# US 9,752,030 B2 · Polyamic acid and polyimide, processes for the production of same, compositions containing same, and uses thereof > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,752,030 B2 - Document ID: US9752030B2 - Status: Granted - Kind: B2 - Application number: 13/203,343 - Filed: 2010-02-26 - Published: 2011-12-29 - Granted: 2017-09-05 - Earliest claimed: 2009-03-04 - Assignees: Mitsui Chemicals, Inc. - Applicants: Kenichi Fukukawa; Masaki Okazaki; Yoshihiro Sakata; Ichiro Fujio; Wataru Yamashita - Inventors: Kenichi Fukukawa; Masaki Okazaki; Yoshihiro Sakata; Ichiro Fujio; Wataru Yamashita - Web page: https://patentgrep.com/patent/US9752030B2 ## CPC - C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors - B32B 15/08: of synthetic resin - B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)} - B32B 27/34: comprising polyamides - B32B 27/36: comprising polyesters - C08G 73/1082: {wholly aromatic in the tetracarboxylic moiety} - C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors - H05K 1/0346: {containing N} - Y10T 428/31681: Next to polyester, polyamide or polyimide [e.g., alkyd, glue, or nylon, etc.] - C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06) - B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D) - H05K: PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS - Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION ## Abstract The purpose of the present invention is to provide a polyimide resin which exhibits higher heat resistance than that of a conventional polyimide resin by controlling the geometric configuration of the constituent units. Provided is a polyamic acid which comprises repeating units represented by general formula (1), wherein the 1,4-bismethylenecyclohexane skeleton units consist of both trans- and cis-form units, and the contents of the trans- and cis-form units are 60 to 100% and 0 to 40% respectively (with the sum total of the trans- and cis-form units being 100%). ## Claims ### Claim 1 A polyimide having at least two different repeating units each represented by general formula (2) and having different R, wherein 1,4-bismethylenecyclohexane skeletons (X) in general formula (2) are a trans isomer represented by formula (X1) or a cis isomer represented by formula (X2), and a content of the trans isomer is 63% to 91%, and a content of the cis isomer is 9% to 37%, with respect to the total content of the cis and trans isomers being 100%, where the at least two different repeating units include a repeating unit having R represented by the following formula (R1) and a repeating unit having R represented by the following formula (R2), where —Y— represents a single bond. ### Claim 2 (depends on 1) The polyimide according to claim 1, wherein the content of the trans isomer is 80% to 91%, and the content of the cis isomer is 9% to 20%, with respect to the total content of the cis and trans isomers being 100%. ### Claim 3 (depends on 1) The polyimide according to claim 1, wherein a logarithmic viscosity of the polyimide in a 9:1 (weight ratio) mixture solvent of p-chlorophenol and phenol is 0.1 to 3.0 dl/g, as measured at 35° C. and at a polyimide concentration of 0.5 g/dl. ### Claim 4 (depends on 1) A polyimide film comprising the polyimide according to claim 1. ### Claim 5 (depends on 4) The polyimide film according to claim 4, wherein a glass transition temperature is 250° C. or above. ### Claim 6 (depends on 4) A metal clad laminate obtained by laminating together the polyimide film according to claim 4 and a metal foil. ### Claim 7 (depends on 1) A polyimide resin composition comprising the polyimide according to claim 1 and a coloring agent. ### Claim 8 (depends on 7) The polyimide resin composition according to claim 7, wherein the coloring agent is a whitening agent. ### Claim 9 (depends on 8) The polyimide resin composition according to claim 8, wherein the whitening agent is titanium oxide. ### Claim 10 (depends on 8) A light reflector comprising the polyimide resin composition according to claim 8 as a light reflecting material. ### Claim 11 (depends on 1) A display substrate material comprising the polyimide according to claim 1. ### Claim 12 (depends on 1) A circuit board material comprising the polyimide according to claim 1. ### Claim 13 (depends on 1) A coating material comprising the polyimide according to claim 1. ### Claim 14 (depends on 7) A display substrate material comprising the polyimide resin composition according to claim 7. ### Claim 15 (depends on 7) A circuit board material comprising the polyimide resin composition according to claim 7. ### Claim 16 (depends on 7) A coating material comprising the polyimide resin composition according to claim 7. ### Claim 17 A process for producing a polyimide comprising: reacting together 1,4-bis(aminomethyl)cyclohexane and at least two different tetracarboxylic dianhydrides each represented by formula (3) and having different R, to thereby obtain a polyamic acid, wherein a content of a trans isomer of the 1,4-bis(aminomethyl)cyclohexane represented by formula (Y1) is 63% to 91%, and a content of a cis isomer of the 1,4-bis(aminomethyl)cyclohexane represented by formula (Y2) is 9% to 37%, with respect to the total content of the cis and trans isomers being 100%, where the at least two different repeating units include a repeating unit having R represented by the following formula (R1) and a repeating unit having R represented by the following formula (R2), where —Y— represents a single bond, and thermally or chemically imidizing the polyamic acid.