(WO2019232180) Cationic surfactants comprising an ether link 机翻标题: 暂无翻译,请尝试点击翻译按钮。

源语言标题
(WO2019232180) Cationic surfactants comprising an ether link
公开号/公开日
WO2019/232180 / 2019-12-05
申请号/申请日
WOUS2019/034604 / 2019-05-30
发明人
LALGUDI, Ramanathan S.CAIN, Robert J.VALLURI, Manoj Kumar;
申请人
BATTELLE MEMORIAL INSTITUTE;
主分类号
IPC分类号
C07C-041/03 C07C-213/06 C07C-217/00 C09K-008/035 C09K-008/584 C11D-001/42 C11D-001/60 C11D-001/62
摘要
(WO2019/232180) A cationic surfactant and a method of making the cationic surfactant are described. The method comprises reacting a lipophilic bio-based material having at least one epoxy functional group and a hydrophilic organic compound having at least one cationic functional group and at least one hydroxyl functional group to form a reaction product containing a stable ether linkage connecting the lipophilic bio-based material to the organic compound. At least a portion of the cationic functional groups is neutralized or ion exchanged with an organic acid. Incorporation of the simple organic acid reduces the surfactant's aquatic toxicity and acts as a substrate to encourage co-digestion of the surfactant molecule, making the compound more biodegradable.
机翻摘要
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地址
代理人
(WO2019232180) PRIOR, Patricia L. ([US])
代理机构
;
优先权号
2018US-62677965
主权利要求
(WO2019/232180) What is claimed is: 1. A method of making a cationic surfactant comprising:   reacting a lipophilic bio-based material having at least one epoxy functional group with a hydrophilic organic compound having at least one cationic functional group and at least one hydroxyl functional group to form a reaction product containing an ether linkage connecting the lipophilic bio-based material to the organic compound. 2. The method of claim 1 further comprising:   neutralizing the cationic functional group in the reaction product ; or ion exchanging the counter ion in the cationic functional group. 3. The method of any one of claims 1-2 wherein the lipophilic bio-based material having at least one epoxy functional group comprises epoxidized soybean oil, epoxidized canola oil, epoxidized linseed oil, epoxidized high oleic soybean oil, epoxidized olive oil, epoxidized peanut oil, epoxidized palm oil, epoxidized hemp oil, epoxidized algal oil, epoxidized marine oils epoxidized microorganism oils, vemonia oil, epoxidized methyl soyate, epoxidized methyl oleate, epoxidized methyl linolinate, epoxidized methyl linoleate, vernolic acid, or combinations thereof. 4. The method of any one of claims 1-3 wherein the organic compound comprises an amine, a phosphine, a guanidine derivative, or an onium compound. 5. The method of claim 4 wherein the organic compound is the amine and wherein the amine comprises 2,4,6-Tris dimethylaminomethyl phenol, 2-Dimethylaminoethanol, N-Methyldiethanolamine, 3 -Dimethylamino-l -propanol, 3 -(Dimethylamino)-l, 2-propanediol, 2- (Diethylamino)ethanol, 2-Dimethylamino-2-methylpropanol, 4-(Dimethylamino)-l -butanol, N- Ethyldiethanolamine, Triethanolamine, 3 -Diethylamino-l -propanol, 2-{ [2- (Dimethylamino)ethyl]methylamino}ethanol, 4-Diethylamino-2-butyn-l-ol, Tropine, 2- (Diisopropylamino)ethanol, 2-(Methylphenylamino)ethanol, 3-(Dimethylamino)benzyl alcohol, N-Phenyl diethanolamine, 2-(N-Ethyl-N-m-toluidino)ethanol, 2,2 '-(4- Methylphenylimino)diethanol, 3-(Dibenzylamino)-l-propanol, or combinations thereof. 6. The method of claim 4 wherein the organic compound is the phosphine and wherein the phosphine comprises (4-hydroxyphenyl)diphenylphosphine,   tris(hydroxymethyl)phosphine. 7. The method of claim 4 wherein the organic compound is the guanidine derivative. 8. The method of claim 4 wherein the organic compound is the onium compound and wherein the onium compound comprises an ammonium compound, an ox onium compound, a fluoronium compound, a phosphonium compound, a sulfonium compound, a chloronium compound, an arsonium compound, a selenonium compound, a boronium   compound, a stilbonium compound, a telluronium compound, an iodonium compound, or bismuthonium compound, or combinations thereof. 9. The method of any one of claims 1-8 wherein the reaction takes place in the presence of a catalyst. 10. The method of any one of claims 1-9 wherein the reaction takes place in the presence of a solvent. 11. The method of any one of claims 1-10 wherein the cationic functional group is neutralized using carbon dioxide or a carboxylic acid or the cationic functional group is ion exchanged with a carboxylic acid. 12. The method of any one of claims 1-11 wherein the cationic functional group is neutralized using a carboxylic acid comprising acetic acid, formic acid, proprionic acid, butyric acid, malic acid, lactic acid, citric acid, or combinations thereof; or wherein the cationic functional group is ion exchanged using a carboxylic acid comprising acetic acid, formic acid, proprionic acid, butyric acid, malic acid, lactic acid, citric acid, or combinations thereof. 13. The method of any one of claims 1-12 wherein at least 70 mol% of the cationic functional groups are neutralized or ion exchanged. 14. The method of any one of claims 1-13 wherein the cationic functional group is neutralized and wherein a hydrophilic to lipophilic balance is in a range of 4 to 40. 15. A cationic surfactant comprising:   a reaction product of a lipophilic bio-based material having at least one epoxy functional group and a hydrophilic organic compound having at least one cationic functional group and at least one hydroxyl functional group, wherein the lipophilic bio-based material is connected to the organic compound by an ether linkage. 16. The cationic surfactant of claim 15 wherein at least a portion of the cationic functional groups are neutralized or ion exchanged. 17. The cationic surfactant of any one of claims 15-16 wherein the lipophilic bio-based material having at least one epoxy functional group comprises epoxidized soybean oil, epoxidized canola oil, epoxidized linseed oil, epoxidized high oleic soybean oil, epoxidized olive oil, epoxidized peanut oil, epoxidized palm oil, epoxidized hemp oil, epoxidized algal oil, epoxidized marine oils epoxidized microorganism oils, vemonia oil, epoxidized methyl soyate, epoxidized methyl oleate, epoxidized methyl linolinate, epoxidized methyl linoleate, vernolic acid or combinations thereof, and wherein the organic compound comprises an amine, a phosphine, a guanidine derivative, or an onium compound. 18. The cationic surfactant of any one of claims 15-17 wherein the cationic functional groups are neutralized with a carboxylic acid comprising acetic acid, formic acid, proprionic acid, butyric acid, malic acid, lactic acid, citric acid, or combinations thereof; or wherein the cationic functional group is ion exchanged using a carboxylic acid comprising acetic acid, formic acid, proprionic acid, butyric acid, malic acid, lactic acid, citric acid, or   combinations thereof. 19. The cationic surfactant of any one of claims 15-18 wherein at least 70% of the cationic functional groups are neutralized or ion exchanged. 20. The cationic surfactant of any one of claims 15-19 wherein the cationic functional groups are neutralized and wherein a hydrophilic to lipophilic balance is in a range of 4 to 40.
法律状态
PENDING
专利类型码
A1
国别省市代码
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