# US 2020/0399433 A1 · Improvement of impact properties of dynamically cross-linked networks by using reactive impact modifiers

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- Number: US 2020/0399433 A1
- Document ID: US20200399433A1
- Status: Published application
- Kind: A1
- Application number: 16/464,464
- Filed: 2017-11-29
- Published: 2020-12-24
- Earliest claimed: 2016-11-30
- Assignees: Sabic Global Technologies B.V.
- Applicants: Sabic Global Technologies B.V.
- Inventors: Ramon GROOTE; Johannes Gerardus Petrus GOOSSENS
- Web page: https://patentgrep.com/patent/US20200399433A1

## CPC

- C08J 3/24: Crosslinking, e.g. vulcanising, of macromolecules (mechanical aspects B29C35/00; crosslinking agents C08K)
- C08G 63/78: Preparation processes
- C08G 63/85: Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof {(C08G63/823 takes precedence)}
- C08G 63/914: {derived from polycarboxylic acids and polyhydroxy compounds}
- C08G 63/916: {Dicarboxylic acids and dihydroxy compounds}
- C08L 63/00: Compositions of epoxy resins; Compositions of derivatives of epoxy resins
- C08L 67/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C08L67/06 takes precedence)
- C08J 2367/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds; (C08J2367/06 takes precedence)
- C08J 2463/02: Polyglycidyl ethers of bis-phenols
- 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)
- 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)

## Abstract

Provided are pre-dynamically cross-linked compositions including a networking impact modifier additive. Compositions include a pre-dynamic cross-linked polymer composition including polyester chains joined by a coupler component and one or more networking impact modifier additives. Methods of making the compositions are also described.

## Claims

### Claim 1

A polymer composition, comprising:
a pre-dynamic cross-linked polymer composition comprising polyester chains joined by a coupler component; and
one or more networking impact modifier additives.

### Claim 2 (depends on 1)

The polymer composition of claim 1, wherein the pre-dynamic cross-linked polymer composition is produced by reacting at least a coupler component comprising at least two reactive groups with a chain component comprising a polyester and with one or more networking impact modifier additives, in the presence of one or more catalysts.

### Claim 3 (depends on 1)

The polymer composition of claim 1, wherein the one or more networking impact modifier additives forms dynamic covalent bonds with one or more of carboxylic acid end groups or terminal hydroxyl groups of the polyester chains polymer composition.

### Claim 4 (depends on 1)

The polymer composition of claim 1, wherein the composition, when subjected to a curing process, forms a dynamic cross-linked polymer composition that (a) has a plateau modulus of from about 0.01 MPa to about 1000 MPa when measured by dynamic mechanical analysis at a temperature above a melting temperature of the polyester chains of the pre-dynamic cross-linked composition and (b) exhibits a capability of relaxing internal residual stresses at a characteristic timescale of between 0.1 and 100,000 seconds above a glass transition temperature of the polyester chains, as measured by stress relaxation rheology measurement.

### Claim 5 (depends on 4)

The polymer composition of claim 4, wherein the curing process comprises heating the pre-dynamic cross-linked composition to a temperature of from about 170° C. to about 250° C. for up to about 8 hours.

### Claim 6 (depends on 4)

The polymer composition of claim 4, wherein the one or more networking impact modifier additives further comprises an epoxy-functionalized (co)polymer.

### Claim 7 (depends on 6)

The polymer composition of claim 6, wherein the epoxy-functionalized (co)polymer comprises a glycidyl methacrylate poly(ethylene-acrylate) copolymer.

### Claim 8 (depends on 4)

The polymer composition of claim 4, wherein the one or more networking impact modifier additives further comprises a maleic anhydride copolymer.

### Claim 9 (depends on 8)

The polymer composition of claim 8, wherein the maleic anhydride copolymer is a maleic anhydride poly(ethylene-acrylate) copolymer.

### Claim 10 (depends on 1)

The polymer composition of claim 1, wherein the one or more networking impact modifier additives is present in an amount between 2 wt. % and 20 wt. %.

### Claim 11

A method of preparing a pre-dynamic cross-linked polymer composition, comprising:
reacting (a) a coupler component and (b) a chain component comprising a polyester having one or more reactive end groups; and
adding one or more networking impact modifier additives comprising one or more groups reactive with the one or more reactive end groups of the chain component, under such conditions that the one or more networking impact modifier additives covalently bond to the one or more reactive end groups of the chain component,
the reacting being performed in the presence of at least one catalyst that promotes formation of the pre-dynamic cross-linked composition, and
the pre-dynamic cross-linked composition when subjected to a curing process (a) exhibits a plateau modulus of from about 0.01 MPa to about 1000 MPa when measured by dynamic mechanical analysis at a temperature above a melting temperature of the polyester of the pre-dynamic cross-linked composition and (b) exhibits a capability of relaxing internal residual stresses at a characteristic timescale of between 0.1 and 100,000 seconds above a glass transition temperature of the polyester, as measured by stress relaxation rheology measurement.

### Claim 12 (depends on 11)

The method of claim 11, further comprising a curing process that comprises heating the pre-dynamic cross-linked composition of from about 170° C. to about 250° C. for up to about 8 hours to form a dynamically cross-linked composition.

### Claim 13 (depends on 11)

The method of claim 11, wherein the one or more networking impact modifier additives comprises a maleic anhydride poly(ethylene-acrylate) copolymer or a glycidyl methacrylate poly(ethylene-acrylate) copolymer.

### Claim 14 (depends on 11)

The method of claim 11, wherein the one or more networking impact modifier additives is present in an amount between 2 wt. % and 20 wt. %.

### Claim 15 (depends on 11)

The method of claim 11, wherein the reacting occurs at a temperature in which the chain component is in a melted state.

### Claim 16 (depends on 11)

The method of claim 11, wherein the one or more networking impact modifier additives forms dynamic covalent bonds with one carboxylic acid end groups or terminal hydroxyl groups of the chain component.

### Claim 17 (depends on 11)

The method of claim 11, wherein the one or more networking impact modifier additives gives rise to a dispersed phase throughout the polymer composition within which the one or more impact modifier additives is dispersed.

### Claim 18 (depends on 11)

A method of forming an article that comprises a pre-dynamic cross-linked polymer composition, comprising:
preparing a pre-dynamic cross-linked polymer composition according to the method of claim 11; and
subjecting the pre-dynamic cross-linked polymer composition to one or more of a compression molding process, a profile extrusion process, or a blow molding process so as to form the article.

### Claim 19 (depends on 11)

A method of forming an article that comprises a pre-dynamic cross-linked polymer composition, comprising:
subjecting the pre-dynamic cross-linked polymer composition according to claim 11 to one or more of a compression molding process, a profile extrusion process, or a blow molding process so as to form the article.

### Claim 20 (depends on 19)

The method of claim 19, further comprising subjecting the pre-dynamic cross-linked polymer composition to a curing process that comprises heating the pre-dynamic cross-linked composition of from about 170° C. to about 250° C. for up to about 8 hours to form a dynamically cross-linked composition.