(45)  Date of Patent:  Feb.16,2021  (IO)  Patent No.:  US 10,919,920 B2  c12)  United States Patent  Zhu  et al.  (54)  METHOD FOR THE MANUFACTURE OF  ALKOXYSILYL-CONTAINING  THIOCARBOXYLIC ACID ESTERS  5,096,993 A  3/1992 Smith et al.  5,100,997  A  3/1992 Reisch et al.  5,106,874 A  4/1992 Porter et al.  5,116,931 A  5/1992 Reisch et al.  6,159,695  A  *  12/2000 McGovern ........... B0lJ 20/3242  427/299  6,169,194 Bl*  1/2001 Thompson ........... B0lJ 20/3242  204/600  6,608,125 B2  8/2003 Cruse et al.  6,777,569 Bl  8/2004 Westmeyer et al.  8,008,520 B2  8/2011  Cruse et  al.  9,346,920 B2 *  5/2016 Takada.  C09D 183/08  2012/0225231 Al  9/2012 York  2014/0107366 Al*  4/2014 Lewis ................... C07F 7/1804  556/479  2019/0048032 Al*  2/2019 Albert ................... C07F 7/1876  2020/0017 533 Al *  1/2020 Bertin ................... C07F 7/1804  CN  CN  103709188 A  *  4/2014  103709188 A  4/2014  3,829,505 A  8/1974 Johnston et al.  3,941,849 A  3/1976 Herold  3,992,427  A  * 11/1976 Chandra ............... C07F 7/1876  4,242,490 A  4,335,188 A  4,687,851 A  4,985,491 A  12/1980 Duncan et al.  6/ 1982 Igi et al.  8/ 1987 Laughner  l/ 1991 Reisch  556/453  28 Claims, No Drawings  (57)  ABSTRACT  (56)  References Cited  U.S. PATENT DOCUMENTS  Related U.S. Application Data  (65)  Prior Publication Data  OTHER PUBLICATIONS  FOREIGN PATENT DOCUMENTS  There is provided herein a method for the manufacture of  alkoxysilyl-containing thiocarboxylic acid ester which com› prises reacting a thioester with a mercapto-functional alkox› ysilane and/or an alkali metal salt, an alkaline earth metal  salt, a trisubstituted ammonium salt of an alkoxysilyl-func› tional thiolate which uses economical and readily available  reagents, avoids the use of phosgene or thionyl chloride  reagents and produces byproducts that may be recycled.  Primary Examiner  - Alexander R Pagano  (74)  Attorney, Agent, or Firm  - James C. Abruzzo  * cited by examiner  Dang, English-Language Machine Translation of CN 103709188  (2014) (Year: 2014).*  Voronkov et al.; "Acyliodides in organic synthesis. Reaction of  acetyl iodide with thiols; Russian Journal of Organic Chemistry";  47(12): Dec. 2011; 1789-1791.  International Search Report and Written Opinion from PCT/US2020/  029195 dated Jun. 30, 2020.  ( 58)  Field of Classification Search  CPC ..................................................... C07F 7/1876  See application file for complete search history.  (52)  U.S. Cl.  CPC ..................................  C07F  711876  (2013.01)  (51)  Int. Cl.  C07F  7118  (2006.01)  (60)  Provisional application No. 62/840,752, filed on Apr.  30, 2019.  US 2020/0347084 Al  Nov. 5, 2020  Apr. 22, 2020  (22)  Filed:  (21)  Appl. No.:  16/855,011  ( *)  Notice:  Subject to any disclaimer, the term ofthis  patent is extended or adjusted under 35  U.S.C. 154(b) by  O  days.  (73)  Assignee:  Momentive Performance Materials  Inc.,  Waterford, NY (US)  (72)  Inventors:  Yanjun Zhu,  Rye Brook, NY (US);  Linda Vecere,  Fishkill, NY (US)  (71)  Applicant:  Momentive Performance Materials  Inc.,  Waterford, NY (US)  USO 10919920B2 