Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J3/00—Processes of treating or compounding macromolecular substances
  • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
  • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/22—Amides or hydrazides
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
  • C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
  • C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
  • C08F20/52—Amides or imides
  • C08F20/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
  • C08F20/56—Acrylamide; Methacrylamide
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
  • C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/16—Amines or polyamines
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/34—Higher-molecular-weight carboxylic acid esters
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B11/00—Recovery or refining of other fatty substances, e.g. lanolin or waxes
• • 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
  • C11D1/02—Anionic compounds
  • C11D1/04—Carboxylic acids or salts thereof
  • C11D1/08—Polycarboxylic acids containing no nitrogen or sulfur
• • 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
  • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
  • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
• • 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
  • C11D1/66—Non-ionic compounds
  • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols
• • D—TEXTILES; PAPER
  • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
  • D01C—CHEMICAL OR BIOLOGICAL TREATMENT OF NATURAL FILAMENTARY OR FIBROUS MATERIAL TO OBTAIN FILAMENTS OR FIBRES FOR SPINNING; CARBONISING RAGS TO RECOVER ANIMAL FIBRES
  • D01C3/00—Treatment of animal material, e.g. chemical scouring of wool
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
  • D06L1/00—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods
  • D06L1/12—Dry-cleaning or washing fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods using aqueous solvents
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
  • C08J2333/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers
  • C08J2333/24—Homopolymers or copolymers of amides or imides
  • C08J2333/26—Homopolymers or copolymers of acrylamide or methacrylamide

Definitions

• This invention relates to surfactants and in particular to novel surfactants based on derivatives of substituted succinic acids and to particular end uses for these surfactants.
• EP 0107199 B relates to polvoxyalkylene glycol hemi-esters of CQ to C12 alk(en)yl substituted succinic acids and their salts. These materials are described as anionic surfactants with particular utility at acidic pHs and having hard water tolerance.
• This invention is based on the discovery of compounds which can be derived from alkenyl succinic anhydrides having particularly C14 to C22 alk(en)yl groups and/or substituents of functional groups elsewhere around the molecule give materials which have significantly and surprisingly different properties. In particular they perform well as non-ionic surfactants, particularly in aqueous systems, having unexpected cloud point properties indicating good performance at elevated temperatures and have good behaviour in alkaline conditions. Also the surfactants of this invention have good biodegradation properties.
• the present invention accordingly provides a compound of the formulae (I) or (II):
• R and R 1 is C5 to C22 alkenyl or alkyl and the other is hydrogen;
• A is - 0 - or - R ⁇ -; where R ⁇ is hydrogen or Ci to C alkyl, particularly methyl or ethyl; n is 2 to 100 (and as it is an average it may be non-integral); m is 2 or 3 (and may vary along the polvoxyalkylene chain); R 2 is hydrogen or C]_ to C5 alkyl; A 1 is - 0 -, - 0- or -NR 4 - where R 4 is hydrogen or C*
• Y is a cation, particularly H + , and alkali metal cation especially a sodium or potassium cation, or an ammonium ion (especially NHz,-* " , an amine ammonium or an alkanolamine ammonium ion); and when A 1 is - 0 - or -NR 4 -:
• Y is a C*_ to Cs alkyl group (R 3 ) or a group of the formula (C m H2m°)n- ⁇ where m, n and R 2 are independently as defined above; provided that when A is - 0 - or A 1 is - 0 ⁇ the total number of carbon atoms in the groups R, R 1 and any groups R 2 and R 3 is at least 13, and is desirably 13 to 50; or
• the free acid forms of compounds of the formulae (I) and (II) in are defined with Y as a H + cation.
• Y a H + cation.
• this includes both the ionised form of the free acid that will typically predominate at relatively alkaline pHs and the non-ionised form, that will typically predominate at relatively acidic pHs.
• a and A 1 are desirably both - 0 -, both - NR 4 -, particularly - NH -, or A is - NR 4 -, particularly - NH -, and A 1 is - 0 -. Accordingly, the following particular sub-groups of compounds of the formula (I) form specific aspects of the invention (see also below about R and R**-).
• Y, m, n and R 2 are as defined above formula (I); and R and R 1 are as defined above for formula (I), but particularly where one of R and R 1 is a C1 to C22- especially a C1 to C20» alkenyl or alkyl group and the other is hydrogen.
• the compounds of the general formula (II) can be considered as di(substituted succinyl) functional derivatives of a polyoxyalkylene moiety.
• the respective groups A and A 1 and Y will be the same.
• both groups A are - 0 - or - NR 4 -, particularly - NH -, and both groups A 1 are - 0" with Y being a cation.
• the alk(en)yl groups in the groups R and R**- will usually be the same.
• Y is a cation, it is desirably H + , an alkali metal cation or an ammonium cation, particularly H + , an amine ammonium cation, such as tetramethylammonium or an alkanolamine ammonium ion e.g. H0.CH2CH .NH3 + ; where Y is a Ci to C5 alkyl group, it is particularly a methyl, ethyl or (straight or branched) butyl group.
• R 2 in formulae (I) and (II) is desirably either H or a methyl, ethyl, propyl or butyl (including branched propyl and butyl) group. Where R 2 is H, the products tend to be relatively more
• the compounds of the invention include at least one polyoxyalkylene chain made up of residues of ethylene glycol and/or
• the chain may be a homopolymer chain of either ethylene glycol residues or of propylene glycol residues or a block or random copolymer chain containing both ethylene glycol and propylene glycol residues. In compounds including more than one polyoxyalkylene chain, the chains can be the same or different.
• polyoxyalkylene chain defined as the group (C m H2mO) n in formula (I) (including la, lb and Ic) and (II).
• the chain length of this group i.e. the value of the parameter n, will generally be chosen to provide the desired properties in the intended product.
• the polyoxyalkylene chain is a
• polyethylene glycol chain it will usually have 3 to 50, particularly 3 to 35 e.g. 10 to 35, ethylene glycol residues and where it is a polyoxypropylene chain it will usually have 10 to 50 and more preferably 12 to 20 propylene glycol residues.
• the chain is a block or random copolymer of ethylene and propylene glycol residues
• the chain length chosen will typically correspond to the above ranges but numerically according to the proportion of ethylene and propylene glycol residues in the chain. Of course, numerical values of the > repeat length of the polyoxyalkylene chain are average values. As is common to surfactants containing a polyoxyalkylene chain, the longer
• compounds where the group R or R 1 is an alkenyl group are more desirable than those where the group is alkyl.
• Compounds where the group R or R 1 is an alkenyl group, particularly a C14 to C20 alkenyl group form a specific aspect of the invention.
• the compounds of this invention, and particularly those where the group R or R 1 is a C1 to C22 alkenyl or alkyl group have properties that are entirely unexpected in that the cloud point tends to rise with increasing length of the chain R or R , particularly where this chain is an alkenyl chain. The step from C12 to £3.4 chains is often particularly notable.
• the cloud point may tend to fall back somewhat, but often stays significantly above that for compounds with a chain length of say C ⁇ _2. This trend in cloud point indicates increasing water solubility of the compounds with increasing chain length which is completely unexpected and runs counter to previous experience with surfactants. However, at longer chain lengths the compounds tend to be less effective wetters, which is consistent with the increasingly hydrophobic nature of the group R/R 1 .
• surfactants are usually most effective at or near their cloud points.
• Higher cloud points indicate materials that are likely to be effective at comparably higher temperatures and surfactants are often used at moderately superambient temperatures.
• the longer chain lengths are linked with increased oil solubility so the cloud point behaviour indicates that better oil , solubility is likely to be linked to higher effective temperatures.
• the product is typically a mixture of isomers corresponding to the two senses of the anhydride ring opening reaction.
• the alkenyl or alkyl chain seems to have a minor steric effect on the isomer ratio with the isomer ration being typically about 60:40, the major isomer arising from nucleophilic attack at the anhydride carbonyl group remote from the alkenyl or alkyl group.
• Y is a different cation
• Y is an alkali metal or ammonium cation formation of the salts is straightforward by reaction with the corresponding base e.g. alkali metal such as sodium or potassium, hydroxide or carbonate, ammonia or amine, including alkanolamines such as ethanolamine.
• alkali metal such as sodium or potassium
• hydroxide or carbonate ammonia or amine
• alkanolamines such as ethanolamine.
• a 1 is other than -0 ⁇ i.e. Y is other than a cation
• further reaction is by preparation of an ester, particularly an ester with a C_ to C5 or polyalkylene glycol alkyl ether alcohol.
• esters and the corresponding amides can be made from esters with short chain alcohols, especially methyl or ethyl esters, by trans-esterification or amidation with the corresponding alcohol (YOH) or amine (YNH2) (where Y is as defined above).
• the esterification of the free acid can be carried out in a conventional manner for example using an acid catalyst which may be sulphuric, toluene sulphonic or a phosphoric acid.
• Phosphoric acids can be particularly useful as, after neutralisation, they may be a useful component of detergent compositions which include the surfactants of this invention.
• the compounds of the invention may be made by other methods.
• the anhydride may be reacted with a lower alcohol and the resulting half ester esterified with a polyalkylene glycol or polyalkylene glycol alkyl ether or condensed with an alkylene oxide and if desired end capped with a further lower alcohol.
• the poly ⁇ alkylene glycol chain length can be controlled by using a polyalkylene glycol or polyalkylene glycol alkyl ether of a narrow range of molecular weight, whereas the latter process gives a wide distribution of chain lengths.
• Alkenyl succinic anhydrides may be produced by reacting maleic anhydride preferably with an excess of an olefin having 6 to 22, particularly 14 to 22, carbon atoms for example a 50 to 200Z excess at a temperature in the range 150 to 400°C and preferably 180 to 250°C and removing excess olefin for example by distillation which is suitably carried out under vacuum. No catalyst is necessary, but is is preferred than an antioxidant be present.
• These anhydrides are well known commercial materials. In alkenyl succinic anhydrides prepared as described above the double bond normally lies in the 2-position in the alkenyl substituent.
• the unsaturated products can be hydrogenated or, and preferably, the intermediate alkenyl succinic anhydride can be hydrogenated to give an alkyl succinic anhydride.
• the hydrogenation is carried out over a hydrogenation catalyst such as Raney nickel or a Pd/C catalyst. Temperatures of from 15 to 100°C and pressures of 0 - 200 bar absolute may be used and, if desired a solvent may be present.
• the hydrogenation reaction on an alkenyl succinic anhydride may be carried out at 20°C using 5Z w/w of Pd/C catalyst over a period of for example 6 to 24 hours.
• the R, R 1 alkyl or alkenyl group of the compounds of the invention has a straight chain. Where the chain is not straight it is desirable that it has at most a total of two and preferably only one branch(es) on average. Preferably the whole molecule comprises at most three branches in total in all alkyl and alkenyl groups present.
• the products are readily made with low odour and, since polyalkylene glycols and polyalkylene glycol alkyl ether or their amine derivatives are readily transportable can be made at locations distant from alkylene oxide plants if they are used as reactants.
• Compounds according to the invention have emulsification properties and wetting and dispersion capabilities. These include use in oil in water emulsions for metal working fluids, based on semi-soluble oil and synthetics and for crude oil transportation and fuel systems, emollients for personal (skin) care; domestic detergent composition for example laundry liquids; the dispersion or organic and inorganic powders in paints and coatings (e.g. filler and pigments) and agrochemical formulations (e.g. pesticides); wetters in so-called industrial and institutional cleaning products (e.g. traffic film removers, bottle washes).
• industrial and institutional cleaning products e.g. traffic film removers, bottle washes.
• the surfactants of this invention include wool scouring and as inverting agents in the manufacture of acrylamide or similar products. These applications are described in more detail below.
• the woollen fleece includes, in addition to the wool fibre, a variety of materials including wool wax. Wool wax is a complex mixture of fatty materials secreted onto the wool by the skin of the sheep. Wool wax is removed from the wool, prior to use of the wool in textiles, by washing the wool with an aqueous mix including surfactants typically at moderately elevated temperatures e.g. 40 to 80°C, particularly 50 to 70°C. This process is called wool scouring.
• the surfactants of this invention are very effective wool scouring surfactants, in particular retaining their activity well after multiple scouring cycles, even when used in scouring wool with very fine fibres e.g. merino wool, which is difficult to scour because the proportion of wool fat is relatively high and the fibres have a high surface area to be treated.
• very fine fibres e.g. merino wool
• R 2 is a C**_ to CQ alkyl group, especially a methyl group are especially effective.
• the surfactant in this application is typically used at a concentration of from 0.1 to 5, particularly from 0.2 to 1.5, g.1-1.
• the invention accordingly includes a method of treating wool to remove wool wax which method comprises washing the wool, containing wool wax, with an aqueous mix including an effective amount of a compound of the formulae (I) or (II) above, in particular a compound of the formula (la) above, especially where m is 2, n is from 3 to 10 and where R 2 is a Ci to CQ alkyl group, particularly a methyl group.
• the invention also includes the use of such compounds of the invention as wool scouring surfactants.
• polymers such as polyacrylamide
• an emulsion polymerisation route in which the polymer is accumulated in an aqueous phase (in which it is soluble).
• aqueous phase in which it is soluble
• polyacrylamides can give aqueous solutions having high viscosities even at low concentrations; this is the basis of their use as thickeners and viscosity enhancers in aqueous systems. If the aqueous phase during polymerisation were the continuous phase, it would rapidly become very viscous, leading to difficulties in agitation and recovery of the product. To avoid this problem, the aqueous phase is normally the dispersed phase in an oil continuous phase i.e.
• a compound within the invention for this end use will depend on the specific operating conditions, we have found that compounds of the formula (la) above, particularly where m is 2, n is from 8 to 25, particularly 10 to 15, and where R 2 is H or a Ci to C5 alkyl group, particularly a methyl, ethyl, propyl or butyl group, are especially effective.
• the amount of surface active agent used to invert such emulsions will depend on the emulsion, in particular the proportion of disperse aqueous phase and the polymer concentration in the aqueous phase. Generally amounts in the range 1 to 5Z of the water in oil emulsion are typical.
• the invention accordingly includes a method of inverting a water in oil emulsion containing polyacrylamide in the aqueous phase which comprises including in the water in oil emulsion a compound of the formulae (I) or (II) above, in particular a compound of the formula (ia) above, especially m is 2, n is from 8 to 25, particularly 10 to 15, and where R 2 is H or a Ci to Cs alkyl group, particularly a methyl, ethyl, propyl or butyl group, and subsequently diluting the water in oil emulsion into water.
• the invention also includes the use of compounds of the invention as polyacrylamide water in oil emulsion inverting agents.
• Draves wetting was assessed using the skein test (ASTM D 2281 - 68); results are in seconds (s) [or minutes (m) - for slow wetters].
• 's' indicates that the substituent is an alkyl group; for R 2 H » hydrogen and a number the length of an alkyl group, for Y H indicates Y • » H + and a number the alkyl chain length.
• n may be rounded values; for compounds of the formula (II) the value for 'n* in this table is n+p in formula (II) as given above (with p » m) .
• Semi aqueous cleaning involves the cleaning of, e.g. metal, components with a solvent followed by a water rinse stage. Frequently solvents derived from terpenes are used in this application.
• Surface active agents can be added to expedite the removal of the solvent from the components being cleaned during the water rinse stage.
• Such surface active agents, or rinse aids as they are known must fulfil two criteria. Firstly they must effect good solvent removal and be soluble in the cleaning solvent. Secondly they must not stabilise mixtures of the solvent and water thus preventing effective separation of the mixture with adverse implications on waste disposal.
• Materials A and B below have the desired surface active properties to be effective rinse aids in semi aqueous cleaning formulations. They are also soluble in terpene solvents. Surprisingly tests have demonstrated that they exhibit rapid and more effective solvent and water separation as compared to other surfactants commonly used in this application.
• Complete separation means oil layer of 10Z and a water layer of 90Z of 0 the total volume.
• the following mixture was polymerised by heating to about 40°C using as the primary emulsifier a commercially available polymeric surfactant sold under the trade name "HYPERMER” 2296.

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• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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• Colloid Chemistry (AREA)

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