Thermally crosslinkable–decrosslinkable system using diepoxy crosslinkers containing sulfonate ester moiety

Shin, Yeong‐Deuk; Kawaue, Akiya; Okamura, Hitoshi; Shirai, Masamitsu

doi:10.1016/j.reactfunctpolym.2004.06.008

Cited by 22 publications

(8 citation statements)

References 16 publications

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“…1 H NMR spectra of homopolymer and copolymers. EKT equation is the same as KT equation shown in Equation (2). The difference between KT and EKT methods is the calculation of F and G. In EKT method, they are calculated through The EKT plot is given as Figure 2.…”

Section: Monomer Reactivity Ratio Calculationsmentioning

confidence: 99%

“…Functional groups give special characteristics to the polymers and can provide an approach to the subsequent modification of the polymers for specific applications. [1][2][3][4][5][6] Recently Degirmenci et al, synthesized mid-and end-chain cyclohexene functionalized polystyrene and poly(ε-caprolactone) and by epoxidation of the cyclohexene group. They obtained macromonomers with cyclohexene oxide functionality with potential for applications in photoinitiated cationic polymerization.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Copolymerization of cyclohexene-3-yl methyl methacrylate with styrene: synthesis, characterization, monomer reactivity ratios, and thermal properties

Barim

Yayla

Degirmenci

2014

Designed Monomers and Polymers

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A methacrylate monomer, cyclohexene-3-yl methyl methacrylate (CHMA) was synthesized by reaction of 3-cyclohexene-1-methanol with methacryloyl chloride in the presence of triethylamine at 0-5°C. The homopolymer of CHMA and its copolymer with styrene (St) were prepared by free radical polymerization. The Fourier transform infrared (FT-IR), 1 H NMR, and 13 C NMR spectroscopic techniques were used to characterize the homopolymers and copolymers.1 H NMR spectra were used to determine the compositions of the copolymers. Linearization methods such as Kelen-Tüdös, Extended Kelen-Tüdös, and a non-linear least squares method were all used to determine the reactivity ratios of the monomers. The effect of copolymer compositions on their thermal behavior was studied by differential thermal analysis and thermogravimetric analysis methods.

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Section: Monomer Reactivity Ratio Calculationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Copolymerization of cyclohexene-3-yl methyl methacrylate with styrene: synthesis, characterization, monomer reactivity ratios, and thermal properties

Barim

Yayla

Degirmenci

2014

Designed Monomers and Polymers

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“…It is known that sulfonate esters thermally decompose to produce sulfonic acid and alkene. In our previous work, we reported that the blended films containing diepoxides having sulfonate ester linkages worked as photo-crosslinkable and thermally degradable resins [16,17]. The thermal decomposition behaviors of sulfonate esters were different from those of carboxylate esters reported previously [14,15].…”

Section: Introductionmentioning

confidence: 87%

“…Demand on the 'reworkable resins', which is decomposable after use, is increasing more and more with respect to environmental aspects [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17]. Development of reworkable resins is one of the most promising technologies to contribute the solution of the environmental problems.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel photo-cross-linkable polymers with redissolution property

Shirai

Kawaue

Okamura

et al. 2004

Polymer

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“…In this point of view, some thermosets which are thermally or chemically degradable under a given condition have been extensively studied. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] We have previously reported the photocurable epoxy resins which can be re-dissolved in solvents by thermal treatments.12-18 The resins consist of epoxy moieties and tertiary ester linkages. Epoxy moieties acted as photocrosslinkable units by photo-induced acid catalyzed polymerization.…”

mentioning

confidence: 99%

Photocrosslinking System Using Highly-Functionalized Epoxy Crosslinkers Having Degradable Property

Okamura

Shin

Shirai

2006

Polym J

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ABSTRACT:Multifunctional crosslinkers having two, three, four and six functionalities were synthesized using a convergent method and were applied to a photocrosslinking system having thermally degradable properties. The multifunctional crosslinkers contained epoxy units and tertiary ester linkages. When the blended films of epoxides/poly-(p-vinylphenol) with a photoacid generator were irradiated and followed by baking at relatively lower temperatures (<100 C), the films became insoluble in solvents. Heating conditions strongly affected the insoluble fraction of the blends. Insoluble fraction of the blended films increased with the number of the epoxy unit of a molecule. The crosslinked films became soluble after prolonged bake at relatively higher treatments (>120 C). The reaction pathway of the blended system was studied by in situ FT-IR measurements. [doi:10.1295/polymj.PJ2006007] KEY WORDS Photocrosslinking / Decrosslinking / Thermal Degradation / Multifunctional / Epoxide / Photoacid Generator / Reworkable resins which are easily removable after use are getting more important in terms of environmental aspects. In this point of view, some thermosets which are thermally or chemically degradable under a given condition have been extensively studied. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18] We have previously reported the photocurable epoxy resins which can be re-dissolved in solvents by thermal treatments.12-18 The resins consist of epoxy moieties and tertiary ester linkages. Epoxy moieties acted as photocrosslinkable units by photo-induced acid catalyzed polymerization. Tertiary ester linkages were thermally cleavable units by heating to produce carboxylic acids and alkenes. The network was destroyed by the scission of tertiary ester linkages. In practical point of view, reactivity, sensitivity, thermal or chemical stability, and re-dissolution property of the polymers must be improved. Multifunctional epoxides are expected to show higher reactivity and sensitivity compared to mono-and difunctional epoxides. We have reported that trifunctional epoxide/poly(p-vinylphenol) (PVP) blended system works as a reworkable resin and the sensitivity of the system is higher than the difunctional epoxide/PVP blended system. 18In this paper, we report the synthesis of novel multifunctional epoxides having tertiary ester linkages. The multifunctional epoxides were synthesized by a convergent technique, where two or three molecules having both epoxy unit and tertiary ester unit in a molecule were linked together via another molecule. The multifunctional epoxides were used as crosslinkers of the system that has photocrosslinking and de-crosslinking properties. The system is a blend of PVP, the crosslinker, and a photoacid generator. The concept of the present system is shown in Figure 1. On irradiation, network formation occurs by the photoinducedacid catalyzed reaction of the epoxy moieties of the crosslinker and PVP. Thermal treatment of the crosslinked polymers induces the cleavage of the tertiary est...

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Thermally crosslinkable–decrosslinkable system using diepoxy crosslinkers containing sulfonate ester moiety

Cited by 22 publications

References 16 publications

Copolymerization of cyclohexene-3-yl methyl methacrylate with styrene: synthesis, characterization, monomer reactivity ratios, and thermal properties

Copolymerization of cyclohexene-3-yl methyl methacrylate with styrene: synthesis, characterization, monomer reactivity ratios, and thermal properties

Synthesis of novel photo-cross-linkable polymers with redissolution property

Photocrosslinking System Using Highly-Functionalized Epoxy Crosslinkers Having Degradable Property

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