JPH0543528A - New amide amine and its production - Google Patents

New amide amine and its production

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Publication number
JPH0543528A
JPH0543528A JP20684591A JP20684591A JPH0543528A JP H0543528 A JPH0543528 A JP H0543528A JP 20684591 A JP20684591 A JP 20684591A JP 20684591 A JP20684591 A JP 20684591A JP H0543528 A JPH0543528 A JP H0543528A
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JP
Japan
Prior art keywords
general formula
represented
alkyl
carbon atoms
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP20684591A
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Japanese (ja)
Other versions
JP2951762B2 (en
Inventor
Toru Kato
Koshiro Sotodani
Osamu Tatezawa
徹 加藤
孝四郎 外谷
修 立澤
Original Assignee
Kao Corp
花王株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication date
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Priority to JP20684591A priority Critical patent/JP2951762B2/en
Publication of JPH0543528A publication Critical patent/JPH0543528A/en
Application granted granted Critical
Publication of JP2951762B2 publication Critical patent/JP2951762B2/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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Abstract

(57) [Summary] [Object] To provide a compound having excellent flexibility and biodegradability, which is suitable as a soft base. [Structure] A novel amidoamine represented by the general formula (I). [Chemical 1] (In the formula, R 1 is an alkyl group or a hydroxyalkyl group having 1 to 6 carbon atoms, R 2 is a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, and R 3 is an alkyl group having 7 to 35 carbon atoms. A linear or branched alkyl group or alkenyl group,
n shows the integer of 1-3. )

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a novel amidoamine and a method for producing the same. More specifically, the present invention relates to a novel amidoamine which is useful as a surfactant and also as a softening agent for cloth, hair and the like, and a method for producing the same.

[0002]

2. Description of the Related Art Conventionally, the problems to be solved by the invention
Compounds used as softeners for cloth and hair are
Although it is a quaternary ammonium salt having two long-chain alkyl groups, it is necessary to develop a soft base having higher biodegradability. An object of the present invention is to obtain a compound having excellent flexibility and biodegradability, which is suitable as a soft base.

[0003]

As a result of intensive studies to solve the above problems, the present inventors have found that a specific novel amidoamine is optimal for the above purpose, and completed the present invention. That is, the present invention provides an amidoamine represented by the general formula (I) and a method for producing the same.

[0004]

[Chemical 8]

(Wherein R 1 is an alkyl group or hydroxyalkyl group having 1 to 6 carbon atoms, R 2 is a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, and R 3 is 7 carbon atoms. To 35 linear or branched alkyl or alkenyl groups, and n represents an integer of 1 to 3.) General formula (I)
Examples of the compound represented by are as follows.

[0006]

[Chemical 9]

[0007]

[Chemical 10]

The amidoamine of the present invention represented by the above general formula (I) is produced by the following method. That is, first, the general formula (II)

[0009]

[Chemical 11]

(Wherein R 1 has the same meaning as described above) and the secondary amino nitrile represented by the general formula (III)

[0011]

[Chemical formula 12]

(In the formula, R 2 has the same meaning as described above.)
Or an alkyl glycidyl ether represented by the general formula (IV)

[0013]

[Chemical 13]

(In the formula, R 2 has the same meaning as described above.) An addition reaction is carried out using 3-chloro-2-hydroxypropyl alkyl ether represented by the general formula (V)

[0015]

[Chemical 14]

An aminonitrile represented by the formula (wherein R 1 and R 2 have the same meanings as described above) is obtained. Then, the hydrogenation reaction of aminonitrile is carried out using a catalyst, and the general formula (VI)

[0017]

[Chemical 15]

An amine represented by the formula (wherein R 1 and R 2 have the same meanings as described above) is obtained. If necessary, cyanoethylation and hydrogenation reactions were repeated using acrylonitrile to obtain the general formula (VII)

[0019]

[Chemical 16]

(Wherein R 1 , R 2 and n have the same meanings as described above), the amine represented by the general formula (VIII) R 3 COOR 4 (VIII) (wherein R 3 is the same as above) Meaning, R 4 represents H or an alkyl group having 1 to 3 carbon atoms.) Amidation is performed using a fatty acid or a fatty acid ester to obtain an amidoamine represented by the general formula (I). ..

More specifically, the production of the amidoamine of the present invention can be explained as follows. In the addition reaction of the alkyl glycidyl ether represented by the general formula (III) to the secondary amino nitrile represented by the general formula (II), 0.8 to 5 times mol of the alkyl glycidyl ether is added to the amino nitrile, and the temperature is increased. 2 to 50-90 ℃
The addition reaction is completed in 30 hours. When 3-chloro-2-hydroxypropylalkyl ether represented by the general formula (IV) is used for the addition reaction, 0.8 to 5 times mol of 3-chloro-2-hydroxypropylalkyl ether with respect to aminonitrile is used. 0.8 to 5 times the molar amount of the alkaline substance is added to the ether and aminonitrile, and the reaction is completed at 50 to 90 ° C. for 2 to 30 hours. Then, this adduct is subjected to hydrogenation reaction in the presence of a catalyst at 60 to 150 ° C. for 1 to 10 hours. If necessary, the addition reaction of acrylonitrile and the hydrogenation reaction are repeated to obtain the amine represented by the general formula (VII). The obtained amine was 0 for the amine.
Using 8 to 2 times the molar amount of the fatty acid or fatty acid ester represented by the general formula (VIII), without catalyst or in the presence of a catalyst, 10
The amidation reaction is carried out at 0 to 220 ° C. for 1 to 20 hours under normal pressure or reduced pressure to obtain an amidoamine represented by the general formula (I).

The secondary aminonitrile represented by the general formula (II) used in the present invention includes N- (2-cyanoethyl) methylamine, N- (2-cyanoethyl) ethylamine and N- (2-cyanoethyl). -N- (2-hydroxyethyl) amine, N- (2-cyanoethyl) butylamine, N- (2-cyanoethyl) hexylamine or a mixture thereof.

In the present invention, 2 represented by the general formula (II)
General formula (II
The alkyl glycidyl ether represented by I) includes octyl glycidyl ether and decyl glycidyl ether.
Ether, dodecyl glycidyl ether, tetradecyl glycidyl ether, hexadecyl glycidyl ether, octadecyl glycidyl ether,
Eicosyl glycidyl ether, docosyl glycidyl ether, 2-ethylhexyl glycidyl ether, 2-butyloctyl glycidyl ether,
2-hexyldecyl glycidyl ether, 2-octyldodecyl glycidyl ether, 2-decyl tetradecyl glycidyl ether, 2-dodecyl hexadecyl glycidyl ether, 2-tetradecyl octadecyl glycidyl ether, 2-hexadecyl eicosyl glycidyl ether, or a mixture thereof. Is mentioned.

The 3-chloro-2-hydroxypropylalkyl ether represented by the general formula (IV) used in the addition reaction to the aminonitrile represented by the general formula (II) in the present invention is 3-chloro- 2-hydroxypropyl octyl ether, 3-chloro-2-hydroxypropyl decyl ether, 3-chloro-2-hydroxypropyl dodecyl ether, 3-chloro-2-hydroxypropyl tetradecyl ether, 3-chloro-2-hydroxypropyl hexa Decyl ether, 3-chloro-2-
Hydroxypropyl octadecyl ether, 3-chloro-2-hydroxypropyl eicosyl ether, 3-chloro-2-hydroxypropyl docosyl ether, 3-
Chloro-2-hydroxypropyl-2-ethylhexyl ether, 3-chloro-2-hydroxypropyl-2-
Butyl octyl ether, 3-chloro-2-hydroxypropyl-2-hexyldecyl ether, 3-chloro-
2-hydroxypropyl-2-octyl dodecyl ether, 3-chloro-2-hydroxypropyl-2-decyl tetradecyl ether, 3-chloro-2-hydroxypropyl-2-dodecyl hexadecyl ether, 3-chloro-2-hydroxy Examples include propyl-2-tetradecyl octadecyl ether, 3-chloro-2-hydroxypropyl-2-hexadecyl eicosyl ether or mixtures thereof.

Examples of the alkaline substance used in the addition reaction to the aminonitrile represented by the general formula (II) in the present invention include sodium hydroxide, potassium hydroxide, sodium hydrogen carbonate, potassium carbonate and the like. These may be used alone or in combination.

Examples of the fatty acid or fatty acid ester represented by the general formula (VIII) used for amidation in the present invention include octanoic acid, decanoic acid, dodecanoic acid, tetradecanoic acid, hexadecanoic acid, octadecanoic acid, eicosanoic acid and docosane. Acid, 2-ethylhexanoic acid, 2-butyloctanoic acid, 2-hexyldecanoic acid, 2-octyldodecanoic acid, 2-decyltetradecanoic acid, 2-dodecylhexadecanoic acid, 2-tetradecyloctadecanoic acid, 2-hexadecyleicosane Examples thereof include acids, methyl esters, ethyl esters, propyl esters, and the like of these fatty acids, or a mixture thereof. Examples of the catalyst used for the amidation of the present invention include sodium methylate, sodium ethylate, potassium methylate, potassium ethylate, sodium hydroxide, potassium hydroxide and the like.

The structure of the amidoamine represented by the general formula (I) of the present invention can be confirmed by infrared absorption spectrum and nuclear magnetic resonance spectrum.

[0028]

INDUSTRIAL APPLICABILITY The amidoamine represented by the general formula (I) provided by the present invention is a novel surfactant and useful as a softening agent base having excellent biodegradability.

[0029]

The present invention will be described in more detail with reference to the following examples, but the present invention is not limited thereto.

Example 1 In a four-necked flask equipped with a stirrer, a thermometer, and a dropping funnel.
59 g of N- (2-cyanoethyl) methylamine and 250 g of octadecyl glycidyl ether were added, and the temperature was raised to 65 ° C. The addition reaction was carried out for 20 hours while maintaining the liquid temperature at 65 to 70 ° C. After the reaction was completed, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then Raney Ni 5
g, sodium hydroxide 1.25g, water 25g, hydrogen pressure
The hydrogenation reaction was carried out for 6 hours while maintaining the temperature at 20 kg / cm 2 and the temperature at 80 ° C. After completion of the reaction, Raney Ni was filtered and the reaction solution was distilled to obtain 167 g of diamine. Boiling point is 235-245
It was ℃ / 0.5mmHg. 100 g of the above diamine and 65 g of octadecanoic acid were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube, and the temperature was raised to 180 ° C. The amidation reaction was carried out at the same temperature for 6 hours while distilling off the produced water to obtain 157 g of the desired product. The following structure was confirmed from the NMR spectrum and IR spectrum.

[0031]

[Chemical 17]

IR spectrum (KBr tablets): 3320 cm -1 , 1640 cm -1 , 1545 cm -1 , 1120 cm -1 Example 2 In a four-necked flask equipped with a stirrer, thermometer and dropping funnel.
59 g of N- (2-cyanoethyl) methylamine and 250 g of octadecyl glycidyl ether were added, and the temperature was raised to 65 ° C. The addition reaction was carried out for 20 hours while maintaining the liquid temperature at 65 to 70 ° C. After the reaction was completed, the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then Raney Ni5
g, sodium hydroxide 1.25g, water 25g, hydrogen pressure
The hydrogenation reaction was carried out for 6 hours while maintaining the temperature at 20 kg / cm 2 and the temperature at 80 ° C. Then, 60 g of acrylonitrile 32 g
The mixture was added at 0 ° C and aged at the same temperature for 1 hour. After completion of the aging, the hydrogenation reaction was carried out at 80 ° C. for 6 hours while maintaining the hydrogen pressure at 20 kg / cm 2 . After completion of the reaction, Raney Ni was filtered to obtain 195 g of triamine. 100 g of the above triamine in a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube,
Methyl hexadecanoate 55g and sodium methylate
0.1 g was added and the temperature was raised to 120 ° C. The amidation reaction was carried out at the same temperature for 6 hours while distilling off the produced methanol to obtain 140 g of the desired product. The following structure was confirmed from the NMR spectrum and IR spectrum.

[0033]

[Chemical 18]

IR spectrum (KBr tablets): 3320 cm -1 , 1645 cm -1 , 1545 cm -1 , 1125 cm -1 Example 3 A four-necked flask equipped with a stirrer, thermometer, dropping funnel, N- (2- Cyanoethyl) methylamine 59 g and 3-chloro-2-hydroxypropyl octadecyl ether 2
80 g was added and the temperature was raised to 65 ° C. Then, while stirring, 65 g of a 48% sodium hydroxide aqueous solution was added over 2 hours while maintaining the liquid temperature at 65 to 70 ° C. After the addition was completed, aging was carried out at the same temperature for 20 hours to complete the addition reaction. After completion of the reaction, the reaction solution was washed with water until the solution became neutral, and then the reaction solution was transferred to an autoclave equipped with a stirrer, a thermometer, and a pressure gauge. Then add Raney Ni 5g, sodium hydroxide 1.25g, water 25g, hydrogen pressure 20kg / cm 2 ,
The hydrogenation reaction was carried out for 6 hours while maintaining the temperature at 80 ° C. After the reaction was completed, Raney Ni was filtered and the reaction solution was distilled.
165 g of diamine were obtained. Boiling point is 235-245 ℃ / 0.5mmH
It was g. 100 g of the above diamine and 65 g of octadecanoic acid were placed in a four-necked flask equipped with a stirrer, a thermometer, and a dehydration tube, and the temperature was raised to 180 ° C. The amidation reaction was performed for 6 hours at the same temperature while distilling off the produced water to remove the desired product.
157 g were obtained. The following structure was confirmed from the NMR spectrum and IR spectrum.

[0035]

[Chemical 19]

IR spectrum (KBr tablets): 3320 cm -1 , 1645 cm -1 , 1548 cm -1 , 1120 cm -1

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 5 Identification code Office reference number FI Technical display location C07C 233/38 7106-4H D06M 13/402

Claims (2)

[Claims]
1. A novel amidoamine represented by the general formula (I). [Chemical 1] (In the formula, R 1 is an alkyl group or a hydroxyalkyl group having 1 to 6 carbon atoms, R 2 is a linear or branched alkyl group or alkenyl group having 8 to 36 carbon atoms, and R 3 is an alkyl group having 7 to 35 carbon atoms. A linear or branched alkyl group or alkenyl group,
n shows the integer of 1-3. )
2. A compound represented by the general formula (II): (In the formula, R 1 represents an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group.) The secondary aminonitrile represented by the general formula (III) (In the formula, R 2 represents a linear or branched alkyl or alkenyl group having 8 to 36 carbon atoms.) Or an alkyl glycidyl ether represented by the general formula (IV): (In the formula, R 2 has the same meaning as described above.) 3
An addition reaction was carried out using -chloro-2-hydroxypropyl alkyl ether to obtain the general formula (V) (In the formula, R 1 and R 2 have the same meanings as described above.) An aminonitrile represented by the general formula (VI): (Wherein R 1 and R 2 have the same meanings as described above), and if necessary, cyanoethylation and hydrogenation reaction are repeated using acrylonitrile to obtain the obtained general formula ( VII) (In the formula, R 1 and R 2 have the same meanings as described above, and n is 1
Indicates an integer of ˜3. ) Is represented by the general formula (VII
I) R 3 COOR 4 (VIII) (wherein R 3 represents a linear or branched alkyl or alkenyl group having 7 to 35 carbon atoms, and R 4 represents H or an alkyl group having 1 to 3 carbon atoms.) The method for producing a novel amidoamine according to claim 1, which comprises amidating with a fatty acid or a fatty acid ester represented by
JP20684591A 1991-08-19 1991-08-19 Novel amidoamine and method for producing the same Expired - Fee Related JP2951762B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP20684591A JP2951762B2 (en) 1991-08-19 1991-08-19 Novel amidoamine and method for producing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP20684591A JP2951762B2 (en) 1991-08-19 1991-08-19 Novel amidoamine and method for producing the same

Publications (2)

Publication Number Publication Date
JPH0543528A true JPH0543528A (en) 1993-02-23
JP2951762B2 JP2951762B2 (en) 1999-09-20

Family

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Family Applications (1)

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Country Status (1)

Country Link
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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995032942A1 (en) * 1994-06-01 1995-12-07 Rhone-Poulenc Chimie Novel polyglycerolated amidoamines
US5820516A (en) * 1995-10-11 1998-10-13 Mazda Motor Corporation Automatic transmission control system
JP2002294278A (en) * 2001-03-28 2002-10-09 Nof Corp Two-hydrophobic chain/two-hydrophilic group type surfactant and use thereof
US6761664B2 (en) 2001-07-27 2004-07-13 Toyota Jidosha Kabushiki Kaisha Shift control device and shift control method for vehicular automatic transmission
US6929581B2 (en) 2002-09-13 2005-08-16 Toyota Jidosha Kabushiki Kaisha Downshifting time torque-down control device and method

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995032942A1 (en) * 1994-06-01 1995-12-07 Rhone-Poulenc Chimie Novel polyglycerolated amidoamines
FR2720742A1 (en) * 1994-06-01 1995-12-08 Rhone Poulenc Chimie Poly:glycerol amido:amine(s)
US5820516A (en) * 1995-10-11 1998-10-13 Mazda Motor Corporation Automatic transmission control system
JP2002294278A (en) * 2001-03-28 2002-10-09 Nof Corp Two-hydrophobic chain/two-hydrophilic group type surfactant and use thereof
US6761664B2 (en) 2001-07-27 2004-07-13 Toyota Jidosha Kabushiki Kaisha Shift control device and shift control method for vehicular automatic transmission
US6929581B2 (en) 2002-09-13 2005-08-16 Toyota Jidosha Kabushiki Kaisha Downshifting time torque-down control device and method

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Publication number Publication date
JP2951762B2 (en) 1999-09-20

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