# US 10,245,617 B2 · Synthesis of surface-functionalized polyamides

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- Number: US 10,245,617 B2
- Document ID: US10245617B2
- Status: Granted
- Kind: B2
- Application number: 15/741,300
- Filed: 2016-07-06
- Published: 2018-07-05
- Granted: 2019-04-02
- Earliest claimed: 2015-07-09
- Assignees: BASF SE
- Applicants: BASF SE
- Inventors: Gijsbrecht Jacobus Maria Habraken; Johannes Klaus Sprafke; Marion da Silva
- Web page: https://patentgrep.com/patent/US10245617B2

## CPC

- B05D 3/107: {Post-treatment of applied coatings}
- B05D 1/36: Successively applying liquids or other fluent materials, e.g. without intermediate treatment
- B05D 3/007: {After-treatment}
- B05D 3/10: by other chemical means
- B05D 3/105: {Intermediate treatments}
- B05D 7/02: to macromolecular substances, e.g. rubber (treatment or coating of shaped articles made of macromolecular substances C08J7/00)
- B05D 7/50: {Multilayers}
- C07B 37/12: Diels-Alder reactions
- C08G 69/48: Polymers modified by chemical after-treatment
- C08J 7/12: Chemical modification
- C08L 77/06: Polyamides derived from polyamines and polycarboxylic acids (C08L77/10 takes precedence)
- B05D 2201/02: Polymeric substrate
- B05D 2505/00: Polyamides
- C08J 2377/00: Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
- C08J 2377/06: Polyamides derived from polyamines and polycarboxylic acids (C08J2377/10 takes precedence)
- C08J 2453/00: Characterised by the use of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives of such polymers
- B05D: PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL (conveying articles or workpieces through baths of liquid B65G, e.g. B65G49/02)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08J: WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H (working, e.g. shaping, of plastics B29)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention relates to a process for producing a surface-functionalized molding (oF) having a functionalized surface (fO). In this process a surface (O) of a molding (F) is brought into contact with a dienophile-containing solution (dL). The surface (O) comprises a polyamide (P) which comprises furan units. These furan units are able to react with the at least one dienophile present in the dienophile-containing solution (dL) to give the surface-functionalized molding (oF) having the functionalized surface (fO).

## Claims

### Claim 1

A process for producing a surface-functionalized molding (oF) having a functionalized surface (fO), comprising the steps of
i) providing a molding (F) having a surface (0) which comprises a polyamide (P), the polyamide (P) comprising diene units of the general formula (I)
in which
R1 and R2 independently of one another are selected from C1-C10 alkanediyl,
ii) contacting the surface (O) of the molding (F) provided in step i) with a dienophile-containing solution (dL) which comprises at least one dienophile, the at least one dienophile comprising at least one dienophile unit which is reactive toward the diene units (I) present in the polyamide (P), to give the surface-functionalized molding (oF) having the functionalized surface (fO).

### Claim 2 (depends on 1)

The process according to claim 1, wherein in step ii) the at least one dienophile unit present in the at least one dienophile reacts with the diene units (I) present in polyamide (P) in a [4+2] cycloaddition to give the surface-functionalized molding (oF).

### Claim 3 (depends on 1)

The process according to claim 1, wherein the dienophile-containing solution (dL) comprises at least one solvent (LM).

### Claim 4 (depends on 3)

The process according to claim 3, wherein the at least one solvent (LM) is selected from the group consisting of acetone, acetonitrile, N-methyl-2-pyrrolidone, dimethylformamide, dimethyl sulfoxide, hexane, toluene, diethyl ether, tetrahydrofuran, methylene chloride, chloroform, 1,2-dichlorobenzene, water, methanol, ethanol, and isopropanol.

### Claim 5 (depends on 3)

The process according to claim 3, wherein the dienophile-containing solution (dL) comprises in the range from 0 to 99.5 wt % of the at least one solvent (LM) and in the range from 0.5 to 100 wt % of the at least one dienophile, based in each case on the total weight of the dienophile-containing solution (dL).

### Claim 6 (depends on 1)

The process according to claim 1, wherein the at least one dienophile unit present in the at least one dienophile is selected from the group consisting of C═C double bonds, C═O double bonds, and C═S double bonds.

### Claim 7 (depends on 1)

The process according to claim 1, wherein the at least one dienophile present in the dienophile-containing solution (dL) comprises at least one structural unit selected from the group consisting of maleimides, benzophenone, acrylates, methacrylates, acrylonitriles, maleic acid, maleic anhydride, and maleic esters.

### Claim 8 (depends on 1)

The process according to claim 1, wherein the at least one dienophile present in the dienophile-containing solution (dL) comprises exactly one dienophile unit.

### Claim 9 (depends on 1)

The process according to claim 1, wherein step ii) is carried out at a temperature in the range from 15 to 150° C.

### Claim 10 (depends on 1)

The process according to claim 1, wherein the at least one dienophile present in the dienophile-containing solution (dL) comprises at least one further functional unit.

### Claim 11 (depends on 10)

The process according to claim 10, wherein the at least one further functional unit is selected from the group consisting of anhydrides, imides, esters, carboxylic acids, amines, alcohols, thiols, and isocyanates.

### Claim 12 (depends on 10)

The process according to claim 10, wherein the following step is carried out subsequent to step ii):
iii) contacting the functionalized surface (fO) of the surface-functionalized molding (oF) obtained in step ii) with at least one functionalizing agent (FM) which comprises at least one reactive unit which is reactive toward the at least one further functional unit present in the at least one dienophile.

### Claim 13 (depends on 12)

The process according to claim 12, wherein the at least one reactive unit present in the at least one functionalizing agent (FM) is selected from the group consisting of amines, alcohols, thiols, isocyanates, carboxylic acids, and anhydrides.

### Claim 14 (depends on 1)

A surface-functionalized molding (oF) obtainable by the process according to claim 1.