CH321386A - Process for the preparation of a new aldehyde condensation product of guanyl melamines - Google Patents
Process for the preparation of a new aldehyde condensation product of guanyl melaminesInfo
- Publication number
- CH321386A CH321386A CH321386DA CH321386A CH 321386 A CH321386 A CH 321386A CH 321386D A CH321386D A CH 321386DA CH 321386 A CH321386 A CH 321386A
- Authority
- CH
- Switzerland
- Prior art keywords
- mixture
- formaldehyde
- aldehyde condensation
- preparation
- condensation product
- Prior art date
Links
- 239000007859 condensation product Substances 0.000 title claims description 8
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims 2
- 229920000877 Melamine resin Polymers 0.000 title 1
- 150000007974 melamines Chemical class 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000007787 solid Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 4
- -1 guanylmelamine hydrochlorides Chemical class 0.000 claims description 4
- 239000000982 direct dye Substances 0.000 claims description 3
- 238000004043 dyeing Methods 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- ZIZMTYLBNDRKDA-UHFFFAOYSA-N 2-(4,6-diamino-1,3,5-triazin-2-yl)guanidine;hydrochloride Chemical compound Cl.NC(N)=NC1=NC(N)=NC(N)=N1 ZIZMTYLBNDRKDA-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- OKHMDSCYUWAQPT-UHFFFAOYSA-N n'-[2-(2-aminoethylamino)ethyl]ethane-1,2-diamine;tetrahydrochloride Chemical compound Cl.Cl.Cl.Cl.NCCNCCNCCN OKHMDSCYUWAQPT-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
<B>Verfahren</B> zur Herstellung <B>eines neuen</B> Aldehydkondensationsproduktes <B>von</B> Guanyhnelaminen Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer Misehung von Aldehydkondensationsprodukten, das da durch gekennzeiehnet ist, da.ss man eine Mi schung von Guanylmelamin-hydrochloriden, wie sie durch Behandlung von Dicyandiamid in einem inerten Lösungsmittel in der Wärme mit gasförmigem Chlorwasserstoff erhältlich ist,
bei erhöhter Temperatur mit wässrigem Formaldehyd umsetzt und anschliessend die entstandene Mischung der Formaldehydkon- densationsprodukte in der Wärme mit Tri- äthylentetramintetrahydroch'lorid weiterkon densiert.
Die Umsetzung der Mischung von Guanyl- inelaminhydrochloriden mit Formaldehyd und die anschliessende Weiterkondensation mit Tri- ätliyientetramin-tetrahydroehlorid können zum Beispiel in der Weise vorgenommen werden,
1a1> man auf 1 Mol einer als Monoguanyl- inelamin-hydrochlorid berechneten Mischung von (_tuanylmelamin-hydrocliloriden bei 70 bis 75" in Gegenwart von Wasser 4 Mol. Formalde hyd einwirken lässt und dann das Formalde- hydkondensat.ionsprodukt mit 1 Mol Triät.hy- lent.et.ramin-tetrahydrochlorid weiterkonden siert.
Die auf diese Weise hergestellte Mischung von Aldehydkondensationsprodukten stellt eine feste, in Wasser lösliche Masse dar, welche zum Wassereehtmachen von Färbungen aus Direktfarbstoffen verwendet werden kann. Im nachfolgenden Beispiel bedeuten Teile Gewichtsteile, falls nichts anderes bemerkt wird; das Verhältnis zwischen Gewichtsteilen und Volumteilen ist das gleiche wie dasjenige zwischen dem Kilogramm und dem Liter. Die Temperaturen sind in Celsiusgraden ange geben.
Beispiel 10,2 Teile der unten näher beschriebenen Mischung von Guanylmelamin-hydrochloriden, enthaltend als Hauptbestandteil Monoguanyl- melamin-hydrochlorid, werden bei 70-75 in 15,6 Teilen genau neutralisierter, 38,3%iger Formaldehydlösung gelöst. Sobald Lösung ein getreten ist, kühlt man ab, fügt 7,3 Teile Triäthylen-tetramin, welche vorher mit konz. Salzsäure neutralisiert worden sind, hinzu und erwärmt in einem Bad von 80-85 bis zur beginnenden Verdickung.
Anschliessend ver dünnt man mit 20 Teilen Wasser und trocknet bei 40-45 unter vermindertem Druck. Das Trocknen soll möglichst schnell erfolgen, um zu verhindern, dass sich unlösliche Anteile bilden. Der so erhaltene feste Rückstand ist in kochendem Nasser löslich.
Das neue Produkt kann zum Wasserecht machen von Färbungen aus Direktfarbstoffen -verwendet werden.
Die oben beschriebene Mischung von Guanylmelaminhydrochloriden kann wie folgt hergestellt werden: Eine Mischung von 160 Teilen wasserfreiem Pyridin und 240 Teilen Nitrobenzol wird bei 90 mit Salzsäuregas gesättigt. Nach dem Er wärmen auf 110 werden bei dieser Tempera tur 100 Teile Dicyandiamid in kleinen An teilen unter Durchleiten von Salzsäuregas ein getragen. Man verfährt dabei in der Weise, dass ein weiterer Zusatz von Dicyandiamid erst erfolgt, wenn die Reaktionsmischung wie der mit Salzsäuregas gesättigt ist.
Nach be endigtem Eintragen erhitzt man weitere 15 Mi nuten auf 110 unter Durchleiten von Salz- säuregas, kühlt auf 50 ab und trennt die aus geschiedenen festen Anteile von der Mutter lauge. Diese festen Reaktionsprodukte wer den bei 90-100 in etwa 700 Teilen Wasser gelöst, worauf man durch Zusatz von Ammo- niaklösung auf einen pH-Wert von 5-9 ein stellt. Nach dem Abtrennen einer geringen Menge fester Verunreinigungen wird die er haltene Lösung auf 5 abgekühlt, worauf man das sich abscheidende Reaktionsprodukt von der 1-Iutterlauge abtrennt und trocknet.
<B> Process </B> for producing <B> a new </B> aldehyde condensation product <B> from </B> guanyhnelamines The subject matter of the present patent is a process for producing a mixture of aldehyde condensation products, which is indicated by the fact .ss one is a mixture of guanylmelamine hydrochlorides, as can be obtained by treating dicyandiamide in an inert solvent in the heat with gaseous hydrogen chloride,
reacts with aqueous formaldehyde at an elevated temperature and then further condenses the resulting mixture of formaldehyde condensation products in the heat with triethylenetetramine tetrahydrochloride.
The reaction of the mixture of guanyl inelamine hydrochlorides with formaldehyde and the subsequent further condensation with triethylamine tetramine tetrahydrochloride can be carried out, for example, in the manner
1a1> 4 mol. Formaldehyde are allowed to act on 1 mol of a mixture calculated as monoguanyl inelamine hydrochloride of (_tuanylmelamine hydrochloride at 70 to 75 "in the presence of water, and then the formaldehyde condensate ion product with 1 mol triet.hy - lent.et.ramin-tetrahydrochloride condensed further.
The mixture of aldehyde condensation products produced in this way represents a solid, water-soluble mass which can be used for making dyeings from direct dyes water-absorbent. In the following example, parts mean parts by weight, unless otherwise noted; the ratio between parts by weight and parts by volume is the same as that between the kilogram and the liter. The temperatures are given in degrees Celsius.
EXAMPLE 10.2 parts of the mixture of guanylmelamine hydrochlorides described in more detail below, containing monoguanyl melamine hydrochloride as the main component, are dissolved at 70-75 in 15.6 parts of exactly neutralized 38.3% formaldehyde solution. As soon as a solution has entered, it is cooled, 7.3 parts of triethylenetetramine, which previously with conc. Hydrochloric acid have been neutralized, added and heated in a bath from 80-85 until the beginning of thickening.
Then ver diluted with 20 parts of water and dried at 40-45 under reduced pressure. The drying should take place as quickly as possible to prevent insoluble fractions from forming. The solid residue thus obtained is soluble in boiling water.
The new product can be used to make dyeings made from direct dyes waterfast.
The above-described mixture of guanylmelamine hydrochlorides can be prepared as follows: A mixture of 160 parts of anhydrous pyridine and 240 parts of nitrobenzene is saturated at 90 ° with hydrochloric acid gas. After he warm to 110 at this tempera ture 100 parts of dicyandiamide are worn in small parts while passing hydrochloric acid gas. The procedure is such that a further addition of dicyandiamide only takes place when the reaction mixture is saturated with hydrochloric acid gas.
After the end of the introduction, the mixture is heated to 110 for a further 15 minutes while passing hydrochloric acid gas through it, cooled to 50 and the separated solid fractions are separated from the mother liquor. These solid reaction products are dissolved in about 700 parts of water at 90-100, whereupon the pH is adjusted to 5-9 by adding ammonia solution. After a small amount of solid impurities has been separated off, the solution obtained is cooled to 5, whereupon the reaction product which separates out is separated off from the 1-Iutter liquor and dried.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1054747X | 1951-04-24 | ||
| CH321386T | 1952-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH321386A true CH321386A (en) | 1957-04-30 |
Family
ID=25736282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH321386D CH321386A (en) | 1951-04-24 | 1952-04-09 | Process for the preparation of a new aldehyde condensation product of guanyl melamines |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH321386A (en) |
-
1952
- 1952-04-09 CH CH321386D patent/CH321386A/en unknown
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