DE1050542B - Process for the production of resins from melamine urea and paraformaldehyde - Google Patents
Process for the production of resins from melamine urea and paraformaldehydeInfo
- Publication number
- DE1050542B DE1050542B DENDAT1050542D DE1050542DA DE1050542B DE 1050542 B DE1050542 B DE 1050542B DE NDAT1050542 D DENDAT1050542 D DE NDAT1050542D DE 1050542D A DE1050542D A DE 1050542DA DE 1050542 B DE1050542 B DE 1050542B
- Authority
- DE
- Germany
- Prior art keywords
- paraformaldehyde
- urea
- condensation
- resins
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 12
- 229920002866 paraformaldehyde Polymers 0.000 title claims description 8
- 229920005989 resin Polymers 0.000 title claims description 8
- 239000011347 resin Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- JZLWSRCQCPAUDP-UHFFFAOYSA-N 1,3,5-triazine-2,4,6-triamine;urea Chemical compound NC(N)=O.NC1=NC(N)=NC(N)=N1 JZLWSRCQCPAUDP-UHFFFAOYSA-N 0.000 title 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
- 235000013877 carbamide Nutrition 0.000 claims description 9
- 229920000877 Melamine resin Polymers 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 7
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 3
- 238000010309 melting process Methods 0.000 claims description 3
- ODGAOXROABLFNM-UHFFFAOYSA-N Polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 claims description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N Thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 2
- 229920001807 Urea-formaldehyde Polymers 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 230000002378 acidificating Effects 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000011780 sodium chloride Substances 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- JDSHMPZPIAZGSV-UHFFFAOYSA-N Melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N cyanoguanidine Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 238000005429 turbidity Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C3/00—Tanning; Compositions for tanning
- C14C3/02—Chemical tanning
- C14C3/08—Chemical tanning by organic agents
- C14C3/18—Chemical tanning by organic agents using polycondensation products or precursors thereof
- C14C3/20—Chemical tanning by organic agents using polycondensation products or precursors thereof sulfonated
-
- 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
- C08G12/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
- C08G12/34—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds and acyclic or carbocyclic compounds
- C08G12/36—Ureas; Thioureas
- C08G12/38—Ureas; Thioureas and melamines
-
- 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
- C08L61/30—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic and acyclic or carbocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
DEUTSCHESGERMAN
Gegenstand der deutschen Patentanmeldung F14878IVb/39c ist die Herstellung von Dicyandiamidharzen aus Dicyandiamid und Paraformaldehyd im Schmelzprozeß unter Mitverwendung von Harnstoff. The subject of German patent application F14878IVb / 39c is the production of dicyandiamide resins from dicyandiamide and paraformaldehyde in the melting process with the use of urea.
Das dort geschützte Verfahren ist dadurch gekennzeichnet, daß die Kondensation in der Schmelze zwischen 70 und 200° C, vorzugsweise zwischen 100 und 130° C, durchgeführt wird und daß vor, während oder nach der Kondensation zur Löslichmachung des Harzes ein nicht saures wasserlösliches Metallsalz von Arylsulfonsäuren, besonders mit Formaldehyd kondensierten Naphthalinsulfonsäuren, zugesetzt wird.The process protected there is characterized in that the condensation in the melt between 70 and 200 ° C, preferably between 100 and 130 ° C, is carried out and that before, during or after condensation to solubilize the resin, a non-acidic, water-soluble metal salt of Arylsulfonic acids, especially naphthalenesulfonic acids condensed with formaldehyde, is added.
Es wurde nun gefunden, daß man zu Kondensationsprodukten mit ähnlichen oder teilweise verbesserten Eigenschaften gelangt, wenn man das Dicyandiamid ganz durch Melamin ersetzt. Außerdem wurde gefunden, daß an Stelle von Harnstoff auch Thioharnstoff sowie substituierte Harnstoffe und Thioharnstoffe für das erfindungsgemäße Verfahren geeignet sind. Ebenso wie nach den deutschen Patentanmeldungen F 14813 IVb/39c, F 14878 IVb/39c kann auch bei der Herstellung dieser Harze das zur Löslichmachung notwendige Agens der Schmelze oder dem Gemisch der Ausgangssubstanz vor dem Schmelzprozeß zügesetzt werden.It has now been found that condensation products with similar or partially improved Properties are achieved when the dicyandiamide is completely replaced by melamine. It was also found that instead of urea also thiourea and substituted ureas and thioureas for the method according to the invention are suitable. Just like after the German patent applications F 14813 IVb / 39c, F 14878 IVb / 39c can also do the solubilization in the production of these resins necessary agent added to the melt or the mixture of the starting substance before the melting process will.
Die erfindungsgemäßen Produkte können ebenfalls zum Gerben und Nachgerben von Häuten und Ledern verwendet werden.The products according to the invention can also be used for the tanning and retanning of hides and leathers be used.
126 Teile Melamin, 60 Teile Harnstoff und 90 Teile Paraformaldehyd werden auf dem siedenden Wasserbad zusammengesdhmolzen und so lange kondensiert, bis eine Probe in Wasser eine weiße Trübung lief ei t, die sich in Lösungen von Dinaphthylmethandisulfonsaurem Natrium klar auflöst und auf Zusatz einiger Tropfen verdünnter Essigsäure eine Fällung liefert.126 parts of melamine, 60 parts of urea and 90 parts of paraformaldehyde are on the boiling water bath melted together and condensed until a sample in water ran a white turbidity, which dissolves clearly in solutions of sodium Dinaphthylmethandisulfonsaurem and on the addition of some Drops of dilute acetic acid provide a precipitate.
126 Teile Melamin, 180 Teile Harnstoff und 90 Teile Paraformaldehyd werden wie im Beisipel 1 zusammengeschmolzen und kondensiert.126 parts melamine, 180 parts urea and 90 parts Paraformaldehyde are melted and condensed as in Example 1.
126 Teile Melamin, 60 Teile Harnstoff, 90 Teile Paraformaldehyd und 60 Teile trockenes, gepulvertes Naphthalinsulfosäureharz werden bei 100° C geschmolzen und bei 120° C so lange kondensiert, bis eine Probe klar in heißem Wasser löslich ist und auf Zugabe einiger Tropfen verdünnter Essigsäure bei 40° C eine Fällung auftritt.126 parts melamine, 60 parts urea, 90 parts paraformaldehyde and 60 parts dry, powdered Naphthalenesulfonic acid resin are melted at 100 ° C and condensed at 120 ° C until a sample is clearly soluble in hot water and upon the addition of a few drops of dilute acetic acid 40 ° C a precipitation occurs.
Verfahren zur HerstellungMethod of manufacture
von Harzen aus Melamin,of melamine resins,
Harnstoff und ParaformaldehydUrea and paraformaldehyde
Anmelder:Applicant:
Farbenfabriken Bayer Aktiengesellschaft, Leverkusen-BayerwerkPaint factories Bayer Aktiengesellschaft, Leverkusen-Bayerwerk
Dr. Bruno Zorn, Köln-Deutz,
und Dr. Gustav Mauthe, Opladen,
sind als Erfinder genannt wordenDr. Bruno Zorn, Cologne-Deutz,
and Dr. Gustav Mauthe, Opladen,
have been named as inventors
126 Teile Melamin, 60 Teile Harnstoff und 45 Teile Paraformaldehyd werden zusammengeschmolzen und bei 120° C so lange kondensiert, bis eine Probe in Wasser trüb, in Naphthalinsulfosäureharzlösung klar löslich ist und auf Zugabe von etwas verdünnter Essigsäure eine Fällung ergibt.126 parts of melamine, 60 parts of urea and 45 parts of paraformaldehyde are melted together and Condensed at 120 ° C until a sample was cloudy in water and clear in naphthalenesulfonic acid resin solution is soluble and results in a precipitate on the addition of a little dilute acetic acid.
Claims (4)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1050542B true DE1050542B (en) | 1959-02-12 |
Family
ID=590919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1050542D Pending DE1050542B (en) | Process for the production of resins from melamine urea and paraformaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1050542B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0063319A1 (en) * | 1981-04-18 | 1982-10-27 | BASF Aktiengesellschaft | Method of making water-soluble or self-dispersing resinous tanning agents and their use |
-
0
- DE DENDAT1050542D patent/DE1050542B/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0063319A1 (en) * | 1981-04-18 | 1982-10-27 | BASF Aktiengesellschaft | Method of making water-soluble or self-dispersing resinous tanning agents and their use |
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