Isoprene → HCID 19842620, compound

HRID 718480Notes

Reaction equation

HRID 718480 reaction equation
CN(CCN(C)C)C.[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([Li])CCC.[CH2:22]=[CH:23][C:24](=[CH2:26])[CH3:25]>C1CCCCC1>[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:22]=[CH:23][C:24](=[CH2:25])[CH3:26].[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6557Isoprene3×HCID 7501Styrene4×HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 178418339Butyllithium

Product 1

HCID 19842620HCID 19842620, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
40 °C

Procedure

In a pressure-resistant reactor, 23.3 kg of cyclohexane, 2.8 millimoles of TMEDA, and 1.5 kg of styrene were introduced, and while the content was stirred at 40° C., 93 millimoles of n-butyllithium was added thereto. Polymerization was carried out for one hour while the temperature was increased to 50° C. The polymerization conversion ratio of styrene was 100%. Subsequently, 5.5 kg of isoprene was continuously added to the reactor over one hour while the temperature was controlled to be maintained at 50° C. to 60° C. After the addition of isoprene was completed, polymerization was carried out for another one hour. The polymerization conversion ratio of isoprene was 100%. Furthermore, 3.4 kg of styrene was continuously added thereto over one hour while the temperature was controlled to be maintained at 50° C. to 60° C. After the addition of styrene was completed, polymerization was carried out for another one hour, and thus a styrene-isoprene-styrene triblock copolymer was formed. The polymerization conversion ratio of styrene was 100%. Thereafter, 186 millimoles of methanol as a polymerization terminator was added thereto and mixed thoroughly therein to terminate the reaction. Incidentally, the amounts of the various reagents used in the reaction are summarized in Table 1. The reaction liquid obtained as described above was treated in the same manner as in Production Example 1, and thus a composition of Production Example 5 (block copolymer) was collected. Also, a portion of the reaction liquid thus obtained was taken, and the same measurements as in Production Example 1 were carried out. These measurement values are presented in Table 2.

Workup

  1. customPolymerization
  2. temperaturewas increased to 50° C
  3. temperatureto be maintained at 50° C. to 60° C
  4. custompolymerization
  5. waitwas carried out for another one hour
  6. waitover one hour while the temperature was controlled
  7. temperatureto be maintained at 50° C. to 60° C
  8. custompolymerization
  9. waitwas carried out for another one hour

Sources & evidence

ORD record
ord-4cfee31a34574da2953e3c4b6bb3943e
Source dataset
uspto-grants-2015_11
Patent number
US09193893B2

Reaction notes

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