One pot synthesis of urea (meth)acrylates
AssigneeEvonik Operations GmbH
InventorsSebastian Bestgen, Silvia Beyer
Life of this patent
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Abstract
A one-pot synthesis of polymerizable and acyclic urea (meth)acrylates, preferably mono(meth)acrylates, can be performed via in-situ synthesis of urea alcohols or amines followed by direct reaction with a (meth)acrylate reactive diluent. The urea alcohol/amine is obtained from isocyanates and alcohols, amines, or hydroxyamines. Subsequently, the reaction with the (meth)acrylate reactive diluent takes place and the urea (meth)acrylate is directly obtained either in solution with the reactive diluent, or as a pure material after removal of the reactive diluent.
Claims20
A one pot process for preparing at least one (meth)acrylate of the general formula (I)
- wherein
- R1 is selected from the group consisting of —H and -Me;
- R2 is selected from the group consisting of —H and a C1-C20 linear, branched or cyclic alkyl or aryl group;
- R2′ is —H;
- R3 is selected from the group consisting of —H;
- a C1-C20 linear, branched or cyclic alkyl or aryl group;
- benzene-sulfonyl;
- tosyl;
- p-chlorophenyl;
- adamantyl;
- 2,6-dimethyl phenyl;
- 3,5-dimethyl phenyl;
- and 2,6-dipropyl phenyl;
- R2 and R3 are the same or different;
- X is selected from the group consisting of —O— and —NH—;
- and
- L is a C2-C20 linear, branched or cyclic alkyl or aryl group, in which optionally, one or more carbon atoms within the carbon chain is replaced by one or more —O—, —NH— or —S— heteroatoms,
- the process comprising:
- reacting, in an initial reaction phase, an aminoalcohol or diamine of the general formula (V)
- wherein X, R2, L are as defined above,
- with an isocyanate of the general formula (VI)
- wherein R3 is as defined above,
- in the presence of a reactive diluent of the general formula (III)
- wherein R4 is C1 to C4 alkyl,
- to obtain, in situ, an intermediate compound of the general formula (II)
- wherein X, R2, R2′, R3, L are as defined above;
- and
- immediately reacting, in a second reaction phase, the intermediate compound with the reactive diluent, to form the at least one (meth)acrylate.
Dependencies are inferred from the claim text.