# US 12,600,820 B2 · Photocurable composition with high silicon content

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- Number: US 12,600,820 B2
- Document ID: US12600820B2
- Status: Granted
- Kind: B2
- Application number: 18/062,374
- Filed: 2022-12-06
- Published: 2024-06-20
- Granted: 2026-04-14
- Earliest claimed: 2022-12-06
- Assignees: Canon Kabushiki Kaisha
- Applicants: Canon Kabushiki Kaisha
- Inventors: Fen Wan; Weijun Liu
- Web page: https://patentgrep.com/patent/US12600820B2

## CPC

- C08G 77/22: containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C09D 183/04: Polysiloxanes
- C08G 77/18: to alkoxy or aryloxy groups
- C09D 183/08: containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
- C08G 77/045: {containing less than 25 silicon atoms}
- C08G 77/20: containing silicon bound to unsaturated aliphatic groups
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- 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)

## Abstract

A photocurable composition can comprise a polymerizable material and a photoinitiator, wherein the polymerizable material may comprise at least one silicon-containing monomer having a structure of formula (1) with R1, R2: —O—Si(CH3)3, alkyl, aryl, or alkylaryl; R3, R4: —O—Si(CH3)3, alkyl, aryl, or alkylaryl; R5: C1-C5-alkyl, aryl, alkylaryl; R6: —R5-X, or X, or —O—Si(CH3)3, or alkyl, or aryl, or alkylaryl; X: acrylate or methacrylate; and n: 0-4. The amount of silicon (Si) in the photocurable composition can be at least 15 wt % based on the total weight of the photocurable composition.

## Claims

### Claim 1

A photocurable composition comprising a polymerizable material and a photoinitiator, wherein
the polymerizable material comprises at least one silicon-containing monomer having a structure of formula (1)
with R1, R2: —O—Si(CH3)3, alkyl, aryl, or alkylaryl
R3, R4: —O—Si(CH3)3, alkyl, aryl, or alkylaryl
R5: C1-C5-alkyl, aryl, alkylaryl
R6: —R5-X, or X, or —O—Si(CH3)3, or alkyl, or aryl, or alkylaryl
X: acrylate or methacrylate
n: 0-4;
an amount of silicon (Si) in the photocurable composition is at least 15 wt % based on the total weight of the photocurable composition; and
a viscosity of the photocurable composition is not greater than 20 mPa·s.

### Claim 2 (depends on 1)

The photocurable composition of claim 1, wherein the amount of Si is at least 20 wt % based on the total weight of the photocurable composition.

### Claim 3 (depends on 1)

The photocurable composition of claim 1, wherein a molecular weight of the silicon-containing monomer is at least 100 g/mol and not greater than 700 g/mol.

### Claim 4 (depends on 1)

The photocurable composition of claim 1, wherein an amount of the at least one silicon-containing monomer of formula (1) is at least 60 wt % based on the total weight of the polymerizable material.

### Claim 5 (depends on 4)

The photocurable composition of claim 4, wherein the amount of the at least one silicon-containing monomer is at least 60 wt % and not greater than 85 wt % based on the total weight of the polymerizable material.

### Claim 6 (depends on 1)

The photocurable composition of claim 1, wherein an amount of the polymerizable material is at least 90 wt % based on the total weight of the photocurable composition.

### Claim 7 (depends on 1)

The photocurable composition of claim 1, wherein the photocurable composition is essentially free of a solvent.

### Claim 8 (depends on 1)

The photocurable composition of claim 1, wherein the at least one silicon-containing monomer includes at least two different silicon-containing monomers.

### Claim 9 (depends on 1)

The photocurable composition of claim 1, wherein the at least one silicon-containing monomer is selected from the group of
methacryloxymethyltris(trimethylsiloxane)silane (SiM1),
1,3-bis(3-methacryloxypropyl)tetrakis(trimethylsiloxy)disiloxane (SiM2),
3-acryloxypropyltris(trimethylsiloxy)silane (SiM3),
(methacryloxymethyl)bis(trimethylsiloxy)methylsilane (SiM4),
3-methacryloxypropylbis(trimethylsiloxy)methylsilane (SiM5),
(3-acryloxypropyl)methylbis(trimethylsiloxy)silane (SiM6),
methacryloxypropyltris(trimethylsiloxy)silane (SiM7),
acryloxymethyltrimethylsilane (SiM8),
acryloxymethyltris(trimethylsiloxy)silane (SiM9),
1,3-bis[(acryloxymethyl)phenethyl]tetramethyldisiloxane (SiM10),
or any combination thereof.

### Claim 10 (depends on 9)

The photocurable composition of claim 9, wherein the at least one silicon-containing monomer includes
methacryloxymethyltris(trimethylsiloxane)silane (SiM1),
1,3-bis(3-methacryloxypropyl)tetrakis(trimethylsiloxy)disiloxane (SiM2), or
3-acryloxypropyl-tris(trimethylsiloxy)silane (SiM3), or any combination thereof.

### Claim 11 (depends on 1)

The photocurable composition of claim 1, wherein the polymerizable material further comprises at least one polymerizable monomer not containing silicon.

### Claim 12 (depends on 11)

The photocurable composition of claim 11, wherein the polymerizable monomer not containing silicon includes an acrylate monomer.

### Claim 13 (depends on 12)

The photocurable composition of claim 12, wherein the acrylate monomer includes benzyl acrylate (BA), isobornyl acrylate (IBOA), 1,5-pentanediol diacrylate (MPDA), dihydrodicyclopentadienyl acrylate (DCPA), tricyclodecane dimethanol diacrylate (A-DCP), 1-phenyl-1,2-ethanediyl ester (PHEDA), or any combination thereof.

### Claim 14 (depends on 1)

A laminate, the laminate comprising a substrate and a photo-cured layer overlying the substrate, wherein the photo-cured layer is formed from the photocurable composition of claim 1.

### Claim 15

A method of forming a photo-cured layer on a substrate, comprising:
applying a layer of a photocurable composition on the substrate, wherein the photocurable composition comprises a polymerizable material and at least one photoinitiator, wherein
the polymerizable material comprises at least one silicon-containing monomer having a structure of formula (1)
with R1, R2: —O—Si(CH3)3, alkyl, aryl, or alkylaryl
R3, R4: —O—Si(CH3)3, alkyl, aryl, or alkylaryl
R5: C1-C5-alkyl, aryl, alkylaryl
R6: —R5-X, or X, or —O—Si(CH3)3, or alkyl, or aryl, or alkylaryl
X: acrylate or methacrylate
n: 0-4; and
an amount of silicon (Si) in the photocurable composition is at least 15 wt % based on the total weight of the photocurable;
bringing the photocurable composition into contact with a template or a superstrate;
irradiating the photocurable composition with light to form a photo-cured layer; and
removing the template or the superstrate from the photo-cured layer.

### Claim 16 (depends on 15)

The method of claim 15, wherein the amount of Si is at least 20 wt % based on the total weight of the photocurable composition.

### Claim 17 (depends on 15)

The method of claim 15, wherein a viscosity of the photocurable composition is not greater than 20 mPa·s.

### Claim 18 (depends on 15)

The method of claim 15, wherein an amount of the polymerizable material is at least 90 wt % based on the total weight of the photocurable composition.

### Claim 19

A method of manufacturing an article, comprising:
applying a layer of a photocurable composition on a substrate, wherein the photocurable composition comprises a polymerizable material and at least one photoinitiator, wherein
the polymerizable material comprises at least one silicon-containing monomer having a structure of formula (1)
with R1, R2: —O—Si(CH3)3, alkyl, aryl, or alkylaryl
R3, R4: —O—Si(CH3)3, alkyl, aryl, or alkylaryl
R5: C1-C5-alkyl, aryl, alkylaryl
R6: —R5-X, or X, or —O—Si(CH3)3, or alkyl, or aryl, or alkylaryl
X: acrylate or methacrylate
n: 0-4; and
an amount of silicon (Si) in the photocurable composition is at least 15 wt % based on the total weight of the photocurable composition;
bringing the photocurable composition into contact with a template or a superstrate;
irradiating the photocurable composition with light to form a photo-cured layer;
removing the template or the superstrate from the photo-cured layer;
forming a pattern on the substrate;
processing the substrate on which the pattern has been formed in the forming; and
manufacturing the article from the substrate processed in the processing.

### Claim 20

A photocurable composition comprising a polymerizable material and a photoinitiator, wherein
the polymerizable material comprises at least one silicon-containing monomer having a structure of formula (1)
with R1, R2: —O—Si(CH3)3, alkyl, aryl, or alkylaryl
R3, R4: —O—Si(CH3)3, alkyl, aryl, or alkylaryl
R5: C1-C5-alkyl, aryl, alkylaryl
R6: —R5-X, or X, or —O—Si(CH3)3, or alkyl, or aryl, or alkylaryl
X: acrylate or methacrylate
n: 0-4;
an amount of silicon (Si) in the photocurable composition is at least 15 wt % based on the total weight of the photocurable composition; and
the at least one silicon-containing monomer includes methacryloxymethyltris(trimethylsiloxane)silane (SiM1), 1,3-bis(3-methacryloxypropyl)tetrakis(trimethylsiloxy)disiloxane (SiM2), 3-acryloxypropyl-tris(trimethylsiloxy)silane (SiM3), or any combination thereof.