GB676618A - Alkylene glycol esters of alginic acid - Google Patents
Alkylene glycol esters of alginic acidInfo
- Publication number
- GB676618A GB676618A GB25104/47A GB2510447A GB676618A GB 676618 A GB676618 A GB 676618A GB 25104/47 A GB25104/47 A GB 25104/47A GB 2510447 A GB2510447 A GB 2510447A GB 676618 A GB676618 A GB 676618A
- Authority
- GB
- United Kingdom
- Prior art keywords
- glycol
- alginic acid
- water
- alkylene
- product
- 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.)
- Expired
Links
- 235000010443 alginic acid Nutrition 0.000 title abstract 26
- 229920000615 alginic acid Polymers 0.000 title abstract 26
- 239000000783 alginic acid Substances 0.000 title abstract 14
- 229960001126 alginic acid Drugs 0.000 title abstract 14
- 150000004781 alginic acids Chemical class 0.000 title abstract 13
- -1 Alkylene glycol esters Chemical class 0.000 title abstract 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 15
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 abstract 10
- 229940072056 alginate Drugs 0.000 abstract 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 9
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 abstract 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 6
- 239000000047 product Substances 0.000 abstract 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 4
- 239000006227 byproduct Substances 0.000 abstract 4
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 229910021529 ammonia Inorganic materials 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 238000010438 heat treatment Methods 0.000 abstract 3
- 229940051250 hexylene glycol Drugs 0.000 abstract 3
- 230000003472 neutralizing effect Effects 0.000 abstract 3
- YSRSBDQINUMTIF-SNVBAGLBSA-N (2r)-decane-1,2-diol Chemical compound CCCCCCCC[C@@H](O)CO YSRSBDQINUMTIF-SNVBAGLBSA-N 0.000 abstract 2
- XWAMHGPDZOVVND-UHFFFAOYSA-N 1,2-octadecanediol Chemical compound CCCCCCCCCCCCCCCCC(O)CO XWAMHGPDZOVVND-UHFFFAOYSA-N 0.000 abstract 2
- RWLALWYNXFYRGW-UHFFFAOYSA-N 2-Ethyl-1,3-hexanediol Chemical compound CCCC(O)C(CC)CO RWLALWYNXFYRGW-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 2
- 230000001476 alcoholic effect Effects 0.000 abstract 2
- 239000012736 aqueous medium Substances 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229940097037 decylene glycol Drugs 0.000 abstract 2
- GHLKSLMMWAKNBM-UHFFFAOYSA-N dodecane-1,12-diol Chemical compound OCCCCCCCCCCCCO GHLKSLMMWAKNBM-UHFFFAOYSA-N 0.000 abstract 2
- 239000003995 emulsifying agent Substances 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- 229960005082 etohexadiol Drugs 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000007787 solid Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 235000013311 vegetables Nutrition 0.000 abstract 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- HDSBZMRLPLPFLQ-UHFFFAOYSA-N Propylene glycol alginate Chemical compound OC1C(O)C(OC)OC(C(O)=O)C1OC1C(O)C(O)C(C)C(C(=O)OCC(C)O)O1 HDSBZMRLPLPFLQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000010775 animal oil Substances 0.000 abstract 1
- 150000007514 bases Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000004140 cleaning Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 229940093476 ethylene glycol Drugs 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000002609 medium Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 239000002480 mineral oil Substances 0.000 abstract 1
- CBFGGFCKMTYCJS-UHFFFAOYSA-N octane-1,8-diol propane-1,2-diol Chemical compound C(CCCCCCCO)O.C(C(C)O)O CBFGGFCKMTYCJS-UHFFFAOYSA-N 0.000 abstract 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 abstract 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000770 propane-1,2-diol alginate Substances 0.000 abstract 1
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 abstract 1
- 229960004063 propylene glycol Drugs 0.000 abstract 1
- 239000012429 reaction media Substances 0.000 abstract 1
- 239000002002 slurry Substances 0.000 abstract 1
- 239000001488 sodium phosphate Substances 0.000 abstract 1
- 229910000162 sodium phosphate Inorganic materials 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 abstract 1
- 239000008158 vegetable oil Substances 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
- C08B37/0084—Guluromannuronans, e.g. alginic acid, i.e. D-mannuronic acid and D-guluronic acid units linked with alternating alpha- and beta-1,4-glycosidic bonds; Derivatives thereof, e.g. alginates
-
- 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
-
- 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
- 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
- C09K23/10—Derivatives of low-molecular-weight sulfocarboxylic acids or sulfopolycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Alkylene glycol esters of alginic acid are prepared for the purpose of modifying the alginic acid to render it water-soluble, by reacting the acid with a 1 : 2 or 1 : 3-alkylene monoxide in the presence of an aqueous medium in which the alkylene monoxide is soluble. This medium may be water or a mixture of water and an inert water-miscible solvent for the alkylene monoxide such as lower monohydric and polyhydric alcohols and ketones. The esterification is normally effected in a closed vessel at temperatures of 35-70 DEG C. Lower 1 : 2- and 1 : 3-alkylene monoxides having less than 6 carbon atoms may be reacted at temperatures of the order of 35 DEG to 50 DEG C. using water alone as reaction medium; the higher monoxides are generally reacted in the presence of the aqueous medium containing the inert water-miscible solvent though the inert solvent may be omitted in the case of the intermediate alkylene monoxides when higher temperatures, e.g. 70 DEG C. are used. If desired, the alginic acid may be reacted with a higher 1 : 2- or 1 : 3- alkylene monoxide, the resulting product freed of by-product glycol and then again reacted with a further quantity of the same or different higher 1 : 2- or 1 : 3-alkylene monoxide. Alternatively, following the first reaction with the higher alkyelene oxide, the product is reacted with a lower 1 : 2- or 1 : 3-alkylene monoxide, removal of by-product glycol at the intermediate stage then being optional. In all the esterifications, the alginic acid may be employed in a partially neutralized but still water-insoluble form, the neutralizing base being one capable of producing a water-soluble alginate; normally, about 5 to 50 per cent of the carboxylic groups are neutralized. Suitable bases are ammonia, lower amines and basic compounds of the alkali metals and magnesium. The alginic acid starting material may be prepared as described in U.S. Specification 1,814,981. The esters are emulsifying agents of animal, vegetable and mineral oils and may be used in foodstuffs (see Group VI), adhesives (see Group V) and in acidic cleaning compounds. In examples: (1) shredded alginic acid containing 55 per cent solids and the remainder water and isopropanol is heated with ethylene oxide under pressure at 48-57 DEG C. to form ethylene glycol alginate; (2) moist alginic acid (50 per cent solid) is partially neutralized with anhydrous ammonia and heated with propylene oxide in a pressure reaction vessel at 35-50 DEG C. yielding propylene glycol alginate; (3) alginic acid is partially neutralized by means of an alcoholic slurry of sodium phosphate, the water content adjusted to 50 per cent and the material then heated in an autoclave at 40 DEG C. with 1 : 2-epoxyhexane, by-product hexylene glycol removed by washing with isopropanol and the product again reacted with 1 : 2-epoxyhexane to yield hexylene glycol alginate; (4) octylene glycol alginate is formed by heating a mixture of partially neutralized alginic acid, water acetone and 1 : 2-epoxyoctane in an autoclave at 50 DEG C., the product being extracted with acetone to remove by-product glycol; (5) decylene glycol alginate is formed by heating partially neutralized alginic acid with water and 1 : 2-epoxydecane in an autoclave at 50 DEG C. and then at 60 DEG C.; (6) dodecylene glycol alginate is prepared by heating partially neutralized alginic acid with water, glycerol and 1 : 2-epoxydodecane in an autoclave at 50 DEG C.; (7) octadecylene glycol alginate is prepared from 1 : 2-epoxyoctadecane by the method of (6); (8) a mixed glycol alginate is prepared by treating the product of (4) with aqueous alcoholic hydrochloric acid to liberate the neutralized carboxylic groups, adjusting the water content of the ester to 50 per cent, particularly neutralizing the free carboxyl groups with gaseous ammonia and then reacting the product with propylene oxide to form a propylene glycol-octylene glycol alginate; ethylene oxide may be used similarly; (9) trimethylene glycol alginate is prepared by partially neutralizing with ammonia alginic acid containing 50 per cent moisture and then reacting with trimethylene oxide in an autoclave at 35-50 DEG C.ALSO:Alkylene glycol alginates, prepared by reacting a 1:2- or 1:3- alkylene monoxide with alginic acid which may be partially neutralized (see Group IV(b)), may be used as emulsifying agents in the production of animal, vegetable and mineral oil-in-water emulsions. Esters mentioned are the ethylene glycol, propylene glycol, hexylene glycol, octylene glycol, decylene glycol, dodecylene glycol, octadecylene glycol, octylene glycol-propylene glycol and trimethylene glycol alginates.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB25104/47A GB676618A (en) | 1947-09-12 | 1947-09-12 | Alkylene glycol esters of alginic acid |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB25104/47A GB676618A (en) | 1947-09-12 | 1947-09-12 | Alkylene glycol esters of alginic acid |
Publications (1)
Publication Number | Publication Date |
---|---|
GB676618A true GB676618A (en) | 1952-07-30 |
Family
ID=10222280
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB25104/47A Expired GB676618A (en) | 1947-09-12 | 1947-09-12 | Alkylene glycol esters of alginic acid |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB676618A (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3948881A (en) * | 1974-07-16 | 1976-04-06 | Uniroyal, Ltd. | Process for the production of alkylene glycol alginates |
FR2324645A1 (en) * | 1975-09-16 | 1977-04-15 | Merck & Co Inc | PROCESS FOR PREPARING PROPYLENE-GLYCOL ALGINATES |
US7008476B2 (en) | 2003-06-11 | 2006-03-07 | Az Electronic Materials Usa Corp. | Modified alginic acid of alginic acid derivatives and thermosetting anti-reflective compositions thereof |
US20160324793A1 (en) * | 2011-06-02 | 2016-11-10 | Massachusetts Institute Of Technology | Modified alginates for cell encapsulation and cell therapy |
US10730983B2 (en) | 2016-06-13 | 2020-08-04 | Massachusetts Institute Of Technology | Biocompatible coatings and hydrogels for reducing foreign body response and fibrosis |
US11266606B2 (en) | 2014-08-01 | 2022-03-08 | Massachusetts Institute Of Technology | Modified alginates for anti-fibrotic materials and applications |
US11318231B2 (en) | 2017-11-06 | 2022-05-03 | Massachusetts Institute Of Technology | Anti-inflammatory coatings to improve biocompatibility of neurological implants |
-
1947
- 1947-09-12 GB GB25104/47A patent/GB676618A/en not_active Expired
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3948881A (en) * | 1974-07-16 | 1976-04-06 | Uniroyal, Ltd. | Process for the production of alkylene glycol alginates |
FR2324645A1 (en) * | 1975-09-16 | 1977-04-15 | Merck & Co Inc | PROCESS FOR PREPARING PROPYLENE-GLYCOL ALGINATES |
US7008476B2 (en) | 2003-06-11 | 2006-03-07 | Az Electronic Materials Usa Corp. | Modified alginic acid of alginic acid derivatives and thermosetting anti-reflective compositions thereof |
US20160324793A1 (en) * | 2011-06-02 | 2016-11-10 | Massachusetts Institute Of Technology | Modified alginates for cell encapsulation and cell therapy |
US10285949B2 (en) * | 2011-06-02 | 2019-05-14 | Massachusetts Institute Of Technology | Modified alginates for cell encapsulation and cell therapy |
US11337930B2 (en) | 2011-06-02 | 2022-05-24 | Massachusetts Institute Of Technology | Modified alginates for cell encapsulation and cell therapy |
US11266606B2 (en) | 2014-08-01 | 2022-03-08 | Massachusetts Institute Of Technology | Modified alginates for anti-fibrotic materials and applications |
US10730983B2 (en) | 2016-06-13 | 2020-08-04 | Massachusetts Institute Of Technology | Biocompatible coatings and hydrogels for reducing foreign body response and fibrosis |
US11318231B2 (en) | 2017-11-06 | 2022-05-03 | Massachusetts Institute Of Technology | Anti-inflammatory coatings to improve biocompatibility of neurological implants |
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