, polyfunctional acids, polyfunctional acid anhydrides, polyfunctional phenols, polyfunctional alcohols, an imidazole, polyfunctional thiols, and combinations thereof.
  • aliphatic amines are dipropenediamine polyethylene amines, such as ethylene diamine, diethylene triamine, triethylene tetramine, and tetraethylene pentamine.
  • Some specific examples are 1 ,2-propylene diamine, 1 ,3- propylene diamine, 1 ,4-butane diamine, 1 ,5-pentane diamine, 1 ,3-pentane diamine, 1,6-hexane diamine, 3,3,5-trimethyl-1 ,6-hexanediamine, 3, 5, 5-trimethyl-1 , 6-hexane diamine, and 2-methyl-1 ,5-pentane diamine.
  • Other examples of aliphatic amines include bis-(3-aminopropyl)-amine and N,N'-bis-(3-aminopropyl)-1 ,2-ethane diamine.
  • cycloaliphatic amines are cyclohexane-based. Some cyclohexane-based examples include 1 ,2-diaminocyclohexane, 1,3- diaminocyclohexane, and 1 ,4-diaminocyclohexane. Some examples of other cycloaliphatic amines are aminoethyl piperazines, such as N-aminoethylpiperazine. Still other examples of cycloaliphatic amines include isophorone diamine and methane diamine of alicyclic polyamine.
  • amine adduct refers to a compound formed by the partial reaction of a multi-functional amine with an epoxide resin, an alkyl monoepoxide, an alkyl diepoxide, an ethylene oxide, a propylene oxide, an acrylonitritrile, or an aldehyde.
  • amine adducts include the partial reaction of a multi-functional amine with an epoxy resin and polyethylene polyamine.
  • Other amine adducts include poly(alkylene oxide)diamines and triamines or other alkylene oxide polymers with amine functional groups.
  • polyfunctional acid anhydrides include succinic anhydride, itaconic anhydride, maleic anhydride, tricarballylic anhydride, a copolymer of maleic anhydride and styrene, and a copolymer of maleic anhydride and a vinyl ether of a polyfunctional acid anhydride.
  • polyfunctional acids include saturated acids such as sebacic acid, azelaic acid, suberic acid, pimelic acid, or unsaturated acids and their adducts such as aconitic caid, maleic acid, and acrylic acid of polyfunctional acids.
  • polyfunctional phenols include novolac phenol resin and resol phenol formaldehyde.
  • polyfunctional alcohols include hydroquinone, 2,2-bis-(4- hydroxyphenyl)-propane (bisphenol A), isomer mixtures of dihydroxydiphenyl methane (bisphenol F), tetrabromobisphenol A, 4,4'-dihydroxydiphenyl cyclohexane, 4,4'- dihydroxy-3,3-dimethyldiphenyl propane, 4,4'-dihydroxydiphenyl, 4,4'- dihydroxybenzophenol, bis-(4-hydroxyphenyl)-1 , 1 -ethane, bis-(4-hydroxyphenyl)-1 , 1 - isobutane, bis-(4-hydroxyphenyl)-methane, bis-(4-hydroxyphenyl)-ether, bis-(4- hydroxyphenyl)-sulfone, and trimethylolpropane tris(3-mercaptopropionate).
  • bisphenol A 2,2-bis-(4- hydroxyphenyl)-propane
  • An example of an imidazole is 1-methylimidazole, 2-phenylimidazole and 2- ethyl-4-methylimidazole.
  • An example of a commercially available crosslinking agent is ANQUAWHITETM 100 (a polyamine curing agent available from Evonik Industries).
  • Other examples may include EPOTUF® 37-685 (an amine-functional epoxy curing agent from Reichhold), or NX-8501 (a water dispersed curing agent from Cardolite).
  • Still other examples may include EPIKURETM Curing Agent 8530-W-75 (a water soluble polyamine adduct in water), EPIKURETM Curing Agent 6870-W-53 (a modified polyamide adduct dispersion), EPIKURETM Curing Agent 8535-W-50 (a modified polyamidoamine adduct solution), available from FIEXION.
  • Each of the heterocyclic compound and the crosslinking agent may be incorporated into the textile coating composition as respective dispersions, and any liquid components of these dispersions become part of the composition’s aqueous vehicle.
  • the heterocyclic compound dispersion is added in a suitable amount so that the desired solids content of the heterocyclic compound is achieved.
  • the crosslinking agent dispersion is added in a suitable amount so that the crosslinking agent is present in a desired active amount.
  • the heterocyclic compound is present in an amount ranging from about 1 wt% active to about 15 wt% active based on a total dry weight of the textile coating composition; and the crosslinking agent is present in an amount ranging from about 1 wt% active to about 10 wt% active based on the total dry weight of the textile coating composition.
  • the heterocyclic compound is present in an amount ranging from about 5 wt% active to 9 wt% active based on a total dry weight of the textile coating composition; and the crosslinking agent is present in an amount ranging from about wt% active to 9 wt% active based on a total dry weight of the textile coating composition.
  • the ratio of the heterocyclic compound to the crosslinking agent is 1:1.
  • the textile coating composition further includes a phosphate salt.
  • the phosphate salts may improve the flame retardant property of the textile coating composition (and the image receiving layer(s) formed therefrom), without deleteriously interacting with the polyurethane binder within the composition.
  • the phosphate salt is a water soluble phosphate salt.
  • the phosphate salt is a metallic inorganic salt.
  • the phosphate salt is a metallic inorganic salt, it may be any of the structures shown below.
  • M represents a metal ion.
  • M may be any metal ion that completes the valence of the inorganic salt.
  • the phosphate salt may be sodium phosphates, such as sec-sodium phosphate (i.e. , sodium phosphate dibasic, disodium phosphate, disodium hydrogen phosphate, or sodium hydrogenphosphate), sodium orthophosphate (i.e., trisodium phosphate), sodium phosphate monobasic monohydrate (i.e., monosodium phosphate or sodium dihydrogen phosphate monohydrate), sodium phosphate dibasic heptahydrate (i.e., disodium hydrogen phosphate heptahydrate), sodium phosphate monobasic (i.e., monosodium dihydrogen orthophosphate or sodium dihydrogen phosphate), sodium phosphate dibasic dehydrate (i.e., disodium hydrogen phosphate dehydrate or di-sodium hydrogen phosphate dehydrate), sodium phosphate dibasic dodecahydrate (i.e., disodium hydrogen phosphate dodecahydrate), sodium phosphate monobasic dihydrate
  • trisodium phosphate dodecahydrate or sodium phosphate dodecahydrate trisodium phosphate dodecahydrate or sodium phosphate dodecahydrate
  • disodium hydrogen phosphate anhydrous disodium hydrogen phosphate dehydrate (i.e., sodium monohydrogen phosphate or, sodium phosphate dibasic dehydrate), or sodium biphosphate.
  • the phosphate salt may be potassium phosphates, such as dipotassium hydrogen phosphate (i.e., dipotassium phosphate, potassium hydrogenphosphate, sec-potassium phosphate, potassium phosphate dibasic, dipotassium hydrogen phosphate anhydrous, potassium monohydrogen phosphate), potassium orthophosphate, tripotassium phosphate (i.e., potassium phosphate tribasic), potassium phosphate monobasic (i.e., monopotassium phosphate), potassium phosphate monobasic monohydrate (i.e., potassium dihydrogen phosphate monohydrate, potassium dihydrogen phosphate), potassium phosphate dibasic heptahydrate (i.e., dipotassium hydrogen phosphate heptahydrate), monopotassium dihydrogen orthophosphate, potassium phosphate dibasic dihydrate (i.e., dipotassium hydrogen phosphate dihydrate or potassium dihydrogen phosphate dihydrate), potassium phosphate dibasic dode
  • Additional examples also include dilithium hydrogen phosphate (i.e., dilithium phosphate, lithium phosphate monobasic, or lithium hydrogenphosphate), lithium carbamoylphosphate dibasic hydrate, trilithium phosphate, lithium dihydrogen phosphate (i.e., lithium phosphate monobasic or monolithium phosphate), or the like.
  • dilithium hydrogen phosphate i.e., dilithium phosphate, lithium phosphate monobasic, or lithium hydrogenphosphate
  • lithium carbamoylphosphate dibasic hydrate trilithium phosphate
  • lithium dihydrogen phosphate i.e., lithium phosphate monobasic or monolithium phosphate
  • Additional examples also include ammonium dihydrogen phosphate (i.e., ammonium phosphate monobasic, monoammonium phosphate or ammonium dihydrogen phosphate), ammonium phosphate dibasic (i.e., ammonium hydrogen phosphate or diammonium hydrogen phosphate, sec-ammonium phosphate), diammonium phosphate, ammonium orthophosphate, monoammonium dihydrogen orthophosphate, triammonium phosphate, triammonium phosphate trihydrate, sodium ammonium hydrogen phosphate tetrahydrate, diammonium hydrogen phosphate dihydrate, ammonium biphosphate, and the like.
  • ammonium dihydrogen phosphate i.e., ammonium phosphate monobasic, monoammonium phosphate or ammonium dihydrogen phosphate
  • ammonium phosphate dibasic i.e., ammonium hydrogen phosphate or diammonium hydrogen phosphate, sec-ammonium phosphate
  • phosphate salts include salts of hydroxyethylidene diphosphonic acid, i.e. etidronate, shown below: where the cation is any that completes the valence of the inorganic salt (e.g., NH 4 + , K + , Li + , Na + , etc.).
  • phosphate salts include salts of nitrilotris(methylene)triphosphonic acid, shown below: where the cation is any that completes the valence of the inorganic salt (e.g., NH 4 + , K + , Li + , Na + , etc.).
  • phosphate salts include salts of 2- Phosphonobutane-1 ,2,4-tricarboxylic acid, shown below: where the cation is any that completes the valence of the inorganic salt (e.g., NH 4 + , K + , Li + , Na + , etc.).
  • the phosphate salt include salts of N,N,N',N'- ethylenediaminetetrakis(methylenephosphonic acid), also shown below: where the cation is any that completes the valence of the inorganic salt (e.g., NH 4 + , K + , Li + , Na + , etc.).
  • the phosphate salt may be incorporated into the textile coating composition as a solution, and any liquid components of the solution becomes part of the composition’s aqueous vehicle.
  • the phosphate salt is present in an amount ranging from about 1 wt% active to about 10 wt% active, based on a total dry weight of the textile coating composition.
  • the textile coating composition may also include additives, such as a filler, a surfactant, and combinations thereof.
  • a filler may be included to improve the ink receiving performance and physical properties, such as the opacity of the image receiving layer that is formed with the textile coating composition.
  • suitable fillers include titanium dioxide (T1O2), precipitated calcium carbonate, ground calcium carbonate, calcium magnesium carbonate, talc, clay (e.g., calcined clay, kaolin clay, or other phyllosilicates), calcium sulfate, alumina (AI2O3), aluminum hydroxide (AIOH 3 ), or combinations thereof.
  • An example of a suitable filler combination is calcium carbonate (precipitated, ground, or combinations thereof) with titanium dioxide.
  • An example of a commercially available filler is SPACERITE® s-3 (fine crystalline, aluminum trihydroxide with uniform particles averaging about one micron in diameter, available from J.M. Huber Corporation).
  • the filler is present in an amount ranging from about 15 wt% active to about 70 wt% active, based on a total dry weight of the textile coating composition. In an example, the filler is present in an amount of about 25 wt% active, based on the total dry weight of the textile coating composition. In another example, the filler is present in an amount of about 50 wt% active.
  • a surfactant may be included to improve the dispersability of the solids in the textile coating composition.
  • the surfactant may be any non-ionic, anionic, or cationic surfactant.
  • non-ionic surfactant may include polyoxyethylene alkyl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyglycerin fatty acid ester, polyoxyethylene alkylamine, polyoxyethylene fatty acid amide, alkylalkanolamide, polyethylene glycol polypropylene glycol block copolymer, acetylene glycol, and a polyoxyethylene adduct of acetylene glycol.
  • non-ionic surfactant may include polyoxyethylenenonyl phenylether, polyoxyethyleneoctyl phenylether, and polyoxyethylenedodecyl.
  • Further examples of the non-ionic surfactant may include silicon surfactants such as a polysiloxane oxyethylene adduct; fluorine surfactants such as perfluoroalkylcarboxylate, perfluoroalkyl sulfonate, and oxyethyleneperfluoro alkylether; and biosurfactants such as spiculisporic acid, rhamnolipid, and lysolecithin.
  • non-ionic surfactants include a silicone-free alkoxylated alcohol surfactant such as, for example, TEGO® Wet 510 (Evonik Industries) and/or a self-emulsifiable wetting agent based on acetylenic diol chemistry, such as, for example, SURFYNOL® SE-F (Evonik Industries)).
  • a silicone-free alkoxylated alcohol surfactant such as, for example, TEGO® Wet 510 (Evonik Industries) and/or a self-emulsifiable wetting agent based on acetylenic diol chemistry, such as, for example, SURFYNOL® SE-F (Evonik Industries)
  • non-ionic surfactants include SURFYNOL® 465 (ethoxylatedacetylenic diol), SURFYNOL® 440 (an ethoxylated low-foam wetting agent) SURFYNOL® CT-211 (now CARBOWET® GA-211 , non-ionic, alkylphenylethoxylate and solvent free), and SURFYNOL® 104 (non-ionic wetting agent based on acetylenic diol chemistry), (all of which are from Evonik Industries); ZONYL® FSO (a.k.a.
  • CAPSTONE® which is a water-soluble, ethoxylated non-ionic fluorosurfactant from E.l. DuPont de Nemours and Company
  • TERGITOL® TMN-3 and TERGITOL® TMN-6 both of which are branched secondary alcohol ethoxylate, non-ionic surfactants
  • TERGITOL® 15-S-3, TERGITOL® 15-S-5, and TERGITOL® 15-S-7 each of which is a secondary alcohol ethoxylate, non-ionic surfactant
  • BYK® 345, BYK® 346, BYK® 347, BYK® 348, BYK® 349 each of which is a silicone surfactant
  • Examples of the cationic surfactant include quaternary ammonium salts, such as benzalkonium chloride, benzethonium chloride, methylbenzethonium chloride, cetalkonium chloride, cetylpyridinium chloride, cetrimonium, cetrimide, dofanium chloride, tetraethylammonium bromide, didecyldimethylammonium chloride, domiphen bromide, alkylbenzyldimethylammonium chlorides, distearyldimethylammonium chloride, diethyl ester dimethyl ammonium chloride, dipalm itoylethyl hydroxyethylmonium methosulfate, and ACCOSOFT® 808 (methyl (1) tallow amidoethyl (2) tallow imidazolinium methyl sulfate available from Stepan Company).
  • Other examples of the cationic surfactant include amine oxides, such as lauryldimethyl
  • anionic surfactant may include alkylbenzene sulfonate, alkylphenyl sulfonate, alkylnaphthalene sulfonate, higher fatty acid salt, sulfate ester salt of higher fatty acid ester, sulfonate of higher fatty acid ester, sulfate ester salt and sulfonate of higher alcohol ether, higher alkyl sulfosuccinate, polyoxyethylene alkylether carboxylate, polyoxyethylene alkylether sulfate, alkyl phosphate, and polyoxyethylene alkyl ether phosphate.
  • anionic surfactant may include dodecylbenzenesulfonate, isopropylnaphthalenesulfonate, monobutylphenylphenol monosulfonate, monobutylbiphenyl sulfonate, monobutylbiphenylsul fonate, and dibutylphenylphenol disulfonate.
  • the surfactant is present in an amount ranging from about 0.1 wt% active to about 3 wt% active, based on a total dry weight of the textile coating composition. In an example, the surfactant is present in an amount of about 0.5 wt% active, based on the total dry weight of the textile coating composition. In another example, the surfactant is present in an amount of about 1.5 wt% actve, based on the total dry weight of the textile coating composition.
  • the textile coating composition further includes an aqueous vehicle.
  • the water may be purified water or deionized water. The amount of water will depend on the desired solids content for the textile coating composition. In an example, the total solids content in the textile coating composition ranges from about 1% to about 10% of the total composition.
  • the method 100 for making the textile coating composition includes generating an aqueous dispersion with a self-crossl inked polyurethane binder particle including a polyurethane polymer with a polymerized sulfonated diamine; a heterocyclic compound that includes at least one ring with at least 3 members; a crosslinking agent to react or interact with the heterocyclic compound; and a phosphate salt (as shown at reference numeral 102); and diluting the aqueous dispersion with water to obtain the textile coating composition having a total solids content ranging from about 1% to about 10% (as shown at reference numeral 104).
  • each of the self-crosslinked polyurethane binder particle, the heterocyclic compound, the crosslinking agent, and the phosphate salt may be part of its own dispersion or solution prior to being incorporated together. It is to be understood that the liquid components from these individual dispersion(s) and solution(s) make up the aqueous portion of the aqueous dispersion. As such, no additional water is added when combining the self-crosslinked polyurethane binder particle, the heterocyclic compound, the crosslinking agent, and the phosphate salt. Water is then added to dilute the aqueous dispersion to the desired solids content.
  • Any example and amount of any of the textile coating composition components as described herein may be used in the method 100.
  • the textile coating composition may include the filler in addition to the other components.
  • the coated textile 30 includes the fabric substrate 32 and an image receiving layer 34 on at least one surface 36A or 36B of the fabric substrate 32, the image receiving layer 34 including: an interpenetrating polymer network, which includes a crosslinked heterocycle and a self-crossl inked polyurethane binder particle including a polyurethane polymer with a polymerized sulfonated diamine; and a phosphate salt.
  • the image receiving layer 34 further includes a filler.
  • the image receiving layer 34 further includes a surfactant.
  • the image receiving layer 34 further includes a filler and/or a surfactant.
  • the fabric substrate 32 may be selected from the group consisting of polyester fabrics, polyester blend fabrics, cotton fabrics, cotton blend fabrics, nylon fabrics, nylon blend fabrics, silk fabrics, silk blend fabrics, wool fabrics, wool blend fabrics, and combinations thereof.
  • the fabric substrate is selected from the group consisting of cotton fabrics and cotton blend fabrics.
  • organic textile fabrics and/or inorganic textile fabrics may be used for the substrate fabric 32.
  • Some types of fabrics that can be used include various fabrics of natural and/or synthetic fibers.
  • the polyester fabrics may be a polyester coated surface.
  • the polyester blend fabrics may be blends of polyester and other materials (e.g., cotton, linen, etc.).
  • the fabric substrate 32 may be selected from nylons (polyamides) or other synthetic fabrics.
  • Example natural fiber fabrics that can be used include treated or untreated natural fabric textile substrates, e.g., wool, cotton (regular plant cotton, organic cotton, pima cotton, supima cotton, and/or slub cotton), silk, linen, jute, flax, hemp, rayon fibers, thermoplastic aliphatic polymeric fibers derived from renewable resources (e.g. cornstarch, tapioca products, sugarcanes), etc.
  • treated or untreated natural fabric textile substrates e.g., wool, cotton (regular plant cotton, organic cotton, pima cotton, supima cotton, and/or slub cotton), silk, linen, jute, flax, hemp, rayon fibers, thermoplastic aliphatic polymeric fibers derived from renewable resources (e.g. cornstarch, tapioca products, sugarcanes), etc.
  • renewable resources e.g. cornstarch, tapioca products, sugarcanes
  • Example synthetic fibers used in the textile fabric substrate 32 can include polymeric fibers such as nylon fibers, polyvinyl chloride (PVC) fibers, PVC-free fibers made of polyester, polyamide, polyimide, polyacrylic, polypropylene, polyethylene, polyurethane (LYCRA®, The Lycra Co.), polystyrene, polyaramid (e.g., KEVLAR®), polytetrafluoroethylene (TEFLON®) (both trademarks of E.l. du Pont de Nemours and Company, Delaware), fiberglass, polytrimethylene, polycarbonate, polyethylene terephthalate, polyester terephthalate, polybutylene terephthalate, or a combination thereof.
  • polymeric fibers such as nylon fibers, polyvinyl chloride (PVC) fibers, PVC-free fibers made of polyester, polyamide, polyimide, polyacrylic, polypropylene, polyethylene, polyurethane (LYCRA®, The Lycra Co.), polystyrene,
  • natural and synthetic fibers may be combined at ratios of 1 : 1 , 1:2, 1:3, 1:4, 1 :5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:11, 1:12, 1:13, 1:14, 1:15, 1:16, 1:17, 1:18, 1:19, 1:20, or vice versa.
  • One example blend includes polyester, cotton, and rayon.
  • the fiber can be a modified fiber from the above-listed polymers.
  • modified fiber refers to one or both of the polymeric fiber and the fabric as a whole having undergone a chemical or physical process such as, but not limited to, copolymerization with monomers of other polymers, a chemical grafting reaction to contact a chemical functional group with one or both the polymeric fiber and a surface of the fabric, a plasma treatment, a solvent treatment, acid etching, or a biological treatment, an enzyme treatment, or anti-microbial treatment to prevent biological degradation.
  • the fabric substrate 32 can contain additives, such as a colorant (e.g., pigments, dyes, and tints), an antistatic agent, a brightening agent, a nucleating agent, an antioxidant, a UV stabilizer, a filler, and/or a lubricant, for example.
  • a colorant e.g., pigments, dyes, and tints
  • fabric substrate are used interchangeably, and do not include materials commonly known as any kind of paper (even though paper can include multiple types of natural and synthetic fibers or mixtures of both types of fibers).
  • Fabric substrates can include textiles in filament form, textiles in the form of fabric material, or textiles in the form of fabric that has been crafted into finished articles (e.g., clothing, blankets, tablecloths, napkins, towels, bedding material, curtains, carpet, handbags, shoes, banners, signs, flags, etc.).
  • the fabric substrate can have a woven or knitted fabric structure.
  • the fabric substrate may be non-woven or tufted.
  • the fabric substrate can be a woven fabric where warp yarns and weft yarns can be mutually positioned at an angle of about 90°.
  • This woven fabric can include fabric with a plain weave structure, fabric with an end-on-end weave, fabric with a voile weave, fabric with an Oxford weave, fabric with twill weave structure where the twill weave produces diagonal lines on a face of the fabric, or a satin weave.
  • the fabric substrate can be a knitted fabric with a loop structure. The loop structure can be a warp-knit fabric, a weft-knit fabric, or a combination thereof.
  • a warp-knit fabric refers to every loop in a fabric structure that can be formed from a separate yarn mainly introduced in a longitudinal fabric direction.
  • a weft-knit fabric refers to loops of one row of fabric that can be formed from the same yarn.
  • the fabric substrate 32 can have a basis weight ranging from 10 gsm to 500 gsm. In another example, the fabric substrate 32 can have a basis weight ranging from 50 gsm to 400 gsm. In other examples, the fabric substrate can have a basis weight ranging from 100 gsm to 300 gsm, from 75 gsm to 250 gsm, from 125 gsm to 300 gsm, or from 150 gsm to 350 gsm.
  • the fabric substrate 32 may be any color. In an example, the fabric substrate 32 is white. In another example, the fabric substrate 32 is a color other than white.
  • the image receiving layer 34 is the dried textile coating composition.
  • the textile coating composition may be applied to one surface 36A of the fabric substrate 32 and dried to form the image receiving layer 34.
  • the textile coating composition may be applied to the surface 36A and dried to form an image receiving layer 34, and the textile coating composition may be applied to the other surface 36B (which is opposed to the surface 36A) to form another image receiving layer 34’.
  • Fig. 5 illustrates an example of a method 200 for making the coated textile 30.
  • This example of the method 200 includes applying a textile coating composition on a surface of a fabric substrate, the textile coating composition including a self- crosslinked polyurethane binder particle including a polyurethane polymer with a polymerized sulfonated diamine; a heterocyclic compound that includes at least one ring with at least 3 members; a crosslinking agent to react or interact with the heterocyclic compound; a phosphate salt; and an aqueous vehicle (reference numeral 202); and drying the textile coating composition to form an image receiving layer on the fabric substrate (reference numeral 204).
  • a textile coating composition including a self- crosslinked polyurethane binder particle including a polyurethane polymer with a polymerized sulfonated diamine; a heterocyclic compound that includes at least one ring with at least 3 members; a crosslinking agent to react or interact with the heterocyclic compound; a phosphat
  • the textile coating composition is applied to a surface 32A and/or 32B of the fabric substrate 32.
  • the textile coating composition may be any of the example formulations set forth herein.
  • the textile coating composition may be applied to one or both surface(s) 36A, 36B of the fabric substrate 32 via analog methods. Analog methods include using an auto analog pretreater, a drawdown coater, a slot die coater, a roller coater, a fountain curtain coater, a blade coater, a rod coater, an air knife coater, a sprayer, a padder, or a gravure application.
  • the textile coating composition may be coated on all or substantially all of the fabric substrate 32.
  • the textile coating composition is applied in an amount ranging from about 0.5 gsm to about 10 gsm.
  • the method 200 then includes drying the textile coating composition to form an image receiving layer 34 on the fabric substrate 32.
  • the textile coating composition is exposed to active drying, which exposes the textile coating composition to warm air or infrared energy.
  • the coating composition is dried at a temperature ranging from about 60°C to about 150°C for a time period ranging from about 10 minutes to about 30 minutes.
  • the coating composition is dried at a temperature of 100°C to about 130°C for a time period ranging from about 15 minutes to about 25 minutes.
  • the temperature and time for drying may depend, in part, upon the running speed and the drying channel length of the drying system that is used.
  • the heterocyclic compound and the crosslinking agent may react with each other or interact with each other form part of the crosslinked polymer network.
  • the crosslinking agent includes a functional group (e.g., amine, etc.) that is able to open heterocyclic rings and form a crosslinked structure between macromolecular chains.
  • the resulting crosslinked polymer is referred to herein as “the crosslinked heterocyclic compound” even though the at least 3 membered ring may be opened during the crosslinking reaction.
  • the crosslinking agent is a catalyst that initiates self-crosslinking by a catalytic homopolymerization reaction of the at least 3 membered ring of the heterocyclic compound.
  • the resulting self-crossl inked polymer is also referred to herein as “the crosslinked heterocyclic compound” even though the at least 3 membered ring may be opened during the crosslinking reaction.
  • the crosslinked heterocyclic compound is formed by a reaction or an interaction between at least one ring of the heterocyclic compound and the crosslinking agent.
  • the crosslinked polymer network may also include the self-crossl inked polyurethane binder particles, which can also crosslink with groups of the heterocyclic compound.
  • the resulting crosslinked polymer network improves the durability of image printed on the coated textile fabric.
  • the resulting image receiving layer(s) 34, 34’ that is/are formed may be a continuous layer that covers all or substantially all of the surface(s) 32A, 32B of the fabric substrate 32.
  • the coated textile 30 is ready for use.
  • the coated textile 30 may be used in textile printing as the printing media.
  • the coated textile 30 may be used in a digital printing process, and thus has digital inkjet inks printed thereon; or may be used in an analog printing process, and thus has ink applied thereto (e.g., via any of the analog methods set forth herein).
  • One example of such a printing method may include inkjet printing an inkjet ink (of any color) on the coated textile fabric 30.
  • the coated textile 30 may generate prints with excellent image quality and durability when used as printing media for inkjet printing.
  • the ink that is applied to the coated textile is a digital inkjet ink, such as a thermal inkjet ink or a piezoelectric inkjet ink.
  • the ink that is applied to the coated textile is a latex based digital inkjet ink.
  • the ink that is applied to the coated textile is a pigment-based inkjet ink.
  • the ink that is applied to the coated textile is a dye-based inkjet ink.
  • the crosslinked polymer network contributes to enhanced image quality and durability of the image.
  • the latex in the ink may become interpenetrated with the crosslinked polymer network, thus forming an interpenetrated polymer network which can further improve the durability of the image.
  • the coated textile also maintains flame retardancy when used as printing media, due to the presence of the phosphate salt.
  • Example 1 One example of a self-crosslinked polyurethane binder particle dispersion was prepared (referred to as Example 1).
  • the example polyurethane binder particles in the dispersion were polyurethane polymers that were stabilized by sulfonated diamines.
  • the example self-crosslinked polyurethane binder particle dispersion was prepared as follows. 72.620 g of polyester polyol (PED; STEPANOL® PC-1015-55, commercially available from Stepan, USA), 20.570 g of isophorone diisocyanate (IPDI), and 80 g of acetone were mixed in a 500 ml 4-neck round bottom flask. A mechanical stirrer with glass rod and a polytetrafluoroethylene (PTFE) blade was attached. The flask was immersed in a constant temperature bath at 75°C. The system was kept under a drying tube. 3 drops of dibutyltin dilaurate (DBTDL) were added to initiate the polymerization.
  • DBTDL dibutyltin dilaurate
  • Polymerization was continued for 6 hours at 75°C. 0.5 g samples were withdrawn for % NCO titration to confirm the reaction. The measured NCO value was 5.10 %. The theoretical % NCO was 5.13%. This generated a pre-polymer solution. The polymerization temperature was reduced to 50°C.
  • TMD 2,2,4-trimethylhexane-1 ,6-diamine
  • A-95 sodium aminoalklysulphonate
  • deionized water 14.819 g
  • One comparative example of a self-crosslinked polyurethane binder particle dispersion was also prepared (referred to as Comp. Ex. 2).
  • the comparative example polyurethane binder particles in the comparative dispersion were polyurethane polymers that were stabilized by both sulfonated diamines and carboxylates.
  • the comparative example self-crosslinked polyurethane binder particle dispersion was prepared as follows. 43.66 g of polypropylene glycol (MW 1000), 192.58 g of polyol 53 (from DSM, Total Solids 70.1%), 12.21 g of dimethylolpropionic acid (DMPA, available from GEO® Specialty Chemicals), and 68 g of extra dry acetone (available from Fisher Scientific), were mixed in a 2000 ml 4-neck round bottom flask. 75.9 g of isophorone diisocyanate (IPDI) and 20 g of dry acetone was added to the flask. A mechanical stirrer with a glass rod and polytetrafluoroethylene (PTFE) blade was attached.
  • IPDI isophorone diisocyanate
  • PTFE polytetrafluoroethylene
  • a condenser was attached.
  • the flask was immersed in a constant temperature bath at 65°C.
  • the system was kept under a dry nitrogen blanket.
  • 12 drops (approximately 0.32 g) of bismuth-based catalyst was warmed in a 50°C oven, and then added to the flask to initiate polymerization. Polymerization was continued for about 6 hours at 65°C.
  • 0.5 g samples were withdrawn for % NCO titration to confirm the reaction, and solids % of the samples taken at 4 and 6 hours were also used to monitor the reaction.
  • the theoretical % NCO should be 4.65%.
  • 12 additional drops of bismuth-based catalyst were added to the flask after 6 hours.
  • Comparative example self-crosslinked polyurethane binder particle dispersions were utilized. These comparative example self-crosslinked polyurethane binder particle dispersions were commercially available, and polyurethane binder particles in the dispersions were stabilized by carboxylates.
  • the commercially available polyurethane binder particle dispersions included SANCURETM 2160 (referred to as Comp. Ex. 3) and SANCURETM 20041 (referred to as Comp. Ex. 4) (both of which are available from Lubrizol), and IMPRANIL® DLN-SD (referred to as Comp. Ex. 5) and DISPERCOLL® U42 (referred to as Comp. Ex. 6) (both of which are available from Covestro).
  • the example polyurethane dispersion and the comparative polyurethane dispersions were then tested for compatibility with phosphate salts.
  • the salts and the polyurethane dispersions were mixed at various ratios, at temperatures within 18°C- 25°C, and were then observed for visual compatibility. The results can be found in Table 1, shown below.
  • Example 1 the sulfonated polyurethane dispersion
  • Example 2 the sulfonated polyurethane dispersion
  • Comparative Ex. 2 through Comparative Ex. 6 showed poor compatibility with the phosphate salt, gelling at low ratios of phosphate salt to polyurethane dispersion.
  • the example coating compositions were then coated onto a polyester fabric substrate via analog methods.
  • the comparative polyurethane dispersions were not used to prepare comparative coating compositions because the polyurethane crashed out of solution, and thus also were not coated onto a polyester fabric substrate.
  • the example coated textiles A and B were then subjected to flame retardancy testing, using the National Fire Protection Association (NFPA) 701 small scale testing regime.
  • NFPA National Fire Protection Association
  • the ignition resistance of a fabric after it is exposed to a flame for 12 seconds is tested.
  • the flaming residue time was measured. Flaming residue time is the amount of time that that a fabric remains lit (has an after flame) after the 12 second exposure.
  • the fabric passes the test if the fabric’s flaming residue is less than 2 seconds.
  • the flaming residue results for coated textiles A and B are shown in Table 3.
  • the weight of the fabric before and after the flame exposure was measured.
  • the fabric is said to have passed the NFPA 701 test if the total weight loss is less than 40% after burning.
  • the weights of the example coated textiles A and B can be also found in Table 3, shown below.
  • Additional samples of the example coated textiles A and B were prepared and used as printing media.
  • the coated textiles had latex inkjet inks printed thereon using an HP LX360 printer.
  • the inks printed included a black ink, a white ink, a magenta ink, a cyan ink, a yellow ink, and combinations thereof to produce green patches, red patches, and blue patches.
  • the inks were applied to the image receiving layer of the coated textiles to generate several patches of varying shape and size (referred to herein as prints A and B). Some areas of the coated textiles were left unprinted for testing the durability of the coated textiles themselves. Different patches of the Prints A and B were tested for image quality (e.g., optical density and gamut) and durability (e.g., rub resistance, scratch resistance, wrinkle/fold).
  • Prints A and B were tested for image quality.
  • the optical density of one black patch was measured using an X-rite spectrodensitometer from X- Rite Inc.
  • Gamut was tested for a 72 color block image.
  • 72 color gamut tests the portion of the color space that is represented or reproduced in the color block, and, can be tested using a Gregtag/Mcbeth Spectrolina Spectroscan or a Barberie.
  • Durability refers to the ability of the coated textile with ink printed thereon to resist creasing when subjected to a variety of tests.
  • the durability tests were all visually inspected for defects, and scored on a scale of 1-5. The scale indicated level of visual defects. The scale and criteria can be seen below, in Table 5.
  • One durability test that was performed was a fold test, in which one set of prints A and B was folded 4 times and then a 1 kg weight was placed on each of the folded textiles for 30 minutes.
  • the folded prints A and B were unfolded and attached to a screen and exposed to an LED light that was positioned behind the screen.
  • This set of prints A and B was then visually observed for folding line and ink broken line defects on the coating composition, which manifest themselves in the form of a distinct line(s) where the fold(s) was/were
  • the folding lines and ink film cracking lines, if any, were evaluated when the LED backlighting illuminated the print.
  • the line(s) may appear white, e.g., when the images are black, and may appear dark, e.g., when the images are lighter color (e.g., yellow, light magenta, etc.).
  • the prints were given a score of 1-5 based on the scale described in Table 5.
  • Another durability test that was performed was a wrinkle test, in which the other set of prints A and B was exposed to wrinkling, including movement and bending in a person’s hands for about 60 seconds.
  • the wrinkled prints A and B were flattened and attached to the screen and exposed to the LED backlight.
  • This set of prints A and B was then visually observed (while the backlight was illuminated) for ink removal or wrinkle line defects and ink film cracking lines, if any, in the coating composition, which manifest themselves in the form of distinct line(s) where the wrinkles(s) was/were.
  • the line(s) may appear white, e.g., when the images are black, and may appear dark, e.g., when the images are lighter colors (e.g., yellow, magenta, etc.).
  • the prints were given a score of 1-5 based on the scale described in Table 5.
  • Both sets of prints A and B exhibited suitable durability after being folded and wrinkles, especially in the black patches and the areas of the coated textiles that were not printed on.
  • Another durability test that was performed was a rub resistance test (i.e. , dry rub test). This test was performed on a dedicated set of the black patches of each of prints A and B from one of the sets.
  • the dry rub test was carried out using an abrasion scrub tester as follows. The dedicated set of the black patches were exposed to a 800 g weight that was loaded on the test header that moves back and forth.
  • the test tip was made of acrylic resin with crock cloth.
  • the test cycle speed was then set to 25 cm/m in and 5 cycles were carried out on each print at an 8 inch length for each cycle.
  • the test probe was in dry (dry rub) mode.
  • the prints were then visually inspected, and graded according to the scale described in Table 5. Defects resulting from the dry rub test would be ink removal, or cracking, or removal of the coating composition.
  • Another durability test that was performed was a scratch test. This test was performed on the dedicated set of cyan, magenta, yellow, and black patches of each of prints A and B from one of the sets. The scratch test was performed by exposing prints A and B to a coin at a 45° angle under a normal force of 250 g, which was then dragged across the prints. Both prints were visually inspected for ink defects, such as ink removal or coating composition removal, and graded according to the scale described in Table 5. The test was performed with a BYK Abrasion Tester (from BYK- Gardner USA, Columbus, MD) with a linear, back-and-forth motion of the angled coin, attempting to scratch off the image-side of the samples, for 5 cycles.
  • BYK Abrasion Tester from BYK- Gardner USA, Columbus, MD
  • ranges provided herein include the stated range and any value or sub-range within the stated range, as if the value(s) or sub- range(s) within the stated range were explicitly recited.
  • a range from about 1 wt% active to about 10 wt% active should be interpreted to include not only the explicitly recited limits of from about 1 wt% active to about 10 wt% active, but also to include individual values, such as about 2.15 wt% active, about 3 wt% active, 5.2 wt% active, 8.77 wt% active, etc., and sub-ranges, such as from about 1.5 wt% active to about 9.5 wt% active, from about 3 wt% active to about 5.7 wt% active, from about 1 wt% active to about 8 wt% active, etc.
  • “about” is utilized to describe a value, this is meant to encompass minor variations (up to +/- 10%) from the stated value.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Un exemple d'une composition de revêtement textile comprend une particule de liant de polyuréthane auto-réticulé. La particule de liant de polyuréthane auto-réticulé comprend un polymère de polyuréthane avec une diamine sulfonée polymérisée. La composition de revêtement textile comprend également un composé hétérocyclique qui comprend au moins un composé hétérocyclique qui comprend au moins un cycle avec au moins 3 éléments, et un agent de réticulation qui est destiné à réagir ou à interagir avec le composé hétérocyclique. La composition de revêtement textile comprend également un sel de phosphate et un véhicule aqueux.
PCT/US2021/023460 2021-03-22 2021-03-22 Composition de revêtement textile WO2022203649A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/US2021/023460 WO2022203649A1 (fr) 2021-03-22 2021-03-22 Composition de revêtement textile

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2021/023460 WO2022203649A1 (fr) 2021-03-22 2021-03-22 Composition de revêtement textile

Publications (1)

Publication Number Publication Date
WO2022203649A1 true WO2022203649A1 (fr) 2022-09-29

Family

ID=83397766

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2021/023460 WO2022203649A1 (fr) 2021-03-22 2021-03-22 Composition de revêtement textile

Country Status (1)

Country Link
WO (1) WO2022203649A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008074589A1 (fr) * 2006-12-21 2008-06-26 Agfa Graphics Nv Procédés d'impression par jet d'encre et ensembles d'encres
WO2020130831A1 (fr) * 2018-12-21 2020-06-25 Stahl International B.V. Procédé de préparation de dispersions aqueuses de polyuréthane, ignifuges, exemptes d'halogène
WO2020131787A1 (fr) * 2018-12-18 2020-06-25 Hewlett-Packard Development Company, L.P. Composition de prétraitement et support imprimable

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008074589A1 (fr) * 2006-12-21 2008-06-26 Agfa Graphics Nv Procédés d'impression par jet d'encre et ensembles d'encres
WO2020131787A1 (fr) * 2018-12-18 2020-06-25 Hewlett-Packard Development Company, L.P. Composition de prétraitement et support imprimable
WO2020130831A1 (fr) * 2018-12-21 2020-06-25 Stahl International B.V. Procédé de préparation de dispersions aqueuses de polyuréthane, ignifuges, exemptes d'halogène

Similar Documents

Publication Publication Date Title
EP3180378A1 (fr) Compositions polymères aqueuses pour l'impression, encres pour l'impression numérique par jet d'encre et impression sur textiles
US11401652B2 (en) Pre-treatment composition and printable medium
US11066782B2 (en) Textile printing
US20220041883A1 (en) Textile printing
US20210324230A1 (en) Coating composition and printable medium
US11794506B2 (en) Coating composition and printable medium
WO2022203649A1 (fr) Composition de revêtement textile
US20220073768A1 (en) Inkjet ink for textile printing
WO2020131026A1 (fr) Compositions de revêtement de tissu
US20230137276A1 (en) Textile printing with silicone pretreat compositions
US20220154028A1 (en) Printing sets
WO2022173425A1 (fr) Ensemble de fluides pour impression textile
US20220403200A1 (en) Multi-fluid kit for textile printing
US20230303881A1 (en) Inkjet fluid set
US20230272241A1 (en) Phosphonium-containing polyurethane compositions
US20230002633A1 (en) Multi-fluid kit for inkjet textile printing
US20240301228A1 (en) Multi-fluid kit for textile printing
US20230064522A1 (en) Fixer fluids
WO2021216056A1 (fr) Ensemble de fluides
US20210363695A1 (en) Textile printing
WO2022132131A1 (fr) Kit multi-fluide pour impression textile
US20220243079A1 (en) White ink compositions
WO2022046100A1 (fr) Compositions de revêtement
EP4100475A1 (fr) Encre pour jet d'encre blanche
WO2021211138A1 (fr) Ensemble de fluides

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 21933426

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 21933426

Country of ref document: EP

Kind code of ref document: A1