DE859460C - Process for the production of condensation products - Google Patents
Process for the production of condensation productsInfo
- Publication number
- DE859460C DE859460C DED4409D DED0004409D DE859460C DE 859460 C DE859460 C DE 859460C DE D4409 D DED4409 D DE D4409D DE D0004409 D DED0004409 D DE D0004409D DE 859460 C DE859460 C DE 859460C
- Authority
- DE
- Germany
- Prior art keywords
- condensation products
- sulfamides
- production
- water
- 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
- 238000000034 method Methods 0.000 title claims description 11
- 239000007859 condensation product Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 claims description 9
- -1 aromatic sulfamides Chemical class 0.000 claims description 7
- 239000002699 waste material Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical class NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229950008177 disulfamide Drugs 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical class OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- DETXZQGDWUJKMO-UHFFFAOYSA-N 2-hydroxymethanesulfonic acid Chemical compound OCS(O)(=O)=O DETXZQGDWUJKMO-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- ZCPJBFXFGWRCLP-UHFFFAOYSA-N benzene;sulfamide Chemical compound NS(N)(=O)=O.NS(N)(=O)=O.C1=CC=CC=C1 ZCPJBFXFGWRCLP-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DEVUYWTZRXOMSI-UHFFFAOYSA-N (sulfamoylamino)benzene Chemical compound NS(=O)(=O)NC1=CC=CC=C1 DEVUYWTZRXOMSI-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000002023 wood Substances 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
-
- 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
- C08G12/24—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with sulfonic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
- Chemical And Physical Treatments For Wood And The Like (AREA)
Description
Verfahren zur Herstellung von Kondensationsprodukten Es wurde gefunden, daß man zu technisch wertvollen Kondensationsprodukten gelangt, wenn man Sulfitablauge mit aromatischen Sulfamiden und Aldehyden, insbesondere Formaldehyd oder Formaldehyd abgebenden Stoffen kondensiert. Durch dieses Verfahren werden die gerberischen Eigenschaften der Sulfitablauge so weitgehend verbessert, daß die Kondensationsprodukte wertvolle Austauschgerbstoffe bilden, während die Ablauge selbst bekanntlich nur als Hilfsgerbstoff angesprochen werden kann.Process for the production of condensation products It has been found that one arrives at technically valuable condensation products if one uses sulphite waste liquor with aromatic sulfamides and aldehydes, especially formaldehyde or formaldehyde emitting substances condensed. Through this process, the tannic characteristics the sulphite liquor is so largely improved that the condensation products are valuable Substitute tanning agents form, while the waste liquor itself is known only as an auxiliary tanning agent can be addressed.
Unter Sulfitablauge sind die beim Aufschluß des Holzes u. dgl. nach dem Sulfitverfahren anfallende Ablauge bzw. deren durch Eindampfen gewonnene Konzentrate oder Trockensubstanzen, welche zweckmäßig in üblicher Weise enteisent und entkälkt sind, zu verstehen. Aromatische Sulfamide bzw. deren Kernsubstitutionsprodukte, die für das Verfahren als Ausgangsstoffe in Betracht kommen, sind beispielsweise Benzolsulfamid, 4-Toluolsulfamid, 4.-Chlorbenzolsulfamid, Benzol-i, 3-disulfamid, Diphenyl-4, 4'-disulfamid, Naphthalin-i, 3, 5-trisulfamid, Carbazoltetrasulfamid, Benzoesäure-3-sulfamid,2-Oxybenzoesäure-5-sulfamid, Benzoesäure-3, 5-disulfamid, Phenol-2, q., 6-trisulfamid, i-Oxynaphthalin-8-sulfamid, i-Oxynaphthalin-8-sulfamid-3-sulfonsäure usw. Ferner sind für das vorliegende Verfahren auch geeignet die aus den gemäß Patent 757 503 erhältlichen harzartigen Sulfochloriden durch Einwirkung von Ammoniak entstehenden Sulfamide u. dgl. Die Kohlenwasserstoffreste der Sulfamide können ganz allgemein Substituenten, wie Methyl-, Äthyl-, Hydroxylgruppen, Halogen und dergleichen, oder auch Heteroatome und Heteroatomgruppen, z. B. Äther-, Sulfon-, Ester-, Sulfonamid-, Carbonamidgruppen usw., enthalten.Sulphite waste liquor is to be understood as meaning the waste liquor resulting from the digestion of wood and the like after the sulphite process or concentrates or dry substances obtained by evaporation, which are expediently de-ironed and limed in the usual way. Aromatic sulfamides or their core substitution products which can be used as starting materials for the process are, for example, benzenesulfamide, 4-toluenesulfamide, 4-chlorobenzenesulfamide, benzene-i, 3-disulfamide, diphenyl-4, 4'-disulfamide, naphthalene-i , 3, 5-trisulfamide, carbazole tetrasulfamide, benzoic acid-3-sulfamide, 2-oxybenzoic acid-5-sulfamide, benzoic acid-3, 5-disulfamide, phenol-2, q., 6-trisulfamide, i-oxynaphthalene-8-sulfamide, i-Oxynaphthalene-8-sulfamide-3-sulfonic acid, etc. Furthermore, the sulfamides formed by the action of ammonia from the resinous sulfochlorides obtainable according to patent 757 503 and the like are also suitable for the present process. such as methyl, ethyl, hydroxyl groups, halogen and the like, or heteroatoms and heteroatom groups, e.g. B. ether, sulfone, ester, sulfonamide, carbonamide groups, etc. contain.
Als Aldehydkomponenten kommen bei diesem Verfahren hauptsächlich Formaldehyd, Acetaldehyd, Glyoxal, Acrolein, Crotonaldehyd, Furfurol usw. in Betracht oder entsprechende aldehy dabgebende Verbindungen, wie Paraformaldehy d, Trioxymethylen, Formaldehydbisulfit, Methylal, Hexamethvientetramin usw.The main aldehyde components used in this process are formaldehyde, Acetaldehyde, glyoxal, acrolein, crotonaldehyde, furfural etc. are considered or equivalent aldehyde-releasing compounds, such as paraformaldehyde, trioxymethylene, formaldehyde bisulfite, Methylal, hexamethvientetramine, etc.
Man kann.das Verfahren auch in der Weise durchführen, daß man zunächst aus den Sulfamiden und den Aldehyden Vorkondensationsprodukte bildet und diese dann auf die Sulfitablauge zur Einwirkung bringt. Als bekannte Kondensationsprodukte dieser Art sind die N-Methylolverbindungen der Sulfamide und deren Halogenwasserstoffsäureester, also die N-Halogenmethylverbindungen der Sulfamide, welche in bekannter Weise durch Einwirkung der Aldehyde auf die Sulfamide, gegebenenfalls unter Anwendung entsprechender Mengen Salzsäure, erhältlich sind.The procedure can also be carried out in such a way that, first of all, Forms precondensation products from the sulfamides and the aldehydes and then these brings to action on the sulphite liquor. As known condensation products of this type are the N-methylol compounds of sulfamides and their hydrohalic acid esters, So the N-halomethyl compounds of the sulfamides, which in a known manner by Effect of the aldehydes on the sulfamides, if necessary with the application of the appropriate Quantities of hydrochloric acid, are available.
Die Umsetzung zwischen den Ausgangsmaterialien und der Sulfitablauge erfolgt in wäßrigem Medium unter Erhitzen auf Temperaturen von etwa ioo'. Die Umsetzung ist vollendet, wenn das Kondensationsprodukt klar wasserlöslich ist. Beispiel i 6.1o Gewichtsteile einer enteisenten und entkälkten, bis zur pulvrigen Beschaffenheit eingedampften Sulfitablauge von 93,6 °;'o Trockengehalt werden mit 36o Raumteilen Wasser bis zur Bildung eines homogenen Sirups verrührt. Nunmehr werden 25o Gewichtsteile N-Methylol-p-toluolsulfamid eingetragen, und die Mischung wird, nachdem sie durch Rühren homogen geworden ist, auf go' erwärmt und bei dieser Temperatur gerührt, bis eine Probe in viel kaltem Wasser klar löslich ist. Das Produkt ist jetzt nach Verdünnung mit Wasser und Einstellung auf den geeigneten pH-Wert zum Gerben verwendbar. Beispiel 2 In die wie in Beispiel i hergestellte Sirupöse Sulfitablauge werden 236 Gewichtsteile eines feingepulverten technischen Gemisches von Benzol-i, 3- und -i, .1-disulfamid, wie es durch energische Sulfonierung von Benzol mit überschüssiger Chlorsulfonsäure und Umsetzung des isolierten Gemisches von Benzoli, 3- und -i, .1-disulfochlorid mit Ammoniak erhalten wird, eingetragen und gut verrührt. Hierauf werden innerhalb -: Stunden 185 Gewichtsteile einer 4o°/oigen wäßrigenFormaldehydlösung bei 2o bis 25' eingerührt, und es wird das Rühren bei Raumtemperatur noch etwa 5 Stunden fortgesetzt. Nunmehr wird auf 9o bis iooo erwärmt und diese Temperatur etwa Stunden aufrechterhalten, worauf eine Probe in Wasser klar löslich sein soll. Ist dieses derFall, so wird die Reaktionsmischung bei Wasserbadtemperatur unter vermindertem Druck zur Trockne eingedampft. Der in einer Ausbeute von 888 Gewichtsteilen erhaltene Rückstand läßt sich leicht zerreiben und bildet dann ein bräunlichgraues, leicht in Wasser lösliches Pulver. Das Erzeugnis ist ein vorzüglicher Austauschgerbstoff.The reaction between the starting materials and the sulphite waste liquor takes place in an aqueous medium with heating to temperatures of about 100 '. The reaction is complete when the condensation product is clearly soluble in water. EXAMPLE 6.1o parts by weight of a de-ironed and decalcified sulphite waste liquor with a dry content of 93.6 °, which has been evaporated to a powdery consistency, is stirred with 36o parts by volume of water until a homogeneous syrup is formed. Now 250 parts by weight of N-methylol-p-toluenesulfamide are added and the mixture, after it has become homogeneous by stirring, is warmed to go 'and stirred at this temperature until a sample is clearly soluble in a lot of cold water. The product can now be used for tanning after it has been diluted with water and adjusted to the appropriate pH value. Example 2 In the syrupy sulphite liquor prepared as in Example i, 236 parts by weight of a finely powdered technical mixture of benzene-i, 3- and -i, .1-disulphamide, as is achieved by vigorous sulphonation of benzene with excess chlorosulphonic acid and reaction of the isolated mixture of Benzoli, 3- and -i, .1-disulfochloride is obtained with ammonia, entered and stirred well. 185 parts by weight of a 40% aqueous formaldehyde solution are then stirred in at 20 to 25 hours within -: hours, and stirring is continued for about 5 hours at room temperature. Now it is heated to 90 to 10000 and this temperature is maintained for about hours, after which a sample should be clearly soluble in water. If this is the case, the reaction mixture is evaporated to dryness at water bath temperature under reduced pressure. The residue obtained in a yield of 888 parts by weight can be easily triturated and then forms a brownish-gray powder which is readily soluble in water. The product is an excellent replacement tanning agent.
In vorstehendem Beispiel kann *das Benzoldisulfamid durch 25o bis 3oo Gewichtsteile Naphthalin-I, 3, 5- oder -i, 3, 6-trisulfamid oder die gleiche Menge eines technischen Gemisches isomerer Naphthalintrisulfamide ersetzt werden. Bei gleicher Arbeitsweise erhält man so ein dem vorbeschriebenen ähnliches Erzeugnis. Beispiel 3 Man ersetzt in Beispiel e das Benzoldisulfamid durch 266 Gewichtsteile eines Sulfamids mit einem Stickstoffgehalt von io,5 °/o, das aus einem gemäß Patent 757 5o3 aus Naphthalin erhaltenen harzartigen Sulfochlorid durch Einwirkung von konzentriertem Ammoniakwasser hergestellt wurde. Die Arbeitsweise ist im übrigen wie in Beispiel 2. Auch hier wird ein pulverförmiger, leicht wasserlöslicher Gerbstoff erhalten.In the example above, * the benzene disulfamide can be replaced by 25o to 300 parts by weight of naphthalene-1, 3, 5- or -i, 3, 6-trisulfamide or the same Amount of a technical mixture of isomeric naphthalene trisulfamides to be replaced. With the same method of operation, a product similar to the one described above is obtained. Example 3 In example e, the benzene disulfamide is replaced by 266 parts by weight of a sulfamide with a nitrogen content of 10.5%, which is obtained from a patent 757 5o3 resinous sulfochloride obtained from naphthalene by the action of concentrated ammonia water. The way it works is by the way as in Example 2. Here, too, a powdery, easily water-soluble tanning agent is used obtain.
Claims (2)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED4409D DE859460C (en) | 1940-07-09 | 1940-07-09 | Process for the production of condensation products |
| NL101403A NL54943C (en) | 1940-07-09 | 1941-05-20 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DED4409D DE859460C (en) | 1940-07-09 | 1940-07-09 | Process for the production of condensation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE859460C true DE859460C (en) | 1952-12-15 |
Family
ID=7030981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED4409D Expired DE859460C (en) | 1940-07-09 | 1940-07-09 | Process for the production of condensation products |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE859460C (en) |
| NL (1) | NL54943C (en) |
-
1940
- 1940-07-09 DE DED4409D patent/DE859460C/en not_active Expired
-
1941
- 1941-05-20 NL NL101403A patent/NL54943C/xx active
Also Published As
| Publication number | Publication date |
|---|---|
| NL54943C (en) | 1943-06-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE848823C (en) | Process for the production of condensation products | |
| DE542286C (en) | Process for the representation of high molecular substances | |
| DE676854C (en) | Process for the production of tanning agents from lignosulfonic acids | |
| DE364040C (en) | Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde | |
| DE368521C (en) | Process for the production of tanning substances | |
| DE700920C (en) | Process for the production of water-soluble substances with a tanning effect | |
| DE867857C (en) | Process for the preparation of the ammonium compounds sulfomethylated phenolic condensation products | |
| DE875945C (en) | Process for the production of stable, water-soluble condensation products from urea and formaldehyde | |
| DE753346C (en) | Process for the production of condensation products | |
| DE858703C (en) | Process for the manufacture of tanning agents | |
| DE860551C (en) | Process for the production of curable water-soluble synthetic resins | |
| DE696777C (en) | Process for the production of water-soluble condensation products from lignosulfonic acids | |
| AT163159B (en) | Process for the production of synthetic resins from lignin | |
| DE696272C (en) | Process for the production of substances with a tanning effect | |
| DE840994C (en) | Process for the production of new amide cores | |
| DE648466C (en) | Process for the production of condensation products with a tanning effect | |
| AT162589B (en) | Process for the production of hardenable binders in durable, aqueous form | |
| DE172877C (en) | ||
| DE961351C (en) | Process for the production of water-soluble, tanning condensation products | |
| DE877759C (en) | Process for the production of condensation products | |
| DE1130822B (en) | Process for the production of lightfast condensation products by aftertreatment of phenol-urea-formaldehyde condensates containing sulfonic acid groups with phenols and formaldehyde | |
| DE1935006A1 (en) | Light-stable formaldehyde condensates | |
| DE2100439B2 (en) | Process for the production of preparations from disperse dyes and the use of these preparations | |
| DE408871C (en) | Process for the preparation of sulfobenzyla ethers from resinous condensation products derived from phenols | |
| DE976615C (en) | Process for the preparation of products from dicyandiamide-formaldehyde condensation products and metal salts of formaldehyde-condensed arylsulfonic acids |