US3696044A - Sequestrant compositions - Google Patents
Sequestrant compositions Download PDFInfo
- Publication number
- US3696044A US3696044A US52088A US3696044DA US3696044A US 3696044 A US3696044 A US 3696044A US 52088 A US52088 A US 52088A US 3696044D A US3696044D A US 3696044DA US 3696044 A US3696044 A US 3696044A
- Authority
- US
- United States
- Prior art keywords
- acid
- sequestering
- acids
- carbon atoms
- polyhydroxy
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title abstract description 45
- 239000003352 sequestering agent Substances 0.000 title abstract description 27
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 239000002253 acid Substances 0.000 abstract description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract description 12
- 150000007513 acids Chemical class 0.000 abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 11
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract description 6
- 150000004715 keto acids Chemical class 0.000 abstract description 6
- 150000002763 monocarboxylic acids Chemical class 0.000 abstract description 6
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract description 4
- 239000011975 tartaric acid Substances 0.000 abstract description 4
- 235000002906 tartaric acid Nutrition 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 3
- 230000014759 maintenance of location Effects 0.000 description 26
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 21
- 229910001424 calcium ion Inorganic materials 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 17
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229950006191 gluconic acid Drugs 0.000 description 11
- 239000000174 gluconic acid Substances 0.000 description 10
- 235000012208 gluconic acid Nutrition 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- AEQDJSLRWYMAQI-UHFFFAOYSA-N 2,3,9,10-tetramethoxy-6,8,13,13a-tetrahydro-5H-isoquinolino[2,1-b]isoquinoline Chemical compound C1CN2CC(C(=C(OC)C=C3)OC)=C3CC2C2=C1C=C(OC)C(OC)=C2 AEQDJSLRWYMAQI-UHFFFAOYSA-N 0.000 description 8
- 239000000176 sodium gluconate Substances 0.000 description 8
- 235000012207 sodium gluconate Nutrition 0.000 description 8
- 229940005574 sodium gluconate Drugs 0.000 description 8
- NAOLWIGVYRIGTP-UHFFFAOYSA-N 1,3,5-trihydroxyanthracene-9,10-dione Chemical compound C1=CC(O)=C2C(=O)C3=CC(O)=CC(O)=C3C(=O)C2=C1 NAOLWIGVYRIGTP-UHFFFAOYSA-N 0.000 description 7
- 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 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000003518 caustics Substances 0.000 description 4
- VBUYCZFBVCCYFD-JJYYJPOSSA-N 2-dehydro-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C(=O)C(O)=O VBUYCZFBVCCYFD-JJYYJPOSSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003599 detergent Substances 0.000 description 3
- IDAGXRIGDWCIET-SDFKWCIISA-L disodium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O IDAGXRIGDWCIET-SDFKWCIISA-L 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical class [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- 229940095064 tartrate Drugs 0.000 description 2
- KWMLJOLKUYYJFJ-GASJEMHNSA-N (2xi)-D-gluco-heptonic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)C(O)=O KWMLJOLKUYYJFJ-GASJEMHNSA-N 0.000 description 1
- WTAHRPBPWHCMHW-PAKKCRSFSA-N 3-dehydro-D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)C(=O)[C@@H](O)C(O)=O WTAHRPBPWHCMHW-PAKKCRSFSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- DSLZVSRJTYRBFB-UHFFFAOYSA-N Galactaric acid Natural products OC(=O)C(O)C(O)C(O)C(O)C(O)=O DSLZVSRJTYRBFB-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-QTBDOELSSA-N L-gulonic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O RGHNJXZEOKUKBD-QTBDOELSSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical class [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229920001273 Polyhydroxy acid Polymers 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- DSLZVSRJTYRBFB-DUHBMQHGSA-N galactaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O DSLZVSRJTYRBFB-DUHBMQHGSA-N 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 229940074439 potassium sodium tartrate Drugs 0.000 description 1
- 230000009919 sequestration Effects 0.000 description 1
- ZNCPFRVNHGOPAG-UHFFFAOYSA-L sodium oxalate Chemical compound [Na+].[Na+].[O-]C(=O)C([O-])=O ZNCPFRVNHGOPAG-UHFFFAOYSA-L 0.000 description 1
- 229940039790 sodium oxalate Drugs 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- OFCZUBZXJNUXBT-UHFFFAOYSA-M sodium;3,4,5,6-tetrahydroxy-2-oxohexanoate Chemical compound [Na+].OCC(O)C(O)C(O)C(=O)C([O-])=O OFCZUBZXJNUXBT-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2086—Hydroxy carboxylic acids-salts thereof
-
- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F5/00—Softening water; Preventing scale; Adding scale preventatives or scale removers to water, e.g. adding sequestering agents
- C02F5/08—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents
- C02F5/10—Treatment of water with complexing chemicals or other solubilising agents for softening, scale prevention or scale removal, e.g. adding sequestering agents using organic substances
Definitions
- sequestrant compositions comprising a mixture of (l) a compound selected from the group consisting of citric acid, tartaric acid, polyhydroxy monocarboxylic acids containing from 6 to 8 carbon atoms, and the water soluble salts of said acids and (2) a compound selected from the group consisting of polyhydroxy dicarboxylic acids containing from 5 to 8 carbon atoms and polyhydroxy monocarboxylic ketoacids containing from 6 to 8 carbon atoms and the water-soluble salts of said acids.
- This invention relates to new compositions of matter. More particularly, this invention relates to novel sequestrant compositions comprising a mixture of sequestering agents.
- Polyhydroxy acids such as gluconic acid
- gluconic acid sodium gluconate in the basic medium
- Gluconic acid is a good sequestrant for calcium ions, but it is not nearly as good as alpha-ketoglucom'c acid and the polyhydroxy polycarboxylic acids such as saccharic acid and mucic acid.
- novel compositions of the present invention comprise a mixture of (1) a compound selected from the group consisting of citric acid, tartaric acid, polyhydroxy monocarboxylic acids containing from 6 to 8 carbon atoms, and the water soluble salts of said acids and 3,696,044 Patented Oct. 3, 1972 ice (2) a compound selected from the group consisting of polyhydroxy dicarboxylic acids containing from 5 to 8 carbon atoms, polyhdroxy monocarboxylic ketoacids containing from 6 to 8 carbon atoms, and the water soluble salts of said acids.
- a preferred class of polyhydroxy monocarboxylic acids and water-soluble salts thereof which may be used as a component of the sequestering compositions of this invention includes the compounds characterized by the following generalized formula COO-X (CHOHL;
- polyhydroxy monocarboxylic ketoacids includeZ-ketogulonic acid, 2-ketogluconic acid, S-ketogluconic acid, Z-ketoglucoheptanoic acid, 3-ketogluconic acid, 4-ketogluconic acid, 3-ketogulonic acid, and 4-ketogulonic acid.
- a preferred keto acid is 2-ketogluconic acid.
- sequestering agents are employed in the free acid form or in the salt form.
- compounds (1) and (2) described above may be employed in free acid form or as a water soluble salt.
- Illustrative examples of such salts include the alkali metal and ammonium salts.
- a preferred class of salts includes the sodium and potassium salts.
- the amounts of compounds (1) and (2) described above which may be employed in the sequestering compositions of this invention may vary a wide range and will depend somewhat on the sepcific combination of sequestering agent used, on the cost of the sequestering agent, and on the particular system in which the the sequestering composition is employed.
- the weight ratio of compound 1) to compound (2) is not more than about 100 and at least about 0.05 and preferably at least about 1.
- a particularly preferred weight ratio of compound (1) to compound (2) is from about 2 to about 10.
- a preferred composition of this invention comprises a mixture of about parts by weight of gluconic acid or water-soluble salt thereof and about 25 parts by weight of saccharic acid or water-soluble salt thereof.
- the calcium sequestering ability of the various compositions is determined by the titration of 0.2 gram of the active material with one percent calcium acetate solution and three percent caustic solution in accordance with a modified version of a test described by Mchevretter et al., Industrial Engineering Chemistry, 45,2782 (1953).
- a two percent stock solution of the sequestring agent is prepared, and ten ml. of this stock solution are diluted with ml. of a six percent sodium hydroxide solution and two ml. of two percent sodium oxalate solution.
- the diluted solution is mechanically stirred, and a standard one percent calcium acetate solution is added from a syringe attached to a constant speed syringe pump until a slight haze is observed in the solution.
- the amount of calcium ion added is a measure of the sequestering power of the sequestering agent under test.
- Sodium gluconate a standard of the industry, is arbitrarily assigned a calcium ion sequestering index of 1.00.
- the calcium ion sequestering power of the other sequestrants are calculated based on sodium gluconate.
- disodium saccharate has an index of 2.72 which indicates that disodium saccharate is 2.72 times as effective as sodium gluconate.
- the calculated calcium ion sequestering power is determined by adding the theoretical calcium ion sequestering power of each component of the sequestering composition.
- the sequestering compositions of this invention may be used in any of the numerous ways known in the art for using sequestering agents.
- the sequestering compositions may be used alone or in combination with wetting agents, surfactants, detergent builders, detergent compositions, and other ingredients which are used in the art in combination with sequestering agents.
- a composition comprising a mixture of (1) a compound selected from the group consisting of citric acid, tartaric acid, polyhydroxy monocarboxylic acids containing from 6 to 8 carbon atoms, and the water soluble salts of said acids and (2) a compound selected from the group consisting of polyhydroxy dicarboxylic acids containing from 5 to 8 carbon atoms, polyhydroxy monocarboxylic ketoacids containing from 6 to 8 carbon atoms, and the water soluble salts of said acids.
- composition of claim 1 wherein the polyhydroxy monocarboxylic acid containing from 6 to 8 carbon atoms 2D has the formula COOX wherein n is an integer from 4 to 6 and wherein X is hydrogen or a cation.
- composition of claim 2 wherein the weight ratio r of compound 1) to compound (2) is at least one. 4. A composition of claim 3 wherein compound (1) has the formula HOH 40 HzOH POWER OF SODIUM SACCHARATE, SODIUM GLUCONATE, AND
- n is an integer having a value of from 4 to 6 and X is hydrogen or cation and wherein compound (2) has the formula wherein m is 3 or 4 and Q and D are independently hydrogen or cation.
- composition of claim 2 wherein the ratio of compound (1) to compound (2) is from 2 to 10.
- composition of claim 8 wherein the ratio of compound (1) to compound (2) is from 2 to 10.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental & Geological Engineering (AREA)
- Hydrology & Water Resources (AREA)
- Water Supply & Treatment (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5208870A | 1970-07-02 | 1970-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3696044A true US3696044A (en) | 1972-10-03 |
Family
ID=21975389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US52088A Expired - Lifetime US3696044A (en) | 1970-07-02 | 1970-07-02 | Sequestrant compositions |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3696044A (en, 2012) |
| JP (1) | JPS5343908B1 (en, 2012) |
| CA (1) | CA946598A (en, 2012) |
| DE (1) | DE2132509A1 (en, 2012) |
| FR (1) | FR2100198A5 (en, 2012) |
| GB (1) | GB1304979A (en, 2012) |
| IT (1) | IT1000014B (en, 2012) |
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969134A (en) * | 1971-02-12 | 1976-07-13 | Henkel & Cie G.M.B.H. | Process for using clear rinsing agents in mechanical dishwashing |
| US4000083A (en) * | 1974-05-06 | 1976-12-28 | B°V° Chemie Combinatie Amsterdam C°C°A° | Sequestering agents |
| US4032460A (en) * | 1975-10-28 | 1977-06-28 | Union Oil Company Of California | Inhibition of scale deposition in high temperature wells |
| US4049547A (en) * | 1976-04-08 | 1977-09-20 | International Minerals & Chemical Corporation | Use of chelating agents for enhancing the settling of slimes |
| US4210550A (en) * | 1978-07-14 | 1980-07-01 | Akzo N.V. | Detergent composition containing an alkali carbonate |
| US4244792A (en) * | 1980-02-26 | 1981-01-13 | Hixson Metal Finishing | Method for stripping anodized aluminum and aluminum alloys |
| US4264418A (en) * | 1978-09-19 | 1981-04-28 | Kilene Corp. | Method for detersifying and oxide coating removal |
| US4277359A (en) * | 1979-04-04 | 1981-07-07 | Mogul Corporation | Water treatment to inhibit corrosion and scale and process |
| US4317735A (en) * | 1980-03-18 | 1982-03-02 | The Dow Chemical Company | Method of inhibiting crosslinking of aqueous xanthan gums in the presence of ferric acid ions |
| US4662827A (en) * | 1984-04-25 | 1987-05-05 | Facet Enterprises, Inc. | Wet motor geroter fuel pump |
| US4724083A (en) * | 1987-05-15 | 1988-02-09 | International Minerals & Chemical Corp. | Method of preventing precipitation of metal compounds |
| US4929364A (en) * | 1987-06-19 | 1990-05-29 | Nalco Chemical Company | Amine/gallic acid blends as oxygen scavengers |
| US4941925A (en) * | 1988-02-26 | 1990-07-17 | Nalco Chemical Company | Cleaner for high pressure cleaning of ferrous and non-ferrous material |
| US4968438A (en) * | 1987-09-18 | 1990-11-06 | Nalco Chemical Company | Gallic acid as an oxygen scavenger |
| US5344590A (en) * | 1993-01-06 | 1994-09-06 | W. R. Grace & Co.-Conn. | Method for inhibiting corrosion of metals using polytartaric acids |
| US5368740A (en) * | 1993-04-23 | 1994-11-29 | Betz Paperchem, Inc. | Methods of controlling scale formation in the presence of metal ions in aqueous systems |
| US5468393A (en) * | 1993-04-23 | 1995-11-21 | Betz Paperchem, Inc. | Methods of controlling scale formation in the presence of metal ions in aqueous systems |
| US5948267A (en) * | 1994-10-07 | 1999-09-07 | Kay Chemical Company | Composition and method for inhibiting chloride-Induced corrosion and limescale formation on ferrous metals and alloys |
| US6042742A (en) * | 1994-10-07 | 2000-03-28 | Whittemore; Michael | Composition and method for inhibiting chloride-induced corrosion of and limescale formation on ferrous metals and alloys |
| US6506258B1 (en) * | 1998-02-20 | 2003-01-14 | Cooperatie Cosun U.A. | Process for controlling scale in the sugar process |
| US20030203707A1 (en) * | 1998-12-04 | 2003-10-30 | Farrow Nigel Richard | Method for removing surface coatings |
| US20050129644A1 (en) * | 2003-03-25 | 2005-06-16 | L'oreal S.A. | Use of hydroxycarboxylic acids and salts thereof as complexing agents in reducing compositions for bleaching or permanently reshaping keratin fibres |
| US7267696B2 (en) | 2003-03-25 | 2007-09-11 | L'oreal S.A. | Composition for dyeing keratinous fibers, comprising a hydroxycarboxylic acid or a salt, ready-to-use composition comprising it, implementation process and device |
| US20100111756A1 (en) * | 2008-10-31 | 2010-05-06 | General Electric Company | Compositions and methods for inhibiting corrosion in aqueous media |
| US20100111757A1 (en) * | 2008-10-31 | 2010-05-06 | General Electric Company | Methods for inhibiting corrosion in aqueous media |
| US7935665B2 (en) | 2002-04-25 | 2011-05-03 | Fujifilm Electronic Materials U.S.A., Inc. | Non-corrosive cleaning compositions for removing etch residues |
| US9315624B2 (en) | 2007-11-15 | 2016-04-19 | The University Of Montana | Hydroxypolyamide gel forming agents |
| US9346736B2 (en) | 2013-03-13 | 2016-05-24 | Rivertop Renewables, Inc. | Oxidation process |
| US9347024B2 (en) | 2011-04-21 | 2016-05-24 | Rivertop Renewables, Inc. | Calcium sequestering composition |
| US9404188B2 (en) | 2010-11-11 | 2016-08-02 | Rivertop Renewables | Corrosion inhibiting composition |
| US9670124B2 (en) | 2013-03-13 | 2017-06-06 | Rivertop Renewables, Inc. | Nitric acid oxidation process |
| US9758462B2 (en) | 2013-03-13 | 2017-09-12 | Rivertop Renewables, Inc. | Nitric acid oxidation processes |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2852828A1 (fr) * | 2003-03-25 | 2004-10-01 | Oreal | Composition de traitement des matieres keratiniques comprenant un acide hydroxycarboxylique et un agent protecteur ou conditionneur |
| JP5934341B2 (ja) * | 2011-04-21 | 2016-06-15 | リバートツプ・リニユーアブルズ・インコーポレイテツド | カルシウム封鎖組成物 |
-
1970
- 1970-07-02 US US52088A patent/US3696044A/en not_active Expired - Lifetime
-
1971
- 1971-06-29 CA CA116,939A patent/CA946598A/en not_active Expired
- 1971-06-30 DE DE19712132509 patent/DE2132509A1/de active Pending
- 1971-07-01 IT IT51340/71A patent/IT1000014B/it active
- 1971-07-01 GB GB3086571A patent/GB1304979A/en not_active Expired
- 1971-07-02 FR FR7124327A patent/FR2100198A5/fr not_active Expired
- 1971-07-02 JP JP4815571A patent/JPS5343908B1/ja active Pending
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969134A (en) * | 1971-02-12 | 1976-07-13 | Henkel & Cie G.M.B.H. | Process for using clear rinsing agents in mechanical dishwashing |
| US4000083A (en) * | 1974-05-06 | 1976-12-28 | B°V° Chemie Combinatie Amsterdam C°C°A° | Sequestering agents |
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Also Published As
| Publication number | Publication date |
|---|---|
| IT1000014B (it) | 1976-03-30 |
| DE2132509A1 (de) | 1972-01-05 |
| JPS5343908B1 (en, 2012) | 1978-11-24 |
| CA946598A (en) | 1974-05-07 |
| FR2100198A5 (en, 2012) | 1972-03-17 |
| GB1304979A (en, 2012) | 1973-01-31 |
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