JP2006096741A - Aminealkylene oxide adduct - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide an aminealkylene oxide adduct little in coloring. <P>SOLUTION: The amine-alkylene oxide adduct expressed by general formula (2) satisfies relational formula (1). Provided that, general formula (2) is R-[(A<SP>1</SP>O)m-(A<SP>2</SP>O)n-H]<SB>k</SB>, in which R is a residue removing hydrogen from an amine having k pieces of active hydrogen; A<SP>1</SP>is a 3-8C alkylene group; A<SP>2</SP>is a 2C or 3-8C alkylene group; m is an integer of 1-10; and n is 0 or an integer of 1-400; and relational formula (1) is 10.0≥C<SB>H</SB>/TAmV, in which C<SB>H</SB>shows a Hazen color number; and TAmV shows a total amine value. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to an alkylene oxide adduct of an amine. Specifically, the present invention relates to an amine alkylene oxide adduct with little coloring and a method for producing the same.

Alkylene oxide adducts can be obtained by adding alkylene oxide to amines using no catalyst or alkali metal hydroxide as a catalyst. Products obtained by this method are colored, and antistatic agents and fiber treatment agents. When used for cleaning agents, etc., they were still not fully satisfactory in terms of color.
In order to solve this problem, a method (for example, Patent Document 1) in which the reaction temperature is limited has been proposed.
JP 2003-96186 A

  However, the amine alkylene oxide adducts produced by these production methods were not sufficiently satisfactory in hue.

As a result of intensive studies to solve the above-mentioned problems, the present inventors have reached the present invention.
That is, the present invention satisfies the following relational expression (1), and is an amine alkylene oxide adduct represented by the general formula (2);
Relational expression
10.0 ≧ C _H / TAmV (1)
(Wherein, C _H is Hazen color number of the amine alkylene oxide adducts, TAmV represents total amine value of the amine alkylene oxide adduct)
General formula
^{R - [(A 1 O)} m- (A 2 O) n-H] k (2)
(Wherein R is a residue obtained by removing hydrogen from an amine having k active hydrogens; A ¹ has 3 to 8 carbon atoms)
An alkylene group, A ² is an alkylene group having 2 or 3 to 8 carbon atoms; m is an integer of 1 to 10, and n is an integer of 0 or 1 to 400)

And it is a manufacturing method of the said amine alkylene oxide adduct which performs this addition reaction on the conditions which satisfy | fill the following relational expression (3).
1.5 ≧ [V _PO + 0.041 × S _R × V _O2 / W _A + 0.034 × V _CHO ] ×
M _A / M _f (3)
[ _Wherein V _PO is the peroxide value of amine (meq / kg), S _R is the space capacity after the amine is charged in the reaction vessel (liter: L), V _O2 is the oxygen concentration in the reaction system at room temperature and normal pressure (ppm), charged amount of _{W a} amine _(g), aldehyde content of _{V CHO} amine (ppm)
, M _A is the molecular weight of the amine, M _f is the molecular weight of the amine alkylene oxide adduct after the reaction]

  The amine alkylene oxide adduct of the present invention is less colored.

The amine alkylene oxide adduct of the present invention satisfies the above relational expression (1). It preferably satisfies the relational expression (1 ′), and more preferably satisfies the relational expression (1 ″). If the relational expression (1) is not satisfied, the amount of use is limited and the sufficient performance may not be exhibited when used in an antistatic agent, a fiber treatment agent, a cleaning agent, or the like, which is not preferable.
8.0 ≧ C _H / TAmV (1 ′)
6.0 ≧ C _H / TAmV (1 ″)
Further, the Hazen unit color number of the amine alkylene oxide adduct is preferably 150 or less, more preferably 100 or less.

  In the general formula (2), R represents a residue obtained by removing hydrogen from an amine having k active hydrogens. The amine is not particularly limited as long as it is a compound having an active hydrogen derived from an amino group in the molecule, but is preferably a compound having 1 to 6 active hydrogens derived from an amino group in the molecule, more preferably 1 The compound having ˜2 is particularly preferable. The active hydrogen equivalent (molecular weight per active hydrogen) of (B) is preferably 15 to 500, more preferably 20 to 200.

Specific examples of the amine include the following (1) to (10).
(1) Aliphatic amines (i) Aliphatic monoamines (preferably having 1 to 48 carbon atoms and 1 functional group);
Primary amines such as monomethylamine, butylamine, octylamine, laurylamine, stearylamine; secondary amines such as dimethylamine, methylbutylamine, methyllaurylamine, distearylamine;
(Ii) an aliphatic polyamine (preferably having 2 to 18 carbon atoms, 2 to 7 functional groups, and a molecular weight of 60 to 500);
C2-C6 alkylenediamine such as ethylenediamine, propylenediamine, trimethylenediamine, tetramethylenediamine, hexamethylenediamine; diethylenetriamine, iminobispropylamine, bis (hexamethylene) triamine, triethylenetetramine, tetraethylenepentamine, Polyalkylene (2 to 6 carbon atoms) polyamine such as pentaethylenehexamine;
(iii) alkyl (C1-4) or hydroxyalkyl (C2-4) substitution of (ii);
Dialkyl (1 to 3 carbon atoms) aminopropylamine, trimethylhexamethylenediamine, aminoethylethanolamine, 2,5-dimethyl-2,5-hexamethylenediamine, methyliminobispropylamine and the like;
(iv) Alicyclic or heterocyclic ring-containing aliphatic polyamines;
3,9-bis (3-aminopropyl) -2,4,8,10-tetraoxaspiro [5,5] undecane and the like;
(v) Aromatic ring-containing aliphatic amines (8 to 15 carbon atoms)
Xylylenediamine, tetrachloro-p-xylylenediamine, etc .;

(2) Alicyclic amines (i) Alicyclic monoamine (preferably having 6 to 48 carbon atoms and 1 functional group);
Cyclohexylamine, etc .;
(Ii) alicyclic polyamines (6 to 15 carbon atoms, 2 to 3 functional groups);
1,3-diaminocyclohexane, isophoronediamine, mensendiamine, 4,4'-methylenedicyclohexanediamine (hydrogenated methylenedianiline), etc .;
(3) heterocyclic amines (preferably having 4 to 15 carbon atoms and 1 to 3 functional groups);
Piperazine, N-aminoethylpiperazine, 1,4-diaminoethylpiperazine, 1,4bis (2-amino-2-methylpropyl) piperazine and the like;
(4) Aromatic amines (preferably having 6 to 20 carbon atoms, 1 to 3 functional groups, and a molecular weight of 100 to 1000);
(I) Unsubstituted aromatic amines Monoamines such as aniline and o-chloroaniline; 1,2-, 1,3- and 1,4-phenylenediamine, 2,4'- and 4,4'-diphenylmethanediamine, crude Diphenylmethanediamine (polyphenylpolymethylenepolyamine), diaminodiphenylsulfone, benzidine, thiodianiline, bis (3,4-diaminophenyl) sulfone, 2,6-diaminopyridine, m-aminobenzylamine, triphenylmethane-4,4 ' , 4 "-triamine, polyamines such as naphthylenediamine;

(Ii) an aromatic amine having a nucleus-substituted alkyl group [C1-C4 alkyl group such as methyl, ethyl, n- and i-propyl, butyl, etc.];
2,4- and 2,6-tolylenediamine, diethyltolylenediamine, 4,4'-diamino-3,3'-dimethyldiphenylmethane, 4,4'-bis (o-toluidine), dianisidine, 1,3 -Dimethyl-2,4-diaminobenzene, 1,4-dibutyl-2,5-diaminobenzene, 2,3-dimethyl-1,4-diaminonaphthalene, 3,3'-diethyl-2,2'-diaminodiphenylmethane 3,3 ′, 5,5′-tetraethyl-4,4′-diaminodiphenyl ether and the like, and mixtures of these isomers in various proportions;
(Iii) an aromatic amine having a nucleus-substituted electron withdrawing group (halogen such as Cl, Br, I and F; alkoxy group such as methoxy and ethoxy; nitro group and the like);
Methylenebis-o-chloroaniline, 4-chloro-o-phenylenediamine, 3-amino-4-chloroaniline, 5-nitro-1,3-phenylenediamine; 4,4'-diamino-3,3'-dimethyl- 5,5'-dibromo-diphenylmethane, bis (4-amino-3-methoxyphenyl) disulfide, 4,4'-methylenebis (2-fluoroaniline) and the like;

(Iv) An aromatic polyamine having a secondary amino group [partial or all of —NH ₂ of the aromatic amine of the above (i) to (iii) is —NH—R ′ (R ′ is an alkyl group such as methyl, ethyl A lower alkyl group such as
4,4'-di (methylamino) diphenylmethane, 1-methyl-2-methylamino-4-aminobenzene and the like;
(5) Polyamide polyamine;
Polyamide polyamine (number average molecular weight) obtained by condensation of dicarboxylic acid (such as dimer acid) and excess (more than 2 moles per mole of acid) polyamine (the above-mentioned alkylene diamine, polyalkylene polyamine, etc. having 2 to 7 functional groups) 331-2,000) etc .;
(6) polyether polyamine;
Hydride of cyanoethylated polyether polyol (number average molecular weight 148 to 4,000), etc .;
(7) epoxy-added polyamine;
Epoxy addition polyamine (number average molecular weight 205-1,000) obtained by adding 1-30 mol of an epoxy compound and 1 mol of monoepoxide to polyamines (the above-mentioned alkylene diamine, polyalkylene polyamine, etc.);

(8) cyanoethylated polyamine;
Cyanoethylated polyamines obtained by addition reaction of acrylonitrile and polyamines (the above alkylenediamine, polyalkylenepolyamine, etc.), (biscyanoethyldiethylenetriamine, etc.) (number average molecular weight 113 to 500), etc .;
(9) Mannich polyamine;
Formaldehyde condensates (number average molecular weight 166) of phenols (phenol, nonylphenol, tris (N, N-dimethylaminomethyl) phenol, etc.) and polyamines (the above aliphatic polyamines having 2 to 7 functional groups, alicyclic polyamines, etc.) ~ 1,000) etc. (10) Other polyamino compounds;
(I) Hydrazines (hydrazine, monoalkylhydrazine, etc.);
(Ii) Dihydrazides (succinic acid dihydrazide, adipic acid dihydrazide, isophthalic acid dihydrazide, terephthalic acid dihydrazide, etc.);
(Iii) Guanidines (butyl guanidine, 1-cyanoguanidine, etc.);
(Iv) dicyandiamide and the like;
And mixtures of two or more of these. Among these, the aliphatic amine of (1) is preferable, more preferably an aliphatic monoamine, particularly preferably a primary or secondary aliphatic monoamine, and the most preferable primary aliphatic. It is a monoamine. Further, the alkyl group portion may be linear or branched.

A ¹ is an alkylene group having 3 to 8 carbon atoms, specifically 1,2-propylene group, 1,2-butylene group, 1,4-butylene group, 1-phenyl-1,2-ethylene group. And preferably a 1,2-propylene group.

A ² is an alkylene group having 2 or 3 to 8 carbon atoms, and specific examples thereof include the same groups as the ethylene group and the groups listed in A ¹ above. An ethylene group is preferred.

m is an integer of 1 to 10, preferably an integer of 1 to 5, and more preferably an integer of 1 to 3. If m exceeds 10, the hydrophilicity of the amine alkylene oxide adduct becomes poor and the use is limited, which is not preferable. n is 0 or an integer of 1 to 400, preferably an integer of 5 to 300, more preferably an integer of 10 to 200. When n exceeds 400, the viscosity becomes high and handling becomes difficult.
k is preferably 1 to 40, more preferably 1 to 20, and particularly preferably 1 to 5. When k exceeds 40, the viscosity increases and handling becomes difficult.
The number average molecular weight is preferably 235 to 200,000, more preferably 409 to 150,000.

The amine alkylene oxide adduct of the present invention is produced by addition reaction of an alkylene oxide to an amine in the absence of a catalyst or in the presence of a catalyst.
The amine can be expressed as R- (H) _k , and R is the same as R in the general formula (2).

The reaction is preferably performed while satisfying the relational expression (3).
The right side of the relational expression (3) represents the magnitude of the aldehyde concentration produced in the reaction system. The left side of the relational expression is 1.5, preferably 1.25, and more preferably 1.0. When the left side of the relational expression (3) is 1.5 or less, it is difficult to produce aldehyde in the reaction system, and coloring is suppressed.

Each value in the above relational expression is obtained as follows.
(Peroxide value measurement method)
The peroxide value is expressed in milliequivalents per gram of iodine that is liberated when potassium iodide is allowed to act on the sample. Peroxide value is obtained by dissolving a sample in a mixed solution of chloroform and glacial acetic acid, reacting with potassium iodide, and using a starch indicator, the iodine produced by reacting with the peroxide is an aqueous sodium thiosulfate solution with a known normality. It is analyzed by a titration method, and is calculated from the titration amount of sodium thiosulfate and converted to milliequivalents of iodine.

(Measurement method of aldehyde content)
Weigh sample accurately in a glass bottle with a lid. Sampling amount is expected aldehyde content is 1
It is 50 g when it is less than 00 ppm, 30 g when it is 100 or more and less than 300 ppm, and 20 g or less when it is 300 ppm or more. When the aldehyde content is unknown, measurement is first performed with a sampling amount of 20 g, and when the measured value is less than 300 ppm, the measurement is performed again with the above sample amount. After sampling, 50 ml (25 ° C.) of hydroxylamine hydrochloride solution (50 g of hydroxylamine hydrochloride dissolved in 150 ml of pure water and added with isopropanol to 1 L) was added with a whole pipette, mixed well, sealed, and sealed. Leave at 30 ° C. for 30 minutes. After cooling to room temperature, 50 mL of methanol is added immediately before titration, and potentiometric titration is performed with an N / 10 methanolic KOH standard solution. At the same time, a blank test is performed.
Aldehyde content (ppm) = (KB) × Y × 2900 / Z
K: Titration ml number of N / 10 methanolic KOH standard solution required for this test B: Titration ml number of N / 10 methanolic KOH standard solution required for blank test Y: Force of N / 10 methanolic KOH standard solution Value Z: Sampling amount (g)

(Measurement method for Hazen unit colors)
Measured according to the method of JIS K0071-1. However, when the color of the sample is darker than the color number 500 of the standard colorimetric tube, the sample is diluted with ion exchange water (or a soluble solvent if insoluble in ion exchange water) and measured. The value obtained by multiplying the measurement color number by the dilution factor is taken as the measurement value.

(Total amine value measurement method)
The total amine value is the number of mg of potassium hydroxide equivalent to perchloric acid required to neutralize amine in 1 g, and represents the content of amine contained in the sample. The measuring method is as follows.
Weigh sample accurately into a glass bottle. The amount of sampling is 7 g when the expected total amine number is less than 0.5, 4.5 g when it is 0.5 or more and less than 2, and 2 g or less when it is 2 or more. After sampling, 50 mL of acetic acid is added to dissolve the sample. Potentiometric titration is performed with N / 100 perchloric acid standard solution. At the same time, a blank test is performed.
Total amine number = (K′−B ′) × Y ′ × 0.56111 / Z
K ′: titration ml number of N / 100 perchloric acid standard solution required for this test B ′: titration ml number of NN / 100 perchloric acid standard solution required for blank test Y ′: N / 100 perchloric acid standard Solution titer Z ': Sampling amount (g)

Examples of the alkylene oxide having 3 to 8 carbon atoms include 1,2-propylene oxide (PO), 1,2- or 2,3-butylene oxide, tetrahydrofuran, styrene oxide and the like. Of these, PO is preferred. The addition form of PO and C2 alkylene oxide (ethylene oxide; EO) may be block or random. Random addition is preferable.
The number of added moles of the alkylene oxide having 3 to 8 carbon atoms is the same as m in the general formula (1). The preferred ones are the same.

The alkylene oxide having 2 or 3 to 8 carbon atoms is the same as the alkylene oxide having 3 to 8 carbon atoms in addition to ethylene oxide (EO). Of these, EO is preferred. The addition form of A ¹ O and A ² O is preferably block addition.
The added mole number of the alkylene oxide having 2 to 8 carbon atoms is the same as n in the general formula (1). The preferred ones are the same.

The reaction between the amine and the alkylene oxide is carried out without a catalyst or in the presence of a catalyst. In the case of using a catalyst, alkali catalysts such as sodium hydroxide, potassium hydroxide, metallic sodium and metallic potassium, and Lewis acid catalysts such as boron trifluoride and tin tetrachloride are exemplified. Among these, an alkali catalyst is preferable, and potassium hydroxide is more preferable.

  The sodium content contained in the alkali catalyst is preferably 500 ppm or less with respect to the weight of the alkali catalyst. More preferably, it is 400 ppm or less. When the sodium content is 500 ppm or less, the reaction between the amine and the alkylene oxide proceeds rapidly, and the resulting adduct is less colored, which is preferable.

  The reaction system is dried at 60 ° C. to 200 ° C., the catalyst is added, and after the inside of the system is dehydrated (preferably moisture of 500 ppm or less), the alkylene oxide is preferably 80 to 200 ° C., more preferably 100 to 180 ° C. Can be reacted. The reaction time is preferably 4 to 48 hours. The end point of the reaction can be controlled by the total amine value.

  EXAMPLES Hereinafter, although an Example demonstrates this invention further, this invention is not limited to this. Below, a part shows a weight part.

Example 1
In a 2 liter stainless steel autoclave with stirring and temperature control function, 185 parts (1.0 mol) of laurylamine (trade name: Farmin 20D, manufactured by Kao Corporation), 2.0% potassium hydroxide (sodium content: 300 ppm) 2.0 The mixture was replaced with nitrogen. The oxygen concentration at this time was 50 ppm. Thereafter, dehydration was performed at 100 ° C. for 1 hour under reduced pressure (1 to 5 mmHg). The peroxide value of laurylamine used at this time was 0.01 meq / kg, and the aldehyde content was 5 ppm. Subsequently, at 130 ° C., 174 parts (3.0 mol) of propylene oxide was introduced so that the gauge pressure was 1 to 3 kgf / cm ^2, and after the reaction, 1496 parts (34.0 mol) of ethylene oxide was added to a gauge pressure of 1 to 1 It introduce | transduced so that it might become 3 kgf / cm < ² >, and the amine alkylene oxide addition product (A-1) was obtained. The reaction time from the start of propylene oxide blowing to the end of the reaction was 12 hours. The right side of the relational expression (3) obtained from the reaction conditions was 0.02. The total amine value of (A-1) was 30.2, the Hazen unit color number was 120, and the right side of the relational expression (1) was 4.0.

Example 2
In a 2 liter stainless steel autoclave with stirring and temperature control function, 269 parts (1.0 mol) of stearylamine (trade name: Amine HTD, manufactured by Lion), potassium hydroxide (sodium content: 300 ppm) 2 0.0 part was added, and the inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 45 ppm. Thereafter, dehydration was performed at 100 ° C. for 1 hour under reduced pressure (1 to 5 mmHg). The peroxide value of stearylamine used at this time was 0.02 meq / kg, and the aldehyde content was 8 ppm. Next, at 130 ° C., 116 parts (2.0 mol) of propylene oxide was introduced so that the gauge pressure was 1 to 3 kgf / cm ^2, and after completion of the reaction, 836 parts (19.0 mol) of ethylene oxide was added to 1 to 1 gauge pressure. It introduce | transduced so that it might become 3 kgf / cm < ² >, and the amine alkylene oxide adduct (A-2) was obtained. The reaction time from the start of propylene oxide blowing to the end of the reaction was 11 hours. The right side of the relational expression (3) obtained from the reaction conditions was 0.07. The total amine number of (A-2) was 45.9, the Hazen unit color number was 100, and the right side of the relational expression (1) was 2.2.

Example 3
In a 2 liter stainless steel autoclave with stirring and temperature control function, 103 parts (1.0 mol) of diethylenetriamine (trade name: DETA, manufactured by Tosoh Corporation) and 2.0 parts of potassium hydroxide (sodium content: 300 ppm) The mixed system was replaced with nitrogen. The oxygen concentration at this time was 55 ppm. The peroxide value of diethylenetriamine used at this time was 0.01 meq / kg, and the aldehyde content was 4 ppm. Next, at 130 ° C., 580 parts (10.0 mol) of propylene oxide was introduced so that the gauge pressure was 1 to 3 kgf / cm ^2, and 1056 parts (24.0 mol) of ethylene oxide was added to the gauge pressure of 1 to 1 after completion of the reaction. Introduced to be 3 kgf / cm ² , an amine alkylene oxide adduct (A-3)
Got. The reaction time from the start of propylene oxide blowing to the end of the reaction was 12 hours. The right side of the relational expression (3) obtained from the reaction conditions was 0.01. The total amine value of (A-3) was 96.8, the Hazen unit color number was 180, and the right side of the relational expression (1) was 1.9.

Example 4
In a 2 liter stainless steel autoclave with stirring and temperature control function, 232 parts (1.0 mol) of pentaethylenehexamine (trade name: manufactured by PEHA Tosoh Corporation), dimer acid (trade name: Tsunodyme 205S, manufactured by Tsukino Food Industry Co., Ltd.) ) 288 parts (0.5 mol) was added, the inside of the mixed system was replaced with nitrogen, and the reaction was carried out at 120 ° C. until the acid value became 4.0 or less. At this time, the peroxide value was 0.01 meq / kg, and the aldehyde content was 3 ppm.
Next, 2.0 parts of potassium hydroxide (sodium content: 300 ppm) was added, and the inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 60 ppm. Thereafter, dehydration was performed at 100 ° C. for 1 hour under reduced pressure (1 to 5 mmHg). Next, at 130 ° C., 812 parts (14.0 mol) of propylene oxide was introduced so that the gauge pressure was 1 to 3 kgf / cm ^2, and 616 parts (14.0 mol) of ethylene oxide was added to the gauge pressure of 1 to 1 after completion of the reaction. It introduce | transduced so that it might become 3 kgf / cm < ² >, and the amine alkylene oxide adduct (A-4) was obtained. The reaction time from the start of propylene oxide blowing to the end of the reaction was 11 hours. The right side of the relational expression (3) obtained from the reaction conditions was 0.03. The total amine value of (A-4) was 172.8, the Hazen unit color number was 180, and the right side of the relational expression (1) was 1.0.

Example 5
An amine alkylene oxide adduct (A-5) was obtained in the same manner as in Example 1 except that potassium hydroxide (sodium content: 1500 ppm) was used instead of potassium hydroxide (sodium content: 300 ppm). The reaction time from the start of propylene oxide blowing to the end of the reaction was 15 hours. The right side of the relational expression (3) obtained from the reaction conditions was 0.02. The total amine value of (A-5) was 30.2, the Hazen unit color number was 200, and the right side of the relational expression (1) was 6.61.

Comparative Example 1
In a 2 liter stainless steel autoclave with stirring and temperature control function, 269 parts (1.0 mol) of stearylamine (trade name: Armin HTD, manufactured by Lion), potassium hydroxide (sodium content: 1500 ppm) 1 0.0 part was added, and the inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 50 ppm. Thereafter, dehydration was performed at 100 ° C. for 1 hour under reduced pressure (1 to 5 mmHg). The peroxide value of stearylamine used at this time was 0.02 meq / kg, and the aldehyde content was 10 ppm. Subsequently, 616 parts (14.0 mol) of ethylene oxide was introduced at 130 ° C. so that the gauge pressure was 1 to 3 kgf / cm ² to obtain an amine alkylene oxide adduct (A-6). The reaction time from the start of blowing ethylene oxide to the end of the reaction was 8 hours. The right side of the relational expression (3) obtained from the reaction conditions was 0.11. The total amine value of (A-6) was 63.4, the Hazen unit color number was 2500, and the right side of the relational expression (1) was 39.4.

Comparative Example 2
In a 2 liter stainless steel autoclave with stirring and temperature control function, 269 parts (1.0 mol) of stearylamine (trade name: Amine HTD, manufactured by Lion), potassium hydroxide (sodium content: 1500 ppm) 2 0.0 part was added, and the inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 100 ppm. Thereafter, dehydration was performed at 100 ° C. for 1 hour under reduced pressure (1 to 5 mmHg). The peroxide value of stearylamine used at this time was 2.0 meq / kg, and the aldehyde content was 210 ppm. Next, at 130 ° C., 116 parts (2.0 mol) of propylene oxide was introduced so that the gauge pressure was 1 to 3 kgf / cm ^2, and after completion of the reaction, 836 parts (19.0 mol) of ethylene oxide was added to 1 to 1 gauge pressure. It introduce | transduced so that it might become 3 kgf / cm < ² >, and the amine alkylene oxide addition product (A-7) was obtained. The reaction time from the start of propylene oxide blowing to the end of the reaction was 15 hours. The right side of the relational expression (3) obtained from the reaction conditions was 2.02. The total amine value of (A-7) was 46.0, the Hazen unit color number was 600, and the right side of the relational expression (1) was 13.1.

Comparative Example 3
Into a 2 liter stainless steel autoclave with stirring and temperature control functions, 320 parts (1.2 mol) of stearylamine (trade name: Armin HTD, manufactured by Lion) and 0.6 part of triethanolamine are added. The inside of the mixed system was replaced with nitrogen. The oxygen concentration at this time was 50 ppm. The peroxide value of stearylamine used at this time was 0.02 meq / kg, and the aldehyde content was 10 ppm. Next, 98 parts (2.2 mol) of ethylene oxide was introduced at 130 ° C. so that the gauge pressure was 1 to 3 kgf / cm ^2, and the temperature was lowered to 90 ° C. after completion of the reaction, and 218 parts (4.9 mol) of ethylene oxide was added. It introduced so that a gauge pressure might be 1-3 kgf / cm < ² >, and the amine alkylene oxide addition product (A-8) was obtained. The reaction time from the start of blowing ethylene oxide to the end of the reaction was 8 hours. The right side of the relational expression (3) obtained from the reaction conditions was 0.16. The total amine value of (A-8) was 104.9, the Hazen unit color number was 2700, and the right side of the relational expression (1) was 25.7.

  Table 1 summarizes the above values. As is apparent from this table, the amine alkylene oxide adducts of Comparative Examples 1 to 3 are highly colored. In contrast, the amine alkylene oxide adducts of Examples 1 to 5 are less colored.

  The amine alkylene oxide adducts of the present invention are less colored and are used as antistatic agents, fiber treatment agents, rust inhibitors, foaming agents or antifoaming agents, wetting agents, penetrating agents, cleaning agents, emulsifying agents, dispersing agents and solubilizing agents. Moreover, it is useful as these base materials.

Claims (7)

An amine alkylene oxide adduct represented by the general formula (2) characterized by satisfying the following relational expression (1).
Relational expression
10.0 ≧ C _H / TAmV (1)
(Wherein, C _H is Hazen color number of the amine alkylene oxide adducts, TAmV represents total amine value of the amine alkylene oxide adduct)
General formula
^{R - [(A 1 O)} m- (A 2 O) n-H] k (2)
(Wherein R is a residue obtained by removing hydrogen from an amine having k active hydrogens; A ¹ has 3 to 8 carbon atoms)
An alkylene group, A ² is an alkylene group having 2 or 3 to 8 carbon atoms; m is an integer of 1 to 10, and n is an integer of 0 or 1 to 400) The amine alkylene oxide adduct according to claim ^1, wherein A ¹ is a propylene group. The amine alkylene oxide adduct according to claim 1 or 2, wherein A ² is an ethylene group. The amine alkylene oxide adduct according to any one of claims 1 to 3, wherein m is an integer of 1 to 5. The method for producing an amine alkylene oxide adduct according to any one of claims 1 to 4, wherein the addition reaction is performed under a condition satisfying the following relational expression (3).
1.5 ≧ [V _PO + 0.041 × S _R × V _O2 / W _A + 0.034 × V _CHO ] ×
M _A / M _f (3)
[ _Wherein V _PO is the peroxide value of amine (meq / kg), S _R is the space capacity after the amine is charged in the reaction vessel (liter: L), V _O2 is the oxygen concentration in the reaction system at room temperature and normal pressure (ppm), charged amount of _{W a} amine _(g), aldehyde content of _{V CHO} amine (ppm)
, M _A is the molecular weight of the amine, M _f is the molecular weight of the amine alkylene oxide adduct after the reaction] 6. The method for producing an amine alkylene oxide adduct according to claim 5, wherein the addition reaction is carried out using an alkali catalyst. The method for producing an amine alkylene oxide adduct according to claim 6, wherein the sodium content in the alkali catalyst is 500 ppm or less.