CA1217205A - Modified alkylenediamine or polyalkylenepolyamine composition and aqueous hydraulic cement slurry employing the composition - Google Patents

Modified alkylenediamine or polyalkylenepolyamine composition and aqueous hydraulic cement slurry employing the composition

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Publication number
CA1217205A
CA1217205A CA 466497 CA466497A CA1217205A CA 1217205 A CA1217205 A CA 1217205A CA 466497 CA466497 CA 466497 CA 466497 A CA466497 A CA 466497A CA 1217205 A CA1217205 A CA 1217205A
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Patent type
Prior art keywords
composition
molecular weight
fluid loss
mixture
average molecular
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Expired
Application number
CA 466497
Other languages
French (fr)
Inventor
Stephen B. Willis
Pamela J. Boyce
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Dow Chemical Co
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Dow Chemical Co
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Classifications

    • CCHEMISTRY; METALLURGY
    • C04CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04BLIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/24Macromolecular compounds
    • C04B24/28Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • CCHEMISTRY; METALLURGY
    • C04CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04BLIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/12Nitrogen containing compounds organic derivatives of hydrazine
    • C04B24/121Amines, polyamines
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/02Polyamines
    • C08G73/0206Polyalkylene(poly)amines
    • C08G73/0213Preparatory process
    • C08G73/022Preparatory process from polyamines and epihalohydrins

Abstract

ABSTRACT OF THE DISCLOSURE
A modified alkylenediamine or polyalkylene-polyamine composition and use of the composition as a fluid loss additive in aqueous hydraulic cement slurries, as a flocculant for water purification, in the treatment of liquid waste, or in the mining industry for the flocculation of solid particles in water or other aqueous media.

Description

;~5 1-- , A MODIFIED ALKYLENEDIA~INE OR
POLYALKYLENEPOLYAMINE COMPOSITION AND
AQUEOUS HYDRAULIC CEM~NT SLURRY
EMPLOYING THE COMPOSITION

The present inverltion resides in a modified alkylenediamine or polyalkylenepolya~ine composition.
The composition is suitable for use as a fluid loss additive in a~ueous hydraulic cement slurry compositions or as a flocculant for water purification, liquid waste treatment, or in the mining industry where such flocculants are added to suspension of solid particles (fines) in water or other agueous media (pulps) to cause the individual particles to collect in th~ form of blocks.

~ ydraulic cements, i.e., any inorganic cement that hardens or sets under water, are customarily admixed with water and e~placed as aqueous slurries.
The amount of water employed may vary rather exten-sively depending largely upon the fluidity o~ theslurry r~quired and upon the necessary ultimate strength. In a great many uses of a hydraulic cement it i5 necessary for the cement slurry to be emplaced within or next to a porous m~dium, for example, earthen strata! e.g., in the cementing off of borehol s, grouting, 31,134B-F

2--dam and tunnel construction and the like. When such is the casa, water filtexs out of the slurry and into the strata during the se~ting period. When ~is occurs to any appreciable extent there usually results an uncon-trolled setting rate, improper placement, impairedstrength properties and usually a contamination of the surrounding strata. All of these undesirable conditions are especially to be avoided in cementing opera~ions associated with oil, gas, water or brine wells. In an effort to lessen the loss of fluid from an aqueous h~draulic cement slurry various materials have been employed. One such material comprises a polyamine compound selected from the polyalkyleneimines, polyalkylenepolyamines or mixtures thereof. A
description of these polyamine compounds and their use in hydraulic cement slurries is taught, for example, in U.S. Patent No. 3,491,049. Although these polyamine compounds are quite satisfactory in environments wherein the temperature of the hydraulic cement slurry does not increase to above about g3C (200F), the fluid loss characteristics of these cement slurries are unacceptable at higher temperatures. U.S. 4,131,578 discloses fluid loss additive compositions suitable for use at tempexatures of 93C (200F) and above.

The composition of the present invention is a~vantageously employed as a fluid loss additive in a cement slurry and is more efficient, i.e. it requires less of the active additives to achieve the same level o water loss or, at the same level of active additives, less water loss occurs while also providing more stable, non-settling, cement slurries.

31,134B-F -2-~7;~i ~3-The present invention particularly resides in a modified alkylenediamine ox polyalkylenepolyamine composition comprising the product resulting from reactillg a modified alkylenediamine or polyalkylene-polyamine composition, characterized in that thecomposition is the reaction product resulting from reacting ~A) at least one of (1) at least one alkylenediamine or ` polyalkylenepolyamine composition having an average molecular weight o~ from 60 to 500;
(2) at least one composition prepared by reacting (a) a polyalkylenepolyamine compo-sition having an average molecular weight of from 60 to 500 with (b) at least one alkylene dihalide;
wherein ~omponent (A-2-a) and component (A-2-b~ are reacted in quantities such that the quantity of (A-2-b) used is less ~han the amount needed to .form a gel by an amount (e~pressed as weight of carbon and hydxogan contained in (A-2-b) of from 0.8% to 5% of the weight of car~on plus .
hydrogen plus nitrogen prese~t in the reaction mixtuxe when a gel would be formed;

(3) mixtures of (1) and ~2); with 31,134B-F -3-~2~72~
--4~

( B ) at least one o f (1) ~ epiphalohydrin ox dihalodxin, n adduct o~
~a~ a~ epihalohydrin or di}lalo-hydrin and ~b ) an ~lklenediamine, poly alkylenepQlyarnine having an a~rexage molec~lar wei~ht of - from 60 to 500 tv mixtu:r~s thereoî;
(3) a mixture of ~a) at least one epihalohydrin, dihalohydrin or mixture thereof;
and (b) at least orle alkylena dih~lide, or (43 a mixt~re o: at least one of (2) and (3 ); and ( ::3 optionally, one or ~ore adduc~s of 51) at least on~s epihalohydrin, d:Lhalo-}~ydrin or mixture thereof; and ( 2 ~ at l~ast one alkylenediamine or polyalk~lenepolyamine haYing an avera~e molecular weight of from 60 to 500 or a mixture thereo~; and wherein compone~ts (A), (B) and ~C) are employe~ in ~uantitie~ ~hich pro~vide a non-gell~d polyamine which gi~en a 1uid loss o~ l~ss than about 60 ml according to tha ~PI R~P 1013 fluid loss ~est. This test is described in the examples.

The i~vention al~o resides in an aqueous hydraulic ceme~t lurry composition comprisins water~
hydra~lic cement, sur~actant and polyalkylenepolyamine 31,134B-F -4_ fluid loss additive; characterized by employing as said fluid loss additive, at least one composition prepared by reacting (A) at least one of (1) at least one alkylenediamine or polyal~ylenepolyamine composition having an average molecular weight of ~rom 60 to 500;
~2) at least one composition prepared by reacting ~a) a polyalkylenepolyamine compo-sition having an average molecula.~ weight of from 60 to 500 with (b) at least one alkylene dihalide;
wherein component ~A-2-a~ and component (A-2-b) are reactPd in qua~tities such that the ~uantity of (A-2-b) used is less than the amount needed to form a gel by an amo~unt (expressed as weight of carbon and hydrogen contained in (A 2-b) of from 0.8% to 5% of the weight of carbon plus hydrogen plus nitrogen present in the reaction mi.xture when a gel would be formed;
(3) mixtures of (1) and (2); with (B) at least one of (1) an epiphalohydrin or dihalodrin, (2) an adduct of (a) an epihalohydrin or dihalo-hydrin and 31,134B-F -5-.

2~7;i~
--6~

(b) an alklenediamine, poly-alkylenepolyamine ha~ing an a~erage molecular weight of from 60 to 500 to mixtures ther~of;
(3) a mixtux of (a~ at least one epihalohydri~t dihalohydrin or mixture ~hereo.;
and (b) at least one alkylene dihalide;
or ~4) mix ures thereof; and ~C) optio~ally, one or more adducts of (1) at least one ~pihalohydrin, dihalo-hydrin or mixture thereof, and (2~. at least one alk~lenediami~e or polyalkyle~epolyamine having an average moleeular weight of from 60 to 500 or a mix~ure thereof; and wherein components (A), ~) a~d (C) are employed in g~antities which provide a non-gelled polyamine which give~ a ~luid lo~s of les~ than about 60 ml according to the ~PI R~ lOB ~luid loss test. ~hls test is de~cxib~d in the examples.

Preferably, compone~ts ~A-l), (~-2-0) and (A-2~b) independently have an a~erage molecular weight of from 150 to 350 and tC-2) has an average molecular weight o~ from 60 to 350; components (B-l~ or (B-2-a) or (B-3 a) or (C-l) is epichlorohydrin; components (B-2 b) or (B-3-b) is sthylene dichloride; co~ponents (A), (B~ and (C) are employed in quantitie~ which provide a non~gelled poly-amine which gives a fluid loss of less than about 45 ml according to the API RP lOB fluid loss test and the viscosity o~ a solution containing 35 percent active 31,134B-F -6 ~6a-material is fro~ 300 to 10,000 cps. More preferably the visc05ity of a solution containing 35% active material is from 2000 to 4000 cps.

In determining the amount of the polyalkylene~
polyamine and alkylene dihalide to employ, a series o~
lab scale reactions are employed with varying ratios of reactants of alkylene dichloride:polyalkylenepolyamine such as, for example, 0.4:1, 0.5:1, 0.6:1, 0.8:1 and 1.1~1 by weight are conducted at a suitable tempexa~ure and water concen~ration. From the lowest ratio that created the gel new propor~ions are selected in the following manner, assuming a ratio of O . 55 :1 produced a gel.

' ~ 31 t 134B-F -6a-Zl~

Assuming that the following arbitrary formulation produces a gel (in grams).

1100 g EDC (~thylene dichloride) 2000 g polyamine 3900 ~ water 7000 g Then the active components, i.e., carbon, hydrogen, nitrogen contained in above formulation (in grams) is 2000 g from polyamine 311 q from EDC
2311 g The amount of car~on plus hydrogen to leave out of the recipe is from 19 g to 115 g which corresponds to 67 to 406 grams of EDC.

The amount of crosslinking agent to be fur~her added is determined by adding small portions of cross-linking agent to à~out 100 grams of ~he first product until the product gels. At that point ~assume 6 grams o 50% active crosslinking agent produced the ~el) a sexies of samples are prepared using 6 g/100 gJ 5 g/100 ~, 4 g/100 g, etc. The ratio which gives a product with a viscosity of from 1000 to 4000, preferably from 2000 to 3000, cps is the one which .
would be used to complete the reaction.

Suitable alkylenediamines and polyalkylene-polyamines which can be employed herein include polyethylenepolyamines having an average molecular 31,134B-F -7-~7~1~5 weight of from 60 to 500, preferably from 150 to 350, which can be prepared by reacting a~ vicinal alkylene dihalide having from 2 to 6 carbon atoms with ammonia or lower alkyleneamines such as, for example, ethyl-enediamine, diethylenetriamine and the like. Suitablemethods of preparation are disclosed by Garm~ et al in U.S. Patent No. 3,210,308. Particularly suit~ble are the bottoms product from ~he preparation of ethylene-diamine from ammonia and ethylene dichloride. By bottoms produc~ it is meant that which results after substantially removing those compounds boiling lower than pentaethylenehexamine from the reaction product resulting from reacting ammonia with ethylene dichloride.

Suitable epihalohydrins and/or dihalohydrins which can be employed herein include those represented by the formulas ~O\ X OH ~
~2 -C~CHzX and H-C--C--C-X
" ,~ , . . .
H R
wherein each R is hydrogen or an alkyl group having ~rom 1 to 4 carbon atoms and each X is independently chlorine or bromine.

The cement slurry also contains an ef~ective amount o~ a surfactant such as, for example, a water dispersable lignosulfate, lignoamine, sulfonic acids, mixtures thereof and the like. An amount of from 0.25 to 5 parts by weight is preferred. An amount of from 0.5 to 1.5 parts by weight i5 most preferred.

If desired the cement slurry compositions may also contain a borate ion releasing compound and/or a 31,134B-F -8-~2~7~

carbonate and/or a bicarbonate as disclosed by Crinkelmeyer et al in U.SO Patent No. 4,131,578.
.

The quantities of components o~ the aqueous cement slurry composition of the present invention are based on 100 parts by weight of hydraulic cement as follows:

~ydraulic Cement --- 100 Water --- 25 to 100, preferably 35 to 50 Fluid Loss Additive --- 0.5 to 8, preferably 0.75 to 3 10 Surfa~tant --- 0.25 to 5, pre~erably 0.5 to 1.5 Borate Ion Releasing Compound --- 0 to 3, prefera~ly 1 to 2 Carbonate or Bicarbonate -- 0 to 3, preferably 0-1 to 0.3 It is to be understood that not all of the pro~uct is regarded as "active". The active portion of the product is the carbon ~ nitrogen ~ hydrogen portion of the aqueous solutions produced. Percent active is calculated as the weight of (carbon ~ nitrogen + hydrogen) divided by the total weight of the amine solution multiplied by 100.

The following examples are illustrative of the invention but are not to be construed as to limiting the ~cope thereo~ in any manner.

A PrePara-tion of Polyalk~lenepolyamine 2200.4 G of water and 1289 grams of a polyalky-lenepolyamine which was the bottoms product re~ulting from removing tetraethylene pentamine and lower boiling 31,134B-F -9 ~7~

products from the reaction product of ammonia and ethylene dichlorida and having an average molecular weight of about 300 and hereafter referred to as poly-amine 300 were mixed in a 5 liter vessel by adding 510.5 g of ethylene dichloride to the vessel. The mixture of reactan~s was stirred and heated at 70C for 16 hours. The viscosity of the resultant solution was F300 cps.

B. Preparation of Crosslinker 82.54 ~ of ~iethylenetriamine and 176 g of water were placed in a l-liter vessel. The temperature of the solution was controlled at about 40C while 370.14 g of epichlorohydrin was added. The reactants were stirred overnigh~ at 40C and a light yellow product was removed from the vessel and refrigerated.

C. Preparation of Crosslinked Po~ymer 134 g of the crosslinker solution prepared in B above was added to 4000 g of the polyalkylenepolyamine prepared in A above. The mixture of reactants was heated to a temperature of from 60 to 70C for 4 hours. An amber solution with a viscosit~ of about 300 cps was removed from the vessel. This material was tested as indicated in D below. The results are seported in Table I.

~5 D. Fluid Loss Testing The fluid loss tests were run according tP
API RP lOB using a Baroid high temperature high pressure fluid loss apparatus and a 325 mesh (U.S.
Standard Sieve Series) stainless s~eel screen. 100 parts by weight Lone star type H cement was mi~ed with 0.5 parts by weight of a surfactant material which is 31,134B-F -10 the condensation product of formaldehyde ~nd mono-naphthalenesulfonic acid. 42 parts by weight of water was mixed with the desired amount of the activ~
polyamine (1~1% by weight of the cement employed). The water and cement were then blended together and digested at 200F ~93.3C) for 20 minutes. The slurry was added to the filtra~ion cell which was preheated to 200F
(93.3C~ and the fluid loss (in cm3/30 min) was measured with 1000 psig (6.89 kPa) nitrogen pressure on the filtration cell. The fluid loss measure was then multiplied by 2 so as to adjust for the size of the screen used with the filtration cell.

EXAMoeLE 2 ~ e A Pre~aration of Crosslinker 503.5 g of Polyamine 300 and 825.5 g of water were placed in a 1-liter vessel. The temperature of the solution was controlled at 30C while 1858 g of epichlorohydrin was added. The reactants were stirred at 70C overnight and an amber product wa~ removed from the flask.

B. Preparation of Crosslinked Pol~mer 10.3 g of crosslinker solution prepared in A
abova was added to 150 g of polyalkylenepolyamine prepared as in Example 1-A. The mixture of reactants 2S was heated to a temperature of from 60 to 70C for 4 hours, An amber solution was removed from the vessel.
It was tested as a fluid loss additive by the procedure described in Example 1-D. The results are given in Table I.

31,134B-F

~$
-~2--To 300 g of polyalkylenepolyamine prepared in Example 1-A was added 8 g of epichlorohydrin. The mixture was reacted at a temperature of 60C in a shaker bath overnight. An amber solutio~ was produced.
This material was tested according to Example 1-D. The results are given in Table I.

EX~MPLE 4 To 250 g of Polyamine 300 was added S40 g of water. 127 g of epichlorohydrin was added and reacted therewith until the viscosity increased -to J3000 cps.
The resultant product was tested as a fluid loss additive according to the procedure of Example l-D.
The results are given in Table I.

EXAMPLE 5 (COMPARATIVE) Example 4 was repeated employing 1~00 g of Polyamine 300 and 618 g of ethylene dichloride. The resultant viscosity was J6000 cps. The product was tested as a fluid loss additive employing the procedure of Example l~D. The results are given in Table I.

1683 g water was mixed with 886 g of polyamine 300 in a 5-liter vessel. A mixture of 380 g e~hylenedichloride (EDC) and 51.2 grams of epichloro-hydrin (EPI ? was added slowly over 4.5 hours to thewater-amine solution. The temperature of the reaction mixture was maintained at a temperature of from 65 to 70C. An additional 50 g of EDC and 4 g of EPI was added in 10 gram portions until the reaction mixture reached a cps viscosity of from 500 to 600 cps. This 31,134B-F -12-72~5 -13~

material was tested as a fluid loss additive (1.2%
polyamine based on cement). The results are given in Table I.

1683 g water and 886 g of polyamine 300 were mi~ed in a 5-liter flask. A mixture of 380 g ethylene-dichloride (EDC) and 51.2 g of epichloroh~drin (EPI) was added slowly over 4.5 hours to the amine-water solution. The temperature of the reaction was maintained at a temperature of from 65 to 70C. 17.5 g of a cross-linker prepared as in Example 2A was added to 150 g of the polyamide-EDC-EPI product. The mixture was reacted at 100C for 30 minutes. The resulting polymer solution had a viscosity J300 cps and was tested as a fluid loss additive (1.2% based on cement~.
The result~ are given in Table 1.

TABT.E I
EXAMPLE NO. FLUID LOSS IN CUBIC CENTIMETERS*
l-A (compar~tive~ J60 mls in F5 min.
l-C 20

- 4 26

5 (comparative) 70.4

6 50-55

7 22 *corrected to API sta~dard screen, i.e. the actual test results have been multiplied by 2.

31,134B-F -13-

Claims (8)

1. A modified alkylenediamine or polyalkylene-polyamine composition, characterized in that the composition is the reaction product resulting from reacting (A) at least one of (1) at least one alkylenediamine or polyalkylenepolyamine composition having an average molecular weight of from 60 to 500;
(2) at least one composition prepared by reacting (a) a polyalkylenepolyamine compo-sition having an average molecular weight of from 60 to 500 with (b) at least one alkylene dihalide;
wherein component (A-2-a) and component (A-2-b) are reacted in quantities such that the quanity of (A-2-b) used is less than the amount needed to form a gel by an amount (expressed as weight of carbon and hydrogen contained in (A-2-b) of from 0.8% to 5% of the weight of carbon plus hydrogen plus nitrogen present in the reaction mixture when a gel would be formed;
(3) mixtures of (1) and (2); with (B) at least one of (1) an epiphalohydrin or dihalodrin, (2) an adduct of (a) an epihalohydrin or dihalo-hydrin and (b) an alklenediamine, poly-alkylenepolyamine having an average molecular weight of from 60 to 500 to mixtures thereof;
(3) a mixture of (a) at least one epihalohydrin, dihalohydrin or mixture thereof;
and (b) at least one alkylene dihalide or (4) a mixture of at least one of (1), (2) and (3); and (C) optionally, one or more adducts of (1) at least one epihalohydrin, dihalo-hydrin or mixture thereof; and (2) at least one alkylenediamine or polyalkylenepolyamine having an average molecular weight of from 60 to 500 or a mixture thereof; and wherein components (A), (B) and (C) are employed in quantities which provide a non-gelled polyamine which given a fluid loss of less than about 60 ml according to the API RP 10B fluid loss test.
2. The composition of Claim 1 characterized in that (i) components (A-1) (A-2-a) and (A-2-b) independently have an average molecular weight of from 150 to 350 and ( C-2 ) has an average molecular weight of from 60 to 350;
(ii) components (B-1) or (B-2-a) or (B-3-a) or (C-1) is epichlorohydrin;
components (b-2-b) or (B-3-b) is ethylene dichloride;
(iv) components (A), (B) and (C) are employed in quantities which provide a non-gelled polyamine which gives a fluid loss of less than about 45 ml according to the API RP 10B fluid loss test and the viscosity of a solution containing 35%
active material is from 300 to 10,000 cps.
3. The composition of Claim 1, characterized in that the viscosity of a solution containing 35%
active material is from 300 to 10,000 cps.
4. The composition of Claim 2 or 3, characterized in that the viscosity of a solution containing 35% active material is from 2000 to 4000 cps.
5. An aqueous hydraulic cement slurry composition comprising water, hydralic cement, surfactant and polyalkylene-polyamine fluid loss additive; characterized by employing as said fluid loss additive, at least one composition prepared by reacting (A) at least one of (1) at least one alkylenediamine or polyalkylenepolyamine composition having an average molecular weight of from 60 to 500;
(2) at least one composition prepared by reacting (a) a polyalkylenepolyamine compo-sition having an average .
molecular weight of from 60 to 500 with (b) at least one alkylene dihalide;
wherein component (A 2-a) and component (A-2-b) are reacted in quantities such that the guantity of (A-2-b) used is less than the amount needed to form a gel by an amount (expressed as weight of carbon and hydrogen contained in (A-2-b) of from 0.8% to 5% of the weight of carbon plus hydrogen plus nitrogen present in the reaction mixture when a gel would be formed;
(3) mixtures of (1) and (2); with (B) at least one of (1) an epiphalohydrin or dihalodrin, (2) an adduct of (a) an epihalohydrin or dihalo-hydrin and (b ) an alklenediamine, poly-alkylenepolyamine having an average molecular weight of from 60 to 500 to mixtures thereof;
(3) a mixture of (a) at least one epihalohydrin, dihalohydrin or mixture thereof;
and (b) at least one alkylene dihalide;
or (4) mixtures thereof; and (C) optionally, one or more adducts of (1) at least one epihalohydrin, dihalo-hydrin or mixture thereof; and (2) at least one alkylenediamine or polyalkylenepolyamine having an average molecular weight of from 60 to 500 or a mixture thereof; and wherein components (A), (B) and (C) are employed in quantities which provide a non-gelled polyamine which given a fluid loss of less than about 60 ml according to the API RP 10B fluid loss test.
6. The composition of Claim 5, characterized in that (i) components (A-1), (A-2-a) and (A-2-b) independently have an average molecular weight of from 150 to 350 and (C-2) has an average molecular weight of from 60 to 350;
(ii) components (B-1) or (B-2-a) or (B-3-a) or (C-1) is epichlorohydrin;
(iii) components (B-2-b) or (B-3-b) is ethylene dichloride;

(iv) components (A), (B) and (C) are employed in quantities which provide a non-gelled polyamine which gives a fluid loss of less than about 45 ml according to the API RP 10B fluid loss test and the viscosity of a solution containing 35%
active material is from 300 to 10,000 cps.
7. The composition of Claim 5, characterized in that the viscosity of a solution containing 35%
active material is from 300 to 10,000 cps.
8. The composition of Claim 6 or 7, charac-terized in that the viscosity of a solution containing 35% active material is from 2000 to 4000 cps.
CA 466497 1983-11-03 1984-10-29 Modified alkylenediamine or polyalkylenepolyamine composition and aqueous hydraulic cement slurry employing the composition Expired CA1217205A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
US06548475 US4461856A (en) 1983-11-03 1983-11-03 Aqueous hydraulic cement slurry
US548,475 1983-11-03
US586,374 1984-03-05
US06586374 US4482667A (en) 1983-11-03 1984-03-05 Modified polyalkylenepolyamines
US06638824 US4519843A (en) 1983-11-03 1984-08-08 Modified polyalkylenepolyamines
US638,824 1984-08-08

Publications (1)

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Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4972025A (en) * 1987-03-24 1990-11-20 Nippon Shokubai Kagaku Kogyo, Co., Ltd. Cement dispersant
US4892589A (en) * 1987-10-30 1990-01-09 Aqualon Company Composition comprising water-soluble, nonionic hydrophobically modified hydroxyethyl cellulose and water-soluble, nonionic hydroxyethyl cellulose
FR2887542B1 (en) * 2004-09-21 2007-10-12 Lafarge Sa Method for inerting impurities
US8834626B2 (en) 2004-09-21 2014-09-16 Lafarge Impurity inerting composition
WO2006032785A3 (en) * 2004-09-21 2007-01-25 Lafarge Sa Method for inerting impurities

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3210308A (en) * 1962-07-06 1965-10-05 Dow Chemical Co Polymeric flocculants
US3247048A (en) * 1962-09-10 1966-04-19 Monsanto Co Nitrogen prepolymers as wet and dry strength improvers for paper
US3491049A (en) * 1965-10-13 1970-01-20 Dow Chemical Co Low water-loss aqueous cement slurry and method of use
US3511314A (en) * 1968-10-28 1970-05-12 Dow Chemical Co Cementing composition and well cementing process employing same
US4131578A (en) * 1975-02-03 1978-12-26 The Dow Chemical Company Aqueous hydraulic cement slurry
US3988279A (en) * 1975-04-23 1976-10-26 Celanese Coatings & Specialties Company Thermosetting concrete-containing epoxy
US4129528A (en) * 1976-05-11 1978-12-12 Monsanto Company Polyamine-epihalohydrin resinous reaction products
US4260700A (en) * 1977-01-24 1981-04-07 The B.F. Goodrich Company Underwater curing of epoxy resin and amine-terminated liquid polymer and product thereof
US4191820A (en) * 1978-01-03 1980-03-04 Basf Wyandotte Corporation Process for preparing polyalkylene polyamine polyethers
DE3003648A1 (en) * 1980-02-01 1981-08-06 Basf Ag A process for zerstellung wasserloeslichen of nitrogen-containing condensation products and their use in papermaking
US4316003A (en) * 1980-10-23 1982-02-16 Shell Oil Company Epoxy resin curing agents

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CA1217205A1 (en) grant
EP0165252A1 (en) 1985-12-27 application
WO1985001935A1 (en) 1985-05-09 application
EP0165252A4 (en) 1986-07-23 application

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