CN102803456A - 织物柔软剂活性组合物 - Google Patents

织物柔软剂活性组合物 Download PDF

Info

Publication number
CN102803456A
CN102803456A CN2011800144943A CN201180014494A CN102803456A CN 102803456 A CN102803456 A CN 102803456A CN 2011800144943 A CN2011800144943 A CN 2011800144943A CN 201180014494 A CN201180014494 A CN 201180014494A CN 102803456 A CN102803456 A CN 102803456A
Authority
CN
China
Prior art keywords
alcohol
fatty acid
weight
mixture
hydroxyethyl
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
CN2011800144943A
Other languages
English (en)
Other versions
CN102803456B (zh
Inventor
H-J·克勒
M·舍普纳
A·奥伊勒
H·雅各布
S·J·梅莱达图
T·L·库尔思
D·G·扬
I·哈曼
G·希克
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.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa GmbH
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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of CN102803456A publication Critical patent/CN102803456A/zh
Application granted granted Critical
Publication of CN102803456B publication Critical patent/CN102803456B/zh
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2003Alcohols; Phenols
    • C11D3/2006Monohydric alcohols
    • C11D3/201Monohydric alcohols linear
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/20Organic compounds containing oxygen
    • C11D3/2093Esters; Carbonates

Landscapes

  • 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)

Abstract

织物柔软剂活性组合物,其包含65-95重量%的双-(2-羟乙基)-二甲基氯化铵脂肪酸酯、2-8重量%的脂肪酸甘油三酯以及3-12重量%的醇,所述双-(2-羟乙基)-二甲基氯化铵脂肪酸酯的脂肪酸部分对胺部分的摩尔比为1.80-1.96,脂肪酸部分的平均链长为16-18个碳分子并且碘值为0-50,所述脂肪酸甘油三酯的脂肪酸部分的平均链长为10-14个碳原子且碘值为0-15,所述醇选自乙醇、1-丙醇和2-丙醇,所述组合物具有低的熔融粘度、在熔融状态对脱烷基作用的高稳定性和低可燃性。

Description

织物柔软剂活性组合物
本发明涉及织物柔软剂活性组合物,其具有低含量的可燃溶剂、低熔融粘度以及在熔融状态下的高稳定性。
已发现带有两个疏水性长链烃部分的季铵盐广泛用作织物柔软剂活性物。平均每分子用两个脂肪酸部分酯化的烷醇胺的季铵盐(通常称为季铵酯)因为其生物可降解性已很大程度上替代了早期的烷基季铵化合物。
已经商业使用的双-(2-羟乙基)二甲基氯化铵脂肪酸二酯难以以纯的状态操作,因为固态容易结块,而熔体在低的熔融温度具有高粘度,在较高的熔融温度具有不能令人满意的稳定性。因此,双-(2-羟乙基)二甲基氯化铵脂肪酸二酯通常作为熔融组合物运输,所述组合物含有13重量%的乙醇或2-丙醇,其在65至75°C的温度下的粘度足够低,可以用于泵送。然而,这样的组合物具有低于30°C的低闪点,因此受到管制并需要额外的安全操作措施。
WO 2007/026314提出用2-40重量%的选自烷基酯或聚酯、烷基酰胺或聚酰胺、脂肪酸、非离子表面活性剂或它们的组合的稀释剂来取代这样的组合物中的可燃溶剂,并具体公开了氢化牛油脂肪、氢化牛油脂肪酸、氢化椰子油、氢化棕榈硬脂、氢化大豆油、乙二醇二硬酸脂酸硬大豆蔗糖酯(ethylene glycol distearate hard soy sucrose ester)、十六酸十六酯和季戊四醇四辛酸酯/四癸酸酯作为合适的稀释剂。WO 2007/026314还提出以0.1-15重量%的量使用额外的偶联剂,所述偶联剂选自多元醇、多元醇非离子表面活性剂的部分酯。然而,WO 2007/026314教导的组合物具有季铵盐脱烷基方面的在熔融状态稳定性低的缺点,导致在以熔融状态运输和操作期间游离酯胺含量的增加。
因此,仍然需要这样的织物柔软剂活性组合物,其具有低的熔融粘度和在熔融状态的高稳定性以及同时具有低可燃性。
已发现基于以下这样的双-(2-羟乙基)二甲基氯化铵脂肪酸酯的织物柔软剂活性组合物显示出人意料的低熔融粘度、在熔融状态对脱烷基作用的高稳定性和低可燃性的组合,所述双-(2-羟乙基)二甲基氯化铵脂肪酸酯由具有特定链长和特定不饱和程度的脂肪酸制得,并具有特定的脂肪酸部分对胺部分的摩尔比,所述组合物包含特定量的脂肪酸部分具有特定的较低链长的脂肪酸甘油三酯,以及特定量的选自乙醇、1-丙醇和2-丙醇的醇。
因此,本发明涉及织物柔软剂活性组合物,其包括:
a)65-95重量%的双-(2-羟乙基)二甲基氯化铵脂肪酸酯,其脂肪酸部分对胺部分的摩尔比为1.80-1.96,所述脂肪酸部分的平均链长为16-18个碳原子并且以游离脂肪酸计算的碘值为0-50;
b)2-8重量%的脂肪酸甘油三酯,其脂肪酸部分的平均链长为10-14个碳原子并且以游离脂肪酸计算的碘值为0-15;和
c)3-12重量%的醇,所述醇选自乙醇、1-丙醇和2-丙醇。
本发明还涉及制备这样的组合物的方法,其包括以下步骤:
a)使包含78-95重量%的双-(2-羟乙基)-甲胺脂肪酸酯、2-9重量%的脂肪酸甘油三酯以及3-13重量%的醇的混合物与过量的氯甲烷在60-120°C的温度下反应以提供反应混合物,所述双-(2-羟乙基)-甲胺脂肪酸酯的脂肪酸部分对胺部分的摩尔比为1.80-1.96,脂肪酸部分的平均链长为16-18个碳分子并且以游离脂肪酸计算的碘值为0-50,所述脂肪酸甘油三酯的脂肪酸部分的平均链长为10-14个碳原子且以游离脂肪酸计算的碘值为0-15,所述醇选自乙醇、1-丙醇和2-丙醇;和
b)通过蒸馏出氯甲烷和所述醇的混合物从步骤a)的反应混合物分离未反应的氯甲烷,从所述氯甲烷和醇的混合物冷凝醇,并将所冷凝的醇返回所述反应混合物以提供3-12重量%的醇含量。
本发明还涉及制备这样的组合物的可选方法,其包括以下步骤:
a)使包含88-98重量%的双-(2-羟乙基)-甲胺脂肪酸酯、2-9重量%的脂肪酸甘油三酯以及0-3重量%的醇的混合物与过量的氯甲烷在60-120°C的温度下反应以提供反应混合物,所述双-(2-羟乙基)-甲胺脂肪酸酯的脂肪酸部分对胺部分的摩尔比为1.80-1.96,脂肪酸部分的平均链长为16-18个碳分子并且以游离脂肪酸计算的碘值为0-50,所述脂肪酸甘油三酯的脂肪酸部分的平均链长为10-14个碳原子且以游离脂肪酸计算的碘值为0-15,所述醇选自乙醇、1-丙醇和2-丙醇;和
b)向步骤a)的反应混合物中加入更多的所述醇以提供3-12重量%的醇含量;和
c)通过蒸馏出氯甲烷和所述醇的混合物从步骤b)的混合物分离未反应的氯甲烷,从所述氯甲烷和醇的混合物冷凝醇,并将所冷凝的醇返回所述反应混合物以提供3-12重量%的醇含量。
本发明的织物柔软剂活性组合物包括65-95重量%的双-(2-羟乙基)二甲基氯化铵脂肪酸酯。所述组合物优选地包括80-90重量%的所述酯。
所述双-(2-羟乙基)二甲基氯化铵脂肪酸酯包括至少一种式(CH3)2N+(CH2CH2OC(=O)R)2Cl-的二酯和至少一种式(CH3)2N+(CH2CH2OH)(CH2CH2OC(=O)R)Cl-的单酯,其中R是脂肪酸部分RCOO的烃基。所述双-(2-羟乙基)二甲基氯化铵脂肪酸酯的脂肪酸部分对胺部分的摩尔比为1.80-1.96,优选为1.85-1.94。所述特定的摩尔比在漂洗循环织物柔软剂中提供了高软化性能。
所述双-(2-羟乙基)二甲基氯化铵脂肪酸酯的脂肪酸部分可以来源于纯脂肪酸或式RCOOH的脂肪酸的混合物,其中R是烃基。所述烃基可以是带支链的或不带支链的,优选是不带支链的。
所述脂肪酸部分具有16-18个碳原子的平均链长以及0-50的以游离脂肪酸计算的碘值。所述平均链长优选为16.5-17.8个碳原子。优选地,脂肪酸部分具有1.0-50,更优选地2-50,更优选地5-40和最优选地15-35的碘值。在所述脂肪酸的混合物中,在各脂肪酸的重量比例的基础上计算所述平均链长。对于支链脂肪酸,链长是指最长的连续的碳原子链。碘值是由ISO 3961的方法确定的100g脂肪酸双键反应所消耗的碘的克数。为了提供所需的平均链长和碘值,脂肪酸部分可以衍生自包含饱和脂肪酸和不饱和脂肪酸的脂肪酸混合物。所述不饱和脂肪酸优选地是单不饱和脂肪酸。所述双-(2-羟乙基)二甲基氯化铵脂肪酸酯优选地包含小于6重量%的多不饱和脂肪酸部分。适合的饱和脂肪酸的实例是棕榈酸和硬脂酸。适合的单不饱和脂肪酸的实例是油酸和反油酸。不饱和脂肪酸部分的双键的顺式-反式比优选地高于55:45,并更优选地高于65:35。通过选择性接触氢化可以减少多不饱和脂肪酸部分的比例,其中所述氢化选择性地氢化-CH=CH-CH2-CH=CH-亚结构中的一个双键,但不氢化单不饱和烃基的双键。对于同时实现所述组合物的高软化性能和低熔点,特定的平均链长和碘值是必要的。如果平均链长小于16个碳原子或碘值高于50,软化性能会不符合要求,然而如果平均链长超过18个碳原子,所述组合物的熔点可能过高。
脂肪酸部分可以衍生自天然或合成来源的脂肪酸,优选地衍生自天然来源的脂肪酸,最优选地衍生自牛油脂肪酸。通过使用已有这种碘值的天然来源的脂肪酸混合物(例如牛油脂肪酸)可以提供所需的碘值。可选地,通过部分氢化具有较高碘值的脂肪酸混合物或甘油三酯混合物可以提供所需的碘值。在另外的优选的实施方案中,通过混合具有较高碘值的脂肪酸混合物和饱和脂肪酸混合物提供所需的碘值。可以通过氢化含有不饱和脂肪酸的脂肪酸混合物或从氢化的甘油三酯混合物(如氢化植物油)获得饱和脂肪酸的混合物。
本发明的织物柔软剂活性组合物还包括2-8重量%,优选3-6重量%的脂肪酸甘油三酯,所述脂肪酸甘油三酯具有平均链长为10-14个碳原子的脂肪酸部分和以游离脂肪酸计算的0-15的碘值。所述脂肪酸部分的平均链长优选为12-13.8个碳原子。所述脂肪酸甘油三酯优选是椰子油或氢化椰子油,最优选是精制椰子油。特定的脂肪酸甘油三酯的量和脂肪酸部分的平均链长对于同时实现所述织物柔软剂活性组合物的低熔点和低可燃性是必要的。出人意料地,所述特定量的脂肪酸甘油三酯还改善了由本发明的织物柔软剂活性组合物制备的漂洗循环柔软剂的软化效率。
本发明的织物柔软剂活性组合物还包含3-12重量%,优选6-10重量%的醇,所述醇选自乙醇、1-丙醇和2-丙醇。所述醇优选是乙醇或2-丙醇,最优选是2-丙醇。对于同时实现所述织物柔软剂活性组合物的低可燃性以及所述组合物在熔融状态对双-(2-羟乙基)二甲基氯化铵脂肪酸酯的脱烷基作用的高稳定性,所述特定量的醇是必要的。能够通过特定量的醇实现的稳定性的改善看起来是针对氯盐的,在现有技术中没有认识到这一点。
脂肪酸甘油三酯和醇的组合量优选是10-15重量%。
本发明的织物柔软剂活性组合物显示在熔融状态对脱烷基作用的高稳定性、低熔融粘度和低可燃性的组合。包含86重量%的双-(2-羟乙基)二甲基氯化铵牛油脂肪酸酯、3重量%的椰子油和9重量%的2-丙醇的织物柔软剂组合物具有根据DIN 53213测定的38℃的闪点。
本发明的织物柔软剂活性组合物可以通过以特定的量混合双-(2-羟乙基)二甲基氯化铵脂肪酸酯、脂肪酸甘油三酯和醇来制备。然而,所述织物柔软剂活性组合物优选地通过本发明两种方法之一制备,所述两种方法共同的地方是在脂肪酸甘油三酯存在下,用过量氯甲烷使双-(2-羟乙基)甲胺脂肪酸酯季铵化,随后在醇的存在下分离过量的氯甲烷。
本发明的第一种方法包括两个步骤。
在第一步骤中,包含78-95重量%的双-(2-羟乙基)甲胺脂肪酸酯、2-9重量%的脂肪酸甘油三酯以及3-13重量%的醇(选自乙醇、1-丙醇、2-丙醇)的混合物和过量的氯甲烷在60-120℃、优选90-110℃的温度下反应。所述氯甲烷的摩尔量大于所述双-(2-羟乙基)甲胺脂肪酸酯的摩尔量,并且氯甲烷对双-(2-羟乙基)甲胺脂肪酸酯的摩尔比优选是1.1-1.5。所述双-(2-羟乙基)甲胺脂肪酸酯的脂肪酸部分对胺部分的摩尔比为1.80-1.96,优选1.82-1.92,所述脂肪酸部分的平均链长为16-18个碳原子,优选16.5-17.8个碳原子,并且以游离脂肪酸计算的碘值为0-50,优选1.0-50,更优选2-50,甚至更优选5-40,并且最优选15-35。所述脂肪酸甘油三酯的脂肪酸部分的平均链长为10-14个碳原子,优选12-13.8个碳原子,以游离脂肪酸计算的碘值为0-15,并且所述脂肪酸甘油三酯优选是椰子油或氢化椰子油。所述反应优选在压力容器中以1-10bar,优选3-8bar的总压力进行。优选地以避免压力增加超过特定上限的速率将氯甲烷加入至双-(2-羟乙基)甲胺脂肪酸酯、脂肪酸甘油三酯和醇的混合物中。优选地进行所述反应直到超过80%,优选超过85%的双-(2-羟乙基)甲胺脂肪酸酯已经反应。合适的反应时间在2-8h的范围内,取决于反应温度和压力。
在第二步骤中,通过蒸馏出氯甲烷和所述醇的混合物从步骤a)的反应混合物分离未反应的氯甲烷,从所述氯甲烷和醇的混合物冷凝醇,并将所冷凝的醇返回所述反应混合物以提供3-12重量%的醇含量。优选地在0.2-1bar的总压力下蒸馏出所述氯甲烷和醇的混合物。优选地在部分冷凝器(partial condenser)中,在氯甲烷和所述醇的沸点之间的温度下,在用于蒸馏的压力下从所述氯甲烷和醇的混合物中冷凝所述醇。可以将全部或部分的所冷凝的醇返回至反应混合物,取决于获得的混合物所需要的醇含量。
本发明的第二种方法包括三个步骤,其与本发明第一种方法的不同在于第一步骤中起始混合物包含88-98重量%的双-(2-羟乙基)甲胺脂肪酸酯和0-3重量%的所述醇,以及在进行将未反应的氯甲烷从所述混合物分离的步骤之前,在额外的步骤中向第一步骤的反应混合物添加更多的醇以提供3-12重量%的醇含量。
本发明的两种方法具有在短的反应时间内提供具有低含量的非季铵化双-(2-羟乙基)甲胺脂肪酸酯的织物柔软剂活性组合物的优点。本发明的第二种方法具有额外的优势,来自醇烷基化的副产物的形成低并且烷基化反应时间进一步减少。
本发明通过以下实施例进行阐述,然而并不旨在通过任何方式限制本发明的范围。
实施例
通过以表1给出的量混合粉末状季铵盐和溶剂并熔融混合物,从椰子油、2-丙醇和双-(2-羟乙基)二甲基氯化铵牛油脂肪酸酯制备织物柔软剂活性组合物,所述双-(2-羟乙基)二甲基氯化铵牛油脂肪酸酯以游离脂肪酸计算的碘值为20,脂肪酸部分对胺部分的摩尔比是1.89,并含有0.044mmol/g双-(2-羟乙基)甲基胺脂肪酸酯、0.041mmol/g双-(2-羟乙基)甲基氯化铵脂肪酸酯和0.111mmol/g脂肪酸。
对在封闭玻璃瓶中100℃储存5天的所述织物柔软剂活性组合物测定储存稳定性。
在90℃下通过使用50mm平行板的
Figure BDA00002153148700061
仪器的StressTech流变仪来测定熔融粘度,其板间距离为1mm,剪切速率为1s-1、10s-1和100s-1
表1织物柔软剂活性组合物的特性
Figure BDA00002153148700062
*不根据本发明

Claims (8)

1.织物柔软剂活性组合物,其包含
a)65-95重量%的双-(2-羟乙基)二甲基氯化铵脂肪酸酯,其脂肪酸部分对胺部分的摩尔比为1.80-1.96,所述脂肪酸部分的平均链长为16-18个碳原子并且以游离脂肪酸计算的碘值为0-50;
b)2-8重量%的脂肪酸甘油三酯,其脂肪酸部分的平均链长为10-14个碳原子并且以游离脂肪酸计算的碘值为0-15;和
c)3-12重量%的醇,所述醇选自乙醇、1-丙醇和2-丙醇。
2.根据权利要求1所述的织物柔软剂活性组合物,其包含3-6重量%的所述脂肪酸甘油三酯和6-10重量%的所述醇。
3.根据权利要求1或2所述的织物柔软剂活性组合物,其中所述脂肪酸甘油三酯和所述醇的组合量是10-15重量%。
4.根据权利要求1-3中任一项所述的织物柔软剂活性组合物,其中所述脂肪酸甘油三酯是椰子油或氢化椰子油。
5.根据权利要求1-4中任一项所述的织物柔软剂活性组合物,其中所述双-(2-羟乙基)二甲基氯化铵脂肪酸酯的脂肪酸部分的以游离脂肪酸计算的碘值为15-35。
6.制备权利要求1所述的织物柔软剂活性组合物的方法,其包括以下步骤:
a)使包含78-95重量%的双-(2-羟乙基)-甲胺脂肪酸酯、2-9重量%的脂肪酸甘油三酯以及3-13重量%的醇的混合物与过量的氯甲烷在60-120°C的温度下反应以提供反应混合物,所述双-(2-羟乙基)-甲胺脂肪酸酯的脂肪酸部分对胺部分的摩尔比为1.80-1.96,脂肪酸部分的平均链长为16-18个碳分子并且以游离脂肪酸计算的碘值为0-50,所述脂肪酸甘油三酯的脂肪酸部分的平均链长为10-14个碳原子且以游离脂肪酸计算的碘值为0-15,所述醇选自乙醇、1-丙醇和2-丙醇;和
b)通过蒸馏出氯甲烷和所述醇的混合物从步骤a)的反应混合物分离未反应的氯甲烷,从所述氯甲烷和醇的混合物冷凝醇,并将所冷凝的醇返回所述反应混合物以提供3-12重量%的醇含量。
7.制备权利要求1的织物柔软剂活性组合物的方法,其包括以下步骤
a)使包含88-98重量%的双-(2-羟乙基)-甲胺脂肪酸酯、2-9重量%的脂肪酸甘油三酯以及0-3重量%的醇的混合物与过量的氯甲烷在60-120°C的温度下反应以提供反应混合物,所述双-(2-羟乙基)-甲胺脂肪酸酯的脂肪酸部分对胺部分的摩尔比为1.80-1.96,脂肪酸部分的平均链长为16-18个碳分子并且以游离脂肪酸计算的碘值为0-50,所述脂肪酸甘油三酯的脂肪酸部分的平均链长为10-14个碳原子且以游离脂肪酸计算的碘值为0-15,所述醇选自乙醇、1-丙醇和2-丙醇;
b)向步骤a)的反应混合物中加入更多的所述醇以提供3-12重量%的醇含量;和
c)通过蒸馏出氯甲烷和所述醇的混合物从步骤b)的混合物分离未反应的氯甲烷,从所述氯甲烷和醇的混合物冷凝醇,并将所冷凝的醇返回所述反应混合物以提供3-12重量%的醇含量。
8.根据权利要求6或7所述的方法,其中在0.2-1bar的总压力下蒸馏出所述氯甲烷和醇的混合物。
CN201180014494.3A 2010-04-01 2011-03-22 织物柔软剂活性组合物 Active CN102803456B (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US31999710P 2010-04-01 2010-04-01
US61/319,997 2010-04-01
PCT/EP2011/054282 WO2011120836A1 (en) 2010-04-01 2011-03-22 Fabric softener active composition

Publications (2)

Publication Number Publication Date
CN102803456A true CN102803456A (zh) 2012-11-28
CN102803456B CN102803456B (zh) 2014-06-11

Family

ID=43984114

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201180014494.3A Active CN102803456B (zh) 2010-04-01 2011-03-22 织物柔软剂活性组合物

Country Status (22)

Country Link
US (1) US8563499B2 (zh)
EP (1) EP2553067B1 (zh)
JP (1) JP5460919B2 (zh)
KR (1) KR101425294B1 (zh)
CN (1) CN102803456B (zh)
AP (1) AP4034A (zh)
AU (1) AU2011234658B2 (zh)
BR (1) BR112012025002B1 (zh)
CA (1) CA2795152C (zh)
DK (1) DK2553067T3 (zh)
EG (1) EG27007A (zh)
ES (1) ES2536849T3 (zh)
IL (1) IL220908A (zh)
MA (1) MA34103B1 (zh)
MX (1) MX2012011005A (zh)
MY (1) MY159502A (zh)
PL (1) PL2553067T3 (zh)
RU (1) RU2526035C1 (zh)
SG (1) SG184397A1 (zh)
UA (1) UA106790C2 (zh)
WO (1) WO2011120836A1 (zh)
ZA (1) ZA201207287B (zh)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105401436A (zh) * 2015-12-18 2016-03-16 苏州富美纺织科技有限公司 织物阻燃整理液的制备方法
CN109762665A (zh) * 2017-11-10 2019-05-17 赢创德固赛有限公司 从甘油三酯油中提取脂肪酸的方法
CN113227338A (zh) * 2018-12-11 2021-08-06 联合利华知识产权控股有限公司 织物调理剂组合物

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8361953B2 (en) 2008-02-08 2013-01-29 Evonik Goldschmidt Corporation Rinse aid compositions with improved characteristics
EP2553066B1 (en) 2010-04-01 2014-04-30 Evonik Degussa GmbH Fabric softener active composition
RU2515236C1 (ru) * 2010-04-01 2014-05-10 Дзе Проктер Энд Гэмбл Компани Мягчитель ткани
BR112012025002B1 (pt) 2010-04-01 2021-02-23 Evonik Operations Gmbh composição ativa amaciante de tecidos, e seus processos de preparação
EP2563889B1 (de) 2010-04-28 2017-03-15 Evonik Degussa GmbH Textilweichmachende zusammensetzung
US8507425B2 (en) 2010-06-29 2013-08-13 Evonik Degussa Gmbh Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making
WO2013113453A1 (en) 2012-01-30 2013-08-08 Evonik Industries Ag Fabric softener active composition
SG11201405008SA (en) 2012-02-21 2014-09-26 Stepan Co Fabric softener compositions
EP2847307B1 (en) 2012-05-07 2016-04-06 Evonik Degussa GmbH Fabric softener active composition and method for making it
CA2888966C (en) * 2012-12-11 2020-09-15 Colgate-Palmolive Company Fabric conditioning composition
BR102014025172B1 (pt) 2013-11-05 2020-03-03 Evonik Degussa Gmbh Método para fabricação de um éster de ácido graxo de metisulfato de tris-(2-hidroxietil)-metilamônio, e composição ativa de amaciante de roupa
WO2016010474A1 (en) * 2014-07-18 2016-01-21 Sophia Morgan Stain remover kit
EP2997959B1 (de) 2014-09-22 2019-12-25 Evonik Operations GmbH Formulierung enthaltend esterquats basierend auf isopropanolamin und tetrahydroxypropylethylenediamin
ES2864951T3 (es) 2014-09-22 2021-10-14 Evonik Degussa Gmbh Emulsión que contiene esterquats líquidos y espesantes poliméricos
CN106795454A (zh) * 2014-10-08 2017-05-31 宝洁公司 织物增强剂组合物
UA119182C2 (uk) 2014-10-08 2019-05-10 Евонік Дегусса Гмбх Активна композиція для пом'якшувача тканини
EP3181667A1 (en) 2015-12-18 2017-06-21 Kao Corporation, S.A. Fabric softener active compositions
WO2017144340A1 (en) 2016-02-26 2017-08-31 Evonik Degussa 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
EP3418353B1 (en) 2017-06-20 2020-08-26 Kao Corporation, S.A. Fabric softener active compositions
EP3418355B1 (en) 2017-06-20 2020-06-03 Kao Corporation, S.A. Fabric softener active compositions
PT3418354T (pt) 2017-06-20 2020-07-07 Kao Corp Sa Composições de substâncias ativas amaciadoras de tecidos
KR102145927B1 (ko) 2018-07-25 2020-08-20 주식회사 그린나노테크 전도성 고분자를 포함하는 유기계 열전 소재 및 이의 제조방법
KR102106269B1 (ko) 2018-07-25 2020-05-04 연세대학교 산학협력단 유기계 열전 소자를 포함한 발전 장치
EP3736320A1 (en) * 2019-05-08 2020-11-11 The Procter & Gamble Company Particles for through the wash laundry softening
US20210106909A1 (en) 2019-06-27 2021-04-15 Benchmark Games International, Llc Arcade game with floor controller

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2007734B (en) * 1977-10-22 1983-04-07 Cargo Fleet Chemical Co Fabric softeners
DE3402146A1 (de) * 1984-01-23 1985-07-25 Henkel KGaA, 4000 Düsseldorf Neue quartaere ammoniumverbindungen, deren herstellung und verwendung als textilweichmacher
WO1994019439A1 (en) * 1993-02-25 1994-09-01 Unilever Plc Use of fabric softening composition
EP0829531A1 (en) * 1996-08-22 1998-03-18 Unilever Plc Fabric conditioning composition
CN1284118A (zh) * 1997-11-24 2001-02-14 宝洁公司 具有增加柔软益处的低溶剂漂洗时加入的织物柔软剂
CN101248166A (zh) * 2005-08-31 2008-08-20 宝洁公司 浓缩型织物软化剂活性物质组合物
WO2009018955A2 (de) * 2007-08-06 2009-02-12 Clariant Finance (Bvi) Limited Zusammensetzungen enthaltend diethanolaminesterquats

Family Cites Families (89)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2430140C3 (de) 1974-06-24 1979-10-04 Rewo Chemische Werke Gmbh, 6497 Steinau Kationaktive Bis-(2-Acyloxypropyl)ammonium-Salze, Verfahren zu deren Herstellung und Mittel auf deren Basis
US4234627A (en) 1977-02-04 1980-11-18 The Procter & Gamble Company Fabric conditioning compositions
ZA785807B (en) * 1977-10-22 1979-09-26 Cargo Fleet Chemical Co Improvements in or relating to fabric softeners
DE2943606A1 (de) 1978-11-03 1980-05-14 Unilever Nv Textilweichmacher und verfahren zu ihrer herstellung
USRE32713E (en) 1980-03-17 1988-07-12 Capsule impregnated fabric
US4514461A (en) 1981-08-10 1985-04-30 Woo Yen Kong Fragrance impregnated fabric
CS246532B1 (cs) 1984-08-01 1986-10-16 Dagmar Mikulcova Avivážní prostředek s antistatickým a změkčujícím účinkem
US4747880A (en) 1984-12-12 1988-05-31 S. C. Johnson & Son, Inc. Dry, granular maintenance product reconstitutable to an aqueous clean and shine product
DE3608093A1 (de) 1986-03-12 1987-09-17 Henkel Kgaa Konfektioniertes textilweichmacher-konzentrat
DE3710064A1 (de) 1987-03-27 1988-10-06 Hoechst Ag Verfahren zur herstellung von quaternaeren esteraminen und ihre verwendung
DE3877422T2 (de) 1987-05-01 1993-05-13 Procter & Gamble Quaternaere isopropylesterammonium-verbindungen als faser- und gewebebehandlungsmittel.
US4789491A (en) * 1987-08-07 1988-12-06 The Procter & Gamble Company Method for preparing biodegradable fabric softening compositions
US4882220A (en) 1988-02-02 1989-11-21 Kanebo, Ltd. Fibrous structures having a durable fragrance
US5137646A (en) 1989-05-11 1992-08-11 The Procter & Gamble Company Coated perfume particles in fabric softener or antistatic agents
ES2021900A6 (es) 1989-07-17 1991-11-16 Pulcra Sa Procedimiento de obtencion de tensioactivos cationicos derivados de amonio cuaternario con funcion amino-ester.
DE3932004A1 (de) 1989-09-26 1991-04-04 Dursol Fabrik Otto Durst Gmbh Trocknungsmittel fuer lackoberflaechen
US5185088A (en) 1991-04-22 1993-02-09 The Procter & Gamble Company Granular fabric softener compositions which form aqueous emulsion concentrates
WO1994007979A1 (en) 1992-09-28 1994-04-14 The Procter & Gamble Company Method for using solid particulate fabric softener in automatic dosing dispenser
DE4243701A1 (de) 1992-12-23 1994-06-30 Henkel Kgaa Wäßrige Textilweichmacher-Dispersionen
WO1994020597A1 (en) * 1993-03-01 1994-09-15 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
US5827451A (en) 1993-03-17 1998-10-27 Witco Corporation Microemulsion useful as rinse aid
US5391325A (en) 1993-09-29 1995-02-21 Exxon Chemical Patents Inc. Non-toxic biodegradable emulsion compositions for use in automatic car washes
US5480567A (en) 1994-01-14 1996-01-02 Lever Brothers Company, Division Of Conopco, Inc. Surfactant mixtures for fabric conditioning compositions
HU221140B1 (en) * 1994-04-07 2002-08-28 Unilever Nv Fabric softening composition
DE4430721A1 (de) 1994-08-30 1996-03-07 Hoechst Ag Autoglanztrocknungsmittel
US5759990A (en) * 1996-10-21 1998-06-02 The Procter & Gamble Company Concentrated fabric softening composition with good freeze/thaw recovery and highly unsaturated fabric softener compound therefor
US5916863A (en) 1996-05-03 1999-06-29 Akzo Nobel Nv High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine
DE69725994T2 (de) 1996-09-19 2004-09-02 The Procter & Gamble Company, Cincinnati Konzentrierte quaternäre ammoniumgewebeweichmacherzusammensetzungen mit kationischen polymeren
US5874396A (en) 1997-02-28 1999-02-23 The Procter & Gamble Company Rinse added laundry additive compositions having color care agents
DE19708133C1 (de) 1997-02-28 1997-12-11 Henkel Kgaa Mittel für die Avivage von Textil- und Keratinfasern sowie die Verwendung von Hydroxycarbonsäureestern zur Herstellung von Avivagemitteln
US6645479B1 (en) 1997-09-18 2003-11-11 International Flavors & Fragrances Inc. Targeted delivery of active/bioactive and perfuming compositions
AU2105999A (en) * 1998-01-09 1999-07-26 Witco Corporation Novel quaternary ammonium compounds, compositions containing them, and uses thereof
ZA991635B (en) * 1998-03-02 1999-09-02 Procter & Gamble Concentrated, stable, translucent or clear, fabric softening compositions.
GB9810655D0 (en) * 1998-05-18 1998-07-15 Unilever Plc Stable ammonium compositions
GB9816659D0 (en) 1998-07-30 1998-09-30 Dow Europ Sa Composition useful for softening, cleaning, and personal care applications and processes for the preparation thereof
EP0990695A1 (de) 1998-09-30 2000-04-05 Witco Surfactants GmbH Weichspülmittel mit farberhaltender Wirkung
EP1018541A1 (de) 1999-01-07 2000-07-12 Goldschmidt Rewo GmbH & Co. KG Klare Weichspülmittelformulierungen
DE19906367A1 (de) 1999-02-16 2000-08-17 Clariant Gmbh Verwendung von Kammpolymeren als Schutzablösepolymere
US6916781B2 (en) * 1999-03-02 2005-07-12 The Procter & Gamble Company Concentrated, stable, translucent or clear, fabric softening compositions
US6458343B1 (en) * 1999-05-07 2002-10-01 Goldschmidt Chemical Corporation Quaternary compounds, compositions containing them, and uses thereof
US6235914B1 (en) 1999-08-24 2001-05-22 Goldschmidt Chemical Company Amine and quaternary ammonium compounds made from ketones and aldehydes, and compositions containing them
CN1377401A (zh) 1999-10-05 2002-10-30 西巴特殊化学品控股有限公司 织物柔软剂组合物
US6200949B1 (en) 1999-12-21 2001-03-13 International Flavors And Fragrances Inc. Process for forming solid phase controllably releasable fragrance-containing consumable articles
GB0002877D0 (en) * 2000-02-08 2000-03-29 Unilever Plc Fabric conditioning composition
FR2806307B1 (fr) 2000-03-20 2002-11-15 Mane Fils V Preparation parfumee solide sous forme de microbilles et utilisation de ladite preparation
EP1199340B1 (en) 2000-10-19 2005-03-09 Soft99 Corporation Paintwork coating composition and coating cloth
CA2439512A1 (en) 2001-03-07 2002-09-19 The Procter & Gamble Company Rinse-added fabric conditioning composition for use where residual detergent is present
GB0106560D0 (en) 2001-03-16 2001-05-02 Quest Int Perfume encapsulates
ES2258506T3 (es) 2001-12-24 2006-09-01 Cognis Ip Management Gmbh Composiciones cationicas para la limpieza de superficies duras.
WO2003061817A1 (de) 2002-01-24 2003-07-31 Bayer Aktiengesellschaft Mikrokapseln enthaltende koagulate
US20030158344A1 (en) 2002-02-08 2003-08-21 Rodriques Klein A. Hydrophobe-amine graft copolymer
US7053034B2 (en) 2002-04-10 2006-05-30 Salvona, Llc Targeted controlled delivery compositions activated by changes in pH or salt concentration
US7381697B2 (en) 2002-04-10 2008-06-03 Ecolab Inc. Fabric softener composition and methods for manufacturing and using
US7087572B2 (en) 2002-04-10 2006-08-08 Ecolab Inc. Fabric treatment compositions and methods for treating fabric in a dryer
US20060277689A1 (en) 2002-04-10 2006-12-14 Hubig Stephan M Fabric treatment article and methods for using in a dryer
US20030215417A1 (en) 2002-04-18 2003-11-20 The Procter & Gamble Company Malodor-controlling compositions comprising odor control agents and microcapsules containing an active material
US20030216488A1 (en) 2002-04-18 2003-11-20 The Procter & Gamble Company Compositions comprising a dispersant and microcapsules containing an active material
US6740631B2 (en) 2002-04-26 2004-05-25 Adi Shefer Multi component controlled delivery system for fabric care products
EP1504082A1 (en) 2002-05-16 2005-02-09 The Procter & Gamble Company Rinse-added fabric treatment composition and methods and uses thereof
EP1393706A1 (en) 2002-08-14 2004-03-03 Quest International B.V. Fragranced compositions comprising encapsulated material
US7585824B2 (en) 2002-10-10 2009-09-08 International Flavors & Fragrances Inc. Encapsulated fragrance chemicals
US20040071742A1 (en) 2002-10-10 2004-04-15 Popplewell Lewis Michael Encapsulated fragrance chemicals
US7125835B2 (en) 2002-10-10 2006-10-24 International Flavors & Fragrances Inc Encapsulated fragrance chemicals
AU2003296763A1 (en) 2002-11-29 2004-06-23 Ciba Specialty Chemicals Holding Inc. Fabric softener compositions comprising homo- and/or copolymers
EP1590427A2 (en) 2003-02-03 2005-11-02 Ciba SC Holding AG Washing agent and fabric softener formulations
US7135451B2 (en) 2003-03-25 2006-11-14 The Procter & Gamble Company Fabric care compositions comprising cationic starch
US6737392B1 (en) * 2003-06-11 2004-05-18 Goldschmidt Chemical Corporation MDEA ester quats with high content of monoester in blends with tea ester quats
US20050014672A1 (en) 2003-07-18 2005-01-20 Shoaib Arif Rinse aid additive and composition containing same
US8058224B2 (en) 2004-02-27 2011-11-15 The Procter & Gamble Company Multiple use fabric conditioning composition with blooming perfume
BRPI0509679A (pt) 2004-04-09 2007-10-09 Unilever Nv granulado para uso em produto de limpeza particulado, processo de fabricação do mesmo e composição detergente
JP2008516105A (ja) * 2004-10-18 2008-05-15 ザ プロクター アンド ギャンブル カンパニー 濃縮布地柔軟剤活性物質組成物
DE102005020551A1 (de) 2005-05-03 2006-11-09 Degussa Ag Feste, redispergierbare Emulsion
DE602006021041D1 (de) 2005-09-22 2011-05-12 Procter & Gamble Weichspülerzusammensetzung mit verringerter stoffeinfärbung
US7572761B2 (en) 2005-11-14 2009-08-11 Evonik Degussa Gmbh Process for cleaning and softening fabrics
ES2441247T3 (es) 2006-02-28 2014-02-03 The Procter & Gamble Company Composiciones para el cuidado de tejidos que comprenden almidón catiónico
ES2294923B1 (es) 2006-03-31 2009-02-16 Kao Corporation, S.A. Composicion para el enjuague y secado de vehiculos.
EP1849855A1 (de) 2006-04-27 2007-10-31 Degussa GmbH Thixotrope Weichspülmittel
WO2008021895A2 (en) * 2006-08-08 2008-02-21 The Procter & Gamble Company Clear and/or translucent fabric enhancers comprising nano-sized particles
EP2126019B1 (en) 2007-02-28 2014-04-09 Unilever PLC Fabric treatment compositions, their manufacture and use
EP2132290A1 (en) * 2007-04-02 2009-12-16 The Procter and Gamble Company Fabric care composition
US8080513B2 (en) 2008-01-11 2011-12-20 The Procter & Gamble Company Method of shipping and preparing laundry actives
US8361953B2 (en) * 2008-02-08 2013-01-29 Evonik Goldschmidt Corporation Rinse aid compositions with improved characteristics
JP2013509988A (ja) 2009-11-06 2013-03-21 ザ プロクター アンド ギャンブル カンパニー 有益剤を含む高効率のカプセル
BR112012025002B1 (pt) 2010-04-01 2021-02-23 Evonik Operations Gmbh composição ativa amaciante de tecidos, e seus processos de preparação
US20110239377A1 (en) 2010-04-01 2011-10-06 Renae Dianna Fossum Heat Stable Fabric Softener
EP2553066B1 (en) 2010-04-01 2014-04-30 Evonik Degussa GmbH Fabric softener active composition
US8183199B2 (en) 2010-04-01 2012-05-22 The Procter & Gamble Company Heat stable fabric softener
RU2515236C1 (ru) 2010-04-01 2014-05-10 Дзе Проктер Энд Гэмбл Компани Мягчитель ткани
US8507425B2 (en) 2010-06-29 2013-08-13 Evonik Degussa Gmbh Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2007734B (en) * 1977-10-22 1983-04-07 Cargo Fleet Chemical Co Fabric softeners
DE3402146A1 (de) * 1984-01-23 1985-07-25 Henkel KGaA, 4000 Düsseldorf Neue quartaere ammoniumverbindungen, deren herstellung und verwendung als textilweichmacher
WO1994019439A1 (en) * 1993-02-25 1994-09-01 Unilever Plc Use of fabric softening composition
EP0829531A1 (en) * 1996-08-22 1998-03-18 Unilever Plc Fabric conditioning composition
CN1284118A (zh) * 1997-11-24 2001-02-14 宝洁公司 具有增加柔软益处的低溶剂漂洗时加入的织物柔软剂
CN101248166A (zh) * 2005-08-31 2008-08-20 宝洁公司 浓缩型织物软化剂活性物质组合物
WO2009018955A2 (de) * 2007-08-06 2009-02-12 Clariant Finance (Bvi) Limited Zusammensetzungen enthaltend diethanolaminesterquats

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105401436A (zh) * 2015-12-18 2016-03-16 苏州富美纺织科技有限公司 织物阻燃整理液的制备方法
CN109762665A (zh) * 2017-11-10 2019-05-17 赢创德固赛有限公司 从甘油三酯油中提取脂肪酸的方法
CN113227338A (zh) * 2018-12-11 2021-08-06 联合利华知识产权控股有限公司 织物调理剂组合物

Also Published As

Publication number Publication date
IL220908A (en) 2015-07-30
MX2012011005A (es) 2012-10-15
UA106790C2 (uk) 2014-10-10
AU2011234658B2 (en) 2014-12-04
CN102803456B (zh) 2014-06-11
AP2012006438A0 (en) 2012-08-31
JP5460919B2 (ja) 2014-04-02
WO2011120836A1 (en) 2011-10-06
CA2795152C (en) 2014-03-18
ES2536849T3 (es) 2015-05-29
BR112012025002B1 (pt) 2021-02-23
US20110245139A1 (en) 2011-10-06
RU2526035C1 (ru) 2014-08-20
JP2013525615A (ja) 2013-06-20
AP4034A (en) 2017-02-12
MY159502A (en) 2017-01-13
US8563499B2 (en) 2013-10-22
PL2553067T3 (pl) 2015-07-31
CA2795152A1 (en) 2011-10-06
AU2011234658A1 (en) 2012-08-09
KR20130019387A (ko) 2013-02-26
ZA201207287B (en) 2013-06-26
EP2553067A1 (en) 2013-02-06
SG184397A1 (en) 2012-11-29
KR101425294B1 (ko) 2014-07-31
DK2553067T3 (en) 2015-05-26
EP2553067B1 (en) 2015-02-18
BR112012025002A2 (pt) 2020-09-01
MA34103B1 (fr) 2013-03-05
EG27007A (en) 2015-03-30

Similar Documents

Publication Publication Date Title
CN102803456B (zh) 织物柔软剂活性组合物
JP5570651B2 (ja) 織物柔軟剤活性組成物
ES2715664T3 (es) Composición activa suavizante de ropa
KR101694599B1 (ko) 섬유 유연제 활성 조성물 및 그의 제조 방법
EP1876224B1 (en) Liquid softener composition
JP6347723B2 (ja) 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
KR101170427B1 (ko) 산화방지제를 이용한 섬유유연제의 제조방법
JP4641827B2 (ja) 透明又は半透明の液体柔軟剤組成物

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
REG Reference to a national code

Ref country code: HK

Ref legal event code: DE

Ref document number: 1178561

Country of ref document: HK

C14 Grant of patent or utility model
GR01 Patent grant
REG Reference to a national code

Ref country code: HK

Ref legal event code: GR

Ref document number: 1178561

Country of ref document: HK

CP01 Change in the name or title of a patent holder
CP01 Change in the name or title of a patent holder

Address after: Essen, Germany

Patentee after: Evonik Operations Limited

Address before: Essen, Germany

Patentee before: EVONIK DEGUSSA GmbH