GB768309A - Process for the production of amides of alginic acid - Google Patents
Process for the production of amides of alginic acidInfo
- Publication number
- GB768309A GB768309A GB8696/55A GB869655A GB768309A GB 768309 A GB768309 A GB 768309A GB 8696/55 A GB8696/55 A GB 8696/55A GB 869655 A GB869655 A GB 869655A GB 768309 A GB768309 A GB 768309A
- Authority
- GB
- United Kingdom
- Prior art keywords
- groups
- acid
- per cent
- ester
- alginic acid
- 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
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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/0052—Preparation of gels
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Molecular Biology (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Abstract
Alginic acid amides are made by reacting alginic esters with one or more compounds HNR1R2, where R1 and R2 are hydrogen or organic residues, e.g. hydrocarbon radicals which may be substituted; the ammonia or amine is used in amount at least 0.5 and preferably 1.5-20 times the weight of alginic ester and the water content of the reaction mixture is not more than 50 per cent by weight of the dry ester. The reaction temperature may be -10 DEG to +50 DEG C., preferably -5 DEG to +40 DEG C. The products form gels on cooling their aqueous solutions containing 0.4-10 per cent of amide by weight. The esters used may be those of mono- or poly-valent aliphatic alcohols of 1-3 carbon atoms, especially those obtained by esterifying alginic acid with diazomethane or alkylene oxides until at least 40 per cent and preferably 60-100 per cent of the carboxylic groups have reacted. The water content of the esters is preferably reduced below 50 per cent by washing with water-soluble organic liquids. Some of the ester groups are probably hydrolysed to carboxylic acid salts at the same time as the others are converted to amide groups, and also some ester groups may remain unconverted. In the examples: (1) alginic acid is esterified with ethylene oxide and the product reacted with ammonia, (2) alginic acid is treated with diazomethane to give a product containing methyl as well as ester groups and the latter reacted with ammonia; (3) the glycol ester of alginic acid is treated with ethanolamine, glycine, glycylglycine, dodecylamine, ethylene diamine and urea to give the corresponding amides, the last two being crosslinked. In general the groups R1 and R2 may be hydrogen or aliphatic, cycloaliphatic or aromatic residues and may contain other atoms, e.g. in the form of hydroxyl, carboxylic acid, carboxylic amide or sulphonic acid groups. Suitable amines other than the above are methylamine, ethylamine, propylamine, propanolamine, octylamine, octadecylamine, cyclohexylamine, amino-sugars, aniline, naphthylamine, benzylamine, anthranilic acid, sulphanilic acid, taurine, hexamethylenediamine and phenylenediamine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE768309X | 1954-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB768309A true GB768309A (en) | 1957-02-13 |
Family
ID=6673686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8696/55A Expired GB768309A (en) | 1954-03-27 | 1955-03-25 | Process for the production of amides of alginic acid |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB768309A (en) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264422A (en) * | 1986-06-30 | 1993-11-23 | Fidia S.P.A. | Esters of alginic acid with steroidal alcohols |
| FR2694894A1 (en) * | 1992-08-20 | 1994-02-25 | Coletica | Use of a transacylation reaction between an esterified polysaccharide and a polyamine or polyhydroxylated substance for the manufacture of microparticles, process and composition. |
| US5336668A (en) * | 1986-06-30 | 1994-08-09 | Fidia, S.P.A. | Esters of alginic acid |
| EP1955750A1 (en) | 2007-02-01 | 2008-08-13 | Lallemand UK Limited | Clarification agent |
| 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 |
| CN115531334A (en) * | 2022-10-26 | 2022-12-30 | 广州朗圣药业有限公司 | Sildenafil citrate tablet and preparation method thereof |
| CN116410901A (en) * | 2023-04-17 | 2023-07-11 | 赣州京善科技合伙企业(有限合伙) | Preparation method and application of bifidobacterium longum freeze-dried powder |
| US12097307B2 (en) | 2015-11-01 | 2024-09-24 | Massachusetts Institute Of Technology | Modified alginates for anti-fibrotic materials and applications |
-
1955
- 1955-03-25 GB GB8696/55A patent/GB768309A/en not_active Expired
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5264422A (en) * | 1986-06-30 | 1993-11-23 | Fidia S.P.A. | Esters of alginic acid with steroidal alcohols |
| US5336668A (en) * | 1986-06-30 | 1994-08-09 | Fidia, S.P.A. | Esters of alginic acid |
| US5416205A (en) * | 1986-06-30 | 1995-05-16 | Fidia, S.P.A. | New esters of alginic acid |
| FR2694894A1 (en) * | 1992-08-20 | 1994-02-25 | Coletica | Use of a transacylation reaction between an esterified polysaccharide and a polyamine or polyhydroxylated substance for the manufacture of microparticles, process and composition. |
| WO1994004261A1 (en) * | 1992-08-20 | 1994-03-03 | Coletica | Utilization of a transacylation reaction between an esterified polysaccharide and a polyaminated or polyhydroxylated substance for fabricating microparticles, microparticles thus obtained, methods and compositions containing them |
| EP1955750A1 (en) | 2007-02-01 | 2008-08-13 | Lallemand UK Limited | Clarification agent |
| US10842753B2 (en) | 2011-06-02 | 2020-11-24 | 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 |
| US10285949B2 (en) * | 2011-06-02 | 2019-05-14 | Massachusetts Institute Of Technology | Modified alginates for cell encapsulation and cell therapy |
| EP4083074A1 (en) * | 2011-06-02 | 2022-11-02 | Massachusetts Institute Of Technology | Modified alginates for cell encapsulation and cell therapy |
| US20160324793A1 (en) * | 2011-06-02 | 2016-11-10 | Massachusetts Institute Of Technology | Modified alginates for cell encapsulation and cell therapy |
| EP3354665A1 (en) * | 2011-06-02 | 2018-08-01 | 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 |
| US12097307B2 (en) | 2015-11-01 | 2024-09-24 | 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 |
| CN115531334A (en) * | 2022-10-26 | 2022-12-30 | 广州朗圣药业有限公司 | Sildenafil citrate tablet and preparation method thereof |
| CN115531334B (en) * | 2022-10-26 | 2023-09-08 | 广州朗圣药业有限公司 | Sildenafil citrate tablet and preparation method thereof |
| CN116410901A (en) * | 2023-04-17 | 2023-07-11 | 赣州京善科技合伙企业(有限合伙) | Preparation method and application of bifidobacterium longum freeze-dried powder |
| CN116410901B (en) * | 2023-04-17 | 2024-02-06 | 赣州京善科技合伙企业(有限合伙) | Preparation method and application of bifidobacterium longum freeze-dried powder |
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