DE364040C - Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde - Google Patents

Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde

Info

Publication number
DE364040C
DE364040C DEF45683D DEF0045683D DE364040C DE 364040 C DE364040 C DE 364040C DE F45683 D DEF45683 D DE F45683D DE F0045683 D DEF0045683 D DE F0045683D DE 364040 C DE364040 C DE 364040C
Authority
DE
Germany
Prior art keywords
formaldehyde
condensation products
production
aryloxyacetic acids
resinous condensation
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
DEF45683D
Other languages
German (de)
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.)
Hoechst AG
Original Assignee
Hoechst 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
Application filed by Hoechst AG filed Critical Hoechst AG
Priority to DEF45683D priority Critical patent/DE364040C/en
Priority to DEF46025D priority patent/DE371148C/en
Application granted granted Critical
Publication of DE364040C publication Critical patent/DE364040C/en
Expired legal-status Critical Current

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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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/28—Chemically modified polycondensates
    • 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
    • C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
    • C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
    • C08G8/08—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ
    • C08G8/18—Condensation polymers of aldehydes or ketones with phenols only of aldehydes of formaldehyde, e.g. of formaldehyde formed in situ with phenols substituted by carboxylic or sulfonic acid groups

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Phenolic Resins Or Amino Resins (AREA)

Description

Verfahren zur Herstellung von harzartigen Kondensationsprodukten aus Aryloxyessigsäuren und Formaldehyd. Es- wurde gefunden, daß man durch vorsichtige Kondensation von Aryloxyessigsäuren mit Formaldehyd oder formaldehydabspaltenden - Körpern, zweckmäßig bei Gegenwart von nur geringen Mengen kondensierender Mittel, unter Vermeidung einer zu langen Kondensationsdauer, harzähnliche Kondensationsprodukte erhält, welche als schon in schwachen Alkalien leichtlösliche Kunstharze wertvolle technische Verwendung finden könnten. So erhält man durch Kondensation von Phenoxyessigsäure, Kresoxyessigsäure, Xylyloxyessigsäure, x- und ß-Naphtoxyessigsäure, Tetrahydro-ß-naphtoxyessigsäure usw. mit Formaldehyd oder diesen abspaltenden Mitteln, zweckmäßig bei Gegenwart von Kondensationsmitteln, wie geringer Mengen Salzsäure, harzartige Kondensationsprodukte, welche nach Befreiung von Säure, Wasser usw. sehr helle Kunstharze von sehr guten Löslichkeitseigenschaften darstellen. Insbesondere haben diese die Eigenschaft, in schwachen Alkalien, z. B. schon in Borax, leichtlöslich zu sein.Process for the production of resinous condensation products Aryloxyacetic acids and formaldehyde. It has been found that by cautious Condensation of aryloxyacetic acids with formaldehyde or formaldehyde-releasing agents - Bodies, expedient in the presence of only small amounts of condensing agents, while avoiding too long a condensation time, resin-like condensation products which is valuable as synthetic resins which are readily soluble in weak alkalis could find technical use. Thus, by condensation of phenoxyacetic acid, one obtains Cresoxyacetic acid, xylyloxyacetic acid, x- and ß-naphthoxyacetic acid, tetrahydro-ß-naphthoxyacetic acid etc. with formaldehyde or these releasing agents, expediently in the presence condensation agents, such as small amounts of hydrochloric acid, resinous condensation products, which after being freed from acid, water, etc., made very light synthetic resins from very good ones Represent solubility properties. In particular, these have the property in weak alkalis, e.g. B. already in borax to be easily soluble.

Durch die Arbeit von Cohn, Chem. Zeitung qo, ig=6, S. 725 bis 727 sind bereits Kondensationsprodukte aus Formaldehyd und Aryloxyessigsäuren bekannt geworden; diese sind aber infolge größerer :Menge angewendeten Kondensationsmittels und insbesondere infolge der zu langen Kondensationsdauer wesentlich höher kondensiert als die Prcdukte des vorliegenden Verfahrens. Die Produkte nach der Cohnschen Arbeitsweise sind daher ebenso wie Phenolformaldehydkondensationsprodukte vom Typus der -Resole und Novolake noch in Natronlauge und auch noch in Ammoniak löslich, aber im Gegensatz zu den Produkten des vorliegenden Verfahrens in Soda und Boraxlösungen unlöslich. Beispiele. i. go g Phenoxyessigsäure werden mit ioo g Formaldehyd 4oprozentig und io g konzentrierter Salzsäure so lange am Rückfiußkühler gekocht, bis sich ein farbloses Öl ausscheidet. Nach: dem Abkühlen wird die wäßrige Schicht abgehoben, das Öl mehrfach mit Wasser gewaschen und im Tiegel bei etwa i2o bis 130' so lange erwärmt, bis eine Probe beim Abkühlen erstarrt. Das entstehende Harz ist springhart, fast farblos, klar und gut löslich in Sprit, Aceton und sonstigen organischen Lösungsmitteln, außerdem gut löslich in Alkalien, auch in Soda und Boraxlösungen.Through the work of Cohn, Chem. Zeitung qo, ig = 6, pp. 725 to 727 condensation products of formaldehyde and aryloxyacetic acids are already known become; but these are due to the larger amount of condensing agent used and especially as a result of the excessively long condensation time, it condenses much more highly than the products of the present process. The products based on the Cohn method are therefore just like phenol-formaldehyde condensation products of the -resole type and novolaks still soluble in caustic soda and also in ammonia, but in contrast insoluble to the products of the present process in soda and borax solutions. Examples. i. go g of phenoxyacetic acid are given 4 percent strength with 100 g of formaldehyde and 10 g concentrated hydrochloric acid boiled on the reflux condenser until a colorless Oil separates. After: cooling, the aqueous layer is lifted off and the oil several times Washed with water and heated in the pan at about 12 to 130 minutes until a Sample solidifies on cooling. The resulting resin is hard as a spring, almost colorless, clear and easily soluble in fuel, acetone and other organic solvents, also soluble in alkalis, also in soda and borax solutions.

2. go g Kresoxyessigsäure werden mit Zoo g Formaldehyd 4oprozentig und io g konzentrierter Salzsäure in der im Beispiel Z angegebenen Weise behandelt. Das entstehende Produkt ist in seinen Eigenschaften dem aus Phenoxyessigsäure hergestellten völlig analog.2. Go g of cresoxyacetic acid become 4% with zoo g of formaldehyde and 10 g of concentrated hydrochloric acid treated in the manner indicated in Example Z. The properties of the resulting product are similar to those made from phenoxyacetic acid completely analog.

Claims (1)

PATENT-ANSPRUCII: Verfahren zur Herstellung von harzartigen Kondensationsprodukten aus Aryloxyessigsäuren und Formaldehyd, dadurch gekennzeichnet, daß man zwecks Gewinnung von in schwachen Alkalien löslichen Produkten Formaldehyd oder formaldehydabspältende Mittel auf die Aryloxyessigsäuren unter Vermeidung einer zu langen Kondensationsdauer, zweckmäßig in Gegenwart nur geringer Mengen eines Kondensationsmittels, einwirken läßt.PATENT-ANSPRUCII: Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde, characterized in that for the purpose of obtaining of products which are soluble in weak alkalis, formaldehyde or formaldehyde-releasing agents Agent based on the aryloxyacetic acids while avoiding too long a condensation time, expediently act in the presence of only small amounts of a condensing agent leaves.
DEF45683D 1919-11-18 1919-11-18 Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde Expired DE364040C (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DEF45683D DE364040C (en) 1919-11-18 1919-11-18 Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde
DEF46025D DE371148C (en) 1919-11-18 1920-01-13 Process for the production of resinous condensation products from aryloxy fatty acids and formaldehyde

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF45683D DE364040C (en) 1919-11-18 1919-11-18 Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde

Publications (1)

Publication Number Publication Date
DE364040C true DE364040C (en) 1922-11-16

Family

ID=7100609

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF45683D Expired DE364040C (en) 1919-11-18 1919-11-18 Process for the production of resinous condensation products from aryloxyacetic acids and formaldehyde

Country Status (1)

Country Link
DE (1) DE364040C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2692866A (en) * 1950-02-15 1954-10-26 Bayer Ag Process for the production of cation-exchanging resins from phenolic ethers and products
DE1154628B (en) * 1958-07-23 1963-09-19 Bayer Ag Process for the production of higher molecular weight condensation products

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2692866A (en) * 1950-02-15 1954-10-26 Bayer Ag Process for the production of cation-exchanging resins from phenolic ethers and products
DE1154628B (en) * 1958-07-23 1963-09-19 Bayer Ag Process for the production of higher molecular weight condensation products

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