IP Library Granted Patent US 8,946,365
Granted Patent B2
US 8,946,365 · App. 13/740,320 · Granted Feb 3, 2015

Low molecular weight polystyrene resin and methods of making and using the same

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Quick Facts
Patent No.
US 8,946,365
App. No.
13/740,320
Granted
Feb 3, 2015
Kind
B2
Abstract

A low z-average molecular weight, high softening point polystyrene resin having a narrow molecular weight distribution, as well as methods of making and using the same, are provided. The use of an inert solvent and/or the order of addition of reactants during polymerization may contribute to the unique properties of the final homopolymeric resin. The polystyrene resin can be partially or fully hydrogenated and may have particular use as a tackifying agent in a variety of hot melt adhesive and rubber compositions.

Claims (18)

1. A process for producing a polystyrene homopolymer resin, said process comprising:

(a) combining at least a solid acid catalyst, an inert solvent, and styrene to thereby form a reaction mixture; and

(b) polymerizing at least a portion of said styrene in said reaction mixture to thereby produce said polystyrene homopolymer resin having a Ring & Ball softening point of at least 85° C. and not more than 110° C., a z-average molecular weight (Mz) from about 500 dalton to about 3,000 dalton, and a polydispersity index from about 1.1 to not more than 1.7,

wherein said inert solvent has an aromatic hydrogen content of not more than 10 percent, as measured by proton NMR; and

wherein said polystyrene homopolymer resin comprises styrenic moieties having not more than 5 weight percent of end-group moieties other than styrenic moieties.

2. The process of claim 1 , wherein said inert solvent has an aromatic hydrogen content of not more than 5 percent, wherein said inert solvent comprises one or more cycloaliphatic hydrocarbon compounds.

3. The process of claim 1 , wherein said weight ratio of said inert solvent to said styrene in said reaction mixture is at least 30:70.

4. The process of claim 1 , wherein during said polymerizing of step (b), the temperature of said reaction mixture changes by not more than 5° C., wherein said average reaction temperature is at least 50° C.

5. The process of claim 1 , wherein said polymerizing of step (b) is carried out at a reaction temperature of at least 40° C. and not more than 105° C.

6. The process of claim 1 , wherein said combining of step (a) includes introducing said styrene into a pre-mixed slurry of said solid acid catalyst and said inert solvent to thereby form said reaction mixture.

7. The process of claim 1 , wherein said reaction mixture comprises at least 3 weight percent and not more than 10 weight percent of said solid acid catalyst, based on the total weight of said styrene in said reaction mixture, wherein the moisture content of said solid acid catalyst is at least 1 weight percent and not more than 8 weight percent, based on the total weight of said solid acid catalyst.

8. The process of claim 1 , further comprising, subsequent to said polymerizing of step (b), separating at least a portion of said polystyrene polymer from said reaction mixture to thereby provide a polystyrene product and a separated reaction mixture and recycling at least a portion of said separated reaction mixture for use in said combining of step (a).

9. The process of claim 1 , further comprising, at least partially hydrogenating at least a portion of said polystyrene homopolymer resin subsequent to said polymerizing of step (b) to thereby provide an at least partially hydrogenated polystyrene polymer having an aromatic hydrogen content of not more than about 15 percent, as measured by proton NMR.

10. The process of claim 9 , further comprising, utilizing at least a portion of said at least partially hydrogenated polystyrene polymer in an adhesive composition selected from the group consisting of hot melt pressure sensitive adhesives, hot melt nonwoven adhesives, and hot melt packaging adhesives.

11. The process of claim 1 , wherein said solvent is an inert solvent having a proton NMR aromaticity of not more than 10 percent, wherein said inert solvent comprises tetramethylcyclohexane, trimethylcyclohexane, hexane, cyclohexane, heptanes, mineral spirits, or combinations thereof.

12. The process of claim 11 , wherein the weight ratio of said inert solvent to said one or more monomers in said reaction mixture is at least 30:70.

13. The process of claim 1 , wherein said polymerizing of step (b) is carried out at an average reaction temperature of at least 40° C. and not more than 105° C. and said reaction temperature changes by not more than 5° C. during said polymerizing of step (b).

14. The process of claim 1 , further comprising, at least partially hydrogenating at least a portion of said polystyrene homopolymer resin subsequent to said polymerizing of step (b) to thereby provide an at least partially hydrogenated polystyrene polymer having an aromatic hydrogen content of at least about 2 percent, as measured by proton NMR.

Assignments (3)
SECURITY INTEREST Recorded May 1, 2026
From: SYNTHOMER ADHESIVE TECHNOLOGIES LLC
To: GLAS TRUST CORPORATION LIMITED, AS SECURITY AGENT
Reel/Frame 075312/0405 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 25, 2022
From: EASTMAN CHEMICAL COMPANY
To: SYNTHOMER ADHESIVE TECHNOLOGIES LLC
Reel/Frame 059701/0618 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 13, 2013
From: CHENG, WEI MIN; RAJESH RAJA, PUTHENKOVILAKOM; KUTSEK, GEORGE JOSEPH; PENN, JOHN B.
To: EASTMAN CHEMICAL COMPANY
Reel/Frame 031324/0160 →