# US 10,370,492 B2 · UV-curable film compositions with improved scratch resistance

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- Number: US 10,370,492 B2
- Document ID: US10370492B2
- Status: Granted
- Kind: B2
- Application number: 14/211,552
- Filed: 2014-03-14
- Published: 2014-09-18
- Granted: 2019-08-06
- Earliest claimed: 2013-03-15
- Assignees: Sabic Global Technologies B.V.
- Applicants: Sabic Global Technologies B.V.
- Inventors: Kwan Hongladarom; Jean-Francois Morizur; Paul Dean Sybert
- Web page: https://patentgrep.com/patent/US10370492B2

## CPC

- C08G 64/42: Chemical after-treatment
- B29C 48/022: {characterised by the choice of material}
- B32B 27/365: {comprising polycarbonates}
- C08G 64/14: containing a chain-terminating or -crosslinking agent
- C08G 64/24: and phenols
- C08L 69/00: Compositions of polycarbonates; Compositions of derivatives of polycarbonates
- Y10T 428/2495: Thickness [relative or absolute]
- Y10T 428/269: including synthetic resin or polymer layer or component
- Y10T 428/31507: Of polycarbonate
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Thin walled products having good scratch resistance are disclosed, as are processes for making such products (e.g. films, sheets, and thin walled articles). The product includes a thin layer formed from (A) a cross-linkable polycarbonate resin having endcaps derived from a monohydroxybenzophenone; and (B) if desired, a base polymeric resin. When exposed to ultraviolet light, crosslinking will occur in the layer with the cross-linkable polycarbonate resin, enhancing the scratch resistance properties of the thin layer and the overall product.

## Claims

### Claim 1

A thin walled product comprising:
a crosslinked layer formed from a photoactive additive that has been exposed to ultraviolet light, the photoactive additive containing photoactive endcap groups derived from monohydroxybenzophenone and endcap groups derived from a non-photoactive end-capping agent;
wherein the photoactive additive is a homopolycarbonate formed from the reaction of:
the monohydroxybenzophenone;
a diol chain extender which is bisphenol A;
a first linker moiety which is phosgene; and
the non-photoactive end-capping agent; and
wherein the photoactive additive has a monohydroxybenzophenone-derived endcap content from 3.0 to 5.0 mol %; and
wherein the photoactive additive does not contain any aliphatic polyester, aliphatic polyether, aliphatic polythioether, aliphatic polyacetal, aliphatic polycarbonate, C-C linked polymer, and polysiloxane segments.

### Claim 2 (depends on 1)

The thin walled product of claim 1, wherein the thin walled product has a scratch rating of B or harder according to ASTM D3363.

### Claim 3 (depends on 2)

The thin walled product of claim 2, further comprising a substrate layer formed from a substrate resin and bonded to the crosslinked layer.

### Claim 4 (depends on 1)

The thin walled product of claim 1, wherein the monohydroxybenzophenone is 4-hydroxybenzophenone.

### Claim 5 (depends on 4)

The thin walled product of claim 4, wherein the photoactive additive has a weight average molecular weight of 15,000 or greater, measured prior to crosslinking.

### Claim 6 (depends on 1)

The thin walled product of claim 1, wherein the non-photoactive end-capping agent is selected from the group consisting of phenol, p-t-butylphenol, p-cumylphenol, octylphenol, and p-cyanophenol.

### Claim 7 (depends on 1)

The thin walled product of claim 1, wherein the reaction that forms the photoactive additive further comprises a secondary linker moiety having at least three functional groups, each of which can react with a linking group of the first linker moiety.

### Claim 8 (depends on 1)

A process for making the thin walled product of claim 1, comprising:
extruding a film layer comprising the photoactive additive; and
exposing the film layer to ultraviolet light to induce crosslinking in the film layer and obtain the thin walled product.

### Claim 9 (depends on 8)

The process of claim 8, wherein the film layer is co-extruded with a substrate resin that forms a substrate layer bonded to the film layer.

### Claim 10 (depends on 8)

The process of claim 8, wherein the thin walled layer has a scratch rating of B or harder according to ASTM D3363.

### Claim 11 (depends on 8)

The process of claim 8, wherein the film layer further comprises a polymeric base resin.

### Claim 12

A thin walled product comprising:
a crosslinked layer formed from a photoactive additive that has been exposed to ultraviolet light, the photoactive additive containing photoactive endcap groups derived from monohydroxybenzophenone;
and
wherein the photoactive additive has a monohydroxybenzophenone-derived endcap content from 3.0 to 5.0 mol %; and
the photoactive additive has a structure of Formula (II):
wherein n′ ranges from 29 to 65, and
wherein the thin walled product further comprises a substrate layer formed from a substrate resin and bonded to the crosslinked layer, and the thin walled product has a scratch rating of B or harder according to ASTM D3363.

### Claim 13 (depends on 12)

The thin walled product of claim 12, wherein the crosslinked layer is from about 2% to about 40% of the thickness of the thin walled product.

### Claim 14 (depends on 12)

The thin walled product of claim 12, wherein the crosslinked layer has a thickness of about 2.5 micrometers to about 12.7 millimeters.

### Claim 15 (depends on 12)

The thin walled product of claim 12, wherein the substrate resin is a polycarbonate film.

### Claim 16 (depends on 12)

The thin walled product of claim 12, wherein the photoactive additive has a weight-average molecular weight of between 17,000 and 80,000 Daltons, as measured by gel permeation chromatography using a UV-VIS detector and polycarbonate standards.

### Claim 17 (depends on 12)

The thin walled product of claim 12, wherein the crosslinked layer further comprises a polymeric base resin which is different from the photoactive addictive.

### Claim 18 (depends on 12)

The thin walled product of claim 12, wherein the crosslinked layer further comprises a flame retardant.