# US 5,705,276 A · Coating compositions of an acrylic fluorocarbon polymer and a fluorinated polyisocyanate

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- Number: US 5,705,276 A
- Document ID: US5705276A
- Status: Granted
- Kind: A
- Application number: 08/698,983
- Filed: 1996-10-28
- Granted: 1998-01-06
- Earliest claimed: 1995-10-16
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Douglas Robert Anton; Michael J. Darmon; William Frank Graham; Richard Ronald Thomas
- Web page: https://patentgrep.com/patent/US5705276A

## CPC

- C08G 18/8087: {containing halogen atoms}
- C08F 8/30: Introducing nitrogen atoms or nitrogen-containing groups
- C08G 18/6279: {containing fluorine atoms}
- Y10T 428/3154: Of fluorinated addition polymer from unsaturated monomers
- Y10T 428/31544: Addition polymer is perhalogenated
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A coating composition containing about 45-80% by weight of a binder and 20-55% by weight of an organic liquid; wherein the binder contains (A) about 40-90% by weight, based on the weight of the binder, of an acrylic polymer containing polymerized hydroxyl containing monomers of the following group of hydroxy alkyl acrylate or methacrylates having 1-4 carbon atoms in the alkyl group, and polymerized alkyl acrylates and methacrylates having 1-18 carbon atoms in the alkyl groups, or styrene or any mixtures of the above and 0.1-5.0% by weight, based on the weight of the acrylic polymer, of polymerized fluoroalkyl containing monomer represented by the formula ##STR1## where R is hydrogen or an alkyl group having 1-2 carbon atoms, n is an integer of 1-11 and R.sub.f is a fluoroalkyl containing group having at least 4 carbon atoms and (B) about 10-60% by weight, based on the weight of the binder, of a fluorinated organic polyisocyanate crosslinking agent.

## Claims

### Claim 1

A substrate coated with a dried and cured layer of a coating composition containing about 45-80% by weight of a binder and 20-55% by weight of an organic liquid; wherein the binder comprises
(A) about 40-90% by weight, based on the weight of the binder, of an acrylic polymer consisting essentially of about 20-45% by weight, based on the weight of the acrylic polymer, of polymerized hydroxyl containing monomers selected from the group consisting of hydroxy alkyl acrylate and hydroxy alkyl methacrylates having 1-4 carbon atoms in the alkyl groups, 50-79.9% by weight, based on the weight of the acrylic polymer, of polymerized monomers selected from the group consisting of alkyl acrylates and alkyl methacrylates having 1-18 carbon atoms in the alkyl groups, styrene and any mixtures of the above and 0.1-5.0% by weight, based on the weight of the acrylic polymer, of polymerized fluoroalkyl containing monomer represented by the formula ##STR9## where R is selected from the group consisting of hydrogen or an alkyl group having 1-2 carbon atoms, n is an integer of 1-11 and R.sub.f is a fluoroalkyl containing group having at least 4 carbon atoms and the acrylic polymer having a weight average molecular weight of about 2,000-20,000 determined by gel permeation chromatography, and
(B) about 10-60% by weight, based on the weight of the binder, of a fluorinated organic polyisocyanate crosslinking agent consisting essentially of an adduct of a fluorinated monofunctional alcohol and an organic polyisocyanate where the fluorinated monofunctional alcohol is represented by the formula ##STR10## where R.sub.f is as defined above, X is a divalent radical, R.sup.3 is H or an alkyl group having 1-4 carbon atoms, n is 1 and m is 1-30 and where about 0.1-33 mole percent of active isocyanate groups are reacted with the fluorinated monofunctional alcohol.

### Claim 2 (depends on 1)

A substrate coated with a pigmented base coat on which is coated a clear layer of the dried and cured coating composition of claim 1.

### Claim 3 (depends on 1)

The coating substrate of claim 1 in which R.sub.f of the fluoroalkyl monomer of the acrylic polymer and the fluorinated organic polyisocyanate is a straight chain or branched chain perfluoroalkyl group having 4-20 carbon atoms.

### Claim 4 (depends on 1)

The coated substrate of claim 1 in which the acrylic polymer consists essentially of polymerized monomers of an alkyl methacrylate having 2-6 carbon atoms in the alkyl groups, an alkyl acrylate having 2-8 carbon atoms in the alkyl group, a hydroxy alkyl acrylate having 2-4 carbon atoms in the alkyl group, styrene and a fluoroalkyl containing monomer wherein R is CH.sub.3 and n is 2.

### Claim 5 (depends on 1)

The coated substrate of claim 1 in which the acrylic polymer consists essentially of butyl methacrylate, butyl acrylate, styrene, hydroxy propyl acrylate and the perfluoroalkyl containing monomer.

### Claim 6 (depends on 1)

The coated substrate of claim 1 in which the fluoroalkyl containing monomer of the acrylic polymer is represented by the formula ##STR11## where R is as defined in claim 1,
R.sup.1 is a perfluoroalkyl group having 4-12 carbon atoms,
R.sup.2 is an alkyl group having 1-4 carbon atoms and n is an integer of 1-4.

### Claim 7 (depends on 1)

The coated substrate of claim 1 in which the fluorinated monofunctional alcohol X is --O--, --CH.sub.2 O--, CH.sub.2 CH.sub.2 O--, --SO.sub.2 N(R.sup.4)CH.sub.2 CH.sub.2 O--, --CH.sub.2 -- where R.sup.4 is H or methyl.

### Claim 8 (depends on 1)

The coated substrate of claim 1 in which the organic polyisocyanate is an aromatic diisocyanate, aliphatic diisocyanate, cycloaliphatic diisocyanate, aromatic triisocyanate, aliphatic triisocyanate, cycloaliphatic triisocyanate or an oligomer of a diisocyanate.

### Claim 9 (depends on 1)

The coated substrate of claim 1 containing about 0.1-10% by weight, based on the weight of the binder, of ultraviolet light stabilizers or an antioxidant or mixtures thereof.