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Electron deficient olefins and curable compositions prepared therefrom

A compound and composition technology, applied in the field of new electron-deficient olefins, can solve the problems that new electron-deficient olefins have not been described before

Inactive Publication Date: 2011-06-01
LOCTITE (R&D) LIMITED
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] As a result of the limitations of the various hitherto known synthesis methods for cyanoacrylates and the susceptibility of novel electron-deficient alkenes and for these reasons, such novel electron-deficient alkenes have not been described hitherto

Method used

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  • Electron deficient olefins and curable compositions prepared therefrom
  • Electron deficient olefins and curable compositions prepared therefrom
  • Electron deficient olefins and curable compositions prepared therefrom

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0160] PRIMENE 81-R imines are prepared by reacting PRIMENE 81-R amines with a stoichiometric equivalent of paraformaldehyde and removing the water of condensation. All imines formed are distillable liquids and exist as stable monomeric imines as 1 H NMR 60 MHz (CDCl 3 )2H s(br)7.45ppm and FTIR(1650cm -1 ) as confirmed.

Embodiment 2

[0162] PRIMENE 81-R iminium-MSA was prepared from PRIMENE 81-R imine by dropwise addition of methanesulfonic acid with stirring at ice-water bath temperature, resulting in a pale yellow iminium salt.

Embodiment 3

[0164]

[0165] To a stirred mixture of cyanoacetic acid (90 g, 1.05 mol), ethyl 2-hydroxymethacrylate (130 g, 1.0 mol), p-toluenesulfonic acid (500 mg) and hydroquinone (200 mg) was added toluene (150 mL), and The mixture was refluxed at a temperature of 150°C to remove water azeotropically.

[0166] After cooling, the reaction product was washed successively with 30% brine and water. The organic layer was dried over anhydrous sodium sulfate, filtered and the solvent was removed by rotary evaporator. The crude reaction product was purified by vacuum distillation (120-126° C. / 0.2 mbar) and the ester of structure A (102 g, 0.52 mol) was isolated in 52% yield. 1 H NMR (60MHz, CDCl 3): δ6.39(s, 1H), 5.89(s, 1H), 4.90(s, 2H), 4.28(q, J=6.0Hz, 2H), 3.50(s, 2H), 1.32(t, J= 6.0Hz, 3H); FT-IR (film): 2983.3, 2935.3, 2264.3, 1753.6, 1719.7, 1640.0, 1448.3, 1368.2, 1310.3, 1177.0, 1027.1, 817.2cm -1 ; GC / MS (EI) m / z (%): 198 (2) [M + +H], 152(40), 129(25), 101(38), 85(100), 83(4...

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Abstract

The present invention relates to novel electron deficient olefins, such as certain 2-cyanoacrylates and methylidene malonates, prepared using an imine or an iminium salt.

Description

technical field [0001] The present invention relates to novel electron deficient alkenes prepared using imines or iminium salts, such as certain 2-cyanoacrylates or methylenemalonates. Background technique [0002] Cyanoacrylate adhesives are known for their fast adhesion and ability to bond very large quantities of substrates. They are marketed as "super glue" type adhesives. They are useful as general-purpose adhesives because they are one-part adhesives, are very economical because only small amounts are effective, and generally do not require any equipment to effect curing. [0003] Traditionally, cyanoacrylate monomers are prepared via the Knoevenagel condensation reaction between a formaldehyde precursor, such as paraformaldehyde, and an alkyl cyanoacetate under the action of a basic catalyst. During this reaction, cyanoacrylate monomers are formed and polymerized in situ into prepolymers. The prepolymer is then thermally cracked or depolymerized to produce cyanoacr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/593C07C255/15C07C255/17C09J4/00
CPCC07C255/23C07C255/15C07C69/73C08K5/13C07C69/593C07C255/17C07C255/19C08F222/30
Inventor C·B·麦卡德勒赵立刚S·L·格拉迪K·D·穆尔纳罕
Owner LOCTITE (R&D) LIMITED
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