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WO2011099810A2 - Procédé de préparation de tensioactif cationique - Google Patents

Procédé de préparation de tensioactif cationique Download PDF

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Publication number
WO2011099810A2
WO2011099810A2 PCT/KR2011/000938 KR2011000938W WO2011099810A2 WO 2011099810 A2 WO2011099810 A2 WO 2011099810A2 KR 2011000938 W KR2011000938 W KR 2011000938W WO 2011099810 A2 WO2011099810 A2 WO 2011099810A2
Authority
WO
WIPO (PCT)
Prior art keywords
acid
reaction
omega
monomeric
cationic surfactant
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.)
Ceased
Application number
PCT/KR2011/000938
Other languages
English (en)
Korean (ko)
Other versions
WO2011099810A3 (fr
Inventor
오세군
김애란
김태실
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
SEB CO Ltd
Original Assignee
SEB CO Ltd
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.)
Filing date
Publication date
Application filed by SEB CO Ltd filed Critical SEB CO Ltd
Publication of WO2011099810A2 publication Critical patent/WO2011099810A2/fr
Publication of WO2011099810A3 publication Critical patent/WO2011099810A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
    • C07C209/14—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups
    • C07C209/20—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of hydroxy groups or of etherified or esterified hydroxy groups with formation of quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C219/00—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C219/02—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C219/04—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C219/06—Compounds containing amino and esterified hydroxy groups bound to the same carbon skeleton having esterified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having the hydroxy groups esterified by carboxylic acids having the esterifying carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms of an acyclic saturated carbon skeleton

Definitions

  • the present invention relates to a method for preparing a cationic surfactant having excellent phase stability, dispersibility and discoloration stability.
  • DDAC dimethyl dialkyl ammonium chloride
  • WO 94/07978 discloses softeners and hair care products prepared using quaternized cationic surfactants derived from triethanolamine, and WO 93/23510.
  • Discloses concentrated fiber softeners and biodegradable fiber softener compositions prepared using cationic surfactants having ester linkages to two hydrophobic groups and WO 92/15745 discloses imidazolines or imidas.
  • Disclosed is a concentrated fabric softener composition prepared using a sleepy ester, a linear fatty alcohol ethoxylate, a polydialkylsiloxane, or the like.
  • WO 94/14935 discloses a concentrated fiber soft dispersant comprising a quaternary ammonium compound prepared using triethanolamine and fatty acids
  • International Patent Publication No. WO 94/13772 discloses A highly concentrated fibrous softener prepared using a small amount of a quaternary ammonium compound comprising an ester group and a nonionic dispersant is disclosed.
  • the fatty acids used in the preparation of the compounds for the preparation of cationic surfactants are fatty acids of oils extracted from palm, palm oil, tallow, etc.
  • the price of fatty acids increases. Accordingly, there is a demand for fatty acid raw materials that can be cheaper and recycle resources.
  • dimer acid represented by the following formula (A) is mainly used to improve the color brightness or stability of the ink using a polyamide resin, such as epoxy, flexo ink, gravure ink, as a main raw material of polyamide. Dimer acid is also applied to the production of coatings, adhesives, castings, or laminating agents made from polyesters, epoxy resins, etc., and other petroleum products additives, surfactants, plasticizers, hydraulic agents, linoleum, rubber additives, pesticides, It is also used as a raw material for foamed plastics.
  • a polyamide resin such as epoxy, flexo ink, gravure ink
  • Dimer acid is also applied to the production of coatings, adhesives, castings, or laminating agents made from polyesters, epoxy resins, etc., and other petroleum products additives, surfactants, plasticizers, hydraulic agents, linoleum, rubber additives, pesticides, It is also used as a raw material for foamed plastics.
  • the dimer acid may be prepared by reacting fatty acids mainly composed of unsaturated fatty acids of oleic acid and linoleic acid such as soybean oil and oil, and in this process, monomeric acid and trimeric acid which are not formed as dimer acid are produced as by-products. Accordingly, the present inventors, by the transesterification reaction and quaternization using the monomer acid produced as a by-product during the production process of the dimer acid, the phase stability, dispersibility and discoloration stability due to isostearic acid and isooleic acid contained in the monomer acid It was found that good compounds can be prepared and used to prepare cationic surfactants to complete the present invention.
  • cationic surfactant comprising a compound of formula 1, comprising quaternizing the product obtained in step 1) with a quaternizing agent selected from the group consisting of dimethyl sulfate, methyl chloride and diethyl sulfate Providing a method for preparing the agent:
  • Ri, R 2 , and R 3 are each independently CH 3 , —CH 2 CH 2 OH or —CH 2 CH 2 0a R 4, wherein R 4 is omega-6 ( ⁇ -6) to omega-12 ( a fatty acid group of d2-22 derived from a monomeric acid including isostearic acid and isooleic acid having a methyl group branched at a carbon position of ⁇ -12);
  • X is halogen, CH 3 S0 4 or C 2 H 6 S0 4 .
  • the present invention provides a method for preparing a cationic surfactant comprising a compound of formula (I):
  • Ri, R 2 , and R 3 are independently of each other CH 3 , —CH 2 CH 2 OH or —CH 2 CH 2 0a) R 4, wherein R 4 is omega-6 ( ⁇ -6) to omega-12 ( ⁇ - the fatty acid group of 22 to 12) in the carbon position of the methyl group attached to the isostearic acid and isophthalic acid-derived monomer containing oleic acid of 12 C;
  • X is halogen, CH 3 S0 4 or C 2 H 6 S0 4 .
  • the process of the present invention comprises the steps of: 1) transesterifying monomeric acid and methyldiethanolamine or triethanolamine; And 2) quaternizing the product obtained in step 1) with a quaternizing agent selected from the group consisting of dimethyl sulfate, methyl chloride and diethyl sulfate.
  • Preparation process of the cationic surfactant comprising the compound of Formula 1 according to the present invention is transesterification reaction using monomeric acid and methyl diethanolamine or triethanolamine (step 1); And quaternization reaction (step 2) using a quaternizing agent selected from the group consisting of dimethylsulfate, methylchloride and diethylsulfate.
  • the monomeric acid may be transesterified using methyldiethanolamine or triethanolamine.
  • the monomeric acid may be a by-product generated during the preparation of dimer acid, and specifically, Douglas A. Burg et al, Journal of the American Oil Chemists' Society (JAOCS), Vol 68, no. 8, p.6 (X)], reacting the dimer acid from about 60% to 80% depending on the reaction conditions by reacting the reaction under a temperature and a high pressure of about 25 CTC using soybean oil or oil. And about 20% to 40% of monomeric acid and trimeric acid may be obtained as a by-product.
  • the dimer acid and trimeric acid may be purified to obtain a monomeric acid.
  • the monomeric acid thus produced may be a fatty acid having a unique isoalkyl structure such as palmitic acid, stearic acid, oleic acid, linoleic acid, and isostearic acid and isooleic acid.
  • a compound of dimer acid, cyclic or aromatic structure may be common depending on the distillation method.
  • isostearic acid represents a structure in which a methyl group is branched at a carbon position of omega-2 ( ⁇ -2) represented by the following formula (2).
  • omega-2 omega-2
  • isostearic acids on the market also have this structure.
  • isostearic acid contained in the monomeric acid used in the present invention is represented by the following general formula (3), which is not an end of the carbon chain, that is, omega-6 ( ⁇ -6) to omega-12 ( ⁇ ) -12) ( For example, the structure in which a methyl group is branched at the carbon position of omega-9 carbon position) is shown.
  • the monomeric acid of the present invention is characterized by containing such isostearic acid and isooleic acid in an amount of 1% by weight or more, preferably 7 to 60% by weight based on the total amount of monomeric acid.
  • the melting point of isostearic acid is below o ° c, and the melting point of general stearic acid is 5 (rc or more). However, the melting point of isostearic acid does not have economic properties due to the high price.
  • the monomeric acid present as a by-product it is possible to utilize the isostearic acid contained in the monomeric acid, thereby preparing a cationic surfactant having excellent physical properties and competitive price and recyclable resources.
  • the transesterification reaction is used to react monomeric acid, methyldiethanolamine or triethanolamine without solvent, and may be performed at a reaction temperature of 160 to 20 CTC for a reaction time of 2 to 8 hours.
  • the monomer acid is preferably used in the amount of 1.5 to 2.2 equivalents of methyl diethan based on amine or triethanolamine.
  • the amount of the monomeric acid is less than 1.5 equivalents, the monoester content is increased, and when the amount of the monomer acid is more than 2.2 equivalents, the amount of the triester is increased, thereby deteriorating physical properties and performance.
  • step 2) of the present invention the product obtained after the transesterification in step 1) is quaternized with a quaternizing agent selected from the group consisting of dimethyl sulfate, methyl chloride and diethyl sulfate in a reaction mixture.
  • a quaternizing agent selected from the group consisting of dimethyl sulfate, methyl chloride and diethyl sulfate in a reaction mixture.
  • the compound of 1 can be prepared. Quaternization reactions can use conventional methods.
  • the quaternized reaction mixture is ethanol (ethyl alcohol), propyl alcohol, hexylene glycol, butyl alcohol, isopropyl alcohol, ethylene glycol as ethylene glycol. ), Glycerine, propylene glycol, propylene glycol, polyethylene glycol, and one or more of two or more common primary, secondary, tertiary or polyhydric alcohols selected from the group consisting of Combined solvents may be used, the amount of which is preferably used in the range of 5 to 40% by weight of the total amount of the semi-agar.
  • the quaternization agent used in the quaternization reaction is methyldiethanolamine of step 1) Or 0.9 to 1.0 equivalent based on triethanolamine.
  • reaction temperature of the quaternized reaction reaction is 40 to 80 ° C, reaction time is preferably performed for 3 to 7 hours.
  • Monomeric acids were prepared using soybean oil according to the method described in Douglas A. Burg et al, Journal of the American Oil Chemists' S c / ey (JAOCS), Vol 68, no. 8, p. 60C>.
  • Example 2 Monomer acids were prepared using eul oil according to the method described in Douglas A. Burg et al, Journal of the American Oil Chemists' 5 c / ey (JAOCS), Vol 68, no. 8, p. 600.
  • Examples 1 and 2 maintain a stable dispersion stability, 5 (maintaining the initial color even if maintained for 1 month in the harsh conditions of rc, while Comparative Examples 1 and 2 according to the harsh conditions It was found that the dispersing stability was also low, such as severe discoloration, phase separation, etc.
  • the present invention has been described above in connection with specific embodiments, but within the scope of the present invention as defined by the appended claims. Those skilled in the art can make various modifications and variations to the present invention.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un procédé de préparation d'un tensioactif cationique contenant un composé de formule chimique 1. Ce procédé consiste à réaliser une estérification sur de l'acide monomérique et de la triéthanolamine ou de la méthyldiméthylamine, et à quaternariser le produit ainsi obtenu au moyen de sulfate de diméthyle ou de chlorure de méthyle. Le tensioactif cationique obtenu par la mise en oeuvre de ce procédé utilise des sous-produits de réaction, ce qui permet de réutiliser les ressources et de réaliser des économies, mais également d'obtenir une stabilité à basse température et une stabilité chromatique améliorées. Le tensioactif selon l'invention peut ainsi être utilisé avantageusement dans des adoucissants, des produits de soins capillaires et analogues.
PCT/KR2011/000938 2010-02-11 2011-02-11 Procédé de préparation de tensioactif cationique Ceased WO2011099810A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR1020100013023A KR100992595B1 (ko) 2010-02-11 2010-02-11 양이온성 계면활성제의 제조방법
KR10-2010-0013023 2010-02-11

Publications (2)

Publication Number Publication Date
WO2011099810A2 true WO2011099810A2 (fr) 2011-08-18
WO2011099810A3 WO2011099810A3 (fr) 2011-12-15

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PCT/KR2011/000938 Ceased WO2011099810A2 (fr) 2010-02-11 2011-02-11 Procédé de préparation de tensioactif cationique

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WO (1) WO2011099810A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119707664A (zh) * 2024-12-24 2025-03-28 安徽虹泰新材料股份有限公司 一种低色泽、低铁含量、低磷含量的二聚酸的制备方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101828352B1 (ko) 2015-11-25 2018-02-12 노승호 양이온성 계면활성제 및 그 제조방법
KR102377574B1 (ko) * 2017-12-12 2022-03-23 주식회사 비제이바이오켐 양이온 계면활성제 및 이를 포함하는 퍼스널케어 조성물

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5916863A (en) 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
AU2003296735A1 (en) * 2003-01-02 2004-07-29 Akzo Nobel N.V. Minimization of volatile organic sulphur byproducts in dimethyl sulfate quaternization of amines made with hypophorous acid
KR20050108004A (ko) * 2004-05-11 2005-11-16 주식회사 엘지생활건강 섬유유연제 조성물
KR100676267B1 (ko) 2006-01-13 2007-01-30 주식회사 엘지생활건강 양이온 계면활성제의 제조방법

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN119707664A (zh) * 2024-12-24 2025-03-28 安徽虹泰新材料股份有限公司 一种低色泽、低铁含量、低磷含量的二聚酸的制备方法

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WO2011099810A3 (fr) 2011-12-15
KR100992595B1 (ko) 2010-11-08

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