IP Library Granted Patent US 11,220,589
Granted Patent B2
US 11,220,589 · App. 16/752,880 · Granted Jan 11, 2022

Method of decreasing aldehyde content in a polymeric material

Inventors: Adrian Carmichael (Yorkshire, GB); Andrew Overend (Bolton, GB); Matthew Jackson (Warrington, GB); Steven Tattum (Lancashire, GB)
Assignee: ColorMatrix Holdings, Inc.
C08K5/20C08K5/16C08L23/02C08L67/02C08L75/04C08K2201/00C08K2201/012C08L2203/10
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Quick Facts
Patent No.
US 11,220,589
App. No.
16/752,880
Granted
Jan 11, 2022
Kind
B2
Abstract

A method of decreasing aldehyde content in polymeric materials, for example in bottles comprising polyethylene terephthalate, uses a compound (A) which comprises first, second and third fragments which comprise a moiety Formula A) (A) and a moiety. (Formula B) NH (B).

Claims (76)

1. A polyester, having a reduced level of acetaldehyde, said polyester incorporating a compound (A) or a product of a reaction between compound (A) and aldehyde, wherein compound (A) includes:

(I) a first fragment which comprises a moiety

and a moiety

NH  (B)

wherein the carbon atom of moiety (A) and the nitrogen atom of moiety (B) are separated by at least one and not more than two atoms;

(II) a second fragment which comprises a moiety

and a moiety

NH  (B)

wherein the carbon atom of moiety (A) and the nitrogen atom of moiety (B) are separated by at least one and not more than two atoms; and

(III) a third fragment which comprises a moiety

and a moiety

NH  (B)

wherein said polyester is polyethylene terephthalate; and

wherein said compound (A) is a liquid at 250° C.

2. A polyester according to claim 1 , wherein the IV of the polyester is greater than 0.5 dL/g.

3. A polyester according to claim 1 , wherein compound (A) includes:

(I) a first fragment which comprises a moiety

and a moiety

NH  (B)

wherein the carbon atom of moiety (A) and the nitrogen atom of moiety (B) are separated by at least one and not more than two atoms;

(II) a second fragment which comprises a moiety

and a moiety

NH  (B)

wherein the carbon atom of moiety (A) and the nitrogen atom of moiety (B) are separated by at least one and not more than two atoms; and

(III) a third fragment which comprises a moiety

and a moiety

NH  (B).

4. A polyester according to claim 1 , wherein the carbon atom of moiety (A) and the nitrogen atom of moiety (B) are separated by two atoms which are both unsaturated carbon atoms.

5. A polyester according to claim 1 , wherein said first fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

wherein moiety (B) in said first fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 .

6. A polyester according to claim 5 , wherein said second fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

wherein moiety (B) of said second fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 ;

wherein said third fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

wherein moiety (B) of said third fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 .

7. A polyester according to claim 1 , wherein said first fragment, said second fragment and said third fragment are bonded to a main fragment of compound (A) via the nitrogen atoms of moiety CO.NH of respective moieties (A) of said first fragment, said second fragment and said third fragment.

8. A polyester according to claim 7 , wherein said main fragment consists of carbon and hydrogen atoms and only one other type of atom which is selected from oxygen and nitrogen atoms.

9. A polyester according to claim 8 , wherein said main fragment is saturated.

10. A polyester according to claim 9 , wherein said main fragment includes no primary amine moieties except primary amine moieties which are separated from a carbonyl moiety by at least one and not more than two atoms.

11. A polyester according to claim 1 , wherein compound (A) includes first, second and third fragments which comprise a moiety

wherein a linking moiety L 2 is arranged between said first, second and third fragments to which said first, second and third fragments are bonded at spaced apart positions, wherein the linking moiety is bonded to the benzene moieties of moiety (AA).

12. A polyester according to claim 1 , wherein:

the carbon atom of moiety (A) and the nitrogen atom of moiety (B) are separated by two atoms which are both unsaturated carbon atoms;

said first fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

moiety (B) in said first fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 ;

said second fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

moiety (B) of said second fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 ;

said third fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4; and

wherein moiety (B) of said third fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 .

13. A polyester according to claim 1 , wherein:

said first fragment, said second fragment and said third fragment are bonded to a main fragment of compound (A) via the nitrogen atoms of moiety CO.NH of respective moieties (A) of said first fragment, said second fragment and said third fragment, wherein said main fragment is saturated;

said main fragment includes substantially no primary amine moieties except primary amine moieties which are separated from a carbonyl moiety by at least one and not more than two atoms.

14. A polyester according to claim 2 , wherein compound (A) includes:

a first fragment which comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4,

wherein moiety (B) in said first fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 ;

a second fragment which comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

wherein moiety (B) of said second fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 ;

a third fragment which comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4.

15. A container or preform for a container, wherein said container or preform comprise a polyester as claimed in claim 1 .

16. A container or preform according to claim 15 , wherein said first fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

wherein moiety (B) in said first fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 ;

wherein said second fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

wherein moiety (B) of said second fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 ;

wherein said third fragment comprises a moiety:

wherein R′ represents a substituent and n1 is 0 to 4;

wherein moiety (B) of said third fragment is NH 2 and/or the NH moiety bonded to the benzene moiety is NH 2 .

Assignments (4)
RELEASE OF SECURITY INTERESTS IN PATENTS RECORDED AT REEL 067697, FRAME 0369. Recorded Jun 24, 2025
From: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
To: AVIENT CORPORATION; COLORMATRIX HOLDINGS, INC.
Reel/Frame 071708/0376 →
SECURITY AGREEMENT Recorded Jun 12, 2025
From: AVIENT CORPORATION; COLORMATRIX HOLDINGS, INC.; COLORMATRIX GROUP, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 071574/0571 →
PATENT SECURITY AGREEMENT (TERM) Recorded Jun 12, 2024
From: AVIENT CORPORATION; COLORMATRIX HOLDINGS, INC.
To: CITIBANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 067699/0676 →
SECURITY INTEREST Recorded Jun 11, 2024
From: AVIENT CORPORATION; COLORMATRIX HOLDINGS, INC.
To: WELLS FARGO CAPITAL FINANCE, LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 067697/0369 →