gamma-Butyrolactone methacrylate → 3-Hydroxy-1-methacryloyloxyadamantane

HRID 1849953

Reaktionsgleichung

Reaktionsgleichung von HRID 1849953
[C:1]([O:6][C:7]1([CH2:12][CH3:13])[CH2:11][CH2:10][CH2:9][CH2:8]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:14]([O:19][CH:20]1[CH:27]2[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:29][C:21]1([CH:30]([CH3:32])[CH3:31])[CH2:22]3)[CH2:26]2)(=[O:18])[C:15]([CH3:17])=[CH2:16].C(OC1CCOC1=O)(=O)C(C)=C.[C:45]([O:50][C:51]12[CH2:60][CH:55]3[CH2:56][CH:57]([CH2:59][C:53]([OH:61])([CH2:54]3)[CH2:52]1)[CH2:58]2)(=[O:49])[C:46]([CH3:48])=[CH2:47]>O1CCCC1>[C:14]([O:19][CH:20]1[CH:27]2[CH2:26][CH:25]3[CH2:24][CH:23]([CH2:22][C:21]1([CH:30]([CH3:32])[CH3:31])[CH2:29]3)[CH2:28]2)(=[O:18])[C:15]([CH3:17])=[CH2:16].[C:1]([O:6][C:7]1([CH2:12][CH3:13])[CH2:11][CH2:10][CH2:9][CH2:8]1)(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:45]([O:50][C:51]12[CH2:58][CH:57]3[CH2:56][CH:55]([CH2:54][C:53]([OH:61])([CH2:59]3)[CH2:52]1)[CH2:60]2)(=[O:49])[C:46]([CH3:48])=[CH2:47]

Komponenten

7

Edukt 4

HCID 11206014gamma-Butyrolactone methacrylateHCID 118565233-Hydroxy-1-methacryloyloxyadamantaneHCID 180005792-Propenoic acid, 2-methyl-, 1-ethylcyclopentyl ester (9CI, ACI)HCID 668625631-Isopropyl-adamantanyl methacrylate

Produkt 2

HCID 118565233-Hydroxy-1-methacryloyloxyadamantaneHCID 131731389Iam ecpma

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 1-ethylcyclopentyl methacrylate (ECPMA, M1; 20 mmol), 1-isopropyl-adamantanyl methacrylate (IAM, M2; 20 mmol), 2-oxo-tetrahydro-furan-3-yl methacrylate (α-GBLMA, M3; 30 mmol), 3-oxo-4,10-dioxa-tricyclo[5.2.1.02,6]dec-8(or 9)-yl methacrylate (ODOTMA, M4; 20 mmol), and 3-hydroxy-adamantanyl methacrylate (HAMA, M5; 10 mmol) dissolved in 30 g of tetrahydrofuran (THF) was degassed by bubbling with nitrogen and charged to a 500 ml flask equipped with a condenser, nitrogen inlet and mechanical stirrer along with an additional 10 g of degassed THF. The solution is brought to reflux, and 6 g of dimethyl-2,2-azodiisobutyrate is dissolved in 5 g of THF and charged in to the flask. The polymerization mixture is then stirred for about 4 hours at reflux, after which time the reaction is diluted with 5 g of THF and the polymerization mixture cooled to room temperature. The polymer is precipitated by addition to 1.0 L of isopropanol, the solid collected by filtration, re-precipitated by dissolving in 50 g THF and dropwise addition to another 1.0 L isopropanol, and the precipitated polymer collected and dried under vacuum at 45° C. for 48 h. to yield photoresist polymer poly(IAM/ECPMA/α-GBLMA/ODOTMA/HAMA) (20:20:30:20:10 ratio, respectively). Mw=8,000.

Aufarbeitung

  1. customwas degassed
  2. customby bubbling with nitrogen
  3. additioncharged to a 500 ml flask
  4. customequipped with a condenser, nitrogen inlet and mechanical stirrer along with an additional 10 g of degassed THF
  5. temperatureto reflux
  6. dissolution6 g of dimethyl-2,2-azodiisobutyrate is dissolved in 5 g of THF
  7. additioncharged in to the flask
  8. temperatureat reflux
  9. additionafter which time the reaction is diluted with 5 g of THF
  10. customThe polymer is precipitated by addition to 1.0 L of isopropanol
  11. filtrationthe solid collected by filtration
  12. customre-precipitated
  13. dissolutionby dissolving in 50 g THF
  14. additiondropwise addition to another 1.0 L isopropanol
  15. customthe precipitated polymer collected
  16. customdried under vacuum at 45° C. for 48 h.

Quellen und Nachweise

ORD-Eintrag
ord-c35fff670b2d45658146bc5328039efc
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08956799B2

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