WO2000001705A2 - Silicone compounds and process for making them - Google Patents
Silicone compounds and process for making them Download PDFInfo
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- WO2000001705A2 WO2000001705A2 PCT/US1999/013087 US9913087W WO0001705A2 WO 2000001705 A2 WO2000001705 A2 WO 2000001705A2 US 9913087 W US9913087 W US 9913087W WO 0001705 A2 WO0001705 A2 WO 0001705A2
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- alkylene oxide
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- 238000000034 method Methods 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 title claims description 36
- 229920001296 polysiloxane Polymers 0.000 title abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000007859 condensation product Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- -1 allyl halide Chemical class 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003995 emulsifying agent Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 abstract description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 7
- 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 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- GCYHRYNSUGLLMA-UHFFFAOYSA-N 2-prop-2-enoxyethanol Chemical compound OCCOCC=C GCYHRYNSUGLLMA-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000005661 hydrophobic surface Effects 0.000 description 2
- 239000000693 micelle Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- GDDVTIGTERZVBW-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethylsilicon Chemical compound C[Si](C)O[Si](C)(C)O[Si](C)(C)C GDDVTIGTERZVBW-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000000126 substance Substances 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
Definitions
- the present invention relates to novel silicone compounds, processes for making them, and to their use as surfactants.
- Silicone surfactants i.e. surfactants containing chains of siloxane groups, are know.
- silicone surfactants are commercially available are (ABA)n linear or comb copolymers, where
- A is a siloxane chain and B is a polyether chain or a combination of hydrocarbyl and polyether chains.
- a comb polymer is one in which pendant chains are disposed at intervals along a polymeric backbone (see R. M. Hill, "Silicone surfactants” in “Specialist surfactants” edited by J. D. Robb, Blackie (1977)).
- US 5,045,584 lists polyoxyalkylene dimethyl polysiloxane copolymers among non-ionic surfactants.
- EP 0630902A discloses silanes having hydrophilic groups. These silanes may be used as surface active agents in aqueous media.
- the hydrophilic group may be a polyether residue.
- the silane contains a single Si group and the silicon atom is linked to the polyether residue through an alkylene chain and not through an oxygen atom.
- EP 0641798A discloses a silane of similar general formula to that given in EP
- Rl to R7 are alkyl groups which may be the same or different, X is an alkylene group, m is zero or an integer in the range 1 to 3, n is an integer in the range 1 to 50, and p is an integer in the range 2 to 4.
- an aqueous emulsion comprising water and a water-immiscible liquid and an effective amount of an emulsifier of formula (A).
- alkyl groups Rl to R7 in the novel compound of the present invention may be the same or different. Preferably they are the same and are methyl groups.
- m (the number of R4R5SiO groups) is one or two.
- the alkylene group X is most conveniently - CH 2 CH 2 . - CH 2 CH 2 CH 2 _, or - CH 2 (CH 3 )CH-, i.e. the group -XO- is preferably derived from ethylene oxide or propylene oxide. Individual X units in a chain of XO units need not be the same, but the -(XO) neighbor- is preferably predominantly derived from ethylene oxide units. The number of units n is preferably in the range 1 to 50., e.g. 6.
- the compound of formula (A) may be produced using a compound of formula (B) e.g. 1,1,1,3,3,5,5-heptamethylsiloxane as a starting material. This may be obtained from Chemical Technologies Inc., 2731 Bartram Road, Briston, PA, USA.
- Compound (B) is reacted with a compound of formula (C).
- Compounds of formula (C) are derived from conventional condensation products of alkylene oxides which are readily available commercially.
- the alkylene oxide derivatives may be converted into compounds of formula (C) by first forming an alkali metal derivative of formula D below.
- alkali metal derivatives of alkylene oxide condensation products may be produced by conventional methods which do not require detailed description here.
- the alkali metal derivatives may be converted into compounds of formula (C) by reaction with an allyl halide of appropriate formula.
- alkylene oxide condensation product which is available does not have the desired number (n) of alkylene oxide groups
- alkali metal derivative of a condensation product containing a lesser number of alkylene oxide units (4) may be formed and reacted with the allyl compound.
- the hydrogen at the end of the chain remote from the allyl group may be halogenated by known techniques, e.g.
- the reaction of (B) and (C) may for example be carried out by heating the liquid reactants together at moderately elevated temperatures e.g. 100° to 130°C, preferably in the presence of a substantially anhydrous solvent e.g. toluene, and a catalyst, e.g. chloroplatinic acid.
- a substantially anhydrous solvent e.g. toluene
- a catalyst e.g. chloroplatinic acid
- the reaction product may be purified by conventional techniques and the present of compound of formula (A) confirmed by techniques such as NMR and infra red spectroscopy.
- Triethylene glycol 300g was introduced into a reactor (500ml), in which a nitrogen atmosphere was maintained, and stirred.
- Sodium (4.6G) was cut into small pieces under toluene and the pieces gradually added to the reactor.
- the reactor was warmed to 50°C to initiate the reaction.
- Sodium pieces were added at a rate to keep the reactor temperature in the range 50° to 100°C.
- the reactor was left overnight while stirring the contents under a nitrogen atmosphere.
- the contents of the reactor were now divided into two equal portions, one of which was retained in the reactor.
- the portion remaining in the reactor was cooled to below 70°C and allyl bromide (10 ml) was added gradually.
- the reactor was left overnight while stirring at a temperature maintained between 50°C and 100°C.
- the chloroplatinic acid mixture consisted of 0.9g of chloroplatinic acid in 50 ml of ethanol. The flask was then heated gently to reflux temperature (115°C) and was left to reflux for 16 hours at this temperature, and then allowed to cool. The contents of the flask were then distilled under vacuum for about 3 hours to leave a residue as the desired product. This was a dark coloured liquid
- Hexaethylene glycol was obtained from a commercial source (Aldrich). This made possible a simplified reaction scheme.
- Example 1 Detailed reaction conditions for individual steps are indicated in Example 1.
- the final product was shown by IR spectroscopy to have no unsaturated carbon - carbon bonds, showing that the allyl group had reacted. NMR showed that the Si-H bond present in the siloxane reactant had disappeared and showed the presence of Si-Me bonds. So confirming the structure deduced from the reaction scheme.
- the limiting tension was found to be 31 mN m " ' and the critical micelle concentration was found to be 3xl0 "5 to 4xl0 "5 mol dm "3 .
- the compounds of the present invention may be utilized as surfactants having desirable surface tension properties that may be utilized in a wide variety of commercial products such as cleaners, polishes, and coatings. Also the inventive process for making said compound may be operated utilizing commercially available starting materials and a simplified reaction scheme.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Silicon Polymers (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Abstract
The present invention provides silicone surfactants with desirable surface orientation properties and having formula (A). The invention also provides a process for making the inventive silicone surfactants.
Description
SILICONE COMPOUNDS AND PROCESS FOR MAKING THEM
Technical Field The present invention relates to novel silicone compounds, processes for making them, and to their use as surfactants.
Background Art
Silicone surfactants, i.e. surfactants containing chains of siloxane groups, are know. Thus silicone surfactants are commercially available are (ABA)n linear or comb copolymers, where
A is a siloxane chain and B is a polyether chain or a combination of hydrocarbyl and polyether chains. A comb polymer is one in which pendant chains are disposed at intervals along a polymeric backbone (see R. M. Hill, "Silicone surfactants" in "Specialist surfactants" edited by J. D. Robb, Blackie (1977)). Thus US 5,045,584 lists polyoxyalkylene dimethyl polysiloxane copolymers among non-ionic surfactants.
Because of their structure the conventional silicone surfactants do not orientate at surfaces in the same way as conventional surfactants based on hydrocarbons.
EP 0630902A discloses silanes having hydrophilic groups. These silanes may be used as surface active agents in aqueous media. The hydrophilic group may be a polyether residue.
However, the silane contains a single Si group and the silicon atom is linked to the polyether residue through an alkylene chain and not through an oxygen atom.
EP 0641798A discloses a silane of similar general formula to that given in EP
0630902A but which as a hydrophilic ionic residue. The surfactants which are the subject of the above two patent specifications do not contain siloxane groups and contain only a single silicon atom.
It would be desirable to provide silicone surfactants which orientate more readily at surfaces, i.e. with a relatively hydrophobic head which is orientated towards the more hydrophobic surface and a relatively hydrophilic tail which was orientated away from the hydrophobic surface. Desirable surfactant characteristics are now provided by the novel silicone compound of the present invention.
Disclosure of the Invention
According to one aspect of the present invention there is provided a novel compound of the formula
(A) wherein Rl to R7 are alkyl groups which may be the same or different, X is an alkylene group, m is zero or an integer in the range 1 to 3, n is an integer in the range 1 to 50, and p is an integer in the range 2 to 4.
According to a further aspect of the present invention, there is provided a process for making a compound of formula (A) which comprises reacting together a compound of formula
(B) With a compound of formula
CH2 = CH — (CH2)q— 0 r [ XO H — H _ -i n
(C) where Rl to R7, X, and m and n have the same meaning as in formula (A), and q is zero, 1 or
According to a further aspect of the present invention, there is provided an aqueous emulsion comprising water and a water-immiscible liquid and an effective amount of an emulsifier of formula (A).
The alkyl groups Rl to R7 in the novel compound of the present invention may be the same or different. Preferably they are the same and are methyl groups.
Preferably m (the number of R4R5SiO groups) is one or two.
The skilled reader will understand that commercial products may contain mixtures of molecular species such that the average value of m or n may not be an integer, although it will be an integer for any individual molecule.
The alkylene group X is most conveniently - CH2 CH2. - CH2 CH2 CH2_, or - CH2(CH3)CH-, i.e. the group -XO- is preferably derived from ethylene oxide or propylene oxide. Individual X units in a chain of XO units need not be the same, but the -(XO)„- is preferably predominantly derived from ethylene oxide units. The number of units n is preferably in the range 1 to 50., e.g. 6.
A specific example of a compound formula (A) is
Me Me Me I
ME - -Si — O — Si — O Si - CH, O CH2CH2O H
Me Me M I e
The compound of formula (A) may be produced using a compound of formula (B) e.g. 1,1,1,3,3,5,5-heptamethylsiloxane as a starting material. This may be obtained from Chemical Technologies Inc., 2731 Bartram Road, Briston, PA, USA.
Compound (B) is reacted with a compound of formula (C). Compounds of formula (C) are derived from conventional condensation products of alkylene oxides which are readily available commercially. The alkylene oxide derivatives may be converted into compounds of formula (C) by first forming an alkali metal derivative of formula D below.
(D) where M is an alkali metal.
The alkali metal derivatives of alkylene oxide condensation products may be produced by conventional methods which do not require detailed description here. The alkali metal derivatives may be converted into compounds of formula (C) by reaction with an allyl halide of appropriate formula. Where the alkylene oxide condensation product which is available does not have the desired number (n) of alkylene oxide groups, and alkali metal derivative of a condensation product containing a lesser number of alkylene oxide units (4) may be formed and reacted with the allyl compound. The hydrogen at the end of the chain remote from the allyl group may be halogenated by known techniques, e.g. reaction with thionyl bromide, and a further quantity of an alkylene oxide condensation product containing(s) alkylene oxide units (where n=r+s) may then be reacted with the halogen to increase the length of the alkylene oxide chain.
The reaction of (B) and (C) may for example be carried out by heating the liquid reactants together at moderately elevated temperatures e.g. 100° to 130°C, preferably in the presence of a substantially anhydrous solvent e.g. toluene, and a catalyst, e.g. chloroplatinic acid.
The reaction product may be purified by conventional techniques and the present of compound of formula (A) confirmed by techniques such as NMR and infra red spectroscopy.
It is believed that compounds of formula (A) are of particular value in the formation of micro-emulsions.
Mode of Carrying Out the Invention Example 1 :
Triethylene glycol (300g) was introduced into a reactor (500ml), in which a nitrogen atmosphere was maintained, and stirred. Sodium (4.6G) was cut into small pieces under toluene and the pieces gradually added to the reactor. The reactor was warmed to 50°C to initiate the reaction. Sodium pieces were added at a rate to keep the reactor temperature in the range 50° to 100°C. The reactor was left overnight while stirring the contents under a nitrogen atmosphere.
The contents of the reactor were now divided into two equal portions, one of which was retained in the reactor.
The portion remaining in the reactor was cooled to below 70°C and allyl bromide (10 ml) was added gradually. The reactor was left overnight while stirring at a temperature maintained between 50°C and 100°C.
Thionyl bromide (21 g) was then added to the reactor, dropwise, and the reactor was stirred for about 1 hour at approximately 80°C.
The other half of the product obtained by reacting tri ethylene glycol with sodium was now added back to the reactor and stirred at approximately 80°C for 24 hours. The reactor contents were then left to cool. They were then mixed with an equal weight of water, and subjected to continuous distillation with a 50:50 mixture of 2,2,4-trimethyl pentane and toluene. The product obtained by extractive reflux distillation was then distilled to remove the solvent, and distillation was continued under vacuum for 6 hours to recover the distillate.
The reaction scheme represented by the above reactions is indicated below. HO (CH2 CH2 O)3H was reacted with sodium to give Na (CH2 CH2O)3H. The reaction of this with allyl bromide (CH,= CH,Br) gave CH2=CH2(CH2 CH2O)3H which, on reaction with thionyl chloride, gave CH2=CH2(CH2 CH2O)3Br which, on reaction with a further quantity of the sodium derivative, gave CH2=CH2(CH2 CH2O)6H which for convenience is referred to below as allyl glycol 1.
Allyl glycol 1 (6.6g, 0.021 moles), a siloxane (1,1,1,3,3,5,5-heptamethyltrisiloxane) (5.5g, 0.025 moles), toluene (30 mis), and chloroplatinic acid mixture (4 drops) were introduced into a 250 ml two necked flask fitted with a thermometer and a reflux condenser.
The chloroplatinic acid mixture consisted of 0.9g of chloroplatinic acid in 50 ml of ethanol. The flask was then heated gently to reflux temperature (115°C) and was left to reflux for 16 hours at this temperature, and then allowed to cool. The contents of the flask were then distilled under vacuum for about 3 hours to leave a residue as the desired product. This was a dark coloured liquid
Me
ME S Ii — O H
Me
Example 2:
Hexaethylene glycol was obtained from a commercial source (Aldrich). This made possible a simplified reaction scheme.
HO(CH2 CH2O)6H was reacted with sodium under nitrogen to give Na(CH2 CH2O)6H which was reacted with allyl bromide to give CH2 :=CH2(CH2 CH2O)6H. This was then reacted with 1,1, 1,3,3, 5,5,-heptamethyl trisiloxane in the presence of chloroplatinic acid to give Me3SiOSi(Me)2OSi(Me)2- (CH2)3O(CH2 CH2O)3H as a dark liquid.
Detailed reaction conditions for individual steps are indicated in Example 1.
The final product was shown by IR spectroscopy to have no unsaturated carbon - carbon bonds, showing that the allyl group had reacted. NMR showed that the Si-H bond present in the siloxane reactant had disappeared and showed the presence of Si-Me bonds. So confirming the structure deduced from the reaction scheme.
The presence of surface activity in a compound is indicated by its effect on surface tension of water. Using a du Nouy tensiometer, the surface tension of water was shown to fall with increasing concentration of the product until a limiting tension was reached
(corresponding to the formation of micelles). The limiting tension was found to be 31 mN m"' and the critical micelle concentration was found to be 3xl0"5 to 4xl0"5mol dm"3.
Industrial Applicability The compounds of the present invention may be utilized as surfactants having desirable surface tension properties that may be utilized in a wide variety of commercial products such as cleaners, polishes, and coatings. Also the inventive process for making said compound may be operated utilizing commercially available starting materials and a simplified reaction scheme.
Claims
1. A novel compound of formula
Rl O XO -H
(A) wherein Rl to R7 are alkyl groups which may be the same or different, X is an alkylene group, m is zero or an integer in the range 1 to 3, n is an integer in the range 1 to 50, and p is an integer in the range 2 to 4.
2. A compound according to claim 1 wherein the groups Rl to R7 are methyl groups.
3. A compound according to either of claims 1 or 2 wherein m is 1 or 2.
4. A compound according to any one of the preceding claims wherein the group -(XO)n- is predominantly derived from ethylene oxide units.
5. A compound according to any one of the preceding claims wherein n is in the range 1 to 50.
6. A compound according to any one of the preceding claims which is
Me Me Me
ME - Si — O — Si — O Si - CH, -- ' —[ I« CH2CH2O H
Me Me Me
7. A process for making a compound of formula (A) which comprises reacting together a compound of formula R2 R4 R6
Rl- -Si ΓÇö O Si ΓÇö O Si ΓÇö H
R3 R5 R7
(B) with a compound of formula
(C) where Rl to R7, X, and m and n have the same meaning as in formula (A), and q is zero, l or 2.
8. A process according to claim 7 wherein the reaction is carried out in the presence of chloroplatinic acid as catalyst.
9. A process for making a compound of formula (A) which comprises making a compound of formula (c) by reacting a compound of formula (D) with an allyl halide.
10. A process for making a compound of formula (A) which comprises making a compound of formula (d) by a. reacting an alkali metal derivative of an alkylene oxide condensation product containing r alkylene oxide units with an allyl halide, b. substituting a terminal hydrogen remote from the allyl group with halogen, and c. reacting the resulting product with an alkali metal derivative of an alkylene oxide condensation product containing s alkylene oxide units, where r+s=n.
11. An aqueous emulsion comprising water and a water-immiscible liquid and an effective amount of an emulsifier of formula (A).
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9814272.2 | 1998-07-01 | ||
| GBGB9814272.2A GB9814272D0 (en) | 1998-07-01 | 1998-07-01 | Silicone compounds and process for making them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2000001705A2 true WO2000001705A2 (en) | 2000-01-13 |
| WO2000001705A3 WO2000001705A3 (en) | 2002-09-19 |
Family
ID=10834776
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1999/013087 WO2000001705A2 (en) | 1998-07-01 | 1999-06-10 | Silicone compounds and process for making them |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB9814272D0 (en) |
| WO (1) | WO2000001705A2 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5461088A (en) * | 1993-08-26 | 1995-10-24 | Ciba-Geigy Corporation | Liquid radiation-curable formulation, in particular for use in stereolithography |
| EP0710688A1 (en) * | 1993-07-23 | 1996-05-08 | Sagami Chemical Research Center | Hydroxysilyl-terminated polyoxyethylene compound, quaternary-salt-terminated block copolymer, and percutaneous absorption promoter |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3485939B2 (en) * | 1993-03-12 | 2004-01-13 | 花王株式会社 | Method for producing phosphodiester salt-modified organo (poly) siloxane |
| JPH07179897A (en) * | 1993-12-24 | 1995-07-18 | Olympus Optical Co Ltd | Water-based detergent and washing method |
| JPH09278891A (en) * | 1996-04-09 | 1997-10-28 | Kao Corp | Nonion-modified organo(poly)siloxane, its production, and detergent composition containing it |
-
1998
- 1998-07-01 GB GBGB9814272.2A patent/GB9814272D0/en not_active Ceased
-
1999
- 1999-06-10 WO PCT/US1999/013087 patent/WO2000001705A2/en active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0710688A1 (en) * | 1993-07-23 | 1996-05-08 | Sagami Chemical Research Center | Hydroxysilyl-terminated polyoxyethylene compound, quaternary-salt-terminated block copolymer, and percutaneous absorption promoter |
| US5461088A (en) * | 1993-08-26 | 1995-10-24 | Ciba-Geigy Corporation | Liquid radiation-curable formulation, in particular for use in stereolithography |
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| CHEMICAL ABSTRACTS, vol. 122, no. 18, 1 May 1995 (1995-05-01) Columbus, Ohio, US; abstract no. 222467, IHARA, TAKESHI ET AL: "Preparation of phosphate group-containing siloxanes for use as emulsifier" XP002114878 & JP 06 263877 A (KAO CORP, JAPAN) 1993 * |
| CHEMICAL ABSTRACTS, vol. 123, no. 26, 25 December 1995 (1995-12-25) Columbus, Ohio, US; abstract no. 344239, TOMITANI, MANABU ET AL: "Water-based detergents containing siloxanes and washing process including recycling of rinsing wastewater" XP002114877 & JP 07 179897 A (OLYMPUS OPTICAL CO, JAPAN) 1993 * |
| CHEMICAL ABSTRACTS, vol. 128, no. 2, 12 January 1998 (1998-01-12) Columbus, Ohio, US; abstract no. 13552, IHARA, TAKESHI ET AL: "Nonionic modified polysiloxane, its production method, and the detergent composition which contains it" XP002114876 & JP 09 278891 A (KAO CORP., JAPAN) 1996 * |
| CHEMICAL ABSTRACTS, vol. 72, no. 4, 26 January 1970 (1970-01-26) Columbus, Ohio, US; abstract no. 14103j, MAKI, H. ET AL.: "syntheses and properties of surfactants containing organometals. IV. Organosilicones" XP002114875 -& DATABASE CHEMABS [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US XP002115341 -& DATABASE REGISTRY [Online] Chemical Abstracts Service Record for RN 26150-08-3, XP002115342 & J. AMER. OIL. CHEM. SOC., vol. 46, no. 12, 1969, pages 635-638, * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9814272D0 (en) | 1998-09-02 |
| WO2000001705A3 (en) | 2002-09-19 |
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