Network polymers containing disulfide bond prepared by addition reactions of multi-functional epoxies, aziridine, or isocyanates with dicarboxylic acids or diols: structure, mechanical properties, and reductive degradation Article Swipe

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Naofumi Naga , Kazumasa Moriyama , Kazuma Hasegawa , Toshiki Tajima , Tamaki Nakano ·

YOU? · · 2025 · Open Access · · DOI: https://doi.org/10.21203/rs.3.rs-7874491/v1

Network polymers containing disulfide bonds were synthesized through ring-opening addition reactions of multi-functional epoxides or a tri-aziridine with dithiodicarboxylic acids. Reactions of tri- or tetra-functional epoxide, namely tris(4-hydroxyphenyl) methane triglycidyl ether (TME) and tetraphenylolethane glycidyl ether (TPE), with dithiodicarboxylic acids of varying methylene chain length, dithiodiglycolic acid (DTGA), 3,3'-dithiodipropionic acid (DTPA), or 4,4'-dithiodibutyric acid (DTBA), in the presence of tetrabutylammonium bromide in dimethyl sulfoxide (DMSO) at 85 ºC afforded the corresponding gels. Gels prepared from DTBA exhibited an enhanced Young’s modulus, attributed to the high extent of reaction conversion. These gels underwent reductive degradation upon immersion in a DMSO solution of dithiothreitol (DTT), while subsequent heating of the resulting solutions regenerated the gel structures through oxidation mediated by DMSO. Ring-opening addition reaction of tri-aziridine, 2,2-bishydroxymethylbutanol-tris[3-(1-aziridinyl)propionate] (3AZ) with dithiodicarboxylic acids in methanol successfully yielded porous polymers via polymerization induced phase separation (PIPS). The resulting materials exhibited porous morphologies composed of interconnected particles with diameters ranging from approximately 1 to 4 µm. The particle size increased with the alkyl length of the dithiodicarboxylic acid, concomitant with a reduction in the Young’s modulus of the porous polymers. In addition, the reaction of tri-functional isocyanate, 1,3,5-Tris[6-(isocyanate)hexyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione (3I) with bis(2-hydroxyethyl) disulfide (HEDS) or DTGA in DMSO produced the corresponding gels. These gels were susceptible to reductive degradation in DMSO solutions of DTT, and notably, the 3I-HEDS gel was degradable under electrochemical reduction. The reaction of 3I with DTGA in tetrahydrofuran (THF) afforded porous polymers exhibiting co-continuous monolithic morphologies consisting of interconnected particles. The morphology was tunable by varying concentration of triethylamine employed as a catalyst. The 3I-DTGA porous polymer likewise underwent reductive degradation upon immersion in THF solution of DTT.

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Chemistry Polymer chemistry Polymer Ether Tetrahydrofuran Polymerization Alkyl Sulfoxide Dimethyl sulfoxide Bromide Dicarboxylic acid Methanol Redox Acetic acid Organic chemistry Cationic polymerization Addition reaction Covalent bond Peroxide Silsesquioxane Cross-link Aryl Alkoxy group Allyl bromide Materials science

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Type: article
Landing Page: https://doi.org/10.21203/rs.3.rs-7874491/v1
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DOI: https://doi.org/10.21203/rs.3.rs-7874491/v1

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Title: Network polymers containing disulfide bond prepared by addition reactions of multi-functional epoxies, aziridine, or isocyanates with dicarboxylic acids or diols: structure, mechanical properties, and reductive degradation

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Publication year: 2025

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Publication date: 2025-11-14

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Authors: Naofumi Naga, Kazumasa Moriyama, Kazuma Hasegawa, Toshiki Tajima, Tamaki Nakano

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Landing page: https://doi.org/10.21203/rs.3.rs-7874491/v1

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Concepts: Chemistry, Polymer chemistry, Polymer, Ether, Tetrahydrofuran, Polymerization, Alkyl, Sulfoxide, Dimethyl sulfoxide, Bromide, Dicarboxylic acid, Methanol, Redox, Acetic acid, Organic chemistry, Cationic polymerization, Addition reaction, Covalent bond, Peroxide, Silsesquioxane, Cross-link, Aryl, Alkoxy group, Allyl bromide, Materials science

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abstract_inverted_index.afforded	69, 237
abstract_inverted_index.composed	148
abstract_inverted_index.dimethyl	63
abstract_inverted_index.employed	257
abstract_inverted_index.enhanced	79
abstract_inverted_index.epoxide,	26
abstract_inverted_index.epoxides	14
abstract_inverted_index.glycidyl	35
abstract_inverted_index.likewise	265
abstract_inverted_index.mediated	117
abstract_inverted_index.methanol	131
abstract_inverted_index.modulus,	81
abstract_inverted_index.notably,	219
abstract_inverted_index.particle	162
abstract_inverted_index.polymers	2, 135, 239
abstract_inverted_index.prepared	74
abstract_inverted_index.presence	58
abstract_inverted_index.produced	202
abstract_inverted_index.reaction	88, 122, 188, 229
abstract_inverted_index.solution	100, 273
abstract_inverted_index.Reactions	21
abstract_inverted_index.Young’s	80, 179
abstract_inverted_index.addition,	186
abstract_inverted_index.catalyst.	260
abstract_inverted_index.diameters	153
abstract_inverted_index.disulfide	4, 196
abstract_inverted_index.exhibited	77, 145
abstract_inverted_index.immersion	96, 270
abstract_inverted_index.increased	164
abstract_inverted_index.materials	144
abstract_inverted_index.methylene	43
abstract_inverted_index.oxidation	116
abstract_inverted_index.particles	151
abstract_inverted_index.polymers.	184
abstract_inverted_index.reactions	11
abstract_inverted_index.reduction	176
abstract_inverted_index.reductive	93, 211, 267
abstract_inverted_index.resulting	109, 143
abstract_inverted_index.solutions	110, 215
abstract_inverted_index.sulfoxide	64
abstract_inverted_index.underwent	92, 266
abstract_inverted_index.attributed	82
abstract_inverted_index.consisting	244
abstract_inverted_index.containing	3
abstract_inverted_index.degradable	224
abstract_inverted_index.exhibiting	240
abstract_inverted_index.monolithic	242
abstract_inverted_index.morphology	249
abstract_inverted_index.particles.	247
abstract_inverted_index.reduction.	227
abstract_inverted_index.separation	140
abstract_inverted_index.structures	114
abstract_inverted_index.subsequent	105
abstract_inverted_index.concomitant	173
abstract_inverted_index.conversion.	89
abstract_inverted_index.degradation	94, 212, 268
abstract_inverted_index.isocyanate,	191
abstract_inverted_index.regenerated	111
abstract_inverted_index.susceptible	209
abstract_inverted_index.synthesized	7
abstract_inverted_index.triglycidyl	30
abstract_inverted_index.Ring-opening	120
abstract_inverted_index.morphologies	147, 243
abstract_inverted_index.ring-opening	9
abstract_inverted_index.successfully	132
abstract_inverted_index.approximately	156
abstract_inverted_index.co-continuous	241
abstract_inverted_index.concentration	254
abstract_inverted_index.corresponding	71, 204
abstract_inverted_index.tri-aziridine	17
abstract_inverted_index.triethylamine	256
abstract_inverted_index.dithiothreitol	102
abstract_inverted_index.interconnected	150, 246
abstract_inverted_index.polymerization	137
abstract_inverted_index.tri-aziridine,	124
abstract_inverted_index.tri-functional	190
abstract_inverted_index.electrochemical	226
abstract_inverted_index.tetrahydrofuran	235
abstract_inverted_index.dithiodiglycolic	46
abstract_inverted_index.multi-functional	13
abstract_inverted_index.tetra-functional	25
abstract_inverted_index.dithiodicarboxylic	19, 39, 128, 171
abstract_inverted_index.tetrabutylammonium	60
abstract_inverted_index.bis(2-hydroxyethyl)	195
abstract_inverted_index.tetraphenylolethane	34
abstract_inverted_index.4,4'-dithiodibutyric	53
abstract_inverted_index.tris(4-hydroxyphenyl)	28
abstract_inverted_index.3,3'-dithiodipropionic	49
abstract_inverted_index.<title>Abstract</title>	0
abstract_inverted_index.2,2-bishydroxymethylbutanol-tris[3-(1-aziridinyl)propionate]	125
abstract_inverted_index.1,3,5-Tris[6-(isocyanate)hexyl]-1,3,5-triazine-2,4,6(1H,3H,5H)-trione	192
cited_by_percentile_year
countries_distinct_count	1
institutions_distinct_count	5
citation_normalized_percentile.value	0.6571683
citation_normalized_percentile.is_in_top_1_percent	False
citation_normalized_percentile.is_in_top_10_percent	False