Compositions – Compositions containing a single chemical reactant or plural... – Organic reactant
Patent
1992-04-21
1993-11-30
Dees, Jose G.
Compositions
Compositions containing a single chemical reactant or plural...
Organic reactant
554116, 554149, 25218225, 25218227, C07C 5100
Patent
active
052667146
DESCRIPTION:
BRIEF SUMMARY
This invention relates to a process for the production of comparatively low-viscosity reaction mixtures containing ester polyols by reaction of epoxidized esters and/or alcohols with carboxylic acids.
The present invention also relates to the mixtures of ester polyols obtainable by the above process which predominantly contain ester polyols bearing free hydroxyl groups in the adjacent position to the ester group.
Polyols are important and versatile raw materials having a broad range of potential applications.
An inexpensive process for the production of polyols is based on the ring-opening reaction of polyepoxidized compounds with protic reactants.
The ring opening of epoxidized oils or fats with alcohols as proton donors is described, for example, in DE-PS 2 900 030, in EP-PS 113 798 and in U.S. Pat. Nos. 3,475,499 and 3,607,778.
The ring opening of epoxidized carboxylic acid esters with polyhydric alcohols is described in one embodiment of DE-OS 33 18 596. Specific reaction conditions are selected to suppress multiple reaction products which are formed by bridge formation of the free hydroxyl groups of the alkoxy radical of the hydroxylalkoxy carboxylic acids containing 2 or more fatty acid molecules. Thus, the epoxidized fatty acid derivative is added to a large excess of polyhydric alcohols, preferably in an excess of from 0.5 mol to more than 10 mol alcohol/mol epoxidized fatty acid derivative.
Acids are normally added as catalysts to accelerate the ring opening of epoxidized compounds with alcohols, but have to be removed after the reaction or remain in the polyol after neutralization with bases and can give rise to cloudy effects and shrinkage where the polyol is used in polyurethane compositions.
In the absence of catalysts, epoxidized oils or fats can be directly ring-opened with carboxylic acids, in which case reaction mixtures modified by hydroxy and acyloxy groups are formed.
The ring opening of soybean oil containing epoxide groups with acrylic acid or methacrylic acid is described, for example, in U.S. Pat. No. 4,016,059. The reaction is carried out by the so-called one-pot method, in which all the reactants are simultaneously reacted, and leads to a reaction mixture containing a hydroxy(meth)acryloxy soybean oil ester. The exact composition of the reaction mixture is determined inter alia by the quantity of acrylic acid used. Where acrylic acid is used in less than an equivalent quantity, based on the epoxide content of the soybean oil, residual contents of epoxide groups of up to 5.2% by weight can occur. Although the residual epoxide content can be reduced to 0.2% where an excess of acrylic acid is used, the reactions are always carried out in the presence of a solvent, such as ethyl benzene.
Comparable reactions of epoxidized soybean oil and acrylic acid inter alia in a molar ratio of 1:3 are described in U.S. Pat. No. 3,125,592, according to which reaction mixtures containing hydroxyacryloxy soybean oil esters are obtained as viscous liquids without solvents by the one-pot method.
Viscous liquids are also obtained in the reaction of epoxidized soybean oil with linseed oil fatty acid or dehydrated ricinoleic acid by the one-pot method (U.S. Pat. No. 2,909,537). Mixtures having undisclosed viscosities are apparently formed irrespective of the fatty acid used and the quantities in which it is used. However, the mixtures obtained contain unreacted linseed oil fatty acid or dehydrated ricinoleic acid which can cause problems, for example where they are subsequently used in polyurethane compositions.
The partial ring opening of epoxidized fats containing more than one epoxide group in the molecule with dicarboxylic acids, polycarboxylic acids or anhydrides thereof in substantially stoichiometric quantities is described in U.S. Pat. No. 3,180,749. In the process claimed in this document, the reaction which is carried out by the one-pot method is said to be terminated before the carboxylic acid has been completely consumed so that at least one unreacted epoxide group remains in each fatty acid m
REFERENCES:
patent: 3125592 (1964-03-01), Nevin
patent: 4118405 (1978-10-01), Hodakawski et al.
Daute Peter
Gruetzmacher Roland
Hoefer Rainer
Kluth Hermann
Stoll Gerhard
Carr Deborah D.
Dees Jos,e G.
Henkel Kommanditgesellschaft auf Aktien
Jaeschke Wayne C.
Millson Jr. Henry E.
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