Hoechst Celanese Corporation

Dupont Electronic Polymers LP

Chem First Electronic Materials L.p.

E.i. Dupont De Nemours and Company

Triquest LP

Hoechst Clanese Corporation

James R Sounik

Michael T Sheehan

William W Wilkison, Iii

Bret F Hann

Keith M Russ

Charles B Hilton

Graham N Mott

Kenneth G Davenport

Apurba Bhattacharya

Jacquelyn Popolo

Mark Elliot Wagman

Keith Joseph Kunitsky

Michael Fryd

Frank L Schadt, Iii

Richard Vicari

Olan S Fruchey

Mohammad Aslam

Garo Khanarian

Thomas M Leslie

George Kvakovszky

Steve W Meyer

Mark A Murphy

Robert Norwood

Debasish Kuila

Lynn Massarelli

George W Clark, Iii

John R Fritsch

A process for preparing proponates which comprises the steps of (i) supplying a solution of methanol containing 4-hydroxyphenylmethylcarbinol, (ii) subjecting said solution to an acid catalyzed displacement reaction for a sufficient period of time and under suitable conditions of temperature and pressure to convert substantially all of said carbinol to 4-hydroxyphenylmethylcarbinol methyl ether in solution, (iii) replacing the methanol in said ether containing solution with a second solvent and (iv) reacting the ether containing ethyl lactate solution with a suitable acid catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form said propanoates. New compositions of matter which comprise the propanoates, prepared in the above manner, have application in the electronic chemicals market such as in a photoresist composition.

Propanoates and processes for preparing the same

The present invention relates to novel photoresist compositions and processes for preparing the same utilizing polymers having a low polydispersity via the use of certain chain transfer agents (CTA) with certain monomers to provide said polymers. The polymers incorporating the chain transfer agents can be homopolymers, or made with additional monomers to provide copolymers. These polymers/copolymers are then converted into photoresist compositions for use as such.

Photoresist compositions and processes for preparing the same

A process for producing a stable polymer such as poly(hydroxystyrene) which comprises the decarboxylation of a corresponding phenolic in the presence of a non-amine basic catalyst and a polar organic solvent, followed by the polymerization thereof.

Methods for preparing polymers from phenolic materials and compositions relating thereto

An anhydrous, liquid phase process for preparing hydroxyl containing polymers of enhanced purity comprising the steps of polymerization, purification, transesterification, purification, catalyst removal, and solvent exchange. The resultant polymer in solution can be used directly, without further processing steps, to prepare a photoresist composition.

Anhydrous, liquid phase process for preparing hydroxyl containing polymers of enhanced purity

Polymers derived from various monomers are purified by fractionalization of the crude polymers in a solvent/non solvent system via reverse precipitation.

Polymer purification

A novel one-pot cost efficient process for the preparation of homo-, co- and terpolymers of p-hydroxystyrene or substituted p-hydroxystyrene and alkyl acrylates. The process involves polymerization of esters of p-hydroxystyrene (or its substituted analogs), alkyl acrylate monomers and/or one or more of ethylenically unsaturated monomers in an alcohol solvent in the presence of a free radical initiator. The reaction mixture containing the so formed polymer is subjected to transesterification conditions using a catalytic amount of catalyst to result in co- and/or terpolymers of p-hydroxystyrene without cleavage of the alkyl ester in the acrylate repeat unit, and then removing the catalyst from the system. Preferred embodiments include homopolymers of p-hydroxystyrene, copolymer of p-hydroxystyrene and tert-butyl acrylate and terpolymer of p-hydroxystyrene, tert-butyl acrylate and styrene. These polymers have a wide variety of applications including as photoresists in microelectronics industry.

Preparation of homo-, co- and terpolymers of substituted styrenes

The invention provides a novel process for improving the glass transition temperatures of polymers by partitioning the polymer between immiscible solvents to remove the low molecular weight polymer from the desired product.

Purification means

A process for preparing a poly(hydroxystyrene) which comprises the steps of (a) heating a carbinol under decomposition conditions in the presence of a solvent for a sufficient period of time to form hydroxystyrene, said solvent having a boiling point in substantially the same range as said hydroxystyrene; and (b) polymerizing said hydroxystyrene under suitable polymerization conditions of pressure and temperature and for a sufficient period of time to form poly(hydroxystyrene).

Process for preparing poly(4-hydroxystyrene)

A process for preparing a polyhydroxystyrene having a novolak type structure which comprises the step of polymerizing a mixture of carboxylic acid and at least one substituted phenyl carbinol whose formula is: ##STR1## wherein (a) R.sub.1 is selected from the group consisting of H, alkyl C.sub.1 -C.sub.20, substituted and unsubstituted phenyl, and C(O)R.sub.8 (where R.sub.8 is alkyl C.sub.1 -C.sub.20); (b) R.sub.2 is selected from the group consisting of H and alkyl C.sub.1 -C.sub.20 ; and (c) R.sub.3 -R.sub.7 are each independently selected from the group consisting of H, alkyl C.sub.1 -C.sub.20, OR.sub.9 (where R.sub.9 is H, alkyl C.sub.1 -C.sub.20, esters thereof, or substituted and unsubstituted phenyl), halogen, BZT, nitro, or amino, with the proviso that at least one of R.sub.3 -R.sub.7 is OR.sub.9, in the presence of a suitable catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form said novolak type polymer.

Process for preparing polyhydroxystyrene with a novolak type structure

The present invention provides a unique and novel way of producing carbinols such as 4-hydroxyphenylmethylcarbinol (HPMC). In this new process, a ketone such as 4-hydroxyacetophenone (4-HAP) is heated under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable catalyst and a basic material, and for a sufficient period of time to form HPMC.

Process for preparing 4-hydroxyphenylmethylcarbinol

The present invention provides a unique and novel way of producing an acetoxystyrene. In this new process which comprises a single step, a mixture of (a) a carbinol, (b) an acetylating agent, and (c) an acid catalyst is dehydrated under suitable dehydration conditions of temperature and pressure to form said acetoxystyrene.

Process for preparing acetoxystyrene

A new polyhydroxystyrene having a novolak type structure which is prepared by the process which comprises the step of polymerizing a mixture of carboxylic acid and at least one substituted phenyl carbinol whose formula is: ##STR1## wherein (a) R.sub.1 is selected from the group consisting of H, alkyl C.sub.1 -C.sub.20, substituted and unsubstituted phenyl, and C(O)R.sub.8 (where R.sub.8 is alkyl C.sub.1 -C.sub.20); (b) R.sub.2 is selected from the group consisting of H and alkyl C.sub.1 -C.sub.20 ; and (c) R.sub.3 -R.sub.7 are each independently selected from the group consisting of H, alkyl C.sub.1 -C.sub.20, OR.sub.9 (where R.sub.9 is H, alkyl C.sub.1 -C.sub.20, esters thereof, or substituted and unsubstituted phenyl), halogen, BZT, nitro, or amino, with the proviso that at least one of R.sub.3 -R.sub.7 is OR.sub.9, in the presence of a suitable catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form said polyhydroxystyrene.

Polyhydroxystyrene with a novolak type structure

The present invention provides a unique and novel way of producing polyhydroxystyrene which comprises the steps of (a) heating 4-hydroxyacetophenone under suitable hydrogenation conditions of temperature and pressure in the presence of a suitable palladium catalyst and a basic material and for a sufficient period of time to form 4-hydroxyphenylmethylcarbinol; (b) heating 4-hydroxyphenylmethylcarbinol under suitable conditions of temperature and pressure and for a sufficient period of time to form said polyhydroxystyrene.

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Corpus Christi, TX, United States of America

James R Sounik