Azobisisobutyronitrile → (4-((2,2-Difluoro-3-(methacryloyloxy)propanoyl)oxy)phenyl)diphenylsulfonium perfluorobutanesulfonate

HRID 1749162

反応式

HRID 1749162 の反応式
CC(N=NC(C#N)(C)C)(C#N)C.C([O:18][C:19]1(C)[CH:26]2CC3C[CH:24]([CH2:28][CH:20]1C3)[CH2:25]2)(=O)C(C)=C.O=C1C([O:36][C:37](=[O:41])[C:38]([CH3:40])=[CH2:39])CCO1.C(OC(O)C1C2C(=CC=CC=2)C=CC=1)(=[O:45])C=C.[F:59][C:60]([F:75])([S:71]([O-:74])(=[O:73])=[O:72])[C:61]([F:70])([F:69])[C:62]([F:68])([F:67])[C:63]([F:66])([F:65])[F:64].[C:76]1([SH+:82][C:83]2[CH:88]=[CH:87][CH:86]=[CH:85][CH:84]=2)[CH:81]=[CH:80][CH:79]=[CH:78][CH:77]=1>C(#N)C.O1CCCC1>[F:75][C:60]([F:59])([S:71]([O-:74])(=[O:73])=[O:72])[C:61]([F:69])([F:70])[C:62]([F:68])([F:67])[C:63]([F:66])([F:65])[F:64].[F:68][C:62]([F:67])([CH2:61][O:36][C:37](=[O:41])[C:38]([CH3:40])=[CH2:39])[C:63]([O:18][C:19]1[CH:20]=[CH:28][C:24]([S+:82]([C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][CH:81]=2)[C:83]2[CH:84]=[CH:85][CH:86]=[CH:87][CH:88]=2)=[CH:25][CH:26]=1)=[O:45]

参加物

7

反応物 5

HCID 6547AzobisisobutyronitrileHCID 98375662-Methyl-2-adamantyl methacrylateHCID 11206014gamma-Butyrolactone methacrylateHCID 22339024Diphenylsulfonium perfluorobutanesulfonateHCID 67252608Hydroxynaphthylmethyl acrylate

生成物 1

HCID 87560271(4-((2,2-Difluoro-3-(methacryloyloxy)propanoyl)oxy)phenyl)diphenylsulfonium perfluorobutanesulfonate

試薬・触媒・溶媒 1

HCID 22177404Acetonitrile tetrahydrofuran溶媒

実験手順

20.0 mmol of Vazo® 52 low-temperature polymerization initiator (E. I. du Pont de Nemours and Company) is added to a solution of 35.7 g (152.3 mmol) 2-methyl-2-adamantyl methacrylate, 25.9 g (152.3 mmol) 2-methyl-acrylic acid 2-oxo-tetrahydro-furan-3-yl ester, 17.4 g (76.2 mmol) hydroxynaphthylmethyl acrylate and 15.1 g (20.0 mmol) of the 4-((2,2-difluoro-3-(methacryloyloxy)propanoyl)oxy)phenyl)diphenylsulfonium perfluorobutanesulfonate in a 100 g acetonitrile:tetrahydrofuran 2:1 mixture. The monomers and initiator solution are degassed for 10 minutes. Under inert atmosphere, 5 mL of the monomer and initiator solution are introduced into a reactor which is preheated to 80° C. (oil bath). The remainder of the monomer and initiator mixture is fed into the reactor at 80° C. over a two hour period. Upon completion of the addition, the reaction mixture is refluxed for two additional hours. The mixture is next cooled to room temperature and the polymerization solution is precipitated into a large amount of diisopropyl ether, filtered and is then dried under vacuum. The resulting crude polymer is dissolved in 25-30 wt % tetrahydrofuran (THF) and precipitated into diisopropyl ether. The precipitated polymer is isolated by filtration and dried overnight at 40° C. under vacuum. The monomer structures for the polymeric bond PAG are summarized in following table.

後処理

  1. customThe monomers and initiator solution are degassed for 10 minutes
  2. additionUnder inert atmosphere, 5 mL of the monomer and initiator solution are introduced into a reactor which
  3. customis preheated to 80° C.
  4. additionUpon completion of the addition
  5. temperaturethe reaction mixture is refluxed for two additional hours
  6. customthe polymerization solution is precipitated into a large amount of diisopropyl ether
  7. filtrationfiltered
  8. customis then dried under vacuum
  9. dissolutionThe resulting crude polymer is dissolved in 25-30 wt % tetrahydrofuran (THF)
  10. customprecipitated into diisopropyl ether
  11. customThe precipitated polymer is isolated by filtration
  12. customdried overnight at 40° C. under vacuum

出典と根拠

ORDレコード
ord-f3f762cfc44c4f48b488011a054ec98c
出典データセット
uspto-grants-2015_10
特許番号
US09156785B2

関連ノート

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