GB2203152A - Surface active silicone compound - Google Patents
Surface active silicone compound Download PDFInfo
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- GB2203152A GB2203152A GB08804404A GB8804404A GB2203152A GB 2203152 A GB2203152 A GB 2203152A GB 08804404 A GB08804404 A GB 08804404A GB 8804404 A GB8804404 A GB 8804404A GB 2203152 A GB2203152 A GB 2203152A
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- United Kingdom
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- silicone compound
- general formula
- compound
- surface active
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 20
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- -1 alkyl lithium compound Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229960004132 diethyl ether Drugs 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract description 22
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- MKFVFIFKKBWIBD-UHFFFAOYSA-N lithium;methane Chemical compound [Li].C MKFVFIFKKBWIBD-UHFFFAOYSA-N 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 2
- FBJAGEQLOUPXHL-UHFFFAOYSA-N 1-sulfanylethanesulfonic acid Chemical compound CC(S)S(O)(=O)=O FBJAGEQLOUPXHL-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000003039 volatile agent Substances 0.000 description 2
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- LGWCCQIZIJQENG-UHFFFAOYSA-N chloro-hex-1-enyl-dimethylsilane Chemical compound CCCCC=C[Si](C)(C)Cl LGWCCQIZIJQENG-UHFFFAOYSA-N 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- ZOZZQPFBMNNPPO-UHFFFAOYSA-N ethyl-dimethyl-propylazanium Chemical compound CCC[N+](C)(C)CC ZOZZQPFBMNNPPO-UHFFFAOYSA-N 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- XURVRZSODRHRNK-UHFFFAOYSA-N o-quinodimethane Chemical group C=C1C=CC=CC1=C XURVRZSODRHRNK-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001181 organosilyl group Chemical class [SiH3]* 0.000 description 1
- MHYFEEDKONKGEB-UHFFFAOYSA-N oxathiane 2,2-dioxide Chemical compound O=S1(=O)CCCCO1 MHYFEEDKONKGEB-UHFFFAOYSA-N 0.000 description 1
- 125000005702 oxyalkylene group Chemical group 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000009736 wetting 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
Abstract
Surface active silicone compounds which have an improved stability at a pH above 8 or below 4, have the general formula <IMAGE> wherein R' when present is H or hydrocarbon, a is 2 or 3 and Z represents a hydrophilic substituent, e.g. a sulphonate or polyoxyalkylene containing group. A typical compound is (Me3Si)3C. CH2.CH.2.O. CO.CH (SO3Na)-CH2.COONa. The compounds are obtained a lithiated silylated methane and a compound with a Z group.
Description
SURFACE ACTIVE SILICONE COMPOUND
This invention relates to surface active silicone compounds and to a method for making these compounds.
Surface active silicone compounds have been known for some time and include such materials as organopolysiloxane polyoxyalkylene copolymers and sulphonate functional polysiloxanes. G.B. Patent Specification No. 1 198 096 for example, describes a polysiloxane having 0.1 to 100 mole percent of units of the formula M[O3SRSi(R' a 03-a1x wherein
2
M is a cation, R' is a certain monovalent group and R is a certain hydroxy-substituted divalent group where the hydroxy substituent is bonded to a carbon atom vicinal to which the -O3S- group is bonded, a is 0, 1 or 2 and x is 1, 2, 3 or 4 and is equal to the valency of said cation, and 0.0 to 99.9 mole percent of units of the formula R"bSiO4 b 7 wherein R" is hydrogen or a monovalent group as for R', and b is 1, 2 or 3.These polysiloxanes are stated to be useful for example in the production of emulsions for use in making polishes, of treating baths of increased wetting properties and of media having increased surface activity.
In G.B. Patent Specification No. 1 143 206 there are described organopolysiloxane polyoxyalkylene copolymers having the general formula Me3SiO(Me2SiO) q [H(0C2H4) ( OC3H6)yO(CH2)SiOMe]pSiMe3 in which q has a value from 3 to 25, x has a value from 1 to 25, z has a value from 0 to 15, z is 2 or 3, g has a value from 1 to 10, at least 25 percent by weight of the oxyalkylene groups being oxyethylene.
Silicone compounds of the types described above are, however, not suitable for use under acidic and basic conditions. The present invention is concerned with certain silicone compounds which show surface activity and are suitable for use in acidic and basic conditions.
The invention provides in one of its aspects silicone compounds represented by the general formula
wherein each R independently represents an alkyl or aryl group having up to 8 carbon atoms, each R' represents a hydrogen atom or a monovalent hydrocarbon group, Z represents a hydrophilic substituent and a has a value of 2 or 3.
In the general formula of the silicone compounds of the invention R may be for example methyl, ethyl, isopropyl, isobutyl or phenyl. R', if present, may be hydrogen or any monovalent hydrocarbon group. Preferably a has a value of 3, and no R' group is present in the compound of the invention. Z may be any group which has hydrophilic character. Such groups include for example sulphonate containing groups, polyoxyalkylene containing groups, phosphate containing groups, betaine groups and sulphate containing groups. The preferred Z groups are those that contain a sulphonate or a polyoxyalkylene group.
These functional groups may be linked directly or indirectly to the carbon atom having the tri-substituted silyl substituents. Preferably the Z group has the general formula R"Q, wherein R" denotes a divalent group, consisting of H, C and optionally N or Si, and Q is the functional unit, which may be for example a sulphonate group with a cation or a polyoxyalkylene group. Examples of the
R" group include n-butylene, o-xylylene, ethyl-propyldimethylammonium and -Si(Me)2(CH2)3-. Examples of Q groups are -SO3Na+ and -(0C2H4)7OH.
The silicone compounds of the invention may be prepared according to a process which comprises (1) the reaction of (R3Si) CH(R3-a with an alkyl lithium compound to form a compound having the general formula (R3Si) C (R')3 Li , and and (2) the direct or indirect reaction of the product of step (1) with a hydrophilic group containing compound, R, R' and a having the denotation mentioned above.
The silicon-containing starting material for step (1) of the method of the invention may be obtained by reacting a silane of the general formula R3SiX, with a lithium compound and a halomethane of the formula XaCHR' wherein R, R' and a are as denoted above and X is a halogen atom.
This halomethane is preferably trichloromethane. In step (1) of the method the compound (R3Si)aCH(R')3 a is reacted with alkyllithium in an appropriate solvent. This step is preferably carried out in a mixture of solvents comprising the solvent in which the alkyllithium compound is supplied.
Such mixtures may include tetrahydrofuran or diethylether.
The reagents used in step (2) will be determined by the type of surface active material one wants to obtain. These reagants may be among others sulphonate group containing compounds, for example 1,3 propane sultone or 1,4 butane sultone or polyoxyalkylene group containing compounds for example allylheptaoxyethylene glycol.By indirect reaction in step (2) is meant that the reaction may also be carried out in several stages, for example, in a first stage the reaction product of step (1) may be reacted with 1,4 dichloromethyl benzene, followed in a second stage by the reaction with sodium sulphite; or in a first stage the product of step (1) may be reacted with dimethyl chloropropylamine, followed in a second stage by the reaction with 1,3 propane sultone; in yet another example the reaction product of step (1) of the method of the invention is reacted with a dialkylchlorosilane in a first stage and is then further reacted in a second stage with a hydrophilic group containing compound having a terminal olefinic unsaturation, for example, allylheptaoxy ethylene glycol.
Surface active agents of the invention have good surface activity. They are also stable in conditions where the pH rises above 8 or falls below 4, where the more conventional surface active material based on silicone compounds break down.
There now follows a number of examples in which all parts and percentages are expressed by weight and Me denotes a methyl group, which illustrate the invention.
Example 1
Preparation of Sulphosuccinate Functional Trisyl
Methane
A 250ml three neck flask fitted with a stirrer, condenser, dropping funnel and nitrogen inlet was charged with 50ml of dry tetrahydrofuran (THF), 6.96g (0.03 mole) of trisyi methane [(Me3Si)3CH] and 21ml of a 1.4M solution of methyl lithium in Et2O. The ingredients were mixed and heated. The diethyl ether was distilled off after 4 hours, leaving the resulting trisyl methane lithium salt [(Me3Si)3C Li+3 in THF. To this solution, cooled to OOC, 1.5g (0.033 mole) of ethylene oxide were slowly added.
Work up with water and crystallisation from methanol gave the trisylpropanol [(Me3Si) 3CCH2CH2OH] in quantitative yield.
A 100ml three neck flask equipped with a condenser, stirrer and nitrogen inlet was charged with 2.76g (0.01 mole) of trisyl propanol, 20g of toluene and 0.98g (0.01 mole) of maleic anhydride. The mixture was slowly heated to 1100C for 30 minutes then stripped under reduced pressure, yielding the maleate monoester (Me3Si)3CCH2CH2-O-CO-CH=CH-COOH as a yellow oil.
To the maleate ester, 5ml of methanol and a solution of N sodium hydroxide in water were added adjusting the pH to between 7 and 8. The solution was then heated to reflux and 0.95g (0.005 mole) of sodium metabisulphite was added.
The mixture was ref fluxed for 4 hours and cooled to ambient temperature. Precipitation with acetone yielded the corresponding sulphosuccinate functional trisyl methane
Example 2
Preparation of Thiosulphate Functional Trisyl Methane
A solution of trisyl methane lithium prepared as described in Example 1 from 17.4g (0.075 mole) of trisyl methane was cooled to OOC. 9.9g (0.082 mole) of allyl bromide were slowly added. After complete addition the mixture was brought to ambient temperature for 20 minutes.
A work up with water and crystallisation from methanol yielded allyl trisyl methane [(Me3Si)3CCH2CH=CH2] in quantitative yield.
A 100ml flask equipped with a stirrer, condenser and nitrogen inlet was charged with 5.44g of the allyl trisyl methane (0.02 mole), 3.2g of mercaptoethane sulphonate (0.02 mole), 10g of H2O and 20g of isopropanol. The mixture was heated to reflux and 0.1% azobutyronitrile was added. The reaction was maintained at reflux for 2 hours.
Stripping off the volatiles at reduced pressure yielded a white solid of the formula (Me3Si)3C-(CH2)3-S-(CH2)2-SO3 Na+ Example 3
A solution of trisyl methane lithium prepared as described in Example 1 from 17.4g (0.075 mole) of trisyl methane, was cooled to 0 C. 0.082 mole of dimethyl hexenyl chlorosilane was slowly added. After complete addition the mixture was brought to ambient temperature for 20 minutes.
A work up with water and crystallisation from methanol yielded hexenyl dimethyl silyl trisyl methane [(Me3Si)3C-Si-(Me2)2-(CH2)4-CH=CH2] .
A 100ml flask equipped with a stirrer, condenser and nitrogen inlet was charged with 3.72g of hexenyl dimethyl silyl trisyl methane (0.01 mole), 1.64g of mercaptoethane sulphonate (0.01 mole), 7g of H2O and 15g of isopropanol.
The mixture was heated to reflux and 0.1% azobutyronitrile was added. The reaction was maintained at reflux for 2 hours. Stripping off the volatiles at reduced pressure yielded a white solid of the formula (Me3Si)3C-Si(Me)2-(CH2)6-S-(CH2)2-SO3 Na+.
Claims (7)
1. A silicone compound represented by the general formula (R3Si) aC1(R') 3-a wherein each R independently represents an alkyl
z or aryl group having up to 8 carbon atoms, each R' represents a hydrogen atom or a monovalent hydrocarbon group, Z represents a hydrophilic substituent and a has a value of 2 or 3.
2. A silicone compound according to Claim 1 where a has a value of 3.
3. A silicone compound according to either one of the preceding claims wherein Z contains a sulphonate or a polyoxyalkylene group.
4. A method for preparing a silicone compound represented by the general formula
wherein each R independently represents an alkyl or aryl group having up to 8 carbon atoms, each R' represents a hydrogen atom or a monovalent hydrocarbon group, Z represents a hydrophilic substituent and a has a value of 2 or 3, which comprises (1) the reaction of (R3Si) aCH(R')3a with an alkyl lithium compound to form a compound having the general formula (R3Si)aC (R')3 aLi+, and (2) the direct or indirect reaction of the product of step (1) with a hydrophilic group containing compound, R, R' and a having the denotation mentioned above.
5. A method according to Claim 4 wherein step (1) is carried out in the presence of a solvent which comprises tetrahydrofuran or diethylether.
6. A method according to either of Claims 5 or 6 wherein step (2) is an indirect reaction.
7. A method substantially as hereinbefore described with reference to any one of Examples 1, 2 and 3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878708552A GB8708552D0 (en) | 1987-04-09 | 1987-04-09 | Surface active silicone compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB8804404D0 GB8804404D0 (en) | 1988-03-23 |
| GB2203152A true GB2203152A (en) | 1988-10-12 |
Family
ID=10615569
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878708552A Pending GB8708552D0 (en) | 1987-04-09 | 1987-04-09 | Surface active silicone compound |
| GB08804404A Withdrawn GB2203152A (en) | 1987-04-09 | 1988-02-25 | Surface active silicone compound |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB878708552A Pending GB8708552D0 (en) | 1987-04-09 | 1987-04-09 | Surface active silicone compound |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB8708552D0 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0367381A2 (en) * | 1988-08-17 | 1990-05-09 | Dow Corning Limited | Carbosilane surfactants |
| EP0630902A1 (en) * | 1993-06-24 | 1994-12-28 | Th. Goldschmidt AG | Silanes containing hydrophilic groups, their preparation and use as surfactants in aqueous media |
| EP0641798A1 (en) * | 1993-09-06 | 1995-03-08 | Th. Goldschmidt AG | Silanes with hydrophylic groups, their preparation and use as surfactant in aqueous media |
| WO1996008249A1 (en) * | 1994-09-14 | 1996-03-21 | Johns Hopkins University | Inhibition of hemoflagellates by camptothecin compounds |
| WO1996008230A1 (en) * | 1994-09-16 | 1996-03-21 | Thera Patent Gmbh & Co. Kg Gesellschaft Für Industrielle Schutzrechte | Hydrophilized dental impression compounds |
-
1987
- 1987-04-09 GB GB878708552A patent/GB8708552D0/en active Pending
-
1988
- 1988-02-25 GB GB08804404A patent/GB2203152A/en not_active Withdrawn
Non-Patent Citations (2)
| Title |
|---|
| J. ORGANOMET. CHEM., VOLUME 290, 1985 P 267 TO 275 * |
| J. ORGANOMET. CHEM., VOLUME 308, 1986 P.261 TO 262. * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0367381A2 (en) * | 1988-08-17 | 1990-05-09 | Dow Corning Limited | Carbosilane surfactants |
| EP0367381A3 (en) * | 1988-08-17 | 1991-01-02 | Dow Corning Limited | Carbosilane surfactants |
| EP0630902A1 (en) * | 1993-06-24 | 1994-12-28 | Th. Goldschmidt AG | Silanes containing hydrophilic groups, their preparation and use as surfactants in aqueous media |
| EP0630901A1 (en) * | 1993-06-24 | 1994-12-28 | Th. Goldschmidt AG | Silanes containing hydrophylic groups, their preparation and use as surfactants in aqueous media |
| EP0641798A1 (en) * | 1993-09-06 | 1995-03-08 | Th. Goldschmidt AG | Silanes with hydrophylic groups, their preparation and use as surfactant in aqueous media |
| WO1996008249A1 (en) * | 1994-09-14 | 1996-03-21 | Johns Hopkins University | Inhibition of hemoflagellates by camptothecin compounds |
| WO1996008230A1 (en) * | 1994-09-16 | 1996-03-21 | Thera Patent Gmbh & Co. Kg Gesellschaft Für Industrielle Schutzrechte | Hydrophilized dental impression compounds |
| AU698620B2 (en) * | 1994-09-16 | 1998-11-05 | 3M Espe Ag | Hydrophilated dental impression compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8804404D0 (en) | 1988-03-23 |
| GB8708552D0 (en) | 1987-05-13 |
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