DE2430899C3 - Verfahren zur Herstellung von niedrigviskosen körperreichen Melaminharz-Lösungen mit geringem Gehalt an freiem Formaldehyd - Google Patents
Verfahren zur Herstellung von niedrigviskosen körperreichen Melaminharz-Lösungen mit geringem Gehalt an freiem FormaldehydInfo
- Publication number
- DE2430899C3 DE2430899C3 DE2430899A DE2430899A DE2430899C3 DE 2430899 C3 DE2430899 C3 DE 2430899C3 DE 2430899 A DE2430899 A DE 2430899A DE 2430899 A DE2430899 A DE 2430899A DE 2430899 C3 DE2430899 C3 DE 2430899C3
- Authority
- DE
- Germany
- Prior art keywords
- weight
- melamine
- alcohol
- solution
- parts
- 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
- 229920000877 Melamine resin Polymers 0.000 title claims description 77
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 70
- 239000004640 Melamine resin Substances 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- 229920005989 resin Polymers 0.000 claims description 57
- 239000011347 resin Substances 0.000 claims description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 27
- 239000007787 solid Substances 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 14
- 229920000728 polyester Polymers 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 229920000180 alkyd Polymers 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 210000003298 dental enamel Anatomy 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 238000005690 transetherification reaction Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 30
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 25
- 239000008096 xylene Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- 239000003973 paint Substances 0.000 description 14
- 238000006266 etherification reaction Methods 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 11
- 239000000523 sample Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 10
- 229930040373 Paraformaldehyde Natural products 0.000 description 9
- 229920002866 paraformaldehyde Polymers 0.000 description 9
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 230000009257 reactivity Effects 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MBHRHUJRKGNOKX-UHFFFAOYSA-N [(4,6-diamino-1,3,5-triazin-2-yl)amino]methanol Chemical compound NC1=NC(N)=NC(NCO)=N1 MBHRHUJRKGNOKX-UHFFFAOYSA-N 0.000 description 3
- 238000010533 azeotropic distillation Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000004922 lacquer Substances 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 239000002966 varnish Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012468 concentrated sample Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide 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
- 230000035484 reaction time Effects 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- SYDYRFPJJJPJFE-UHFFFAOYSA-N [[4,6-bis[bis(hydroxymethyl)amino]-1,3,5-triazin-2-yl]amino]methanol Chemical compound OCNC1=NC(N(CO)CO)=NC(N(CO)CO)=N1 SYDYRFPJJJPJFE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- -1 methylol melamine ethers Chemical class 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000006120 scratch resistant coating Substances 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229920001909 styrene-acrylic polymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
- C08G12/42—Chemically modified polycondensates by etherifying
- C08G12/424—Chemically modified polycondensates by etherifying of polycondensates based on heterocyclic compounds
- C08G12/425—Chemically modified polycondensates by etherifying of polycondensates based on heterocyclic compounds based on triazines
- C08G12/427—Melamine
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/064—Copolymers with monomers not covered by C09D133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Detergent Compositions (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2430899A DE2430899C3 (de) | 1974-06-27 | 1974-06-27 | Verfahren zur Herstellung von niedrigviskosen körperreichen Melaminharz-Lösungen mit geringem Gehalt an freiem Formaldehyd |
| SE7507083A SE422217B (sv) | 1974-06-27 | 1975-06-19 | Sett att framstella lagviskosa, fastsubstansrika melaminhartslosningar med ringa halt fri formsldehyd |
| NO752206A NO144606C (no) | 1974-06-27 | 1975-06-20 | Fremgangsmaate til fremstilling av lavviskoese opploesninger med hoeyt faststoffinnhold av foretrede melamin/formaldehydharpikser med lavt innhold av fritt formaldehyd |
| NL7507408A NL7507408A (nl) | 1974-06-27 | 1975-06-20 | Werkwijze voor de bereiding van laagviskeuze mela- mineharsoplossingen met een groot gehalte aan droge stof en een klein gehalte aan vrij formaldehyde. |
| DK281375A DK281375A (da) | 1974-06-27 | 1975-06-20 | Fremgangsmade til fremstilling af lavviskose melaminharpiksoplosninger med et stort indhold af fast stof og et ringe indhold af frit formaldehyd |
| JP50077023A JPS5813566B2 (ja) | 1974-06-27 | 1975-06-24 | 遊離ホイムアルデヒド含量の少い、低粘稠性の、固形分の多いメラミン樹脂溶液の製造 |
| US05/590,215 US4039493A (en) | 1974-06-27 | 1975-06-25 | Melamine-formaldehyde condensates and mixtures thereof |
| BE157674A BE830632A (fr) | 1974-06-27 | 1975-06-25 | Procede de preparation de solutions concentrees et fluides de resines de melamine a faible teneur en formaldehyde libre |
| LU72823A LU72823A1 (esLanguage) | 1974-06-27 | 1975-06-25 | |
| GB27092/75A GB1483427A (en) | 1974-06-27 | 1975-06-26 | Process for the production of melamine resin solutions |
| CA230,235A CA1050678A (en) | 1974-06-27 | 1975-06-26 | Process for the production of melamine resin solutions |
| IT24801/75A IT1039409B (it) | 1974-06-27 | 1975-06-26 | Procedimento per la preparazione di soluzioni di resine melamminiche di bassa viscosita ricche di sostanze dotate di uno scarso contenuto in formaldeide libera |
| YU01650/75A YU165075A (en) | 1974-06-27 | 1975-06-26 | Process for preparing solutions of melamine resin |
| AT492375A AT348764B (de) | 1974-06-27 | 1975-06-26 | Verfahren zur herstellung von niedrigviskosen koerperreichen melaminharz-loesungen mit geringem gehalt an freiem formaldehyd |
| FR7520032A FR2276331A1 (fr) | 1974-06-27 | 1975-06-26 | Procede de preparation de solutions concentrees et fluides de resines de melamine a faible teneur en formaldehyde libre |
| ES438923A ES438923A1 (es) | 1974-06-27 | 1975-06-27 | Procedimiento para la obtencion de soluciones de resina de melamina de baja viscosidad. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2430899A DE2430899C3 (de) | 1974-06-27 | 1974-06-27 | Verfahren zur Herstellung von niedrigviskosen körperreichen Melaminharz-Lösungen mit geringem Gehalt an freiem Formaldehyd |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2430899A1 DE2430899A1 (de) | 1976-01-15 |
| DE2430899B2 DE2430899B2 (de) | 1980-09-11 |
| DE2430899C3 true DE2430899C3 (de) | 1981-06-19 |
Family
ID=5919111
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2430899A Expired DE2430899C3 (de) | 1974-06-27 | 1974-06-27 | Verfahren zur Herstellung von niedrigviskosen körperreichen Melaminharz-Lösungen mit geringem Gehalt an freiem Formaldehyd |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4039493A (esLanguage) |
| JP (1) | JPS5813566B2 (esLanguage) |
| AT (1) | AT348764B (esLanguage) |
| BE (1) | BE830632A (esLanguage) |
| CA (1) | CA1050678A (esLanguage) |
| DE (1) | DE2430899C3 (esLanguage) |
| DK (1) | DK281375A (esLanguage) |
| ES (1) | ES438923A1 (esLanguage) |
| FR (1) | FR2276331A1 (esLanguage) |
| GB (1) | GB1483427A (esLanguage) |
| IT (1) | IT1039409B (esLanguage) |
| LU (1) | LU72823A1 (esLanguage) |
| NL (1) | NL7507408A (esLanguage) |
| NO (1) | NO144606C (esLanguage) |
| SE (1) | SE422217B (esLanguage) |
| YU (1) | YU165075A (esLanguage) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2915315A1 (de) * | 1979-04-14 | 1980-10-30 | Cassella Ag | Verfahren zur herstellung von veraetherten methylolaminotriazinen |
| CA1157196A (en) * | 1980-06-04 | 1983-11-15 | Robert S. De Ruiter | Alkoxylated amino resins |
| US4374164A (en) * | 1981-12-14 | 1983-02-15 | American Cyanamid Company | High solids polymer resin coating composition containing amino resin cross-linking agent |
| US4458062A (en) * | 1983-02-14 | 1984-07-03 | American Cyanamid Company | Continuously produced melt reacted melamine-formaldehyde resins |
| US4634738A (en) * | 1985-02-26 | 1987-01-06 | Monsanto Company | High solids curable resin coating composition |
| JP2537176B2 (ja) * | 1985-05-24 | 1996-09-25 | 三井東圧化学株式会社 | 熱硬化性塗料用樹脂組成物 |
| US5731081A (en) * | 1991-10-16 | 1998-03-24 | Hollinee Corporation | Glass fiber evaporative cooler media with melamine formaldehyde binder |
| DE102005029683A1 (de) * | 2005-06-20 | 2007-01-04 | Ami-Agrolinz Melamine International Gmbh | Melaminharz |
| EP3390477B1 (en) | 2015-12-16 | 2024-01-17 | prefere Melamines GmbH | Process for manufacturing solutions of alkylated amino formaldehyde resins having a low free formaldehyde content |
| ES2938660T3 (es) * | 2016-10-11 | 2023-04-13 | Ostthueringische Mat Fuer Textil Und Kunststoffe Mbh | Fieltros y telas no tejidas de melamina formaldehído bajos en emisiones |
| KR102522737B1 (ko) * | 2016-12-21 | 2023-04-19 | 바스프 에스이 | 에터화된 멜라민 폼알데하이드 수지의 액체 조성물의 제조 방법 |
| KR102691560B1 (ko) * | 2021-03-02 | 2024-08-02 | 주식회사 동성케미컬 | 멜라민-포름알데히드 발포체 및 이의 제조방법 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT177418B (de) * | 1950-12-04 | 1954-01-25 | Ciba Geigy | Verfahren zur Herstellung verätherter Formaldehydkondensationsprodukte von mindestens zwei NH2-Gruppen enthaltenden Amino-1,3,5-triazinen |
| DE1520692B2 (de) * | 1964-04-09 | 1973-06-07 | Reichhold Albert Chemie Ag, 2000 Hamburg | Verfahren zur herstellung von wasserunloeslichen, in organischen mitteln loeslichen, veraetherten melaminharzen |
| DE1595224B2 (de) * | 1965-02-12 | 1976-12-16 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung eines hitzehaertbaren, keinen freien formaldehyd enthaltenden butanolveraetherten formaldehyd-melamin-kondensationsproduktes und dessen verwendung |
| FR1572406A (esLanguage) * | 1967-04-28 | 1969-06-27 | ||
| US3487048A (en) * | 1967-10-05 | 1969-12-30 | Fiberglas Canada Ltd | Production of water soluble or water dispersible methylated melamine-formaldehyde resins consisting largely of tri-methyl ether of tri-methylol melamine |
| US3562001A (en) * | 1968-02-20 | 1971-02-09 | Commercial Decal Inc | Gloss composition comprising water soluble and water insoluble melamine formaldehyde resins for improving surface of articles made from melamine resins and method of application thereof |
| US3458464A (en) * | 1968-10-01 | 1969-07-29 | Allied Chem | Production of melamine-urea-formaldehyde concentrates |
-
1974
- 1974-06-27 DE DE2430899A patent/DE2430899C3/de not_active Expired
-
1975
- 1975-06-19 SE SE7507083A patent/SE422217B/xx unknown
- 1975-06-20 DK DK281375A patent/DK281375A/da not_active Application Discontinuation
- 1975-06-20 NO NO752206A patent/NO144606C/no unknown
- 1975-06-20 NL NL7507408A patent/NL7507408A/xx not_active Application Discontinuation
- 1975-06-24 JP JP50077023A patent/JPS5813566B2/ja not_active Expired
- 1975-06-25 US US05/590,215 patent/US4039493A/en not_active Expired - Lifetime
- 1975-06-25 LU LU72823A patent/LU72823A1/xx unknown
- 1975-06-25 BE BE157674A patent/BE830632A/xx unknown
- 1975-06-26 CA CA230,235A patent/CA1050678A/en not_active Expired
- 1975-06-26 YU YU01650/75A patent/YU165075A/xx unknown
- 1975-06-26 GB GB27092/75A patent/GB1483427A/en not_active Expired
- 1975-06-26 AT AT492375A patent/AT348764B/de not_active IP Right Cessation
- 1975-06-26 IT IT24801/75A patent/IT1039409B/it active
- 1975-06-26 FR FR7520032A patent/FR2276331A1/fr active Granted
- 1975-06-27 ES ES438923A patent/ES438923A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| US4039493A (en) | 1977-08-02 |
| AT348764B (de) | 1979-03-12 |
| YU165075A (en) | 1982-06-18 |
| SE422217B (sv) | 1982-02-22 |
| FR2276331B1 (esLanguage) | 1982-06-11 |
| NO752206L (esLanguage) | 1975-12-30 |
| SE7507083L (sv) | 1975-12-29 |
| CA1050678A (en) | 1979-03-13 |
| JPS5813566B2 (ja) | 1983-03-14 |
| LU72823A1 (esLanguage) | 1977-03-07 |
| GB1483427A (en) | 1977-08-17 |
| FR2276331A1 (fr) | 1976-01-23 |
| NO144606C (no) | 1981-09-30 |
| NL7507408A (nl) | 1975-12-30 |
| IT1039409B (it) | 1979-12-10 |
| DE2430899B2 (de) | 1980-09-11 |
| BE830632A (fr) | 1975-12-29 |
| DK281375A (da) | 1975-12-28 |
| ES438923A1 (es) | 1977-02-16 |
| NO144606B (no) | 1981-06-22 |
| ATA492375A (de) | 1978-07-15 |
| JPS5118792A (esLanguage) | 1976-02-14 |
| DE2430899A1 (de) | 1976-01-15 |
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| OGA | New person/name/address of the applicant | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |