Coating substrate by polymerization of amine compound and apparatus having polymer coated substrate

1. A method of making a laminate device, the method comprising:

providing an intermediate device comprising a plastic film and a metallic material layer, wherein the plastic film comprising a first plastic surface and a second plastic surface, wherein the metallic material layer is formed over the first plastic surface of the plastic film, wherein the metallic material layer comprises a first surface facing the plastic film and a second surface facing away from the plastic film; and

forming a polymer layer on the second surface of the metallic material layer to provide the laminate device in which the metallic material layer is interposed between the plastic film and the polymer layer,

wherein the polymer layer comprises polymer molecules chemically bonding to the second surface of the metallic material layer as a result of polymerization reactions of at least one monomer on the second surface rather than as a result of coating of a pre-polymerized polymer on the second surface,

wherein the polymerization reactions on the second surface do not involve a binder such that the polymer layer formed from the polymerization reactions does not comprise a binder,

wherein the at least one monomer is selected from the group consisting of compounds represented by any one of Chemical Formulae 1, 2, 3, 4, 5, 6, 7, 8, 9, 10 and 11 and Compound Nos. 204-248:

Compound

No.

Compound

204

1,3-diaminobenzene

205

1,4-diaminobenzene

206

4-(prop-2-en-1-yl)-4H-1,2,4-triazol-3-amine

207

5-amino-3-chloro-4-(prop-2-en-1-yl)-4H-1,2,4-triazole

208

5-amino-3-hydroxy-4-(prop-2-en-1-yl)-4H-1,2,4-triazole

209

5-amino-4-(prop-2-en-1-yl)-4H-1,2,4-triazole-3-carbonitrile

210

5-amino-4-(prop-2-en-1-yl)-4H-1,2,4-triazole-3-thiol

211

4-(prop-2-en-1-yl)-4H-1,2,4-triazol-3,5-diamine

212

5-amino-4-(prop-2-en-1-yl)-4H-1,2,4-triazole-3-

carbaldehyde

213

5-amino-4-(prop-2-en-1-yl)-4H-1,2,4-triazole-3-carboxylic

acid

214

3-amido-5-amino-4-(prop-2-en-1-yl)-4H-1,2,4-triazole

215

5-amino-3-methoxo-4-(prop-2-en-1-yl)-4H-1,2,4-triazole

216

5-amino-3-methoxy-4-(prop-2-en-1-yl)-4H-1,2,4-triazole

217

5-amino-3-nitro-4-(prop-2-en-1-yl)-4H-1,2,4-triazole

218

7-iodopyrazolo[1,5-a]pyrazin-4-amine

219

3-(3-iodo-1-methyl-1 H-pyrazol-5-yl)pyrazin-2-amine

220

5-(4-iodo-1H-pyrazol-1-yl)-1,3-thiazol-2-amine

221

4-iodo-5-(pyridazin-3-yl)-1,2-oxazol-3-amine

222

7-iodo-[1,2]oxazolo[4,5-b]pyridin-3-amine

223

5-(5-iodo-l1-methyl-1H-pyrazol-4-yl)-1,2-oxazol-3-amine

224

9-aminospiro[4.5]dec-8-en-7-one

225

2H,3H,4H,5H,6H,7H-furo[2,3-b]pyridin-3-one

226

5-(aminomethyl)-3-chlorofuran

227

5-(aminomethyl)-3-hydroxofuran

228

5-(aminomethyl)-3-cyanofuran

229

5-(aminomethyl)-3-sulfhydrofuran

230

5-(aminomethyl)-3-aminofuran

231

5-(aminomethyl)-3-formylfuran

232

5-(aminomethyl)-3-carboxofuran

233

5-(aminomethyl)-3-amidofuran

234

5-(aminomethyl)-3-methoxofuran

235

5-(aminomethyl)-3-methoxyfuran

236

5-(aminomethyl)-3-nitrofuran

237

1-[4-(prop-2-en-1-yl)furan-2-yl]methanamine

238

1-[3-chloro-4-(prop-2-en-1-yl)furan-2-yl]methanamine

239

1-[3-hydroxo-4-(prop-2-en-1-yl)furan-2-yl]methanamine

240

1-[3-cyano-4-(prop-2-en-1-yl)furan-2-yl]methanamine

241

1-[3-sulfhydro-4-(prop-2-en-1-yl)furan-2-yl]methanamine

242

1-[3-amino-4-(prop-2-en-1-yl)furan-2-yl]methanamine

243

1-[3-formyl-4-(prop-2-en-1-yl)furan-2-yl]methanamine

244

1-[3-carboxo-4-(prop-2-en-1-yl)furan-2-yl]methanamine

245

1-[3-amido-4-(prop-2-en-1-yl)furan-2-yl]methanamine

246

1-[3-methoxo-4-(prop-2-en-1-yl)furan-2-yl]methanamine

247

1-[3-methoxy-4-(prop-2-en-1-yl)furan-2-yl]methanamine

248

1-[3-nitro-4-(prop-2-en-1-yl)furan-2-yl]methanamine

Chemical

each of L 11 to L 16 is independently either a single bond or a

Formula 1

double bond, at least one of L 11 to L 16 is a double bond,

each of A 11 to A 16 is independently selected from the group

consisting of —C(R 11 R 12 )—, —N(R 13 )—, —O— and

—S—, at least of one of A 1 to A 6 is selected from the group

consistingof —N(R 13 )—, —O— and —S—,

at least of one of A 11 to A 16 is C(R 11 R 12 ),

each of R 11 and R 12 is independently selected from the group

consisting of H, NH 2 , ═NH, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-,

CN, carboxyl, formyl, OH and SH, or forms a carbonyl or

thiocarbonyl group with an adjacent carbon,

R 13 is H or NH 2 ,

with the proviso that (a) any of L 11 -L 16 adjacent a double

bond are single bonds, and any of A 11 -A 16 connected by a

double bond are not —O— or —S—,

(b) if any one of A 11 -A 16 connected by a double bond is

—C(R 11 R 12 )— or —N(R 13 ), R 12 and R 13 are omitted,

(c) at least one of R 11 , R 12 and R 13 is NH 2 ,

Chemical

each of L 21 to L 25 is independently either a single bond or

Formula 2

a double bond, at least one of L 21 to L 25 is a double bond,

each of A 21 to A 25 is independently selected from the group

consisting of —C(R 21 R 22 )—, —N(R 23 )—, —O— and

—S—, at least of one of A 21 to A 25 is selected from the

group consisting of —N(R 23 )—, —O— and —S—,

at least of one of A 21 to A 25 is C(R 21 R 22 ),

each of R 21 and R 22 is independently selected from the

group consisting of H, NH 2 , ═NH, C 1 -C 6 alkyl, C 1 -C 6 alkoxy,

halo-, CN, carboxyl, formyl, OH and SH, or forms a

carbonyl or thiocarbonyl group with an adjacent carbon,

R 23 is H or NH 2 ,

with the proviso that (a) any of L 21 -L 25 adjacent a double

bond are single bonds, and any of A 21 -A 25 connected by a

double bond are not —O— or —S—,

(b) if any one of A 21 -A 25 connected by a double bond is

—C(R 21 R 22 )— or —N(R 23 ), R 22 and R 23 are omitted,

(c) at least one of R 21 , R 22 and R 23 is NH 2

Chemical

each of L 31 to L 36 is independently either a single bond or a

Formula 3

double bond, each of A 31 to A 35 is selected from the group

consisting of —C(R 31 R 32 )—, —N(R 33 )—, —O— and —S—,

at least of one of A 31 to A 35 is selected from the group

consisting of —N(R 33 )—, —O— and —S—,

at least of one of A 31 to A 35 is C(R 31 R 32 ),

each of R 31 and R 32 is independently selected from the group

consisting of H, NH 2 , ═NH, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-,

CN, carboxyl, formyl, OH and SH, or forms a carbonyl or

thiocarbonyl group with an adjacent carbon,

R 33 is H or NH 2 ,

R 34 is H,

with the proviso that (a) any of L 31 to L 36 adjacent a double

bond are single bonds, and any of A 31 to A 35 connected by a

double bond are not —O— or —S—,

(b) if any one of A 31 to A 35 connected by a double bond

is —C(R 31 R 32 )— or —N(R 33 ), R 32 and R 33 are omitted,

(c) if L 31 or L 36 is a double bond, R 34 is omitted,

Chemical

each of L 41 to L 45 is independently either a single bond or a

Formula 4

double bond, each of A 41 to A 44 is selected from the group

consisting of —C(R 41 R 42 )—, —N(R 43 )—, —O— and —S—,

at least of one of A 41 to A 44 is selected from the group

consisting of —N(R 43 )—, —O— and —S—,

at least of one of A 41 to A 44 is C(R 41 R 42 ),

each of R 41 and R 42 is independently selected from the group

consisting of H, NH 2 , ═NH, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo-,

CN, carboxyl, formyl, OH and SH, or forms a carbonyl or

thiocarbonyl group with an adjacent carbon,

R 43 is H or NH 2 ,

R 44 is H,

with the proviso that (a) any of L 41 to L 45 adjacent a double

bond are single bonds, and any of A 41 to A 44 connected by a

double bond are not —O— or —S—,

(b) if any one of A 41 to A 44 connected by a double bond

is —C(R 41 R 42 )— or —N(R 43 ), R 42 and R 43 are omitted,

(c) if L 41 or L 45 is a double bond, R 44 is omitted

Chemical

each R 51 is independently selected from the group

Formula 5

consisting of H, —NH 2 , halo, C 1 -C 6 alkyl, C1-C6 alkoxy,

CN, carboxyl, formyl, OH and SH, each R 52 is independently

selected from the group consisting of H, —NH 2 ,

halo, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, CN, carboxyl, formyl, OH,

SH and ═NH or forms a carbonyl or thiocarbonyl group

with an adjacent carbon to which it is connected,

with the proviso that (a) at least one of R 51 and R 52 is NH 2 ,

(b) if R 52 is —NH 2 , halo, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, CN,

carboxyl, formyl, OH or SH, the other R 52 connected to the

same carbon is H,

(c) if R 52 is ═NH or forms a carbonyl or thiocarbonyl group

with an adjacent carbon, the other R 52 connected to the same

carbon is omitted,

Chemical

each R 61 is independently selected from the group

Formula 6

consisting of H, —NH 2 , halo, C 1 -C 6 alkyl, C1-C6 alkoxy,

CN, carboxyl, formyl, OH and SH, each R 62 is independently

selected from the group consisting of H, —NH 2 , halo,

C 1 -C 6 alkyl, C 1 -C 6 alkoxy, CN, carboxyl, formyl, OH, SH and

═NH or forms a carbonyl or thiocarbonyl group with an

adjacent carbon, with the proviso that (a) at least one of

R 61 and R 62 is NH 2 ,

(b) if R 62 is —NH 2 , halo, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, CN,

carboxyl, formyl, OH or SH, the other R 62 connected to

the same carbon is H,

(c) if R 62 is ═NH or forms a carbonyl or thiocarbonyl group

with an adjacent carbon, the other R 62 connected to the

same carbon is omitted,

Chemical

each of L 71 to L 76 is independently a single or double bond,

Formula 7

L 71 to L 76 have total 0-2 double bonds,

each R 71 and R 72 is selected from the group consisting of

H, —NH 2 , ═NH, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo,

CN, carboxyl, formyl, OH and SH or forms a carbonyl or

thiocarbonyl group with an adjacent carbon, R 73 is

selected from the group consisting of H, —NH 2 , C 1 -C 6 alkyl,

C 1 -C 6 alkoxy, halo, CN, carboxyl, formyl, —OH and

—SH, with the proviso that (a) any of L 71 -L 76 adjacent a

double bond are single bonds,

(b) R 72 connected to a carbon that forms a double bond

among L 71 to L 76 is omitted,

(c) if L 71 or L 76 is a double bond, R 72 is omitted,

(d) if either of R 71 and R 72 is ═NH or forms a carbonyl or

thiocarbonyl group with an adjacent carbon, then the other

of R 71 and R 72 is omitted,

(e) at least one of R 71 to R 73 is —NH 2

Chemical

each of L 81 to L 85 is independently a single or double bond,

Formula 8

L 81 to L 85 have total 0 or 1 double bond,

each of R 81 and R 82 is independently selected from the group

consisting of H, —NH 2 , ═NH, C 1 -C 6 alkyl, C 1 -C 6 alkoxy,

halo, CN, carboxyl, formyl, OH and SH or forms a

carbonyl or thiocarbonyl group with an adjacent carbon,

R 83 is selected from the group consisting of H, —NH 2 , C 1 -C 6

alkyl, C 1 -C 6 alkoxy, halo, CN, carboxyl, formyl, —OH and

—SH, with the proviso that (a) any of L 81 -L 85 adjacent a

double bond are single bonds,

(b) R 82 connected to a carbon that forms a double bond

among L 81 to L 85 is omitted,

(c) if L 81 or L 85 is a double bond, R 83 is omitted,

(d) if either of R 81 and R 82 is ═NH or forms a carbonyl or

thiocarbonyl group with an adjacent carbon, then the

other of R 81 and R 82 is omitted,

(e) at least one of R81 to R83 is —NH2,

Chemical

X a is —NH 2 , —N═CH—OH, or —N═O,

Formula 10

R a1 is hydrogen, C 1 -C 6 lkyl, or —CN,

R a2 and R a3 is independently selected from the group

consisting of hydrogen, C 1 -C 6 alkyl, —CN, —OH,

—NH 2 , —NH—OH, —C(O)R a4 , and —C(O)OR a5 (R a4 and

R a5 is hydrogen or C 1 -C 6 alkyl),

Chemical

R b1 is selected from the group consisting of H, NH 2 , and

Formula 11

NH— acyl.

2. The method of claim 1 , wherein forming the polymer layer comprises contacting the second surface of the metallic material layer with a polymerization composition comprising the at least one monomer, which causes the polymerization reactions, wherein the metallic material layer comprises a metal foil having a thickness in a range between about 1 μm and about 200 μm, wherein the intermediate device further comprises an adhesive layer between the metallic material layer and the plastic film.

3. The method of claim 1 , wherein providing the intermediate device comprises:

providing the plastic film and the metallic material layer; and

laminating the plastic film and the metallic material layer with an adhesive material applied between the plastic film and the metallic material layer to provide an adhesive layer interposed between the plastic film and the metallic material layer.

4. The method of claim 1 , wherein the metallic material layer comprises a deposit of a metallic material formed on the plastic film and has a thickness in a range between about 1 nm and about 50 nm, wherein no distinct layer is interposed between the metallic material layer and the plastic film.

5. The method of claim 1 , wherein providing the intermediate device comprises:

providing the plastic film; and

conducting a vapor deposition of a metallic material to form the metallic material layer on the plastic film.

6. The method of claim 5 , wherein providing the intermediate device further comprises subjecting a surface of the plastic film to a plasma treatment before conducting the vapor deposition, wherein the vapor deposition of the metallic material is performed on the surface of the plastic film.

7. The method of claim 1 , wherein forming the polymer layer comprises contacting the second surface of the metallic material layer with a polymerization composition comprising the at least one monomer, which causes the polymerization reactions, wherein the metallic material layer comprises one or more selected from the group consisting of holes, pores, and defects therein, wherein at least part of the polymer molecules covers or enters the one or more selected from the group consisting of holes, pores, and defects.

8. The method of claim 1 , wherein the polymer layer, as a result of polymerization reactions on the metallic material layer, comprises at least one selected from the group consisting of oligomers, tetramers, trimers, and dimers derived from the at least one monomer in a substantial amount that a commercially available composition of a pre-polymerized polymer having a specific range of polymer molecular weights would not contain.

9. The method of claim 1 , wherein the polymer layer, as a result of polymerization reactions on the metallic material layer, comprises at least one selected from the group consisting of oligomers, tetramers, trimers, and dimers chemically bonded to the second surface of the metallic material layer that would not occur when coating a pre-polymerized polymer composition on the metallic material layer.

10. The method of claim 1 , wherein the metallic material layer comprises a pinhole extending through a thickness of the metallic material layer, wherein at least one of an oligomer and a polymer occupies at least part of a space of the pinhole and is chemically bonded to an interior surface of the pinhole that would not occur when coating a pre-polymerized polymer composition on the metallic material layer.

11. The method of claim 1 , wherein the polymer layer, not as a result of coating of a pre-polymerized polymer composition on the metallic material layer, does not comprise a polymerization inhibitor that a commercially available composition of a pre-polymerized polymer having a specific range of molecular weights would contain to inhibit additional polymerization reactions or cross-linking reactions in the polymer composition.

12. The method of claim 1 , wherein the polymer layer does not comprise a surfactant that would be included in the polymer layer, if the polymer layer is formed by coating of a pre-polymerized polymer, for evenly coating a pre-polymerized polymer on the metallic material layer.

13. The method of claim 1 , wherein the polymer layer is referred to as a first polymer layer, wherein the method further comprises:

forming a second polymer layer on the second plastic surface such that the plastic film is interposed between the second polymer layer and the metallic material layer,

wherein the second polymer layer comprises polymers derived from the at least one monomer as a result of polymerization reactions on the second plastic surface rather than a result of coating a pre-polymerized polymer composition on the second plastic surface, wherein the second polymer layer does not comprise a binder for attaching the second polymer layer to the second plastic surface.

14. The method of claim 13 , wherein each of the first and second polymer layers has a thickness in a range between about 1 μm and about 20 μm.

15. The method of claim 13 , wherein the second polymer layer, as a result of polymerization reactions on the second plastic surface, comprises at least one selected from the group consisting of oligomers, tetramers, trimers, and dimers derived from the at least one monomer in a substantial amount that a commercially available composition of a pre-polymerized polymer having a specific range of polymer molecular weights would not contain.

16. The method of claim 13 , wherein the second polymer layer, as a result of polymerization reactions on the second plastic surface, comprises at least one selected from the group consisting of oligomers, tetramers, trimers, and dimers chemically bonded to the second plastic surface that a commercially available composition of a pre-polymerized polymer having a specific range of polymer molecular weights would not contain.

17. The method of claim 13 , wherein the plastic film comprises an engineering polymer layer with pores, wherein at least one of an oligomer and a polymer stays in at least one of the pores and is chemically bonded to an interior surface of at least one pore that would not occur when coating a pre-polymerized polymer composition on the plastic film.

18. The method of claim 13 , wherein the metallic material layer comprises a metal oxide.

19. The method of claim 13 , wherein the second polymer layer, not as a result of coating of a pre-polymerized polymer composition on the plastic film, does not comprise a polymerization inhibitor that a commercially available composition of a pre-polymerized polymer having a specific range of molecular weights would contain to inhibit additional polymerization reactions or cross-linking reactions in the polymer composition.

20. The method of claim 1 , wherein forming the polymer layer comprises contacting the second surface of the metallic material layer with a polymerization reaction composition that comprises the at least one monomer but does not comprise any of a surfactant, a polymerization initiator and a polymerization inhibitor such that the polymer layer does not comprise a surfactant, a polymerization initiator or a polymerization inhibitor.