DE2740290C2 - - Google Patents
Info
- Publication number
- DE2740290C2 DE2740290C2 DE2740290A DE2740290A DE2740290C2 DE 2740290 C2 DE2740290 C2 DE 2740290C2 DE 2740290 A DE2740290 A DE 2740290A DE 2740290 A DE2740290 A DE 2740290A DE 2740290 C2 DE2740290 C2 DE 2740290C2
- Authority
- DE
- Germany
- Prior art keywords
- parts
- glycoluril
- water
- mixture
- tetramethylolglycoluril
- 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 - Lifetime
Links
- VPVSTMAPERLKKM-UHFFFAOYSA-N glycoluril Chemical class N1C(=O)NC2NC(=O)NC21 VPVSTMAPERLKKM-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 25
- 239000002861 polymer material Substances 0.000 claims description 13
- 230000029936 alkylation Effects 0.000 claims description 10
- 238000005804 alkylation reaction Methods 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 8
- 230000011987 methylation Effects 0.000 claims description 7
- 238000007069 methylation reaction Methods 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000007031 hydroxymethylation reaction Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 230000001476 alcoholic effect Effects 0.000 claims description 4
- 230000006208 butylation Effects 0.000 claims description 4
- 230000006203 ethylation Effects 0.000 claims description 4
- 238000006200 ethylation reaction Methods 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 230000006207 propylation Effects 0.000 claims description 3
- 150000001408 amides Chemical group 0.000 claims 1
- 238000000576 coating method Methods 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- UUGLSEIATNSHRI-UHFFFAOYSA-N 1,3,4,6-tetrakis(hydroxymethyl)-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound OCN1C(=O)N(CO)C2C1N(CO)C(=O)N2CO UUGLSEIATNSHRI-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
- 239000011248 coating agent Substances 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 11
- 239000003973 paint Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003431 cross linking reagent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 9
- 239000000049 pigment Substances 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- 210000003298 dental enamel Anatomy 0.000 description 8
- 239000006188 syrup Substances 0.000 description 8
- 235000020357 syrup Nutrition 0.000 description 8
- 239000008199 coating composition Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229920005862 polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229960002887 deanol Drugs 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 229920001225 polyester resin Polymers 0.000 description 5
- 239000004645 polyester resin Substances 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- -1 Electrocoats Substances 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 125000001046 glycoluril group Chemical group [H]C12N(*)C(=O)N(*)C1([H])N(*)C(=O)N2* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000002739 metals Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- 239000004408 titanium dioxide Substances 0.000 description 4
- XGQJGMGAMHFMAO-UHFFFAOYSA-N 1,3,4,6-tetrakis(methoxymethyl)-3a,6a-dihydroimidazo[4,5-d]imidazole-2,5-dione Chemical compound COCN1C(=O)N(COC)C2C1N(COC)C(=O)N2COC XGQJGMGAMHFMAO-UHFFFAOYSA-N 0.000 description 3
- 229920000178 Acrylic resin Polymers 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000003945 anionic surfactant Substances 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
- 239000004202 carbamide Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000012260 resinous material Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 3
- 229910000165 zinc phosphate Inorganic materials 0.000 description 3
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000010960 cold rolled steel Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 2
- 229940043276 diisopropanolamine Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000011344 liquid material Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004908 Emulsion polymer Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- LPTWEDZIPSKWDG-UHFFFAOYSA-N benzenesulfonic acid;dodecane Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCCCCCCCCCCC LPTWEDZIPSKWDG-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- RZHBMYQXKIDANM-UHFFFAOYSA-N dioctyl butanedioate;sodium Chemical compound [Na].CCCCCCCCOC(=O)CCC(=O)OCCCCCCCC RZHBMYQXKIDANM-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000005217 methyl ethers Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- NOMPUOUIIHWRJU-UHFFFAOYSA-M sodium;4-cyclohexyloxy-4-oxobutanoate Chemical compound [Na+].[O-]C(=O)CCC(=O)OC1CCCCC1 NOMPUOUIIHWRJU-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000005690 transetherification reaction Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 150000005219 trimethyl ethers Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3442—Heterocyclic compounds having nitrogen in the ring having two nitrogen atoms in the ring
- C08K5/3445—Five-membered rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31627—Next to aldehyde or ketone condensation product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31688—Next to aldehyde or ketone condensation product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31949—Next to cellulosic
- Y10T428/31957—Wood
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31942—Of aldehyde or ketone condensation product
- Y10T428/31949—Next to cellulosic
- Y10T428/31964—Paper
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/721,008 US4105708A (en) | 1976-09-07 | 1976-09-07 | Dimethoxymethyl diethoxymethyl glycoluril and coating compositions containing the same as a cross-linking agent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2740290A1 DE2740290A1 (de) | 1978-03-09 |
| DE2740290C2 true DE2740290C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-03-18 |
Family
ID=24896139
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772740290 Granted DE2740290A1 (de) | 1976-09-07 | 1977-09-07 | Praktisch vollstaendig hydroxymethylierte glykolurilderivate |
Country Status (12)
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0021770A1 (en) * | 1979-06-18 | 1981-01-07 | Scm Corporation | A thermosetting powder coating composition and process for preparing same |
| US4442257A (en) * | 1981-05-18 | 1984-04-10 | Scm Corporation | Low temperature cure latexes |
| US4444941A (en) * | 1981-05-18 | 1984-04-24 | Scm Corporation | Low temperature cure latexes |
| FR2624546B1 (fr) * | 1987-12-15 | 1993-11-26 | Saint Gobain Vitrage | Vitrage antifeu et procede de fabrication |
| DE4001139C2 (de) * | 1989-04-19 | 2003-04-17 | Deutsches Textilforschzentrum | Verfahren zur Isolierung von organischen Verbindungen |
| US5180835A (en) * | 1991-06-25 | 1993-01-19 | American Cyanamid Company | Process for the preparation of monomeric tetramethoxymethylglycoloril |
| JP2006507398A (ja) * | 2002-11-25 | 2006-03-02 | ワールド・プロパティーズ・インコーポレイテッド | 硬化性カバーコート組成物、その組成物から得られる硬化生成物及びその硬化生成物の製造方法 |
| HUE038015T2 (hu) | 2006-03-30 | 2018-09-28 | Fmc Corp | Acetilén karbamid származék-polikarbamid polimerek, és ezek mikrokapszulái és kiszerelései szabályozott kibocsátáshoz |
| US20080124532A1 (en) * | 2006-11-29 | 2008-05-29 | Basf Corporation | Materials and oligomers in low voc coatings |
| US20090053420A1 (en) * | 2007-08-20 | 2009-02-26 | Basf Corporation | Thermosetting coating compositions with multiple cure mechanisms |
| US20100323112A1 (en) | 2009-06-18 | 2010-12-23 | Basf Corporation | Method for improving sag resistance |
| US20110135832A1 (en) | 2009-12-04 | 2011-06-09 | Basf Coatings Ag | Method and composition for refinish coatings |
| US8969612B2 (en) | 2009-12-10 | 2015-03-03 | Soane Energy, Llc | Low interfacial tension surfactants for petroleum applications |
| CA2783831C (en) * | 2009-12-10 | 2016-03-22 | David Soane | Low interfacial tension surfactants for petroleum applications |
| JP6223352B2 (ja) | 2011-12-09 | 2017-11-01 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | ハイソリッド塗料および塗装方法 |
| WO2013089968A1 (en) | 2011-12-12 | 2013-06-20 | Basf Coatings Gmbh | High solids coating and process for coating |
| US9403182B2 (en) | 2011-12-12 | 2016-08-02 | Basf Coatings Gmbh | High solids coating and process for coating |
| US20150210795A1 (en) | 2014-01-30 | 2015-07-30 | Basf Coatings Gmbh | Amphiphilic carbamate-functional copolymers and coatings containing them |
| US9376378B2 (en) | 2014-05-08 | 2016-06-28 | Basf Coatings Gmbh | Method using zirconium catalyst for producing carbamate-functional materials |
| US9334234B2 (en) | 2014-05-08 | 2016-05-10 | Basf Coatings Gmbh | Method using titanium catalyst for producing carbamate-functional materials |
| US9938429B2 (en) | 2014-07-18 | 2018-04-10 | BASF Coating GmbH | Coatings with flexible hyperbranched polyols |
| JP6743144B2 (ja) | 2015-11-03 | 2020-08-19 | ビーエーエスエフ コーティングス ゲゼルシャフト ミット ベシュレンクテル ハフツングＢＡＳＦ Ｃｏａｔｉｎｇｓ ＧｍｂＨ | 反応性希釈剤としてのバイオベースのヒドロキシウレタン |
| WO2018046334A1 (en) | 2016-09-08 | 2018-03-15 | Basf Coatings Gmbh | Coatings with radiation-curable hyperbranched polymers |
| WO2018046335A1 (en) | 2016-09-08 | 2018-03-15 | Basf Coatings Gmbh | Radiation-curable hyperbranched polymers with dicarboxylic acid cores |
| WO2018050509A2 (en) | 2016-09-15 | 2018-03-22 | Basf Coatings Gmbh | Coatings with wax-modified hyperbranched and flexible hyperbranched polyols |
| US20190106592A1 (en) | 2017-10-11 | 2019-04-11 | Basf Coatings Gmbh | Hyperbranched polymers for organic pigment dispersions and water-sensitive pigments |
| BR112021023697A2 (pt) | 2019-07-16 | 2022-01-04 | Basf Coatings Gmbh | Métodos para fabricar uma dispersão de poliuretano de um componente e para revestir um substrato com o material de revestimento, dispersão de poliuretano de um componente, material de revestimento de um componente, substrato revestido, revestimento de multicamadas, e, substrato revestido de multicamadas |
| CA3148170A1 (en) | 2019-08-28 | 2021-03-04 | Han Bin Wang | A cardanol-derivatives modified polymer and a coating composition comprising the same |
| WO2021136800A1 (en) | 2019-12-30 | 2021-07-08 | Basf Coatings Gmbh | Coatings containing branched polyester polyols as plasticizers |
| EP4615896A1 (en) | 2022-11-08 | 2025-09-17 | BASF Coatings GmbH | Scratch resistant one-pack coating material |
| WO2024120824A1 (en) | 2022-12-05 | 2024-06-13 | Basf Coatings Gmbh | A metallic effect coating composition and its applications thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1519044A1 (de) | 1951-01-28 | 1969-04-17 | Basf Ag | Verfahren zum Herstellen von UEberzuegen auf Metallteilen |
| DE920965C (de) * | 1952-08-06 | 1954-12-06 | Basf Ag | Verfahren zur Herstellung von AEthern des Tetramethylolglyoxaldiureins |
| BE620252A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1961-07-13 | |||
| US3766204A (en) * | 1971-06-18 | 1973-10-16 | Allied Chem | Oxyalkylated derivatives of glycolurils |
| FR2171484A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-02-01 | 1973-09-21 | Nobel Hoechst Chimie | |
| JPS5523835B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-11-14 | 1980-06-25 | ||
| US4009134A (en) * | 1973-10-09 | 1977-02-22 | The General Tire & Rubber Company | Aqueous alkaline dispersion of vinyl pyridine copolymer, polymethylol glycoluril, and R-F novolak |
| CA1089145A (en) * | 1976-02-02 | 1980-11-04 | Girish G. Parekh | Organic metal finishes |
-
1976
- 1976-09-07 US US05/721,008 patent/US4105708A/en not_active Expired - Lifetime
-
1977
- 1977-08-08 CA CA284,287A patent/CA1091236A/en not_active Expired
- 1977-08-11 GB GB33815/77A patent/GB1603842A/en not_active Expired
- 1977-08-24 AR AR268925A patent/AR218032A1/es active
- 1977-08-31 BR BR7705806A patent/BR7705806A/pt unknown
- 1977-08-31 NL NL7709595A patent/NL7709595A/xx not_active Application Discontinuation
- 1977-09-05 MX MX170470A patent/MX148864A/es unknown
- 1977-09-06 IT IT50899/77A patent/IT1090325B/it active
- 1977-09-06 FR FR7726988A patent/FR2363602A1/fr active Pending
- 1977-09-06 BE BE180690A patent/BE858428A/xx not_active IP Right Cessation
- 1977-09-07 DE DE19772740290 patent/DE2740290A1/de active Granted
- 1977-09-07 JP JP10687677A patent/JPS5363487A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4105708A (en) | 1978-08-08 |
| CA1091236A (en) | 1980-12-09 |
| MX148864A (es) | 1983-06-28 |
| AR218032A1 (es) | 1980-05-15 |
| NL7709595A (nl) | 1978-03-09 |
| BE858428A (fr) | 1978-03-06 |
| GB1603842A (en) | 1981-12-02 |
| FR2363602A1 (fr) | 1978-03-31 |
| IT1090325B (it) | 1985-06-26 |
| JPS5363487A (en) | 1978-06-06 |
| BR7705806A (pt) | 1978-06-27 |
| DE2740290A1 (de) | 1978-03-09 |
| JPS6363545B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-12-07 |
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