CN113121771A - Air-entraining modified naphthalene water reducer and preparation method thereof - Google Patents
Air-entraining modified naphthalene water reducer and preparation method thereof Download PDFInfo
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- CN113121771A CN113121771A CN201911404904.XA CN201911404904A CN113121771A CN 113121771 A CN113121771 A CN 113121771A CN 201911404904 A CN201911404904 A CN 201911404904A CN 113121771 A CN113121771 A CN 113121771A
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- 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
- C08G14/00—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00
- C08G14/02—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes
- C08G14/04—Condensation polymers of aldehydes or ketones with two or more other monomers covered by at least two of the groups C08G8/00 - C08G12/00 of aldehydes with phenols
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- 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
- C04B24/226—Sulfonated naphtalene-formaldehyde condensation products
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- 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
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/30—Water reducers, plasticisers, air-entrainers, flow improvers
- C04B2103/302—Water reducers
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- 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
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/30—Water reducers, plasticisers, air-entrainers, flow improvers
- C04B2103/304—Air-entrainers
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- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
The invention provides an air-entraining modified naphthalene water reducing agent and a preparation method thereof. Compared with the traditional naphthalene water reducer, the air-entraining modified naphthalene water reducer prepared by the invention not only obviously improves the water reducing and slump retaining effects, but also has certain air-entraining performance, and greatly improves the state of concrete.
Description
Technical Field
The invention relates to an air-entraining modified naphthalene water reducer and a preparation method thereof, belonging to the field of concrete admixtures.
Background
The concrete water reducing agent is an indispensable additive for high-performance concrete, and refers to an additive capable of reducing the mixing water consumption under the condition that the concrete and cement consumption is not changed. The concrete admixture has the largest dosage and the widest application, can reduce the water consumption, improve the strength and the durability of the concrete, and improve the workability and the fluidity of the concrete.
At present, the naphthalene water reducer with the largest amount is used in China, but the naphthalene water reducer is used as a second-generation water reducer, and compared with a third-generation polycarboxylic acid water reducer, the naphthalene water reducer has the advantages of good cement adaptability and low price, but the water reducer has much poor water reducing performance and quick concrete slump loss due to the structural defects of the naphthalene water reducer, and the naphthalene water reducer does not have certain air entraining performance like a polycarboxylic acid water reducer and can improve the state of concrete, so the application prospect of the naphthalene water reducer is influenced.
Patent CN103382092A provides a preparation method of a traditional naphthalene water reducer, which is to sulfonate naphthalene with concentrated sulfuric acid, and then condense and neutralize the sulfonated product to obtain the traditional naphthalene water reducer.
The structure of the naphthalene water reducer is changed, so that the condition that the slump loss of the concrete is too fast is improved, and the state of the concrete is improved, so that the performance requirements of the market on products can be better met. Both patent CN106117482A and patent CN106186781A mention that naphthalene water reducing agent is modified, and phosphate groups are introduced into a new structure in the method for preparing the modified naphthalene water reducing agent, so that the modified naphthalene water reducing agent has certain effect on slump retention. Patent CN106117482A discloses a modified naphthalene water reducer prepared by polymerization of sulfonated hydroxymethylphenol, amino hydroxy benzene sulfonic acid, concentrated sulfuric acid, phosphoric acid, formaldehyde, etc. Patent CN106186781A is the modified naphthalene polymer obtained by polymerization using unsaturated dicarboxylic acid, styrene, sodium hypophosphite and naphthalene homologues. Both are modified only for the purpose of improving slump retention and water-reducing rate.
Patent CN105236798A provides a preparation method of a water reducing agent, and the water reducing rate of the obtained modified naphthalene water reducing agent is improved compared with that of the traditional naphthalene water reducing agent. The patent CN105236798A discloses that sulfonated methylnaphthalene material, p-hydroxybenzene sulfonic acid material and the like are used for concentrated sulfation and then condensed with formaldehyde to obtain the modified naphthalene water reducer. The method is mainly used for improving the workability and the slump retention and solving the problem of high air content.
The existing modification technology modifies the naphthalene water reducer, improves the water reducing rate, slump retaining performance and workability of concrete, but has limited air entraining function, general water reducing rate effect and little slump loss improvement.
Disclosure of Invention
The invention provides an air-entraining modified naphthalene water reducer and a preparation method thereof, aiming at solving the problems of limited air-entraining function, general water reducing rate and quick slump loss when the existing naphthalene water reducer is applied to concrete.
The air-entraining modified naphthalene water reducer has efficient water reducing effect on concrete, has much better water reducing and slump retaining effects than the traditional naphthalene water reducer, has certain air entraining performance, and shows better adaptability to water reducers, air entraining agents, retarders and the like.
The air-entraining modified naphthalene water reducer disclosed by the invention contains phosphate radicals besides the sulfonate radicals, can improve the slump retaining effect of a product, has a certain side chain, can provide a certain steric hindrance effect to increase water reduction, and also has a certain air-entraining function.
The air-entraining modified naphthalene water reducer is obtained by polymerizing naphthalene sulfonic acid, naphthol phosphate, sodium alkyl naphthalene sulfonate and formaldehyde, wherein the molar ratio of the four substances is 1: (0.1-10): (0.05-0.1): (1.27-12.21). The alkyl group of the alkyl naphthalene sodium sulfonate is an integer of 8-14 in number of carbon atoms.
The structure of the air-entraining modified naphthalene water reducer disclosed by the invention conforms to a general formula (I);
wherein R is1And R2One is H and the other is-O-PO3Na2；
m is an integer of 1-35; s is an integer of 1-35; n is an integer of 8-14; and p is an integer of 1-10.
The naphthalene sulfonic acid is prepared by reacting concentrated sulfuric acid with naphthalene.
The preparation method of the naphthalenesulfonic acid comprises the following steps: adding naphthalene into a reaction kettle, heating to 150-160 ℃, and adding concentrated sulfuric acid for sulfonation to obtain naphthalenesulfonic acid.
The alkyl sodium naphthalene sulfonate has a structure conforming to the general formula (II)
The naphthol phosphate is prepared by reacting naphthol with phosphorus oxychloride.
The preparation method of the naphthol phosphate comprises the following specific steps: dissolving naphthol in toluene, adding phosphorus oxychloride, heating to 80-90 ℃, slowly dripping pyridine for 30min, and preserving heat for 15min after dripping. Cooling, precipitating, distilling under reduced pressure, hydrolyzing, filtering, and vacuum drying to obtain naphthol phosphate;
wherein the naphthol is 1-naphthol or 2-naphthol.
The preparation method of the air-entraining modified naphthalene water reducer comprises the following specific steps:
and (2) after controlling the temperature to be 95-100 ℃, adding naphthalenesulfonic acid, naphthol phosphate and alkyl sodium naphthalenesulfonate, dropwise adding formaldehyde for 30min, reacting for 4-10 h after dropwise adding, cooling after the reaction is finished, and adjusting the pH to 6-8 by using sodium hydroxide to obtain the air entraining modified naphthalene water reducer.
The molecular structure of the air-entraining modified naphthalene water reducer is greatly different from that of the traditional naphthalene water reducer. Compared with the traditional naphthalene-based high-efficiency water reducing agent, the product of the invention has good water reducing and slump retaining effects, also has a certain air entraining effect, and shows good adaptability to water reducing agents, air entraining agents, retarders and the like.
Detailed Description
The technical solutions of the present invention are further described in detail with reference to the following examples, which are provided by way of illustration and are intended to enable persons skilled in the art to understand the contents of the present invention and to implement the present invention, but the examples do not limit the scope of the present invention. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
In the application embodiment of the invention, the adopted cement is 52.5 R.P.II cement for the small open field. The cement mortar test is carried out according to the relevant regulations of national standard GB8076-2008 'concrete admixture'. The raw materials used in the examples are all commercial products, wherein the reagents (analytically pure) and the organic solvents (chemically pure) are all purchased from national drug group chemical reagents, and the naphthalene-based superplasticizer is from Jiangsu Subo New materials, Inc.
Synthesis example 1
(1) Preparation of naphthol phosphate: dissolving 1mol of 2-naphthol in 300ml of toluene, adding 1mol of phosphorus oxychloride, heating to 80-90 ℃, slowly dripping 1mol of pyridine for 30min, and preserving heat for 15min after dripping. Cooling, precipitating, distilling under reduced pressure, hydrolyzing, filtering, and vacuum drying to obtain 2-naphthol phosphate.
(2) Preparing an air-entraining modified naphthalene water reducer: adding 0.1mol of naphthalene into a reaction kettle, heating to 150-160 ℃, adding 0.13mol of concentrated sulfuric acid for sulfonation to obtain beta-naphthalenesulfonic acid, then cooling to 95-100 ℃, adding 0.01mol of 2-naphthol phosphate and 0.005mol of sodium dodecyl naphthalene sulfonate, dropwise adding 0.127mol of formaldehyde for 30min, reacting for 4h after dropwise addition, cooling after the reaction is finished, and adjusting the pH to 6-8 by using sodium hydroxide to obtain the air entraining modified naphthalene water reducer.
Synthesis example 2
(1) Preparation of naphthol phosphate: dissolving 1mol of 2-naphthol in 300ml of toluene, adding 1mol of phosphorus oxychloride, heating to 80-90 ℃, slowly dripping 1mol of pyridine for 30min, and preserving heat for 15min after dripping. Cooling, precipitating, distilling under reduced pressure, hydrolyzing, filtering, and vacuum drying to obtain 2-naphthol phosphate.
(2) Preparing an air-entraining modified naphthalene water reducer: adding 0.1mol of naphthalene into a reaction kettle, heating to 150-160 ℃, adding 0.13mol of concentrated sulfuric acid for sulfonation to obtain beta-naphthalenesulfonic acid, then cooling to 95-100 ℃, adding 0.05mol of 2-naphthol phosphate and 0.006mol of sodium octaalkylnaphthalenesulfonate, dropwise adding 0.172mol of formaldehyde for 30min, reacting for 6h after dropwise adding is finished, cooling after the reaction is finished, and adjusting the pH value to 6-8 by using sodium hydroxide to obtain the air entraining modified naphthalene water reducer.
Synthesis example 3
(1) Preparation of naphthol phosphate: dissolving 1mol of 2-naphthol in 300ml of toluene, adding 1mol of phosphorus oxychloride, heating to 80-90 ℃, slowly dripping 1mol of pyridine for 30min, and preserving heat for 15min after dripping. Cooling, precipitating, distilling under reduced pressure, hydrolyzing, filtering, and vacuum drying to obtain 2-naphthol phosphate.
(2) Preparing an air-entraining modified naphthalene water reducer: adding 0.1mol of naphthalene into a reaction kettle, heating to 150-160 ℃, adding 0.13mol of concentrated sulfuric acid for sulfonation to obtain beta-naphthalenesulfonic acid, then cooling to 95-100 ℃, adding 0.1mol of 2-naphthol phosphate and 0.007mol of sodium dodecyl sulfate, dropwise adding 0.228mol of formaldehyde for 30min, reacting for 8h after dropwise addition, cooling after the reaction is finished, and adjusting the pH to 6-8 by using sodium hydroxide to obtain the air entraining modified naphthalene water reducer.
Synthesis example 3
(1) Preparation of naphthol phosphate: dissolving 1mol of 1-naphthol in 300ml of toluene, adding 1mol of phosphorus oxychloride, heating to 80-90 ℃, slowly dripping 1mol of pyridine for 30min, and preserving heat for 15min after dripping. Cooling, precipitating, distilling under reduced pressure, hydrolyzing, filtering, and vacuum drying to obtain 1-naphthol phosphate.
(2) Preparing an air-entraining modified naphthalene water reducer: adding 0.1mol of naphthalene into a reaction kettle, heating to 150-160 ℃, adding 0.13mol of concentrated sulfuric acid for sulfonation to obtain beta-naphthalenesulfonic acid, then cooling to 95-100 ℃, adding 0.5mol of 1-naphthol phosphate and 0.008mol of sodium tetradecyl naphthalenesulfonate, dropwise adding 0.669mol of formaldehyde for 30min, reacting for 10h after dropwise adding, cooling after the reaction is finished, and adjusting the pH to 6-8 by using sodium hydroxide to obtain the air entraining modified naphthalene water reducer.
Synthesis example 4
(1) Preparation of naphthol phosphate: dissolving 1mol of 1-naphthol in 300ml of toluene, adding 1mol of phosphorus oxychloride, heating to 80-90 ℃, slowly dripping 1mol of pyridine for 30min, and preserving heat for 15min after dripping. Cooling, precipitating, distilling under reduced pressure, hydrolyzing, filtering, and vacuum drying to obtain 1-naphthol phosphate.
(2) Preparing an air-entraining modified naphthalene water reducer: adding 0.1mol of naphthalene into a reaction kettle, heating to 150-160 ℃, adding 0.13mol of concentrated sulfuric acid for sulfonation to obtain beta-naphthalenesulfonic acid, then cooling to 95-100 ℃, adding 1mol of 1-naphthol phosphate and 0.009mol of tetradecyl naphthalene sodium sulfonate, dropwise adding 1.220mol of formaldehyde for 30min, reacting for 7h after dropwise addition, cooling after the reaction is finished, and adjusting the pH value to 6-8 by using sodium hydroxide to obtain the air-entraining modified naphthalene water reducer.
Synthesis example 5
(1) Preparation of naphthol phosphate: dissolving 1mol of 2-naphthol in 300ml of toluene, adding 1mol of phosphorus oxychloride, heating to 80-90 ℃, slowly dripping 1mol of pyridine for 30min, and preserving heat for 15min after dripping. Cooling, precipitating, distilling under reduced pressure, hydrolyzing, filtering, and vacuum drying to obtain 2-naphthol phosphate.
(2) Preparing an air-entraining modified naphthalene water reducer: adding 0.1mol of naphthalene into a reaction kettle, heating to 150-160 ℃, adding 0.13mol of concentrated sulfuric acid for sulfonation to obtain beta-naphthalenesulfonic acid, then cooling to 95-100 ℃, adding 1mol of 2-naphthol phosphate and 0.01mol of tetradecyl naphthalene sodium sulfonate, dropwise adding 1.221mol of formaldehyde for 30min, reacting for 6h after dropwise addition, cooling after the reaction is finished, and adjusting the pH value to 6-8 by using sodium hydroxide to obtain the air-entraining modified naphthalene water reducer.
Comparative example 1
A water-reducing agent was synthesized by following substantially the same procedure as in Synthesis example 1 except that: no naphthol phosphate is added, but the condensation reaction is carried out on the naphthalene sulfonic acid, the alkyl sodium naphthalene sulfonate and the formaldehyde.
Comparative example 2
A water-reducing agent was synthesized by following substantially the same procedure as in Synthesis example 1 except that: sodium alkylnaphthalenesulfonate is not added, but only naphthalenesulfonic acid, naphthol phosphate and formaldehyde are subjected to condensation reaction.
Comparative example 3
A water-reducing agent was synthesized by following substantially the same procedure as in Synthesis example 1 except that: naphthol is not phosphorylated, but naphthol, naphthalenesulfonic acid, sodium alkylnaphthalenesulfonate and formaldehyde are subjected to a condensation reaction.
Comparative example 4
The naphthalene series high-efficiency water reducing agent is provided by Jiangsu Subo new material company Limited.
Application example 1
The air-entraining modified naphthalene water reducing agents prepared in synthetic examples 1 to 5 and comparative examples 1 to 4 were subjected to a cement mortar fluidity test. The fluidity of the cement mortar is carried out according to national standard GB/T8077 and 2012, the homogeneity test method of the concrete admixture, and the comparison results are shown in Table 1.
TABLE 1 mortar fluidity test comparison
From the results shown in table 1, it can be seen that the air-entraining modified naphthalene water reducing agent prepared by the present invention has the initial air content much higher than that of the conventional naphthalene water reducing agent, the mixing amount is much smaller than that of the conventional naphthalene water reducing agent, and the mortar loss after 30min is much better than that of the conventional naphthalene water reducing agent under the condition of the same initial fluidity in cement mortar.
As can be seen from comparative examples 1 and 3, the initial gas content is much better than that of the traditional naphthalene series, because the sodium alkyl naphthalene sulfonate is added, the air entraining performance is better; from comparative example 2, it can be seen that the mortar flow loss after 30min is small, which indicates that the mortar has a certain slump retaining property after the introduction of phosphate groups.
The air-entraining modified naphthalene water reducer prepared by the invention not only obviously improves the water reducing and slump retaining effects, but also has certain air-entraining performance, and greatly improves the state of concrete.
Claims (8)
1. An air-entraining modified naphthalene water reducer is characterized in that the air-entraining modified naphthalene water reducer is obtained by polymerizing naphthalene sulfonic acid, naphthol phosphate, alkyl naphthalene sodium sulfonate and formaldehyde; the molar ratio of these four substances is 1: (0.1-10): (0.05-0.1): (1.27 to 12.21); the alkyl group of the alkyl naphthalene sodium sulfonate is an integer of 8-14 in number of carbon atoms.
2. The air-entraining modified naphthalene based water reducer according to claim 1 which is characterized in that the structure of the air-entraining modified naphthalene based water reducer conforms to the general formula (I);
wherein R is1Or R2Is H, the other is-O-PO3Na2；
m is an integer of 1-35; s is an integer of 1-35; n is an integer of 8-14; and p is an integer of 1-10.
3. The air-entraining modified naphthalene based water reducer according to claim 1 characterized in that said naphthalene sulfonic acid is prepared by reacting concentrated sulfuric acid with naphthalene.
4. The air-entraining modified naphthalene based water reducer according to claim 3, characterized in that the preparation method of the naphthalene sulfonic acid is as follows: adding naphthalene into a reaction kettle, heating to 150-160 ℃, and adding concentrated sulfuric acid for sulfonation to obtain naphthalenesulfonic acid.
5. The air entraining type modified naphthalene water reducing agent according to claim 1, characterized in that the naphthol phosphate is prepared by reacting naphthol with phosphorus oxychloride.
6. The air-entraining modified naphthalene water reducer according to claim 5, which is characterized in that the preparation method of the naphthol phosphate comprises the following specific steps: dissolving naphthol in toluene, adding phosphorus oxychloride, heating to 80-90 ℃, slowly dripping pyridine for 30min, and preserving heat for 15min after dripping; cooling, precipitating, distilling under reduced pressure, hydrolyzing, filtering, and vacuum drying to obtain naphthol phosphate;
wherein the naphthol is 1-naphthol or 2-naphthol.
7. The air-entraining modified naphthalene based water reducer according to claim 1 wherein the sodium alkyl naphthalene sulfonate has a structure according to the general formula (II)
8. The preparation method of the air-entraining modified naphthalene water reducer as claimed in any one of claims 1 to 7, which is characterized by comprising the following specific steps: adding naphthalenesulfonic acid, naphthol phosphate and alkyl sodium naphthalenesulfonate at the temperature of 95-100 ℃, dropwise adding formaldehyde for 30min, reacting for 4-10 h after dropwise adding, cooling after the reaction is finished, and adjusting the pH value to 6-8 by using sodium hydroxide to obtain the air entraining modified naphthalene water reducer.
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