CS256713B1 - Nitrogen derivatives of acrylic esters - Google Patents
Nitrogen derivatives of acrylic esters Download PDFInfo
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- CS256713B1 CS256713B1 CS676185A CS676185A CS256713B1 CS 256713 B1 CS256713 B1 CS 256713B1 CS 676185 A CS676185 A CS 676185A CS 676185 A CS676185 A CS 676185A CS 256713 B1 CS256713 B1 CS 256713B1
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Abstract
Riešenie popisuje dusíkaté deriváty esterov kyseliny akrylovej obecného vzorca, kde představuje Ri zbytok odvodený od imida- zolu, piperidinu, morfolínu, alebo pyrolidí- nu a R2 je etyl alebo hydroxymetyl. Neutra- lizáciou s kyselinou mravčou alebo octovou je ich možné previesť na příslušné soli. Zlúčeniny sú vhodné ako surovina k príprave polymérov.The present invention provides nitrogen derivatives of acrylic acid esters of the formula wherein R 1 is a moiety derived from imidazole, piperidine, morpholine, or pyrrolidine, and R 2 is ethyl or hydroxymethyl. By neutralization with formic or acetic acid, they can be converted into the corresponding salts. The compounds are useful as a raw material for preparing polymers.
Description
256713
Vynález sa týká dusíkatých derivátov es-terov kyseliny akrylovej a ich solí s kyse-linou mravčou a octovou.
Akryláty obsahujúce vo svojej štruktúreatóm dusíka sú známe á našli významnépriemyselné uplatnenie. Možno ich připra-vit působením akrylačného činidla ako Jekyselina akrylová či jej halogenid, anhyd-rid alebo ester na příslušný dusíkatý deri-vát alebo působením diakrylátov na primár-né aminy alebo polyamíny.
Zistili sme, že či už problémy s odstraňo-váním kondenzačných produktov, citlivostna vlhkost alebo vedlejších reakcií je mož-né v podstatnej miere odstránlť při výroběamínoakrylátov podlá vynálezu.
Predmetom vynálezu sú dusíkaté derivá-ty esterov kyseliny akrylovej obecného vzor-ca
O O
II II ( CH2=CHCOCH2)2 C CH2OCCH2CH2R1 R2 kde představuje
alebo
"O a R2—C2H5 alebo CH2OH, a ich soli s kyselinou mravčou a octovou. Přípravu týchto zlúčenín je možné usku-točniť působením imidazolu, piperidínu, mor-folínu a pyrolidínu na pentaeritritroltriakry-látu alebo trimetylolpropántriakrylátu v mo-lárnom pomere 1 : 1. Neutralizáciou s kyse-linou mravčou a octovou je ich možné v pří-pade potřeby previesť na příslušné hydro-filné soli. Priebeh adície a kontrolu koneč-ného produktu je možné najpresnejšie určo-vat stanovováním obsahu nenasýtených vá-zieb akrylátu.
Zlúčeniny vyrobitelné podlá vynálezu súvhodné ako surovina k přípravě polymérov.
Vynález je dalej objasněný formou príkla-dov. Příklad 1 Příprava zlúčeniny vzorca (CH2=CHCOOCH2)2(C2H5) -C CH2OOCCH2CH2R1
Do banky sa předložilo 40 g 50 %-néhoroztoku trimetylolpropántriakrylátu v metyl-alkohole. Za miešania za normálnej teplotysa přidal příslušný amin vo formě '50 %-né-ho roztoku v metylalkohole tak, aby teplo-ta uvolněná pri reakcií neprestúpila 45 °Ca násada sa miešala 2 h. Za vákua sa od-destiloval metylalkohol. Množstvá roztokovamínov a vlastnosti produktov sú uvedenév tabulka 1.
Tabulka 1 amin navážka (g) aminové číslo[mg KOH/g) akrylový ekvi-valent(mól/100 g) nD20 imidazol 9,2 307,3 0 5480 1,4973 piperidín 11,6 146,9 0,5237 1,4813 morfolín 11,8 146,5 0,5220 1,4832 pyrolidín 9,6 153,1 0,5436 1,4775 Příklad 2 Příprava zlúčeniny vzorca· (CH2--CHCOOCH2 )2 (HOCH2) -C CH2OOCCH2CH2R1 roztoku pentaeritritoltriakrylátu v metylal-kohole a postupom ako v příklad 1 pří-slušný amin vo formě 50 %-ného roztoku vmetylalkohole. Množstvo roztoku aminu avlastnosti produktu sú uvedené v tabulke2.
Do banky sa předložilo 40 g 50 %-ného
256713
The invention relates to nitrogen derivatives of esters of acrylic acid and their salts with formic acid and acetic acid.
Acrylates containing nitrogen in their structure are known and have found significant industrial application. They can be prepared by the action of an acrylating agent such as acrylic acid or its halide, anhydride or ester on the corresponding nitrogenous derivative or by the action of diacrylates on primary amines or polyamines.
We have found that whether problems with the removal of condensation products, sensitive moisture or side reactions can be substantially eliminated in the manufacture of the amine acrylates of the invention.
The present invention provides nitrogen derivatives of acrylic acid esters of the general formula
OO
II II (CH 2 = CHCOCH 2) 2 C CH 2 OCH 2 CH 2 R 1 R 2 where it represents
or
"O and R 2 - C 2 H 5 or CH 2 OH, and salts thereof with formic acid and acetic acid. The preparation of these compounds can be accomplished by treatment with imidazole, piperidine, morpholine and pyrrolidine on pentaeritritroltriacrylate or trimethylolpropane triacrylate in a 1: 1 molar ratio. Neutralization with formic acid and acetic acid can be effected, if desired, into the corresponding hydrophilic salts, and the addition and control of the final product can be determined most accurately by determining the unsaturated content of the acrylate.
Compounds produced according to the invention suitable as a raw material for preparing polymers.
The invention is further illustrated by the following examples. Example 1 Preparation of Compound of Formula (CH 2 = CHCOOCH 2) 2 (C 2 H 5) -C CH 2 OOCCH 2 CH 2 R 1
40 g of a 50% strength solution of trimethylolpropane triacrylate in methyl alcohol were charged to the flask. With stirring under normal temperature, the appropriate amine was added in the form of a 50% solution in methanol so that the temperature released in the reactions did not exceed 45 ° C and the batch was stirred for 2 h. Methanol was distilled off under vacuum. The amounts of solutionamines and product properties are shown in Table 1.
Table 1 amine weight (g) amine number [mg KOH / g) acrylic equivalent (mole / 100 g) nD20 imidazole 9.2 307.3 0 5480 1.4973 piperidine 11.6 146.9 0.5237 1, 4813 morpholine 11.8 146.5 0.5220 1.4832 pyrrolidine 9.6 153.1 0.5436 1.4775 Example 2 Preparation of a compound of formula (CH2 - CHCOOCH2) 2 (HOCH2) -C CH2OOCCH2CH2R1 solution of pentaeritritol triacrylate in methylal and by proceeding as in Example 1, the corresponding amine in the form of a 50% solution in methyl alcohol. The amount of amine solution and product properties are shown in Table 2.
40 g of 50% strength was introduced into the flask
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS676185A CS256713B1 (en) | 1985-09-23 | 1985-09-23 | Nitrogen derivatives of acrylic esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS676185A CS256713B1 (en) | 1985-09-23 | 1985-09-23 | Nitrogen derivatives of acrylic esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS256713B1 true CS256713B1 (en) | 1988-04-15 |
Family
ID=5415362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS676185A CS256713B1 (en) | 1985-09-23 | 1985-09-23 | Nitrogen derivatives of acrylic esters |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS256713B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019199436A (en) * | 2018-05-16 | 2019-11-21 | 東洋インキＳｃホールディングス株式会社 | Morpholine ring-containing (meth)acrylate compound and polymerizable composition using same |
-
1985
- 1985-09-23 CS CS676185A patent/CS256713B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2019199436A (en) * | 2018-05-16 | 2019-11-21 | 東洋インキＳｃホールディングス株式会社 | Morpholine ring-containing (meth)acrylate compound and polymerizable composition using same |
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