Abstract: The invention relates to a hardening resin composition including a monomer represented by the formulas (1) or (2), a monomer represented by the formula (3), and epoxyacrylate or epoxymethacrylate. This composition is easily hardened at low temperature, weak in odor, small in shrinkage in hardening, excellent during durability against water and hot water, and thus suitable as the flooring material for a food processing factory, refrigerated warehouse, and cold storage. ##STR1## where R.sup.1 to R.sup.6, p and r are as defined.

Abstract: A molded article is produced by metathesis polymerization of a mixture containing at least one metathesis polymerizable monomer, a metathesis polymerization catalyst and an organic or inorganic filler material which has been treated with a vinyl-substituted silane coupler having at least one hydrolyzable group in addition to the vinyl group.

Abstract: A process for the production of thermoset polymers comprising contacting at least one monomer of the formulae: ##STR1## with a metathesis catalyst system which comprises a tungsten catalyst and a tin or silicon hydride cocatalyst.

Abstract: A resin composition for use as a paint contains a copolymer prepared by copolymerizing a monomer (I) represented by the following formula (I): ##STR1## wherein either one of X.sub.1 and X.sub.2 stands for an acryloyloxy or methacryloyloxy group, the other being a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R.sub.1 to R.sub.10 each stand for a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; and n is an integer of 1 to 4; with an .alpha.,.beta.-ethylenically unsaturated monomer having a reactive functional group and an .alpha.,.beta.-ethylenically unsaturated monomer having no reactive functional group. A monomer mixture for preparing the copolymer contains 5 to 95 wt % of the monomer (I).

Abstract: The present invention relates to a high surface hardness transparent resin having excellent scratch resistance, heat resistance and chemical resistance, a glazing material, a protective cover for display devices, an optical lens and a hard coat material comprising the aforesaid resin, and a novel polymerizable monomer which is useful as a raw material of the above-mentioned resin.The monomer is represented by the formula (I) ##STR1## (wherein R is an aliphatic residue having or not having an halogen atom, an oxygen atom, an alicyclic ring, a heterocyclic ring or an aromatic ring, an alicyclic residue, or a heterocyclic residue, n is an integer of 1 to 4, when n=1, X is oxygen or sulfur, when n.gtoreq.2, X's are all oxygen or all sulfur, one X is oxygen while the other X or X's are sulfur, one X is sulfur while the other X or X's are oxygen, or two X's are oxygen while the other X's are sulfur).

Abstract: This invention relates to a two component catalyst system for polymerization of metathesis polymerizable cycloolefins, comprising(a) a tungsten compound of the formula WOCl.sub.4-x (OAr).sub.x wherein Ar represents a hindered phenyl ring having bulky alkyl, alkoxyl halogen or aryl groups in the 2,6 position, i.e., diisopropyl or phenyl group and x=1, 2 or 3; and(b) an activator compound that is triphenyl tin hydride or trialkyl tin hydride, preferably a tributyltin hydride.Among the preferred molecules or groups that are substituted on the phenyl ring of the tungsten compound include chlorine, bromine, phenyl, methoxy and isopropyl. Ar may also represent a multisubstituted phenyl group such as 2,4-dichloro-6-methyl phenyl.

Abstract: A process is described for the polymerization of dicyclopentadiene using a novel catalyst system comprising (a) a tungsten compound which is the reaction product of a tungsten halide with a phenol which is not substituted with a bulky alkyl group at positions ortho with respect to the hydroxyl group, and (b) a trihydrocarbyl tin hydride.

Abstract: Disclosed is a method of moderating the catalyst activation characteristics of an alkyl aluminum compound by the use of hydrocarbon substituted acetylene. Preferred compounds are phenylacetylene, hexyne-1-and hexyne-2.

Abstract: A cross-linked copolymer containing repeating units derived from a mixture comprising the following monomers: ##STR1## and occasionally other repeating units derived from other metathesis polymerizable cyclic compounds such as dicyclopentadiene, a process for producing the copolymer, a process for producing a molded article from the copolymer and a polymerizable composition therefor.

Abstract: This invention pertains to the use of pyridinium isopoly and heteropoly molybdates and tungstates as catalysts in a metathesis catalyst system in polymerization of norbornene-type monomers by ring opening polymerization. Polymerization can be by reaction injection molding in absence of a solvent whereby a thermoset polymer is produced or by solution polymerization in presence of a suitable solvent whereby a thermosetting or a thermoplastic polymer is produced. The monomers are selected from polycycloolefins containing at least on enorbornene group and mixtures thereof.

Abstract: A process for producing a polymer by ring-opening polymerization of a norbornene-type monomer, which comprises starting the ring-opening polymerization in the presence of a Ziegler-type catalyst consisting essentially of an organometallic compound of a metal belonging to the groups I to III of the periodic table and titanium tetrahalide, carrying out the ring-opening polymerization until the norbornene-type monomer shows a conversion ratio of not less than 60%, and then adding a tungsten and/or molybdenum-based metathesis catalyst to the polymerization reaction system to continue the ring-opening polymerization.

Abstract: Disclosed is a process for the polymerization of norbornene derivatives which comprises contacting the monomer(s) with a catalytic system comprising the following two components:(1) a tungsten compound which is the product of combining a tungsten halide with a para-trihalomethylphenol which can be described by the formula ##STR1## in which each R is selected from alkyl and halide, and (2) a compound of the general formula: ##STR2## in which at least two of R.sup.1, R.sup.2 and R.sup.3 are selected from unsubstituted and substituted C.sub.1-20 hydrocarbyl.

Abstract: An elastic crosslinked metathesis polymer composition is disclosed comprised of a copolymer of a norbornene-type compound which metathesis polymerizes to a linear polymer and a norbornene-type compound having a second double bond of similar reactivity which forms a crosslinked polymer, and a hydrocarbon-based extending oil. Norbornene and dicyclopentadiene are typical comonomers. Polymerization is carried out by a RIM or resin injection molding process.

Abstract: A process for preparing molded objects wherein a liquid reaction mass comprised of a metathesis polymerizable cycloolefin, a metathesis polymerization catalyst, a catalyst activator and a reaction rate moderator are charged to a mold wherein polymerization will take place, the improvement wherein said catalyst activator comprises a dialkylzinc compound. Significantly increased gel and cure times are obtained with the dialkylzinc compounds as compared to the use of aluminum alkyl activator compounds. The gel and cure times may be further controlled by the addition of a phenolic compound to the tungsten or molybdenum compound or by the addition of a Lewis base.

Abstract: A process is disclosed for preparing a blend of a metathesis polymer and a radical polymer wherein a norbornene polymer is metathesis polymerized in the presence of a vinyl compound having two double bonds in conjugated relationship. Also included in the system is a compound capable of being reduced to a radical by the reduced valence transition metal element which serves as the catalyst of the metathesis polymerization. Examples of such compounds are specific chlorinated organic and chlorinated inorganic compounds.

Abstract: Dielectric supports for electronic components, such as circuit boards, are provided which are comprised of two or more bulk polymerized norbornene-type monomers. The monomers may be easily processed into circuit boards, etc. by reaction injection molding. The copolymers obtained exhibit high heat distortion temperatures and good dielectric properties and a balance of properties that make them, for example, well suited for molded wire board materials.

Abstract: A cross-linked copolymer containing repeating units derived from a mixture comprising the following monomers: ##STR1## and occasionally other repeating units derived from other metathesis polymerizable cyclic compounds such as dicyclopentadiene, a process for producing the copolymer, a process for producing a molded article from the copolymer and a polymerizable composition therefor.

Abstract: A cross-linked copolymer containing repeating units derived from dicyclopentadiene and metathesis polymerizable halogen-containing cycloalkenes, a process for producing the copolymer, a process for producing a molded article from the copolymer and a polymerizable composition therefor.

Abstract: This invention is a process for preparing a polymer which comprises contacting pure dicyclopentadiene with a pure tungsten catalyst complex, such as WCl.sub.3 (2,6-diisopropylphenoxy).sub.3, when tributyl tin hydride or triphenyl tin hydride is used as the activator for the polymerization. This process affords a method of polymerization of dicyclopentadiene in which the mixture gels slowly without the use of a rate moderator at 80.degree. C. (in from about 15 seconds to as much as two minutes or more) and furthermore cures quite slowly (in about 3-6 minutes). This delay makes these compositions particularly applicable to reaction injection molding processes. Moreover, both the tungsten complexes and the tin activator compounds employed in this invention are relatively insensitive to oxygen and water.

Abstract: Process for production of a molded article comprising polymerizing a norbornene monomer having bicyclic or higher cyclic structure in the presence of a metathesis catalyst system and a viscosity modifier having room temperature viscosity of 300 to 50,000 cps which viscosity modifier comprises a ring-opened polymer and unreacted norbornene monomer having bicyclic or higher cyclic structure.

Abstract: A rubber compounding material incorporating a cyclopentadiene-based pertroleum resin prepared by thermally copolymerizing 100 parts by weight of a cyclopentadiene-based feed or dicyclopentadiene-based feed with about 5 to 100 parts by weight of an .alpha.-olefin having from 6 to 16 carbon atoms at a temperature of from about 200.degree. to 300.degree. C. for a period of from about 10 minutes to 10 hours in the presence or absence of a solvent.A rubber composition is also disclosed, composed of this rubber compounding material in combination with a diene-based polymer.In rubber compositions for tires, the compounding material and rubber composition of the present invention greatly improve resistance to cutting and chipping of the tread.

Abstract: This invention is directed to the use of microencapsulated blowing agents in the bulk polymerization of cycloolefin monomers by ring-opening polymerization. These microencapsulated blowing agents aid in filling molds during reaction injection molding procedures such that both surfaces of the article being molded remain in contact with their respective mold surfaces eliminating sink marks in these surfaces. In addition, the microencapsulants may be introduced at higher levels which provide structural foams with the polymers from cycloolefin monomers.

Abstract: Process for preparing a pore-free polynorbornene product by bulk polymerizing a monomer charge containing at least one norbornene monomer having tricyclic or higher cyclic structure with a metathesis catalyst by controlling maximum exotherm temperature to a level of 160.degree. C. or below or by controlling the temperature difference to 80.degree. C. or below between the inner and exterior temperatures during the cooling period of said product from the maximum exotherm to the glass transition temperature of said product.

Abstract: The present invention provides a method for producing addition copolymers of ethylene and cycloolefin monomers of the norbornene-type, such as norbornene and tetracyclododecene. Copolymers having a uniform structure with uniform glass transition temperature values are provided by performing the copolymerization reaction in bulk with a catalyst system soluble in the cycloolefin monomers.

Abstract: Methods of preparing storage stable components useful for metathesis bulk polymerization of cycloolefin monomers are provided. These components contain cycloolefins with norbornene-functional groups and cocatalysts activated with a halometal compound. In these methods, the cocatalyst is completely formed before the halometal activator is added to prevent the formation of unwanted hydrogen halides, which catalyze undesired crosslinking reactions which destabilize the cocatalyst component. Bulk polymerization systems are provided wherein these storage stable cocatalyst components are paired with catalyst components that together form the complete metathesis catalyst system. For some embodiments, storage stability is aided by the removal of water.

Abstract: Disclosed is a method of delaying the metathesis polymerization of strained ring cycloolefins by addition of certain phosphorus-containing compounds including various aryl phosphates, aliphatic phosphates, aliphatic phosphites, aryl phosphites, aryl phosphines and alkyl phosphines.

Abstract: A cross-linked copolymer comprising repeating units derived from a mixture comprising metathesis polymerizable cyclic compounds such as dicyclopentadiene and carboxylic acid esters of which the acid residue and alcohol residue have individually at least one norbornene-moiety, a process for producing the copolymer, a process for producing a molded article from the copolymer and a polymerizable composition therefor.

Abstract: This invention pertains to the use of organoammonium, organophosphonium, organoarsonium heteropolymolybdates and heteropolytungstates, and mixtures thereof, as catalysts in a metathesis catalyst system in polymerization of cycloolefin monomers by ring opening polymerization. Polymerization can be by reaction injection molding in absence of a solvent whereby a thermoset polymer is produced or by solution polymerization in presence of a suitable solvent whereby a thermosetting or a thermoplastic polymer is produced. The cycloolefin monomers are selected from monocycloolefins except cyclohexane, polycycloolefins containing at least one norbornene group, and mixtures thereof.

Abstract: This invention pertains to the use of organophosphonium and organoarsonium molybdates and tungstates as catalysts in a metathesis catalyst system in polymerization of cycloolefin monomers by ring opening polymerization. Polymerization can be by reaction injection molding in absence of a solvent whereby a thermoset polymer is produced or by solution polymerization in presence of a suitable solvent whereby a thermosetting or a thermoplastic polymer is produced. The cycloolefin monomers are polycycloolefins containing at least one norbornene group, and mixtures thereof.

Abstract: A metathesis polymerization catalyst composition comprising a binuclear catalyst, wherein said binuclear catalyst is a mixture of at least two transition metal components, wherein a first transition metal component is a halide complex of tungsten, an oxyhalide complex of tungsten or a mixture thereof and a second transition metal component is a halide complex of a transition metal selected from the group consisting of high valent transition metals belonging to Groups IV or V of the Periodic Table, from about 1 to about 3 moles of phenolic compound per mole of tungsten component, activated by a metathesis catalyst activator and containing a rate moderator.

Abstract: A process for producing a colored cross-linked molded article by metathesis polymerizing in a mold a mixture comprising metathesis polymerizable monomers such as dicyclopentadiene and a metathesis polymerizable multi-part composition therefor.

Abstract: A method for preparing a resin having light color comprises the steps of: hydrogenating a compound represented by the formula (1) ##STR1## wherein l, m and n are integers of 0.ltoreq.l.ltoreq.3, 0.ltoreq.m.ltoreq.8 and l.ltoreq.n.ltoreq.3, respectively, and R.sup.1 and R.sup.6 each represent a hydrogen atom or a hydrocarbon residue having 1 to 3 carbon atoms, with or without R.sup.5 and R.sup.6 forming a ring, in the presence of a Ziegler catalyst containing a transition metal compound of the groups IV to VI of the Periodic Table and an organometallic compound of the groups I to III of the Periodic Table in combination to obtain a norbornene compound represented by the formula (2) ##STR2## wherein l, m, n and R.sup.1 and R.sup.6 are the same as above; and polymerizing the norbornene compound to give the resin having light color.

Abstract: An active energy ray-curable composition substantially comprising at least one of (meth)acrylates and oligomers thereof represented by the following general formula (I) ##STR1## wherein R represents a hydrogen atom or a methyl group, X represents an alkylene group in which at least one hydrogen atom may be replaced by a hydroxyl group, m is 0 or an integer of 1 to 4, Y represents a hydrocarbon group having a cyclic hydrocarbon moiety therein, and n is 1 or 2. The composition is useful as an adhesive, particularly as one in the production of optical discs.

Abstract: Disclosed is a method of reducing the activation rate of an alkyl aluminum activator in the metathesis polymerization of polycyclic cycloolefins. Activation rate is reduced by use of a bidentate Lewis base as the reaction rate moderator.

Abstract: Disclosed is a method of delaying the metathesis polymerization of strained ring cycloolefins by addition of certain nitrogen-containing compounds including various aromatic amines or mixtures thereof.

Abstract: Nodular copolymer and method of preparing a nodular copolymer by preparing a copolymer chain and coupling it with a coupling agent. The copolymers which form the nodular copolymer are formed of first and second segments, of which the second segments, containing the coupling agent, react to form the nodular region. The nodular copolymer is particularly useful as a lube oil additive.

Abstract: A process for preparing molded objects wherein a liquid reaction mass comprised of a metathesis polymerizable cycloolefin, a metathesis polymerization catalyst, a catalyst activator and a reaction rate moderator are charged to a mold wherein polymerization will take place, the improvement wherein said catalyst activator comprises a dialkylzinc compound. Significantly increased gel and cure times are obtained with the dialkylzinc compounds as compared to the use of aluminum alkyl activator compounds. The gel and cure times may be further controlled by the addition of a phenolic compound to the tungsten or molybdenum compound or by the addition of a Lewis base.

Abstract: Liquid, low viscosity, graft polyols comprising the liquid reaction product of a vegetable oil or unsaturated fatty carbon compound having at least eight carbon atoms, at least one hydroxyl group, and at least one double bond, said compound having other than terminal unsaturation a cyclopentadienyl compound and a terminally unsaturated monomer having at least one hydroxyl group, when cured with a polyisocyanate, melamine, or formaldehyde compound, or when esterified with a polybasic acid composition to form an alkyd resin, yield high solids or solventless polyurethane compositions useful as coatings, adhesives, potting or molding compounds.

Abstract: Process of polymerization of unsaturated hydrocarbons, with an initial induction period, by means of a catalyst constituted by a halogeno-phenate of tungsten, of which the phenate group carries one or more substituents, in the presence of an organometallic co-catalyst; the halogeno-phenate is chosen from amongst those represented by the formula ##STR1## where X is a halogen, especially Cl or Br, n is a whole number 2, 3 or 4, R.sup.1 is H or a C.sub.1 to C.sub.8 straight- or branched-chain alkoxy group, R.sup.2 is H or a C.sub.3 to C.sub.9 branched-chain alkyl group, R.sup.1 and R.sup.2 never being hydrogen simultaneously.

Abstract: A process for producing a high softening point hydrocarbon resin, which comprises polymerizing (a) an oil fraction having a boiling point within a range of from 140.degree. to 220.degree. C. selected among cracked oil fractions obtained by thermal cracking of petroleum and (b) a turpentine oil in the presence of a cationic polymerization catalyst, wherein the oil fraction (a) is adjusted to have a conjugated diolefin content of at most 1.5% by weight and a dicyclopentadiene (non-conjugated diolefin) content of from 7 to 17% by weight, the turpentine oil (b) is selected from the group consising of .alpha.-pinene, .beta.-pinene, dipentene and mixtures thereof and used in an amount of from 5 to 15% by weight, the cationic polymerization catalyst is at least one member selected from the group consisting of boron trifluoride, aluminum trichloride and complexes thereof, and the polymerization is conducted at a temperature of from 0.degree. to 70.degree. C.

Abstract: According to the invention, there are provided an optical resin and a process for preparing such a resin. The optical resin is obtained by polymerizing a feed monomer comprising at least a diester of dicarboxylic acid represented by the general formula (1) of: ##STR1## wherein R.sub.1 and R.sub.2 each represent the same or different groups and stand for an alkyl or alkenyl group having 1 to 12 carbon atoms, a cycloalkyl group having 3 to 12 carbon atoms or an ester residue having at least one aromatic ring.

Abstract: Disclosed is an improved method for making a thermoset polymer wherein a plurality of reactant streams, one of which contains the activator of a metathesis catalyst system combined with a moderator, and a second of which contains the catalyst of the metathesis catalyst system and at least one of which contains dicyclopentadiene are combined to form a reaction mixture, and the reaction mixture is then injected into a mold where polymerization occurs. The improvement comprises adding to the reaction mixture 1-25 mols of a cationic polymerization initiator per 1000 mols of dicyclopentadiene.

Abstract: Articles having shape recovering properties and methods of using them are disclosed. An article is formed from a composition containing a norbornene polymer by forming said polymer into an article having a first shape, then deforming the article in the solid state to a second shape and cooling the article to a first temperature at or below the glass transition temperature of the polymer to retain said second shape, and finally heating said article to a temperature above the first temperature to recover the first shape.

Abstract: Disclosed is a method of reducing the activation rate of an alkyl aluminum activator in the metathesis polymerization of polycyclic cycloolefins. Activation rate is reduced by use of a bidentate Lewis base as the reaction rate moderator.

Abstract: A polyunsaturated hydrocarbon polymer-compatible anti-oxidant composition is provided which comprises a mixture of at least one sterically hindered phenolic compound and at least one aryl amine compound in a molar ratio ranging from about 0.1 to about 10.

Abstract: The invention is a process for preparing a polymer which comprises contacting dicyclopentadiene with a catalyst comprising a phenolic substituted tungsten halide and a trialkyltin hydride or triphenyltin hydride and recovering said polymer. The invention is also a polymer of dicyclopentadiene as prepared in the process of the invention and a catalyst used in the process of the invention to prepare said polymer.

Abstract: Disclosed is a method of making a cross-linked poly(dicyclopentadiene) with a metathesis-catalyst system, where the metathesis-catalyst system contains an organoaluminum or organoaluminum halide activator and a pentavalent tantalum catalyst. In a preferred embodiment, the cross-linked polymer is formed by combining, in a first place, a plurality of reactant streams, one reactant stream which contains the activator, a second reactant stream which contains the catalyst and at least one reactant stream which contains dicyclopentadiene; then injecting the combined reactant streams into a second place, such as a mold, where polymerization occurs. Use of the pentavalent tantalum catalyst results in the formation of a cross-linked polymer having less color and greater transparency than cross-linked poly(dicyclopentadiene) made without a pentavalent tantalum catalyst.

Abstract: Disclosed is the incorporation into a two-part metathesis-catalyst system of a halogen containing hydrocarbyl additive, where the hydrocarbyl additive contains at least one trihalogen substituted atom or at least one activated halogen atom. The use of this catalyst system to polymerize dicyclopentadiene results in a thermoset polymer containing low levels of residual monomer. Also disclosed is a preferred embodiment of dicyclopentadiene polymerization where the two parts of the metathesis-catalyst system, plus dicyclopentadiene are combined in the mixing head of a reaction injection molding machine and then injected into a mold where the dicyclopentadiene rapidly sets up into a thermoset polymer.

Abstract: Polymers formed from anhydrides of the formula I ##STR1## in which R.sub.1 and R.sub.2 independently of one another are hydrogen or methyl.The novel polymers are suitable for use as curing agents for polyepoxide compounds.

Abstract: A high flash point cycloolefin composition, including at least 50% by weight dicyclopentadiene, the composition having a flash point of greater than 100.degree. F. and a viscosity of from about 3 cps to about 3000 cps at about 70.degree. F. and about 1 atmosphere pressure. The cycloolefin composition is used in a method of preparation of cycloolefin for polymerization by metathesis catalysis to form a substantially crosslinked thermoset polymer by: distilling the cycloolefin to form distilled cycloolefin, and contacting the distilled cycloolefin and an adsorbent.