US 12,441,841 B2
Optically transparent polyimides
John McNamara, El Sobrante, CA (US); John D. Harvey, Akron, OH (US); Matthew J. Graham, Akron, OH (US); and Carolyn Scherger, Akron, OH (US)
Assigned to Akron Polymer Systems, Inc., Akron, OH (US)
Appl. No. 16/652,541
Filed by Akron Polymer Systems, Inc., Akron, OH (US)
PCT Filed Oct. 3, 2018, PCT No. PCT/US2018/054260
§ 371(c)(1), (2) Date Mar. 31, 2020,
PCT Pub. No. WO2019/156717, PCT Pub. Date Aug. 15, 2019.
Claims priority of provisional application 62/568,745, filed on Oct. 5, 2017.
Prior Publication US 2020/0239635 A1, Jul. 30, 2020
Int. Cl. C08G 73/10 (2006.01); C08L 79/08 (2006.01); C12P 13/00 (2006.01)
CPC C08G 73/1007 (2013.01) [C08G 73/1082 (2013.01); C08L 79/08 (2013.01); C12P 13/001 (2013.01); C08G 2150/00 (2013.01); C08G 2170/00 (2013.01); C08L 2203/12 (2013.01); C08L 2203/16 (2013.01); C08L 2203/20 (2013.01); C08L 2310/00 (2013.01)] 13 Claims
 
1. A polyimide derived from monomers comprising: one or more aliphatic polyamines; and
one or more aliphatic dianhydrides or tetracarboxylic acids thereof, one or more aromatic dianhydrides or tetraacids thereof or one or more aromatic dianhydrides or tetraacids thereof and one or more aliphatic dianhydrides or tetracarboxylic acids thereof, or a mixture thereof,
wherein:
the one or more aliphatic dianhydrides or tetracarboxylic acids thereof are selected from the group consisting of 2,3,4,5-tetrahydrofurantetracarboxylic dianhydride; 5-(2,5-dioxotetrahydrofural)-3-methyl-3-cyclohexane-1,2-dicarboxylic dianhydride and 3,3′,4,4′-bicyclohexyltetracarboxylic acid dianhydride (H-BPDA);
the one or more aromatic dianhydrides or tetraacids thereof are selected from the group consisting of
1,4,5,8-naphthalenetetracraboxylic dianhydride; 2,3,6,7-aphthalenetetracraboxylic dianhydride;
3,3′,4,4′-dimethyldiphenylsilanetetracarboxylic dianhydride;
3,3′,4,4′-tetraphenylsilanetetracarboxylic dianhydride; p-phenylene bis(triphenylphthalic acid)dianhydride; and
m-phenylene-bis(triphenylphthalic acid)dianhydride; and
the one or more aliphatic polyamines are selected from the group consisting of 1,2-diaminoethane (1,2-DAE); 1,3-diaminopropane (1,3-DAP); 1,4-diaminobutane (1,4-DAB); 1,5-diaminopentane (1,5-DAP); N-(3-aminopropyl)-1,4-butadiamine, N,N′-bis(3a-minopropyl)-1,4-butanediamine; N-(3-aminopropyl)-1,3-propanediamine; and N1-(3-(3-aminopropylamino)propyl)butane-1,4-diamine; and
wherein the polyimide has an optical transmittance on at least 70 percent at 400 nanometers and above,
wherein the total content of aromatic dianhydride(s) is defined by a percentage equivalent weight of the polyimide that does not exceed 40 percent, and
wherein the polyimide has a glass transition temperature in the range of 140° C. to 200° C., and the equivalent ratio of polyamine and dianhydride is 1:1.