KR20210014784A - Anhydrodugar alcohol composition having acid functional group added thereto and dispersant for concrete comprising the same, and concrete composition comprising the dispersant - Google Patents

Abstract

The present invention relates to an anhydrosugar alcohol composition to which an acid functional group is added, a dispersant for concrete comprising the same, and a concrete composition comprising the dispersant. More specifically, an anhydrosugar alcohol composition or a crosslinked anhydrosugar alcohol composition is reacted with an acidic substance in a specific weight ratio. The anhydrosugar alcohol composition comprises (i) a monoanhydrosugar alcohol, (ii) a dianhydrosugar alcohol, and (iii) a polymer of at least one of the monoanhydrosugar alcohol and the dianhydrosugar alcohol. The present invention relates to an acid-added anhydrosugar alcohol composition, wherein the content of a dianhydrosugar alcohol is within a specific content range, a concrete dispersant comprising the same, wherein the dispersibility and physical properties of concrete can be improved and economic feasibility can be improved through cost reduction, and a concrete composition comprising the dispersant.

Description

Anhydrodugar alcohol composition having acid functional group added thereto and dispersant for concrete comprising the same, and concrete composition comprising the dispersant}

The present invention relates to an anhydrosugar alcohol composition to which an acid functional group is added, a dispersant for concrete comprising the same, and a concrete composition comprising the dispersant, and more specifically, to an anhydrosugar alcohol composition or a crosslinked anhydrosugar alcohol composition and an acidic It is prepared by reacting a substance in a specific weight ratio, wherein the anhydrosugar alcohol composition comprises a polymer of at least one of (i) a monosaccharide alcohol, (ii) a dianhydrosugar alcohol, and (iii) a monohydrosugar alcohol and a dianhydrosugar alcohol, wherein , An acid-added anhydrosugar alcohol composition in which the content of dianhydrosugar alcohol is within a specific content range, and a dispersant for concrete that includes the same and improves the dispersibility and physical properties of concrete as well as improves economic efficiency through cost reduction, and It relates to a concrete composition containing this dispersant.

Concrete is a main material for modern construction and civil works, and various additives are used to improve its strength and dispersibility. As such additives for concrete, there have been attempts to increase economic efficiency by using copolymer-modified lignin derived from by-products of the papermaking process (e.g., Korean Patent Laid-Open Nos. 10-2015-0101815, 10-2013-0012301 Etc).

However, the above-described conventional additives for concrete are still insufficient in terms of improving the dispersibility and properties of concrete. Therefore, there is a need to develop a dispersant for concrete that can replace an expensive organic dispersant that has been used in the past, improve economic efficiency through cost reduction, and at the same time improve dispersing power and properties of concrete.

Hydrogenated sugar (also referred to as “sugar alcohol”) refers to a compound obtained by adding hydrogen to a reducing end group of a sugar, and generally has the formula of HOCH2(CHOH)nCH2OH (where n is an integer of 2 to 5). It has, and is classified into tetritol, pentitol, hexitol, and heptitol (4, 5, 6 and 7 carbon atoms, respectively) according to the number of carbon atoms. Among them, hexitol having 6 carbon atoms includes sorbitol, mannitol, iditol, galactitol, and the like, and sorbitol and mannitol are particularly effective substances.

Anhydrosugar alcohol has the form of a diol having two hydroxy groups in the molecule, and can be prepared using hexitol derived from starch (e.g., Korean Patent No. 10-1079518, Korean Patent Laid-Open No. 10 -2012-0066904). Since anhydrosugar alcohol is an eco-friendly material derived from renewable natural resources, research on its manufacturing method has been underway with much interest from a long time ago. Among these anhydrosugar alcohols, isosorbide prepared from sorbitol has the widest industrial application range.

The use of anhydrosugar alcohol is very diverse, such as treatment of heart and vascular diseases, adhesives for patches, pharmaceuticals such as mouthwash, solvents for compositions in the cosmetic industry, and emulsifiers in the food industry. In addition, it can raise the glass transition temperature of polymer materials such as polyester, PET, polycarbonate, polyurethane, epoxy resin, etc., has the effect of improving the strength of these materials, and is an eco-friendly material derived from natural products. useful. In addition, it is known that it can be used as an eco-friendly solvent for adhesives, eco-friendly plasticizers, biodegradable polymers, and water-soluble lacquers.

As such, anhydrosugar alcohol is receiving a lot of attention due to its various possibilities, and its use in actual industries is gradually increasing.

An object of the present invention is an anhydrosugar alcohol-based composition capable of improving the dispersing power and physical properties of concrete while improving economic efficiency through cost reduction when used as a dispersant component for concrete, and a dispersant for concrete containing the same, and the dispersant. It is to provide a concrete composition containing.

In order to solve the above technical problem, the present invention is an acid-added anhydrosugar alcohol composition prepared from the reaction of an anhydrosugar alcohol composition or a crosslinked anhydrosugar alcohol composition with an acidic substance, and the amount of the acidic substance used in the reaction This, based on 100 parts by weight of the anhydrosugar alcohol composition, 0.2 parts by weight to 19 parts by weight, the anhydrosugar alcohol composition is (i) anhydrosugar alcohol; (ii) dianhydrosugar alcohol; And (iii) one or more polymers of dianhydrosugar alcohol and dianhydrosugar alcohol; wherein the content of dianhydrosugar alcohol in the anhydrosugar alcohol composition is greater than 5% by weight, based on 100% by weight of the total anhydrosugar alcohol composition, and 95 An acid-added anhydrosugar alcohol composition of less than a weight percent is provided.

According to another aspect of the present invention, a method of preparing an acid-added anhydrosugar alcohol composition, comprising the step of reacting an anhydrosugar alcohol composition or a crosslinked anhydrosugar alcohol composition with an acidic substance, the acidic substance used in the reaction The amount of, based on 100 parts by weight of the anhydrosugar alcohol composition, is 0.2 parts by weight to 19 parts by weight, and the anhydrosugar alcohol composition comprises (i) a monohydrosugar alcohol; (ii) dianhydrosugar alcohol; And (iii) one or more polymers of dianhydrosugar alcohol and dianhydrosugar alcohol; wherein the content of dianhydrosugar alcohol in the anhydrosugar alcohol composition is greater than 5% by weight, based on 100% by weight of the total anhydrosugar alcohol composition, and 95 A method of making an acid-added anhydrosugar alcohol composition that is less than weight percent is provided.

According to another aspect of the present invention, a dispersant for concrete is provided, comprising 1 to 29 parts by weight of the acid-added anhydrosugar alcohol composition of the present invention based on a total of 100 parts by weight of the dispersant.

According to another aspect of the invention, cement; And a concrete composition containing; and the dispersant for concrete of the present invention is provided.

When the acid-added anhydrosugar alcohol composition according to the present invention is used as a dispersant component for concrete, it can replace the expensive organic dispersant that has been used in the past, thereby improving economic efficiency through cost reduction, and at the same time, dispersing power and physical properties of concrete. Can improve.

Hereinafter, the present invention will be described in more detail.

[Acid-added anhydrosugar alcohol composition]

The acid-added anhydrosugar alcohol composition of the present invention is prepared from the reaction of an anhydrosugar alcohol composition or a crosslinked anhydrosugar alcohol composition with an acidic substance.

The anhydrosugar alcohol composition comprises i) a monohydrosugar alcohol, ii) a dianhydrosugar alcohol, and iii) a polymer of at least one of a monohydrosugar alcohol and a dianhydrosugar alcohol.

Anhydrosugar alcohol can be prepared by dehydrating a hydrogenated sugar derived from a natural product. Hydrogenated sugar (also referred to as “sugar alcohol”) refers to a compound obtained by adding hydrogen to a reducing end group of a sugar, and generally HOCH ₂ (CHOH) _n CH ₂ OH (where n is an integer of 2 to 5 ), and classified into tetritol, pentitol, hexitol and heptitol (4, 5, 6 and 7 carbon atoms, respectively) according to the number of carbon atoms. Among them, hexitol having 6 carbon atoms includes sorbitol, mannitol, iditol, galactitol, and the like, and sorbitol and mannitol are particularly effective substances.

One or more of a monohydric alcohol, a dianhydrosugar alcohol, and one or more polymers of a monohydrosugar alcohol and a dianhydrosugar alcohol (i.e., a polymer of a monohydrosugar alcohol and/or a dianhydrosugar alcohol), preferably Two or more, more preferably all of them, can be obtained in the process of preparing anhydrosugar alcohol by dehydrating a hydrogenated sugar (eg, hexitol such as sorbitol, mannitol, or iditol).

Anhydrosugar alcohol is an anhydrosugar alcohol formed by removing one water molecule from the inside of a hydrogenated sugar, and has a tetraol form with four hydroxyl groups in the molecule.

In the present invention, the type of the monohydric alcohol is not particularly limited, but preferably may be monohydric hexitol, more specifically 1,4-anhydrohexitol, 3,6-anhydrohexitol , 2,5-anhydrohexitol, 1,5-anhydrohexitol, 2,6-anhydrohexitol, or a mixture of two or more thereof.

A dianhydrosugar alcohol is an anhydrosugar alcohol formed by removing two water molecules from the inside of a hydrogenated sugar.It has a diol form having two hydroxyl groups in the molecule, and can be prepared using hexitol derived from starch. Imusudan alcohol is an eco-friendly material derived from renewable natural resources, and research on its manufacturing method has been underway with much interest from a long time ago. Among these dianhydrosugar alcohols, isosorbide prepared from sorbitol has the widest industrial application range.

In the present invention, the type of the dianhydrosugar alcohol is not particularly limited, but preferably may be dianhydrosugar hexitol, and more specifically, 1,4-3,6-dianhydrohexitol. The 1,4-3,6-dianhydrohexitol may be isosorbide, isomannide, isoidide, or a mixture of two or more thereof.

In the present invention, at least one polymer of the dianhydrose alcohol and the dianhydrose alcohol (i.e., the polymer of the dianhydrose alcohol and/or the dianhydrose alcohol) is a condensation reaction of a dianhydrosugar alcohol, a condensation reaction of a dianhydrose alcohol, or a dianhydrose It may be a condensation polymer prepared from a condensation reaction of alcohol and dianhydrosugar alcohol. In the condensation reaction, the condensation position and the condensation sequence between the monomers are not particularly limited, and may be selected without limitation within a range generally predictable by a person skilled in the art.

In one embodiment of the present invention, for example, one or more polymers of the monohydric alcohol and dianhydrose alcohol may be one or more selected from the group consisting of polymers represented by the following Chemical Formulas 1 to 5, but this is between monomers in the condensation reaction. It is only an example of a polymer prepared according to the condensation position and the condensation sequence, but is not limited thereto.

[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 1 to 5,

a to d are each independently an integer of 0 to 25 (specifically, an integer of 0 to 10, more specifically an integer of 0 to 5), provided that a+b+c+d is 2 to 100 (specifically Examples are 2 to 50, more specifically, 2 to 20).

The anhydrosugar alcohol composition contains the dianhydrosugar alcohol in an amount of more than 5% to less than 95% by weight, based on 100% by weight of the total composition. If the dianhydrosugar alcohol content in the anhydrosugar alcohol composition is 5% by weight or less or 95% by weight or more, a concrete composition may be prepared using a dispersant for concrete containing an acid-added anhydrosugar alcohol composition prepared from such anhydrosugar alcohol composition. In this case, not only the dispersion power of the concrete is poor, but also the workability is poor due to the high viscosity.

In one embodiment, the anhydrosugar alcohol composition contains 1 to 50% by weight, specifically 2 to 40% by weight, and more specifically 3 to 30% by weight, based on 100% by weight of the total composition. , More specifically, it may be included in 4 to 20% by weight, even more specifically 5 to 20% by weight.

In one embodiment, the anhydrosugar alcohol composition includes, for example, 6 to 94% by weight, specifically 7 to 93% by weight, and more specifically 8 to 92% by weight, based on 100% by weight of the total composition. , More specifically, it may be included in 9 to 91% by weight, even more specifically 10 to 90% by weight.

In one embodiment, the anhydrosugar alcohol composition includes, for example, 1 to 93% by weight, specifically 2 to 92% by weight, of one or more polymers of the monohydric alcohol and dianhydrosugar alcohol based on 100% by weight of the total composition. Specifically, it may be included in 3 to 90% by weight, more specifically 4 to 85% by weight, even more specifically 5 to 80% by weight, and even more specifically 5 to 70% by weight.

In one embodiment, the number average molecular weight (Mn: g/mol) of the anhydrosugar alcohol composition may be 160 or more, 165 or more, 170 or more, or 174 or more, and also 445 or less, 440 or less, 430 or less, 420 or less, 410 It may be less than or equal to 400 or less than or equal to 399.

In one embodiment, the number average molecular weight (Mn) of the anhydrosugar alcohol composition may be 160 to 445, specifically 165 to 440, more specifically 170 to 400, and even more specifically It may be 175 to 399, and more specifically, it may be 175 to 395.

In one embodiment, the polydispersity index (PDI) of the anhydrosugar alcohol composition may be 1.25 or more, 1.30 or more, or 1.33 or more. In addition, it may be 3.15 or less, 3.10 or less, 3.0 or less, 2.90 or less, 2.80 or less, or 2.75 or less.

In one embodiment, the polydispersity index (PDI) of the anhydrosugar alcohol composition may be 1.25 to 3.15, specifically 1.30 to 3.10, more specifically 1.30 to 3.0, and more specifically May be 1.33 to 2.80, and even more specifically 1.34 to 2.75.

In one embodiment, the hydroxyl value (Hydroxyl value: mgKOH/g) of the anhydrosugar alcohol composition may be 645 or more, 650 or more, 655 or more, 659 or more, or 660 or more, and also 900 or less, 895 or less, 892 or less, or May be 891 or less.

In one embodiment, the hydroxyl value (Hydroxyl value) of the anhydrosugar alcohol composition may be 645 to 900, specifically 650 to 900 or less, more specifically 655 to 895, and more specifically May be 660 to 892, and even more specifically 660 to 891.

In a preferred embodiment, the anhydrosugar alcohol composition comprises (i) a number average molecular weight (Mn) of 160 to 445, (ii) a polydispersity index (PDI) of 1.25 to 3.15, and (iii) 645 to 900 mgKOH/g It satisfies the hydroxyl value of

According to one embodiment of the present invention, the anhydrosugar alcohol composition satisfying the conditions of the number average molecular weight (Mn), polydispersity index (PDI), and hydroxyl value described above is, the -OH group per molecule in the composition. An average number of 2.6 to 5.0 may be additionally satisfied.

In this embodiment, the average number of -OH groups per molecule in the anhydrosugar alcohol composition may be 2.6 or more, 2.7 or more, or 2.8 or more, and also 5.0 or less, 4.9 or less, 4.8, 4.7 or less or 4.6 It can be no more than dogs.

More specifically, the average number of -OH groups per molecule in the anhydrosugar alcohol composition may be 2.7 to 4.9, more specifically 2.7 to 4.7, and even more specifically 2.8 to 4.6. have.

In one embodiment, the anhydrosugar alcohol composition may be prepared by heating a hydrogenated sugar under an acid catalyst for dehydration reaction, and thin film distillation of the obtained dehydration reaction product. More specifically, the dehydration reaction may be carried out by heating a hydrogenated sugar such as sorbitol to 125 to 150° C. under an acid catalyst such as sulfuric acid, for example, at a reduced pressure of 25 to 40 torr, and the resulting dehydration reaction is required. After neutralization with a Si base, the thin film may be distilled at a temperature of 150 to 175° C. under a reduced pressure condition of 2 mbar or less using a thin film still (SPD), but is not limited thereto.

In the present invention, the crosslinked anhydrosugar alcohol composition is prepared by reacting the anhydrosugar alcohol composition described above with a crosslinking agent.

In one embodiment, the crosslinking agent is 1 selected from the group consisting of epihalohydrin (e.g., epichlorohydrin), diamine compounds, dicarboxylate compounds, diester compounds, or mixtures thereof. It is possible to use species or a mixture of two or more.

In one embodiment, the amount of the crosslinking agent used in the preparation of the crosslinked anhydrosugar alcohol composition may be 0.1 to 29 parts by weight, specifically 0.2 to 25 parts by weight, based on 100 parts by weight of the anhydrosugar alcohol composition. Specifically, it may be 0.5 to 20 parts by weight, and more specifically, it may be 1 to 10 parts by weight.

In one embodiment, the crosslinked anhydrosugar alcohol composition is heated by heating a mixture of an anhydrosugar alcohol composition and a crosslinking agent in the presence of a catalyst (eg, a base catalyst such as NaOH) (eg, 2 to 10 at 80 to 140°C). Time).

In the present invention, as the acidic substance, the hydroxy group of one or more polymers of dianhydrosugar alcohol, dianhydrosugar alcohol, and/or dianhydrosugar alcohol and dianhydrosugar alcohol in the anhydrosugar alcohol composition or crosslinked anhydrosugar alcohol composition described above Compounds capable of reacting and introducing acid functional groups into their molecular structures are used.

The acidic substances are organic acids, inorganic acids, or mixtures thereof, and they have one or more acid functional groups. Specifically, the acidic substance is carboxylic acid, carboxylic acid anhydride, carboxylic acid salt, sulfonic acid, sulfonic acid anhydride, sulfonic acid salt, sulfinic acid, sulfonic acid anhydride, sulfinic acid salt, phosphoric acid, phosphate, phosphorous acid, phosphorous acid It may be one or a mixture of two or more selected from the group consisting of salts, nitric acid, nitrate salts, nitrous acid, nitrite salts, sulfuric acid, sulfuric acid salts, sulfurous acid, sulfite salts, or mixtures thereof.

In one embodiment, the acidic substance is maleic acid, maleic anhydride (maleic anhydride), maleic acid salt, tripolyphosphoric acid, tripolyphosphate salt (eg, sodium tripolyphosphate), sulfonic acid, sulfonic acid anhydride, sulfonic acid salt, or a mixture thereof. It may be one or a mixture of two or more selected from the group consisting of.

In the present invention, the amount of the acidic substance used in the reaction with the anhydrosugar alcohol composition or the crosslinked anhydrosugar alcohol composition is based on 100 parts by weight of the anhydrosugar alcohol composition (when a crosslinked anhydrosugar alcohol composition is used, crosslinking Based on 100 parts by weight of the previous anhydrosugar alcohol composition), from 0.2 parts by weight to 19 parts by weight. When the amount of the acidic substance used in the reaction is less than 0.2 parts by weight or more than 19 parts by weight based on 100 parts by weight of the anhydrosugar alcohol composition, concrete using a dispersant for concrete containing the acid-added anhydrosugar alcohol composition thus prepared When the composition is prepared, not only the dispersing power of the concrete is poor, but also the workability is poor due to the high viscosity.

In one embodiment, the amount of the acidic substance used in the reaction with the anhydrosugar alcohol composition or the crosslinked anhydrosugar alcohol composition is 0.3 parts by weight or more, 0.4 parts by weight or more, or 0.5 parts by weight based on 100 parts by weight of the anhydrosugar alcohol composition. May be more than 18 parts by weight, 17 parts by weight or less, 16 parts by weight or less, 15 parts by weight or less, 14 parts by weight or less, 13 parts by weight or less, 12 parts by weight or less, 11 parts by weight or less, or 10 parts by weight or less have.

In one embodiment, the amount of the acidic substance used in the reaction with the anhydrosugar alcohol composition or the crosslinked anhydrosugar alcohol composition is, based on 100 parts by weight of the anhydrosugar alcohol composition, 0.3 to 18 parts by weight, 0.3 to 15 parts by weight. It may be parts by weight, 0.4 parts by weight to 15 parts by weight, 0.5 parts by weight to 15 parts by weight, or 0.5 parts by weight to 10 parts by weight.

According to another aspect of the present invention, a method of preparing an acid-added anhydrosugar alcohol composition, comprising the step of reacting an anhydrosugar alcohol composition or a crosslinked anhydrosugar alcohol composition with an acidic substance, the acidic substance used in the reaction The amount of, based on 100 parts by weight of the anhydrosugar alcohol composition, is 0.2 parts by weight to 19 parts by weight, and the anhydrosugar alcohol composition comprises (i) a monohydrosugar alcohol; (ii) dianhydrosugar alcohol; And (iii) one or more polymers of dianhydrosugar alcohol and dianhydrosugar alcohol; wherein the content of dianhydrosugar alcohol in the anhydrosugar alcohol composition is greater than 5% by weight, based on 100% by weight of the total anhydrosugar alcohol composition, and 95 A method of making an acid-added anhydrosugar alcohol composition that is less than weight percent is provided.

In one embodiment, the acid-added anhydrosugar alcohol composition of the present invention is prepared by mixing and heating an anhydrosugar alcohol composition and an acidic substance in the presence of a catalyst (e.g., a base catalyst such as NaOH or an acid catalyst such as HCl). For example, it can be prepared by reacting at 60 to 140° C. for 2 to 10 hours).

In another embodiment, the acid-added anhydrosugar alcohol composition of the present invention is prepared by heating the anhydrosugar alcohol composition with a crosslinking agent in the presence of a catalyst (e.g., a base catalyst such as NaOH) (e.g., at 80 to 140°C. After making a crosslinked anhydrosugar alcohol composition (for 2 to 10 hours), cooling it (for example, below 60°C), an acidic substance is added thereto and heating for 2 to 10 hours (for example, 60 To 140° C. for 2 to 10 hours).

In one embodiment, the number average molecular weight of the acid-added anhydrosugar alcohol composition of the present invention may be 200 to 4,000 g/mol when prepared by reacting an uncrosslinked anhydrosugar alcohol composition with an acid. When the sugar alcohol composition is reacted with an acid, it may be 200 to 6,000 g/mol, but is not limited thereto.

[Dispersant for concrete and concrete composition containing the same]

When the acid-added anhydrosugar alcohol composition of the present invention as described above is used as a dispersant for concrete, the acid functional group part is dissociated and has a negative charge, so that the dispersibility of the concrete composition can be improved. Further, by crosslinking the anhydrosugar alcohol composition with a crosslinking agent and then introducing an acid functional group, a dispersant for concrete with improved physical properties can be obtained.

Accordingly, according to another aspect of the present invention, there is provided a dispersant for concrete comprising the acid-added anhydrosugar alcohol composition of the present invention.

In the dispersant for concrete of the present invention, the acid-added anhydrosugar alcohol composition of the present invention is contained in an amount of 1 to 29 parts by weight, based on a total of 100 parts by weight of the dispersant. If the content of the acid-added anhydrosugar alcohol composition in the dispersant for concrete is less than 1 part by weight based on the total 100 parts by weight of the dispersant, the effect of using the acid-added anhydrosugar alcohol composition of the present invention cannot be expected. Conversely, it exceeds 29 parts by weight. When a concrete composition is manufactured using such a dispersant for concrete, not only the dispersing power of the concrete is poor, but also the workability is poor due to the high viscosity.

In one embodiment, the content of the acid-added anhydrosugar alcohol composition in the dispersant for concrete is 2 parts by weight or more, 3 parts by weight or more, 4 parts by weight or more, 5 parts by weight or more, 6 parts by weight, based on a total of 100 parts by weight of the dispersant. Parts by weight or more, 7 parts by weight or more, 8 parts by weight or more, 9 parts by weight or more, or 10 parts by weight or more, and also 28 parts by weight or less, 27 parts by weight or less, 26 parts by weight or less, 25 parts by weight or less, 24 parts by weight or less , 23 parts by weight or less, 22 parts by weight or less, 21 parts by weight or less, or 20 parts by weight or less.

In one embodiment, the content of the acid-added anhydrosugar alcohol composition in the dispersant for concrete is 1 to 25 parts by weight, 2 to 25 parts by weight, 3 to 25 parts by weight, based on the total 100 parts by weight of the dispersant. Parts, 4 parts by weight to 20 parts by weight, or 5 parts by weight to 20 parts by weight.

In the dispersant for concrete of the present invention, in addition to the acid-added anhydrosugar alcohol composition, one or more components commonly used to exhibit the function of a dispersant for concrete may be further included. For example, the dispersant for concrete of the present invention may further include a surfactant (more specifically, an anionic surfactant), but is not limited thereto.

According to another aspect of the invention, cement; And a concrete composition containing; and the dispersant for concrete of the present invention is provided.

In one embodiment, the content of the dispersant for concrete in the concrete composition may be 0.2 to 10 parts by weight based on 100 parts by weight of cement, and more specifically, 0.3 to 8 parts by weight, 0.4 to 5 parts by weight, or 0.5 to 3 It may be parts by weight, but is not limited thereto.

The concrete composition of the present invention, in addition to the above components, may further include one or more aggregates, such as sand, crushed sand, or gravel, which are usually added to water and concrete compositions, and in addition, it is usually added to the concrete composition. One or more admixtures (here, admixtures refer to materials present in an amount of 1% by weight or more based on the total 100% by weight of the concrete composition, for example, slag, fly ash, etc.) to achieve the object of the present invention. It may further include within the range.

Hereinafter, the present invention will be described in more detail through Examples and Comparative Examples. However, the scope of the present invention is not limited to these.

[Example]

<Preparation of an acid-added anhydrosugar alcohol composition>

Example A1: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of alcohol composition and anhydrous Maleic acid 0.5 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

1,000 g of sorbitol powder (D-sorbitol) was placed in a three-neck glass reactor equipped with a stirrer, and the internal temperature of the reactor was heated to 110° C. under a vacuum condition of 3 mmHg to dissolve, and then 5 g of concentrated sulfuric acid (95%) and methane sulfonic acid ( 70%) 10 g of mixed acid was added, and the reaction temperature was raised to 145°C. Thereafter, dehydration was performed under vacuum for 3 hours to convert sorbitol to isosorbide, an anhydrosugar alcohol. Then, after lowering the temperature of the reactor to 110° C., 20 g of sodium hydroxide solution (50%) was added to the dehydration reaction solution to neutralize. Distillation was performed through a thin film still under vacuum of 4 mbar while raising the temperature of the neutralized anhydrosugar alcohol solution to 190°C. After separating the isosorbide-containing distillate, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide (dianhydrose alcohol), 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. I did. The anhydrosugar alcohol composition had a number average molecular weight of 393 g/mol and a polydispersity index of 2.75.

200 g of the anhydrosugar alcohol composition obtained above, 1 g of maleic anhydride and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the reaction was carried out for 5 hours. After completion of the reaction, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added anhydrosugar alcohol composition.

Example A2: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of alcohol composition and anhydrous Maleic acid 10 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 397 g/mol and a polydispersity index of 2.74.

200 g of the anhydrosugar alcohol composition obtained above, 20 g of maleic anhydride and 1 g of sodium hydroxide solution (50%) were put into a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the reaction was carried out for 5 hours. After the reaction was completed, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added anhydrosugar alcohol composition.

Example A3: Illegal Allowance Alcohol 50 % By weight Containing Anhydrosugar 100 parts by weight of alcohol composition and anhydrous Maleic acid 0.5 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

Except that the distillation temperature was changed from 190°C to 145°C, and the distillation pressure was changed from 4 mbar to 10 mbar, isosorbide was 50% by weight and sorbitan (alcohol) 240 g of an anhydrosugar alcohol composition containing 10% by weight and 40% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 175 g/mol and a polydispersity index of 1.34.

200 g of the anhydrosugar alcohol composition obtained above, 1 g of maleic anhydride and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the reaction was carried out for 5 hours. After the reaction was completed, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added anhydrosugar alcohol composition.

Example A4: Illegal Allowance Alcohol 90 % By weight Containing Anhydrosugar 100 parts by weight of alcohol composition and anhydrous Maleic acid 0.5 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

Except that the distillation temperature was changed from 190°C to 210°C, and the distillation pressure was changed from 4 mbar to 15 mbar, it was carried out in the same manner as in Example A1, and isosorbide 90% by weight, sorbitan (alcohol) 5 240 g of an anhydrosugar alcohol composition containing 5% by weight and 5% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 161 g/mol and a polydispersity index of 1.26.

200 g of the anhydrosugar alcohol composition obtained above, 1 g of maleic anhydride and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the reaction was carried out for 5 hours. After the reaction was completed, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added anhydrosugar alcohol composition.

Example A5: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin One Parts by weight After crosslinking reaction, anhydrous Maleic acid 0.5 Parts by weight Acid-added crosslinked anhydrosugar alcohol composition prepared by reaction

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 395 g/mol and a polydispersity index of 2.71.

200 g of the anhydrosugar alcohol composition obtained above, 2 g of epichlorohydrin, and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to 60° C., and 1 g of maleic anhydride was added to the reactor. After that, the temperature inside the reactor was raised to 80°C again. After completion of the temperature increase to 80 ℃, the reaction was further carried out for 5 hours. After completion of the additional reaction, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added crosslinked anhydrosugar alcohol composition.

Example A6: Illegal Allowance Alcohol 50 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin One Parts by weight After crosslinking reaction, anhydrous Maleic acid 0.5 Parts by weight Acid-added crosslinked anhydrosugar alcohol composition prepared by reaction

Except that the distillation temperature was changed from 190°C to 145°C, and the distillation pressure was changed from 4 mbar to 10 mbar, isosorbide was 50% by weight and sorbitan (alcohol) 240 g of an anhydrosugar alcohol composition containing 10% by weight and 40% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 180 g/mol and a polydispersity index of 1.33.

200 g of the anhydrosugar alcohol composition obtained above, 2 g of epichlorohydrin, and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to 60° C., and 1 g of maleic anhydride was added to the reactor. After that, the temperature inside the reactor was raised to 80°C again. After completion of the temperature increase to 80 ℃, the reaction was further carried out for 5 hours. After completion of the additional reaction, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added crosslinked anhydrosugar alcohol composition.

Example A7: Illegal Allowance Alcohol 90 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin One Parts by weight After crosslinking reaction, anhydrous Maleic acid 0.5 Parts by weight Acid-added crosslinked anhydrosugar alcohol composition prepared by reaction

Except that the distillation temperature was changed from 190°C to 230°C, and the distillation pressure was changed from 4 mbar to 15 mbar, it was carried out in the same manner as in Example A1, and 90% by weight of isosorbide, sorbitan (alcohol) 5 240 g of an anhydrosugar alcohol composition containing 5% by weight and 5% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 163 g/mol and a polydispersity index of 1.28.

200 g of the anhydrosugar alcohol composition obtained above, 2 g of epichlorohydrin, and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to 60° C., and 1 g of maleic anhydride was added to the reactor. After that, the temperature inside the reactor was raised to 80°C again. After completion of the temperature increase to 80 ℃, the reaction was further carried out for 5 hours. After completion of the additional reaction, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added crosslinked anhydrosugar alcohol composition.

Example A8: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin 10 Parts by weight After crosslinking reaction, anhydrous Maleic acid 0.5 Parts by weight Acid-added crosslinked anhydrosugar alcohol composition prepared by reaction

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 390 g/mol and a polydispersity index of 2.71.

200 g of the anhydrosugar alcohol composition obtained above, 20 g of epichlorohydrin, and 1 g of sodium hydroxide solution (50%) were put into a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to 60° C., and 1 g of maleic anhydride was added to the reactor. After that, the temperature inside the reactor was raised to 80°C again. After completion of the temperature increase to 80 ℃, the reaction was further carried out for 5 hours. After completion of the additional reaction, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added crosslinked anhydrosugar alcohol composition.

Example A9: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin One Parts by weight After crosslinking reaction, anhydrous Maleic acid 10 Parts by weight Acid-added crosslinked anhydrosugar alcohol composition prepared by reaction

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 396 g/mol and a polydispersity index of 2.73.

200 g of the anhydrosugar alcohol composition obtained above, 2 g of epichlorohydrin, and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to 60° C., and 20 g of maleic anhydride was added to the reactor. After that, the temperature inside the reactor was raised to 80°C again. After completion of the temperature increase to 80 ℃, the reaction was further carried out for 5 hours. After completion of the additional reaction, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added crosslinked anhydrosugar alcohol composition.

Example A10: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar Alcohol composition 100 With parts by weight Sodium tripolyphosphate 1 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 399 g/mol and a polydispersity index of 2.72.

100 g of the anhydrosugar alcohol composition obtained above, 1 g of sodium tripolyphosphate and 1 g of hydrochloric acid were placed in a reactor, and the temperature inside the reactor was raised to 70°C. After completion of the temperature increase to 70 ℃, the reaction was carried out for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature, thereby obtaining 95 g of an acid-added anhydrosugar alcohol composition.

Comparative example A1: Illegal Allowance Alcohol 5 % By weight Containing Anhydrosugar 100 parts by weight of alcohol composition and anhydrous Maleic acid 0.5 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

Except that the distillation temperature was changed from 190°C to 160°C, and the distillation pressure was changed from 4 mbar to 0.42 mbar, it was carried out in the same manner as in Example A1, and isosorbide 5% by weight, sorbitan (anhydrous sugar alcohol) 170 g of an anhydrosugar alcohol composition containing 20% by weight and 75% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 448 g/mol and a polydispersity index of 3.18.

100 g of the anhydrosugar alcohol composition obtained above, 0.5 g of maleic anhydride and 0.5 g of sodium hydroxide solution (50%) were put into a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the reaction was performed for 5 hours. After the reaction was completed, the reaction product was cooled to room temperature, thereby obtaining 90 g of an acid-added anhydrosugar alcohol composition.

Comparative example A2: Illegal Allowance Alcohol 95 % By weight Containing Anhydrosugar 100 parts by weight of alcohol composition and anhydrous Maleic acid 0.5 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

Except that the distillation temperature was changed from 190°C to 230°C, and the distillation pressure was changed from 4 mbar to 15 mbar, it was carried out in the same manner as in Example A1, and isosorbide 95% by weight, sorbitan (no sugar alcohol) 2 480 g of an anhydrosugar alcohol composition containing 3% by weight and 3% by weight of their polymer was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 152 g/mol and a polydispersity index of 1.13.

200 g of the anhydrosugar alcohol composition obtained above, 1 g of maleic anhydride and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the reaction was carried out for 5 hours. After the reaction was completed, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added anhydrosugar alcohol composition.

Comparative example A3: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of alcohol composition and anhydrous Maleic acid 0.1 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 395 g/mol and a polydispersity index of 2.69.

200 g of the anhydrosugar alcohol composition obtained above, 0.2 g of maleic anhydride and 1 g of sodium hydroxide solution (50%) were put into a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the reaction was carried out for 5 hours. After the reaction was completed, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added anhydrosugar alcohol composition.

Comparative example A4: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of alcohol composition and anhydrous Maleic acid 20 Parts by weight Prepared by reaction, acid-added Anhydrosugar Alcohol composition

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 389 g/mol and a polydispersity index of 2.74.

200 g of the anhydrosugar alcohol composition obtained above, 40 g of maleic anhydride and 1 g of sodium hydroxide solution (50%) were put into a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the reaction was carried out for 5 hours. After completion of the reaction, the reaction product was cooled to room temperature to obtain 210 g of an acid-added anhydrosugar alcohol composition.

Comparative example A5: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin 30 Parts by weight After crosslinking reaction, anhydrous Maleic acid 0.5 Parts by weight Acid-added crosslinked anhydrosugar alcohol composition prepared by reaction

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 392 g/mol and a polydispersity index of 2.68.

200 g of the anhydrosugar alcohol composition obtained above, 60 g of epichlorohydrin and 1 g of sodium hydroxide solution (50%) were put into a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to 60° C., and 1 g of maleic anhydride was added to the reactor. After that, the temperature inside the reactor was raised to 80°C again. After completion of the temperature increase to 80 ℃, the reaction was further carried out for 5 hours. After completion of the additional reaction, the reaction product was cooled to room temperature to obtain 220 g of an acid-added crosslinked anhydrosugar alcohol composition.

Comparative example A6: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin One Parts by weight After crosslinking reaction, anhydrous Maleic acid 0.1 Parts by weight Acid-added crosslinked anhydrosugar alcohol composition prepared by reaction

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 394 g/mol and a polydispersity index of 2.74.

200 g of the anhydrosugar alcohol composition obtained above, 2 g of epichlorohydrin, and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to 60° C., and 1 g of maleic anhydride was added to the reactor. After that, the temperature inside the reactor was raised to 80°C again. After completion of the temperature increase to 80 ℃, the reaction was further carried out for 5 hours. After completion of the additional reaction, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added crosslinked anhydrosugar alcohol composition.

Comparative example A7: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin One Parts by weight After crosslinking reaction, anhydrous Maleic acid 20 Parts by weight Acid-added crosslinked anhydrosugar alcohol composition prepared by reaction

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 390 g/mol and a polydispersity index of 2.79.

200 g of the anhydrosugar alcohol composition obtained above, 2 g of epichlorohydrin, and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to 60° C., and 40 g of maleic anhydride was added to the reactor. After that, the temperature inside the reactor was raised to 80°C again. After completion of the temperature increase to 80 ℃, the reaction was further carried out for 5 hours. After completion of the additional reaction, the reaction product was cooled to room temperature, thereby obtaining 190 g of an acid-added crosslinked anhydrosugar alcohol composition.

Comparative example A8: Illegal Allowance Alcohol 10 % By weight Containing Anhydrosugar 100 parts by weight of the alcohol composition and Epichlorohydrin One Parts by weight Crosslinked, prepared by crosslinking reaction Anhydrosugar Alcohol composition

In the same manner as in Example A1, 240 g of an anhydrosugar alcohol composition containing 10% by weight of isosorbide, 20% by weight of sorbitan (anhydrosugar alcohol), and 70% by weight of a polymer thereof was obtained. The anhydrosugar alcohol composition had a number average molecular weight of 399 g/mol and a polydispersity index of 2.77.

200 g of the anhydrosugar alcohol composition obtained above, 2 g of epichlorohydrin, and 1 g of sodium hydroxide solution (50%) were placed in a reactor, and the temperature inside the reactor was raised to 80°C. After completion of the temperature increase to 80 ℃, the crosslinking reaction was performed for 5 hours. After completion of the crosslinking reaction, the reaction product was cooled to room temperature to obtain 190 g of a crosslinked anhydrosugar alcohol composition.

The composition ratio and physical property values of the anhydrosugar alcohol compositions prepared in Examples A1 to A10 and Comparative Examples A1 to A8 are shown in Table 1 below.

[Table 1]

< Anhydrosugar Measurement method of physical properties of alcohol composition>

Number average molecular weight (Mn) and Polydispersity Indices( PDI )

Each of the anhydrosugar alcohol compositions prepared in Examples A1 to A10 and Comparative Examples A1 to A8 was dissolved in 1 to 3 parts by weight to 100 parts by weight of N,N-dimethylformamide, and then gel permeation chromatography (Gel Permeation Chromatography). , GPC) The number average molecular weight (Mn) and the polydispersity index (PDI) were measured using an apparatus (Agilent Corporation). The column used at this time is PLgel 3μm MIXED-E 300x7.5mm (Agilent Corporation), the column temperature is 50℃, and the developing solvent used is N,N-dimethylformamide containing 0.05 M NaBr, 0.5 mL/min. It was spilled and used, and polystyrene (Aldrich Corporation) was used as a standard material.

Hydroxyl value

In accordance with ASTM D-4274D, a hydroxyl value test standard, each anhydrosugar alcohol composition prepared in Examples A1 to A10 and Comparative Examples A1 to A8 and an excess of phthalic anhydride were esterified under an imidazole catalyst. Thereafter, the remaining phthalic anhydride was titrated with 0.5 N sodium hydroxide (NaOH) to measure the hydroxyl value of the anhydrosugar alcohol composition.

< Anhydrosugar Preparation of dispersant for concrete containing alcohol composition>

Example B1: Example Acid-added of A1 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Example A1 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B2: Example Acid-added of A2 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Example A2 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B3: Example Acid-added of A3 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Example A3 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B4: Example Acid-added of A4 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Example A4 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B5: Example Acid-added crosslinking of A5 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Example A5 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B6: Example Acid-added crosslinking of A6 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Example A6 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B7: Example Acid-added crosslinking of A7 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Example A7 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B8: Example Acid-added crosslinking of A8 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Example A8 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B9: Example Acid-added crosslinking of A9 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Example A9 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B10: Example Acid-added of A10 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Example A10 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Example B11: Example Acid-added of A1 Anhydrosugar Alcohol composition 20 Parts by weight And anionic surfactant 80 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 20 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Example A1 and 80 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B1: Dispersant for concrete consisting only of anionic surfactants

A dispersant for concrete was prepared consisting only of anionic surfactant (Dongnam Corporation (manufactured)).

Comparative example B2: Example Acid-added of A1 Anhydrosugar Alcohol composition 30 Parts by weight And anionic surfactant 70 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 30 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Example A1 and 70 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B3: Example Acid-added crosslinking of A5 Anhydrosugar Alcohol composition 30 Parts by weight And anionic surfactant 70 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 30 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Example A5 and 70 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B4: Comparative example Acid-added of A1 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Comparative Example A1 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B5: Comparative example Acid-added of A2 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Comparative Example A2 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B6: Comparative example Acid-added of A3 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Comparative Example A3 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B7: Comparative example Acid-added of A4 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added anhydrosugar alcohol composition obtained in Comparative Example A4 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B8: Comparative example Acid-added crosslinking of A5 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Comparative Example A5 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B9: Comparative example Acid-added crosslinking of A6 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Comparative Example A6 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B10: Comparative example Acid-added crosslinking of A7 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the acid-added crosslinked anhydrosugar alcohol composition obtained in Comparative Example A7 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

Comparative example B11: Comparative example Crosslinking of A8 Anhydrosugar Alcohol composition 10 Parts by weight And anionic surfactant 90 Parts by weight Dispersant for concrete containing

A dispersant for concrete was prepared by mixing 10 parts by weight of the crosslinked anhydrosugar alcohol composition obtained in Comparative Example A8 and 90 parts by weight of an anionic surfactant (manufactured by Dongnam Corporation).

<Preparation of a concrete composition containing a dispersant for concrete>

Example C1 to C11 and Comparative example C1 to C11: Preparation of concrete composition

Water 165 kg/m ³ , cement 423 kg/m ³ , slag 47 kg/m ³ , sand 313 kg/m ³ , crushed sand 480 kg/m ³ and gravel 889 kg/m ³ Concrete compositions of Examples C1 to C11 and Comparative Examples C1 to C11 were prepared by adding each of the dispersants for concrete prepared in Examples B1 to B11 and Comparative Examples B1 to B11. At this time, the prepared concrete compositions included 1 part by weight of a dispersant for concrete, based on 100 parts by weight of a binder, and the binder refers to a mixture of cement and slag.

Physical properties were evaluated for the concrete compositions of Examples C1 to C11 and Comparative Examples C1 to C11, and the results are shown in Table 2 below.

<Method of evaluating performance of concrete composition>

(1) Concrete slump test

Concrete water reducing performance was evaluated for the concrete compositions prepared in Examples C1 to C11 and Comparative Examples C1 to C11. Specifically, the concrete composition prepared above was mixed for 120 seconds using a forced pan mixer, and then, according to ASTM C 1611 standard, an initial slump of concrete and a slump test after 30 minutes were performed.

More specifically, immediately after preparation of each of the prepared concrete compositions, the slump cone on the watertight plate was filled while compacting, and then the slump cone was removed. (Initial slump measurement). The larger the diameter of the concrete spread, the better the dispersibility of the concrete.

In addition, after each of the prepared concrete compositions was stored for 30 minutes, the slump cone was filled while being compacted, and the slump cone was removed, and the difference between the initial height of the concrete and the height of the slump cone was measured (slump after 30 minutes). The greater the difference between the height of the concrete and the height of the slump cone, the better the dispersibility of the concrete.

(2) Initial air volume measurement in concrete

Initial air volume was measured for the concrete compositions prepared in Examples C1 to C11 and Comparative Examples C1 to C11 according to the KS F 2421 standard.

(3) concrete viscosity measurement

The viscosity of the concrete composition was measured using the T50 method. Specifically, the time until the concrete composition spreads and reaches a diameter of 50 cm was measured. The shorter the measured time is, the lower the viscosity is, which means excellent fluidity.

[Table 2]

As shown in Table 2, in the case of the concrete compositions of Examples C1 to C11 according to the present invention, the initial slump was 600 mm or more, and after 30 minutes, the slump was 150 mm or more, so that the dispersibility of the concrete was excellent, and the T50 was The viscosity was low in less than 5.89 seconds, so the workability was excellent, and the initial air volume was 1.0% to 1.2%, which satisfies the general initial air volume of concrete.

However, in the case of Comparative Example C1 in which the conventional anionic surfactant, which is a dispersant for concrete, was used alone, the dispersibility of the concrete composition was excellent, but the T50 was 8.98 seconds, and the workability was poor due to the problem of high viscosity.

On the other hand, Comparative Examples C2 to C10 including an acid-added anhydrosugar alcohol composition or an acid-added crosslinked anhydrosugar alcohol composition, but not corresponding to the present invention, and a comparative example including an acid-added crosslinked anhydrosugar alcohol composition It can be seen that all C11s have poor dispersing power due to low initial slump and low slump after 30 minutes, as well as high T50, and still have high viscosity problems, resulting in poor workability.

In short, according to the present invention, while improving the dispersing power of the concrete composition, by solving the problem of high viscosity of the conventional dispersant for concrete, it is possible to improve workability, and can bring an effect of improving economic efficiency according to cost reduction.

Claims (16)

An acid-added anhydrosugar alcohol composition prepared from the reaction of an anhydrosugar alcohol composition or a crosslinked anhydrosugar alcohol composition with an acidic substance,
The amount of the acidic substance used in the reaction is 0.2 to 19 parts by weight, based on 100 parts by weight of the anhydrosugar alcohol composition,
The anhydrosugar alcohol composition comprises (i) a monosaccharide alcohol; (ii) dianhydrosugar alcohol; And (iii) a polymer of at least one of a monohydrate alcohol and a dianhydrosugar alcohol; and
The content of dianhydrosugar alcohol in the anhydrosugar alcohol composition is more than 5% by weight and less than 95% by weight, based on 100% by weight of the total anhydrosugar alcohol composition,
Acid-added anhydrosugar alcohol composition. The method of claim 1, further comprising: (i) alcohol; (ii) dianhydrosugar alcohol; And (iii) a polymer of at least one of a monosugar alcohol and a dianhydrosugar alcohol; At least one of which is obtained in the process of preparing anhydrosugar alcohol by dehydrating a hydrogenated sugar, acid-added anhydrosugar alcohol composition. The acid-added anhydrosugar alcohol composition according to claim 1, wherein the monosaccharide alcohol is hexitol monosaccharide. The acid-added anhydrosugar alcohol composition according to claim 1, wherein the dianhydrosugar alcohol is dianhydrosugar hexitol. The acid according to claim 1, wherein at least one polymer of dianhydrosugar alcohol and dianhydrosugar alcohol is a condensation polymer prepared from a condensation reaction of a dianhydrose alcohol, a condensation reaction of a dianhydrose alcohol, or a condensation reaction of a dianhydrose alcohol and a dianhydrose alcohol. -Added anhydrosugar alcohol composition. The acid-added anhydrosugar alcohol composition according to claim 1, wherein at least one polymer selected from the group consisting of polymers represented by the following formulas 1 to 5 is one or more polymers of monohydric alcohol and dianhydrosugar alcohol:
[Formula 1]

[Formula 2]

[Formula 3]

[Formula 4]

[Formula 5]

In Formulas 1 to 5,
a to d are each independently an integer of 0 to 25, provided that a+b+c+d is 2 to 100. The method of claim 1, wherein the anhydrosugar alcohol composition comprises (i) a number average molecular weight (Mn) of 160 to 445, (ii) a polydispersity index (PDI) of 1.25 to 3.15, and (iii) 645 to 900 mgKOH/g. Satisfying the hydroxyl value (Hydroxyl value), acid-added anhydrosugar alcohol composition. The acid-added anhydrosugar alcohol composition according to claim 1, wherein the average number of -OH groups per molecule in the anhydrosugar alcohol composition is 2.6 to 5.0. The acid-added anhydrosugar alcohol composition according to claim 1, wherein the crosslinked anhydrosugar alcohol composition is prepared by reacting the anhydrosugar alcohol composition defined in claim 1 with a crosslinking agent. The acid-added anhydrosugar alcohol composition according to claim 9, wherein the content of the crosslinking agent for crosslinking the anhydrosugar alcohol composition is 0.1 to 29 parts by weight based on 100 parts by weight of the anhydrosugar alcohol composition. The acid-addition according to claim 9, wherein the crosslinking agent is one or a mixture of two or more selected from the group consisting of epihalohydrin, diamine compounds, dicarboxylate compounds, diester compounds, or mixtures thereof. Anhydrosugar alcohol composition. The acid-added anhydrosugar alcohol composition according to claim 1, wherein the acidic substance is an organic acid, an inorganic acid, or a mixture thereof. The acidic substance according to claim 1, wherein the acidic substance is carboxylic acid, carboxylic acid anhydride, carboxylic acid salt, sulfonic acid, sulfonic acid anhydride, sulfonic acid salt, sulfinic acid, sulfonic acid anhydride, sulfinic acid salt, phosphoric acid, phosphate, phosphorous acid. , Phosphorous acid salt, nitric acid, nitrate salt, nitrous acid, nitrite salt, sulfuric acid, sulfate salt, sulfurous acid, sulfurous acid salt, or a mixture of two or more selected from the group consisting of, acid-added anhydrosugar alcohol composition . As a method for preparing an acid-added anhydrosugar alcohol composition,
Including the step of reacting an anhydrosugar alcohol composition or a crosslinked anhydrosugar alcohol composition and an acidic substance,
The amount of the acidic substance used in the reaction is 0.2 to 19 parts by weight, based on 100 parts by weight of the anhydrosugar alcohol composition,
The anhydrosugar alcohol composition comprises (i) a monosaccharide alcohol; (ii) dianhydrosugar alcohol; And (iii) a polymer of at least one of a monohydrate alcohol and a dianhydrosugar alcohol; and
The content of dianhydrosugar alcohol in the anhydrosugar alcohol composition is more than 5% by weight and less than 95% by weight, based on 100% by weight of the total anhydrosugar alcohol composition,
A method for preparing an acid-added anhydrosugar alcohol composition. A dispersant for concrete comprising 1 to 29 parts by weight of the acid-added anhydrosugar alcohol composition of any one of claims 1 to 13, based on a total of 100 parts by weight of the dispersant. cement; And a concrete composition comprising a; dispersant for concrete of claim 15.