Liquid hydroxy-terminated polyesters

• US 3,957,753 A
• Filed: 05/22/1974
• Issued: 05/18/1976
• Est. Priority Date: 09/17/1968
• Status: Expired due to Term

• Current Assignee: Inter-Polymer Corporation
• Original Assignee: Inter-Polymer Corporation
• Inventors: Cook, William H., Hostettler, Fritz, Lombardi, Frank G.
• Primary Examiner(s): Myers, Jane S.
• Application Number:
  US05/472,289
• Time in Patent Office: 727 Days
• Field of Search: 260/484 A, 260/210 R
• US Class Current: 560/189
• CPC Class Codes: C08G 18/4286 prepared from a combination of hydroxycarboxylic acids and/or lactones with polycarboxylic acids or ester forming derivatives thereof and polyhydroxy compounds
• CPC Class Codes: C08G 2110/0008 flexible
• CPC Class Codes: C08G 2110/0066 ≥ 150kg/m3
• CPC Class Codes: C08G 2110/0083 prepared using water as the sole blowing agent
• CPC Class Codes: C08G 63/06 derived from hydroxycarboxylic acids
• CPC Class Codes: C08G 63/60 derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds

Abstract

Solid and microcellular polyurethane elastomers prepared by reacting (a) liquid polyesters containing from about 25 percent by weight to about 70 percent by weight of the epsilon-oxycaproyl unit, the balance of the polyester being derived from the reaction of at least one dicarboxylic acid with at least two glycols selected from the group consisting of ethylene glycol 1,3-propanediol, 1,4-butanediol and 1,5-pentanediol, (b) an organic polyisocyanate, and optionally (c) a chain-extender comprising water, glycols, amino alcohols, or diamines. If the liquid polyester (a) is branched, for example, by addition of small quantities of a triol, the reaction with the organic polyisocyanate may be conducted in the absence of a chain-extender. Processes for producing these elastomers are also disclosed.

Novel liquid, substantially primary hydroxyl-terminated, linear and branched polyesters containing from about 25 percent by weight to as much as about 70 percent by weight of the epsilonoxycaproyl unit ##EQU1## the balance of the polyester being derived from the reaction of at least one dicarboxylic acid with at least two straight chain glycols selected from the group consisting of ethylene glycol, 1,3-propanediol, 1,4-butanediol and 1,5-pentanediol. These polyesters have a true melting point no higher than about 30°C. Also provided are processes for producing these polyesters.

Claims

1. Substantially primarily hydroxyl terminated linear and branched polyester polyols which remain liquid at ambient temperature prepared by the process which comprises simultaneously and substantially completely reacting:

i. e-caprolactone, 6-hydroxycaproic acid, a lower oligomer of 6-hydroxycaproic acid or mixture of the foregoing in an amount sufficient to provide from about 25 to 70 percent by weight of the oxycaproyl unit ##EQU4## ii. at least one dicarboxylic acid or dicarboxylic acid anhydride selected from the group consisting of adipic acid, succinic acid, glutaric acid, sebacic acid, pimelic acid and azelaic acid, their anhydrides and mixtures thereof; and

iii. at least two different glycols selected from the group consisting of ethylene glycol, 1,3-propanediol, 1,4-butanediol and 1,5-pentanediol, the molar ratio of the glycols being in the range of from about 1/3 to about 3.

2. The polyesterpolyols of claim 1 having a true melting point not exceeding about 30°

C.

3. The polyesterpolyols of claim 1 formed by contacting the reactants at a temperature of about 100°

to 300°

C.

4. The polyesterpolyols of claim 3 formed by contacting the reactants in the presence of about 5 parts per million to about 0.3 percent of the total charge of a catalyst selected from the group consisting of polyesterification catalysts and ester interchange catalysts.

5. The polyesterpolyols of claim 1 formed by adding to the reactants from about 0.1% to 5.0% by weight of the total charge of reactants, of a polyol branching agent selected from the group consisting of glycerol, 1,2,6-hexanetriol, trimethylolethane, trimethylolpropane, triethanolamine, pentaerythritol and alphamethylglucoside.