三羟甲基丙烷三缩水甘油醚

化合物

三羟甲基丙烷三缩水甘油醚(英语:trimethylolpropane triglycidyl ether,简称TMPTGE)是缩水甘油醚家族中的一种有机化学品,化学式为 C15H26O6,主要用途是用作环氧树脂的改性剂和活性稀释剂。[1][2][3][4][5][6][7]

三羟甲基丙烷三缩水甘油醚
IUPAC名
2-[2,2-bis(oxiran-2-ylmethoxymethyl)butoxymethyl]oxirane
别名 1-(2,3-Epoxypropoxy)-2,2-bis((2,3-epoxypropoxy)methyl)butane
识别
CAS号 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
性质
化学式 C15H26O6
摩尔质量 302.36 g·mol−1
危险性
GHS危险性符号
《全球化学品统一分类和标签制度》(简称“GHS”)中腐蚀性物质的标签图案《全球化学品统一分类和标签制度》(简称“GHS”)中有害物质的标签图案《全球化学品统一分类和标签制度》(简称“GHS”)中对人体有害物质的标签图案
GHS提示词 Danger
H-术语 H315, H317, H318, H319, H334, H335, H412
P-术语 P261, P264, P264+265, P271, P272, P273, P280, P284, P302+352, P304+340, P305+351+338, P305+354+338, P317, P319
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

别名

  • XY636
  • 2-乙基-2-(羟甲基)-1,3-丙二醇与氯甲基环氧乙烷的聚合物

生产

1,1,1-三羟甲基丙烷环氧氯丙烷路易斯酸催化剂反应生成卤代醇。下一步是用氢氧化钠脱氢氯化,形成了三缩水甘油醚。[8][9]

用途

分子具有3个环氧乙烷官能团,其主要用途是改性和降低环氧树脂的粘度。[10]这些活性稀释剂改性环氧树脂可进一步配制成CASE应用: 涂料(Coating)、[11]粘合剂(Adhesives)、[12]密封剂(Sealants)[13]弹性体(Elastomers)。稀释剂的使用确实会影响环氧树脂的机械性能和微观结构。[14][15]使用这种稀释剂可以制备具有高抗冲击性的环氧树脂涂层。[16]还可通过光引发机制用这种材料生产含氟聚合物,[17]以及生产生物相容性材料。[18]

相关

参考

  1. ^ PubChem. 1-(2,3-Epoxypropoxy)-2,2-bis[(2,3-epoxypropoxy)methyl]butane. pubchem.ncbi.nlm.nih.gov. [2022-04-11]. (原始内容存档于2024-05-20) (英语). 
  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]. (原始内容存档于2024-05-20). 
  4. ^ Trimethylolpropane triglycidyl ether, CAS Number: 3454-29-3. www.chemindustry.com. [2022-04-12]. (原始内容存档于2024-05-20). 
  5. ^ Substance Information - ECHA. echa.europa.eu. [2022-04-12]. (原始内容存档于2023-11-28) (英国英语). 
  6. ^ Trimethylolpropane triglycidyl ether. www.carbosynth.com. [2022-04-12]. (原始内容存档于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 (英语). 
  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”,发表于1992-11-10,指定于Ciba-Geigy Corp. 
  10. ^ Monte, Salvatore J., Pritchard, Geoffrey , 编, 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, (原始内容存档于2022-04-11) (英语) 
  11. ^ WO application 2019238867,Bevinakatti, Hanamanthsa & Mojahedul Islam,“Herbicidal formulations comprising glyphosate and cote-based adjuvants”,发表于2019-12-19,指定于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]. (原始内容存档于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 (英语). 
  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 (英语). 
  16. ^ US 8062468,Finter, Jürgen; Andreas Kramer & Jan Olaf Schulenburg et al.,“Low-temperature impact resistant thermosetting epoxide resin compositions with solid epoxide resins”,发表于2011-11-22,指定于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 (英语). 
  18. ^ Journal of Electrochemical Science and Technology. www.jecst.org. [2022-04-12]. (原始内容存档于2024-05-20). 

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