# US 10,501,587 B2 · Processes for producing an antimicrobial masterbatch and products thereof

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- Number: US 10,501,587 B2
- Document ID: US10501587B2
- Status: Granted
- Kind: B2
- Application number: 15/213,589
- Filed: 2016-07-19
- Published: 2018-01-25
- Granted: 2019-12-10
- Earliest claimed: 2016-07-19
- Assignees: The Cupron Corporation
- Applicants: Cupron Inc.
- Inventors: Vikram Kanmukhla
- Web page: https://patentgrep.com/patent/US10501587B2

## CPC

- C08J 3/22: using masterbatch techniques
- B29B 9/065: {under-water, e.g. underwater pelletizers}
- B29C 48/022: {characterised by the choice of material}
- B29C 48/04: Particle-shaped (making granules B29B9/00)
- B29C 48/05: Filamentary, e.g. strands
- C08J 3/226: {using a polymer as a carrier}
- D01F 1/103: {Agents inhibiting growth of microorganisms}
- D01F 6/84: from copolyesters
- B29B 9/06: in the form of filamentary material, e.g. combined with extrusion
- B29K 2033/04: Polymers of esters
- B29K 2067/00: Use of polyesters {or derivatives thereof}, as moulding material
- B29K 2067/003: {PET, i.e. poylethylene terephthalate}
- B29K 2067/006: {PBT, i.e. polybutylene terephthalate}
- B29K 2067/04: {Polyesters derived from hydroxycarboxylic acids}
- B29K 2067/043: {PGA, i.e. polyglycolic acid or polyglycolide}
- B29K 2067/046: {PLA, i.e. polylactic acid or polylactide}
- B29K 2075/00: Use of {PU, i.e.} polyureas or polyurethanes {or derivatives thereof}, as moulding material
- B29K 2077/00: Use of {PA, i.e.} polyamides, e.g. polyesteramides {or derivatives thereof}, as moulding material
- B29K 2505/10: Copper
- B29K 2505/14: Noble metals, e.g. silver, gold or platinum
- C08J 2367/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence)
- C08J 2467/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08J2467/06 takes precedence)
- D01F 6/62: from polyesters
- D10B 2401/13: anti-allergenic or anti-bacterial
- 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)
- B29B: PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29C: SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING (making preforms B29B11/00; making laminated products by combining previously unconnected layers which become one product whose layers will remain together B32B37/00 - B32B41/00)
- D01F: CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- B29K: INDEXING SCHEME ASSOCIATED WITH SUBCLASSES B29B, B29C OR B29D, RELATING TO MOULDING MATERIALS OR TO MATERIALS FOR {MOULDS, } REINFORCEMENTS, FILLERS OR PREFORMED PARTS, e.g. INSERTS
- D10B: INDEXING SCHEME ASSOCIATED WITH SUBLASSES OF SECTION D, RELATING TO TEXTILES

## Abstract

A masterbatch may be blended with virgin polymer to add desired color or other properties to the virgin polymer prior to further processing. Methods and processes for producing an antimicrobial and/or antiviral polymeric masterbatch that may be used to add antimicrobial, antiviral and/or antifungal properties to a virgin polymer without significantly degrading the properties of the virgin polymer. The masterbatch may be extruded into pellets or formed into other particles for subsequent blending with the virgin polymer to add antimicrobial and antiviral properties to the polymeric materials. The method includes a heat treatment after compounding the base polymer with the antimicrobial, antiviral and/or antifungal are compounded together. The heat treatment comprises heating the masterbatch blend to a temperature between the glass transition temperature and the melting point of the base polymer.

## Claims

### Claim 1

A method of producing an antimicrobial masterbatch, comprising:
compounding antimicrobial particles with a base polymer wherein the ratio of antimicrobial particles to base polymer is between 1 to 7 and 1 to 1 to produce an antimicrobial polymer, wherein the antimicrobial polymer comprises antimicrobial particles in a concentration from 12 wt. % to 50 wt. %;
adding a water scavenger during the compounding of the antimicrobial particles with the base polymer, wherein the compounding includes blending the antimicrobial particles, the base polymer, and the water scavenger to produce a polymer blend and extruding the polymer blend; and
after compounding, heating the polymer blend to react the polymer in the masterbatch with hydroxyl groups attached to the antimicrobial particles to a reaction temperature between the glass transition temperature and the melting temperature of the base polymer to produce an antimicrobial masterbatch.

### Claim 2 (depends on 1)

The method of claim 1, wherein the heating results in an increase in the intrinsic viscosity of the polymer in the antimicrobial polymer.

### Claim 3 (depends on 1)

The method of claim 1, wherein the reaction temperature is from 100° C. below the melting temperature to the melting temperature of the polymer in the antimicrobial polymer.

### Claim 4 (depends on 1)

The method of claim 1, wherein the reaction temperature is from 100° C. below the melting temperature to a temperature 10° C. below the melting temperature of the polymer in the antimicrobial polymer.

### Claim 5 (depends on 1)

The method of claim 1, wherein the reaction temperature is from 60° C. below the melting temperature to a temperature 20° C. below the melting temperature of the polymer in the antimicrobial polymer.

### Claim 6 (depends on 1)

The method of claim 1, comprising:
blending the antimicrobial masterbatch with a thermoplastic polymer at a let-down ratio between 3% and 10% to produce an antimicrobial polymer.

### Claim 7 (depends on 6)

The method of claim 6, wherein the thermoplastic polymer is the same polymer as the base polymer.

### Claim 8 (depends on 6)

The method of claim 6, wherein the thermoplastic polymer is a different polymer than the base polymer.

### Claim 9 (depends on 6)

The method of claim 6, comprising:
blending the antimicrobial masterbatch with a thermoplastic polymer at a let-down ratio between 5.5% and 7.5% to produce an antimicrobial polymer.

### Claim 10 (depends on 6)

The method of claim 6, wherein the antimicrobial polymer comprises antimicrobial particles in the range from 1.5 wt. % to 4 wt. % of antimicrobial particles.

### Claim 11 (depends on 10)

The method of claim 10, comprising extruding the antimicrobial polymer to produce an antimicrobial fiber.

### Claim 12 (depends on 11)

The method of claim 11, wherein the yield of extruding the antimicrobial polymer is greater than 80%, wherein yield is calculated by the weight of the antimicrobial fiber produced divided by the weight of the antimicrobial polymer that was extruded.

### Claim 13 (depends on 1)

The method of claim 1, wherein the base polymer is one of a polyester, polyethylene terephthalate, polybutylene terephthalate, and polytrimethylene terephthalate, polylactic acid, polyglycolide, and polylactic-co-glycolic acid, polyamides or nylon including, but not limited to, nylon-6 (polycaprolactum) and Nylon 66, polyurethanes, a thermoplastic polymer or copolymer, and combinations thereof.

### Claim 14 (depends on 13)

The method of claim 13, wherein the base polymer has an intrinsic viscosity between 0.6 and 0.85.

### Claim 15 (depends on 1)

The method of claim 1, wherein the base polymer is polyethylene terephthalate.

### Claim 16 (depends on 1)

The method of claim 1, wherein the water scavenger is a phosphite.

### Claim 17 (depends on 1)

The method of claim 1, wherein after compounding, the intrinsic viscosity of the polymer in the antimicrobial polymer is reduced to between 0.35 and 0.5.

### Claim 18 (depends on 1)

The method of claim 1, wherein after compounding, the intrinsic viscosity of the polymer in the antimicrobial polymer is reduced to between 0.4 to 0.5.

### Claim 19 (depends on 1)

The method of claim 1, wherein the intrinsic viscosity of the polyester polymer increases into a range from 0.6 to 0.85.

### Claim 20 (depends on 1)

The method of claim 1, wherein the intrinsic viscosity of the polyester polymer increases into a range from 0.6 to 0.7.

### Claim 21

A method of forming an antimicrobial fiber, comprising:
compounding water-insoluble copper compound particles with a polyester polymer wherein the ratio of antimicrobial metal particles to polyester polymer is between 1 to 7 and 1 to 1 to produce an antimicrobial polyester, wherein the water-insoluble copper compound particles have hydroxyl groups attached to a surface of the insoluble copper compound particles and the compounding includes blending the water-insoluble copper compound particles and the polyester polymer to produce a polymer blend;
after compounding, heating the polymer blend to react the polyester polymer in the antimicrobial polymer with the hydroxyl groups attached to the surface of the insoluble copper compound particles to a reaction temperature between the glass transition temperature and the melting temperature of the polyester polymer in the antimicrobial polymer and polymerize the polyester polymer in the polymer blend to produce an antimicrobial masterbatch;
blending the antimicrobial masterbatch with a thermoplastic polymer to produce an antimicrobial polymer; and
extruding the antimicrobial polymer to produce an antimicrobial fiber, wherein a portion of the water-insoluble copper compound particles are exposed and protruding from surfaces of the polymeric material, wherein the water-insoluble copper oxide particles release at least one of Cu+ ions and Cu++ ions upon contact with a fluid.

### Claim 22 (depends on 21)

The method of claim 21, wherein the reaction temperature is from 100° C. below the melting temperature to a temperature 10° C. below the melting temperature of the polymer in the antimicrobial polymer.

### Claim 23 (depends on 21)

The method of claim 21, wherein the reaction temperature is from 60° C. below the melting temperature to a temperature 20° C. below the melting temperature of the polymer in the antimicrobial polymer.