Ketal ester derivatives
The present disclosure relates to the preparation of acrylate, alkacrylate, allyl, and polycarbonate derivatives of hydroxy ketal esters, and uses thereof.
1. A compound having the structure P2:
wherein
R 2 is a covalent bond or a linear, branched, or cyclic alkyl, alkenyl, or alkynyl group having 1 to 18 carbon atoms, or an aryl or alkaryl group having between 7 and 36 carbon atoms;
R 3 is hydrogen, alkynyl, or a linear, branched, or cyclic alkyl or alkenyl group having 1 to 18 carbon atoms, or an aryl or alkaryl group having from 7 to 36 carbon atoms;
R 4 is silyl, silane, or siloxane, or a hydrocarbon group having the formula
wherein
a is 0 or 1 and
R 5 , R 6 , R 7 , R 8 , R 9 , and R 10 are independently hydrogen, alkynyl, a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms, a linear or branched alkenyl group having 1 to 18 carbon atoms, an aryl group, or an alkaryl group having from 7 to 18 carbon atoms;
R 11 is a monovalent, divalent, or multivalent linear, branched, or cyclic alkyl group having 1 to 36 carbon atoms, a linear or branched alkenyl group having 1 to 36 carbon atoms, an aryl group, or alkaryl group having from 7 to 36 carbon atoms, or a ketal residue comprising the structure
wherein R 2′ , R 3′ , and R 4′ are as defined for R 2 , R 3 , and R 4 respectively;
R 12 is hydrogen or a linear or branched alkyl group having between 1 and 8 carbons;
α is an integer of 1 to about 100, and where there is more than one α, the values of α are the same or different; and
β is an integer of 1 to about 10.
2. The compound of claim 1 wherein R 11 further comprises one or more additional functional groups comprising halogen, tertiary amine, carbonate, ether, carboxylic acid, carboxylic ester, carbonyl, urethane, imide, amide, or a combination thereof.
3. The compound of claim 1 wherein R 2 is —(CH 2 ) 2 —, R 3 is —CH 3 , and R 4 is the residue of glycerol.
4. The compound of claim 1 wherein R 11 is the residue of a diacid, the diacid comprising oxalic acid, malonic acid, succinic acid, adipic acid, pimellic acid, suberic acid, dodecane-dioic acid, azelaic acid, a dimer acid, sebacic acid, or o, m, or p-phthalic acid.
5. The compound of claim 4 wherein β is 1.
6. The compound of claim 4 wherein β is 2.
7. The compound of claim 2 wherein R 11 is the ketal residue and R 2 is —(CH 2 ) 2 —, R 3 is —CH 3 , and R 4 is the residue of 1,2-propanediol or 1,2-ethanediol.
8. The compound of claim 7 wherein one or more a is between about 1 and 4.