CA2272759C - High solids polyurethane-urea dispersions having improved storage stability - Google Patents
High solids polyurethane-urea dispersions having improved storage stability Download PDFInfo
- Publication number
- CA2272759C CA2272759C CA002272759A CA2272759A CA2272759C CA 2272759 C CA2272759 C CA 2272759C CA 002272759 A CA002272759 A CA 002272759A CA 2272759 A CA2272759 A CA 2272759A CA 2272759 C CA2272759 C CA 2272759C
- Authority
- CA
- Canada
- Prior art keywords
- acid
- urea
- groups
- molecular weight
- polyurethane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000006185 dispersion Substances 0.000 title claims abstract description 102
- 239000007787 solid Substances 0.000 title claims abstract description 40
- 229920003226 polyurethane urea Polymers 0.000 title claims abstract description 34
- 238000003860 storage Methods 0.000 title description 13
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 47
- 239000002253 acid Substances 0.000 claims abstract description 43
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 39
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 27
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 229920005862 polyol Polymers 0.000 claims abstract description 7
- 150000003077 polyols Chemical class 0.000 claims abstract description 7
- 239000008199 coating composition Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 21
- 229920000728 polyester Polymers 0.000 claims description 14
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 11
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 claims description 9
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 9
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 9
- 229920000515 polycarbonate Polymers 0.000 claims description 9
- 239000004417 polycarbonate Substances 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 claims description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 4
- 229920001223 polyethylene glycol Polymers 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 150000002009 diols Chemical class 0.000 description 19
- 238000000576 coating method Methods 0.000 description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000010408 film Substances 0.000 description 9
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 8
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 8
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 8
- 239000004814 polyurethane Substances 0.000 description 8
- 229940113165 trimethylolpropane Drugs 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 229920000570 polyether Polymers 0.000 description 6
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 5
- 229920002396 Polyurea Polymers 0.000 description 5
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 5
- -1 aromatic isocyanates Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229920002635 polyurethane Polymers 0.000 description 5
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 229960002887 deanol Drugs 0.000 description 4
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- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- 125000003010 ionic group Chemical group 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 239000000049 pigment Substances 0.000 description 4
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000005056 polyisocyanate Substances 0.000 description 3
- 229920001228 polyisocyanate Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- VYZKQGGPNIFCLD-UHFFFAOYSA-N 3,3-dimethylhexane-2,2-diol Chemical compound CCCC(C)(C)C(C)(O)O VYZKQGGPNIFCLD-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VMOWKUTXPNPTEN-UHFFFAOYSA-N n,n-dimethylpropan-2-amine Chemical compound CC(C)N(C)C VMOWKUTXPNPTEN-UHFFFAOYSA-N 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
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- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- FDYWJVHETVDSRA-UHFFFAOYSA-N 1,1-diisocyanatobutane Chemical compound CCCC(N=C=O)N=C=O FDYWJVHETVDSRA-UHFFFAOYSA-N 0.000 description 1
- NNOZGCICXAYKLW-UHFFFAOYSA-N 1,2-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC=C1C(C)(C)N=C=O NNOZGCICXAYKLW-UHFFFAOYSA-N 0.000 description 1
- GHXPTDPKJYFMOE-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)cyclohexane Chemical compound O=C=NCC1CCCCC1CN=C=O GHXPTDPKJYFMOE-UHFFFAOYSA-N 0.000 description 1
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- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920003009 polyurethane dispersion Polymers 0.000 description 1
- 229920006264 polyurethane film Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- C08G18/08—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
- C08G18/0804—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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Manufacturing & Machinery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19824484A DE19824484A1 (de) | 1998-06-02 | 1998-06-02 | Festkörperreiche Polyurethandispersionen mit hoher Applikationssicherheit |
| DE19824484.3 | 1998-06-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2272759A1 CA2272759A1 (en) | 1999-12-02 |
| CA2272759C true CA2272759C (en) | 2007-08-07 |
Family
ID=7869585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002272759A Expired - Fee Related CA2272759C (en) | 1998-06-02 | 1999-05-28 | High solids polyurethane-urea dispersions having improved storage stability |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6084051A (enExample) |
| EP (1) | EP0962476B1 (enExample) |
| JP (1) | JP4620196B2 (enExample) |
| AT (1) | ATE293645T1 (enExample) |
| CA (1) | CA2272759C (enExample) |
| DE (2) | DE19824484A1 (enExample) |
| ES (1) | ES2241207T3 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10004723A1 (de) * | 2000-02-03 | 2001-08-09 | Bayer Ag | Wässrige Sperrschicht auf Basis von Polyurethan-Disperionen |
| CA2363642C (en) * | 1999-02-25 | 2009-12-01 | Bayer Aktiengesellschaft | Aqueous barrier coat based on polyurethane dispersions |
| DE10011277A1 (de) * | 2000-03-08 | 2001-09-13 | Bayer Ag | Abziehlack |
| DE10052875A1 (de) * | 2000-08-14 | 2002-02-28 | Bayer Ag | Wässrige Dispersionen |
| ITMI20012779A1 (it) * | 2001-12-21 | 2003-06-21 | Alcantara Spa | Procedimento per la preparazione di un materiale tessile composito e il materiale tessile composito cosi' ottenuto di elevata durabilita' e' |
| JP2004075781A (ja) * | 2002-08-13 | 2004-03-11 | Nippon Polyurethane Ind Co Ltd | アロファネート変性ブロックポリイソシアネートの製造方法 |
| US20070020463A1 (en) * | 2004-12-23 | 2007-01-25 | Trainham James A | Flexible polymer coating and coated flexible substrates |
| US20040116594A1 (en) * | 2002-12-11 | 2004-06-17 | Debkumar Bhattacharjee | Polyurethane prepolymer, stable aqueous dispersions with high solids containing the same and method of using and preparing the aqueous dispersions |
| US20040185231A1 (en) * | 2003-02-28 | 2004-09-23 | Dimmick William Joseph | Polymer coated surfaces having inlaid decorative sheets |
| JP4461222B2 (ja) * | 2003-03-04 | 2010-05-12 | セイコーエプソン株式会社 | 顔料分散水性記録液および印刷物 |
| US7045573B2 (en) * | 2003-04-21 | 2006-05-16 | Bayer Materialscience Llc | Polyurethane dispersion (PUD) with improved isopropanol resistance, flexibility and softness |
| US20060149020A1 (en) * | 2003-04-21 | 2006-07-06 | Eduard Mayer | Polyurethane dispersion (PUD) with improved isopropanol resistance, flexibility and softness |
| US20040249106A1 (en) * | 2003-06-03 | 2004-12-09 | Gindin Lyubov K. | Modified polyurethanes |
| AT412648B (de) | 2003-06-27 | 2005-05-25 | Surface Specialties Austria | Wasserverdünnbare polyurethandispersionen |
| US7342068B2 (en) * | 2003-11-18 | 2008-03-11 | Air Products And Chemicals, Inc. | Aqueous polyurethane dispersion and method for making and using same |
| US20070149750A1 (en) * | 2003-11-26 | 2007-06-28 | Bayer Materialscience Llc | Solid powder coating crosslinker |
| US20050113548A1 (en) * | 2003-11-26 | 2005-05-26 | Roesler Richard R. | Solid powder coating crosslinker |
| US6894138B1 (en) | 2003-11-26 | 2005-05-17 | Bayer Materialscience Llc | Blocked polyisocyanate |
| JP2006022221A (ja) * | 2004-07-08 | 2006-01-26 | Sanyo Chem Ind Ltd | ポリウレタン樹脂エマルション |
| JP2006089576A (ja) * | 2004-09-22 | 2006-04-06 | Sanyo Chem Ind Ltd | ポリウレタン樹脂水性分散体 |
| JP4249109B2 (ja) * | 2004-09-30 | 2009-04-02 | 三洋化成工業株式会社 | ポリウレタン樹脂エマルション |
| DE102004060139A1 (de) * | 2004-12-13 | 2006-06-29 | Bayer Materialscience Ag | Festkörperreiche Polyurethanpolyharnstoff-Dispersionen |
| US20070185003A1 (en) * | 2006-01-18 | 2007-08-09 | Invista North America S.A.R.L. | Non-textile polymer compositions and methods |
| DE102005019430A1 (de) * | 2005-04-25 | 2006-10-26 | Bayer Materialscience Ag | N-Methylpyrrolidon-freie Polyurethan-Dispersionen auf Basis von Dimethylolpropionsäure |
| DE102005040130A1 (de) * | 2005-08-25 | 2007-03-01 | Bayer Materialscience Ag | Polyurethanpolyharnstoff-Dispersionen |
| KR100726973B1 (ko) * | 2006-02-27 | 2007-06-14 | 한밭대학교 산학협력단 | 청색 발광 형광체 및 그 제조방법 |
| US20100048811A1 (en) * | 2008-08-20 | 2010-02-25 | Marc Chilla | Process for the production of polyurethane urea resin dispersions |
| US9617453B2 (en) | 2009-12-14 | 2017-04-11 | Air Products And Chemicals, Inc. | Solvent free aqueous polyurethane dispersions and methods of making and using the same |
| 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 |
| BR112013022349A2 (pt) | 2011-03-01 | 2018-06-19 | Roidec India Chemicals P Ltd | dispersão de poliuretano com base de óleo natural |
| US9217021B2 (en) * | 2011-07-08 | 2015-12-22 | Defensin Therapeutics Aps | Oral treatment of inflammatory bowel disease |
| KR20150120403A (ko) * | 2013-02-22 | 2015-10-27 | 바스프 에스이 | 수성 폴리우레탄 제형의 제조 방법 |
| JP6805826B2 (ja) * | 2014-06-20 | 2020-12-23 | 宇部興産株式会社 | 水性ポリウレタン樹脂分散体 |
| CN109071750B (zh) | 2016-03-08 | 2022-08-02 | 生活实验公司 | 持久化妆品组合物 |
| BR112020004127A2 (pt) | 2017-09-13 | 2020-09-01 | Living Proof, Inc. | composições protetoras de cor |
| EP3681920B1 (en) | 2017-09-13 | 2025-06-25 | Living Proof, Inc. | Long lasting cosmetic compositions |
| CN111356501A (zh) | 2017-11-20 | 2020-06-30 | 生活实验公司 | 实现持久化妆品性能的属性 |
| BR112020021902B1 (pt) | 2018-04-27 | 2024-02-20 | Living Proof, Inc | Composições cosméticas de poliuretano-ureia para tratamento capilar, método de preservação da ondulação no cabelo humano e os usos de poliuretano-ureia |
| WO2021087769A1 (zh) * | 2019-11-05 | 2021-05-14 | 万华化学集团股份有限公司 | 一种聚氨酯或聚氨酯-脲的水分散体及其制备方法和应用 |
| CN112778487A (zh) * | 2019-11-05 | 2021-05-11 | 万华化学集团股份有限公司 | 一种聚氨酯或聚氨酯-脲的水分散体及其制备方法和应用 |
| WO2025137885A1 (zh) * | 2023-12-26 | 2025-07-03 | 万华化学集团股份有限公司 | 一种聚氨酯或聚氨酯脲的水分散体及其制备方法和应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3922493A1 (de) * | 1989-07-08 | 1991-01-17 | Bayer Ag | Verfahren zur herstellung von waessrigen dispersionen von polyurethanen und ihre verwendung als beschichtungsmittel fuer beliebige substrate |
| DE4013546A1 (de) * | 1990-04-27 | 1991-10-31 | Henkel Kgaa | Verwendung von essigsaeureestern bei der herstellung von polyurethandispersionen |
| JP3145453B2 (ja) * | 1991-12-04 | 2001-03-12 | 大日精化工業株式会社 | ウレタン尿素樹脂水性分散体及びこれを用いた水性印刷インキ |
| DE4140486A1 (de) * | 1991-12-09 | 1993-06-17 | Basf Ag | Waessrige polyurethandispersionen |
| JP3653821B2 (ja) * | 1995-10-06 | 2005-06-02 | 大日本インキ化学工業株式会社 | 水分散性ポリウレタンの製造方法 |
| JPH09165429A (ja) * | 1995-12-15 | 1997-06-24 | Sekisui Chem Co Ltd | ウレタンエマルジョンの製造方法 |
| DE19611850A1 (de) * | 1996-03-26 | 1997-10-02 | Bayer Ag | Verwendung von ionischen und nichtionischen wäßrigen Polyurethandispersionen auf Basis von 1-Methyl-2,4- und/oder -2,6-diisocyanatocyclohexan als Bindemittel für Glasfaserschlichten sowie spezielle ionische und nichtionische wäßrige Polyurethandispersionen auf Basis von 1-Methyl-2,4- und/oder -2,6-diisocyanatocyclohexan |
| EP0792899B1 (de) * | 1996-03-01 | 2003-05-02 | Bayer Ag | In Wasser lösliche oder dispergierbare Polyurethanharnstoffe, ein Verfahren zu deren Herstellung und ihre Verwendung zur Beschichtung beliebiger Substrate |
-
1998
- 1998-06-02 DE DE19824484A patent/DE19824484A1/de not_active Withdrawn
-
1999
- 1999-05-20 DE DE59911923T patent/DE59911923D1/de not_active Expired - Lifetime
- 1999-05-20 ES ES99109891T patent/ES2241207T3/es not_active Expired - Lifetime
- 1999-05-20 EP EP99109891A patent/EP0962476B1/de not_active Expired - Lifetime
- 1999-05-20 AT AT99109891T patent/ATE293645T1/de active
- 1999-05-25 US US09/318,356 patent/US6084051A/en not_active Expired - Lifetime
- 1999-05-28 CA CA002272759A patent/CA2272759C/en not_active Expired - Fee Related
- 1999-05-31 JP JP15219699A patent/JP4620196B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2000034331A (ja) | 2000-02-02 |
| EP0962476B1 (de) | 2005-04-20 |
| ES2241207T3 (es) | 2005-10-16 |
| EP0962476A1 (de) | 1999-12-08 |
| DE59911923D1 (de) | 2005-05-25 |
| JP4620196B2 (ja) | 2011-01-26 |
| DE19824484A1 (de) | 1999-12-09 |
| ATE293645T1 (de) | 2005-05-15 |
| US6084051A (en) | 2000-07-04 |
| CA2272759A1 (en) | 1999-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |