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：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：US20210128432A1

公开(公告)日：2021-05-06

申请号：US17145999

申请日：2021-01-11

Applicant: Stepan Company

Inventor： James A. Faunce ,  Renata A. Butikas ,  Randal J. Bernhardt ,  Sarah E. Kovach ,  Teresa Germain ,  Patrick Shane Wolfe ,  Leonard Frank Zaporowski ,  Anatoliy A. Dameshek

IPC: A61K8/41 ,  A61K8/9789 ,  A61K8/37 ,  A61Q5/02

Abstract: Esterquat compositions are disclosed that comprise, based on the weight of the composition, 0% to about 70% by weight of a solvent, and about 30% to 100% by weight of a mixture comprising about 50% to about 80% by weight, based on the weight of the mixture, of esterquats and about 20% to about 50% by weight, based on the weight of the mixture, of mono- and diglycerides. The esterquat compositions can be prepared by the direct esterification of a natural oil with an alkanolamine, followed by quaternization in the presence of the solvent. The esterquat compositions can be formulated into hair care compositions that provide improved wet and dry combing properties.

公开(公告)号：US10982174B2

公开(公告)日：2021-04-20

申请号：US16601726

申请日：2019-10-15

Applicant: STEPAN COMPANY

Inventor： Randal J. Bernhardt ,  Xue Min Dong

IPC: C11D1/65 ,  A61K8/41 ,  A61Q5/02 ,  A61Q19/10 ,  A01N25/04 ,  A61K8/46 ,  A61K8/49 ,  A61Q19/00 ,  C09K8/584 ,  C11D11/00 ,  C11D1/02 ,  C11D1/62

Abstract: Synergistic surfactant blends are disclosed. In one aspect, the blend comprises an anionic surfactant and a metathesis-based cationic surfactant comprising a quaternized derivative. The quaternized derivative is a quaternized fatty amine, quaternized fatty amidoamine, imidazoline quat, or esteramine quat made from a metathesis-derived C10-C17 monounsaturated acid or its ester derivative. Also disclosed are synergistic surfactant blends comprising a cationic surfactant and a metathesis-based anionic surfactant comprising a sulfonated derivative. The sulfonated derivative is a fatty ester sulfonate, fatty acid sulfonate, sulfoestolide, fatty amide sulfonate, sulfonated fatty ester alkoxylate, imidazoline quat sulfonate, sulfonated amidoamine oxide, or sulfonated amidoamine betaine. The synergistic blends have a negative β value or a reduced interfacial tension (IFT) when compared with an expected IFT value calculated from the individual surfactant components. Blends of the invention also exhibit surprisingly favorable solubility profiles. The surfactant blends are useful for laundry detergents, dish detergents, household or industrial cleaners, personal care products, agricultural products, building materials, oil recovery compositions, emulsion polymers, and other practical applications.

公开(公告)号：US20170211016A1

公开(公告)日：2017-07-27

申请号：US15482932

申请日：2017-04-10

Applicant: STEPAN COMPANY

Inventor： Randal J. Bernhardt ,  Xue Min Dong

IPC: C11D1/65 ,  C11D11/00 ,  C09K8/584

CPC classification number: C11D1/65 ,  A01N25/04 ,  A61K8/416 ,  A61K8/466 ,  A61K8/4946 ,  A61K2800/596 ,  A61Q5/02 ,  A61Q19/00 ,  A61Q19/10 ,  C09K8/584 ,  C11D1/02 ,  C11D1/62 ,  C11D1/652 ,  C11D11/0017 ,  C11D11/0023

Abstract: Synergistic surfactant blends are disclosed. In one aspect, the blend comprises an anionic surfactant and a metathesis-based cationic surfactant comprising a quaternized derivative. The quaternized derivative is a quaternized fatty amine, quaternized fatty amidoamine, imidazoline quat, or esteramine quat made from a metathesis-derived C10-C17 monounsaturated acid or its ester derivative. Also disclosed are synergistic surfactant blends comprising a cationic surfactant and a metathesis-based anionic surfactant comprising a sulfonated derivative. The sulfonated derivative is a fatty ester sulfonate, fatty acid sulfonate, sulfoestolide, fatty amide sulfonate, sulfonated fatty ester alkoxylate, imidazoline quat sulfonate, sulfonated amidoamine oxide, or sulfonated amidoamine betaine. The synergistic blends have a negative β value or a reduced interfacial tension (IFT) when compared with an expected IFT value calculated from the individual surfactant components. Blends of the invention also exhibit surprisingly favorable solubility profiles. The surfactant blends are useful for laundry detergents, dish detergents, household or industrial cleaners, personal care products, agricultural products, building materials, oil recovery compositions, emulsion polymers, and other practical applications.

公开(公告)号：US20170158617A1

公开(公告)日：2017-06-08

申请号：US15403288

申请日：2017-01-11

Applicant: Stepan Company

Inventor： Dave R. Allen ,  Marcos Alonso ,  Randal J. Bernhardt ,  Aaron Brown ,  Kelly Buchek ,  Sangeeta Ganguly-Mink ,  Brian Holland ,  Gary Luebke ,  Renee Luka ,  Andrew D. Malec ,  Ronald A. Masters ,  Dennis S. Murphy ,  Irene Shapiro ,  Patti Skelton ,  Brian Sook ,  Michael R. Terry ,  Gregory Wallace ,  Laura Lee Whitlock ,  Michael Wiester ,  Patrick Shane Wolfe ,  Lena Titievsky

IPC: C07C233/09 ,  A01N25/30 ,  A01N37/18 ,  A01N41/04 ,  A01N25/04 ,  C09D7/12 ,  A61K8/46 ,  A61Q19/10 ,  A61Q5/12 ,  C11D11/00 ,  C09K8/524 ,  C07C309/70 ,  A61K8/42

CPC classification number: C07C233/09 ,  A01N25/02 ,  A01N25/04 ,  A01N25/30 ,  A01N33/12 ,  A01N37/18 ,  A01N37/44 ,  A01N41/04 ,  A61K8/416 ,  A61K8/42 ,  A61K8/44 ,  A61K8/466 ,  A61K8/92 ,  A61Q5/02 ,  A61Q5/12 ,  A61Q17/005 ,  A61Q19/10 ,  A62D1/0071 ,  B01F17/0028 ,  B01F17/0057 ,  C07C69/533 ,  C07C69/593 ,  C07C209/12 ,  C07C211/21 ,  C07C219/08 ,  C07C231/12 ,  C07C233/20 ,  C07C233/38 ,  C07C237/16 ,  C07C303/18 ,  C07C309/15 ,  C07C309/70 ,  C07D233/24 ,  C08G65/2615 ,  C08K5/01 ,  C08K5/20 ,  C08K5/42 ,  C09D7/45 ,  C09D7/63 ,  C09K8/00 ,  C09K8/524 ,  C09K8/54 ,  C09K15/28 ,  C11C3/00 ,  C11C3/08 ,  C11D1/002 ,  C11D1/04 ,  C11D1/28 ,  C11D1/62 ,  C11D1/652 ,  C11D1/66 ,  C11D1/74 ,  C11D1/83 ,  C11D1/90 ,  C11D1/92 ,  C11D1/94 ,  C11D3/48 ,  C11D11/0017 ,  C07C211/63 ,  C07C211/64 ,  C07C309/14 ,  A01N33/18 ,  A01N39/04 ,  A01N43/653 ,  A01N51/00 ,  A01N57/20 ,  A01N43/40 ,  A01N43/56 ,  A01N53/00

Abstract: Fatty amide compositions and their derivatives are disclosed. The fatty amides comprise a reaction product of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with a primary or secondary amine. Derivatives made by reducing, quaternizing, sulfonating, alkoxylating, sulfating, and sulfitating the fatty amide are also included. The amine reactant can be diethylenetriamine or (2-aminoethyl)ethanolamine, which provide imidazoline amides or esters, respectively. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The compositions are valuable for cleaners, fabric treatment, hair conditioning, personal care, antimicrobial compositions, agricultural uses, and oil field applications.

公开(公告)号：US20160024003A1

公开(公告)日：2016-01-28

申请号：US14867251

申请日：2015-09-28

Applicant: Stepan Company

Inventor： Dave R. Allen ,  Marcos Alonso ,  Randal J. Bernhardt ,  Aaron Brown ,  Sangeeta Ganguly-Mink ,  Andrew Malec ,  Teresa Manuel ,  Ronald A. Masters ,  Lawrence A. Munie ,  Dennis S. Murphy ,  Patti Skelton ,  Brian Sook ,  Michael R. Terry ,  Jeremy Aaron Weitgenant ,  Laura Lee Whitlock ,  Michael Wiester ,  Patrick Shane Wolfe

IPC: C07C309/69 ,  C11D1/90 ,  C11D1/92 ,  C07C211/63 ,  C07C229/12 ,  C07C233/36 ,  A01N33/12 ,  A01N37/44 ,  A01N41/04 ,  A61K8/41 ,  A61K8/44 ,  A61K8/46 ,  A61Q5/02 ,  A61Q5/12 ,  C09K15/28 ,  C09K15/22 ,  A62D1/02 ,  C09K8/54 ,  C09K8/60 ,  C04B24/16 ,  C04B24/12 ,  C11D1/62

CPC classification number: C07C309/69 ,  A01N25/02 ,  A01N25/04 ,  A01N25/30 ,  A01N33/12 ,  A01N37/18 ,  A01N37/44 ,  A01N41/04 ,  A61K8/416 ,  A61K8/42 ,  A61K8/44 ,  A61K8/447 ,  A61K8/466 ,  A61K8/92 ,  A61Q5/02 ,  A61Q5/12 ,  A61Q19/10 ,  A62D1/0071 ,  B01F17/0028 ,  B01F17/0057 ,  C04B24/121 ,  C04B24/124 ,  C04B24/16 ,  C07C6/04 ,  C07C41/03 ,  C07C43/11 ,  C07C67/26 ,  C07C69/533 ,  C07C69/593 ,  C07C209/12 ,  C07C211/21 ,  C07C211/63 ,  C07C219/08 ,  C07C229/12 ,  C07C231/12 ,  C07C233/36 ,  C07C237/16 ,  C07C303/18 ,  C08G65/2615 ,  C08K5/01 ,  C08K5/20 ,  C09K8/00 ,  C09K8/54 ,  C09K8/60 ,  C09K15/22 ,  C09K15/28 ,  C11C3/00 ,  C11C3/08 ,  C11D1/002 ,  C11D1/04 ,  C11D1/28 ,  C11D1/62 ,  C11D1/652 ,  C11D1/74 ,  C11D1/83 ,  C11D1/90 ,  C11D1/92 ,  C11D1/94 ,  C11D3/48 ,  C07C211/64 ,  C07C233/38 ,  C07C309/14 ,  A01N33/18 ,  A01N39/04 ,  A01N43/653 ,  A01N51/00 ,  A01N57/20 ,  A01N43/40 ,  A01N43/56 ,  A01N53/00

Abstract: Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amines, wherein the fatty amine is made by reducing the amide reaction product of of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and a secondary amine, are disclosed. Quaternary ammonium, betaine, or sulfobetaine compositions derived from fatty amidoamines, wherein the amidoamine is made by reacting of a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives and an aminoalkyl-substituted tertiary amine, are also disclosed. The quaternized compositions are advantageously sulfonated or sulfitated. In one aspect, the ester derivative of the C10-C17 monounsaturated acid or octadecene-1,18-dioic acid is a lower alkyl ester. In other aspects, the ester derivative is a modified triglyceride N made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin. The quaternary ammonium, betaine, and sulfobetaine compositions and their sulfonated or sulfitated derivatives are valuable for a wide variety of end uses, including cleaners, fabric treatment, hair conditioning, personal care (liquid cleansing products, conditioning bars, oral care products), antimicrobial compositions, agricultural uses, and oil field applications.

Abstract translation: 衍生自脂肪胺的季铵，甜菜碱或磺基甜菜碱组合物，其中脂肪胺是通过还原由复分解衍生的C10-C17单不饱和酸，十八碳烯-1,18-二酸或其酯衍生物的酰胺反应产物 和仲胺。 衍生自脂肪酰氨基胺的季铵，甜菜碱或磺基甜菜碱组合物，其中酰氨基胺是由易位素衍生的C 10 -C 17单不饱和酸，十八碳烯-1,18-二酸或其酯衍生物和氨基烷基取代的叔碳酸酯 胺也被公开。 季铵化组合物有利地被磺化或硫酸化。 一方面，C10-C17单不饱和酸或十八碳烯-1,18-二酸的酯衍生物是低级烷基酯。 在其它方面，酯衍生物是通过天然油或不饱和甘油三酸酯通过天然油与烯烃的交叉复分解而制备的改性甘油三酯N。 季铵，甜菜碱和磺基甜菜碱组合物及其磺化或亚硫酸盐衍生物对于各种最终用途是有价值的，包括清洁剂，织物处理，头发调理，个人护理（液体清洁产品，调理棒，口腔护理产品），抗微生物剂 组合物，农业用途和油田应用。

公开(公告)号：US20150094383A1

公开(公告)日：2015-04-02

申请号：US14395082

申请日：2013-04-12

Applicant: Stepan Company

Inventor： Randal J. Bernhardt ,  Xue Min Dong

IPC: C11D1/65 ,  C09K8/584 ,  A01N25/04 ,  A61Q19/00 ,  A61K8/46 ,  A61K8/49

CPC classification number: C11D1/65 ,  A01N25/04 ,  A61K8/416 ,  A61K8/466 ,  A61K8/4946 ,  A61K2800/596 ,  A61Q5/02 ,  A61Q19/00 ,  A61Q19/10 ,  C09K8/584 ,  C11D1/02 ,  C11D1/62 ,  C11D1/652 ,  C11D11/0017 ,  C11D11/0023

Abstract: Synergistic surfactant blends are disclosed. In one aspect, the blend comprises an anionic surfactant and a metathesis-based cationic surfactant comprising a quaternized derivative. The quaternized derivative is a quaternized fatty amine, quaternized fatty amidoamine, imidazoline quat, or esteramine quat made from a metathesis-derived C10-C17 monounsaturated acid or its ester derivative. Also disclosed are synergistic surfactant blends comprising a cationic surfactant and a metathesisbased anionic surfactant comprising a sulfonated derivative. The sulfonated derivative is a fatty ester sulfonate, fatty acid sulfonate, sulfoestolide, fatty amide sulfonate, sulfonated fatty ester alkoxylate, imidazoline quat sulfonate, sulfonated amidoamine oxide, or sulfonated amidoamine betaine. The synergistic blends have a negative value or a reduced interfacial tension (IFT) when compared with an expected IFT value calculated from the individual surfactant components. Blends of the invention also exhibit surprisingly favorable solubility profiles.

Abstract translation: 公开了协同表面活性剂共混物。 一方面，共混物包含阴离子表面活性剂和包含季铵化衍生物的基于复分解的阳离子表面活性剂。 季铵化衍生物是由复分解衍生的C10-C17单不饱和酸或其酯衍生物制成的季铵化脂肪胺，季铵化脂肪酰氨基胺，咪唑啉季铵盐或酯胺季铵盐。 还公开了包含阳离子表面活性剂和包含磺化衍生物的易位素阴离子表面活性剂的协同表面活性剂共混物。 磺化衍生物是脂肪酯磺酸盐，脂肪酸磺酸盐，磺基甲基醚，脂肪酰胺磺酸盐，磺化脂肪酸酯烷氧基化物，咪唑啉季磺酸盐，磺化酰氨基胺氧化物或磺化酰氨基胺甜菜碱。 当与由各个表面活性剂组分计算的预期IFT值相比时，协同共混物具有负值或降低的界面张力（IFT）。 本发明的共混物也表现出令人惊讶的有利的溶解度曲线。

公开(公告)号：US11560530B2

公开(公告)日：2023-01-24

申请号：US16374819

申请日：2019-04-04

Applicant: Stepan Company

Inventor： Randal J. Bernhardt ,  Wilma Gorman ,  Ronald Masters

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

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：US11142729B2

公开(公告)日：2021-10-12

申请号：US16536863

申请日：2019-08-09

Applicant: Stepan Company

Inventor： Brian Holland ,  Randal J. Bernhardt ,  Branko Sajic ,  Rick Tabor

IPC: C11D1/00 ,  C11D11/00 ,  C11D1/14 ,  C11D1/22 ,  C11D1/29 ,  C11D1/34 ,  C11D1/72 ,  C11D1/75 ,  C11D1/83 ,  C11D1/90 ,  C11D1/92 ,  C11D3/30 ,  C11D3/386

Abstract: Detergents useful for cold-water cleaning and mid-chain headgroup and alkylene-bridged surfactants useful therein are disclosed. The mid-chain headgroup surfactant has a C14-C30 alkyl chain and a polar group bonded to a central zone carbon of the alkyl chain. The alkylene-bridged surfactant has a C12-C18 alkyl chain, a polar group, and a C1-C2 alkylene group bonded to the polar group and a central zone carbon of the C12-C18 alkyl chain. Preferred surfactants in these classes are alcohol sulfates, alcohol ethoxylates, ether sulfates, sulfonates, arylsulfonates, alcohol phosphates, amine oxides, quaterniums, betaines, and sulfobetaines. Surprisingly, detergents formulated with the surfactants provide outstanding cold-water performance in removing greasy stains such as bacon grease, butter, cooked beef fat, or beef tallow from soiled articles.