DE459700C - Process for the production of non-deliquescent condensation products from sulphite cellulose waste liquor - Google Patents
Process for the production of non-deliquescent condensation products from sulphite cellulose waste liquorInfo
- Publication number
- DE459700C DE459700C DEA44688D DEA0044688D DE459700C DE 459700 C DE459700 C DE 459700C DE A44688 D DEA44688 D DE A44688D DE A0044688 D DEA0044688 D DE A0044688D DE 459700 C DE459700 C DE 459700C
- Authority
- DE
- Germany
- Prior art keywords
- parts
- sulphite cellulose
- waste liquor
- deliquescent
- 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.)
- Expired
Links
- 229920002678 cellulose Polymers 0.000 title claims description 16
- 239000001913 cellulose Substances 0.000 title claims description 16
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 title claims description 15
- 239000007859 condensation product Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000002699 waste material Substances 0.000 title description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 150000004982 aromatic amines Chemical class 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- 150000002989 phenols Chemical class 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000126 substance Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- JBCSOBKDUKAJHR-UHFFFAOYSA-N ClO.NC1=CC=CC=C1 Chemical compound ClO.NC1=CC=CC=C1 JBCSOBKDUKAJHR-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005406 washing 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
- C14C3/24—Chemical tanning by organic agents using lignin derivatives, e.g. sulfate liquor
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Treating Waste Gases (AREA)
- Disinfection, Sterilisation Or Deodorisation Of Air (AREA)
Description
Verfahren zur Herstellung von nicht zerfließlichen Kondensationsprodukten aus Sulfitcelluloseablauge Die Sulfitcelluloseablauge findet eine überaus vielseitige Verwendung, unter anderem zu Klebstoffen, als Faserschutz, Beiz-, Gerb-und Waschmittel usw. Man benutzt meist eine eingedampfte Lauge von sirupartiger Beschaffenheit, da ein zur Trockne eingedampftes Erzeugnis sehr hygroskopisch ist und hald, zumal bei der Aufbewahrung in feuchten Räumen, zii einer harten, dunklen, verharzten Masse zusammenbackt, derer: Verarbeitung unbequem ist.Process for the production of non-deliquescent condensation products from sulphite cellulose waste liquor The sulphite cellulose waste liquor is extremely versatile Use, among other things, for adhesives, as fiber protection, staining, tanning and washing agents etc. One usually uses an evaporated lye with a syrupy consistency, since a product that has evaporated to dryness is very hygroscopic and always remains, especially for storage in damp rooms, for a hard, dark, resinous mass caked, which: Processing is inconvenient.
Da der Versand der Lauge im Hinblick auf die mitgeführte Wassermenge unwirtschaftlich ist und der Gebrauch der sirupartigen Lauge mit Nachteilen verknüpft bleibt, hat man sich bemüht, Wege zu finden, um aus der Sulfitcelluloseablauge leicht zu handhabende, pulverförmig bleibende, an der Luft nicht zerfiießliche, jedoch leicht in Lösung zu bringende Erzeugnisse zu gewinnen.Because the shipping of the lye in terms of the amount of water carried is uneconomical and the use of the syrupy liquor has disadvantages remains, efforts have been made to find ways to get out of the sulphite cellulose liquor easily to be handled, remaining in powder form, non-dissolving in the air, however to obtain products that are easy to dissolve.
Die Erfindung öffnet einen gangbaren Weg hierzu. Das gefundene Verfahren besteht darin. die in der Lauge enthaltenen Ligninsulfosäuren mit Harnstoff, mit aromatischen Aminen oder mit Plienolen der Benzolreihe einerseits und Aldehvden oder Ketonen anderseits einer Kondensation zu unterwerfen.The invention opens a feasible way to do this. The method found consists in it. the lignosulfonic acids contained in the lye with urea, with aromatic amines or with plienols of the benzene series on the one hand and aldehydes or to subject ketones to condensation on the other hand.
Nach der britischen Patentschrift a4 196 vom Jahre igi4 hat man zwar Sulfitcelluloseablauge mit Oxyarylverbindungen behandelt, hierbei jedoch nicht feste Präparate, sondern nur flüssige Gerbmittel gewonnen. Nach der amerikanischen Patentschrift i 143 174 wird die in der Sulfitcelluloseablauge vorhandene Ligninsulfosäure mit Phenol und Acetaldehyd, der aus dem durch Vergären der Sulfitcelluloseablauge gebildeten Alkohol entstanden ist, kondensiert. Die Verwendung des Acetaldehyds wird daher hier nicht beansprucht.According to the British patent specification A4 196 from the year igi4 one has Sulphite cellulose waste liquor treated with oxyaryl compounds, but not solid Preparations, but only obtained liquid tanning agents. According to the American patent specification i 143 174 is the lignosulphonic acid present in the sulphite cellulose waste liquor Phenol and acetaldehyde, which is formed from the fermentation of the sulphite cellulose waste liquor Alcohol formed, condensed. The use of the acetaldehyde is therefore not claimed here.
Beispiel i i5o Teile eingedickte Sulfitcelluloseablauge (etwa a8° Be) werden mit io Teilen Formaldehyd 3oprozentig und i3 Teilen Anilinchlorhydrat, in Wasser gelöst, verrührt. Das Gemisch wird erwärmt, und schließlich wird durch Zusatz von Salzsäure und konzentrierter Chlornatriumlösung das gelbe Kondensationsprodukt ausgefällt. Man erhält 6o Teile eines lufttrockenen Präparates, das sich leicht unter Zusatz von Alkalicarbonat, Alkalihydroxyd oder Ammoniak in Wasser, außerdem in starker Essigsäure und Ameisensäure löst, dagegen unlöslich in Wasser, Salzsäure, Alkohol, Aceton ist.Example 150 parts of concentrated sulphite cellulose waste liquor (about a8 ° Be) with 10 parts formaldehyde 3% and 13 parts aniline chlorohydrate, dissolved in water, stirred. The mixture is heated, and finally is through Addition of hydrochloric acid and concentrated sodium chloride solution to the yellow condensation product failed. 60 parts of an air-dry preparation are obtained which are easy to remove with the addition of alkali carbonate, alkali hydroxide or ammonia in water, moreover dissolves in strong acetic acid and formic acid, but insoluble in water, hydrochloric acid, Alcohol, acetone is.
Beispiel e aoo Teile eingedickte Sulfitcelluloseablauge werden mit io Teilen Formaldehyd 3oprozentig und io Teilen Phenol unter Erwärmen verrührt. Dann werden 23 Teile Salzsäure 20° Be zugesetzt. Es wird weitererhitzt und schließlich durch Zusatz von konzentrierter Chlornatriumlösung das braune Kondensationsprodukt abgeschieden. Die Ausbeute beträgt etwa 8o Teile lufttrockene Substanz, die sich gegenüber Lösungsmitteln wie das Kondensationsprodukt des Beispiels i verhält. Beispiel 3 Zoo Teile eingedickte Sulfitcelluloseablauge werden mit i 5 Teilen ß-Naphthylamin, das unter Salzsäurezusatz in heißem Wasser gelöst wurde, und mit io Teilen Formaldehyd 3oprozentig verrührt. Nachdem der anfangs entstandene Niederschlag sich wieder gelöst hat, scheidet sich bei weiterem Erwärmen das gelbe Kondensationsprodukt ab. Man gewinnt etwa 13o Teile lufttrockene Substanz von den im Beispiel i genannten Eigenschaften.Example e aoo parts of concentrated sulphite cellulose liquor are mixed with 10 parts formaldehyde 3 percent and 10 parts of phenol with heating stirred. Then 23 parts of hydrochloric acid 20 ° Be are added. It continues to be heated and finally the brown condensation product by adding concentrated sodium chloride solution deposited. The yield is about 80 parts of air-dry substance that can be found to solvents as the condensation product of Example i behaves. example 3 parts of concentrated sulphite cellulose liquor are mixed with 5 parts of ß-naphthylamine, which was dissolved in hot water with the addition of hydrochloric acid, and with 10 parts of formaldehyde 3 percent mixed. After the initially formed precipitate has dissolved again the yellow condensation product separates out on further heating. Man gains about 130 parts of air-dry substance from the properties mentioned in example i.
Beispiel 4 ioo Teile eingedickte Sulfitcelluloseablauge werden mit 6 Teilen Aceton, 6 Teilen Harnstoff. in Wasser gelöst, und 32 Teilen Natriumhydroxydlösung 34° Be nacheinander verrührt. Das Gemisch wird erhitzt, und schließlich wird durch Zusatz von Salzsäure und Chlornatrium das gelbe Kondensationsprodukt abgeschieden. Die Ausbeute beträgt etwa 5o Teile lufttrockene Substanz von den im Beispiel i genannten Eigenschaften.Example 4 100 parts of concentrated sulphite cellulose liquor are mixed with 6 parts of acetone, 6 parts of urea. dissolved in water, and 32 parts of sodium hydroxide solution 34 ° Be stirred one after the other. The mixture is heated, and finally is through Addition of hydrochloric acid and sodium chloride separates the yellow condensation product. The yield is about 50 parts of air-dry substance from those mentioned in Example i Properties.
Beispiel s i So Teile eingedickte Sulfitcelluloseablauge werden nacheinander mit i i Teilen 4-Aminoi-methylbenzol (in heißem Wasser unter Salzsäurezusatz gelöst) und io Teilen Formaldehyd 3oprozentig verrührt. Durch Erwärmen wird das rotbraune Kondensationsprodukt abgeschieden. Man erhält etwa 6o Teile lufttrockene Substanz, die in Wasser, Salzsäure, Alkohol unlöslich ist, sich dagegen in Aceton, starker Essigsäure und Ameisensäure und unter Zusatz von Alkalicarbonat, Alkalihydroxyd oder Ammoniak in Wasser löst. Beispiel 6 Zoo Teile eingedickte Sulfitcelluloseablauge werden nacheinander mit io Teilen Benzaldehyd und 15 Teilen ß-Naphthylamin, in heißem Waser unter Salzsäurezusatz gelöst, . verrührt. Man erwärmt die Masse und scheidet durch Zusatz von Salzsäure und Chlornatriumlösung das gelbe Kondensationsprodukt ab. Die Ausbeute beträgt etwa i2o Teile lufttrockene Substanz von den im Beispiels genannten Eigenschaften.Example s i So parts of thickened sulfite cellulose liquor are successively with i i parts of 4-aminoim-methylbenzene (dissolved in hot water with the addition of hydrochloric acid) and 10 parts of formaldehyde 3 percent. When heated, it becomes red-brown Condensation product deposited. About 60 parts of air-dry substance are obtained, which is insoluble in water, hydrochloric acid, and alcohol, but is stronger in acetone Acetic acid and formic acid and with the addition of alkali carbonate, alkali hydroxide or dissolves ammonia in water. Example 6 Zoo parts concentrated sulphite cellulose liquor are successively with 10 parts of benzaldehyde and 15 parts of ß-naphthylamine, in hot Water dissolved with the addition of hydrochloric acid,. stirred. The mass is heated and separated the yellow condensation product is formed by adding hydrochloric acid and sodium chloride solution away. The yield is about 12o parts air-dry substance from those in the example mentioned properties.
Beispiel ? Zoo Teile eingedickte Sulfitcelluloseablauge verrührt man nacheinander mit i i Teilen Resorcin und io Teilen Formaldehyd 3oprozentig, erhitzt die Masse und scheidet schließlich durch Zusatz von Salzsäure und Natriumchloridlösung das Kondensationsprodukt ab. Man gewinnt etwa 8o Teile lufttrockene Substanz von den im Beispiel i genannten Eigenschaften.Example ? Zoo parts of concentrated sulphite cellulose waste liquor are stirred one after the other with i i parts resorcinol and io parts formaldehyde 3%, heated the mass and finally separates by adding hydrochloric acid and sodium chloride solution the condensation product from. About 80 parts of air-dry substance are obtained from the properties mentioned in example i.
Beispiel 8 ioo Teile eingedickte Sulfitcelluloseablauge verrührt man nacheinander mit io Teilen Formaldehyd, 6 Teilen Harnstoff, in Wasser gelöst,- lind 3z Teilen Natriumhydroxydlösung 34° Be. Man erhitzt die Masse und scheidet durch Zusatz von Salzsäure und Chlornatriumlösung das graue Kondensationsprodukt ab. Man erhält etwa 6o Teile lufttrockene Substanz mit den im Beispiel i genannten Löslichkeitseigenschaften.Example 8 100 parts of concentrated sulphite cellulose waste liquor are stirred up successively with 10 parts of formaldehyde, 6 parts of urea, dissolved in water, - lind 3z parts of sodium hydroxide solution 34 ° Be. The mass is heated and separated Addition of hydrochloric acid and sodium chloride solution to remove the gray condensation product. Man contains about 60 parts of air-dry substance with the solubility properties mentioned in Example i.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA44688D DE459700C (en) | 1925-04-09 | 1925-04-09 | Process for the production of non-deliquescent condensation products from sulphite cellulose waste liquor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEA44688D DE459700C (en) | 1925-04-09 | 1925-04-09 | Process for the production of non-deliquescent condensation products from sulphite cellulose waste liquor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE459700C true DE459700C (en) | 1929-04-13 |
Family
ID=6934326
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEA44688D Expired DE459700C (en) | 1925-04-09 | 1925-04-09 | Process for the production of non-deliquescent condensation products from sulphite cellulose waste liquor |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE459700C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE921776C (en) * | 1943-07-02 | 1954-12-30 | Bakelite Ges M B H | Process for the production of a resinous, thermosetting condensation product from sulphite waste liquor |
| DE1247649B (en) * | 1956-10-11 | 1967-08-17 | Waldhof Zellstoff Fab | Process for the production of small particle size lignin condensation products |
| DE1299861B (en) * | 1961-02-10 | 1969-07-24 | West Virginia Pulp & Paper Co | Reinforcing agent for natural or synthetic rubber |
-
1925
- 1925-04-09 DE DEA44688D patent/DE459700C/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE921776C (en) * | 1943-07-02 | 1954-12-30 | Bakelite Ges M B H | Process for the production of a resinous, thermosetting condensation product from sulphite waste liquor |
| DE1247649B (en) * | 1956-10-11 | 1967-08-17 | Waldhof Zellstoff Fab | Process for the production of small particle size lignin condensation products |
| DE1299861B (en) * | 1961-02-10 | 1969-07-24 | West Virginia Pulp & Paper Co | Reinforcing agent for natural or synthetic rubber |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2148893A (en) | Process for preparing tanning agents | |
| DE459700C (en) | Process for the production of non-deliquescent condensation products from sulphite cellulose waste liquor | |
| US2266265A (en) | Manufacture of resinous condensation products from amide-like compounds and purified lignin-sulphonic acids | |
| DE934820C (en) | Process for the production of dry starch preparations which are soluble in cold water | |
| US2191737A (en) | Production of water-soluble condensation products | |
| DE889225C (en) | Process for the production of condensation products | |
| Dorée et al. | Contributions to the Study of Lignin: Part I. Metalignin, a New Type of Alkali Lignin | |
| DE686111C (en) | Process for the production of water-soluble condensation products from lignosulfonic acids | |
| DE480898C (en) | Process for the preparation of powdery, non-deliquescent products from sulphite cellulose waste liquor | |
| DE707006C (en) | Process for the production of water-soluble condensation products | |
| DE364040C (en) | Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde | |
| DE820440C (en) | Process for the preparation of aminocarboxylic acids by hydrolysis of their lactams | |
| DE1053517B (en) | Process for the preparation of condensation products containing sulfo groups from phenols and formaldehyde | |
| DE734279C (en) | Process for the production of cation-exchanging synthetic resins | |
| DE417972C (en) | Process for the production of tanning substances | |
| CH95457A (en) | Process for converting the resinous phenol-formaldehyde condensation product into an easily pulverizable resin. | |
| DE413157C (en) | Process for tanning animal skins | |
| SU52209A1 (en) | The method of obtaining the condensation products of urea or thiourea | |
| DE858703C (en) | Process for the manufacture of tanning agents | |
| DE699129C (en) | Process for the production of water-soluble substances with a tanning effect | |
| DE388766C (en) | Process for the preparation of soluble resinous condensation products from phenols and formaldehyde | |
| DE970611C (en) | Process for the production of condensation products | |
| DE871964C (en) | Process for the production of cation-exchanging synthetic resins | |
| DE753346C (en) | Process for the production of condensation products | |
| DE487654C (en) | Process for the preparation of condensation products from aromatic amines and formaldehyde |