Classifications

• • 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
  • C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
  • C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
• • 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
  • C04B24/16—Sulfur-containing compounds
  • C04B24/20—Sulfonated aromatic compounds
  • C04B24/22—Condensation or polymerisation products thereof
• • 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
  • C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
  • C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
  • C08G16/025—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds
  • C08G16/0275—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds containing sulfur in the ring

Definitions

• This invention relates to a non-air entraining water-reducing agent for use with mortar and/or concrete.
• This water-reducing agent comprises a high molecular weight condensate of formaldehyde with naphthalene sulfonic acid and socyanuric acid, or the respective neutralized salts thereof.
• high-range water-reducing agents are used with high cement content mixes, and if added at the time the concrete is being mixed, increase the workability of the concrete, increase the efficiency of the cement, and reduce the amount of water required in the concrete, as well as increase the strength of the concrete at all ages measured. Such agents also increase the quality of the concrete by reducing the tendency of the concrete to form cracks or fissures. Therefore, high-range water-reducing agents are extremely beneficial in the dispersion of crushed rock, mortar, and cement in manufactured concrete.
• water-reducing agents are utilized to stop slump loss associated with transporting of ready mix concrete, to improve the water reducing character stics, to improve concrete flowability, and to improve ultimate quality.
• High-range water-reducing agents are used to produce high strength concrete, particularly with concrete used in secondary products such as prestressed members, and as agents to improve concrete flowability for ease of placement.
• Japanese Patent announcement SHO 54-1331 reports that water reduction in concrete is obtained from the use of tris (hydroxyal yl) isocyanurate by itself, or in combination with other known commercial high-range water-reducing agents.
• the use of tr s (hydroxyalkyl) isocyanurate alone shows little water reduction in concrete, and water reducing characteristics are in fact diminished as the quantity of tris (hydroxyalkyl) isocyanurate increases in commercial compounds.
• the present invention as a result of an earnest study of water-reducing agents utilized with mortar or concrete, is able to offer a water-reducing agent with performance that greatly reduces the amount of slump loss of concrete when a combination of naphthalene sulfonic acid and isocyanuric acid compounds is used as a product of a co-reaction and/or condensation with formaldehyde.
• this invention relates to a water-reducing agent utilized with mortar and concrete, of which the primary components are condensates of formaldehyde, naphthalene sulfonic acid, and at least one type of isocyanuric acid composition selected from a group which includes isocyanuric acid, tris (hydroxyalk l) isocyanurate, tris (carboxy) isocyanurate, and tris (alkyl) isocyanurate.
• the neutralized salts of the. two acids may be used in place of the acids themselves.
• 0.01-0.5 mol of sulfuric acid is used as a catalyst, preferably within the range of 0.04-0.4 mol, and 0.01-0.5 mol of isocyanuric acid composition, preferably the range of 0.02-0.3 mol is added.
• 0.08-2.0 mol of formaldehyde (ordinarily as a solution of 37 percent formalin in water), preferably within the range of 0.9-1.5 mol, is added to the reaction mixture.
• the temperature of the reaction mixture is held between 100-140° C, preferably 110-130" C, from 1-10 hours, preferably 3-8 hours, until the reaction is completed.
• the reaction is completed when the non-reacted naphthalene sulfonic acid and the non-reacted isocyanuric acid composition are analyzed by means of HLC, and 90 percent or more of the naphthalene sulfonic acid and the isocyanuric acid composition have reacted.
• neutralization is accomplished through ordinary means with caustic soda or calcium hydroxide.
• the reaction fluid is adjusted to a pH of 8-10. Following the removal, if necessary, of the undissolved components, the water-reducing agent s ready for use.
• naphthalene sulfonic acid utilization may be made of such mono sulfonic acid types as beta-naphthalene sulfonic acid, alpha-naphthalene sulfonic acid, etc., poly sulfonic acids such as di -sulfonic acid, or tri -sulfonic acid, as well as compounds or mixtures of these.
• Naphthalene sulfonic acids can also be obtained from naphthalene sulfate salts. However, in these instances, if the acid sulfate reacting liquor is used directly in the joint condensation reaction of this invention, a catalyst of sulfuric acid is obtained without the need for duplication as an added benefit.
• the isocyanuric acid compositions may be used independently as reactants or as mixtures.
• a by-product of producing an isocyanuric acid compound may be utilized which waste fluids have an isocyanuric acid composition of 10 percent or more.
• formaldehyde may, of course, be utilized.
• gaseous formaldehyde may be dissolved directly in water to produce formalin for the condensation reaction described.
• the water-reducing agents of this invention may be used in concrete or mortars the ratio of 0.01-10 percent, with respect to the hydraulic cement. When compared with other commercial water-reducing agents, there is an improvement in the water reducing capabil ty, and there is a reduction in the degree of slump loss with extended mixing time.
• the formal ehyde, condensate of the naphthalene sulfonic acid and the isocyanuric acid compounds, various organic functions of these adducts, and the number of molecules can be changed to generate various types of molecular formulae.
• the water-reduc ng agent of this invention can utilize isocyanuric acid waste fluids, a characteristic which makes it possible to produce a product at a cost which normally is less than that of presently marketed commercial water-reducing agents.
• Example 1 115 grams of naphthalene is heated to melting, and, while maintaining the temperature between 120-130° C, 115 grams of 98 percent sulfuric acid is added over a 1 hour time period. The temperature is slowly increased to 160° C over a 1 hour period, and the reaction is maintained at between 155-160° C for 4 hours or more. Following this, the reaction is allowed to cool to • approximately 100° C. To this sulfonate reaction liquor, 46 grams of tris (2-hydroxyethyl ) isocyanurate is added, and the temperature is maintained at 80-90° C, while 73 grams of 37 percent formalin are added over a 2 hour time period.
• Example 2 In a similar manner as was described in example 1, naphthalene is sulfonated by means of concentrated sulfuric acid. An approximately 30% by weight solution of tris (2-hydroxyethyl ) isocyanurate, remaining after precipitation of the isocyanurate from the mother liquor, s added in an amount of 23 grams of solids for each 115 grams of naphthalene. Subsequently, 73 grams of 37% formalin are added, and the temperature is held at between 80-90° C for 2 hours, followed by an increase to 115-120° C where it is held for approximately 5 hours, in an atmosphere of nitrogen (3-5 atmospheres), until completion of the reaction. The resulting reactant fluid is treated in the same manner as described in example 1. The results of the concrete tests using the above described product demonstrate improved performance even when the additions are made of residues including tris (hydroxyethyl ) isocyanate.
• Example 3 Tris (2-carboxyethyl ) isocyanurate is added to the completely reacted sulfonate liquor, as was the tris (2- ydroxyethyl ) isocyanurate of example 1. Condensation with formalin is accomplished under the same conditions, resulting in a substance having good performance in concrete, as shown in Table 1.
• Example 4 The 46 grams of tris (2-hydroxyethyl ) isocyanurate of example 1 is increased to 69 grams, and condensation s achieved in the same manner by the addition of 73 grams of 37% formalin under pressure in the reaction flask. Following the neutral zation of the condensate liquor, concrete tests were performed.
• Comparative Example 1 A commercial high performance water-reducing agent, the sodium salt of a beta-naphthalene sulfonic acid - formaldehyde condensation, was tested in concrete.
• Comparative Example 2 A commercial high performance water-reducing agent, the sodium salt of formaldehyde condensed melamine sulfonate, was tested in concrete.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Health & Medical Sciences (AREA)
• Ceramic Engineering (AREA)
• Materials Engineering (AREA)
• Structural Engineering (AREA)
• Curing Cements, Concrete, And Artificial Stone (AREA)
• Phenolic Resins Or Amino Resins (AREA)
• Plural Heterocyclic Compounds (AREA)

Priority Applications (3)

Applications Claiming Priority (2)

Publications (1)

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ID=17125336

Family Applications (1)

Country Status (7)

Cited By (4)

Families Citing this family (3)

Citations (2)

• 1983
  • 1983-12-27 JP JP24487883A patent/JPS60141660A/ja active Granted
• 1984
  • 1984-12-19 DE DE8585900540T patent/DE3470027D1/de not_active Expired
  • 1984-12-19 AU AU38312/85A patent/AU578925B2/en not_active Expired - Fee Related
  • 1984-12-19 WO PCT/US1984/002074 patent/WO1985002838A1/en not_active Ceased
  • 1984-12-19 BR BR8407247A patent/BR8407247A/pt unknown
  • 1984-12-19 EP EP19850900540 patent/EP0166774B1/en not_active Expired
  • 1984-12-27 CA CA000471033A patent/CA1228607A/en not_active Expired

Patent Citations (2)

Non-Patent Citations (2)

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