JP5992605B2 - 織物柔軟剤活性組成物およびその製造方法 - Google Patents
織物柔軟剤活性組成物およびその製造方法 Download PDFInfo
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- JP5992605B2 JP5992605B2 JP2015510712A JP2015510712A JP5992605B2 JP 5992605 B2 JP5992605 B2 JP 5992605B2 JP 2015510712 A JP2015510712 A JP 2015510712A JP 2015510712 A JP2015510712 A JP 2015510712A JP 5992605 B2 JP5992605 B2 JP 5992605B2
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- fatty acid
- hydroxyethyl
- tris
- acid ester
- amine
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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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
-
- 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
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2003—Alcohols; Phenols
- C11D3/2006—Monohydric alcohols
- C11D3/201—Monohydric alcohols linear
-
- 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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
a)少なくとも1種のトリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート脂肪酸エステル65〜98質量%、
b)前記組成物の全アミン価7〜20mgKOH/gを提供する量の少なくとも1種のトリス(2−ヒドロキシエチル)アミン脂肪酸エステル、および
c)メタノール1〜1500ppm
を含む前記組成物を対象とする。
例1:
市販のトリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート獣脂脂肪酸エステルのメタノール含有量
第1表は、ヘッドスペースGCにより測定された、市販のトリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート獣脂脂肪酸エステルのメタノール含有量を示している。
トリス(2−ヒドロキシエチル)アミン獣脂脂肪酸エステルの製造
ヨウ素価38およびトリエタノールアミン1115g(7.47モル)を有する獣脂脂肪酸3513g(12.82モル)の混合物を、撹拌しながら190℃に加熱して、この反応混合物から水を蒸留した。この温度で2時間後、圧力を段階的に20mbarに下げ、前記混合物を190℃および20mbarでさらに3時間撹拌した。その後、前記反応混合物を60℃に冷却した。生じたトリス(2−ヒドロキシエチル)アミン獣脂脂肪酸エステルは、酸価3.6mgKOH/g、および全アミン価95.2mgKOH/gを有していた。
例3:
ジメチルスルフェート167.7g(1.33モル)を、少量ずつ撹拌しながら、例2のトリス(2−ヒドロキシエチル)アミン獣脂脂肪酸エステル818g(1.387モル)に加え、反応混合物を冷却して70〜90℃の範囲の温度を保った。すべてのジメチルスルフェートを添加した後、前記反応混合物を1時間80〜90℃で撹拌した。その後、2−プロパノール109.5gを加えて、前記混合物を均一になるまで撹拌した。生じた組成物は、全アミン価3.4mgKOH/gを有しており、この組成物の質量に対してメタノール4450ppmを含んでいた。
例3を、ジメチルスルフェート160.44g(1.272モル)、例2のトリス(2−ヒドロキシエチル)アミン獣脂脂肪酸エステル808.8g(1.369モル)、および2ープロパノール107.47gを使用して繰り返した。生じた組成物は、全アミン価6.0mgKOH/gを有しており、この組成物の質量に対して、メタノール3000ppmを含んでいた。
例3を、ジメチルスルフェート144.55g(1.146モル)、例2のトリス(2−ヒドロキシエチル)アミン獣脂脂肪酸エステル755.4g(1.282モル)、および2−プロパノール100.0gを使用して繰り返した。生じた組成物は、全アミン価8.9mgKOH/gを有しており、この組成物の質量に対してメタノール1400ppmを含んでいた。
例3を、ジメチルスルフェート135.1g(1.072モル)、例2のトリス(2−ヒドロキシエチル)アミン獣脂脂肪酸エステル780.1g(1.324モル)、および2−プロパノール102.0gを使用して繰り返した。生じた組成物は、全アミン価17.2mgKOH/gを有しており、この組成物の質量に対してメタノール155ppmを含んでいた。
特許US6,995,131の第43欄37〜53行に記載の、部分的に水素化されたキャノーラ脂肪酸に由来するアシル基を有するジ(アシルオキシエチル)(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェートの製造を繰り返した。生じた組成物は、この組成物の質量に対してメタノール5500ppmを含んでいた。
Claims (14)
- 織物柔軟剤活性組成物であって、
a)少なくとも1種のトリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート脂肪酸エステル65〜98質量%、
b)前記組成物の全アミン価7〜20mgKOH/gを提供する量の少なくとも1種のトリス(2−ヒドロキシエチル)アミン脂肪酸エステル、および
c)メタノール1〜1500ppm
を含む前記組成物。 - メタノール10〜800ppmを含む、請求項1に記載の織物柔軟剤活性組成物。
- 前記トリス(2−ヒドロキシエチル)アミン脂肪酸エステルを、前記組成物の全アミン価8〜13mgKOH/gを提供する量で含む、請求項1または2に記載の織物柔軟剤活性組成物。
- 前記トリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート脂肪酸エステルおよび前記トリス(2−ヒドロキシエチル)アミン脂肪酸エステルが、同一の脂肪酸部分を有している、請求項1から3までのいずれか1項に記載の織物柔軟剤活性組成物。
- 前記トリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート脂肪酸エステルが、脂肪酸部分の窒素に対する平均モル比1.4〜2.0を有している、請求項1から4までのいずれか1項に記載の織物柔軟剤活性組成物。
- 前記トリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート脂肪酸エステルの脂肪酸部分に相当する前記脂肪酸が、0.5〜120のヨウ素価を有している、請求項1から5までのいずれか1項に記載の織物柔軟剤活性組成物。
- 前記トリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート脂肪酸エステルの脂肪酸部分が、16〜18個の炭素原子の平均鎖長を有している、請求項1から6までのいずれか1項に記載の織物柔軟剤活性組成物。
- 前記トリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート脂肪酸エステルが、ポリ不飽和脂肪酸部分10モル%未満を含んでいる、請求項1から7までのいずれか1項に記載の織物柔軟剤活性組成物。
- エタノール、1−プロパノール、2−プロパノール、エチレングリコール、ジエチレングリコール、プロピレングリコール、ジプロピレングリコール、エチレングリコールのC1〜C4アルキルモノエーテル、およびプロピレングリコールのC1〜C4アルキルモノエーテルから選択される溶媒を35質量%までさらに含む、請求項1から8までのいずれか1項に記載の織物柔軟剤活性組成物。
- トリス(2−ヒドロキシエチル)メチルアンモニウムメチルスルフェート脂肪酸エステル65〜98質量%、およびメタノール1〜1500ppmを含む織物柔軟剤活性組成物の製造方法であって、少なくとも1種のトリス(2−ヒドロキシエチル)アミン脂肪酸エステルを、反応混合物が全アミン価7〜20mgKOH/gを有するまで、ジメチルスルフェートのアミン窒素に対するモル比0.79〜0.94でジメチルスルフェートと反応させる前記方法。
- 前記トリス(2−ヒドロキシエチル)アミン脂肪酸エステルを、ジメチルスルフェートと60〜95℃の温度で反応させる、請求項10に記載の方法。
- 前記トリス(2−ヒドロキシエチル)アミン脂肪酸エステルが、脂肪酸部分の窒素に対する平均モル比1.4〜2.0を有する、請求項10または11に記載の方法。
- 前記トリス(2−ヒドロキシエチル)アミン脂肪酸エステルの脂肪酸部分が、0.5〜120のヨウ素価を有している、請求項10から12までのいずれか1項に記載の方法。
- 前記トリス(2−ヒドロキシエチル)アミン脂肪酸エステルの脂肪酸部分が、16〜18個の炭素原子の平均鎖長を有している、請求項10から13までのいずれか1項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12166976.6 | 2012-05-07 | ||
EP12166976 | 2012-05-07 | ||
PCT/EP2013/058427 WO2013167376A1 (en) | 2012-05-07 | 2013-04-24 | Fabric softener active composition and method for making it |
Publications (2)
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JP2015517610A JP2015517610A (ja) | 2015-06-22 |
JP5992605B2 true JP5992605B2 (ja) | 2016-09-14 |
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JP2015510712A Active JP5992605B2 (ja) | 2012-05-07 | 2013-04-24 | 織物柔軟剤活性組成物およびその製造方法 |
Country Status (11)
Country | Link |
---|---|
US (1) | US9441187B2 (ja) |
EP (1) | EP2847307B1 (ja) |
JP (1) | JP5992605B2 (ja) |
KR (1) | KR101694599B1 (ja) |
CN (1) | CN104471044B (ja) |
BR (1) | BR112014027174B1 (ja) |
DK (1) | DK2847307T3 (ja) |
ES (1) | ES2580031T3 (ja) |
MX (1) | MX366465B (ja) |
PL (1) | PL2847307T3 (ja) |
WO (1) | WO2013167376A1 (ja) |
Cited By (1)
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JP2015089889A (ja) * | 2013-11-05 | 2015-05-11 | エボニック インダストリーズ アクチエンゲゼルシャフトEvonik Industries AG | トリス−(2−ヒドロキシエチル)−メチルアンモニウムメチルスルファート脂肪酸エステルの製造方法 |
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JP6482829B2 (ja) * | 2014-11-18 | 2019-03-13 | 花王株式会社 | カチオン性界面活性剤の製造方法 |
EP3420062B1 (en) | 2016-02-26 | 2020-05-27 | Evonik Operations GmbH | Amides of aliphatic polyamines and 12-hydroxyoctadecanoic acid and lipase stable thickener compositions |
RU2740475C2 (ru) | 2016-12-06 | 2021-01-14 | Эвоник Корпорейшн | Органофильные глины и буровые растворы, содержащие их |
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CN111051485A (zh) | 2017-09-06 | 2020-04-21 | 赢创运营有限公司 | 特别用于生产织物柔软剂配制物的包含季铵化合物的微乳剂 |
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JP2015089889A (ja) * | 2013-11-05 | 2015-05-11 | エボニック インダストリーズ アクチエンゲゼルシャフトEvonik Industries AG | トリス−(2−ヒドロキシエチル)−メチルアンモニウムメチルスルファート脂肪酸エステルの製造方法 |
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MX2014013397A (es) | 2015-01-19 |
KR101694599B1 (ko) | 2017-01-09 |
CN104471044B (zh) | 2017-07-25 |
BR112014027174B1 (pt) | 2021-04-06 |
ES2580031T3 (es) | 2016-08-18 |
EP2847307B1 (en) | 2016-04-06 |
WO2013167376A1 (en) | 2013-11-14 |
DK2847307T3 (en) | 2016-07-25 |
EP2847307A1 (en) | 2015-03-18 |
BR112014027174A2 (pt) | 2017-06-27 |
PL2847307T3 (pl) | 2016-10-31 |
MX366465B (es) | 2019-07-10 |
JP2015517610A (ja) | 2015-06-22 |
KR20150013490A (ko) | 2015-02-05 |
US20150080286A1 (en) | 2015-03-19 |
CN104471044A (zh) | 2015-03-25 |
US9441187B2 (en) | 2016-09-13 |
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