CA2253119A1 - Hydrophilizing agent precursor, a process for its preparation and its use as a dispersing agent for aqueous polyurethane dispersion - Google Patents
Hydrophilizing agent precursor, a process for its preparation and its use as a dispersing agent for aqueous polyurethane dispersion Download PDFInfo
- Publication number
- CA2253119A1 CA2253119A1 CA002253119A CA2253119A CA2253119A1 CA 2253119 A1 CA2253119 A1 CA 2253119A1 CA 002253119 A CA002253119 A CA 002253119A CA 2253119 A CA2253119 A CA 2253119A CA 2253119 A1 CA2253119 A1 CA 2253119A1
- Authority
- CA
- Canada
- Prior art keywords
- polyurethane dispersion
- hydrophilizing agent
- agent
- precursor
- hydrophilizing
- 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.)
- Abandoned
Links
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 38
- 229920003009 polyurethane dispersion Polymers 0.000 title claims abstract description 14
- 239000002243 precursor Substances 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title claims description 20
- 239000002270 dispersing agent Substances 0.000 title abstract description 22
- 238000002360 preparation method Methods 0.000 title abstract description 8
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims abstract description 20
- -1 acyclic diamines Chemical class 0.000 claims description 18
- 238000000576 coating method Methods 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 10
- 230000003472 neutralizing effect Effects 0.000 claims description 9
- 239000004814 polyurethane Substances 0.000 claims description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- 229920002635 polyurethane Polymers 0.000 claims description 8
- 239000004753 textile Substances 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 239000004033 plastic Substances 0.000 claims description 4
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 3
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 3
- 239000000123 paper Substances 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 9
- 238000006845 Michael addition reaction Methods 0.000 abstract description 5
- 239000000203 mixture Substances 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 150000007942 carboxylates Chemical class 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WHIVNJATOVLWBW-PLNGDYQASA-N (nz)-n-butan-2-ylidenehydroxylamine Chemical compound CC\C(C)=N/O WHIVNJATOVLWBW-PLNGDYQASA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001728 carbonyl compounds Chemical class 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 2
- 239000004922 lacquer Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 150000004692 metal hydroxides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000521257 Hydrops Species 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000003010 ionic group Chemical group 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011527 polyurethane coating Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002023 wood 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
-
- 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
- C08G18/10—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
- C08G18/40—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
- C08G18/40—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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/80—Masked polyisocyanates
- C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
- C08G18/807—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with nitrogen containing compounds
- C08G18/8077—Oximes
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
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)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Paints Or Removers (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Polyurethanes Or Polyureas (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Dental Preparations (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Pens And Brushes (AREA)
- Developing Agents For Electrophotography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19750186.9 | 1997-11-13 | ||
| DE19750186A DE19750186A1 (de) | 1997-11-13 | 1997-11-13 | Hydrophilierungsmittel, ein Verfahren zu dessen Herstellung sowie dessen Verwendung als Dispergator für wäßrige Polyurethan-Dispersionen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2253119A1 true CA2253119A1 (en) | 1999-05-13 |
Family
ID=7848533
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002253119A Abandoned CA2253119A1 (en) | 1997-11-13 | 1998-11-09 | Hydrophilizing agent precursor, a process for its preparation and its use as a dispersing agent for aqueous polyurethane dispersion |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP0916647B1 (https=) |
| JP (1) | JP4143192B2 (https=) |
| KR (1) | KR100585925B1 (https=) |
| AT (1) | ATE286498T1 (https=) |
| CA (1) | CA2253119A1 (https=) |
| CZ (1) | CZ295390B6 (https=) |
| DE (2) | DE19750186A1 (https=) |
| DK (1) | DK0916647T3 (https=) |
| ES (1) | ES2236860T3 (https=) |
| NO (1) | NO323973B1 (https=) |
| PT (1) | PT916647E (https=) |
| SI (1) | SI0916647T1 (https=) |
| TW (1) | TW444037B (https=) |
Cited By (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7041768B2 (en) | 2003-02-26 | 2006-05-09 | Bayer Materialscience Ag | Polyurethane coating systems |
| US7074852B2 (en) * | 2003-06-27 | 2006-07-11 | Bayer Materialscience Ag | Blocked polyisocyanates |
| US7087676B2 (en) | 2003-06-27 | 2006-08-08 | Bayer Materialscience Ag | Blocked polyisocyanates |
| US7091280B2 (en) | 2002-01-17 | 2006-08-15 | Bayer Aktiengesellschaft | Stabilized aqueous polyurethane-polyurea dispersions |
| US7276554B2 (en) | 2004-01-16 | 2007-10-02 | Bayer Materialscience Ag | Coating material composition |
| US7345110B2 (en) | 2004-04-08 | 2008-03-18 | Bayer Materialscience Ag | Process for the continuous production of an aqueous polyurethane dispersion |
| US7361723B2 (en) | 2004-03-17 | 2008-04-22 | Bayer Materialscience Ag | Low-viscosity allophanates containing actinically curable groups |
| US7381785B2 (en) | 2004-03-17 | 2008-06-03 | Bayer Meterialscience Ag | Preparation of new radiation-curing binders |
| US7485681B2 (en) | 2006-09-29 | 2009-02-03 | Bayer Materialscience Ag | Aqueous coating compositions based on polyurethane dispersions |
| US7659338B2 (en) | 2003-12-22 | 2010-02-09 | Bayer Materialscience Ag | Dispersions |
| US7972982B2 (en) | 2008-03-14 | 2011-07-05 | Bayer Materialscience Ag | Aqueous dispersion of anionically modified polyurethane ureas for coating a sheet-form textile material |
| US8071659B2 (en) | 2007-08-25 | 2011-12-06 | Bayer Materialscience Ag | Process for preparing low-viscosity allophanates containing actinically curable groups |
| US8106140B2 (en) | 2007-08-25 | 2012-01-31 | Bayer Materialscience Ag | Process for preparing low-viscosity allophanates containing actinically curable groups |
| US8114931B2 (en) | 2003-09-18 | 2012-02-14 | Bayer Materialscience Ag | Aqueous adhesive dispersions |
| US8231976B2 (en) | 2008-04-28 | 2012-07-31 | Bayer Materialscience Ag | Block-resistant, radiation-curable coating systems based on high molecular mass, aqueous polyurethane dispersions |
| US8343601B1 (en) | 2011-07-06 | 2013-01-01 | Bayer Materialscience Llc | Waterborne polyurethane coating compositions |
| US8354151B1 (en) | 2011-07-06 | 2013-01-15 | Bayer Materialscience Llc | Waterborne polyurethane coating compositions |
| US8629195B2 (en) | 2006-04-08 | 2014-01-14 | Bayer Materialscience Ag | Production of polyurethane foams |
| US8853295B2 (en) | 2009-02-12 | 2014-10-07 | Allnex Ip S.A.R.L. | Process for the preparation of particularly reactive and low-viscosity allophanates having actinic-curable groups and the use thereof for the preparation of particularly scratch-resistant coatings |
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| US7091280B2 (en) | 2002-01-17 | 2006-08-15 | Bayer Aktiengesellschaft | Stabilized aqueous polyurethane-polyurea dispersions |
| US7041768B2 (en) | 2003-02-26 | 2006-05-09 | Bayer Materialscience Ag | Polyurethane coating systems |
| US7074852B2 (en) * | 2003-06-27 | 2006-07-11 | Bayer Materialscience Ag | Blocked polyisocyanates |
| US7087676B2 (en) | 2003-06-27 | 2006-08-08 | Bayer Materialscience Ag | Blocked polyisocyanates |
| US8114931B2 (en) | 2003-09-18 | 2012-02-14 | Bayer Materialscience Ag | Aqueous adhesive dispersions |
| US7659338B2 (en) | 2003-12-22 | 2010-02-09 | Bayer Materialscience Ag | Dispersions |
| US7276554B2 (en) | 2004-01-16 | 2007-10-02 | Bayer Materialscience Ag | Coating material composition |
| US7361723B2 (en) | 2004-03-17 | 2008-04-22 | Bayer Materialscience Ag | Low-viscosity allophanates containing actinically curable groups |
| US7381785B2 (en) | 2004-03-17 | 2008-06-03 | Bayer Meterialscience Ag | Preparation of new radiation-curing binders |
| US7960446B2 (en) | 2004-03-17 | 2011-06-14 | Bayer Materialscience Ag | Low-viscosity allophanates containing actinically curable groups |
| US7345110B2 (en) | 2004-04-08 | 2008-03-18 | Bayer Materialscience Ag | Process for the continuous production of an aqueous polyurethane dispersion |
| US8629195B2 (en) | 2006-04-08 | 2014-01-14 | Bayer Materialscience Ag | Production of polyurethane foams |
| US7485681B2 (en) | 2006-09-29 | 2009-02-03 | Bayer Materialscience Ag | Aqueous coating compositions based on polyurethane dispersions |
| US8933146B2 (en) | 2007-08-11 | 2015-01-13 | Bayer Materialscience Ag | Process for producing hard coating systems based on aqueous polyurethane dispersions |
| US8106140B2 (en) | 2007-08-25 | 2012-01-31 | Bayer Materialscience Ag | Process for preparing low-viscosity allophanates containing actinically curable groups |
| US8071659B2 (en) | 2007-08-25 | 2011-12-06 | Bayer Materialscience Ag | Process for preparing low-viscosity allophanates containing actinically curable groups |
| US7972982B2 (en) | 2008-03-14 | 2011-07-05 | Bayer Materialscience Ag | Aqueous dispersion of anionically modified polyurethane ureas for coating a sheet-form textile material |
| US9410013B2 (en) | 2008-04-03 | 2016-08-09 | Covestro Deutschland Ag | Hot melts |
| US9469716B2 (en) | 2008-04-18 | 2016-10-18 | Covestro Deutschland Ag | Single-component polyurethane system comprising aqueous or water-soluble polyurethanes |
| US8231976B2 (en) | 2008-04-28 | 2012-07-31 | Bayer Materialscience Ag | Block-resistant, radiation-curable coating systems based on high molecular mass, aqueous polyurethane dispersions |
| US8853295B2 (en) | 2009-02-12 | 2014-10-07 | Allnex Ip S.A.R.L. | Process for the preparation of particularly reactive and low-viscosity allophanates having actinic-curable groups and the use thereof for the preparation of particularly scratch-resistant coatings |
| US9034985B2 (en) | 2009-02-13 | 2015-05-19 | Bayer Materialscience Ag | Aqueous coating systems based on physically drying urethane acrylates |
| US8865832B2 (en) | 2009-10-31 | 2014-10-21 | Bayer Materialscience Ag | Tin-free aqueous polyurethane dispersions |
| US9676894B2 (en) | 2010-03-02 | 2017-06-13 | Covestro Deutschland Ag | Aqueous polyurethane dispersions |
| US9321893B2 (en) | 2010-03-09 | 2016-04-26 | Covestro Deutschland Ag | Radiation-curable whipped foams |
| US9206331B2 (en) | 2010-04-14 | 2015-12-08 | Covestro Deutschland Ag | Aqueous polyurethane-polyurea dispersions |
| US9034472B2 (en) | 2011-01-20 | 2015-05-19 | Allnex Ip S.A.R.L. | Non-aqueous polyurethane coating compositions |
| US9273210B2 (en) | 2011-03-29 | 2016-03-01 | Covestro Deutschland Ag | Use of an aqueous preparation for the coating of wood surfaces to achieve a natural-touch effect |
| US9364577B2 (en) | 2011-05-04 | 2016-06-14 | Covestro Deutschland Ag | Hydrophilic polyurethane foam with low volume swelling |
| US8354151B1 (en) | 2011-07-06 | 2013-01-15 | Bayer Materialscience Llc | Waterborne polyurethane coating compositions |
| US8343601B1 (en) | 2011-07-06 | 2013-01-01 | Bayer Materialscience Llc | Waterborne polyurethane coating compositions |
| US9546490B2 (en) | 2011-08-09 | 2017-01-17 | Covestro Deutschland Ag | Method for reinforcing a building component |
| USRE48584E1 (en) | 2011-08-09 | 2021-06-08 | Covestro Deutschland Ag | Method for reinforcing a building component |
| US8932722B2 (en) | 2011-10-14 | 2015-01-13 | Allnex Ip S.A.R.L. | Process for the preparation of low-viscosity, water-dilutable urethane (meth)acrylates |
| US9631117B2 (en) | 2011-10-14 | 2017-04-25 | Allnex Ip S.A.R.L. | Process for the preparation of low-viscosity, water-dilutable urethane (meth)acrylates |
| US9783926B2 (en) | 2011-10-18 | 2017-10-10 | Covestro Deutschland Ag | Process for the coating of textiles |
| US9624621B2 (en) | 2011-10-21 | 2017-04-18 | Covestro Deutschland Ag | Process for the production of coated textiles |
| US9195215B2 (en) | 2011-11-29 | 2015-11-24 | Bayer Intellectual Property Gmbh | Holographic medium having a protective layer |
| US10717805B2 (en) | 2015-04-21 | 2020-07-21 | Covestro Deutschland Ag | Process for producing polyisocyanurate plastics |
| US11286331B2 (en) | 2015-04-21 | 2022-03-29 | Covestro Deutschland Ag | Hydrophilically modified polyisocyanurate plastic and process for production thereof |
| US10590226B2 (en) | 2015-04-21 | 2020-03-17 | Covestro Deutschland Ag | Solids based on polyisocyanurate polymers produced under adiabatic conditions |
| US10752724B2 (en) | 2015-04-21 | 2020-08-25 | Covestro Deutschland Ag | Process for producing polyisocvanurate plastics having functionalized surfaces |
| US10597484B2 (en) | 2015-04-21 | 2020-03-24 | Covestro Deutschland Ag | Polyisocyanurate plastics having high thermal stability |
| US10752723B2 (en) | 2015-04-21 | 2020-08-25 | Covestro Deutschland Ag | Polyisocyanurate polymer and process for the production of polyisocyanurate polymers |
| US11390707B2 (en) | 2015-04-21 | 2022-07-19 | Covestro Deutschland Ag | Polyisocyanurate polymers and process for the production of polyisocyanurate polymers |
| US11286332B2 (en) | 2015-04-21 | 2022-03-29 | Covestro Deutschland Ag | Hydrophobically modified polyisocyanurate plastic and method for production thereof |
| US10752727B1 (en) | 2015-07-10 | 2020-08-25 | Covestro Deutschland Ag | Process and apparatus for continuous production of aqueous polyurethane dispersions |
| US11511211B2 (en) | 2016-06-28 | 2022-11-29 | Covestro Deutschland Ag | Distillative separation of ketazine from polyurethane dispersions |
| US10934386B2 (en) | 2016-07-28 | 2021-03-02 | Covestro Deutschland Ag | Polyurethane dispersions of low hardness |
| US11981095B2 (en) | 2016-11-25 | 2024-05-14 | Stratasys, Inc. | Method for producing an at least partially coated object |
| US11685805B2 (en) | 2016-12-19 | 2023-06-27 | Covestro Deutschland Ag | Aqueous dispersion of polyurethane |
| WO2019206693A1 (en) * | 2018-04-25 | 2019-10-31 | Basf Se | Aqueous dispersion of a polyurethane comprising a dicarboxylate with one or two secondary amino group |
| US12577445B2 (en) | 2019-09-04 | 2026-03-17 | Covestro Deutschland Ag | Dispersion adhesives |
Also Published As
| Publication number | Publication date |
|---|---|
| DE59812469D1 (de) | 2005-02-10 |
| EP0916647B1 (de) | 2005-01-05 |
| DK0916647T3 (da) | 2005-03-29 |
| EP0916647A2 (de) | 1999-05-19 |
| ES2236860T3 (es) | 2005-07-16 |
| KR19990045231A (ko) | 1999-06-25 |
| NO985277L (no) | 1999-05-14 |
| JPH11228811A (ja) | 1999-08-24 |
| EP0916647A3 (de) | 2003-04-09 |
| NO985277D0 (no) | 1998-11-12 |
| JP4143192B2 (ja) | 2008-09-03 |
| SI0916647T1 (en) | 2005-04-30 |
| TW444037B (en) | 2001-07-01 |
| DE19750186A1 (de) | 1999-05-20 |
| CZ367798A3 (cs) | 1999-06-16 |
| PT916647E (pt) | 2005-05-31 |
| NO323973B1 (no) | 2007-07-30 |
| KR100585925B1 (ko) | 2006-07-25 |
| CZ295390B6 (cs) | 2005-07-13 |
| ATE286498T1 (de) | 2005-01-15 |
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| EEER | Examination request | ||
| FZDE | Discontinued |