Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
1999-12-09
2001-05-08
Carr, Deborah D. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S629000, C568S648000
Reexamination Certificate
active
06229054
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field Of The Invention
The invention is in the field of phenol chemistry.
2. Description Of The Background Art
The disclosed novel compound is derived from cardanol, a product obtained by treating cashew nut shell liquid (CNSL). CNSL consists primarily of anacardic acid which is decarboxylated when heated in the presence of acid, giving the meta-substituted phenol, cardanol, used in this invention. (See FIG.
1
). Without further refining the resulting product contains a minor amount of a related compound, cardol. (See FIG.
2
).
CNSL derivatives have found many industrial uses in, for example, epoxy curing agents, phenolic resins, surfactants, and emulsion breakers. These surfactant-emulsification compounds are oxalkylated to increase their molecular weight and modify their solubility or hydrophilic/lipophilic balance. For example a British patent GB 2,262,525 discloses ethoxylating cardanol with ethylene oxide to form a family of compounds of the formula C
15
H
31−2x
C
6
H
4
O(C
2
H
4
O)
n
H, where n is 3 or more, to produce the desired surface-active properties in which there is a balance between the hydrophilic and lipophilic ends of the molecule.
U.S. Pat. No. 2,448,767 disclosed a method of hydroxyethylation wherein ethylene carbonate or ethylene sulfite was reacted with phenols or other active hydrogencontaining compounds, such as thiophenols, amines, alcohols, thioalkohols, and carboxylic acids. The disclosed catalysts included an acid (concentrated sulfuric acid or an alkyl ether of sulfuric acid), a base (alkali carbonates), or the alkali salt of a phenol.
U.S. Pat. No. 2,967,892 disclosed that alkali metal hydroxides were effective catalysts in the hydroxyalkylation reactions of chloromethylethylene carbonate with phenols. U.S. Pat. No. 2,987,555 disclosed that alkali metal hydrides were effective catalysts in the hydroxyalkylation reactions of ethylene carbonate with phenols.
U.S. Pat. No. 4,310,706 disclosed the use of imidazole and its derivatives as catalysts for the reaction of phenols or thiophenols and cyclic organic carbonate compounds with high yields and good monohydroxyalkylation selectivity.
These prior art processes have not been used with cardanol before. Because of the unique molecular structure of cardanol (a long unsaturated side alkyl chain on the benzene ring), the principles disclosed in the prior art processes do not apply in the case of cardanol. For example, these teachings would imply that the use of basic catalysts could produce a significant amount undesirable by-product of secondary reactions between the hydroxyalkylphenyl ether and the carbonate reactant.
SUMMARY OF THE INVENTION
The present invention comprises a process for the hydroxyalkylation of cardanol with cyclic organic carbonates in the presence of organic or inorganic catalysts and a novel composition of matter produced by that process. The unique molecular structure of cardanol allows the use of a variety of organic or inorganic basic catalysts, including triethylamine, imidazole, sodium hydroxide and sodium carbonate, in the hydroxyalkylation reaction without forming quantities of undesirable side-products. According to this invention, the final product, monohydroxyalkylcardanyl ether, can be obtained with high yield and high purity. The product has a light color and its color stability is enhanced by replacing the phenol's hydroxyl group with a more stable hydroxyalkoxyl group.
The novel compound disclosed here is produced by hydroxyalkylating cardol with the cyclic organic carbonates (ethylene carbonate or propylene carbonate) by heating the constituents in the presence of a catalyst. This reaction produces the novel compound having the formula
C
15
H
31−2x
C
6
H
4
O(C
2
H
4
)OH (with ethylene carbonate)
(See FIG.
3
.)or
C
15
H
31−2x
C
6
H
4
O(C
3
H
6
)OH (with propylene carbonate)
(See FIG.
4
.), where x is 1, or 2 depending on the number of double bonds in the meta-substituted aliphatic side chain. Carbon dioxide is evolved in the process.
The product is a useful constituent as a modifier in coatings, adhesives, sealants, rubbers, plastics, elastomers, composites and ink because it is a high boiling point, low viscosity liquid whose benzene ring and long side chain structure makes it compatible with many different resins such as alkyds, urethanes, and acrylics. It is an effective constituent of epoxy curing agents. Its high boiling point makes it a stable plasticizer, lending flexibility to, for example, solvent-free epoxy anticorrosive coatings. As a coating constituent it is very light in color and more color stable than other cardanol compounds. Its high boiling point and long chain structure, with one or more unsaturated bonds, produces a plasticizer with good leaching stability. The compound's stability is enhanced by replacement of the phenol's hydroxyl group with a more stable hydroxyl group. This replacement produces greater color stability and reduces the potential for producing contact dermatitis.
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patent: 5059723 (1991-10-01), Dressler
patent: 5068460 (1991-11-01), Sumner
patent: 5525201 (1996-06-01), Diaz-Arauzo
patent: 828496 (1960-02-01), None
patent: 2262525 (1993-06-01), None
Chen Meng J.
Dai Zhisheng
Cardolite Corporation
Carr Deborah D.
Friedman Allen N.
McCarter & English LLP
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