Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2002-08-22
2004-03-16
Lambrin, Deborah C. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
active
06706887
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a process for the preparation of alkylimidazolidone (meth)acrylates.
BACKGROUND
Alkylimidazolidone acrylates and methacrylates are known for their role in the constitution of polymers which can be used as coatings and adhesives, in the treatment of paper and of textiles, for their use as agents for leather treatment and in the production of emulsion paints.
European patent application No. 236 994 relates to the preparation of esters of (meth)acrylic acid by reacting an alkyl (meth)acrylate with a heterocyclic alcohol in the presence of a catalyst that is a titanium alkoxide or a titanium, zirconium, iron or zinc chelate, combined with a 1,3-dicarbonyl compound, which may be a metal chelate of a 1,3-diketone, in particular an acetylacetonate.
Such a catalyst has the major disadvantage of generating intensely coloured products.
European patent application No. 433 135 relates to a process for the synthesis of an alkylimidazoline (meth)acrylate, in which an alkyl (meth)acrylate is reacted with a heterocyclic alcohol in the presence of a catalyst chosen from dialkyl tin oxides, dialkyl tin dialkoxides and dialkyl tin diesters.
Such a catalyst requires high reaction temperatures and often causes violent polymerizations with formation of a very hard expanded polymer.
European patent application No. 453 638 also relates to the synthesis of an alkylimidazoline (meth)acrylate in the presence of dialkyl tin oxide.
The subject of European patent application No. 571 851 is a process for the preparation of alkylimidazoline (meth)acrylate, by transesterification of an alkyl (meth)acrylate by means of a heterocyclic alcohol, in the presence of a catalytic system which is a combination of a catalyst based on lithium, for example in oxide, alkoxide, acetate, chloride or bromide form, and a catalyst based on calcium, such as calcium oxide.
European patent application No. 619 309 relates to the preparation of alkylimidazoline (meth)acrylate by reacting an alkyl (meth)acrylate with a heterocyclic alcohol in the presence of a catalyst chosen from the chelates of calcium with 1,3-dicarbonyl compounds, such as calcium acetylacetonate. The products obtained by the process described in that document has an excessively strong colour.
Finally, European patent application No. 902 017 mentions the use of a catalyst that may be lithium, lithium carbonate or lithium hydroxide in the preparation of a monomer from, in particular, hydroxyethyloxazolidine and methyl methacrylate.
However, the use of such catalytic systems does not make it possible to simultaneously achieve the following main objectives:
a high conversion of the heterocyclic alcohol;
a low content of by-products;
a high kinetic;
a low thermal level; and
a faint colouring of the final product.
The subject of the invention is a process for the preparation of alkylimidazoline (meth)acrylate, a process which makes it possible to achieve the objectives mentioned above.
Specifically, the subject of the invention is a process for the preparation of compound (I):
wherein:
R
1
is a hydrogen atom or a methyl group; and
A and B represent, independently of each other, a straight- or branched-chain alkylene group having from 2 to 5 carbon atoms;
by reacting at least one (meth)acrylate (II):
wherein:
R
1
has the abovementioned meaning; and
R
2
is a straight- or branched-chain alkyl group having from 1 to 4 carbon atoms;
with a heterocyclic alcohol (III):
wherein A and B have the abovementioned meanings;
in the presence of a catalyst comprising at least one compound (a) which is a chelate formed of lithium and of a 1,3-dicarbonyl compound.
The subject of the invention is also a composition comprising compound (I) obtained by the process according to the invention in solution in (meth)acrylate (II).
Finally, the subject of the invention is also the use of the above-mentioned composition in the preparation of polymers that can be used as coatings and adhesives, in the treatment of paper and of textiles, as agent for leather treatment and in the production of paints with high wet adhesion characteristics.
DETAILED DESCRIPTION
The preparation process according to the invention, as has been described above, makes use of a catalyst comprising at least one compound (a) which is a chelate formed of lithium and of a 1,3-dicarbonyl compound.
Examples of 1,3-dicarbonyl compounds include but are not limited to the following:
a &bgr;-ketonic acid ester, such as acetylacetic ester;
a 1,3-diketone, such as acetylacetone, 3-methylacetylacetone, benzoylacetone, dibenzoylmethane, 2,4-hexanedione, 3,5-heptanedione, 3-phenylacetylacetone, 4,4,4-trifluoro-1-phenyl-1,3-butanedione, 2,2,6,6-tetramethyl-3,5-heptanedione, 1,1,1-trifluoro-5,5-dimethyl-2,4-hexanedione and 1,1,1-trifluoro-2,4-pentanedione.
Lithium acetylacetonate is most particularly preferred as compound (&agr;).
Examples of reagent (II) include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl and isobutyl acrylates and methacrylates.
Preferably, reagent (II) is methyl methacrylate or acrylate.
An example of reagent (III) is 1-(2-hydroxyethyl)imidazolidyl-2-one, among others.
The quantity of compound (a) used for carrying out the process according to the invention is usually defined relative to the quantity of heterocyclic alcohol.
Thus, the molar ratio of compound (a) to the heterocyclic alcohol (III) is generally between 0.05 and 0.3 percent, and preferably between 0.05 and 0.15 percent.
In an advantageous variant of the process according to the invention, compound (a) is not used alone as catalyst, but rather in the form of a mixture together with a second compound (b). Computer (b) may be chosen from magnesium alkoxides, sodium alkoxides, calcium alkoxides, calcium acetylacetonate, calcium oxide and calcium hydroxide.
As alkoxides, examples include methoxides, ethoxides, propoxides, isopropoxides, butoxides and isobutoxides.
With regard to the quantity of compound (b), it may be less than that of compound (a).
Typically, the quantity of compound (b) is chosen such that the molar ratio of compound (b) to the heterocyclic alcohol (III) is between 0.01 and 0.1 percent, and preferably between 0.01 and 0.05 percent.
The reaction between reagent (II) and reagent (III) is generally carried out in the presence of an excess of either of these reagents.
It is, however, preferable to use more of reagent (II) than reagent (III).
Thus, it is desirable that the molar ratio of the (meth)acrylate (III) to the heterocyclic alcohol (III) is greater than 1, preferably between 1.1 and 7, more preferably between 2 and 5.
In this manner, a composition comprising a solution of compound (I) in (meth)acrylate (II) is obtained as the product of the reaction, for example:
a solution of 1-ethylimidazolidyl-2-one acrylate in methyl acrylate; or alternatively
a solution of 1-ethylimidazolidyl-2-one methacrylate in methyl methacrylate.
Such a composition, which has a colour of less than 100 APHA, may be advantageously used directly in certain applications such as the manufacture of paints with high wet adhesion characteristics, the treatment of leather or the manufacture of coatings.
The process according to the invention may be carried out in the presence of one or more polymerization inhibitors, which may be chosen from phenothiazine, hydroquinone, the monomethyl ether of hydroquinone, di-tert-butyl-para-cresol, para-phenylenediamine, TEMPO (2,2,6,6-tetramethyl-1-piperidinyloxy) and di-tert-butylcatechol.
These compounds may be optionally combined with metal chelators such as EDTA, oxalic acid or the products marketed under the trademark VERSENEX.
The content of polymerization inhibitor is generally between 0.05 and 0.5%, this percentage being expressed as weight of inhibitor (to which the weight of the associated chelator(s) is added where appropriate) relative to the weight of heterocyclic alcohol (III).
Regarding the operating conditions, the process is usually carried out at a temperature of between 70 and 120° C., and preferably between 85 and 100
Dupont Bernard
Paul Jean-Michel
Atofina
Lambrin Deborah C.
Shiao Robert
Welsh & Katz Ltd.
LandOfFree
Process for the preparation of alkylimidazolidone... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for the preparation of alkylimidazolidone..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of alkylimidazolidone... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3187839