# US 10,118,997 B2 · Fine powder of polyamide from renewable materials and method for making such a powder

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- Number: US 10,118,997 B2
- Document ID: US10118997B2
- Status: Granted
- Kind: B2
- Application number: 15/412,644
- Filed: 2017-01-23
- Published: 2017-05-11
- Granted: 2018-11-06
- Earliest claimed: 2008-02-15
- Assignees: Arkema France
- Applicants: Arkema France
- Inventors: Karine Loyen; Eric Labonne
- Web page: https://patentgrep.com/patent/US10118997B2

## CPC

- C08J 3/12: Powdering or granulating
- A61K 8/022: {Powders; Compacted Powders}
- A61K 8/0245: {Specific shapes or structures not provided for by any of the groups of A61K8/0241}
- A61K 8/25: Silicon; Compounds thereof
- A61K 8/88: Polyamides
- A61K 47/34: Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers (A61K47/10 takes precedence)
- A61Q 1/10: for eyes, e.g. eyeliner, mascara
- A61Q 1/12: Face or body powders for grooming, adorning or absorbing
- C08G 69/08: derived from amino-carboxylic acids
- C08G 69/26: derived from polyamines and polycarboxylic acids
- C08K 3/36: Silica
- C09D 5/08: Anti-corrosive paints
- C09D 7/65: macromolecular (C09D7/41-C09D7/48 take precedence)
- C09D 7/69: {Particle size larger than 1000 nm}
- G06Q 30/02: Marketing; Price estimation or determination; Fundraising
- G06Q 50/188: {Electronic negotiation}
- A61K 9/1694: {resulting in granules or microspheres of the matrix type containing more than 5% of excipient}
- A61K 2800/412: Microsized, i.e. having sizes between 0.1 and 100 microns
- A61K 2800/652: The particulate/core comprising organic material
- C08G 69/02: Polyamides derived from amino-carboxylic acids or from polyamines and polycarboxylic acids
- C08G 69/04: Preparatory processes
- 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 2377/02: Polyamides derived from omega-amino carboxylic acids or from lactams thereof (C08J2377/10 takes precedence)
- C08L 77/00: Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain (of polyhydrazides C08L79/06; of polyamideimides or polyamide acids C08L79/08); Compositions of derivatives of such polymers
- Y10T 428/2982: Particulate matter [e.g., sphere, flake, etc.]
- 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)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61Q: SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- 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)
- 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)
- G06Q: INFORMATION AND COMMUNICATION TECHNOLOGY [ICT] SPECIALLY ADAPTED FOR ADMINISTRATIVE, COMMERCIAL, FINANCIAL, MANAGERIAL OR SUPERVISORY PURPOSES; SYSTEMS OR METHODS SPECIALLY ADAPTED FOR ADMINISTRATIVE, COMMERCIAL, FINANCIAL, MANAGERIAL OR SUPERVISORY PURPOSES, NOT OTHERWISE PROVIDED FOR
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

The present invention relates to a powder of polyamide PA (homopolyamide or copolyamide) derived at least partially from renewable materials, in which the particles have a nonspherical shape and a volume median diameter of less than or equal to 20 μm. The present invention also relates to a process for preparing such a powder.

## Claims

### Claim 1

A polyamide (PA) powder comprising a homopolyamide or copolyamide derived at least partially from renewable materials, in which particles of the powder have a nonspherical, irregular shape, without sharp edges, and a volume median diameter within the range of from 5 to 20 μm, an absorption capacity, measured according to the DIN ISO 787N standard, within the range of from 55 to 110 g of oil/100 g of polyamide powder and a breaking strength of said powder, when it is compacted only by compression under one tonne, within the range of from 100 to 600 Newtons.

### Claim 2 (depends on 1)

The polyamide powder according to claim 1, comprising at least one molecule of: 11-aminoundecanoic acid, n-heptyl-11-aminoundecanoic acid, sebacic acid, decanediamine, a difatty acid, a dimer of a fatty acid or mixtures thereof.

### Claim 3 (depends on 1)

The polyamide powder according to claim 1, wherein the PA is PA 11, PA 10.10 or a copolyamide comprising at least one of the following monomers: 11, 10.10, 10.36, 6.10, 10.T or mixtures thereof.

### Claim 4 (depends on 1)

The polyamide powder according to claim 1, wherein said polyamide is entirely derived from renewable materials.

### Claim 5 (depends on 1)

The polyamide powder according to claim 1, in which the particles have a specific surface area within the range of from 1 to 20 m2/g.

### Claim 6 (depends on 1)

The polyamide powder according to claim 1, in which the particles have a volume median diameter within the range of from 5 to 15 μm.

### Claim 7 (depends on 1)

The polyamide powder according to claim 1, wherein its absorption capacity, measured according to the DIN ISO 787N standard, within the range of from 60 to 90 g of oil/100 g of polyamide powder and a breaking strength of said powder, when it is compacted only by compression under one tonne, within the range of from 150 to 500 Newtons.

### Claim 8 (depends on 1)

The polyamide powder according to claim 1, wherein a breaking strength of said powder, when it is compacted only by compression under one tonne, within the range of from 150 to 500 Newtons.

### Claim 9 (depends on 1)

The polyamide powder according to claim 1, wherein it comprises 14C.

### Claim 10 (depends on 1)

The polyamide powder according to claim 1, comprising at least 20% by mass of carbon of renewable origin.

### Claim 11 (depends on 1)

The polyamide powder according to claim 1, comprising at least 0.2×10−10% by mass of 14C.

### Claim 12 (depends on 1)

A product comprising the polyamide powder of claim 1, wherein said product is a cosmetic, pharmaceutical or perfumery product, coating, paint, anticorrosive composition, additive for paper, object formed by melt agglomeration or radiation sintering, electrophoresis gel, multilayer composite material, packaging, toy, textile, automobile part or electronics industry part.

### Claim 13 (depends on 12)

The product according to claim 12, wherein said polyamide powder is a compacting agent in pressed cosmetic formulations.

### Claim 14 (depends on 12)

The product according to claim 12 wherein said polyamide powder is a matifying agent.

### Claim 15 (depends on 1)

A process for preparing a polyamide powder according to claim 1, comprising:
milling at ambient temperature a prepolymer powder having an inherent viscosity of less than 0.5 (0.5 g/dl in metacresol at 25° C.), said milling being carried out by means of an opposed air jet mill.

### Claim 16 (depends on 15)

The process according to claim 15, in which the prepolymer has an inherent viscosity within the range of from 0.25 to 0.5.

### Claim 17 (depends on 15)

The process according to claim 15, further comprising adding fumed silica to the prepolymer powder before it is milled.

### Claim 18 (depends on 15)

The process according to claim 15, further comprising, before the milling:
manufacturing a prepolymer of PA having a number-average molecular mass of less than 5000 g/mol, and having a viscosity of less than 0.5 (0.5 g/dl in metacresol at 25° C.).

### Claim 19 (depends on 15)

The process according to claim 15, further comprising, after the milling:
raising the viscosity of the milled prepolymer powder, to the final viscosity desired for the powder.

### Claim 20 (depends on 19)

The process according to claim 19, in which the viscosity rise is performed by solid-phase polycondensation in a dryer.

### Claim 21 (depends on 15)

The process according to claim 15, conducted in a solvent.

### Claim 22 (depends on 15)

The process according to claim 15, in which the final particle size of the PA powder is adjusted directly by adjusting the milling speed.

### Claim 23 (depends on 22)

The process according to claim 22, in which the adjustment of the milling speed is carried out by means of a selector integrated into the mill.

### Claim 24 (depends on 12)

The product of claim 12, wherein said product is a cosmetic powder containing an additive comprising pigments, fillers, antioxidants or powder binders.

### Claim 25 (depends on 24)

The product according to claim 24, wherein said additive comprises silica powder.

### Claim 26 (depends on 24)

The product according to claim 24, wherein said product constitutes a face powder or an eye shadow.