DE618110C - Process for the production of curable and soluble condensation products from aromatic amines and formaldehyde - Google Patents
Process for the production of curable and soluble condensation products from aromatic amines and formaldehydeInfo
- Publication number
- DE618110C DE618110C DEA66455D DEA0066455D DE618110C DE 618110 C DE618110 C DE 618110C DE A66455 D DEA66455 D DE A66455D DE A0066455 D DEA0066455 D DE A0066455D DE 618110 C DE618110 C DE 618110C
- Authority
- DE
- Germany
- Prior art keywords
- formaldehyde
- curable
- condensation products
- production
- aromatic amines
- 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
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 6
- 239000007859 condensation product Substances 0.000 title claims description 4
- 150000004982 aromatic amines Chemical class 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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
- C08G12/04—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds
- C08G12/06—Amines
- C08G12/08—Amines aromatic
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
Verfahren zur Herstellung härtbarer und löslicher Kondensationsprodukte aus aromatischen Aminen und Formaldehyd Gegenstand des Hauptpatents 598 444 ist ein Verfahren zür Herstellung härtbarer und löslicher Kondensationsprodukte, bei dem die Einwirkung von Formaldehyd auf Anilin in alkoholischer Lösung bei Gegenwart einer mehrbasischen organischen Säure, insbesondere Phthalsäure, geg'eb'enenfalls unter Zusatz einer Kontaktsubstanz erfolgt.Process for the production of curable and soluble condensation products from aromatic amines and formaldehyde is the subject of main patent 598 444 a process for the production of curable and soluble condensation products which the action of formaldehyde on aniline in alcoholic solution in the presence a polybasic organic acid, in particular phthalic acid, if necessary takes place with the addition of a contact substance.
Die vorliegende Erfindung betrifft eine weitere Ausbildung dieses Verfahrens, die darin besteht, daß an Stelle des Anilins hier [3-Naphthylamin zur Umsetzung gebracht wird.The present invention relates to a further embodiment of this Process which consists in that instead of the aniline here [3-naphthylamine for Implementation is brought.
Beispiel 42,9 g ß-Naphthylamin, 9,9 g Phthalsäure und o, i g Natriumstannichlorid werden in ioo ccm Alkohol gelöst. Diese Lösung wird auf 40` erwärmt und mit ioo ccm einer Boo/oigen Formaldehydlösung versetzt. Durch die Reaktionswärme steigt die Temperatur ungefähr bis auf 75° an; unter tüchtigem Rühren läßt man langsam erkalten. Nach 2 Stunden wird zur Vervollständigung der Abscheidung des Harzes destilliertes Wasser zugegeben, bis ein weiterer Zusatz keinen Niederschlag mehr hervorruft. Dann läßt man 24 Stunden absitzen, gießt die wäßTige Mutterlauge ab, sammelt das Harz und wäscht es. Auch ohne Zusatz von Wasser setztsich das gebildete Harz nach geraumer Zeit von selbst ab. Das erhaltene Harz ist bei gewöhnlicher Temperatur pulverförmig, und @es unterscheidet sich somit von den Harzen, die aus Anilin, Toluidin u. dgl. in derselben Weise hergestellt werden. Die mit den letzteren erhältlichen Harze sind klebrig und zähflüssig und machen eine Reinigung mit 40 % igem Alkohol notwendig. Eine solche Behandlung erübrigt sich im vorliegenden Falle. Das pulverförmige Harz ist in Benzol, Aceton, Chloroform, Anilin :oder einem Gemisch von 2 Teilen Benzol und i Teil Alkohol löslich. Auch in Eisessig löst es sich auf. Man kann die Lösung zur Imprägnierung von Füllstoffen benutzen und beispielsweise 45 g getrocknetes Holzmehl mit einer Lösung tränken, die -45 g Harz und 75 ccm Benzol :enthält. Nach dem Verdunsten des Lösungsmittels wird das Harz durch Hitze unter Druck gehärtet, beispielsweise bei etwa ioo bis i5o° und einem Druck von Zoo bis 5oo at.Example 42.9 g of β-naphthylamine, 9.9 g of phthalic acid and 0.1 g of sodium stannous chloride are dissolved in 100 cc alcohol. This solution is heated to 40 'and ioo ccm of a boo / oigen formaldehyde solution. The heat of reaction increases the temperature up to about 75 °; leave slowly while stirring vigorously to cool off. After 2 hours, distillation is carried out to complete the deposition of the resin Water added until another addition no longer causes precipitation. then It is allowed to settle for 24 hours, the aqueous mother liquor is poured off and the resin is collected and washes it. Even without the addition of water, the resin formed sets after a considerable amount of time Time by itself. The resin obtained is powdery at ordinary temperature, and @it is thus different from the resins made from aniline, toluidine and the like. can be made in the same way. The resins obtainable with the latter are sticky and viscous and require cleaning with 40% alcohol. Such a treatment is unnecessary in the present case. The powdery resin is in benzene, acetone, chloroform, aniline: or a mixture of 2 parts benzene and i part alcohol soluble. It also dissolves in glacial acetic acid. One can have the solution use to impregnate fillers and, for example, 45 g dried Soak wood flour with a solution that contains -45 g of resin and 75 cc of benzene: To the evaporation of the solvent, the resin is hardened by heat under pressure, for example at about 100 to 150 degrees and a pressure of zoo to 500 at.
Claims (1)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1930598444D DE598444C (en) | 1930-05-15 | 1930-05-15 | Process for the production of curable and soluble condensation products from aromatic amines and formaldehyde |
| DEA66455D DE618110C (en) | 1930-09-08 | 1930-09-08 | Process for the production of curable and soluble condensation products from aromatic amines and formaldehyde |
| DE1930639881D DE639881C (en) | 1930-05-15 | 1930-09-08 | Process for the production of condensation products from formaldehyde and aniline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA66455D DE618110C (en) | 1930-09-08 | 1930-09-08 | Process for the production of curable and soluble condensation products from aromatic amines and formaldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE618110C true DE618110C (en) | 1935-09-02 |
Family
ID=6944135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA66455D Expired DE618110C (en) | 1930-05-15 | 1930-09-08 | Process for the production of curable and soluble condensation products from aromatic amines and formaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE618110C (en) |
-
1930
- 1930-09-08 DE DEA66455D patent/DE618110C/en not_active Expired
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