IP Library Granted Patent US 9,940,852
Granted Patent B2
US 9,940,852 · App. 15/025,095 · Granted Apr 10, 2018

Rosin esters and compositions thereof

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Quick Facts
Patent No.
US 9,940,852
App. No.
15/025,095
Granted
Apr 10, 2018
Kind
B2
Abstract

Rosin esters are provided. The rosin esters can exhibit improved color (e.g., the rosin ester can have a neat Gardner color of 8.5 or less), improved oxidative stability (e.g., when 1000 ppm or less of an antioxidant is present in combination with the rosin ester, the rosin ester can exhibit an oxidative-induction time at 130° C. of at least 75 minutes), improved color stability (e.g., the rosin ester can exhibit less than a 10% change in neat Gardner color when heated to a temperature of 160° C. for a period of three hours), or combinations thereof. Also provided polymeric compositions comprising the rosin esters, as well as methods of making the rosin esters.

Claims (14)

1. A rosin ester comprising at least 70% by weight of an esterified dehydroabietic acid and an esterified dihydroabietic acid, wherein, when 1000 ppm or less of an antioxidant is present in combination with the rosin ester, the rosin ester exhibits an oxidative-induction time at 130° C. of at least 75 minutes, as measured using the methods specified in ASTM D5483-05(2010) wherein the rosin ester has a weight average molecular weight of at least 800 g/mol as determined using gel permeation chromatography as determined by ASTM D5296-05.

2. The rosin ester of claim 1 , wherein the weight ratio of the esterified dehydroabietic acid to the esterified dihydroabietic acid ranges from 1.3:1 to 1:2.6.

3. A rosin ester comprising at least 70% by weight of an esterified dehydroabietic acid and an esterified dihydroabietic acid,

wherein, when 1000 ppm or less of an antioxidant is present in combination with the rosin ester, the rosin ester exhibits an oxidative-induction time at 130° C. of at least 10 minutes as measured using the methods specified in ASTM D5483-05(2010), and

wherein the weight ratio of the esterified dehydroabietic acid to the esterified dihydroabietic acid ranges from 1:0.70 to 1:0.25,

wherein the rosin ester has a weight average molecular weight of at least 800 g/mol as determined using gel permeation chromatography as determined by ASTM D5296-05.

4. The rosin ester of claim 3 , wherein the rosin ester exhibits less than a 10% change in neat Gardner color when heated to a temperature of 160° C. for a period of three hours.

5. A composition comprising

(a) a polymer derived from one or more ethylenically-unsaturated monomers, or a blend of two or more polymers derived from one or more ethylenically-unsaturated monomers, and

(b) a rosin ester comprising at least 70% by weight of an esterified dehydroabietic acid and an esterified dihydroabietic acid, wherein the weight ratio of the esterified dehydroabietic acid to the esterified dihydroabietic acid ranges from 1.3:1 to 1:2.6, wherein the rosin ester has a weight average molecular weight of at least 800 g/mol as determined using gel permeation chromatography as determined by ASTM D529605.

6. The composition of claim 5 , wherein the polymer is a copolymer.

7. A composition comprising

(a) 45% by weight to 75% by weight of an oil, and

(b) 25% by weight to 55% by weight of a rosin ester defined by claim 1 .

Assignments (7)
RELEASE OF SECURITY INTEREST IN PATENTS Recorded Jul 24, 2024
From: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
To: KRATON CHEMICAL, LLC; KRATON CORPORATION
Reel/Frame 068671/0836 →
SECURITY INTEREST Recorded Mar 18, 2022
From: KRATON CHEMICAL, LLC; KRATON POLYMERS LLC; KRATON POLYMERS U.S. LLC
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 059525/0804 →
SECURITY INTEREST Recorded Mar 18, 2022
From: KRATON CHEMICAL, LLC; KRATON POLYMERS LLC; KRATON POLYMERS U.S. LLC
To: GOLDMAN SACHS BANK USA, AS COLLATERAL AGENT
Reel/Frame 059864/0455 →
RELEASE OF SECURITY INTEREST Recorded Mar 16, 2022
From: BANK OF AMERICA, N.A.
To: KRATON POLYMERS U.S. LLC; KRATON CHEMICAL, LLC F/K/A ARIZONA CHEMICAL COMPANY, LLC; KRATON POLYMERS LLC; KRATON CORPORATION; KRATON CHEMICAL B.V.
Reel/Frame 059910/0017 →
SECURITY INTEREST Recorded Apr 16, 2020
From: KRATON POLYMERS U.S. LLC; KRATON CHEMICAL, LLC F/K/A ARIZONA CHEMICAL COMPANY, LLC; KRATON POLYMERS LLC; KRATON CORPORATION
To: BANK OF AMERICA, N.A.
Reel/Frame 053020/0101 →
CHANGE OF NAME Recorded Apr 1, 2020
From: ARIZONA CHEMICAL COMPANY, LLC
To: KRATON CHEMICAL, LLC
Reel/Frame 052282/0011 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 14, 2017
From: WILLIAMS, PAUL A; NELSON, LLOYD A
To: ARIZONA CHEMICAL COMPANY, LLC
Reel/Frame 044121/0576 →