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1. (WO2017002016) PLASTIC SURFACES HAVING ENHANCED HARDNESS AND METHODS OF MAKING THE SAME
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CLAIMS

What is claimed is:

1. A method of enhancing hardness of a plastic surface, the method comprising:

coating a surface of a solid plastic form comprising a filler, a polyester, or a combination thereof, with a flowable curable coating composition comprising

a) an alicyclic epoxy group-containing siloxane resin having a weight average molecular weight of about 1,000 to about 4,000 and a (Mw/Mn) of about 1.05 to about 1.4,

b) an epoxy-functional organosiloxane and an organosiloxane comprising a isocyanate group or an isocyanurate group, or

both a) and b); and

curing the curable coating composition, to provide a hardened film on the solid plastic form surface.

2. The method of claim 1, wherein the epoxy-functional organosiloxane has the structure:


wherein

at each occurrence, Ra is independently substituted or unsubstituted (Ci-Cio)alkyl, La is substituted or unsubstituted (Ci-C3o)hydrocarbyl interrupted by 0, 1, 2, or 3 groups independently chosen from -0-, -S-, substituted or unsubstituted -NH-, -(Si(ORa)2)ni-, -(0-CH2-CH2)ni-, and -(0-CH2-CH2-CH2)ni-, wherein nl is about 1 to about 1,000.

3. The method of any one of claims 1-2, wherein the organosiloxane comprising an isocyanate group has the structure (Rb)4_pSi(Rc)p, wherein

p is 1 to 4,

at each occurrence, Rb is independently chosen from substituted or unsubstituted (Ci-Cio)alkyl and substituted or unsubstituted (Ci-Cio)alkoxy, and

at each occurrence, Rc is -Lb-NCO, wherein Lb is a substituted or unsubstituted (Ci-C3o)hydrocarbyl interrupted by 0, 1, 2, or 3 groups independently chosen from -0-, -S-, substituted or unsubstituted -NH-, -(Si(ORb)2)n2-, -(0-CH2-CH2)n2-, and -(0-CH2-CH2-CH2)n2-, wherein n2 is about 1 to about 1,000.

The method of any one of claims 1-3, wherein the organosiloxane comprising yanurate group has the structure:


wherein

at each occurrence, Rd is chosen from -H and -Lc-Si(Re)3, wherein at least one Rd is -Lc-Si(Re)3,

at each occurrence, Lc is independently a substituted or unsubstituted (Q- C3o)hydrocarbyl interrupted by 0, 1, 2, or 3 groups independently chosen from -0-, -S-, substituted or unsubstituted -NH-, -(Si(Re)2)n3-, -(0-CH2-CH2)n3-, and -(0-CH2-CH2-CH2)n3-, wherein n3 is about 1 to about 1,000, and

at each occurrence, Re is chosen from substituted or unsubstituted (Ci-Cio)alkyl and substituted or unsubstituted (Ci-Cio)alkoxy.

5. The method of any one of claims 1-4, wherein the bis(organosiloxane)-functional amine has the structure Rf3Si-Ld-NH-Ld-SiRf3, wherein

at each occurrence, R is chosen from substituted or unsubstituted (Ci-Cio)alkyl and substituted or unsubstituted (Ci-Cio)alkoxy, and

at each occurrence, Ld is independently a substituted or unsubstituted (Ci-C3o)hydrocarbyl interrupted by 0, 1, 2, or 3 groups independently chosen from -0-, -S-, substituted or unsubstituted -NH-, -(Si(Rf)2)n4-, -(0-CH2-CH2)n4-, and -(0-CH2-CH2-CH2)n4-, wherein n4 is about 1 to about 1,000.

6. The method of any one of claims 1-5, wherein the siloxane resin is a hydrolysis and condensation reaction product of

(i) an alkoxysilane comprising an alicyclic epoxy group and an alkoxy group having the structure R 1 nSi(OR2 )4_n alone, wherein R 1 is (C3-C6)cycloalkyl(Ci-C6)alkyl wherein the cycloalkyl group comprises an epoxy group, R is (Ci-C7)alkyl, and n is 1-3, or

(ii) the alkoxysilane having the structure R 1 nSi(OR 2 )4_n and an alkoxysilane having the structure R 3 mSi(OR 4 )4_m, wherein R 3 is chosen from (Ci-C2o)alkyl, (C3-C8)cycloalkyl, (C2-C2o)alkenyl, (C2-C20)alkynyl, (C6-C2o)aryl, an acryl group, a methacyl group, a halogen group, an amino group, a mercapto group, an ether group, an ester group, a carbonayl group, a carboxyl group, a vinyl group, a nitro group, a sulfone group, and an alkyd group, R4 is (Ci-C7)alkyl, and m is 0 to 3,

wherein hydrolysis and condensation reaction is carried out in the presence of water and an optional catalyst.

7. The method of any one of claims 1-6, wherein the flowable curable coating composition further comprises a reactive monomer capable of reacting with the alicyclic epoxy group to form cros slinking.

8. The method of claim 6, wherein the catalyst is present and is chosen from acidic catalysts, basic catalysts, ion exchange resins, and combinations thereof.

9. The method of any one of claims 1-8, wherein the hardened film has a thickness of about 1 micrometer to about 100 micrometers.

10. The method of any one of claims 1-9, wherein the hardened film on the solid plastic form surface has a hardness of about 3B to about 9H.

11. The method of any one of claims 1-10, wherein the hardened film on the solid plastic form surface has a hardness of about HB to about 8H.

12. The method of any one of claims 1-11, wherein the solid plastic form comprises at least one of an acrylonitrile butadiene styrene (ABS) polymer, an acrylic polymer, a celluloid polymer, a cellulose acetate polymer, a cycloolefin copolymer (COC), an ethylene-vinyl acetate (EVA) polymer, an ethylene vinyl alcohol (EVOH) polymer, a fluoroplastic, an ionomer, an acrylic/PVC alloy, a liquid crystal polymer (LCP), a polyacetal polymer (POM or acetal), a polyacrylate polymer, a polymethylmethacrylate polymer (PMMA), a polyacrylonitrile polymer (PAN or acrylonitrile), a poly amide polymer (PA or nylon), a polyamide-imide polymer (PAI), a polyaryletherketone polymer (PAEK), a polybutadiene polymer (PBD), a polybutylene polymer (PB), a polybutylene terephthalate polymer (PBT), a polycaprolactone polymer (PCL), a

polychlorotrifluoroethylene polymer (PCTFE), a polytetrafluoroethylene polymer (PTFE), a polyethylene terephthalate polymer (PET), a polycyclohexylene dimethylene terephthalate polymer (PCT), a polycarbonate polymer (PC), a polyhydroxyalkanoate polymer (PHA), a polyketone polymer (PK), a polyester polymer, a polyethylene polymer (PE), a

polyetheretherketone polymer (PEEK), a polyetherketoneketone polymer (PEKK), a

polyetherketone polymer (PEK), a polyetherimide polymer (PEI), a polyethersulfone polymer (PES), a polyethylenechlorinate polymer (PEC), a polyimide polymer (PI), a polylactic acid polymer (PLA), a polymethylpentene polymer (PMP), a polyphenylene oxide polymer (PPO), a polyphenylene sulfide polymer (PPS), a polyphthalamide polymer (PPA), a polypropylene polymer, a polystyrene polymer (PS), a polysulfone polymer (PSU), a polytrimethylene terephthalate polymer (PTT), a polyurethane polymer (PU), a polyvinyl acetate polymer (PVA), a polyvinyl chloride polymer (PVC), a polyvinylidene chloride polymer (PVDC), a

polyamideimide polymer (PAI), a polyarylate polymer, a polyoxymethylene polymer (POM), and a styrene-acrylonitrile polymer (SAN).

13. The method of any one of claims 1-12, wherein the solid plastic form comprises at least one of polycarbonate polymer (PC) and polymethylmethacrylate polymer (PMMA).

14. The method of any one of claims 1-13, wherein the filler is about 0.001 wt% to about 50 wt% of the solid plastic form.

15. The method of any one of claims 1-14, wherein the polyester is about 0.001 wt% to about 50 wt% of the solid plastic form.

16. The method of any one of claims 1-15, wherein the polyester comprises a repeating unit having the structure:


wherein

R 8° and FT 9 are independently substituted or unsubstituted (Ci-C2o)hydrocarbylene.

17. The method of claim 16, wherein R 8 and R 9 independently have the structure:

18. A method of enhancing hardness of a plastic surface, the method comprising:

coating a surface of a solid polycarbonate form comprising glass fibers, a polyester, or a combination thereof, with a flowable curable coating composition, comprising

a) an alicyclic epoxy group-containing siloxane resin having a weight average molecular weight of about 1,000 to about 4,000 and a (Mw/Mn) of about 1.05 to about 1.4, b) an epoxy-functional organosiloxane and an organosiloxane comprising a isocyanate group or an isocyanurate group, or

both a) and b); and

curing the curable coating composition, to provide a hardened film on the solid polycarbonate form surface having a hardness of about 3B to about 9H, wherein the solid polycarbonate form is about 50 wt% to about 100 wt% polycarbonate.

19. A solid plastic form having enhanced surface hardness, the plastic form comprising: a hardened film on a surface of the solid plastic form, the hardened film comprising a cured reaction product of a flowable curable coating composition comprising

a) an alicyclic epoxy group-containing siloxane resin having a weight average molecular weight of about 1,000 to about 4,000 and a (Mw/Mn) of about 1.05 to about 1.4, b) an epoxy-functional organosiloxane and an organosiloxane comprising a isocyanate group or an isocyanurate group, or

both a) and b);

wherein the solid plastic form comprises a filler, a polyester, or a combination thereof, and the hardened film on the surface of the solid plastic form has a hardness of about 3B to about 9H.

20. A mobile phone component, a television component, an appliance component, an automobile component, a window, a display film, an anti-scattering film or sheet, or a combination thereof, comprising the plastic form comprising the hardened film of claim 19.