雙酚A二縮水甘油醚

雙酚A二縮水甘油醚
	IUPAC名; 5,5-Dimethyl-3,7-dioxa-1,9(2)-bis(oxirana)-4,6(2,4)-dibenzenanonaphane
別名	Diglycidyl ether of bisphenol A; 2,2-Bis(4-glycidyloxyphenyl)propane; Epoxide A
識別
縮寫	BADGE; DGEBA
CAS號	1675-54-3
PubChem	2286
ChemSpider	2199
SMILES	CC(C)(C1=CC=C(C=C1)OCC2CO2)C3=CC=C(C=C3)OCC4CO4;
InChI	1/C21H24O4/c1-21(2,15-3-7-17(8-4-15)22-11-19-13-24-19)16-5-9-18(10-6-16)23-12-20-14-25-20/h3-10,19-20H,11-14H2,1-2H3;
InChIKey	LCFVJGUPQDGYKZ-UHFFFAOYAQ
EINECS	216-823-5
KEGG	C14348
MeSH	C019273
性質
化學式	C21H24O4
摩爾質量	340.41 g·mol−1
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

雙酚A二縮水甘油醚（英語：bisphenol A diglycidyl ether，簡稱BADGE或DGEBA）是一種有機化合物，也是一種液態環氧樹脂。^[1]^[2]^[3]^[4]^[5]該化合物是一種無色粘稠液體（商業樣品可能呈現淡稻草色），是許多環氧樹脂配方的關鍵成分。^[6]^[7]再加入雙酚A、催化劑並加熱，可生產出分子量更高的固體雙酚A縮水甘油醚環氧樹脂。^[8]

雙酚A二縮水甘油醚環氧樹脂的結構：n通常在0~25範圍內，表示聚合亞基的數量

製備和反應

雙酚A二縮水甘油醚通過環氧氯丙烷對雙酚A進行O-烷基化反應製備而成。反應主要生成雙酚A二縮水甘油醚和一些低聚物。聚合度可低至0.1。^[9]此類環氧樹脂中的環氧化物含量很受關注。該參數通常用環氧值表示，即1千克樹脂中環氧化物當量（Eq./kg），或者用當量重量表示，即含有 1摩爾環氧化物樹脂的克重（g/mol）。由於不對稱環氧化物具有手性，因此雙環氧化物由三種立體異構體組成，但這些立體異構體並不分離。

雙酚 A 二縮水甘油醚會緩慢水解為2,2-二[4(2,3-二羥基丙氧基)苯基]丙烷（2,2-bis(4-(2,3-dihydroxypropoxy)phenyl)propane，bis-HPPP）。

同樣，DGEBA與丙烯酸反應生成乙烯基酯。反應的結果是環氧開環，在分子的每個末端生成不飽和酯。這種材料通常用苯乙烯稀釋，然後轉化為樹脂。

環氧樹脂是一種熱固性聚合物，使用固化劑進行交聯。環氧樹脂最常見的固化劑是多胺、氨基酰胺和酚類化合物。^[10]

安全

BADGE反應性高，與水或HCl接觸後會形成多種物質，其中的許多化合物（包括 BADGE本身）也被強烈懷疑是一種內分泌干擾物。^[11]醚水解會釋放出雙酚A，而雙酚A也被強烈懷疑是一種內分泌干擾物。^[12]^[13]20世紀90年代起，人們開始關注在一些食品罐頭內襯中使用BADGE環氧樹脂的問題。^[12]^[14]以雙酚A二縮水甘油醚為基礎的環氧塗料被廣泛用於與食品接觸的罐頭內壁塗層，因此屬於食品容器。已對這些材料及其類似物和共軛物進行了廣泛的測試，並制定了分析方法。^[15]^[16]

參考

^ Ellis, Bryan. Chemistry and Technology of Epoxy Resins. Dordrecht: Springer Netherlands. 1993. ISBN 978-94-011-2932-9. OCLC 851368739.
^ Bisphenol A Liquid Epoxy Resins | Business & Products. DIC Corporation. [2023-01-11] （英語）.
^ Epoxy: A Complete Guide. Copps Industries. [2023-01-11].
^ PubChem. Bisphenol A diglycidyl ether. pubchem.ncbi.nlm.nih.gov. [2023-01-11] （英語）.
^ 2,2-Bis(4-glycidyloxyphenyl)propane 1675-54-3 | TCI AMERICA. www.tcichemicals.com. [2023-01-11].
^ Hofer, Arnold; Schneider, Hildegard, and Siegenthaler, Nikolaus (1996) "Epoxy resin mixtures containing advancement catalysts", 美國專利第5,521,261號.
^ Pham, Ha Q.; Marks, Maurice J., Epoxy Resins, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a09_547.pub2
^ Ashcroft, W. R., Ellis, Bryan , 編, Curing agents for epoxy resins, Chemistry and Technology of Epoxy Resins (Dordrecht: Springer Netherlands), 1993: 37–71 [2023-01-11], ISBN 978-94-010-5302-0, doi:10.1007/978-94-011-2932-9_2 （英語）
^ Mark, Herman. Epoxy Resins. Encyclopedia of Polymer Science and Technology. 16 October 2013. ISBN 9780470073698.
^ Forrest, M.J.: Coatings and Inks for Food Contact Materials, in RAPRA review reports, vol. 16, no. 6 (2005), p.8
^ Wang, Dongqi; Zhao, Haoduo; Fei, Xunchang; Synder, Shane Allen; Fang, Mingliang; Liu, Min. A comprehensive review on the analytical method, occurrence, transformation and toxicity of a reactive pollutant: BADGE. Environment International. October 2021, 155: 106701. PMID 34146765. doi:10.1016/j.envint.2021.106701 . hdl:10356/161451 .
^ ^12.0 ^12.1 Walfried Rauter, Gerald Dickinger, Rudolf Zihlarz and Josef Lintschinger, "Determination of Bisphenol A diglycidyl ether (BADGE) and its hydrolysis products in canned oily foods from the Austrian market", Z. Lebensm. Unters. Forsch. A 208 (1999) 208–211
^ Leitlinie zur hygienischen Beurteilung von organischen Beschichtungen im Kontakt mit Trinkwasser (Beschichtungsleitlinie) [Guideline for public health evaluation of organic chemical coatings in contact with drinking water (coating guideline)] (PDF). www.umweltbundesamt.de. 16 March 2016 [6 October 2019]. （原始內容 (PDF)存檔於9 January 2017）（德語）.
^ Berdasco, Nancy Anne M.; Waechter, John M., Bingham, Eula; Cohrssen, Barbara; Powell, Charles H. , 編, Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds, Patty's Toxicology (Hoboken, NJ, USA: John Wiley & Sons, Inc.), 2012-08-17: 491–528 [2022-07-28], ISBN 978-0-471-12547-1, doi:10.1002/0471435139.tox083.pub2 （英語）
^ Lestido-Cardama, Antía; Sendón, Raquel; Rodríguez Bernaldo de Quirós, Ana. Tentative identification of BADGE derivatives in epoxy type coatings in a model sample: a beverage can. Journal of Coatings Technology and Research. 2022-11-01, 19 (6): 1893–1900. ISSN 1935-3804. S2CID 251912604. doi:10.1007/s11998-022-00662-6 （英語）.
^ Beszterda, Monika; Tądrowska, Magdalena; Frański, Rafał. Multi-detection method for the fast screening of bisphenol A diglycidyl ether conjugates in the can-coating material. Journal of Coatings Technology and Research. 2022-11-01, 19 (6): 1901–1907. ISSN 1935-3804. S2CID 252213795. doi:10.1007/s11998-022-00668-0 （英語）.

Template:PPAR modulators

[1] Ellis, Bryan. Chemistry and Technology of Epoxy Resins. Dordrecht: Springer Netherlands. 1993. ISBN 978-94-011-2932-9. OCLC 851368739.

[2] Bisphenol A Liquid Epoxy Resins | Business & Products. DIC Corporation. [2023-01-11] （英語）.

[3] Epoxy: A Complete Guide. Copps Industries. [2023-01-11].

[4] PubChem. Bisphenol A diglycidyl ether. pubchem.ncbi.nlm.nih.gov. [2023-01-11] （英語）.

[5] 2,2-Bis(4-glycidyloxyphenyl)propane 1675-54-3 | TCI AMERICA. www.tcichemicals.com. [2023-01-11].

[6] Hofer, Arnold; Schneider, Hildegard, and Siegenthaler, Nikolaus (1996) "Epoxy resin mixtures containing advancement catalysts", 美國專利第5,521,261號.

[Ullmann2-7] Pham, Ha Q.; Marks, Maurice J., Epoxy Resins, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a09_547.pub2

[8] Ashcroft, W. R., Ellis, Bryan , 編, Curing agents for epoxy resins, Chemistry and Technology of Epoxy Resins (Dordrecht: Springer Netherlands), 1993: 37–71 [2023-01-11], ISBN 978-94-010-5302-0, doi:10.1007/978-94-011-2932-9_2 （英語）

[9] Mark, Herman. Epoxy Resins. Encyclopedia of Polymer Science and Technology. 16 October 2013. ISBN 9780470073698.

[Coatings_and_Inks2-10] Forrest, M.J.: Coatings and Inks for Food Contact Materials, in RAPRA review reports, vol. 16, no. 6 (2005), p.8

[11] Wang, Dongqi; Zhao, Haoduo; Fei, Xunchang; Synder, Shane Allen; Fang, Mingliang; Liu, Min. A comprehensive review on the analytical method, occurrence, transformation and toxicity of a reactive pollutant: BADGE. Environment International. October 2021, 155: 106701. PMID 34146765. doi:10.1016/j.envint.2021.106701 . hdl:10356/161451 .

[rauter2-12] 12.0 ^12.1 Walfried Rauter, Gerald Dickinger, Rudolf Zihlarz and Josef Lintschinger, "Determination of Bisphenol A diglycidyl ether (BADGE) and its hydrolysis products in canned oily foods from the Austrian market", Z. Lebensm. Unters. Forsch. A 208 (1999) 208–211

[Coating_Guideline2-13] Leitlinie zur hygienischen Beurteilung von organischen Beschichtungen im Kontakt mit Trinkwasser (Beschichtungsleitlinie) [Guideline for public health evaluation of organic chemical coatings in contact with drinking water (coating guideline)] (PDF). www.umweltbundesamt.de. 16 March 2016 [6 October 2019]. （原始內容 (PDF)存檔於9 January 2017）（德語）.

[14] Berdasco, Nancy Anne M.; Waechter, John M., Bingham, Eula; Cohrssen, Barbara; Powell, Charles H. , 編, Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds, Patty's Toxicology (Hoboken, NJ, USA: John Wiley & Sons, Inc.), 2012-08-17: 491–528 [2022-07-28], ISBN 978-0-471-12547-1, doi:10.1002/0471435139.tox083.pub2 （英語）

[15] Lestido-Cardama, Antía; Sendón, Raquel; Rodríguez Bernaldo de Quirós, Ana. Tentative identification of BADGE derivatives in epoxy type coatings in a model sample: a beverage can. Journal of Coatings Technology and Research. 2022-11-01, 19 (6): 1893–1900. ISSN 1935-3804. S2CID 251912604. doi:10.1007/s11998-022-00662-6 （英語）.

[16] Beszterda, Monika; Tądrowska, Magdalena; Frański, Rafał. Multi-detection method for the fast screening of bisphenol A diglycidyl ether conjugates in the can-coating material. Journal of Coatings Technology and Research. 2022-11-01, 19 (6): 1901–1907. ISSN 1935-3804. S2CID 252213795. doi:10.1007/s11998-022-00668-0 （英語）.

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製備和反應

安全

相關

參考