Telechelic polyindane compounds with reactive end-groups and method of fabricating thereof

Abstract

New functionalized polyindane is disclosed herein as well as methods of fabricating thereof.

Description

TELECHELIC POLYINDANE COMPOUNDS WITH REACTIVE END-GROUPSAND METHOD OF FABRICATING THEREOFCROSS REFERENCE TO RELATED APPLICATION

[0001] This is a patent application being filed under the Patent Cooperation Treaty and claiming priority to the U.S. provisional patent application serial number 63 / 622,232 filed January 18, 2024, entitled “Polyindane Compounds with Reactive End-Groups and Method of Fabricating Thereof,” the entire contents of which is incorporated herein by reference.FIELD OF THE INVENTION

[0002] The present invention relates to the field of functional polyindane resins that are useful in manufacturing of printed circuit boards and copper clad laminate which possess improved dielectric properties. In particular, the present invention relates to methods of fabricating of novel telechelicpolyindane compounds useful for such purposes.BACKGROUND

[0003] The development of high-frequency electronic components has necessitated the development of high-performance thermosetting resins for printed circuit boards (PCB) copper-clad laminates (CCL), particularly those allowing the reduction of transmission loss at high-frequencies. This may be achieved by use of materials possessing low permittivity and dielectric tangent. Such dielectric properties should also be stable when exposed to ambient humidity. Therefore, hydrophobic compositions are more desirable due to their dielectric stability. It is additionally desirable for such materials to exhibit high heat resistance, i.e., high thermal decomposition onset temperatures, and high glass transition temperatures, since electronic components and assemblies are exposed to high- temperatures during processing steps such as solder-reflow.

[0004] Therefore, there is a need for thermosetting resin compositions that have low dielectric constant (Dk), low dissipation factor (Df), low moisture uptake, and high glass transition (Tg) temperature. This need is being driven by the shift to ever higher signal frequencies used in microelectronic components and component assemblies.

[0005] Historically, epoxy resins that have been the standard thermoset materials used for the manufacture of copper-clad laminates (CCL) printed circuit boards (PCB). Epoxy thermosets, however, have relatively high Dk and Df properties, and their use for high frequency applications often result in unacceptable levels of signal loss. For example, the industry standard “FR-4” epoxy, which has been used for several decades epoxy in the production of PCBs, has a Dk of about 3.9 and a Df of about 0.10. These poor electrical properties, therefore, make epoxy thermoset resins unsuitable for use in the manufacture of the new generations of microelectronic component assemblies and printed circuit boards.

[0006] A recent improvement has been achieved that can make up for some of the deficient properties of the epoxy resins. Thermoset resins based on combinations of Sabie’s SA-9000 [a difunctional, methacrylate terminated, polyphenylene ether (PPE)], and triallyl isocyanurate (TAIC) show much better dielectric performance. This combination, when properly catalyzed and cured, has a Dk of about 2.9 and a Df around 0.004. While this approach provides a significant improvement over the standard epoxy thermosets, the PPE-TAIC materials will not be sufficient to meet the demand for the even better dielectric properties that will be required as the signal frequencies continue to rise above the low gigahertz (GHz) range.

[0007] One promising class of materials that may overcome the deficiencies of both epoxy and the PPE-TAIC resins are polyindane resins. The discovery of polyindanes dates-back-to 1958 (Bunner, et.al., J. Poly. Sci., Vol. XXVII, Issue No. 118, p. 629-631). Most of the early work in this area was based on the polymerization of 1,4-diisopropenyl benzene (l,4-DIPB).Thel,4-DIPB monomer is a solid at room temperature. This property has some value in terms of providing a path toward purifying the monomer via recrystallization. However, the cationic polymerization of this isomer is reported to onlyyield oligomeric products, with an upper limit Mnmolecular weight of about 5,000 Daltons. Crivello, (Chem. Mater. 1993, 5, 210-213), was the first to report that polyindanes with Mn molecular weight values of around 19,000 Daltons could be achieved through use of the 1,3 -diisopropenyl benzene (1,3-DIPB) isomer. The 1,3-DIPB monomer is a liquid at room temperature that boils at 231 °C. The 1,3-DIPB is commercially available at purities of about 99% and at prices that make it competitive with the current PCB and CCL resin materials.

[0008] Nuyken, et.al. [Makromol. Chem., 192, 1969 - 1979, (1991)], described telechelic polyindanes. Both aromatic carboxylic acid-terminated, and aromatic amine-terminated PI telechelics were generated via multiple synthetic steps. Nuyken identified the optimum temperature range for the polymerization of DIPBs to be between 10°C and 25°C. Polymerizations at temperatures above 25°C can result in the formation of unsaturated moieties distributed along the PI backbone. Such defects can not only decrease the thermal stability, but also have a negative impact on the dielectric properties of the resulting PI.

[0009] Shimono and Okamoto (W02020 / 217676 Al) described the synthesis of telechelic PI oligomers in which the terminal groups are 2,6-dimethylaniline moieties.

[0010] The end groups were then converted to maleimide functions to provide polymerizable compounds. The process used to make the telechelic amine precursor, however, requires a temperature of 220°C. Therefore, the functional oligomers of this invention will almost certainly contain unsaturated defects in the backbone.

[0011] Tian, et.al. (US 11,873,369 B2), covers the polymerization of mixed 1,3-DIPB and 1,4-DIPB monomers to yield branched, aryl-isopropenyl-terminated PI structures. Variable levels of gel are produced via the method described. The reaction temperature used to make these compounds was 45 °C, which is well above the recommended temperature window of 10°C to 25°C required to avoid unsaturated residues in the backbone.

[0012] McCarthy et.al. (US 6,153,721) covers the preparation of polyindanebisphenols (PIBPs). The 4-isopropenylphenol (IPP) end-capper was produced by the NaOH catalyzed cracking of bisphenol- A at 225 °C under reduced pressure. The crude IPP was co-distilled with the phenol side product. This co-distillate was then used without further purification in an acid catalyzed co-polymerization with 1,3-DIPB conducted at “room temperature.” The polymerization of DIPB is highly exothermic, yet there was no mention of the temperature control to maintain the reaction temperature below 25 °C.

[0013] Ingratta, et.al. (US2018 / 0171124 Al) describe the use of olefin “terminators” that can be used to control the molecular weight of polyindanes. No reference was made in this publication of the use hetero-reactive functional groups in the olefin “terminators.”

[0014] We have found that a number of hetero-bifunctional monomers can be used to successfully terminate polyindane oligomers and polymers. These end-cappers always contain an olefin, cycloalkene, or cycloalkadiene functional group that is capable of reacting with and terminating the growing polyindane chain and another polymerizabe functionality that is inert to the cationic step growth mechanism.

[0015] The reactive, telecheic polyindanes are simple to synthesize in one step at low temperature. The electron withdrawing carbonyl groups present in maleimide, acrylate and methacrylate, for example, make them non-reactive under cationic polymerization conditions These same functional groups, however, are very reactive in free-radical cures. The latent reactivity of the non-olefnic reactive residues allows the preparation of viable PI thermosets by a simple, low-cost synthesis.

[0016] Polyindanes have attractive properties for use as base resins in the manufacture of PCB and CCL boards. Since this class of materials is based upon a pure hydrocarbon backbone it has very low moisture uptake. It also has been reported to have a low Dk of 2.6, which is close to that of the very low Dk resin polystyrene (2.55). Unlike polystyrene which has a glass transition temperature of 100° C, polyindane has a Tgin the range of 210°C to 300°C. Another attractive property of polyindane is that it has good solubility in aromatic, aliphatic, and cycloaliphatic solvents.

[0017] Accordingly, the present patent application discloses such improved adhesive compositions based on derivatives of polyindane as well as methods of fabricating thereof.SUMMARY

[0018] It has been found that it is possible to make end-functional polyindane resins using a low temperature, high yield process. This approach is based on the use of reactive chain-terminator molecules that also bear an independently reactive functional group.

[0019] More specifically, there are provided novel polymers based on polyindane and further end-capped with certain functional groups described below in detail. Such poly indane polymers have the structures shown by Formula 1, Formula 2, Formula 3, Formula 4, or Formula 5 below:Formula 1wherein R is selected from succinic anhydride, nadic anhydride, 2-hydroxy- phenol, 3,5-dimethyl-4-hydroxyphenol, 3-methoxy-4-hydroxyphenol, 3,5-dimethoxy-4- phenol, acrylate, methacrylate, maleimide, citraconimide, 4-oxyphenyl maleimide, 2,6- dimethylphenyl-4-oxyphenyl maleimde, 2-phenyl-4-oxyphenyl maleimide, 2- methoxyphenyl-4-oxyphenyl maleimide, 4-oxyphenyl citraconimide, 4-oxyphenyl itaconimide, 4-oxyphenylamine, N-formamide, 1 -imidazole, benzoxazine, and N -phenylbenzoxazine.Formula 2wherein R is selected from 4-acetoxyphenyl, 4-aminophenyl, maleimide, N- imidazole, and formamide.wherein in each of Formulae 1-5 “n” is an integer having the value between 10 and 200.

[0020] In other embodiments, there are provided methods for synthesizing such polymers.

[0021] In yet other embodiments, compositions may include, in addition to poly indane, a co-monomer, such as a bismaleimide of dimer diamine, an imide-extended bisfurfuryl imide, or a polybutadiene.DETAILED DESCRIPTIONA. Terms and Definitions

[0022] The section headings used herein are for organizational purposes only and are not to be construed as limiting the subject matter described. It is to be understood that both the foregoing general description and the following detailed description are exemplary and explanatory only and are not restrictive of the invention claimed. As used herein, the use of the singular includes the plural unless specifically stated otherwise. As used herein, “or” means “and / or” unless stated otherwise. Furthermore, use of the terms “including” and “comprising” as well as other forms, such as “includes,” “included,” “comprises,” or “comprising” are not limiting.

[0023] Unless specific definitions are provided, the nomenclatures utilized in connection with, and the laboratory procedures and techniques of chemistry described herein are those known in the art. Standard chemical symbols are used interchangeably with the full names represented by such symbols. Thus, for example, the terms “hydrogen” and “H” are understood to have identical meaning. Standard techniques may be used for chemical syntheses, chemical analyses, and formulation.

[0024] As used herein, “polyindane” is a polymer or oligomer comprising indane (also known as benzocyclopentane); indane being a product comprised of ortho-fused benzene and cyclopentane rings and having the structure:where polymeric chains of polyindaneare formed by polymerization of 1,4-diisopropenyl benzene or 1,3-diisopropenyl benzene.

[0025] As used herein, the term “telechelic” refers to polymers or oligomers capable of entering into further polymerization or other reactions through its two reactive end- groups, which are either identical on each end of the macromolecular chain, or co- polymerizable with each other; accordingly, telechelic polymers or oligomers are thermosettable, or cross-linkable, or otherwise allowing the introduction of additional moieties, as desired.

[0026] As used herein, “polymer” refers to a product consisting of macromolecules, composed of at least 10 repeating subunits, “homopolymer” refers to a polymer molecule the bulk of which is composed entirely of identical monomer units (not including the endcapping moieties).

[0027] As used herein, “oligomer” refers to a product consisting of macromolecules, composed of between 2 and 9 repeating subunits.

[0028] As used herein, “cationic polymerization” refers to a type of chain growth polymerization initiated by a cationic initiator (typically, protic acids or Lewis acids in combination with a polar or non-polar solvent), to form a polymer.

[0029] As used herein, the term dielectric constant (Dk) is defined as an ability of a substance to hold electric flux and is expressed as the ratio of the electric permittivity of the substance to the electric permittivity of the free space.

[0030] As used herein, the term, the term low dissipation factor (Df) refers to the efficiency of a material as an electrically insulating material, and is defined as a ratio between the electric permittivity and the electric conductivity of an electrically insulating material.

[0031] As used herein, the term glass transition (Tg) is defined as the transition below which a polymer changes from a rigid, glassy state to a rubbery or viscous state.B. Embodiments

[0032] Embodiments disclosed herein provide novel polymers based on polyindane. Surprisingly, it was found that it is possible to leverage the properties of the polyindane backbone by making telechelic functional derivatives. It has been also found that it is possible to make end-functional polyindane resins using a low temperature, high yield process. This approach is based on the use of reactive chain-terminator molecules that also bear an independently reactive functional group. Since the cationic polymerization of DIPB monomers operates by a step-growth mechanism, both ends of the resulting polymers will bear the desired functional groups. Furthermore, the relative concentrationsof the DIBP and reactive chain-terminators will dictate the final molecular weight of the telechelic polyindane resins.

[0033] Telechelic polyindanes that are the subject of the present disclosure may be obtained as a result of polymerization of a diisopropenylbenzene, for example, by cationic polymerization of meta (i.e., l,3)-diisopropenylbenzene. As a result, polyindane polymers having the structures shown by Formula 1, Formula 2, Formula 3, Formula 4, or Formula 5 below as shown below can be obtained:Formula 1wherein R is selected from succinic anhydride, nadic anhydride, 2-hydroxy- phenol, 3,5-dimethyl-4-hydroxyphenol, 3-methoxy-4-hydroxyphenol, 3,5-dimethoxy-4- phenol, acrylate, methacrylate, maleimide, citraconimide, 4-oxyphenyl maleimide, 2,6- dimethylphenyl-4-oxyphenyl maleimde, 2-phenyl-4-oxyphenyl maleimide, 2- methoxyphenyl-4-oxyphenyl maleimide, 4-oxyphenyl citraconimide, 4-oxyphenyl itaconimide, 4-oxyphenylamine, N-formamide, 1 -imidazole, benzoxazine, and N -phenylbenzoxazine.Formula 2wherein R is selected from 4-acetoxyphenyl, 4-aminophenyl, maleimide, N- imidazole, and formamide.Formula 3Formula 4wherein in each of Formulae 1-5 “n” is an integer having the value between 10 and 200, such as between 20 and 150, for example, 100. The molecular weight of the so obtained polyindanes can be between about 2,000 Daltons and about 30,000 Daltons, for example, about 15,000 Daltons. The polymers have the Tgwithing about 210°C to about 250°C range and is soluble in a variety of aliphatic, cycloaliphatic, and aromatic solvents.

[0034] In some embodiments the polyindane polymer obtained as described above is a homopolymer, i.e., each of the “n” units within the brackets in the above formulae is the same. If desired, in some other embodiments such units may be different. It should be understood that the reaction method mentioned above (i.e., cationic polymerization of 1,3-diisopropenylbenzene) resulting in polymers of Formulae 1-5 above is provided herein strictly for the purposes of illustration and no limitation is intended or implied. In fact, polyindane may be obtained by another method of polymerization, and the diisopropenylbenzene used as a starting material is not necessarily the meta-isomer, i.e., the ara-isomer (i.e., 1 ,4-diisopropenylbenzene) may be used instead in some embodiments, if desired. Those having ordinary skill in the art will determine the type of the starting diisopropenylbenzene as well as the most suitable method of polymerization of the same.

[0035] The polyindane polymer obtained as described above is then further functionalized by introducing end capping groups, i.e., the end capping groupsterminating the polyindane chain on both ends. The end capping groups envisioned by the disclosure are reactive. A variety of functional end capping groups can be so used. Some non-limiting examples of such groups are designated below as “functional polyindaneend-cappers” and are as shown below:Functional Polyindane End-cappers

[0036] One example of a polyindane functionalized via end capping is an a,a- dimethylbenzylamine-terminated polyindane oligomer having the following structure:

[0037] Those having ordinary skill in the art may choose other end-capping groups for the same purpose. The end capping groups, such as those shown above, can be introduced in the polyindane polymer according to known synthetic methods of organic and polymer chemistries. For example, in one embodiment, the functionalized end capped polyindane polymers can be obtained via cationic polymerization of either 1,3- or 1.4- diisopropenylbenzene or mixtures thereof, together with a compound supplying functional end capping groups shown above. For instance, if a bismaleimido-terminated polyindane is to be obtained, then 1,3- or 1.4-diisopropenylbenzene (to provide the polyindane moeiety) can be cationically polymerized in the presence of N-allylmaleimide (to provide the bismaleimide functional moieties as end capping groups). Or, if an a,a- dimethylbenzylamine-terminated poly indane is to be obtained, then 1,3- or 1.4- diisopropenylbenzene can be cationically polymerized in the presence 3-isopropenyl-a,a- dimethylbenzylamine (to provide the dimethylbenzylamine functional moieties as end capping groups).

[0038] Based on the above, and depending on which telechelic polyindane compound is desired, those having ordinary skill in the art will choose the most appropriate isomer, or combination of isomers, of diisopropenylbenzene and the most appropriate compound providing functional end-capping groups. The choice of the most appropriate synthetic method is also within the purview of those having ordinary skill in the art. Some of such methods are described in detail in the “Examples” portion of the present application, below.

[0039] Other embodiments of the invention provide for additional compounds to be used in combination with polyindanes described above. Indeed, while the polyindane compounds have high glass transition temperatures, this property contributes to significant brittleness in the cured resins. Therefore, it is desirable to improve toughnessof the polyindane-based compositions for real world applications. To do so, the compositions may be formulatedto include co-monomers having lower Tg.The compositions comprising both polyindanes and such co-monomers may have the contents of polyindanes at between about 40 mass % and about 60 mass %, such as about 50 mass %. One such monomer thathas been successfully used to toughen the polyindanesis the bismaleimide of the hydrogenated of the dimer diamine (Formula A) having the following formula:Formula A

[0040] The backbone of the dimer diamine may be fully hydrogenated (which is designated as X-BMI). Another possible toughener is the non-hydrogenated backbone version of the bismaleimide designated as UX-BMI (Formula B):Formula B

[0041] Another useful toughener is the imide-extended cousin of FormulaA. This compound is available from Designer Molecules, Inc. under the designation of BMI- 1700. A representative structure of this compound is shown below as Formula C:Formula C

[0042] Examples of maleimide-terminated polyindanes co-cured with dimerdiamine bismaleimides are shown in Table 1. References to examples (provided below) are made in Table 1 indicating which polyindane was used in the formulated mixtures. For example, in the first entry in the column “formulated mixture” shown in Table 1 , The “50:50 X-BML5 to 1 PI-BMI from Example 1” refers a composition comprised of 50 mass % of X-BMI (Formula A above) and 50 mass % of 5 to 1 PI-BMI (described in Example 1 below).Table 1

[0043] As can be seen from Table 1, the lowest Df results, in this series of tests, were obtained when the saturated (X-BMI) compound was used as the toughener. An intermediate polyindane chain length had the best Df seen in the mixtures tested in Table 1. When the dimer diamine bismal eimide is used as a toughener, at least 50 weight percent of this monomer must be formulated with the poly indane BMI to provide sufficient toughness in the cured thermoset.

[0044] Another series of test films were made to explore the pre- and post-humidity dissipation factor properties of the telechelic polyindanes of this invention. All of these compositions were formulated with co-monomers in order to make tough films. The test results for these compositions are shown in Table 2.Table 2aSee Example 2,bBased on method from Example 5, TorinnlaC Imide-extended BMI,dA branched chain18-carbon aliphatic mo no -methacrylate,eA branched chain 13-carbon aliphatic monomaleimide.It should be especially noted that all of the films shown in Table 2 were quite stable in terms of their Df when exposed to 50% humidity at 50°C for 24 hours.

[0045] It has been also found that efficient toughening agents can be made via imide- extended bisfurfuryl imides. The furfurylimide end groups on these oligomers readily react with maleimide monomers via a Diels Alder cycloaddition reaction. One feature of this reaction is that the Diels Alder addition is thermally reversible. The temperature at which this retro-Diels Alder reaction occurs is between 100°C and 120°C. The retro-Diels Alder, thus occurs just after the solvent removal is complete in the CCL prepreg formation process. Some examples of bisfurfurylimides contemplated as toughening agents are shown below (Formula D and Formula E):Formula E

[0046] Additional toughening oligomers are available from Nippon Soda Co. LTD. These materials are partially hydrogenated, high- vinyl content polybutadiene molecules represented by FormulaF. The compounds available are their BL3015 and BL3040 (which represent 85% and 60% hydrogenation, respectively).Nippon Soda's Partially hydrogenated high vinyl content polybutadieneFormula F

[0047] Yet another category of toughening compounds contemplated for this invention include thermoplastic elastomers (TPEs). Triblock polymers comprise one important class of these compounds. These TPEs incorporate terminal hard segments and elastomeric mid-blocks. Typically, the hard blocks consist of polystyrene segments, while the soft segments comprise polybutadiene (SBS), polyisoprene (SIS) or hydrogenated polybutadiene (SEBS). The SEBS has better electrical properties (e.g. lower Dk and Df) and greater stability toward oxidation.

[0048] Unfortunately, these TPE compounds have proven to be incompatible with the telechelic polyindanes of this invention. The incompatibility is usually not apparent when the TPIs and TPEs are dissolved in a common solvent, but it becomes obvious when the solvent is removed. This incompatibility appears as significant phase separation in the dried sample. In order to make the TPE compounds viable as tougheners for the TPIs of this invention it is necessary to find molecules that can act as compatibilizers for these immiscible hydrocarbon resins. One example of a class of compatibilizers that we have developed is show below:Formula G

[0049] These compatibilizer compounds can be referred to as PI-PPEs. The polyphenylene segments are completely miscible with styrene hard segments of the TPE and help to form a dispersion of the TPE in the polyindane phase. The polyindane segments of the PI-PPE are both miscible and co-curable with the telechelic polyindanes of this invention. The distinct properties of the two segments in these compatibilizers is what allows them to bridge the “compatibility gap” between the polyindanes and the TPE hydrocarbon phases. The (minor) elastomeric phase of the TPEs thus becomes uniformly dispersed as micellular structures within the brittle main phase of the telechelic polyindane.

[0050] The methacrylate functional group shown in FormulaG may, of course, be replaced by any of the other free-radically-polymerizable end-capping groups described in this invention.

[0051] The weight fraction of the TPE dispersed within the PI matrix, on a solids basis, is about 5 to 25 weigh percent. The weight fraction of the compatibilizer within the TPE is preferably about 5 to 35%.EXAMPLES

[0052] To further illustrate and elucidate some featuresand advantages of the embodiments disclosed herein, the following non-limiting examples of formulations that were actually prepared are provided.Example 1: “5 to 1” Bismaleimido-terminated polyindane oligomer

[0053] The term: “5 to 1” in the title of the example refers to the molar ratio between 1,3- diisopropenyl benzene and N-allylmaleimide used in this synthesis. Accordingly, 50 mb of toluene was used to dissolve 47.6 g (300 mmole) 1,3 -diisopropenyl benzene and 8.1 g(60 mmole) N-allylmaleimide. This solution was placed in an addition funnel. The funnel was attached to a jacketed resin reactor. Toluene (180 mL) and 5.0 mL 93% H2SO4 were placed in the reactor along with a magnetic stir bar. This mixture was stirred magnetically and the stirred suspension was cooled to 10° C via a recirculating chiller.

[0054] The solution in the addition funnel was then added dropwise to the stirred suspension in the reactor. This reaction was exothermic, so the addition rate was controlled at about one drop per every one to two seconds, in order to maintain the pot temperature at 10 to 11° C throughout the course of the addition. The addition was complete after 105 minutes. Stirring was continued for 63 hours. The chiller was turned off after the monomer addition was complete, but recirculation through the jacket was continued as the contents of the reactor were allowed to increase to room temperature. The acid catalyst was neutralized via the addition of 100 mL of saturated NaHCCh solution. The progress of the neutralization was monitored via CO2 release using a bubbler. The stirring was stopped once no CO2 was detected. The pH of the aqueous phase was confirmed to be greater than 7. The toluene and water were removed on a Rotovap and the solids were dissolved in 100 mL THF. This solution was filtered to remove any inorganics. The THF solution was then precipitated into a vigorously stirred solution of 700 mL MeOH plus 70 mL H2O.

[0055] The solids were collected on a fritted glass funnel and rinsed with additional MeOH. The product was a white, free-flowing powder after an oven dry, followed by an overnight vacuum oven dry at 100°C. The product weighed 54.9g (98.6% of theory). An FTIR was run on this product. There were absorptions at 2954, 1710, 1138, 826, 728, 698, and 623 wavenumbers. The absorptions at 1710, 826, and 698 wavenumbers confirmed that terminal allyl maleimide had incorporated into the polymer.

[0056] A portion of the product was mixed with 2% by weight dicumyl peroxide (DCP) and the mixed solids were dissolved in THF. The THF was then removed and the dried mixture was tested via DSC. The test mix had a primary cure peak at 130.2°C (with a cure energy of 7.5 J / g). There was a secondary cure peak at 273.1 °C (cure energy = 17.4J / g). A second DSC run was done on the cured sample, and the Tgof the cured sample was found to be 236.2°C.Example 2: “30 to 1” Bismaleimido-terminated polyindane oligomer

[0057] Toluene (50 mL) was used to dissolve 47.6 g (300 mmole) 1,3 -diisopropenyl benzene (1,3-DIPB) and 1.35 g (10 mmole) N-allylmaleimide (NAM). This solution was placed in an addition funnel. The funnel was attached to a jacketed resin reactor. Toluene (180 mL) and 5.0 mL 93% H2SO4 were placed in the reactor along with a magnetic stir bar. This mixture was stirred magnetically and the stirred suspension was cooled to 22°C via a recirculating chiller. The solution of 1,3-DIPB, NAM, and 50 mL toluene was dripped into the stirred pot mixture at a rate of one to two drops per second. The temperature was maintained at 22 ± 1 °C over the course of the addition. The mix was allowed to continue to stir at room temperature for another 63.5 hours.

[0058] The mixture was then transferred to a separatory funnel and then extracted with 100 mL deionized water, followed by 10 mL saturated aqueous NaHCCh and then 5x25 mL brine. The toluene and residual water were removed using a rotary evaporator and the solids were then dissolved in 100 mL THE. This solution was then precipitated into a magnetically stirred solution of 70 mL H2O in 700 mL MeOH. The solids were collected on a medium porosity glass fritted funnel and then were rinsed with additional MeOH. The dried solids were a white powder that weighed 45.6g (93.2% of theory).

[0059] An FTIR was run on this product. There were absorptions at 2954, 1711, 1455, 1362, 1069, 862, 826, and 702 wavenumbers. A portion of the solid was mixed with two percent DCP and cured. The Tgof the cured sample was found to be 237.2°C via DSC.Example 3: “250 to 1” Bismaleimido-terminated polyindane oligomer

[0060] The term: “250 to 1” in the title of the example refers to the molar ratio between 1,3-DIPB and NAM used in this synthesis. Accordingly, 50 mL of toluene was used to dissolve 39.6 g (250mmole) 1,3-DIPB and 135mg (l.Ommole) NAM. This solution was placed in an addition funnel. The funnel was attached to a jacketed resin reactor. Toluene (180 mL) and 5.0 mL 93% H2SO4 were placed in the reactor along with a magnetic stir bar. This mixture was stirred magnetically and the stirred suspension was cooled to 22°C via a recirculating chiller.

[0061] The solution in the addition funnel was then added dropwise to the stirred suspension in the reactor. This reaction was exothermic, so the addition rate was controlled at about one drop per every one to two seconds, to maintain the pot temperature at 22 ± 1°C throughout the course of the addition. The addition was complete after 93 minutes. Stirring was continued for 62 hours. The chiller was turned off after the monomer addition was complete, but the recirculation through the jacket continued as the contents of the reactor were allowed to increase to room temperature. The contents of the reactor were then transferred to a separatory funnel. The funnel was placed into a 55°C oven to assist the separation. The clear, red H2SO4, bottom phase was then removed and the residual acid catalyst was rinsed out with 3 x 25 mL brine washes followed by neutralization with 15 mL of saturated NaHCO3 solution. The toluene phase was then washed with 2 x 25 mL rinses of deionized H2O. The pH of the final rinse aqueous wash was confirmed to be greater than 7. The toluene solution was then precipitated into a vigorously stirred solution of 630 mL MeOH that also contained 70 mL H2O.

[0062] The solids were collected on a fritted glass funnel and rinsed with additional MeOH. The product was a white, free-flowing powder after an oven dry, followed by an overnight vacuum oven dry at 100°C. The product weighed 39.74 g (100.0% of theory).An FTIR was run on this product. There were absorptions at 2954, 2862, 1058, 882, and 702, wavenumbers. The absorptions associated with the terminal allyl maleimide were too weak to be clearly visible by FTIR.Example 4: “15 to 1” Dimethylbenzylamine-terminated polyindane oligomer

[0063] Toluene (50 mL) plus 20 gram of dichloromethane was used to dissolve 47.6 g (300 mmole) 1,3-DIPB and 3.5g (20 mmole) 3-isopropenyl-a,a-dimethylbenzylamine. This solution was placed in an addition funnel. The funnel was attached to a jacketed resin reactor. Toluene (180 mL) and 5.0 mL 93% H2SO4 were placed in the reactor along with a magnetic stir bar. This mixture was stirred magnetically and the stirred suspension was cooled to 20° C via a recirculating chiller.

[0064] The solution in the addition funnel was then added dropwise to the stirred suspension in the reactor. This reaction was exothermic, so the addition rate was controlled at about one drop per every one to two seconds, to maintain the pot temperature at 19 to 21° C throughout the course of the addition. The addition was complete after 111 minutes. Stirring was continued for 64 hours. The chiller was turned off after the monomer addition was complete, but the recirculation through the jacket was continued as the contents of the reactor were allowed to increase to room temperature. The acid catalyst was neutralized via a slurry of 50 mL H2O and 15 grams NaHCO The progress of the neutralization was monitored via CO2 release using a bubbler. The stirring was stopped once no CO2 was detected. The pH of the aqueous phase was confirmed to be greater than 7. The toluene solution was extracted with 100 mL deionized H2O and the aqueous phase was discarded. The toluene and residual water were then removed on a Rotovap and the solids were dissolved in 150 mL THF. This solution was filtered to remove any remaining traces inorganic solids. The THF solution was then precipitated into a vigorously stirred solution of IL MeOH.

[0065] The solids were collected on a fritted glass funnel and rinsed with additional MeOH. The product was a white, free-flowing powder after an oven dry, followed by an overnight vacuum oven dry at 100°C. The product weighed 50.2g (98.2% of theory). An FTIR was run on this product. There were absorptions at 2956, 2862, 1458, 1068, 905, 792, and 704 wavenumbers. The absorptions at 1458, 1068, and 704 wavenumbers were consistent with the presence of aliphatic, primary amine that had incorporated into the end groups of the polymer.Example 5: “5 to 1” Dimethacrylate-terminatedpolyindane oligomer

[0066] Toluene (50 mb) was used to dissolve 47.6 g (300 mmole) 1,3-DIPB and 7.6 g (60 mmole) N-allylmethacrylate. This solution was placed in an addition funnel. The funnel was attached to a jacketed resin reactor. Toluene (100 mL) and 5.0 mL MeSOH were placed in the reactor along with a magnetic stir bar. This mixture was stirred magnetically and the contents of the addition funnel were added drop-wise over the course of 59 minutes. The pot temperature was maintained at 13 ± 1.5 °C over the course of the reaction via a recirculating chiller. The mix was allowed to continue stirring at room temperature for another 44 hours.

[0067] Triethylamine (8.5 g) was then added to the solution in the pot and the mix was stirred for another 20 minutes before the solution / suspension was transferred to a 500 mL separatory funnel. There were two phases in the funnel that were allowed to settle overnight. The lower (NEtTMSA salt) phase was then removed and was found to weigh 16.0g (equal to theory). The toluene phase was extracted with 3x25 mL brine and then with25 mL D,I. H2O.

[0068] The residual H2O was azeotropicallyand the toluene solution concentrated to about 160g using a rotary evaporator. This solution was then precipitated into 800 mLmagnetically stirred isopropyl alcohol. The precipitated solids were then collected on a medium-frit glass funnel. The solids were then dried to yield 42.04g (76.2% of theory) of a white powder. An FTIR was run on this product. There were absorptions at 2956, 1722, 1457, 1363, 884, 791, and 704 wavenumbers.

[0069] A portion of the product was mixed with 2% by weight DCP and the mixed solids were dissolved in THF. The THF was then removed and the dried mixture was tested via DSC. The test mix had a primary cure peak at 194.5°C (with a cure energy of 34.1 J / g). There was a secondary cure peak at 260.2°C (cure energy = 3.8 J / g). A second DSC run was done on the cured sample, and the Tgwas found to be 221.3°C.Example 6: “10 to 1” Tetraallyl-ester- terminated polyindane oligomer

[0070] A combination of 47.6 g (300 mmole) 1,3-diisopropenyl benzene and 4.2 g (30 mmole) Allylsuccinic anhydride were dissolved in 25mL toluene. This solution was placed in an addition funnel. The funnel was attached to a jacketed resin reactor. Toluene (75 mL) and 5.0 mL MeSChH were placed in the reactor along with a magnetic stir bar. This mixture was stirred magnetically and the contents of the addition funnel were added drop-wise over the course of 43 minutes. The pot temperature was maintained at 19+ 1°C over the course of the reaction via a recirculating chiller. The mix was allowed to continue stirring at room temperature for another 64 hours.

[0071] The contents of the reactor were then transferred to a 500 mL, 1-neck flask. A stir bar along with 4.6g (80 mmole) allyl alcohol was added. A Dean-Stark trap plus condenser was attached to the flask. The reaction mix was refluxed for two hours and 1.4 mL “H2O” (1.1 mL = theory) was collected in the trap (note: some allyl alcohol codistilled). The mixture was cooled and 8.5g NEb was added and the new mixture was stirred at RT for another 20 minutes. The mixture was then transferred to a separatory funnel and the lower (N Eb* MS A) salt phase was removed as a red liquid. The toluenephase was rinsed with 3x25 mL brine, dried with 12g MgSO-i, and the solution was then passed over 20g silica gel. The solution was then concentrated to about 150g via a rotary evaporator, and then precipitated into 700 mL isopropyl alcohol. The precipitated solids were then collected on a medium-frit glass funnel. The solids were dried to yield 43.0g (79.6% of theory) of a cream-colored powder. An FTIR was run on this product. There were absorptions at 2954, 1732, 1455, 1363, 883, 825, 792, 753, and 706 wave- numbers.

[0072] The product was mixed with 2% by weight DCP and the mixed solids were dissolved in THF. The THF was then removed and the dried mixture was tested via DSC. The test mix had a cure peak at 195°C (with a cure energy of 61.2 J / g). A second DSC run was done on the cured sample, and the Tgwas found to be 206.7°C.Example 7: “4 to 1” Bis-C36-maleimido-terminated polyindane oligomer

[0073] A combination of 31.6 g (200 mmole) 1,3-diisopropenyl benzene and 7.0 g (50 mmole) Allylsuccinic anhydride were dissolved in 50 mL toluene. This solution was placed in an addition funnel. The funnel was attached to a jacketed resin reactor. Toluene (200 mL) and 5.0 mL H2SO4 were placed in the reactor along with a magnetic stir bar. This mixture was stirred magnetically and the contents of the addition funnel were added drop-wise over the course of 96 minutes. The pot temperature was maintained at 20 ±1°C over the course of the reaction via a recirculating chiller. The mix was allowed to continue stirring at room temperature for another 2.5 hours. Then 26.8g (50 mmole) Priamine 1075 was added to the reactor. An 11°C exotherm was generated by this addition. The polyamic acid that was generated was not sufficiently soluble in toluene by itself, so 80 mL of NMP was added as a co-solvent. The reactor contents were then transferred to a 1 liter, 1-neck boiling flask along with another 5.0 mL H2SO4 catalyst, and a stir bar. A trap and condenser was attached and the mix was refluxed for 8.0 hours.A total of 1.1 mL H2O was collected (0.9 mL had been expected). The reaction mix was cooled to about 40°C and 6.9g (70 mmole) of maleic anhydride was added. Reflux was then resumed and continued for 15 hours. Another 1.5 mL of H2O was collected (which may have included some NMP). The reaction mix was then cooled and transferred to a separatory funnel. The solution was then extracted with 8x25 mL brine to remove the NMP from the solution. The toluene was then removed and the residue was dissolved in 100 mL of THF. This solution was then precipitated into 800 mL MeOH. The solids were collected on a medium glass frit funnel, rinsed with additional MeOH and then dried to give 37.5g (55.3% of theory) of a beige powder. An FTIR was run on this product. There were absorptions at 2954, 2923, 2855, 1708, 1458, 1407, 1362, 1069, 905, 827, 791, and 700 wave-numbers.

[0075] The product was mixed with 2% by weight DCP and the mixed solids were dissolved in THF. The THF was then removed and the dried mixture was tested via DSC. The test mix had a cure peak at 171.5°C (with a cure energy of 72.5 J / g). A second DSC run was done on the cured sample, and the Tgwas found to be 149.2°C.

[0075] A film of this oligomer, catalyzed with 2% DCP, was cast from a 50% solution in toluene. The film was dried overnight at 65 °C in an air-circulating oven, and then cured one hour at 200°C. The post-cured film had a Dk of 2.541 and a Df of 0.00204. This film was placed in a humidity chamber that was controlled at 50°C and 50% humidity for 24 hours. The post humidity Dk was 2.557 and the Df was 0.00275.Example 8: “30 to 1” Bis-C36-maleimido-terminated polyindane oligomer

[0076] A combination of 47.6 g, 300 mmole) 1,3-DIPB and 1.4 g (10 mmole)Allylsuccinic anhydride were dissolved in 50 mL toluene. This solution was placed in an addition funnel. The funnel was attached to a jacketed resin reactor. Toluene (200 mL)and 5.0 mL MSA were placed in the reactor along with a magnetic stir bar. This mixture was stirred magnetically and the contents of the addition funnel were added drop-wise over the course of 128 minutes. The pot temperature was maintained at 19.5 ± 2.5°C over the course of the reaction via a recirculating chiller. The mix was allowed to continue stirring at room temperature overnight for another 16 hours. Then, 10 mmole, 5.4g, Priamine 1075 was added to the reactor along with another 18g of MSA and 15g of NEts. The mix was then transferred to a 500 mL, 1-neck flask. A trap and condenser was attached and the mix was stirred at reflux for two hours. A total of 1.3 mL H2O was collected. The reaction mix was cooled to about 40°C and 1.4g (14mmole) of maleic anhydride was added. Reflux was then resumed and continued for 15.8 hours. Another 0.2 mL of H2O was collected (0.18 = theory). The reaction mix was then cooled and transferred to a separatory funnel. The upper (toluene) phase and the lower (NEtTMSA salt) phase were both a light-yellow color. The lower phase was extracted with 4x25 mL toluene. The combined toluene solution plus extracts was allowed to sit at RT over the weekend. This solution was then passed over 25g silica gel. The solution was then concentrated to about 130g and then precipitated into 600 mL IPA. The solids were then collected on a medium fritted-glass funnel, rinsed with IPA, and then dried to give 49.5g (90.0% of theory) of a yellow- white powder. An FTIR was run on this product. There were absorptions at 2956, 2924, 2864, 1711, 1596, 1455, 1361, 1086, 893, 826, 790, and 703 wave- numbers.

[0077] The product was mixed with 2% by weight DCP and the mixed solids were dissolved in THF. The THF was then removed and the dried mixture was tested via DSC. The test mix had a cure peak at 177.3°C (with a cure energy of 61.8 J / g). A second DSC run was done on the cured sample, and the Tgwas found to be 138.5°C.Example 9: “5 to 1” BisVinylnorbornane-terminated polyindane oligomer

[0078] A solution of 47.6g (300 mmole) 1,3-DIPB, 7.2g (60 mmole) 5-vinyl-2- norbornene (VNB), and 50 mL was placed into an addition funnel. The funnel was attached to a jacketed resin reactor that had been charged with 5.0 mL MSA, 100 mL toluene, and a magnetic stir bar. This solution was dripped into the magnetically stirred suspension of MSA in toluene at about two drops per second. The temperature of the reactor contents was maintained at 17+1 °C over the course of the addition. The addition was complete after 34 minutes. The solution in the pot was had a dark-red color. Stirring was continued at RT for another 21.2 hours. Then, 9.0g NEE was added and the solution color changed from a dark-red to a light orange within 15 seconds of stirring. The mix was transferred to a 500 mL separatory funnel. The funnel was then placed in an aircirculating oven that was set at 85°C. The lower (NEtTMSA salt) phase was removed and the toluene phase was extracted with 2x25 mL brine. The toluene phase was dried with 12g of MgSO4and then stirred with 15g basic, activated AI2O3. The toluene solution was then passed over 25g SiCL gel. The solution was concentrated to about 250g using a rotary evaporator, and then precipitated into 1200 mL IP A. The solids were recovered and dried to give 46.3g (84.5% of theory) of a white powder. An FTIR was run on this product. There were absorptions at 2956, 2926, 2865, 1599, 1458, 1362, 1087, 893, 826, 791, and 704 wave- numbers.

[0079] The oligomer was mixed at a 4: 1 ratio with X-BMI (Formula A) and 2% DCP and this mix was dissolved in toluene to give a 50% by weight solution. About 25 mg of this solution was placed in a DSC pan and the toluene was removed overnight in an air circulating oven set at 70°C. The test mix had a cure peak at 162.7°C (with a cure energy of 74.2 J / g). A second DSC run was done on the cured sample, and the Tgwas found to be 95.9°C.

[0080] The toluene solution from above was drawn down onto a glass plate fitted with a release liner. The film was dried overnight at 65°C, and then cured for an hour at 200°C. The cured film was a flexible, clear-amber solid. The post cure Dk was 2.193, and the Df was 0.00185. The film was measured again after 24 hours exposure to 50°C at 50% relative humidity. The post humidity dielectric measurements were Dk = 2.311, and Df = 0.00201.Example 10: Synthesis of Bisfurfurylimide reactive toughener

[0081] A bisfurfurylimide reactive toughener was prepared according to FormulaD (where n = 0). Accordingly, 52.0 g (100 mmole) bisphenol-A dianhydride (BP AD A), 150 mb toluene, 50 mb NMP, 26.8 g (50 mmole) Priamine 1075, and a stir bar were charged into a 1-neck, 500 mb flask. The mixture was warmed and the solids were brought into solution. A Dean-Stark trap and condenser were attached. The mixture was stirred at reflux for 6.0 hours. A total of 2.0 mb H2O was collected in the trap (expected 1.8 mb). The solution was then cooled to RT and 14.6 g (150 mmole) furfurylamine was added to the stirred solution. The trap and condenser were reattached and the solution was refluxed overnight (14.25 hours) to collect another 2.1 mb H2O (theory was again 1.8 mb). The toluene was stripped off and the product dissolved in NMP was precipitated into 700 mb of methanol. The product had formed a “bubblegum-like” semi-solid at the bottom of the flask when precipitated. The methanol plus NMP was decanted off and then stirred and rinsed with additional methanol. The product was dried in a recirculating air oven at 100°C until it reached constant weight. A total of 66.4 g (78.2% of theory) of a red, glassy solid was recovered. An FTIR analysis of this compound showed prominent absorptions at 2923, 2853, 1710, 1600, 1474, 1387, 1230, 1172, 1912, 838, and 746 wavenumbers.

[0082] A Diels-Alder extended test composition was made from this compound. The Example 10 molecule (5.0 g, 5.9 meq.) was dissolved in 10 mb toluene along with 5.0 g (14.6 meq.) of UX-BMI inside of a 100 mb flask. Then, 200 mg DCP catalyst was added and the solution was rotated in a 60°C water bath for 90 minutes. A portion of the solution was transferred to a Teflon mold and dried overnight at 100°C. The dried residue was a tacky, red solid. An FTIR scan showed a strong carbonyl peak at 1703 cm'1. Absorbances characteristic of the maleimide group were also present, but the intensity of the peaks was significantly diminished compared to the original UX-BMI. A DSC scanwas done on the adduct and it was found to have a cure energy of 150.4 J / g, an onset of 144.7°C, and a cure peak at 161.0°C. One other feature of this DSC scan was a “Tg-like” transition prior to the cure centered at 110.13°C. this transition was believed to correspond to a retro-Diels-Alder reaction in the adduct.

[0083] Films were cast, dried, and cured from the catalyzed solution described above and the dielectric properties were measured. The cured film was a flexible, clear, red-amber solid. The post cure Dk was 2.527, and the Df was 0.00190. The film was measured again after 24 hours exposure to 50°C at 50% relative humidity. The post humidity dielectric measurements were Dk = 2.553, and Df = 0.00213.Example 11 : Synthesis of the compatibilizer precursor

[0084] Sabie’s SA120 (117.7 g, 50 mmole) was dissolved in 200 mb toluene inside a 1 liter, 1-neck flask to form a viscous, red solution. Allyl bromide (9.1 g, 75 mmole) was then added to this solution, along with 20.8 g (150 mmole) potassium carbonate, and 1.5 g of the phase transfer catalyst tetrabutylammonium bromide (TBAB). A condenser was attached to the flask and the mixture was magnetically stirred at reflux for 39.5 hours. Another 300 mb toluene was then added along with 50 g of basic, activated alumina. This mix was stirred for 2.5 hours and the mix was passed over 50 g silica gel contained in a medium glass-fritted funnel. The silica gel was rinsed with additional toluene. The light-red toluene solution was then concentrated to about 300 g on a rotary evaporator. This solution was then precipitated into 2 L of magnetically stirred isopropyl alcohol. The solids were then collected on a medium glass-fritted funnel, rinsed with IP A, and then dried in an air circulating oven, followed by a vacuum oven. The yield of an orangewhite solid was 103.6 g (86.5% of theory). An FTIR analysis of this compound showed prominent absorptions at 2919, 1602, 1468, 1305, 1185, 1019, and 854 wavenumbers.Example 12: Synthesis of the methacrylate function diblock compatibilizer

[0085] A solution was prepared that contained 47.6 g (300 mmole) 1,3-DIPB, 47.9 g (20 mmole) of the compatibilizer precursor shown above, 10.1 g (80 mmole) allyl methacrylate, and 100 mL toluene. This moderately viscous, red solution was placed into an addition funnel. The funnel was attached to a jacketed resin reactor that had been charged with 100 mL toluene and 5 mL MSA. The mix in the reactor was stirred magnetically and cooled to 16°C. The solution in the addition funnel was then dripped in over the course of 40 minutes. The pot temperature was maintained at 17±1°C during the addition. The solution in the reactor was a dark-red color. The solution was then allowed to stir at room temperature for another 42.25 hours. Triethylamine (10.0 g) was then added to the reactor and the mix was allowed to stir for another 40 minutes before the entire solution in the reactor was transferred to a 500 mL separatory funnel. The funnel was placed in an 85°C oven in order to assist in the resolution of the (NEts’MSA) salt phase from the toluene phase. The salt phase was drawn off and discarded. The toluene phase was rinsed with two 25 mL portions of brine. The toluene solution was dried with 12 g of MgSChand then passed over 35 g of silica gel. The toluene solution was then concentrated and then precipitated into 2 L of isopropyl alcohol. The recovered and dried orange- white solids weighed 88.2 g (83.5% of theory). An ETIR analysis of this compound showed prominent absorptions at 2955, 2920, 1600, 1468, 1185, 1019, 959and 854 wavenumbers.

[0086] While the embodiments of this invention have been described with respect to these specific examples for purposes of clarity and illustration, it should be clear that those having ordinary skill in the art, in-light-of the present disclosure, may be able to devise modifications and variations without departing from the spirit or scope of the appended claims.

Claims

CLAIMSWHAT IS CLAIMED IS:

1. A telechelic polyindane compound comprising polyindane moiety and two functional moieties end capping the compound, wherein the two end capping moieties are the same or are co-polymerizable functional groups.

2. The compound of claim 1 , wherein the polyindane moiety is a homopolymer.

3. The compound of claim 1, selected from the group consisting of polyindane polymers having Formula 1, Formula 2, Formula 3, Formula 4, or Formula 5:Formula 1wherein in Formula 1 R is independently selected from the group consisting of succinic anhydride, nadic anhydride, 2-hydroxyphenol, 3,5- dimethyl-4-hydroxyphenol, 3-methoxy-4-hydroxyphenol, 3,5-dimethoxy-4- phenol, acrylate, methacrylate, maleimide, citraconimide, 4-oxyphenyl maleimide, 2,6-dimethylphenyl-4-oxyphenyl maleimde, 2-phenyl-4- oxyphenyl maleimide, 2-methoxyphenyl-4-oxyphenyl maleimide, 4- oxyphenyl citraconimide, 4-oxyphenyl itaconimide, 4-oxyphenylamine, N- formamide, 1 -imidazole, benzoxazine, and N-phenylbenzoxazine;Formula 2wherein in Formula 2 R independently selected from the group consisting of 4-acetoxyphenyl, 4-aminophenyl, maleimide, N-imidazole, and formamide;Formula 3and any combinations thereof, wherein in each of Formulas 1-5 n is an integer having the value between 2 and 250.

4. The compound of claim 1 , wherein the two functional end-capping moieties are selected from the group consisting of:Functional Polyindane End-cappers5. The compound of claim 1, wherein the functional moiety is selected from the group consisting of the bismaleimide moiety and the a,a- dimethylbenzylamine moiety.

6. The compound of claim 1, wherein the compound has the structure selected from the group consisting of:and7. A composition, comprising the telechelic polyindane compound of claim 1 and a co-monomer selected from the group consisting of the bismaleimide of dimer diamine and a co-monomer of a different class.

8. The composition of claim 7, wherein bismaleimide of dimer diamine is selected from the group consisting of fully hydrogenated bismaleimide of dimer diamine having the Formula A:Formula A and a partially unsaturated bismaleimide of dimer diamine having the Formula B:Formula B and an imide-extended cousin of Formula A having the Formula C:Formula C9. The composition of claim 7, wherein the co-monomer of a different class is selected from the group consisting of imide-extended bisfurfuryl imide compounds having the Formulas D or E, and a partially hydrogenated polybutadiene having the Formula F:Nippon Soda's Partially hydrogenated high vinyl content polybutadieneFormula F10. The composition of claim 7, wherein the contents of the telechelic polyindane compound is between about 40 mass % and about 60 mass %.

11. The composition of claim 7, wherein the contents of the telechelic polyindane compound is between about 40 mass% and about 60 mass %.

12. A method for synthesizing a telechelic polyindane compound end-capped with functional moieties, the method comprising reacting a diisopropenylbenzene with a compound comprising the functional moieties, under conditions suitable for carrying the process, to obtain the end capped telechelicpolyindane compound thereby.

13. The method of claim 12, wherein the end-capped telechelicpolyindane compound is a homopolymer.

14. The method of claim 12, wherein the diisopropenylbenzene is 1,3- diisopropenyl benzene.

15. The method of claim 12, wherein the diisopropenylbenzene is 1,4- diisopropenyl benzene.

16. The method of claim 12, wherein the compound is obtained by cationic polymerization.

17. The method of claim 12, wherein the wherein the end-capping functional moieties are independently selected from the group consisting of:Functional Polyindane End-cappers18. The method of claim 12, wherein the functional moiety is selected from the group consisting of the bismaleimide moiety and the a,a- dimethylbenzylamine moiety.

19. The method of claim 12, wherein the telechelicpolyindane compound has the structure selected from the group consisting of:

Images