# US 10,501,604 B2 · Polylactic acid resin composition

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- Number: US 10,501,604 B2
- Document ID: US10501604B2
- Status: Granted
- Kind: B2
- Application number: 14/779,145
- Filed: 2014-04-02
- Published: 2016-02-25
- Granted: 2019-12-10
- Earliest claimed: 2013-04-04
- Assignees: SK Chemicals Co., Ltd.
- Applicants: SK Chemicals Co., Ltd.
- Inventors: Young-Man Yoo; Jae-il Chung; Kye Yune Lee; Sung-wan Jeon; Min-young Kim
- Web page: https://patentgrep.com/patent/US10501604B2

## CPC

- C08K 5/5393: Phosphonous compounds, e.g. R—P(OR')2
- C08G 18/6208: {Hydrogenated polymers of conjugated dienes}
- C08G 63/08: Lactones or lactides
- C08G 81/027: {containing polyester or polycarbonate sequences}
- C08K 5/005: {Stabilisers against oxidation, heat, light, ozone}
- C08K 5/12: of cyclic polycarboxylic acids
- C08K 5/36: Sulfur-, selenium-, or tellurium-containing compounds {(C08K5/0091 takes precedence)}
- C08K 5/521: Esters of phosphoric acids, e.g. of H3PO4
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- C08J 5/18: Manufacture of films or sheets
- C08J 2367/04: Polyesters derived from hydroxy carboxylic acids, e.g. lactones (C08J2367/06 takes precedence)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)

## Abstract

The present invention relates to a polylactic acid resin composition having eco-friendly properties, which can be effectively used as a packaging material due to improved flexibility and moisture resistance, as well as superior general properties such as mechanical properties, transparency, heat resistance, an anti-blocking property, and film processability. The inventive polylactic acid resin composition comprises a polylactic acid resin comprising a hard segment comprising a polylactic acid repeating unit and a soft segment comprising a polyolefin-based polyol repeating unit in which polyolefin-based polyol structural units are linked in a linear or branched manner via a urethane bond or an ester bond, wherein the organic carbon content (% Cbio) of biomass-based carbon, as defined in Equation 1, is at least 60 wt %; and an antioxidant.

## Claims

### Claim 1

A polylactic acid resin composition comprising:
a polylactic acid resin comprising a hard segment comprising a polylactic acid repeating unit of Formula 1 and a soft segment comprising a polyolefin-based polyol repeating unit in which polyolefin-based polyol structural units of Formula 2 are linked in a linear or branched manner via a urethane bond, wherein the organic carbon content (% Cbio) of biomass-based carbon, as defined in Equation 1, is at least 60 wt %, wherein, in Formulae 1 and 2, n is an integer from 700 to 5,000, and m+1 is an integer from 5 to 200; and
an antioxidant:
% Cbio=(weight ratio of 14C isotope to 12C of the total carbon content in the polylactic acid resin)/(weight ratio of 14C isotope to 12C of the total carbon content in a biomass-based carbon standard material), wherein the antioxidant is used in an amount of 100 to 3,000 ppmw based on the amount of the monomers for forming the polylactic acid repeating unit, and [Equation 1]
wherein the polylactic acid resin is prepared by reacting an isocyanate containing compound with polyolefin-based polyol structural units of Formula 2 to form the soft segments, and then reacting the soft segments with the polylactic acid repeating units of Formula 1.

### Claim 2 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the 14C isotope content based on the total weight of carbon in the polylactic acid resin is 7.2×10−11 to 1.2×10−10 wt %.

### Claim 3 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the soft segment has the organic carbon content (% Cbio) of biomass-based carbon, as defined in Equation 1, of at least 70 wt %.

### Claim 4 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the polylactic acid resin has a number average molecular weight of 50,000 to 200,000, and a weight average molecular weight of 100,000 to 400,000.

### Claim 5 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the polylactic acid resin has a glass transition temperature (Tg) of 20 to 55° C., and a melting temperature (Tm) of 145 to 178° C.

### Claim 6 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the urethane bond is formed by a reaction between the terminal hydroxyl group of the polyolefin-based polyol structural unit; and diisocyanate or di- or higher functional isocyanate compound.

### Claim 7 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the polylactic acid resin comprises a block copolymer in which the terminal carboxyl group of the polylactic acid repeating units contained in the hard segment is linked to the terminal hydroxyl group of the polyolefin-based polyol structural units contained in the soft segment via an ester bond.

### Claim 8 (depends on 7)

The polylactic acid resin composition of claim 7, wherein the polylactic acid resin further comprises a polylactic acid homopolymer which is remaining uncoupled with the polyolefin-based polyol repeating unit.

### Claim 9 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the polymer of the polyolefin-based polyol repeating unit has a number average molecular weight of 1,000 to 100,000.

### Claim 10 (depends on 6)

The polylactic acid resin composition of claim 6, wherein the molar ratio of the terminal hydroxyl group of the polyolefin-based polyol structural unit to the isocyanate group of diisocyanate or di- or higher functional isocyanate compound is 1:0.50 to 1:0.99.

### Claim 11 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the polylactic acid resin comprises the hard segment in an amount of 65 to 95 parts by weight and the soft segment in an amount of 5 to 35 parts by weight per 100 parts by weight of the total polylactic acid resin.

### Claim 12 (depends on 1)

The polylactic acid resin composition of claim 1, which has a color-b value of less than 10.

### Claim 13 (depends on 1)

The polylactic acid resin composition of claim 1, which comprises residual monomers in an amount of less than 1 wt % based on the total weight of polylactic acid resin.

### Claim 14 (depends on 1)

The polylactic acid resin composition of claim 1, wherein the antioxidant comprises at least one antioxidant selected from the group consisting of a hindered phenol-based antioxidant, an amine-based antioxidant, a thio-based antioxidant, and a phosphite-based antioxidant.