Compositions containing rosin esters and ethylene polymers

• US 10,344,164 B2
• Filed: 03/24/2016
• Issued: 07/09/2019
• Est. Priority Date: 03/26/2015
• Status: Active Grant

• Current Assignee: Kraton Chemical LLC (DL Holdings Co., Ltd.)
• Original Assignee: Kraton Chemical LLC (DL Holdings Co., Ltd.)
• Inventors: Lange, Jos H. M., Schaapman, Mark C, Hinc, Justyna J.
• Primary Examiner(s): Jones, Robert S
• Application Number:
  US15/561,395
• Publication Number:
  US 20180105693A1
• Time in Patent Office: 1,202 Days
• CPC Class Codes: C08K 5/005 Stabilisers against oxidation, heat, light, ozone
• CPC Class Codes: C08L 2205/03 containing three or more polymers in a blend
• CPC Class Codes: C08L 23/0853 Vinylacetate
• CPC Class Codes: C08L 23/0869 Acids or derivatives thereof
• CPC Class Codes: C08L 91/06 Waxes
• CPC Class Codes: C08L 93/04 Rosin
• CPC Class Codes: C09F 1/04 Chemical modification, e.g. esterification resin soaps C11D
• CPC Class Codes: C09J 123/0853 Vinylacetate
• CPC Class Codes: C09J 123/0869 Acids or derivatives thereof
• CPC Class Codes: C09J 193/04 Rosin

Abstract

Disclosed are compositions which include an ethylene polymer derived from at least one polar monomer with one or more ester groups, which polymerize with ethylene, (e.g., a copolymer, or low molecular weight copolymer having a relatively high melt index, derived from ethylene and vinyl acetate and/or a copolymer, or low molecular weight copolymer having a relatively high melt index, derived from ethylene and «-buty! acrylate) and a rosin ester. The rosin ester can have a low hydroxy! number (e.g., a hydroxy! number six or five or less), a low acid number (e.g., an acid number of ten or less), a relatively low PAN number (e.g., a PAN number less than twenty-two or in between eight and twenty), a relatively high third moment or third power average molecular weight (Mz), (e.g., an Mz value in between 2500 and 12000 g/mol), a low sulfur content (e.g., a sulfur content lower than 600 ppm prior to antioxidant addition) or combinations thereof. The compositions can exhibit a high heat stress resistance (e.g., a heat stress pass temperature value higher than 52° C. or in between 48° C. and 60° C.) and/or improved viscosity stability and/or color stability upon thermal aging and/or improved compatibility.

Claims

1. A composition comprising,

(a) a polymer derived from ethylene polymer derived from at least one polar monomer with one or more ester groups, which polymerize with ethylene, and

(b) a rosin ester having a hydroxyl number of seven or less, an M_z value between 2500 and 12000 and less than 800 ppm sulfur,

wherein the rosin ester is obtained by

esterifying a rosin and

stripping off volatiles.

2. The composition of claim 1, wherein the rosin ester has a first sum of palladium, nickel and platinum ppm content value (A1), and a first iodine ppm content value (B1);

and the rosin has a second sum of palladium, nickel and platinum ppm content value (A2), and a second iodine ppm content ppm value (B2);

wherein A1 is lower than or equal to A2; and

B1 is lower than or equal to B2.

3. The composition of claim 1, wherein the rosin ester has an acid number of fifteen or less.

4. The composition of claim 3, wherein the sum of the hydroxyl number and the acid number is eighteen or less.

5. The composition of claim 1, wherein the rosin ester has a PAN number of twenty-five or less.

6. The composition of claim 1, wherein the rosin ester has a Gardner color of ten or less.

7. The composition of claim 1, wherein the rosin ester is derived from a polyhydric alcohol.

8. The composition of claim 1, wherein the rosin ester is derived from an alcohol, a rosin, and up to 10 weight %, by weight of all reactants, of one or more carboxylic acid functional organic compounds;

wherein the one or more carboxylic acid functional organic compounds have an average number of rotatable bonds of twelve or less than twelve.

9. The composition of claim 8, wherein the one or more carboxylic acid functional organic compounds includes a dicarboxylic acid or a polycarboxylic acid.

10. The composition of claim 1, wherein the rosin ester has a Mw value of 1700 to 4000 g/mol, and a M_n value of 1100 to 2000 g/mol.

11. The composition of claim 1, wherein the rosin ester has a softening point higher than 100°

C.

12. The composition of claim 1, wherein the polar monomer comprises a vinyl alkanoate monomer, acrylate ester monomer, methacrylate ester monomer, or mixtures thereof.

13. The composition of claim 1, further comprising one or more waxes.

14. The composition of claim 1, further comprising one or more antioxidants.

15. The composition of claim 1 wherein the rosin is tall oil rosin.

16. The composition of claim 1, wherein the rosin ester has a turbidimetric light transmission percentage that exceeds 75% within a temperature range of 80°

C. to 180°

C., after thermal aging at 177°

C. for 10 hours.

17. The composition of claim 1, wherein the rosin ester is derived from an alcohol, a rosin, and from 2 to 25 weight %, by weight of all reactants, of one or more dicarboxylic acid functional organic compounds, wherein the one or more dicarboxylic acid functional organic compounds have two to twelve rotatable bonds.

18. The composition of claim 1, which is a thermoplastic road marking formulation, a tire formulation, or an adhesive formulation.

19. The composition of claim 1, which is a hot-melt adhesive formulation.