JP3320484B2 - Bleach activator and bleach composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a bleaching activator and a bleaching composition, and more particularly to a bleaching activator having high bleaching activity for both hydrophilic stains and hydrophobic stains. The present invention relates to a bleaching composition containing:

[0002]

2. Description of the Related Art In general, stains requiring bleaching are roughly classified into hydrophilic stains such as tea stains and hydrophobic stains such as yellowish underwear. As bleaching agents for bleaching such stains, chlorine bleaching agents and oxygen bleaching agents are used. However, chlorine bleach has limited fiber that can be used, cannot be used for color and pattern, and has a unique smell. It is beginning to spread.

As the oxygen-based bleaching agent, sodium percarbonate and sodium perborate are particularly used from the viewpoint of bleaching performance and stability. However, these oxygen bleaching agents have a lower bleaching power than chlorine bleaching agents, and various bleaching activators are used in combination. For example, tetraacetylethylenediamine, tetraacetylglycoluril, glucose pentaacetate, triacetylglycerol and the like are used as typical bleach activators. These bleach activators react with an inorganic peroxide such as sodium percarbonate or sodium perborate in a washing bath or bleach bath to produce peracetic acid, a bleaching active species. Peracetic acid is highly water-soluble and has a low affinity for hydrophobic stains, so it is effective for hydrophilic stains,
There is a problem that the effect is small for hydrophobic dirt.

In addition, when the acetyl group of the above-mentioned bleach activator is changed to a lipophilic alkanoyl group, for example, when trioctanoin or tetraoctanoylethylenediamine is used as a bleach activator, ordinary washing or bleaching is carried out. Under mild conditions, there is a problem that the amount of organic peracid produced is very small, and therefore no bleaching activity is exhibited.

Also, sodium alkanoyloxy-p-benzenesulfonate (JP-B-63-12520), which has a lipophilic alkanoyl group and is effective for both hydrophilic and hydrophobic stains, Glycolate ester peracid precursor (JP-A-63-152696)
Alternatively, trimethyl- (2-alkanoyloxyethyl) -ammonium chloride (JP-A-61-179300)
No.) are disclosed. However, sodium alkanoyloxy-p-benzenesulfonate and the precursor of the glycolate ester peracid decompose the organic peracid produced by the by-produced sodium p-phenolsulfonate during the bleaching, and can be used to decompose trimethyl- (2 -Alkanoyloxyethyl) -ammonium chloride is a cation, and thus forms a complex with an anionic detergent, thus causing a problem such as a decrease in bleaching activity.

[0006]

SUMMARY OF THE INVENTION The present invention provides a bleaching activator having a high bleaching effect on both hydrophilic stains and hydrophobic stains, and a bleaching agent composition containing the same. It was made for the purpose of providing.

[0007]

The present inventors have conducted intensive studies to obtain a bleaching activator having a high bleaching power and a bleaching agent composition containing the same, which overcome the above-mentioned problems.
The inventors have found that an ester compound having a specific electron withdrawing group at the β-position on the alcohol side has extremely excellent performance as a bleach activator, and have completed the present invention.

That is, the present invention comprises a bleaching activator comprising a compound represented by the general formula (I), and a hydrogen peroxide or a compound which generates hydrogen peroxide in an aqueous solution. The present invention provides a bleaching composition characterized by:

[0009]

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[0010] wherein, X ', Z'; -SO 3 -, -SO 3 M, -OS
^{_{O 3 -, -OSO 3 M,}} -OR 6, -N + (R 6) 3, -N + (R 6) 3 · A -, -OCO
R ⁷ , —COO ⁻ , —COOM, —NO ₂ or a halogen atom , which may be the same or different. Here, R ⁶ represents an optionally substituted alkyl group having 1 to 20 carbon atoms, an alkenyl group, a hydroxyalkyl group, or an optionally substituted aryl group, and R ⁷ represents an optionally substituted carbon number. And represents an alkyl group, an alkenyl group or a hydroxyalkyl group of 1 to 3 . M represents an alkali metal, alkaline earth metal, ammonium salt or alkanol ammonium salt, and A represents an inorganic or organic anion. R ⁸ ,
R ⁹ , B, n; R ⁸ may have a substituent or
Optionally branched C 4-18 alkyl groups, alkenyl
Or a substituted or unsubstituted hydroxyalkyl group.
Represents an aryl group, R ⁹ is an alkylene group having 1 to 3 carbon atoms
Show. B is a methylene group,

[0011]

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And n represents a number of 0 or 1.

Wherein X ′ and Z ′ are both —OCOR ⁷ and n is
Except when it is 0. ] Above general formula (I) compound represented by having an electron withdrawing group as defined above in an alcohol side of the α- position of esters, R ⁸ - (BR ⁹⁾ groups represented by _n -COO- coupled with electron-withdrawing ^{ability, R 8 - (BR 9)} n -COO- group represented by is likely to form an organic peracid eliminated.

[0014] Examples of the compound represented by the general formula (I), in particular X 'is -N ⁺ (R ⁶⁾ ₃ or _{^{-N + (R 6) 3 ·}} A -, Z' is -S
_{^{O 3 -, -SO 3 M,}} -OSO 3 -, -OSO 3 M, -COO - or -COOM (R
⁶ , A and M have the same meanings as described above).

The compound represented by the above general formula (I) can be derived from, for example, epichlorohydrin.

[0016]

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(Wherein each of R ⁸ , R ⁹ , B and n has the same meaning as described above), a sulfobetaine, a sulfatobetaine, a carbobetaine compound,

[0018]

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(Wherein, R ⁸ , R ⁹ , B and n have the same meanings as described above). Among these, sulfobetaine, sulfatobetaine and carbobetaine compounds are clearly different from the cationic compounds disclosed in JP-A-61-179300. When a cationic compound is used in an anionic detergent, the bleaching activity is significantly reduced due to complex formation. However, each of the betaine compounds in the present invention does not show the formation of these complexes, and exhibits high bleaching activity even in an anionic detergent.

In the general formula (I), X ′ and
Z 'is -OCOR ⁷ (R ⁷ has the same meaning as described above ), and n is 1
Specific examples of the compound represented by are the following compounds .

[0021]

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(Wherein, R ⁸ , R ⁹ and B have the same meanings as described above.)
And n is 1. ) This compound is esterified with acetic acid glycerin, followed by the formula R ⁸ - in (BR ⁹⁾ _n -COOH (wherein, R ^8, R ⁹ and B indicates the same meaning as above, n represents 1
By performing the esterification with the compound represented by any)
Can be synthesized.

Among the compounds represented by the above general formula (I),
In particular, the sulfobetaines, sulfatobetaines, carbobetaines of (a) to (d) and the glycerin derivative of (k) have high bleaching activity and are preferred.

[0024] react with these formulas in the wash bath of the compound represented by the formula (I), or hydrogen peroxide in a mild condition that bleaching bath, R ⁸ - has the structure (BR ⁹⁾ _n -COOOH It produces an organic peracid, which becomes a bleaching active species. This organic peracid R ⁸
The structure of-(BR ⁹ ) _n -COOOH affects bleaching activity. For example,
When the organic peracid is peracetic acid (CH ₃ COOOH), it is effective for hydrophilic stains, but is less effective for hydrophobic stains such as oil stains because peracetic acid is hydrophilic. In addition, organic peracids having a long-chain alkyl group are effective for oily stains,
Has little effect on lipophilic stains. In the present invention, produced come R ⁸ - (BR ⁹⁾ to adjust the balance between hydrophilicity and lipophilicity of _n -COOOH, i.e. R balance of hydrophilicity and lipophilicity were adjusted ⁸ - (BR ⁹⁾ By using a compound represented by the general formula (I) having a group represented by _n- COO- as a bleaching activator, a bleaching composition having high bleaching activity for both hydrophilic and hydrophobic stains Could be provided.

The general formula (I) of the formula R ⁸ - (BR ⁹⁾ In the group represented by _n -COO-, R ⁸ good number of carbon atoms which may have or may or branched have a substituent 4 to 18, more preferably 6 to 12 alkyl groups, alkenyl groups, hydroxyalkyl groups or optionally substituted aryl groups, R ⁹ is an alkylene group having 1 to 3 carbon atoms, and B is methylene Group or

[0026]

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And n is a number of 0 or 1. Here, R ⁶ may have 1 to 20 carbon atoms which may be substituted.
Alkyl group, alkenyl group, hydroxyalkyl group,
Or an aryl group which may be substituted, and A is an inorganic or organic anion. More specific formula R ⁸ - (B-
R ⁹ ) _n -COO- includes C ₅ H ₁₁ COOH and C ₇ H ₁₅ CO
_{OH, C 9 H 19 COOH,} C 11 H 23 COOH, iso-C 8 H 17 COOH, aliphatic carboxylic acid residues of branched or straight chain, such as 2-ethylhexanoic acid or benzoic acid, salicylic acid, phthalic acid, Aromatic carboxylic acid residues such as terephthalic acid and phenoxyacetic acid, or C ₈ H ₁₇ OCH ₂ COOH, C ₁₀ H ₂₁ OCH ₂ COO
H, C ₁₂ H ₂₅ OCH ₂ COOH, C ₈ H ₁₇ OC ₂ H ₄ COOH, C ₁₀ H ₂₁ OC ₂ H ₄ COOH
, An ether carboxylic acid residue such as C ₁₂ H ₂₅ OC ₂ H ₄ COOH,
Or C ₇ H ₁₅ COOCH ₂ COOH, C ₉ H ₁₉ COOCH ₂ COOH, C ₁₁ H ₂₃
COOCH ₂ COOH, C ₇ H ₁₅ OCOC ₂ H ₄ COOH, C ₉ H ₁₉ OCOC ₂ H ₄ COOH, C
₁₁ H ₂₃ OCOC ester carboxylic acid residue, such as ₂ H ₄ COOH or _{C 7 H 15 CONHCH 2 COOH,} , C 9 H 19 CONHCH 2 COOH, C 11 H 23 CON
HCH ₂ COOH, C ₇ H ₁₅ NHCOC ₂ H ₄ COOH, C ₉ H ₁₉ NHCOC ₂ H ₄ COOH
Amide carboxylic acid residues such as, C ₁₁ H ₂₃ NHCOC ₂ H ₄ COOH,
further

[0028]

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And the like.

The bleaching composition of the present invention comprises, as essential components, a bleaching activator comprising the compound represented by the above general formula (I) and hydrogen peroxide or a compound which generates hydrogen peroxide in an aqueous solution. contains. Specific examples of the compound that generates hydrogen peroxide in an aqueous solution include sodium percarbonate,
Sodium tripolyphosphate / hydrogen peroxide adduct, sodium pyrophosphate / hydrogen peroxide adduct, urea / hydrogen peroxide adduct, or 4Na ₂ SO ₄ .2H ₂ O ₂ .NaCl, sodium perborate monohydrate, perborate Examples include sodium tetrahydrate, sodium peroxide, calcium peroxide and the like. Of these, sodium percarbonate, sodium perborate monohydrate and sodium perborate tetrahydrate are particularly preferred.

The compounding ratio of the hydrogen peroxide in the bleach composition of the present invention or the compound (a) generating hydrogen peroxide in an aqueous solution and the compound (b) represented by the general formula (I) is as follows:
(A) / (B) (molar ratio) = 99.9 / 0.1 to 20/80, more preferably 99/1 to 50/50.

The bleaching composition of the present invention can be used as a bleaching agent, a bleaching detergent or the like, and can contain known components usually added in addition to the above essential components. For example, as the builder, sulfate, carbonate, bicarbonate, silicate, water-soluble inorganic builder such as phosphate, water-insoluble inorganic builder such as zeolite, ethylenediaminetetraacetate, nitrilotriacetate, tartrate, Organic builders such as citrate can be used. Magnesium salts such as magnesium sulfate, magnesium silicate, magnesium chloride, magnesium silicofluoride, magnesium oxide, magnesium hydroxide and the like, and silicates such as sodium silicate which are known as stabilizers for peroxides or hydrogen peroxide adducts Can be used. If necessary, carboxymethylcellulose, polyvinylpyrrolidone, anti-redeposition agents such as polyethylene glycol, alkyl sulfates, alkane sulfonates, alkyl ether sulfates, alkyl benzene sulfonates, α-olefin sulfonates, higher fatty acid soaps Such as anionic surfactants, polyoxyethylene alkylphenol ether,
Nonionic surfactants such as polyoxyethylene alkyl ethers, mono- or diethanolamides of higher fatty acids, amine oxides, amphoteric surfactants such as betaine,
Enzymes such as protease, lipase, amylase and cellulase, optical brighteners, dyes, pigments, fragrances and the like can be added. Further, the bleaching composition of the present invention can also be used by mixing with a conventionally known clothing detergent.

[0033]

The bleaching composition of the present invention exhibits an excellent bleaching effect on both hydrophilic stains and hydrophobic stains.

[0034]

EXAMPLES The present invention will be described below with reference to production examples and examples, but the present invention is not limited to these examples.

Production Example 1: Synthesis of Compound (1)

[0036]

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A 35-liter two-necked flask equipped with a dropping funnel, a thermometer, a cooling tube, and a mechanical stirrer was charged with 35.
500g (MW 104.0, 1.68mol)
And heated to 60 ° C. 155.6 g (MW 92.5, 1.68 mol) of epichlorohydrin was added dropwise from the dropping funnel over about 2 hours. After aging at 80 ° C for 2 hours, cool to room temperature, 30%
663.0 g (MW 59.1, 3.4 mol) of an aqueous trimethylamine solution was charged and the temperature was raised to 60 ° C. After aging at 60 ° C. for 5 hours, excess trimethylamine and water were distilled off under reduced pressure using an evaporator. The obtained crystals were dried overnight at 80 ° C. using a vacuum drier, and 321.3 g of 3- (trimethylammonio) -2-hydroxy-1-propanesulfonate (MW 197.1, 1.
63 mol). The yield was 97%. Next, 100 g (0.51 mol) of 3- (trimethylammonio) -2-hydroxy-1-propanesulfonate and 300 g of DMF were charged into a 1-liter four-necked flask equipped with a dropping funnel, a thermometer, a cooling tube, and a mechanical stirrer. Then, 82.5 g (MW 162.7, 0.51 mol) of caprylic chloride was dropped from the dropping funnel over about 30 minutes. After aging at 60 ° C. for 2 hours, DMF was distilled off under reduced pressure using an evaporator. The resulting crystals were washed several times with acetone, and dried to give compound (1) 149.1.
g (MW 323.3, 0.43 mol). The yield was 85% and the purity was 94%.

Production Example 2: Synthesis of compound (2)

[0039]

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D was placed in a 1-liter four-necked flask equipped with a dropping funnel, a thermometer, a cooling tube, and a mechanical stirrer.
L-carnitine hydrochloride 100 g (MW 197.0, 0.51 mol) and DM
F300g and lauric chloride from dropping funnel
110.7 g (MW 218.8, 0.51 mol) was added dropwise over about 30 minutes.
After aging at 60 ° C. for about 1 hour, DMF was distilled off under reduced pressure using an evaporator. After washing several times with acetone, dry
157.4 g (MW 343.5, 0.38 mol) of (2) was obtained. 74% yield, purity
82%.

Production Example 3: Synthesis of compound (3)

[0042]

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In a 2 liter four-necked flask equipped with a dropping funnel, a thermometer, a cooling tube and a mechanical stirrer, 35
500g (MW 104.0, 1.68mol)
And heated to 60 ° C. 155.6 g (MW 92.5, 1.68 mol) of epichlorohydrin was added dropwise from the dropping funnel over about 2 hours. After aging at 80 ° C. for 2 hours, the mixture was cooled to room temperature, and charged with 211.7 g (MW 126.0, 1.68 mol) of sodium sulfite powder and 500 g of ion-exchanged water. After aging at 90 ° C for 7 hours, water was distilled off under reduced pressure using an evaporator, and the obtained crystals were dried at 80 ° C for 24 hours using a reduced-pressure drier to give 2-hydroxy-
Sodium 1,3-propanedisulfonate 542g (MW 26
4.0, 1.68 mol). The yield was 99% and the purity was 82%.
Next, 122 g (0.38 mol) of sodium 2-hydroxy-1,3-propanedisulfonate, 71.7 g of dimethyloctylamine
g (MW 157.3, 0.46 mol) and DMF 300 g dropping funnel,
1 equipped with thermometer, cooling pipe and mechanical stirrer
A 4-liter four-necked flask was charged, and 42.9 g (MW 112.9, 0.38 mol) of chloroacetyl chloride was dropped from the dropping funnel over about 1 hour under ice cooling. After aging for 2 hours, 59.8 g (0.38 mol) of dimethyloctylamine was added and reacted at 60 ° C. for about 5 hours. After DMF was distilled off under reduced pressure using an evaporator, the residue was washed several times with acetone to remove by-product amine hydrochloride. It was further dissolved in methanol, and the precipitated salt was separated by filtration, and methanol in the filtrate was distilled off under reduced pressure using an evaporator. The obtained crystals were dried at 50 ° C. for 5 hours in a reduced pressure drier to obtain 96.7 g of Compound (3) (MW 439.2, 0.2 g).
19 mol). The yield was 51% and the purity was 88%.

Production Example 4: Synthesis of compound (4)

[0045]

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In a 2 liter four-necked flask equipped with a dropping funnel, a thermometer, a cooling tube and a mechanical stirrer, 35
500g (MW 104.0, 1.68mol)
And heated to 60 ° C. 155.6 g (MW 92.5, 1.68 mol) of epichlorohydrin was added dropwise from the dropping funnel over about 2 hours. After aging at 80 ° C. for 2 hours, water was distilled off under reduced pressure using an evaporator, and dried at 80 ° C. for 24 hours using a reduced pressure drier to obtain 326.8 g of sodium 3-chloro-2-hydroxy-1-propanesulfonate (MW 196.5, 1.66). mol).
The yield was 99%. Next, 3-chloro-2-hydroxy-
100 g (0.51 mol) of sodium 1-propanesulfonate,
Sodium acetate 41.7 g (MW 82.0, 0.51 mol) and DMF 3
00 g was charged into a 1-liter four-necked flask equipped with a dropping funnel, a thermometer, a cooling tube, and a mechanical stirrer,
The reaction was performed at 150 ° C. for about 4 hours. After cooling, 96.1 g (0.61 mol) of dimethyloctylamine was charged, and 57.5 g (0.51 mol) of chloroacetyl chloride was added dropwise from the dropping funnel over about 1 hour under ice cooling. After aging for 1 hour, 80.1 g (0.51 mol) of dimethyloctylamine was added and reacted at 60 ° C. for 5 hours. D
After the MF was distilled off under reduced pressure, the residue was washed several times with acetone to remove the by-produced amine hydrochloride.
Compound (4) was recrystallized from acetone to 135.5.
g (MW 395.2, 0.33 mol). The yield was 64% and the purity was 95%.

Production Example 5: Synthesis of compound (5)

[0048]

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A 2-liter 5-neck flask equipped with two dropping funnels, a condenser, a pH electrode, and a mechanical stirrer was charged with 100 g of β-alanine (MW 89.1, 1.12 mol) and 0.5 liter of ion-exchanged water, and a 5% aqueous NaOH solution was added. The pH was adjusted to 9 with. Lauric acid chloride from dropping funnel
245.6 g (MW 218.8, 1.12 mol) was simultaneously dropped from another dropping funnel with a 5% aqueous NaOH solution, and
The solution was added dropwise over about 2 hours so as to maintain H9 to 10. 2
After aging for a period of time, a 35% aqueous HCl solution was added until the pH reached 3, whereby crystals were precipitated. The crystals are collected by filtration, washed several times with ion-exchanged water and acetone, and dried to give 3
213.2 g of lauroylaminopropionic acid (MW 271.4,
0.79 mol). The yield was 70%. Then dropping funnel, condenser, thermometer, methanol in a 1-liter four-necked flask fitted with a mechanical stirrer 100g and BF ₃ -
2 g of an ether complex was charged, and the temperature was raised to reflux. About 92.5 g (1.0 mol) of epichlorohydrin was added from the dropping funnel to about 2
It was dropped over time. After aging for 10 hours under reflux, methanol was distilled off under reduced pressure and distilled to give 102.1 g of 3-methoxy-2-hydroxy-1-chloropropane (MW 124.5, 0.8
2 mol). The yield was 82%.

Next, 100 g (0.37 mol) of the previously synthesized 3-lauroylaminopropionic acid, 45.9 g (0.37 mol) of 3-methoxy-2-hydroxy-1-chloropropane, xylene 20
0 g and 1 g of p-toluenesulfonic acid were charged into a 1-liter three-necked flask equipped with a Dean-Stark dehydrating tube, a thermometer, and a mechanical stirrer, and heated to reflux. The reaction was carried out for about 15 hours while distilling off the generated water. Thereafter, the mixture was neutralized with p-toluenesulfonic acid and an equivalent amount of NaOH, and xylene was distilled off under reduced pressure. Next, 300 g of ion-exchanged water, 200 g of ethanol and sodium sulfite
72.7 g (MW 196.5, 0.37 mol) was charged and reacted at 90 ° C. for about 5 hours. Thereafter, water and ethanol were distilled off under reduced pressure, dissolved in methanol, and the precipitated inorganic salt was separated by filtration. The filtrate was concentrated, and the obtained crystals were washed several times with acetone and dried to obtain 102.1 g of a compound (5) (MW 493.5, 0.18 mol).
l) Got it. The yield was 49% and the purity was 87%.

Production Example 6: Synthesis of compound (6)

[0052]

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100 g of sodium 3-chloro-2-hydroxy-1-propanesulfonate (0.51
mol), 138.4 g (MW 271.4, 0.51 mol) of 3-lauroylaminopropionic acid synthesized in Production Example 5, 200 g of xylene, D
300 g of MF and 1 g of p-toluenesulfonic acid were charged into a 1-liter three-necked flask equipped with a Dean-Stark dehydrating tube, a thermometer, and a mechanical stirrer, and heated to reflux. The reaction was carried out for about 15 hours while distilling off the generated water. Then, p-toluenesulfonic acid and an equivalent amount of NaOH
And xylene and DMF were distilled off under reduced pressure. The resulting crystals were washed several times with acetone to give Compound (6) 2
34.5 g (MW 449.9, 0.41 mol) were obtained. The yield was 80% and the purity was 78%.

Production Example 7: Synthesis of compound (7)

[0055]

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(At least one of X ¹ , Y ¹ and Z ¹ is C ₈ H ₁₇ N
⁺ (CH ₃ ) ₂ · Cl ^-- CH ₂ COO- and a mixture of CH ₃ COO-) glycerin in a 1-liter four-necked flask equipped with a dropping funnel, a condenser, a thermometer, and a mechanical stirrer 94.1 g (MW 94.1, 1.0 mol) was charged and the temperature was raised to 120 ° C. 204.2 g of acetic anhydride from the dropping funnel (MW 102.1, 2.0m
ol) was added dropwise over about 5 hours. After aging at 120 ° C. for 5 hours, acetic acid produced as a by-product was distilled off under reduced pressure. After cooling the residue to 10 ° C., 188.8 g of dimethyloctylamine (MW 157.3, 1.2 mol
l) was added, and 112.9 g (MW 112.9, 1.0 mol) of chloroacetyl chloride was added dropwise from the dropping funnel over about 1 hour under ice cooling. One hour after aging, 200 g of acetone and 157.3 g (1.0 mol) of dimethyloctylamine were added and reacted at 60 ° C. for 5 hours. After cooling, the mixture was allowed to stand and separated into a viscous liquid portion and an acetone layer. The acetone layer was removed by decantation, and the viscous liquid was washed several times with acetone. By drying this, 341.8 g of compound (7) (average MW
411.8, 0.83 mol). The yield was 83%.

Production Example 8: Synthesis of compound (8)

[0058]

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(At least one of X ² , Y ² and Z ² is C ₉ H ₁₉ C
A mixture of OOCH ₂ COO- and the balance CH ₃ COO-) 94.1 g (M) of glycerin in a 1-liter four-necked flask equipped with a dropping funnel, a condenser, a thermometer, and a mechanical stirrer.
W 94.1, 1.0 mol) and heated to 120 ° C. About 204.2 g (MW 102.1, 2.0 mol) of acetic anhydride was added to the dropping funnel for about 5 minutes.
It was dropped over time. After aging at 120 ° C. for 5 hours, acetic acid produced as a by-product was distilled off under reduced pressure. After cooling the residue to 10 ° C, 101.2 g (MW 101.2, 1.0 mol) of triethylamine was added, and chloroacetyl chloride 112.9 g (MW
112.9, 1.0 mol) was added dropwise over about 1 hour. One hour after aging, 300 g of acetone is added, and crystals of triethylamine hydrochloride precipitate. This was filtered off and acetone was distilled off under reduced pressure.

This residue and sodium caprate 194.3
g (MW 194.3, 1.0 mol) and 300 g of DMF were charged into a 1-liter three-necked flask equipped with a cooling tube, a thermometer, and a mechanical stirrer, and reacted at 150 ° C. for about 6 hours. After the precipitated NaCl was separated by filtration, DMF was distilled off under reduced pressure, and the residue was distilled to obtain 323.9 g of Compound (8) (average MW 39
0.3, 0.83 mol). The yield was 83%.

Examples 1 to 8 The bleaching performance of the compounds (1) to (8) synthesized in the above Production Examples was measured by the following method. Table 1 shows the results. <Measurement method for bleaching performance> Sodium percarbonate is dissolved in 300 ml of water at 20 ° C so that the available oxygen becomes 0.05%, and 0.0833% of a commercially available heavy detergent is added.
Was added so that 1/16 of the hydrogen peroxide in this solution
Compound (1) synthesized in the above Production Example so as to have an equivalent amount
(8) was added, and immersion bleaching was performed for 30 minutes using five pieces of various contaminated cloths prepared by the following method, washed with water, dried, and the bleaching rate was determined by the following formula.

[0062]

(Equation 1)

The reflectance was NDR-10 manufactured by Nippon Denshoku Industries Co., Ltd.
Measured using a 460 nm filter at 1 DP.・ Preparation method of black tea cloth 80g of Nitto black tea (yellow package) is boiled with 3 liters of ion exchange water for about 15 minutes, rubbed with bleached cotton after desizing, and dipped cotton gold cloth # 2003 in this liquid. Boil for a minute. It was lowered from the fire as it was, allowed to stand for about 2 hours, allowed to dry naturally, washed with water until the washing solution became colorless, dehydrated, pressed, made into a 10 cm × 10 cm test piece, and subjected to an experiment.・ Curry-contaminated cloth Filtration of Otsuka Pharmaceutical Bon Curry.
And heated for about 15 minutes. After leaving for about 2 hours,
It was washed with water and dried naturally. After pressing, a test piece of 10 cm × 10 cm was used for the experiment. -Blood-contaminated cloth Emper 111 was washed twice with a general detergent, washed with water, dehydrated and pressed, and then used as a test piece of 10 cm x 10 cm, which was subjected to an experiment.

Comparative Examples 1-3 Instead of the bleach activators synthesized in the Production Examples, conventional bleach activators such as tetraacetylethylenediamine and triacetylglycerol were used, or without adding the bleach activator, The bleaching performance was measured in the same manner as in Examples 1 to 8. Table 1 shows the results.

[0065]

[Table 1]

As is apparent from Table 1, since the black tea-stained cloth is a hydrophilic stain, the product of the present invention shows almost the same bleaching performance as the comparative product. On soiling, the products according to the invention show a better bleaching activity than the comparative products.

──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. ⁷ , DB name) C11D 7/54 C11D 7/26 C11D 7/32 C11D 7/34 D06L 3/00

Claims (3)

(57) [Claims] 1. A bleaching activator comprising a compound represented by the general formula (I). Embedded image Wherein, X ', Z'; -SO 3 -, -SO 3 M, -OSO 3 -, -OSO 3 M, -OR 6, -N + (R
_{^{6) 3, -N + (R}} 6) 3 · A -, -OCOR 7, -COO -, -COOM, an -NO ₂ or a halogen atom, these may be the same or different. Here, R ⁶ has 1 to 5 carbon atoms which may be substituted.
20 alkyl group, an alkenyl group, a hydroxyalkyl group, or an optionally substituted aryl group, R ⁷ represents an optionally substituted alkyl group having 1 to 3 carbon atoms which may have, an alkenyl group or hydroxyalkyl group . M represents an alkali metal, alkaline earth metal, ammonium salt or alkanol ammonium salt, and A represents an inorganic or organic anion. R ⁸ , R ⁹ , B, n; R ⁸ has a substituent
4 to 18 carbon atoms which may be present or may be branched
Alkyl group, alkenyl group, hydroxyalkyl group or
Represents an aryl group which may be substituted, and R ⁹ has 1 carbon atom
Represents alkylene groups of 1 to 3. Further B is a methylene group, ## STR2 ## And n represents a number of 0 or 1. However, if X 'and Z'
Except when both are -OCOR ⁷ and n is 0. ] 2. X ′ is -N ⁺ (R ⁶ ) ₃ or -N ⁺ (R ⁶ ) ₃ .A ⁻ , Z ′ is
_{^{-SO 3 -, -SO 3 M,}} -OSO 3 -, -OSO 3 M, -COO - or -COOM
(R ^6, A and M described above show the same meaning as) a bleach activator according to claim 1, wherein the. 3. A bleaching composition comprising the bleaching activator according to claim 1 and hydrogen peroxide or a compound generating hydrogen peroxide in an aqueous solution.