CA2164284A1 - Process for bleaching alkyl polyglycosides - Google Patents
Process for bleaching alkyl polyglycosidesInfo
- Publication number
- CA2164284A1 CA2164284A1 CA002164284A CA2164284A CA2164284A1 CA 2164284 A1 CA2164284 A1 CA 2164284A1 CA 002164284 A CA002164284 A CA 002164284A CA 2164284 A CA2164284 A CA 2164284A CA 2164284 A1 CA2164284 A1 CA 2164284A1
- Authority
- CA
- Canada
- Prior art keywords
- process according
- bleaching
- alkyl
- thorough mixing
- heating
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000004061 bleaching Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 title claims description 22
- 239000007787 solid Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000002156 mixing Methods 0.000 claims abstract description 7
- 239000007800 oxidant agent Substances 0.000 claims abstract description 7
- 150000002191 fatty alcohols Chemical class 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 4
- -1 alkyl poly-glycoside Chemical class 0.000 claims description 3
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical group [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 claims description 2
- 150000002402 hexoses Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229960001922 sodium perborate Drugs 0.000 claims description 2
- 229940045872 sodium percarbonate Drugs 0.000 claims description 2
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical group [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims 4
- 150000002972 pentoses Chemical group 0.000 claims 1
- 229940099408 Oxidizing agent Drugs 0.000 abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005858 glycosidation reaction Methods 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000009896 oxidative bleaching Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001805 pentosyl group Chemical group 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/56—Glucosides; Mucilage; Saponins
-
- 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
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Disclosed is a process for bleaching low-moisture and low-fatty-alcohol alkyl polyglycosides using solid oxidiz-ing agents with thorough mixing for example in a kneader or in an extruder at temperatures of 80 to 160C. By employing the solid oxidizing agent, water is not needed. Therefore the bleaching can be conducted at temperatures over 100C.
In addition, the use of bases is eliminated.
In addition, the use of bases is eliminated.
Description
21 642~4 _ O.Z 4901 Process for Bleaching Alkyl Polyglycosides The invention relates to a process for bleaching low-moisture and low-fatty-alcohol alkyl polyglycosides using solid oxidizing agents with thorough mixing at temperatures in the range from 80 to 160C. The thorough mixing is performed, e.g.
in a kneader or in an extruder.
Alkyl polyglycosides are prepared from natural raw materials and are nontoxic and readily degradable surface-active materials. They are therefore used as detergents, cleaning agents, emulsifiers and dispersants. However, they only have the desired interfacial properties when the alkyl groups have at least 8 carbon atoms. The alkyl polyglycosides for the purposes of this invention have with the formula:
R' - C ~ Zn' in which R' represents an unbranched or branched, saturated or unsaturated aliphatic hydrocarbon radical having 8 to 18 carbon atoms or mixtures thereof and Zn represents a poly-glycosyl radical having a polymerization degree n of 1.1 to 3 of hexose or pentose units or mixtures thereof.
Preference is given to alkyl polyglycosides having alkyl radicals having 12 to 16 carbon atoms and a polyglycosyl radical having a polymerization degree n of 1.1 to 2.
Particular preference is given tc alkyl polyglycosides having a polyglycosyl radical in which n is 1.1 to 1.5 and very particularly preferably n is 1.2 to 1.4. The preferred glycosyl radical is a glucosyl radical. Alkyl polyglycosides having long-chain alkyl groups are generally prepared by single- or multi-stage syntheses. A single-stage preparation process id described inter alia in DE-A-41 01 252.
A two-stage preparation process is described, for example in EP-A-0 306 652, according to which an n-butyl glycoside is first prepared by glycosidation with n-butanol and thereupon the desired long-chain alkyl polyglycoside is prepared by transglycosidation with a long-chain alcohol.
When the reaction is complete, the alkyl polyglyco-sides are present dissolved in long-chain alcohols. These alcohols must then be separated off if it is desired to obtain products completely soluble in water.
In the case of relatively high aesthetic requirements, alkyl polyglycosides are products which must be sub~ected to a bleaching reaction in order to obtain sufficiently light-colcured products. This bleaching is generally carried out using hydrogen peroxide with aqueous alkyl polyglycoside solutions. A disadvantage in this process is the poor space-time yields, especially if, for complete decomposition of the residual peroxide, the aqueous alkyl polyglycoside solutions must still be kept at elevated temperature for a relatively long time. The product can be damaged by this, and dark colours and decomposition products, some of which have an unpleasant odour, occur. Moreover, there is the risk of foam development which can no longer be controlled.
Wo 91/19723 describes a route for alkyl polyglycoside bleaching, where the material which is virtually free of fatty alcohol and water is kneaded at temperatures of 50 to 150C with aqueous hydrogen peroxide and a base, e.g. sodium hydroxide solution. The above-described disadvantages of the alkyl ..
polyglycoside bleaching in aqueous solution no longer occur in this bleaching method. It is a disadvantage that the bleaching is not possible in this manner at temperatures significantly above 100C. However, often low-fatty-alcohol and low-moisture products can be kneaded only at temperatures above 100C.
Difficulties can further arise in the addition of sodium hydroxide solution. A certain acidification effect during the bleaching reaction must be compensated for by the addition of base. Controlled addition of the sodium hydroxide solution would only be effected at great expense, because the pH cannot be measured directly in the melt. Addition by hand always introduces the risk of overdosing or underdosing, as a result of which the bleaching result would rapidly worsen.
A major object according to the present invention is therefore to find a process which permits the oxidizing bleach-ing in a melt without the problems described above with the addition ¢f hydrogen peroxide and sodium hydroxide solution.
It has now been found that very good bleaching results can be achieved even at temperatures above 100C if solid bleaching agents such as sodium percarbonate or sodium perbGrate are used, instead of the aqueous hydrogen peroxide solution.
The present invention therefore provides a process for bleaching low-moisture and low-fatty-alcohol alkyl poly-glycosides, which is characterized in that solid oxidizing agents are added and the bleaching is carried out at tempera-tures of 80 to 160C with thorough mixing.
According to the process of the present invention, preferably temperatures of 90 to 150C are employed, and very particularly preferably, temperatures of 100 to 140C. The alkyl polyglycoside (APG) used is preferably the alkyl poly-glucoside.
The substances can be incorporated withcut difficulty into viscose APG (temperature 80-160C) using, e.g.
extruders or kneading machines, so that homogeneous products result. An addition of alkali during bleaching is superfluous, since when these bleaching agents are used there is no pH
decrease. The products obtained are very light in colour and are markedly low in odour. Addition of small amounts of water before bleaching can further improve the result. The content of water can be 0 to 10% by weight, but it is preferably between 0 and 5%. The fatty alcohol content in the alkyl polyglycoside subjected to bleaching is 0 to 10% by weight, preferably 0 to 5%, values of 0 to 2.5% being very particularly preferred. The fatty alcohol is typically a fatty alcohol having 8 to 18 carbon atoms.
For better understanding the present invention, an example is described hereinunder. However, it should never be considered that the present invention is limited to the example.
Example Solid APG containing about 15% fatty alcohol and about 4.5% water is molten in 500 g portions at a temperature of 95C. A solution of 50% of this APG in demineralized water has aniodine colour number of 52 and a pH value of 7.2.
.
An extruder with a capacity of 600 milliliters, as being used for test extrusion purposes of plastic material, is heated to 95C. The APG melt is filled in in 100 g portions.
On 100 g of molten APG a 1,5 g portion of solid sodium perborate is added. The extrusion speed is regulated to about 2.5 kg an hour. The mixture is extruded on a running belt for cooling down, so that a line of solid APG with a crGsscut of 8 milli-meters in diameter is resulting.
The solid APG is collected and dissolved in warm demineralized water, using a water APG weight ratio of 1:1.
The resulting APG solution is nearly odourless and has an iodine colour number of 2.3. The measured pH value of the solution is 7.7.
in a kneader or in an extruder.
Alkyl polyglycosides are prepared from natural raw materials and are nontoxic and readily degradable surface-active materials. They are therefore used as detergents, cleaning agents, emulsifiers and dispersants. However, they only have the desired interfacial properties when the alkyl groups have at least 8 carbon atoms. The alkyl polyglycosides for the purposes of this invention have with the formula:
R' - C ~ Zn' in which R' represents an unbranched or branched, saturated or unsaturated aliphatic hydrocarbon radical having 8 to 18 carbon atoms or mixtures thereof and Zn represents a poly-glycosyl radical having a polymerization degree n of 1.1 to 3 of hexose or pentose units or mixtures thereof.
Preference is given to alkyl polyglycosides having alkyl radicals having 12 to 16 carbon atoms and a polyglycosyl radical having a polymerization degree n of 1.1 to 2.
Particular preference is given tc alkyl polyglycosides having a polyglycosyl radical in which n is 1.1 to 1.5 and very particularly preferably n is 1.2 to 1.4. The preferred glycosyl radical is a glucosyl radical. Alkyl polyglycosides having long-chain alkyl groups are generally prepared by single- or multi-stage syntheses. A single-stage preparation process id described inter alia in DE-A-41 01 252.
A two-stage preparation process is described, for example in EP-A-0 306 652, according to which an n-butyl glycoside is first prepared by glycosidation with n-butanol and thereupon the desired long-chain alkyl polyglycoside is prepared by transglycosidation with a long-chain alcohol.
When the reaction is complete, the alkyl polyglyco-sides are present dissolved in long-chain alcohols. These alcohols must then be separated off if it is desired to obtain products completely soluble in water.
In the case of relatively high aesthetic requirements, alkyl polyglycosides are products which must be sub~ected to a bleaching reaction in order to obtain sufficiently light-colcured products. This bleaching is generally carried out using hydrogen peroxide with aqueous alkyl polyglycoside solutions. A disadvantage in this process is the poor space-time yields, especially if, for complete decomposition of the residual peroxide, the aqueous alkyl polyglycoside solutions must still be kept at elevated temperature for a relatively long time. The product can be damaged by this, and dark colours and decomposition products, some of which have an unpleasant odour, occur. Moreover, there is the risk of foam development which can no longer be controlled.
Wo 91/19723 describes a route for alkyl polyglycoside bleaching, where the material which is virtually free of fatty alcohol and water is kneaded at temperatures of 50 to 150C with aqueous hydrogen peroxide and a base, e.g. sodium hydroxide solution. The above-described disadvantages of the alkyl ..
polyglycoside bleaching in aqueous solution no longer occur in this bleaching method. It is a disadvantage that the bleaching is not possible in this manner at temperatures significantly above 100C. However, often low-fatty-alcohol and low-moisture products can be kneaded only at temperatures above 100C.
Difficulties can further arise in the addition of sodium hydroxide solution. A certain acidification effect during the bleaching reaction must be compensated for by the addition of base. Controlled addition of the sodium hydroxide solution would only be effected at great expense, because the pH cannot be measured directly in the melt. Addition by hand always introduces the risk of overdosing or underdosing, as a result of which the bleaching result would rapidly worsen.
A major object according to the present invention is therefore to find a process which permits the oxidizing bleach-ing in a melt without the problems described above with the addition ¢f hydrogen peroxide and sodium hydroxide solution.
It has now been found that very good bleaching results can be achieved even at temperatures above 100C if solid bleaching agents such as sodium percarbonate or sodium perbGrate are used, instead of the aqueous hydrogen peroxide solution.
The present invention therefore provides a process for bleaching low-moisture and low-fatty-alcohol alkyl poly-glycosides, which is characterized in that solid oxidizing agents are added and the bleaching is carried out at tempera-tures of 80 to 160C with thorough mixing.
According to the process of the present invention, preferably temperatures of 90 to 150C are employed, and very particularly preferably, temperatures of 100 to 140C. The alkyl polyglycoside (APG) used is preferably the alkyl poly-glucoside.
The substances can be incorporated withcut difficulty into viscose APG (temperature 80-160C) using, e.g.
extruders or kneading machines, so that homogeneous products result. An addition of alkali during bleaching is superfluous, since when these bleaching agents are used there is no pH
decrease. The products obtained are very light in colour and are markedly low in odour. Addition of small amounts of water before bleaching can further improve the result. The content of water can be 0 to 10% by weight, but it is preferably between 0 and 5%. The fatty alcohol content in the alkyl polyglycoside subjected to bleaching is 0 to 10% by weight, preferably 0 to 5%, values of 0 to 2.5% being very particularly preferred. The fatty alcohol is typically a fatty alcohol having 8 to 18 carbon atoms.
For better understanding the present invention, an example is described hereinunder. However, it should never be considered that the present invention is limited to the example.
Example Solid APG containing about 15% fatty alcohol and about 4.5% water is molten in 500 g portions at a temperature of 95C. A solution of 50% of this APG in demineralized water has aniodine colour number of 52 and a pH value of 7.2.
.
An extruder with a capacity of 600 milliliters, as being used for test extrusion purposes of plastic material, is heated to 95C. The APG melt is filled in in 100 g portions.
On 100 g of molten APG a 1,5 g portion of solid sodium perborate is added. The extrusion speed is regulated to about 2.5 kg an hour. The mixture is extruded on a running belt for cooling down, so that a line of solid APG with a crGsscut of 8 milli-meters in diameter is resulting.
The solid APG is collected and dissolved in warm demineralized water, using a water APG weight ratio of 1:1.
The resulting APG solution is nearly odourless and has an iodine colour number of 2.3. The measured pH value of the solution is 7.7.
Claims (9)
1. A process for bleaching an alkyl polyglycoside of the formula:
R' - O - Zn (wherein R' is an unbranched or branched saturated or unsaturated aliphatic hydrocarbon radical having 8 to 18 carbon atoms, and Zn is a polyglycosyl radical having a polymerization degree n of 1.1 to 3 of hexose or pentose units), which comprises:
adding a solid oxidizing agent to the alkyl poly-glycoside having a water content of 0 to 10% by weight and a fatty alcohol content of 0 to 10% by weight, and heating the resulting mixture at 80 to 160°C with thorough mixing.
R' - O - Zn (wherein R' is an unbranched or branched saturated or unsaturated aliphatic hydrocarbon radical having 8 to 18 carbon atoms, and Zn is a polyglycosyl radical having a polymerization degree n of 1.1 to 3 of hexose or pentose units), which comprises:
adding a solid oxidizing agent to the alkyl poly-glycoside having a water content of 0 to 10% by weight and a fatty alcohol content of 0 to 10% by weight, and heating the resulting mixture at 80 to 160°C with thorough mixing.
2. A process according to claim 1, wherein the solid oxidizing agent is sodium percarbonate.
3. A process according to claim 1, wherein the solid oxidizing agent is sodium perborate.
4. A process according to any one of claims 1 to 3, wherein the heating is carried out at a temperature of 90 to 150°C.
5. A process according to claim 4, wherein the heating is carried out at a temperature of 100 to 140°C.
6. A process according to any one of claims 1 to 5, wherein up to 5% of water is added to the alkyl polyglycoside before the heating step.
7. A process according to any one of claims 1 to 6, wherein the alkyl polyglycoside is an alkyl polyglucoside.
8. A process according to any one of claims 1 to 7, wherein the thorough mixing is performed in a kneader.
9. A process according to any one of claims 1 to 8, wherein the thorough mixing is performed in an extruder.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4443084A DE4443084A1 (en) | 1994-12-03 | 1994-12-03 | Process for bleaching alkyl polyglycosides |
| DEP4443084.1 | 1994-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2164284A1 true CA2164284A1 (en) | 1996-06-04 |
Family
ID=6534844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002164284A Abandoned CA2164284A1 (en) | 1994-12-03 | 1995-12-01 | Process for bleaching alkyl polyglycosides |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP0719784A3 (en) |
| JP (1) | JPH08231578A (en) |
| KR (1) | KR960022550A (en) |
| CN (1) | CN1130190A (en) |
| CA (1) | CA2164284A1 (en) |
| DE (1) | DE4443084A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180222934A1 (en) * | 2017-02-06 | 2018-08-09 | Logos Technologies, Llc | Decolorization of concentrated rhamnolipid composition |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3839318A (en) * | 1970-09-27 | 1974-10-01 | Rohm & Haas | Process for preparation of alkyl glucosides and alkyl oligosaccharides |
| DE3232791A1 (en) * | 1982-09-03 | 1984-03-08 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING ALKYL GLUCOSIDES |
| US4959468A (en) * | 1987-06-12 | 1990-09-25 | Henkel Kommanditgesellschaft Auf Aktien | Color stabilization method for glycoside products |
| DE3729844A1 (en) | 1987-09-05 | 1989-03-23 | Huels Chemische Werke Ag | METHOD FOR PRODUCING ALKYLOLIGOGLYCOSIDES |
| DE3804599A1 (en) * | 1988-02-13 | 1989-08-24 | Basf Ag | METHOD FOR PURIFYING LONG CHAIN ALKYL GLUCOSIDES |
| DE4019175A1 (en) | 1990-06-15 | 1992-01-02 | Henkel Kgaa | METHOD FOR BRIGHTENING DISCOLORED SURFACE ACTIVE ALKYL GLYCOSIDES AND TREATMENT OF THE BLEACHED GOODS |
| DE4101252A1 (en) | 1991-01-17 | 1992-07-23 | Huels Chemische Werke Ag | METHOD FOR PRODUCING ALKYLGLYCOSIDES AND ALKYLPOLYGLYCOSIDES |
-
1994
- 1994-12-03 DE DE4443084A patent/DE4443084A1/en not_active Withdrawn
-
1995
- 1995-10-11 EP EP95116016A patent/EP0719784A3/en not_active Withdrawn
- 1995-11-30 CN CN95120993A patent/CN1130190A/en active Pending
- 1995-12-01 JP JP7314381A patent/JPH08231578A/en not_active Withdrawn
- 1995-12-01 CA CA002164284A patent/CA2164284A1/en not_active Abandoned
- 1995-12-02 KR KR1019950046135A patent/KR960022550A/en not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20180222934A1 (en) * | 2017-02-06 | 2018-08-09 | Logos Technologies, Llc | Decolorization of concentrated rhamnolipid composition |
| US10829507B2 (en) * | 2017-02-06 | 2020-11-10 | Stepan Company | Decolorization of concentrated rhamnolipid composition |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0719784A3 (en) | 1996-09-11 |
| EP0719784A2 (en) | 1996-07-03 |
| JPH08231578A (en) | 1996-09-10 |
| DE4443084A1 (en) | 1996-06-05 |
| CN1130190A (en) | 1996-09-04 |
| KR960022550A (en) | 1996-07-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0165721B1 (en) | Glycoside color regulation | |
| US4847368A (en) | Method of manufacturing alkyloligoglycosides | |
| JP3139686B2 (en) | Process for producing alkyl glycoside and alkyl polyglycoside | |
| US4306062A (en) | Process for the preparation of sucrose monoesters | |
| CZ5895A3 (en) | Continuous bleaching of alkyl polygycosides and products obtained therefrom | |
| CA2164284A1 (en) | Process for bleaching alkyl polyglycosides | |
| US5212292A (en) | Process for the preparation of light-colored alkyl polyglycosides | |
| JP3081240B2 (en) | Bleaching of discolored surface active alkyl glycosides and method of treating bleached material | |
| US4866165A (en) | Process for the preparation of alkyloligoglycosides | |
| US5432275A (en) | Continuous bleaching of alkylpolyglycosides | |
| US6204369B1 (en) | Process for the preparation of alykl polyglycosides | |
| JP2001515469A (en) | Method for producing alkyl polyglycoside | |
| US5457190A (en) | Process for the preparation of glycosides | |
| US4739043A (en) | Method for the synthesis of alkyl, cycloalkyl or alcenyl aldosides or polyaldosides | |
| CA2157545A1 (en) | Process for preparing alkyl polyglycosides | |
| US5510482A (en) | Process for bleaching discolored surface-active alkyl glycosides and for working up the bleached material | |
| JPH05155895A (en) | Preparation of light-colored alkyl polyglycoside | |
| US5641873A (en) | Process for preparing alkyl oligoglycosides | |
| WO2001009153A1 (en) | Process for reducing cycle times in reactions during the production of alkyl polyglycosides | |
| US5668275A (en) | Process for bleaching alkyl polyglycosides | |
| EP1817321A1 (en) | Process for the production of esters of sugars and sugar derivatives | |
| JPH0665276A (en) | Preparation of alkyl polyglycoside | |
| TH8364EX (en) | A process for producing excellent alkyl glycosides in paints. | |
| JPS5598245A (en) | Melamine-based resin molding material composition |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |