AU2010232930B2 - Polyurethane dispersion, method of producing the same, coated articles, and method for coating articles - Google Patents
Polyurethane dispersion, method of producing the same, coated articles, and method for coating articles Download PDFInfo
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- AU2010232930B2 AU2010232930B2 AU2010232930A AU2010232930A AU2010232930B2 AU 2010232930 B2 AU2010232930 B2 AU 2010232930B2 AU 2010232930 A AU2010232930 A AU 2010232930A AU 2010232930 A AU2010232930 A AU 2010232930A AU 2010232930 B2 AU2010232930 B2 AU 2010232930B2
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- Prior art keywords
- polyols
- polyurethane dispersion
- prepolymers
- coating
- natural oil
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- 229920003009 polyurethane dispersion Polymers 0.000 title claims abstract description 59
- 238000000576 coating method Methods 0.000 title claims abstract description 48
- 238000000034 method Methods 0.000 title claims abstract description 42
- 239000011248 coating agent Substances 0.000 title claims abstract description 34
- 229920005862 polyol Polymers 0.000 claims abstract description 100
- 150000003077 polyols Chemical class 0.000 claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 50
- -1 adipate polyols Chemical class 0.000 claims abstract description 41
- 150000002009 diols Chemical class 0.000 claims abstract description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000004094 surface-active agent Substances 0.000 claims abstract description 18
- 239000012948 isocyanate Substances 0.000 claims abstract description 15
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 15
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 229920002635 polyurethane Polymers 0.000 claims abstract description 7
- 239000004814 polyurethane Substances 0.000 claims abstract description 7
- 239000003921 oil Substances 0.000 claims description 43
- 235000019198 oils Nutrition 0.000 claims description 43
- 239000000758 substrate Substances 0.000 claims description 27
- 239000003999 initiator Substances 0.000 claims description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 14
- 239000006185 dispersion Substances 0.000 claims description 12
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
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- 229920000728 polyester Polymers 0.000 claims description 9
- 239000008199 coating composition Substances 0.000 claims description 8
- 239000000470 constituent Substances 0.000 claims description 8
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 7
- 239000003925 fat Substances 0.000 claims description 7
- 229920000570 polyether Polymers 0.000 claims description 7
- 239000008158 vegetable oil Substances 0.000 claims description 6
- 239000010775 animal oil Substances 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 235000019871 vegetable fat Nutrition 0.000 claims description 4
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000002023 wood Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 239000000178 monomer Substances 0.000 description 9
- 239000004970 Chain extender Substances 0.000 description 8
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 7
- 235000010469 Glycine max Nutrition 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 125000003010 ionic group Chemical group 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
- 208000008469 Peptic Ulcer Diseases 0.000 description 5
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000007373 indentation Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
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- 239000002245 particle Substances 0.000 description 5
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- 229940086542 triethylamine Drugs 0.000 description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 125000002091 cationic group Chemical group 0.000 description 4
- 239000004567 concrete Substances 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
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- 239000003960 organic solvent Substances 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 238000010926 purge Methods 0.000 description 4
- 239000000600 sorbitol Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 239000001361 adipic acid Substances 0.000 description 3
- 235000011037 adipic acid Nutrition 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 3
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
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- 238000006386 neutralization reaction Methods 0.000 description 3
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- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 description 2
- OHOVKSFZYUUKHT-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)heptanoic acid Chemical compound CCCCCC(CO)(CO)C(O)=O OHOVKSFZYUUKHT-UHFFFAOYSA-N 0.000 description 2
- ASUUYDBHVNPPRZ-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)octanoic acid Chemical compound CCCCCCC(CO)(CO)C(O)=O ASUUYDBHVNPPRZ-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
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- 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
- C08G18/6662—Compounds of group C08G18/42 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/40—Layered products comprising a layer of synthetic resin comprising polyurethanes
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- 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
-
- 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
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- 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
- C08G18/36—Hydroxylated esters of higher fatty acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2475/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Dispersion Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16502409P | 2009-03-31 | 2009-03-31 | |
| US61/165,024 | 2009-03-31 | ||
| PCT/US2010/023458 WO2010114643A1 (en) | 2009-03-31 | 2010-02-08 | Polyurethane dispersion, method of producing the same, coated articles, and method for coating articles |
Publications (2)
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| AU2010232930A1 AU2010232930A1 (en) | 2011-10-27 |
| AU2010232930B2 true AU2010232930B2 (en) | 2014-02-06 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2010232930A Active AU2010232930B2 (en) | 2009-03-31 | 2010-02-08 | Polyurethane dispersion, method of producing the same, coated articles, and method for coating articles |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9512262B2 (https=) |
| EP (1) | EP2414414B1 (https=) |
| JP (1) | JP5916601B2 (https=) |
| KR (1) | KR101710217B1 (https=) |
| CN (1) | CN102985457B (https=) |
| AU (1) | AU2010232930B2 (https=) |
| BR (1) | BRPI1006464B1 (https=) |
| WO (1) | WO2010114643A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010117838A1 (en) * | 2009-03-31 | 2010-10-14 | Dow Global Technologies Inc. | Polyurethane dispersion, method of producing the same, coated articles, and method for coating articles |
| US20130338307A1 (en) * | 2011-03-01 | 2013-12-19 | Roidec India Chemical (P) Ltd | Natural oil based poly-urethane dispersion |
| WO2012117414A1 (en) * | 2011-03-01 | 2012-09-07 | Roidec India Chemicals (P) Ltd. | Process for the preparation of a natural oil based poly-urethane dispersion |
| GB201402585D0 (en) | 2014-02-14 | 2014-04-02 | Croda Int Plc | Polyurethane dispersions |
| MY203264A (en) * | 2014-05-26 | 2024-06-20 | Univ Kebangsaan Malaysia | Method to produce natural oil-based polyurethane prepolymer |
| WO2020047216A1 (en) * | 2018-08-30 | 2020-03-05 | Checkerspot, Inc. | Hydroformylated triglycerides and uses thereof |
| KR20220016901A (ko) * | 2019-06-04 | 2022-02-10 | 다우 글로벌 테크놀로지스 엘엘씨 | 감열성 수성 폴리우레탄 분산제 및 이의 제조 방법 |
| CN110982414B (zh) * | 2019-12-18 | 2021-07-23 | 万华化学集团股份有限公司 | 一种食品接触水性木器涂料及其制备方法 |
| WO2021247368A1 (en) * | 2020-06-01 | 2021-12-09 | Checkerspot, Inc. | Triglyceride oils, polyols, and uses thereof |
| CA3193399A1 (en) * | 2020-09-22 | 2022-03-31 | Kristeen Esther JOSEPH | Water-based polyurethane dispersions and their preparation |
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| DE10016548A1 (de) | 2000-04-03 | 2001-10-11 | Bayer Ag | Polyurethan-Dispersionen |
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| WO2009117665A2 (en) * | 2008-03-20 | 2009-09-24 | Dow Global Technologies Inc. | Prepolymers made from natural oil based polyols |
-
2010
- 2010-02-08 JP JP2012503440A patent/JP5916601B2/ja active Active
- 2010-02-08 KR KR1020117025635A patent/KR101710217B1/ko active Active
- 2010-02-08 BR BRPI1006464-8A patent/BRPI1006464B1/pt not_active IP Right Cessation
- 2010-02-08 WO PCT/US2010/023458 patent/WO2010114643A1/en not_active Ceased
- 2010-02-08 AU AU2010232930A patent/AU2010232930B2/en active Active
- 2010-02-08 CN CN201080023196.6A patent/CN102985457B/zh active Active
- 2010-02-08 US US13/262,572 patent/US9512262B2/en active Active
- 2010-02-08 EP EP10703779.8A patent/EP2414414B1/en active Active
Patent Citations (2)
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| DE4020455A1 (de) * | 1990-06-27 | 1992-01-02 | Henkel Kgaa | Waessrige polyurethandispersion, deren herstellung und verwendung in der lederzurichtung |
| EP1849810A1 (en) * | 2006-04-27 | 2007-10-31 | Cytec Surface Specialties Austria GmbH | Oil based aqueous polyurethane dispersions |
Also Published As
| Publication number | Publication date |
|---|---|
| US20120035318A1 (en) | 2012-02-09 |
| CN102985457A (zh) | 2013-03-20 |
| WO2010114643A1 (en) | 2010-10-07 |
| EP2414414A1 (en) | 2012-02-08 |
| US9512262B2 (en) | 2016-12-06 |
| CN102985457B (zh) | 2014-10-29 |
| KR101710217B1 (ko) | 2017-02-24 |
| BRPI1006464B1 (pt) | 2020-02-11 |
| JP2012522102A (ja) | 2012-09-20 |
| BRPI1006464A2 (pt) | 2016-02-10 |
| KR20120000572A (ko) | 2012-01-02 |
| JP5916601B2 (ja) | 2016-05-11 |
| AU2010232930A1 (en) | 2011-10-27 |
| EP2414414B1 (en) | 2013-11-06 |
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