EP0165252A1 - Composition modifiee de diamine d'alcene ou de polyamine de polyalcene et pate de ciment hydraulique aqueuse utilisant cette composition - Google Patents

Composition modifiee de diamine d'alcene ou de polyamine de polyalcene et pate de ciment hydraulique aqueuse utilisant cette composition

Info

Publication number
EP0165252A1
EP0165252A1 EP84903921A EP84903921A EP0165252A1 EP 0165252 A1 EP0165252 A1 EP 0165252A1 EP 84903921 A EP84903921 A EP 84903921A EP 84903921 A EP84903921 A EP 84903921A EP 0165252 A1 EP0165252 A1 EP 0165252A1
Authority
EP
European Patent Office
Prior art keywords
composition
average molecular
molecular weight
mixture
polyalkylenepolyamine
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP84903921A
Other languages
German (de)
English (en)
Other versions
EP0165252A4 (fr
Inventor
Stephen B. Willis
Pamela J. Boyce
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Chemical Co
Original Assignee
Dow Chemical Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from US06/548,475 external-priority patent/US4461856A/en
Priority claimed from US06/586,374 external-priority patent/US4482667A/en
Priority claimed from US06/638,824 external-priority patent/US4519843A/en
Application filed by Dow Chemical Co filed Critical Dow Chemical Co
Publication of EP0165252A1 publication Critical patent/EP0165252A1/fr
Publication of EP0165252A4 publication Critical patent/EP0165252A4/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/24—Macromolecular compounds
    • C04B24/28—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
    • C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
    • C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
    • C04B24/12—Nitrogen containing compounds organic derivatives of hydrazine
    • C04B24/121—Amines, polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular 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
    • C08G73/02—Polyamines
    • C08G73/0206—Polyalkylene(poly)amines
    • C08G73/0213—Preparatory process
    • C08G73/022—Preparatory process from polyamines and epihalohydrins

Definitions

  • 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.
  • 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.
  • 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.
  • 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
  • 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
  • (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
  • 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
  • component (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
  • 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).
  • 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.
  • 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
  • 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.
  • 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.
  • 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:
  • Fluid Loss Additive 0.5 to 8, preferably 0.75 to 3 Surfactant --- 0.25 to 5, preferably 0.5 to 1.5
  • Carbonate of Bicarbonate 0 to 3 preferably
  • active 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.
  • 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
  • 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 cm 3 /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 1-A 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 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 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.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Ceramic Engineering (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Materials Engineering (AREA)
  • Structural Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Curing Cements, Concrete, And Artificial Stone (AREA)

Abstract

Composition modifiée de diamine d'alcène ou de polyamine de polyalcène et utilisation de cette composition en tant qu'additif de perte liquide dans des pâtes de ciment hydrauliques aqueuses, en tant qu'agent de floculation pour l'épuration de l'eau, dans le traitement des déchets liquides, ou dans l'industrie minière pour la floculation de particules solides dans l'eau ou d'autres milieux aqueux.
EP19840903921 1983-11-03 1984-10-29 Composition modifiee de diamine d'alcene ou de polyamine de polyalcene et pate de ciment hydraulique aqueuse utilisant cette composition. Withdrawn EP0165252A4 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US548475 1983-11-03
US06/548,475 US4461856A (en) 1983-11-03 1983-11-03 Aqueous hydraulic cement slurry
US06/586,374 US4482667A (en) 1983-11-03 1984-03-05 Modified polyalkylenepolyamines
US586374 1984-03-05
US638824 1984-08-08
US06/638,824 US4519843A (en) 1983-11-03 1984-08-08 Modified polyalkylenepolyamines

Publications (2)

Publication Number Publication Date
EP0165252A1 true EP0165252A1 (fr) 1985-12-27
EP0165252A4 EP0165252A4 (fr) 1986-07-23

Family

ID=27415533

Family Applications (1)

Application Number Title Priority Date Filing Date
EP19840903921 Withdrawn EP0165252A4 (fr) 1983-11-03 1984-10-29 Composition modifiee de diamine d'alcene ou de polyamine de polyalcene et pate de ciment hydraulique aqueuse utilisant cette composition.

Country Status (6)

Country Link
EP (1) EP0165252A4 (fr)
BR (1) BR8407149A (fr)
CA (1) CA1217205A (fr)
IT (1) IT1177106B (fr)
NO (1) NO852648L (fr)
WO (1) WO1985001935A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3809964C2 (de) * 1987-03-24 1994-08-25 Nippon Catalytic Chem Ind Zement-Dispergiermittel, Verfahren zu seiner Herstellung und seine Verwendung
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
FR2887541B1 (fr) * 2004-09-21 2007-10-12 Lafarge Sa Compositions d'inertage d'impuretes
ATE532756T1 (de) 2004-09-21 2011-11-15 Lafarge Sa Verfahren zur inertisierung von unreinheiten
WO2006032786A2 (fr) * 2004-09-21 2006-03-30 Lafarge Compositions d'inertage d'impuretes
AU2012370954B2 (en) 2012-02-22 2016-08-11 Gcp Applied Technologies Inc. Functionalized polyamines for clay mitigation
ES2596438T3 (es) 2012-05-04 2017-01-09 Gcp Applied Technologies Inc. Método para tratar arcilla y agregados arcillosos y composiciones destinadas a ello

Family Cites Families (12)

* 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
CH451513A (de) * 1965-03-26 1968-05-15 Ciba Geigy Verfahren zur Herstellung von neuen härtbaren stickstoffhaltigen Kondensationsprodukten
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 (de) * 1980-02-01 1981-08-06 Basf Ag, 6700 Ludwigshafen Verfahren zur zerstellung von wasserloeslichen, stickstoffhaltigen kondensationsprodukten und deren verwendung bei der papierherstellung
US4316003A (en) * 1980-10-23 1982-02-16 Shell Oil Company Epoxy resin curing agents

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
No relevant documents have been disclosed *
See also references of WO8501935A1 *

Also Published As

Publication number Publication date
NO852648L (no) 1985-07-02
IT8423439A1 (it) 1986-05-02
EP0165252A4 (fr) 1986-07-23
IT1177106B (it) 1987-08-26
WO1985001935A1 (fr) 1985-05-09
CA1217205A (fr) 1987-01-27
IT8423439A0 (it) 1984-11-02
BR8407149A (pt) 1985-10-08

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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Inventor name: BOYCE, PAMELA, J.

Inventor name: WILLIS, STEPHEN, B.