# US 2008/0188692 A1 · Derivatized polyhydroxystyrenes with a novolak type structure and processes for preparing the same

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- Number: US 2008/0188692 A1
- Document ID: US20080188692A1
- Status: Published application
- Kind: A1
- Application number: 12/080,871
- Filed: 2008-04-07
- Published: 2008-08-07
- Earliest claimed: 2005-04-22
- Assignees: DuPont Electronic Polymers L.P.
- Inventors: Michael T. Sheehan; Edward G. Zey
- Web page: https://patentgrep.com/patent/US20080188692A1

## CPC

- C09D 125/18: Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
- C08G 61/04: only aliphatic carbon atoms
- C08G 2261/312: Non-condensed aromatic systems, e.g. benzene
- G03F 7/023: Macromolecular quinonediazides; Macromolecular additives, e.g. binders {(G03F7/0226 takes precedence)}
- G03F 7/038: Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021)
- Y02P 20/582: Recycling of unreacted starting or intermediate materials
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)
- Y02P: CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS

## Abstract

A process for preparing derivatized poly(4-hydroxystryrene) having a novolak type structure 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) polymerizing said ether containing solution in the presence of a suitable acid catalyst for a sufficient period of time and under suitable conditions of temperature and pressure to form a novolak type polymer. New compositions of matter which comprise the derivatized poly(4-hydroxystyrene) prepared in the above manner and which have application in the electronic chemicals market such as in a photoresist composition, and in other areas such as in varnishes, printing inks, epoxy resins, copying paper, tackifiers for rubber, crude oil separators, and the like.

## Claims

### Claim 1

A composition of matter having the following structure:
wherein n is from about 1 to about 10.

### Claim 2

A composition of matter comprising a derivatized poly(4-hydroxystyrene) characterized by having from about 6% to about 40% linearity, a polydispersity of less than about 2.0, and a molecular weight of less than about 10,000.

### Claim 3 (depends on 1)

A primary photoresist composition for patterning electronic circuitry based on the composition of matter set forth in claim 1.

### Claim 4 (depends on 1)

A curing agent for an epoxy resin based on the composition of matter set forth in claim 1.

### Claim 5 (depends on 1)

A varnish incorporating the composition of matter set forth in claim 1.

### Claim 6 (depends on 1)

A printing ink incorporating the composition of matter set forth in claim 1.

### Claim 7 (depends on 1)

A tackifier for rubber incorporating the composition of matter set forth in claim 1.

### Claim 8 (depends on 1)

A crude oil separator incorporating the composition of matter set forth in claim 1.

### Claim 9 (depends on 1)

A solder mask or photoimageable coverlay for rigid or flexible printed circuit boards incorporating the composition of matter set forth in claim 1.