IP Library Granted Patent US 11,254,848
Granted Patent B2
US 11,254,848 · App. 14/122,736 · Granted Feb 22, 2022

Propylene/ethylene copolymer film for heat seal

Inventors: Li-Min Tau (Lake Jackson, TX); Chai-Jing Chou (Sugar Land, TX); John Kaarto (Missouri City, TX); Peter S. Martin (Houston, TX); William G. Sheard (Missouri City, TX)
Assignee: W.R. GRACE & CO.-CONN.
C09K3/1006B32B27/08B65D25/14C08F210/06C08J5/18C08J2323/08Y10T428/31938
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Quick Facts
Patent No.
US 11,254,848
App. No.
14/122,736
Granted
Feb 22, 2022
Kind
B2
Abstract

The present disclosure provides compositions, films and articles containing a random propylene/ethylene copolymer and a substituted phenylene aromatic diester. Polymerization with an improved catalyst system increases the amount of ethylene incorporated into the random propylene/ethylene copolymer backbone which results in improved thermal properties, improved optical properties, and improved heat seal properties.

Claims (143)

1. A film comprising:

a catalytically polymerized random propylene/ethylene copolymer the catalyst comprising a substituted 1,2-phenylene aromatic diester internal electron donor having the structure (II)

wherein R 1 -R 14 are the same or different and each of R 1 -R 14 is selected from the group consisting of hydrogen, substituted hydrocarbyl group having 1 to 20 carbon atoms, unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof, wherein at least one of R 1 -R 14 is not hydrogen;

the random propylene/ethylene copolymer having:

(A) an ethylene incorporation index from greater than 0.65 to 0.85; and

(B) a xylene solubles content and total ethylene content according to the following equation

wt

%

xylene

solubles

-

wt

%

total

ethylene

wt

%

total

ethylene

<0.8

;

and

(C) a Koenig B-value from 0.90 to 1.0; and

wherein the random propylene/ethylene copolymer has an ethylene ratio from greater than 2.0 up to 4.0, wherein the ethylene ratio is defined as follows:

ethylene ratio=[ethylene present in XI (wt %)]/[ethylene present in XS (wt %)];

wherein XI is the xylene insoluble portion of said copolymer and XS is the xylene soluble portion of said copolymer.

2. The film of claim 1 wherein the substituted phenylene aromatic diester is 3-methyl-5-tert-butyl-1,2-phenylene dibenzoate.

3. An article comprising:

a heat seal comprising a first seal portion in contact with a second seal portion, the first seal portion and the second seal portion each being a component of a layer,

wherein the layer comprises a catalytically polymerized random propylene/ethylene copolymer comprising a substituted 1,2-phenylene aromatic diester internal electron donor having the structure (II)

wherein R 1 -R 14 are the same or different and each of R 1 -R 14 is selected from the group consisting of hydrogen, substituted hydrocarbyl group having 1 to 20 carbon atoms, unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof, wherein at least one of R 1 -R 14 is not hydrogen;

the random propylene/ethylene copolymer having:

(A) an ethylene incorporation index from greater than 0.65 to 0.85; and

(B) a xylene solubles content and total ethylene content according to the following equation

wt

%

xylene

solubles

-

wt

%

total

ethylene

wt

%

total

ethylene

<0.8

;

(C) a Koenig B-value from 0.90 to 1.0; and

wherein the random propylene/ethylene copolymer has an ethylene ratio from greater than 2.0 up to 4.0, wherein the ethylene ratio is defined as follows:

ethylene ratio=[ethylene present in XI (wt %)]/[ethylene present in XS (wt %)];

wherein XI is the xylene insoluble portion of said copolymer and XS is the xylene soluble portion of said copolymer.

4. The article of claim 3 wherein each of the first seal portion and the second seal portion is a component of a single film.

5. The article of claim 3 wherein the first seal portion is a component of a first film and the second seal portion is a component of a second film.

6. The article of claim 3 wherein the layer is a biaxially oriented film.

7. The article of claim 3 wherein the layer is a seal layer of a multilayer film.

8. A container comprising:

a film comprising a catalytically polymerized random propylene/ethylene copolymer, the catalyst comprising a substituted 1,2-phenylene aromatic diester internal electron donor having the structure (II);

wherein R 1 -R 14 are the same or different and each of R 1 -R 14 is selected from the group consisting of hydrogen, substituted hydrocarbyl group having 1 to 20 carbon atoms, unsubstituted hydrocarbyl group having 1 to 20 carbon atoms, alkoxy group having 1 to 20 carbon atoms, a heteroatom, and combinations thereof, wherein at least one of R 1 -R 14 is not hydrogen;

the random propylene/ethylene copolymer having:

(A) an ethylene incorporation index from greater than 0.65 to 0.85; and

(B) a xylene solubles content and total ethylene content according to the following equation

wt

%

xylene

solubles

-

wt

%

total

ethylene

wt

%

total

ethylene

<0.8

;

(C) a Koenig B-value from 0.90 to 1.0;

wherein the random propylene/ethylene copolymer has an ethylene ratio from greater than 2.0 up to 4.0, wherein the ethylene ratio is defined as follows:

ethylene ratio=[ethylene present in XI (wt %)]/[ethylene present in XS (wt %)]; and

wherein XI is the xylene insoluble portion of said copolymer and XS is the xylene soluble portion of said copolymer and

a heat seal sealing a first film portion to a second film portion and defining a container interior.

9. The container of claim 8 wherein the first film portion and the second film portion each are a component of a single film.

10. The container of claim 8 where the first film portion is a component of a first film and the second film portion is a component of a second film.

11. The container of claim 8 comprising a comestible located in the container interior.

Assignments (12)
NOTES SECURITY INTEREST Recorded Jan 29, 2026
From: W. R. GRACE & CO.-CONN.; ADVANCED REFINING TECHNOLOGIES LLC
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 074532/0229 →
SECURITY AGREEMENT (NOTES) Recorded Aug 19, 2025
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS NOTES COLLATERAL AGENT
Reel/Frame 072520/0653 →
SECURITY INTEREST Recorded Feb 17, 2023
From: W.R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 062792/0510 →
RELEASE OF SECURITY INTEREST Recorded Sep 23, 2021
From: GOLDMAN SACHS BANK USA
To: W. R. GRACE & CO.-CONN.
Reel/Frame 057594/0026 →
TERM LOAN SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 057594/0104 →
NOTES SECURITY AGREEMENT Recorded Sep 23, 2021
From: W. R. GRACE & CO.-CONN.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 057594/0156 →
RELEASE OF SECURITY AGREEMENT RECORDED AT REEL/FRAME NO.: 032159/0384 Recorded Apr 3, 2018
From: GOLDMAN SACHS BANK USA, AS THE COLLATERAL AGENT
To: W.R. GRACE & CO.-CONN.
Reel/Frame 045832/0887 →
SECURITY INTEREST Recorded Apr 3, 2018
From: W. R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 045828/0683 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 22, 2014
From: TAU, LI-MIN; CHOU, CHAI-JING; KAARTO, JOHN; MARTIN, PETER S.; SHEARD, WILLIAM G.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 032950/0275 →
CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE NAME TO "W. R. GRACE & CO. - CONN." PREVIOUSLY RECORDED ON REEL 032554 FRAME 0730. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNEE NAME WAS PREVIOUSLY INCORRECTLY LISTED IN THE RECORDATION COVER SHEET DATED 3/28/2014 AS "W. R. GRACE & CO. CONN.". Recorded Apr 2, 2014
From: DOW GLOBAL TECHNOLOGIES LLC; UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: W. R. GRACE & CO. - CONN.
Reel/Frame 032589/0554 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2014
From: DOW GLOBAL TECHNOLOGIES LLC; UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
To: W. R. GRACE & CO. CONN.
Reel/Frame 032554/0730 →
SECURITY AGREEMENT Recorded Feb 4, 2014
From: W.R. GRACE & CO.-CONN.
To: GOLDMAN SACHS BANK USA, AS THE COLLATERAL AGENT
Reel/Frame 032159/0384 →