# US 11,299,613 B2 · Ethylene-alpha-olefin copolymer-triallyl phosphate composition

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- Number: US 11,299,613 B2
- Document ID: US11299613B2
- Status: Granted
- Kind: B2
- Application number: 16/488,777
- Filed: 2018-02-21
- Published: 2020-02-27
- Granted: 2022-04-12
- Earliest claimed: 2017-02-28
- Assignees: Dow Global Technologies LLC
- Applicants: Dow Global Technologies LLC
- Inventors: Bharat I. Chaudhary
- Web page: https://patentgrep.com/patent/US11299613B2

## CPC

- C08L 23/0815: {with aliphatic 1-olefins containing one carbon-to-carbon double bond}
- C08L 23/16: Ethylene-propylene or ethylene-propylene-diene copolymers
- C08F 210/16: Copolymers of ethene with alpha-alkenes, e.g. EP rubbers
- C08F 210/18: with non-conjugated dienes, e.g. EPT rubbers
- C08K 5/01: Hydrocarbons {(C08K5/0091 takes precedence)}
- C08K 5/14: Peroxides
- C08K 5/3435: Piperidines
- C08K 5/375: containing six-membered aromatic rings {(C08K5/3725 takes precedence)}
- C08K 5/521: Esters of phosphoric acids, e.g. of H3PO4
- C09D 7/63: organic
- C09D 123/16: {Elastomeric} ethylene-propylene or ethylene-propylene-diene copolymers {, e.g. EPR and EPDM rubbers}
- H01B 3/441: {from alkenes}
- C08F 2810/20: leading to a crosslinking, either explicitly or inherently
- C08L 2201/08: Stabilised against heat, light or radiation or oxydation
- C08L 2203/202: use in electrical wires or wirecoating
- C08L 2205/02: containing two or more polymers of the same C08L -group
- C08L 2312/00: Crosslinking
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED 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)
- H01B: CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES (selection for magnetic properties H01F1/00; waveguides H01P {; printed circuits H05K})

## Abstract

A peroxide-curable ethylene copolymer composition comprising (A) a crosslinkable ethylene/alpha-olefin copolymer, (B) an effective amount of triallyl phosphate (TAP), (C) an organic peroxide; and, optionally, (D) a supplemental polymer; wherein the (A) crosslinkable ethylene/alpha-olefin copolymer is made by copolymerizing ethylene and an olefin-functional comonomer in the presence of a molecular catalyst useful therefor. Also provided are a cured product made from the composition, methods of making and using same, and articles containing same.

## Claims

### Claim 1

A peroxide-curable ethylene copolymer composition comprising 54.00 to 99.00 weight percent (wt %) of (A) a crosslinkable ethylene/alpha-olefin copolymer, which is made by a process comprising copolymerizing ethylene and an alpha-olefin comonomer in the presence of a molecular catalyst used for copolymerizing ethylene and the alpha-olefin comonomer, and which (A) crosslinkable ethylene/alpha-olefin copolymer has a density from 0.850 to 0.890 grams per cubic centimeter (g/cm3) measured according to ASTM D792 and is optionally characterized by at least one of properties (a) to (c): (a) a flexural modulus (2% secant) of from >0 to 6,500 psi (>0 to 45 MPa) measured according to ASTM D790-15e2, (b) a glass transition temperature (Tg) of −130° to −20° C. measured by differential scanning calorimetry (DSC) according to ASTM 3418-15, and (c) a melt index (190° C., 2.16 kilograms (kg), “I2”) of 0.5 decigram per minute (dg/min.) to 50 dg/min. measured according to ASTM D1238-04; from 0.950 to 5.00 wt % of (B) triallyl phosphate (TAP); from 0.050 to 5.00 wt % of (C) an organic peroxide; and from 0.00 to 40 wt % of (D) a supplemental polymer selected from an ethylene/unsaturated carboxylic ester copolymer, a polyethylene homopolymer, a non-(molecular catalyst)-formed ethylene/alpha-olefin copolymer, and a propylene-based polymer; with the proviso that the total weight of constituents (A) and (D) is 80.00 to 99.00 wt %; wherein all wt % are based on total weight of the peroxide-curable ethylene copolymer composition and total weight of the peroxide-curable ethylene copolymer composition is 100.0 wt %; wherein the alpha-olefin comonomer is a (C3-C20)alpha-olefin and the (A) crosslinkable ethylene/alpha-olefin copolymer is an ethylene(C3-C20)alpha-olefin bipolymer; wherein the peroxide-curable ethylene copolymer composition further comprises:
from 0.20 to 0.50 wt % constituent (E) wherein (E) is 2,2′-thiobis(2-t-butyl-5-methylphenol,
from 0.30 to 0.50 wt % constituent (F) wherein (F) is alpha-methyl styrene dimer (AMSD),
from 0.10 to 0.30 wt % constituent (H) wherein (H) is 1,3,5-triazine-2,4,6-triamine, N2,N2″-1,2-ethanediylbis[N2-[3-[[4,6-bis[butyl(1,2,2,6,6-pentamethyl-4-piperidinyl)amino]-1,3,5-triazin-2-yl]amino]propyl]-N′,N″-dibutyl-N′,N″-bis(1,2,2,6,6-pentamethyl-4-piperidinyl)-, and
from 0.40 to 0.80 wt % constituent (J) wherein (J) is a poly(ethylene glycol) having a Mn of 15000 to 25000 g/mol.

### Claim 2 (depends on 1)

The composition of claim 1 further described by any one of limitations (i) to (iv): (i) the (A) crosslinkable ethylene/alpha-olefin copolymer is from 90 to 99 wt % of the peroxide-curable ethylene copolymer composition, and the peroxide-curable ethylene copolymer composition is free of (lacks) the (D) supplemental polymer; (ii) the (A) crosslinkable ethylene/alpha-olefin copolymer is from 58.00 to 90.00 wt % and the (D) supplemental polymer is from 40.0 to 1.0 wt % of the peroxide-curable ethylene copolymer composition; (iii) the (D) supplemental polymer is a polypropylene homopolymer; and (iv) both (ii) and (iii).

### Claim 3 (depends on 1)

The composition of claim 1 further described by any one of limitations (i) to (iv): (i) the (B) triallyl phosphate (TAP) is from 1.01 to 4.54 wt %; (ii) the (B) triallyl phosphate (TAP) is from 1.05 to 4.00 wt %; (iii) the (B) triallyl phosphate (TAP) is from 1.10 to 3.00 wt %; (iv) the (B) triallyl phosphate (TAP) is from 1.50 to 4.600 wt %; wherein all wt % are based on total weight of the peroxide-curable ethylene copolymer composition.

### Claim 4 (depends on 1)

The composition of claim 1 further described by any one of limitations (i) to (v): (i) the (C) organic peroxide is from 1.0 to 4.0 wt % based on total weight of the peroxide-curable ethylene copolymer composition; (ii) the (C) organic peroxide is a compound of formula RO—O—O—RO, wherein each RO independently is a (C1-C20)alkyl group or (C6-C20)aryl group; (iii) the (C) organic peroxide is bis(1,1-dimethylethyl) peroxide; bis(1,1-dimethylpropyl) peroxide; 2,5-dimethyl-2,5-bis(1,1-dimethylethylperoxy) hexane; 2,5-dimethyl-2,5-bis(1,1-dimethylethylperoxy) hexyne; 4,4-bis(1,1-dimethylethylperoxy) valeric acid; butyl ester; 1,1-bis(1,1-dimethylethylperoxy)-3,3,5-trimethylcyclohexane; benzoyl peroxide; tert-butyl peroxybenzoate; di-tert-amyl peroxide (“DTAP”); bis(alpha-t-butyl-peroxyisopropyl) benzene (“BIPB”); isopropylcumyl t-butyl peroxide; t-butylcumylperoxide; di-t-butyl peroxide; 2,5-bis(t-butylperoxy)-2,5-dimethylhexane; 2,5-bis(t-butylperoxy)-2,5-dimethylhexyne-3,1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane; isopropylcumyl cumylperoxide; butyl 4,4-di(tert-butylperoxy) valerate; di(isopropylcumyl) peroxide; or dicumyl peroxide; (iv) the (C) organic peroxide is dicumyl peroxide; and (v) a combination of (i) and any one of (ii) to (iv).

### Claim 5 (depends on 1)

The composition of claim 1 wherein the peroxide-curable ethylene copolymer composition further comprises at least one of constituents (K) to (O): (K) a colorant; (L) a liquid aromatic or saturated hydrocarbon (LASH); (M) a methyl radical scavenger; (N) a scorch retardant; and (O) a filler.

### Claim 6 (depends on 1)

A method of making a peroxide-curable ethylene copolymer composition of claim 1, the method comprising contacting the amounts of constituents (A) to (C), and any optional constituents (D) and (K) to (O), to give the peroxide-curable ethylene copolymer composition.

### Claim 7 (depends on 1)

A crosslinked ethylene/alpha-olefin copolymer product that is a product of curing the peroxide-curable ethylene copolymer composition of claim 1.

### Claim 8 (depends on 7)

A manufactured article comprising a shaped form of the product of claim 7.

### Claim 9 (depends on 7)

A coated conductor comprising a conductive core and an insulation layer at least partially covering the conductive core, wherein at least a portion of the insulation layer comprises the crosslinked ethylene/alpha-olefin copolymer product of claim 7.

### Claim 10 (depends on 9)

A method of conducting electricity, the method comprising applying a voltage across the conductive core of the coated conductor of claim 9 so as to generate a flow of electricity through the conductive core.