WO1994013669A1 - Bisnadimides - Google Patents
Bisnadimides Download PDFInfo
- Publication number
- WO1994013669A1 WO1994013669A1 PCT/AU1993/000622 AU9300622W WO9413669A1 WO 1994013669 A1 WO1994013669 A1 WO 1994013669A1 AU 9300622 W AU9300622 W AU 9300622W WO 9413669 A1 WO9413669 A1 WO 9413669A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- bisnadimide
- solvent
- optionally substituted
- aryl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/24—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs
- C08J5/241—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres
- C08J5/243—Impregnating materials with prepolymers which can be polymerised in situ, e.g. manufacture of prepregs using inorganic fibres using carbon fibres
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/58—[b]- or [c]-condensed
- C07D209/72—4,7-Endo-alkylene-iso-indoles
- C07D209/76—4,7-Endo-alkylene-iso-indoles with oxygen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1003—Preparatory processes
- C08G73/1007—Preparatory processes from tetracarboxylic acids or derivatives and diamines
- C08G73/101—Preparatory processes from tetracarboxylic acids or derivatives and diamines containing chain terminating or branching agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/12—Unsaturated polyimide precursors
- C08G73/128—Unsaturated polyimide precursors the unsaturated precursors containing heterocyclic moieties in the main chain
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J179/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen, with or without oxygen, or carbon only, not provided for in groups C09J161/00 - C09J177/00
- C09J179/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C09J179/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C09J179/085—Unsaturated polyimide precursors
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F11/00—Chemical after-treatment of artificial filaments or the like during manufacture
- D01F11/10—Chemical after-treatment of artificial filaments or the like during manufacture of carbon
- D01F11/14—Chemical after-treatment of artificial filaments or the like during manufacture of carbon with organic compounds, e.g. macromolecular compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Definitions
- the invention is concerned with bisnadimides and polymers, particularly high temperature resistant matrix polymers for composites, made therefrom.
- thermostable polyimide matrix resins developed for the aerospace industry has been the Polymerizable Monomeric Reactants (PMR)-type, produced by workers in NASA, USA. These resins are monomeric mixtures of aromatic examines with nadic anhydride and aromatic dianhydride based esters. These mixtures were reported to react at intermediate temperatures to give nadimide capped oligomers of Formula (I) as shown below.
- PMR Polymerizable Monomeric Reactants
- aromatic diamine monomers present in the resins often have toxicity and stability problems, for example, diaminodiphenylmethane - the most commonly used aromatic diamine in industry.
- Ar is an optionally substituted aryl, optionally substituted bridged or bonded di- or poly- aryl or optionally substituted heteroaryl group;
- Ar' is an optionally substituted aryl or heteroaryl group which provides for good conjugation between the nitrogen containing groups;
- X is hydrogen, halogen or an alkyl group; and
- m is 0 to 6 which comprises reacting a diaminobisimide of the Formula (HI)
- good conjugation means that during formation of the ⁇ aminobisimide precursor from a diamine of Formula (IV) shown below, substitution of an electron-withdrawing group on one of the nitrogen atoms suppresses the reactivity of the other nitrogen atom during the reaction.
- aromatic diamine of the Formula (IV) is stericaUy hindered, such as in compounds of Formulae (V) and (VI)
- R ⁇ , R ⁇ , R ⁇ and R° are the same or different and each may be selected from alkyl, aryl, heteroaryl, nitro and halogen groups.
- Ar or Ar' may be substituted with one or more alkyl, alkoxy, alkylthio, aryl, heteroaryl, aryloxy, carboxy, alkylthio, alkylamino, dialkylamino, amino, nitro, cyano or halo groups.
- Aryl means an aromatic carbocylic group, such as phenyl, naphthyl, and the like.
- “Bridged or bonded di- or poly- aryl” means a group consisting of two or more aromatic carboxylic ring systems, such as phenyl, naphthyl or the like joined by a bond, such as in biphenyl, or a bridging group, such as in sulphonyldiphenyl.
- 'Bridging group includes for example SO2, CO, CH 2 and O such as in compounds of the Formula (Vila)
- R ⁇ is a divalent group such as -SO2-, -CO-, -CH 2 - and -O-.
- the group Ar' maybe selected from the groups listed above for Ar. However, because of the constraints imposed by the requirement of "good conjugation” (as defined above) some bridged di- or poly- aryl groups may not be suitable. Thus for Ar', the bridging group (if present) must provide good conjugation between the amino groups of the diamine moiety (IV). For example in groups of the Formula (VLIb)
- R* is CH 2 or where the diamine is 3,3'-sulphonyldianiline
- the diamine is 3,3'-sulphonyldianiline
- benzidine and 4,4'-sulphonyldianilines have sufficient conjugation and give the desired predominantly monomeric diaminobisimide compound and hence a substantially monomeric bisnadimide.
- Heteroaryl means aromatic monocyclic or polycyclic groups containing at least one heteroatom such as nitrogen, oxygen or sulfur.
- suitable “heteroaryl” groups are: 3- to 8- membered, more preferably 5- or 6- membered heteromonocychc groups containing 1 to 4 nitrogen atom(s), for example, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, triazinyl; condensed heterocyclic groups containing 1 to 5 nitrogen atom(s), for example, indolyl, isoindolyl, indolizinyl, benzimidazolyl, quinolyl, isoquinolyl, indazolyl, benzotriazolyl, etc.; 3- to 8- membered heteromonocychc groups containing 1 or 2 sulfur atom(s) and 1 to 3 nitrogen atom(s), for example, thiazo
- the alkyl group may be straight chain or branched and contain 1 to 20 carbon atoms. Suitable alkyl groups are methyl, ethyl, propyl, iro-propyl, /rbutyl, ir ⁇ -butyl, ter bvLtyl, /rpentyl, ⁇ -pentyi, neo-pentyl, n-octyl, iso-octyl, decyl, cetyl, stearyl, and the like.
- Alkoxy and “alkylthio” mean groups in which the alkyl moiety is a branched or unbranched saturated hydrocarbon group containing from one to eight carbon atoms, such as methyl, ethyl, propyl, is ⁇ -propyl, wbutyl, iro-butyl, tertbutyl and the like.
- Alkanoyl may be formyl, acetyl, propionyl, butyryl, valeryl, is ⁇ valeryl, pivaloyl, hexanoyl, and the like.
- the diaminobisimide of the Formula (III) is produced by the process disclosed in International Patent Pubhcation No. WO 92/06078 as such a compound is substantially free of oligomeric, amidic and uncyclized impurities.
- diarninobisimide of the Formula (HI) used in the method of the invention may be produced by any suitable known process.
- the reaction is preferably carried out using nadic anhydride or an alkyl- substituted nadic anhydride in the molten state as the solvent.
- the reaction may also be performed in the presence of a solvent such as an organic solvent, for example, dimethyl formamide, dimethylacetamide or xylene. If a solvent is used, because pure cyclized bisnadimides are formed and can be separated from the solvent as solids, unlike the case in standard PMR type resins, the products can be cured into final resins and composites without the porosity problems caused by strongly bound solvents.
- the reaction is performed at elevated temperatures, such as, for example, above about 120 °C.
- elevated temperatures such as, for example, above about 120 °C.
- Excess optionally substituted nadic anhydride maybe removed from the final product by washing with a suitable solvent, such as, for example, ethanol or hot water.
- a suitable solvent such as, for example, ethanol or hot water.
- the bisnadimides of Formula (II) are also novel and form another aspect of the present invention.
- the invention also provides bisnadimides of Formula (II) whenever prepared by a method as defined above.
- the bisnadimides of the invention which are substantially free of ohgomeric, amidic and uncyclized impurities, may be used in a curable formulation to produce impregnated fibre reinforced materials and to form crosslinked polyimide polymers which can be used in advanced composite materials.
- the PMR composition containing a toxic, reactive diamine of conventional practice is replaced by a safe, stable bisnadimide which can be readily handled during composite fabrication. Furthermore, on a weight of resin basis, much lower quantities of volatile cyclization products are evolved during the curing step as at least half the groups are already cyclized.
- the bisnadimides of the invention can be reacted with or without curing agents to form crosslinked polyimide polymers which are useful for a variety of applications including adhesives, bars, films, electronic encapsulation, moulded components and composites.
- the bisnadimides of Formula (II) may be converted into crosslinked polyimide polymers having improved properties.
- the invention further provides a curable formulation which comprises a bisnadimide of the Formula (II) as defined above.
- the bisnadimides of the invention are particularly useful in the manufacture of fibre reinforced composite materials.
- curable formulations containing the bisnadimides of the invention maybe applied to reinforcing cloth such as uni-directional or woven carbon fibre either from solution (preferably a lower aliphatic ketone or halogenated hydrocarbon solvent) or from a hot melt. Apphcation may be performed manually or by machine and includes techniques involving transfer from a precoated transfer medium. Therefore, the present invention also provides an impregnated fibre reinforced material (commonly known as a "prepreg") wherein the fibre reinforcements are coated with a curable formulation as defined above.
- prepreg impregnated fibre reinforced material
- a crosslinked polyimide polymer which is formed from a bisnadimide monomer of Formula (II) as defined above.
- a method for the preparation of the crosslinked polyimide polymer defined above which comprises heating a bisnadimide of Formula (II) as defined above.
- the bisnadimides are preferably heated to temperatures above about 250 °C. The heating may occur under pressure.
- trans-stilbene is a particularly good curing additive for the bisnadimides of the invention.
- Such additives provide cyclizable and aromatizable double bond compounds which are capable of reacting with reactive groups liberated by the bisnadimide type cure.
- Another additive particularly useful in the production of void-free resin bars from the bisnadimides of the invention is the addition of a small percentage of hydroquinone or other additives to prevent " ⁇ skinning" and hence entrapment of residual volatiles during the early stages of cure.
- the impregnated fibre reinforced material defined above are also suitable for use in the production of advanced composite materials.
- the impregnated fibre materials may be laid down by any suitable known method for making composite materials, such as, for example, vacuum bagging on a caul plate or an appropriate tool.
- the present invention also provides an advanced composite material which comprises an assembly of reinforcing fibres in a matrix of a crosslinked polyimide polymer as defined above.
- the bisnadimides of the invention can be used in an appropriate resin formulation for resin transfer moulding or for the manufacture of sheet moulded material. Another envisaged apphcation is in pultrusion.
- Bisnadimide resin CBR-116, Formula (II) wherein XisH, Aris C ⁇ H 3 COC I 3 and Ar' is 1 disubstituted methyldiethylphenyl
- a mixture of 400g of nadic anhydride and 200g of 5,5'-carbonylbis ⁇ 2-[3- amino(methyldiethyl)phenyl] ⁇ -lH-isoindole-l ⁇ (2H)-dione prepared by the method described in International Patent Pubhcation No. WO 92/06078 were mixed together as finely divided solids and then heated slowly with stirring to 180 °C.
- the nadic anhydride melted at about 160 ⁇ C and dissolved the diamine as well as reacting with it to liberate water. After heating with stirring for 8 hours the toffee-like mixture was cooled, ground and washed with very hot water to remove the large excess of unreacted anhydride.
- a matrix resin formulation was prepared for coating carbon fibre by dissolving
- a 20% (w/v) solution of the bisnadimide of Example 6 in methylene chloride was coated on to a carbon fibre cloth to give approximately a 40% resin content on the fibres after drying, the cloth was laid up in a 5 layer test part and cured in a heated press from 25 °C to 180 °C in 0.5 h, 180 ⁇ C/l h, 200 "C/1.5 h, 250 °C/6 h and 315 °C/2 h.
Abstract
Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP6513555A JPH08504196A (en) | 1992-12-07 | 1993-12-07 | Bisnadimide |
AU56190/94A AU5619094A (en) | 1992-12-07 | 1993-12-07 | Bisnadimides |
EP94901690A EP0672044A4 (en) | 1992-12-07 | 1993-12-07 | Bisnadimides. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AUPL623292 | 1992-12-07 | ||
AUPL6232 | 1992-12-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994013669A1 true WO1994013669A1 (en) | 1994-06-23 |
Family
ID=3776584
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/AU1993/000622 WO1994013669A1 (en) | 1992-12-07 | 1993-12-07 | Bisnadimides |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0672044A4 (en) |
JP (1) | JPH08504196A (en) |
AU (1) | AU5619094A (en) |
CA (1) | CA2150566A1 (en) |
NZ (1) | NZ258488A (en) |
WO (1) | WO1994013669A1 (en) |
Cited By (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20080300374A1 (en) * | 2007-05-31 | 2008-12-04 | The Boeing Company | Dinadic phenyl amine reactive endcaps |
US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
US9533954B2 (en) | 2010-12-22 | 2017-01-03 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
US9533984B2 (en) | 2013-04-19 | 2017-01-03 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
US9611267B2 (en) | 2012-06-13 | 2017-04-04 | Incyte Holdings Corporation | Substituted tricyclic compounds as FGFR inhibitors |
US9708318B2 (en) | 2015-02-20 | 2017-07-18 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
US9890156B2 (en) | 2015-02-20 | 2018-02-13 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
US10611762B2 (en) | 2017-05-26 | 2020-04-07 | Incyte Corporation | Crystalline forms of a FGFR inhibitor and processes for preparing the same |
US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
US11174257B2 (en) | 2018-05-04 | 2021-11-16 | Incyte Corporation | Salts of an FGFR inhibitor |
US11274181B2 (en) | 2017-09-18 | 2022-03-15 | Chevron Oronite Company Llc | Polyimide dispersants and methods of making and using thereof |
US11407750B2 (en) | 2019-12-04 | 2022-08-09 | Incyte Corporation | Derivatives of an FGFR inhibitor |
US11466004B2 (en) | 2018-05-04 | 2022-10-11 | Incyte Corporation | Solid forms of an FGFR inhibitor and processes for preparing the same |
US11566028B2 (en) | 2019-10-16 | 2023-01-31 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
US11607416B2 (en) | 2019-10-14 | 2023-03-21 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
US11897891B2 (en) | 2019-12-04 | 2024-02-13 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2862557A (en) * | 1957-06-12 | 1957-12-19 | E. I. Dupont De Nemours And Company | New cyclopentene derivatives and their use in the preparation of di-glutamic acid |
AU5057272A (en) * | 1971-12-28 | 1974-07-04 | Fuji Photo Film Co Ltd | Photographic element and process of forming yellow photographic images |
US3998786A (en) * | 1973-05-25 | 1976-12-21 | University Of Notre Dame Du Lac | Process for preparing aromatic polyimides, polyimides prepared thereby |
AU8628091A (en) * | 1990-10-03 | 1992-04-28 | Commonwealth Scientific And Industrial Research Organisation | Epoxy resins based on diaminobisimide compounds |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5210213A (en) * | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
CA1204760A (en) * | 1982-11-18 | 1986-05-20 | Hong-Son Ryang | Silicone-polyimide copolymers, condensation vulcanizable compositions obtained therefrom, and methods for making |
JP2600294B2 (en) * | 1988-06-11 | 1997-04-16 | ダイキン工業株式会社 | New curable fluorinated polyimide |
EP0357558B1 (en) * | 1988-09-02 | 1994-02-02 | Ciba-Geigy Ag | Bisimides of allyl-substituted or methallyl-substituted bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid |
JPH08504197A (en) * | 1992-12-07 | 1996-05-07 | コモンウェルス・サイエンティフィック・アンド・インダストリアル・リサーチ・オーガニゼイション | Polymerizable Monomer Reactor (PMR) Type Resin |
-
1993
- 1993-12-07 CA CA002150566A patent/CA2150566A1/en not_active Abandoned
- 1993-12-07 EP EP94901690A patent/EP0672044A4/en not_active Withdrawn
- 1993-12-07 WO PCT/AU1993/000622 patent/WO1994013669A1/en not_active Application Discontinuation
- 1993-12-07 NZ NZ258488A patent/NZ258488A/en unknown
- 1993-12-07 JP JP6513555A patent/JPH08504196A/en active Pending
- 1993-12-07 AU AU56190/94A patent/AU5619094A/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2862557A (en) * | 1957-06-12 | 1957-12-19 | E. I. Dupont De Nemours And Company | New cyclopentene derivatives and their use in the preparation of di-glutamic acid |
AU5057272A (en) * | 1971-12-28 | 1974-07-04 | Fuji Photo Film Co Ltd | Photographic element and process of forming yellow photographic images |
US3998786A (en) * | 1973-05-25 | 1976-12-21 | University Of Notre Dame Du Lac | Process for preparing aromatic polyimides, polyimides prepared thereby |
AU8628091A (en) * | 1990-10-03 | 1992-04-28 | Commonwealth Scientific And Industrial Research Organisation | Epoxy resins based on diaminobisimide compounds |
Non-Patent Citations (1)
Title |
---|
See also references of EP0672044A4 * |
Cited By (41)
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---|---|---|---|---|
US20080300374A1 (en) * | 2007-05-31 | 2008-12-04 | The Boeing Company | Dinadic phenyl amine reactive endcaps |
US9533954B2 (en) | 2010-12-22 | 2017-01-03 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
US10213427B2 (en) | 2010-12-22 | 2019-02-26 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
US10813930B2 (en) | 2010-12-22 | 2020-10-27 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
US10131667B2 (en) | 2012-06-13 | 2018-11-20 | Incyte Corporation | Substituted tricyclic compounds as FGFR inhibitors |
US11840534B2 (en) | 2012-06-13 | 2023-12-12 | Incyte Corporation | Substituted tricyclic compounds as FGFR inhibitors |
US9611267B2 (en) | 2012-06-13 | 2017-04-04 | Incyte Holdings Corporation | Substituted tricyclic compounds as FGFR inhibitors |
US11053246B2 (en) | 2012-06-13 | 2021-07-06 | Incyte Corporation | Substituted tricyclic compounds as FGFR inhibitors |
US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
US9745311B2 (en) | 2012-08-10 | 2017-08-29 | Incyte Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
US9533984B2 (en) | 2013-04-19 | 2017-01-03 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
US10040790B2 (en) | 2013-04-19 | 2018-08-07 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
US10947230B2 (en) | 2013-04-19 | 2021-03-16 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
US11530214B2 (en) | 2013-04-19 | 2022-12-20 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
US10450313B2 (en) | 2013-04-19 | 2019-10-22 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
US10738048B2 (en) | 2015-02-20 | 2020-08-11 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
US11014923B2 (en) | 2015-02-20 | 2021-05-25 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
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Also Published As
Publication number | Publication date |
---|---|
AU5619094A (en) | 1994-07-04 |
JPH08504196A (en) | 1996-05-07 |
EP0672044A4 (en) | 1997-08-20 |
NZ258488A (en) | 1997-02-24 |
CA2150566A1 (en) | 1994-06-23 |
EP0672044A1 (en) | 1995-09-20 |
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