KR101756318B1 - Monomer and polymer for dispersant and manufacturing method of the same - Google Patents

Monomer and polymer for dispersant and manufacturing method of the same Download PDF

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KR101756318B1
KR101756318B1 KR1020150125892A KR20150125892A KR101756318B1 KR 101756318 B1 KR101756318 B1 KR 101756318B1 KR 1020150125892 A KR1020150125892 A KR 1020150125892A KR 20150125892 A KR20150125892 A KR 20150125892A KR 101756318 B1 KR101756318 B1 KR 101756318B1
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carbon atoms
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hydrogen
formula
alkylene group
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KR20170029094A (en
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권오일
전재익
유찬용
김경환
김돈영
전영주
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이지스 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/062—Polyethers
    • 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
    • C04B24/008—Aldehydes, ketones
    • 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
    • C04B24/04—Carboxylic acids; Salts, anhydrides or esters thereof
    • C04B24/045—Esters, e.g. lactones
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/061—Polyesters; Polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/54—Aqueous solutions or dispersions

Abstract

More particularly, the present invention relates to a polymer constituting a polycarboxylic acid-based dispersant, a monomer used for the polymerization, and a process for producing the same. The present invention also relates to a cement dispersant comprising such a polymer and a cement dispersant for the production of mortar or concrete using the same.

Description

TECHNICAL FIELD [0001] The present invention relates to a monomer, a polymer and a method for producing the same,

More particularly, the present invention relates to a polymer constituting a polycarboxylic acid-based dispersant, a monomer used for the polymerization, and a process for producing the same. The present invention also relates to a cement dispersant comprising such a polymer and a cement dispersant for the production of mortar or concrete using the same.

The polycarboxylic acid-based water reducing agent as a dispersant for cement is known to have excellent performance unlike conventionally known lignin water reducing agents and naphthalene based water reducing agents.

For example, the concrete admixture disclosed in Korean Patent No. 855533 is known to have excellent workability of the cement composition due to characteristics such as reduction of concrete viscosity, improvement of slump retention and inhibition of bleeding in the cement composition.

However, the reduction of fluidity and slump loss over time can not be completely resolved, and this need to be improved.

Furthermore, the polycarboxylic acid-based water reducing agent has been difficult to synthesize due to its complicated structure, and thus it has been a stumbling block to various applications.

Korean Patent No. 855533 (2008.08.26)

SUMMARY OF THE INVENTION The present invention has been made to solve the above-mentioned problems, and it is an object of the present invention to provide a monomer for the production of a polycarboxylic acid-based cement dispersant having a novel structure.

Another object of the present invention is to provide a dispersant comprising a polymer obtained by polymerizing the monomer.

Another object of the present invention is to provide a mortar or concrete containing the dispersant.

Another object of the present invention is to provide a process for producing the above monomers.

Another object of the present invention is to provide a polymer obtained by polymerizing the monomer.

Another object of the present invention is to provide a dispersant comprising the polymer.

Another object of the present invention is to provide a process for producing the above polymer.

The monomers for the production of the dispersant of the present invention are characterized by being represented by the following formula (1)

Figure 112015086484112-pat00001

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, and n represents an average molar number of oxyalkylene groups added,

On the other hand, the dispersant of the present invention may include a copolymer obtained by polymerizing the above-mentioned monomer for producing a dispersant as a monomer for copolymerization.

Meanwhile, the mortar or concrete of the present invention may include the above-mentioned dispersant.

The method for preparing a monomer for preparing a dispersant of the present invention represented by the general formula (1) comprises reacting a compound represented by the following general formula (2) and a compound represented by the following general formula (3)

[Chemical Formula 1]

Figure 112015086484112-pat00002

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,

Figure 112015086484112-pat00003

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;

Figure 112015086484112-pat00004

Wherein X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms.

Also, the compound of Formula 1 may be prepared by reacting at 25 to 130 ° C.

The compound of Formula 1 may be prepared by reacting the compound of Formula 1 at 25 to 130 ° C in the presence of a polymerization inhibitor.

The compound of Formula 1 may be prepared by reacting in the presence of an acidic catalyst.

On the other hand, the polymer of the present invention represented by the following formula (6) can be produced by reacting a macromonomer represented by the following formula (1) with at least one of a compound represented by the following formula (2), a compound represented by the following formula Which is characterized in that it is obtained by reacting:

[Chemical Formula 1]

Figure 112015086484112-pat00005

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,

(2)

Figure 112015086484112-pat00006

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;

Figure 112015086484112-pat00007

Wherein R10, R11 and R12 are hydrogen, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms or allyl of 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, or 1 Secondary, or tertiary amine;

Figure 112015086484112-pat00008

Wherein R13 and R14 are hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms or allyl having 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, A tertiary amine;

Figure 112015086484112-pat00009

Wherein o, p, q and r represent the average number of moles, 0? O, p, r? 400, and 0.1 ≤ q ≤ 400, and o + p ≥ 0.1.

The weight average molecular weight of the polymer of the present invention represented by Formula 6 may be 10,000 to 300,000.

Further, the polymer of the present invention represented by the above formula (6) may be q + r? O + p.

The polymer of the present invention represented by the above formula (6) may be used in an amount of 0.1 to 400: 0 to 400: 0 to 400: 0 to 400, preferably 10 to 100: 0 to 70: 150: 0 to 150, and o + p? 0.1.

Meanwhile, the dispersant of the present invention may include the polymer of the present invention represented by the above formula (6).

Meanwhile, the mortar or concrete of the present invention may include the above-mentioned dispersant.

On the other hand, the process for producing the polymer of the present invention represented by the following formula (6) is characterized by comprising the following steps:

(A) obtaining a macromonomer represented by the formula (1) obtained by reacting a compound represented by the following formula (2) and a compound represented by the following formula (3)

[Chemical Formula 1]

Figure 112015086484112-pat00010

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,

(2)

Figure 112015086484112-pat00011

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;

(3)

Figure 112015086484112-pat00012

Wherein X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms; And

(B) a polymer obtained by reacting at least one of the compound represented by the formula (2), the compound represented by the following formula (4) and the compound represented by the following formula (5) with the macromonomer represented by the formula Obtaining a polymer;

[Chemical Formula 4]

Figure 112015086484112-pat00013

Wherein R10, R11 and R12 are hydrogen, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms or allyl of 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, or 1 Secondary, or tertiary amine;

[Chemical Formula 5]

Figure 112015086484112-pat00014

Wherein R13 and R14 are hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms or allyl having 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, A tertiary amine;

[Chemical Formula 6]

Figure 112015086484112-pat00015

Wherein o, p, q and r represent the average number of moles, 0? O, p, r? 400, and 0.1 ≤ q ≤ 400, and o + p ≥ 0.1.

The monomers for the polycarboxylic acid dispersant of the present invention can simplify the synthesis technique of the polymer and make it possible to apply it as a dispersant with remarkably improved performance. Specifically, it has an effect of improving the workability by increasing dispersing and holding power between cement molecules, suppressing slump loss, having excellent fluidity, and shortening the concrete mixing time by 20% or more. Also, the mortar / concrete admixture using the cement dispersant of the present invention has an effect of providing a proper concrete condition and an appropriate compressive strength with time.

1 shows a < 1 > H-NMR spectrum of the monomer prepared in Example 1. Fig.
2 shows the < 1 > H-NMR spectrum of the monomer prepared in Example 2. Fig.
3 shows a < 1 > H-NMR spectrum of the monomer prepared in Example 3. Fig.
4 shows a < 1 > H-NMR spectrum of the monomer prepared in Example 4. Fig.
5 shows the < 1 > H-NMR spectrum of the monomer prepared in Example 5. Fig.
6 shows a1H-NMR spectrum of the monomer prepared in Example 6. Fig.
7 shows a < 1 > H-NMR spectrum of the monomer prepared in Example 7. Fig.

As used herein, the terms " alkylene " and " alkenylene " mean straight or branched chain alkylene and straight or branched chain alkenylene.

Hereinafter, preferred embodiments of the present invention will be described in detail. In the following description, numerous specific details, such as specific elements, are set forth in order to provide a thorough understanding of the present invention, and it is to be understood that the present invention may be practiced without these specific details, It will be obvious to those who have knowledge of. In the following description of the present invention, a detailed description of known functions and configurations incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

The monomer for producing a dispersant of the present invention is characterized by being represented by the following formula (1)

[Chemical Formula 1]

Figure 112015086484112-pat00016

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, and n represents an average molar number of oxyalkylene groups added,

On the other hand, the dispersant of the present invention may include a copolymer obtained by polymerizing the above-mentioned monomer for producing a dispersant as a monomer for copolymerization.

Meanwhile, the mortar or concrete of the present invention may include the above-mentioned dispersant.

The method for preparing a monomer for preparing a dispersant of the present invention represented by the general formula (1) comprises reacting a compound represented by the following general formula (2) and a compound represented by the following general formula (3)

[Chemical Formula 1]

Figure 112015086484112-pat00017

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,

(2)

Figure 112015086484112-pat00018

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;

(3)

Figure 112015086484112-pat00019

Wherein X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms.

Also, the compound of Formula 1 may be prepared by reacting at 25 to 130 ° C.

The compound of Formula 1 may be prepared by reacting the compound of Formula 1 at 25 to 130 ° C in the presence of a polymerization inhibitor.

The compound of Formula 1 may be prepared by reacting in the presence of an acidic catalyst.

On the other hand, the polymer of the present invention represented by the following formula (6) can be produced by reacting a macromonomer represented by the following formula (1) with at least one of a compound represented by the following formula (2), a compound represented by the following formula Which is characterized in that it is obtained by reacting:

[Chemical Formula 1]

Figure 112015086484112-pat00020

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,

(2)

Figure 112015086484112-pat00021

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;

[Chemical Formula 4]

Figure 112015086484112-pat00022

Wherein R10, R11 and R12 are hydrogen, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms or allyl of 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, or 1 Secondary, or tertiary amine;

[Chemical Formula 5]

Figure 112015086484112-pat00023

Wherein R13 and R14 are hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms or allyl having 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, A tertiary amine;

[Chemical Formula 6]

Figure 112015086484112-pat00024

Wherein o, p, q and r represent the average number of moles, 0? O, p, r? 400, and 0.1 ≤ q ≤ 400, and o + p ≥ 0.1.

When the macromonomer represented by the formula (1) is finally copolymerized with the polymer represented by the formula (6), the holding performance is enhanced and the mixing time is shortened according to the influence of the acid group (acidic group) at X and the terminal.

The weight average molecular weight of the polymer of the present invention represented by Formula 6 may be 10,000 to 300,000.

Further, the polymer of the present invention represented by the above formula (6) may be q + r? O + p.

The polymer of the present invention represented by the above formula (6) may be used in an amount of 0.1 to 400: 0 to 400: 0 to 400: 0 to 400, preferably 10 to 100: 0 to 70: 150: 0 to 150, and o + p? 0.1.

Meanwhile, the dispersant of the present invention may include the polymer of the present invention represented by the above formula (6).

Meanwhile, the mortar or concrete of the present invention may include the above-mentioned dispersant.

On the other hand, the process for producing the polymer of the present invention represented by the following formula (6) is characterized by comprising the following steps:

(A) obtaining a macromonomer represented by the formula (1) obtained by reacting a compound represented by the following formula (2) and a compound represented by the following formula (3)

[Chemical Formula 1]

Figure 112015086484112-pat00025

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,

(2)

Figure 112015086484112-pat00026

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;

(3)

Figure 112015086484112-pat00027

Wherein X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms; And

(B) a polymer obtained by reacting at least one of the compound represented by the formula (2), the compound represented by the following formula (4) and the compound represented by the following formula (5) with the macromonomer represented by the formula Obtaining a polymer;

[Chemical Formula 4]

Figure 112015086484112-pat00028

Wherein R10, R11 and R12 are hydrogen, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms or allyl of 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, or 1 Secondary, or tertiary amine;

[Chemical Formula 5]

Figure 112015086484112-pat00029

Wherein R13 and R14 are hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms or allyl having 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, A tertiary amine;

[Chemical Formula 6]

Figure 112015086484112-pat00030

Wherein o, p, q and r represent the average number of moles, 0? O, p, r? 400, and 0.1 ≤ q ≤ 400, and o + p ≥ 0.1.

The macromonomer represented by the formula (1) is synthesized through the reaction between the compound represented by the formula (2) and the compound represented by the formula (3), and the control of the synthesis is determined by the acid catalyst and the moles to be reacted. Methane sulfonic acid, p-toluene sulfonic acid, hydrochloric acid, sulfuric acid, etc. may be used as the acid catalyst. The reaction temperature and time are preferably from 25 to 200 ° C for 0.5 to 150 hours, particularly preferably from 25 to 130 ° C for from 0.5 to 80 hours. The reaction time is preferably in the above range in order to ensure proper polymerization. It is also preferable that the polymerization temperature also has the above range in order to ensure the progress of the polymerization and to prevent chain breaking.

In order to confirm the progress of the reaction, the acid value was measured and the reaction rate was calculated as follows, and when the reaction rate was 99% or more, the completion time was set.

Figure 112015086484112-pat00031

When n is less than 400 in the macromonomer represented by the general formula (1), the side chain length is appropriate at the time of the synthesis to prevent the viscosity from being excessively increased. As a result, the polymerization reaction can proceed easily, and the dispersibility of the polymer of the formula (6) as the final structure is also excellent.

The compound represented by the general formula (2) is an additive for the ring opening reaction shown in the compound represented by the general formula (3), and has an acid group in the side chain through reaction with an acid anhydride. When preparing the polymer represented by the general formula (6), the macromonomer represented by the general formula (1) and the compound represented by the general formula (2) can be used at the same time.

X is selected from the group consisting of maleic acid anhydride, succinic acid anhydride, 1,8-naphthalic acid anhydride, 4-methylphthalic anhydride, phthalic anhydride, (2-Dodecen-1-yl) succinic Itaconic acid anhydride, trans-1,2-cyclohexanedicarboxylic acid anhydride, 2,3-Dimethylmaleic acid anhydride, Homophthalic acid anhydride, Hexahydro-4-methylphthalic anhydride, 3,3-Tetramethyleneglutaric acid anhydride, Phenylsuccinic acid anhydride, 4-Methylphthalic anhydride, 2-Octen-1-ylsuccinic acid anhydride, N-Methylisatoic acid anhydride, 4-Pyridinedicarboxylic acid anhydride, Bromomaleic acid anhydride, 4-Methylphthalic anhydride, 4-Bromo-1,8-naphthalic acid anhydride, 4-Amino-1,8-naphthalic acid anhydride, Tetrachlorophthalic acid anhydride, 3-Hydroxyphthalic acid anhydride, 2,3-Dichloromaleic acid anhydride, Acid anhydrides, 5-bromoisatoic acid anhydrides, and 3,6-dichlorophthalic acid anhydrides.

The compound represented by the general formula (3) is applied to the reaction with an unsaturated (poly) oxyalkylene ether through a ring-opening reaction with an acid anhydride (acid anhydride) and can be applied to the present invention by substituting an acidic group at the terminal group.

The compound represented by the formula (4) and the compound represented by the formula (5) constituting the polymer represented by the formula (6) may be used alone or both of them may be used at the same time and the degree of polymerization may be controlled according to the average molar ratio.

In addition, the polymerization of these reactions can be controlled by the polymerization inhibitor with an average molecular weight. The polymerization inhibitor usable in the present invention is, for example, a quinone polymerization inhibitor such as hydroquinone, methoxyhydroquinone, benzoquinone, and p- Cole; Alkylphenol polymerization inhibitors such as 2,6-di-tert-butylphenol, 2,4-di-tert-butylphenol, 2-tert- Butyl-4-methylphenol, and 2,4,6-tri-tert-butylphenol; Amine based polymerization inhibitors such as alkylated diphenylamines, N, N'-diphenyl-p-phenylenediamine, and phenothiazine; N-oxyl polymerization inhibitors such as 4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl; And copper dithiocarbamate-based polymerization inhibitors such as copper dimethyldithiocarbamate, copper diethyldithiocarbamate, and copper dibutyldithiocarbamate. They may be used alone or in combination of two or more species. A quinone-based polymerization inhibitor and an N-oxyl-based polymerization inhibitor are preferable, and hydroquinone, methoxyhydroquinone, benzoquinone, p-tert-butylcatechol, phenothiazine, and 4-hydroxy- More preferred is 6-tetramethylpiperidine-N-oxyl. The addition amount of the polymerization inhibitor is determined depending on the total amount of the reactants to be added to the reaction, and is preferably 0.005 to 1% by weight based on the total weight of the reactants.

The structure of formula (6) is a polymer obtained by copolymerizing two or more monomers, and is a polymer obtained by chemically reacting a macromonomer represented by formula (1), a compound represented by formula (2), a compound represented by formula (4) to be. The mixing ratio of the compound represented by each formula is in the range of the molar ratio and the sum of the molar ratios of the macromonomer represented by the formula (1) and the compound represented by the formula (2) is larger than the sum of the molar ratios of the compound represented by the formula And the polymer represented by the formula (6) necessarily contains the macromonomer represented by the formula (1) and the compound represented by the formula (2) may be used together. The compound represented by the general formula (4) and the compound represented by the general formula (5) may be used either singly or in combination, and at least one of the compound represented by the general formula (4) and the compound represented by the general formula (5)

The polymerization is controlled by the ratio of the average number of moles, and the molar ratio of the macromonomer represented by the formula (1): the compound represented by the formula (2): the compound represented by the formula (4): the compound represented by the formula (5) is 0.1 to 400: 0 to 400: 0 to 400. Particularly preferred is a macromonomer represented by the formula (1): the compound represented by the formula (2): the compound represented by the formula (4): the molar ratio of the compound represented by the formula (5) is 10 to 100: 0 to 70: 0 to 150: By weight. The compound represented by the general formula (4) and the compound represented by the general formula (5) must be contained in at least one of the polymers of the general formula (6), and the ratio thereof prevents the dispersion performance from deteriorating and the viscosity from becoming too high, It is preferable to be in the above range.

In the polymerization of the monomer component, a chain transfer agent and a polymerization initiator may be used. As the chain transfer agent, any appropriate substance can be used, and specifically thiol chain transfer agents such as thioglycerol, mercaptoethanol, 2-mercaptopropionic acid, 3-mercaptopropionic acid and thiomalic acid can be used. As the polymerization initiator, persulfates such as ammonium persulfate, sodium persulfate and potassium persulfate, and peroxide type polymerization initiators such as hydrogen peroxide water and benzoyl peroxide can be used.

Since the polymer represented by the formula (6) prepared by the above-mentioned method has an acidic functional group at the end of its side chain, the reaction between the cement and water at the time of mixing the concrete is greatly enhanced by the cubic repulsion by the side chain and the predetermined electrostatic repulsive force. Can be improved. In addition, the mixing time can be reduced due to the anions derived from the acidic functional groups at the side chain terminals, and the maintenance performance is improved through de-esterfication after a certain period of time.

The cement dispersant prepared as described above may be used alone or in combination with other additives such as AE agent, AE water reducing agent which improves work performance or freezing and thawing resistance performance, a fluidizing agent which improves fluidity by using water reducing effect, Shrinkage reducing agents that reduce shrinkage, accelerators and retardants that control the setting and curing time, rust inhibitors that inhibit the corrosion of reinforcing bars by chloride, separating reducers that prevent the separation of cement and aggregate, waterproofing agents that increase the water resistance, A foaming agent for promoting the weight reduction, a foaming agent for lighter weight, and a thickener for improving the viscosity and cohesive action, and may be made of a mortar-concrete admixture.

Hereinafter, embodiments of the present invention will be described.

Example

Example  1: Synthesis of Compound (1)

CH 2 = C (CH 3) -CH 2 -O- (CH 2 -CH 2 -O) 60 -H 1117.36 g: Place the (EO 60 mol), and heated to 60 ℃. At this time, the water contained in the compound was recovered in a vacuum to completely remove moisture. Then 42.35 g of succinic anhydride and 5.8 g of methanesulfonic acid were added. When the addition was completed, the temperature was heated to 90 占 폚. After heating for about 22 hours, the acid value reached 23.42 ml / g (reaction rate 99.4%) and the reaction was terminated.

Examples 2 to 8: Synthesis of Compound (1)

The reaction was carried out by changing the ether compound, the acid anhydride and the reaction time according to Table 1. The procedure was carried out in the same manner as in Example 1, and the reaction results are shown in Table 1 below.

Example 9 Synthesis of Compound (1) (3) - Use of polymerization inhibitor

(EO: 30 mol) of CH 2 = C (CH 3 ) -CH 2 -O- (CH 2 -CH 2 -O) 30 -H was added and heated to 60 ° C. At this time, the water contained in the compound was recovered in a vacuum to completely remove moisture. Then 42.35 g of succinic anhydride, 5.8 g of methanesulfonic acid and 0.3 g of phenothiazine were added. When the addition was completed, the temperature was heated to 80 占 폚. After heating for about 6 hours, the acid value reached 23.47 ml / g (reaction rate 99.2%) and the reaction was terminated.

Example 10 Synthesis of Compound (1) (4)

After placing a thermometer and a stirrer in a glass reactor, 300 g of the macromonomer prepared in Example 1 and 11.55 g of 1-hexanol were placed, and the mixture was subjected to a reduced pressure while heating the mixture to 90 ° C. After 5 hours of reaction, the mixture was terminated and cooled to below 50 ° C to obtain the product CH 2 ═C (CH 3 ) -CH 2 -O- (CH 2 -CH 2 -O) 60 -CO-CH 2 -CH 2 -CO-O 310 g of -CH 2 - (CH 2) 5 -OH were obtained.

Example 11: Synthesis of Compound (1)

After a thermometer and a stirrer were installed in a glass reactor, 500 g of the macromonomer prepared in Example 1 and 19.42 g of lauryl alcohol were placed, and the reaction was performed under reduced pressure while the temperature was being raised to 90 ° C. After 5 hours of reaction, the mixture was terminated and cooled to below 50 ° C to obtain the product CH 2 ═C (CH 3 ) -CH 2 -O- (CH 2 -CH 2 -O) 60 -CO-CH 2 -CH 2 -CO-O 500 g of -CH 2 - (CH 2) 11 -OH were obtained.

Preparation Example 1: Preparation of Polymer for Dispersant (1)

After a thermometer, a stirrer, a reflux condenser, and a dropping funnel were installed in a glass reactor, 207 g of the macromonomer prepared in Example 1 and 90 g of ion-exchanged water were charged, and the temperature was heated to 70 캜. When the target temperature was reached, 1.59 g of 3-mercaptopropionic acid, 6.36 g of acrylic acid, 6.3 g of methacrylic acid, and 0.94 g of sodium pyruvate were added dropwise over a period of 4 to 5 hours. After aging for 3 hours, the reaction was terminated, and the obtained reaction mixture was cooled to 50 DEG C or lower to obtain 310 g of a copolymer aqueous solution.

Production Example 2: Preparation of Polymer for Dispersant (2)

Except that 207 g of the macromonomer prepared in Example 4 was used, thereby obtaining 311.2 g of an aqueous copolymer solution.

Production Example 3: Preparation of Polymer for Dispersant (3)

Except that 207 g of the macromonomer prepared in Example 10 was used, to obtain 301 g of an aqueous copolymer solution.

Production Example 4: Preparation of Polymer for Dispersant (4)

Except that 207 g of the macromonomer prepared in Example 11 was used to obtain 308 g of an aqueous copolymer solution.

Production Example 5: Preparation of Polymer for Dispersant (5)

After a thermometer, a stirrer, a reflux condenser, and a dropping funnel were installed in a glass reactor, 207 g of the macromonomer prepared in Example 1 and 90 g of ion-exchanged water were charged, and the temperature was heated to 70 캜. When the target temperature was reached, 1.59 g of 3-mercaptopropionic acid, 6.36 g of acrylic acid, 6.3 g of methacrylic acid, 4.33 g of maleic anhydride, and 0.94 g of peracetic acid were added dropwise over a period of 4 to 5 hours. After aging for 3 hours, the reaction was terminated, and the obtained reaction mixture was cooled to 50 ° C or lower to obtain 307 g of an aqueous copolymer solution.

Comparative Example: Preparation of Polymer for Dispersant (6)

A thermometer, a stirrer, a reflux condenser, and a dropping funnel were placed in a glass reactor, and 210 g of a methallyl (poly) alkylene glycol ether compound, 17.05 g of maleic acid and 100 g of ion-exchanged water were placed and heated to 80 캜. Then, 9.8 g of hydrogen peroxide solution was added to the reaction vessel. Then, 9 g of acrylic acid, 0.635 g of L-ascorbic acid and 6.03 g of ion-exchanged water were added dropwise for 3 hours and 3.5 hours, respectively. After completion of the dropwise addition, the reaction product was maintained at 65 ° C for 1 hour. When the reaction was completed, the reaction product was adjusted to pH 7 with aqueous NaOH solution to obtain 349.5 g of a copolymer aqueous solution.

Production Example 5

Concrete formulation was carried out with the following composition:

    - Water: 165 kg

    - Cement (general Portland cement): 423 kg

    - Fly-ash: 47 kg

    - aggregate 1 (type: washing machine): 760 kg

    - aggregate 2 (type: 25 mm crushed stone): 946 kg

The test was conducted in the following manner to measure the initial flow value, the flow value after 60 minutes, and the respective air amounts after thoroughly mixing the prepared concrete at the above-mentioned mixing ratio.

Test Example 1: Slump test (KS F 2402)

1) The inside of the slump cone was wiped with a wet rag and placed on a watertight flat plate.

2) The sample was put about 1/3 of the volume of the slump cone (about 7 ㎝ in depth) and evenly smoothed 25 times over the entire surface with a compaction rod.

3) Samples were put in 2/3 (depth of about 16 ㎝) of the volume of slump cone and plastered 25 times with compaction bars. At this time, the depth of the compaction rod into the concrete was about 9 ㎝.

4) Finally, overflow the sample into the slump cone and tweak it 25 times with the compaction rod.

5) The surface of the sample was matched to the top surface of the slump cone and flattened.

6) I pulled up the slump cone.

7) The length of the concrete slope was measured with a precision of 5 ㎜.

Test Example 2: Air quantity test (KS F 2409)

1) The sample was divided into three layers of almost the same height, each layer was evenly divided ten times, and the side of the container was knocked about five times with a wooden hammer.

2) Next, the excess sample was used to make it flat. After thoroughly wiping the top of the flange of the container and the lower flange of the cover, the cover was attached to the container so that the inside and the outside of the cover could be ventilated, the air pressure was tightened tightly and the air pressure in the air room was matched to the initial pressure.

3) After about 5 seconds, the operator panel was fully opened. I pressed the side of the container with a wooden hammer so that the pressure of each part of the concrete was well filled in every corner. After the operating plate was sufficiently opened again, the reading of the pressure gauge of the pressure gauge was read to one decimal place from when the needle was stabilized.

practice
Yes
Ether compound EO
confiscation reaction
time mountain
anhydride Reaction rate
(%) Yield
(%) One
CH 2 = C (CH 3 ) -CH 2 -O- (CH 2 -CH 2 -O) 60 -H

60mol 22h Seosin acid
anhydride 99.4 98 2 8h Maleic acid
anhydride 99.8 99.2 3 60h Phthalic acid
anhydride 95.1 80.6 4
CH 2 ═C (CH 3 ) -CH 2 CH 2 -O- (CH 2 -CH 2 -O) 60 -H 20h Seosin acid
anhydride 99.6 99.4 5 4h Maleic acid
anhydride 99.9 99.9 6 60h Phthalic acid
anhydride 97.5 91.2 7 CH 2 ═C (CH 3 ) -CH 2 -O- (CH 2 -CH 2 -O) 30 -H 30mol 7h Seosin acid
anhydride 99.2 96.8 8 CH 2 ═C (CH 3 ) -CH 2 -O- (CH 2 -CH 2 -O) 15 -H 15mol 5h Seosin acid
anhydride 99.3 97.9 9 CH 2 ═C (CH 3 ) -CH 2 -O- (CH 2 -CH 2 -O) 30 -H 30mol 6h Seosin acid
anhydride 99.2 98.8

Admixture addition amount and time-dependent flow value, air quantity, compressive strength change
division
Addition amount
(%)
Flow (mm)
Air
(%) Early 60 minutes Production Example 1 1.0 600 x 600 450 × 450 3.1 Production Example 2 1.0 600 × 620 500 x 500 3.2 Production Example 3 1.0 600 x 600 450 × 450 3.1 Production Example 4 1.0 600 × 620 500 x 500 3.2 Comparative Example 1.0 500 x 500 350 x 350 3.5

Referring to Tables 1 and 2, as a result of conducting a non-hardened concrete test at the same addition amount, it can be confirmed that the initial flow values of the samples of Production Examples 1 to 4 are superior to those of Comparative Examples. Also, after 60 minutes, the performance was superior to the comparative example, and the air amount was also superior to the comparative example.

While the present invention has been described in connection with what is presently considered to be practical exemplary embodiments, it is to be understood that the invention is not limited to the disclosed embodiments, but, on the contrary, Of course it is possible. Accordingly, the scope of the present invention should not be construed as being limited to the above-described embodiments, but should be determined by equivalents to the appended claims, as well as the following claims.

Claims (17)

A monomer for producing a dispersant represented by the following formula (1):
[Chemical Formula 1]
Figure 112017021814839-pat00032

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, and n represents an average molar number of oxyalkylene groups added, A dispersant comprising a copolymer obtained by polymerizing a monomer for producing a dispersant of claim 1 as a monomer for copolymerization. A mortar or concrete comprising the dispersant of claim 2. Reacting a compound represented by the following formula (2) with a compound represented by the following formula (3): < EMI ID =
[Chemical Formula 1]
Figure 112017021814839-pat00033

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,
(2)
Figure 112017021814839-pat00034

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;
(3)
Figure 112017021814839-pat00035

Wherein X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms. The method of claim 4,
Wherein the compound of Formula 1 is prepared by reacting at 25 to 130 占 폚. The method of claim 4,
Wherein the compound of Formula 1 is prepared by reacting at 25 to 130 占 폚 in the presence of a polymerization inhibitor. The method of claim 4,
Wherein the compound of Formula 1 is prepared by reacting in the presence of an acidic catalyst. A polymer represented by the following formula (6), obtained by reacting a macromonomer represented by the following formula (1) with at least one of a compound represented by the following formula (2), a compound represented by the following formula (4)
[Chemical Formula 1]
Figure 112017021814839-pat00036

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,
(2)
Figure 112017021814839-pat00037

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;
[Chemical Formula 4]
Figure 112017021814839-pat00038

Wherein R10, R11 and R12 are hydrogen, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms or allyl of 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, or 1 Secondary, or tertiary amine;
[Chemical Formula 5]
Figure 112017021814839-pat00039

Wherein R13 and R14 are hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms or allyl having 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, A tertiary amine;
[Chemical Formula 6]
Figure 112017021814839-pat00040

Wherein o, p, q and r represent the average number of moles, 0? O, p, r? 400, and 0.1 ≤ q ≤ 400, and o + p ≥ 0.1. The method of claim 8,
Wherein the polymer represented by the formula (6) has a weight average molecular weight of 10,000 to 300,000. The method of claim 8,
q + r < = o + p. The method of claim 8,
p: 0.1 to 400: 0 to 400: 0 to 400: 0 to 400, and o + p? 0.1. A dispersant comprising the polymer of claim 8. A mortar or concrete comprising the dispersant of claim 12. A process for preparing a polymer comprising the steps of:
(A) obtaining a macromonomer represented by the formula (1) obtained by reacting a compound represented by the following formula (2) and a compound represented by the following formula (3)
[Chemical Formula 1]
Figure 112017021814839-pat00041

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms, Z is hydrogen, An alkoxy group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, an organic amine having 1 to 30 carbon atoms, an alkali metal or an alkaline earth metal, n is an average number of moles of oxyalkylene groups added,
(2)
Figure 112017021814839-pat00042

Wherein R 1, R 2 and R 3 are hydrogen, an alkyl group having 1 to 30 carbon atoms or an alkenyl group having 2 to 30 carbon atoms, R 4 is a single bond, an alkylene group having 1 to 15 carbon atoms or an alkenylene group having 2 to 15 carbon atoms , R5 is an alkylene group or an alkenylene group having 2 to 10 carbon atoms, n is an average molar number of addition of oxyalkylene groups and is 1 to 400;
(3)
Figure 112017021814839-pat00043

Wherein X is an alkylene group having 1 to 20 carbon atoms, an alkenylene group having 2 to 20 carbon atoms, or a phenylene group having 6 to 20 carbon atoms; And
(B) a polymer obtained by reacting at least one of the compound represented by the formula (2), the compound represented by the following formula (4) and the compound represented by the following formula (5) with the macromonomer represented by the formula Obtaining a polymer;
[Chemical Formula 4]
Figure 112017021814839-pat00044

Wherein R10, R11 and R12 are hydrogen, alkyl of 1 to 30 carbon atoms, alkenyl of 2 to 30 carbon atoms or allyl of 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, or 1 Secondary, or tertiary amine;
[Chemical Formula 5]
Figure 112017021814839-pat00045

Wherein R13 and R14 are hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms or allyl having 3 to 30 carbon atoms, M is hydrogen, a monovalent or divalent metal or ammonia, A tertiary amine;
[Chemical Formula 6]
Figure 112017021814839-pat00046

Wherein o, p, q and r represent the average number of moles, 0? O, p, r? 400, and 0.1 ≤ q ≤ 400, and o + p ≥ 0.1. 15. The method of claim 14,
Wherein the polymer represented by the formula (6) has a weight average molecular weight of 10,000 to 300,000. 15. The method of claim 14,
q + r < = o + p. The method of claim 8,
wherein q is from 0 to 400: 0 to 400: 0 to 400, and o + p is from 0.1.
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