# US 10,501,626 B2 · Dynamically vulcanized polyarylene sulfide composition

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- Number: US 10,501,626 B2
- Document ID: US10501626B2
- Status: Granted
- Kind: B2
- Application number: 15/350,164
- Filed: 2016-11-14
- Published: 2017-03-02
- Granted: 2019-12-10
- Earliest claimed: 2012-04-13
- Assignees: Ticona LLC
- Applicants: Ticona LLC
- Inventors: Rong Luo; Joseph J. Grenci; Christopher McGrady; Xinyu Zhao
- Web page: https://patentgrep.com/patent/US10501626B2

## CPC

- C08L 81/02: Polythioethers; Polythioether-ethers
- B29C 48/022: {characterised by the choice of material}
- B29C 48/06: Rod-shaped
- B29C 48/09: Articles with cross-sections having partially or fully enclosed cavities, e.g. pipes or channels
- B29C 48/287: {Raw material pre-treatment while feeding (B29C48/78 takes precedence)}
- B29C 48/91: Heating, e.g. for cross linking
- B32B 1/08: Tubular products
- B32B 27/20: using fillers, pigments, thixotroping agents
- B32B 27/286: {comprising polysulphones; polysulfides}
- B65D 1/0215: {multilayered (B65D81/3837 takes precedence)}
- B65D 25/14: Linings or internal coatings (of containers made by folding or erecting blanks made of paper B65D5/56 {; linings for domestic water storage heaters F24H1/183})
- B65D 31/04: {with multiple walls (B65D81/3881 takes precedence; for shock absorbing purposes B65D81/03)}
- C08L 81/04: Polysulfides
- F16L 9/133: the walls consisting of two layers
- F16L 9/147: comprising only layers of metal and plastics with or without reinforcement
- F16L 11/00: Hoses, i.e. flexible pipes
- F16L 57/04: against fire or other external sources of extreme heat
- F16L 57/06: against wear (F16L57/04 takes precedence)
- F16L 58/04: Coatings characterised by the materials used (F16L58/16 takes precedence)
- F27B 14/00: Crucible or pot furnaces
- B29B 15/122: {with a matrix in liquid form, e.g. as melt, solution or latex}
- B29K 2081/04: {Polysulfides, e.g. PPS, i.e. polyphenylene sulfide or derivatives thereof}
- B29K 2105/0005: {containing compounding ingredients (releasing, lubricating or separating agents B29C33/56, fibers B29K2105/08, B29K2105/12; fillers B29K2105/16, recycled material B29K2105/26)}
- B32B 2307/558: Impact strength, toughness
- B32B 2307/7265: Non-permeable
- B32B 2597/00: Tubular articles, e.g. hoses, pipes
- C08L 2203/10: used for bottles
- C08L 2203/12: used for fibers
- C08L 2203/202: use in electrical wires or wirecoating
- Y10T 428/1352: Polymer or resin containing [i.e., natural or synthetic]
- Y10T 428/1393: Multilayer [continuous layer]
- Y10T 428/1397: Single layer [continuous layer]
- Y10T 428/2958: Metal or metal compound in coating
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- 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)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B65D: CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
- F16L: PIPES; JOINTS OR FITTINGS FOR PIPES; SUPPORTS FOR PIPES, CABLES OR PROTECTIVE TUBING; MEANS FOR THERMAL INSULATION IN GENERAL
- F27B: FURNACES, KILNS, OVENS OR RETORTS IN GENERAL; OPEN SINTERING OR LIKE APPARATUS
- 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
- 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
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

Polyarylene sulfide compositions are described that exhibit high strength and flexibility. Methods for forming the polyarylene sulfide compositions are also described. Formation methods include dynamic vulcanization of a polyarylene sulfide composition that includes an impact modifier dispersed throughout the polyarylene sulfide. A crosslinking agent is combined with the other components of the composition following dispersal of the impact modifier throughout the composition. The crosslinking agent reacts with the impact modifier to form crosslinks within and among the polymer chains of the impact modifier. The compositions can exhibit excellent physical characteristics at extreme temperatures and can be used to form, e.g., tubular member such as pipes and hoses and fibers.

## Claims

### Claim 1

A method for forming a polyarylene sulfide composition, the method comprising:
feeding a polyarylene sulfide to a melt processing unit having a length, wherein the polyarylene sulfide is a linear polyarylene sulfide containing less than about 1 mol. % of cross-linking units based on the total monomer units of the polyarylene sulfide;
feeding an impact modifier to the melt processing unit, the polyarylene sulfide and the impact modifier mixing in the melt processing unit along a blending length of the melt processing unit such that the impact modifier becomes distributed throughout the polyarylene sulfide, the impact modifier comprising a reactive epoxy functionality, the ratio of the length of the melt processing unit to the blending length of the melt processing unit being from about 5 to abut 40; and
feeding a polyfunctional crosslinking agent to the melt processing unit at the end of the blending length of the melt processing unit, the crosslinking agent being fed to the melt processing unit following distribution of the impact modifier throughout the polyarylene sulfide, the crosslinking agent comprising reactive functionality that is reactive to the reactive epoxy functionality of the impact modifier; and
allowing the crosslinking agent and the impact modifier to react within the melt processing unit to form a crosslinked epoxy-functionalized impact modifier; wherein the composition exhibits a tensile elongation at break of about 50% or more as determined in accordance with ISO Test no. 527 at a temperature of 23° C. and at a speed of 50 mm/min.

### Claim 2 (depends on 1)

The method according to claim 1, further comprising feeding a disulfide compound to the melt processing unit, the disulfide compound comprising reactive functionality at one or more terminal ends of the disulfide compound.

### Claim 3 (depends on 2)

The method according to claim 2, wherein the reactive functionality of the disulfide compound is the same as the reactive functionality of the crosslinking agent.

### Claim 4 (depends on 2)

The method according to claim 2, wherein the disulfide compound and the crosslinking agent are added in conjunction with one another.

### Claim 5 (depends on 1)

The method according to claim 1, further comprising forming the polyarylene sulfide composition according to a formation method comprising one or more of extrusion, injection molding, blow-molding, thermoforming, foaming, compression molding, hot-stamping, fiber spinning, and pultrusion.

### Claim 6 (depends on 1)

The method according to claim 1, further comprising extruding the polyarylene sulfide composition, wherein the extrusion process utilizes a compression ratio of between about 2.5:1 and about 4:1.

### Claim 7 (depends on 6)

The method according to claim 6, wherein the extrusion process utilizes a barrel having a length and a diameter, the ratio of the barrel length to the barrel diameter being from about 16 to about 24.

### Claim 8 (depends on 6)

The method according to claim 6, the extrusion process utilizing an extruder having at least four zones, the temperature of the first zone being from about 276° C. to about 288° C., the temperature of the second zone being from about 282° C. to about 299° C., the temperature of the third zone being from about 282° C. to about 299° C., and the temperature of the fourth zone being from about 540° C. to about 580° C.

### Claim 9 (depends on 6)

The method according to claim 6, the extrusion process utilizing a die, the temperature of the die being from about 293° C. to about 310° C.

### Claim 10 (depends on 6)

The method according to claim 6, the extrusion process having a head pressure that is from about 690 kPa to about 6900 kPa.

### Claim 11 (depends on 1)

The method according to claim 1, wherein the epoxy-functionalized impact modifier is present in an amount of 20 wt. % to 40 wt. %.

### Claim 12 (depends on 1)

The method according to claim 1, wherein the crosslinking agent is present in an amount of 0.75 wt. % to 1.75 wt. %.

### Claim 13 (depends on 1)

The method according to claim 1, wherein the polyarylene sulfide is present in an amount of 20 wt. % to about 90 wt. %.

### Claim 14 (depends on 1)

The method according to claim 1, wherein the crosslinking agent includes a dicarboxylic acid or salt thereof.

### Claim 15 (depends on 14)

The method according to claim 14, wherein the crosslinking agent includes terephthalic acid.

### Claim 16 (depends on 1)

The method according to claim 1, wherein the epoxy-functionalized impact modifier includes methacrylic monomer units.

### Claim 17 (depends on 16)

The method according to claim 16, the epoxy-functionalized impact modifier further includes α-olefin monomer units.

### Claim 18 (depends on 16)

The method according to claim 16, wherein the epoxy-functionalized monomer units include epoxy-functionalized methacrylic monomer units.

### Claim 19 (depends on 11)

The method according to claim 11, wherein the crosslinking agent is present in an amount of 1 wt. % to 2 wt. %.

### Claim 20 (depends on 19)

The method according to claim 19, wherein the composition exhibits a tensile elongation at break of about 70% or more as determined in accordance with ISO Test no. 527 at a temperature of 23° C. and at a speed of 50 mm/min.

### Claim 21 (depends on 1)

The method according to claim 1, wherein the ratio of the length of the melt processing unit to the blending length of the melt processing unit is from about 8 to about 40.

### Claim 22 (depends on 1)

The method according to claim 1, wherein the ratio of the length of the melt processing unit to the blending length of the melt processing unit is from about 10 to about 40.