WO2023242311A1 - Composition de revêtement aqueuse à faible brillant présentant des propriétés mécaniques améliorées - Google Patents
Composition de revêtement aqueuse à faible brillant présentant des propriétés mécaniques améliorées Download PDFInfo
- Publication number
- WO2023242311A1 WO2023242311A1 PCT/EP2023/066043 EP2023066043W WO2023242311A1 WO 2023242311 A1 WO2023242311 A1 WO 2023242311A1 EP 2023066043 W EP2023066043 W EP 2023066043W WO 2023242311 A1 WO2023242311 A1 WO 2023242311A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- coating composition
- polyurethane
- aqueous self
- crosslinking coating
- diol
- Prior art date
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- 239000008199 coating composition Substances 0.000 title claims abstract description 44
- 239000002245 particle Substances 0.000 claims abstract description 48
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- 238000004132 cross linking Methods 0.000 claims abstract description 35
- 239000000178 monomer Substances 0.000 claims abstract description 31
- 229920002635 polyurethane Polymers 0.000 claims abstract description 27
- 239000004814 polyurethane Substances 0.000 claims abstract description 27
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 22
- 229920000642 polymer Polymers 0.000 claims abstract description 20
- 125000000468 ketone group Chemical group 0.000 claims abstract description 10
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 9
- 150000002009 diols Chemical class 0.000 claims description 43
- 239000000203 mixture Substances 0.000 claims description 23
- 239000002562 thickening agent Substances 0.000 claims description 19
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- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000011248 coating agent Substances 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000004970 Chain extender Substances 0.000 claims description 6
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- 238000000034 method Methods 0.000 claims description 6
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- IBVAQQYNSHJXBV-UHFFFAOYSA-N adipic acid dihydrazide Chemical compound NNC(=O)CCCCC(=O)NN IBVAQQYNSHJXBV-UHFFFAOYSA-N 0.000 claims description 4
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- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 3
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- 239000012299 nitrogen atmosphere Substances 0.000 description 4
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- 238000002360 preparation method Methods 0.000 description 4
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- 125000000129 anionic group Chemical group 0.000 description 3
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- 238000009826 distribution Methods 0.000 description 3
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
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- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 3
- 229940117969 neopentyl glycol Drugs 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 1
- IFDVQVHZEKPUSC-UHFFFAOYSA-N cyclohex-3-ene-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCC=CC1C(O)=O IFDVQVHZEKPUSC-UHFFFAOYSA-N 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- VEIOBOXBGYWJIT-UHFFFAOYSA-N cyclohexane;methanol Chemical compound OC.OC.C1CCCCC1 VEIOBOXBGYWJIT-UHFFFAOYSA-N 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- SWRGUMCEJHQWEE-UHFFFAOYSA-N ethanedihydrazide Chemical compound NNC(=O)C(=O)NN SWRGUMCEJHQWEE-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- PBZROIMXDZTJDF-UHFFFAOYSA-N hepta-1,6-dien-4-one Chemical compound C=CCC(=O)CC=C PBZROIMXDZTJDF-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- LMHJFKYQYDSOQO-UHFFFAOYSA-N hydroxydecanoic acid Natural products CCCCCC(O)CCCC(O)=O LMHJFKYQYDSOQO-UHFFFAOYSA-N 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000012688 inverse emulsion polymerization Methods 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- XPOXIRBXYPGDNE-UHFFFAOYSA-N methanediamine Chemical compound N[CH]N XPOXIRBXYPGDNE-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229960000380 propiolactone Drugs 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012966 redox initiator Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000012748 slip agent Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 229960001124 trientine Drugs 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- LXNOENXQFNYMGT-UHFFFAOYSA-N xi-5-Hydroxydodecanoic acid Chemical compound CCCCCCCC(O)CCCC(O)=O LXNOENXQFNYMGT-UHFFFAOYSA-N 0.000 description 1
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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4854—Polyethers containing oxyalkylene groups having four carbon atoms in the alkylene group
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation 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
- 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
- C08G18/34—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
- C08G18/70—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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/0086—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the application technique
- D06N3/0088—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the application technique by directly applying the resin
- D06N3/0093—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof characterised by the application technique by directly applying the resin by applying resin powders; by sintering
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/04—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/04—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06N3/042—Acrylic polymers
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
- D06N3/14—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes
- D06N3/142—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes mixture of polyurethanes with other resins in the same layer
- D06N3/144—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes mixture of polyurethanes with other resins in the same layer with polyurethane and polymerisation products, e.g. acrylics, PVC
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
- D06N3/14—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes
- D06N3/147—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyurethanes characterised by the isocyanates used
- D06N3/148—(cyclo)aliphatic polyisocyanates
Definitions
- low gloss coating compositions are obtained by addition of inorganic matting agents, such as amorphous or crystalline silica.
- inorganic matting agents such as amorphous or crystalline silica.
- siliceous particles poses serious health risks and therefore their use should be avoided.
- Aqueous polyurethane dispersions represent a safe valid alternative to the traditional inorganic matting agents.
- WO 2010/015494 discloses anionic polyurethane dispersions based on a polyglycol ether, poly(tetramethyleneglycol), that provide films having low gloss and soft touch atthe same time; soft touch effect or velvet effect is another superficial characteristic which is more and more appreciated by the market.
- films obtained from the anionic polyurethane dispersions described WO 2010/015494 show limited mechanical properties; particularly, they result impaired or damaged when contacted with organic solvents.
- WO2016/102596 suggests an aqueous coating composition comprising dispersed polymer particles, wherein the dispersed polymer particles are polyurethane-vinyl polymer hybrid particles obtained by free- radical polymerization of at least one vinyl monomer in the presence of a polyurethane.
- the present invention relates to an aqueous self-crosslinking coating composition
- an aqueous self-crosslinking coating composition comprising dispersed polymer particles, wherein: i) the dispersed polymer particles are polyurethane-vinyl polymer hybrid particles obtained by free-radical polymerization of at least one vinyl monomer and at least one ketone group containing vinyl monomer in the presence of a polyurethane, ii) the polyurethane and the vinyl polymer in the hybrid particles are present in a weight ratio of polyurethane to vinyl polymer ranging from 1:4 to 20:1, iii) the polyurethane is obtained by the reaction of at least the fol lowing components: a) from 5 to 40 % by weight (wt%) of at least one aliphatic or cycloaliphatic diisocyanate, b) from 0.5 to 5 wt% of at least one diol having at least one carboxylic or carboxylate group, c) from 40 to 90 wt
- the present invention relates to a method for coating leather or artificial leather comprising: providing an aqueous self-crosslinking coating composition comprising dispersed polymer particles as described above, applying it to their upper (finished and exposed to sight) surface and drying.
- the process for preparing the aqueous self-crosslinking coating composition of the present invention comprises the following steps: i) reaction of components a) to e) and optionally e) and f) to form a polyurethane prepolymer, ii) forming an aqueous dispersion of the polyurethane prepolymer in water, iii) chain extending the prepolymer with component d) to obtain a polyurethane dispersion, iv) polymerizing at least one vinyl monomer and at least one ketone group containing vinyl monomer in the polyurethane dispersion in the presence of a radical initiator to obtain a dispersion of polyurethane-vinyl polymer hybrid particles, v) adding a thickener and, optionally, a surfactant in water before forming the aqueous dispersion of the polyurethane prepolymer in water, or after any of the steps ii) to iv), vi) adding a dihydrazide
- the carboxylic water dispersing groups of component b) are preferably fully or partially in the form of a salt. Conversion to the salt form is effected by neutralisation with a base, preferably after the preparation of the prepolymer and before its dispersion in water.
- the base is preferably ammonia, an amine or an inorganic base.
- Suitable amines include tertiary amines, for example triethylamine or N,N- dimethylethanolamine.
- Suitable inorganic bases include alkali hydroxides and carbonates, for example lithium hydroxide, sodium hydroxide, or potassium hydroxide.
- Component c) is at least one diol with molecular weight between 500 and 5,000 g/mol.
- the amount of component c) relative to the total amount of components used to prepare the polyurethane is from 40 to 90 wt%, preferably from 50 to 70 wt%.
- nonionic polyether diols may be used as component c.
- polyester diols may be used as component c.
- polycarbonate diols may be used as component c.
- polyester diols are those obtainable from diol-initiated polymerization of hydroxy carboxylic acids containing from 2 to 26, and preferably from 4 to 12 carbon atoms, or a lactone thereof.
- the hydroxy carboxylic acids may be saturated or unsaturated, linear or branched.
- Componentf is at least one aliphatic or cycloaliphatic polyisocyanate having average functionality above 2.
- Said at least one vinyl monomer does not contain ketone groups and is selected among methyl methacrylate, methyl acrylate, ethyl methacrylate, ethyl acrylate, butyl acrylate, butyl methacrylate, styrene or mixtures thereof. Methyl methacrylate is preferred.
- Said at least one vinyl monomer represents at least 50 wt%, preferably at least 70 wt% of the total amount of the other vinyl monomer(s) used to prepare the vinyl polymer.
- the mean particle size (D[0.9]) of the dispersed polymer particles is less than 25 micron, preferably less than 15 micron.
- D[0.9] means that the first 90 volume % of the particle size distribution has a mean particle size Y.
- the particle size and particle size distribution are measured by laser diffraction using a Mastersizer 3000 from Malvern.
- acrylic thickeners refers to thickeners synthesized from acrylic monomers, that is monomers derived from acrylic acid, methacrylic acid and mixtures thereof.
- Suitable acrylic emulsion thickeners based on methacrylic acid and ethyl acrylate are alkali swellable acrylic emulsion thickeners (ASE), possibly including hydrophobic polyethoxylated monomers (such as (meth)acrylic esters of ethoxylated C1-C22 fatty alcohols) (HASE) and/or polyethylenically unsaturated monomers (crosslinkers)
- ASE alkali swellable acrylic emulsion thickeners
- HASE hydrophobic polyethoxylated monomers
- crosslinkers polyethylenically unsaturated monomers
- the surfactant can be chosen between non-ionic and anionic surfactants, but is preferably a non-ionic surfactant, more preferably a linear or branched aliphatic ethoxylated alcohol.
- the aqueous self-crosslinking coating composition of the present invention can be advantageously used in the finishing of leather and artificial leather, in the superficial coating of woven fabrics, paper, plastics, such as polycarbonates and PVC, wood and metals.
- the 60° gloss of the aqueous coating composition after drying is ⁇ 10, preferably ⁇ 2.
- the 85° gloss of the aqueous coating composition after drying is ⁇ 60, preferably ⁇ 20. Koniq hardness
- the prepolymer is cooled down at 65°C and triethylamine (TEA) is added under stirring to partially or fully neutralize the carboxylic groups present in the prepolymer backbone.
- TEA triethylamine
- the radical polymerization is initiated by the addition of 0.350 g of tert-butyl hydroperoxide and 0.350 g of Bruggolite® E28 (formaldehyde free sodium salt of an organic sulfinic acid derivative, commercially available from L. Bruggemann GmbH & Co. KG) simultaneously. Then 20 g of demineralized water are added.
- the resulting urethane/acrylic Hybrid dispersion is filtered with a 150 pm canvas and brought to a dry content of 31.3% and has a pH around 7.9 and a viscosity of 343 cps.
- the dispersion has a D (0.5) mean particle size of 6.0 pm and D (0.9) mean particle size of 16.3 pm.
- Example 4 is an 80/20 urethane/vinyl self-crosslinking modification of Comparative Example 1.
- Methylmethacrylate and diacetonacrylamide monomers are polymerised in the presence of the polyurethane dispersion prepared in the Comparative Example 1.
- the radical polymerization is initiated by the addition of 0.245 g of tert-butyl hydroperoxide and 0.230 g of Bruggolite® E28 (formaldehyde free sodium salt of an organic sulfinic acid derivative, commercially available from L. Bruggemann GmbH & Co. KG) simultaneously. Than 0.643 g of adipic acid dihydrazide in 13 g of demineralized water are added.
- the resulting self-crosslinking urethane/acrylic hybrid dispersion is filtered with a 150 pm canvas and brought to a dry content of 31.3% and has a pH around 7.9 and a viscosity of 343 cps.
- the dispersion has a D (0.5) mean particle size of 4.5 pm and D (0.9) mean particle size of 14.2 pm.
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Abstract
La présente invention concerne une composition aqueuse de revêtement auto-réticulante comprenant des particules polymères dispersées, dans laquelle : i) les particules polymères dispersées sont des particules hybrides polyuréthane-polymère vinylique obtenues par polymérisation à radicaux libres d'au moins un monomère vinylique et d'au moins un groupe cétone contenant un monomère vinylique en présence d'un polyuréthane, ii) le polyuréthane et le polymère vinylique dans les particules hybrides sont présents dans un rapport pondéral polyuréthane/polymère vinylique allant de 1 : 4 à 20 : 1.
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005058995A1 (fr) * | 2003-12-17 | 2005-06-30 | Dsm Ip Assets B.V. | Compositions aqueuses de revetement d'urethanne-vinyl antitaches |
WO2010015494A2 (fr) | 2008-08-08 | 2010-02-11 | Lamberti Spa | Dispersions aqueuses de polyuréthanes anioniques |
WO2013091209A1 (fr) * | 2011-12-22 | 2013-06-27 | Dow Global Technologies Llc | Nouveau procédé pour la fabrication de dispersions hybrides de polyuréthane/acrylique réticulables |
WO2016102596A1 (fr) | 2014-12-23 | 2016-06-30 | Dsm Ip Assets B.V. | Composition aqueuse de revêtement ayant un toucher doux après séchage |
WO2018172526A1 (fr) * | 2017-03-23 | 2018-09-27 | Lamberti Spa | Dispersions aqueuses de polyuréthane |
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- 2023-06-15 WO PCT/EP2023/066043 patent/WO2023242311A1/fr unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005058995A1 (fr) * | 2003-12-17 | 2005-06-30 | Dsm Ip Assets B.V. | Compositions aqueuses de revetement d'urethanne-vinyl antitaches |
WO2010015494A2 (fr) | 2008-08-08 | 2010-02-11 | Lamberti Spa | Dispersions aqueuses de polyuréthanes anioniques |
WO2013091209A1 (fr) * | 2011-12-22 | 2013-06-27 | Dow Global Technologies Llc | Nouveau procédé pour la fabrication de dispersions hybrides de polyuréthane/acrylique réticulables |
WO2016102596A1 (fr) | 2014-12-23 | 2016-06-30 | Dsm Ip Assets B.V. | Composition aqueuse de revêtement ayant un toucher doux après séchage |
WO2018172526A1 (fr) * | 2017-03-23 | 2018-09-27 | Lamberti Spa | Dispersions aqueuses de polyuréthane |
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