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US 4,379,895 AGranted
Acid-capped polyester resins
AssigneeThe Goodyear Tire & Rubber Company
InventorsHarlan W. Frerking, Jr., Mellis M. Kelley
Life of this patent
Estimating the term…
Abstract
A polyester resin having a low intrinsic viscosity and suitable for use as a powdered resin is modified by being capped with organic acids. The resins are made from the reaction of diesters with diols with up to 30 mole percent of the diester being replaced with various diacids. The polyester is capped following the condensation reaction stage, but before any finishing stage. The polyester resins have an acid number of from 1 to 100 and allow greater flexibility in the type of acid functionality than previously available.
Claims18
A process for preparing an acid capped polyester resin, suitable for use in powdered polyester resins, comprising the steps of:
- reacting a diester with a diol, said diester selected from the group consisting of an alkyl diester having from 4 to 50 carbon atoms, an alkyl substituted aryl diester having from 10 to 24 carbon atoms, and combinations thereof, said diester optionally containing from about 0.01 percent to about 30 mole percent of a diacid selected from the group consisting of an alkyl dicarboxylic acid having from 2 to 16 carbon atoms, an aryl dicarboxylic acid having from 8 to 16 carbon atoms, an alkyl substituted aryl dicarboxylic acid having from 9 to 16 carbon atoms, a dimer acid having from 34 to 40 carbon atoms, and combinations thereof;
- said diol having from 2 to 50 carbon atoms;
- the mole ratio of said diol to said diester and diacid ranging from about 1.20 to about 2.5, and forming the polyester resin having hydroxyl groups thereon;
- adding from about 0.01 to 1 mole of an acid for each hydroxyl equivalent in said polyester resin, said acid selected from the group consisting of an alkyl dicarboxylic acid having from 2 to 20 carbon atoms;
- a dimer acid having from 34 to 40 carbon atoms, an acid of Formula No. 1;
- an acid of Formula No. 2;
- and combinations thereof;
- ##STR4## where A is an aromatic compound having from 6 to 18 carbon atoms, where R is an alkyl having from 1 to 18 carbon atoms, or a carboxylic acid group, or hydrogen, where R.sub.1 and R.sub.2 are an alkyl having from 1 to 18 carbon atoms, and where R.sub.3 is an alkyl having from 1 to 18 carbon atoms, or an alkyl carboxylic acid group having from 1 to 18 carbon atoms, or hydrogen, and wherein R.sub.1 and R.sub.2 can be the same or different;
- heating and reacting said acid with said polyester resin at a temperature of from about 180.degree. C. to about 280.degree. C. to acid cap said polyester;
- and
- carrying out said reaction until said polyester resin acid number is from about 1 to about 100 and the amount of remaining free acid is less than 20 percent of the added amount.
8 more elements
An acid capped polyester resin suitable for use as a powdered polyester resin, comprising:
- an acid capped polyester resin, said acid capped polyester resin having an acid number of from about 1 to about 100;
- said acid capped polyester resin made by reacting an acid with a polyester having hydroxyl groups thereon;
- said acid capped polyester made by adding from about 0.01 to 1 mole of an acid for each hydroxyl equivalent in said polyester resin, said acid selected from the group consisting of an alkyl dicarboxylic acid having from 2 to 20 carbon atoms, a dimer acid having from 34 to 40 carbon atoms, an acid of Formula No. 1, or an acid of Formula No. 2 ##STR5## where A is an aromatic compound having from 6 to 18 carbon atoms, where R is an alkyl having from 1 to 18 carbon atoms, or a carboxylic acid group, or hydrogen, wherein R.sub.1 and R.sub.2 are an alkyl having from 1 to 18 carbon atoms, and where R.sub.3 is an alkyl having from 1 to 18 carbon atoms, or an alkyl carboxylic acid group having from 1 to 18 carbon atoms, or hydrogen, wherein R.sub.1 and R.sub.2 can be the same or different;
- said reaction of said capping acid with said polyester having hydroxyl groups being carried out at a temperature of from about 180.degree. C. to about 280.degree. C. and to an extent such that the amount of remaining free acid is less than 20 percent of the added amount;
- said polyester resin made by reacting a diester with a diol, said diester selected from the group consisting of an alkyl diester having from 4 to 50 carbon atoms, an alkyl substituted aryl diester having from 10 to 24 carbon atoms, and combinations thereof, said diester optionally containing from about 0.01 percent to about 30 mole percent of a diacid selected from the group consisting of an alkyl dicarboxylic acid having from 2 to 16 carbon atoms, an aryl dicarboxylic acid having from 8 to 16 carbon atoms, an alkyl substituted aryl dicarboxylic acid having from 9 to 16 carbon atoms, a dimer acid having from about 34 to about 40 carbon atoms, and combinations thereof, said diol having from 2 to 50 carbon atoms;
- the mole ratio of said diol to said diester and diacid ranging from about 1.20 to about 2.5, and forming a polyester having hydroxyl groups thereon.
3 more elements
Dependencies are inferred from the claim text.