WO1985001935A1 - A modified alkylenediamine or polyakylenepolyamine composition and aqueous hydraulic cement slurry employing the composition - Google Patents

A modified alkylenediamine or polyakylenepolyamine composition and aqueous hydraulic cement slurry employing the composition Download PDF

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WO1985001935A1
WO1985001935A1 PCT/US1984/001743 US8401743W WO8501935A1 WO 1985001935 A1 WO1985001935 A1 WO 1985001935A1 US 8401743 W US8401743 W US 8401743W WO 8501935 A1 WO8501935 A1 WO 8501935A1
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composition
average molecular
molecular weight
mixture
polyalkylenepolyamine
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PCT/US1984/001743
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French (fr)
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Stephen B. Willis
Pamela J. Boyce
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The Dow Chemical Company
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    • 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

A modified alkylenediamine or polyalkylenepolyamine composition and use of the composition as a fluid loss addivite 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

A MODIFIED ALKYLENEDIAMINE OR POLYALKYLENEPOLYAMINE COMPOSITION AND AQUEOUS HYDRAULIC CEMENT SLURRY EMPLOYING THE COMPOSITION

The present invention resides in a modified alkylenediamine or polyalkylenepolyamine composition. The composition is suitable for use as a fluid loss additive in aqueous hydraulic cement slurry compositions or as a floccuiant 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 aqueous media (pulps) to cause the individual particles to collect in the form of blocks.

Hydraulic cements, i.e., any inorganic cement that hardens or sets under water, are customarily admixed with water and emplaced as aqueous slurries. The amount of water employed may vary rather extensively depending largely upon the fluidity of the slurry required and upon the necessary ultimate strength. In a great many uses of a hydraulic cement it is necessary for the cement slurry to be emplaced within or next to a porous medium, for example, earthen strata, e.g., in the cementing off of boreholes, grouting, dam and tunnel construction and the like. When such is the case, water filters out of the slurry and into the strata during the setting period. When this occurs to any appreciable extent there usually results an uncontrolled setting rate, improper placement, impaired strength properties and usually a contamination of the surrounding strata. All of these undesirable conditions are especially to be avoided in cementing operations associated with oil, gas, water or brine wells. In an effort to lessen the loss of fluid from an aqueous hydraulic 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 93ºC (200°F), 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 temperatures of 93°C (200°F) and above.

The composition of the present invention is advantageously 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 of water loss or, at the same level of active additives, less water loss occurs while also providing more stable, non-settling, cement slurries. The present invention particularly resides in a modified alkylenediamine or polyalkylenepolyamine composition comprising the product resulting from reacting a modified alkylenediamine or polyalkylenepolyamine 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 composition 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 quantity 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 dihalohydrin and

(b) an alklenediamine, polyalkylenepolyamine 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, dihalohydrin 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 described in the examples.

The invention also resides in an aqueous hydraulic cement slurry composition comprising water, hydraulic cement, surfactant and polyalkylenepolyamine 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 composition 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 quantity 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 dihalohydrin and (b) an alklenediamine, polyalkylenepolyamine 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, dihalohydrin 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 gives a fluid loss of less than about 60 ml according to the API RP 10B fluid loss test described in the examples.

In determining the amount of the polyalkylenepolyamine and alkylene dihalide to employ, a series of 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 temperature and water concentration. From the lowest ratio that created the gel new proportions are selected in the following manner, assuming a ratio of 0.55:1 produced a gel. Assuming that the following arbitrary formulation produces a gel ( in grams).

1100 g EDC (ethylene dichloride) 2000 g polyamine 3900 g water

7000 g

Then the active components, i.e., carbon, hydrogen, nitrogen contained in above formulation (in grams ) is

2000 g from polyamine

311 g from EDC 2311 g

The amount of carbon 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 further added is determined by adding small portions of crosslinking agent to about 100 grams of the first product until the product gels. At that point (assume 6 grams of 50% active crosslinking agent produced the gel) a series of samples are prepared using 6 g/100 g, 5 g/100 g, 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 polyalkylenepolyamines which can be employed herein include polyethylenepolyamines having an average molecular 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, ethylenediamine, diethylenetriamine and the like. Suitable methods of preparation are disclosed by Garms et al in U.S. Patent No. 3,210,308. Particularly suitable are the bottoms product from the preparation of ethylenediamine from ammonia and ethylene dichloride. By bottoms product 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

Figure imgf000010_0001
wherein each R is hydrogen or an alkyl group having from 1 to 4 carbon atoms and each X is independently chlorine or bromine.

The cement slurry also contains an effective amount of 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 is most preferred.

If desired the cement slurry compositions may also contain a borate ion releasing compound and/or a carbonate and/or a bicarbonate as disclosed by Crinkelmeyer et al in U.S. Patent No. 4,131,578.

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

Hydraulic Cement --- 100

Water 25 to 100, preferably 35 to 50

Fluid Loss Additive 0.5 to 8, preferably 0.75 to 3 Surfactant --- 0.25 to 5, preferably 0.5 to 1.5

Borate Ion Releasing Compound --- 0 to 3, preferably 1 to 2

Carbonate of Bicarbonate 0 to 3, preferably

0.3

It is to be understood that not all of the product 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 scope thereof in any manner.

EXAMPLE 1

A. Preparation of Polyalkylenepolyamine

2200.4 G of water and 1289 grams of a polyalkylenepolyamine which was the bottoms product resulting from removing tetraethylene pentamine and lower boiling products from the reaction product of ammonia and ethylene dichloride and having an average molecular weight of about 300 and hereafter referred to as polyamine 300 were mixed in a 5-liter vessel by adding 510.5 g of ethylene dichloride to the vessel. The mixture of reactants was stirred and heated at 70°C for 16 hours. The viscosity of the resultant solution was <300 cps.

B. Preparation of Crosslinker 82.54 g of eiethylenetriamine and 176 g of water were placed in a 1-liter vessel. The temperature of the solution was controlled at about 40°C while 370.14 g of epichlorohydrin was added. The reactants were stirred overnight at 40°C and a light yellow product was removed from the vessel and refrigerated.

C. Preparation of Crosslinked Polymer

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 70°C for 4 hours. An amber solution with a viscosity of about 300 cps was removed from the vessel. This material was tested as indicated in D below. The results are reported in Table I.

D. Fluid Loss Testing

The fluid loss tests were run according to

API RP 10B using a Baroid high temperature high pressure fluid loss apparatus and a 325 mesh (U.S.

Standard Sieve Series) stainless steel screen. 100 parts by weight Lone Star type H cement was mixed with

0.5 parts by weight of a surfactant material which is the condensation product of formaldehyde and mononaphthalenesulfonic acid. 42 parts by weight of water was mixed with the desired amount of the active polyamine (1.1% by weight of the cement employed). The water and cement were then blended together and digested at 200°F (93.3°C) for 20 minutes. The slurry was added to the filtration cell which was preheated to 200°F (93.3ºC) 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.

EXAMPLE 2

A. Preparation 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 30°C while 1858 g of epichlorohydrin was added. The reactants were stirred at 70°C overnight and an amber product was removed from the flask.

B. Preparation of Crosslinked Polymer

10.3 g of crosslinker solution prepared in A above was added to 150 g of polyalkylenepolyamine prepared as in Example 1-A. The mixture of reactants was heated to a temperature of from 60° to 70°C 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. EXAMPLE 3

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

EXAMPLE 4

To 250 g of polyamine 300 was added 640 g of water. 127 g of epichlorohydrin was added and reacted therewith until the viscosity increased to >3000 cps. The resultant product was tested as a fluid loss additive according to the procedure of Example 1-D. The results are given in Table I.

EXAMPLE 5 (COMPARATIVE)

Example 4 was repeated employing 1200 g of Polyamine 300 and 618 g of ethylene dichloride. The resultant viscosity was >6000 cps. The product was tested as a fluid loss additive employing the procedure of Example 1-D. The results are given in Table I.

EXAMPLE 6

1683 g water was mixed with 886 g of polyamine 300 in a 5-liter vessel. A mixture of 380 g ethylenedichloride (EDC) and 51.2 grams of epichlorohydrin (EPI). was added slowly over 4.5 hours to the water-amine solution. The temperature of the reaction mixture was maintained at a temperature of from 65° to 70°C. 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 material was tested as a fluid loss additive (1.2% polyamine based on cement). The results are given in Table I.

EXAMPLE 7 1683 g water and 886 g of polyamine 300 were mixed in a 5-liter flask. A mixture of 380 g ethylenedichloride (EDC) and 51.2 g of epichlorohydrin (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 70°C. 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 100°C for 30 minutes. The resulting polymer solution had a viscosity >300 cps and was tested as a fluid loss additive (1.2% based on cement). The results are given in Table 1.

Figure imgf000015_0001

Claims

1. A modified alkylenediamine or polyalkylenepolyamine 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 composition 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 quantity 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 dihaiodrin,
(2) an adduct of
(a) an epihalohydrin or dihalohydrin and (b) an alklenediamine, polyalkylenepolyamine 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, dihalohydrin 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 described in the examples.
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; (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 Iss of less than about 45 ml according to the
API RP 10B fluid loss test described in the examples 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 polyalkyle polyamine fluid loss additive; characterized by employing as said fluid loss additvie, 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 composition 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 quantity 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 dihalohydrin and (b) an alklenediamine, polyalkylenepolyamine 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, dihalohydrin 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 described in the examples.
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 described in the examples 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, characterized in that the viscosity of a solution containing 35% active material is from 2000 to 4000 cps.
PCT/US1984/001743 1983-11-03 1984-10-29 A modified alkylenediamine or polyakylenepolyamine composition and aqueous hydraulic cement slurry employing the composition WO1985001935A1 (en)

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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

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US8834626B2 (en) 2004-09-21 2014-09-16 Lafarge Impurity inerting composition
WO2006032785A2 (en) * 2004-09-21 2006-03-30 Lafarge Method for inerting impurities
FR2887541A1 (en) * 2004-09-21 2006-12-29 Lafarge Sa Composition for inerting clays in the sand used for hydraulic compositions, e.g. to prevent adverse effects on concrete properties, contains at least 50 wt. percent of a cationic polymer as active substance
FR2887542A1 (en) * 2004-09-21 2006-12-29 Lafarge Sa Method for inerting impurities
WO2006032785A3 (en) * 2004-09-21 2007-01-25 Lafarge Sa Method for inerting impurities
WO2006032786A3 (en) * 2004-09-21 2007-03-01 Lafarge Sa Impurity inerting compositions
US8257490B2 (en) 2004-09-21 2012-09-04 Lafarge Method for inerting impurities
WO2013124003A1 (en) * 2012-02-22 2013-08-29 W R Grace & Co.-Conn Functionalized polyamines for clay mitigation
CN104245619A (en) * 2012-02-22 2014-12-24 格雷斯公司 Functionalized polyamines for clay mitigation
CN104245619B (en) * 2012-02-22 2017-03-29 Gcp应用技术有限公司 A functionalized polyamine clay alleviated
US9950953B2 (en) 2012-02-22 2018-04-24 Gcp Applied Technologies Inc. Functionalized polyamines for clay mitigation
US9994483B2 (en) 2012-02-22 2018-06-12 Gcp Applied Technologies Inc. Functionalized polyamines for clay mitigation

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EP0165252A1 (en) 1985-12-27 application
CA1217205A (en) 1987-01-27 grant
EP0165252A4 (en) 1986-07-23 application

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