WO1996003644B1 - Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof - Google Patents
Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereofInfo
- Publication number
- WO1996003644B1 WO1996003644B1 PCT/US1995/008809 US9508809W WO9603644B1 WO 1996003644 B1 WO1996003644 B1 WO 1996003644B1 US 9508809 W US9508809 W US 9508809W WO 9603644 B1 WO9603644 B1 WO 9603644B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- distance
- chelate
- formula
- compound
- contacting
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims 4
- 150000001509 aspartic acid derivatives Chemical class 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract 26
- 239000013522 chelant Substances 0.000 claims abstract 22
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 229910021645 metal ion Inorganic materials 0.000 claims abstract 7
- 238000004061 bleaching Methods 0.000 claims abstract 4
- 229910052751 metal Inorganic materials 0.000 claims abstract 4
- 239000002184 metal Substances 0.000 claims abstract 4
- 238000005406 washing Methods 0.000 claims abstract 4
- 239000002253 acid Substances 0.000 claims abstract 3
- 238000004140 cleaning Methods 0.000 claims abstract 3
- 230000008021 deposition Effects 0.000 claims abstract 3
- 238000007747 plating Methods 0.000 claims abstract 3
- 102000004190 Enzymes Human genes 0.000 claims abstract 2
- 108090000790 Enzymes Proteins 0.000 claims abstract 2
- 229910019142 PO4 Inorganic materials 0.000 claims abstract 2
- 238000006065 biodegradation reaction Methods 0.000 claims abstract 2
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 230000006866 deterioration Effects 0.000 claims abstract 2
- 238000002845 discoloration Methods 0.000 claims abstract 2
- 238000005553 drilling Methods 0.000 claims abstract 2
- 239000007789 gas Substances 0.000 claims abstract 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 235000015097 nutrients Nutrition 0.000 claims abstract 2
- 230000003647 oxidation Effects 0.000 claims abstract 2
- 238000007254 oxidation reaction Methods 0.000 claims abstract 2
- 239000003208 petroleum Substances 0.000 claims abstract 2
- 235000021317 phosphate Nutrition 0.000 claims abstract 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims abstract 2
- 229920000642 polymer Polymers 0.000 claims abstract 2
- 238000011084 recovery Methods 0.000 claims abstract 2
- 230000006641 stabilisation Effects 0.000 claims abstract 2
- 238000011105 stabilization Methods 0.000 claims abstract 2
- 239000004753 textile Substances 0.000 claims abstract 2
- 239000003599 detergent Substances 0.000 claims 7
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 6
- 229910052802 copper Inorganic materials 0.000 claims 6
- 239000010949 copper Substances 0.000 claims 6
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 claims 6
- 239000012530 fluid Substances 0.000 claims 4
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000000243 solution Substances 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- -1 carboxyl hydroxy groups Chemical group 0.000 claims 2
- 150000001879 copper Chemical class 0.000 claims 2
- 229910001431 copper ion Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 238000000367 ab initio method Methods 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 150000003863 ammonium salts Chemical class 0.000 claims 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N aspartic acid group Chemical group N[C@@H](CC(=O)O)C(=O)O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
- 239000007844 bleaching agent Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- MMCOUVMKNAHQOY-UHFFFAOYSA-N carbonoperoxoic acid Chemical group OOC(O)=O MMCOUVMKNAHQOY-UHFFFAOYSA-N 0.000 claims 1
- 125000002091 cationic group Chemical group 0.000 claims 1
- 239000008139 complexing agent Substances 0.000 claims 1
- 229910001447 ferric ion Inorganic materials 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 claims 1
- 238000004458 analytical method Methods 0.000 abstract 1
Abstract
Chelants represented by formula (Ib) are determined to be biodegradable when Distance A is from 3.8 x 10-10 to 4.6 x 10-10m, Distance B is from 5.1 x 10-10 to 5.9 x 10-10m, and Distance C is from 4.3 to 6.7 x 10-10m. Compounds meeting these criteria are referred to as compounds of Formula 2. In addition to methods of analysis and computer systems therefor, the invention includes a method of chelating a metal ion to form a chelate and biodegrading the chelate comprising step (a) contacting the metal ion with at least one compound of Formula 2 to form a chelate and (b) contacting the resultant chelate or chelant with microbes of the type specified in ASTM 2667-89, ISO 5815 or effective enzymes thereof under conditions and for a time sufficient for biodegradation wherein either (i) the chelate formed in step (a) is formed in a process of removing deposits, scale, or rust; cleaning or washing; controlling metal initiated or catalyzed oxidation or deterioration including spoilage, discoloration, or rancidification; textile treatment; paper making; stabilization of polymers or phosphates; or petroleum drilling, production or recovery; or (ii) the chelate formed in step (a) is before step (b) used as a redox catalyst, in a process of photographic bleaching, bleach-fixing or developing; in electroless deposition or plating; in removing acid or oxide gases including H¿2?S, NOx, SOx, CO and CO2; or in providing agricultural nutrients.
Claims
1. An analytical process for determining
biodegradability of compounds having a moiety of the formula:
wherein each of R2 is independently hydrogen or an unsubstituted alkyl, aryl, alkaryl, or aralkyl group or an alkyl, aryl, alkaryl, or aralkyl group substituted witn a hydroxyl, carboxyl, sulfonyl, phosphoryl, amino, imide, or amino group and wherein the distance between the carboxyl carbon atoms is designated "Distance A", the distance between carboxv 1 double bonded oxygen atoms is designated "Distance B", and the distance between carboxyl hydroxy oxygen atoms is designated "Distance C" comprising: determining from computer computations, in at least one energetically feasible conformation of a compound having a moiety of Formula la, that the compound is biodegradable when all of the following conditions are met:
(a) Distance A is within a range of from about 3.81 x 10-10 m to about 3.66 x 10-10 m;
(b) Distance B is within a range of from about 5.13 x 10-10 m to about 5.52 x 10-10 m;
(c) Distance C is within a range of from about 5.28 x 10-10 m to about 6.09 x 10-10 m; and
(d) the lowest unoccupied molecular orbital, hereinafter referred to as LUMO, is on at least one carboxyl carbon atom of the moiety of Formula la.
2. The process of Claim 1 wherein each of R2 are independently methyl or hydrogen.
3. The process of Claim 1 wherein the determination of the energetically feasible conformations is performed by computerized computations using semiclassical, semiempirical, or ab initio methods.
4. The process of Claim 3 wherein the energetically feasible conformations are input into a programmed digital computer having a means for determining Distance A, Distance B and Distance C and comparing them with the ranges specified in steps (a), (b), and (c) .
5. A computer system comprising:
(a) means for, in a molecular structure of a compound having a moiety of Formula la, wherein the distance between the carboxyl carbon atoms is designated "Distance A", the distance between carboxyl double bonded oxygen atoms is designated
"Distance B", and the distance between carboxyl hydroxy groups "Distance C", ascertaining Distance A, Distance B and Distance C in at least one energetically feasible conformation of the compound;
(b) means for determining whether Distance A is at least about 3.81 x 10- 10 m but less than or equal to about 3.86 x 10-10 m;
(c) means for determining whether Distance B is at least about 5.13x 10- 10 m but less than or equal to about 5.52 x 10- 10 m; and
(d) means for determining whether Distance C is at least about 5.28 x 10- 10 m but less than or equal to about 6.09 x 10- 10 m; and
(e) means for determining whether the lowest unoccupied molecular orbital, hereinafter referred to as LUMO, is on at least one carboxyl carbon atom of the aspartic acid group.
6. The computer system of Claim 5 additionally comprising an output means for outputting at least an indication of a compound found to have Distance A, Distance B and Distance C within their respective ranges stated in Steps (b), (c) and (d) respectively.
7. The computer system of Claim 6 further comprising a means for changing the structure.
8. A method of chelatmg a metal ion to form a chelate and biodegrading the chelate comprising step (a) contacting the metal ion with at least one compound having a moiety of Formula la wherein Distance A is at least about 3.81 x 10- 10 m but less than or equal to about 3.86 x 10- 10 m; Distance B is at least about 5.13 x 10- 10 m but less than or equal to about 5.52 x 10- 10 and Distance C is at least about 5.28 x 10- 10 m but less than or equal to about 6.09 x 10-10 m; and the lowest unoccupied molecular orbital, hereinafter referred to as LUMO, is on at least one carboxyl carbon atom of the moiety of Formula la, such compounds hereinafter referred to as compounds of Formula 2, to form a chelate and (b) contacting the resultant chelate or chelant with microbes of the type specified in ASTM 2667-85, ISO 5815 or effective enzymes thereof under conditions and for a time sufficient for biodegradation wherein either (I) the chelate formed in step (a) is formed in a process of cleaning or washing; removing deposits, scale, or rust; controlling metal initiated or catalyzed oxidation or deterioration including spoilage, discoloration, or rancidification; textile treatment; paper making; stabilization of polymers or phosphates; or petroleum drilling, production or recovery; or (n) the chelate formed in step (aj is before step (b) used as a redox catalyst, in a process of photographic bleaching, bleach-flxing or developing; in electroless deposition or plating; in removing acid or oxide gases including H2S, NCx, SOx, CO and CO2; or in providing agricultural nutrients.
9. The method of Claim 8 wherein the metal ion is ferric ion and wherein after step (a) and before step (b), the resulting ferric chelate of Formula 2 is used in bleaching or bleach-flxing an exposed color photographic material which includes contacting said material with a bleaching or bleach- fixing solution containing a bleaching agent comprising tne ferric chelate.
10. The method of Claim 8 wherein the metal ion is copper ion and wherein after step (a) and before step (b), the resulting copper chelate is used in a process of electroless deposition of copper upon a non-metallic surface receptive to the deposited copper including a step of contacting the non-metallic surface with an aqueous solution comprising a soluble copper salt and a compound of Formula 2.
11. The method of Claim 8 wherein the metal ion is copper ion and wherein after step (a) and before step (b), the resulting copper chelate is used in a process cf electroless copper plating which comprises immersing a receptive surface to be plated in an alkaline, autocatalytic copper bath comprising water, a water soluble copper salt, and a complexing agent which is a compound of Formula 2 for cupric ion.
12. The method of Claim 8 wherein step (a) occurs in a process for removing iron oxide deposits from a surface including a step of contacting the deposits with a solution comprising an ammoniated compound of Formula 2.
13. A method of Claim 8 wherein step (a) occurs in a process for cleaning a hard surface comprising contacting the surface with a composition of a compound of Formula 2.
14. The method of Claim 13 wherein the composition additionally contains an organic solvent having a boiling point of at least about 90°C.
15. The method of Claim 8 wherein step (a) occurs m a process for washing articles which comprises contacting the articles with an aqueous washing system consisting essentially cf water, an organic detergent surfactant selected from the group consisting of anionic detergents, cationic detergents, nonionic detergents, ampholytic detergents, zwitterionic detergents, and mixtures of such detergents and at least one water-soluble salt of an acid of Formula 2 selected from the group consisting of alkali metal salts, ammonium salts, and alkyl ammonium salts.
16. A method of Claim 8 wherein after step (a) and before step (b) the chelate is used in a process of removing H2S from a fluid comprising contacting said fluid with an aqueous solution at a pH suitable for removing H2S wherein said solution contains at least one higher valence polyvalent metal chelate of a compound of Formula 2.
17. A method of Claim 8 wherein after step (a) and before step (b) the chelate is used in a process of removing NOx from a fluid comprising contacting the fluid with an aqueous solution of at least one lower valence state polyvalent metal chelate of Formula 2.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ290516A NZ290516A (en) | 1994-07-27 | 1995-07-14 | An analytical process using computer software for determining the biodegradability of aspartic acid derivatives; chelating a metal ion then biodegrading the chelate |
| JP50578596A JP3504668B2 (en) | 1994-07-27 | 1995-07-14 | Determination of biodegradability of aspartic acid derivatives, biodegradable chelants, their use and compositions |
| CA002194184A CA2194184C (en) | 1994-07-27 | 1995-07-14 | Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof |
| DE69515671T DE69515671T3 (en) | 1994-07-27 | 1995-07-14 | DETERMINATION OF BIODEGRADABILITY OF ASPARAGIC ACID DERIVATIVES, DEGRADABLE CHELATE FORMATORS, USES AND COMPOSITIONS THEREOF |
| EP95927158A EP0772771B2 (en) | 1994-07-27 | 1995-07-14 | Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof |
| AU31270/95A AU697099C (en) | 1994-07-27 | 1995-07-14 | Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof |
| MX9700622A MX9700622A (en) | 1994-07-27 | 1995-07-14 | Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28106094A | 1994-07-27 | 1994-07-27 | |
| US08/281,060 | 1994-07-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996003644A1 WO1996003644A1 (en) | 1996-02-08 |
| WO1996003644B1 true WO1996003644B1 (en) | 1996-02-29 |
Family
ID=23075779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1995/008809 WO1996003644A1 (en) | 1994-07-27 | 1995-07-14 | Determining biodegradability of aspartic acid derivatives, degradable chelants, uses and compositions thereof |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US5776763A (en) |
| EP (2) | EP0772771B2 (en) |
| JP (1) | JP3504668B2 (en) |
| DE (1) | DE69515671T3 (en) |
| ES (1) | ES2143060T5 (en) |
| MX (1) | MX9700622A (en) |
| NZ (1) | NZ290516A (en) |
| WO (1) | WO1996003644A1 (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0968658A1 (en) * | 1998-07-02 | 2000-01-05 | Akzo Nobel N.V. | Feed additives comprising ethylene diamine disuccinic acid as a chelant |
| WO2002010741A2 (en) * | 2000-07-28 | 2002-02-07 | Lion Bioscience Ag | Regional intestinal permeability model |
| AU2001278056A1 (en) * | 2000-07-28 | 2002-02-13 | Lion Bioscience Ag | System and method for predicting adme/tox characteristics of a compound |
| EP2013324A2 (en) * | 2006-04-21 | 2009-01-14 | Dow Global Technologies Inc. | Formulations with unexpected cleaning performance incorporating a biodegradable chelant |
| MX324478B (en) | 2008-04-28 | 2014-10-14 | Dow Global Technologies Inc | Polyalkylene glycol lubricant composition. |
| RU2687174C1 (en) * | 2018-06-13 | 2019-05-07 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Санкт-Петербургский государственный технологический институт (технический университет)" | Method of determining resistance of organic polymers to degradation induced by various factors |
| US11525086B2 (en) | 2019-05-06 | 2022-12-13 | Gpcp Ip Holdings Llc | Paper sheet mulches and methods of making the same |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3158635A (en) * | 1959-03-18 | 1964-11-24 | Stauffer Chemical Co | Bis-adduction products and methods of preparing same |
| DK17885D0 (en) * | 1985-01-14 | 1985-01-14 | Karlsson Karl Anders | ANTIVIRAL AGENT |
| US4704233A (en) † | 1986-11-10 | 1987-11-03 | The Procter & Gamble Company | Detergent compositions containing ethylenediamine-N,N'-disuccinic acid |
| US4855931A (en) * | 1988-03-25 | 1989-08-08 | Yale University | Stochastic method for finding molecular conformations |
| JPH02151650A (en) * | 1988-12-02 | 1990-06-11 | Polyplastics Co | Thermoplastic polyester resin composition |
| EP0431189A4 (en) * | 1989-06-30 | 1992-04-22 | Hitachi, Ltd. | Method of assisting material design and apparatus therefor |
| CA2002536C (en) * | 1989-11-08 | 1996-02-20 | Peter H. Buist | Dynamic molecular model |
| HUT65361A (en) * | 1989-12-29 | 1994-05-02 | Univ Technologies Int | Method for modelling tertiary structures of biologically active ligands including agonists and antagonists thereto and novel synthetic antagonists based on angiotensin |
| US5220055A (en) * | 1990-10-23 | 1993-06-15 | Nippon Shokubai Co., Ltd. | Process for producing aminocarboxylic acid salts |
| CZ90793A3 (en) † | 1990-11-14 | 1994-06-15 | Procter & Gamble | Preparations free of phosphates and with oxygen-containing bleaching systems for automatic dish washers, and process for preparing thereof |
| US5362412A (en) * | 1991-04-17 | 1994-11-08 | Hampshire Chemical Corp. | Biodegradable bleach stabilizers for detergents |
| US5208369A (en) * | 1991-05-31 | 1993-05-04 | The Dow Chemical Company | Degradable chelants having sulfonate groups, uses and compositions thereof |
| JP3086979B2 (en) † | 1992-02-17 | 2000-09-11 | コニカ株式会社 | Bleaching solution or bleach-fixing solution and processing method of silver halide color photographic light-sensitive material using these processing solutions |
| DE4211713A1 (en) † | 1992-04-08 | 1993-10-14 | Basf Ag | New amino di:carboxylic-N,N-di:acetic acid deriv., useful as complexing agents - is prepd. from amino di:carboxylic acids, formaldehyde and hydrocyanic acid, or alkali metal cyanide, with amino di:carboxylic acid-N,N-di:acetonitrile as intermediate |
| GB9216408D0 (en) † | 1992-08-01 | 1992-09-16 | Procter & Gamble | Stabilized bleaching compositions |
-
1995
- 1995-07-14 EP EP95927158A patent/EP0772771B2/en not_active Expired - Lifetime
- 1995-07-14 DE DE69515671T patent/DE69515671T3/en not_active Expired - Lifetime
- 1995-07-14 MX MX9700622A patent/MX9700622A/en unknown
- 1995-07-14 ES ES95927158T patent/ES2143060T5/en not_active Expired - Lifetime
- 1995-07-14 EP EP99115425A patent/EP0959352A1/en not_active Ceased
- 1995-07-14 NZ NZ290516A patent/NZ290516A/en not_active IP Right Cessation
- 1995-07-14 JP JP50578596A patent/JP3504668B2/en not_active Expired - Lifetime
- 1995-07-14 WO PCT/US1995/008809 patent/WO1996003644A1/en active IP Right Grant
-
1996
- 1996-03-04 US US08/607,253 patent/US5776763A/en not_active Expired - Lifetime
-
1997
- 1997-09-18 US US08/932,972 patent/US5854060A/en not_active Expired - Lifetime
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