DE745099C - Process for the manufacture of products from formaldehyde, other aldehydes and ammonium salts - Google Patents

Process for the manufacture of products from formaldehyde, other aldehydes and ammonium salts

Info

Publication number
DE745099C
DE745099C DEI66157D DEI0066157D DE745099C DE 745099 C DE745099 C DE 745099C DE I66157 D DEI66157 D DE I66157D DE I0066157 D DEI0066157 D DE I0066157D DE 745099 C DE745099 C DE 745099C
Authority
DE
Germany
Prior art keywords
formaldehyde
products
parts
aldehydes
urea
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
Application number
DEI66157D
Other languages
German (de)
Inventor
Dr Hans Scheuermann
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DE1938I0060291 priority Critical patent/DE688302C/en
Application filed by IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Priority to DEI66157D priority patent/DE745099C/en
Priority to DEI65315D priority patent/DE730337C/en
Priority to DEB6687D priority patent/DE912398C/en
Priority to NL104361A priority patent/NL56699C/en
Application granted granted Critical
Publication of DE745099C publication Critical patent/DE745099C/en
Expired legal-status Critical Current

Links

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
    • C08G12/10—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with acyclic or carbocyclic compounds with acyclic compounds having the moiety X=C(—N<)2 in which X is O, S or —N
    • C08G12/12—Ureas; Thioureas
    • 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
    • C08G12/46—Block or graft polymers prepared by polycondensation of aldehydes or ketones on to macromolecular compounds
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/47—Condensation polymers of aldehydes or ketones
    • D21H17/49—Condensation polymers of aldehydes or ketones with compounds containing hydrogen bound to nitrogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paper (AREA)
  • Coloring (AREA)

Description

Verfahren zur Herstellung von Erzeugnissen aus Formaldehyd, anderen Aldehyden und Ammoniumsalzen Zusatz zum Patent 6883o2 In dem Hauptpatent 688 3o2 ist ein Verfahren zur Herstellung von Erzeugnissen durch Umsetzung von Formaldehyd, anderen Aldehyden und Ammoniumsalzen beschrieben.Process for the manufacture of products from formaldehyde, other Aldehydes and ammonium salts Addition to the patent 6883o2 In the main patent 688 3o2 is a process for the production of products by converting formaldehyde, other aldehydes and ammonium salts.

Im Zusatzpatent 730 337 ist beschrieben, daß die nach dem Hauptpatent erhältlichen Erzeugnisse erheblich verbessert werden können, wenn man die Umsetzung in Gegenwart von Harnstoff vornimmt oder die nach dem Verfahren des Hauptpatentes erhaltenen Erzeugnisse noch mit Harnstoff umsetzt, wobei man solche Mengen Harnstoff verwendet, daß noch lösliche Erzeugnisse entstehen. Es wurde nun gefunden, daß man ebenfalls Kondensationsprodukte von ausgezeichneten Eigenschaften erhält, wenn man bei der Herstellung der Erzeugnisse aus Fornaldehyd, anderen Aldehvden und Ammoniumsalzen wasserlösliche Kondensationsprodukte aus Formaldehyd und Harnstoff mitverwendet. Solche wasserlöslichen Kondensationsprodukte sind beispielsweise Mono- oder Dimethylolharnstoff oder die aus diesen durch Wasserabspaltung oder Wasser- und Formaldehydabspaltung erhältlichen höhermolekularen, noch wasserlöslichen Stoffe. Man kann die wasserlöslichen Kondensationsprodukte aus Formaldehyd und Harnstroff während der Unsetzung zugegen sein lassen oder mit ihnen die aus Fornaldehy d, anderen Aldehyden und Ammoniumsalzen nach dem Verfahren des Hauptpatents erhaltenen Erzeugnisse nachbehandeln.In the additional patent 730 337 it is described that after the main patent available products can be vastly improved if one can implement in the presence of urea or according to the method of the main patent The products obtained are still reacted with urea, such amounts being urea used that still soluble products arise. It has now been found that one also obtained condensation products of excellent properties if one in the manufacture of products from formaldehyde, other aldehydes and ammonium salts water-soluble condensation products of formaldehyde and urea are also used. Such water-soluble condensation products are, for example, mono- or dimethylolurea or from these by elimination of water or elimination of water and formaldehyde available higher molecular weight, still water-soluble substances. One can use the water soluble Condensation products Formaldehyde and urea during the Let unsettling be present or with them those from Fornaldehy d, other aldehydes post-treatment of products obtained by the process of the main patent and ammonium salts.

Die so erhältlichen Erzeugnisse sind farbheller,haltbarer, und temperaturbeständiger als die Erzeugnisse, die nur aus Formaldehyd. anderen Aldehyden und Ammoniumsalzen ohne Mitverwendung von Harnstoff bzw.. Harnstoff - Formaldehyd - Kondensationsprodukten erhalten werden, was z. B. bei ihrer Verwendung für die Papierleimung oder für das Fixieren von Gerbstoffen sehr vorteilhaft ist.The products available in this way are lighter in color, more durable and more temperature-resistant than the products made from formaldehyde only. other aldehydes and ammonium salts without the use of urea or urea - formaldehyde condensation products be obtained what z. B. when used for paper sizing or for Fixing tannins is very beneficial.

Die in den Beispielen angegebenen Teile sind Gewichtsteile. Beispiel I In 2oo Teile einer 3o%igen wäßrigen F ormaldehylösung, deren pH-Wert 8,1 beträgt, rührt man 1 5 Teile Harnstoff ein und erhitzt ½ Stunde lang auf d.5 . Dann läßt man erkalten, gibt zu der so erhaltenen Lösung, die neben Formaldehyd noch Methylolverbindungen des Harnstoffs enthält. 66 Teile Ammonitunsulfat und 3o Teile Acetaldehyd, läßt das Gemisch etwa 48 Stunden lang bei Zimmertemperatur stehen und gibt dann zu der schwach gelb gefärbten Lösung so lange Na tronlauge oder Ammoniak, bis der pH-Wert etwa 5 bis 6 beträgt. Diese kann als solche zum Fixieren von Gerbstoffen oder Farbstoffen verwendet -werden oder zur Trockne eingedampft werden. -wobei ein Pulver erbalten wird, das sich in Wasser wieder klar auflöst.The parts given in the examples are parts by weight. example I In 2oo parts of a 3o% aqueous formaldehyde solution, the pH of which is 8.1, 1 5 parts of urea are stirred in and heated to d.5 for ½ hour. Then lets it is cooled, and the methylol compounds in addition to formaldehyde are added to the solution thus obtained of urea. 66 parts of ammonite sulfate and 3o parts of acetaldehyde leaves the mixture stand for about 48 hours at room temperature and then add to the pale yellow colored solution so long sodium hydroxide solution or ammonia until the pH value is about 5 to 6. This can be used as such to fix tannins or dyes -be used or evaporated to dryness. -which resulted in a powder that dissolves clear again in water.

Beispiel Zu einer durch halbstündiges Kochen einer Mischung von 2ooTeilen einer 3o%igen wäßrigen Formaldehydlösung vorn pH-Wert 4,5 und I5 Teilen Harnstoff erhaltenen wäßrigen Lösung, die neben löslichem Harnstofi-Formaldehyd-Kondensationsprodukt noch Formakdehyd enthält, gibt man bei Zimmertemperatur 66 Teile Antnoniumsulfat oder 53 Teile Ammoniumchlorid und 3o Teile Acetaldehyd und läßt das Gemisch I bis 2 Tage stehen.Example For one by boiling a mixture of 2oo parts for half an hour a 30% strength aqueous formaldehyde solution with a pH of 4.5 and 15 parts of urea obtained aqueous solution, in addition to soluble urea-formaldehyde condensation product still contains formakdehyde, 66 parts of antonium sulfate are added at room temperature or 53 parts of ammonium chloride and 3o parts of acetaldehyde and leaves the mixture I bis Stand for 2 days.

Die Eigenschaften der so erhaltenen Lösung entsprechen etwa denen der Lösung nach Beispiel I, Beispiel 3 In ein Gemisch von 6oo Teilen einer 3o%igen wäßrigen Formaldehvdlösung und I2o Teilen Acetaldehyd werden unter Rühren und unter Abführung der Reaktionswärme durch Kühlung bei 2o bis 3o° 264 Teile Ammoniumsulfat eingetragen. plan läßt las Genisch noch 2 Tabe bei 20 bis 30' stehen und läßt dann unter Rühren eine wäßrige Lösung eines Harnstoff-Formaldehyd-Kondensationsprodtrktes zufließen, die durch ½stündiges Erhitzen von 2oo Teilen einer 3o%igen wäßrigen Formaldehydlösung (pH = 8,I) mit 6o Teilen Harnstoff auf 45' erhalten wurde. Die bei der Vereinigung der Lösungen zunächst auftretende gelartige Ausscheidung ist nach zweitägigem Stehen wieder verschwunden. Die dann entstandene Lösung hat ähnlicheEigenschaftenwie dienach dem Beispiel I. Beispiel 4 In 2oo Teile einer 3o%igen wäßrigen Formaldehydlösung. deren pH-Wert 8,I beträgt, rührt man I,5 Teile Harnstoff ein und erhitzt das Gemisch ½ Stunde lang auf 45°. Dann gibt man zu der erhaltenen Lösung 66 Teile Ammoniumsulfat und 48.5 Teile Crotonaldehyd und erwärntI Stunde lang unter Rückflußkühlung zum Sieden. Nach dem Abkühlen auf Zinmertemperatur erhält man eine Lösung mit ähnlichen Eigenschaften wie nach Beispiel I.The properties of the solution obtained in this way correspond approximately to those the solution according to Example I, Example 3 In a mixture of 600 parts of a 3o% aqueous formaldehyde solution and I2o parts of acetaldehyde are stirred and added Removal of the heat of reaction by cooling at 2o to 3o ° 264 parts of ammonium sulfate registered. plan leaves genisch for another 2 tabs at 20 to 30 'and then leaves an aqueous solution of a urea-formaldehyde condensation product with stirring flow by heating 2oo parts of a 3o% aqueous formaldehyde solution for ½ hour (pH = 8, I) with 60 parts of urea per 45 'was obtained. The one at the union The gel-like excretion that initially occurs is after standing for two days disappeared again. The resulting solution has properties similar to those afterwards to Example I. Example 4 In 2oo parts of a 30% strength aqueous formaldehyde solution. whose pH is 8.1, 1.5 parts of urea are stirred in and the mixture is heated ½ hour at 45 °. 66 parts of ammonium sulfate are then added to the solution obtained and 48.5 parts of crotonaldehyde and refluxed for 1 hour Boil. After cooling to Zinmer's temperature, a solution with similar ones is obtained Properties as in example I.

Claims (1)

PATENTANSPRUCH: weitere Ausbildung des Verfahrens zur Herstellung von Erzeugnissen aus Formaldehyd, anderen Aldehyden und Ammnoniun salzen nach Patent 68s 3o2, dadurch gekennzeichnet, daß, man die Umsetzung in Gegenwart wasserlöslicher Kondensatioiisprodtikte aus F()i-inalrlelivd und Harnstoff vornimmt oder init diesen dic nach dein Verfahren des Hauptpatent: erhaltenen Erzeugnisse nachbehandelt. Zur Abgrenzung des Anmeldungsgegenstandes vom Stand der Technik sind im l?rteilungsverfahren keine Druckschriften in Betracht gezogen -worden.PATENT CLAIM: further development of the manufacturing process of products made from formaldehyde, other aldehydes and ammonium salts according to patent 68s 3o2, characterized in that the reaction is carried out in the presence of water-soluble Condensation products from F () i-inalrlelivd and urea or with these dic according to the process of the main patent: obtained products after-treated. To the The delimitation of the subject of the application from the state of the art are in the notification procedure no publications were considered.
DEI66157D 1938-01-20 1938-12-18 Process for the manufacture of products from formaldehyde, other aldehydes and ammonium salts Expired DE745099C (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DE1938I0060291 DE688302C (en) 1938-01-20 1938-01-20 Process for the manufacture of products from formaldehyde, other carbonyl compounds and ammonium salts
DEI66157D DE745099C (en) 1938-01-20 1938-12-18 Process for the manufacture of products from formaldehyde, other aldehydes and ammonium salts
DEI65315D DE730337C (en) 1938-01-20 1939-07-28 Process for the production of products from formaldehyde, other carbonyl compounds, ammonium salts and urea
DEB6687D DE912398C (en) 1938-12-18 1941-05-02 Process for the production of products from formaldehyde, other carbonyl compounds, ammonium salts and urea
NL104361A NL56699C (en) 1938-12-18 1942-01-15 Process for preparing products from formaldehyde, other carbonyl compounds, ammonium salts and urea.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE1938I0060291 DE688302C (en) 1938-01-20 1938-01-20 Process for the manufacture of products from formaldehyde, other carbonyl compounds and ammonium salts
DEI66157D DE745099C (en) 1938-01-20 1938-12-18 Process for the manufacture of products from formaldehyde, other aldehydes and ammonium salts
DEI65315D DE730337C (en) 1938-01-20 1939-07-28 Process for the production of products from formaldehyde, other carbonyl compounds, ammonium salts and urea

Publications (1)

Publication Number Publication Date
DE745099C true DE745099C (en) 1944-02-26

Family

ID=41137784

Family Applications (3)

Application Number Title Priority Date Filing Date
DE1938I0060291 Expired DE688302C (en) 1938-01-20 1938-01-20 Process for the manufacture of products from formaldehyde, other carbonyl compounds and ammonium salts
DEI66157D Expired DE745099C (en) 1938-01-20 1938-12-18 Process for the manufacture of products from formaldehyde, other aldehydes and ammonium salts
DEI65315D Expired DE730337C (en) 1938-01-20 1939-07-28 Process for the production of products from formaldehyde, other carbonyl compounds, ammonium salts and urea

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DE1938I0060291 Expired DE688302C (en) 1938-01-20 1938-01-20 Process for the manufacture of products from formaldehyde, other carbonyl compounds and ammonium salts

Family Applications After (1)

Application Number Title Priority Date Filing Date
DEI65315D Expired DE730337C (en) 1938-01-20 1939-07-28 Process for the production of products from formaldehyde, other carbonyl compounds, ammonium salts and urea

Country Status (1)

Country Link
DE (3) DE688302C (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE931408C (en) * 1949-10-29 1955-08-08 Franz Dr Koehler Process for the production of nitrogen-containing, water-soluble condensation products

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
None *

Also Published As

Publication number Publication date
DE688302C (en) 1940-02-17
DE730337C (en) 1943-01-11

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