PROCESS ECONOMICS PROGRAM

Transcription

1 PROCESS ECONOMICS PROGRAM SRI lnternatlonal Menlo Park, California Abstract Process Economics Program Report No. 93A THERMOSETTING MATRIX RESINS (October 1990) This report is a supplement to PEP Report 93 (March 1976). It presents a review of technology of thermosetting matrix resins for composites, advanced composites in particular. The matrix resins include glycidyl ether and glycidyl amine epoxy resins, polyimide prepolymers, and vinylesters. The following eight processes for producing these thermosetting resins are evaluated and presented in this report: Tetraglycidyl ether of tetraphenylol ethane Triglycidyl ether of p-aminophenol Triglycidyl amine of methylenediamine Triglycidyl amine of methylenediamine directly from the diamine from aniline Tetraglycidyl amine of ar,ar-bis(4-aminophenyl)-p-diisopropylbenzene Bismaleimide of methylenediamine Acetylene terminated polyimide prepolymer DGEBA (diglycidyl ether of bisphenol A)-based vinylester. Also presented are updated economics for liquid and solid bisphenol A-based epoxy resins and epoxy novolac resins from PEP Report 38A, Supplement A, Epoxy Resins (February 1984). PEP 87 YRC

2 Report No. 93A THERMOSETTING MATRIX RESINS SUPPLEMENT A by YU-REN CHIN with contributions by CHEE-HORNG CHANG JEN-LIAN LIOU MING-KUNG SHEN KUN-LUNG YEN a Cl m A private report by the October 1990 PROCESS ECONOMICS PROGRAM Menlo Park, California 94025

3 I For detailed marketing data and information, the reader is referred to one of the SRI programs specializing in marketing research. The CHEMCAL ECONOMlCS HANDBOOK Program covers most major chemicals and chemical products produced in the United States and the WORLD PETROCHEMCALS Program covers major hydrocarbons and their derivatives on a worldwide basis. In addition, the SRI D/RECTORY OF CHEMICAL PRODUCERS services provide detailed lists of chemical producers by company, product, and plant for the United States and Western Europe I I 1 ii

4 CONTENTS 1 INTRODUCTION l-l 2 SUMMARY... 2-l GENERAL ASPECTS Epoxy Resins... 2-l Polyimides... 2-l TECHNICAL ASPECTS Epoxy Resins Polyimides INDUSTRY STATUS... 3-l EPOXY RESINS... 3-l Surface Coatings Electrical/Electronic Composites Construction/Adhesives POLYIMIDES... 3-l 1 4 REVIEW OF TECHNOLOGY... EPOXY RESINS... Chemistry... Diglycidyl Ethers... Polyglycidyl Ethers... Epoxy Novolac Resins... Solid Epoxy Resins... Modified Epoxy Resins... Aminophenols... Polyglycidyl Amines... Purification of Epoxy Resins... Curing Agents and Epoxy Resin Compositions... 4-l 4-l iii -

5 CONTENTS (Continued) 4 REVIEW OF TECHNOLOGY (Concluded) BlSMALElMlDES AND POLYlMlDES Bismaleimides... 4-l 0 Allylnadic lmides Polyimide Prepolymers... 4-l 1 PMR Polyimides Acetylene Terminated Pclyimide Prepolymers... 4-l 2 Tetracarboxylic Dianhydrides and Aromatic Diamines... 4-l 3 VINYL ESTERS ECONOMICS OF GLYCIDYLETHER EPOXY RESINS... PRODUCTION OF TETRAGLYCIDYL ETHER... Process Description... Production of Tetraphenylol Ethane... Production and Purification of Tetraglycidyl Ether... Process Discussion... Cost Estimates... UPDATED ECONOMICS OF OTHER EPOXY RESINS... Diglycidyi Ether of Bisphenol A... BPA-based Solid Epoxy Resins... BPA-Based Epoxy Resin Solutions... Epoxy Novolac Resins... 5-l l ECONOMICS OF POLYGLYCIDYL AMINES... 6-l PRODUCTION OF TRIGLYCIDYL P-AMINOPHENOL... 6-l Process Description... 6-l Production of p-aminophenol Production and Purification of TGPAP Solvent Recovery Process Discussion Cost Estimates iv -

6 CONTENTS (Continued) 6 ECONOMICS OF POLYGLYCIDYL AMINES (Concluded) PRODUCTION OF TETRAGLYCIDYL METHYLENEDIANILINE... Process Description--TGMDA from Methylenedianiline... Production of TGMDA... Product Purification and Solvent Recovery... Process Discussion--TGMDA from Methylenedianiline... Cost Estimates--TGMDA from Methylenedianiline... Process Description--TGMDA from Aniline... Production of Tetrachlorohydrin... Production of TGMDA... Process Discussion--TGMDA from Aniline... Cost Estimates--TGMDA from Aniline... Economic Comparison... PRODUCTION OF TETRAGLYCIDYL BAPPB (TGBAPPB)... Process Description... Production of TGBAPPB... Product Purification and Solvent Recovery... Process Discussion... Cost Estimates... 7 ECONOMICS OF POLYIMIDE PREPOLYMERS... PRODUCTION OF BISMALEIMIDE OF MDA... Process Description... Production of BMI-MDA... Recovery of Solvent and By-product... Process Discussion... Cost Estimates... PRODUCTION OF ACETYLENE-TERMINATED POLYIMIDE PREPDLYMER l 7-l 7-l Process Description... Production of MNPB... Production of APA... Production of APB... 7-l Production of Polyimide Prepolymer Process Discussion Cost Estimates, v-

7 CONTENTS (Concluded) 8 ECONOMICS OF VINYLESTER RESINS... 8-l PRODUCTlON OF DGEBA-BASED VINYLESTER RESIN... 8-l process Description... 8-l process Discussion Cost Estimates PRODUCTION OF EPN-BASED VINYLESTER RESIN APPENDIX A: PATENT SUMMARY TABLES A-l APPENDIX B: CURING AGENTS FOR EPOXY RESINS AND EPOXY RESIN COMPOSITIONS B-l APPENDIX C: TECHNOLOGY FOR THE PRODUCTiON OF TETRACARBOXYLIC DIANHYDRIDES AND AROMATIC DIAMINES C-l TETRACARBOXYLIC DlANHYDRlDE c-3 P-PHENYLENEDIAMINE *... c-3 DlAMlNODlPHENYL ETHER c-3 3-AMINOPHENYLACETYLENE AND 1,3-BIS(3-AMINOPHENOXY)BENZENE..... c-4 APPENDIX D: DESIGN AND COST BASES... D-l DESIGN CONDITIONS... D-3 COST BASES... D-3 CAPITAL INVESTMENT... D-3 PRODUCTION COSTS... D-4 EFFECT OF OPERATING LEVEL ON PRODUCTION COSTS... D-5 APPENDIX E: CITED REFERENCES E-l APPENDIX F: PATENT REFERENCES BY COMPANY F-l APPENDIX G: PROCESS FLOW DIAGRAMS G-l - vi -

8 5.1 PRODUCTION OF TETRAGLYCIDYL ETHER OF TETRAPHENYLOL ETHANE FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN G TETRAGLYCIDYL ETHER OF TETRAPHENYLOL ETHANE FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE a*... 5-l TRIGLYCIDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND ERCHLOROHYDRIN ,,......, G TRIGLYCIDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND EPICHLOROHYDRIN EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE METHYLENEDIANILINE AND EPICHLOROHYDRIN G METHYLENEDIANILINE AND EPICHLOROHYDRIN EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE ANILINE, FORMALDEHYDE, AND EPICHLOROHYDRIN G ANILINE, FORMALDEHYDE, AND EPICHLOROHYDRIN EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE TETRAGLYCIDYL METHYLENEDIANILINE EFFECT OF ANILINE AND MDA PRICES ON THE TGMDA PRODUCT VALUE TETRAGLYCIDYL AMINE FROM BAPPB AND EPICHLOROHYDRIN G TETRAGLYCIDYL AMINE FROM BAPPB AND EPlCHLOROHYDRlN EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE BISMALEIMIDE OF MDA FROM MDA AND MALEIC ANHYDRIDE G BISMALEIMIDE OF MDA FROM MDA AND MALEIC ANHYDRIDE EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE vii -

9 FIGURES (Concluded) ACETYLENE TERMINATED POLYIMIDE PREPOLYMER FROM APB, APA, AND BTDA ACETYLENE TERMINATED POLYIMIDE PREPOLYMER FROM APA, APB, AND BTDA EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE VINYLESTER RESIN FROM METHACRYLIC ACID AND DGEBA-BASED RESINS VINYLESTER RESIN FROM METHACRYLIC ACID AND DGEBA-BASED RESINS EFFECT OF OPERATING LEVEL AND PLANT CAPACITY ON PRODUCT VALUE G G-25 6-l VIII -

10 TABLES 2.1 GLYCIDYLETHER EPOXY RESINS SUMMARY OF ECONOMICS POLYGLYCIDYLAMINES SUMMARY OF ECONOMICS , POLYIMIDES SUMMARY OF ECONOMICS VINYLESTER RESINS SUMMARY OF ECONOMICS U.S. PRODUCERS OF EPOXY RESINS (END OF 1989) n WESTERN EUROPEAN PRODUCERS OF EPOXY RESINS (AS OF END OF 1989) JAPANESE PRODUCERS OF EPOXY RESINS (AS OF END OF 1969) a PRODUCERS OF EPOXY RESINS IN OTHER REGIONS (AS OF END OF 1969) PRODUCERS OF THERMOSET POLYIMIDES (AS OF END OF 1989) n....a...*... 3-l WESTERN EUROPEAN PRODUCERS OF THERMOSET POLYIMIDES (AS OF END OF 1989).a JAPANESE PRODUCERS OF THERMOSET POLYIMIDES (AS OF END OF 989) a a GLYCIDYLETHER EPOXY RESINS PATENT SUMMARY A ADVANCED EPOXY RESINS PATENT SUMMARY A MODIFIED EPOXY RESINS PATENT SUMMARY A P-AMINOPHENOL PATENT SUMMARY a.. A-l 1 - ix -

11 TABLES (Continued) POLYGLYCIDYLAMINES PATENT SUMMARY......*...a... PURIFICATION OF EPOXY RESINS PATENT SUMMARY BISMALEIAMIDES PATENT SUMMARY *...*... BIS (ALLYLNADIC) IMIDES PATENT SUMMARY *...a...*... ACETYLENE-TERMINATED POLYIMIDES PATENT SUMMARY VINYLESTER RESINS PATENT SUMMARY ,,... TETRAGLYCIDYL ETHER OF TETRAPHENYLOL ETHANE FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN DESIGN BASES AND ASSUMPTIONS..a...,.. TETRAGLYCIDYL ETHER OF TETRAPHENYLOL ETHANE FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN STREAM FLOWS *...*...*... PRODUCTION OF THE TETRAGLYCIDYLETHER OF TETRAPHENYLOL FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN MAJOR EQUIPMENT #......*... PRODUCTION OF THE TETRAGLYCIDYLETHER OF TETRAPHENYLOL FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN UTlLlTlES SUMMARY , ,. TETRAGLYCIDYL ETHER OF TETRAPHENYLOL ETHANE FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN TOTAL CAPlTAL INVESTMENT TETRAGLYCIDYLETHER OF TETRAPHENYLOL ETHANE FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN CAPlTAL INVESTMENT BY SECTION TETRAGLYCIDYL ETHER OFTETRAPHENYLOLETHANE FROM PHENOL, GLYOXAL, AND EPICHLOROHYDRIN PRODUCTION COSTS * DIGLYCIDYL ETHER OF BISPHENOL A BY BATCH PROCESS TOTAL CAPlTAL INVESTMENT , A-13 A-17 A-19 A-23 A-24 A x-

12 TABLES (Continued) 5.9 DIGLYCIDYL ETHER OF BISPHENOL A BY BATCH PROCESS PRODUCTION COSTS..,...,...,...,...**..., DIGLYCIDYL ETHER OF BISPHENOL A BY CONTINUOUS PROCESS TOTAL CAPITAL INVESTMENT DIGLYCIDYL ETHER OF BISPHENOL A BY CONTINUOUS PROCESS PRODUCTION COSTS * SOLID EPOXY RESINS FROM DGEBA AND BISPHENOL A TOTAL CAPITAL INVESTMENT * SOLID EPOXY RESINS FROM DGEBA AND BISPHENOL A (GRADE A) PRODUCTION COSTS HIGH M W EPOXY RESIN SOLUTION FROM DGEBA AND BISPHENOL A TOTAL CAPITAL INVESTMENT HIGH M W EPOXY RESIN SOLUTION FROM DGEBA AND BISPHENOL A (SOLUTION A) PRODUCTION COSTS #...# LIQUID EPOXY NOVOLAC RESINS BY CONVENTIONAL PROCESS TOTAL CAPITAL INVESTMENT,.., ,.....,., LIQUID EPOXY NOVOLAC RESINS BY CONVENTIONAL PROCESS PHENOL BASED PRODUCTION COSTS , LIQUID EPOXY NOVOLAC RESINS BY CONVENTIONAL PROCESS 0-CRESOL BASED PRODUCTION COSTS * SOLID EPOXY NOVOLAC RESINS BY ALTERNATIVE PROCESS TOTAL CAPlTAL INVESTMENT * SOLID EPOXY NOVOLAC RESINS BY ALTERNATIVE PROCESS PHENOL BASED PRODUCTION COSTS SOLID EPOXY NOVOLAC RESINS BY ALTERNATIVE PROCESS 0-CRESOL BASED PRODUCTION COSTS xi -

13 TABLES (Continued) TRIGLYCIDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND EPICHLOROHYDRIN DESIGN BASES AND ASSUMPTIONS * TRIGLYCIDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND EPICHLOROHYDRIN STREAM FLOWS TRIGLYCIDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND EPICHLOROHYDRIN MAJOR EQUIPMENT.a.,..., TRIGLYCIDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND EPICHLOROHYDRIN UTILITIES SUMMARY e,...,..., TRIGLYCIDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND EPICHLOROHYDRIN TOTAL CAPlTAL INVESTMENT..,...*,...*...* TRIGLYCIDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND EPICHLOROHYDRIN CAPITAL INVESTMENT BY SECTION * TRlGLYClDYL P-AMINOPHENOL FROM NITROBENZENE, HYDROGEN, AND EPICHLOROHYDRIN PRODUCTION COSTS **...* METHYLENEDIANIUNE AND EPICHLOROHYDRIN DESIGN BASES AND ASSUMPTIONS METHYLENEDIANILINE AND EPICHLOROHYDRIN STREAM FLOWS *...* METHYLENEDIANILINE AND EPICHLOROHYDRIN MAJOR EQUIPMENT METHYLENEDIANILINE AND EPICHLOROHYDRIN UTILITIES SUMMARY *...*...* METHYLENEDIANIUNE AND ERCHLOROHYDRIN TOTAL CAPlTAL INVESTMENT xii -

14 TABLES (Continued) METHYLENEDIANILINE AND EPICHLOROHYDRIN CAPITAL INVESTMENT BY SECTION.....a... METHYLENEDIANILINE AND EPlCHLOROHYDRlN PRODUCTION COSTS,.,.,...,,..,...*...*... ANILINE, FORMALDEHYDE, AND EPICHLOROHYDRIN DESIGN BASES AND ASSUMPTIONS ANILINE, FORMALDEHYDE, AND EPICHLOROHYDRIN STREAM FLOWS *...*...*... ANILINE, FORMALDEHYDE, AND EPlCHLOROHYDRlN MAJOR EQUIPMENT ANILINE FORMALDEHYDE AND EPICHLOROHYDRIN UTILITIES SUMMARY *...*... ANILINE, FORMALDEHYDE, AND EPICHLOROHYDRIN TOTAL CAPITAL INVESTMENT **..*...* ANILINE, FORMALDEHYDE, AND EPICHLOROHYDRIN CAPITAL INVESTMENT BY SECTION *...*... ANILINE, FORMALDEHYDE, AND EPICHLOROHYDRIN PRODUCTION COSTS *...*.. TETRAGLYCIDYL AMINE FROM BAPPB AND EPICHLOROHYDRIN DESIGN BASES AND ASSUMPTIONS ,... TETRAGLYCIDYL AMINE FROM BAPPB AND EPICHLOROHYDRIN STREAM FLOWS TETRAGLYCIDAL AMINE FROM BAPPB AND EPICHLOROHYDRIN MAJOR EQUIPMENT..*.*...,...,... TETRAGLYCIDYL AMINE FROM BAPPB AND EPICHLOROHYDRIN UTILITIES SUMMARY ,...., XIII -

15 TABLES (Continued) TETRAGLYCIDYL AMINE FROM BAPPB AND EPlCliLOROHYDRlN TOTAL CAPlTAL INVESTMENT TETRAGLYClDYL AMINE FROM BAPPB AND EPlCHLOROHYDRlN CAPiTAL INVESTMENT BY SECTION TETRAGLYCiDYL AMINE FROM BAPPB AND EPlCHLOROHYDRiN PRODKWNWSTS BiSMALEIMiDE OF MDA FROM MDA AND MALEIC ANHYDWDE DESIGN BASES AND ASSUMPTiCNS BiSMALElMlDE OF MDA FROM MDA AND MALEIC ANHYDFUDE STREAM FLOWS BlSMALElMlDE OF MDA FROM MDA AND MALEIC ANHYDRiDE MAJOR EQUIPMENT BiSMALElMlDE OF MDA FROM MDA AND MALElC ANHYDRIDE UTiLiTiES SUMMARY BiSMALElMlDE OF MDA FROM MDA AND MALEiC ANHYDRiDE TOTAL CAF ltal INVESTMENT l 2 BiSMALElMlDE OF MDA FROM MDA AND MALElC ANHYDRiDE CAPiTAL INVESTMENT BY SECTlON BiSMALElMiDE OF MDA FROM MDA AND MALElC ANHYDiUDE -cosrs ACETYLENE-TERMINATED FROM APA, APB, AND BTDA POLYIMIDE PREPOLYMER DESK% BASES AND ASSUMPTlONS ACETYLENE-TERMINATED POLYIMIDE PREFOLYMER FROM APA. APB, AND BTDA STREAM FLOWS ACETYLENE-TERMINATED FOLYlMlDE PREPOLYMER FROM APA. APB, AND BTDA MAJOR EQUIPMENT ACETYLENE-TERMINATED POLYIMIDE PREPOLYMER FROM APA, APB, AND BTDA UTieS SUMMARY ACETYLENE-TERMINATED POLYIMIDE PREPOLYMER FROM APA, APB, AND BTDA TOTAL CAPlTAL INVESTMENT xiv -

16 TABLES (Continued) 7.13 ACETYLENE-TERMINATED POLYIMIDE PREPOLYMER FROM APA, APB, AND BTDA CAPITAL INVESTMENT BY SECTION ACETYLENE-TERMINATED POLYIMIDE PREPOLYMER FROM APA, APB, AND BTDA PRODUCTION COSTS I VINYLESTER RESIN FROM METHACRYLIC ACID AND DGEBA-BASED RESINS DESIGN BASES AND ASSUMPTIONS B VINYLESTER RESIN FROM METHACRYLIC ACID AND DGEBA-BASED RESINS STREAM FLOWS * VINYLESTER RESIN FROM METHACRYLIC ACID AND DGEBA-BASED RESINS MAJOR EQUIPMENT *...*..**. B VINYLESTER RESIN FROM METHACRYLIC ACID AND DGEBA-BASED RESINS UTILITIES SUMMARY..**...*... B VINYLESTER RESIN FROM METHACRYLIC ACID AND DGEBA-BASED RESINS TOTAL CAPITAL INVESTMENT *...*.... *....,.. B-B 8.6 VINYLESTER RESIN FROM METHACRYLIC ACID AND DGEBA-BASED RESINS PRODUCTION COSTS B VINYLESTER RESIN FROM METHACRYLIC ACID AND EPN-BASED RESIN PRODUCTION COSTS ,....., CURING AGENTS FOR EPOXY RESINS PATENT SUMMARY **...,,.,. B EPOXY RESIN COMPOSITIONS PATENT SUMMARY.....*...*...*... B-9 c.1 BENZOPHENONE TETRACARBOXYLIC DIANHYDRIDE PATENT SUMMARY , ,.,..., C-5 C.2 P-PHENYLENEDIAMINE PATENT SUMMARY C-7 -xv-

17 TABLES (Concluded) C.3 WRIFICATION OF P-PHENYLENEDIAMINE PATENT SUMMARY c-15 C.4 DIAMINODIPHENYL ETHER FROM DINITRODIPHENYL ETHER PATENT SUMMARY C-l 7 C.5 1,3-BIS (3-AMINOPHENOXY) BENZENE AND 3-AMINOPHENYL ACETYLENE PATENT SUMMARY *... c-19 - xvi -