Method of preparing an organosilicon compound

{
  "publication_number": "US6326506B1",
  "country": "US",
  "kind": "B1",
  "title": "Method of preparing an organosilicon compound",
  "abstract": "A method of preparing an organosilicon compound comprising effecting a hydrosilylation reaction between (a) unsaturated compounds with terminal unsaturated groups and (b) silane compounds described by formula HSiR 0 m W 3−m, where W is selected from the group consisting of C 1 to C 6 alkoxy groups, C 6 to C 10 aryloxy groups, and halogen atoms, R 0 is an organic group, and m is 0, 1, or 2 in the presence of (c) a platinum catalyst and (d) an auxiliary catalyst selected from the group consisting of (1) silyl esters of acids derived from oxo acids of sulfur; (2) amide compounds having N - Si bonds; (3) urea compounds; (4) silyl esters of carbamic acid; (5) phosphoric acid compounds; and (6) cyclic compounds selected from the group consisting of (i) hydroxypyridine compounds, (ii) 8-hydroxyquinoline compounds, (iii) oxazolidinone compounds, and (iv) N-hydroxysuccinimide compounds.",
  "claims": [
    "1. A method of preparing an organosilicon compound comprising effecting a hydrosilylation reaction between (a) unsaturated compounds with terminal unsaturated groups and (b) silane compounds described by formula HSiR 0 m W 3−m, where W is selected from the group consisting of C 1 to C 6 alkoxy groups, C 6 to C 10 aryloxy groups, and halogen atoms, R 0 is an organic group, and m is 0, 1, or 2 in the presence of (c) a platinum catalyst and (d) an auxiliary catalyst selected from the group consisting of (1) silyl esters of acids derived from oxo acids of sulfur; (2) amide compounds having N - Si bonds; (3) urea compounds; (4) silyl esters of carbamic acid; (5) phosphoric acid compounds; and (6) cyclic compounds described by the following formulas selected from the group consisting of (i) hydroxypyridine compounds, (ii) 8-hydroxyquinoline compounds, (iii) oxazolidinone compounds, and (iv) N-hydroxysuccinimide compounds: where R 9, R 10, R 11, R 12, R 13, and R 14 are each independently selected from the group consisting of hydrogen atoms, halogen atoms, C 1 to C 10 alkyl groups, C 6 to C 10 aryl groups, C 1 to C 10 alkoxy groups, and groups described by R 2 3 Si -, where each R 2 is independently selected from the group consisting of C 1 to C 10 hydrocarbon groups, C 1 to C 10 alkoxy groups, chlorine atoms, and hydrogen atoms with a maximum of 2 hydrogen atoms present; and X is a hydrogen atom or a group described by R 2 3 Si -, where R 2 is the same as described above.",
    "2. A method of preparing organosilicon compounds according to claim 1, where (d)(1) through (d)(5) of the auxiliary compounds are described by general formulas (d)(1): R 1 S(═O) 2 OSiR 21 3, where R 1 is selected from the group consisting of C 1 to C 10 alkyl groups, C 6 to C 18 aryl groups, groups described by R 18 2 N -, where each R 18 is independently selected from the group consisting of C 1 to C 10 alkyl groups, C 6 to C 18 aryl groups, hydrogen atom with a maximum of 1 hydrogen atom present, C 1 to C 10 haloalkyl groups, C 6 to C 18 haloaryl groups, halogen atoms, C 1 to C 10 alkoxy groups, and siloxy groups described by formula R 30 3 SiO -, where each R 30 is an independently selected C 1 to C 6 alkyl groups; and each R 21 is independently selected from the group consisting of C 1 to C 10 hydrocarbon groups, C 1 to C 10 alkoxy groups, chlorine atoms, hydrogen atoms with a maximum of 2 hydrogen atoms present, and R 1 S(═O) 2 O -, where R 1 is the same as described above; (d)(2): R 3 C(═O)NR 4 SiR 22 3, where R 3 is selected from the group consisting of C 1 to C 10 alkyl groups, C 6 to C 18 aryl groups, C 1 to C 10 haloalkyl groups, and C 6 to C 18 haloaryl groups; R 4 is a C 1 to C 10 hydrocarbon group or hydrogen atom; and each R 22 is independently selected from the group consisting of C 1 to C 10 hydrocarbon groups, C 1 to C 10 alkoxy groups, chlorine atoms, hydrogen atoms with a maximum of 2 hydrogen atoms present, and R 3 C(═O)NR 4 -, where R 3 and R 4 are the same as above; (d)(3): R 5 R 6 NC(═O)NR 4 X 1, where R 5 and R 6 are each independently selected from the group consisting of hydrogen atoms, C 1 to C 10 alkyl groups, C 6 to C 18 aryl groups, C 1 to C 10 haloalkyl groups, C 6 to C 18 haloaryl groups, and silyl groups described by R 3 Si -, where each R is an independently selected C 1 to C 3 alkyl group or hydrogen atom with a maximum of 2 hydrogen atoms present, R 4 is the same as described above; X 1 is selected from the group consisting of R 23 3 Si - and hydrogen atoms, where each R 23 is independently selected from the group consisting of C 1 to C 10 hydrocarbon groups, C 1 to C 10 alkoxy groups, chlorine atoms, hydrogen atoms with a maximum of 2 hydrogen atoms present, and R 5 R 6 NC(═O) -, where R 5 and R 6 are the same as described above; (d)(4): R 7 R 8 NC(═O)OSiR 24 3, where R 7 and R 8 are each independently selected from the group consisting of C 1 to C 10 alkyl groups, C 6 to C 18 aryl groups, and hydrogen atoms with a maximum of 1 hydrogen atom present; and each R 24 is independently selected from the group consisting of C 1 to C 10 hydrocarbon groups, C 1 to C 10 alkoxy groups, chlorine atoms, hydrogen atoms with a maximum of 2 hydrogen atoms present, and R 7 R 8 NC(═O) -, where R 7 and R 8 are the same as described above; and (d)(5): (R 16 O) 3 P(═O), where each R 16 is independently selected from the group consisting of hydrogen atoms with a maximum of 2 hydrogen atoms present, C 1 to C 10 alkyl groups, C 6 to C 18 aryl groups, C 1 to C 10 haloalkyl groups, C 6 to C 18 haloaryl groups, and a maximum of 2 silyl groups represented by R 25 3 Si -, where each R 25 is independently selected from the group consisting of C 1 to C 10 hydrocarbon groups, C 1 to C 10 alkoxy groups, chlorine atoms, hydrogen atoms with a maximum of 2 hydrogen atoms present, and (R 15 O) 2 P(═O)O -, where each R 15 is independently selected from the group consisting of hydrogen atoms with a maximum of 2 hydrogen atoms present, C 1 to C 10 alkyl groups, C 6 to C 18 aryl groups, C 1 to C 10 haloalkyl groups, and C 6 to C 18 haloaryl groups.",
    "3. A method of preparing organosilicon compounds according to claim 1, where component (d) is an in situ formed auxiliary catalyst.",
    "4. A method of preparing organosilicon compounds according to claim 1, where component (a) is selected from the group consisting of styrene or styrene derivative and allyl compounds.",
    "5. A method of preparing organosilicon compounds according to claim 1, where component (b) is selected from the group consisting of trimethoxysilane, methyldimethoxysilane, dimethylmethoxysilane, triethoxysilane, methyldiethoxysilane, dimethylethoxysilane, dimethylchlorosilane, methyldichlorosilane, and trichlorosilane.",
    "6. A method of preparing organosilicon compounds according to claim 1, where (d)(1) is selected from the group consisting of silyl esters of alkylsulfonic acids and silyl esters of arylsulfonic acids.",
    "7. A method of preparing organosilicon compounds according to claim 1, where (d)(2) is selected from the group consisting of N-dialkylsilylacetamides and N-dialkylsilyl-N-alkylacetamides.",
    "8. A method of preparing organosilicon compounds according to claim 1, where (d)(3) is selected from the group consisting of urea and N,N′-bis(trialkylsilyl)ureas.",
    "9. A method of preparing organosilicon compounds according to claim 1, where (d)(4) is a trialkylsilyl-N,N-dialkylcarbamate.",
    "10. A method of preparing organosilicon compounds according to claim 1, where (d)(5) is a trialkyl phosphate.",
    "11. A method of preparing organosilicon compounds according to claim 1, where (d)(6) is selected from the group consisting of 2-hydroxypyridine, 8-hydroxyquinoline, oxazolidinone, 3-trimethylsilyl-2-oxazolidinone, and N-hydroxysuccinimide.",
    "12. A method of preparing organosilicon compounds according to claim 1, where component (d) comprises 0.01 to 20 Wt. %, relative to the total weight of components (a) and (b).",
    "13. A method of preparing organosilicon compounds according to claim 1, where component (d) comprises 0.05 to 10 Wt. %, relative to the total weight of components (a) and (b).",
    "14. A method of preparing organosilicon compounds according to claim 1, where component (d) is an in situ formed auxiliary catalyst formed from a metal salt compound."
  ],
  "cpc": [
    "C07F 7/14",
    "C07F 7/0829",
    "C07F 7/1876"
  ],
  "assignees": [
    "DOW CORNING ASIA LTD"
  ],
  "filing_date": "2001-06-11",
  "publication_date": "2001-12-04",
  "grant_date": "2001-12-04",
  "priority_date": "2001-06-11",
  "application_number": "US-87774201-A",
  "family_id": "25370619",
  "citations": [
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  ]
}