IP Library Granted Patent US 9,458,362
Granted Patent B2
US 9,458,362 · App. 14/243,066 · Granted Oct 4, 2016

Adhesive compositions containing a block copolymer with polymyrcene

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Quick Facts
Patent No.
US 9,458,362
App. No.
14/243,066
Granted
Oct 4, 2016
Kind
B2
Abstract

The invention relates to a novel block copolymer comprising at least one polymeric monoalkenyl arene block and at least one polymeric myrcene block having a low and stable viscosity and having good adhesive properties when used in an adhesive composition or as a damping material. An adhesive composition is also described, preferably containing an SMS triblock optionally mixed with an SM diblock. The adhesive composition comprises: 1) a block copolymer having at least one polymeric monoalkenyl arene block and at least one polymeric myrcene block; 2) a tackifier; 3) optional plasticizer; and 4) optionally a stabilizer. Compared with adhesive compositions comprising SIS block copolymers, those comprising SMS block copolymers have lower and more stable viscosity.

Claims (4)

1. A block copolymer composition comprising at least one polymeric block of monoalkenyl arene and at least one polymeric block of myrcene, said composition having 50 wt. % or less monoalkenyl arene and a melt flow rate of greater than about 50 grams/10 min. at 200° C. and 5 kg weight according to ASTM D1238, said at least one block of monoalkenyl arene having a molecular weight of 10-20 kg/mol., and said at least one block of myrcene having a molecular weight of 40-220 kg/mol., said block copolymer composition has the general structure (S-M-S′) n X or (S-M) n X where S and S′ are polymeric blocks of monoalkenyl arene, M is a polymeric block of myrcene, and n is an integer from 1 to about 5, and X is the residue of a coupling agent, said at least one polymeric block of monoalkenyl arene contains at least 95 wt. % styrene with up to 5 wt. % of alpha-methylstyrene, methylstyrene, p-tertbutylstyrene, dimethylstyrene, or mixtures of these, based on the total weight of the monoalkenyl arene in said block copolymer, wherein said block copolymer composition has a viscosity retention greater than 80% for 24 hours, at 160° C. and a vinyl content ranging from about 5 mol. % to 50 mol. %.

2. An adhesive composition comprising 100 parts by weight of a block copolymer of two end blocks of monoalkenyl arene and a mid-block of myrcene having a vinyl content ranging from about 5 mol. % to 50 mol. %; from about 30 to 250 parts by weight of a tackifier, based on 100 parts of said block copolymer; from about 0.1 to 80 parts by weight of a plasticizer, based on 100 parts of said block copolymer; and from about 0.1 to 3 parts by weight of a stabilizer, based on 100 parts of said block copolymer, the molecular weight of each monoalkenyl arene block is from about 10 to 20 kg/mol., the molecular weight of said polymyrcene block is from 40 to 220 kg/mol., said tackifier is selected from the group of C 5 hydrocarbon resins, hydrogenated C 5 hydrocarbon resins, styrenated C 5 resins, C 9 hydrocarbon resins, hydrogenated C 9 hydrocarbon resins, styrenated C 9 resins, C 5 /C 9 hydrocarbon resins, a modified C 5 , C 9 , or C 5 /C 9 resin, terpenes, rosin ester, rosin derivatives or a mixture of two or more of these, said plasticizer is selected from the group of mineral or naphthenic oil, said block copolymer contains at least 50 wt. % of said myrcene, and said monoalkenyl arene is at least 10 wt. %, based on the total weight of said block copolymer.

3. A process for producing a coupled block copolymer of monoalkenyl arene and myrcene, comprising introducing into a reactor styrene and an organolithium initiator; polymerizing said monoalkenyl arene to form a polymeric block of monoalkenyl arene; introducing myrcene into said reactor; continuing polymerization of said myrcene to form a polymeric diblock of styrene and myrcene or introducing additional styrene to the polymeric diblock of styrene and myrcene to form a triblock of styrene and myrcene; introducing a coupling agent into said reactor and coupling said diblock or triblock copolymer of styrene and myrcene, forming (S-M-S) n X or (S-M) n X where S is polymeric blocks of styrene, M is a polymeric block of myrcene, and n is an integer from 1 to about 5, and X is the residue of a coupling agent, wherein said polystyrene content is 50 wt. % or less, and the molecular weight of a styrene block is 10-20 kg/mol. and the molecular weight of said myrcene block is 40-220 kg/mol., further comprising the step of introducing an amount of butadiene sufficient to introduce at least one molecule of butadiene per myrcene block between the steps of polymerizing said myrcene and introducing a coupling agent, and wherein the block copolymer has a vinyl content of about 5 mol. % to about 50 mol. %.

4. The process of claim 3 , wherein the amount of butadiene is up to 3 wt. %, based on the total weight of the coupled block copolymer.

Assignments (10)
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 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NO. 8837224 TO PATENT NO. 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 11, 2022
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 060344/0919 →
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 →
RELEASE OF SECURITY INTEREST Recorded Mar 15, 2022
From: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
To: KRATON POLYMERS U.S. LLC
Reel/Frame 059366/0611 →
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 →
PATENT SECURITY AGREEMENT Recorded Jan 7, 2016
From: KRATON POLYMERS U.S. LLC
To: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH, AS COLLATERAL AGENT
Reel/Frame 037457/0843 →
CORRECTIVE ASSIGNMENT TO CORRECT THE PATENT NUMBER 8837224 TO PATENT NUMBER 7737224 PREVIOUSLY RECORDED AT REEL: 037448 FRAME: 0453. ASSIGNOR(S) HEREBY CONFIRMS THE SECURITY INTEREST. Recorded Jan 6, 2016
From: KRATON POLYMERS U.S. LLC; ARIZONA CHEMICAL COMPANY, LLC
To: BANK OF AMERICA, N.A.
Reel/Frame 037448/0453 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 2, 2014
From: DUPONT, MARTINE; STOL, MARIANNE
To: KRATON POLYMERS U.S. LLC
Reel/Frame 032580/0511 →