CA1112976A - Emulsifiers - Google Patents
EmulsifiersInfo
- Publication number
- CA1112976A CA1112976A CA356,139A CA356139A CA1112976A CA 1112976 A CA1112976 A CA 1112976A CA 356139 A CA356139 A CA 356139A CA 1112976 A CA1112976 A CA 1112976A
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- emulsifier
- emulsifier according
- alkyl
- emulsifiers
- emulsified
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- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Colloid Chemistry (AREA)
Abstract
Abstract of Disclosure Emulsifiers including straight chain alkylsulphonic acid ethanol- and isopropanol amides and tensides are used for producing an emulsion.
Description
'f6 This application is a divisional of Canadian application Serial No. 248,779, filed March 25, 1976.
The present invention relates to biodegradable non-ionogenic emulsifiers with a high emulsifying effect and a wide range of applications.
For ecological reasons biodegradable emulsifiers are attaining ever greater importance. Known biodegradable non-ionogenic emulsifiers include fatty acid glycerides, fatty acid esters of mono- and polysaccharides and sugar alcohols as well as alkyloxylated, especially ethoxylated natural or synthetic fatty alcohols, acids and acid amides.
However, for many applications these emulsifiers cannot prove satisfactory, since the stability of the emulsions produced with these emulsifiers or the effectiveness with regard to the required quantity of emulsifier and with regard to the emulsion production often leave much to be desired. With ethoxylated products a usable emulsifying effect is only obtained -with fairly high degrees of ethoxylation. But biodegradability deteriorates with an increasing degree of ethoxylation.
The invention relates to biodegradable emulsifiers including straight chain alkyl sulphonic acid ethanol- and isopropanol amides and tensides which emulsifiers avoid the disadvantages mentioned.
According to the present invention, there is provided an emulsifier comprising a compound of the formula I
1 (I) wherein R represents a straight chain C8 to C30 alkyl radical which is unsubstituted or substituted by chlorine, and R
represents a hydrogen atom or a methyl radical, and an anion-active, cation-active or non-ionogenic tenside.
The present invention also provides an emulsified composition comprising water, at least one oil-soluble compound in solution, and an emulsifier as described above.
The present invention further provides a process for the production of emulsified compositions characterized in that an oily and an aqueous phase are emulsified by the use of an emulslfier as described above.
Preferably, R represents a straight chain C10-C20 alkyl radical, optionally substituted with chlorine.
The ethanol- and isopropanol-amides can be produced according to known processes from the alkyl- or ehloroalkyl-sulphonie aeid esters or preferably from the sulphonie aeid ehlorides by reaetion with ethanolamine or isopropanolamine (see Houben-Weyl, 4th Edition, vol. IX, p 398).
The alkylsulphonie aeid ehlorides ean be regarded as espeeially preferred starting materials for reaetion with ethanolamine and isopropanol -amine, being formed by the sulphoehlorination of straight ehain alkanes or ehloroalkanes having 8 - 30 C-atoms, preferably 10 and 20 C-atoms. The individual steps of sulphoehlorination are familiar to all skilled men, e.g. from F. Asinger on the ehemistry and teehnology of paraffin hydroearbons, 1956, Akademie-Verlag-Berlin, pp. 395-474.
.. ~ . .
The production of the alkylsulphonic acid ethanol-and isopropanol amides can however also be carried out from the sulphone amides, which are reacted with ethylene oxide or propylene oxide or with ethylene- or propylene chlorohydrine in a manner known from the literature to form the alkylsulphonic acid ethanol- or isopropanolamides.
The emulsifiers according to the invention are biodegradable. Depending on their carbon number they are oil-viscous or wax-like. In their pure form they are only soluble in water with some difficulty, but dissolve well in organic solvents such as methanol, ethanol, benzene, toluene, petro-ether, ligroine, acetone and acetic acid ester. Tensides facilitate the usability of alkylsulphonic acid alkanol amides in water by working with water to form a solution.
This combination of alkylsulphonic acid alkanol amides and tensides has an increased emulsifying effect over the alkylsulphonic acid alkanol amides alone. All conventional anion-active, cation-active and non-ionogenic tensides can be used here, e.g. salts of fatty acids or other surface-active carboxylates, alkylsulphates, alkylsulphonates, quaternary ammonium salts, amine oxides, esters of mono- and polysaccharides and alkoxylated alcohols, phenols, alkylphenols, alkylcarboxylic acids, alkylcarboxylic acid amides and alkylsulphonic acid amides.
These various tensides are described in detail in K.
Lindner's "Tenside, Textilhilfsmittel, Waschrohstoffe", Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 1964 and are familiar to every skilled man. However, alkarylsulphonates or alkylsulphonates are used in preference, with the latter occurring to a large extent as alkali- or alkanolamine salts as by-products in the production of alkanol amides and being contained in the emulsi-fiers according to the invention.
The production of the emulsions can be effected by the stirring together of the oily and aqueous phase with the emulsifier or by other conventional pub]ished processes (P. Becker, Emulsions: Theory and Practice, Reinhold Publishing Corp., New York, 1957, p. 209, Houben-Weyl, vol. I 2, p. 97).
It proves to be of advantage here that the alkylsulphonic acid alkanolamides are soluble in organic solvents, so that they can also be applied in an organic phase. Thus the emulsifier can be prepared in the oily or aqueous phase and second phase can be stirred in. Alternatively, the emulsifier-free phase can be prepared and the emulsifier-containing oily or aqueous phase can be emulsified while stirring after the addition of the emulsifier of the invention simultaneously by stirring. Finally, it is also possible to produce the emulsions by any other feed process.
A particular advantage of the emulsifiers of the invention is that as a rule in the production of the emulsions only simple stirrers are necessary. This achieves a considerable simplification of the process in comparison with other biodegradable emulsifiers.
A further advantage relative to other emulsifiers is that emulsions produced with the alkylsulphonic acid alkanol-amides have only a very slight tendency to foaming. This proves to be especially favourable when the emulsions are produced with high power or turbine stirrers, because if high-foam emulsifying systems are used with this method the foam generated is too great for practical use.
The emulsifiers according to the invention can be added in the desired quantity to the phase to be emulsified.
The quantities employed are determined according to the desired emulsifying effect. It can fluctuate within wide limits and depends on the phase to be emulsified. Preferably 0.01 - 50%
by weight, and in particular 0.1 - 20% by weight of alkyl-sulphonic acid alkanolamide compound are used relative to thephase to be emulsified.
The emulsions produced with the emulsifiers according to the invention exhibit outstanding emulsion stabilities. In the event of separation due to a long period of storage, this is reversible, light stirring restores the original emulsion.
A very great variety of emulsions can be produced with the emulsifiers according to the invention. But they are preferably used in those areas in which non-ionogenic emulsifiers are described, e.g. for the emulsification of anti-aging agents, softeners and other auxiliaries for the rubbersector, of biologically effective substances in the plant protection field and of dyeing, textile and leather auxiliaries and in polymerisation technology.
The emulsifiers according to the invention can also be used in emulsion polymerisation, in which case, the tensides are preferably alkali- or alkanol-amine salts of alkyl or alkylarylsulphonic acids. They lead to separation-free latices without hindering radical polymerisation in the case of high monomer conversions. In cases in which with current emulsi-Eiers no coagulate-free latices are obtained, it is possible by means of the partial replacement of the emulsifier used by the emulsi-fier according to the invention, to arrive at separation-free latices. In addition, higher monomer conversions are often achieved by also using the emulsifiers according to the invention in emulsion polymerisation.
Monomers for aqueous emulsion polymerisation include all radically polymerisable olefinically unsaturated compounds, e.g. mono- and diolefines, such as ethylene, propylene, butadiene, isoprene, 2-chlorobutadiene-1,3, styrene, vinyl toluene ~-methylstyrene, chlorostyrene, vinylsulphonic acid and divinylbenzene; vinyl halides such as vinyl chloride and vinylidene chloride; vinyl esters of straight-chain and branched chain aliphatic carboxylic acids, such as vinyl acetate, propionate, _-butyrate, -pivalate, -laurate and -stearate;
vinyl ethers such as vinylmethyl-, -ethyl-, -n-butyl- and -sec.
-butylethers; esters of the acrylic and methacrylic acids of mono or polyolene, such as methylacrylate and -methacrylate, ethylacrylate and -methacrylate, butylacrylates and -methacry-lates, hexylacrylates and -methylacrylates, 2-ethylhexyl-acrylate and -methacrylate, _-decylacrylate and -methacrylate, _-dodecylmethacrylate, glycolmono-acrylate and -methacrylate, butanediole-1,4-acrylate and -methacrylate, ethyleneglycol-bis-acrylate and -methacrylate and trimethylolpropane-tris-acrylate and -methacrylate; diesters and semi-esters of ~ 3~ ~
unsaturated dicarboxylic acids, such as maleic, fumaric and itaconic acid-di- and mono-methyl-, -ethyl-, butyl- and hexylester, ~,~-unsaturated di- and monocarboxylic acid, such as acrylic, methacrylic, crotonic, maleic, fumaric and itaconic acid; amides, methylolamides, and alkoxymethylarnides of these ~,~-unsaturated di- and monocarboxylic acids, such as acryl-amide, methacrylamide, maleic acid amide, maleic acid imide, methylene-bis-acrylic and methacrylic amide; N-methylolacryl-and methacrylamide, N-methoxymethylacryl- and methacrylamide;
allyl compounds such as diallylphthalate and heterocyclic compounds such as N-vinyl phthalimide, n-vinyl-pyrrolidone and N-vinylimidazol. The monomers can be used alone or in combination with one another.
The emulsion polymerisation can be initiated with radical forming substances, preferably with organic peroxide compounds, which are used in quantities of from 0.01 to 2% by weight, relative to monomers. Depending on the monomer combination, in order to lower the molecular weight of the polymer, small quantities of regulators can also be used, e.g. mercaptans, halide hydrocarbons. The emulsion poly-merisation is possible in two ways: the total quantity of themonomers and the greater part of the aqueous phase containing the emulsifiers can be prepared, polymerisation can be started by the addition of an initiator and in the course of poly-merisation the rest of the aqueous phase can be added continuously or at intervals. It is also possible to employ the "Monomer feed" technique, by which only a part of the monomers and the aqueous phase containing the emulsifying agent are prepared and then artcr polymerisation is started the rest of the monomers and the aqueous phasc are added evenly or at intervals according to the proportion o-f the reaction. The proportion of monomers added can be pre-emulsified in the aqueous phase. Both processes are known.
The following example illustrates the invention:
Example 200 g Styrene, ~00 g demineralised water, 8 g Na-alkyl-sulphonate (mersolate * K 30) and 2 g of a straight chain C12-C18-alkylsulphonic acid ethanolamide mixture were prepared in a 2 litre three necked flask with stirrer and reflux condenser. The contents of the flask were flushed with nitrogen and then heated to 95C and activated with a solution of 0.2 g potassium peroxidisulphate in 10 g demineralised water. After the initiation of the reaction the mixture was stirred for half an hour and then within one hour the following solutions were added evenly at 95C internal temperature:
1) a solution of 0.4 g potassium peroxidisulphate in 100 g water; and
The present invention relates to biodegradable non-ionogenic emulsifiers with a high emulsifying effect and a wide range of applications.
For ecological reasons biodegradable emulsifiers are attaining ever greater importance. Known biodegradable non-ionogenic emulsifiers include fatty acid glycerides, fatty acid esters of mono- and polysaccharides and sugar alcohols as well as alkyloxylated, especially ethoxylated natural or synthetic fatty alcohols, acids and acid amides.
However, for many applications these emulsifiers cannot prove satisfactory, since the stability of the emulsions produced with these emulsifiers or the effectiveness with regard to the required quantity of emulsifier and with regard to the emulsion production often leave much to be desired. With ethoxylated products a usable emulsifying effect is only obtained -with fairly high degrees of ethoxylation. But biodegradability deteriorates with an increasing degree of ethoxylation.
The invention relates to biodegradable emulsifiers including straight chain alkyl sulphonic acid ethanol- and isopropanol amides and tensides which emulsifiers avoid the disadvantages mentioned.
According to the present invention, there is provided an emulsifier comprising a compound of the formula I
1 (I) wherein R represents a straight chain C8 to C30 alkyl radical which is unsubstituted or substituted by chlorine, and R
represents a hydrogen atom or a methyl radical, and an anion-active, cation-active or non-ionogenic tenside.
The present invention also provides an emulsified composition comprising water, at least one oil-soluble compound in solution, and an emulsifier as described above.
The present invention further provides a process for the production of emulsified compositions characterized in that an oily and an aqueous phase are emulsified by the use of an emulslfier as described above.
Preferably, R represents a straight chain C10-C20 alkyl radical, optionally substituted with chlorine.
The ethanol- and isopropanol-amides can be produced according to known processes from the alkyl- or ehloroalkyl-sulphonie aeid esters or preferably from the sulphonie aeid ehlorides by reaetion with ethanolamine or isopropanolamine (see Houben-Weyl, 4th Edition, vol. IX, p 398).
The alkylsulphonie aeid ehlorides ean be regarded as espeeially preferred starting materials for reaetion with ethanolamine and isopropanol -amine, being formed by the sulphoehlorination of straight ehain alkanes or ehloroalkanes having 8 - 30 C-atoms, preferably 10 and 20 C-atoms. The individual steps of sulphoehlorination are familiar to all skilled men, e.g. from F. Asinger on the ehemistry and teehnology of paraffin hydroearbons, 1956, Akademie-Verlag-Berlin, pp. 395-474.
.. ~ . .
The production of the alkylsulphonic acid ethanol-and isopropanol amides can however also be carried out from the sulphone amides, which are reacted with ethylene oxide or propylene oxide or with ethylene- or propylene chlorohydrine in a manner known from the literature to form the alkylsulphonic acid ethanol- or isopropanolamides.
The emulsifiers according to the invention are biodegradable. Depending on their carbon number they are oil-viscous or wax-like. In their pure form they are only soluble in water with some difficulty, but dissolve well in organic solvents such as methanol, ethanol, benzene, toluene, petro-ether, ligroine, acetone and acetic acid ester. Tensides facilitate the usability of alkylsulphonic acid alkanol amides in water by working with water to form a solution.
This combination of alkylsulphonic acid alkanol amides and tensides has an increased emulsifying effect over the alkylsulphonic acid alkanol amides alone. All conventional anion-active, cation-active and non-ionogenic tensides can be used here, e.g. salts of fatty acids or other surface-active carboxylates, alkylsulphates, alkylsulphonates, quaternary ammonium salts, amine oxides, esters of mono- and polysaccharides and alkoxylated alcohols, phenols, alkylphenols, alkylcarboxylic acids, alkylcarboxylic acid amides and alkylsulphonic acid amides.
These various tensides are described in detail in K.
Lindner's "Tenside, Textilhilfsmittel, Waschrohstoffe", Wissenschaftliche Verlagsgesellschaft mbH, Stuttgart 1964 and are familiar to every skilled man. However, alkarylsulphonates or alkylsulphonates are used in preference, with the latter occurring to a large extent as alkali- or alkanolamine salts as by-products in the production of alkanol amides and being contained in the emulsi-fiers according to the invention.
The production of the emulsions can be effected by the stirring together of the oily and aqueous phase with the emulsifier or by other conventional pub]ished processes (P. Becker, Emulsions: Theory and Practice, Reinhold Publishing Corp., New York, 1957, p. 209, Houben-Weyl, vol. I 2, p. 97).
It proves to be of advantage here that the alkylsulphonic acid alkanolamides are soluble in organic solvents, so that they can also be applied in an organic phase. Thus the emulsifier can be prepared in the oily or aqueous phase and second phase can be stirred in. Alternatively, the emulsifier-free phase can be prepared and the emulsifier-containing oily or aqueous phase can be emulsified while stirring after the addition of the emulsifier of the invention simultaneously by stirring. Finally, it is also possible to produce the emulsions by any other feed process.
A particular advantage of the emulsifiers of the invention is that as a rule in the production of the emulsions only simple stirrers are necessary. This achieves a considerable simplification of the process in comparison with other biodegradable emulsifiers.
A further advantage relative to other emulsifiers is that emulsions produced with the alkylsulphonic acid alkanol-amides have only a very slight tendency to foaming. This proves to be especially favourable when the emulsions are produced with high power or turbine stirrers, because if high-foam emulsifying systems are used with this method the foam generated is too great for practical use.
The emulsifiers according to the invention can be added in the desired quantity to the phase to be emulsified.
The quantities employed are determined according to the desired emulsifying effect. It can fluctuate within wide limits and depends on the phase to be emulsified. Preferably 0.01 - 50%
by weight, and in particular 0.1 - 20% by weight of alkyl-sulphonic acid alkanolamide compound are used relative to thephase to be emulsified.
The emulsions produced with the emulsifiers according to the invention exhibit outstanding emulsion stabilities. In the event of separation due to a long period of storage, this is reversible, light stirring restores the original emulsion.
A very great variety of emulsions can be produced with the emulsifiers according to the invention. But they are preferably used in those areas in which non-ionogenic emulsifiers are described, e.g. for the emulsification of anti-aging agents, softeners and other auxiliaries for the rubbersector, of biologically effective substances in the plant protection field and of dyeing, textile and leather auxiliaries and in polymerisation technology.
The emulsifiers according to the invention can also be used in emulsion polymerisation, in which case, the tensides are preferably alkali- or alkanol-amine salts of alkyl or alkylarylsulphonic acids. They lead to separation-free latices without hindering radical polymerisation in the case of high monomer conversions. In cases in which with current emulsi-Eiers no coagulate-free latices are obtained, it is possible by means of the partial replacement of the emulsifier used by the emulsi-fier according to the invention, to arrive at separation-free latices. In addition, higher monomer conversions are often achieved by also using the emulsifiers according to the invention in emulsion polymerisation.
Monomers for aqueous emulsion polymerisation include all radically polymerisable olefinically unsaturated compounds, e.g. mono- and diolefines, such as ethylene, propylene, butadiene, isoprene, 2-chlorobutadiene-1,3, styrene, vinyl toluene ~-methylstyrene, chlorostyrene, vinylsulphonic acid and divinylbenzene; vinyl halides such as vinyl chloride and vinylidene chloride; vinyl esters of straight-chain and branched chain aliphatic carboxylic acids, such as vinyl acetate, propionate, _-butyrate, -pivalate, -laurate and -stearate;
vinyl ethers such as vinylmethyl-, -ethyl-, -n-butyl- and -sec.
-butylethers; esters of the acrylic and methacrylic acids of mono or polyolene, such as methylacrylate and -methacrylate, ethylacrylate and -methacrylate, butylacrylates and -methacry-lates, hexylacrylates and -methylacrylates, 2-ethylhexyl-acrylate and -methacrylate, _-decylacrylate and -methacrylate, _-dodecylmethacrylate, glycolmono-acrylate and -methacrylate, butanediole-1,4-acrylate and -methacrylate, ethyleneglycol-bis-acrylate and -methacrylate and trimethylolpropane-tris-acrylate and -methacrylate; diesters and semi-esters of ~ 3~ ~
unsaturated dicarboxylic acids, such as maleic, fumaric and itaconic acid-di- and mono-methyl-, -ethyl-, butyl- and hexylester, ~,~-unsaturated di- and monocarboxylic acid, such as acrylic, methacrylic, crotonic, maleic, fumaric and itaconic acid; amides, methylolamides, and alkoxymethylarnides of these ~,~-unsaturated di- and monocarboxylic acids, such as acryl-amide, methacrylamide, maleic acid amide, maleic acid imide, methylene-bis-acrylic and methacrylic amide; N-methylolacryl-and methacrylamide, N-methoxymethylacryl- and methacrylamide;
allyl compounds such as diallylphthalate and heterocyclic compounds such as N-vinyl phthalimide, n-vinyl-pyrrolidone and N-vinylimidazol. The monomers can be used alone or in combination with one another.
The emulsion polymerisation can be initiated with radical forming substances, preferably with organic peroxide compounds, which are used in quantities of from 0.01 to 2% by weight, relative to monomers. Depending on the monomer combination, in order to lower the molecular weight of the polymer, small quantities of regulators can also be used, e.g. mercaptans, halide hydrocarbons. The emulsion poly-merisation is possible in two ways: the total quantity of themonomers and the greater part of the aqueous phase containing the emulsifiers can be prepared, polymerisation can be started by the addition of an initiator and in the course of poly-merisation the rest of the aqueous phase can be added continuously or at intervals. It is also possible to employ the "Monomer feed" technique, by which only a part of the monomers and the aqueous phase containing the emulsifying agent are prepared and then artcr polymerisation is started the rest of the monomers and the aqueous phasc are added evenly or at intervals according to the proportion o-f the reaction. The proportion of monomers added can be pre-emulsified in the aqueous phase. Both processes are known.
The following example illustrates the invention:
Example 200 g Styrene, ~00 g demineralised water, 8 g Na-alkyl-sulphonate (mersolate * K 30) and 2 g of a straight chain C12-C18-alkylsulphonic acid ethanolamide mixture were prepared in a 2 litre three necked flask with stirrer and reflux condenser. The contents of the flask were flushed with nitrogen and then heated to 95C and activated with a solution of 0.2 g potassium peroxidisulphate in 10 g demineralised water. After the initiation of the reaction the mixture was stirred for half an hour and then within one hour the following solutions were added evenly at 95C internal temperature:
1) a solution of 0.4 g potassium peroxidisulphate in 100 g water; and
2) a solution of 0.2 g triethanolamine in 80 g water. After the termination of the addition process the mixture was restirred for a further two hours at 95C.
A polymer emulsion was obtained which was free from coarse or fine precipitates and the monomer conversion was 100%.
In a comparision test under otherwise identical reaction *Trade mark - 8 -' `:
conditions, in which however no alkylsulphonic acid ethanolamidewas used, 10 g mersolate K 30 being used exclusively as the emulsifier, only a 98% monomer yield was achieved. In addition, this comparision contained a larger quantity of coagulate.
A polymer emulsion was obtained which was free from coarse or fine precipitates and the monomer conversion was 100%.
In a comparision test under otherwise identical reaction *Trade mark - 8 -' `:
conditions, in which however no alkylsulphonic acid ethanolamidewas used, 10 g mersolate K 30 being used exclusively as the emulsifier, only a 98% monomer yield was achieved. In addition, this comparision contained a larger quantity of coagulate.
Claims (6)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. An emulsifier comprising a compound of the formula I:
(I) wherein R represents a straight chain C8 to C30 alkyl radical which is unsubstituted or substituted by chlorine, and R1 represents a hydrogen atom or a methyl radical, and an anion-active, cation-active or non-ionogenic tenside.
(I) wherein R represents a straight chain C8 to C30 alkyl radical which is unsubstituted or substituted by chlorine, and R1 represents a hydrogen atom or a methyl radical, and an anion-active, cation-active or non-ionogenic tenside.
2. An emulsifier according to claim 1, wherein R
represents a straight chain C10 to C20 alkyl radical which is unsubstituted or substituted by chlorine.
represents a straight chain C10 to C20 alkyl radical which is unsubstituted or substituted by chlorine.
3. An emulsifier according to either of claims 1 or 2 in which the tenside is a salt of a fatty acid or other surface-active carboxylate, alkylsulphate, alkyl-sulphonate, quaternary ammonium salt, amine oxide, ester of mono- and poly-saccharide and alkoxylated alcohol, phenol, alkylphenol, alkylcarboxylic acid, alkylcarboxylic acid amide and alkyl-sulphonic acid amide.
4. An emulsifier according to claim 2 wherein the tenside is an alkarylsulphonate or alkylsulphonate.
5. An emulsified composition comprising water, at least one oil-soluble compound in solution, and an emulsifier according to any of claims 1, 2 or 4.
6. A process for the production of emulsified compositions characterized in that an oily and an aqueous phase are emulsified by the use of an emulsifier according to any of claims 1, 2 or 4.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA356,139A CA1112976A (en) | 1975-03-27 | 1980-07-14 | Emulsifiers |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2513690A DE2513690C3 (en) | 1975-03-27 | 1975-03-27 | Use of straight-chain alkyl sulfonic acid ethanol amides and alkyl sulfonic acid isopropanol amides as emulsifiers |
| DEP2513690.7 | 1975-03-27 | ||
| CA248,779A CA1091537A (en) | 1975-03-27 | 1976-03-25 | Alkylsulphonic acid amides as emulsifiers |
| CA356,139A CA1112976A (en) | 1975-03-27 | 1980-07-14 | Emulsifiers |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1112976A true CA1112976A (en) | 1981-11-24 |
Family
ID=27164389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA356,139A Expired CA1112976A (en) | 1975-03-27 | 1980-07-14 | Emulsifiers |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA1112976A (en) |
-
1980
- 1980-07-14 CA CA356,139A patent/CA1112976A/en not_active Expired
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