category: Функциональные и интеллектуальные материалы
УДК 621.792
СОВРЕМЕННЫЕ ТЕНДЕНЦИИ РАЗВИТИЯ КРЕМНИЙОРГАНИЧЕСКИХ ГЕРМЕТИКОВ И КОМПАУНДОВ ЗА РУБЕЖОМ (обзор)
Приведен литературный и патентный обзор с целью оценки тенденций развития кремнийорганических эластомеров за рубежом. Рассмотрены современные наполнители для кремнийорганических каучуков, модификации кремнийорганических герметиков, а также основные направления в исследованиях катализа процесса гидросилирования за рубежом.
Keywords: полимеры, герметики, катализаторы гидросилирования, гибридные системы.
ЛИТЕРАТУРА
1. Скляров Н.М. Путь длиною в 70 лет – от древесины до суперматериалов /Под общ. ред.
Е.Н. Каблова. М.: МИСиС–ВИАМ. 2002. 488 с.
2. Савенкова А.В., Тихонова И.В., Требукова Е.Д.. Тепломорозостойкие герметики /В сб.: Авиационные материалы на рубеже ХХ–XXI веков. М.: ВИАМ. 1994. С. 432–439.
3. Петрова А.П., Донской А.А., Чалых А.Е., Щербина А.А. Клеящие материалы. Герметики: Справочник. СПб.: НПО «Профессионал». 2008. 589 с.
4. Минаков В.Т., Савенкова А.В., Донской А.А. Кремнийорганические герметики //Российские полимерные новости. 2003. V. 8. №4. С. 37–41.
5. Pohmer K., Steinberger H. Silicone rubbers: innovative – high performance – efficient //Organosilicon Chemistry IV. Wiley-VCH. 2000. P. 699–709.
6. Zhao M., Feng Y., Li G., Li Y., Wang Y., Han Y., Sun X., Tan X. Synthesis of an adhesion-enhancing polysiloxane containing epoxy groups for addition-cure silicone light emitting diodes encapsulant //Polym. Adv. Technol. 2014. №25 (9). P. 927–933.
7. Pan K., Zeng X., Li H., Lai X. Synthesis of Siloxanes Containing Vinyl and Epoxy Group and its Enhancement for Adhesion of Addition-Cure Silicone Encapsulant //J. Macromol. 2013. №50 (11). P. 1126–1132.
8. Polysiloxane blends has good adhesion to substrates, able release from molds; homo- or copolymers of polysiloxane, polysilsesquioxanes, or polysilicates; bonding to metallic, plastic and thermoplastic substrates: pat. 7288322 US; pabl. 30.10.2007.
9. Caseri W., Pregosin P.S. Hydrosilylation chemistry and catalysis with CiS–PtCl2(PhCH=CH2)2 //Organometallics. 1988. №7 (6). P. 1373–1380.
10. Addition curable self-adhesive silicone rubber composition: pat. 8937123 US; pabl. 20.01.2015.
11. Preparation of silicone rubber elastomers: pat. 8329831 US; pabl. 11.12.2012.
12. Silicone rubber composition with improved fluidity: pat. 5352724 US; pabl. 04.10.1994.
13. Liquid silicone rubber composition of low specific gravity: pat. 6297291 US; pabl. 02.01.2001.
14. Peeters L. Low viscosity, high strength and fast curing //Adhesion, adhesives, sealants. 2013. №10(1). P. 14–17.
15. Silicone-acrylic copolymer: pat. 0012653 US; pabl. 04.02.14.
16. Kownacki I., Marciniec B., Steinberger H., Kubicki M., Hoffmann M., Ziarko A., Szubert K., Majchrzak M., Rubinsztajn S. Effect of triorganophosphites on platinum catalyzed curing of silicon rubber //Appl. Catalysis A. 2009. V. 362 (1–2). P. 106–114.
17. Addition-curable fluorosilicone rubber composition: pat. 2700677 EP; pabl. 26.02.14.
18. Gerlach E., Romanowski R., Jones B.A., Netto T.J. New technology to produce silicone sponge without chemical blowing agents or volatile organics /Proceedings of «Blowing agents and foaming processes» conference. 2004. P. 197–204.
19. High resilient silicone foam and process for preparing same: pat. 7393879 US; pabl. 01.07.2008.
20. Hydrosilation reaction utilizing a (cyclopentadiene)(sigma-aliphatic) platinum complex and a free radical photoinitiator: pat. 6376569 US; pabl. 23.04.2002.
21. Photoinitiators for hydrosilation of polysiloxanes; release agents: pat. 4510094 US; pabl. 09.04.1985.
22. Irradiation-curable silicone compositions, photo-active platinum (IV) compounds, and method: pat. 6150546 US; pabl. 21.11.2000.
23. Cyclopentadienylplatinum (iv) compounds having a trisubstituted-silyl aliphatic group attached to platinum by carbon-platinum linkages as hydrosilylation catalysts in irradiation-curable silicones: pat. 6127446 US; pabl. 03.10.2000.
34. Mayer T., Burget D., Mignani G., Fouassier J. P. Photohydrosilylation reaction of silicone polymers. Platinum-based photocatalysts: Trimethyl(β-dicarbonyl) platinum IV complexes //J. Polymer Sci. A. 1996. №34 (15). P. 3141–3146.
25. Wang F., Neckers D.C. Photoactivated hydrosilylation reaction of alkynes //Organomet J. Chem. 2003. №665 (1–2). P. 1–6.
26. Maciejewski H., Wawrzyńczak A., Dutkiewicz M., Fiedorow R. Silicone waxes–synthesis via hydrosilylation in homo- and heterogeneous systems //Molec J. Catalysis. 2006. №257 (1–2).
P. 141–148.
27. Brook A. Silicon in Organic, Organometallic, and Polymer Chemistry //Wiley. 2000. V. 123. №5. P. 403–405.
28. Ru sulfoxide complexes, their preparation and use: pat. 0098435 US; pabl. 28.04.2011.
29. Chauhan M., Hauck B.J., Keller L.P., Boudjouk P. Hydrosilylation of alkynes catalyzed by platinum on carbon //J. Organomet. Chem. 2002. №645 (1–2). P. 1–13.
30. Jiménez R., Martínez-Rosales J.M., Cervantes J. The activity of Pt/SiO2 catalysts obtained by the sol-gel method in the hydrosilylation of 1-alkynes //Canadian Journal of Chemistry. 2003. №81 (11). P. 1370–1375.
31. Alonso F., Buitrago R., Moglie Y., Ruiz-Martinez J., Sepulveda-Escribano A., Yus M. Hydrosilylation of alkynes catalysed by platinum on titania //J. Organomet. Chem. 2011. №696 (1).
P. 368–372.
32. Reddy C.B., Shil A.K., Guha N.R., Sharma D., Das P. Solid Supported Palladium(0) Nanoparticles: An Efficient Heterogeneous Catalyst for Regioselective Hydrosilylation of Alkynes and Suzuki Coupling of β-Arylvinyl Iodides //Catalysis Letters. 2014. №144 (9). P. 1530–1536.
33. High activity catalyst for hydrosilylation reactions and methods of making the same: pat. 0051357 US; pabl. 19.02.2015.
34. Activation of metal salts with silylhydrides and their use in hydrosilylation reactions: pat. 0343311 US; pabl. 20.11.2014.
35. Unsaturated ketones as accelerators for hydrosilation: pat. 5424470 US; pabl. 13.06.1995.
36. Acetylenic alcohols and ethers as accelerators for hydrosilation: pat. 5449802 US; pabl. 12.09.1995.
37. Aldehydes as accelerators for hydrosilation: pat. 5616763 US; pabl. 01.04.1997.
38. Addition-curable silicone rubber composition: pat. 6274658 US; pabl. 14.08.2001.
39. Method for maintaining catalytic activity during a hydrosilylation reaction: pat. 5359113 US; pabl. 25.10.1994.
40. Hydrosilylation of unsaturated organic compounds in presence of platinum-based catalyst involves adding organic per-acid e.g. peracetic acid, during the reaction to activate or reactivate the catalyst: pat. 10133008 DE; pabl. 27.06.2002.
41. Hydrosilylation process and polymers produced by the process: pat. 6303728 US; pabl. 16.10.2001.
42. Promoted hydrosilation reactions: pat. 6590117 US; pabl. 08.07.2003.
43. Process and composition for promoting hydrosilylation reactions using sterically hindered nitrogen-containing and phosphorus-containing compounds: pat. 5191103 US; pabl. 02.03.1993.
Е.Н. Каблова. М.: МИСиС–ВИАМ. 2002. 488 с.
2. Савенкова А.В., Тихонова И.В., Требукова Е.Д.. Тепломорозостойкие герметики /В сб.: Авиационные материалы на рубеже ХХ–XXI веков. М.: ВИАМ. 1994. С. 432–439.
3. Петрова А.П., Донской А.А., Чалых А.Е., Щербина А.А. Клеящие материалы. Герметики: Справочник. СПб.: НПО «Профессионал». 2008. 589 с.
4. Минаков В.Т., Савенкова А.В., Донской А.А. Кремнийорганические герметики //Российские полимерные новости. 2003. V. 8. №4. С. 37–41.
5. Pohmer K., Steinberger H. Silicone rubbers: innovative – high performance – efficient //Organosilicon Chemistry IV. Wiley-VCH. 2000. P. 699–709.
6. Zhao M., Feng Y., Li G., Li Y., Wang Y., Han Y., Sun X., Tan X. Synthesis of an adhesion-enhancing polysiloxane containing epoxy groups for addition-cure silicone light emitting diodes encapsulant //Polym. Adv. Technol. 2014. №25 (9). P. 927–933.
7. Pan K., Zeng X., Li H., Lai X. Synthesis of Siloxanes Containing Vinyl and Epoxy Group and its Enhancement for Adhesion of Addition-Cure Silicone Encapsulant //J. Macromol. 2013. №50 (11). P. 1126–1132.
8. Polysiloxane blends has good adhesion to substrates, able release from molds; homo- or copolymers of polysiloxane, polysilsesquioxanes, or polysilicates; bonding to metallic, plastic and thermoplastic substrates: pat. 7288322 US; pabl. 30.10.2007.
9. Caseri W., Pregosin P.S. Hydrosilylation chemistry and catalysis with CiS–PtCl2(PhCH=CH2)2 //Organometallics. 1988. №7 (6). P. 1373–1380.
10. Addition curable self-adhesive silicone rubber composition: pat. 8937123 US; pabl. 20.01.2015.
11. Preparation of silicone rubber elastomers: pat. 8329831 US; pabl. 11.12.2012.
12. Silicone rubber composition with improved fluidity: pat. 5352724 US; pabl. 04.10.1994.
13. Liquid silicone rubber composition of low specific gravity: pat. 6297291 US; pabl. 02.01.2001.
14. Peeters L. Low viscosity, high strength and fast curing //Adhesion, adhesives, sealants. 2013. №10(1). P. 14–17.
15. Silicone-acrylic copolymer: pat. 0012653 US; pabl. 04.02.14.
16. Kownacki I., Marciniec B., Steinberger H., Kubicki M., Hoffmann M., Ziarko A., Szubert K., Majchrzak M., Rubinsztajn S. Effect of triorganophosphites on platinum catalyzed curing of silicon rubber //Appl. Catalysis A. 2009. V. 362 (1–2). P. 106–114.
17. Addition-curable fluorosilicone rubber composition: pat. 2700677 EP; pabl. 26.02.14.
18. Gerlach E., Romanowski R., Jones B.A., Netto T.J. New technology to produce silicone sponge without chemical blowing agents or volatile organics /Proceedings of «Blowing agents and foaming processes» conference. 2004. P. 197–204.
19. High resilient silicone foam and process for preparing same: pat. 7393879 US; pabl. 01.07.2008.
20. Hydrosilation reaction utilizing a (cyclopentadiene)(sigma-aliphatic) platinum complex and a free radical photoinitiator: pat. 6376569 US; pabl. 23.04.2002.
21. Photoinitiators for hydrosilation of polysiloxanes; release agents: pat. 4510094 US; pabl. 09.04.1985.
22. Irradiation-curable silicone compositions, photo-active platinum (IV) compounds, and method: pat. 6150546 US; pabl. 21.11.2000.
23. Cyclopentadienylplatinum (iv) compounds having a trisubstituted-silyl aliphatic group attached to platinum by carbon-platinum linkages as hydrosilylation catalysts in irradiation-curable silicones: pat. 6127446 US; pabl. 03.10.2000.
34. Mayer T., Burget D., Mignani G., Fouassier J. P. Photohydrosilylation reaction of silicone polymers. Platinum-based photocatalysts: Trimethyl(β-dicarbonyl) platinum IV complexes //J. Polymer Sci. A. 1996. №34 (15). P. 3141–3146.
25. Wang F., Neckers D.C. Photoactivated hydrosilylation reaction of alkynes //Organomet J. Chem. 2003. №665 (1–2). P. 1–6.
26. Maciejewski H., Wawrzyńczak A., Dutkiewicz M., Fiedorow R. Silicone waxes–synthesis via hydrosilylation in homo- and heterogeneous systems //Molec J. Catalysis. 2006. №257 (1–2).
P. 141–148.
27. Brook A. Silicon in Organic, Organometallic, and Polymer Chemistry //Wiley. 2000. V. 123. №5. P. 403–405.
28. Ru sulfoxide complexes, their preparation and use: pat. 0098435 US; pabl. 28.04.2011.
29. Chauhan M., Hauck B.J., Keller L.P., Boudjouk P. Hydrosilylation of alkynes catalyzed by platinum on carbon //J. Organomet. Chem. 2002. №645 (1–2). P. 1–13.
30. Jiménez R., Martínez-Rosales J.M., Cervantes J. The activity of Pt/SiO2 catalysts obtained by the sol-gel method in the hydrosilylation of 1-alkynes //Canadian Journal of Chemistry. 2003. №81 (11). P. 1370–1375.
31. Alonso F., Buitrago R., Moglie Y., Ruiz-Martinez J., Sepulveda-Escribano A., Yus M. Hydrosilylation of alkynes catalysed by platinum on titania //J. Organomet. Chem. 2011. №696 (1).
P. 368–372.
32. Reddy C.B., Shil A.K., Guha N.R., Sharma D., Das P. Solid Supported Palladium(0) Nanoparticles: An Efficient Heterogeneous Catalyst for Regioselective Hydrosilylation of Alkynes and Suzuki Coupling of β-Arylvinyl Iodides //Catalysis Letters. 2014. №144 (9). P. 1530–1536.
33. High activity catalyst for hydrosilylation reactions and methods of making the same: pat. 0051357 US; pabl. 19.02.2015.
34. Activation of metal salts with silylhydrides and their use in hydrosilylation reactions: pat. 0343311 US; pabl. 20.11.2014.
35. Unsaturated ketones as accelerators for hydrosilation: pat. 5424470 US; pabl. 13.06.1995.
36. Acetylenic alcohols and ethers as accelerators for hydrosilation: pat. 5449802 US; pabl. 12.09.1995.
37. Aldehydes as accelerators for hydrosilation: pat. 5616763 US; pabl. 01.04.1997.
38. Addition-curable silicone rubber composition: pat. 6274658 US; pabl. 14.08.2001.
39. Method for maintaining catalytic activity during a hydrosilylation reaction: pat. 5359113 US; pabl. 25.10.1994.
40. Hydrosilylation of unsaturated organic compounds in presence of platinum-based catalyst involves adding organic per-acid e.g. peracetic acid, during the reaction to activate or reactivate the catalyst: pat. 10133008 DE; pabl. 27.06.2002.
41. Hydrosilylation process and polymers produced by the process: pat. 6303728 US; pabl. 16.10.2001.
42. Promoted hydrosilation reactions: pat. 6590117 US; pabl. 08.07.2003.
43. Process and composition for promoting hydrosilylation reactions using sterically hindered nitrogen-containing and phosphorus-containing compounds: pat. 5191103 US; pabl. 02.03.1993.
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