USRE28325E - Oh cooh - Google Patents

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USRE28325E
USRE28325E US25882172A USRE28325E US RE28325 E USRE28325 E US RE28325E US 25882172 A US25882172 A US 25882172A US RE28325 E USRE28325 E US RE28325E
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    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/06—Inorganic compounds
    • C11D9/18—Water-insoluble compounds

Definitions

  • the present invention relates to sequestering agents and, more particularly, sequestering agents consisting of an ether chelating molecule having carboxylic acid, [phosphoric acid and/or sulfonic acid] groups thereon.
  • sequestering agents utilized up to the present time, have not proven as eflicient or as selective of particular ions as desirable in many cases.
  • sequestering agents While it has often been desirable in the separation of metals to utilize sequestering agents which show an afiinity for particular metals, such sequestering agents have not been available for all the separations desired.
  • M is selected from the group consisting of 0H COOH A I as, and
  • X, Y, and Z are selected from the group consisting of H, COOH, and OH; a, b, and c are integers of from 0 to l, at least one member of a, b, and c being 1;
  • G is selected from the group consisting of Re. 28,325 Reissued Jan. 28, 1975 COOH A, B, and D are selected from the group consisting of CH COOH, [CH SO H,] A, B and D together having no more than two of the units COOH, H, [SO H, PO H J CHOHCOOH,
  • the present compounds are more efiicient sequestering agents than are the citrates, tartrates and other similar materials.
  • the present compounds are more useful in metal separations than are the conventional amine sequestering agents, e.g. ethylene diamine tetraacetic acid, since magnesium, calcium, strontium, barium, tin, vanadium, molybdenum, uranium, ferric, and cobaltous ions show a greater affinity for oxygen electron sharing than for nitrogen electron sharing.
  • the present compounds are particularly useful in ion exchange resins for multivalent metal separations.
  • Example 1 R 0H bHoooH 0- cHi)z0-d-0 0 OH dine 0 OH
  • Example 2 CO CH CHiCO OH
  • Example 3 ethylene glycol dlmulonate
  • 160 gm. sodium carbonate (1 mole) 160 gm. of diethyl malonate (1 mole)
  • 450 gm. thiophene-free benzene distilled from sodium.
  • 160 gm. of bromine were added slowly over the course of 6 hours. The temperature was maintained at 303S C. After an additional 2 hours stirring, all of the bromine color was gone.
  • the bromodiethyl malonate was separated from salts by filtration.
  • the reactor was heated to 37 C. and the glycol feed was started. Temperature was maintained by occasional immersion in a methanol bath at 40 C. After one hour all of the diethylene glycol /6 mol) was added. After an additional 10 minutes, no further cooling was required.
  • the batch was heated over the course of one hour to 54 C.
  • the lithium adduct was a gray thick slurry-solution.
  • the bromo diethyl malonate was then started, but after onehalf hour the slurry became extremely thick. It was found that an additional 500 cc. of distilled tetrahydrofurane and a temperature of 70 C. would maintain a fluidized mixture while the additional bromomalonate was added. The bromomalonate was added at 70 C. over an 8-hour period. The mixture was cooled and exposed to the atmosphere for 24 hours in an open tray. Water was added to separate a benzene layer. This benzene layer was found to contain the lithiums parafiin wax. The remainder of the mixture was thinned with 200 cc. of methanol and filtered. cc.
  • the eflluent was evaporated and found to be malonic acid.
  • the second fraction was passed through an ion-exchange column and evaporated.
  • the product was a thick yellow liquid with some crystals.
  • the product was dissolved in acetone and the acetone evaporated.
  • the product was titrated with sodium hydroxide, found 70.3 gm. per carboxyl (77 g. theoretical).
  • the product was titrated with ferric chloride at a pH of 4, salicylic acid indicator, found l.l moles Fe ion per 310 gms. (one mole theoretically).
  • the third fraction was apparently either decarboxylated malonateglycol-malonate, or partly reacted glycol malonate.
  • Two fractions were isolated therefrom, fraction (a) insoluble in cold acetone, sodium hydroxide titre 230 gm. per carboxyl; and fraction (b) soluble in acetone, 120 gm. per carboxyl.
  • Example 12 00011 00 OH H-(J-O-(CI-hh- H OOH OOH Citric acid is reacted with HBr to form citric bromide which in turn is reacted with alkaline salicylic acid.
  • Example 16 CHBCOOH CHaCOOH
  • Example 17 Example 18 C O OH CHQC O OH 0-CHz-CH-CHr-N OOH CHaCOOH
  • M M--O-(CHX),(CHY) (CHZ) G wherein M is selected from the group consisting of X, Y, and Z are selected from the group consisting of H, COOH, and OH;
  • a, b, and c are integers of from 0 to 1, at least one member of a, b, and c being 1;
  • G is selected from the group consisting of COOII A, B, and D are selected from the group consisting of CH COOH, CH SO H, A, B and D together having no more than two of the units COOH, H, -SO H, PO H -CHOHCOOH,
  • E and F are selected from the group consisting of CH COOH, CH(COOH)z, H, -CH CH OH, -CH CH OCH CH OH,
  • p being an integer of from 0 to 2.
  • HaCCOOH 0-fL-COOH 15000011 16 The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
  • G is selected from the group consisting 0] COOH and O(CHX),,(CHY),,(CHZ),.OM
  • A, B and D are selected from the group consisting of CH COOH, CH 50,11, -COOH, --H,
  • G is selected from the group consisting ofi' COOH and O-(CHX),(CHY) (CHZ) O-M A, B and D being selected from the group consisting of -CH COOH, --COOH, H, CHOHCO0H,
  • G being selected from the group consisting of:
  • A, B and D being selected from the group consisting of: CH;COOH, CO0H, -H, CHOHCO0H, and (CHZ) (CHY) (CHX) 0-M with no more than two of the units A, B and D being (CHZ) (CHY) (CHX),,OM.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Hydrology & Water Resources (AREA)
  • General Chemical & Material Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Abstract

THEREFROM WHICH COMPRISES CONTACTING SAID LIQUID MEDIA WITH A SEQUESTERING AGENT OF THE FORMULA:

M-O-(CHX)A(CHY)B(CHZ)C-G

WHERIN M IS SELECTED FROM THE GROUP CONSISTING OF

-C(-A)(-B)-D , 2-(HO-)PHENYL ,AND 2-(HOOC-)PHENYL

X=Y=-H,-COOH Z=--OH,-COOH A=B=O,1 C=O,1 WITH AT LEAST ONE OF A, B, AND C BEING 1; G IS SELECTED FROM THE GROUP CONSISTING OF

-O-C(-A)(-B)-D , -C(-A)(-D)-Y , -O-(2-(HO-)PHENYL) ,

-O-(2-(HOOC-)PHENYL)

AND-O-(CHX)A(CHY)B(CHZ)C-O-M A,B AND D AARE SELECTED FROM THE GROUP CONSISTING OF -CH2COOH,-CH2SO3H,-COOH,-H -SO2H,-PO2H2, -CHOHCOOH,

2-(HOOC-)PHENYL , 2-(HO-)PHENYL

AND -(CHZ)C(CHY)B(CHX)A-O-M WITH NO MORE THAN TWO OF THE UNITS A, B AND D BEING -COOH,-H -SO3H, -PO3H2, -CHORCOOH,

2-(HOOC-)PHENYL , 2-(HO-)PHENYL

AND NO MORE THAN ONE OF THE UNITS A, B AN D BEING -(CHZ)C(CHY)B(CHX)A-O-M.

Description

XR RE28325 United States Patent Int. Cl. C02b 5/06 US. Cl. 210-58 14 Claims Matter enclosed in heavy brackets appears in the original patent but forms no part of this reissue specification; matter printed in italics indicates the additions made by reissue.
This is a continuation-in-part of application Serial No. 765,924, tiled October 8, 1958, and now abandoned.
The present invention relates to sequestering agents and, more particularly, sequestering agents consisting of an ether chelating molecule having carboxylic acid, [phosphoric acid and/or sulfonic acid] groups thereon.
sequestering agents, utilized up to the present time, have not proven as eflicient or as selective of particular ions as desirable in many cases. In addition, while it has often been desirable in the separation of metals to utilize sequestering agents which show an afiinity for particular metals, such sequestering agents have not been available for all the separations desired.
It is therefore an object of the present invention to overcome the disadvantages inherent in the prior art, such as those indicated above.
It is another object of the present invention to provide sequestering agents useful for the textile and soap industries in the preparation of cleaning products.
It is another object of the present invention to provide a new group of metal deactivators and carriers in both aqueous and organic solutions.
It is another object of the present invention to provide new sequestering agents.
It is another object of the present invention to provide sequestering agents which are easily and inexpensively synthesized.
It is another object of the present invention to utilize as sequestering agents, materials which comprise an ether chelating molecule having acid groups thereon.
These and other objects and the nature and advantages of the present invention will be apparent from the following description.
The compounds of the present invention fall within the general formula:
wherein M is selected from the group consisting of 0H COOH A I as, and
X, Y, and Z are selected from the group consisting of H, COOH, and OH; a, b, and c are integers of from 0 to l, at least one member of a, b, and c being 1;
G is selected from the group consisting of Re. 28,325 Reissued Jan. 28, 1975 COOH A, B, and D are selected from the group consisting of CH COOH, [CH SO H,] A, B and D together having no more than two of the units COOH, H, [SO H, PO H J CHOHCOOH,
COOH OH and no more than one unit of (CHZ) (CHY);,(CHX) O-M [E and F are selected from the group consisting of CH COOH, CH(COOH)z, H, CH CH OH, CH CH OCH CH OH on on on cmo u-' $0011 i cin).,rono
(CH SO H, and no more than one unit of omcmN and p is an integer of from 0 to 2.]
These materials are all broadly ethers and may be synthesized by the conventional ether producing reactions, such as the Williamson ether synthesis.
The present compounds are more efiicient sequestering agents than are the citrates, tartrates and other similar materials. In addition, the present compounds are more useful in metal separations than are the conventional amine sequestering agents, e.g. ethylene diamine tetraacetic acid, since magnesium, calcium, strontium, barium, tin, vanadium, molybdenum, uranium, ferric, and cobaltous ions show a greater affinity for oxygen electron sharing than for nitrogen electron sharing. In addition, the present compounds are particularly useful in ion exchange resins for multivalent metal separations.
The following specific examples are presented by way of illustration only and are not intended as limiting the invention. The compounds of Examples 1, 2, 3, 5, 6, 7, 8, 9, 10, 12 and 13 are produced by the Williamson ether synthesis and when tested provide good sequestering agents.
Example 1 R 0H bHoooH 0- cHi)z0-d-0 0 OH dine 0 OH Example 2 CO CH CHiCO OH Example 3 ethylene glycol dlmulonate To a. three-neck flask, fitted with stirrer, dropping funnel, thermometer, and N, inlet was charged 160 gm. sodium carbonate (1 mole), 160 gm. of diethyl malonate (1 mole) and 450 gm. thiophene-free benzene distilled from sodium. 160 gm. of bromine were added slowly over the course of 6 hours. The temperature was maintained at 303S C. After an additional 2 hours stirring, all of the bromine color was gone. The bromodiethyl malonate was separated from salts by filtration. To another three-neck flask fitted with stirrer, thermometer, nitrogen inlet, reflux condenser and dropping funnel, was charged 1 mole of lithium dispersion in wax and 250 cc. of sodium dried benzene. Diethylene glycol dried 8 hours in a 60 C. vacuum oven was then added dropwise. The reactor was heated to 37 C. and the glycol feed was started. Temperature was maintained by occasional immersion in a methanol bath at 40 C. After one hour all of the diethylene glycol /6 mol) was added. After an additional 10 minutes, no further cooling was required. The batch was heated over the course of one hour to 54 C. The lithium adduct was a gray thick slurry-solution. The bromo diethyl malonate was then started, but after onehalf hour the slurry became extremely thick. It was found that an additional 500 cc. of distilled tetrahydrofurane and a temperature of 70 C. would maintain a fluidized mixture while the additional bromomalonate was added. The bromomalonate was added at 70 C. over an 8-hour period. The mixture was cooled and exposed to the atmosphere for 24 hours in an open tray. Water was added to separate a benzene layer. This benzene layer was found to contain the lithiums parafiin wax. The remainder of the mixture was thinned with 200 cc. of methanol and filtered. cc. of 20% hydrogen peroxide was added, stirred in, 300 cc. water was then stirred in and the mix allowed to settle for 18 hours. The upper layer was discarded and the lower layer was hydrolyzed with a solution of 90 gm. sodium hydroxide, 90 gm. water, 200 cc. methanol. The mixture exothermed and was allowed to stand 18 hours. Water was added to dissolve the mixture and the mixure was heated. The 600 cc. of solution was filtered and heated an additional 4 hours at 60-70 C. Alcohol was then added continuously and three fractions were filtered off. The least soluble fraction was passed through an acidified Dowex 50 (sulfonated polystyrene) ion exchange column. The eflluent was evaporated and found to be malonic acid. The second fraction was passed through an ion-exchange column and evaporated. The product was a thick yellow liquid with some crystals. The product was dissolved in acetone and the acetone evaporated. The product was titrated with sodium hydroxide, found 70.3 gm. per carboxyl (77 g. theoretical). The product was titrated with ferric chloride at a pH of 4, salicylic acid indicator, found l.l moles Fe ion per 310 gms. (one mole theoretically). The third fraction was apparently either decarboxylated malonateglycol-malonate, or partly reacted glycol malonate. Two fractions were isolated therefrom, fraction (a) insoluble in cold acetone, sodium hydroxide titre 230 gm. per carboxyl; and fraction (b) soluble in acetone, 120 gm. per carboxyl.
4 [Example 5 Clip- H CH COOH Example 6 CHnP 03H,
HO O C- O(CH;)1N
HzCOOH CHaS OaH Example 7 CHaCHa-N CH COOH Example 8 CHzCHzO CHzCHzOH [Example 9 Example 10 CHICHI OH Example 11 COOH COOH This compound is found to have good sequestering properties.
Example 12 00011 00 OH H-(J-O-(CI-hh- H OOH OOH Citric acid is reacted with HBr to form citric bromide which in turn is reacted with alkaline salicylic acid.
CONa HOH Br- COOH H2 COOH COOH ail-C OOH -O-C-COOH NaOH NaBr The compounds of the following Examples 15 and 17 are also prepared by the Williamson ether synthesis and are found to be excellent sequestering agents:
Example 16 CHBCOOH CHaCOOH Example 17 Example 18 C O OH CHQC O OH 0-CHz-CH-CHr-N OOH CHaCOOH It will be obvious to those skilled in the art that various changes may be made without departing from the spirit of the invention and therefore the invention is not limited to what is described in the specification, but only as indicated in the appended claims.
What is claimed is:
[1. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
M--O-(CHX),(CHY) (CHZ) G wherein M is selected from the group consisting of X, Y, and Z are selected from the group consisting of H, COOH, and OH;
a, b, and c are integers of from 0 to 1, at least one member of a, b, and c being 1;
G is selected from the group consisting of COOII A, B, and D are selected from the group consisting of CH COOH, CH SO H, A, B and D together having no more than two of the units COOH, H, -SO H, PO H -CHOHCOOH,
and no more than one unit of E and F are selected from the group consisting of CH COOH, CH(COOH)z, H, -CH CH OH, -CH CH OCH CH OH,
'(CH2) PO3H2, (CHQ)DSO3H, and E and F [O- gether having no more than one unit of -crncH,N
p being an integer of from 0 to 2.]
2. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
3. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
COOH
CHaCOOH H- -O(CHCOOH);O H
HaCOOH therefrom which comprises contacting said media with a sequestering agent of the formula:
[6. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
CH PO;H:
H H OCHOHN OH HICOOH CH OOOH [7. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
[8. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
COOH
H -o cu) 2- H crncoon oon ClhCH -N CH(COOH):
[9. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
C O O H CHACHQ O CH CHaOH HO-O-(CHOHh-N OOH CH;
[10. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
8 [11. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
CHsCOOH JOOH): CHICOOH 12. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
COOH COOH 13. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
COOH C OOH H-JJ-O-(Clhh- H OOH OOH 14. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
15. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
OOOH
HaCCOOH 0-fL-COOH 15000011 16. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
CHgC OOH 0-CHz-CHy-O-C-C O OH CHgCOOH [17. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
coon orneoon nd-o-cm-oa-cmn on H cmooon 18. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
v 9; Q a [1-9. The method of treating liquid media to chelate ions therefrom which comprises contacting said media with a sequestering agent of the formula:
COOH
CH, C 0H 5 O-Cm-C H CH,-N
O OH CH: C O OH 20. The method of treating a liquid media to chelate ions therefrom which comprises contacting said liquid media with a sequestering agent of the formula:
MO-(CHX),,(CHY) ,(CHZ) G wherein M is selected from the group consisting of OH 000H 2 B, and i X Y=--H, COOH Z =-OH -C OOH a: b =0, 1 c=0, 1
with at least one of a, b and c being I; G is selected from the group consisting 0] COOH and O(CHX),,(CHY),,(CHZ),.OM
A, B and D are selected from the group consisting of CH COOH, CH 50,11, -COOH, --H,
-SO H, PO H CHOHCOOH,
COOH OH and -(CHZ) (CHY);,(CHX) -0M with no more than two of the units A, B and D being CO0H, -H -S0 H, PO H --CHOHCOOH,
C0 OH OH iii) MO(CHX) )CHY) (CHZ) -G wherein M is selected from the group consisting of 1 0 a b 0, 1 0:0, I
with at least one of a, b and c being I; G is selected from the group consisting ofi' COOH and O-(CHX),(CHY) (CHZ) O-M A, B and D being selected from the group consisting of -CH COOH, --COOH, H, CHOHCO0H,
COOH OH iii) and -(CHX),,(CHY) ,(CHZ) OM with no more than two units of A, B and D being --CO0H, H CHOHCO0H,
COOH 0H s w s and no more than one unit of A, B and D being -(CHZ) (CHY) ,(CHX) OM.
22. The method of treating a liquid media to chelate ions therefrom which comprises contacting said liquid media with a sequestering agent of the formula:
wherein M is A l F B X Y=H. COOH; Z=OH, CO0H; a=b=0, 1 0:0, I
with at least one of a, b and c being I; G being selected from the group consisting of:
and 0-(CHX),,(CHY];,(CHZ) -O-M A, B and D being selected from the group consisting of: CH;COOH, CO0H, -H, CHOHCO0H, and (CHZ) (CHY) (CHX) 0-M with no more than two of the units A, B and D being (CHZ) (CHY) (CHX),,OM.
23. The method of treating a liquid media to chelate ions therefrom which comprises contacting said liquid media with a sequestering agent of the formula:
M-ocHx cHY cHz ,-o
wherein M is 1 1 X: Y=H; Re. 22,352 g 1 2,936,242 1 3,128,287 with at least I of a, b and 0 being I; 59,418 A, B and D being selected from the group consisting 2,240,957 of: -H, -CO0H, -CH;COOH, with no more 2,311,003 than two of the units A, B and D being the same; 3 G being selected from the group consisting of 2,727,867 2,868,724 2,894,905 3,130,153 3 1 3,234,124 -Y, -0- -B,
References Cited The following references, cited by the Examiner, are of record in the patented file of this patent or the original patent.
12 UNITED STATES PATENTS Teeters 102-1 Brauer 106-35 Berg 252-351 X Lawrence 210-58 Munz 252-117 Tucker 210-58 Ryznar 252-321 Denman 252-321 Zech 210-58 Bernard 210-58 Keller 210-58 Irani 210-38 FOREIGN PATENTS 6/1939 Germany.
US. Cl. X.R.
252-180, 189; 260-429 I, 507 R, 513 N, 519, 520,
THOMAS G. WYSE, Primary Examiner
US25882172 1958-10-08 1972-06-01 Oh cooh Expired USRE28325E (en)

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US76592458A 1958-10-08 1958-10-08
US356629A US3293176A (en) 1964-04-01 1964-04-01 Method of chelating with an ethergroup-containing sequestering agent
US25882172 USRE28325E (en) 1958-10-08 1972-06-01 Oh cooh

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4143125A (en) 1976-12-27 1979-03-06 Monsanto Company Calculus-inhibiting compositions and method
US4182905A (en) 1974-05-17 1980-01-08 Monsanto Company Chemical compounds
US4663071A (en) 1986-01-30 1987-05-05 The Procter & Gamble Company Ether carboxylate detergent builders and process for their preparation
US4798907A (en) 1988-02-26 1989-01-17 The Procter & Gamble Company Controlled temperature process for making 2,2'-oxodisuccinates useful as laundry detergent builders

Citations (13)

* Cited by examiner, † Cited by third party
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US22352A (en) * 1858-12-21 And james r
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