# US 5,352,755 A · Blocked isocyanates

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- Number: US 5,352,755 A
- Document ID: US5352755A
- Status: Granted
- Kind: A
- Application number: 08/079,904
- Filed: 1993-06-23
- Granted: 1994-10-04
- Earliest claimed: 1984-02-29
- Assignees: The Baxenden Chemical Co.
- Inventors: Anthony H. Hughes; Arthur Topham
- Web page: https://patentgrep.com/patent/US5352755A

## CPC

- C07D 231/12: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C08G 18/10: Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
- C08G 18/808: {Monoamines}
- C09D 5/4496: {characterised by the nature of the curing agents}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- 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 blocked polyisocyanate of the formula R--Y.sub.m where R is an m valent aliphatic, cycloaliphatic, heterocyclic or aromatic residue; each Y, which may be the same or different, is ##STR1## where R.sub.1 is, or, when n is more than 1, each R.sub.1, which may be the same or different, is an alkyl, alkenyl, aralkyl, N-substituted carbamyl, phenyl, NO.sub.2, halogen or ##STR2## group where R.sub.2 is a C.sub.1 -C.sub.4 alkyl group; n is 0, 1, 2 or 3; and m is an integer greater than 1 is useful in paint compositions.

## Claims

### Claim 1

In a storage-stable coating composition curable by heat unblocking at 100.degree. C. to 120.degree. C., said composition comprising an active hydrogen-containing compound and a blocked polyisocyanate of the formula:
R--Y.sub.m
wherein m is an integer greater than 1, Y is a blocking group and R is an m-valent aromatic residue of an isocyanate compound selected from the group consisting of .omega., .omega.'-diisocyanato-1,3-dimethyl benzene, .omega., .omega.'-diisocyanato-1,4-dimethyl benzene, .omega., .omega.'-diisocyanato-diethyl benzene, .omega., .omega.'-diisocyanato-dimethyl toluene, .omega., .omega.'-diisocyanato-diethyl toluene, 1,3-bis-(2-isocyanato-prop-2-yl) benzene, and 1,4-bis-(2-isocyanato-prop-2-yl) benzene or R is an m-valent residue of a polyisocyanate reaction product of an isocyanate and an active hydrogen-containing compound selected from the group consisting of water, a lower molecular weight polyol having a molecular weight less than or equal to 300 and a medium molecular weight polyol having a molecular weight greater than 300 and less than 8000 or R is an m-valent residue of an isocyanurate, the improvement whereby said composition is curable by heat unblocking at 100.degree. C. to 120.degree. C., and each Y, which may be the same or different, is ##STR8## wherein R.sub.1 is, or, where n is more than 1, each R.sub.1, which may be the same or different, is a C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkenyl, phenyl C.sub.1 -C.sub.4 alkenyl, phenyl, NO.sub.2, halogen or a ##STR9## group where R.sub.2 is a C.sub.1 -C.sub.4 alkyl group; and n is 0, 1, 2 or 3, provided that, when R is an aromatic residue the groups Y are not directly attached to an aromatic nucleus.

### Claim 2 (depends on 1)

A composition according to claim 1 wherein R is an aromatic residue of an isocyanate compound selected from the group consisting of: .omega., .omega.'-diisocyanato-1,3-dimethyl benzene, .omega., .omega.'-diisocyanato-1,4-dimethyl benzene, .omega., .omega.'-diisocyanato-diethyl benzene, .omega., .omega.'-diisocyanato-dimethyl toluene, .omega., .omega.'-diisocyanato-diethyl toluene, 1,3-bis-(2-isocyanato-prop-2-yl) benzene, and 1,4-bis-(2-isocyanato-prop-2-yl) benzene.

### Claim 3 (depends on 2)

A composition according to claim 2 wherein R is the residue of 1,3-bis-(2-isocyanato-prop-2-yl) benzene.

### Claim 4 (depends on 1)

A composition according to claim 1 wherein R is a residue of a polyisocyanate reaction product of an isocyanate and an active hydrogen-containing compound selected from the group consisting of water, a lower molecular weight polyol having a molecular weight less than or equal to 300 and a medium molecular weight polyol having a molecular weight greater than 300 and less than 800.

### Claim 5 (depends on 4)

A composition according to claim 4 wherein said active hydrogen-containing compound is a lower molecular weight polyol selected from the group consisting of ethylene glycol, propylene glycol, 1,3-butylene glycol, neopentyl glycol, 2,2,4-trimethyl-1,3-butylene glycol, neopentyl glycol, 2,2,4-trimethyl-1,3-pentane diol, hexamethylene glycol, cyclohexane dimenthanol, hydrogenated bisphenol-A, trimethylol propane, trimethylol ethane, 1,2,6-hexane triol, glycerine, sorbitol and pentaerythritol.

### Claim 6 (depends on 1)

A composition according to claim 1 wherein R is a residue of an isocyanurate.

### Claim 7 (depends on 1)

A composition according to claim 1 wherein, in said blocked polyisocyanate, at least one Y is ##STR10##

### Claim 8 (depends on 7)

A composition according to claim 7 wherein in at least one Y is ##STR11##

### Claim 9 (depends on 1)

A composition according to claim 1 wherein, in said blocked polyisocyanate, m is from 2 to 6.

### Claim 10 (depends on 1)

A composition according to claim 1 wherein, in said blocked polyisocyanate, R is a divalent radical derived from isophorone of the formula ##STR12##

### Claim 11 (depends on 1)

A composition according to claim 1 wherein said blocked polyisocyanate has a biuret structure or an allophanate group.

### Claim 12 (depends on 1)

A composition according to claim 1 wherein said active hydrogen-containing compound is an amine or an alcohol.

### Claim 13 (depends on 12)

A composition according to claim 12 wherein said active hydrogen-containing compound is 1,4-butanediol.

### Claim 14 (depends on 1)

A composition according to claim 1 further comprising a catalyst.

### Claim 15 (depends on 14)

A composition according to claim 14 wherein said catalyst is dibutyl tin dilaurate or tri-ethylene diamine.

### Claim 16 (depends on 1)

A composition according to claim 1 wherein said active hydrogen-containing compound is a pigment carrier containing active hydrogen groups, said composition further comprising a pigment.

### Claim 17 (depends on 16)

A composition according to claim 16 having 0.5 to 2 blocked isocyanate groups per active hydrogen-containing group.