JP2001172237A - New compound and its manufacturing method - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compound usable as a raw material for a polymer having a specific character fully exhibiting its effect on various specific uses such as a specific monomer preferably used as a raw material for a water-soluble polymer having excellent characters e.g. acquiring force to a hardness ingredient such as calcium ion or the like and dispersing action to inorganic particles and acquiring force against to a heavy metal and provide its manufacturing method. SOLUTION: The compound is preferably expressed by general formula (1) and is obtained by reacting a primary or a secondary amine or ammonia with an epoxybutene, having a carbon - carbon double bond, hydroxy and amino. R5 and R6 are each H or an organic group in the formula.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a compound having a carbon-carbon double bond, a hydroxyl group and an amino group, and a method for producing the same.

[0002]

BACKGROUND OF THE INVENTION In a wide variety of fields, very different polymers are used in very different applications. For example, a polycarboxylic acid-based polymer represented by an acrylic acid homopolymer, a maleic acid homopolymer, or an acrylic acid / maleic acid copolymer has an ability to capture a hardness component such as calcium ions and an inorganic particle. It is known that the dispersing action is extremely excellent, and taking advantage of these features, for example, fiber treatment agents, wood pulp bleaching aids, hydrogen peroxide stabilizers, inorganic pigment dispersants, scale inhibitors, detergent compositions It is used for various purposes such as objects.

[0003] Although these polycarboxylic acid-based polymers have the above-mentioned characteristics, their ability to capture heavy metals is inadequate, and at present, they are not always sufficient for the above-mentioned applications. It is known that organic chelating agents such as ethylenediaminetetraacetate, nitrilotriacetate, or organic phosphonic acid chelating agents are relatively high in terms of the capturing power for heavy metals. However, the effect on the above-mentioned application is extremely insufficient because the capturing power for the hardness component such as calcium ions is insufficient and the dispersing action on the inorganic particles is completely insufficient.

[0004] Therefore, for the above-mentioned applications, an agent having a sufficiently high scavenging power for heavy metals and an extremely excellent scavenging power for hardness components such as calcium ions and a dispersing action for inorganic particles, ie, calcium ions, etc. There is an urgent need for the development of a polymer that utilizes the characteristics of being extremely excellent in the ability to capture hard components and the action of dispersing inorganic particles, and has the ability to capture heavy metals.

[0005]

SUMMARY OF THE INVENTION Accordingly, the present inventors solve the above-mentioned problem, that is, the problem of developing a polymer having specific characteristics which can exert its effects for various specific applications. To this end, the design of a monomer as a raw material of the polymer was considered to be particularly important, and intensive studies were conducted. As a result, primary or secondary amines specific to epoxybutenes,
Alternatively, it has been found that a specific compound having a carbon-carbon double bond, a hydroxyl group and an amino group obtained by reacting ammonia and a method for producing the same are very useful.

Accordingly, an object of the present invention is to provide a water-soluble polymer which has an excellent ability to scavenge hardness components such as calcium ions and a dispersing action to inorganic particles, and has a scavenging ability to heavy metals. Provide a compound which is a raw material of a polymer having specific characteristics and exerts its effects for various specific applications including a specific monomer suitably used as a raw material, and a method for producing the same. Is to do.

[0007]

Means for Solving the Problems In order to solve the above problems, the present invention provides the following configurations. A compound having a carbon-carbon double bond, a hydroxyl group and an amino group, obtained by reacting an epoxybutene with a primary or secondary amine or ammonia. In the general formula (2), R ₅ , which is a substituent of an amino group,
And R ₆ is a compound having a specific structure. A method for producing a compound having a carbon-carbon double bond, a hydroxyl group and an amino group by reacting an epoxybutene with a primary or secondary amine or ammonia. More specifically, for example, a specific structure obtained by reacting at least one compound selected from taurine, iminodiacetic acid, aspartic acid and salts thereof, diethanolamine, and ethylenediamine with 3,4-epoxy-1-butene is used. Compound having.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION A compound having a carbon-carbon double bond, a hydroxyl group and an amino group and a method for producing the same according to the present invention will be described in detail below.

[Compound] The compound of the present invention is a carbon-carbon double bond obtained by reacting an epoxybutene represented by the following general formula (1) with a primary or secondary amine or ammonia. And a compound having a hydroxyl group and an amino group.

[0010]

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Here, R ¹ , R ² , R ³ and R ⁴ are each independently hydrogen or an organic group.

Preferably, for example, in the general formula (1), 3,4-epoxy-1-butene in which all of R ¹ , R ² , R ³ and R ⁴ are hydrogen, A compound having a carbon-carbon double bond, a hydroxyl group and an amino group, obtained by reacting a primary or secondary amine or ammonia, and more preferably a compound represented by the following general formula (2) .

[0013]

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Here, R ⁵ and R ⁶ are each independently hydrogen or an organic group. Further, for example, a water-soluble polymer, particularly a polycarboxylic acid polymer, is useful, such as a fiber treating agent, a wood pulp bleaching aid, a hydrogen peroxide stabilizer, an inorganic pigment dispersant, a scale inhibitor, and a detergent composition. When used as a raw material of a polymer used for various applications, preferably, in the above general formula (2), R ⁵ and R ⁶ are not hydrogen at the same time and are independently listed below. The compound is a substituent. An organic group having a hydrogen carboxylic acid group or a salt of these acid groups; An organic group having a sulfonic acid group or a salt of these acid groups. It is a compound having at least one substituent of any one of an organic group having a hydroxyl group and an organic group having an amino group. Here, the organic group includes, for example, an alkenyl group, an alkynyl group and an aromatic group.

The salt of the acid group is not particularly limited. Examples thereof include alkali metal salts such as sodium, potassium and lithium, alkaline earth metal salts such as calcium and magnesium, ammonium salts, monoethanolamine, and the like. Organic amine salts such as triethanolamine are exemplified.

These compounds have various functional groups in addition to a hydroxyl group and an amino group in a carbon-carbon double bond and a side chain, and for example, have a hardness such as calcium ion which is useful for the above-mentioned applications. It is very preferable as a raw material for a polymer that has a very good trapping power for components and a dispersing action for inorganic particles and also has a trapping power for heavy metals.

Further, when used as a raw material of a polymer for the above applications, most preferably, in the general formula (2), R ⁵ and R ⁶ are not simultaneously hydrogen, but are independently hydrogen or The compound is any one of the substituents shown below.

[0018]

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Here, X ^{1 to} X ⁷ independently of each other,
Hydrogen or an alkali metal salt, an alkaline earth metal salt, an ammonium salt, or an organic amine salt. R ⁷ and R ⁸ are
They are not hydrogen at the same time and are independently hydrogen or organic groups.

In the above, alkali metals include, for example, sodium, potassium, lithium and the like, alkaline earth metals include calcium, magnesium and the like, and organic amines include monoethanolamine and triethanolamine. And the like.

Specifically, for example, the following compounds are shown, and the structures of the substituents R ⁵ and R ⁶ in the general formula (2) are more specifically shown.

In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0023]

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X ¹ is hydrogen, or an alkali metal salt, an alkaline earth metal salt, an ammonium salt, or an organic amine salt. Examples of the alkali metal include sodium, potassium, lithium and the like, examples of the alkaline earth metal include calcium and magnesium, and examples of the organic amine include monoethanolamine and triethanolamine. These may be used alone or as a mixture of two or more.

In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0026]

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X ⁴ and X ⁵ are hydrogen or an alkali metal salt, an alkaline earth metal salt, an ammonium salt or an organic amine salt. Examples of the alkali metal include sodium, potassium, lithium and the like, examples of the alkaline earth metal include calcium and magnesium, and examples of the organic amine include monoethanolamine and triethanolamine. These may be used alone or as a mixture of two or more.

In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0029]

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X ⁶ and X ⁷ are hydrogen or an alkali metal salt, an alkaline earth metal salt, an ammonium salt or an organic amine salt. Examples of the alkali metal include sodium, potassium, lithium and the like, examples of the alkaline earth metal include calcium and magnesium, and examples of the organic amine include monoethanolamine and triethanolamine. These may be used alone or as a mixture of two or more.

In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0032]

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X ³ is hydrogen, or an alkali metal salt, an alkaline earth metal salt, an ammonium salt, or an organic amine salt. Examples of the alkali metal include sodium, potassium, lithium and the like, examples of the alkaline earth metal include calcium and magnesium, and examples of the organic amine include monoethanolamine and triethanolamine. These may be used alone or as a mixture of two or more.

In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0035]

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X ¹ is hydrogen, or an alkali metal salt, an alkaline earth metal salt, an ammonium salt, or an organic amine salt. Examples of the alkali metal include sodium, potassium, lithium and the like, examples of the alkaline earth metal include calcium and magnesium, and examples of the organic amine include monoethanolamine and triethanolamine. These may be used alone or as a mixture of two or more.

In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0038]

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X ² is hydrogen, or an alkali metal salt, an alkaline earth metal salt, an ammonium salt, or an organic amine salt. Examples of the alkali metal include sodium, potassium, lithium and the like, examples of the alkaline earth metal include calcium and magnesium, and examples of the organic amine include monoethanolamine and triethanolamine. These may be used alone or as a mixture of two or more.

More specifically, for example, the following compounds are shown, and the structures of the substituents R ⁵ and R ⁶ in the general formula (2) are more specifically shown.

[0041]

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In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

Embedded image In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0043]

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In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0045]

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In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0047]

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In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

Embedded image In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0049]

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In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0051]

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In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0053]

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In the general formula (2), R ⁵ and R ⁶ are the substituents shown below.

[0055]

Embedded image [Method for Producing Compound] Next, a method for producing the compound of the present invention will be described. The method for producing a compound having a carbon-carbon double bond, a hydroxyl group and an amino group according to the present invention includes:
For example, a primary or secondary amine or ammonia is reacted with epoxybutenes in a solvent and under stirring.

<Epoxybutenes> The epoxybutenes used in the present invention are not particularly limited as long as they are compounds described in the general formula (1), and may be appropriately selected according to the purpose.
Specifically, 3,4-epoxy-1-butene, 3,4-
Epoxy-3-methyl-1-butene, 3,4-epoxy-1-pentene, 3,4-epoxy-3-methylpentene and the like. Further, other than the general formula (1), 5,6-epoxy-1-hexene, vinylcyclohexene mono-epoxide and the like can also be used. If the reaction conditions and the polymerizability and physical properties of the compound to be produced are not affected, the above-mentioned reaction may be carried out on at least one epoxybutene selected from the listed starting materials.

From the viewpoint of easiness of synthesis or easiness of handling, preferably, R in formula (1)
3,4-epoxy wherein all of R ¹ , R ² , R ³ and R ⁴ are hydrogen
1-butene.

<Primary or secondary amine or ammonia> The primary or secondary amine or ammonia used in the present invention is not particularly limited, and may be appropriately selected according to the purpose.

The obtained compound is, for example, a fiber treating agent,
Wood pulp bleaching aid, hydrogen peroxide stabilizer, inorganic pigment dispersant, scale inhibitor, detergent composition, etc., water-soluble polymer,
In particular, as a raw material of the polymer used for various applications where the polycarboxylic acid polymer is useful, as described above,
In addition to the carbon-carbon double bond, the hydroxyl group and the amino group, having various functional groups is very effective for the above-mentioned application in capturing power for hardness components such as calcium ions and dispersing action for inorganic particles. It is very preferable as a raw material for a polymer that has both excellent and heavy metal capturing power. Therefore, in obtaining the compound of the present invention,
A primary or secondary amine having at least one functional group selected from a hydroxyl group, a carboxyl group and a sulfonic acid group, or at least two or more having at least one primary or secondary amine It is preferable to use the above amine having an amino group to react with epoxybutenes.

More preferably, the above-mentioned primary or secondary amine having at least one functional group selected from a hydroxyl group, a carboxyl group, and a sulfonic acid group, or at least one or more of the primary or secondary amine is a primary or secondary amine. Examples of the amine having at least two or more amino groups having a diamine include amino acids such as taurine derivatives, iminodiacetic acid derivatives, and aspartic acid derivatives, and salts thereof, and organic compounds such as diethanolamine derivatives and ethylenediamine derivatives. Use of an alkanolamine, an organic dialkanolamine or an organic diamine is particularly preferable, and examples thereof include taurine, iminodiacetic acid, aspartic acid and salts thereof, diethanolamine and ethylenediamine.

Most preferably, 3,4-epoxy-1-butene is used as the epoxybutene, and taurine, iminodiacetic acid, aspartic acid and salts thereof, diethanolamine and ethylenediamine are used as the amine component. The reaction may be carried out using at least one raw material selected from various amine raw materials as long as the reaction is not hindered and there is no problem in the polymerizability and physical properties of the compound to be produced.

<Solvent> In the present invention, for example, when a solvent is used, the solvent is not particularly limited, and the solubility of the epoxybutenes and the primary or secondary amine or ammonia used,
It may be appropriately set in consideration of the solubility of the compound obtained by the reaction and the like.

When the obtained compound is used as a raw material for a water-soluble polymer for use in the above applications, it is preferably an aqueous solvent, more preferably water. In order to improve the solubility of epoxybutenes and primary or secondary amines or ammonia, other aqueous organic solvents may be appropriately added in an amount of 30% by weight or less. Specifically, one or two or more of lower alcohols such as methanol, ethanol, and isopropyl alcohol; amides such as dimethylformamide; ethers such as diethyl ether and dioxane; . This is because the water-soluble polymer is usually polymerized in an aqueous solvent,
When the compound of the present invention is produced in an organic solvent, an operation such as recovery of the organic solvent is required, which is not preferable from the viewpoint that the production process becomes complicated and economically disadvantageous. When prepared with an aqueous solvent, particularly preferably water,
It is very preferable because the polymerization step can be used as it is.

<Method of Adding Raw Materials at the Time of Reaction> In the present invention, when a solvent is used, for example, the method of adding the raw materials at the time of the reaction, that is, the epoxybutenes and the primary or secondary amine or ammonia ( Hereinafter, the method for adding the “amine component” is simply not limited, and the reactivity of the epoxybutenes and the amine component used, or the solvent of the amine component used and the compound obtained after the reaction, is added to the solvent. May be set as appropriate in consideration of the solubility of the compound. Here, specifically, epoxy butenes of 3,4
-Epoxy-1-butene will be described as an example.

The method for adding 3,4-epoxy-1-butene and the amine component is as follows. 3,4-Epoxy-1-butene is initially charged all at once, and the amine component is initially charged all at once. 3,4-Epoxy-1-butene is initially charged all at once, and the amine component is partially initially charged and partially dropped. 3,4-Epoxy-1-butene is initially charged all at once, and the entire amount of the amine component is dropped. Initially, 3,4-epoxy-1-butene is partially charged and partially dropped, and the entire amount of the amine component is dropped. 3,4-Epoxy-1-butene is initially charged and partially dropped, and the amine component is partially charged and partially dropped. 3,4-Epoxy-1-butene is partially initially charged and partially dropped, and the amine component is initially charged all together. 3,4-Epoxy-1-butene is dripped in the entire amount, and the amine component is dripped in the entire amount. The whole amount of 3,4-epoxy-1-butene is dropped, the amine component is partially charged initially, and then partially dropped. The entire amount of 3,4-epoxy-1-butene is added dropwise, and the amine component is initially charged at once.

Here, when a primary amine or ammonia is used as an amine component, or when an amine component has two or more primary or secondary amines or ammonia, 3,4-epoxy-amine is added to the reaction system. When 1-butene is present in a large excess, there is a possibility that a plurality of 3,4-epoxy-1-butenes may react with these amine components, so that reaction control may not be performed. Therefore, in such a case, it is preferable to sequentially react 3,4-epoxy-1-butene, and it is preferable that unreacted 3,4-epoxy-1-butene is present in a large excess in the reaction system. Therefore, it may be appropriately set in consideration of the reactivity with the amine component, but 3,4-epoxy-1-butene is used in an amount of 50%.
It is preferable to drop at least 80% by weight, more preferably at least 80% by weight, and most preferably to drop the whole amount.

As described above, the solvent is an aqueous solvent,
Particularly preferably, when water is used, 3,4-epoxy-1
-Butene is not soluble in water. Therefore, unreacted 3, 4
-Epoxy-1-butene is phase-separated in the reaction system without stirring, becomes dispersed in an aqueous solvent under stirring, and the reaction proceeds at these interfaces. Therefore, in order to increase reactivity, that is, to increase the surface area of the interface, 3,4-epoxy-1-
Since it is preferable to disperse butene in a micro state,
It is preferred to produce under stirring. In this case, when the amine component used is compatible with 3,4-epoxy-1-butene, the amine component may be taken into the 3,4-epoxy-1-butene phase. The amine component incorporated in the 3,4-epoxy-1-butene phase is not preferable because it becomes substantially the same as the above-mentioned reaction system having a large excess of 3,4-epoxy-1-butene. Therefore, in an aqueous solvent,
Particularly preferably, when the reaction is carried out with water, unreacted 3,3
Since it is not preferable that a large amount of 4-epoxy-1-butene is present in the reaction system, it is preferable that 50% by weight or more of 3,4-epoxy-1-butene is dropped, and 80% by weight or more. Is more preferably added, and the entire amount is most preferably added dropwise.

On the other hand, the method of adding the amine component is not particularly limited, and may be appropriately set according to the reactivity of the amine component used and the solubility in the solvent.

As described above, when the primary amine or ammonia is used as the amine component, or when the amine component has two or more primary or secondary amines or ammonia, the amine component is contained in the reaction system. Since it is preferable that the amine component is present in an excess amount, the initial charge of the amine component is preferably 50% by weight or more, more preferably 80% by weight or more, and most preferably the initial charge.

Further, when an aqueous solvent, particularly preferably water, is used as the solvent, unreacted 3,3
Since it is preferable that an excess amount of the amine component is present in order to reduce the amount of 4-epoxy-1-butene, the amine component is preferably initially charged at least 50% by weight, more preferably at least 80% by weight, most preferably. Is the initial preparation of the whole amount.

In summary, 3,4-epoxy-1-
The method of adding the butene and amine components is not particularly limited, but in 3,4-epoxy-1-butene, preferably 50% by weight or more of the amount used is dropped, preferably 80% by weight or more. More preferably, the total amount is dropped, and the initial charge is preferably 50% by weight or more in the amine component, and more preferably 8% by weight.
The initial charge is 0% by weight or more, and most preferably the initial charge is the entire amount.

<Drip time> The drop time of the above-mentioned components is not particularly limited, and is preferably within the above-mentioned preferable range in view of the reactivity of the components to be dropped and the reaction temperature and reaction system to be described later. What is necessary is just to set suitably within the range which can be adjusted to pH etc.

<Others> The reaction temperature in the production method of the present invention is preferably 50 ° C. or lower, more preferably 40 ° C. or lower. It is. If it exceeds 50 ° C,
When an aqueous solvent is used as the solvent, 3,4-epoxy-
1-butene is not preferred because it may react with water.

The pH in the reaction system is optional,
Generally, the ring opening reaction of an epoxide with an amino group is preferably 7 or more, more preferably 8 or more, and still more preferably 10 or more, because the higher the pH, the higher the reactivity. If the pH is less than 7, the reactivity may be significantly deteriorated. The pH adjuster is not particularly limited, and a normal pH adjuster such as sodium hydroxide or potassium hydroxide may be used as needed.

The concentration is not particularly limited, but is preferably at least 10% by weight, more preferably at least 20% by weight, in terms of the solid content of the compound obtained after the reaction. If it is less than 10% by weight, productivity is extremely low, which is not preferable.

The reaction pressure may be any of normal pressure (atmospheric pressure), pressurization and decompression.

Although a catalyst is basically unnecessary, any catalyst which does not adversely affect the reaction may be used as needed.

[0078]

EXAMPLES Hereinafter, the present invention will be described specifically with reference to examples, but the present invention is not limited to these examples. “%” Indicates “% by weight”.

Example 1 As epoxybutenes,
4-epoxy-1-butene, and L-
Sodium aspartate was used. That is, reflux cooling
2.5-liter SUS separator equipped with a stirrer and stirrer
358 g of ion-exchanged water in a rubble flask, 48% hydroxyl
Charge 333 g of sodium chloride aqueous solution, and add L-asparagine
266 g of acid were added. Then, with stirring, the liquid temperature should be 40 ° C or lower
140 g of 3,4-epoxy-1-butene while keeping below
Was gradually added dropwise. After dropping, react for 1 hour at 40 ° C.
3,4-epoxy-1-butene-L-aspartic acid
An aqueous solution of the derivative monomer was obtained. Also, from this aqueous solution
After removing water, 3,4-epoxy-1-butene-L-A
Spartic acid derivative monomer was isolated. 3,4-epo
Xyl-1-butene-L-aspartic acid derivative monomer
about, ¹The result of performing the H-NMR measurement is as follows.
there were.¹ H-NMR (D_TwoO): δ 2.22 to 2.46 (4
H), δ 3.35 (2H), δ 5.18 (2H), δ
5.63 (1H) From the above results, 3,4-epoxy-1-butene-L-A
The structure of the sparginate derivative monomer is represented by the general formula (2)
It became clear that the following cases were applicable.

[0080]

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(Example 2) As epoxybutenes,
4-Epoxy-1-butene and iminodiacetic acid sodium salt were used as amine components. That is, 358 g of ion-exchanged water and 333 g of a 48% aqueous sodium hydroxide solution were charged into a 2.5-liter SUS separable flask equipped with a reflux condenser and a stirrer, and 266 g of iminodiacetic acid was added.
Was added. Thereafter, 140 g of 3,4-epoxy-1-butene was gradually dropped while maintaining the liquid temperature at 40 ° C. or lower while stirring. After the completion of the dropwise addition, the reaction was carried out at 40 ° C. for 1 hour.
-An aqueous solution of an epoxy-1-butene-iminodiacetic acid derivative monomer was obtained. Further, water was removed from the aqueous solution to isolate a 3,4-epoxy-1-butene-iminodiacetic acid derivative monomer. ¹ H-NMR of 3,4-epoxy-1-butene-iminodiacetic acid derivative monomer
The results of the measurement were as follows. ¹ H-NMR (D ₂ O): δ 3.15 (6H), δ 3.4
6 (1H), δ5.12 (2H), δ5.63 (1H) From the above results, the structure of the 3,4-epoxy-1-butene-iminodiacetic acid derivative monomer is represented by R ⁵ in the general formula (2). : CH ₂ COONa R ⁶ : CH ₂ COONa.

Example 3 As epoxybutenes,
4-Epoxy-1-butene and diethanolamine as an amine component were used. That is, 163 g of ion-exchanged water was charged into a 2.5-liter SUS separable flask equipped with a reflux condenser and a stirrer, and 53 g of diethanolamine was added. Thereafter, 35 g of 3,4-epoxy-1-butene was gradually added dropwise while stirring at a temperature of 40 ° C. or lower. After the completion of the dropwise addition, the mixture was reacted at 40 ° C. for 1 hour,
An aqueous solution of a 3,4-epoxy-1-butene-diethanolamine derivative monomer was obtained. Further, water was removed from the aqueous solution to isolate a 3,4-epoxy-1-butene-diethanolamine derivative monomer. The results of ¹ H-NMR measurement of the 3,4-epoxy-1-butene-diethanolamine derivative monomer were as follows. ¹ H-NMR (D ₂ O): δ2.59 (6H), δ3.5
2 (5H), δ5.14 (2H), δ5.65 (1H) From the above results, the structure of the 3,4-epoxy-1-butene-diethanolamine derivative monomer is represented by the general formula (2)
In _{^{R 5: CH 2 CH 2 OH}} R 6: revealed that the case for CH ₂ CH ₂ OH.

Example 4 As an epoxybutene, 3,
4-epoxy-1-butene, and NH as an amine component
_{2 -CH 2 -CH 2 -NH-CH} 2 -CH (OH) -CH = C
H ₂ was used. That is, 371 g of ion-exchanged water was charged into a 2.5-liter SUS separable flask equipped with a reflux condenser and a stirrer, and 60 g of ethylenediamine was added. Thereafter, 140 g of 3,4-epoxy-1-butene was gradually dropped while maintaining the liquid temperature at 40 ° C. or lower while stirring. After the completion of the dropwise addition, the reaction was carried out at 40 ° C. for 1 hour.
-An aqueous solution of an epoxy-1-butene-ethylenediamine derivative monomer was obtained. Further, water was removed from the aqueous solution to isolate a bis 3,4-epoxy-1-butene-ethylenediamine derivative monomer. The results of ¹ H-NMR measurement of the bis 3,4-epoxy-1-butene-ethylenediamine derivative monomer were as follows. ¹ H-NMR (D ₂ O): δ 2.50 (8H), δ 3.3
8 (2H), δ5.09 (4H), δ5.60 (2H) From the above results, bis 3,4-epoxy-1-butene-
It became clear that the structure of the ethylenediamine derivative monomer corresponds to the following case in the general formula (2).

[0084]

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Example 5 As an epoxybutene, 3,
4-epoxy-1-butene, and L-
Glutamate sodium salt was used. That is, 392 g of ion-exchanged water and 333 g of a 48% sodium hydroxide aqueous solution were charged into a 2.5-liter SUS separable flask equipped with a reflux condenser and a stirrer, and 294 g of L-glutamic acid was added. Thereafter, 140 g of 3,4-epoxy-1-butene was gradually dropped while maintaining the liquid temperature at 40 ° C. or lower while stirring. After completion of the dropwise addition, the mixture was reacted at 40 ° C. for 1 hour to obtain an aqueous solution of 3,4-epoxy-1-butene-L-glutamic acid derivative monomer. Further, water was removed from the aqueous solution to isolate a 3,4-epoxy-1-butene-L-glutamic acid derivative monomer. This compound corresponds to the following case in the general formula (2).

[0086]

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(Example 6) As epoxybutenes,
Taurine was used as 4-epoxy-1-butene and an amine component. Specifically, 407 g of ion-exchanged water and a 48% aqueous sodium hydroxide solution 16 were placed in a 2.5-liter SUS separable flask equipped with a reflux condenser and a stirrer.
7 g was charged, and 250 g of taurine was added. Thereafter, 140 g of 3,4-epoxy-1-butene was gradually dropped while maintaining the liquid temperature at 40 ° C. or lower while stirring. After dropping,
The reaction was carried out at 40 ° C. for 1 hour to obtain an aqueous solution of a 3,4-epoxy-1-butene-taurine derivative monomer. Further, water was removed from the aqueous solution to give 3,4-epoxy-1-
The butene-taurine derivative monomer was isolated. This compound is represented by the formula (2): R ⁵ : H R ⁶ : CH ₂ CH ₂
This corresponds to the case of SO ₃ Na.

(Example 7) As epoxybutenes,
4-epoxy-1-butene and ethylenediamine as an amine component were used. That is, 317 g of ion-exchanged water was charged into a 2.5-liter SUS separable flask equipped with a reflux condenser and a stirrer, and ethylenediamine 1
20 g were added. Thereafter, 140 g of 3,4-epoxy-1-butene was gradually dropped while maintaining the liquid temperature at 40 ° C. or lower while stirring. After the completion of the dropwise addition, the mixture was reacted at 40 ° C. for 1 hour,
An aqueous solution of a 3,4-epoxy-1-butene-ethylenediamine derivative monomer was obtained. Further, water was removed from the aqueous solution to isolate a 3,4-epoxy-1-butene-ethylenediamine derivative monomer. This compound corresponds to the case where R ⁵ : HR ⁶ : CH ₂ CH ₂ NH _{2 in} the general formula (2).

[0089]

The compound of the present invention has a carbon-carbon double bond, a hydroxyl group and an amino group, and is suitably used, for example, as a raw material of a polymer for various purposes. Further, it can also be used as a modifying monomer or a modifying compound utilizing a carbon-carbon double bond. It can also be used as a reactive monomer having a special functional group.

For example, a primary or secondary amine having at least one functional group such as a hydroxyl group, a carboxyl group, or a sulfonic acid group, or at least one having a primary or secondary amine has The compound having a carbon-carbon double bond, a hydroxyl group, and an amino group having various structures according to the present invention obtained by using an amine having at least two or more amino groups may be used as a fiber treatment agent, a wood pulp bleaching aid, It is very suitably used as a raw material of a polymer used for applications such as a hydrogen oxide stabilizer, an inorganic pigment dispersant, a scale inhibitor, and a detergent composition.

Further, according to the method for producing a compound of the present invention, various specific compounds can be quantitatively and easily produced according to the above objects.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification code FI Theme coat ゛ (Reference) C08F 26/02 C08F 26/02 F term (Reference) 4H006 AA01 AA02 AB46 AB72 AB83 AC41 AC52 BE14 BN10 BN90 BS10 BS70 NB10 NB27 4J100 AN02P AN03P AN06P BA03P BA29P CA01 CA03 JA11 JA13 JA15

Claims (5)

[Claims] 1. A carbon-carbon double bond, a hydroxyl group and an amino group, which are obtained by reacting a primary or secondary amine or ammonia with an epoxybutene represented by the following general formula (1): Compounds having. Embedded image Here, R ¹ , R ² , R ³ and R ⁴ are each independently hydrogen or an organic group. 2. The compound according to claim 1, which is represented by the following general formula (2). Here, R ⁵ and R ⁶ are each independently hydrogen or an organic group. 3. In the general formula (2), R ⁵ and R ⁶ are
An organic group having a hydrogen carboxylic acid group or a salt of these acid groups independently of each other without being simultaneously hydrogen. An organic group having a sulfonic acid group or a salt of these acid groups. The compound according to claim 1, which is a substituent of any one of an organic group having a hydroxyl group and an organic group having an amino group. 4. In the following general formula (2): A compound in which R ⁵ and R ⁶ are not hydrogen at the same time and are independently hydrogen or any of the substituents shown below. Embedded image Here, X ^{1 to} X ⁷ are each independently hydrogen, an alkali metal salt, an alkaline earth metal salt, an ammonium salt,
It is an organic amine salt. R ⁷ and R ⁸ are not simultaneously hydrogen, but are each independently hydrogen or an organic group. 5. A compound having a carbon-carbon double bond, a hydroxyl group and an amino group by reacting an epoxybutene represented by the following general formula (1) with a primary or secondary amine or ammonia. Production method. Embedded image Here, R ¹ , R ² , R ³ and R ⁴ are each independently hydrogen or an organic group.