DE2529086C3 - Verfahren zur Herstellung von Alkylenglykolalginaten - Google Patents
Verfahren zur Herstellung von AlkylenglykolalginatenInfo
- Publication number
- DE2529086C3 DE2529086C3 DE2529086A DE2529086A DE2529086C3 DE 2529086 C3 DE2529086 C3 DE 2529086C3 DE 2529086 A DE2529086 A DE 2529086A DE 2529086 A DE2529086 A DE 2529086A DE 2529086 C3 DE2529086 C3 DE 2529086C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- algae
- treated
- alga
- 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
- 235000010443 alginic acid Nutrition 0.000 title claims description 104
- 229920000615 alginic acid Polymers 0.000 title claims description 104
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 33
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims description 30
- -1 alkylene glycol Chemical compound 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims 2
- 241000195493 Cryptophyta Species 0.000 claims description 115
- 238000005886 esterification reaction Methods 0.000 claims description 81
- 230000032050 esterification Effects 0.000 claims description 79
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 78
- 239000002253 acid Substances 0.000 claims description 68
- 239000000783 alginic acid Substances 0.000 claims description 64
- 229960001126 alginic acid Drugs 0.000 claims description 64
- 150000004781 alginic acids Chemical class 0.000 claims description 62
- 125000002947 alkylene group Chemical group 0.000 claims description 45
- 239000000047 product Substances 0.000 claims description 42
- 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 claims description 34
- 239000000243 solution Substances 0.000 claims description 34
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 32
- 229940072056 alginate Drugs 0.000 claims description 32
- 238000006386 neutralization reaction Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 17
- 239000000284 extract Substances 0.000 claims description 13
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 239000012928 buffer substance Substances 0.000 claims description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 239000002002 slurry Substances 0.000 claims description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 9
- 241000199919 Phaeophyceae Species 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- 241001466453 Laminaria Species 0.000 claims description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229910017604 nitric acid Inorganic materials 0.000 claims description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 241000512259 Ascophyllum nodosum Species 0.000 claims description 4
- 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 claims description 4
- 241001598113 Laminaria digitata Species 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 229910021538 borax Inorganic materials 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 235000010339 sodium tetraborate Nutrition 0.000 claims description 4
- 241000199897 Alaria esculenta Species 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003929 acidic solution Substances 0.000 claims description 3
- 239000006286 aqueous extract Substances 0.000 claims description 3
- 159000000011 group IA salts Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 238000002955 isolation Methods 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 235000010755 mineral Nutrition 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 239000011591 potassium Substances 0.000 claims description 3
- 239000004328 sodium tetraborate Substances 0.000 claims description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 claims description 2
- 239000008098 formaldehyde solution Substances 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 241000894007 species Species 0.000 claims description 2
- AEMOLEFTQBMNLQ-BZINKQHNSA-N D-Guluronic Acid Chemical compound OC1O[C@H](C(O)=O)[C@H](O)[C@@H](O)[C@H]1O AEMOLEFTQBMNLQ-BZINKQHNSA-N 0.000 claims 1
- AEMOLEFTQBMNLQ-VANFPWTGSA-N D-mannopyranuronic acid Chemical compound OC1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H]1O AEMOLEFTQBMNLQ-VANFPWTGSA-N 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 claims 1
- 241000004455 Fucus spiralis Species 0.000 claims 1
- 241000227647 Fucus vesiculosus Species 0.000 claims 1
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 claims 1
- 241000500881 Lepisma Species 0.000 claims 1
- 241001491705 Macrocystis pyrifera Species 0.000 claims 1
- AEMOLEFTQBMNLQ-UHFFFAOYSA-N beta-D-galactopyranuronic acid Natural products OC1OC(C(O)=O)C(O)C(O)C1O AEMOLEFTQBMNLQ-UHFFFAOYSA-N 0.000 claims 1
- 229910000022 magnesium bicarbonate Inorganic materials 0.000 claims 1
- 235000014824 magnesium bicarbonate Nutrition 0.000 claims 1
- 239000002370 magnesium bicarbonate Substances 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 230000001932 seasonal effect Effects 0.000 claims 1
- 238000010992 reflux Methods 0.000 description 19
- 238000010306 acid treatment Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000000605 extraction Methods 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000001556 precipitation Methods 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000004679 hydroxides Chemical class 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 239000003513 alkali Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000013505 freshwater Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000000770 propane-1,2-diol alginate Substances 0.000 description 3
- 235000010409 propane-1,2-diol alginate Nutrition 0.000 description 3
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 2
- 241000512260 Ascophyllum Species 0.000 description 2
- 241001474374 Blennius Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000661 sodium alginate Substances 0.000 description 2
- 235000010413 sodium alginate Nutrition 0.000 description 2
- 229940005550 sodium alginate Drugs 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- DBTMGCOVALSLOR-DEVYUCJPSA-N (2s,3r,4s,5r,6r)-4-[(2s,3r,4s,5r,6r)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@H](O)[C@@H]2O)O)O[C@H](CO)[C@H]1O DBTMGCOVALSLOR-DEVYUCJPSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 239000005717 Laminarin Substances 0.000 description 1
- 229920001543 Laminarin Polymers 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 235000013847 iso-butane Nutrition 0.000 description 1
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000013535 sea water Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- MSXHSNHNTORCAW-MPGIDXPLSA-M sodium;(3s,4s,5s,6r)-3,4,5,6-tetrahydroxyoxane-2-carboxylate Chemical compound [Na+].O[C@@H]1OC(C([O-])=O)[C@@H](O)[C@H](O)[C@@H]1O MSXHSNHNTORCAW-MPGIDXPLSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 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
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA204,887A CA1019326A (en) | 1974-07-16 | 1974-07-16 | Process for the production of alkylene glycol alginates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2529086A1 DE2529086A1 (de) | 1976-01-29 |
| DE2529086B2 DE2529086B2 (de) | 1979-12-13 |
| DE2529086C3 true DE2529086C3 (de) | 1980-08-21 |
Family
ID=4100671
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2529086A Expired DE2529086C3 (de) | 1974-07-16 | 1975-06-30 | Verfahren zur Herstellung von Alkylenglykolalginaten |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3948881A (enExample) |
| JP (1) | JPS5119800A (enExample) |
| CA (1) | CA1019326A (enExample) |
| DE (1) | DE2529086C3 (enExample) |
| DK (1) | DK321075A (enExample) |
| ES (1) | ES439475A1 (enExample) |
| FR (1) | FR2278706A1 (enExample) |
| GB (1) | GB1514223A (enExample) |
| NO (1) | NO140719C (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1057746A (en) * | 1975-09-16 | 1979-07-03 | Merck And Co. | Propylene glycol alginic acid esters |
| US4226855A (en) * | 1976-12-16 | 1980-10-07 | Mitsubishi Chemical Industries Ltd. | Plant viral disease preventive alginate containing compositions |
| IT1203814B (it) * | 1986-06-30 | 1989-02-23 | Fidia Farmaceutici | Esteri dell'acido alginico |
| US5264422A (en) * | 1986-06-30 | 1993-11-23 | Fidia S.P.A. | Esters of alginic acid with steroidal alcohols |
| SK43694A3 (en) * | 1991-10-28 | 1995-01-12 | Procter & Gamble | Drinking system thickener/emulsifier |
| US7128929B1 (en) * | 1999-04-29 | 2006-10-31 | Scherr George H | Alginate foam compositions |
| KR100501584B1 (ko) * | 2000-02-03 | 2005-07-18 | (주)케이비피 | 저분자 폴리만유로네이트의 제조방법, 혈청지질개선제로서의 이의 신규 용도 및 이를 함유하는 기능성식품 및 건강 보조 식품 |
| KR100447085B1 (ko) * | 2001-11-08 | 2004-09-04 | 바램제약주식회사 | 마그네슘이온, 칼슘이온 또는 철이온이 고농도로 결합된알긴산의 제조 방법 |
| US20040062845A1 (en) * | 2001-11-30 | 2004-04-01 | Krawczyk Gregory R. | Beverage emulsion stabilizer |
| DE602004009969D1 (de) * | 2003-01-08 | 2007-12-27 | Univ De Los Lagos | Produktives Verfahren zur Herstellung einer auf Algen basierenden organischen Ergänzung für die Pflanzendüngung |
| PE20060468A1 (es) * | 2004-04-26 | 2006-07-06 | Cp Kelco Aps | Composicion dermoprotectora para controlar la alcalinidad de la piel que comprende polisacaridos de acido carboxilico |
| AU2007224137A1 (en) * | 2006-03-01 | 2007-09-13 | Fmc Biopolymer As | Biodegradable foam |
| ATE552867T1 (de) * | 2006-06-16 | 2012-04-15 | Fmc Biopolymer As | Alginatbeschichtete collagenmatrix- zellvorrichtung, herstellungsverfahren dafür und verwendungen davon |
| JP5328780B2 (ja) * | 2007-06-13 | 2013-10-30 | エフ エム シー コーポレーション | アルギネート被覆多糖ゲル含有発泡体複合物、その製法および用途 |
| US20090060943A1 (en) * | 2007-08-31 | 2009-03-05 | O'mara Brendan Joseph | Syndrome X Composition and Method of Lowering Blood Pressure and Glycemic Index |
| WO2013031030A1 (en) | 2011-09-01 | 2013-03-07 | L'oreal | Cosmetic sheet |
| WO2016113716A1 (en) * | 2015-01-16 | 2016-07-21 | Steer Engineering Private Limited | A biodegradable plastic like material obtained from a seaweed |
| US10785999B2 (en) | 2019-02-01 | 2020-09-29 | Ajinomoto Foods North America, Inc. | Rice dough compositions and gluten-free rice noodles made therefrom |
| WO2021217560A1 (en) | 2020-04-30 | 2021-11-04 | L'oreal | Kit for caring for the skin |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1814981A (en) * | 1927-08-06 | 1931-07-14 | Kelco Co | Process of preparing alginic acid and compounds thereof |
| US2128551A (en) * | 1934-01-11 | 1938-08-30 | Algin Corp Of America | Method of treating seaweed |
| US2036934A (en) * | 1934-04-21 | 1936-04-07 | Kelco Co | Process for making alginic acid and product |
| US2036922A (en) * | 1935-01-31 | 1936-04-07 | Kelco Co | Alginic acid and process of making same |
| US2426125A (en) * | 1944-04-03 | 1947-08-19 | Kelco Co | Manufacture of glycol alginates |
| US2494911A (en) * | 1945-12-22 | 1950-01-17 | Kelco Co | High-stability glycol alginates and their manufacture |
| US2494912A (en) * | 1947-01-20 | 1950-01-17 | Kelco Co | Higher alkylene glycol esters of alginic acid |
| GB676618A (en) * | 1947-09-12 | 1952-07-30 | Kelco Co | Alkylene glycol esters of alginic acid |
| NL296818A (enExample) * | 1962-08-21 | |||
| US3396158A (en) * | 1964-11-02 | 1968-08-06 | Norsk Inst For Tang Og Tarefor | Preparation of alginic acid by extraction of algae |
| US3772266A (en) * | 1972-10-19 | 1973-11-13 | Kelco Co | Process for the preparation of propylene glycol alginate from partially neutralized alginic acid |
-
1974
- 1974-07-16 CA CA204,887A patent/CA1019326A/en not_active Expired
- 1974-10-25 US US05/518,126 patent/US3948881A/en not_active Expired - Lifetime
-
1975
- 1975-06-09 GB GB24643/75A patent/GB1514223A/en not_active Expired
- 1975-06-18 NO NO752170A patent/NO140719C/no unknown
- 1975-06-24 JP JP50078471A patent/JPS5119800A/ja active Pending
- 1975-06-30 DE DE2529086A patent/DE2529086C3/de not_active Expired
- 1975-07-15 DK DK321075A patent/DK321075A/da unknown
- 1975-07-15 FR FR7522110A patent/FR2278706A1/fr active Granted
- 1975-07-16 ES ES439475A patent/ES439475A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NO140719C (no) | 1979-10-24 |
| DK321075A (da) | 1976-01-17 |
| NO752170L (enExample) | 1976-01-19 |
| DE2529086A1 (de) | 1976-01-29 |
| DE2529086B2 (de) | 1979-12-13 |
| GB1514223A (en) | 1978-06-14 |
| NO140719B (no) | 1979-07-16 |
| FR2278706A1 (fr) | 1976-02-13 |
| CA1019326A (en) | 1977-10-18 |
| JPS5119800A (enExample) | 1976-02-17 |
| FR2278706B1 (enExample) | 1977-12-09 |
| US3948881A (en) | 1976-04-06 |
| ES439475A1 (es) | 1977-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |