The Dow Chemical Company

Dow Global Technolgoies LLC

Robert A Devries

Ying Hung So

Edmund J Stark

Hughie R Frick, Deceased

Robert L McGee

Edward Otto Shaffer, Ii

Michael J Radler

Mitchell G Dibbs

Hughie R Frick

R Garth Pews

Zenon Lysenko

Duane R Romer

Richard E Campbell, Jr

John C Schultz

Michael E Mills

James P Godschalx

Pulikkottil Jacob Thomas

Paul H Townsend, Iii

Gregory F Schmidt

Gary R Buske

Steven J Martin

Ernest L Ecker

Daniel A Batzel

Reed A Shick

Carol E Mohler

Raul A Pabon, Jr

Dennis W Smith, Jr

Mary L Ash

Herbert C Jackson, Jr

Richard P DeCaire

Bonnie Frick

Joseph N Carr

G Thomas Wells

The invention is a curable cyclobutarene based polymer comprising acid functional pendant groups. The cured polymer displays excellent qualities of toughness, adhesion, dielectric constant, and low stress. The preferred system is soluble in an aqueous base and can be used to generate patterned films with excellent resolution without the need to handle organic developer solvents.

Acid functional polymers based on benzocyclobutene

This invention is a method comprising preparing a sample by coating a thin film of a precursor material, which is free of fluorescent probe molecules onto a substrate and subjecting the precursor material to conditions to attempt to cause cure of the precursor to an organic, aromatic, polymer having a dielectric constant of less than 3.0, exposing the sample to radiation having a wavelength in the range of 200 to 500 nm, detecting a resulting emission of radiation, and comparing the emission to the emission for a known cured, non-oxidized standard for the polymer.

Method for determination of cure and oxidation of spin-on dielectric polymers

An oligomer, uncured polymer or cured polymer comprising the reaction product of one or more polyfunctional compounds containing two or more cyclopentadienone groups and at least one polyfunctional compound containing two or more aromatic acetylene groups wherein at least some of the polyfunctional compounds contain three or more reactive groups. Such oligomers and uncured polymers may be cured to form cured polymers which are useful as dielectrics in the microelectronics industry, especially for dielectrics in integrated circuits.

Polyphenylene oligomers and polymers

This invention relates to a novel process for preparing vinylsiloxane-BCBs (vinylsiloxane-benzocyclobutenes) comprising reacting a hydrolyzable hydrosilating reagent with an acetylene-BCB in the presence of a catalyst, then hydrolyzing the hydrolyzable vinylsilane-BCB to form a vinylsiloxane-BCB.

Preparation of a vinylsiloxane-benzocylobutene from a hydrolyzable

A method for determining the configuration of a resin portion of an article comprising exposing the article to a light source at a first wavelength and measuring emission of light at a second, different wavelength; wherein the resin contains a moiety containing a structure of the formula: ##STR1## or a moiety which is a reaction product of said moiety in a quantity sufficient to impart fluorescent properties to said resin.

Method of optical inspection

A crude vinylically unsaturated product formed from a palladium-complex-catalyzed reaction of a reactant halide selected from the group consisting of aryl, allyl, vinyl, and benzyl halides, and a reactant olefin having a vinylic hydrogen, wherein the reaction is carried out in the presence of a hydrogen halide acceptor, is purified by first contacting the crude product with a base that is stronger than the hydrogen halide acceptor, then heating the stronger base-contacted product. The purified product shows a marked reduction in concentration bromine and palladium impurities. The product can then be further purified by such methods as chromatography, crystallization, or distillation to achieve a product that is more suitable for applications where very low levels of inorganic impurities are required.

Process for purifying vinylically unsaturated compounds prepared using a

This invention relates to a novel process for preparing vinylsilane-BCBs (vinylsilane-benzocyclobutenes) comprising reacting a hydrosilating reagent with an acetylene-BCB in the presence of a catalyst. The invention also relates to a novel mixture of isomers of DVS-bisBCB (1,3-divinyl-1,1,3,3-tetramethyldisiloxane bisbenzocyclobutene) as well as novel partially or fully cured polymers derived from the vinylsilane BCBs.

Preparation of vinylsilane-benzocyclobutenes

An olefinic polymer is grafted with a vinyl arylcyclobutene such as 4-vinylbenzocyclobutene. The arylcyclobutene grafted olefinic polymers are useful in a number of industrial applications including electronics, and as coatings, membranes, fibers, structural composites, adhesives, and wrapping and packaging films.

Arylcyclobutene grafted polyolefins

A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an organic hydrogen halide acceptor and (c) a diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from organosilicon compounds, hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a combination thereof.

Process for preparing vinylically-unsaturated compounds

This invention is a process for the production of acetylated aromatic products, including acetyl benzoeyclobutenes, in one step and in high yield. The process comprises contacting an aryl halide with an alkyl vinyl ether in the presence of a zerovalent palladium catalyst complex and a hydrogen halide acceptor in a aqueous solvent mixture containing at least about one molar equivalent of water based on moles of the aryl halide.

Production of acetylated aromatic compounds

A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an inorganic hydrogen halide acceptor and (c) a diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a combination thereof.

Process for preparing vinylically-unsaturated compounds (II)

A process for preparing a 3- or 4-hydroxybenzocyclobutene comprises reacting a 3- or 4-halogenzocyclobutene reactant with an alkali metal hydroxide by heating in an aqueous alcohol medium at a temperature from about 50.degree. C. to a temperature at which dimerization or oligomerization of a benzocyclobutene reactant or product is a significant side reaction, in the presence of a metal-containing catalyst, for a time sufficient to convert the halobenzocyclobutene reactant to the hydroxybenzocyclobutene product.

Process for preparing hydroxybenzocyclobutenes

A process for purifying an impure vinylically-unsaturated organosilicon product compound prepared by reaction between a vinylically-unsaturated organosilicon precursor and a halogenated organic compound in the presence of a homogeneous zerovalent palladium catalyst complex, the catalyst complex including an organophosphine or organoarsine ligand, in the presence of a hydrogen halide acceptor in an essentially anhydrous diluent, comprising treating a mixture containing the impure vinylically-unsaturated organosilicon product compound with a peroxide for a time sufficient to oxidize organophosphine or organoarsine impurities present in a mixture being treated. The peroxide can be selected from aqueous hydrogen peroxide or organic peroxides. The thus-treated mixture can be further treated by chromatography over silica gel or alumina. In optional embodiments, chromatography over silica gel or alumina can precede treatment with the peroxide.

Process for purifying vinylically-unsaturated organosilicon compounds

A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an inorganic hydrogen halide acceptor and (c) diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom, silicon atom or a combination thereof.

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Midland, MI, United States of America

Robert A Devries