AT70369B - Process for the preparation of water-soluble condensation products, which dissolve poorly soluble components of natural tannins with ease. - Google Patents
Process for the preparation of water-soluble condensation products, which dissolve poorly soluble components of natural tannins with ease.Info
- Publication number
- AT70369B AT70369B AT70369DA AT70369B AT 70369 B AT70369 B AT 70369B AT 70369D A AT70369D A AT 70369DA AT 70369 B AT70369 B AT 70369B
- Authority
- AT
- Austria
- Prior art keywords
- water
- ease
- preparation
- condensation products
- soluble
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title description 2
- 238000000034 method Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 title 1
- 229920001864 tannin Polymers 0.000 title 1
- 239000001648 tannin Substances 0.000 title 1
- 235000018553 tannin Nutrition 0.000 title 1
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- 229910052601 baryte Inorganic materials 0.000 description 1
- 239000010428 baryte Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000001180 sulfating effect Effects 0.000 description 1
- 238000006277 sulfonation reaction 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
Es wurde gefunden, dass man zu Kondensationsprodukten von hervorragender technischer Bedeutung gelangt, wenn man Naphtalinsulfosäuren oder ihre Homologen bei An-oder Ab- wesenheit von kondensierend wirkenden Mitteln, wie z. B. Schwefelsäure, Salzsäure, Eisessig usw., mit Formaldehyd oder formaldehydent wickelnden Stoffen-unter solchen Bedingungen, insbesondere bei solcher Temperatur, solange und in solchen Mengenverhältnissen behandelt, dass im wesentlichen nur wasserlösliche Verbindungen erhalten werden. Im Falle der Verwendung von Schwefelsäure ist beispielsweise ein allzu grosser Überschuss derselben sowie eine zu lange Einwirkung, namentlich in der Wärme, zu venneiden.
Man kann zu derartigen Produkten auch gelangen, wenn man die wasserunlöslichen Einwirkungsprodukte von Formaldehyd bzw. formaldehydentwickelnden Mitteln auf Naphtalin oder seine Homologen, wie sie z. B. durch Einwirkung von mehr als Molekül Formaldehyd auf 1 Molekül Naphtalin bei Gegenwart von Säuren oder anderweitig erhältlich sind, durch Behandeln mit sulfierend wirkenden Mitteln in wasserlösliche Verbindungen überführt.
Die so erhältlichen Substanzen haben unter anderem die wertvolle Eigenschaft, dass sie die schwerlöslichen Bestandteile natürlicher Gerbstoffe mit Leichtigkeit lösen.
Beispiel 1.
10 Teile Naphtalin werden mit 12#5 Teilen 98%iger Schwefelsäure solange auf 130 bis 1400 erhitzt, bis die Sulfierung beendet ist. Man kühlt alsdann auf etwa 80 bis 90 ab, fügt zu dem noch
Schwefelsäure enthaltenden Reaktionsgemisch unter kräftigem Umrühren portionenweise 4 Teile 30gewichtsprozentigen Formaldehyd bei einer Temperatur von 60 bis 1000 hinzu und hält bei dieser Temperatur. Nach einiger Zeit wird die Masse immer dicker, so dass sie sich gegen Ende der Reaktion nur noch sehr schwer rühren lässt. Man setzt deshalb gegen Schluss der Operation zweckmässig noch soviel Wasser zu, dass das Reaktionsgemisch noch beweglich bleibt, und lührt solange, bis der Folmaldehydgtruch verschwunden ist.
Das so erhaltene Produkt wird beim
Erkalten fest und stellt alsdann eine harzige, wenig gefärbte, in kaltem Wasser leicht lösliche
Masse dar. An Stelle von Schwefelsaure können bei der Kondensation auch andere kondensierend
EMI1.2
Analog verfährt man bei der Kondensation von reiner Naphtalinsulfosäure mit Formaldehyd in Abwesenheit von Kondensationsniittein.
Beispiel 9.
EMI1.3
gelöst und mit Baryt oder Kalk in üblicher Weise von überschüssiger Schwefelsäure befreit. Man erhält so eine Lösung der Su ! fosäure ; die Alkalisalze sind ebenso wie die freie Sulfosäure in Wasser leicht löslich. Beispiel 3.
B e i s p i e l 3.
250 Teile Methylnaphtalin werden mit 250 Teilen konzentrierter Schwefelsäure bei 130
EMI1.4
Weise. Die so erhältliche Sulfosäure ist amorph bzw. zäh und sirupös ; ihre Alkalisalze sind wie die freie Säure in Wasser leicht löslich.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
EMI1.1
It has been found that condensation products of outstanding technical importance are obtained if naphthalene sulfonic acids or their homologues are used in the presence or absence of agents having a condensing action, such as. B. sulfuric acid, hydrochloric acid, glacial acetic acid, etc., with formaldehyde or formaldehyde developing substances treated under such conditions, in particular at such temperature, as long and in such proportions that essentially only water-soluble compounds are obtained. In the case of the use of sulfuric acid, for example, an excessively large excess of it and too long exposure to it, especially in heat, should be avoided.
Such products can also be obtained if the water-insoluble action products of formaldehyde or formaldehyde-developing agents on naphthalene or its homologues, such as those used, for. B. by the action of more than one molecule of formaldehyde to 1 molecule of naphthalene in the presence of acids or otherwise obtainable, converted into water-soluble compounds by treatment with sulfating agents.
The substances obtainable in this way have, among other things, the valuable property that they easily dissolve the poorly soluble components of natural tanning agents.
Example 1.
10 parts of naphthalene are heated to 130 to 1400 with 12 # 5 parts of 98% strength sulfuric acid until the sulfonation has ended. You then cool down to about 80 to 90, adds to that
Sulfuric acid-containing reaction mixture, with vigorous stirring, add 4 parts of 30 weight percent formaldehyde in portions at a temperature of 60 to 1000 and hold at this temperature. After a while the mass becomes thicker and thicker, so that towards the end of the reaction it is very difficult to stir. It is therefore advisable to add enough water towards the end of the operation that the reaction mixture still remains mobile, and stir until the folmaldehyde residue has disappeared.
The product thus obtained is at
It cools down and then turns into a resinous, slightly colored, easily soluble in cold water
Mass. Instead of sulfuric acid, others can also condense during the condensation
EMI1.2
A similar procedure is used for the condensation of pure naphthalene sulfonic acid with formaldehyde in the absence of condensation agents.
Example 9.
EMI1.3
dissolved and freed from excess sulfuric acid in the usual way with barite or lime. So you get a solution of the Su! phosic acid; the alkali salts, like the free sulfonic acid, are easily soluble in water. Example 3.
Example 3.
250 parts of methylnaphthalene are mixed with 250 parts of concentrated sulfuric acid at 130
EMI1.4
Wise. The sulfonic acid obtainable in this way is amorphous or tough and syrupy; their alkali salts, like the free acid, are easily soluble in water.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1005X | 1913-02-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT70369B true AT70369B (en) | 1915-11-10 |
Family
ID=87929954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT70369D AT70369B (en) | 1913-02-22 | 1913-08-16 | Process for the preparation of water-soluble condensation products, which dissolve poorly soluble components of natural tannins with ease. |
Country Status (2)
| Country | Link |
|---|---|
| AT (1) | AT70369B (en) |
| NL (1) | NL1005C (en) |
-
1913
- 1913-07-25 NL NL3036A patent/NL1005C/en active
- 1913-08-16 AT AT70369D patent/AT70369B/en active
Also Published As
| Publication number | Publication date |
|---|---|
| NL1005C (en) | 1916-01-03 |
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