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Rosin esters and compositions thereof

A technology of rosin ester and composition, which is applied in the field of rosin ester and its composition, and can solve the problems that rosin ester does not have proper performance, poor stability, etc.

Inactive Publication Date: 2016-08-31
ARIZONA CHEM CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Although suitable for many applications, many existing rosin esters do not have suitable properties for specific applications
In particular, many commercially available rosin esters are colored (e.g. yellow or tan) and exhibit poor stability

Method used

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  • Rosin esters and compositions thereof
  • Rosin esters and compositions thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0087] 500 g of tall oil rosin having a Gardner color (pure) of 5.5 and an acid number of 180.7 ( HYR, commercially available from Arizona Chemical) was charged to a four-necked flask (2 L) and heated to 200°C under a nitrogen atmosphere. After the rosin was completely melted, the rosin was stirred, and pentaerythritol (57.4 g) and 1425 (1.98 g) was added. The reaction mixture was heated to 275°C (heating rate 30°C / hour) and maintained at this temperature for 7.5 hours. The crude rosin ester was withdrawn and analyzed to have a Gardner color (pure) of 5.6, an acid value of 13.8, a softening point of 97.1° C. and an oxidation induction time of 0.5 minutes.

[0088] Without further purification, the crude rosin ester was hydrogenated at 650 psi and 260°C for 6 hours using 2 wt% palladium on carbon (5 wt% palladium). The catalyst was then removed by filtration to yield a rosin ester having a Gardner color (pure) of 1.4, an acid value of 11.2, a softening point of 98.0°C, and...

Embodiment 2

[0090] The procedure in Example 1 was repeated except that solvent was added during the hydrogenation reaction.

[0091] Crude rosin esters were prepared as described in Example 1. Without further purification, the crude rosin ester was hydrogenated at 650 psi and 260° C. for 6 hours using 2 wt % palladium on carbon (5 wt % palladium) in 50 wt % dimethylcyclohexane. The catalyst was then removed by filtration and the solvent was removed by distillation. The resulting rosin ester exhibited a Gardner color (pure) of 0.8, an acid value of 11.4, a softening point of 97.4°C, a PAN number of 0, and an oxidation induction time of 43.0 minutes. The color stability of the rosin esters was also tested. Incubated at 160°C for 3 hours, the rosin ester exhibited a Gardner color (pure) of 0.8. It was determined that the weight ratio of esterified dehydroabietic acid and esterified dihydroabietic acid in the obtained rosin ester was 1:1.6.

Embodiment 3

[0093] 500 g of tall oil rosin was charged into a four-necked flask (1 L). Place the flask under vacuum for 10 to 15 minutes. The vacuum was then released with nitrogen, and the flask was heated to 180°C with stirring. Will (Poly-tert-butylphenol disulfide 1.74 g, 0.31 wt%, commercially available from Arkema, Inc) was added to the reaction flask. The reaction flask contents were then stirred for 5 to 10 minutes. Catalyst (bis(((3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)methyl)-ethylcalcium phosphate), 1.98 g) and pentaerythritol (57.4 g) were added, And the reactants were heated to 270°C at a rate of 35°C / hour. The reaction temperature was maintained at 275°C until the acid number of the mixture was less than 15. Take out the crude rosin ester.

[0094] Without further purification, the crude rosin ester was hydrogenated at 450 psi and 260°C for 6 hours using 1.5 wt% palladium on carbon (5 wt% palladium). The catalyst was then removed by filtration in toluene and the ...

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Abstract

Rosin esters are provided. The rosin esters can exhibit improved color (e.g., the rosin ester can have a neat Gardner color of 4 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 DEG C of at least 30 minutes), improved color stability (e.g., the rosin ester can retain a neat Gardner color of 5 or less when heated to a temperature of 160 DEG C for a period of three hours), or combinations thereof. The invention also provides polymeric compositions comprising the rosin esters, as well as methods of making the rosin esters.

Description

technical field [0001] This application relates generally to rosin esters and methods of making and using them. Background technique [0002] Rosin esters, including those derived from polyols, have been known for over 50 years (see, eg, US Patent No. 1,820,265 to Bent et al.). Rosin esters are generally derived from rosin (which is primarily an isomeric C 20 tricyclic monocarboxylic acid) with an alcohol such as glycerol or pentaerythritol. The resulting rosin esters are used as additives in a variety of applications including, for example, as tackifiers in hot melt and pressure sensitive adhesives, modifiers for rubber and various plastics, emulsifiers for synthetic rubbers , the base material for chewing gum, resins in coating compositions such as traffic paints and inks, and sizing agents for papermaking. [0003] While suitable for many applications, many existing rosin esters do not possess suitable properties for particular applications. In particular, many commer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09F1/04C08L93/04
CPCC08L93/04C09F1/04C09J193/04C08L23/0853C08L91/06C08L53/00C09D193/04
Inventor 劳埃德·A·纳尔逊保罗·A·威廉斯哈里·杰罗尔德·米勒马克·德帕特尔利恩·鹏
Owner ARIZONA CHEM CO
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