Isoprene → HCID 19842620, compound

HRID 1888839Notes

Reaction equation

HRID 1888839 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].CO[Si](OC)(OC)OC>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

7

Reactant 5

HCID 6557Isoprene3×HCID 7501Styrene2×HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 12682TetramethoxysilaneHCID 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, 3.26 millimoles of TMEDA, and 3.70 kg of styrene were added, and while the mixture was stirred at 40° C., 217.4 millimoles of n-butyllithium was added thereto. While the temperature was elevated to 50° C., polymerization was carried out for one hour. The polymerization conversion ratio for styrene was 100%. Subsequently, while the temperature was controlled to be maintained at 50° C. to 60° C., 6.3 C kg of isoprene was continuously added to the reactor over one hour. After completion of the addition of isoprene, polymerization was carried out for another one hour. The polymerization conversion ratio for isoprene was 100%. Subsequently, 18.5 millimoles of tetramethoxysilane was added to the reactor as a coupling agent, and a coupling reaction was carried out for 2 hours. Thus, a branched styrene-isoprene-styrene block copolymer was formed. Thereafter, 434.8 millimoles of methanol was added to the system as a polymerization terminator, the resulting mixture was thoroughly mixed, and the reaction was terminated. A portion of the reaction liquid thus obtained was taken out, and the same analyses as in Production Example 6 were carried out. These values are presented in Table 5. The subsequent operation was carried out in the same manner as in Production Example 6, and a block copolymer composition of Comparative Production Example 8 was collected.

Workup

  1. customwas elevated to 50° C.
  2. custompolymerization
  3. temperatureto be maintained at 50° C. to 60° C.
  4. waitwas carried out for another one hour
  5. customa coupling reaction
  6. waitwas carried out for 2 hours

Sources & evidence

ORD record
ord-a8c1d8ad5ba340f59a9bc0139b9aba87
Source dataset
uspto-grants-2013_08
Patent number
US08501869B2

Reaction notes

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