公开(公告)号：US11760889B2

公开(公告)日：2023-09-19

申请号：US16929420

申请日：2020-07-15

Applicant: STEPAN COMPANY

Inventor： David R. Allen ,  Marcos Alonso ,  Mary Beddaoui ,  Randal J. Bernhardt ,  Aaron Brown ,  Scott Dillavou ,  Xue Min Dong ,  Wilma Gorman ,  John C. Hutchison ,  Gary Luebke ,  Renee Luka ,  Franz Luxem ,  Andrew D. Malec ,  Ronald A. Masters ,  Dennis S. Murphy ,  Nicholas Pendleton ,  Irma Ryklin ,  Patti Skelton ,  Brian Sook ,  Chris Spaulding ,  Krista Turpin ,  Gregory Wallace ,  Michael Wiester ,  Patrick Shane Wolfe

IPC: C09D7/45 ,  A01N25/30 ,  A61K8/46 ,  C11D1/14 ,  C11D1/29 ,  B01F17/00 ,  C04B38/10 ,  C07C29/147 ,  C07C41/06 ,  C07C303/14 ,  C07C303/32 ,  C07C309/08 ,  C07C309/10 ,  C11D1/37 ,  C11D1/66 ,  C09D7/63 ,  C09K23/00

CPC classification number: C09D7/45 ,  A01N25/30 ,  A61K8/463 ,  A61K8/466 ,  C04B38/10 ,  C07C29/147 ,  C07C41/06 ,  C07C303/14 ,  C07C303/32 ,  C07C309/08 ,  C07C309/10 ,  C09D7/63 ,  C09K23/00 ,  C09K23/018 ,  C11D1/143 ,  C11D1/146 ,  C11D1/29 ,  C11D1/37 ,  C11D1/66 ,  A61K2800/10 ,  A01N25/30 ,  A01N37/34 ,  A01N43/40 ,  A01N43/56 ,  A01N43/653 ,  A01N43/70 ,  A01N47/30 ,  A01N51/00

Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives. Microscopy studies indicate that the unsaturated sodium sulfates in particular have a lamellar phase that should enable formulation at high actives levels. Sulfate compositions comprising 40 to 60 wt. % of a monounsaturated fatty primary alcohol sulfate and 40 to 60 wt. % of a secondary hydroxyalkyl primary alcohol sulfate are also disclosed. The derivatives and sulfate compositions are valuable for many end-use applications, including, for example, agricultural dispersants, water-soluble herbicides, anionic emulsifiers for agricultural use, hard surface cleaners, light-duty liquid detergents, personal cleansers, gas well foamers for oilfield applications, laundry detergents, enhanced oil recovery compositions, latex paints, and specialty foams.

公开(公告)号：US10287530B2

公开(公告)日：2019-05-14

申请号：US15606285

申请日：2017-05-26

Applicant: Stepan Company

Inventor： David R. Allen ,  Randal J. Bernhardt ,  Aaron Brown ,  Gregory P. Dado ,  Xue Min Dong ,  Wilma Gorman ,  Ronald Masters ,  Patti Skelton

IPC: C11D1/14 ,  C07C305/10 ,  A01N25/00 ,  A01N25/30

Abstract: Surfactant compositions comprising an alkoxylate, a sulfate, or ether sulfate of a C10-C12 monounsaturated alcohol are disclosed. The alkoxylate, sulfate, or ether sulfate may derive from undecylenic acid or undecylenic alcohol. Compared with their saturated analogs, the monounsaturated alkoxylates, sulfates, and ether sulfates are less irritating, making them valuable for personal care, laundry, cleaners, and other household applications. Microscopy studies show that the alkoxylates, sulfates, and ether sulfates have favorable phase behavior over a wide range of actives levels, expanding opportunities for products with greater compaction. When combined with cationic surfactants, the alkoxylates, sulfates, and ether sulfates exhibit synergy, and they have improved solubility compared with their saturated analogs. The surfactants find value for the personal care, laundry and cleaning, emulsion polymerization, agricultural products, oilfield applications, and specialty foams industries.

公开(公告)号：US09708251B2

公开(公告)日：2017-07-18

申请号：US14395829

申请日：2013-03-13

Applicant: Stepan Company

Inventor： David R. Allen ,  Marcos Alonso ,  Mary Beddaoui ,  Randal J. Bernhardt ,  Aaron Brown ,  Xue Min Dong ,  Wilma Gorman ,  John Hutchison ,  Gary Luebke ,  Renee Luka ,  Franz Luxem ,  Andrew D. Malec ,  Ronald A Masters ,  Dennis S Murphy ,  Patti Skelton ,  Brian Sook ,  Chris Spaulding ,  Michael Wiester ,  Patrick Shane Wolfe

IPC: A61K47/00 ,  C07C309/10 ,  C11D1/14 ,  C11D1/29 ,  A01N25/30 ,  A61K8/46 ,  B01F17/00 ,  C04B38/10 ,  C07C29/147 ,  C07C303/14 ,  C07C303/32 ,  C07C309/08 ,  C11D1/37 ,  C07C41/06 ,  C09D7/12 ,  C11D1/66 ,  C07C41/03

CPC classification number: C07C309/10 ,  A01N25/30 ,  A61K8/463 ,  A61K8/466 ,  A61K2800/10 ,  B01F17/0057 ,  B01F17/0092 ,  C04B38/10 ,  C07C29/147 ,  C07C41/03 ,  C07C41/06 ,  C07C303/14 ,  C07C303/32 ,  C07C309/08 ,  C09D7/63 ,  C11D1/143 ,  C11D1/146 ,  C11D1/29 ,  C11D1/37 ,  C11D1/66 ,  A01N37/34 ,  A01N43/40 ,  A01N43/56 ,  A01N43/653 ,  A01N43/70 ,  A01N47/30 ,  A01N51/00 ,  C07C43/1785 ,  C07C33/025

Abstract: Unsaturated fatty alcohol alkoxylates, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol alkoxylate is made by reducing a metathesis-derived monounsaturated alkyl ester, followed by alkoxylation of the resulting monounsaturated alcohol. Microscopy reveals that the monounsaturated alkoxylates have isotropic and lamellar phases over a wider range of actives levels compared with their saturated analogs. This attribute expands formulating latitude for many end-use applications. The unsaturated fatty alcohol alkoxylates are valuable in, for example, agricultural solvents, nonionic emulsifiers for agricultural compositions, hard surface cleaners, laundry detergents, specialty foams, additives or surfactants for paints or coatings, and surfactant compositions for enhanced oil recovery.

公开(公告)号：US20170267946A1

公开(公告)日：2017-09-21

申请号：US15606285

申请日：2017-05-26

Applicant: Stepan Company

Inventor： David R. Allen ,  Randal J. Bernhardt ,  Aaron Brown ,  Gregory P. Dado ,  Xue Min Dong ,  Wilma Gorman ,  Ronald Masters ,  Patti Skelton

IPC: C11D1/14 ,  C07C305/10 ,  A01N25/00 ,  A01N25/30

CPC classification number: C11D1/146 ,  A01N25/00 ,  A01N25/30 ,  C07C305/10

Abstract: Surfactant compositions comprising an alkoxylate, a sulfate, or ether sulfate of a C10-C12 monounsaturated alcohol are disclosed. The alkoxylate, sulfate, or ether sulfate may derive from undecylenic acid or undecylenic alcohol. Compared with their saturated analogs, the monounsaturated alkoxylates, sulfates, and ether sulfates are less irritating, making them valuable for personal care, laundry, cleaners, and other household applications. Microscopy studies show that the alkoxylates, sulfates, and ether sulfates have favorable phase behavior over a wide range of actives levels, expanding opportunities for products with greater compaction. When combined with cationic surfactants, the alkoxylates, sulfates, and ether sulfates exhibit synergy, and they have improved solubility compared with their saturated analogs. The surfactants find value for the personal care, laundry and cleaning, emulsion polymerization, agricultural products, oilfield applications, and specialty foams industries.

公开(公告)号：US20140194646A1

公开(公告)日：2014-07-10

申请号：US14146662

申请日：2014-01-02

Applicant: Stepan Company

Inventor： David R. Allen ,  Anatoliy A. Dameshek ,  Branko Sajic ,  Irene Shapiro ,  Xue Min Dong ,  Christopher D. Smith ,  Jacqueline M. Pytel ,  Jeremy Weitgenant

IPC: C07C67/08

CPC classification number: C07C67/08 ,  A61K8/37 ,  A61Q5/02 ,  A61Q15/00 ,  A61Q19/10 ,  C07B2200/07 ,  C07C67/03 ,  C07C69/68

Abstract: Provided are alkyl lactyllactate compositions that can be prepared from (1) lactide or alternatively lactic acid, and (2) a hydroxyl containing compound such as an alcohol, preferably a fatty alcohol or an alkoxylated alcohol, with (3) an acid catalyst. Preferably, the fatty alcohol contains from about 6 to 18 carbon atoms, such as lauryl alcohol. The alkyl lactyllactates can be used as surfactants, emulsifiers, skin feel agents, film formers, thickeners, rheological modifiers, etc., for personal care and other application areas. Compositions containing at least one alkyl lactyllactate are also provided. The compositions can further contain at least one surfactant.

Abstract translation: 本发明提供可由（1）丙交酯或乳酸制备的乳酸乳糖酯组合物，和（2）含羟基化合物如醇，优选脂肪醇或烷氧基化醇与（3）酸催化剂。 优选地，脂肪醇含有约6至18个碳原子，例如月桂醇。 乳酸乳酸烷基酯可用作个人护理和其他应用领域的表面活性剂，乳化剂，皮肤感觉剂，成膜剂，增稠剂，流变改性剂等。 还提供了含有至少一种乳糖基乳酸酯的组合物。 组合物还可以含有至少一种表面活性剂。

公开(公告)号：US10745347B2

公开(公告)日：2020-08-18

申请号：US14395835

申请日：2013-03-13

Applicant: Stepan Company

Inventor： David R. Allen ,  Marcos Alonso ,  Mary Beddaoui ,  Randal J. Bernhardt ,  Aaron Brown ,  Scott Dillavou ,  Xue Min Dong ,  Wilma Gorman ,  John C. Hutchison ,  Gary Luebke ,  Renee Luka ,  Franz Luxem ,  Andrew D Malec ,  Ronald A. Masters ,  Dennis S. Murphy ,  Nicholas Pendleton ,  Irma Ryklin ,  Patti Skelton ,  Brian Sook ,  Chris Spaulding ,  Krista Turpin ,  Gregory Wallace ,  Michael Wiester ,  Patrick Shane Wolfe

IPC: C07C309/10 ,  C07C29/147 ,  C07C309/08 ,  A01N25/30 ,  B01F17/00 ,  C11D1/37 ,  C04B38/10 ,  C07C303/32 ,  C07C303/14 ,  C09D7/63 ,  A61K8/46 ,  C11D1/14 ,  C11D1/29 ,  C07C41/06 ,  C11D1/66

Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.

公开(公告)号：US20190225915A1

公开(公告)日：2019-07-25

申请号：US16374819

申请日：2019-04-04

Applicant: Stepan Company

Inventor： David R. Allen ,  Randal J. Bernhardt ,  Aaron Brown ,  Gregory P. Dado ,  Xue Min Dong ,  Wilma Gorman ,  Ronald Masters ,  Patti Skelton

IPC: C11D1/14 ,  A01N25/00 ,  A01N25/30 ,  C07C305/10

Abstract: Surfactant compositions comprising an alkoxylate, a sulfate, or ether sulfate of a C10-C12 monounsaturated alcohol are disclosed. The alkoxylate, sulfate, or ether sulfate may derive from undecylenic acid or undecylenic alcohol. Compared with their saturated analogs, the monounsaturated alkoxylates, sulfates, and ether sulfates are less irritating, making them valuable for personal care, laundry, cleaners, and other household applications. Microscopy studies show that the alkoxylates, sulfates, and ether sulfates have favorable phase behavior over a wide range of actives levels, expanding opportunities for products with greater compaction. When combined with cationic surfactants, the alkoxylates, sulfates, and ether sulfates exhibit synergy, and they have improved solubility compared with their saturated analogs. The surfactants find value for the personal care, laundry and cleaning, emulsion polymerization, agricultural products, oilfield applications, and specialty foams industries.

公开(公告)号：US20150087724A1

公开(公告)日：2015-03-26

申请号：US14395829

申请日：2013-03-13

Applicant: Stepan Company

Inventor： David R. Allen ,  Marcos Alonso ,  Mary Beddaoui ,  Randal J. Bernhardt ,  Aaron Brown ,  Xue Min Dong ,  Wilma Gorman ,  John Hutchison ,  Gary Luebke ,  Renee Luka ,  Franz Luxem ,  Andrew D. Malec ,  Ronald A Masters ,  Dennis S Murphy ,  Patti Skelton ,  Brian Sook ,  Chris Spaulding ,  Michael Wiester ,  Patrick Shane Wolfe

IPC: C07C29/147 ,  C09D7/12 ,  C11D1/66 ,  C07C41/06 ,  A01N25/30

CPC classification number: C07C309/10 ,  A01N25/30 ,  A61K8/463 ,  A61K8/466 ,  A61K2800/10 ,  B01F17/0057 ,  B01F17/0092 ,  C04B38/10 ,  C07C29/147 ,  C07C41/03 ,  C07C41/06 ,  C07C303/14 ,  C07C303/32 ,  C07C309/08 ,  C09D7/63 ,  C11D1/143 ,  C11D1/146 ,  C11D1/29 ,  C11D1/37 ,  C11D1/66 ,  A01N37/34 ,  A01N43/40 ,  A01N43/56 ,  A01N43/653 ,  A01N43/70 ,  A01N47/30 ,  A01N51/00 ,  C07C43/1785 ,  C07C33/025

Abstract: Unsaturated fatty alcohol alkoxylates, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol alkoxylate is made by reducing a metathesis-derived monounsaturated alkyl ester, followed by alkoxylation of the resulting monounsaturated alcohol. Microscopy reveals that the monounsaturated alkoxylates have isotropic and lamellar phases over a wider range of actives levels compared with their saturated analogs. This attribute expands formulating latitude for many end-use applications. The unsaturated fatty alcohol alkoxylates are valuable in, for example, agricultural solvents, nonionic emulsifiers for agricultural compositions, hard surface cleaners, laundry detergents, specialty foams, additives or surfactants for paints or coatings, and surfactant compositions for enhanced oil recovery.

Abstract translation: 公开了不饱和脂肪醇烷氧基化物，其制备方法及其使用方法。 在一个方面，单不饱和脂肪醇烷氧基化物是通过还原衍生的单不饱和烷基酯，然后将所得的单不饱和醇进行烷氧基化来制备的。 显微镜显示，与其饱和类似物相比，单不饱和烷氧基化物在更广泛的活性水平范围内具有各向同性和层状相。 该属性扩展了许多最终用途应用程序的自由度。 不饱和脂肪醇烷氧基化物在例如农用溶剂，用于农业组合物的非离子乳化剂，硬表面清洁剂，衣物洗涤剂，特种泡沫，用于油漆或涂料的添加剂或表面活性剂以及用于提高油采收率的表面活性剂组合物中是有价值的。

公开(公告)号：US20150087521A1

公开(公告)日：2015-03-26

申请号：US14395835

申请日：2013-03-13

Applicant: Stepan Company

Inventor： David R. Allen ,  Marcos Alonso ,  Mary Beddaoui ,  Randal J. Bernhardt ,  Aaron Brown ,  Scott Dillavou ,  Xue Min Dong ,  Wilma Gorman ,  John C. Hutchison ,  Gary Luebke ,  Renee Luka ,  Franz Luxem ,  Andrew D Malec ,  Ronald A. Masters ,  Dennis S. Murphy ,  Nicholas Pendleton ,  Irma Ryklin ,  Patti Skelton ,  Brian Sook ,  Chris Spaulding ,  Krista Turpin ,  Gregory Wallace ,  Michael Wiester ,  Patrick Shane Wolfe

IPC: C07C309/10 ,  C07C29/147 ,  C07C309/08 ,  A01N25/30 ,  B01F17/00 ,  C11D1/37 ,  C04B38/10 ,  C07C303/32 ,  C07C303/14

CPC classification number: C07C309/10 ,  A01N25/30 ,  A61K8/463 ,  A61K8/466 ,  A61K2800/10 ,  B01F17/0057 ,  B01F17/0092 ,  C04B38/10 ,  C07C29/147 ,  C07C41/06 ,  C07C303/14 ,  C07C303/32 ,  C07C309/08 ,  C09D7/63 ,  C11D1/143 ,  C11D1/146 ,  C11D1/29 ,  C11D1/37 ,  C11D1/66 ,  A01N37/34 ,  A01N43/40 ,  A01N43/56 ,  A01N43/653 ,  A01N43/70 ,  A01N47/30 ,  A01N51/00

Abstract: Sulfate and sulfonate derivatives of unsaturated fatty alcohols, processes for making them, and methods of using them are disclosed. In one aspect, a monounsaturated fatty alcohol composition is made by reducing a metathesis-derived monounsaturated alkyl ester. The fatty alcohol composition is then converted to a sulfate or sulfonate derivative by one or more of alkoxylation, sulfation, sulfonation, and sulfitation. Of particular interest are the sulfate and ether sulfate derivatives.

Abstract translation: 公开了不饱和脂肪醇的硫酸酯和磺酸酯衍生物，其制备方法及其使用方法。 在一个方面，单不饱和脂肪醇组合物通过还原来自复分解衍生的单不饱和烷基酯来制备。 然后通过烷氧基化，硫酸化，磺化和硫酸化中的一种或多种将脂肪醇组合物转化成硫酸盐或磺酸盐衍生物。 特别感兴趣的是硫酸盐和醚硫酸盐衍生物。