IP Library Granted Patent US 10,815,341
Granted Patent B2
US 10,815,341 · App. 15/761,850 · Granted Oct 27, 2020

Polymeric materials

Inventors: Andrew Overend (Bolton, GB); David Loftus (Formby, GB); Philip Winrow (Ormskirk, GB); Chun Yee Lew (Liverpool, GB)
Assignee: COLORMATRIX HOLDINGS, INC.
C08J3/2056C08K5/12C08L67/04C08L77/02D01F1/10C08J2367/02C08K3/04C08K5/3412C08L2203/12D01F6/62
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Quick Facts
Patent No.
US 10,815,341
App. No.
15/761,850
Granted
Oct 27, 2020
Kind
B2
Abstract

A liquid formulation for addition to a polymeric material comprises a vehicle, an additive (e.g. a colourant) and carbonyl bis (1-caprolactan)). The liquid formulation may be used to colour melt spun fibre (e.g. PET or polyamide).

Claims (63)

1. A liquid formulation for addition to a polymeric material, said liquid formulation comprising a vehicle, an additive and carbonyl bis (1-caprolactan)) (herein referred to as CBC), wherein said vehicle has a flash point of at least 285° C., a % weight retention of greater than 85 wt % and a number average molecular weight in the range 750-1250 g/mol; and/or wherein said vehicle is a liquid at STP, has a boiling point at atmospheric pressure of 760 mmHg of greater than 300° C. and less than 1150° C. and a melting point of less than 0° C.

2. A formulation according to claim 1 , wherein said vehicle includes a moiety —OCOR 50 wherein R 50 includes at least 5 —CH 2 — moieties and includes less than 24 —CH 2 — moieties; and the sum of the number of —CH 2 — moieties in all R 50 groups of moieties —OCOR 50 is at least 15.

3. A formulation according to claim 1 , wherein said vehicle is selected from groups (A) to (I) defined as follows:

Group A—Pentaerythritol tri or tetra esters where the ester is derived or derivable from reaction of pentaerythritol with a carboxylic acid with a carbon chain length of C 12 to C 22 ;

Group B—Alkoxylated pentaerythritol tri or tetra esters where the ester is derived or derivable from the reaction of an alkoxylated pentaerythritol with a carboxylic acid with a carbon chain length of C 12 to C 22 ;

Group C—Dipentaerythritol penta or hexa esters where the ester is derived from the reaction of dipentaerythritol with a carboxylic acid with a carbon chain length of C 5 to C 18 ;

Group D—Alkoxylated dipentaerythritol penta or hexa esters where the ester is derived or derivable from the reaction of an alkoxylated dipentaerythritol with a carboxylic acid with a carbon chain length of C 5 to C 16 ;

Group E—Trimethylolpropane triesters where the ester is derived or derivable from the reaction of trimethylolpropane with a carboxylic acid with a carbon chain length of C 8 to C 22 ;

Group F—Alkoxylated trimethylolpropane triesters where the ester is derived or derivable from the reaction of an alkoxylated trimethylolpropane with a carboxylic acid with a carbon chain length of C 8 to C 22 ;

Group G—Esters of the tri-carboxylic acid of general formula:

where R 9 , R 10 and R 11 independently represent a hydrogen atom, an ester group or an optionally-substituted, preferably unsubstituted, alkyl group;

Group H—Aliphatic dicarboxylic acid species containing between 2 and 22 carbon atoms in the main structural backbone;

Group I—Fatty acid diesters of hydroxyl terminated polyester plasticisers derived from adipic acid and an alky diol; acetylated monoglycerides from hydrogenated castor oil; and ethoxylated fatty acid diesters.

4. A formulation according to claim 3 , wherein said vehicle is selected from Group A.

5. A formulation according to claim 1 , wherein said vehicle is of general formula

wherein each R 20 independently represents a C 11 to C 21 optionally-substituted, linear or branched, saturated or unsaturated alkyl group; and R 21 comprises a moiety R 20 COO— or an hydroxy group.

6. A formulation according to claim 1 , wherein said vehicle is a pentaerythritol tetra ester.

7. A formulation according to claim 1 , wherein said vehicle is pentaerythritol tetraisostearate.

8. A formulation according to claim 1 , wherein said liquid formulation includes at least 2 wt % of CBC.

9. A liquid formulation for addition to a polymeric material, said liquid formulation comprising a vehicle, an additive and carbonyl bis (1-caprolactan)) (herein referred to as CBC), wherein said liquid formulation includes:

30-80 wt % of one or more vehicles;

5-60 wt % of one or more colourants;

3-25 wt % of CBC.

10. A formulation according to claim 1 , wherein, in said liquid formulation, the ratio of the total weight of colourants divided by the weight of CBC is at least 2 and is less than 10.

11. A formulation according to claim 1 , wherein, in said liquid formulation, said CBC includes particles having a 1 μm or greater median particle diameter.

12. A method of introducing an additive into a polymeric material, the method comprising:

(i) selecting a polymeric material;

(ii) contacting the polymeric material with said additive, carbonyl bis (1-caprolactam) (CBC) and vehicle; and

(iii) melt-processing said polymeric material;

wherein said vehicle is selected from groups A to (I) defined as follows:

Group A—Pentaerythritol tri or tetra esters where the ester is derived or derivable from reaction of pentaerythritol with a carboxylic acid with a carbon chain length of C 12 to C 22 ;

Group B—Alkoxylated pentaerythritol tri or tetra esters where the ester is derived or derivable from the reaction of an alkoxylated pentaerythritol with a carboxylic acid with a carbon chain length of C 12 to C 22 :

Group C—Dipentaerythritol penta or hexa esters where the ester is derived from the reaction of dipentaerythritol with a carboxylic acid with a carbon chain length of C 5 to C 18 ;

Group D—Alkoxylated dipentaerythritol penta or hexa esters where the ester is derived or derivable from the reaction of an alkoxylated dipentaerythritol with a carboxylic acid with a carbon chain length of C 5 to C 16 ;

Group E—Trimethylolpropane triesters where the ester is derived or derivable from the reaction of trimethylolpropane with a carboxylic acid with a carbon chain length of C 8 to C 22 ;

Group F—Alkoxylated trimethylolpropane triesters where the ester is derived or derivable from the reaction of an alkoxylated trimethylolpropane with a carboxylic acid with a carbon chain length of C 8 to C 22 ;

Group G—Esters of the tri-carboxylic acid of general formula:

where R 9 , R 10 and R 11 independently represent a hydrogen atom, an ester group or an optionally-substituted, preferably unsubstituted, alkyl group;

Group H—Aliphatic dicarboxylic acid species containing between 2 and 22 carbon atoms in the main structural backbone;

Group I—Fatty acid diesters of hydroxyl terminated polyester plasticisers derived from adipic acid and an alky diol; acetylated monoglycerides from hydrogenated castor oil; and ethoxylated fatty acid diesters.

13. A formulation according to claim 1 , wherein said liquid formulation includes:

40-70 wt% of pentaerythritol tetraisostearate;

20-50 wt% of one or more colourants;

3-20 wt% of CBC.

14. A liquid formulation according to claim 9 , wherein said vehicle is selected from groups (A) to (I) defined as follows:

Group A—Pentaerythritol tri or tetra esters where the ester is derived or derivable from reaction of pentaerythritol with a carboxylic acid with a carbon chain length of C 12 to C 22 ;

Group B—Alkoxylated pentaerythritol tri or tetra esters where the ester is derived or derivable from the reaction of an alkoxylated pentaerythritol with a carboxylic acid with a carbon chain length of C 12 to C 22 ;

Group C—Dipentaerythritol penta or hexa esters where the ester is derived from the reaction of dipentaerythritol with a carboxylic acid with a carbon chain length of C 5 to C 18 ;

Group D—Alkoxylated dipentaerythritol penta or hexa esters where the ester is derived or derivable from the reaction of an alkoxylated dipentaerythritol with a carboxylic acid with a carbon chain length of C 5 to C 16 ;

Group E—Trimethylolpropane triesters where the ester is derived or derivable from the reaction of trimethylolpropane with a carboxylic acid with a carbon chain length of C 8 to C 22 ;

Group F—Alkoxylated trimethylolpropane triesters where the ester is derived or derivable from the reaction of an alkoxylated trimethylolpropane with a carboxylic acid with a carbon chain length of C 8 to C 22 ;

Group G—Esters of the tri-carboxylic acid of general formula:

where R 9 , R 10 and R 11 independently represent a hydrogen atom, an ester group or an optionally-substituted, preferably unsubstituted, alkyl group;

Group H—Aliphatic dicarboxylic acid species containing between 2 and 22 carbon atoms in the main structural backbone;

Group I—Fatty acid diesters of hydroxyl terminated polyester plasticisers derived from adipic acid and an alky diol; acetylated monoglycerides from hydrogenated castor oil; and ethoxylated fatty acid diesters.

15. A formulation according to claim 14 , wherein said liquid formulation includes 30-80 wt % of a pentaerythritol tetra ester.

16. A formulation according to claim 14 , wherein said liquid formulation includes:

40-70 wt % of pentaerythritol tetraisostearate;

20-50 wt % of one or more colourants;

3-20 wt % of CBC.

17. A formulation according to claim 15 , wherein, in said liquid formulation, the ratio of the total weight of colourants divided by the weight of CBC is at least 2 and is less than 10; and, in said liquid formulation, said CBC includes particles having a median particle diameter of between ≥1 μm and ≤200 μm.

18. A formulation according to claim 1 , wherein said liquid formulation includes less than 25 wt % of CBC.

19. A formulation according to claim 1 , wherein, in said liquid formulation said CBC includes particles having a median particle diameter 200 μm or less.

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 Mar 21, 2018
From: OVEREND, ANDREW; LOFTUS, DAVID; WINROW, PHILIP; LEW, CHUN YEE
To: COLORMATRIX HOLDINGS, INC.
Reel/Frame 045299/0316 →