# US 10,246,571 B2 · Polyfunctional amines with hydrophobic modification for controlled crosslinking of latex polymers

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- Number: US 10,246,571 B2
- Document ID: US10246571B2
- Status: Granted
- Kind: B2
- Application number: 14/943,903
- Filed: 2015-11-17
- Published: 2016-07-21
- Granted: 2019-04-02
- Earliest claimed: 2015-01-20
- Assignees: Ennis Paint, Inc.
- Applicants: Ennis Paint, Inc.
- Inventors: Haibo Li
- Web page: https://patentgrep.com/patent/US10246571B2

## CPC

- C09D 7/45: Anti-settling agents
- C07C 209/68: from amines, by reactions not involving amino groups, e.g. reduction of unsaturated amines, aromatisation, or substitution of the carbon skeleton
- C07C 215/08: with only one hydroxy group and one amino group bound to the carbon skeleton
- C07C 227/02: Formation of carboxyl groups in compounds containing amino groups, e.g. by oxidation of amino alcohols
- C07C 229/16: to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
- C07D 251/30: Only oxygen atoms
- C07D 403/14: containing three or more hetero rings
- C08F 220/14: Methyl esters {, e.g. methyl (meth)acrylate}
- C08G 59/1477: {containing nitrogen}
- C08G 73/0206: {Polyalkylene(poly)amines}
- C08K 5/3492: Triazines
- C08K 5/34924: {containing cyanurate groups; Tautomers thereof}
- C08K 5/34926: {also containing heterocyclic groups other than triazine groups}
- C09D 5/024: {characterised by the additives}
- C09D 5/14: Paints containing biocides, e.g. fungicides, insecticides or pesticides (C09D5/16 takes precedence)
- C09D 7/63: organic
- C09D 133/12: Homopolymers or copolymers of methyl methacrylate
- C09D 153/02: Vinyl aromatic monomers and conjugated dienes
- E01F 9/518: formed in situ, e.g. by painting, by casting into the road surface or by deforming the road surface
- C08K 5/103: with polyalcohols
- C08K 5/17: Amines; Quaternary ammonium compounds
- C08K 5/175: {containing COOH-groups; Esters or salts thereof}
- C09D 5/00: Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced {(electrically insulating plastics, resins or waxes H01B3/30)}; Filling pastes
- 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)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- E01F: ADDITIONAL WORK, SUCH AS EQUIPPING ROADS OR THE CONSTRUCTION OF PLATFORMS, HELICOPTER LANDING STAGES, SIGNS, SNOW FENCES, OR THE LIKE

## Abstract

Polyfunctional amine structures exhibiting at least one hydrophobic moiety selected from the group consisting of; hydrophobic epoxides, hydrophobic glycidyl ethers and hydrophobic (meth)acrylates are described which provide crosslinking capabilities for latex polymer compositions. These crosslinkers not only exhibit latent crosslinking properties but also improved hydrophobicity when compared with existing latex formulations. Latent crosslinking provides advantages associated with fast interactions between the anionic latex charge and the cationic charge associated with these hydrophobically modified polyfunctional amine crosslinkers. Once the latex is coated onto a substrate, the volatile base evaporates and the groups react to form a crosslinked coating with both improved hydrophobic and wash-off properties.

## Claims

### Claim 1

A polyfunctional amine comprising recurring units derived from the reaction of one bi- or tri-glycidyl moiety and a single, di-, or tri-functional amino monomer(s), or combination of, mono/tri, mono/tetra, bi/bi, bi/tri, bi/tetra, tri/tri, tri/tetra, and tetra/tetra functional amino monomers resulting in one or more polyfunctional amines
wherein I-x-2-b′ is a hydrophobic crosslinking agent and comprises at least three pH responsive amino group sites configured to accept or release proton(s) in response to a change in pH, and comprises at least one NH and/or one —NH2 site providing reactive sites for hydrophobic compounds that introduce at least one hydrophobic moiety into hydrophobic modifications of I-x-b-2′ structures represented by formulae I-x-b-2′ a, I-x-b-2′b, I-x-b-2′c and I-x-b-2′d:
wherein said structures of formulae I-x-b-2′a, I-x-b-2′b, I-x-b-2′c and I-x-b-2′d have at least one hydrophobic moiety introduced into said structures from the group consisting of: hydrophobic epoxides, hydrophobic glycidyl ethers and hydrophobic (meth)acrylates.

### Claim 2 (depends on 1)

The polyfunctional amine of claim 1, wherein said hydrophobic moiety is provided by post modification reactions with said epoxides, glycidyl ethers and (meth)acyrlates at ambient temperature and pressure.

### Claim 3 (depends on 1)

A latex formulation comprising the polyfunctional amine of claim 1.

### Claim 4 (depends on 3)

The latex formulation of claim 3, wherein said hydrophobic moiety is provided by carrying out post modification reactions with said epoxides, glycidyl ethers and (meth)acrylates at ambient temperature and pressure.