双酚A二缩水甘油醚

双酚A二缩水甘油醚
	IUPAC名; 5,5-Dimethyl-3,7-dioxa-1,9(2)-bis(oxirana)-4,6(2,4)-dibenzenanonaphane
别名	Diglycidyl ether of bisphenol A; 2,2-Bis(4-glycidyloxyphenyl)propane; Epoxide A
识别
缩写	BADGE; DGEBA
CAS号	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
性质
化学式	C21H24O4
摩尔质量	340.41 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

双酚A二缩水甘油醚（英语：bisphenol A diglycidyl ether，简称BADGE或DGEBA）是一种有机化合物，也是一种液态环氧树脂。^[1]^[2]^[3]^[4]^[5]该化合物是一种无色粘稠液体（商业样品可能呈现淡稻草色），是许多环氧树脂配方的关键成分。^[6]^[7]再加入双酚A、催化剂并加热，可生产出分子量更高的固体双酚A缩水甘油醚环氧树脂。^[8]

双酚A二缩水甘油醚环氧树脂的结构：n通常在0~25范围内，表示聚合亚基的数量

制备和反应

双酚A二缩水甘油醚通过环氧氯丙烷对双酚A进行O-烷基化反应制备而成。反应主要生成双酚A二缩水甘油醚和一些低聚物。聚合度可低至0.1。^[9]此类环氧树脂中的环氧化物含量很受关注。该参数通常用环氧值表示，即1千克树脂中环氧化物当量（Eq./kg），或者用当量重量表示，即含有 1摩尔环氧化物树脂的克重（g/mol）。由于不对称环氧化物具有手性，因此双环氧化物由三种立体异构体组成，但这些立体异构体并不分离。

双酚 A 二缩水甘油醚会缓慢水解为2,2-二[4(2,3-二羟基丙氧基)苯基]丙烷（2,2-bis(4-(2,3-dihydroxypropoxy)phenyl)propane，bis-HPPP）。

同样，DGEBA与丙烯酸反应生成乙烯基酯。反应的结果是环氧开环，在分子的每个末端生成不饱和酯。这种材料通常用苯乙烯稀释，然后转化为树脂。

环氧树脂是一种热固性聚合物，使用固化剂进行交联。环氧树脂最常见的固化剂是多胺、氨基酰胺和酚类化合物。^[10]

安全

BADGE反应性高，与水或HCl接触后会形成多种物质，其中的许多化合物（包括 BADGE本身）也被强烈怀疑是一种内分泌干扰物。^[11]醚水解会释放出双酚A，而双酚A也被强烈怀疑是一种内分泌干扰物。^[12]^[13]20世纪90年代起，人们开始关注在一些食品罐头内衬中使用BADGE环氧树脂的问题。^[12]^[14]以双酚A二缩水甘油醚为基础的环氧涂料被广泛用于与食品接触的罐头内壁涂层，因此属于食品容器。已对这些材料及其类似物和共轭物进行了广泛的测试，并制定了分析方法。^[15]^[16]

参考

^ 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] （英语）.
^ Epoxy: A Complete Guide. Copps Industries. [2023-01-11].
^ PubChem. Bisphenol A diglycidyl ether. pubchem.ncbi.nlm.nih.gov. [2023-01-11] （英语）.
^ 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", 美国专利第5,521,261号.
^ 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 , 编, 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 （英语）
^ 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]. （原始内容 (PDF)存档于9 January 2017）（德语）.
^ Berdasco, Nancy Anne M.; Waechter, John M., Bingham, Eula; Cohrssen, Barbara; Powell, Charles H. , 编, 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 （英语）
^ 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 （英语）.
^ 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 （英语）.

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] （英语）.

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

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

[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", 美国专利第5,521,261号.

[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 , 编, 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 （英语）

[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]. （原始内容 (PDF)存档于9 January 2017）（德语）.

[14] Berdasco, Nancy Anne M.; Waechter, John M., Bingham, Eula; Cohrssen, Barbara; Powell, Charles H. , 编, 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 （英语）

[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 （英语）.

[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 （英语）.

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制备和反应

安全

相关

参考