海因环氧树脂是由海因或其衍生物经缩水甘油化而得到的含有乙内酰脲杂环的新型特种环氧树脂,保持了环氧树脂的原有应用性能,同时乙内酰脲的杂环结构又赋予其优异的电绝缘性、耐热性、耐候性和耐磨性等特性,具有广阔的应用前景。总结了1,3-二缩水甘油基海因、缩水甘油醚类海因环氧树脂和大分子海因环氧树脂3种类型海因环氧树脂的制备方法,简要介绍了近年来关于海因环氧树脂的基本性能研究,并对其在电子封装材料、覆铜板的基板材料、绝缘材料、材料抗菌剂及其它领域的应用进行了阐述,最后探讨了海因环氧树脂在工业重防腐领域中的应用潜力。
Hydantoin epoxy resin is a new type of special epoxy resin,which was glycidylated hydantoin and its derivatives.It maintains the performance of ordinary epoxy resin.More over,heterocyclic structure of hydan-toin makes hydantoin epoxy resin with good electrical isolation,heat resistance,weather resistance and abrasion performance.In this review,the preparation of 1 ,3-glycidyl hydantoin,glycidyloxy hydantoin epoxy resin and hydantoin epoxy resin with high molecular weight were reviewed.The current research status about the per-formances of hydantoin epoxy resin was reviewed.The application of hydantoin epoxy resin in the fields of elec-tronic packaging materials,substrate material of copper clad laminate,insulation material,antibacterial agent and so on were described.The development trend of hydantoin epoxy resin was further predicted.
参考文献
[1] | Frigione M E;Mascia L;Acierno D .Oligomeric and pol-ymeric modifiers for toughening of epoxy resins[J].Euro-pean Polymer Journal,1995,31(11):1021-1029. |
[2] | Bateman J H.Hydantoin and its derivatives[M].New York:John Wiley and Sons,Inc,1980:692-711. |
[3] | Lopez C A;Trigo G G .The chemistry of hydantoins[J].ADVANCES IN HETEROCYCLIC CHEMISTRY,1985,38:177-228. |
[4] | Jones G L;Wimbish G H;McIntosh W E .Phenytoin:basic and clinical pharmacology[J].Medicinal Research Reviews,1983,3(04):383-434. |
[5] | Elnagar H Y;Peters B C;Spielman E E et al.Process for producing N-halogenated hydantoins[P].US:7999118,2011-08-16. |
[6] | Tezon J G;Vazquez M H;Blaquier J A .Androgen-con-trolled subcellular distribution of its receptor in the rat ep-ididymis:5-dihydrotestosterone induced translocation isblocked by antiandrogens[J].ENDOCRINOLOGY,1982,111:2039-2046. |
[7] | Habermeier J .Epoxidharzeaus hydantoinen[J].Macromo-lecular Materials and Engineering,1977,63(01):63-104. |
[8] | Catsiff E H;Coulehan R E;Diprima J F.Epoxy resin chemistry[M].Washington:American Chemical Society,1979:115-135. |
[9] | Habermeier J;Baumann D .Epoxide resin mixtures of hetero-cyclic N,N-diglycidyl compounds[P].US:3809660,1974-05-07. |
[10] | Habermeier J;Porret D .Certain diglycidyl esters of N-heterocyclic compounds[P].US:3686174,1972-04-22. |
[11] | Habermeier J;Porret D .Diglycidyl derivatives of com-pounds containing two N-heterocyclic rings[P].US:3726895,1973-04-10. |
[12] | Batzer H;Habermeier J;Porret D .Diglycidyl com-pounds of monohydroxyalkyl hydantoins[P].US:3772326,1973-11-13. |
[13] | Jain R K;Chandra S.Hydantoin based epoxy resins[J].Pigment and Resin Technology,1992(05):13-17. |
[14] | Ma C Y .Method for synthesizing water-soluble hydan-toin epoxy resin[P].CN:101307131,2008-11-19. |
[15] | 马承银,吴元雄,孟杰.5,5-二甲基海因环氧树脂的合成[J].合成树脂及塑料,2008(06):29-32. |
[16] | Wu Y X .Study on the preparation and the properties of hydantoin epoxy resin coatings[D].Changsha:Hunan University,2009. |
[17] | Qin Z Y .Synthetic method of flame retardant type gly-colylurea epoxide resin[P].CN:101624439,2011-12-14. |
[18] | Zhou N L;Xia X X;Liu L X.Studies on hydantoin de-rivatives(Ⅰ)[J].Thermosetting Resin,1998(03):13-16. |
[19] | Lee T M;Chen K M .Hydantoin or barbituric acid-ex-tended epoxy resin[P].US:005130407,1992-07-14. |
[20] | Swarup S.A comparative study of bispheno l-A,hydan-toin and cyanuric acid based epoxy resins using XRD[J].Materials Sciences and Applications,2011(02):1516-1519. |
[21] | Zhang W;Liu Y X.Study on improving the toughness of hydantoin epoxy resin/anhydride system[A].Bejing,2006:553-556. |
[22] | Mikio K;Toshiaki T;Yuki E .Epoxy compound with nitrogen-containing ring[P].US:0172522,2013-07-04. |
[23] | Nie Z;Guo W Q;Fei D J et al.Reaction kinetics,ther-mal and mechanical properties of 1,3-diglycidyl-5,5-dimethyl hydantoin cured with PA and PSPA[J].Poly-mer Materials Science and Engineering,2012,28(07):55-59. |
[24] | 郝志勇,李玲.苯并(口恶)嗪/海茵环氧树脂体系固化反应的研究[J].化工新型材料,2008(11):72-73,80. |
[25] | Li L;Tian J L;Chen J N.Non-isothermal curing kinetic benzoxazine/hydantoin epoxy resin system[A].Jeju Is-land,2011:1-4. |
[26] | 李玲,田晋丽,陈剑楠.海因环氧树脂/HHPA体系的制备与性能[J].材料工程,2012(03):52-55. |
[27] | 李玲,田晋丽.海因环氧树脂/DDS体系的制备与性能[J].高分子材料科学与工程,2011(09):161-163,167. |
[28] | Zhu R C;Zhu X K .Application of epoxy resin system in the LED package[R].Yueyang:Chinese Epoxy Resin Application Technology Institute “Fifteenth Acadamic Forum of Epoxy Resin Application Technology”,2011. |
[29] | Denl H;Reeh U .Casting resin compositions for sealing opto-electronic components[P].US:4178274,1979-12-11. |
[30] | Kasai M;Takeyama T;Endo Y .Epoxy compound with nitrogen-containing ring[P].US:2013/0172522,2013-07-04. |
[31] | Haitko D A .Optoelectronic device[P].US:2007/0295956,2007-12-27. |
[32] | Wang J H;Zhao X Q;Tang Y H et al.A hydantoin epoxy resin composition for semiconductor device pack-age[P].CN:102372901,2012-03-14. |
[33] | Li Z H .A halogen-free flame retardant epoxy resin com-position and its application in flexible copper clad lami-nate[P].CN:101633770,2010-01-27. |
[34] | Hao Z Y .Research on halogen-free and non-phosphorus flame-retardant key resin materials used in CCL[D].Taiyuan:North University of China,2008. |
[35] | Reighter D H;Pa R .Concrete electrical insulator[P].US:4126598,1978-11-21. |
[36] | Tamte R;Fialla P .High-temperature resistant electri-cally insulating coating powder[P].WO:85/05627,1985-12-19. |
[37] | Zhou J;Huang S X;Chen Q S et al.Thermal insula-tion pouring glue and the preparation method[P].CN:102093665,2011-06-15. |
[38] | 亢真真,焦玉超,张冰,梁杰.卤胺抗菌材料的研究和应用[J].上海师范大学学报(自然科学版),2012(05):540-550. |
[39] | Worley S D;Liang J;Chen Y J et al.Biocidal N-halamine epoxides[P].WO:2006/099567,2006-09-21. |
[40] | Hasan B. Kocer;Idris Cerkez;S. D. Worley .Polymeric Antimicrobial N-Halamine Epoxides[J].ACS applied materials & interfaces,2011(8):2845-2850. |
[41] | Idris Cerkez;Hasan B. Kocer;S. D. Worley;R. M. Broughton;T. S. Huang .Epoxide tethering of polymeric N-halamine moieties[J].Cellulose,2012(3):959-966. |
[42] | Liang J;Chen YJ;Ren XH;Wu R;Barnes K;Worley SD;Broughton RM;Cho U;Kocer H;Huang TS .Fabric treated with antimicrobial N-halamine epoxides[J].Industrial & Engineering Chemistry Research,2007(20):6425-6429. |
[43] | Liang J;Wu R;Wang JW;Barnes K;Worley SD;Cho U;Lee J;Broughton RM;Huang TS .N-halamine biocidal coatings[J].Journal of industrial microbiology & biotechnology,2007(2):157-163. |
[44] | Tan Z S .A epoxy resin system used in the production of megawatt wind blade and the preparation method[P].CN:102702686,2012-10-03. |
[45] | Liu X T;Meng X Q;Yang G .A room temperature cur-able epoxy resin composition and its preparation method[P].CN:102977557,2013-03-20. |
[46] | Schmid R;Schmitter A;Gutekunst F et al.Mixtures of glycidylated hydantoins and polyhydric phenols and the use thereof for the preparation of plastic[P].US:4246366,1981-06-20. |
[47] | Sameer H;Eldin H T .A water-soluble hydantoin epox-ide/polyamine system as a wet-strength additive for pa-per[J].Journal of Applied Polymer Science,1981,26:1431-1436. |
[48] | Kuznetsov A;Figovsky O;Kim I et al.Composition for impregnation of floors[P].SU:1070144,1980-01-30. |
[49] | Figovsky O;Beilin D;Leykin A .Advanced patented protective nanomaterials and coatings[J].International Letters of Chemistry Physics and Astronomy,2013,10(01):102-109. |
[50] | Weiss J;Portchester N Y .Top coat composition to im-prove marine antifouling performance[P].US:4177302,1979-12-04. |
[51] | Speranza G P .Epoxy resin composition containing a cu-ring agent which is a reaction product of hydantoins formaldehyde and an mine[P].US:4581423,1986-04-08. |
[52] | Ohashi J J .Curableresin composition[P].WO:2005/016988,2005-02-24. |
[53] | Habermeier J;Knecht E;Gisler R .Carboxylic acid dian-hydrides based on trimellitic anhydride[P].US:4286097,1981-08-25. |
[54] | Rong Li;Pei Hu;Xuehong Ren .Antimicrobial N-halamine modified chitosan films[J].Carbohydrate Polymers: Scientific and Technological Aspects of Industrially Important Polysaccharides,2013(1):534-539. |
[55] | Wegmann A. .CHEMICAL RESISTANCE OF WATERBORNE EPOXY/AMINE COATINGS[J].Progress in Organic Coatings: An International Review Journal,1997(1/4):231-239. |
[56] | Chen W;Zhang H C;Wu Y et al.Preparation of the epoxy/polyacrylate complex latex I:effect of the acrylate monomers and their polymerizing on swelling behaviour of the epoxy latex particles[J].Journal of Functional Materials,2012,43(12):1651-1653. |
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