# US 2014/0197580 A1 · Method for producing a bio-pet polymer

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- Number: US 2014/0197580 A1
- Document ID: US20140197580A1
- Status: Published application
- Kind: A1
- Application number: 14/343,457
- Filed: 2012-09-07
- Published: 2014-07-17
- Earliest claimed: 2011-09-08
- Assignees: SociéTé Anonyme Des Eaux MinéRales D'Evian Et En AbréGé “S.A.E.M.E”
- Inventors: Francoise Poulat
- Web page: https://patentgrep.com/patent/US20140197580A1

## CPC

- C08G 63/199: Acids or hydroxy compounds containing cycloaliphatic rings
- B29D 22/003: {Containers for packaging, storing or transporting, e.g. bottles, jars, cans, barrels, tanks}
- C08G 63/183: Terephthalic acids
- C08G 63/78: Preparation processes
- C08G 63/80: Solid-state polycondensation
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- B29D: PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE (making granules B29B9/00; making preforms B29B11/00)

## Abstract

The invention relates to a method for producing a bio-PET polymer comprising the following steps: Step A) providing at least one diacid compound, comprising a terephtalate compound; Step B) providing at least one diol compound, comprising monoethylene glycol; wherein—at least one of the terephtalate compound and/or the monoethylene glycol is obtained from at least one bio-based material, and—at least one of the diacid compound and/or the diol compound further comprises at least one crystallization retarding compound; and Step C) copolymerizing a mixture of the diacid compound and the diol compound to obtain a bio-PET polymer comprising diacid units and diol units, comprising up to 7.5 mol % of unit(s) corresponding to the at least one crystallization retarding compound, based on the total number of moles of diacid units contained in the bio-PET. The invention also relates to a method for producing a bio-PET packaging element, comprising the following steps:—performing the method described above; and—Step D) converting the bio-PET into the bio-PET packaging element.

## Claims

### Claim 1

A method for producing a bio-PET polymer comprising the following steps:
Step A) providing at least one diacid compound, comprising a terephtalate compound;
Step B) providing at least one diol compound, comprising monoethylene glycol; wherein:
at least one of the terephtalate compound and/or the monoethylene glycol is obtained from at least one bio-based material, and
at least one of the diacid compound and/or the diol compound further comprises at least one crystallization retarding compound; and
Step C) copolymerizing a mixture of the diacid compound and the diol compound comprising the at least one crystallization retarding compound, to obtain a bio-PET polymer comprising diacid units and diol units, comprising up to 7.5 mol % of unit(s) corresponding to the at least one crystallization retarding compound, based on the total number of moles of diacid units contained in the bio-PET.

### Claim 2 (depends on 1)

The method according to claim 1, wherein the at least one crystallization retarding compound comprises isophtalic acid and/or 1,4-cyclohexanedimethanol.

### Claim 3 (depends on 1)

The method according to claim 1, wherein the molar ratio in the bio-PET between units corresponding to the diacid compound(s) and units corresponding to the diol compound(s) is from 0.9 to 1.1.

### Claim 4 (depends on 1)

The method according to claim 1, wherein the crystallization retarding compound is a diacid being isophtalic acid, and wherein
the molar amount of isophtalic acid compared the total amount of diacid compound is of from 1.5% to 3.5%, and
the molar amount of terephtalate compound compared the total amount of diacid compound is of from 96.5% to 98.5%.

### Claim 5 (depends on 1)

The method according to claim 1, wherein the crystallization retarding compound is 1,4-cyclohexanedimethanol, and wherein
the molar amount of 1,4-cyclohexanedimethanol compared the total amount of diol compound is of from 1.5% to 7.5%, and
the molar amount of terephtalate compound compared the total amount of diol compound is of form 92.5% to 98.5%.

### Claim 6 (depends on 1)

The method according to claim 1, wherein at least a part of the monoethylene glycol is obtained from a bio-material.

### Claim 7 (depends on 6)

The method according to claim 6, wherein the bio-material, from which monoethylene glycol is obtained, is produced from one of the following raw materials:
plant;
plant waste.

### Claim 8 (depends on 1)

The method according to claim 1, wherein the terephthalate compound is terephthalic acid or dimethylterephtalate.

### Claim 9 (depends on 1)

The method according to claim 1, wherein at least a part of the terephtalate compound is obtained from a bio-material.

### Claim 10 (depends on 9)

The method according to claim 9, wherein the bio- material, from which the terephtalate compound is obtained, is produced from a biomass comprising terpene, terpenoid or a mixture thereof, or from para-xylene obtained from a bio-material, or from muconic acid obtained by a microbiological process from a biomass.

### Claim 11 (depends on 1)

The method according to claim 1, wherein step C) comprises the following steps:
Step C1) melt polymerization, and
Step C2) solid state polymerization.

### Claim 12 (depends on 1)

A method for producing a bio-PET packaging element, comprising the following steps:
performing the method of claim 1; and
Step D) converting the bio-PET into the bio-PET packaging element.

### Claim 13 (depends on 12)

The method according to claim 12, wherein:
the packaging element is a bottle and step D) is carried out by injection blow molding or injection stretch blow molding, or
the packaging element is a cup and step D) is carried out by thermoforming, or
the packaging element is a film and step D) is carried out by extruding and stretching.

### Claim 14 (depends on 13)

The method according to claim 13, wherein step D) comprises the following sub-steps:
injecting the bio-PET into a preform mould to form a preform;
heating the preform at least above the glass transition point of the bio-PET;
blowing the preform into a mould, to obtain a bio-PET bottle.

### Claim 15 (depends on 14)

The method according to claim 14, wherein after the sub-step of injecting and prior to the sub-step of heating the preform, the sub-step of cooling the preform is implemented.

### Claim 16 (depends on 14)

The method according to claim 14, wherein the sub-step of injecting comprises:
melting the bio-PET in a single or double-screw injection-moulding machine at a temperature of 270° C. to 285° C.,
feeding the melted bio-PET under pressure of 2.5·107 Pa to 5·107 Pa, into a mould at a temperature of 260° C. to 285° C.

### Claim 17 (depends on 14)

The method according to claim 14, wherein the bio-PET packaging element is a bottle and is filled with carbonated drinks, natural still water, mineral still water, natural sparkling water or mineral sparkling water.

### Claim 18 (depends on 7)

The method according to claim 7, wherein:
the plant is selected from beet, sugar cane, maize, wheat, citrus fruits, and woody plant;
the plant waste is selected from sawdust, wheat straw, wheat corns, natural fibres, cellulosics, lignocellulosics, and hemicelluloses.
