Isoprene → HCID 19842620, compound

HRID 1631415Notes

Reaction equation

HRID 1631415 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].Cl[Si](Cl)(Cl)Cl>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 24816Silicon tetrachlorideHCID 178418339Butyllithium

Product 1

HCID 19842620HCID 19842620, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
40 °C

Procedure

Ina pressure resistant reactor, 23.3 kg of cyclohexane, 4.00 millimoles of TMEDA, and 1.33 kg of styrene were added, and while the mixture was stirred at 40° C., 134.4 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% by weight. Subsequently, while the temperature was controlled to be maintained at 50° C. to 60° C., 7.00 kg of isoprene was continuously added to the reactor for 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%. Thereafter, 13.4 millimoles of tetrachlorosilane 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, which would serve as a block copolymer B. After this coupling reaction, 64.5 millimoles of methanol was added to the reactor as a polymerization terminator, and a polymerization termination reaction was carried out for one hour. The active terminal of a portion of the styrene-isoprene block copolymer having an active terminal was deactivated, and thereby a styrene-isoprene diblock copolymer which would serve as the polymer C (block copolymer C1) was formed. Thereafter, while the temperature was controlled to be maintained at 50° C. to 60° C., 1.67 kg of styrene was continuously added to the reactor for one hour. After completion of the addition of styrene, polymerization was carried out for another one hour, and thus a styrene-isoprene-styrene block copolymer was formed, which would serve as a block copolymer A. The polymerization conversion ratio for styrene was 100%. Subsequently, 268.8 millimoles of methanol was added to the system as a polymerization terminator, the resulting mixture was thoroughly mixed, and the reaction was terminated. The amounts of the various reagents used in the reaction are summarized in Table 1. A portion of the reaction liquid thus obtained was taken out and was subjected to the same analyses as in Reference Example 1. These values are presented in Table 2. To 100 parts of the reaction liquid obtained as described above (containing 30 parts of the polymer components), 0.3 part of 2,6-di-tert-butyl-p-cresol was added as an antioxidant and was mixed with the reaction liquid. The mixed solution was added dropwise in small amounts into hot water which was heated to 85° C. to 95° C., to thereby volatilize the solvent, and a precipitate was thus obtained. This precipitate was pulverized and dried with hot air at 85° C. Thus, a composition of Reference Example 3 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-cc508d2e7400459cbaf2ac1dfb2b75f3
Source dataset
uspto-grants-2014_07
Patent number
US08791196B2

Reaction notes

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