# US 2014/0154626 A1 · Epoxy-functional radiation-curable composition containing an epoxy-functional siloxane oligomer for enhanced film retention and adhesion during solvent development

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- Number: US 2014/0154626 A1
- Document ID: US20140154626A1
- Status: Published application
- Kind: A1
- Application number: 14/119,950
- Filed: 2012-05-23
- Published: 2014-06-05
- Earliest claimed: 2011-05-25
- Assignees: Dow Corning Corporation
- Inventors: Duane Raymond Bujalski; Jon Vierling Degroot, JR.; David J. Deshazer; Shedric Oneal Glover; Karen L. Hueston; John Ladouce
- Web page: https://patentgrep.com/patent/US20140154626A1

## CPC

- G03F 7/0757: {Macromolecular compounds containing Si-O, Si-C or Si-N bonds (G03F7/0752 takes precedence)}
- C08L 83/06: containing silicon bound to oxygen-containing groups (C08L83/12 takes precedence)
- C09D 183/06: containing silicon bound to oxygen-containing groups (C09D183/12 takes precedence)
- G02B 6/1221: {made from organic materials}
- G02F 1/0063: {Optical properties, e.g. absorption, reflection or birefringence (materials for non-linear optics G02F1/355)}
- G03C 1/00: Photosensitive materials (photosensitive materials for multicolour processes G03C7/00; for diffusion transfer processes G03C8/00; photosensitive glass C03C4/04)
- G03F 7/20: Exposure; Apparatus therefor (photographic printing apparatus for making copies G03B27/00)
- G02F 2202/023: curable
- 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)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)
- G02B: OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02F: OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G03C: PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES (for photomechanical purposes G03F); PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY (photographic processes characterised by the use or manipulation of apparatus classifiable per se in subclass G03B, see G03B; photomechanical production of textured or patterned surfaces G03F; electrophotography, magnetography G03G)

## Abstract

The present invention provides a silicone composition that includes an epoxy-functional organopolysiloxane resin and an epoxy-functional organosiloxane oligomer, and a method of preparing optical waveguides using the silicon composition. The present invention also provides a cured silicon composition, and an optical waveguide that includes the cured silicon composition.

## Claims

### Claim 1

A silicone composition, comprising:
(A) an epoxy-functional organopolysiloxane resin having the average unit formula
(R1R2R3SiO1/2)a(R4R5SiO2/2)b(R6SiO3/2)c(SiO4/2)d (I)
wherein R1, R2, R3, R4, R5, and R6 are organic groups independently selected from C1-6 monovalent aliphatic hydrocarbon groups, C6-10 monovalent aromatic hydrocarbon groups, and monovalent epoxy-substituted organic groups, 0≦a<0.4, 0<b<0.5, 0<c<1, 0≦d<0.4, 0.1≦b/c≦0.3, a+b+c+d=1, the resin has a number-average molecular weight of at least about 2000, at least about 15 mol % of the organic groups are C6 to C10 monovalent aromatic hydrocarbon groups, and about 2 to about 50 mol % of siloxane units have epoxy-substituted organic groups;
(B) an epoxy-functional organosiloxane oligomer having an average of at least two epoxy-substituted organic groups per molecule and a molecular weight not greater than about 1500;
(C) a cationic photoinitiator, and
(D) optionally, an organic solvent.

### Claim 2 (depends on 1)

The silicone composition of claim 1, wherein the epoxy-functional organosiloxane oligomer has a formula selected from
R8R72SiO(R72SiO)mSiR72R8 (II)
and R9Si(OSiR72R8)3 (IV)
wherein R7 is C1-8 alkyl, R8 is an epoxy-substituted organic group, R9 is R7 or —OSiR72R8, m is 0 or a positive integer, and n is from 3 to 10.

### Claim 3 (depends on 1)

The silicone composition of claim 1, wherein the epoxy-functional organosiloxane oligomer has the formula:
R8R72SiO(R72SiO)mSiR72R8 (II)
wherein m is 0 and R8 is 3,4-epoxycyclohexylethyl.

### Claim 4 (depends on 1)

The silicone composition of claim 1, further comprising a photosensitizer.

### Claim 5 (depends on 1)

A cured silicone composition, comprising the silicone composition of claim 1 subjected to a curing process.

### Claim 6 (depends on 5)

The cured silicone composition of claim 5, wherein the cured composition is flexible.

### Claim 7 (depends on 5)

The cured silicone composition of claim 5, wherein the cured silicone composition is a light-transmitting component of an optical waveguide.

### Claim 8 (depends on 5)

An optical waveguide, comprising the cured silicone composition of claim 5.

### Claim 9

A method of preparing a flexible planar optical waveguide assembly, comprising the steps of:
(i) applying a first silicone composition to a surface of a substrate to form a first silicone film, the first silicone composition comprising
(A) an epoxy-functional organopolysiloxane resin having the average unit formula
(R1R2R3SiO1/2)a(R4R5SiO2/2)b(R6SiO3/2)c(SiO4/2)d (I)
wherein R1, R2, R3, R4, R5, and R6 are organic groups independently selected from C1-6 monovalent aliphatic hydrocarbon groups, C6-10 monovalent aromatic hydrocarbon groups, and monovalent epoxy-substituted organic groups, 0≦a<0.4, 0<b<0.5, 0<c<1, 0≦d<0.4, 0.1≦b/c≦0.3, a+b+c+d=1, the resin has a number-average molecular weight of at least about 2000, at least about 15 mol % of the organic groups are C6 to C10 monovalent aromatic hydrocarbon groups, and about 2 to about 50 mol % of siloxane units have epoxy-substituted organic groups,
(B) an epoxy-functional organosiloxane oligomer having an average of at least two epoxy-substituted organic groups per molecule and a molecular weight not greater than about 1500,
(C) a cationic photoinitiator, and
(D) optionally, an organic solvent; and
(ii) exposing at least one selected region of the first silicone film to radiation having a wavelength of from about 150 to about 800 nm to produce a partially exposed film having at least one exposed region and at least one non-exposed region;
(iii) removing the non-exposed region of the partially exposed film with a developing solvent to form a patterned film;
(iv) heating the patterned film for an amount of time sufficient to form at least one silicone core having a refractive index of from about 1.45 to about 1.60 at about 23° C. for light having a wavelength of about 589 nm; wherein the substrate has a refractive index less than the refractive index of the silicone core;
(v) optionally covering the substrate and the silicone core with a second silicone composition to form a second silicone film; and
(vi) optionally curing the second silicone film to form a clad layer, wherein the clad layer has a refractive index less than the refractive index of the silicone core.

### Claim 10 (depends on 9)

The method of claim 9, further comprising, subsequent to exposing step (ii) and prior to removing step (iii):
(ii-2) heating the partially exposed film for an amount of time such that the exposed region is substantially insoluble in a developing solvent and the non-exposed region is soluble in the developing solvent.

### Claim 11 (depends on 9)

The method of claim 9, wherein the second silicone composition comprises:
(A) an epoxy-functional organopolysiloxane resin having the average unit formula
(R1R2R3SiO1/2)a(R4R5SiO2/2)b(R6SiO3/2)c(SiO4/2)d (I)
wherein R1, R2, R3, R4, R5, and R6 are organic groups independently selected from C1-6 monovalent aliphatic hydrocarbon groups, C6-10 monovalent aromatic hydrocarbon groups, and monovalent epoxy-substituted organic groups, 0≦a<0.4, 0<b<0.5, 0<c<1, 0≦d<0.4, 0.1≦b/c≦0.3, a+b+c+d=1, the resin has a number-average molecular weight of at least about 2000, at least about 15 mol % of the organic groups are C6 to C10 monovalent aromatic hydrocarbon groups, and about 2 to about 50 mol % of siloxane units have epoxy-substituted organic groups;
(B) an epoxy-functional organosiloxane oligomer having an average of at least two epoxy-substituted organic groups per molecule and a molecular weight not greater than about 1500;
(C) a cationic photoinitiator; and
(D) an organic solvent.

### Claim 12

A method of preparing a flexible planar optical waveguide assembly, comprising the steps of:
(i) applying a first silicone composition to a surface of a substrate to form a first silicone film;
(ii) curing the first silicone film to form a lower clad layer;
(iii) applying a second silicone composition to the lower clad layer to form a second silicone film;
(iv) exposing at least one selected region of the second silicone film to radiation having a wavelength of from about 150 to about 800 nm to produce a partially exposed film having at least one exposed region and at least one non-exposed region;
(v) removing the non-exposed region of the partially exposed film with a developing solvent to form a patterned film;
(vi) heating the patterned film for an amount of time sufficient to form at least one silicone core having a refractive index of from about 1.45 to about 1.60 at about 23° C. for light having a wavelength of 589 nm; wherein the lower clad layer has a refractive index less than the refractive index of the silicone core;
(vii) optionally covering the lower clad layer and the silicone core with a third silicone composition to form a third silicone film; and
(viii) optionally curing the third silicone film to form an upper clad layer, wherein the upper clad layer has a refractive index less than the refractive index of the silicone core,
wherein at least one of the first silicone composition and the second silicone composition comprises, and the third silicon composition optionally comprises:
(A) an epoxy-functional organopolysiloxane resin having the average unit formula
(R1R2R3SiO1/2)a(R4R5SiO2/2)b(R6SiO3/2)c(SiO4/2)d (I)
wherein R1, R2, R3, R4, R5, and R6 are organic groups independently selected from C1-6 monovalent aliphatic hydrocarbon groups, C6-10 monovalent aromatic hydrocarbon groups, and monovalent epoxy-substituted organic groups, 0≦a<0.4, 0<b<0.5, 0<c<1, 0≦d<0.4, 0.1≦b/c≦0.3, a+b+c+d=1, the resin has a number-average molecular weight of at least about 2000, at least about 15 mol % of the organic groups are C6 to C10 monovalent aromatic hydrocarbon groups, and about 2 to about 50 mol % of siloxane units have epoxy-substituted organic groups,
(B) an epoxy-functional organosiloxane oligomer having an average of at least two epoxy-substituted organic groups per molecule and a molecular weight not greater than about 1500,
(C) a cationic photoinitiator, and
(D) optionally, an organic solvent.

### Claim 13 (depends on 12)

The method of claim 12, further comprising, subsequent to exposing step (iv) and prior to removing step (v):
(iv-2) heating the partially exposed film for an amount of time such that the exposed region is substantially insoluble in a developing solvent and the non-exposed region is soluble in the developing solvent.

### Claim 14 (depends on 9)

The method of claim 9, wherein the optional steps of covering and curing are performed.

### Claim 15 (depends on 9)

A flexible planar optical waveguide assembly prepared according to the method of claim 9.

### Claim 16 (depends on 5)

The cured silicone composition of claim 5, wherein the silicone composition is cured using radiation.

### Claim 17 (depends on 5)

The cured silicone composition of claim 5, wherein the silicone composition is cured using UV light.

### Claim 18 (depends on 5)

The cured silicone composition of claim 5, wherein the silicone composition is cured using heat.

### Claim 19 (depends on 9)

The method of claim 9, further comprising (v) covering the substrate and the silicone core with a second silicone composition to form a second silicone film and (vi) curing the second silicone film to form a clad layer, wherein the clad layer has a refractive index less than the refractive index of the silicone core.

### Claim 20 (depends on 12)

The method of claim 12, further comprising (vii) covering the lower clad layer and the silicone core with a third silicone composition to form a third silicone film and (viii) curing the third silicone film to form an upper clad layer, wherein the upper clad layer has a refractive index less than the refractive index of the silicone core.