DE2456469C2 - Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als Beschichtungsmittel - Google Patents
Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als BeschichtungsmittelInfo
- Publication number
- DE2456469C2 DE2456469C2 DE2456469A DE2456469A DE2456469C2 DE 2456469 C2 DE2456469 C2 DE 2456469C2 DE 2456469 A DE2456469 A DE 2456469A DE 2456469 A DE2456469 A DE 2456469A DE 2456469 C2 DE2456469 C2 DE 2456469C2
- Authority
- DE
- Germany
- Prior art keywords
- water
- groups
- reaction
- acid
- polyisocyanate
- 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
Links
- 239000005056 polyisocyanate Substances 0.000 title claims description 44
- 229920001228 polyisocyanate Polymers 0.000 title claims description 44
- 238000000034 method Methods 0.000 title claims description 32
- 239000011248 coating agent Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 13
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 13
- -1 alkali metal salts Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 8
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 238000007259 addition reaction Methods 0.000 claims description 5
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 30
- 239000006185 dispersion Substances 0.000 description 25
- 239000002981 blocking agent Substances 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 238000004821 distillation Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920003009 polyurethane dispersion Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000005442 diisocyanate group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 150000003077 polyols Chemical class 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 150000003839 salts Chemical group 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 2
- LTMRRSWNXVJMBA-UHFFFAOYSA-N 2,2-diethylpropanedioic acid Chemical compound CCC(CC)(C(O)=O)C(O)=O LTMRRSWNXVJMBA-UHFFFAOYSA-N 0.000 description 2
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 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
- 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
- 229920000877 Melamine resin Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 125000003010 ionic group Chemical group 0.000 description 2
- 150000002690 malonic acid derivatives Chemical class 0.000 description 2
- JOWMUPQBELRFRZ-UHFFFAOYSA-N n-carbamoylformamide Chemical group NC(=O)NC=O JOWMUPQBELRFRZ-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229960003080 taurine Drugs 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- QKOWXXDOHMJOMQ-UHFFFAOYSA-N 1,3,5-tris(6-isocyanatohexyl)biuret Chemical compound O=C=NCCCCCCNC(=O)N(CCCCCCN=C=O)C(=O)NCCCCCCN=C=O QKOWXXDOHMJOMQ-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- WSGRBPMAPUKFBQ-UHFFFAOYSA-N 1-(methylamino)ethanesulfonic acid;sodium Chemical compound [Na].CNC(C)S(O)(=O)=O WSGRBPMAPUKFBQ-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- NETIXPOFUYPXNI-UHFFFAOYSA-N 2-aminopropane-2-sulfonic acid Chemical compound CC(C)(N)S(O)(=O)=O NETIXPOFUYPXNI-UHFFFAOYSA-N 0.000 description 1
- YDCRNMJQROAWFT-UHFFFAOYSA-N 5-hydroxyhexanoic acid Chemical compound CC(O)CCCC(O)=O YDCRNMJQROAWFT-UHFFFAOYSA-N 0.000 description 1
- SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- USDJGQLNFPZEON-UHFFFAOYSA-N [[4,6-bis(hydroxymethylamino)-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(NCO)=NC(NCO)=N1 USDJGQLNFPZEON-UHFFFAOYSA-N 0.000 description 1
- 238000002679 ablation Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229920003180 amino resin Polymers 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 229960002684 aminocaproic acid Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000013861 fat-free Nutrition 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 229940099990 ogen Drugs 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 229960003104 ornithine Drugs 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000010409 thin film 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
- 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
- 238000005829 trimerization reaction Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
- C07C273/1872—Preparation of compounds comprising a -N-C(O)-N-C(O)-N- moiety
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2456469A DE2456469C2 (de) | 1974-11-29 | 1974-11-29 | Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als Beschichtungsmittel |
| GB44902/75A GB1521326A (en) | 1974-11-29 | 1975-10-30 | Process for the production of water-soluble or water-dispersible blocked polyisocyanates |
| CA239,015A CA1065093A (en) | 1974-11-29 | 1975-11-04 | Process for the production of water-soluble or water-dispersible blocked polyisocyanates |
| US05/630,112 US4098933A (en) | 1974-11-29 | 1975-11-10 | Process for the production of water-soluble or water-dispersible blocked polyisocyanates |
| JP50141257A JPS583491B2 (ja) | 1974-11-29 | 1975-11-27 | スイヨウセイ マタハ ミズブンサンセイブロツクドポリイソシアネ−ト ノ セイホウ |
| SE7513379A SE424873B (sv) | 1974-11-29 | 1975-11-27 | Sett att framstella i vatten losliga eller dispergerbara blockerade polyisocyanater |
| NL7513879A NL7513879A (nl) | 1974-11-29 | 1975-11-27 | Werkwijze ter bereiding van in water oplosbare respectievelijk dispergeerbare geblokkeerde po- lyisocyanaten. |
| IT52425/75A IT1052424B (it) | 1974-11-29 | 1975-11-27 | Procedimento per la produzione di poliisocianati bloccati solubili o disperdibili in acqua |
| BE162242A BE836027A (fr) | 1974-11-29 | 1975-11-27 | Procede de preparation de polyisocyanates bloques solubles ou dispersables dans l'eau |
| FR7536589A FR2292724A1 (fr) | 1974-11-29 | 1975-11-28 | Procede de preparation de polyisocyanates bloques solubles ou dispersables dans l'eau |
| ES443041A ES443041A1 (es) | 1974-11-29 | 1975-11-28 | Procedimiento para la obtencion de poliisocianatos bloquea- dos solubles o dispersables en agua. |
| AU87136/75A AU8713675A (en) | 1974-11-29 | 1975-12-01 | Production of water-soluble or water-dispersible blocked polyisocyanates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2456469A DE2456469C2 (de) | 1974-11-29 | 1974-11-29 | Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als Beschichtungsmittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2456469A1 DE2456469A1 (de) | 1976-08-12 |
| DE2456469C2 true DE2456469C2 (de) | 1983-01-13 |
Family
ID=5932057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2456469A Expired DE2456469C2 (de) | 1974-11-29 | 1974-11-29 | Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als Beschichtungsmittel |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4098933A (esLanguage) |
| JP (1) | JPS583491B2 (esLanguage) |
| AU (1) | AU8713675A (esLanguage) |
| BE (1) | BE836027A (esLanguage) |
| CA (1) | CA1065093A (esLanguage) |
| DE (1) | DE2456469C2 (esLanguage) |
| ES (1) | ES443041A1 (esLanguage) |
| FR (1) | FR2292724A1 (esLanguage) |
| GB (1) | GB1521326A (esLanguage) |
| IT (1) | IT1052424B (esLanguage) |
| NL (1) | NL7513879A (esLanguage) |
| SE (1) | SE424873B (esLanguage) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2712931A1 (de) * | 1977-03-24 | 1978-09-28 | Veba Chemie Ag | Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen - enthaltende verbindungen |
| JPS53126058A (en) * | 1977-04-11 | 1978-11-02 | Dai Ichi Kogyo Seiyaku Co Ltd | Water-soluble or-dispersible reactive urethane composition |
| DE2732662A1 (de) * | 1977-07-20 | 1979-02-01 | Veba Chemie Ag | Isocyanuratgruppen - und endstaendig- blockierte isocyanatgruppen-enthaltende verbindungen |
| DE2853937A1 (de) * | 1978-12-14 | 1980-07-03 | Bayer Ag | Verfahren zur herstellung von wasserdispergierbaren oder -loeslichen blockierten polyisocyanaten, die nach dem verfahren erhaeltlichen blockierten polyisocyanate, sowie diese blockierte polyisocyanate als isocyanatkomponente enthaltende lackbindemittel |
| JPS56819A (en) * | 1979-05-17 | 1981-01-07 | Mitui Toatsu Chem Inc | Thermosetting polyurethane resin and coating agent |
| DE2929224A1 (de) * | 1979-07-19 | 1981-02-05 | Huels Chemische Werke Ag | Herstellung von freie nco- und endstaendig mit epsilon -caprolactam blockierte nco-gruppen enthaltenden isophorondiisocyanataddukten, sowie danach hergestellte verbindungen |
| US4322327A (en) * | 1979-10-19 | 1982-03-30 | Mitsubishi Petrochemical Co., Ltd. | Slow-curing water-curable urethane prepolymer composition |
| US4421826A (en) * | 1980-05-08 | 1983-12-20 | W. R. Grace & Co. | Polyurethane polymer amine salt as a dyeing aid, particularly for polyolefin fibers |
| US4326043A (en) * | 1981-01-19 | 1982-04-20 | Basf Wyandotte Corporation | Process for the preparation of polyisocyanurate dispersions modified with halogenated alcohols and compositions prepared therefrom |
| US4359541A (en) * | 1981-01-19 | 1982-11-16 | Basf Wyandotte Corporation | Process for the preparation of polyisocyanurate dispersions and compositions prepared therefrom |
| US4433017A (en) * | 1981-09-17 | 1984-02-21 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Thermally reactive water-soluble blocked urethane prepolymer |
| DE3137748A1 (de) * | 1981-09-23 | 1983-03-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von hitzeaktivierbare vernetzer enthaltenden waessrigen dispersionen oder loesungen von polyurethan-polyharnstoffen, die nach dem verfahren erhaeltlichen dispersionen oder loesungen, sowie ihre verwendung zur herstellung von ueberzuegen |
| US4608304A (en) * | 1982-09-30 | 1986-08-26 | Mobay Corporation | Glass fibers coated with aqueously dispersed coating compositions |
| US4522851A (en) * | 1982-09-30 | 1985-06-11 | Mobay Chemical Corporation | Process for coating aqueous dispersion of epoxy resin and blocked polyisocyanate containing chemically incorporated anionic hydrophilic groups |
| DE3326188A1 (de) * | 1983-07-20 | 1985-01-31 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von organischen polyisocyanaten mit zumindest teilweise blockierten isocyanatgruppen, die nach dem verfahren erhaeltlichen verbindungen und ihre verwendung zur herstellung von polyurethanen, einbrennlacken oder waessrigen polyisocyanatloesungen bzw. -dispersionen |
| DE3345448A1 (de) * | 1983-12-15 | 1985-06-27 | Bayer Ag, 5090 Leverkusen | Waessrige polyurethan-einbrennlacke und ihre verwendung zur herstellung von lackfilmen und beschichtungen |
| AT383820B (de) * | 1985-09-25 | 1987-08-25 | Vianova Kunstharz Ag | Verfahren zur herstellung selbstvernetzender kathionischer lackbindemittel und deren verwendung |
| DE3735198A1 (de) * | 1987-10-17 | 1989-05-03 | Bayer Ag | In wasser loesliche oder dispergierbare, blockierte polyisocyanate, ein verfahren zu ihrer herstellung und ihre verwendung |
| US4925885A (en) * | 1988-01-12 | 1990-05-15 | Mobay Corporation | Aqueous compositions for use in the production of crosslinked polyurethanes |
| US5389718A (en) * | 1990-07-30 | 1995-02-14 | Miles Inc. | Two-component aqueous polyurethane dispersions |
| US5191012A (en) * | 1991-03-28 | 1993-03-02 | Miles Inc. | Aqueous dispersions of encapsulated polyisocyanates |
| CA2072931C (en) * | 1991-07-23 | 2003-12-30 | Robin E. Tirpak | A process for the preparation of aqueous dispersions containing both blocked polyisocyanates and polyhydroxyl compounds |
| US5296160A (en) * | 1991-07-23 | 1994-03-22 | Miles Inc. | Aqueous dispersions of blocked polyisocyanates |
| US5508370A (en) * | 1991-10-17 | 1996-04-16 | Bayer Aktiengesellschaft | Water-dispersible blocked isocyanates, method of manufacture, and use thereof |
| DE4213527A1 (de) * | 1992-04-24 | 1993-10-28 | Bayer Ag | Wäßrige Überzugsmittel für elastische Einbrennlackierungen |
| US5254611A (en) * | 1992-06-30 | 1993-10-19 | Henkel Corporation | Water dispersable urethane acrylate oligomer |
| DE4221924A1 (de) * | 1992-07-03 | 1994-01-13 | Bayer Ag | In Wasser lösliche oder dispergierbare Polyisocyanatgemische und ihre Verwendung in Einbrennlacken |
| US5558900A (en) * | 1994-09-22 | 1996-09-24 | Fan; You-Ling | One-step thromboresistant, lubricious coating |
| DE19519396A1 (de) * | 1995-05-26 | 1996-11-28 | Huels Chemische Werke Ag | Neue blockierte Polyisocyanate sowie ein Verfahren zu ihrer Herstellung |
| US5798409A (en) * | 1995-10-03 | 1998-08-25 | Minnesota Mining & Manufacturing Company | Reactive two-part polyurethane compositions and optionally self-healable and scratch-resistant coatings prepared therefrom |
| GB9520317D0 (en) * | 1995-10-05 | 1995-12-06 | Baxenden Chem Ltd | Water dispersable blocked isocyanates |
| DE19615116A1 (de) * | 1996-04-17 | 1997-10-23 | Bayer Ag | Wäßrige bzw. wasserverdünnbare blockierte Polyisocyanate für die Herstellung von wäßrigen 1K-PUR-Klarlacken mit wesentlich verringerter Thermovergilbung |
| DE59700752D1 (de) * | 1996-10-29 | 1999-12-30 | Degussa | Stabile und feststoffreiche wässrige Dispersionen von blockierten Polyisocyanaten |
| DE19715416A1 (de) * | 1997-04-14 | 1998-10-15 | Ciba Sc Pfersee Gmbh | Umsetzungsprodukte von Isocyanaten mit Hydroxyverbindungen für die Textilveredelung |
| US6265468B1 (en) | 1998-10-22 | 2001-07-24 | Vianova Resins, Inc. | Aqueous polyurethane dispersions and coatings prepared therefrom |
| AU2587200A (en) | 1998-11-06 | 2000-05-29 | Goex Corporation | Transparent static dissipative coating compositions |
| US6416696B1 (en) | 1999-12-16 | 2002-07-09 | Bayer Corporation | Aqueous mixed pMDI/phenolic resin binders for the production of wood composite products |
| US6291578B1 (en) | 1999-12-16 | 2001-09-18 | Bayer Corporation | Blocked polyisocyanates containing phenolic groups |
| KR100698425B1 (ko) * | 2000-02-28 | 2007-03-26 | 바이엘 악티엔게젤샤프트 | 고 고형분의 가열건조형 에나멜용 수성 코팅제 |
| JP5009463B2 (ja) * | 2001-05-21 | 2012-08-22 | 三菱樹脂株式会社 | 塗布フィルム |
| US6512039B1 (en) | 2001-11-16 | 2003-01-28 | Lord Corporation | Adhesives for bonding peroxide-cured elastomers |
| DE10216945A1 (de) * | 2002-04-17 | 2003-11-06 | Bayer Ag | Selbstvernetzende PUR-Dispersionen |
| US7026428B2 (en) * | 2002-06-17 | 2006-04-11 | Bayer Aktiengesellschaft | Blocked polyisocyanates |
| DE10260298A1 (de) * | 2002-12-20 | 2004-07-01 | Bayer Ag | Hydrophilierte blockierte Polysocyanate |
| DE10306243A1 (de) * | 2003-02-14 | 2004-08-26 | Bayer Ag | Einkomponenten-Beschichtungssysteme |
| DE10346548A1 (de) * | 2003-10-02 | 2005-05-12 | Bayer Materialscience Ag | Selbstvernetzende PUR-Dispersionen |
| US20060122357A1 (en) * | 2004-12-08 | 2006-06-08 | Thomas Faecke | Continuous method for manufacturing an acid functional blocked solid isocyanate |
| DE102005030225A1 (de) * | 2005-06-29 | 2007-01-04 | Bayer Materialscience Ag | Selbstvernetzende PUR-Dispersionen |
| DE102005036654A1 (de) * | 2005-08-04 | 2007-02-15 | Bayer Materialscience Ag | Selbstvernetzende PUR-Dispersionen mit Uretdionstruktur |
| DE102006059680A1 (de) * | 2006-12-18 | 2008-06-19 | Bayer Materialscience Ag | Colöserfreie, selbstvernetzende PUR-Dispersionen |
| DE102007054002A1 (de) | 2007-11-13 | 2009-05-14 | Bayer Materialscience Ag | Nicht-ionisch hydrophilierte Bindemittel-Dispersionen |
| CN103974998A (zh) | 2011-12-06 | 2014-08-06 | 道康宁公司 | 可固化有机硅组合物、固化材料、制成品、方法和用途 |
| ES2716126T3 (es) | 2015-03-06 | 2019-06-10 | Covestro Deutschland Ag | Dispersión acuosa de poliuretano-urea que contiene grupos ácidos libres |
| ES2708202T3 (es) | 2015-06-25 | 2019-04-09 | Covestro Deutschland Ag | Dispersiones de poliuretano desprovistas de urea |
| JP2017095533A (ja) * | 2015-11-18 | 2017-06-01 | 旭化成株式会社 | ブロックポリイソシアネート組成物、熱硬化性組成物、及び硬化物 |
| JP6713748B2 (ja) * | 2015-10-22 | 2020-06-24 | 旭化成株式会社 | ブロックポリイソシアネート組成物 |
| EP3348593B1 (en) * | 2015-09-11 | 2019-08-21 | Asahi Kasei Kabushiki Kaisha | Blocked polyisocyanate composition, one-component coating composition, coating film, and coated article |
| MX2019014869A (es) | 2017-06-26 | 2020-02-07 | Advansix Resins & Chemicals Llc | Metodos y composiciones para dispersiones de poliuretano usando solventes derivados de caprolactama. |
| EP3590988A1 (de) | 2018-07-05 | 2020-01-08 | Covestro Deutschland AG | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
| WO2019180127A1 (de) | 2018-03-23 | 2019-09-26 | Covestro Deutschland Ag | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
| EP3590987A1 (de) | 2018-07-05 | 2020-01-08 | Covestro Deutschland AG | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
| EP3543271A1 (de) | 2018-03-23 | 2019-09-25 | Covestro Deutschland AG | Wässrige uretdiongruppenhaltige zusammensetzungen und verfahren zu deren herstellung |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE859156C (de) * | 1943-01-21 | 1952-12-11 | Bayer Ag | Verfahren zur Herstellung von Additionsprodukten aus Isocyanaten und sauren Salzen der schwefligen Saeure |
| DE922711C (de) * | 1943-04-29 | 1955-01-24 | Bayer Ag | Verfahren zur UEberfuehrung von Verbindungen mit reaktionsfaehigen Wasserstoffatomen in ihre Umsetzungsprodukte mit Isocyansaeureestern |
| DE830639C (de) * | 1950-02-22 | 1952-02-07 | Bayer Ag | Verfahren zur Herstellung von Isocyanat-Umsetzungsprodukten |
| DE1012601B (de) * | 1955-06-24 | 1957-07-25 | Bayer Ag | Verfahren zur Herstellung von Additionsverbindungen |
| DE1029151B (de) * | 1956-03-01 | 1958-04-30 | Bayer Ag | Verfahren zur Herstellung von wasserloeslichen, verkappten Isocyanaten |
| NL300468A (esLanguage) * | 1962-11-24 | |||
| US3384506A (en) * | 1964-05-18 | 1968-05-21 | Thiokol Chemical Corp | Hydrophilic urethane compositions and process for preparation of moisture containing breathable fabrics |
| DE1570556C3 (de) * | 1965-04-03 | 1979-09-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von anionische Gruppen aufweisenden Polyurethanen |
| US3514316A (en) * | 1967-01-23 | 1970-05-26 | Koppers Co Inc | Method of coating metal with coal tar pitch and article produced thereby |
| JPS4928653B1 (esLanguage) * | 1970-04-21 | 1974-07-29 | ||
| US3883483A (en) * | 1971-08-02 | 1975-05-13 | Ppg Industries Inc | Electrodepositable cationic thermosetting coating compositions |
| US3939222A (en) * | 1971-10-26 | 1976-02-17 | Bayer Aktiengesellschaft | Production of polyurethane plastics |
| DE2221756C3 (de) * | 1972-05-04 | 1980-06-26 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von lösungsmittelbeständigen, lichtechten, knick- und reibfesten Polyurethanüberzügen auf textlien Substraten, Leder oder Kunstleder oder von Folien |
| CH575969A5 (esLanguage) * | 1972-12-14 | 1976-05-31 | Hoechst Ag | |
| US3933759A (en) * | 1974-12-20 | 1976-01-20 | E. I. Du Pont De Nemours & Company | Heat-activatable, storage-stable polyurethane powders |
-
1974
- 1974-11-29 DE DE2456469A patent/DE2456469C2/de not_active Expired
-
1975
- 1975-10-30 GB GB44902/75A patent/GB1521326A/en not_active Expired
- 1975-11-04 CA CA239,015A patent/CA1065093A/en not_active Expired
- 1975-11-10 US US05/630,112 patent/US4098933A/en not_active Expired - Lifetime
- 1975-11-27 NL NL7513879A patent/NL7513879A/xx not_active Application Discontinuation
- 1975-11-27 BE BE162242A patent/BE836027A/xx unknown
- 1975-11-27 SE SE7513379A patent/SE424873B/xx unknown
- 1975-11-27 JP JP50141257A patent/JPS583491B2/ja not_active Expired
- 1975-11-27 IT IT52425/75A patent/IT1052424B/it active
- 1975-11-28 ES ES443041A patent/ES443041A1/es not_active Expired
- 1975-11-28 FR FR7536589A patent/FR2292724A1/fr active Granted
- 1975-12-01 AU AU87136/75A patent/AU8713675A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1521326A (en) | 1978-08-16 |
| BE836027A (fr) | 1976-05-28 |
| FR2292724B1 (esLanguage) | 1980-03-07 |
| JPS583491B2 (ja) | 1983-01-21 |
| CA1065093A (en) | 1979-10-23 |
| DE2456469A1 (de) | 1976-08-12 |
| IT1052424B (it) | 1981-06-20 |
| SE424873B (sv) | 1982-08-16 |
| NL7513879A (nl) | 1976-06-01 |
| AU8713675A (en) | 1977-06-09 |
| SE7513379L (sv) | 1976-05-31 |
| ES443041A1 (es) | 1977-04-01 |
| FR2292724A1 (fr) | 1976-06-25 |
| JPS5177695A (en) | 1976-07-06 |
| US4098933A (en) | 1978-07-04 |
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| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |