IP Library Granted Patent US 10,557,017
Granted Patent B2
US 10,557,017 · App. 15/754,084 · Granted Feb 11, 2020

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.
C08K5/20C08L23/02C08L67/02C08L75/04C08K2201/012C08L2203/10
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Quick Facts
Patent No.
US 10,557,017
App. No.
15/754,084
Granted
Feb 11, 2020
Kind
B2
Abstract

A method of decreasing aldehyde content in a polymeric material such as polyethylene terephthalate which includes contacting the polymeric material with a compound including first, second and third fragments each having a moiety and a moiety NH.

Claims (82)

1. A method of decreasing aldehyde content in a polymeric material, the method comprises the step of contacting the polymeric material with a compound (A) which 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).

2. A method 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.

3. A method of decreasing aldehyde content in a polymeric material, the method comprises the step of contacting the polymeric material with a compound (A) which 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 moeity (B) are separated by at least one and not more than two atoms;

and 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 (C) is NH 2 ;

(II) a second fragment which comprises a moiety

and a moiety

NH   (B)

wherein the carbon atom of moiety (A) and the 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 method according to claim 3 , 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 .

5. A method according to claim 1 , wherein when compound (A) is not a polymer it has a molecular weight of at least 400 Daltons; or when compound (A) is a polymer it has a number average molecular weight (Mn) determined by GPC of at least 450 Daltons.

6. A method according to claim 1 , wherein said compound (A) is a liquid at 250° C.

7. A method 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 method according to claim 7 , wherein said main fragment has a molecular weight of more than the molecular weight of said first fragment.

9. A method according to claim 8 , 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.

10. A method according to claim 8 , wherein said main fragment is saturated.

11. A method according to claim 7 , wherein 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.

12. A method according to claim 7 , wherein said main fragment includes:

(i) a moiety:

wherein R 2 and R 3 independently represent a hydrogen atom or an optionally-substituted alkyl group;

wherein R 4 , R 5 , R 6 and R 7 independently represent a hydrogen atom or an optionally-substituted alkyl group; (iii) atoms selected from carbon, hydrogen, oxygen and nitrogen atoms only; and/or

(iv) a moiety:

wherein R 8 , R 9 , R 10 and R 11 independently represent a hydrogen atom or an optionally-substituted, alkyl group.

13. A method according to claim 7 , wherein said main fragment includes a moiety:

wherein R 8 , R 9 , R 10 and R 11 independently represent a hydrogen atom or an optionally-substituted alkyl group.

14. A method 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).

15. A method according to claim 1 , wherein said polymeric material contacted in the method is selected from a polyester, a polyurethane and a polyolefin.

16. A method according to claim 1 , wherein said compound (A) is associated with an organic liquid carrier which is compatible with said polymeric material; wherein the wt % of compound (A) in said mixture is less than 60% wt %.

17. A method of making an article from a polymeric material, the method comprising:

(a) selecting a compound (A);

(b) contacting the polymeric material with said compound (A); and

(c) forming said polymeric material into an article;

wherein said article comprises a container or preform for a container;

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).

18. A method according to claim 3 , wherein:

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

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 (C) is NH 2 .

19. A method according to claim 1 , wherein:

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

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;

said polymeric material contacted in the method is a polyester.

Assignments (5)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 19, 2019
From: CARMICHAEL, ADRIAN; OVEREND, ANDREW; JACKSON, MATTHEW; TATTUM, STEVEN
To: COLORMATRIX HOLDINGS, INC.
Reel/Frame 050436/0960 →
Priority Claims (1)
GB 1514937.0 · Aug 21, 2015 · national
Continuity (1)
Related Publication 20180244897A1 · Aug 30, 2018