三羥甲基丙烷三縮水甘油醚

三羥甲基丙烷三縮水甘油醚
	IUPAC名; 2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane
別名	1-(2,3-Epoxypropoxy)-2,2-bis((2,3-epoxypropoxy)methyl)butane
識別
CAS號	3454-29-3
PubChem	103015
ChemSpider	93067
SMILES	CCC(COCC1CO1)(COCC2CO2)COCC3CO3;
InChI	1S/C15H26O6/c1-2-15(9-16-3-12-6-19-12,10-17-4-13-7-20-13)11-18-5-14-8-21-14/h12-14H,2-11H2,1H3;
InChIKey	QECCQGLIYMMHCR-UHFFFAOYSA-N
EINECS	222-384-0
ChEBI	189372
性質
化學式	C15H26O6
摩爾質量	302.36 g·mol−1
危險性
	GHS危險性符號;
GHS提示詞	Danger
H-術語	H315, H317, H318, H319, H334, H335, H412
P-術語	P261, P264, P264+265, P271, P272, P273, P280, P284, P302+352, P304+340, P305+351+338, P305+354+338, P317, P319
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

三羥甲基丙烷三縮水甘油醚（英語：trimethylolpropane triglycidyl ether，簡稱TMPTGE）是縮水甘油醚家族中的一種有機化學品，化學式為 C₁₅H₂₆O₆，主要用途是用作環氧樹脂的改性劑和活性稀釋劑。^[1]^[2]^[3]^[4]^[5]^[6]^[7]

別名[編輯]

XY636
2-乙基-2-(羥甲基)-1,3-丙二醇與氯甲基環氧乙烷的聚合物

生產[編輯]

1,1,1-三羥甲基丙烷和環氧氯丙烷與路易斯酸催化劑反應生成鹵代醇。下一步是用氫氧化鈉脫氫氯化，形成了三縮水甘油醚。^[8]^[9]

用途[編輯]

分子具有3個環氧乙烷官能團，其主要用途是改性和降低環氧樹脂的粘度。^[10]這些活性稀釋劑改性環氧樹脂可進一步配製成CASE應用：塗料（Coating）、^[11]粘合劑（Adhesives）、^[12]密封劑（Sealants）^[13]和彈性體（Elastomers）。稀釋劑的使用確實會影響環氧樹脂的機械性能和微觀結構。^[14]^[15]使用這種稀釋劑可以製備具有高抗衝擊性的環氧樹脂塗層。^[16]還可通過光引發機制用這種材料生產含氟聚合物，^[17]以及生產生物相容性材料。^[18]

參考[編輯]

^ PubChem. 1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane. pubchem.ncbi.nlm.nih.gov. [2022-04-11]. （原始內容存檔於2024-05-20）（英語）.
^ 2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane | C15H26O6 | ChemSpider. www.chemspider.com. [2022-04-12].
^ CAS Common Chemistry. commonchemistry.cas.org. [2022-04-12]. （原始內容存檔於2024-05-20）.
^ Trimethylolpropane triglycidyl ether, CAS Number: 3454-29-3. www.chemindustry.com. [2022-04-12]. （原始內容存檔於2024-05-20）.
^ Substance Information - ECHA. echa.europa.eu. [2022-04-12]. （原始內容存檔於2023-11-28）（英國英語）.
^ Trimethylolpropane triglycidyl ether. www.carbosynth.com. [2022-04-12]. （原始內容存檔於2024-05-20）.
^ Jagtap, Ameya Rajendra; More, Aarti. Developments in reactive diluents: a review. Polymer Bulletin. 2022-08-01, 79 (8): 5667–5708. ISSN 1436-2449. S2CID 235678040. doi:10.1007/s00289-021-03808-5 （英語）.
^ Crivello, James V. Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization. Journal of Polymer Science Part A: Polymer Chemistry. 2006, 44 (21): 6435–6448. Bibcode:2006JPoSA..44.6435C. ISSN 0887-624X. doi:10.1002/pola.21761.
^ US 5162547,Roth, Martin; Heinz Wolleb & Marc-Andre Truffer,「Process for the preparation of glycidyl ethers」,發表於1992-11-10,指定於Ciba-Geigy Corp.
^ Monte, Salvatore J., Pritchard, Geoffrey , 編, Diluents and viscosity modifiers for epoxy resins, Plastics Additives: An A-Z reference, Polymer Science and Technology Series 1 (Dordrecht: Springer Netherlands), 1998, 1: 211–216 [2022-03-29], ISBN 978-94-011-5862-6, doi:10.1007/978-94-011-5862-6_24, （原始內容存檔於2022-04-11）（英語）
^ WO application 2019238867,Bevinakatti, Hanamanthsa & Mojahedul Islam,「Herbicidal formulations comprising glyphosate and cote-based adjuvants」,發表於2019-12-19,指定於Nouryon Chemicals International BV
^ Hao, Xiu; Fan, Dong-Bin. Preparation and characterization of epoxy-crosslinked soy protein adhesive. Journal of Adhesion Science and Technology. 2018-12-17, 32 (24): 2682–2692. ISSN 0169-4243. S2CID 105550538. doi:10.1080/01694243.2018.1517488.
^ 14228-73-0 | CAS DataBase. www.chemicalbook.com. [2022-04-11]. （原始內容存檔於2022-04-11）.
^ Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas. The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings. Journal of Coatings Technology and Research. 2023-07-01, 20 (4): 1207–1221. ISSN 1935-3804. S2CID 256749849. doi:10.1007/s11998-022-00737-4 （英語）.
^ Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali. The effect of reactive diluent on mechanical properties and microstructure of epoxy resins. Polymer Bulletin. 2019-08-01, 76 (8): 3905–3927. ISSN 1436-2449. S2CID 105389177. doi:10.1007/s00289-018-2577-6 （英語）.
^ US 8062468,Finter, Jürgen; Andreas Kramer & Jan Olaf Schulenburg et al.,「Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins」,發表於2011-11-22,指定於Sika Technology AG
^ Trusiano, Giuseppe; Vitale, Alessandra; Bonneaud, Céline; Pugliese, Diego; Dalle Vacche, Sara; Joly-Duhamel, Christine; Friesen, Chadron M.; Bongiovanni, Roberta. Vinyl ethers and epoxides photoinduced copolymerization with perfluoropolyalkylether monomers. Colloid and Polymer Science. 2021-03-01, 299 (3): 509–521. ISSN 1435-1536. PMC 7952294 . PMID 33785978. doi:10.1007/s00396-020-04723-3 （英語）.
^ Journal of Electrochemical Science and Technology. www.jecst.org. [2022-04-12]. （原始內容存檔於2024-05-20）.

外部網站[編輯]

[1] PubChem. 1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane. pubchem.ncbi.nlm.nih.gov. [2022-04-11]. （原始內容存檔於2024-05-20）（英語）.

[2] 2-({2,2-Bis[(2-oxiranylmethoxy)methyl]butoxy}methyl)oxirane | C15H26O6 | ChemSpider. www.chemspider.com. [2022-04-12].

[3] CAS Common Chemistry. commonchemistry.cas.org. [2022-04-12]. （原始內容存檔於2024-05-20）.

[4] Trimethylolpropane triglycidyl ether, CAS Number: 3454-29-3. www.chemindustry.com. [2022-04-12]. （原始內容存檔於2024-05-20）.

[5] Substance Information - ECHA. echa.europa.eu. [2022-04-12]. （原始內容存檔於2023-11-28）（英國英語）.

[6] Trimethylolpropane triglycidyl ether. www.carbosynth.com. [2022-04-12]. （原始內容存檔於2024-05-20）.

[7] Jagtap, Ameya Rajendra; More, Aarti. Developments in reactive diluents: a review. Polymer Bulletin. 2022-08-01, 79 (8): 5667–5708. ISSN 1436-2449. S2CID 235678040. doi:10.1007/s00289-021-03808-5 （英語）.

[8] Crivello, James V. Design and synthesis of multifunctional glycidyl ethers that undergo frontal polymerization. Journal of Polymer Science Part A: Polymer Chemistry. 2006, 44 (21): 6435–6448. Bibcode:2006JPoSA..44.6435C. ISSN 0887-624X. doi:10.1002/pola.21761.

[9] US 5162547,Roth, Martin; Heinz Wolleb & Marc-Andre Truffer,「Process for the preparation of glycidyl ethers」,發表於1992-11-10,指定於Ciba-Geigy Corp.

[10] Monte, Salvatore J., Pritchard, Geoffrey , 編, Diluents and viscosity modifiers for epoxy resins, Plastics Additives: An A-Z reference, Polymer Science and Technology Series 1 (Dordrecht: Springer Netherlands), 1998, 1: 211–216 [2022-03-29], ISBN 978-94-011-5862-6, doi:10.1007/978-94-011-5862-6_24, （原始內容存檔於2022-04-11）（英語）

[11] WO application 2019238867,Bevinakatti, Hanamanthsa & Mojahedul Islam,「Herbicidal formulations comprising glyphosate and cote-based adjuvants」,發表於2019-12-19,指定於Nouryon Chemicals International BV

[12] Hao, Xiu; Fan, Dong-Bin. Preparation and characterization of epoxy-crosslinked soy protein adhesive. Journal of Adhesion Science and Technology. 2018-12-17, 32 (24): 2682–2692. ISSN 0169-4243. S2CID 105550538. doi:10.1080/01694243.2018.1517488.

[13] 14228-73-0 | CAS DataBase. www.chemicalbook.com. [2022-04-11]. （原始內容存檔於2022-04-11）.

[14] Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas. The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings. Journal of Coatings Technology and Research. 2023-07-01, 20 (4): 1207–1221. ISSN 1935-3804. S2CID 256749849. doi:10.1007/s11998-022-00737-4 （英語）.

[15] Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali. The effect of reactive diluent on mechanical properties and microstructure of epoxy resins. Polymer Bulletin. 2019-08-01, 76 (8): 3905–3927. ISSN 1436-2449. S2CID 105389177. doi:10.1007/s00289-018-2577-6 （英語）.

[16] US 8062468,Finter, Jürgen; Andreas Kramer & Jan Olaf Schulenburg et al.,「Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins」,發表於2011-11-22,指定於Sika Technology AG

[17] Trusiano, Giuseppe; Vitale, Alessandra; Bonneaud, Céline; Pugliese, Diego; Dalle Vacche, Sara; Joly-Duhamel, Christine; Friesen, Chadron M.; Bongiovanni, Roberta. Vinyl ethers and epoxides photoinduced copolymerization with perfluoropolyalkylether monomers. Colloid and Polymer Science. 2021-03-01, 299 (3): 509–521. ISSN 1435-1536. PMC 7952294 . PMID 33785978. doi:10.1007/s00396-020-04723-3 （英語）.

[18] Journal of Electrochemical Science and Technology. www.jecst.org. [2022-04-12]. （原始內容存檔於2024-05-20）.

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