EP0342199A1 - Polyetherurethane, procede pour sa fabrication, adjuvant d'egalisation et emploi du polyetherurethane - Google Patents
Polyetherurethane, procede pour sa fabrication, adjuvant d'egalisation et emploi du polyetherurethaneInfo
- Publication number
- EP0342199A1 EP0342199A1 EP88901245A EP88901245A EP0342199A1 EP 0342199 A1 EP0342199 A1 EP 0342199A1 EP 88901245 A EP88901245 A EP 88901245A EP 88901245 A EP88901245 A EP 88901245A EP 0342199 A1 EP0342199 A1 EP 0342199A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- atoms
- parts
- polyether urethane
- same
- agent according
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 239000000654 additive Substances 0.000 title abstract description 31
- 230000000996 additive effect Effects 0.000 title abstract description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 239000003973 paint Substances 0.000 claims abstract description 7
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 17
- 229920000570 polyether Polymers 0.000 claims description 17
- -1 ether diol Chemical class 0.000 claims description 15
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 12
- 229920001281 polyalkylene Polymers 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 239000013067 intermediate product Substances 0.000 claims description 4
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 4
- 229920000180 alkyd Polymers 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 2
- 150000003673 urethanes Chemical class 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000011230 binding agent Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 15
- 239000008367 deionised water Substances 0.000 description 13
- 229910021641 deionized water Inorganic materials 0.000 description 13
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 9
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000004658 ketimines Chemical group 0.000 description 7
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 6
- 239000012362 glacial acetic acid Substances 0.000 description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 150000003335 secondary amines Chemical group 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KQEIJFWAXDQUPR-UHFFFAOYSA-N 2,4-diaminophenol;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=C(O)C(N)=C1 KQEIJFWAXDQUPR-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 238000004070 electrodeposition Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- MIJDSYMOBYNHOT-UHFFFAOYSA-N 2-(ethylamino)ethanol Chemical compound CCNCCO MIJDSYMOBYNHOT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 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 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000007591 painting process Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229920006301 statistical copolymer Polymers 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4825—Polyethers containing two hydroxy groups
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4488—Cathodic paints
- C09D5/4492—Cathodic paints containing special additives, e.g. grinding agents
-
- 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
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/47—Levelling agents
Definitions
- the film defects such as craters and the like, which are well known to the person skilled in the art, can then occur due to the incompatibility between the lacquer binder and the contamination.
- silicone oils can be water-miscible or immiscible. They can also be modified with reactive groups, e.g. with hydroxyl or amino groups. What this group of additives has in common, however, is that although they can eliminate the surface defects, they generally cause serious adhesion problems for subsequent layers of paint such as fillers and topcoats.
- Japanese patent application J 6 1115 974 describes a reaction product made from a polyepoxy resin modified with dimer fatty acid with polyoxyalkylene polyamine. This product is intended to suppress the tendency of KTL materials to crater.
- EP 70 550 describes a reaction product of a polyepoxy resin with a polyoxylalkylene polyamine with primary amino groups. This material is also intended to improve the KTL films by eliminating or at least minimizing the tendency to crater. But these products also lead to sustained interim liability problems for fillers and top coats.
- Polyether urethane process for its preparation, leveling agents and use of the polyether urethane
- the invention relates to a polyether urethane, a process for its preparation, a leveling aid and the use of the polyether urethane.
- KTL Cationic electrocoating
- Electrocoating baths of the type described above are e.g. disclosed in the following patent documents: U.S. Patent 3,799,854; U.S. Patent 3,984,299; U.S. Patent 4,031,050; U.S. Patent 4,252,703; U.S. Patent 4,332,711 and German Patent 3108073.
- these impurities are removed with in the polyether urethane according to the invention and its use in particular in aqueous, cathodically depositable electrocoat materials.
- the polyalkylene ether diols are reaction products of water, aliphatic or aromatic diols and monoepoxides.
- the molecular weight can be varied within wide limits via the stoichiometry. Molecular weights between 500 and 8000 are preferred for the purpose according to the invention, in particular molecular weights between 1000 and 5000 are preferred.
- the person skilled in the art is familiar with the suitable monoepoxides. These include e.g. Ethylene oxide, propylene oxide and butylene oxide. These can be used individually or as a mixture. If a polyalkylene ether from various monoepoxides is desired, this is the case
- aliphatic diols are suitable as aliphatic diols; diols with primary hydroxyl groups, ie diols such as ethylene glycol or diethylene glycol, are preferred.
- Resorzinol, bisphenol A and bisphenol F have proven particularly useful as aromatic diols.
- Aromatic and aliphatic diisocyanates are suitable for chain extension of the polyalkylene ether diols. These classes of substances are also familiar to the person skilled in the art, so that only a few suitable types are to be mentioned here as representative. These include tolylene diisocyanate, 4,4'-diisocyanatodiphenylmethane, hexamethylene diisocyanate and isophorone diisocyanate. These isocyanates are reacted at room temperature or at elevated temperature, if appropriate in the presence of solvents which cannot react with isocyanate groups. The reaction can be accelerated with the usual catalysts for the isocyanate-hydroxyl group reaction.
- Organotin compounds such as dibutyltin dilaurate are particularly suitable.
- KTL binders reduce the tendency to craters and, on the other hand, can react via functional groups with the auxiliary in the KTL binder during the stoving process.
- These additives are reaction products of polyalkyl ether diols with aromatic and / or aliphatic diisocyanates in a molar ratio of approximately n: (n + 1); the remaining isocyanate groups are further modified with secondary amines in a second reaction step.
- the invention thus relates to a polyether urethane of the general formula
- R 1 H or an alkyd radical having 1 to 8 carbon atoms
- R 2 the alkylene radical with 2 to 10 C atoms or a cycloalkylene radical with 6 to 20 C atoms or an arylene radical with 6 to 20 C atoms R 3 ,
- R 4 an optionally substituted alkyl radical with 1 to 8 carbon atoms or a common ring, the members of which are R 3 and
- the invention further relates to a process for the preparation of a polyether urethane in which a polyalkylene ether diol with an excess of aromatic and / or aliphatic diisocyanates is converted into an intermediate product with terminal isocyanate groups and then these isocyanate groups are reacted with secondary amines, a leveling agent for aqueous lacquers consisting of or containing The polyalkylene ether diols are reacted with the diisocyanates in such stoichiometric amounts that the intermediate product has terminal isocyanate groups.
- the ratio of polyalkylene ether to diisocyanate is approximately n: (n + 1).
- terminal I socyanate groups are then reacted further with secondary amines in a subsequent reaction step.
- the suitable secondary amines belong to the dialkylamines such as dimethylamine or dibutylamine, to the alkylalkanolamines such as methylethanolamine or ethylethanolamine, to the dialkanolamines such as diethanolamine.
- Polyamines with a secondary amino group and further primary amino groups are also suitable.
- the primary amino groups must be blocked before the reaction with the intermediate products containing isocyanate groups, in order to prevent undesired chain extension or gelling.
- a well known method for blocking primary amino groups is the reaction with ke tonen.
- a polyamine modified in this way is the diketimine from diethylene triamine and methyl isobutyl ketone.
- the additives can be added during the production of the KTL binders, but they can also be converted separately into the aqueous solution by adding organic acids and water. If required, this aqueous solution can now be added to the KTL bath in suitable amounts, preferably between 1 and 20 parts by weight of the additive (solid) on KTL binder (solid).
- the KTL binders and pigment pastes used correspond to Example 2 (binder dispersion) of DE-PS 3108073 and Example 7 (pigment paste) of EP 102501 B1.
- the diisocyanate is initially charged with methyl isobutyl ketone (MIBK) in a suitable reaction vessel under nitrogen, heated to 50 ° C. and mixed with dibutyltin dilaurate.
- MIBK methyl isobutyl ketone
- the polyalkylene ether diol is then run in at a rate such that the temperature does not exceed 70.degree.
- the secondary amine is added. The temperature is allowed to rise to 90 ° C and is held until all isocyanate groups have reacted.
- MIBK methyl isobutyl ketone
- Pluriol PE 3100 polyalkylene ether diol from BASF AG, copolymer based on ethylene oxide-propylene oxide,
- Pluriol PE 6200 Polyethylene ether diol from BASF AG, copolymer based on ethylene oxide - propylene oxide,
- Dianol 3310 Polyalkylene ether diol from AKZO based on ethoxylated bisphenol A, molecular weight 1020
- Example 2 of DE-PS 3108073 The preparation of the binder dispersion is described in Example 2 of DE-PS 3108073. This dispersion without additives serves as a comparison dispersion.
- additive Ib 203.5 parts of additive I are mixed with 7.22 parts of glacial acetic acid and 338.1 parts of deionized water. This additive mixture is then slowly stirred into 4500 parts of binder dispersion. A solid of 30% is then adjusted with a further 1193.2 parts of water. The additive content is 9.5% solid on solid. Dispersion Ib
- the production takes place analogously to la.
- the weights are:
- the additive content is 13% solid on solid.
- the production takes place analogously to la.
- the weights are:
- the additive content is 6% solid on solid.
- the production takes place analogously to la.
- the weights are:
- the additive content is 9.5% solid on solid.
- the production takes place analogously to la.
- the weights are:
- the production takes place analogously to la.
- the weights are:
- the additive content is 13% solid on solid.
- 1675 parts of deionized water are placed in a suitable vessel and 25 parts of 10% acetic acid are added. 2279 parts of the binder dispersion and 775 parts of the pigment paste are stirred into this and made up with 246 parts of deionized water. The paint baths of the deposits are aged for 3 days with stirring.
- the films were deposited on zinc-phosphated steel sheets, which were connected as cathode, at 300 V for 2 min. After the usual post-treatment, the films were baked at 175 ° C for 20 minutes.
- Liability 1 0.5 0 0.5 0 1 0 0.5
- the KTL tapes were then contaminated with 0.1% ASTM oil. The oil was stirred in one day. The baths were then separated as described above.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Excavating Of Shafts Or Tunnels (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Polyétheruréthane de formule générale (I), dans laquelle R1 est H ou un résidu alkyle avec 1 à 8 atomes de carbone, R2 est un résidu alkylène avec 2 à 10 atomes de carbone ou un résidu cycloalkylène avec 6 à 20 atomes de carbone ou bien un résidu arylène avec 6 à 20 atomes de carbone, R3 et R4 sont un résidu alkyle, éventuellement substitué, avec 1 à 8 atomes de carbone ou un composé cyclique commun dont les côtés sont R3 et R4, n vaut entre 2 et 180 et m vaut entre 1 et 15. Sont également décrits un procédé pour produire ledit polyétheruréthane, un adjuvant d'égalisation pour des vernis aqueux, ainsi que l'emploi du polyétheruréthane comme adjuvant d'égalisation dans des vernis électrophorétiques aqueux séparables cathodiquement.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3701547 | 1987-01-21 | ||
| DE19873701547 DE3701547A1 (de) | 1987-01-21 | 1987-01-21 | Polyetherurethan, verfahren zu seiner herstellung, verlaufshilfsmittel und verwendung des polyetherurethans |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0342199A1 true EP0342199A1 (fr) | 1989-11-23 |
Family
ID=6319160
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19880100762 Expired - Lifetime EP0279198B1 (fr) | 1987-01-21 | 1988-01-20 | Composition pour le trempage électro-phorétique |
| EP88901245A Pending EP0342199A1 (fr) | 1987-01-21 | 1988-01-20 | Polyetherurethane, procede pour sa fabrication, adjuvant d'egalisation et emploi du polyetherurethane |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19880100762 Expired - Lifetime EP0279198B1 (fr) | 1987-01-21 | 1988-01-20 | Composition pour le trempage électro-phorétique |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5879754A (fr) |
| EP (2) | EP0279198B1 (fr) |
| JP (1) | JPH0649841B2 (fr) |
| AT (1) | ATE78269T1 (fr) |
| BR (1) | BR8807325A (fr) |
| DE (2) | DE3701547A1 (fr) |
| ES (1) | ES2042604T3 (fr) |
| WO (1) | WO1988005445A1 (fr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3741538A1 (de) * | 1987-12-08 | 1989-06-22 | Bayer Ag | Polyurethanharnstoffe |
| AT392074B (de) * | 1988-10-13 | 1991-01-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von bindemittelkombinationen fuer kathodisch abscheidbare lacke |
| DE3919547A1 (de) * | 1989-06-15 | 1990-12-20 | Ruetgerswerke Ag | Haertungsmittel fuer epoxidharze |
| DE3924694A1 (de) * | 1989-07-26 | 1991-01-31 | Basf Lacke & Farben | Verfahren zum beschichten elektrisch leitfaehiger substrate, waessriger lack, verfahren zur herstellung eines urethangruppenhaltigen adduktes und urethangruppenhaltiges addukt |
| US5389720A (en) * | 1990-05-25 | 1995-02-14 | Miles Inc. | Aqueous polyisocyanate dispersions |
| DE4215480A1 (de) * | 1992-05-11 | 1993-11-18 | Hoechst Ag | Elektrotauchlackbad enthaltend ein Urethan |
| DE4311923A1 (de) * | 1993-04-10 | 1994-10-13 | Huels Chemische Werke Ag | Zweikomponentig zu verarbeitende Beschichtungszusammensetzung zur Herstellung von PUR-Elastomeren |
| PL335694A1 (en) | 1997-03-17 | 2000-05-08 | Dow Chemical Co | Polyurethane latexes, methods of obtaining them and polymers produced from such latexes |
| NO20001904L (no) * | 1999-04-14 | 2000-10-16 | Dow Chemical Co | Polyuretanfilmer fremstilt ved elektrolytisk utfelling fra polyuretandispersjoner |
| NO20001903L (no) | 1999-04-14 | 2000-10-16 | Dow Chemical Co | Polyuretan-filmer fremstilt fra polyuretan-dispersjoner |
| DE10353638A1 (de) * | 2003-11-17 | 2005-06-23 | Basf Coatings Ag | Strukturviskose, wässrige Dispersionen, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US7828994B2 (en) * | 2004-10-26 | 2010-11-09 | Ortec, Inc. | Conductive paint compositions for forming conductive coatings on substrates |
| EP1792925B1 (fr) * | 2005-12-01 | 2015-10-07 | Henkel AG & Co. KGaA | Nouveau matériau formant des structures supramoleculaires, procédé et utilisations |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1069383B (de) * | 1954-08-13 | 1959-11-19 | E. I. Du Pont De Nemours And Company, Wilmington, Del. (V. St. A.) | Verfahren zur Stabilisierung kautschukartiger Produkte |
| DE1078321B (de) * | 1957-08-13 | 1960-03-24 | Bayer Ag | Verfahren zur Herstellung von homogenen verformten Elastomeren oder Schaumstoffen |
| US3799854A (en) | 1970-06-19 | 1974-03-26 | Ppg Industries Inc | Method of electrodepositing cationic compositions |
| US3984299A (en) | 1970-06-19 | 1976-10-05 | Ppg Industries, Inc. | Process for electrodepositing cationic compositions |
| BE791999A (fr) * | 1971-11-30 | 1973-03-16 | Witco Chemical Corp | Solution de laque de polyurethane derivant du di-isocyanate de toluene et son procede de fabrication ( |
| US4046729A (en) * | 1975-06-02 | 1977-09-06 | Ppg Industries, Inc. | Water-reduced urethane coating compositions |
| US4009307A (en) * | 1975-07-24 | 1977-02-22 | Ppg Industries, Inc. | Polyurea-urethane coatings |
| US4155892A (en) * | 1975-10-03 | 1979-05-22 | Rohm And Haas Company | Polyurethane thickeners for aqueous compositions |
| US4137276A (en) * | 1977-08-19 | 1979-01-30 | National Starch And Chemical Corporation | Flexible film laminating adhesives |
| US4136070A (en) * | 1977-10-31 | 1979-01-23 | E. I. Du Pont De Nemours And Company | Cathodic electrodeposition of paints |
| AT356779B (de) | 1978-03-13 | 1980-05-27 | Herberts & Co Gmbh | Kathodisch abscheidbares waesseriges elektro- tauchlack-ueberzugsmittel |
| DE2843790A1 (de) * | 1978-10-06 | 1980-04-17 | Bayer Ag | Verfahren zur herstellung von waessrigen dispersionen oder loesungen von polyurethan-polyharnstoffen, die nach diesem verfahren erhaeltlichen dispersionen oder loesungen, sowie ihre verwendung |
| JPS5580436A (en) | 1978-12-11 | 1980-06-17 | Shell Int Research | Thermoplastic resin binding composition* preparing same* and using same as coating material |
| AT366400B (de) * | 1979-04-09 | 1982-04-13 | Vianova Kunstharz Ag | Verfahren zur herstellung kathodisch abscheidbarer lackbindemittel |
| DE3108073C2 (de) | 1981-03-04 | 1983-10-06 | Basf Farben + Fasern Ag, 2000 Hamburg | Wasserdispergierbare Bindemittel für kationische Elektrotauchlacke |
| DE3300545A1 (de) * | 1983-01-10 | 1984-07-12 | Basf Farben + Fasern Ag, 2000 Hamburg | Wasserdispergierbare bindemittel fuer kationische elektrotauchlacke und verfahren zu ihrer herstellung |
| US4522986A (en) * | 1984-07-20 | 1985-06-11 | General Motors Corporation | Urea flow control agents for urethane paint prepared by reaction of an isocyanate-terminated prepolymer and an ethanolamine |
| DE3438563A1 (de) * | 1984-10-20 | 1986-04-24 | Bayer Ag, 5090 Leverkusen | Waessrige loesungen oder dispersionen von polyisocyanat-additionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als beschichtungsmittel oder als leimungsmittel fuer papier |
| US4742095A (en) * | 1985-07-25 | 1988-05-03 | Mobay Corporation | Continuous process for the production of aqueous polyurethane-urea dispersions |
| DE3613492A1 (de) * | 1986-04-22 | 1987-10-29 | Bayer Ag | Verfahren zur herstellung von waessrigen dispersionen von polyurethan-polyharnstoffen, die nach diesem verfahren erhaeltlichen dispersionen und ihre verwendung als oder zur herstellung von beschichtungsmitteln |
| AT388924B (de) * | 1987-11-03 | 1989-09-25 | Vianova Kunstharz Ag | Verfahren zur herstellung von kationischen lackbindemitteln auf basis von polyetherurethanen und deren verwendung |
-
1987
- 1987-01-21 DE DE19873701547 patent/DE3701547A1/de not_active Withdrawn
-
1988
- 1988-01-20 AT AT88100762T patent/ATE78269T1/de not_active IP Right Cessation
- 1988-01-20 EP EP19880100762 patent/EP0279198B1/fr not_active Expired - Lifetime
- 1988-01-20 JP JP63501455A patent/JPH0649841B2/ja not_active Expired - Lifetime
- 1988-01-20 DE DE88100762T patent/DE3872728D1/de not_active Expired - Lifetime
- 1988-01-20 ES ES88100762T patent/ES2042604T3/es not_active Expired - Lifetime
- 1988-01-20 EP EP88901245A patent/EP0342199A1/fr active Pending
- 1988-01-20 BR BR888807325A patent/BR8807325A/pt not_active IP Right Cessation
- 1988-01-20 WO PCT/EP1988/000035 patent/WO1988005445A1/fr not_active Ceased
-
1994
- 1994-08-22 US US08/293,906 patent/US5879754A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01503239A (ja) | 1989-11-02 |
| WO1988005445A1 (fr) | 1988-07-28 |
| JPH0649841B2 (ja) | 1994-06-29 |
| DE3872728D1 (en) | 1992-08-20 |
| ES2042604T3 (es) | 1993-12-16 |
| ATE78269T1 (de) | 1992-08-15 |
| BR8807325A (pt) | 1990-03-01 |
| US5879754A (en) | 1999-03-09 |
| EP0279198A1 (fr) | 1988-08-24 |
| DE3701547A1 (de) | 1988-08-04 |
| EP0279198B1 (fr) | 1992-07-15 |
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