State of the Art Organic Matrices for High- performance...

State of the Art Organic Matrices for High-performance Composites: A Review

High performance polymers are commonly and widely used in advanced technolo-gies and cover large varieties of applications such as micro and nanoelectronics,civil and military transportation, defense, etc. It is important for these technologies

to design tailor-made high tech materials by focusing on molecular structure/processabil-ity/properties relationships of high performance polymers such as heterocyclic polymersknown for their outstanding thermal properties and their good mechanical behaviour oreven functionalized polymers or inorganic polymers. Nowadays, there is a strongdemand of such resins since the development of composites and recently nanocompos-ite materials. Of the high temperature polymers commercially available, one can citepoly(arylene ethers), polybenzimidazoles, resins from cyanates, resin from bis-maleimides, organofluoro polymers, certain silicones and liquid crystalline polyesters.Polyimides and poly(arylene ether)s have attracted the attention of scientists and engi-neers more than other polymers. This attention is not only due to the attractive combina-tion of properties but also because polyimides and poly(arylene ether)s can be readily tai-lor-made for specific applications. This article gives an account of developments in hightemperature organic polymers during the last 5 years with major emphasis on linear,hyperbranched or dendritic structures concerning polyimides family, polyphenylquinoxa-lines and end-capped polymers such as bis-maleimides, PMR-15 and acetylene-termi-nated resins, highlighting the chemical structure with their ultimate physico-mechanicalproperties and focusing on the parameters which govern their processability.Processability and different applications will be presented as films (membranes for fuelcell), photosensitive products (microelectronics) or prepregs.

polyheterocyclic polymers;functional polymers;high-temperature polymers;linear and thermoset structures.

A B S T R A C T

Key Words:

CONTENT

Marc J.M. Abadie*1, Vanda Yu. Voytekunas1, and Alexander L. Rusanov2

(1) Laboratory of Polymer Science & Advance Organic Materials-LEMP/MAO, UniversitØMontpellier 2, Sciences et Techniques du Languedoc, Montpellier 34095, France (2) Institute of Organo-Element Compounds INEOS, A.N. Nesmeyanov Institute,

Russian Academy of Science, Moscow-119991, Russia

Received 21 June 2005; accepted 23 January 2006

- Introduction- Linear structures

- Polyimides- Polyphenylquinoxalines- Nanocomposites

- Hyperbranched and dendritic struc-tures

- Three-dimensional structures- PMR-15- Acetylene-terminated resin- Bismaleimides

- Conclusion

Iranian Polymer Journal

15 (1), 2006, 65-77

(*) To whom correspondence should be addressed.E-mail: [email protected]

Available online at: http://journal.ippi.ac.ir

66

State of the Art Organic Matrices for High-performance... Abadie M.J.M. et al.

Iranian Polymer Journal / Volume 15 Number 1 (2006)

INTRODUCTIONThe quest for high temperature organic polymers,materials that perform at 200oC or higher, began in thelate 1950s, to meet the demands primarily of the aero-space and microelectronics industries. Heterocyclicand aromatic polymers were introduced during the1960s in order to match the thermal stability require-ments of the aerospace industry. Aromatic and hetero-cyclic rings offer conjugated rigid structures with hightransition temperature and strong linkage, allowinggood resistance in harsh environments. Since then,many families of high temperature polymers have beenreported and several of them have reached commercial-ization.

Therefore, aromatic polyimides play an importantrole in the field of high temperature polymers and areimportant classes of polymers that have found applica-tion as high performance polymers due to their ther-mooxidative stability, electrical properties, high radia-tion and solvent resistance and high mechanicalstrength [1-5].

Of the high temperature polymers commerciallyavailable, one can cite poly(arylene ethers), polybenz-imidazoles, resins from cyanates, resin from bismaleimides, organofluoro polymers, certain siliconesand liquid crytalline polyesters. Polyimides andpoly(arylene ether)s have attracted the attention of sci-entists and engineers more than other polymers. Thisattention is not only due to the attractive combinationof properties but also because polimides and poly(ary-lene ether)s can be readily tailor-made for specificapplications. Within certain limits, properties such aschemical inertness, dielectric constant, color, glasstransition (Tg) or crystalline melt (Tm) temperature,coefficient of thermal expansion (CTE), oxidative sta-bility and solubility can be controlled by the chemicalstructure of the polymer. A recent book [6] offers thepossibility of calculating some physical properties ofpolymers on the basis of the chemical structure of therepeat unit using simulation program CHEOPS.Mechanical manipulation can also improve certainproperties such as tensile strength, modulus and CTE,for example of films and fibres. In addition, molecularweight and molecular weight distribution control andend-capping can alter properties such as viscosity andtoughness.

For the past decades, increasing need in the high

technology industries such as microelectronics, aero-space, defense, membranes, consumer sports, electron-ics, electrical, automotives and life science/medicalindustry etc., has been the driving force for the devel-opment of new polymeric systems combining thermalstability with specific functional properties.

The feature of polyimides and other heterocyclicpolymers are now well recognized and used for longterm temperature durability in the range 200-300oC.

This article presents a review of different classes ofheterocyclic polymers including polyimides family,polyphenylquinoxalines and end-capped structuressuch as PMR-15, bis-maleimides and acetylene-termi-nated resin (ATR), linear and hyperbranched structuresand dendrimers, highlighting the chemical structurewith their ultimate physico-mechanical properties andfocusing on the parameters which govern their process-ability.

LINEAR STRUCTURES

PolyimidesThe most common technique for the fabrication ofpolyimides (PI) is forming the soluble precursor, apoly(amic-acid) PAA, casting films and then thermallydehydrating into the final imide form [7]. One of thebest examples is the formation of Kaptonfi fromDuPont de Nemours, which results from a polyconden-sation reaction of a dianhydride, pyromellitic dianhy-dride PMDA and a diamine, oxidianiline ODA(PMDA/ODA polyimide) (Scheme I).

However, it suffers from insolubility and high soft-ening temperatures that makes its processing impossi-ble or expensive. This process leads to other problemssuch as inefficient cyclization, difficult removal ofwater and the formation of microvoids in the finalmaterial.

The key reasons for insolubility and the non-melt-ing character of the wholly aromatic polyimides are thelack of flexibility and strong interchain interation dueto high symmetry and highly polar groups and alsosometime hydrogen bonding [8]. In polyimides, stronginteractions originate from intra- and interchain chargetransfer complex (CTC) formation and electronicpolarization which is supported by the strong electronacceptor character of imides and electron donor charac-

State of the Art Organic Matrices for High-performance...Abadie M.J.M. et al.

Iranian Polymer Journal / Volume 15 Number 1 (2006) 67

ter of amine segments. These interactions can be weak-ened by the disruption of the coplanarity and conjuga-tion, by reduction of the symmetry and by alteration ofelectronic character of each segment.

In the last few decades, many studies have beenconducted to control these interactions in order to pro-duce more tractable polyimides which can be processedby conventional techniques such as melt processing orcasting from volatile organic solvents while maintain-ing thermooxidative stability. The majority of thesestudies involved three main structure modifications totailor the properties :

- incorporation of thermally stable but flexible ornon symmetrical linkages in the backbone.

- introduction of large polar and non-polar sub-stituents pendant from the polymer backbone.

- disruption of symmetry and recurrence of regular-ity through copolymerization [9].

Incorporation of flexible linkages such as -O-,-CH2-, -SO2- and hexafluoroisopropylidene groups(6F) into the backbone introduces �kinks� to the mainchain which decrease the rigidity of the polymer back-bone and inhibit packing, thus reducing the interchaininteraction and H-bonding and leading to enhanced sol-ubility [10]. Ultemfi from GE is a good example withgood mouldability and mechanical properties alongwith reasonable thermal properties.

Isomeric structures also distort linearity of the

chain and increase the interchain distance which lowersthe energy necessary for rotation. This lowers the Tgand the softening and or/Tm and increases solvent pen-etration and solubilization of polymer [11]. For exam-ple, going from the all para structure of Kevlarfi tometa-linked Nomexfi , solubility improves drasticallyalong with ca 100oC decrease in the melting point(from ca 530oC to ca 435oC).

Introducing aromatic and non-aromatic but ther-mally stable cardo-, spiro- or multicyclic structure asfluorene or adamantyl into the polymer backbone isalso a promising method for property modification inpolyimides [12].

Bulky substituents can impart a significant increasein both Tg and thermooxidative stability while provid-ing good solubility, especially with non-symmetrical orflexible units in the backbone [13]. Basically, bulkysubstituents decrease crystallinity and packing efficien-cy by distortion of backbone symmetry and also restrictsegmental mobility. The severity of the effect dependson the number, size and polarity of the substituents.

An interesting approach to overcome a trade-offbetween thermal properties and the solubility andprocessability since the same structural feature thatenhances one decreases the other was to control chainflexibility and segmental mobility through the incorpo-ration of diamines shown in Scheme II:

These are highly substituted (hindered) diamines

Scheme I

68



which reduce C-N bond rotation or extended bis(etheramine)s which combine flexible ether linkages andortho-substituents (methyl, tert-butyl) that hinder inter-nal C-O bond rotation or break the full aromaticity andplanarity with a cardo-cyclohexene unit. Polyimideswith enhanced solubility along with high Tg and thermalstability have been synthesized from these sterically hin-dered diamines. Substitution at the ortho position of C-Nbonds leads to this unique property combination which isvery desirable for new application areas and fabricationopportunities that are not available for insoluble poly-imides. Ortho-substitution at the C-N site is proposed toprevent coplanarity of the donor and acceptor units,weakening the intra- and interchain interactions and the

packing, rendering these polymers soluble. High glasstransition temperatures were therefore obtained as thesegmental mobility was hindered dramatically by theortho substituents to the nitrogens. [14].

A few years ago, an original way for obtaining newtype of polyimides was initiated by using TNT deriva-tives in the framework of NATO program so-calledScience for Peace (SfP) [15]. A wide range of amineswas obtained containing fluoride, sulphur, particularlyhydroxyl-containing diamines (HDA)s such as 3,5-diamino-4’-hydroxydiphenyl ether. This product wasprepared using a 3-stage process: TNT dimethylation(oxidation/decarboxylation), substitution of one nitrogroup in 1,3,5-trinitrobenzene (TNB) formed with

Scheme II

Scheme III



hydroquinone and reduction of 3,5-dinitro-4’-hydroxy-diphenylether thus obtained (Scheme III). These wereused for the preparation of new organo-soluble hydrox-ylated polyimides (HPI)s [15], new fluorinated [16]and sulphur [17] polyimides based on TNT derivatives.

Hydroxylated polyimides are of great interestbecause of the presence of phenolic hydroxyl groups inthese polymers results in interesting and potentiallyuseful properties, e.g. high glass transition temperature,good solubility in organic solvents, high degree ofwater uptake due to hydrogen bonding. In addition,phenolic hydroxyl groups may be used for the introduc-tion of unsaturated groups into the polyimide macro-molecules and as a result, for the preparation of pho-toactive polymers like negative photoresists [18].

An interesting approach was developed to reinforcedomestic plastics by grafting polyimides and develop-ing new polymer systems by additional thermal poly-merization of different acrylates containing polyimides.Different systems of polyimide have been dissolved inmethyl methacrylate or styrene and have been success-fully copolymerized either by thermal or UV radicalprocess [19-21].

PolyphenylquinoxalinesPolyphenylquinoxalines (PPQs) are a family of aromat-ic condensation polymers known for their outstandingthermal and chemical stability. The most knownmethod for the PPQs preparation is the interaction ofbis(o-phenylenediamines) with bis(α-diketones) inprotogenic solvents [22,23].

The pendant phenyl groups and chains isomerismimprove the solubility and processing characteristics ofthese polymers over the unsubstituted polymers. Thesepolymers have also been shown to possess excellentthermooxidative stability and thermohydrolytic stabili-ty [24].

The most known PPQ commercialized in the USAand France is polymer based on 3,3’- diaminobenzidine(DAB) and 1,4-bis(phenylglyoxalyl)benzene (BPGB).In Russia, the main attention was paid to the PPQ’sbased on 3,3’;4’,4-tetraaminodiphenyl ether (TADE).This monomer, which was firstly described by Stille etal. [25] and commercialized in pilot scale in Russia ismore nucleophilic and less toxic when compared withDAB. In addition, incorporation of the ether groups inthe PPQ’s macromolecules leads to the improved flexi-bility of the target polymers. As comonomers of TADE

there were used 4,4’-bis(phenylglyoxalyl)diphenylether (BPGDPE) [26] and especially BPGB [27,28].

Very simple and inexpensive route for the prepara-tion of BPGB developed by our group is based on theinteraction of terephthalic acid dichloride with two-foldmolar amount of styrene with subsequent oxidation ofthe 1,4-distyrylbenzene thus formed [27,28].PPQs of general formula (Scheme IV) are soluble inCHCl3, m-cresol and benzyl alcohol.

They demonstrate good film-forming properties, mod-erate glass transition temperatures (250-280oC), excel-lent thermooxidative and thermohydrolytic stability.This stability makes these polymers candidates fordevelopment as proton exchange membranes (PEMs)to be used in fuel cells [29]. In addition to thermohy-drolytic stability, PEMs require high protonic conduc-tivity and in order to achieve this they also require highwater uptake. Aromatic condensation polymers do notpossess these properties, but ionomers derived fromthem may have them.

NanocompositesThe nano-scale technology is also an ongoing focus ofintense research. It concerns a new emerging field of R& D where organic polymer/inorganic hybrid ornanocomposites materials (ceramer) would exhibitproperties of combination of both ceramics (retentionof mechanical properties at high temperature, low ther-mal expansion) and organic polymers (toughness, duc-tility and processability). Some recent results on poly-imide/clay nanocomposite were recently presented atSTEPI 6 and properties have been compared to com-mercial polyether-imide ULTEMfi 1000 (from GE) and

Scheme IV

70



polyimide KAPTONfi H (from DuPont) products [30].

HYPERBRANCHED AND DENDRITICSTRUCTURES

In 1941 Flory introduced the concept of hyperbranchedmacromolecules that still remains an area of intenseresearch interest. Hyperbranched polymers and den-drimers, which are termed as "dendritic macromole-cules" have received much attention in recent years [31].Perfectly defined structures can be obtained only whenmonomer condensation are done step-by-step. At eachstep, the trifunctional molecule AB2 reacts selectivelyvia A with only one of the two B functions of anothermolecule because the second B function has been pro-tected (Scheme V). When the B function that could notreact is deprotected, the reaction can be continued and astructure without default, so-called dendrimer, can beobtained (Scheme VI). Condensation without protectingfunctions yields structures called hyperbranched.

One of the main interest of this class of structuralpolymer is that thermal properties (glass transition, heatstability) are unaffected by polymer architecture, butbranched structures are more soluble than the linearstructure [32]. Because of their unique architecture,these polymers show attractive properties such as lowviscosity and excellent solubility in organic solvents,which make them as good candidate for impregnationof carbon fibres for producing laminate composites.

Publications dealing with hyperbranched poly-imides are recent and not very numerous. Different sys-tems have been investigated, ABx in one [33] or twostep reaction [34], unsymmetrical BB’2 monomer andan A2 monomer (for which in situ AB’2 intermediateformation during polymerization was suggested toresemble the AB2 polymerization) [35] or A2 + B3 [36,37]. Although the A2 + B3 polymerization approachshows many advantages such as facile preparation andscaling up, easy to tailor structure, over the AB2 poly-merization approach, it has an intrinsic problem thatgelation is unavoidable over a certain conversion in a1:1 molar monomer feed ratio, as pointed out by Floryover 50 years ago.

THREE-DIMENSIONAL STRUCTURESInitially developed linear systems were obtained bypolycondensation reactions and exhibited very high

glass transition temperature which presented problemsin processing. In an attempt to overcome these difficul-ties, research has focused on reactive oligomersexhibiting the required Tg and flow characteristics.

PMR-15Up to now composites based on epoxy resin matriceshave dominated the technology. However, their appli-cation is limited to maximum use temperature of about130�C. There are many applications that require mate-rials that may be used at temperatures substantially inexcess of this, particularly in the aerospace industry.While the processing of thermoplastic polyimides isoften difficult during composite fabrication, the use ofoligomeric imides with reactive end-caps has greatlyimproved the processability of polyimide composites.A leading candidate for high temperature resin is theNASA developed polyimide "PMR-15". PMR standsfor "Polymerization of Monomeric Reactants" andrefers to the way in which carbon fibres are impregnat-ed with a solution of the monomers which are thenpolymerized in-situ. Using the ester-acid route, thePMR approach ensures easy processing of imideoligomers. As a result, PMR-15, an addition curingpolyimide based on 3,3’,4,4’-benzophenonetetracar-boxylic acid dimethyl ester and methylene dianiline(MDA) with nadic ester as the endcap has been recog-nized as the state-of-the-art high temperature resin forcomposite application at 288oC (550�F). The chemistryof the cure process is shown in Scheme VII:

PMR-15 is a processable, high-temperature poly-mer developed at the NASA Lewis Research Center inthe 1970’s principally for aeropropulsion applications.Use of fibre-reinforced polymer matrix composites inthese applications can lead to substantial weight sav-ings, thereby leading to improved fuel economy,increased passenger and payload capacity, and bettermaneuverability. PMR-15 is used fairly extensively in

Scheme V



military and commercial aircraft engines componentsseeing service temperatures as high as 500 oF (260oC),such as the outer bypass duct for the F-404 engine. Thecurrent world-wide market for PMR-15 materials(resins, adhesives, and composites) is of the order of $6to 10 million annually.

However, PMR-15 is prepared with a monomer,methylenedianiline (MDA), which is a known animaland suspect human carcinogen. The Occupational Safe-ty and Health Administration (OSHA) and the Environ-mental Protection Agency (EPA) heavily regulate theuse of MDA in the workplace and require certain engi-neering controls be used whenever MDA-containingmaterials (e.g., PMR-15) are being handled andprocessed. Implementation of these safety measures forthe handling and disposal of PMR-15 materials coststhe aircraft engine manufacturing industry millions ofdollars annually.

Under the Advanced Subsonic Technology (AST)Program, researchers at NASA Lewis, General Elec-tric, DuPont, Maverick Composites, and St. NorbertCollege have been working to develop and identifyreplacements for PMR-15 that do not rely upon the useof carcinogenic or mutagenic starting materials. Thiseffort involves toxicological screening (Ames’ testing)of new monomers as well as an evaluation of the prop-

erties and high-temperature performance of polymersand composites prepared with these materials. A num-ber of diamines have been screened for use in PMR-15replacements. Three diamines, BAX, CO-BAX, andBAPP, passed the Ames’ testing (Scheme VIII).

Graphite-reinforced composites prepared withpolyimides containing these diamines were evaluatedagainst a PMR-15 control in terms of their high-tem-perature stability (weight loss after 125 h in air at316oC and 5-atm pressure) and glass-transition temper-ature (an indication of high-temperature mechanicalperformance). Of these three materials systems, boththe BAX and CO-BAX composites had stabilities andglass-transition temperatures comparable to those ofPMR-15. Further evaluation of the processability ofthese materials as well as their long-term stability andmechanical performance at 288oC (550�F) is inprogress (Figure 1).

By replacing methylene diamine (MDA) in PMR-15 (Tg = 348oC) with 2,2’-dimethylbenzidine (DMBZ,i.e. m-Toluidine), whose non-coplanar conformation isknown to enhance the processability of addition poly-imides, raises the glass transition temperature of theresulting polyimide (DMBZ-15) to Tg = 414oC [38].Apparently, the two methyl substituents on thebiphenyl moiety of DMBZ impart a higher rotational

Scheme VI

72



barrier to the polymer. Due to higher Tg, DMBZ-15composites exhibited better mechanical properties thanPMR-15 composites beyond 300-400oC for shortexcursion (Figure 2).

Acetylene-terminated Resisn (ATR)End-capped oligomers with acetylene functions poly-merize without releasing volatile products. The result-ing networks take up water to a relatively slight extentand have good thermal resistance. As in the case for alloligomers, mechanical properties are mainly controlledby the structure of groups located between acetylenefunctions. Even so, there are some disadvantages whenusing these oligomers :

- The synthesis of the reactant bearing the acetylene

function is a multi-step synthesis and make the productcostly. The most classical process uses a Palladiumbased catalyst that catalysis an oxidizing degradationeven at low concentration in the polymerized network,

- The processing window is very narrow since poly-merisation starts at low temperature (120oC), thus atthe same time as oligomer melting,

- The polymerization enthalpy is relatively high(130 kJ per function).

In spite of this, National Starch has marketedTHERMIDfi 600, an oligoimide that could be used asa composite or adhesive matrix up to 315oC. The searchfor a broader processability window is the reasonbehind the study of different types of oligomers withphenyl acetylene groups [39], within the chain [40-42]

(a)

Figure 1. Comparison of the glass-transition temperature and thermal-oxidative stability of graphite-reinforced composites pre-pared with non-MDA PMR-15 replacements. Left: Weight loss after 125 h in air at 316oC and 5 atm. Right: Glass-transition tem-perature.

5

4

3

2

1

0

1.38

2.21

1.0

4.72 PMR-15AMB-21BAXCO-BAX

400

300

200

100

0

350oC

240oC

340oC355oC

(b)

Figure 2. One hot-wet cycle = 93oC water soak to >1% weight gain, dry out at 288oC to <0.1% moisture

700

232oC 288oC 5hot/wet

600

500

400

300

200

100

023oC

PMR-15DMBZ-15



Scheme VII

Scheme VIII

74



Scheme X

Scheme IX



or at the extremities [43]. Example of this type ofoligoimides is PETITfi 5 developed by Cytec Fiberitefor composites and adhesive matrices (Scheme IX).

Bismaleimides Bismaleimide resins are still of increasing interest tothe aerospace and electronic industry as matrix resinsfor fibre composites. Bismaleimides chemistry wasfirst introduced and developed by Rh�ne-Poullenc -KERIMIDfi 601 [44]. Bis-maleimide-based networkpolymers possess high glass transition temperaturesand high thermal stability and rigidity. At the sametime, these polymers are very brittle, and the process-ing of the bismaleimides as such to fabricate articles isstrongly complicated by high curing temperatures andlimited durability. To overcome these problems, it iscommon practice to use reactive diluents (reactivecomonomers) to improve resin processability.

Consequently, the ideal comonomer would functionboth as a reactive diluent, i.e. liquid at room tempera-ture, and as toughening agent. The key issue to use acomonomer is that the comonomer undergoes a linearchain extension reaction with the BMI to reduce thecrosslinking density in the fully cured resin. Therefore,the use of 2,2’-diallylbisphenol-A (DABPA) as acomonomer capable of entering the Michael reactionwith bis-maleimides. The technological properties ofthe system based on 4,4í-(N,Ní-bismaleimide)diphenyl-methane (BMDM) and DABPA turned to be excellent,but the different reactions involved are quite complex,i.e. -ene and -diene addition reaction, Michael reaction,Diels-Alder reaction, homopolymerisation, copolymer-ization, reverse Diels-Alder reaction, etc. [45]. Thebrittleness was also substantially reduced, with retain-ing the high heat resistance (Scheme X).

The bismaleimide systems can be cured thermallyeither in excess of bis-maleimides or diamines.

Recent works on BMDP/DABPA shown that it waspossible to crosslink the system by electron-beam (EB)or by UV at room temperature [46].

CONCLUSION

Aromatic and heterocyclic rings offer conjugated rigidstructures with high glass transition temperature andstrong linkages, allowing good resistance in harsh envi-

ronments. However, it is always a compromise to bemade to match at the same time the thermal stabilityrequirements and processability which is needed forindrustrial applications.

REFERENCES

1. Sroog C.E., Polyimides, J. Polym. Sci., Macromol. Rev.,11, 161-208 (1976)

2. Cassidy P.E., Thermal Stable Polymers, Marcel & Dekker,New York (1980).

3. Besanov M.I., Koton M.M., Kudriatsev V.V., Laius L.A.,Polyimides: Thermally Stable Polymers, ConsultantBureau, New York (1987).

4. Vallerani E., Marchese P., Fornari B., Frontiers of PolymerResearch, Pascal P.N., Nigam J.N. (Eds.), Plenum, NewYork (1991).

5. Ghosh M.K., Mittal K.L. (Eds.), Polyimides: Fundamen-tals and Applications, Marcel & Dekker, New York (1996,1999 & 2003).

6. Askadskii A.A., Computional Materials Science of Poly-mers, Cambridge Int. Sci., Cambridge CB1 3AZ, UK(2003).

7. Hsiao S.H., Huang P.C., Synthesis and characterization ofaromatic poly(ether sulfone imide)s derived from sulfonylbis(ether anhydride)s and aromatic diamines, J. Polym.Sci., Part A: Polym. Chem., 36, 1649-1656 (1998).

8. Clair T.L.St., Polyimides, Wilson D., Stenzenberger H.D.,Hergenrother P.M. (Eds.), Chapman and Hall, New York,58-78 (1990).

9. Harris F.W., Lanier L.H., Structure-Solubility Relation-ships in Polymers, Harris F.W., Seymour R.B. (Eds), Aca-demic, New York, 183-198 (1997).

10. Fang F.Si.L., Ge J.J., Honigfort P.S., Chen J.C., HarrisF.W., Cheng S.Z.D., Diamine architecture effects on glasstransitions, relaxation processes and other material prop-erties in organo-soluble aromatic polyimide films, Poly-mer, 40, 4571-4583 (1999).

11. Mikroyannidis J.A., Tsivgoulis G.M., Synthesis andcharacterization of soluble, blue-fluorescent polyamidesand polyimides containing substituted p-terphenyl as wellas long aliphatic segments in the main chain, J. Polym.Sci., Part A: Polym. Chem., 37, 3646-3656 (1999).

12. Liaw D.J., Liaw B.Y., Synthesis and properties of newpolyimides derived from 1,1-bis[4-(4-aminophenoxy)phenyl]cyclododecane, Polymer, 40, 3183-3189 (1999).

76



13. Hsiao S.H., Li C.T., Synthesis and characterization ofnew adamantane-based cardo polyamides, J. Polym. Sci.,Part A: Polym. Chem., 37, 1435-1442 (1999).

14. Yagci H., Ostrowski C., Mathias L.J., Synthesis and char-acterization of novel aromatic polyimides from 4,4-bis(p-aminophenoxymethyl)-1-cyclohexene, J. Polym. Sci.,Part A: Polym. Chem., 37, 1189-1197 (1999).

15. Abadie M.J.M., Izri I., Sheveleva T.S., Rusanov A.L.,Polyimides and High Performance Polymers-STEPI 4,Abadie M.J.M., Sillion B. (Eds.), Montpellier, 163-168(1996).

16. Rusanov A.L., Komorova L.G., Progozhina M.P., Askad-skii A.A., Shevelev S.A., Dutov M.D., Korolev M.A.,Sapozhnikov O.Yu., Polyimides and High PerformancePolymers-STEPI 5, Abadie M.J.M., Sillion B. (Eds.),Montpellier, 89-96 (1999).

17. Rusanov A.L., Sheveleva T.S., Prigozhina M.P.,Komorova L.G., Shevelev S.A., Dutov M.D., KorolevM.A., Sapozhnikov O.Yu., Polyimides and High Perfor-mance Polymers-STEPI 5, Abadie M.J.M., Sillion B.(Eds.), Montpellier, 97-105 (1999).

18.Voytekunas V.Yu., Komarova L.G., Rusanov A.L.,Prigozhina M.P., Abadie M.J.M., Polyimides and HighPerformance Polymers-STEPI 6, Abadie M.J.M., SillionB. (Eds.), Montpellier, 82-92 (2002).

19. Vygodskii Y.S., Sakharova A.A., Matieva A.M., The for-mulation of polymers by polymerization-polycondensa-tion processes: polyimide based systems, High Perform.Polym., 11, 379-386 (1999).

20. Voytekunas V.Yu., Abadie M.J.M., Matieva A.M.,Vygodskii Y.S., Polyimides and High Performance Poly-mers, STEPI 6, Abadie M.J.M., Sillion B. (Eds.), Mont-pellier, 123-136 (2002).

21. Voytekunas V.Yu., Abadie M.J.M., Matieva A.M.,Vygodskii Y.S., Photopolymerization of methyl methacry-late in the presence of polyimide, Polym. Sci., Series B,45, 67-70 (2003).

22. Hergenrother P.M., J. Macromol. Sci., Revs., C6, 1(1971)

23. Rusanov A.L., Tugushi D.S., Korshak V.V, Progress inPolyheteroarylenes Chemistry, Tbilissi State University,Tbilissi, 180- (1988).

24. Korshak V.V., Pavlova S.A., Gribkova P.N., Berlin A.M.,Vlasova I.V., Krongauz E.S., Vysokomolek. Soyed., A17,2407- (1975).

25. Stille J.K.,Williamson J.R., Arnold F.E., Polyquinoxa-lines II*, J. Polym. Sci., A3, 1013-1030 (1964).

26. Ogliaruso M.A., Shadoff L.A., Becker E.J., Bistetracy-clones and Bishexaphenylbenzenes, J. Org. Chem., 28,2725-2728 (1963).

27. Yusubov M.S., Filimonov V.D., Savchenko T.I., Belo-moina N.M., Krongauz E.S., Rusanov A.L., Kogan A.S,Tkachenko A.S., US Patent, 1, 660,345 (1991).

28. Yusubov M.S., Savchenko T.I., Filimonov V.D., KovalikV.M., Belomoina N.M., Rusanov A.L., Krongauz E.S.,Kogan A.S., Tkachenko A.S., US Patent, 1, 824,390(1992).

29. Rusanov A.L., Likhachev D.Yu., Mullen K., Proton-con-ducting electrolyte membranes based in aromatic conden-sation polymers, Russ. Chem. Revs., 71, 761-774 (2002).

30. Vora R.H., Pallathadka P.K., Goh S.H., Polyimides andHigh Performance Polymers, STEPI 6, Abadie M.J.M.,Sillion B. (Eds.), Montpellier, 191-207 (2002).

31. Voit B., New developments in hyperbranched polymers,J. Polym. Sci., Part A : Polym. Chem., 38, 2505-2525(2000).

32. Frechet J.M.J., Functional polymers and dendrimers:Reactivity, molecular architecture, and interfacial energy,Science, 263, 1710-1715 (1994).

33. Thomson D.S., Markoski L.J., Moore J.S., Rapid synthe-sis of hyperbranched aromatic polyetherimides, Macro-molecules, 32, 4764-4768 (1999)

34. Yamanaka K., Jikei M., Kakimoto M.A., Synthesis ofhyperbranched aromatic polyimides via polyamic acidmethyl ester precursor, Macromolecules, 33, 1111-1114(2000).

35. Gao C., Yan D., Polyaddition of B2 and BB2 typemonomers to A2 type monomer.1. Synthesis of highlybranched copoly(sulfone-amine)s, Macromolecules, 34,156-161 (2001).

36. Fang J., Kita H., Okamoto K.I., Hyperbranched poly-imides for gas separation applications. 1. Synthesis andcharacterization, Macromolecules, 33, 4639-4646 (2000).

37. Hao J., Jikei M., Kakimoto M., Preparation of hyper-branched aromatic polyimides via A2+B3 approach,Macromolecules, 35, 5372-5381 (2002).

38. Chuang K.C., Bowles K.J., Scheiman D.A., Papadopou-los D.S., Hardy-Green D., Polyimides and Other HighTemperature Polymers, Mittal K.L. (Ed.), Vol. 1, 113-127(2001)

39. Meyer G.W., Pack S.J., Lee Y.J., McGrath J.E., Newhigh-performance thermosetting polymer matrix materialsystems, Polymer, 36, 11, 2303-2309 (1995).

40. Takeichi T., Suefuji K., Zuo M., Nakamura K., Ando S.,

State of the Art Organic Matrices for High-performance...Marc J.M. Abadie et al.


Polyimides and High Performance Polymers, STEPI 5,Abadie M.J.M., Sillion B. (Eds.), Montpellier, 46-51(1999).

41. Nakamura K., Ando S., Takeichi T., Thermal analysis andsolid-state 13C NMR study of crosslink in polyimidescontaining acetylene groups in the main chain, Polymer,42, 4045-4054 (2001).

42. Rusanov A.L., Keshtov M.L., Khokhlov A.R., KeshtovaS.V., Peregudov A.S., New phenylated fluoro-containingpoly(phenylenes), Polymer Sci., Series A, 43, 343-349(2001).

43. Abadie M.J.M., Sillion B. (Eds), Telechelic phenyl-acetylene oligo-imides based on 2,4,6 trinitrotoluenederivatives, In: Polyimides and High Performance Poly-mers, STEPI 7 (2006).

44. Mallet M.A., Darmory F.P., Bis-maleimide oligomers-Access to high performance polymers, Amer. Chem. Soc.,Div., Coat. Plast. Chem. Prepr., 34, 173 (1974).

45. Rozenberg B.A., Boiko G.N., Morgan R.J., Shin E.E.,The cure mechanism of the 4,4í-(N,Ní-bismaleimide)diphenylmethane-2,2í-Diallylbisphenol a system, Polym.Sci., Series A, 43, 386-399 (2001).

46. Abadie M.J.M., Xiong Y., Boey F.Y.C., UV photo curingof N,Ní-bismaleimido-4,4?-diphenylmethane, Eur. Polym.J., 39, 1243-1247 (2003).

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