CN105411870B - Alkyl lactyllactate and preparation method thereof - Google Patents

Abstract

The present invention provides alkyl lactyllactate compositions, the alkyl lactyllactate composition can be from (1) lactide or optional lactic acid, (2) compound of hydroxyl such as alcohol, preferably fatty alcohol or alkoxylated alcohol are prepared in the presence of (3) acid catalyst.Preferably, the fatty alcohol includes about 6 to about 18 carbon atoms, such as laruyl alcohol.The alkyl lactyllactate can be used as surfactant, emulsifier, skin sense agent, film forming agent, thickener, rheology modifier etc. for personal care field and other application field.The present invention also provides the compositions containing at least one alkyl lactyllactate.The composition can also include at least one surfactant.

Description

Alkyl lactyllactate and preparation method thereof

The application is the Chinese invention patent application (applying date: on July 6th, 2007；Application number: 200780033126.7 (states Border application number: PCT/US2007/072975)；Denomination of invention: alkyl lactyllactate and preparation method thereof) divisional application.

Related application

This application claims U.S. Provisional Patent Applications 60/819,145 (submission on July 6th, 2006), 60/842,476 The priority of (submitting on September 6th, 2006) and 60/896,205 (submission on March 21st, 2007).Face herein by above-mentioned When the whole instruction applied be incorporated herein by reference.This application involves the co-pending submitted with the application in phase same date Application, and the attorney docket of the application be 17730WO02.

The research or development that federal government subsidizes

[without applicatory]

Technical field

Technology of the present invention relates generally to alkyl lactyllactate (alkyl lactyllactate), and compound is such as Lauryl lactyllactate, and comprising or the incorporation compound composition.Technology of the present invention also generally relates to make The improved method of the standby alkyl lactyllactate compound and its derivative and composition, the composition include or mix There is described alkyl lactyllactate compound or derivatives thereof.

Background technique

In personal care field, it is desirable to which surfactant is mild, salt-free (salt-free) and 100% activity Object.Other ideal attributes include: in room temperature in liquid form, there is unazotized structure, in low-temperature mixed application Allotment ability in (cold-mix application) and have performance good with existing surfactant as or than showing Some better abilities of surfactant.

For household cleaning product, industrial and public cleaning product (institutional cleaning Product), surfactant and solvent are the important components in these products.The ideal attribute of the said goods includes following Ability: emulsification suspends or permeates grease soils or oily soil, and suspension or dispersed particle, with clean surface；Then it prevents The dirt, grease or particle are redeposited on the surface just cleaned.For example, laundry detergent products ideally should be from Clothing removes dirt and retains the dirt of removing in the solution, so that dirt is removed with slurry (wash water), Rather than it is redeposited on washed clothing.

Preferably also with following ability: being carried out to the blistering of different household products, industrial products and public product Control, this depends on desired final use application.For example, manual dish washing detergent (the dish washing of liquid Detergent) preferably there is the ability blistered in the presence of the dirt removed from tableware.However, for for efficiently washing Wash the laundry detergent or dish washing detergent in machine (washing machine), it is desirable to which low blistering is most preferably cleaned and kept away to realize Exempt from excess foam formation.Other ideal properties of the above-mentioned consumer goods include the ability for clarifying the preparation and the energy for improving stability Power.For hard surface cleaner, it is generally desirable to have following ability: moisten various surface types and be coupled or soil suspension with Make the surface without streak and/or the residue of form membrane.

Unexpectedly, it has been found that the alkyl lactyllactate of the technology of the present invention can satisfy in ideal attribute above It is one or more.The alkyl lactyllactate can be incorporated to for example various compositions and neutralized and be used as surfactant, cream Agent, skin sense agent (skin feel agent), film forming agent, rheology modifier (rheological modifier), solvent, every From agent (release agent), lubricant, conditioner and dispersing agent etc..Above-mentioned composition can be used in final use application, institute Stating final use application includes but is not limited to personal care articles and household cleaning product and industrial and public cleaning product.It Can be used for oily field application, gypsum foaming agent, paint and coating, adhesive or other need cold tolerance (cold Tolerance performance) or need pass the winter (winteration) application (such as need cold climate performance without Application comprising other volatile components).

United States Patent (USP) 2,350,388 and 2,371,281 (Claborn) (" Claborn patent ") generally describes cream Acyl lactic acid alkyl ester can be prepared by the following method according to described in its: in the presence of acid catalyst and in anhydrous conditions, will The mixture of dry lactide and absolute alcohol heats about 6 to 8 hours at 70 DEG C to 90 DEG C.The Claborn patent is also general Ground describes alkyl lactyllactate, declares that it has the property for being ideally used to solvent and plasticizer, and other for manufacturing The property of plasticizer.

However, the method for preparing alkyl lactyllactate as described in Claborn patent needs in the reactive mixture Using solvent, the solvent is excessive alcohol or inert organic liquid, such as benzene.The Claborn patent also needs to be higher than 70 DEG C reaction temperature.However, it is desirable that cancel the use of solvent in the reaction process for preparing alkyl lactyllactate, and/ Or with the method that can be carried out in more low reaction temperatures.Moreover, the Claborn patent does not recognize chirality to gained cream The control and influence of acyl lactic acid alkyl ester property.The Claborn patent does not teach how that preparation has different chiralitys yet Alkyl lactyllactate.In addition, the Claborn patent does not recognize selection (such as primary alconol and secondary alcohol or the tertiary alcohol of alcohol；Rouge Fat alcohol and lower alcohol) influence to product yield, product purity and product characteristics.In addition, the Claborn patent is not realized To also without disclose can be used as surfactant, emulsifier, skin sense agent, film forming agent, thickener, rheology modifier etc. for The alkyl lactyllactate of people's nursing field and other application field.As such, it would be desirable to have following methods: the method energy The alkyl lactyllactate product for enough preparing the higher purity of more preferable yield, without distillation or other purifying.It is also desirable that It prepares and uses the alkyl lactyllactate with selected chirality to obtain or improve certain desired final products properties.

United States Patent (USP) 3,144,341 (Thompson) (" Thompson patent ") is disclosed by making stearyl alcohol or cetanol With lactic acid (Lactic acid CH₃CHOHCOOH) the prepared dilactic acid stearyl ester of reaction and dilactic acid cetyl.Usually The dilactic acid stearyl ester so prepared and dilactic acid cetyl are described as emulsifier, the emulsifier is especially suited as Shortening agent in cake (cake) mixture etc..The Thompson patent claims that reaction product is cream in the 3rd column 29-31 row The mixture of acyl stearyl lactate ester (stearyl lactyllactate) and stearyl lactate ester (stearyl lactate), it is described Dilactic acid stearyl ester and stearyl lactate ester be known respectively as dilactic acid stearyl ester (stearyl lactoyl lactate) and Stearyl lactate ester (stearyl lactate).The Thompson patent also declares stearyl lactate ester in the 3rd column 56-57 row Dilactic acid stearyl ester not as desired is effective.The document the 1st column 31-54 row suggest every mole stearyl alcohol (or Cetanol) 2.1 moles of lactic acid is used, but the lactoyl carried out using the lactic acid of additional molar is implied in the 3rd column 57-59 row The reaction of stearyl lactate ester does not provide apparent benefit.The Thompson patent also uses catalyst without introduction or hint In reacting for the alcohol and lactic acid.Because alkyl lactyllactate is considered more efficient, and energy compared with lactic acid alkyl ester Better performance and stability are enough provided, so preferably having improved method, the improved method can be through lactic acid Route preparation contains the alkyl lactyllactate product of more high proportion dilactic acid ester component compared with lactate component.

Summary of the invention

In one aspect, technology of the present invention provides the alkyl lactyllactate with following general formula structure:

Wherein R is alkyl or alkoxylated alkyl.R can be derived from the compound of hydroxyl, such as alcohol, and preferably primary Alcohol.

Preferably, the alkyl lactyllactate of the technology of the present invention is presented specific chiral, and the alkyl lactyllactate can To be such as L- dilactic acid ester, D- dilactic acid ester, the L prepared by such as Study of Meso-Lactide, D/D, L racemic lactoyl cream Acid esters or the L prepared by such as rac-lactide, L/D, D racemic dilactic acid ester or their mixture.It is a kind of preferred Alcohol be fatty alcohol, such as the fatty alcohol containing about 6 to about 18 carbon atoms.

According to some embodiments, it is preferable that at least one alkyl lactyllactate of the technology of the present invention be have it is following General formula structure L- alkyl lactyllactate:

According to some other embodiments, it is preferable that one or more alkyl lactyllactates are handed over by meso third The L of ester preparation, D/D, L racemic dilactic acid ester, or the lactoyl prepared by L- lactide and the mixture of Study of Meso-Lactide The mixture of lactate.

According to some embodiments, at least one alkyl lactyllactate of the technology of the present invention can use following general formula knot Structure indicates:

Wherein R includes about 2 to about 6 carbon atoms, optionally about 2 to about 4 carbon atoms, preferably from about 2 to about 3 carbon originals Son, R¹Comprising about 1 to about 22 carbon atom, optionally about 1 to about 18 carbon atom, optionally about 6 to about 18 carbon atoms can About 12 to about 14 carbon atoms of selection of land, optionally about 1 to about 6 carbon atom (such as 4 carbon atoms), and the number of repetitive unit Mesh (n) can be about 0 to about 100.When n is 0, the alkyl in the dilactic acid ester is not alkoxylated.When n is not 0 When, the alkyl lactyllactate includes at least one alkoxy base (alkoxylate group).Personal nursing is answered It is preferably from about 1 to about 12 with the application of, care and household or other clean applications, n, optionally about 1 to about 9, optionally about 1 to about 6, Optionally about 2 to about 4.

Preferably, the compound for being used to prepare the hydroxyl of the alkyl lactyllactate of technology of the present invention includes at least One primary hydroxyl (OH).When the compound of the hydroxyl includes two or more primary hydroxyls, can be formed containing two or more The compound of a dilactic acid ester group.For example, when using compound (such as glycerol or ethoxylation containing two primary hydroxyls Glycerol) when being used as bridging molecule, some embodiments of technology according to the present invention, the alkyl lactyllactate can be with following General formula structure indicate:

According to some embodiments, the R group in above formula preferably includes about 2 to about 24 carbon atoms, even more preferably about 2 To about 8 carbon atoms.For example, the R group can be derived from glycerol or alkoxylated glycerol.

On the other hand, technology of the present invention provides one or more methods for preparing alkyl lactyllactate.Extremely A kind of few method includes such as following steps: providing at least one mixture, the mixture includes at least one lactide, extremely A kind of compound (such as fatty alcohol or alkoxylated alcohol) of few hydroxyl and at least one acid catalyst；And described third is set to hand over The compound of ester and hydroxyl is in room temperature reaction or in pyroreaction.The compound of the lactide and hydroxyl can be by equal Mole (equivalent molar amount) use.Reaction temperature can be about 15 DEG C to about 150 DEG C, preferably from about 20 DEG C to about 100 DEG C, even more preferably about 30 DEG C to about 70 DEG C, most preferably about 40 DEG C to about 60 DEG C.The acid catalyst can be with It is such as H₂SO₄, HCl, p-methyl benzenesulfonic acid (pTSA) orIonomer (Ionomer it) (is available from E.I.du Pont de Nemours and Company) or their mixture.Lactide used can be in solid form Or liquid form, and can be L- lactide, D- lactide, Study of Meso-Lactide or rac-lactide or theirs is mixed Close object.Preferably, lactide used is L- lactide or Study of Meso-Lactide or their mixture.Preferably, described third Lactide is prepared by fermentation method.For at least some applications, L- lactide is most preferred.The compound of the hydroxyl can be Fatty alcohol, such as the fatty alcohol containing about 6 to about 18 carbon atoms.Preferably, the compound of the hydroxyl is primary alconol.Preferably One example of fatty alcohol is laruyl alcohol.It is further preferred that not using any solvent in the method, and prepared lactoyl Lactic acid alkyl ester is clarification uniform liquid.

The another embodiment for preparing the method for the alkyl lactyllactate of the technology of the present invention is, right for relative quantity In compound (such as fatty alcohol or alkoxylated alcohol) component of at least one hydroxyl of every equivalent, work as using at least about 4 At least one lactic acid component of amount is condensed.Preferably, using catalyst.The example of preferred catalyst is to toluene sulphur Acid.Reaction temperature can be about 120 DEG C to about 200 DEG C.Preferably, any solvent is not used in the reaction.

It yet still another aspect, technology of the present invention provides composition, the composition includes at least one dilactic acid Arrcostab.The composition can be Aquo System or other forms.The composition can also include one or more surfaces Activating agent.The composition can also include buffer.Above-mentioned buffer for example may include it is enough (such as by weight about 0.1% to citric acid/sodium citrate, lactic acid/ammonium lactate or their mixture about 0.75%).Preferably, the buffering System answers enough offers, stablizes the pH of gained preparation at least 4 weeks in 50 DEG C of stability tests.Required buffer is just True amount can be determined by conventional steps/test that is known to those skilled in the art and understanding, and be depended on final The level of one or more alkyl lactyllactates and/or other active matters used in purposes preparation.Preferably, the lactoyl Alkyl in lactic acid alkyl ester includes about 6 to about 18 carbon atoms, even more preferably about 12 to about 14 carbon atoms, such as laurel Base.It is highly preferred that the alkyl lactyllactate is L- alkyl lactyllactate.Most preferably, the composition is substantially free of The alkyl lactyllactate of other stereoisomers.

Detailed description of the invention

Figures 1 and 2 show that the viscosity salt of the exemplary composition of the alkyl lactyllactate with or without the technology of the present invention is rung Answer curve (viscosity salt response curve).

The frothing capacity of the exemplary composition of alkyl lactyllactate of the display of Fig. 3 and 4 with or without the technology of the present invention Test (being free of any oil) result.

Figures 5 and 6 show the clean body of the exemplary composition of the alkyl lactyllactate with or without the technology of the present invention (body wash) performance comparison.

Fig. 7 shows the comparative studies result of the stability of the composition containing buffer and the composition without buffer.

Fig. 8 show with without the technology of the present invention lauryl lactyllactate (" LLL " or " L3 ") reference composition compared with, The hand washing of the exemplary composition of the lauryl lactyllactate containing the technology of the present invention with different gross activity object concentration is tested (hand wash test) result.

Fig. 9 shows the viscosity salt response curve of four kinds of compositions, primary surfactant contained by four kinds of compositions (primary surfactant) is 4:1 or 14:1 to the ratio of auxiliary surfactant (secondary surfactant).? In every kind of composition, the gross activity object amount of surfactant is 15%.Primary surfactant used is lauryl polyoxyethylene (2) ether sodium sulfate (sodium lauryl 2mole ether sulphate) (SLES-2 or CS-230).Auxiliary surface used Activating agent is cocamidopropyl betaine (cocamidopropyl betaine) (CAPB or HCG) or L3.

Figure 10 shows specialized review hand washing result of study (the expert panel hand wash study of three kinds of soap samples result)。

The manual blistering test result of the three kinds of soap samples of display of Figure 11 and 12.

Figure 13 and 14 shows the specialized review skin sensing test result of three kinds of soap samples.

Figure 15, which is shown, contains three kinds of different primary surfactants and L3 for three kinds compared with the reference composition containing CS-230 and HCG Composition manual blistering test result.

Figure 16, which is shown, contains three kinds of different masters for three kinds compared with three kinds containing the composition of three kinds of different primary surfactants and HCG The manual blistering test result of the composition of surfactant and L3.

Figure 17, which is shown, contains three kinds of different masters for three kinds compared with three kinds containing the composition of three kinds of different primary surfactants and HCG The viscosity salt response curve of the composition of surfactant and L3.

Figure 18-20 shows that the hand washing frothing result of three serial compositions, three serial compositions include SLES-2 (CS-230) is used as primary surfactant and HCG, L3, cocoyl monoethanolamine (cocamide Monoethanolamide), both sexes acetate (amphoacetate), sulfosuccinate (sulfosuccinate) or they Combination as auxiliary surfactant.

Figure 21 shows the frothing capacity test (without any oil) of three kinds of compositions containing lauryl lactyllactate as a result, institute State lauryl lactyllactate by (1) L- lactide or (2) 15:85 L- lactide and Study of Meso-Lactide mixture or (3) Prepared by rac-lactide.

Figure 22 shows the viscosity salt response curve of three kinds of compositions containing lauryl lactyllactate, the dilactic acid laurel Ester by (1) L- lactide or (2) 15:85 L- lactide and Study of Meso-Lactide mixture or (3) rac-lactide institute Preparation.

Specific embodiment

According to some embodiments, the alkyl lactyllactate of the technology of the present invention can have following general formula structure (I):

In general formula structure (I), R includes alkyl or alkoxylated alkyl.R can be derived from least one hydroxyl Compound, such as alcohol.Term " compound of hydroxyl " used in this application generically refers to containing at least one hydroxyl The compound of (" OH ").

Preferably, the alkyl lactyllactate of the technology of the present invention is presented specific chiral, and the alkyl lactyllactate can To be such as L- dilactic acid ester, D- dilactic acid ester, the L prepared by such as Study of Meso-Lactide, D/D, L- racemic lactoyl Lactate or the L prepared by such as rac-lactide, L/D, D- racemic dilactic acid ester or their mixture.According to At least some applications, L- dilactic acid ester is most preferred.The alkyl lactyllactate can be by lactide and hydroxyl Compound is prepared (" lactide method "), and the compound of the hydroxyl is, for example, fatty alcohol or alkoxylated alcohol.The lactoyl Lactic acid alkyl ester directly can also prepare (" lactic acid method ") by lactic acid.Preferably, the lactide or skill of the present invention are used to prepare The lactic acid of the alkyl lactyllactate of art is prepared by fermentation method known in the art.

The compound for being used to prepare the hydroxyl of the alkyl lactyllactate of the technology of the present invention can be straight chain, branch , it is saturated or unsaturated, and natural or synthetic raw material (feed stock) can be derived from.The change of the hydroxyl The alkyl closed in object can preferably include about 1 to about 22 carbon atom, optionally about 6 to about 18 carbon atoms, optionally about 12 to about 18 carbon atoms, optionally about 12 to about 14 carbon atoms.The compound of the hydroxyl preferably includes at least one A primary hydroxyl.Preferably, at least one embodiment of technology, lactide selectively can contain hydroxyl with described according to the present invention Primary hydroxyl reaction in the compound of base.The compound of the hydroxyl is preferably substantially free of secondary hydroxyl or tert-hydroxyl.It does not wish Prestige is bound by any specific theory, it has been unexpectedly found that when the lactide for example with equimolar than with hydroxyl When compound is reacted, secondary hydroxyl alcohol or tert-hydroxyl alcohol can result in aggregation problem.It is highly preferred that according to some embodiment party Case, the compound of the hydroxyl are primary fatty alcohols, and most preferably C₁₂To C₁₄Fatty alcohol, in manufacture the technology of the present invention Aggregation problem is avoided when one or more alkyl lactyllactates.

Have also been discovered that, for such as personal care applications, care and household application and other clean applications in purposes, Fatty alcohol, especially C₁₂Or C₁₄Alcohol or C₁₂/C₁₄Alcohol is capable of providing and improved and ideal foaming property, soil release performance is presented Matter, skin perception matter and/or physical property (such as tackifying (viscosity building), dissolubility and allotment property (formulatability)) alkyl lactyllactate.While not wishing to be bound by any particular theory, but it is of the invention The dilactic acid C of technology₁₂/C₁₄Ester is believed to mention at least some final uses using (such as clean body, shampoo etc.) For optimal overall performance.By C₁₆Or C₁₆/C₁₈The alkyl lactyllactate of preparation, which is recognized as, can generate better feeling, But for example generate less foam.In addition, dilactic acid C₁₂/C₁₄Ester is liquid in room temperature, and dilactic acid C₁₆/C₁₈Ester exists Room temperature is solid.When using lower alcohol, resulting alkyl lactyllactate still is able to provide good frothing capacity, still Their tackifying may be than dilactic acid C₁₂/C₁₄Ester wants poor.The example of suitable fatty alcohol includes laruyl alcohol and stearyl alcohol.

Appoint moreover it is preferred that not used in the lactide method of the technology of the present invention of the alkyl lactyllactate needed for preparing What solvent.The purpose of the technology of the present invention is to prepare dilactic acid alkyl at least some applications, such as personal care applications Cancel the use of solvent in the reaction process of ester.However, usually, because viscosity or product are distributed (product Distribution relationship), solventless method may be difficult to operate.In technology of the present invention, unexpectedly It was found that obtained reaction product can have ideal dilactic acid ester to lactate by using solvent-free reaction system Or the distribution (distribution) of high polymer (higher polymer).It is preferably based on the total weight of the reaction product, The alkyl lactyllactate product of the lactide method preparation of technology comprises more than about 90% at least one lactoyl cream through the invention Acid alkyl ester and less than about 10% one or more lactic acid alkyl esters, one or more high polymers and other impurity compositions.

As a further example, the compound of the hydroxyl of the technology of the present invention can be alkoxylated alcohol, such as ethoxy The alcohol of base, propenoxylated alcohol or not only ethoxylation but also propenoxylated alcohol.The compound of the hydroxyl is worked as and lactide (in situ) alkoxylate can be carried out in situ when reaction.Selectively, can be used carried out it is alkoxylated containing hydroxyl The compound of base.For example, the laruyl alcohol of ethoxylation can be used to prepare to ethoxylated lauryl dilactic acid ester (LLL (EO)), every mole of ethoxylated lauryl dilactic acid ester (such as LLL (1EO), LLL (2EO) or LLL (3EO)) includes The ethyoxyl (ethoxylate) (EO) of specific quantity, the second of preferably from about 1mol to about 12mol (such as 1mol, 2mol or 3mol) Oxygroup (EO).

For alkoxylate more particularly to change the polarity of alkyl lactyllactate molecule, this can make resulting dilactic acid ester Molecule is more soluble in water and can influence its hydrophilic/lipophilic balance (HLB).Alkoxylate can also influence surfactant and exist Accumulation (packing) in micella.Alkoxylate can also influence the wetting power of the alkyl lactyllactate, cloud point and its Its surfactant properties.It is not intended to be bound by any specific theory, alkoxylate is believed to give with rudimentary table The lotion or microemulsion of face bioactivator activity object (lower surfactant active) are steady with improved clarity and preferably It is qualitative.Also the clean-up performance of dilactic acid ester surfactant can be influenced, and improves the energy of finishing surfactant properties Power.

According to some embodiments, the alkyl lactyllactate of the technology of the present invention can use following general formula structure (II) table Show:

In general formula structure (II), R preferably includes about 2 to about 6 carbon atoms, even more preferably about 2 to about 4 carbon originals Son, most preferably about 2 to about 3 carbon atoms, R¹About 1 to about 22 carbon atom is preferably included, optionally about 1 to about 18 carbon Atom, optionally about 6 to about 18 carbon atoms, optionally about 12 to about 14 carbon atoms, optionally about 1 to about 6 carbon atom (such as 4 carbon atoms) and the number (n) of repetitive unit can preferably be about 0 to about 100.When n is 0, R¹Preferably Comprising about 12 to about 18 carbon atoms, optionally about 12 to about 14 carbon atoms.When n is not 0, the alkyl lactyllactate Comprising at least one alkoxy, and preferably, n is about 1 to about 12, optionally about 1 to about 6, optionally about 2 to about 4；R¹It is excellent Selection of land includes about 1 to about 6 carbon atom (such as butanol+1EO, butanol+2EO, ethyl alcohol+2EO, hexanol+2EO), selectively, R¹ Include about 6 to about 18 carbon atoms.

In some embodiments, the R in R group or general formula structure (II) above in general formula structure (I)¹Group can be with The dihydric alcohol of primary hydroxyl (OH) or the polyalcohol containing two or more primary hydroxyls derived from there are two tools.In some other implementations In scheme, R group can derive the dihydric alcohol of at least one self-contained primary hydroxyl or the polyalcohol containing at least one primary hydroxyl.Example Such as, when using the compound (glycerol or the glycerol of ethoxylation) containing two primary hydroxyls as the bridging molecule, according to this The alkyl lactyllactate of some embodiments of inventive technique can be indicated with following general formula structure (III):

According to some embodiments, above R group in formula (III) preferably may include about 2 to about 24 carbon atoms, Preferably from about 2 to about 8 carbon atoms and R can be alkyl or alkoxylated alkyl.For example, R group can be derived from it is sweet Oil or the glycerol of ethoxylation.

Can by various forms of lactides for example L- lactide, D- lactide, Study of Meso-Lactide, rac-lactide or Their mixture is used to prepare the alkyl lactyllactate of the technology of the present invention.L- lactide, Study of Meso-Lactide or they Mixture is preferred.It is highly preferred that lactide used in technology of the present invention is prepared by lactic acid or derivatives thereof, it is described Lactic acid or derivatives thereof is by fermentation method known in the art such as carbohydrate fermentation method (carbohydrate Fermentation process) or biological fermentation process (biofermentation process) it is prepared.It can be used for preparing The lactic acid derivative of lactide includes the obtained lactate of such as lactic fermentation and ammonium lactate.

In at least one embodiment of the technology of the present invention, for preparation with for example better foaming characteristic and/or more The alkyl lactyllactate of good tackifying, the mixture or L- lactide of L- lactide and Study of Meso-Lactide are most preferably 's.Therefore, it for some personal care applications, is prepared by L- lactide and the mixture or L- lactide of Study of Meso-Lactide Dilactic acid ester is most preferred.In some other embodiments, by the dilactic acid alkyl of Study of Meso-Lactide preparation Ester can be preferably.For example, the application of light-duty laundry (LDL) detergent, heavy duty detergent laundry (HDL) detergent are applied, The lactoyl cream by Study of Meso-Lactide preparation can be preferably used in some soap bar (soap bar) applications or some solvent applications Acid alkyl ester.The mixture and Study of Meso-Lactide of L- lactide and Study of Meso-Lactide are usually liquid form in room temperature, and L- lactide, rac-lactide and D- lactide are solid in room temperature.It is not intended to be bound by any specific theory, observe To under identical reaction conditions, the mixture of Study of Meso-Lactide and L- lactide reacts faster than pure L- lactide.

The reaction temperature for preparing the alkyl lactyllactate of the technology of the present invention can be about 15 DEG C to about 150 DEG C, optionally About 20 DEG C to about 100 DEG C, optionally about 25 DEG C to about 75 DEG C, optionally about 30 DEG C to about 70 DEG C.According at least some embodiment party Case (such as prepare alkyl lactyllactate) for personal care applications, the reaction temperature is preferably from about 40 DEG C to about 60 DEG C, optionally about 50 DEG C to about 60 DEG C, optionally about 40 DEG C to about 50 DEG C.

Preferably, acid catalyst is used in the reaction of compound of lactide and hydroxyl.The example packet of acid catalyst It includes but is not limited to H₂SO₄, HCl, p-methyl benzenesulfonic acid (pTSA) andIonomer (is available from E.I.du Pont de Nemours and Company).According at least some embodiments, based on the weight of lactide in reaction mixture, the present invention The amount of catalyst required for one or more methods of technology is about 1.0 weight % or less, optionally about 0.01 weight % To about 0.4 weight %.

For at least some embodiments of the technology of the present invention, especially for personal care applications, by L- lactide system Standby alkyl lactyllactate is most preferred.For some personal care applications, can also be preferably used by L- lactide The alkyl lactyllactate prepared with the mixture of Study of Meso-Lactide.Unexpectedly, it has been found that being handed over by meso third Ester or the racemic alkyl lactyllactate of rac-lactide preparation are compared, by the mixing of L- lactide and Study of Meso-Lactide Object or the alkyl lactyllactate of L- lactide preparation have better foaming characteristic and/or better tackifying.As use L- third When lactide and the mixture of Study of Meso-Lactide, the total weight based on L- lactide and Study of Meso-Lactide, in the mixture The amount of L- lactide can be about 50% to about 100%, and optionally about 0% to about 70%, optionally about 15% to about 70%.Under The scheme in face illustrates the method for being used to prepare the technology of the present invention of L- alkyl lactyllactate.In this exemplary arrangement, In the H as catalyst₂SO₄In the presence of, make L- lactide and C_6-18Fatty alcohol (ROH) is small in 50 DEG C of reactions about 12 to 24 When, to prepare L- alkyl lactyllactate.

Other lactides such as D- lactide, Study of Meso-Lactide and rac-lactide can be prepared with different three-dimensionals Learn the alkyl lactyllactate of (stereoisomer).In at least one embodiment of the technology of the present invention, handed over by meso third The alkyl lactyllactate of ester preparation is preferred.In following exemplary arrangement, in the H as catalyst₂SO₄Presence Under, make Study of Meso-Lactide and C_12-18Fatty alcohol (ROH) reacts about 12 to 24 hours in 50 DEG C, to prepare L, disappears outside D/D, L- Revolve alkyl lactyllactate.Another form of racemic alkyl lactyllactate (L, L/D, D) can be by making racemic third Lactide is reacted with the fatty alcohol to be prepared.

It has been found that the method for technology of the present invention sufficiently can reduce or avoid the generation of by-product, and exceed to anticipate Improve the yield and product purity of target alkyl lactyllactate in material ground.For example, it has been found that the third of technology is handed over according to the present invention The reacting for compound (such as L- lactide with laruyl alcohol) of ester and hydroxyl can be preferably available about 95% or higher receipts Rate, and in the case where without further purification, based on the total weight of products therefrom mixture, one in the product mixtures Kind or the purity of a variety of alkyl lactyllactates can preferably reach about 90% or more, optionally about 95% or more.Base In the total weight of products therefrom mixture, the amount of the lactic acid alkyl ester by-product or residue alcohol preferably less than about 5% (such as In about 1% to about 5% range).

At least one embodiment of technology according to the present invention, it is in high temperature (such as 50 DEG C) that equimolar lactide is such as solid The L- lactide of body and at least one fatty alcohol and catalytic amount (weight based on the lactide, by weight approximatively about 0.01% to about 1%) sulfuric acid mixing.The lactide and one or more alcohol of different mol ratio can be used, such as can make With excessive lactide or excessive one or more alcohol.However, at least some embodiments of the technology of the present invention, equivalent Lactide and one or more alcohol be preferred.After such as about 12 to 24 hours (such as about 16 hours), when mixed It closes object to become between the muddy uniform liquid between clarification to be preferably when clarifying uniform liquid, reaction stops.If mixture It is muddy, then mixture can be continued heating a period of time in high temperature (such as 50-60 DEG C), to generate preferred clarification Uniform liquid.In general, reaction temperature is lower, the reaction time needed is longer.The mixture can be used for personal nursing and answer With in other application.Remaining sulfuric acid can be left in them, or can be for example, by washing, being adsorbed onto alkali alumina It is removed on (basic alumina) or silica gel medium (silica media) or with alkali neutralization by remaining sulfuric acid.

At least one other embodiment of technology according to the present invention by lactide and can have two or more hydroxyls The compound of hydroxyl the alkyl lactyllactate of the technology of the present invention is prepared with 1:1 or the condensation of higher molar ratio.Containing hydroxyl The compound of base can be fatty alcohol or alkoxylated alcohol, and can be containing two or more hydroxyls (preferably two or Multiple primary hydroxyls) polyalcohol or alkoxylated polyalcohol.Preferably, using the lactide and hydroxyl of equimolar amounts Compound.Selectively, the compound or excessive lactide of excessive hydroxyl can be used, but at least some Using it is less preferable for doing so.

Selectively, the alkyl lactyllactate of the technology of the present invention (such as Pfansteihl, D-ALPHA-Hydroxypropionic acid or outside can be disappeared by lactic acid Revolve lactic acid) and hydroxyl compound for example alcohol preparation.Gained reaction product generally comprises one or more alkyl lactyllactates With the mixture of one or more lactic acid alkyl esters.Technology offer of the present invention is improved to prepare lactoyl cream through lactic acid route The method of acid alkyl ester.In technology of the present invention, the method that can will prepare alkyl lactyllactate through lactic acid route Referred to as lactic acid method, and the method through lactide route can be known as lactide method.It has been found that the method institute with the prior art Getable one or more alkyl lactyllactates compare the ratio of one or more lactic acid alkyl esters, the technology of the present invention Reaction product prepared by one or more lactic acid methods has the one or more alkyl lactyllactates unexpectedly improved To the ratio of one or more lactic acid alkyl esters.

The compound (including primary alconol, secondary alcohol or tertiary alcohol) that hydroxyl as described above can be used to react with lactic acid.? It is found that at least in some embodiments, by using primary alconol, one or more dilactic acids in reaction product can be improved The ratio of Arrcostab and one or more lactic acid alkyl esters.It is similar with above-mentioned lactide method, it is preferable that be prepared using lactic acid Any solvent is not used in the method for the alkyl lactyllactate of the technology of the present invention.Unexpectedly, it has been found that by using The lactic acid method of the technology of the present invention of solvent-free reaction system, obtained reaction product can have ideal dilactic acid ester pair The distribution of lactate and/or high polymer.It is preferably based on one of product or a variety of alkyl lactyllactates and lactic acid alkyl The total weight of ester, alkyl lactyllactate product prepared by the lactic acid method of the technology of the present invention include at least about 40% a kind of or more Alkyl lactyllactate is planted, optionally at least about 50% one or more alkyl lactyllactates, and such as GC (gas-chromatography) Analysis is measured, and is more preferably higher than the dilactic acid alkyl that about 0.8:1 is most preferably from above about 1:1 with greater than about 0.5:1 Ratio of the ester to lactic acid alkyl ester.

The lactic acid method of the technology of the present invention is different from the prior art, is a difference in that for example using catalyst (such as to toluene Sulfonic acid) and/or used lactic acid and one or more hydroxyls compound ratio it is higher.This two response variables can Increase the amount of the one or more alkyl lactyllactates (such as lauryl lactyllactate (L3)) generated in reaction, and reduces institute The amount of the one or more lactic acid alkyl esters (such as Lauryl lactate (L2)) generated.The example of workable catalyst include but It is not limited to sulfuric acid (H₂SO₄), HCl, methanesulfonic acid, etherate of trifluoroboron (BF₃Etherate), p-methyl benzenesulfonic acid (pTSA), phosphoric acid WithIonomer.Methanesulfonic acid, etherate of trifluoroboron and pTSA are preferred.In at least one embodiment, PTSA is most preferred.Preferably for compound (such as fatty alcohol or a variety of rouge of one or more hydroxyls of every equivalent The mixture of fat alcohol), using the lactic acid of at least about 4 equivalents, the lactic acid of at least about 6 equivalents is optionally used, optionally using extremely The lactic acid of few about 8 equivalents.

At least for some applications (such as personal care applications) of the technology of the present invention, Pfansteihl is preferred, but D-ALPHA-Hydroxypropionic acid or racemic lactic acid can be used.Preferably, the lactic acid is prepared with fermentation method.The reaction temperature of the lactic acid method is excellent About 120 DEG C to about 200 DEG C are selected as, optionally about 180 DEG C to about 185 DEG C.

The alkyl lactyllactate composition obtained using the lactic acid method of the technology of the present invention is different from the prior art (such as beauty State's patent 3,144,341) lactic acid method obtained in alkyl lactyllactate composition, and the former have significantly higher cream Acyl lactic acid ester content.For example, the total weight based on alkyl lactyllactate and lactic acid alkyl ester in desired reaction product, this hair The reaction product of the lactic acid method of bright technology can preferably include at least about 40% alkyl lactyllactate, optionally at least about 50% alkyl lactyllactate.In comparative study, it has been found that based on alkyl lactyllactate and lactic acid alkyl in reaction product The total weight of ester, reaction product prepared by lactic acid method described in United States Patent (USP) 3,144,341 only includes about 20% or less Alkyl lactyllactate.Lactic acid method institute because the amount of the alkyl lactyllactate component is higher, with the prior art The alkyl lactyllactate composition of preparation is compared, alkyl lactyllactate composition prepared by the lactic acid method of the technology of the present invention Different and/or better properties can be presented.For example, when the reaction product of the lactic acid method of the technology of the present invention is used for personal shield Ought to use or care and household application in when, compared with the reaction product of the lactic acid method of the prior art, the former can result in improved Tackifying.

The alkyl lactyllactate of the technology of the present invention can in different forms, this depends on starting material.For example, it can To be the chiral dilactic acid ester for reacting preparation with alcohol by chiral lactide (L- lactide or D- lactide), pass through meso Lactide or rac-lactide react the racemic dilactic acid ester of preparation with alcohol, by L- lactide and Study of Meso-Lactide Mixture reacted with alcohol preparation alkyl lactyllactate mixture and cream is made by using the method for the technology of the present invention Acid reacts the lactic acid alkyl ester of preparation and the mixture of alkyl lactyllactate with alcohol.The alcohol preferably include at least one primary Hydroxyl.It is highly preferred that the alcohol is fatty alcohol.

Unexpectedly, it has been found that the alkyl lactyllactate of the technology of the present invention such as lauryl lactyllactate is for being used as Surfactant is ideal.The preferred alkyl lactyllactate of the technology of the present invention is derived from natural and to be substantially free of Salt.The alkyl lactyllactate of the technology of the present invention preferably has specific chirality, and can be L- dilactic acid ester, D- cream Acyl lactate, L, D/D, L- racemic dilactic acid ester, L, L/D, D- racemic dilactic acid ester or their mixture.Root According at least some embodiments, the total weight based on products therefrom, dilactic acid prepared by the lactide method of the technology of the present invention Alkyl ester product is one or more preferably comprising more than about 90% one or more alkyl lactyllactates and less than about 10% Lactic acid alkyl ester.Selectively, the alkyl lactyllactate of the technology of the present invention can be the lactic acid legal system of technology through the invention The mixture of standby one or more alkyl lactyllactates and one or more lactic acid alkyl esters.Preferably, such as gas-chromatography Analysis is measured, and it is optimal that there is mixture of reaction products prepared by lactic acid method greater than about 0.5:1 to be more preferably higher than about 0.8:1 It is selected as the dilactic acid ester of greater than about 1:1 (for example, about 1.4:1) and the ratio of lactate.It is not intended to be bound by any specific reason By in some applications for example in hard surface cleaner, comprising some lactic acid alkyl ester quilts in surface activator composition It is regarded to improve the performance of composition by improving the ability that surfactant is accumulated in micella.

At least some preferred alkyl lactyllactate compounds of the technology of the present invention are clarified colorless liquids in room temperature, and And be free from nitrogen, it is salt-free and 100% active matter.Preferably, the lactoyl can be prepared in low-temperature mixed application Lactic acid alkyl ester.At least some alkyl lactyllactates of the technology of the present invention are capable of providing improved performance (such as better skin Sense, improved decortication (skin sloughing), enhancing foaming characteristic, improved tackifying etc.), improved cost structure (example Amount such as by reducing active matter) and/or improved stability.In addition, at least some of described alkyl lactyllactate as Conventional auxiliary surfactant is equally mild, or than conventional auxiliary surfactant milder, the conventional auxiliary surface is living Property agent is, for example, alkyl ether sulfate, glycine betaine, both sexes acetate, amide or sulfosuccinate.The lactoyl of the technology of the present invention Lactic acid alkyl ester is also used as emulsifier or skin sense agent.For household cleaning product, industrial and public cleaning product, because Surfactant properties as described above, at least some of alkyl lactyllactate of the technology of the present invention are capable of providing improved Property.In addition, they can also improve such as wetting power or other surface modification powers, and facilitate dirt/particle or The emulsification or dispersion of other formulation ingredients.

At least some alkyl lactyllactates of the technology of the present invention can be used as rheology modifier with as needed improving or Reduce the viscosity of composition.It has been found that by the way that at least one alkyl lactyllactate of the technology of the present invention is incorporated into surface In surfactant system, it can make surfactant system that there is comparable viscosity number, and the level of electrolyte (such as NaCl) is Significantly lower.On the other hand, it has also been found that, by the way that at least one alkyl lactyllactate of the technology of the present invention is incorporated into In fabric softener, the viscosity of the fabric softener composition can be reduced significantly.

The example of the personal care articles and other application that may include the alkyl lactyllactate of the technology of the present invention include but It is not limited to:

● personal cleansing product (such as soap slab, bubble bath, shampoo, body wash, facial cleanser (facial Cleaner), hand soaps, shower gels (shower gel), wipe articles (wipe), baby cleansing product (baby cleansing Product) etc.)；

● cream (cream)/lotion (lotion) (such as lotion, anti-aging skin care cream with preventing coating protection effect (anti-aging cream) (AHA (alpha-hydroxy acid), BHA (beta hydroxy acid)), blast lotion (lightening lotion) increase White lotion (brightening lotion), the lotion containing antioxidant, tanned lotion (tanning lotion) etc.)；

● cosmetic product (cosmetic product) (such as cosmetics (make-up), mascara, lipstick)；

● hair treatment articles (such as hair conditioner, hair sprays (hair spray), hair gel etc.)；

● (dish washing detergent is washed for household product or industrial goods or public article (institutional product) Clothing detergent, heavy duty detergent, light-duty detergent, fabric softener, spot inorganic agent (spot treatment), hard table Surface cleaning agent, degreasing agent and/or disinfectant are (such as those of table top, utensil, ground and wall degreasing agent in kitchen And/or disinfectant), bathroom detergent and disinfectant be (such as washroom (toilet), bathtub, shower bath, ground and wall Those of wall bathroom detergent and disinfectant), polisher etc.)；

● antiperspirant/deodorant (solid, ballpoint (roll-on) etc.)；And

● bath oil and gloss agent (hair shine).

Total weight based on product, personal cleanliness's articles or household product such as shampoo, soap bar or hard surface cleaner are excellent Selection of land includes about 0.01% to about 30%, optionally about 0.01% to about 20%, and optionally about 0.01% to about 10%, optionally About 0.1% to about 2%, the optionally alkyl lactyllactate of about 0.01% to about 0.5% the technology of the present invention.Based on the total of product Weight, the dish washing detergent (dish detergent) or laundry detergent of liquid preferably include about 0.1% to about 40%, can Selection of land about 0.1 to about 30%, optionally about 0.1 to about 25%, optionally about 0.1 to about 20%, optionally about 1 to about 25%, The optionally alkyl lactyllactate of about 3 to about 20% the technology of the present invention.

Total weight based on product, cream/lotion product preferably include about 0.01% to about 75%, and optionally about 0.01% To about 60%, optionally about 0.01% to about 50%, optionally about 0.01% to about 40%, optionally about 0.01% to about 30% The alkyl lactyllactate of the technology of the present invention.

Bath oil or gloss agent product preferably include by weight about 0.01% to about 100%, optionally about 1% to At least one alkyl lactyllactate of about 80% the technology of the present invention.

Total weight based on product, hair treatment articles such as hair conditioner, hair gel or hair sprays preferably wrap Containing about 0.01% to about 35%, optionally about 0.01% to about 25%, optionally about 0.01% to about 15% the technology of the present invention At least one alkyl lactyllactate.

Total weight based on product, Solid antiperspirant preferably include about 0.01% to about 80%, and optionally about 0.01% To about 50%, optionally at least one alkyl lactyllactate of about 0.01% to about 35% the technology of the present invention.

On the other hand, based on the total weight of product, ballpoint antiperspirant preferably includes about 0.01% to about 20%, optionally About 0.01% to about 10%, optionally at least one alkyl lactyllactate of about 0.01% to about 5% the technology of the present invention.

The cleaning compositions of alkyl lactyllactate comprising the technology of the present invention are preferably also comprising at least one or more of Other organic or inorganic surfactants, such as anionic surfactant, cationic surfactant, non-ionic surface are living Property agent, amphoteric surfactant or zwitterionic surfactant, their derivative or their mixture.These surfaces are living Property agent be it is known in the art, describe in such as United States Patent (USP) 3,929,678 (Laughlin et al.), be incorporated into this herein Text is as reference.The example of workable cationic surfactant also includes United States Patent (USP) 4,295,217 (Murphy) and 4, The two, is incorporated herein by reference by cationic surfactant those of described in 222,905 (Cockrell) herein.According to Some embodiments, one of cleaning compositions or a variety of other surfactants can be accounted in terms of the weight of cleaning compositions About 1% to about 95%, optionally about 2% to about 70%, optionally about 2% to about 30%, optionally about 3% to about 10%.

The example for the common nonionic surfactant that can be used together with the technology of the present invention includes but is not limited to alkyl Phenol ethoxylate (alkyl phenol ethoxylate), alcohol alkoxylates C8-18EO2-12 (alcohol Alkoxylate C8-18EO 2-12), alkyl dimethyl amine oxide or alkylamidopropyl group dimethylamine oxide (alkyl amidopropyl dimethyl amine oxide), MEA (monoethanolamine) type or DEA (diethanol amine) type alkanol Amide, alkyl polyglycoside (alkyl polyglycoside), ethoxylated alkanolamide and their mixture.For laundry group It closes object and hard-surface cleaning compositions, alcohol alkoxylates and amine oxide is e.g. preferred.

The example of anionic surfactant includes but is not limited to alcohol sulfate, alcohol alkoxy sulfate (alcohol Alkoxy sulfate), alkylbenzene sulfonate, alhpa olefin sulfonate, α sulfo group C₈To C₁₈Fatty acid methyl ester (mono-salt and/or disalt) Or α sulfo group C₈To C₁₈Fatty-acid ethyl ester (mono-salt and/or disalt) (alpha sulfo methyl or ethyl esters of C8through C18fatty acids (mono and/or di-salts)), sulfosuccinate and their mixture.It is excellent Selection of land, the alkyl in anionic surfactant have about 8 to about 18 carbon atoms.The counter ion of anionic surfactant can To be such as sodium, potassium, triethanolamine (triethanol amine), monoethanolamine (monoethanol amine), ammonia (ammonia), magnesium etc..For the dish washing detergent of laundry detergent and liquid, preferred anionic surfactant include but It is not limited to alkylbenzene sulfonate, alkyl ethoxy sulfate and α sulfo group C_12-18Fatty acid methyl ester (alpha sulfo methyl ester C12-18).For hard-surface cleaning compositions, preferred anionic surfactant includes such as alkyl benzene sulphonate Salt, alcohol sulfate and alkyl ethoxy sulfate.

The example of amphoteric surfactant includes but is not limited to sulfobetaines (sultaine), glycine betaine, alkyl-dimethyl Base glycine betaine or alkylamidopropyl group dimethyl betaine, alkyl dimethyl amine oxide or alkylamidopropyl group dimethyl Amine oxide, alkyl both sexes (list or two) acetic acid mono-sodium salt or disodium salt (mono-or di-sodium alkyl ampho (mono-or di) acetate), propionate (proprionate), sarcosinate and their mixture.For the meal of liquid Has detergent, preferred amphoteric surfactant includes such as glycine betaine and amine oxide.For laundry detergent and hard surface Cleaning compositions, preferred amphoteric surfactant include such as amine oxide.

It can include but is not limited to dioxane with the example of quaternary ammonium compound associated with the alkyl lactyllactate of the technology of the present invention Base alkyl dimethyl ammonium chloride, zephiran/alkyl diethyl benzyl ammonium chloride (alkyl dimethyl Benzyl/ethyl benzyl ammonium chloride), zephiran and their mixture.When When the product of alkyl lactyllactate containing the technology of the present invention is hard surface disinfectant or sanitizer, preferably by the season Ammonium compound is positioned as antimicrobial articles, and should kill target organism with effective quantity use.

Foam is provided and is removed from skin and hair because anionic surfactant and zwitterionic surfactant have Degranulation dirt is without leading to ability that is dry or stimulating, so they are combined with the alkyl lactyllactate of the technology of the present invention Preferred surfactant for cleaning compositions.Available anionic surfactant especially includes United States Patent (USP) 3,929, Institute in anionic surfactant and United States Patent (USP) 4,199,483 (Jones) those of described in 678 (Laughllin et al.) Anionic surfactant those of is stated, is herein incorporated herein by reference this two patents.

When the alkyl lactyllactate of the technology of the present invention is used as by least one embodiment of technology according to the present invention When people nurses cosurfactant (co-surfactant) in liquid cleansing composition, the personal nursing cleaning liquid group It closes object and preferably includes about 0.1% to about 95%, optionally about 1% to about 70%, optionally about 1% to about 30%, optionally About 1% to about 10%, optionally about 1% to about 5% other surfactants；About 0.1% to about 15%, optionally about 0.1% to about 5%, optionally at least one alkyl lactyllactate of about 0.1% to about 2% the technology of the present invention.It will for example, working as When sigma pump foam maker (finger pump foamer) is used as packaging system (packaging system), it can be used Low-down least concentration.Sigma pump foam maker known to those skilled in the art is can be with low-down surfactant Concentration delivers the very effective packaging system of excellent foam.It can reduce with above-mentioned delivery system (delivery system) Production cost.

The example of preferred detergent system (detergent system) for personal care cleansing agent is this field What technical staff was easy to know, and may include the combination of anionic surfactant and amphoteric ion cosurfactant. United States Patent (USP) 5,705,147 (Shapiro et al.) provides the above-mentioned surfactant for being used to prepare personal care cleansing agent Detailed description is incorporated into herein herein as reference.For example, being mixed when by the alkyl lactyllactate of technology of the present invention It is of the present invention when into the preparation containing surfactant mixture described in United States Patent (USP) 5,705,147 (Shapiro et al.) The alkyl lactyllactate of technology can enhance the organoleptic attribute (organoleptic of viscosity, fluid ability and foam stability characteristics).The brief list of typical surfactant for personal nursing detergent may include alkylsurfuric acid Salt and aryl-sulfate, alkylsulfonate and arylsulphonate, alkyl ether sulfate and aryl ether sulfate, as glycine betaine Aliphatic quaternary ammonium compound known in the art derivative.

The detergent composition of total weight based on preparation, the alkyl lactyllactate containing the technology of the present invention preferably includes About 0.01% to about 10%, optionally about 0.1% to about 5% active matter is at least one alkyl lactyllactate.

For example, the heavy duty liquid detergent preparation or light dirt type liquid detergent preparation of the technology of the present invention preferably include Lauryl lactyllactate (L3) as cosurfactant (is available from Stepan Company, Northfield, IL, commodity It is entitled) and anionic surfactant L3.In above-mentioned application, the total weight based on preparation, one The amount of kind or a variety of lauryl lactyllactates can be such as 1.5% activity for the heavy duty detergent laundry formulations without enzyme Object；It can be such as 3% or 1.5% for light-duty laundry formulations or manual dishwashing formulations.Yin suitable for above-mentioned preparation The example of ionic surface active agent include but is not limited to dodecyl benzene sulfonate, polyoxyethylene lauryl ether (3EO) sodium sulphate, Polyoxyethylene lauryl ether (2EO) sodium sulphate and 2- sulfomethyl palmitate sodium (sodium methyl-2- Sulfopalmitate)/2- sulfo group palm acid disodium (disodium 2-sulfopalmitate).

As another example, lauryl lactyllactate can be used as super dishwashing detergent formulations (ultra dish Wash detergent formulation) in auxiliary surfactant, based on its dosage of total preparation be less than about 0.5% activity Object, such as based on total preparation be down to about 0.1% active matter.When lauryl lactyllactate is only in preparation to help surface-active When agent, and in the application for being used together lauryl lactyllactate with other cosurfactants, above range is to close Suitable.On the contrary, the total weight based on preparation, one or more auxiliary tables that conventional super dishwashing detergent formulations are generally comprised The amount of face activating agent is about 0.5% active matter to about 3.5% active matter.

The alkyl lactyllactate of the technology of the present invention can be used as helping in the composition containing different primary surfactants Surfactant, the primary surfactant are, for example, alkyl sulfate, alkyl ether sulfate, alkene sulfonate, benzene sulfonamide Alkali metal salt, alkali salt, amine salt or the ammonium salt of acid, alkylbenzene sulfonate and above-mentioned substance.The example of primary surfactant Including but not limited to NaLS (SLS), sodium laureth sulfate (SLES), sodium cocosulfate (sodium coco sulfate), lauryl glucose carboxylic acid sodium (sodium lauryl glucose carboxylate), the moon Osmanthus base glucoside sodium (sodium lauryl glucoside), polyoxyethylene lauryl ether ammonium sulfate, triethanolamine lauryl base sulphur Hydrochlorate (triethanolamine lauryl sulfate), poly- Plantacare 818 carboxylate (poly decyl glucoside ) and the combination of the derivative and above-mentioned substance of above-mentioned substance carboxylate.The alkyl lactyllactate of the technology of the present invention is available It is combined in the conventional or new auxiliary surfactant of substitution or with conventional or new auxiliary surfactant, it is described conventional or new Auxiliary surfactant be, for example, amide, glycine betaine, sulfobetaines and alkyl polyglucoside (alkyl polyglucoside).The example for the auxiliary surfactant that can be replaced or be supplemented with the alkyl lactyllactate of the technology of the present invention Including but not limited to cocamidopropyl betaine, acyl lactate (acyl lactylate) such as lauroyl lactoyl Sodium lactate (sodium lauroyl lactylate), both sexes acetate such as N- cocoamidoethyl-N- Hydroxy-ethylamino Sodium acetate (sodium cocoamphoacetate), sulfosuccinate such as sulfosuccinic acid two (2- ethylhexyl) sodium (sodium di (2-ethylhexyl) sulfosuccinate), lauryl glucoside (lauryl glucoside), cocounut oil acyl The derivative of base sodium glutamate, the amide based on monoethanol and diethanol such as cocoyl monoethanolamine and above-mentioned substance and above-mentioned The combination of substance.

Unexpectedly, it has been found that containing this hair compared with the surfactant blend without alkyl lactyllactate The surfactant blend of the alkyl lactyllactate (such as lauryl lactyllactate) of bright technology or containing the technology of the present invention The surfactant blend of the mixture of alkyl lactyllactate has significant lower critical micelle concentration (CMC).For example, Compared with the comparative surfactant solution of the alkyl lactyllactate without the technology of the present invention, the lactoyl containing the technology of the present invention The composition of lactic acid alkyl ester shows the reduction of critical micelle concentration, reduces about 5% to about 99%, optionally about 30% to about 99%, optionally about 85% to about 99%.Comparative surfactant solution can be composition, and the composition includes and institute The similar face bioactivator activity object of the essentially identical concentration of the composition of the technology of the present invention of research, but do not include the technology of the present invention Alkyl lactyllactate.And it is therefore not desirable to it is bound by any specific theory, at least some dilactic acids of the technology of the present invention Arrcostab is believed to the mildness for improving detergency and potentially improving primary surfactant.

In general, surfactant tends to take up the space of air/water or liquid/liquid interface.Each surface-active Agent molecule occupies certain surface area, and occupied surface area is controlled by the molecular structure of surfactant.In surfactant In the case where mixture, area occupied by each molecule (area/molecule) depends not only on each individual surfactant The molecular structure of molecule, but also depend on how different molecular arranges and how to interact each other.When When intermolecular interaction reduces total repulsive force, each surfactant molecule can occupy smaller face in interface Product.This phenomenon is referred to as " reducing area/molecule (recude area/molecule) ".

Unexpectedly, it has been found that in surfactant blend, at least some dilactic acids of the technology of the present invention Arrcostab (such as lauryl lactyllactate) can improve packing of molecules and reduction of the primary surfactant at air/water interface " area/molecule ".For example, compared with the comparative surfactant solution of the alkyl lactyllactate without the technology of the present invention, The composition of some alkyl lactyllactates containing the technology of the present invention shows the reduction of area occupied by each molecule, reduces About 2% to about 80%, optionally about 10% to about 60% (such as 35% or 45%).

Furthermore, it has surprisingly been found that with the conventional surfactants for containing such as glycine betaine or amide and SLES-2 System is compared, the surfactant body of alkyl lactyllactate and primary surfactant (such as SLES-2) containing the technology of the present invention System can be such that air/water interface is quickly saturated and have lower dynamic surface tension (dynamic surface Tesion) (dosage is identical).And it is therefore not desirable to it is bound by any specific theory, at least some lactoyls cream of the technology of the present invention Acid alkyl ester is believed to potentially improve quick blistering (flash foam) and the foam volume of surfactant system (foam volume).It is also unexpectedly found that, is prepared by L- lactide and the mixture or L- lactide of Study of Meso-Lactide Dilactic acid ester can preferably generate foam than racemic dilactic acid ester.

At least one embodiment of technology according to the present invention includes this hair in Aquo System (aqueous system) The alkyl lactyllactate of bright technology and the composition of primary surfactant can also be comprising buffer (buffer) to improve State the high-temperature stability of composition.Times suitable for personal care articles, household product or industrial goods and public article can be used What primary surfactant and buffer.The example of buffer system include but is not limited to citric acid/sodium citrate buffer, lactic acid/ Ammonium lactate buffer or their combination.Be not intended to be bound by any specific theory, in the technique of the present invention it is observed that It arrives, the high-temperature stability of the composition can be greatlyd improve by using buffer.For clean applications, every kind of surface is living Property agent system can have the different buffer systems of various concentration.The known test that can be understood by those skilled in the art Determine the appropriate amount of required buffer, and the amount depends on dilactic acid ester and other active matters used in preparation Level.Generally, based on the weight of preparation, the level of the buffer can be about 0% to about 1%, optionally about 0.1% to About 0.75%, optionally about 0.1% to about 0.5%.

Other than Aquo System, the alkyl lactyllactate of the technology of the present invention can also be configured to solid form, coagulated The personal care articles or other application of glue form or other forms.For example, can be by the alkyl lactyllactate of the technology of the present invention It is added in soap bar as cosurfactant.With the conventional auxiliary surfactant such as Cocamidopropyl sweet tea for soap bar Dish alkali is compared with cocoyl monoethanolamine, at least some alkyl lactyllactates of the technology of the present invention (such as be available from The trade name of Stepan CompanyThe lauryl lactyllactate (L3) of L3) improvement can be presented Frothing capacity and the orientations (directional) of most of skin sense attributes is improved.It has been found that the technology of the present invention is at least Some alkyl lactyllactates (such as the lactoyl cream prepared by L- lactide and the mixture or L- lactide of Study of Meso-Lactide Acid alkyl ester) plasticity of soap bar during processing can be improved, this is implied to the fracture (cracking) of item, broken (clipping) and peel off (peeling) play the role of it is positive without influencing rinsability and wet feeling (wet feel) characteristic.

Some embodiments of technology, the total weight based on soap bar, soap bar preferably include (1) about according to the present invention The alkyl lactyllactate of 0.01% to about 30% the technology of the present invention, (2) about 0 to about 50% synthetic surfactant, (3) about 0 To the mixture of about 30% at least one α sulfonated alkyl ester, at least one alpha-sulfonated fatty acid or above-mentioned substance, (4) about 30% to About 95%C₆-C₂₂Soap, (5) about 0.5% to about 30%C₆-C₂₂Fatty acid, (6) about 0.1% to about 5% electrolyte, (7) about 0.5% to about 15% polyalcohol, and (8) about 3% to about 22% water.

It alternatively it can be based on the total weight of soap bar, the soap bar may include (1) about 0.01% to about 10% skill of the present invention The alkyl lactyllactate of art, (2) about 0 to about 20% synthetic surfactant, (3) about 0 to about 15% at least one α sulfolane The mixture of base ester, at least one alpha-sulfonated fatty acid or above-mentioned substance, (4) about 30% to about 95%C₆-C₂₂Soap, (5) about 0.5% To about 10%C₆-C₂₂Fatty acid, (6) about 0.1% to about 3% electrolyte, (7) about 0.5% to about 10% polyalcohol, and (8) are about 3% to about 22% water.

It alternatively it can be based on the total weight of soap bar, the soap bar may include (1) about 0.01% to about 5% skill of the present invention The alkyl lactyllactate of art, (2) about 0 to about 10% synthetic surfactant, (3) about 0 to about 10% at least one α sulfolane The mixture of base ester, at least one alpha-sulfonated fatty acid or above-mentioned substance, (4) about 30% to about 95%C₆-C₂₂Soap, (5) about 0.5% To about 5%C₆-C₂₂Fatty acid, (6) about 0.1% to about 2% electrolyte, (7) about 0.5% to about 6% polyalcohol, and (8) about 3% To about 22% water.

According at least one other embodiment, one or more alkyl lactyllactates of the technology of the present invention be may include In all purpose cleaner concentrate, its dosage of the total weight based on the concentrate is for example, about 0.01% to about 10% activity Object, optionally about 0.1% to about 5% active matter.

According at least one other embodiment, one or more alkyl lactyllactates of the technology of the present invention be may include In instant detergent, its dosage of the total weight based on the detergent is for example, about 0.01% to about 10% active matter, can About 0.1% to about 5% active matter of selection of land.

One or more alkyl lactyllactates of the technology of the present invention also may be embodied in glass cleaner, based on described Its dosage of the total weight of detergent is for example, about 0.01% to about 2% active matter.

In addition, one or more alkyl lactyllactates of the technology of the present invention may be embodied in bathroom detergent, it is based on Its dosage of the total weight of the detergent is for example, about 0.01% to about 10% active matter.

Moreover, one or more alkyl lactyllactates of the technology of the present invention also may be embodied in liquid scrub clean agent In (liquid scouring cleaner), its dosage of the total weight based on the detergent is for example, about 0.01% to about 10% active matter.

One or more alkyl lactyllactates of the technology of the present invention also may be embodied in dishwashing detergent powder or tableware is washed It washs in gel (dishwashing powder or gel), its dosage of the total weight based on the preparation is for example, about 0.01% To about 5% active matter.

One or more alkyl lactyllactates of the technology of the present invention can also be added to carpet spotter (carpet Traffic spotter) in, its dosage of the total weight based on the composition is for example, about 0.1% to about 8% active matter.

Following abbreviations can be used in the application, in particular in embodiment:

SLES-2 or CS-230: lauryl polyoxyethylene (2) ether sodium sulfate, it can be withCS-230 (26% active matter

Sodium laureth sulfate) derive from Stepan Company

LMDO: lauroyl aminocarbonyl propyl amine/myristamide propyl amine oxide, it can be with

LMDO (33% active matter) derives from Stepan Company

HCG or CAPB: cocamidopropyl betaine, it can be withHCG (31% active matter)

Commercially available from Stepan Company

LL: dilactic acid ester

C₁₂LL or LLL or L3: lauryl lactyllactate, it can be with trade nameL3 (100% active matter)

Commercially available from Stepan Company

C₁₈LL or SLL: dilactic acid stearyl ester

L2: Lauryl lactate

NEODOL 25:C_12-15Fatty alcohol (can be with trade name25 commercially available from Shell Oil Company)

NEODOL 45:C_14-15Fatty alcohol (can be with trade name45 commercially available from Shell Oil Company)

NEODOL 67:C_16-17Fatty alcohol (can be with trade name67 commercially available from Shell Oil Company)

BRIJ 78: polyoxyethylene (20) stearyl ether (can with trade name BRIJ 78 from ICI Americas,

Commercially available from Incorporated)

IPP: isopropyl palmitate, it can be commercially available from HallStar Company, Chicago, IL

GMS: glycerin monostearate, it can be withGMS PURE (100% active matter)

Commercially available from HallStar Company

Cetyl Alcohol: cetanol, also referred to as palmityl alcohol

NaCl: sodium chloride

CMC: critical micelle concentration

COMF: cocoyl monoethanolamine (Cocamide MEA), it can be withCOMF (100%

Active matter) commercially available from Stepan Company

SLS: NaLS, it can be withWA-Extra (29% active matter) from

Commercially available from Stepan Company

DCFAS or SCS: sodium cocosulfate, it can be withDCFAS (100% active matter) from

Commercially available from Stepan Company

SLL-FB: lauroyl dilactic acid sodium, it can be withSLL-FB is from Stepan Company

It is commercially available

CS-370: lauryl polyoxyethylene (3) ether sodium sulfate, it can be withCS-370 (70% active matter)

Commercially available from Stepan Company

CS-270: lauryl polyoxyethylene (2) ether sodium sulfate, it can be withCS-270 (70% active matter)

Commercially available from Stepan Company

16 2- sulfomethyl palmitate sodium of MES/2- sulfo group palm acid disodium, can be commercially available from Stepan Company

By reference to the following example, it is better understood with technology and its advantages of the present invention.These realities are provided The purpose for applying example is to describe the specific embodiment of the technology of the present invention.Applicant comes not by these specific embodiments are provided Limit the scope and spirit of the technology of the present invention.It will be understood by those skilled in the art that the full scope of technology of the present invention includes Theme defined in any transformation of appended claims and these claims, modification or equivalent form.

Embodiment

Viscosity salt response test method (Viscosity Salt Response Test Method)

The method of the viscosity salt response of the measurement composition used in embodiments herein can be as described below:

1. surface activator composition needed for preparation, and its pH is adjusted to about 5 to about 6.

2. sample composition is poured into a series of bottles with the amount of about 100 grams of solution.

3. different amounts of anhydrous sodium chloride is added in the solution.Solution is sufficiently mixed until salt is completely dissolved.

4. a pair sample is centrifuged or is ultrasonically treated, and is balanced to 25 DEG C.

5. using Brookfield Viscometer Helipath Stand (Brookfield Engineering Laboratories, Inc., Middleboro, MA) use mandrel 4 with the viscosity of the measurement sample of speed 20.

Shaking blistering method of testing (Shake Foam Test Method)

The method of the frothing capacity of the measurement composition can be as described below used in embodiments herein:

1. preparing 0.2% active matter sample solution in 25 DEG C of tap water (tap water).If active matter is horizontal (active level) is unknown, then prepares 0.2% solid solution (0.2%solid solution).

2. 0.2% sample solution of 100.0g+/- 0.01g is added in 500mL measuring graduates.Make initial foam most It is few.

3. 2.0g+/- 0.01g castor oil is added in the measuring graduates, and plug is placed on the graduated cylinder.

4. the measuring graduates is placed in shaking frothing machine (shake foam machine), and by clip (clamp) It is fixed at the rubber stopper.

5. being set to shaking frothing machine to overturn the graduated cylinder 10 times.

6. settling foam 15 seconds.Read total foam height (including substrate i.e. 100mL solution).

7. after five minutes, reading again foam height as in step 6 and recording.

Skin sense method of testing (skin feel test method)

Skin sense method of testing can also be known as hand-washing method of testing.People is evaluated into method of testing (human in-vivo in body Panel test method) for evaluating clean body preparation (body wash formulation) in embodiment.According to This method, hand washing test using warm (about 95 ℉ to 105 ℉ or about 35 DEG C) hardness be about such as 150ppm (1.8/1Ca: Mg tap water) carries out.In testing, if test product is the body cleansing composition of liquid, by 1mL test product point It is assigned to the wet palm of evaluation member (panelist).Member at foam by washing one's hands the product treatment 30 seconds for evaluation, Then it rinses 15 seconds.If the test product is soap bar, the hand that member moistens them with water-wet is evaluated；By in their hand Half rotation (half bar rotation) that 5 soap bars are carried out in the palm carrys out their hand of prewashing；Their hand 25 seconds is handled to produce Raw foam；Then their hand is rinsed 15 seconds.Washing procedure is repeated once.Foam is collected in meter glass and surveyed Amount.Hand is rinsed 15 seconds at circulating water (running water) and is dried with paper handkerchief (paper towel).Then it evaluates into Member is easy to the property applied (ease of application), wet stage (skin sense) property to test product according to 1 to 5 grade Can and drying stage (skin sense) performance be classified, 1 is worst and 5 be best.

The people can be used for the application wide scope of evaluation clean body preparation, spatter property in body evaluation method of testing Energy and skin sensibility.Selection has neutral, stemness and moist skin type (normal, dry and moist skin type) Evaluation member for each test, skin type using NOVA moisture meter (moisture meter) (can be from Nova Commercially available from Instruments, Incorporated) it measures.NOVA reading represents dry skin less than 100；The reading of 110-130 Represent neutral skin；130 or higher readings represent moist skin.Evaluation member is required to evaluate experiment using above procedure Preparation (experimental formulation) and control formulation.For example, in some experiments, by 12% lauryl polyoxy second Alkene (2) ether sodium sulfate (SLES-2/CS-230) and 3% cocamidopropyl betaine (CAPB/HCG) (its be considered as Most popular surfactant system in body wash) it is used as reference substance.The experimental preparation tested may include not The surfactant activity object (such as 12%, 13%, 14% or 15% active matter by weight) of same amount, and contained main table Face activating agent and auxiliary surfactant can have different ratios (such as 4:1 or 14:1).Formulate application form (questionnaire) come record evaluation member body wash application during and application after reaction.

According to the application form, member is evaluated firstly the need of record environment temperature and ambient humidity and his or her NOVA skin type.Then evaluation member needs to answer 14 following problems:

1. being easy to the property applied: 1=is difficult；5=is easy

2. quick blistering/generation: 1=is difficult；5=is easy

3. it is creamy (creamy) abundant to steep scale (bubble size): 1=；Rare loose of 5=

4. foam volume: 1=almost non-foam；The a large amount of foam of 5=

5. foam feels (foam feel): 1=does not lubricate；5=lubricates very much

6. general impression: 1=is bad；5=is good

7. rinsability: 1=is difficult rinse；5=easily and readily rinse

8. wet feel (wet feel): 1=clean (squeaky clean) reluctantly；5=is clean or substantially clean

Tackiness (tackiness): 1=9. during dry tacky viscosity；5=is not tacky or inviscid

10. the skin-tightening degree (tightness) when dry: 1=is very tight；5=is not tight

11. skin moisturization (skin moisturizing): 1=is very dry；5=is not dried

12. skin softness: 1=is coarse；5=is very soft

13. overall inno logo: 1=is bad；5=is good

14. the general impression after 2-3 minutes: 1=is bad；5=is good

Record the data from evaluation member's assessment.Other than the essential information of evaluation member, application form is formulated to obtain Take evaluation member for the repercussion of product application, wet stage and drying stage.Evaluation member be required to experiment test sample/ The performance of every attribute illustrated herein of preparation and reference substance is evaluated, 1 to be worst and 5 be best.As described above, can be used Preparation with various gross activity surfactant concentrations (such as 15% active matter), the primary surfactant that the preparation includes There is different ratios (such as 4:1 ratio) from auxiliary surfactant.The pH of preparation is adjusted using citric acid or sodium hydroxide It is about 5 or about 6.By all experimental preparations and lauryl polyoxyethylene (2) ether sodium sulfate/cocamidopropyl betaine (CS- 230/HCG) reference substance or another control sample compare.For every kind of performance, between experiment with computing sample and reference substance Scoring distinctions.Average from evaluation member is used to determine directional properties between laboratory sample and a kind of reference substance (directiona performance).If the total score difference between laboratory sample and reference substance be it is positive, show to test The performance of sample is directionally better than reference substance.If the total score difference tested between body wash and reference substance is zero, tie There is same performance with reference substance by being laboratory sample preparation.If the difference between laboratory sample and reference substance be it is negative, Conclusion is that the performance test of laboratory sample is poor according to product.

Embodiment 1: preparation of the lauryl lactyllactate in room temperature

By laruyl alcohol (19.2g, 0.10mol,C 12/98, Cognis) it is fitted into the flask of nitrogen flushing. L- lactide (14.4g, 0.10mol, Aldrich) is added in solid form, and stirs mixture.A drop sulfuric acid is added, and Gained slurries are stirred at room temperature 3 days, obtain supernatant liquid later.NMR test shows that lactide converts completely.It is resulting Product is lauryl lactyllactate (LLL or C₁₂It LL), is dilactic acid C₁₂-C₁₄The mixture of ester.

Embodiment 2: dilactic acid C₁₂-C₁₈Preparation of the ester in high temperature

By C₁₂-C₁₈Alcohol (20.8g, 0.10mol,Technisch, Cognis) it is packed into the flask that nitrogen rinses In.L- lactide (14.4g, 0.10mol, Aldrich) is added in solid form, and stirs mixture.A drop sulfuric acid is added, And stir gained slurries 20 hours at 50 DEG C, supernatant liquid is obtained later.NMR test shows that lactide converts completely. Resulting product is dilactic acid C₁₂-C₁₈Ester (C₁₂-C₁₈LL mixture).

Embodiment 3: it is surveyed to using composition of the alkyl lactyllactate as auxiliary surfactant to carry out the response of viscosity salt Examination

It prepares a series of compositions (5), every kind of composition includes 12 weight % active matter SLES-2 (CS-230) and 3 weights It measures the auxiliary surfactant of % active matter (4:1 ratio).The auxiliary surfactant is (1) HCG (reference substance), (2) C₁₂-C₁₈LL、 (3)C₁₆LL、(4)C₁₈LL or (5) C₁₈(oil base) LL.

The viscosity salt response of these compositions is tested according to viscosity salt response test method as described above, is as a result being schemed It is shown in 1.

The results show that CS-230 is as primary surfactant and C₁₂-C₁₈LL、C₁₈(oil base) LL, C₁₆LL or C₁₈LL makees Supplemented by the composition of surfactant improve viscosity in the presence of proper amount of NaCl electrolyte.As a result it also shows, when When NaCl concentration is lower, CS-230 is as primary surfactant and C₁₂-C₁₈LL、C₁₈(oil base) LL or C₁₆LL is as auxiliary surface Composition ratio CS-230/HCG (control) composition of activating agent has higher viscosity number, and is based on CS-230 and C₁₈The group of LL Closing object has comparable viscosity number when NaCl concentration is low or higher with reference composition.Therefore, and based on CS-230's and HCG Composition is compared, and CS-230 and C is based on₁₂-C₁₈LL, it is based on CS-230 and C₁₈(oil base) LL is based on CS-230 and C₁₆The group of LL Closing object needs lesser amount of NaCl so as to desired viscosity.It is used in the composition of preparation the technology of the present invention by reducing Salt, also reduce the weight and corrosivity of the composition, thus cause improved products processing and longer equipment life.

Embodiment 4: it is surveyed to using composition of the alkyl lactyllactate as auxiliary surfactant to carry out the response of viscosity salt Examination

It prepares a series of compositions (5), every kind of composition includes 12 weight % active matter SLES-2 (CS-230) and 3 weights It measures the auxiliary surfactant of % active matter (4:1 ratio).Auxiliary surfactant in this embodiment is (1) HCG (reference substance), (2) C₁₂LL, (3) NEODOL 25LL, (4) NEODOL 45LL or (5) NEODOL 67LL.

The viscosity salt response of these compositions is tested according to viscosity salt response test method as described above, is as a result being schemed It is shown in 2.

The results show that being reached for the 15% active compositions containing CS-230 and LLL (4:1 ratio) in the dosage of NaCl To before about 1%, viscosity increases with the increase of NaCl electrolyte concentration.As a result it also shows, with (the 4:1 ratio containing CS-230/HCG Example) 15% active compositions compare, for the 15% active compositions containing CS-230/LLL (4:1 ratio), in NaCl Comparable viscosity number can be obtained in the case that the level of electrolyte is significantly lower.Similarly, the results show that with CS-230 is based on It is compared with the composition of HCG, when the alkyl lactyllactate that use is prepared by NEODOL 25, NEODOL 45 or NEODOL 67 When, ideal viscosity number can be obtained in the case where the level of NaCl electrolyte is significantly lower.It is managed as described above, reducing Salt required for the viscosity number thought is for example raw in terms of the storage of raw material itself and in the packaging facilities to corrosion-susceptible Significant advantage is provided in terms of producing the consumer goods.By reducing salt used in the composition of preparation the technology of the present invention, the composition Weight and corrosivity be also reduced, so as to cause easier product treatment and longer equipment life.

Embodiment 5: to use alkyl lactyllactate as auxiliary surfactant composition carry out frothing capacity test

A series of 6 kinds of compositions are prepared, every kind of composition includes 12 weight % active matter SLES-2 (CS-230) and 3 weights It measures the auxiliary surfactant of % active matter (4:1 ratio).Any oil is not added to the composition.The auxiliary surfactant is (1) HCG (reference substance), (2) C₁₂-C₁₈LL、(3)C₁₆LL、(4)C₁₈LL、(5)C₁₈(oil base) LL or (6) C₁₂LL。

The frothing capacity of every kind of composition passes through shaking blistering method of testing (also referred to as graduated cylinder Turnover testing method as described above (cylinder inversion test method)) it is tested.The frothing result of 6 kind composition of the record without castor oil (initial result and the result after 5 minutes) is simultaneously shown in FIG. 3.

It is without castor oil the results show that CS-230 is as main surface compared with CS-230/HCG (reference substance) composition Activating agent and C₁₂-C₁₈LL、C₁₆LL、C₁₈LL、C₁₈(oil base) LL or C₁₂LL has as the Experimental composition of auxiliary surfactant There is comparable or greater foam height.As a result it also shows, for the dilactic acid without castor oil tested in this embodiment Alkyl ester compositions, CS-230/C₁₂LL composition has optimal overall performance.Moreover, with CS-230/HCG reference composition It compares, CS-230/C₁₂LL composition has significant preferable frothing capacity.

Also the composition for being mixed with castor oil is tested.The results show that in the presence of castor oil, with CS- 230/HCG (reference substance) composition is compared, and CS-230 is as primary surfactant and C₁₂-C₁₈LL、C₁₆LL or C₁₂LL is as auxiliary The composition of surfactant has comparable or better frothing capacity.Moreover, the results show that in the presence of castor oil, With CS-230/HCG (reference substance) composition tested in this embodiment and contain CS-230 and other alkyl lactyllactates Composition as auxiliary surfactant is compared, and CS-230 and C is based on₁₆The composition of LL has optimal overall frothing capacity. Finally, the results show that in the presence of castor oil, with the CS-230 that is tested as primary surfactant and other dilactic acids Arrcostab is compared as the composition of auxiliary surfactant with CS-230/HCG (reference substance) composition, includes dilactic acid C₁₈Ester With dilactic acid C₁₈The composition of (oil base) ester has worst frothing capacity.

Embodiment 6: to use alkyl lactyllactate as auxiliary surfactant composition carry out frothing capacity test

A series of 5 kinds of compositions are prepared, every kind of composition includes 12 weight % active matter SLES-2 (CS-230) and 3 weights It measures the auxiliary surfactant of % active matter (4:1 ratio).Any oil is not added to the composition.The auxiliary surfactant is (1) HCG (reference substance), (2) C₁₂LL, (3) NEODOL25LL, (4) NEODOL 45LL or (5) NEODOL 67LL.

The frothing capacity of every kind of composition is tested by shaking blistering method of testing as described above.Castor oil will be free of The frothing results (initial result and the result after 5 minutes) of 5 kinds of compositions be shown in FIG. 4.

The results show that compared with CS-230/HCG (reference substance) composition, being based in the case where not adding castor oil CS-230 and C₁₂The composition of LL has better frothing capacity.As a result it also shows, in the case where not adding castor oil, with CS-230/HCG (reference substance) composition is compared, and the lactoyl cream prepared by NEODOL 25, NEODOL 45 or NEODOL 67 is included The composition of acid alkyl ester and CS-230 have comparable frothing capacity.

Also the composition added with castor oil is tested.The results show that in the presence of castor oil, comprising by The composition of alkyl lactyllactate and CS-230 prepared by NEODOL 25, NEODOL 45 or NEODOL 67 has phase each other When performance, compared with CS-230/HCG (reference substance) composition, every kind in these compositions all directionally have it is lower (i.e. slightly worse) frothing capacity.In the presence of castor oil, compared with CS-230/HCG (reference substance) composition, it is based on CS-230 And C₁₂The composition of LL still shows substantially preferable frothing capacity.As a result it also shows, the presence of citric acid/sodium citrate buffer To containing CS-230 and C₁₂The frothing capacity of the composition (composition is containing castor oil or is free of castor oil) of LL does not have significant Influence.

Embodiment 7: the composition based on alkyl lactyllactate and the softness between the composition based on HCG The comparison of (softness performance) and wet performance (moisturization performance)

A series of 5 kinds of body cleansing compositions are prepared, every kind of composition includes 12 weight % active matter SLES-2 (CS- And the 3 auxiliary surfactants of weight % active matter (4:1 ratio) 230).The auxiliary surfactant is that (1) HCG (is used as control Product), (2) C₁₂LL, (3) dilactic acid C₁₆Ester (C₁₆Lactylate), (4) oil base LL (oleyl LL) or (5) C₁₂-C₁₈LL。

The softness and wet performance of every kind of composition are tested using skin sense method of testing as described above.They with contain The relative result that the composition of HCG/CS-230 (reference substance) is compared is shown in FIG. 5.

The results show that with CS-230/HCG (reference substance) composition and based on CS-230/C₁₈The composition of (oil base) LL and Based on CS-230/C₁₂-C₁₈The composition of LL is compared, and CS-230/C is based on₁₂The composition of LL and be based on CS-230/ dilactic acid C₁₆The composition of ester has better softness and wet performance.

Embodiment 8: 25LL containing NEODOL, NEODOL 45LL, NEODOL 67LL or LLL body wash with contain HCG Body wash softness and wet performance comparison

5 kinds of body cleansing compositions are prepared, every kind of composition includes 12 weight % active matter SLES-2 (CS-230) and 3 weights It measures the auxiliary surfactant of % active matter (4:1 ratio).The auxiliary surfactant be (1) HCG (reference substance), (2) LLL (i.e. C₁₂LL), (3) NEODOL 25LL, (4) NEODOL45LL or (5) NEODOL 67LL.

Softness of the every kind of composition during clean body and wet is tested using skin sense method of testing as described above Lubricant nature energy.The relative result that they are compared with the composition containing HCG/CS-230 (reference substance) is shown in FIG. 6.

The results show that compared with CS-230/HCG (reference substance) composition, composition containing CS-230/LLL and contain CS- The composition of 230/NEODOL 67LL has better softness and wet performance.It is combined with CS-230/HCG (reference substance) Object is compared, and the composition based on CS-230/NEODOL 25LL and the composition based on CS-230/NEODOL 45LL have quite Softness and wet performance.

Embodiment 9: to containing and the stability of the LLL preparation without buffer compares research

Two kinds of LLL compositions are prepared, one kind is another containing buffer to be free of buffer.Buffer used is 0.5% Active matter sodium citrate/citric acid and 0.5% active matter ammonium lactate/lactic acid system.

In room temperature and in the stability of 50 DEG C of research, two kinds of compositions, 4 weeks are lasted.PH value in relation to two kinds of compositions and viscous The result of degree is recorded in Fig. 7.

The results show that containing buffer i.e. 0.5% active matter sodium citrate/citric acid and 0.5% active matter ammonium lactate/lactic acid CS-230/LLL composition compared with the same combination without buffer, with more stable pH and glued at 50 DEG C through 4 weeks Degree.

Embodiment 10: dilactic acid stearyl ester is in oil-in-water emulsion as the comparative study of assistant for emulsifying agent

In this embodiment the formula (formulation) as shown in following table prepare two kinds of oil-in-water (O/W) latex As and B。

Table 1

Formula	A	B (reference substance)
			Ingredient	Weight % active matter	Weight % active matter
Deionization (D.I.) water	In right amount to 100	In right amount to 100
			BRIJ 78	1.0	1.0
Dilactic acid stearyl ester	1.5	0
			IPP	10.0	10.0
GMS	1.5	1.5
			Cetanol	2.0	2.0
Preservative	In right amount	In right amount
At 25 DEG C of initial viscosities (cps)	7,200	6,000
			In 25 DEG C of viscosity (cps) after 3 days	8,600	6,000

Difference between two kinds of lotions is that latex A includes 1.5 weight % dilactic acid stearyl esters (SLL) and compares lotion B Without dilactic acid stearyl ester (SLL).It measures the viscosity (initial viscosity and the viscosity after 3 days) of two kinds of compositions and is recorded in In table.

The results show that dilactic acid stearyl ester improves the viscosity of oil-in-water emulsion.The above results allow to by more The mode of cost efficiency and cost-effectiveness (cost effective and cost efficient) uses above-mentioned dilactic acid alkane Base ester prepares final products, this is because the amount of said components used is less.

Embodiment 11: the preparation of dilactic acid palm ester

By palmityl alcohol (24.2g, 0.10mol,C 14/98, Cognis) it is fitted into the flask of nitrogen flushing. L- lactide (14.4g, 0.10mol, Aldrich) is added in solid form, and stirs mixture.A drop sulfuric acid is added, and Gained slurries are stirred about 30 hours at about 35 DEG C, obtain supernatant liquid later.NMR test shows that lactide turns completely Change.Resulting product is dilactic acid palm ester (C₁₆LL)。

Embodiment 12: the preparation of dilactic acid grease (oleyl lactyllactate)

By oleyl alcohol (26.7g, 0.10mol, HD90/95V, Cognis) it is fitted into the flask of nitrogen flushing.It will L- lactide (14.4g, 0.10mol, Aldrich) is added in solid form, and stirs mixture.Two drop sulfuric acid are added, and will Gained slurries stir about 20 hours at about 50 DEG C, obtain supernatant liquid later.NMR test shows that lactide turns completely Change.Resulting product is dilactic acid grease (C₁₈(oil base) LL).

Embodiment 13: the preparation of the different stearyl ester of dilactic acid

Isooctadecanol (13.1g, 0.05mol, Jarchem Industries, Inc., Newark, NJ) is packed into nitrogen punching In the flask washed.L- lactide (7.5g, 0.05mol, Aldrich) is added in solid form, and stirs mixture.It is added one Sulfuric acid is dripped, and gained slurries are stirred about 16 hours at about 50 DEG C, obtains supernatant liquid later.NMR test shows lactide Convert completely.Resulting product is the different stearyl ester (C of dilactic acid₁₈(iso stearyl) LL).

Embodiment 14: softness and the wet performance test of the composition containing different gross activity objects

Prepare a series of 5 kinds of body cleansing compositions.Reference composition includes 12 weight % active matter SLES-2 (CS- And 3 weight % active matter CAPB (HCG) (4:1 ratio) 230).Other 4 kinds of body cleansing compositions include that active weight ratio is The SLES-2 of the 14:1 and C of the technology of the present invention₁₂LL.The amount of gross activity object in 4 kinds of compositions is respectively 15 weight %, 14 weights Measure %, 13 weight % and 12 weight %.

The softness and wet performance of every kind of composition are tested using skin sense method of testing as described above.Three evaluations The relative result being compared with reference composition that member tests (three-panelist test) is shown in FIG. 8.

The results show that with CS-230/HCG (reference substance) composition, (composition includes the (activity of 15% active matter in total Object ratio is 4:1)) it compares, the CS-230 and C for being 14:1 based on ratio₁₂LL and include 15%, 14% or 13% active matter in total Composition all show better softness and wet performance and higher blistering (i.e. foam height).With CS-230/ HCG (reference substance) composition is compared, and containing 12% active matter in total, (ratio is the CS-230 and C of 14:1₁₂LL the technology of the present invention) Composition show comparable softness and wet performance and higher blistering.The result shows that compared with using CAPB, Only need less amount of C₁₂Comparable softness, wet performance and foam height can be obtained in LL.As a result it also shows, for body Body cleaning compositions, in order to obtain with the comparable performance of composition based on SLES-2 and CAPB, it is only necessary to less amount of total work Property object.This can reduce cost, reduce the weight of final products, and the body wash of the technology of the present invention is made to be more environment friend Alright.

Embodiment 15: to use lauryl lactyllactate or cocamidopropyl betaine as auxiliary surfactant Composition being compared property viscosity salt response test

Prepare a series of 5 kinds of body cleansing compositions.Two kinds in the composition include 12 weight % active matters SLES-2 (CS-230) is used as primary surfactant and 3 weight % active matter CAPB or C₁₂LL is as auxiliary surfactant (4:1 ratio Example).Other two kinds of compositions include 14 weight % active matter SLES-2 and 1 weight % active matter CAPB or C₁₂LL (14:1 ratio Example).A kind of last composition includes 15 weight % active matter SLES-2 and is free of any auxiliary surfactant.

The viscosity salt response of these compositions is tested according to viscosity salt response test method as described above, is as a result being schemed It is shown in 9.

The results show that the composition containing 15% active matter (SLES-2) glues when not using any auxiliary surfactant Degree is still almost as water equally dilute (water thin) (have the viscosity similar to water and be about 1cps at 25 DEG C), even It is also such when using 2.5 weight %NaCl electrolyte.On the other hand, in the presence of proper amount of NaCl electrolyte, contain CAPB or C₁₂The composition of the auxiliary surfactant of LL has increased viscosity.As a result also indicate that, when NaCl concentration is lower, with than Example is that the SLES-2/CAPB composition of 4:1 is compared, the SLES-2 and C for being 4:1 based on ratio₁₂The composition of LL has higher Viscosity number, and when NaCl concentration is low or higher, compared with ratio is the SLES-2/CAPB composition of 14:1, it is based on ratio The SLES-2 and C of 14:1₁₂The composition of LL has higher viscosity number.Therefore, as shown in Figure 9, if clean body combines The desired viscosity of object is lower than 15000cps, then for being based on SLES-2 and C₁₂The composition of LL, with based on SLES-2 and The composition of CAPB is compared, and in order to reach desired viscosity, needs the NaCl amount of much less.The present invention is used to prepare by reducing The salt of the composition of technology also reduces the corrosivity of the composition, therefore at least results in easier product treatment and more Long equipment life.

In addition, result is surprisingly shown, when NaCl amount used is 1.75% or higher, and contain 3 weight % The composition of active matter CAPB and 12 weight % active matter SLES-2 are compared, and 1 weight % active matter C is contained₁₂LL and 14 weight % The composition of active matter SLES-2 has higher or comparable viscosity number.Therefore, it glues desired by the body cleansing composition When degree is higher than 15000cps, when auxiliary surfactant used is C₁₂LL rather than when CAPB, in order to use equal amount NaCl In the case where reach desired viscosity, need less amount of auxiliary surfactant.

Embodiment 16: manual blistering (hand foaming) test and skin sensing examination of soap bar

Three kinds of bar samples are tested in this embodiment.Sample A (reference substance) is the commercially available soap bar being molded again.Sample B It is the commercially available soap bar for being handled with 2 weight % lauryl lactyllactates (L3) and being molded again again.Sample C using following substance from Prepared by head: 80/20 butter/cocounut oil soap base (tallow/coco soap base), the trip of 2% palm glycerol tristearate From fatty acid (palm stearin free fatty acid (FFA)), 4% glycine betaine, 2%L3.With commercially available soap bar (sample Product A) compare, sample C include 2% palm glycerol tristearate FFA (rather than 5-6% in sample A) and include 2%L3 with And 2%2- sulfolauric acid methyl esters sodium (sodium methyl 2-sulfolaurate) and 2- sulfolauric acid disodium (disodium2-solfolaurate) mixture (can be withBSS-45 is from Stepan Company It is commercially available).Compared with commercially available soap bar (sample A), sample C contains 2% palm glycerol tristearate free fatty acid (rather than sample 5-6% contained by product A) and contain 2%L3.

The manual blistering of every kind of composition is carried out with skin sensing examination using skin sense method of testing as described above.In Figure 10- Various comparative manual frothing results (comparative hand foaming result) are shown in 12, are shown in Figure 13-14 Various comparative skin sense results out.

In Figure 13, " rinsability " refers to the ability that product is easy to be removed after application；" wet to feel " refers to product Leave the ability felt, felt after the use of sense or basic cleaning after clean use after inadequate clean use；" tackiness " refers to humid period Between or dry converting during stickiness feeling on skin；" degree of tautness " refer to it is dry after degrees of tensions on skin；" drying " is Refer to dermal sensation dehydration and with the degree of delamination (flaking) and furfur (scaling)；And " flexibility " refers on skin Comfortable silk smooth felling feel.

The results show that adding L3 into commercially available soap bar gives significantly improving for frothing capacity, and give most of skin sense categories Property (skin feel attribute) certain improvement (i.e. orientation improve).It has been found that L3 does not influence the rinse of commercially available soap bar Property and wet sense quality.In addition, the reduction of FFA concentration does not have a negative impact to the physical property of the soap bar in sample C. In addition, observing during the processing of sample C, L3 improves the plasticity of soap bar, this imply to preventing soap bar rupture generate just Face is rung.

Embodiment 17: to different being compared property of primary surfactant viscosity salt response investigations and blistering research by hand

Three kinds of body cleansing compositions are prepared, these three body cleansing compositions include three kinds of different main surface activity Agent, and include the lauryl lactyllactate (L3) of the technology of the present invention as auxiliary surfactant, primary surfactant and auxiliary surface The active matter ratio of activating agent is 14:1.The formula of three kinds of compositions is as shown in following table.

Table 2: the composition containing different primary surfactants

Using containing 12 weight % active matter SLES-2 (CS-230) and 3 weight % active matter CAPB (HCG) (4:1 ratio) Composition is as reference substance.Three kinds of comparative compositions are also prepared for, these three comparative compositions are replaced comprising CAPB (HCG) L3 is as auxiliary surfactant, but other aspects are identical as formula shown in table 2.

Skin sense method of testing as described above is used first, is compareed with CS-230/HCG (reference substance) composition, to this Three kinds of compositions of inventive technique carry out blistering test by hand.Comparative manual frothing result is recorded in Figure 15.Then, make It with skin sense method of testing as described above, is compareed with respective comparative composition, studies three kinds of combinations of the technology of the present invention Object.Manual frothing result is shown in FIG. 16.

The results show that containing SLES-2, SLS or SCS (DCFAS) conduct compared with CS-230/HCG (reference substance) composition Primary surfactant and L3 show preferably manual frothing capacity as three kinds of compositions of auxiliary surfactant.With it is each From comparative composition compare, the composition containing 14 weight % active matter SLES-2 or SLS and 1.0 weight % active matter L3 With better manual frothing capacity, the comparative composition contains 14 weight % active matter SLES-2 or SLS and 1.0 weights Measure % active matter HCG.

According to viscosity salt response test method as described above, the skill of the present invention for using L3 as auxiliary surfactant is tested The viscosity salt of the composition of art responds and uses HCG (a kind of glycine betaine) as the comparative composition of auxiliary surfactant The response of viscosity salt.As a result it is shown in FIG. 17.

Embodiment 18: being compared property of the composition blistering research by hand to the surfactant containing different auxiliary

In this embodiment, a series of six (6) kind composition is prepared for for hand-washing blistering test.Six kinds of compositions It is formulated as follows:

1.CS-230/HCG (reference substance): including 12 weight % active matter SLES-2 (CS-230) and 3 weight % active matters CAPB (HCG) (4:1 ratio)；

2.CS-230/L3 (12% active matter): include 12 weight % gross activity objects (CS-230 and L3 that ratio is 14:1)；

3.CS-230/L3 (15% active matter): comprising 14 weight % active matter CS-230 and 1 weight % active matter L3 (14: 1 ratio)；

4.CS-230/ amide: including 14 weight % active matter CS-230 and 1 weight % active matter COMF (cocoyl list Ethanol amine) (14:1 ratio)；

5.CS-230/ both sexes acetate: including 14 weight % active matter CS-230 and 1 weight % active matter N- lauramide Base ethyl-N-hvdroxv ethylamino sodium acetate (sodium lauryl amphoacetate) (" am ") (14:1 ratio)；

6.CS-230/ sulfosuccinate: including 14 weight % active matter CS-230 and 1 weight % active matter sulfosuccinic Sour lauryl sodium (sodium lauryl sulfosuccinate) (" ss ") (14:1 ratio)；

The manual blistering test of six kinds of compositions using skin sense method of testing as described above (also referred to as hand washing method of testing) into Row.Comparative manual frothing result is recorded in Figure 18.

The results show that when being used to prepare body cleansing composition, with HCG, both sexes acetate and sulfosuccinate phase Than the L3 of technology of the present invention has basic preferable manual frothing capacity.

Embodiment 19: manual to the being compared property of composition containing HCG, L3, both sexes acetate and/or sulfosuccinate Blistering research

In this embodiment, prepare a series of six kinds of (6) compositions for hand-wash blistering test.Six kinds of compositions are matched Side is as follows:

1.CS/HCG (reference substance): including 12 weight % active matter SLES-2 (CS-230) and 3 weight % active matter CAPB (HCG) (4:1 ratio)；

2.CS/L3 (4:1): including 12 weight % active matter CS-230 and 3 weight % active matter L3 (4:1 ratio)；

3.CS/L3 (14:1): including 14 weight % active matter CS-230 and 1 weight % active matter L3 (14:1 ratio)；

4.CS/HCG/L3: including 12 weight % active matter CS-230 and 3 weight % active matter auxiliary surfactant (4:1 ratio Example), wherein the auxiliary surfactant includes the HCG and L3 that ratio is 1:1；

5.CS/HCG/am: including 12 weight % active matter CS-230 and 3 weight % active matter auxiliary surfactant (4:1 ratio Example), wherein the auxiliary surfactant includes HCG the and N- lauroyl amido ethyl-N-hvdroxv ethylamino second that ratio is 1:1 Sour sodium (" am ")；

6.CS/HCG/ss: including 12 weight % active matter CS-230 and 3 weight % active matter auxiliary surfactant (4:1 ratio Example), wherein the auxiliary surfactant includes the HCG and sulfosuccinic acid lauryl sodium (" ss ") that ratio is 1:1；

The manual blistering test of six kinds of compositions is carried out using skin sense method of testing as described above.Based on three evaluation members Comparative manual frothing result be shown in FIG. 19.

The results show that when being used alone or being combined with HCG, the L3 and HCG of technology of the present invention, both sexes acetate or Sulfosuccinate, which is compared, has preferably manual frothing capacity.

Embodiment 20: it blisters by hand to the being compared property of body cleansing composition containing HCG, L3 and/or both sexes acetate Research

In this embodiment, prepare a series of four kinds of (4) compositions for hand-wash blistering test.Four kinds of compositions are matched Side is as follows:

1.CS-230/HCG (reference substance): including 12 weight % active matter SLES-2 (CS-230) and 3 weight % active matters CAPB (HCG) (4:1 ratio)；

2.CS-230/L3: including 12 weight % active matter CS-230 and 3 weight % active matter L3 (4:1 ratio)；

3.CS-230/HCG/ both sexes acetate: including 12 weight % active matter CS-230 and the 3 auxiliary surfaces of weight % active matter Activating agent (4:1 ratio), wherein the auxiliary surfactant includes HCG the and N- lauroyl amido ethyl-N- hydroxyl that ratio is 1:1 Base ethylamino sodium acetate；And

4.CS-230/L3/ both sexes acetate: including 12 weight % active matter CS-230 and the 3 auxiliary surfaces of weight % active matter Activating agent (4:1 ratio), wherein the auxiliary surfactant includes L3 the and N- lauroyl amido ethyl-N- hydroxyl that ratio is 1:1 Base ethylamino sodium acetate.

The manual blistering test of four kinds of compositions using skin sense method of testing as described above (also referred to as hand washing method of testing) into Row.Comparative craft frothing result is shown in FIG. 20.

The results show that when used alone, the L3 of technology of the present invention has basic preferably manual compared with HCG Steep performance.As a result it also shows, when being combined with the ratio of 1:1 and both sexes acetate, the L3 of the technology of the present invention and the ratio with 1:1 Still there is basic preferably manual frothing capacity compared with HCG associated with both sexes acetate.

Embodiment 21: the preparation of the soap bar preparation comprising LLL

It uses and two kinds of synthetic detergent soap bars with formula shown in table 3 is prepared with the law of procedure: (1) weighing all list Component, and they are mixed into resulting mixture in one gallon of bucket；(2) by gained in 3 Kun grinders (3-roll mill) Mixture homogenization；(3) gained blend is transferred to laboratory Sigma plodder (lab sigma plodder), uses cold water Bucket (barrel) temperature is fully controlled at about 30 DEG C to about 35 DEG C, heat caused by squeeze pressure is eliminated；(4) by addendum cone housing (head cone jacket) is heated to about 45 DEG C, promotes the extrusion by the centrum (cone)；And (5) cut extrudate It cuts and is molded into soap bar.

Table 3

Two kinds of compound soap bars (combo soap bar) with formula shown in table 4: (1) Kun are prepared using following procedure Roll (roll-milling) butter/coconut oil soap dry bulb (tallow/coco soap dry pellet)；(2) using wing paddle high speed Blender (hydrofoil impeller) with 300ppm glycerol, fatty acid, L3,In BSS-45 altogether It mixes to uniform；(3) additive component is weighed；(4) whole components are mixed into soap blend in one gallon of bucket；(5) Kun rolls Gained soap blend, while moisture is tested using karr Fischer moisture measuring method (Karl Fisher)；(6) if desired, By moisture regulation to 12% while Kun rolls；And (7) squeeze out and extrudate are molded into soap bar.

Table 4

A. this is α sulfonated alkyl ester/alpha-sulfonated fatty acid SME/SFA blend.

The overall observation conclusion of the performance of four kinds of soap bars is, compared with the commercially available soap bar containing glycine betaine, dilactic acid laurel (it can be with for esterL3 derives from Stepan Company) improve synthetic detergent soap bar and compound soap Skin sense, foaming characteristic and the plasticity of both items.

Embodiment 22: it prepares a series of with different amounts of salicylic cleaning compositions

In this embodiment, the formula preparation according to shown in table 5 has 0.5% salicylic blistering detergent certainly (self-foaming wash), with 1.0% salicylic standard detergent (regular wash) and with 2.0% bigcatkin willow The gel detergent (gel wash) of acid.Combination process includes the steps that as described below.

In the suitable vessel with heating and stirring ability be packed into deionization (D.I.) water, propylene glycol andAS-40 CG-P.The material being loaded into while mixing is heated to 45-50 DEG C.It is incited somebody to action while stirringL3 is added in mixture.It holds the mixture in 45-50 DEG C while stirring is clarified up to complete. Then, salicylic acid is added while stirring up to clarification and all substances dissolution completely, while temperature is maintained about 45 DEG C To about 50 DEG C.Composition is cooled to room temperature while stirring.Then, the pH of composition is adjusted to hope with sodium hydroxide Value (about 5), and with sodium chloride adjust viscosity.

Table 5

Embodiment 23: all natural body wash (all natural body wash) and clear body wash The preparation of (clear body wash)

In this embodiment, preparing two kinds using program described herein has the body being formulated as shown in table 6 clear Clean product.By deionized water,WA-Extra、SLL-FB and L3 is added in the suitable vessel with mixed, heating efficiency and cooling capacity and mixes.It heats the mixture to about 130-135℉.When reaction solution clarification, reaction solution is cooled to room temperature.During cooling, flax is added in about 90 ℉ to mention It takes object (flax extract) and is uniformly mixed.If desired, preservative, fragrance and dyestuff is added and is uniformly mixed.If needed It wants, viscosity can be adjusted with sodium chloride, and if desired, sodium hydroxide or lemon acid for adjusting pH can be used.

Two kinds of prepared body cleansing compositions are all natural body wash and clear body wash respectively.It is " complete Naturally " refer to that all the components in composition all derive from natural materials.

Table 6

Embodiment 24: the preparation of skin lotion (skin lotion)

In this embodiment, the skin lotion that there is formula shown in table 7 using following program preparations is similar to.

Prepare water phase: by deionized water and78 are fitted into container and are sufficiently mixed into aqueous mixture.By water phase Mixture is heated to about 170-175 ℉.It prepares oily phase: being added in another containerL3, IPP, whale Ceryl alcohol and GMS are simultaneously mixed into oil mixture.Oil mixture is heated to about 170-175 ℉.Water phase one is quickly stirred on one side While oil is mutually slowly added into water phase.Make resulting emulsifying mixture about 20-25 minutes, is subsequently cooled to about 80 ℉. If desired, any preservative, colorant or dyestuff can be slowly added into.Citric acid or sodium hydroxide can be used gained group The pH for closing object is adjusted to desired value.

Table 7

Embodiment 25: the preparation of Solid antiperspirant

In this embodiment, there is the Solid antiperspirant of formula shown in the following table 8 using following procedure preparation: suitable Following component, that is, 245Fluid, Lanette 18Deo, Ozokerite Wax and Castor Oil Wax MP- are mixed in container 80, it is mixed and heated to about 70 DEG C.When all the components melting, talcum (Talc) and Reach AZP is added and is sufficiently mixed big About 20 minutes.Then mixture is cooled to about 45 DEG C, is then poured into container and is cooled to environment temperature.

Table 8

Embodiment 26: to use alkyl lactyllactate as auxiliary surfactant detergent composition carry out foaming characteristic It can test and detergency ability test

It is expected that the frothing capacity of the L3 as the component in detergent formulations is, the addition generation of L3 is suitable with control formulation Or frothing capacity more better than control formulation.A kind of formula for heavy duty detergent that L3 is added is shown in the following table 9.

Table 9

The attribute of alkyl lactyllactate composition based on the result and the technology of the present invention, L3 are believed to be added Into detergent formulations such as heavy duty detergent, instead of anionic surfactant as auxiliary surfactant, or with yin from Sub- surfactant is together as auxiliary surfactant.It is additionally considered that and is added to L3 together with different anionic surfactants The improvement of collaboration can be generated in detergent formulations to clean-up performance.

Embodiment 27: to use alkyl lactyllactate as auxiliary surfactant detergent composition carry out performance examination It tests

A series of 5 kinds of light duty liquid dishwashing detergent formulations (dish detergent formulation) is prepared, Every kind of preparation includes 17.51 weight % active matter sodium alkyl benzene sulfonates, 8.17 weight % active matter methyl ester sulfonates, 4.32 weights Measure % active matter alkyl ether sulfate and the 3 auxiliary surfactants of weight % active matter (10:1 ratio).The auxiliary surfactant It is (1)40-CO (reference substance), (2)LMDO (reference substance), (3) L3、(4)40-CO andThe blend of L3 or (5)LMDO andThe blend of L3.

All formulations are clear in room temperature.The viscosity results of every kind of preparation are shown in the following table 10.

Table 10

Mixer blistering test (mixer foam test) result is shown in the following table 11.

Table 11

The experimental error for estimating mixer blistering test is +/- 0.2g.ContainThe sample of L3 with it is right It is the same good to obtain according to formulations display.

Baumgartner test result is shown in the following table 12.

Table 12

The experimental error of Baumgartner test is about +/- 5.0% grease removal.Although all containThe result of the sample of L3 is lower than LMDO reference substance and 40-CO reference substance as a result, still and reference substance Result compare, the test result of the sample of the blend containing L3 and LMDO is in experimental error.

Microplate test (mini-plate test) result is shown in the following table 13.

Table 13

The experimental error of microplate test is +/- 1 microplate.In order to be compared, it should be noted that sometimes with " plate (plate) " such test is recorded instead of " microplate (mini-plate) " and a microplate is equal to three plates.? In above-mentioned test, containThe sample of L3 shows the same good with reference substance.

Shaking foaming test result is shown in the following table 14.

Table 14

The experimental error of above-mentioned test is about +/- 20ml.All " having dirt " the result is that equal.It answers considerable It is that, based on very high shaking frothing result in the case where no any dirt, the blend that L3:LMDO is 50:50 is presented Some synergistic effects out.

Embodiment 28: the preparation of ballpoint antiperspirant

Ballpoint anti-perspiration formulation shown in table 15 is prepared using program as described below: deionized water and aluminium chloride are mixed And 150 ℉ -155 ℉ are heated to about under moderate-speed mixer.In about 150 ℉ to about 155 ℉, BRIJ is added while quick stirring 72,78 and of BRIJL3." the mixing of chiral L3/ meso L3/L2 and L3 in table 15 and other tables Object (chiral L3/meso L3/mixture of L2/L3) " refers to that L3 used can be for example by L- lactide or D- third The chiral L3 of lactide preparation, the mixture of the L2 and L3 that are prepared by the racemic L3 of Study of Meso-Lactide preparation, by lactic acid method or The mixture of above-mentioned substance.

Then the mixture of the ingredient is heated to about 160 ℉ to about 165 ℉, and kept within this temperature range about 15 minutes.Then mixture is cooled to room temperature.Preservative and fragrance is added in room temperature.If desired, can with citric acid or The pH of product is adjusted to 3.5-4.0 by sodium hydroxide.

Table 15

Embodiment 29:UA/UVB protects the preparation of lotion (UA/UVB protective lotion)

Use program preparation as described below that there is the protection lotion of formula shown in table 16: by by deionized water and BRIJ 78 is fitted into container to prepare water phase.Gained mixture is mixed and heated to about 170 ℉ -175 ℉.In another appearance In device, pass through byL3, cetanol andGMS PURE mixes to prepare oily phase.It will Sun-screening agent (sunscreen agent) (PARSOL MCX, 587 ESCALOL, PARSOL 1789, ESCALOL 567) is added to In oily phase, then by oily heat phase to about 170 ℉ -175 ℉.The mixing speed of water phase is improved, and oil is mutually slowly added into In water phase.By emulsifying mixture about 20-25 minutes, and it is cooled to about 80 ℉.If desired, preservative, dyestuff and perfume (or spice) is added Material.PH is adjusted to about 5.5-6.5 with citric acid or sodium hydroxide.

Table 16

Embodiment 30: the preparation of the sun-proof W/O lotion with titanium dioxide

Use program preparation as described below that there is the sun-screening agent of formula shown in the following table 17: by mixing deionized water and STEPANQUAT^TMML prepares water phase.By mixing Silicone DC-345,L3、ABIL EM- 90, MT-100T and SALCARE SC-95 prepares oily phase.Then water phase is added in oily phase, and is sufficiently mixed about 15- 20 minutes.Then preservative, dyestuff and fragrance is added, and with 5000rpm mixing about 3-5 minutes in homogenizer.

Table 17

Embodiment 31: exempt from the preparation of tanned lotion (sunless tanning lotion)

There is the tanned lotion (tanning lotion) of formula shown in table 18 using program preparation as described below.Pass through Deionized water and glycerol are mixed to prepare water phase.By heated aqueous to about 160 ℉.By by BRIJ 78, L3、GMS PURE, Lipocol C (Lipo) cetanol andS mixes to prepare oily phase. By oily heat phase to about 165 ℉, then oil is mutually added in water phase while about 165 ℉ are on one side quick stirring, lasts about 20- 25 minutes.Mixture is cooled to room temperature.During cooling, Glydant is added in 120 ℉.It has been pre-mixed in 95 ℉ addition The dihydroxyacetone (DHA) of water.Mixture is sufficiently mixed, pH is then adjusted to about 5.5-6.0.

Table 18

Embodiment 32: the preparation of the skin lotion containing antioxidant

There is the skin lotion of formula shown in table 19 using program preparation as described below: by mixing in a reservoir Ionized water and BRIJ 78 prepare water phase, by heated aqueous to about 170 ℉ -175 ℉.By being incited somebody to action in another containerL3, cetanol andGMS PURE mixes to prepare oily phase.Extremely by oily heat phase About 170 ℉ -175 ℉.Oil is mutually slowly added into water phase while quickly stirring water phase.By emulsifying mixture about 20- 25 minutes, and it is cooled to 80 ℉.Then Palimitate-A and vitamin E acetate is added.If desired, anti-corrosion can be added Agent, colorant (color) and dyestuff.The pH of mixture can be adjusted to about 5.5-6.5 with citric acid or sodium hydroxide.

Table 19

Embodiment 33: the preparation of hair conditioner (hair conditioner)

Use program preparation as described below that there is the hair conditioner of formula shown in the following table 20: by deionized water and Lexamine S-13 is added in the suitable vessel with heating efficiency, cooling capacity and mixed.It heats the mixture to about 155℉-160℉(62℃-72℃).It will CETAC and cetanol are added to mixed It closes in object.By emulsifying mixture about 30 minutes, and it is cooled to about 120 ℉ to about 125 ℉ (48 DEG C -52 DEG C).It will be soluble in water Potassium chloride is added in mixture, is then addedL3.If desired, will with citric acid or sodium hydroxide The pH of mixture is adjusted to about 3.5-4.5.If desired, preservative, colorant and fragrance is added, and mixture is cooled to room Temperature.

Table 20

Embodiment 34: the preparation of shampoo (shampoo)

There is the shampoo of formula shown in table 21 using program preparation as described below: Polyquaternium-10 is added to In ionized water, then it is addedAM、WA、EGAS and L3.About 160 ℉ to about 165 ℉ are heated the mixture to, and are kept for about 20-25 minutes in the temperature.Then mixture is cold But to room temperature.During cooling, glycerol and SILPLEX J-2S is added in 100 ℉, and is sufficiently mixed.Anti-corrosion is added in room temperature Agent, fragrance and dyestuff.The pH of mixture is adjusted to about pH 5.5-6.5 with citric acid or sodium hydroxide, will be mixed with ammonium chloride For the viscosity-adjusting agent of object to desired viscosity, the desired viscosity is about 5,000 to about 11,000cps, even more preferably about 8,000 To about 10,000cps.

Table 21

Embodiment 35: lauryl lactyllactate product is prepared from lactic acid

By about 169g (1.6mol) lactic acid, 47mL (0.2mol) C_12-14Fatty alcohol and 5g (account for gross mass 2.4%) pTSA It is placed in 500mL four-neck flask, the 500mL four-neck flask is furnished with overhead type mechanical agitator (overhead mechanical stirrer)、N₂Entrance and exit, thermocouple/temperature controller/heating mantle (thermocouple/temp controller/ Heating mantel) and have Dean-Stark trap (Dean-Stark trap) condenser.By reaction mixture It is stirred and heated to 185 DEG C.After the temperature stirs about 4 hours, it is collected into 50mL water through the above-mentioned time, reaction is mixed Object it is cooling and obtain sample for detect react and whether complete.It washs and uses by mixture cooling and with salt water (3 × 80mL) and is full And NaHCO₃(aqueous solution) neutralizes.Mixture is through Na₂SO₄It dries and filters.

GC is analysis shows that reaction product includes the lauryl lactyllactate (L3) and Lauryl lactate that ratio is about 1:0.7 (L2)。

Embodiment 36: the superficiality Quality Research of the surfactant blend containing lauryl lactyllactate

Testing lauryl lactyllactate (L3) in this embodiment reduces the critical micell of seven kinds of conventional surfactants Concentration (CMC) and surface area/molecule effect.The L3 tested is with trade nameL3 derives from Stepan Company.Seven kinds of surfactants of test are shown in the following table 22.

Table 22

Seven kinds of the formula preparation according to shown in table 23A and 23B contains only one of seven kinds of conventional surfactants or two Kind contrast surface surfactant composition (reference substance 1-7) and nine kinds containing one or both of conventional surfactants and this hair The sample surfaces surfactant composition (sample 1A-C and 2-7) of the L3 of bright technology.With Kr ü ss K12 tensile measurer (Kr ü ss K12tensiometer) (Kruss USA, Matthews, NC, USA) measures every kind of surfactant group by automatic Titration Close the CMC of object.Temperature is controlled at 25 DEG C.Surface area occupied by each molecule is calculated according to Gibbs equation.Test result exists It is shown in table 23A and 23B.

Table 23A: the surface nature of the surfactant blend containing lauryl lactyllactate

Table 23B: the surface nature of the surfactant blend containing lauryl lactyllactate

Surprisingly it has been found that for every kind of conventional surfactants of test, with the table for being free of lauryl lactyllactate Face surfactant blend is compared, and the surfactant blend containing lauryl lactyllactate has significantly lower critical micell dense It spends (CMC).It has also been unexpectedly found that in the surfactant blend containing lauryl lactyllactate, dilactic acid laurel Ester is effectively reduced " area/molecule "." area/molecule " reduced shows to improve surfactant at air/water interface Packing of molecules.The unexpected collaboration property of the surfactant blend containing lauryl lactyllactate as the result is shown.

Effect of the lauryl lactyllactate in terms of reducing CMC is especially unexpected.Such as 4 institute of reference substance 4 and sample Show, compared with the composition for containing only PAS-8S, the reduction of CMC is more than 99% in the blend of L3 and PAS-8S.It has also been found that cream Acyl Lauryl lactate can be compatible with different types of surfactant, different types of surfactant include for example yin from Sub- surfactant, nonionic surfactant, cationic surfactant and amphoteric surfactant.On all these surfaces Lauryl lactyllactate, which has shown that, in active species reduces CMC and area/molecule ability.Sample 1A-C and 2-4 are said Anionic surfactant blend is illustrated.It is living that sample 5-7 respectively illustrates amphoteric surfactant blend, non-ionic surface Property agent blend and cationic surfactant blend.CMC's is reduced to about 30% to about 99% in these examples.Face Product/molecule is reduced to about 10% to about 60%.

Embodiment 37: the rheological characteristic Quality Research of the fabric softener containing lauryl lactyllactate

The ability that lauryl lactyllactate is used as rheology modifier is had studied in this experiment.Reference composition only includes sulphur Sour methyl ester methyl two [tallowoxyloxyethyl] -2- hydroxyethyl ammonium (methyl bis [ethyl (tallowate)] -2- Hydroxyethyl ammonium methyl sulfate), it can be withVT-90 is from Stepan Commercially available from Company.Two kinds of samples of the technology of the present invention include that ratio is respectively 4:1 and 3:2VT-90 and The blend of lauryl lactyllactate.Viscosity of three kinds of compositions at 20 DEG C, 30 DEG C and 40 DEG C is tested, as a result in the following table 24 In show.

Table 24: the rheological equationm of state of the fabric softener containing lauryl lactyllactate

Result shown in table 24 illustrates the viscosity lowering energy of the lauryl lactyllactate in fabric softener.Pass through Lauryl lactyllactate is added in fabric softener, reduces the viscosity of surfactant system significantly.

Embodiment 38: the comparative viscosity salt response investigations and blistering research of different chiral lauryl lactyllactates

Three kinds of compositions are prepared for, every kind of composition includes 12 weight % active matter SLES-2 (CS-230) and 3 weight % Following active matter: the L- lauryl lactyllactate (" using the L3 of L- lactide ") that is prepared by L- lactide, by L- lactide (15%) and the lauryl lactyllactate of the mixture of Study of Meso-Lactide (85%) preparation (" uses L- lactide/meso third The L3 " of lactide) or by rac-lactide prepare racemic lauryl lactyllactate (" using the L3 of rac-lactide "). Any oil is not added to the composition.

The frothing capacity of every kind of composition passes through shaking blistering method of testing (also referred to as graduated cylinder Turnover testing as described above Method) it is tested.The frothing result (initial result and the result after 5 minutes) of three kinds of compositions without any oil of record And it is shown in FIG. 21.

It is without any oil the results show that Experimental composition containing the L3 for using L- lactide or containing use L- lactide/ The Experimental composition of the L3 of Study of Meso-Lactide be it is comparable, the two all than containing the L3 for using rac-lactide composition tool There is higher foam height.

The viscosity salt response of three kinds of compositions is tested according to viscosity salt response test method as described above, is as a result being schemed It is shown in 22.Preferably increase the results show that using L- lactide/Study of Meso-Lactide L3 to have using the L3 ratio of L- lactide Viscosity, and it is better than the L3 using rac-lactide using the tackifying of L- lactide/Study of Meso-Lactide L3.

Embodiment 39: the comparative study of the lactic acid method of the lactic acid method and the technology of the present invention of United States Patent (USP) 3,144,341

The lactic acid method of United States Patent (USP) 3,144,341 (' 341 patent) is reproduced in this embodiment, and by itself and the present invention The lactic acid method of technology compares.According to ' 341 patents, any catalyst, and the equivalent of lactic acid and laruyl alcohol are not used Molar ratio (equivalent molar ratio) is about 2.1:1.Six experiments (experiment 1-6) of the lactic acid method of the technology of the present invention It is carried out using the method similar with described in example 3 above 5.For experiment each of 1-5, using NAFION, pTSA, As catalyst, the equivalent molar ratio of lactic acid used and laruyl alcohol is about 4:1 for methanesulfonic acid, etherate of trifluoroboron or phosphoric acid. Experiment 6 uses pTSA as catalyst, and the equivalent molar ratio of lactic acid used and laruyl alcohol is about 8:1.It analyzes to obtain by GC The ratio of L2 and L3 in every kind of reaction product are simultaneously shown in the following table 25.

Table 25

Method	Laruyl alcohol equivalent	Lactic acid equivalent	Catalyst	The ratio of L2:L3
					United States Patent (USP) 3,144,341	1	2.1	Nothing	2.3:1
Experiment 1	1	4	NAFION	1.2:1
					Experiment 2	1	4	pTSA	0.9:1
Experiment 3	1	4	Methanesulfonic acid	1.1:1
					Experiment 4	1	4	Etherate of trifluoroboron	1:1
Experiment 5	1	4	Phosphoric acid	1.3:1
					Experiment 6	1	8	pTSA	0.7:1

The results show that compared with the product obtained by the method for ' 341 patents, what the lactic acid method of the technology of the present invention obtained Product may include the ratio of much higher L3 and L2.

The technology of the present invention is described with so comprehensive, clear, concise and accurate wording now, so that any this field skill Art personnel can implement the technology of the present invention.It should be understood that described above is the preferred embodiments of the invention, and can be with The present invention is modified in the case where not departing from the purport or range of the technology of the present invention of the appended claims elaboration.

In particular it relates to following aspect:

1. a kind of method for preparing alkyl lactyllactate, the described method comprises the following steps:

Mixture comprising lactide, the compound of at least one hydroxyl and at least one acid catalyst is provided；And

Make temperature of the compound of the lactide and at least one hydroxyl at about 20 DEG C to about 70 DEG C of range Reaction.

2. the method as described in 1, wherein the temperature is in the range of about 40 DEG C to about 60 DEG C.

3. the method as described in 1, wherein at least one acid catalyst is H₂SO₄, HCl, p-methyl benzenesulfonic acid,Ionomer or their mixture.

4. the method as described in 1, wherein the lactide be L- lactide, Study of Meso-Lactide, rac-lactide or Their mixture.

5. the method as described in 1, wherein the lactide is L- lactide.

6. the method as described in 1, wherein the lactide is the mixture of L- lactide and Study of Meso-Lactide.

7. the method as described in 6, wherein the total weight based on the mixture, the mixture includes about 15% to about 70% L- lactide and the Study of Meso-Lactide of about 85% to about 30%.

8. the method as described in 1, wherein the lactide is derived from the lactic acid of fermentation method preparation.

9. the method as described in 1, wherein the molecule of the compound of at least one hydroxyl includes at least one primary hydroxyl Base.

10. the method as described in 9, wherein the compound of at least one hydroxyl is substantially free of secondary hydroxyl and tertiary hydroxyl Base.

11. the method as described in 1, wherein the compound of at least one hydroxyl is fatty alcohol.

12. the method as described in 11, wherein the fatty alcohol includes about 6 to about 18 carbon atoms.

13. the method as described in 11, wherein the fatty alcohol includes about 12 to about 14 carbon atoms.

14. the method as described in 11, wherein the fatty alcohol is laruyl alcohol.

15. the method as described in 1, wherein the compound of at least one hydroxyl is alkoxylated.

16. the method as described in 15, wherein the compound of the alkoxylated hydroxyl is preformed.

17. the method as described in 15, wherein the compound of at least one hydroxyl is in situ alkoxylated.

18. the method as described in 1, wherein not adding any solvent to the reaction mixture.

19. the method as described in 18, wherein the compound of the lactide and at least one hydroxyl is with equimolar Amount exists.

20. the method as described in 1, the method also includes forming the step of clarifying homogeneous liquid.

21. the method as described in 1, wherein the method provides at least about 95% yield.

22. product prepared by the method as described in 1.

23. the product as described in 22, based on the total weight of the product, the product includes at least the one of at least about 90% Kind alkyl lactyllactate.

24. the product as described in 23, based on the total weight of the product, the product includes at least the one of at least about 95% Kind alkyl lactyllactate.

25. the product as described in 23, wherein at least one alkyl lactyllactate includes at least one L- lactoyl cream Acid alkyl ester.

26. the product as described in 25, wherein at least one alkyl lactyllactate is substantially free of the dilactic acid Other stereoisomers of Arrcostab.

27. the product as described in 23, wherein at least one alkyl lactyllactate includes at least one L, D/D, L- Racemic alkyl lactyllactate.

28. the product as described in 23, wherein at least one alkyl lactyllactate includes at least one L- lactoyl cream Acid alkyl ester and at least one L, D/D, L- racemic alkyl lactyllactate.

29. the product as described in 22, based on the total weight of the product, the product includes at least the one of less than about 5% Kind of lactic acid alkyl ester and less than about 5% at least one hydroxyl compound.

30. the composition comprising the product as described in 22.

31. a kind of method for preparing alkyl lactyllactate, the described method comprises the following steps:

The mixture comprising lactic acid, the compound of at least one hydroxyl and at least one acid catalyst is provided, wherein institute State the amount of the compound of lactic acid and at least one hydroxyl are as follows: at least one hydroxyl of every equivalent There is the lactic acid of at least about 4 equivalents in compound；And the lactic acid and the compound of at least one hydroxyl is made to exist The thermotonus that range is about 120 DEG C to about 200 DEG C.

32. the method as described in 31, wherein at least one acid catalyst include methanesulfonic acid, etherate of trifluoroboron, P-methyl benzenesulfonic acid, phosphoric acid,Ionomer, sulfuric acid or their mixture.

33. the method as described in 31, wherein at least one acid catalyst includes p-methyl benzenesulfonic acid.

34. the method as described in 31, wherein the lactic acid is Pfansteihl, D-ALPHA-Hydroxypropionic acid, racemic lactic acid or their mixing Object.

35. the method as described in 31, wherein the lactic acid is Pfansteihl.

36. the method as described in 31, wherein the lactic acid is prepared by fermentation method.

37. the method as described in 31, wherein the molecule of the compound of at least one hydroxyl include at least one primary Hydroxyl.

38. the method as described in 37, wherein the compound of at least one hydroxyl is substantially free of secondary hydroxyl and tertiary hydroxyl Base.

39. the method as described in 31, wherein the compound of at least one hydroxyl is at least one fatty alcohol.

40. the method as described in 39, wherein at least one fatty alcohol includes about 6 to about 18 carbon atoms.

41. the method as described in 39, wherein at least one fatty alcohol includes about 12 to about 14 carbon atoms.

42. the method as described in 39, wherein at least one fatty alcohol is laruyl alcohol.

43. the method as described in 31, wherein the compound of at least one hydroxyl is alkoxylated.

44. the method as described in 43, wherein the compound of at least one hydroxyl is in situ alkoxylated.

45. the method as described in 43, wherein the compound of the alkoxylated hydroxyl is preformed.

46. the method as described in 31, wherein not adding any solvent to the reaction mixture.

47. the method as described in 31, the method also includes forming the step of clarifying homogeneous liquid.

48. product prepared by the method as described in 31.

49. the product as described in 48, based at least one of product alkyl lactyllactate and at least one lactic acid The total weight of Arrcostab, the product include at least about 40% at least one alkyl lactyllactate.

50. the product as described in 48, based at least one of product alkyl lactyllactate and at least one lactic acid The total weight of Arrcostab, the product include at least about 50% at least one alkyl lactyllactate.

51. the composition comprising the product as described in 48.

52. a kind of composition, it includes at least one alkyl lactyllactates with following general formula structure:

Wherein R includes about 2 to about 6 carbon atoms, R¹It is about 0 to about 100 comprising about 6 to about 22 carbon atoms and n.

53. the composition as described in 52 also includes at least one surfactant.

54. the composition as described in 53, wherein at least one surfactant includes anionic surfactant, institute It states anionic surfactant and is selected from alkyl sulfate, alkyl alkoxy sulfate, alkyl alkoxy carboxylates, alkyl phosphoric acid Salt, alkoxy phosphates, alkylsulfonate, sulfonation alkyl methyl salt or the salt of alkyl ethyl ester of sulfonation, sulfonation Salt, alkyl sulfoacetate, alkylbenzene sulfonate, alhpa olefin sulfonate, paraffin sulfonate, the alkyl hydroxyethyl sulfonic acid of fatty acid Salt, acyl lactate, sulfosuccinate, both sexes acetate, sarcosinate, poly- Plantacare 818 carboxylate, lauryl The combination of glucose carboxylate, the derivative of alkyl-glutamic acid salt and above-mentioned substance and above-mentioned substance.

55. the composition as described in 53, wherein at least one surfactant includes nonionic surfactant, institute It states nonionic surfactant and is selected from fatty acid amide, the fatty acid amide of ethoxylation, alkylol, alkyl alcohol ethoxylates Object, alkylphenol ethoxylate, propylene glycol ester, polyglycerol ester, glycol ester, the diol ester of ethoxylation, polypropylene glycol ester, alkane The group of base glucoside, alkyl polyglycoside, alkyl glucose amide, the derivative of sorbitan ester and above-mentioned substance and above-mentioned substance It closes.

56. the composition as described in 53, wherein at least one surfactant is selected from glycine betaine, amine oxide, sulphur The combination of the derivative and above-mentioned substance of base glycine betaine and above-mentioned substance.

57. the composition as described in 53, wherein at least one surfactant includes that cationics or cation are poly- Object is closed, the cationics or cationic polymer are selected from alkylpolyoxyethylene, dialkyl dimethyl ammonium halide, trialkyl Methyl ammonium halide, polyquaternium, quaternized cellulose, quaternized guar gum, esterquats, amidoamine quaternary ammonium compound With the combination of alkyl amidopropyl quaternary ammonium compound and the derivative and above-mentioned substance of above-mentioned substance.

58. the composition as described in 52 also includes buffer.

59. the composition as described in 58, wherein the total weight based on the composition, the amount of the buffer is about 0% to about 1%.

60. the composition as described in 52, wherein R includes about 2 to about 3 carbon atoms.

61. the composition as described in 52, wherein R¹Include about 10 to about 18 carbon atoms.

62. the composition as described in 52, wherein R¹Include about 12 to about 14 carbon atoms.

63. the composition as described in 52, wherein n is about 1 to about 12.

64. the composition as described in 52, wherein n is about 1 to about 9.

65. the composition as described in 52, wherein at least one alkyl lactyllactate is at least one L- lactoyl cream Acid esters.

66. the composition as described in 52, wherein at least one alkyl lactyllactate is at least one L, D/D, L- Racemic dilactic acid ester.

67. the composition as described in 52, wherein at least one alkyl lactyllactate is by L- lactide and meso It is prepared by the mixture of lactide.

68. the composition as described in 67, wherein the total weight based on the mixture, the mixture include about 15% to About 70% L- lactide.

69. the composition as described in 52, wherein at least one alkyl lactyllactate is lauryl lactyllactate.

70. the composition as described in 52, wherein at least one alkyl lactyllactate is contained by lactic acid and at least one It is prepared by the compound of hydroxyl.

71. the composition as described in 70, wherein the compound of the hydroxyl is alcohol.

72. the composition as described in 71, wherein the alcohol is fatty alcohol.

73. the composition as described in 70, wherein the lactic acid is Pfansteihl.

74. the composition as described in 52, wherein the composition is the form of rheology modifier.

75. the composition as described in 52, wherein the composition is the form of emollient or wetting agent.

76. the composition as described in 52, wherein the composition is the shape of surfactant or surfactant blend Formula.

77. the composition as described in 52, wherein the composition is the form of soap bar.

78. the composition as described in 52, wherein the composition is the form of product emulsion.

79. the composition as described in 52, wherein the composition is that facial cleanser, body wash, shampoo, skin care are washed The form of agent or shower gels.

80. the composition as described in 79, wherein the body wash is from blistering body wash.

81. the composition as described in 79, wherein the body wash is all natural body wash.

82. the composition as described in 79, wherein the body wash is clear body wash.

83. the composition as described in 79, wherein the body wash is gel body wash.

84. the composition as described in 52, wherein the composition is the form of wipe articles.

85. the composition as described in 52, wherein the composition is the form of baby cleansing product or baby treatment product.

86. the composition as described in 52, wherein the composition is the form of household product.

87. the composition as described in 52, wherein the composition is the form of antiperspirant.

88. the composition as described in 52, wherein the composition is the form of laundry detergent or dish washing detergent.

89. the composition as described in 52, wherein the composition is industrial or public cleaning product.

90. the composition as described in 52, wherein the composition is hard surface cleaner.

91. a kind of composition, it includes:

At least one alkyl lactyllactate with following general formula structure:

Wherein R is alkyl or alkoxylated alkyl；And

At least one surfactant.

92. the composition as described in 91, the composition also includes water, wherein the composition with contain at least one It surfactant but is compared without the comparative surface activator composition of alkyl lactyllactate, in terms of critical micelle concentration The reduction of about 5% to about 99% is showed, wherein in the composition and in the comparative surface activator composition, The total concentration by weight of surfactant activity object is essentially identical.

93. the composition as described in 92, wherein the composition shows at least about 15% in terms of critical micelle concentration Reduction.

94. the composition as described in 91, wherein R includes the alkyl of about 6 to about 22 carbon atoms.

95. the composition as described in 94, wherein R also includes about 1 to about 12 for alkyl lactyllactate described in every mole Mole the alkoxy with about 2 to about 6 carbon atoms.

96. the composition as described in 95, wherein the alkoxy is ethyoxyl or propoxyl group or their combination.

97. the composition as described in 91, wherein R includes the alkyl of about 10 to about 18 carbon atoms.

98. the composition as described in 91, wherein R includes the alkyl of about 12 to about 14 carbon atoms.

99. the composition as described in 91, wherein at least one alkyl lactyllactate is L- dilactic acid ester.

100. the composition as described in 91, wherein at least one alkyl lactyllactate is by Study of Meso-Lactide system Standby racemic dilactic acid ester.

101. the composition as described in 91, wherein at least one alkyl lactyllactate is by L- lactide and interior to disappear Revolve the mixture preparation of lactide.

102. the composition as described in 101, wherein the total weight based on the mixture, the mixture includes about 15% To about 70% L- lactide.

103. the composition as described in 91, wherein at least one alkyl lactyllactate is lauryl lactyllactate.

104. the composition as described in 91, wherein at least one alkyl lactyllactate be by make lactic acid at least A kind of compound of hydroxyl carries out reaction preparation.

105. the composition as described in 104, wherein the lactic acid is Pfansteihl.

106. the composition as described in 105, wherein the Pfansteihl is prepared by fermentation method.

107. the composition as described in 104, the composition also includes at least one lactic acid alkyl ester, the lactic acid alkyl Ester be the compound in the lactic acid and at least one hydroxyl reaction during generate.

108. the composition as described in 107, wherein at least one alkyl lactyllactate is at least one cream Weight percent in the total amount of acyl lactic acid alkyl ester and at least one lactic acid alkyl ester is at least about 40%.

109. the composition as described in 91, wherein at least one surfactant includes at least one alkylsurfuric acid Salt, alkyl alkoxy sulfate, alkyl alkoxy carboxylates, alkylphosphonic, alkoxy phosphates, alkylsulfonate, Salt, alkyl sulfoacetate, the alkylbenzene of the salt of the alkyl ethyl ester of the salt or sulfonation of the alkyl methyl of sulfonation, the fatty acid of sulfonation Sulfonate, alhpa olefin sulfonate, paraffin sulfonate, alkyl isethionate, acyl lactate, sulfosuccinate, two Property acetate, sarcosinate, poly- Plantacare 818 carboxylate, lauryl glucose carboxylate, alkyl-glutamic acid salt, fatty acid acyl Amine, alkylol, alkyl alcohol ethoxylates, alkylphenol ethoxylate, propylene glycol ester, gathers the fatty acid amide of ethoxylation Glyceride, glycol ester, the diol ester of ethoxylation, polypropylene glycol ester, alkyl glucoside, alkyl polyglycoside, alkyl glucose amide, Sorbitan ester, glycine betaine, amine oxide, sulfobetaines, alkylpolyoxyethylene, dialkyl dimethyl ammonium halide, Trialkyl methyl ammonium halide, polyquaternium, quaternized cellulose, quaternized guar gum, esterquats, amidoamines season The combination of ammonium compound, the derivative of alkyl amidopropyl quaternary ammonium compound and above-mentioned substance and above-mentioned substance.

110. the composition as described in 91, wherein the composition is the form of soap bar.

111. the composition as described in 91, wherein the composition is the form of product emulsion.

112. the composition as described in 91, wherein the composition is Common detergents, household product, industrial Or public cleaning product, hard surface cleaner, wetting agent, facial cleanser, body wash, shampoo, skin lotion or shower are solidifying The form of glue.

113. the composition as described in 91, wherein the composition is surfactant, surfactant blend or cream The form of agent.

114. the composition as described in 91, the composition also includes water, wherein the composition with containing described at least one It plants surfactant but the comparative surface activator composition without alkyl lactyllactate is compared, occupied in each molecule The reduction that about 2% to about 80% is showed in terms of area, wherein in the composition and in the comparative surfactant In composition, the total concentration by weight of surfactant activity object is essentially identical.

115. the composition as described in 114, wherein the composition shows about in terms of the area that each molecule occupies The reduction of 5% to about 60%.

116. a kind of alkyl lactyllactate compound, the alkyl lactyllactate compound is that by lactide and have Derived from the polyalcohol of two or more primary hydroxyls.

117. the alkyl lactyllactate compound as described in 116, the compound has following general formula structure:

118. the alkyl lactyllactate compound as described in 117, wherein R group includes about 2 to about 24 carbon atoms.

119. the alkyl lactyllactate compound as described in 117, wherein R group includes about 2 to about 8 carbon atoms.

120. the alkyl lactyllactate compound as described in 116, wherein the polyalcohol is glycerol or ethoxylation Glycerol.

121. a kind of substantially pure L- alkyl lactyllactate product, the L- alkyl lactyllactate product includes at least A kind of L- alkyl lactyllactate compound with following general formula structure:

Wherein R includes alkyl or alkoxylated alkyl.

122. the L- alkyl lactyllactate product as described in 121, wherein the alkyl or alkoxylated alkyl derivative From the compound of hydroxyl.

123. the L- alkyl lactyllactate product as described in 122, wherein the compound of the hydroxyl is fatty alcohol.

124. the L- alkyl lactyllactate product as described in 122, wherein the compound of the hydroxyl includes at least one A primary hydroxyl.

125. the L- alkyl lactyllactate product as described in 124, wherein the compound of the hydroxyl be substantially free of it is secondary Hydroxyl or tert-hydroxyl.

126. the L- alkyl lactyllactate product as described in 121, wherein R includes having about 1 to about 22 carbon atom Alkyl.

127. the L- alkyl lactyllactate product as described in 126, wherein at least one L- lactoyl described in every mole Lactic acid alkyl ester compound, R also include about 1 to about 100 mole of at least one alkoxy.

128. the L- alkyl lactyllactate product as described in 127, wherein at least one L- lactoyl described in every mole Lactic acid alkyl ester compound, R also include about 1 to about 12 mole of at least one alkoxy.

129. the L- alkyl lactyllactate product as described in 127, wherein at least one alkoxy includes about 2 to about 6 carbon atoms.

130. the L- alkyl lactyllactate product as described in 121, wherein R includes having about 6 to about 18 carbon atoms Alkyl.

131. the L- alkyl lactyllactate product as described in 121, wherein R includes the alkane of about 12 to about 14 carbon atoms Base.

132. the L- alkyl lactyllactate product as described in 121, wherein R is derived from laruyl alcohol.

133. the L- alkyl lactyllactate product as described in 132 is substantially pure L- lauryl lactyllactate.

134. the L- alkyl lactyllactate product as described in 121, wherein being based on the L- alkyl lactyllactate product Total weight, the amount of at least one L- alkyl lactyllactate compound is at least about 90%.

135. the L- alkyl lactyllactate product as described in 121, wherein being based on the L- alkyl lactyllactate product Total weight, the amount of at least one L- alkyl lactyllactate compound is at least about 95%.

136. a kind of alkyl lactyllactate with following general formula structure:

Wherein R includes alkoxylated alkyl.

137. the alkyl lactyllactate as described in 136, wherein R includes the alkyl with about 1 to about 22 carbon atom.

138. the alkyl lactyllactate as described in 137, wherein for alkyl lactyllactate described in every mole, R is also wrapped Containing about 1 to about 100 mole of at least one alkoxy.

139. the alkyl lactyllactate as described in 138, wherein for alkyl lactyllactate described in every mole, R is also wrapped Containing about 1 to about 12 mole of at least one alkoxy.

140. the alkyl lactyllactate as described in 138, wherein at least one alkoxy includes about 2 to about 6 carbon Atom.

A kind of 141. alkyl lactyllactates with following general formula structure:

Wherein R includes alkyl or alkoxylated alkyl, the alkyl or alkoxylated alkyl derivative self-contained about 12 to The fatty alcohol of about 14 carbon atoms.

Claims (12)

1. a kind of composition, it includes:

At least one alkyl lactyllactate with following general formula structure:

Wherein R is alkyl or alkoxylated alkyl, and wherein R includes the alkyl of 6 to 22 carbon atoms；It is living at least one surface Property agent；Wherein the composition in Aquo System and is Common detergents, household product, industrial or public clear Clean product, hard surface cleaner, wetting agent, facial cleanser, body wash, shampoo, skin lotion or shower gels form.

2. composition as described in claim 1, wherein the alkoxy is ethyoxyl or propoxyl group or their combination.

3. composition as described in claim 1, wherein at least one alkyl lactyllactate be L- dilactic acid ester, by The racemic dilactic acid ester of Study of Meso-Lactide preparation or the cream prepared by L- lactide and the mixture of Study of Meso-Lactide Acyl lactate.

4. composition as described in claim 1, wherein at least one surfactant includes at least one alkylsurfuric acid Salt, alkyl alkoxy sulfate, alkyl alkoxy carboxylates, alkylphosphonic, alkoxy phosphates, alkylsulfonate, Salt, alkyl sulfoacetate, the alkylbenzene of the salt of the alkyl ethyl ester of the salt or sulfonation of the alkyl methyl of sulfonation, the fatty acid of sulfonation Sulfonate, alhpa olefin sulfonate, paraffin sulfonate, alkyl isethionate, acyl lactate, sulfosuccinate, two Property acetate, sarcosinate, poly- Plantacare 818 carboxylate, lauryl glucose carboxylate, alkyl-glutamic acid salt, fatty acid acyl Amine, fatty alcohol, alkyl alcohol ethoxylates, alkylphenol ethoxylate, propylene glycol ester, gathers the fatty acid amide of ethoxylation Glyceride, glycol ester, the diol ester of ethoxylation, polypropylene glycol ester, alkyl glucoside, alkyl polyglycoside, alkyl glucose amide, Sorbitan ester, glycine betaine, amine oxide, sulfobetaines, alkylpolyoxyethylene, dialkyl dimethyl halide, Trialkyl methyl ammonium halide, polyquaternium, quaternized cellulose, quaternized guar gum, esterquats, amidoamines season The combination of ammonium compound, the derivative of alkyl amidopropyl quaternary ammonium compound and above-mentioned substance or above-mentioned substance.

5. a kind of alkyl lactyllactate compound, the alkyl lactyllactate compound be by lactide, tool there are two or Derived from the polyalcohol of more primary hydroxyls, wherein the compound protects in Aquo System and for Common detergents, household Reason product, industrial or public cleaning product, hard surface cleaner, wetting agent, facial cleanser, body wash, shampoo, shield The form of skin lotion or shower gels.

6. alkyl lactyllactate compound as claimed in claim 5, the compound has following general formula structure:

7. alkyl lactyllactate compound as claimed in claim 6, wherein R group includes about 2 to about 24 carbon atoms.

8. alkyl lactyllactate compound as claimed in claim 5, wherein the polyalcohol is glycerol or ethoxylation Glycerol.

9. composition as described in claim 1, wherein at least one alkyl lactyllactate is lauryl lactyllactate, The composition is preferably the form of product emulsion.

10. composition as described in claim 1, wherein the composition is personal cleaning compositions and the surface-active Agent is at least one anionic surfactant or zwitterionic surfactant or their combination.

11. composition as described in claim 1, wherein the composition is personal cleaning compositions and the surface-active Agent is alkyl sulfate, aryl-sulfate, alkylsulfonate, arylsulphonate, alkyl ether sulfate, aryl ether sulfate or sweet tea At least one of dish alkali.

12. a kind of method for preparing soap bar, comprising the following steps:

(1) component for the soap bar is weighed, and they are mixed into resulting mixture in one gallon of bucket, wherein the component With at least one alkyl lactyllactate with following general formula structure:

Wherein R is alkyl or alkoxylated alkyl；At least one surfactant；And water, wherein the composition is general Logical detergent, household product, industrial or public cleaning product, hard surface cleaner, wetting agent, facial cleanser, body Body cleaning product, shampoo, skin lotion or shower gels form；

(2) in 3 Kun grinders by gained mixture homogenization to form blend；

(3) gained blend is transferred to laboratory Sigma plodder, is fully controlled barrel temperature at about 30 DEG C extremely with cold water About 35 DEG C, eliminate heat caused by squeeze pressure；

(4) addendum cone housing is heated to about 45 DEG C, promotes the extrusion by the centrum；And

(5) extrudate is cut and is molded into soap bar.