WO1983003252A1 - Surfactants and preparation method thereof - Google Patents
Surfactants and preparation method thereof Download PDFInfo
- Publication number
- WO1983003252A1 WO1983003252A1 PCT/FR1983/000038 FR8300038W WO8303252A1 WO 1983003252 A1 WO1983003252 A1 WO 1983003252A1 FR 8300038 W FR8300038 W FR 8300038W WO 8303252 A1 WO8303252 A1 WO 8303252A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- dare
- mole
- surfactants
- amine
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/12—Acyclic radicals, not substituted by cyclic structures attached to a nitrogen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/22—Carbohydrates or derivatives thereof
- C11D3/221—Mono, di- or trisaccharides or derivatives thereof
Definitions
- the present invention relates to surface-active agents which can find various applications, for example as agents for reducing oil-water phases, in detergent formulations 5 or in cosmetic formulations.
- the invention also relates to a process for the preparation of these surfactants.
- the invention precisely presents natural products with exceptional surfactant properties, the production of which is remarkable for its simplicity.
- These surfactants result from the combination of a fatty amine and a dare, in the presence of an acid, in a dehydrated medium and without solvent.
- fatty amines aliphatic, saturated or unsaturated, primary or secondary fatty acids can advantageously be used, preferably having from 8 to 22 carbon atoms, preferably from 12 to 18. These amines can be used individually or as a mixture , in its pure state or in a more complex mixture. In this connection, let us cite tallow amines, coca amines, etc. Furthermore, they can be used in the form of free amines or in the form of derivatives such as hydrochlorides, acetates, etc. As dares, reducible and / or enolisable doses are used principally (aldoses, ketoses).
- monosaccharides such as xylose, glucose, fructose, galactose, sorbose, disaccharides such as lactose, altose, sucrose and other polyoses which hydrolyse in an acid medium.
- dares can be used individually or as a mixture, such as for example invert sugar from the sugar industry, isoglucose or corn syrup rich in fructose, maltodextrins, etc.
- the acid any strong mineral or organic acid can be used, such as hydrochloric acid and acetic acid.
- acid-reactive salts that is to say salts of strong acids and weak bases, such as for example ammonium and amine salts. In this regard, let us mention ammonium chloride and amine hydrochlorides.
- the pH is acidic.
- the pH can be, for example, between 7 and 9, as less than 7, depending on the needs and the surfactant sought.
- the conditions of their combination assume the absence of solvent.
- the environment must be deficient in water, that is to say as dehydrated as possible.
- the mixture can be heated to between 50 and 90 ° C, preferably under resulting pressure.
- the target is thus a final water content not exceeding 10 to 15%, preferably around 5%.
- the mixture obtained is used as it is as a surfactant.
- OMP Reaction products are known between fatty amines and certain oses, following the work of John G. Eric his exposed in US Patents 2,815,339 and US 2,815,340, as well as in J. Am. Chem. Soc. 1955 _7_7 2839.
- the products obtained differ from the surfactants according to the invention, and the operating conditions used are quite different.
- Erickson indeed operates in the presence of solvents (water, various alcohols, etc.) and without an acid catalyst.
- the products thus obtained are characterized by their low solubility in water, their instability in an alkaline medium and their poor foaming power.
- the surfactants "according to the invention are characterized by good foaming power, a solid to pasty texture, an amber color, good solubility in water, and in water-alcohol mixtures at least. up to a concentration of 5%.
- surfactants can be used in detergent formulations, for example for washing machines, in cosmetic formulations, in particular for shampoos and shaving creams, as well as more generally as oil-water emulsifiers.
- detergent formulations for example for washing machines
- cosmetic formulations in particular for shampoos and shaving creams
- oil-water emulsifiers as well as more generally as oil-water emulsifiers.
- the desired surfactant is obtained by bringing the mixture to 60 ° C. until homogenized, then by
- the surfactant obtained has the following characteristics: - texture: solid, pasty,
- the desired surfactant is obtained after bringing the mixture to 70 ° C for 75 minutes.
- the desired surfactant is obtained after having brought the mixture to 80 ° C. for 60 minutes until homogenization.
- the desired surfactant is obtained after having brought the mixture to 90 ° C. for 90 minutes until homogenization.
- the desired surfactant is obtained after bringing the mixture to 90 ° C for 60 minutes until homogenized.
- the desired surfactant is obtained after having brought the mixture to 70 ° C. for 60 minutes until homogenization.
- Example 8 One mixes:
- the surfactant is obtained after having brought the mixture to 70 ° C. for 60 minutes until homogenization.
- the desired surfactant is obtained after having brought the mixture to 80 ° C. under reduced pressure for 60 minutes until homogenization.
Abstract
The surfactant is produced by combining a fat amine and a ose, in the presence of an acid and in a dehydrated medium and without solvant. The said amine and the ose are contacted at a temperature comprised between 50 and 90?oC. The combination product is a remarkable surfactant.
Description
AGENTS TENSIO-ACTIFS SURFACTANTS
ET PROCEDE . DE PREPARATION DE TELSAND METHOD. FOR PREPARING SUCH
AGENTSAGENTS
....
La présente invention concerne des agents tensio-actifs pouvant trouver des applications di¬ verses, par exemple comme agents é ulgateurs de phases huiles-eau, dans des formulations détergentes 5 ou encore dans des formulations cosmétiques. L'in¬ vention concerne également un procédé de préparation de ces agents tensio-actifs.The present invention relates to surface-active agents which can find various applications, for example as agents for reducing oil-water phases, in detergent formulations 5 or in cosmetic formulations. The invention also relates to a process for the preparation of these surfactants.
On.connait tout l'intérêt que présentent les agents tensio-actifs d'origine naturelle et bio- 10 dégradables, comparés aux agents d'origine synthéti¬ que, qui parfois entrent mal dans le cycle biologi¬ que et peuvent se retrouver accumulés dans la chaî¬ ne agricole ou alimentaire.We know all the interest of surfactants of natural origin and biodegradable, compared to synthetic agents, which sometimes enter the biological cycle badly and can be found accumulated in the agricultural or food chain.
L'invention présente précisément des produits 15 naturels à propriétés tensio-actives exceptionnelles, dont l'obtention est remarquable par sa simplicité. Ces agents tensio-actifs résultent de la combinaison entre une aminé grasse et un ose, en présence d'un acide, en milieu déshydraté et sans solvant. Le pro¬The invention precisely presents natural products with exceptional surfactant properties, the production of which is remarkable for its simplicity. These surfactants result from the combination of a fatty amine and a dare, in the presence of an acid, in a dehydrated medium and without solvent. The pro¬
20 cédé de préparation consiste donc à faire réagir une aminé grasse et un ose dans les conditions précitées.20 yield of preparation therefore consists in reacting a fatty amine and a dare under the aforementioned conditions.
•\ • \
Comme aminés grasses, on peut utiliser des ami¬ nés grasses aliphatiques, saturées ou insaturées, pri¬ maires ou secondaires, ayant avantageusement de 8 à 22 atomes de carbone, de préférence de 12 à 18. Ces aminés peuvent être utilisées individuellement ou en mélange, à l'état pur ou en mélange plus complexe.
Citons à ce propos les aminés de suif, les aminés de co¬ prah, etc. Par ailleurs, elles peuvent être employées sous forme d'aminés libres ou sous forme de dérivés tels que chlorhydrates, acétates, etc. Comme oses, on utilise principc-lement des oses ré¬ ducteurs et/ou énolisables (aldoses, cétoses) . Citons à ce propos des monosaccharides tels que le xylose, le glucose, le fructose, le galactose, le sorbose, les disac- charides tels que le lactose, le altose, le saccharose et d'autres polyoses qui s'hydrolysent en milieu acide.As fatty amines, aliphatic, saturated or unsaturated, primary or secondary fatty acids can advantageously be used, preferably having from 8 to 22 carbon atoms, preferably from 12 to 18. These amines can be used individually or as a mixture , in its pure state or in a more complex mixture. In this connection, let us cite tallow amines, coca amines, etc. Furthermore, they can be used in the form of free amines or in the form of derivatives such as hydrochlorides, acetates, etc. As dares, reducible and / or enolisable doses are used principally (aldoses, ketoses). In this connection, mention may be made of monosaccharides such as xylose, glucose, fructose, galactose, sorbose, disaccharides such as lactose, altose, sucrose and other polyoses which hydrolyse in an acid medium.
Ces oses peuvent être utilisés individuellement ou en mé¬ lange, tel que par exemple le sucre inverti de l'indus¬ trie sucrières, 1*isoglucose ou sirop de maïs riche en fructose, des maltodextrines, etc. Comme acide, on peut utiliser tout acide minéral ou organique fort, tel que l'acide chlorhydrique et l'a¬ cide acétique. On peut également employer des sels à ré¬ action acide, c'est-à-dire des sels d'acides forts et de bases faibles, comme par exemple des sels d'ammonium et d'aminés. Citons à ce propos le chlorure d'ammonium et les chlorhydrates d'aminés.These dares can be used individually or as a mixture, such as for example invert sugar from the sugar industry, isoglucose or corn syrup rich in fructose, maltodextrins, etc. As the acid, any strong mineral or organic acid can be used, such as hydrochloric acid and acetic acid. It is also possible to use acid-reactive salts, that is to say salts of strong acids and weak bases, such as for example ammonium and amine salts. In this regard, let us mention ammonium chloride and amine hydrochlorides.
Le fait de se trouver "en présence d'un acide" ne signifie pas nécessairement que le pH soit acide. Ainsi, le pH peut être, par exemple, compris entre 7 et 9, comme inférieur à 7, selon les besoins et l'agent tensio-ac¬ tif recherché.Being "in the presence of an acid" does not necessarily mean that the pH is acidic. Thus, the pH can be, for example, between 7 and 9, as less than 7, depending on the needs and the surfactant sought.
Les conditions de leur combinaison supposent l'ab¬ sence de solvant. En outre, le milieu doit être déficient en eau, c'est-à-dire aussi déshydraté que possibe. On peut chauffer le mélange entre 50 et 90° C de préférence sous pression résulte. On vise ainsi une te¬ neur en eau finale n'excédant pas 10 à 15%, de préféren¬ ce voisine à 5%. Le mélange obtenu est utilisé tel quel comme agent tensio-actif.The conditions of their combination assume the absence of solvent. In addition, the environment must be deficient in water, that is to say as dehydrated as possible. The mixture can be heated to between 50 and 90 ° C, preferably under resulting pressure. The target is thus a final water content not exceeding 10 to 15%, preferably around 5%. The mixture obtained is used as it is as a surfactant.
OMP
On connaît des produits de réaction entre les aminés grasses et certains oses, à la suite des tra¬ vaux de John G. Eric son exposés dans les brevets U.S. 2 815 339 et U.S. 2 815 340, ainsi que dans J. Am. Chem. Soc. 1955 _7_7 2839. Cependant, les pro¬ duits obtenus diffèrent des agents tensio-actifs selon l'invention, et les conditions opératoires mises en oeuvre sont toutes autres. Erickson opère en effet en présence de solvants (eau, alcools divers, etc.) et sans catalyseur acide. Les produits ainsi obtenus se caractérisent par leur faible solubilité dans l'eau, leur instabilité en milieu alcalin et leur pouvoir moussant médiocre. Les agents tensio- actifs" selon l'invention se caractérisent, eux, par un bon pouvoir moussant, une texture solide à p⬠teuse, une couleur ambrée, une bonne solubilité dans l'eau, et dans les mélanges eau-alcool au moins jusqu' une concentration de 5%.OMP Reaction products are known between fatty amines and certain oses, following the work of John G. Eric his exposed in US Patents 2,815,339 and US 2,815,340, as well as in J. Am. Chem. Soc. 1955 _7_7 2839. However, the products obtained differ from the surfactants according to the invention, and the operating conditions used are quite different. Erickson indeed operates in the presence of solvents (water, various alcohols, etc.) and without an acid catalyst. The products thus obtained are characterized by their low solubility in water, their instability in an alkaline medium and their poor foaming power. The surfactants "according to the invention are characterized by good foaming power, a solid to pasty texture, an amber color, good solubility in water, and in water-alcohol mixtures at least. up to a concentration of 5%.
Ces agents tensio-actifs peuvent être utilisés dans des formulations détergentes, par exemple pour machines à laver, dans des formulations cosmétiques, notamment pour shampoings et crèmes à raser, ainsi que plus généralement comme agents émulgateurs huile- eau. Les exemples ci-après illustrent l'invention.These surfactants can be used in detergent formulations, for example for washing machines, in cosmetic formulations, in particular for shampoos and shaving creams, as well as more generally as oil-water emulsifiers. The following examples illustrate the invention.
Exemple 1Example 1
Dans un réacteur de 1 litre, on introduit, dans les proportions indiquée, les produits suivants :The following products are introduced into the 1 liter reactor in the proportions indicated:
- dodécylamine 92,5 g (0,5 mole), - acide chlorhydrique 36% 50,0 g (0,5 mole en HC1 pur)- dodecylamine 92.5 g (0.5 mole), - hydrochloric acid 36% 50.0 g (0.5 mole in pure HC1)
- glucose 90,0 g- glucose 90.0 g
On obtient l'agent tensio-actif désiré en portant le mélange à 60° C jusqu'à homogénéisation, puis enThe desired surfactant is obtained by bringing the mixture to 60 ° C. until homogenized, then by
5151
O PI
agitant de façon continue à cette température pendant 4 heures sous pression réduite (40 mb) .O PI stirring continuously at this temperature for 4 hours under reduced pressure (40 mb).
L'agent tensio-actif obtenu a les caractéristi¬ ques suivantes : - texture: solide, pâteux,The surfactant obtained has the following characteristics: - texture: solid, pasty,
- humidité: 5%,- humidity: 5%,
- couleur: ambrée- color: amber
- solubilité: totale dans l'eau et mélange eau-alcool jusqu'à une concentration de 10%, - pouvoir moussant (test de Ross-Miles.: au temπs O min., hauteur de mousse: 10 cm, au temps 5 min., hauteur de mousse: 9,5 cm, - stabilité: bonne stabilité dans un domaine de pH com¬ pris entre 3 et 9. A titre de comparaison, on homogénéise un mélange de 74 g de dodéc lamine (0,4 mole) et de 36 g de glu¬ cose (0,2 mole) dans 200 ml d'éthanol et 140 ml d'eau, puis on laisse reposer à teπinérature ambiante pendant 15 jours. (Conditions d1Erickson) . On filtre et on recueille un précipité (64 g sec) qui constitue le produit cherché et présente les carac¬ téristiques suivantes :- solubility: total in water and water-alcohol mixture up to a concentration of 10%, - foaming power (Ross-Miles test: at temπs O min., foam height: 10 cm, at time 5 min ., foam height: 9.5 cm, - stability: good stability in a pH range between 3 and 9. For comparison, a mixture of 74 g of dodecamine (0.4 mol) is homogenized and 36 g of glu¬ cose (0.2 mole) in 200 ml of ethanol and 140 ml of water, then left to stand at room temperature for 15 days. (Conditions of 1 Erickson). Filter and collect a precipitate (64 g dry) which constitutes the sought product and has the following characteristics:
- texture: poudre,- texture: powder,
- couleur: blanc à jaunâtre, - solubilité: très peu soluble dans l'eau et l'alcool.- color: white to yellowish, - solubility: very slightly soluble in water and alcohol.
- analyse: après recristallisation, analyse correspon¬ dant à la formule
- analysis: after recrystallization, analysis corresponding to the formula
- pouvoir moussant: médiocre,- foaming power: poor,
- stabilité: dissociation du produit à pH 9. Exemple 2- stability: dissociation of the product at pH 9. Example 2
On mélange:We blend:
- dodécylamine 18,5 g (0,10 mole),- dodecylamine 18.5 g (0.10 mole),
- acide chlorhydrique 36% 5,0 g (0,05 mole HCl pur) ,
- glucose 18 , 0 g (0 , 10 mole) .- hydrochloric acid 36% 5.0 g (0.05 mole pure HCl), - glucose 18.0 g (0.10 mole).
On obtient l'agent tensio-actif désiré après avoir porté le mélange à 70° C pendant 75 minutes.The desired surfactant is obtained after bringing the mixture to 70 ° C for 75 minutes.
Exemple 3 On mélange:Example 3 We mix:
- dodécylamine 18,5 g (0,10 mole),- dodecylamine 18.5 g (0.10 mole),
- chlorure d'ammonium 2,8 g (0,05 mole),- ammonium chloride 2.8 g (0.05 mole),
- glucose- 18,0 g (0,10 mole).- glucose - 18.0 g (0.10 mole).
On obtient l'agent tensio-actif désiré après avoir porté le mélange à 70° C pendant 75 minutes jusqu'à homogénéisation. ' Exemple 4The desired surfactant is obtained after having brought the mixture to 70 ° C. for 75 minutes until homogenization. 'Example 4
On mélange:We blend:
- octadécylamine 28,0 g (0,10 mole), - acide chlorhydrique 36% 5,0 g (0,05 mole) ,- octadecylamine 28.0 g (0.10 mole), - hydrochloric acid 36% 5.0 g (0.05 mole),
- glucose 18,0 g (0,10 mole).- glucose 18.0 g (0.10 mole).
On obtient l'agent tensio-actif désiré après av^ir porté le mélange à 80° C pendant 60 minutes jusqu'à homogénéisation.The desired surfactant is obtained after having brought the mixture to 80 ° C. for 60 minutes until homogenization.
- Exemple 5 On mélange:- Example 5 We mix:
- dodécylamine 18,5 g (0,10 mole),- dodecylamine 18.5 g (0.10 mole),
- acide hlorhydriqu-e 36% 10,0 g (0,10 mole) ,- 36% hydrochloric acid 10.0 g (0.10 mole),
- lactose 3,0 g (0,09 mole) . On obtient l'agent tensio-actif désiré après avoir porté le mélange à 90° C pendant 90 minutes jusqu'à homogénéisation.- lactose 3.0 g (0.09 mole). The desired surfactant is obtained after having brought the mixture to 90 ° C. for 90 minutes until homogenization.
Exemple 6Example 6
On mélange: - dodécylamine 18,5 g (0,10 mole).The following are mixed: - dodecylamine 18.5 g (0.10 mole).
PI
- acide acétique glacial 6,0 g (0,10 mole) ,PI - glacial acetic acid 6.0 g (0.10 mole),
- lactose 3,0 g (0,09 mole) ,- lactose 3.0 g (0.09 mole),
On obtient l'agent tensio-actif désiré après avoir porté le mélange à 90° C pendant 60 minutes jusqu'à homogénéisation.The desired surfactant is obtained after bringing the mixture to 90 ° C for 60 minutes until homogenized.
Exemple 7Example 7
On mélange:We blend:
- dodécylamine 18,5 g (0,10 mole),- dodecylamine 18.5 g (0.10 mole),
- acide chlorhydrique 36% 10,0 g (0,10 mole), - fructose 18,0 g (0,10 mole).- 36% hydrochloric acid 10.0 g (0.10 mole), - fructose 18.0 g (0.10 mole).
On obtient l'agent tensio-actif désiré après avoir porté le mélange à 70° C pendant 60 minutes jusqu'à homogénéisation.The desired surfactant is obtained after having brought the mixture to 70 ° C. for 60 minutes until homogenization.
Exemple 8 On mélange:Example 8 One mixes:
- dodécylamine 18,5 g,- dodecylamine 18.5 g,
- acide chlorhydrique 36% 5,0 g,- hydrochloric acid 36% 5.0 g,
- sucre inverti 18,0 g.- invert sugar 18.0 g.
On obtient l'agent tensio-actif après avoir porté le mélange à 70° C pendant 60 minutes jusqu'à homogénéisation.The surfactant is obtained after having brought the mixture to 70 ° C. for 60 minutes until homogenization.
Exemple 9Example 9
On mélange:We blend:
- aminés de suif 27,0 g, - acide chlorhydrique 36% 5,0 g,- tallow amines 27.0 g, - hydrochloric acid 36% 5.0 g,
- glucose 18,0 g.- glucose 18.0 g.
On obtient l'agent tensio-actif désiré après avoir porté le mélange à 80° C pendant 60 minutes jusqu'à homogénéisation.
Exemple 10The desired surfactant is obtained after having brought the mixture to 80 ° C. for 60 minutes until homogenization. Example 10
On mélange:We blend:
- dodécylamine 18,5 g- dodecylamine 18.5 g
- acide chlorhydrique 36% 10,5 g- hydrochloric acid 36% 10.5 g
- saccharose 18,0 g- sucrose 18.0 g
On obtient l'agent tensio-actif désiré après avoir porté le mélange à 80° C sous pression rédui¬ te pendant 60 minutes jusqu'à homogénéisation.
The desired surfactant is obtained after having brought the mixture to 80 ° C. under reduced pressure for 60 minutes until homogenization.
Claims
1. Agents tensio-actifs de combinaison entre une a iné grasse et un ose, en présence d'un aci¬ de en milieu déshydraté et sans solvant.1. Surfactants of combination between a fatty ine and a dare, in the presence of an acid in dehydrated medium and without solvent.
2. Procédé de préparation d'agents tensio-ac- tifs, caractérisé en ce qu'on combine, en présen¬ ce d'un acide, en milieu déshydraté et sans sol¬ vant, une a iné grasse et un ose.2. Process for the preparation of surfactants, characterized in that, in the presence of an acid, in a dehydrated medium and without a solvent, a fat and a dare are combined.
3. Procédé selon la revendication 2, caracté¬ risé en ce que l'aminé grasse est une aminé pri- maire ou secondaire ayant de 8 à 22 atomes de car¬ bone.3. Method according to claim 2, caracté¬ ized in that the fatty amine is a primary or secondary amine having from 8 to 22 carbon atoms.
4. Procédé selon la revendication 2, caractérisé en ce que l'aminé grasse est choisie dans le grou¬ pe contenant les aminés de suif et les aminés de coprah.4. Method according to claim 2, characterized in that the fatty amine is chosen from the group containing the amines of tallow and the amines of copra.
5. Procédé selon la revendication 2, caracté¬ risé en ce que l'ose est un ose réducteur ou éno- lisable.5. Method according to claim 2, caracté¬ ized in that the daring is a reducing or enosable dare.
6. Procédé selon la revendication 2, caracté- risé en ce que l'ose est un aldose ou un cétose monomère ou dimère.6. Method according to claim 2, characterized in that the ose is an aldose or a monomeric or dimeric ketose.
7. - Procédé selon la revendication 2, caractéri¬ sé en ce que l'ose est choisi dans le groupe compre¬ nant le sucre inverti, l'isoglucose, les polyoses hydrolysables en milieu acide et les maltodextrines.7. - Method according to claim 2, caractéri¬ se in that the dare is chosen from the group comprising the invert sugar, isoglucose, polyoses hydrolysable in acid medium and maltodextrins.
8. Procédé selon la revendication 2, caractérisé en ce que l'acide est l'acide chlorhydrique ou acé¬ tique. 8. Method according to claim 2, characterized in that the acid is hydrochloric acid or acé¬ tick.
9. Procédé selon la revendication 2, carac¬ térisé en ce que l'acide est un sel acide d'une base plus faible, tel que les sels d'ammonium et d'aminés.9. The method of claim 2, charac¬ terized in that the acid is an acid salt of a weaker base, such as ammonium and amine salts.
10. Procédé selon la revendication 2 carac¬ térisé en ce que l'aminé grasse et l'ose sont mis en contact à une température comprise entre 50 et 90° C .10. The method of claim 2 carac¬ terized in that the fatty amine and the dare are brought into contact at a temperature between 50 and 90 ° C.
//
OJ PI OJ PI
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8204290A FR2523150A1 (en) | 1982-03-11 | 1982-03-11 | SURFACTANTS AND PROCESS FOR THE PREPARATION OF SUCH AGENTS |
| FR82/04290820311 | 1982-03-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1983003252A1 true WO1983003252A1 (en) | 1983-09-29 |
Family
ID=9271982
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/FR1983/000038 WO1983003252A1 (en) | 1982-03-11 | 1983-03-03 | Surfactants and preparation method thereof |
Country Status (3)
| Country | Link |
|---|---|
| EP (1) | EP0102979A1 (en) |
| FR (1) | FR2523150A1 (en) |
| WO (1) | WO1983003252A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861374A (en) * | 1986-10-30 | 1989-08-29 | Eriksson Jan Olof | Non-abrasive polish or cleaning composition and process for its preparation |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2181929A (en) * | 1937-09-21 | 1939-12-05 | Du Pont | Maltosamine and process for preparing it |
| US2808401A (en) * | 1952-11-12 | 1957-10-01 | Gen Mills Inc | Reaction products of primary fatty amines and aldose sugars |
| US2815339A (en) * | 1952-11-26 | 1957-12-03 | Gen Mills Inc | Reaction products of primary fatty amines and ketose sugars |
| US2815340A (en) * | 1953-08-03 | 1957-12-03 | Gen Mills Inc | Reaction products of fatty amines and reducing disaccharides |
-
1982
- 1982-03-11 FR FR8204290A patent/FR2523150A1/en active Granted
-
1983
- 1983-03-03 EP EP19830900841 patent/EP0102979A1/en not_active Withdrawn
- 1983-03-03 WO PCT/FR1983/000038 patent/WO1983003252A1/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2181929A (en) * | 1937-09-21 | 1939-12-05 | Du Pont | Maltosamine and process for preparing it |
| US2808401A (en) * | 1952-11-12 | 1957-10-01 | Gen Mills Inc | Reaction products of primary fatty amines and aldose sugars |
| US2815339A (en) * | 1952-11-26 | 1957-12-03 | Gen Mills Inc | Reaction products of primary fatty amines and ketose sugars |
| US2815340A (en) * | 1953-08-03 | 1957-12-03 | Gen Mills Inc | Reaction products of fatty amines and reducing disaccharides |
Non-Patent Citations (1)
| Title |
|---|
| CHEMICAL ABSTRACTS, Vol. 93, 1980, Columbus, Ohio (US), J. FERNANDEZ-BOLANOS et al.: "Surfactants.II. 1-(n-Alkylamino)-1-Deoxy-D-Izxohexuloses and 1-(n-Alkylamino)-1-Deoxy-D-Glucoheptuloses", see page 1019, Abstract 72158a, AN. Quim., 1979, 75(12)1010-12 (Span.) * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4861374A (en) * | 1986-10-30 | 1989-08-29 | Eriksson Jan Olof | Non-abrasive polish or cleaning composition and process for its preparation |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0102979A1 (en) | 1984-03-21 |
| FR2523150B1 (en) | 1984-05-04 |
| FR2523150A1 (en) | 1983-09-16 |
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