The Dow Chemical Company

W Frank Richey

Katherine S Clement

David A Babb

Marlin E Walters

Bobby R Ezzell

Emmett L Tasset

Donald J Perettie

Larry D Bratton

Alvin P Kennedy

Eric S Moyer

Marius W Sorenson

Zdravko P Jezic

George M St George

Eckel R Lane

Edward R Peterson

Paul M Puckett

Steven L Brewster

V Rao Durvasula

William O Perry

Hong A Nguyen

Zdravko Jezie

David B Babb

Eckel Lan

A laminate has at least two layers, at least one of which comprises a polymer having more than one perfluorocyclobutane group. Such polymers impart qualities of environmental or protection, chemical and solvent resistance, hydrolytic stability, lubricity, low dielectric, hydrostatic stability, weatherability, flame resistance, chemical resistance, hydrolytic stability, lubricity, environmental protection, scratch resistance, solvent resistance, surface passivation, water repellancy, lower surface refractive index, lower surface coefficient of friction, fluid barrier properties, oil repellancy, thermal stability, and/or reduced moisture pick-up. Additionally, the coatings are optically clear, easy to apply either neat, in a solvent or otherwise, have relatively low cure temperatures for their temperature resistance, and exhibit insulating and planarizing capabilities.

Resin transfer molding process for composites

The invention involves aromatic polyhydroxy compounds, including triaromatic bisphenols and tris-[1,1,1-(4-hydroxyphenyl)] toluenes, and a process for the preparation thereof by reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene, and a large portion of the yield is para isomer. Suitable halo-compounds include aromatic dihalo-compounds having at least one aliphatic substituent having two alpha-halogen atoms and at least one beta halogen atom, halo-styrenes having structures corresponding to such aromatic dihalo-compounds except that an alpha-halogen atom and a beta hydrogen atom are removed and there is a double bond between the alpha and beta carbon atoms, trihalotoluenes, and dihalocyanotoluenes.

Aromatic polyhydroxy compounds and process for the preparation thereof

A polymer has at least one photoactive site and more than one perfluorocyclobutane group. New monomers containing photoactive sites or photoactive precursors and at least one perfluorovinyl group are useful for making such polymers. Processes of making such polymers and the monomers from which they are made are disclosed. The polymers are useful in coatings, photoresists, and the like.

Photodefinable polymers containing perfluorocyclobutane groups

A laminate has at least two layers, at least one of which comprises a polymer having more than one perfluorocyclobutane group. Such polymers impart qualities of enviornmental or protection, chemical and solvent resistance, hydrolytic stability, lubricity, low dielectric, hydrostatic stability, weatherability, flame resistance, chemical resistance, hydrolytic stability, lubricity, environmental protection, scratch resistance, solvent resistance, surface passivation, water repellancy, lower surface refractive index, lower surface coefficient of friction, fluid barrier properties, oil repellancy, thermal stability, and/or reduced moisture pick-up. Additionally, the coatings are optically clear, easy to apply either neat, in a solvent or otherwise, have relatively low cure temperatures for their temperature resistance, and exhibit insulating and planarizing capabilities.

Laminates of polymer shaving perfluorocyclobutane rings

Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.

Chlorination process, alkylation of products of said process and some

The invention involves aromatic polyhydroxy compounds, including triaromatic bisphenols and tris-1,1,1-(4-hydroxyphenyl)] toluenes, and a process for the preparation thereof by reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene, and a large portion of the yield is para isomer. Suitable halo-compounds include aromatic dihalo-compounds having at least one aliphatic substituent having two alpha-halogen atoms and at least one beta halogen atom, halo-styrenes having structures corresponding to such aromatic dihalo-compounds except that an alpha-halogen atom and a beta hydrogen atom are removed and there is a double bond between the alpha and beta carbon atoms, trihalotoluenes, and dihalocyanotoluenes.

A process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having aromatic polyester, aromatic polyamide, or polyimide groups or combination thereof, at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed. Chain extending oligomers of polymers having poor processing characteristics by this process results in polymers which are more easily processed. For instance, perfluorocyclobutane groups formed in an extruder to chain lengthen polyimide oligomers, in effect, render polyimides extrudable. The polymer formed by the method preferably has polyimide groups. New monomers and polymers having imide and perfluorovinyl or perfluorocyclobutane structures, respectively, are prepared.

Perfluorocyclobutane ring-containing polymers

Laminates of polymers having perfluorocyclobutane rings and polymers

Active methine compounds are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylonium hydroxide. Chlorinated products, preferably tertiary alkyl chloro compounds, are produced. The tertiary alkyl chloro compounds are useful in elimination reactions, preferably reactions with base, to form unsaturated compounds, particularly compounds having a vinylidene or exomethylene group.

Chlorination and elimination process and some products thereof

A compound having at least one perfluorovinyl group and at least one functional group is suitable for reacting with and/or forming polymers. The compound is preferably of Formula I:

Reactive compounds containing perfluorovinyl groups

A process for preparing a polymer having perfluorocyclobutane rings by the steps of (a) contacting monomers having at least two dimerizable perfluorovinyl groups; and (b) exposing the monomers to sufficient heat and for a sufficient time that a polymer containing perfluorocyclobutane rings is formed. The invention includes polymers having a backbone comprising hydrocarbyl groups, perfluorocyclobutane rings and non-carbon atoms and polymers of at least 10,000 molecular weight having repeating units [O-(CFR.sub.f).sub.n -O-perfluorocyclobutane].

The invention is a process for the preparation of triaromatic bisphenols reacting a phenolic compound, e.g. phenol, with a suitable halo-compound, for instance 1,1-dichloroethylbenzene, 1-chlorostyrene, or mixtures thereof. The reaction may be conducted in the presence or absence of a solvent; an excess of the phenolic compound can serve as the solvent. The product is conveniently recovered by removing the by-product HCl, excess phenolic compound, excess solvent and cooling. Yields of bis-1,1-(4-hydroxyphenyl)-1-phenylethane which are greater than 90% of theoretical have been obtained by the reaction of phenol and 1,1-dichloroethylbenzene and a large portion of the yield is para isomer. Suitable halo-compounds include aromatic dihalo-compounds having at least one aliphatic substituent having two alpha-halogen atoms and at least one beta halogen atom, halo-styrenes having structures corresponding to such aromatic dihalo-compounds except that an alpha-halogen atom and a beta hydrogen atom are removed and there is a double bond between the alpha and beta carbon atoms, trihalotoluenes, and dihalocyanotoluenes.

Process for the preparation of bisphenols

Inorganic and organic hypohalites are used to obtain good selectivity to alpha halogenation of alkyl aromatic compounds. Alkali and alkaline earth hypohalites must be used in conjunction with a phase transfer medium. Useful organic hypohalites are the tertiary alkyl hypohalites, which are employed in the presence of free radical generating media such as light or compounds which produce free radicals thermally. At least one mole of hypohalite reactant must be used for every alpha hydrogen in the alkyl aromatic compound. A new bisphenol which contains biphenyl functionality has been made as well as an aromatic polyester derived therefrom.

Method for the selective alpha halogenation of alkylaromatic compounds

A laminated structure comprising a copper metal substrate adhered to a polyimide polymer by the use of first and second adhesive resin layers.

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Lake Jackson, TX, United States of America

W Frank Richey