Novel polyesteramides, processes for the preparation thereof, and polyesteramide compositions

Patent metadata

Field	Value
Publication number	US-2020354571-A1
Application number	US-201916960663-A
Country	US
Kind code	A1
Filing date	Jan 17, 2019
Priority date	Jan 23, 2018
Publication date	Nov 12, 2020
Grant date	—

Abstract

The present application discloses novel polyesteramides comprising cycloalkyl diols and/or cycloalkyl dialkanols with tunable properties based on the monomers and monomerratios used to prepare the polyesteramides and varying the reaction conditions. The present application also discloses compositions and articles.

First claim

1 . A polyesteramide comprising:
(a) a diamine component comprising:
1 to 99 mole % of diamine residues derived from a diamine chosen from (C 2-20 )alkyl diamine, CH 2 ((C 3-8 )cycloalkyl-NH 2 ) 2 , H 2 N—((C 1-3 )alkyl) 0-1 -(C 3-8 )cycloalkyl-((C 1-3 )alkyl) 0-1 -NH 2 , 6- to 8-membered heterocycyl containing 2 nitrogen heteroatoms, or H 2 N—((C 1-3 )alkyl) 0-1 -(C 6-10 )bicycloalkyl-((C 1-3 )alkyl) 0-1 -NH 2 wherein the bicycyloalkyl is unbridged or bridged;
(b) a diol component comprising:
1 to 99 mole % of diol residues derived from a diol which is (C 3-8 )cycloalkyl diol; and
(c) a diacid component comprising:
10 to 100 mole % of diacid residues derived from a diacid chosen from HO 2 C—(C 2-40 )alkylene-CO 2 H, or HO 2 C—(C 3-10 )cycloalkyl-CO 2 H;
wherein each cycloalkyl is unsubstituted or substituted by 1-4 (C 1-3 )alkyl, wherein the total mole % of the diacid component is 100 mole %, and wherein the total mole % of the combined diol and diamine component is 100 mole %.

2 . The polyesteramide of claim 1 , wherein the diol is chosen from cyclobutane-1,3-diol, 2,4-dimethylcyclobutane-1,3-diol, 2,4-diethylcyclobutane-1,3-diol, 2,2-dimethylcyclobutane-1,3-diol, 2,2,4,4-tetramethylcyclobutane-1,3-diol.

3 . The polyesteramide of claim 2 , wherein the diol is 2,2,4,4-tetramethylcyclobutane-1,3-diol.

4 . The polyesteramide of claim 3 , wherein the 2,2,4,4-tetramethylcyclobutane-1,3-diol is a mixture comprising greater than 50 mole % of cis-2,2,4,4-tetramethylcyclobutane-1,3-diol based on the total 2,2,4,4-tetramethylcyclobutane-1,3-diol.

5 . The polyesteramide of claim 2 , wherein the diacid is chosen from succinic acid, glutaric acid, adipic acid, heptanedioic acid, octanedioic acid, nonanedioic acid, decanedioic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, hexadecanedioic acid, octadecanedioic acid, eicosanedioic acid, 9-[(Z)-non-3-enyl]-10-octylnonadecanedioic acid, 9-nonyl-10-octylnonadecanedioic acid, cyclobutane-1,3-dicarboxylic acid, cyclopentane-1,3-dicarboxylic acid, cyclohexane-1,4-dicarboxylic acid, cyclohexane-1,3-dicarboxylic acid, cycloheptane-1,4-dicarboxylic acid, cyclooctane-1,5-dicarboxylic acid, or cyclooctane-1,4-dicarboxylic acid.

6 . The polyesteramide of claim 5 , wherein the diacid is chosen from adipic acid, 1,12-dodecanedioic acid, azelaic acid, sebacic acid, 1,18-octadecanedioic acid, 9-nonyl-10-octylnonadecanedioic acid, cyclohexane-1,3-dicarboxylic acid or cyclohexane-1,4-dicarboxylic acid.

7 . The polyesteramide of claim 1 , wherein the diamine is chosen from 4,4′-methylenebis(2-methylcyclohexylamine), 4,4′-methylenebis(cyclohexylamine), 1,6-hexanediamine, 2,4,5-trimethyl-1,6-hexanediamine, 5-amino-1,3,3-trimethylcyclohexanemethylamine, 1,4-bis(aminomethyl)cyclohexane, or 2,2,4,4-tetramethyl-1,3-cyclobutanediamine.

8 . The polyesteramide of claim 7 , wherein the diamine is chosen from 4,4′-methylenebis(2-methylcyclohexylamine), or 4,4′-methylenebis(cyclohexylamine).

9 . The polyesteramide of claim 1 , wherein the polyesteramide further comprises branching agent residues derived from a compound chosen from trimellitic acid, trimethylolpropane, trimethylolethane, glycerol, pentaerythritol, citric acid, tartaric acid, 3-hydroxyglutaric acid, glycerineerythritol, threitol, dipentaerythritol, sorbitol, trimellitic anhydride, pyromelltic dianhydride, trimesic acid, or dimethylol propionic acid.

10 . The polyesteramide of claim 9 , wherein the branching agent residues are present from about 0.001 to about 10 weight % based on the total weight of the polyesteramide.

11 . The polyesteramide of claim 1 , further comprises silane residues derived from an epoxy silane or an isocyanate silane.

12 . The polyesteramide of claim 1 , wherein the polyesteramide has a glass transition temperature in the range of from about −30° C. to about 20° C.

13 . The polyesteramide of claim 1 , wherein the polyesteramide has a glass transition temperature in the range of from about 20° C. to about 90° C.

14 . The polyesteramide of claim 1 , wherein the polyesteramide has a glass transition temperature in the range of from about 90° C. to about 130° C.

15 . The polyesteramide of claim 1 , wherein the polyesteramide has a glass transition temperature in the range of from about 130° C. to about 200° C.

16 . The polyesteramide of claim 1 , wherein the polymer has an inherent viscosity of from about 0.3 dL/g to about 2.0 dL/g as determined according to ASTM D2857-70.

17 . A composition comprising a polyesteramide of claim 1 .

18 . The composition of claim 17 , wherein the composition further comprises an additive chosen from antioxidants, colorants, mold release agents, flame retardants, plasticizers, nucleating agents, UV stabilizers, UV absorbers, thermal stabilizers, glass fibers, carbon fibers, fillers, impact modifiers, an epoxy silane, or an isocyanate silane.

19 . The composition of claim 17 , further comprising a polymer chosen from a polyesteramide other than those of claim 1 , cellulose esters, polyvinyl chloride, a nylon, a polyester, a polyamide, a polyvinyl alcohol, a polyvinyl acetate, a polyvinyl butyral, a polystyrene, a polystyrene copolymer, a styrene acrylonitrile copolymer, an acrylonitrile butadiene styrene copolymer, a poly(methylmethacrylate), an acrylic copolymer, a poly(ethery-imide), a polyphenylene oxide, a polyphenylene sulfide, a polysulfone, a polysulfone ether, or a poly(ether-ketone) of an aromatic dihydroxy compound.

20 . An article comprising the polyesteramide of claim 1 .

21 . (canceled)

22 . The article of claim 20 , wherein the article is a film or sheet.

Assignees

• Eastman Chem Co

Inventors

• Cannon Joshua Seth
• Crawford Emmett Dudley
• George Scott Ellery
• Gunes Kaan
• Zheng Pinguan

Classifications

• B32B2313/00

  Elements other than metals · CPC title

• B32B2307/412

  Transparent · CPC title

• B32B2367/00

  Polyesters, e.g. PET, i.e. polyethylene terephthalate · CPC title

• B32B17/10036

  comprising two outer glass sheets · CPC title

• B32B2250/03

  3 layers · CPC title