Gaf Corporation

Rhodia Limited

Rhone-Poulenc, Inc.

Isp Investments Inc.

Gaf Chemicals Corporation

Rhone-Poulenc Surfactants and Specialties, L.p.

David J Tracy

Robert B Login

Ratan K Chaudhuri

Ruoxin Li

Manilal S Dahanayake

Mohamed M Hashem

Michael W Helioff

Jiang Yang

Robert Lee Reierson

Jean-Marc Ricca

Ji Li

Paritosh M Chakrabarti

Lindley S Wood

Peter Lees

Bharat Desai

Walter F Hoffstadt

Fulvio J Vara

Rama K Haldar

Paul Frank D'Angelo

Thomas Rizzo

Mitchell B Ferguson

Gordon Wall

Novel nonionic gemini surfactants are extremely effective emulsifiers for oil-in-water emulsions that provide improved detergency at even low concentration levels. The surfactants are characterized by the formula:

Nonionic gemini surfactants

A novel class of anionic surfactants with improved surfact active properties is comprised of two hydrophilic and two hydrophobic groups represented by the formula: ##STR1## The surfactants exhibit unusually low critical micelle concentration (cmc) and pC-20 values in aqueous media.

Anionic surfactants having multiple hydrophobic and hydrophilic groups

Imadazoline-based amphoacetates of higher purity, containing essentially negligible amounts of unalkylated amido amines, lower amounts of glycolic acid salts and monochloroacetate salts, superior to currently available conventional amphoacetates, are provided. This is demonstrated by their improved surface-active properties. Lower inherent irritation properties may be expected due to improved purity. The higher purity amphoacetates can be obtained via processes utilizing precise pH control during the reaction of imidazoline, or its open-chain derivatives, with alkylating agents, e.g. sodium monochloroacetate. The pH can be controlled by adding the base slowly or automatically in response to a pH metering device to maintain a constant pH, or by a series of staged additions which are calculated to maintain pH within a stated range. The reaction may also be carried out by conducting the initial hydrolysis of the imidazoline ring structure, followed by alkylation. These higher-purity amphoacetates contain essentially fully alkylated products and lower amounts of glycolic acid derivatives, even though a ratio of SMCA to substituted imidazoline, or its open-ring derivative, of less than 1.5:1.0 and close to 1.0:1.0 is used.

High purity imidazoline-based amphoacetate surfactants

Blends of N-acyl aminoalkane sulfonates and amphoteric and/or anionic surfactants can be prepared by quenching a molten reaction mixture of an aminoalkane sulfonate amidated with a fatty acid with an aqueous solution comprising an amphoteric and/or anionic surfactant. N--acyl aminoalkane sulfonates can be purified by quenching a molten reaction mixture in isopropanol.

N-acylaminoalkane sulfonate and amphoteric surfactant blends and methods

The present invention comprises a new, improved class of anionic gemini surfactants consisting of two hydrophilic groups and two hydrophobic moieties joined by a bridge that possess improved surfactant functionalities yet may be characterized as mild for use in personal care products and environmentally benign. These compounds may be represented by the general structural formula as follows: ##STR1## wherein R, R.sub.1, R.sub.2, and R.sub.3 are selected from the group consisting of straight or branched chain C.sub.1 to C.sub.22 alkyl, aryl or hydrogen, and each R moiety can be the same or different; R.sub.4 and R.sub.5 are selected from the group comprising a straight or branched chain C.sub.1 to C.sub.6 alkyl with the further proviso that when either is a C.sub.6 it may exist as a cyclohexyl ring; R.sub.6 and R.sub.7 are selected from the group consisting of straight or branched chain C.sub.2 to C.sub.6 alkyl or aryl with the further proviso that R.sub.6 and R.sub.7 may be the same or different and wherein X is selected from the group comprising --S--, --S--S--, --D.sub.1 --R.sub.8 --D-- or --R.sub.8 --D.sub.1 --R.sub.8 -- wherein R.sub.8 is a straight or branched chain C.sub.1 to C.sub.10 alkyl or aryl and D.sub.1 is selected from the group consisting of --O--, --S--, --S--S--, --SO.sub.2 --; Y is --PO.sub.4 or --SO.sub.3 and can be the same or different and Z is selected from the group consisting of Na, K, alkali or alkaline earth metals, ammonium, their salts and mixtures thereof.

Anionic gemini surfactants and methods for their preparation

Process for the preparation of high purity imidazoline based

Novel nonionic gemini surfactants are extremely effective emulsifiers for oil-in-water emulsions that provide improved detergency at even low concentration levels. The surfactants are characterized by the formula: ##STR1## wherein R.sub.1 is independently H or a C.sub.1 to C.sub.22 alkyl, R.sub.2 is C.sub.6 to C.sub.22 alkyl and R.sub.3 is D.sub.1 --R.sub.4 --D.sub.1 or R.sub.4 --D.sub.1 --R.sub.4 wherein R.sub.4 is independently a C.sub.1 -C.sub.10 alkyl group, --O--R.sub.5 --O--, or aryl, e.g. phenyl, and D.sub.1 is independently --O--, an amide group �--C(O)N(R.sub.6)--!, an amino group �--N(R.sub.6)--!, --O--R.sub.5 --O--, or aryl. (EO).sub.a (PO).sub.b is a polyether group and Z is a C.sub.1 -C.sub.4 alkyl, or an alkylaryl or hydrogen wherein EO represents ethyleneoxy radicals, PO represents propyleneoxy radicals, a and b are numbers of from 0 to 100, a is preferably from about 0 to about 30 and b is preferably from about 0 to 10, wherein a plus b is at least one, and the EO and PO alkyl or alkylaryl.

Mild and environmentally benign bis-alkylphenol alkoxylated gemini surfactants of the formula: ##STR1## wherein R independently represents alkali, R.sub.1 independently represents hydrogen EO represents ethyleneoxy radicals alkyl, R.sub.2 independently represents hydrogen, --SO.sub.3 M, --P(O) (OM).sub.2, --CH.sub.2 COOM, --CH.sub.2 CHOHCH.sub.2 --SO.sub.3 HM, wherein M represents hydrogen, alkyl or alkaline earth metal, ammonium or an organic base salt; R.sub.3 represents alkylene of from one to about 10 carbon atoms or --C(O)--R.sub.4 --C(O)-- wherein R.sub.4 represents alkylene or aryl, and --O--R.sub.5 --O-- wherein R.sub.5 represents aliphatic or aromatic moieties with the proviso that when R.sub.3 is alkylene, then R.sub.2 is not hydrogen, and a and b are numbers ranging from one to about 100, with the proviso that when R.sub.2 is hydrogen, b is not zero.

According to the invention, an improved class of amphoteric surfactant having improved surfactant properties characterized as mild and environmentally safe has been provided comprising compounds of the formula: ##STR1## The amphoteric surfactant of the subject invention have at least two hydrophobic moieties and at least two hydrophilic groups per molecule and are useful as emulsifiers, detergents, dispersants and solubilizing agents.

Amphoteric surfactants having multiple hydrophobic and hydrophilic groups

Novel nonylphenol nonionic gemini surfactants are extremely effective emulsifiers for oil-in-water emulsions that provide improved detergency at even low concentration levels and are characterized by the formula: ##STR1## wherein R and R.sub.1 are both either H or a C.sub.4 -C.sub.22 alkyl, aryl, or alkylaryl with the stipulation that they cannot both be H at the same time; and R.sub.2 is independently --COR.sub.3 CO--, --CH.sub.2 N(R.sub.4)CH.sub.2 --; CH.sub.2 N(R.sub.5)R.sub.6 (R.sub.5)NCH.sub.2 --, or R.sub.7 --D--R.sub.7 wherein R.sub.3 independently represents a C.sub.1 -C.sub.6 alkyl, branched alkyl or aryl; R.sub.4 represents a C.sub.1 to C.sub.4 alkyl, aryl, alkylaryl, hydroxy alkyl, haloalkyl or H, R.sub.5 represents a C.sub.1 to C.sub.10 alkyl or aryl and R.sub.6 independently represents a C.sub.1 to C.sub.10 alkyl, aryl, or alkylaryl, R.sub.7 is a C.sub.2 to C.sub.4 alkyl and D independently represents --S--, --SO-- and SO.sub.2 with the stipulation that R.sub.5 and R.sub.6 can form a heterocyclic ring; EO represents ethylene oxy-radicals, x and y are whole numbers and x+y equals a number from 2 to 200 inclusive.

Nonylphenol nonionic gemini surfactants

A surfactant composition comprising compounds of the general formula: ##STR1## wherein R(CO).sub.n -- and R.sub.1 (CO).sub.n can be the same or different and comprise a C.sub.1 to C.sub.30 alkyl, or alkyl aryl and R.sub.2 is a C.sub.1 to C.sub.10 alkylene, arylene and the hydroxy-substituted derivatives thereof, a polyether (--O(R.sub.4 O).sub.x --) wherein R.sub.4 is a C.sub.2 to C.sub.4 alkyl and x is a whole number of from 1 to about 100; --S--, --SO.sub.2 --, --O--, --S--S--, --O--R.sub.5 --O-- or --S--R.sub.5 --S wherein R.sub.5 is a C.sub.1 to C.sub.10 alkyl, aryl or alkyl aryl, --N(R.sub.6)-- or --(NR.sub.6) R.sub.7 (NR.sub.6)-- wherein R.sub.6 is a C.sub.2 to C.sub.6 alkyl and R.sub.7 is a C.sub.2 to C.sub.6 alkyl or aryl with the further stipulation that R.sub.6 and R.sub.7 may form a heterocyclic ring, X is O or NZ wherein Z is a C.sub.1 to C.sub.10 alkyl, aryl, alkylaryl or hydrogen, and Y and Y.sub.1 represents an alcohol-containing group having at least two and preferably more hydroxyl groups.

Nonionic gemini surfactants having multiple hydrophobic and hydrophilic

A novel class of nonionic gemini surfactants and methods for their preparation consist of compounds with three hydrophilic heads and two lipophilic tails of the general formula: ##STR1## wherein R.sub.1 and R.sub.3 independently represents a C.sub.1 to C.sub.22 straight or branched chain alkyl, alkylene, aryl or alkylaryl, or hydrogen, with the proviso that both cannot be hydrogen; R.sub.2 represents a C.sub.1 to C.sub.5 straight or branched chain alkyl, alkylene or hydrogen, (Y) represents ##STR2## wherein R.sub.4 represents C.sub.1 to C.sub.3 alkyl or hydrogen and may be the same or different; X represents --(CH.sub.2).sub.a -- wherein a is a whole number of from 1 to 5; --S--, --S--S--, --SO.sub.2, --(CH.sub.2).sub.a SO.sub.2 (CH.sub.2).sub.a --,--O--, --C.dbd.O, or --CH.sub.2 --NR--CH.sub.2 -- wherein R is a C.sub.1 to C.sub.3 straight or branched chain alkyl, alkylene or hydrogen and x, y, and z are whole numbers of from about 6 to about 300. The surfactants exhibit excellent surface active functionality, low cmc and pC.sub.20 values and provide superior efficacies when combined with conventional single chain surfactants.

Nonionic gemini surfactants with three hydrophilic heads and two

A process for preparing blends or slurries of acyloxyalkane sulfonate salts is provided. The salts have the formula:

Acyloxyalkane sulfonate and amphoteric surfactant blend compositions and

Novel nonionic gemini surfactants are extremely effective emulsifiers for oil-in-water emulsions that provide improved detergency at even low concentration levels. The surfactants are characterized by the formula: ##STR1## wherein R.sub.1 is independently H or a C.sub.1 to C.sub.22 alkyl, R.sub.2 is H or C.sub.1 to C.sub.22 alkyl and R.sub.3 is D.sub.1 --R.sub.4 --D.sub.1 or R.sub.4 --D.sub.1 --R.sub.4 wherein R.sub.4 is independently a C.sub.1 -C.sub.10 alkyl group, --C(O)--, --R.sub.5 �O(EO).sub.a (PO).sub.b !--, --O--R.sub.5 --O--, or aryl, e.g. phenyl, and D.sub.1 is independently --O--, --S--, --S--S--, --SO.sub.2 --, --C(O)--, a polyether group �--O(EO).sub.a (PO).sub.b --!, an amide group �--C(O)N(R.sub.6)--!, an amino group �--N(R.sub.6)--!, --O--R.sub.5 --O--, or aryl. (EO).sub.a (PO).sub.b is a polyether group and Z is a C.sub.1 -C.sub.4 alkyl, or an alkylaryl or hydrogen wherein EO represents ethyleneoxy radicals, PO represents propyleneoxy radicals, a and b are numbers of from 0 to 100, a is preferably from about 0 to about 30 and b is preferably from about 0 to 10, and wherein a plus b is at least one.

According to the invention, an improved class of amphoteric surfactants having improved surfactant properties charaterized as mild and environmentally benign has been provided comprising a compound of the general formula: ##STR1## wherein R independently represents a C.sub.5 to C.sub.22 alkyl or acyl (RCO--); R.sub.1 represents a C.sub.1 to C.sub.6 alkyl; R.sub.2 independently represents --O--; R.sub.3 represents a C.sub.2 to C.sub.20 alkylene, arylene, or alkylarylene and M is Na, K, NH.sub.4, an organic base, or hydrogen. In addition to the novel compounds per se, the invention also provides new methods for the preparation of the amphoteric gemini surfactants as well as improved synergistic compositions that are obtained when the amphoteric geminis are blended with other surfactants.

Growing community of inventors

Lincoln Park, NJ, United States of America

David J Tracy