Composition containing polyaldehyde compounds and method for producing the same

Abstract

To provide a polyaldehyde compound-containing composition that is less prone to heat-induced coloration, and a method for producing the same.SOLUTION: A polyaldehyde compound-containing composition contains a polyaldehyde compound blended with a predetermined amount of a low-molecular-weight aldehyde compound. Consequently, the polyaldehyde compound-containing composition is less prone to heat-induced coloration in its solid state.SELECTED DRAWING: None

Description

Technical Field

[0001] The present invention relates to a polyaldehyde compound-containing composition and a method for producing the same.

Background Art

[0002] Polyaldehyde compounds obtained from carbohydrates such as starch, dextrin, and oligosaccharides using an oxidizing agent such as periodate have a large number of highly reactive aldehyde groups and can easily bond to hydroxyl groups and amino groups. Therefore, they are known to be excellent as paper strength enhancers (Patent Document 1). In addition, binder compositions combined with polyaldehyde compounds and polyamines or polyamides are known (Patent Documents 2 and 3).

Prior Art Documents

Patent Documents

[0003]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0004] As a result of the study by the present inventors, it has been found that the polyaldehyde compounds of Patent Documents 1 to 3 have a problem that coloring occurs due to heating in a solid state because the reactivity of the aldehyde group is high. Therefore, the present invention provides a polyaldehyde compound-containing composition in which coloring due to heating in a solid state is reduced.

Means for Solving the Problems

[0005] As a result of diligent research, the inventors have discovered that by including a certain amount of a low molecular weight aldehyde compound in a polyaldehyde compound, a polyaldehyde compound-containing composition can be obtained in which discoloration due to heating in the solid state is reduced, thus completing the present invention.

[0006] The present invention is as follows:

[0007] [1] A polyaldehyde compound-containing composition having an aldehyde compound content of 50 to 2000 mg / kg with 1 to 6 carbon atoms. [2] A composition containing the polyaldehyde compound described in [1], wherein the degree of oxidation is 80% or higher. [3] The polyaldehyde compound-containing composition according to [1] or [2], wherein the polyaldehyde compound contained in the polyaldehyde compound-containing composition is at least one compound selected from the group consisting of starch, maltodextrin, maltose, and trehalose, in which a unit having two aldehyde groups is partially formed. [4] Color of the powder after heating for 6 hours in an atmosphere of 105℃ * and b before heating * The difference Δb * A polyaldehyde compound-containing composition according to any of [1] to [3], wherein the value is 0.0 to 3.0. [5] A method for producing a polyaldehyde compound-containing composition from carbohydrates, comprising the step of washing the polyaldehyde compound-containing composition obtained by oxidizing the carbohydrates with a periodate with a solvent containing an organic solvent. [6] A method for producing the polyaldehyde compound-containing composition according to [5], characterized in that the carbohydrate is a disaccharide, trisaccharide to decasaccharide or polysaccharide. [7] A method for producing a polyaldehyde compound-containing composition according to [5] or [6], characterized in that the organic solvent contains alcohols. [Effects of the Invention]

[0008] According to the present invention, it is possible to provide a polyaldehyde compound-containing composition in which discoloration due to heating in the solid state is reduced. [Modes for carrying out the invention]

[0009] The present invention will be described below.

[0010] [Polyaldehyde compound-containing composition] The polyaldehyde compound-containing composition of the present invention can be obtained, for example, by oxidizing a carbohydrate with an oxidizing agent such as a periodate.

[0011] The polyaldehyde compound-containing composition of the present invention contains a polyaldehyde compound and an aldehyde compound having 1 to 6 carbon atoms in an amount of 50 to 2000 mg / kg.

[0012] If the content of aldehyde compounds with 1 to 6 carbon atoms in a polyaldehyde compound-containing composition is less than 50 mg / kg, the stability of the polyaldehyde compound-containing composition decreases, and discoloration upon heating increases. Although the details of the mechanism are not clear, it is presumed that strong intermolecular forces act between the aldehyde compounds with 1 to 6 carbon atoms and the polyaldehyde compound, improving stability and reducing discoloration upon heating. Alternatively, it is presumed that stabilization is due to the protection of the aldehyde group by hydration through hemialdalization, or by the promotion of protection through acetalization or hemiacetalization with hydroxyl groups. Furthermore, if the polyaldehyde compound-containing composition contains more than 2000 mg / kg of aldehyde compounds with 1 to 6 carbon atoms, the stability of the polyaldehyde compound-containing composition becomes significantly lower, discoloration occurs upon heating, and low molecular weight aldehydes are highly toxic, thus posing a safety problem. The polyaldehyde compound-containing composition preferably contains aldehyde compounds with 1 to 6 carbon atoms in a range of 50 mg / kg to 1650 mg / kg, and more preferably in the range of 50 mg / kg to 510 mg / kg.

[0013] Examples of aldehyde compounds with 1 to 6 carbon atoms include formic acid, formaldehyde, acetaldehyde, propionaldehyde, butanal, pentanal, and hexanal.

[0014] The aldehyde compound having 1 to 6 carbon atoms contained in the polyaldehyde compound-containing composition may be one generated by oxidizing a saccharide with an oxidizing agent, or may be an added one.

[0015] The degree of oxidation of the polyaldehyde compound-containing composition of the present invention can be measured by the method using hydroxylamine hydrochloride described in Pharmaceutical Research, Vol.8, 400 - 402 (1991). That is, an aldehyde is reacted with hydroxylamine hydrochloride, the generated hydrochloric acid is quantified with sodium hydroxide (endpoint pH 5), and it can be calculated by the following general formula (1).

[0016] Degree of oxidation (%) = (V_NaOH × C_NaOH) / (s_sample × Mw) × 1 / 2 × 100 …(1)

[0017] In the formula, VNaOH represents the amount of sodium hydroxide up to the endpoint, CNaOH = 0.1 mol / l, S_sample represents the dry weight of the sample, and Mw represents the molecular weight of a dialdehyde glucose unit of 160 g / mol.

[0018] From the viewpoint of improving the performance as a paper strength enhancer due to an increase in crosslinking points, the degree of oxidation of the polyaldehyde compound-containing composition of the present invention is preferably 80% to 100%, and more preferably 90 to 100%. [Saccharide] The saccharide according to the embodiment of the present invention is a compound having a glucose unit and is represented by the general formula C m (H2O) n as described. Examples of carbohydrates include monosaccharides, disaccharides, trisaccharides, and decasaccharides (so-called oligosaccharides), and polysaccharides. Examples of monosaccharides include glucose, fructose, galactose, and mannose. Examples of disaccharides include sucrose, lactose, maltose, trehalose, and cellobiose. Examples of oligosaccharides include stachyose, maltotriose, maltotetraose, and maltopentaose. Examples of polysaccharides include starch, cyclodextrin, cellulose, dextran, β-glucan, dextrin, glycogen, pullulan, α-glucan, glycosaminoglycan, chitin, proteoglycan, polyuronide, chitosan, carrageenan, hemicellulose, mannan, galactan, xylan, inulin, and fructan. The carbohydrates are preferably disaccharides, trisaccharides to decasaccharides, or polysaccharides.

[0019] [Polyaldehyde compounds] The polyaldehyde compounds of the present invention can be obtained, for example, by oxidizing a carbohydrate with an oxidizing agent such as a periodate. The polyaldehyde compounds are compounds in which, in the glucopyranose units of the carbohydrate molecular chain, the spaces between adjacent carbon atoms are mainly cleaved, and both adjacent carbinol groups (>C-OH) are converted into aldehyde groups, forming a unit with a structure having two aldehyde groups.

[0020] The degree of oxidation of the polyaldehyde compound of the present invention is preferably 80% to 100%, and more preferably 85% to 100%, from the viewpoint of improving its performance as a paper strength enhancer by increasing the number of crosslinking points.

[0021] The amount of polyaldehyde compound contained in the polyaldehyde compound-containing composition of the present invention is preferably 80% to 100% by mass.

[0022] The amount of water contained in the polyaldehyde compound-containing composition of the present invention is preferably 0% to 20% by mass.

[0023] [Method for producing a polyaldehyde compound-containing composition]

[0024] In the present invention, it is preferable that the aldehyde group of the polyaldehyde compound is introduced by treating the carbohydrate with an oxidizing agent that cleaves some of the bonds between adjacent carbon atoms in the glucopyranose ring in the molecular skeleton and converts both or one of the adjacent carbinol groups into an aldehyde group.

[0025] As the oxidizing agent, at least one selected from the group consisting of periodic acid and periodate salts (hereinafter also referred to as periodic acid (salt)) is preferred due to its ease of handling. Examples of periodate salts include sodium periodate, potassium periodate, ammonium periodate, rubidium periodate, and cesium periodate. As the periodic acid (salt), sodium periodate is preferred due to its ease of handling.

[0026] Other oxidizing agents include cerium(IV) nitrate, lead tetraacetate, combinations of cobalt(II) acetate and oxygen, combinations of iodine and mercury(II) oxide, and combinations of silver nitrate and potassium peroxodisulfate.

[0027] When periodic acid (salt) is applied to carbohydrates, typically, the glucopyranose units in the carbohydrate molecular chain undergo cleavage mainly between adjacent carbon atoms, and both adjacent carbinol groups (>C-OH) are converted into aldehyde groups, forming a unit with two aldehyde groups (hereinafter also referred to as "a unit with two aldehyde groups"). Oxidation reactions using periodic acid (salt) will be explained in detail later.

[0028] When periodic acid (salt) is used as the oxidizing agent, the amount of oxidizing agent added for introducing the aldehyde group is preferably in the range of 0.1 mmol to 10.0 mmol per gram of carbohydrate, and more preferably in the range of 0.15 mmol to 5.0 mmol.

[0029] While there are no particular limitations on the oxidation treatment method with periodic acid (salt), it is generally known that reactions of carbohydrates with periodic acid (salt) can cause side reactions such as the cleavage of glycosidic bonds in carbohydrates, and that periodic acid (salt) itself is unstable to light. To reduce these effects, it is desirable to carry out the oxidation treatment in the dark, for example, by adding periodic acid (salt) to the carbohydrate dispersion at 0-80°C and stirring as appropriate. While there are no particular limitations on the oxidation treatment time with periodic acid (salt), it is preferable to continue stirring for about 48 hours to allow the reaction to proceed completely.

[0030] Furthermore, the polyaldehyde compounds used in the present invention are not limited to the above-described method as long as they have an aldehyde group.

[0031] [Solvents used for washing compositions containing polyaldehyde compounds] By washing a polyaldehyde compound-containing composition obtained by oxidizing carbohydrates, the amount of aldehyde compounds with 1 to 6 carbon atoms in the polyaldehyde compound-containing composition can be adjusted. Water or an organic solvent can be used as the solvent for washing the polyaldehyde compound-containing composition.

[0032] Suitable organic solvents include alcohols, ketones, esters, ethers, cellosolves, aromatic hydrocarbons, aliphatic hydrocarbons, sulfones, and the like.

[0033] Examples of alcohols include methanol, ethanol, 1-propanol, isopropyl alcohol, n-butanol, s-butanol, t-butanol, n-amyl alcohol, s-amyl alcohol, t-amyl alcohol, allyl alcohol, isoamyl alcohol, isobutyl alcohol, 2-ethylbutanol, 2-octanol, n-octanol, cyclohexanol, tetrahydrofurfuryl alcohol, furfuryl alcohol, n-hexanol, n-heptanol, 2-heptanol, 3-heptanol, benzyl alcohol, methylcyclohexanol, ethylene glycol, ethylene glycol monomethyl ether, glycerin, diethylene glycol, and propylene glycol.

[0034] Examples of ketones include acetone, methyl ethyl ketone, diethyl ketone, cyclohexanone, methyl isobutyl ketone, and methyl-n-propyl ketone.

[0035] Examples of esters include ethyl acetoacetate, ethyl benzoate, methyl benzoate, isobutyl formate, ethyl formate, propyl formate, methyl formate, isobutyl acetate, ethyl acetate, propyl acetate, methyl acetate, methyl salicylate, diethyl oxalate, diethyl tartrate, dibutyl tartrate, ethyl phthalate, methyl phthalate, butyl phthalate, γ-butyrolactone, ethyl malonate, and methyl malonate.

[0036] Examples of ethers include methyl glycol, methyl diglycol, methyl triglycol, methyl polyglycol, isopropyl glycol, isopropyl diglycol, butyl glycol, butyl diglycol, butyl triglycol, isobutyl glycol, isobutyl diglycol, butyl diglycol acetate, hexyl glycol, hexyl diglycol, 2-ethylhexyl glycol, 2-ethylhexyl diglycol, allyl glycol, phenyl glycol, phenyl diglycol, benzyl glycol, benzyl diglycol, methylpropylene glycol, methylpropylene diglycol, methylpropylene triglycol, propylpropylene glycol, propylpropylene diglycol, butylpropylene glycol, butylpropylene diglycol, butylpropylene triglycol, phenylpropylene glycol, methylpropylene glycol acetate, dimethyl glycol, dimethyl diglycol, dimethyl triglycol, methyl ethyl diglycol, diethyl diglycol, dibutyl diglycol, and dimethylpropylene diglycol.

[0037] Examples of cellosolves include methyl cellosolve and ethyl cellosolve.

[0038] Examples of aromatic hydrocarbons include benzene, toluene, and xylene.

[0039] Examples of aliphatic hydrocarbons include hexane and cyclohexane.

[0040] Examples of sulfones include sulfolane, dimethyl sulfone, ethyl methyl sulfone, ethyl isopropyl sulfone, 3-methylsulfolane, and dimethyl sulfoxide.

[0041] The aforementioned solvents can be used alone or in combination.

[0042] Since the polyaldehyde compound-containing composition can contain an appropriate amount of low molecular weight aldehyde compounds, it is preferable that the washing solvent contains water or alcohol, and it is particularly preferable that it contains alcohol. [Examples]

[0043] [ refer to Example 1] 10.0 g of starch (dry weight) was added to 300 g of water, and sulfuric acid was added while stirring to adjust the pH to 4.0. 13.2 g of sodium periodate was added to this solution, and the mixture was reacted at 60°C for 5 hours. After neutralizing the reaction solution, inorganic salts were removed by filtration and washing with water, and the resulting slurry was freeze-dried to remove water and obtain a crude product. 100 g of methanol was added to the prepared crude product and stirred, then filtered to collect the purified product. The obtained purified product was dried to obtain a starch-derived polyaldehyde compound-containing composition.

[0044] [ refer to Example 2] Except for replacing methanol with water:methanol = 1:1 refer to A composition containing a starch-derived polyaldehyde compound was obtained in the same manner as in Example 1. [ refer to Example 3] refer to A composition containing a starch-derived polyaldehyde compound was obtained by adding 50 g of a water:methanol = 1:1 mixed solvent to the purified product obtained in the same manner as in Example 2, stirring, filtering, and then drying the recovered solid.

[0045] [ refer to Example 4] 10.0 g of maltodextrin (DE: 13-17) by dry weight was added to 300 g of water, and sulfuric acid was added while stirring to adjust the pH to 4.0. 13.2 g of sodium periodate was added to this solution and the mixture was reacted at 60°C for 5 hours. Then, inorganic salts were removed by electrodialysis, and the resulting aqueous solution was freeze-dried to remove water and obtain a crude product. 100 g of methanol was added to the prepared crude product and stirred, and the purified product was collected by filtration. The obtained purified product was dried to obtain a composition containing a polyaldehyde compound derived from maltodextrin.

[0046] [ refer to Example 5] Except for replacing methanol with water:methanol = 1:1 refer to A composition containing a polyaldehyde compound derived from maltodextrin was obtained in the same manner as in Example 4. [ refer to Example 6] refer to A maltodextrin-derived polyaldehyde compound-containing composition was obtained by adding 50 g of a water:methanol = 1:1 mixed solvent to the purified product obtained in the same manner as in Example 5, stirring, filtering, and drying the recovered solid.

[0047] [Examples 1 ] 10.0 g of maltose (dry weight) was added to 300 g of water, and sulfuric acid was added while stirring to adjust the pH to 4.0. 13.2 g of sodium periodate was added to this solution, and the mixture was reacted at 40°C for 5 hours. After that, inorganic salts were removed by electrodialysis, and the resulting aqueous solution was freeze-dried to remove water and obtain a crude product. 100 g of 2-propanol was added to the prepared crude product and stirred, and the product was filtered to recover the purified product. The obtained purified product was dried to obtain a maltose-derived polyaldehyde compound-containing composition.

[0048] [Examples 2 ] The only difference from the example is that 2-propanol was replaced with water:2-propanol=1:1. 1 A composition containing a polyaldehyde compound derived from maltose was obtained in the same manner. [Examples 3 ] Examples 2 To the purified product obtained in the same manner, 50 g of a mixed solvent of water:2-propanol=1:1 was added and stirred, and the recovered solid was filtered and dried to obtain a maltose-derived polyaldehyde compound-containing composition.

[0049] [Examples 4 ] 10.0 g of trehalose (dry weight) was added to 300 g of water, and sulfuric acid was added while stirring to adjust the pH to 4.0. 13.2 g of sodium periodate was added to this solution, and the mixture was reacted at 40°C for 5 hours. After that, inorganic salts were removed by electrodialysis, and the resulting aqueous solution was freeze-dried to remove water and obtain a crude product. 100 g of 2-propanol was added to the prepared crude product and stirred, and the purified product was collected by filtration. The obtained purified product was dried to obtain a trehalose-derived polyaldehyde compound-containing composition.

[0050] [Examples 5 ] The only difference from the example is that 2-propanol was replaced with water:2-propanol=1:1. 4 Similarly, a composition containing a polyaldehyde compound derived from trehalose was obtained. [Examples 6 ] Examples 5 A trehalose-derived polyaldehyde compound-containing composition was obtained by adding 50 g of a mixed solvent of water:2-propanol=1:1 to the purified product obtained in the same manner, stirring, filtering, and drying the recovered solid.

[0051] [Comparative Example 1] 10.0 g of starch (dry weight) was added to 300 g of water, and sulfuric acid was added while stirring to adjust the pH to 4.0. 13.2 g of sodium periodate was added to this solution, and the mixture was reacted at 60°C for 5 hours. After that, inorganic salts were removed by filtration and washing with water, and the resulting slurry was freeze-dried to remove moisture and obtain a composition containing a starch-derived polyaldehyde compound.

[0052] [Comparative Example 2] refer to The purified product obtained in the same manner as in Example 2 was mixed with 100 g of water:methanol = 1:1 solvent and stirred, then filtered to recover the solid. Further, 300 g of water:methanol = 1:1 solvent was added to the solid and stirred, then filtered to recover the solid, and the resulting solid was dried to obtain a starch-derived polyaldehyde compound-containing composition.

[0053] [Comparative Example 3] 10.0 g of maltodextrin (DE: 13-17) by dry weight was added to 300 g of water, and sulfuric acid was added while stirring to adjust the pH to 4.0. 13.2 g of sodium periodate was added to this solution, and the mixture was reacted at 60°C for 5 hours. After that, inorganic salts were removed by filtration and washing with water, and the resulting slurry was freeze-dried to remove water and obtain a composition containing a polyaldehyde compound derived from maltodextrin.

[0054] [Comparative Example 4] refer to The purified product obtained in the same manner as in Example 5 was mixed with a water:methanol = 1:1 solvent and stirred, then filtered to recover the solid. Furthermore, 300 g of the water:methanol = 1:1 solvent was added to the solid, and the mixture was stirred at 30°C for 1 hour, then filtered to recover the solid, and the resulting solid was dried to obtain a maltodextrin-derived polyaldehyde compound-containing composition.

[0055] [Comparative Example 5] 10.0 g of maltose (dry weight) was added to 300 g of water, and sulfuric acid was added while stirring to adjust the pH to 4.0. 13.2 g of sodium periodate was added to this solution, and the mixture was reacted at 40°C for 5 hours. After that, inorganic salts were removed by filtration and washing with water, and the resulting slurry was freeze-dried to remove water and obtain a maltose-derived polyaldehyde compound-containing composition.

[0056] [Comparative Example 6] Examples 2The purified product obtained in the same manner was mixed with a water:2-propanol=1:1 solvent and stirred, then filtered to recover the solid. Furthermore, 300g of the water:2-propanol=1:1 mixed solvent was added to the solid and stirred, then filtered to recover the solid, and the resulting solid was dried to obtain a maltose-derived polyaldehyde compound-containing composition.

[0057] [Comparative Example 7] 10.0 g of trehalose (dry weight) was added to 300 g of water, and sulfuric acid was added while stirring to adjust the pH to 4.0. 13.2 g of sodium periodate was added to this solution, and the mixture was reacted at 40°C for 5 hours. After that, inorganic salts were removed by electrodialysis, and the resulting aqueous solution was freeze-dried to remove water, thereby obtaining a trehalose-derived polyaldehyde compound-containing composition.

[0058] [Comparative Example 8] Examples 5 The purified product obtained in the same manner was mixed with a water:2-propanol=1:1 solvent and stirred, then filtered to recover the solid. Furthermore, 300 g of the water:2-propanol=1:1 mixed solvent was added to the solid and stirred, then filtered to recover the solid, and the resulting solid was dried to obtain a trehalose-derived polyaldehyde compound-containing composition.

[0059] Refer to Examples 1-6. Example 1~ 6 The polyaldehyde compound-containing compositions prepared in Comparative Examples 1 to 8 were analyzed by the following method.

[0060] [Measurement of oxidation level] The degree of oxidation of the prepared polyaldehyde compound-containing composition is, Pharmaceutical The measurement was performed using the hydroxylamine hydrochloride method described in Research, Vol. 8, 400-402 (1991). Specifically, the aldehyde was reacted with hydroxylamine hydrochloride, the resulting hydrochloric acid was quantified with sodium hydroxide (endpoint pH 5), and the result was calculated using the following formula (1).

[0061] Degree of oxidation (%) = (V_NaOH × C_NaOH) / (s_sample × Mw) × 1 / 2 × 100 …(1)

[0062] In the formula, VNaOH = amount of sodium hydroxide to the endpoint, CNaOH = 0.1 mol / l, S sample = dry weight of the sample, and Mw = 160 g / mol. It represents the molecular weight of the dialdehyde glucose unit.

[0063] [Quantitative determination of aldehyde compounds] Gas chromatography-mass spectrometry (GC-MS) was used for the quantitative determination and identification of aldehyde compounds with 1 to 6 carbon atoms. An Agilent Technologies 5973 GC-MS system was used, and a DB-5MS column was employed. Helium was used as the carrier gas. The injection port temperature was 250°C, and the column temperature was increased from 40°C at a rate of 20°C per minute, ultimately reaching 230°C. For the mass spectrometry section, electron bombardment was used for ionization with a voltage of 70 eV. The ion source temperature was 200°C, and the scan speed was 0.8 sec / scan.

[0064] [Stability Assessment] A heat resistance test was conducted by placing a powdered polyaldehyde compound-containing composition in a glass petri dish and heating it in a 105°C atmosphere for 6 hours, and the color of the powder was measured. * The difference between before and after heating is Δb. * The following was calculated. Chromaticity was measured using a spectrophotometer NR555 manufactured by Nippon Denshoku Industries Co., Ltd.

[0065] The analysis results are shown in Table 1.

[0066] [Table 1]

[0067] As described above, Examples 1 to 1 of the present invention 6 The polyaldehyde compound-containing composition obtained by this process, which contains 50 to 2000 mg / kg of aldehyde compounds with 1 to 6 carbon atoms, exhibits improved stability and reduced discoloration due to heating in the solid state. [Industrial applicability]

[0068] The polyaldehyde compound-containing composition of the present invention exhibits reduced discoloration upon heating, making it suitable for use as a paper strength enhancer and the like.

Claims

1. A polyaldehyde compound-containing composition having a content of 50 to 2000 mg / kg of an aldehyde compound having 1 to 6 carbon atoms, wherein the polyaldehyde compound contained in the polyaldehyde compound-containing composition is at least one compound selected from the group consisting of maltose and trehalose, in which a unit having two aldehyde groups is partially formed.

2. A polyaldehyde compound-containing composition according to claim 1, wherein the degree of oxidation is 80% or more.

3. Color b of powder after heating for 6 hours in an atmosphere of 105°C ＊ and the powder b before heating ＊ The difference Δb ＊ The polyaldehyde compound-containing composition according to claim 1 or claim 2, wherein the amount is 0.0 to 3.

0.

4. A method for obtaining a polyaldehyde compound-containing composition from maltose or trehalose, comprising the step of washing the polyaldehyde compound-containing composition obtained by oxidizing maltose or trehalose with a periodate with a solvent containing an organic solvent, A method for producing a polyaldehyde compound-containing composition, characterized in that the polyaldehyde compound-containing composition obtained through the above-mentioned process has a content of 50 to 2000 mg / kg of aldehyde compounds having 1 to 6 carbon atoms.

5. A method for producing a polyaldehyde compound-containing composition according to claim 4, characterized in that the organic solvent contains alcohols.

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