US2583322A - Lithium 3-thia-7, 7, dimethyl-7-trimethylsiloxy-7-silaheptanoate - Google Patents
Lithium 3-thia-7, 7, dimethyl-7-trimethylsiloxy-7-silaheptanoate Download PDFInfo
- Publication number
- US2583322A US2583322A US111094A US11109449A US2583322A US 2583322 A US2583322 A US 2583322A US 111094 A US111094 A US 111094A US 11109449 A US11109449 A US 11109449A US 2583322 A US2583322 A US 2583322A
- Authority
- US
- United States
- Prior art keywords
- thia
- lithium
- trimethylsiloxy
- dimethyl
- silaheptanoate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title description 5
- 229910052744 lithium Inorganic materials 0.000 title description 5
- CBWZSWHMXNPSRT-UHFFFAOYSA-N 6-[dimethyl(trimethylsilyloxy)silyl]hexanoic acid Chemical compound C[Si](CCCCCC(=O)O)(O[Si](C)(C)C)C CBWZSWHMXNPSRT-UHFFFAOYSA-N 0.000 title description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 239000000344 soap Substances 0.000 description 8
- 239000003599 detergent Substances 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- -1 alkenyl silane Chemical compound 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- WDZDMCOHOFKYKV-UHFFFAOYSA-N 2-(2-trimethylsilylethylsulfanyl)acetic acid Chemical compound C[Si](C)(C)CCSCC(O)=O WDZDMCOHOFKYKV-UHFFFAOYSA-N 0.000 description 1
- ZSQIFJYPQYHDCH-UHFFFAOYSA-N 2-(3-trimethylsilylpropylsulfanyl)acetic acid Chemical compound C[Si](C)(C)CCCSCC(O)=O ZSQIFJYPQYHDCH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003879 lubricant additive Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F13/00—Compounds containing elements of Groups 7 or 17 of the Periodic Table
- C07F13/005—Compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/02—Iron compounds
- C07F15/025—Iron compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/04—Nickel compounds
- C07F15/045—Nickel compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/06—Cobalt compounds
- C07F15/065—Cobalt compounds without a metal-carbon linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
Definitions
- the present invention relates to alkali salts of organosilicon compounds. It is particularly concerned with water soluble compounds useful as detergents and emulsifying agents and having the general formula wherein n is from to 10, preferably 0 to 1, m is an integer of from 2 to 3 and M is an alkali metal, particularly lithium, sodium or potassium.
- compositions employed in the manufacture of the detergents include the following:
- an acid of the above type is neutralized with a solution of an alkali metal base and the alkali metal salt recovered by evaporation of the solvent.
- the product appears to have substantially the same detergent properties as ordinary organic acid soaps of the same or substantially the same molecular weight. Due to the presence of the sulfur atom, the soaps of the present invention may also be used in ore floatation processes such as are employed in the recovery of lead, copper, silver, gold and other heavy metals. They may also be employed as lubricant additives in lubricating oils.
- Example 1 A solution of 3-thia-7-trimethylsiloxy-7,7-dimethyl-7-silaheptanoic acid in 95 percent ethyl alcohol was neutralized by the addition of an equivalent quantity of 0.5 N sodium hydroxide. The water and alcohol solvents were removed by heating on a steam bath followed by heating to dryness in a vacuum oven at 75 C.
- Aqueous solutions of the resultant soap exhibited good detergent properties in tests including the washing of soiled white cloth and the removal of dirt from ones hands. Considerable stable foam was obtained upon shaking of the aqueous solutions.
- a similar soap was obtained by substituting KOI-I for the NaOH.
- Example 2 A quantity of 3-thia-7-trimethylsiloxy-7 ,7 -dimethyl-7-silaheptanoic acid was neutralized by the addition of a solution of lithium hydroxide and the resultant lithium soap recovered by evaporating the solvent.
- This soap differs from the lithium soap prepared from stearic acid in that it is soluble in acetone. It formed a large quantity of foam in distilled Water and was precipitated from aqueous solutions thereof by ions such as calcium and magnesium.
- Example 3-thia-6,6-dimethylheptanoic acid and 3-thia-7-sila-7,7-dimethyloctanoic acid were respectively neutralized by the addition of 0.5 N sodium hydroxide solution.
- the products were aqueous solutions of the sodium salts of the acids having foaming and detergent properties similar to the soaps of the previous examples.
- the compounds herein described have also been employed as emulsifying agents for preparing aqueous emulsions of liquid organopolysiloxanes, such as, methyl polysiloxane oils.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
Patented Jan. 22, 1952 LITHIUM 3-THIA-7,7,D1IMETHYL-7-TRI- METHYLSILOXY-7 -SILAHEPTANOATE Charles A. Burkhard, Alplaus, N. Y., assignor to General Electric Company, a corporation of New York No Drawing. Application August 18, 1949, Serial No. 111,094
1 Claim. 1
The present invention relates to alkali salts of organosilicon compounds. It is particularly concerned with water soluble compounds useful as detergents and emulsifying agents and having the general formula wherein n is from to 10, preferably 0 to 1, m is an integer of from 2 to 3 and M is an alkali metal, particularly lithium, sodium or potassium.
Representative acids employed in the manufacture of the detergents include the following:
1. 3-thia-6-sila-6,6-dimethylheptanoic acid (CH3) aSiCH2CI-I2SCH2CO2H 2. 3-thia-7-sila-7,7-dimethy1octanoic acid (CHa) 3SICH2CH2CH2SCH2CO2H 3. 3 thia 7,7 dimethyl 7 trimethylsiloxy- 7-silaheptanoic acid (CH3) aSiOSi (CH3)2 (CH2) 3SCH2CO2H These acids and their preparation by the reaction of thioglycolic acid and a suitable alkenyl silane or siloxane of the formula wherein R is a vinyl or allyl group are specifically described and claimed in my copending application SerialNo. 111,091 filed concurrently herewith and assigned to the same assignee as the present invention.
In accordance with the present invention, an acid of the above type is neutralized with a solution of an alkali metal base and the alkali metal salt recovered by evaporation of the solvent. The product appears to have substantially the same detergent properties as ordinary organic acid soaps of the same or substantially the same molecular weight. Due to the presence of the sulfur atom, the soaps of the present invention may also be used in ore floatation processes such as are employed in the recovery of lead, copper, silver, gold and other heavy metals. They may also be employed as lubricant additives in lubricating oils.
In order that those skilled in the art better may understand how the present invention may be carried into effect, the following illustrative examples are given:
Example 1.A solution of 3-thia-7-trimethylsiloxy-7,7-dimethyl-7-silaheptanoic acid in 95 percent ethyl alcohol was neutralized by the addition of an equivalent quantity of 0.5 N sodium hydroxide. The water and alcohol solvents were removed by heating on a steam bath followed by heating to dryness in a vacuum oven at 75 C.
Analysis of the product for sulfur gave 9.99 and 10.08%; calculated 10.60.
Aqueous solutions of the resultant soap exhibited good detergent properties in tests including the washing of soiled white cloth and the removal of dirt from ones hands. Considerable stable foam was obtained upon shaking of the aqueous solutions. A similar soap was obtained by substituting KOI-I for the NaOH.
Example 2.A quantity of 3-thia-7-trimethylsiloxy-7 ,7 -dimethyl-7-silaheptanoic acid was neutralized by the addition of a solution of lithium hydroxide and the resultant lithium soap recovered by evaporating the solvent. This soap differs from the lithium soap prepared from stearic acid in that it is soluble in acetone. It formed a large quantity of foam in distilled Water and was precipitated from aqueous solutions thereof by ions such as calcium and magnesium.
Example 3.-3-thia-6,6-dimethylheptanoic acid and 3-thia-7-sila-7,7-dimethyloctanoic acid were respectively neutralized by the addition of 0.5 N sodium hydroxide solution. The products were aqueous solutions of the sodium salts of the acids having foaming and detergent properties similar to the soaps of the previous examples.
While the invention has been particularly described with reference to the use of the designated acids, it will be obvious the hydrolyzable esters thereof can be substituted therefor.
The compounds herein described have also been employed as emulsifying agents for preparing aqueous emulsions of liquid organopolysiloxanes, such as, methyl polysiloxane oils.
What I claim as new and desire to secure by Letters Patent of the United States is:
Lithium 3-thia-7,7-dimethyl-7-trimethylsiloxy- 7-silaheptanoate.
CHARLES A. BURKHARD.
REFERENCES CITED The following references are of record in tne file of this patent:
UNITED STATES PATENTS Name Date Burke July 18, 1950 OTHER REFERENCES Number (1945), page 356, Interscience, publisher, New
York.
Swartz et al.: "Surface Acting Agents" (1949), page 41, Interscience, publisher, New York.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US111094A US2583322A (en) | 1949-08-18 | 1949-08-18 | Lithium 3-thia-7, 7, dimethyl-7-trimethylsiloxy-7-silaheptanoate |
| GB19426/50A GB688407A (en) | 1949-08-18 | 1950-08-03 | Improvements in and relating to alkali metal salts of organosilicon compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US111094A US2583322A (en) | 1949-08-18 | 1949-08-18 | Lithium 3-thia-7, 7, dimethyl-7-trimethylsiloxy-7-silaheptanoate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2583322A true US2583322A (en) | 1952-01-22 |
Family
ID=22336565
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US111094A Expired - Lifetime US2583322A (en) | 1949-08-18 | 1949-08-18 | Lithium 3-thia-7, 7, dimethyl-7-trimethylsiloxy-7-silaheptanoate |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2583322A (en) |
| GB (1) | GB688407A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3392182A (en) * | 1963-02-28 | 1968-07-09 | Goldschmidt Ag Th | Novel organosilicon compounds and process for their preparation |
| US3481962A (en) * | 1964-07-30 | 1969-12-02 | Bayer Ag | Process for the production of organosiloxanes |
| US11014097B2 (en) * | 2016-12-14 | 2021-05-25 | Ecolab Usa Inc. | Functionalized silicones for froth flotation |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515857A (en) * | 1946-11-26 | 1950-07-18 | Du Pont | Compounds having a carboxyalkylthio or a carbalkoxyalkylthio group bonded to siliconthrough hydrocarbon |
-
1949
- 1949-08-18 US US111094A patent/US2583322A/en not_active Expired - Lifetime
-
1950
- 1950-08-03 GB GB19426/50A patent/GB688407A/en not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2515857A (en) * | 1946-11-26 | 1950-07-18 | Du Pont | Compounds having a carboxyalkylthio or a carbalkoxyalkylthio group bonded to siliconthrough hydrocarbon |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3392182A (en) * | 1963-02-28 | 1968-07-09 | Goldschmidt Ag Th | Novel organosilicon compounds and process for their preparation |
| US3481962A (en) * | 1964-07-30 | 1969-12-02 | Bayer Ag | Process for the production of organosiloxanes |
| US11014097B2 (en) * | 2016-12-14 | 2021-05-25 | Ecolab Usa Inc. | Functionalized silicones for froth flotation |
Also Published As
| Publication number | Publication date |
|---|---|
| GB688407A (en) | 1953-03-04 |
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