US5266690A — Preparation of alkylpolyglycosides

Claim 1

Independent Claim 164 words

A method of producing an alkyl polyglycoside composition having enhanced surfactant properties and a purified alkyl monoglycoside composition, in which the alkyl group contains from about 8 to about 20 carbon atoms comprising (a) providing a reaction mixture of alkyl monoglycoside and alkyl polyglycoside having an essentially Flory distribution resulting from the reaction of an alkyl alcohol and a saccharide in the presence of an acid catalyst; (b) molecularly distilling said reaction mixture under conditions so as to separate monoglycoside from the polyglycoside; and (c) recovering from the molecular distillation (i) a highly concentrated, purified alkyl monoglycoside stream essentially free from polyglycoside and (ii) an alkyl polyglycoside composition containing polyglycosides having DPs of 2 and higher originally present in said reaction mixture and having an HLB in the range of about 10 to about 16 and an average DP at least about 1.8 and at least about 0.2 units higher than the average DP of the reaction mixture before separation of the alkyl monoglycoside.

Claim 2

Independent Claim 164 words

A method of producing an alkyl polyglycoside composition having enhanced surfactant properties and a purified alkyl monoglycoside composition, in which the alkyl group contains from about 8 to about 20 carbon atoms comprising (a) providing a reaction mixture of alkyl monoglycoside and alkyl polyglycoside having an essentially Flory distribution resulting from the reaction of an alkyl alcohol and a saccharide in the presence of an acid catalyst; (b) molecularly distilling said reaction mixture under conditions so as to separate monoglycoside from the polyglycoside; and (c) recovering from the molecular distillation (i) a highly concentrated, purified alkyl monoglycoside stream essentially free from polyglycoside and (ii) an alkyl polyglycoside composition containing polyglycosides having DPs of 2 and higher originally present in said reaction mixture and having an HLB in the range of about 10 to about 16 and an average DP at least about 1.8 and at least about 0.2 units higher than the average DP of the reaction mixture before separation of the alkyl monoglycoside.

Claim 3

Dependent Claim 22 words

A method as defined in claim 1, wherein said highly concentrated, purified alkyl monoglycoside has an average DP less than about 1.1.

Claim 4

Dependent Claim 30 words

A method as defined in claim 1, wherein said alkyl polyglycoside composition after separation of monoglycoside from the reaction mixture has an average DP of about 1.8 to about 3.

Claim 5

Independent Claim 32 words

A method as defined in claim wherein the amount by weight of monoglycoside separated from the reaction mixture is at least half the amount of monoglycoside present in the original reaction mixture.

Claim 6

Dependent Claim 48 words

A method as defined in claim 4, wherein said original reaction mixture before the molecular distillation has an average DP of about 1.3 to about 1.7 and said alkyl polyglycoside composition recovered after the molecular distillation has an average DP within the trapezoidal area ABCDE of FIG. 4.

Claim 7

Dependent Claim 30 words

A method as defined in claim 4, wherein the amount of monoglycoside present in the alkyl polyglycoside composition after separation of monoglycoside therefrom is less than about 30% by weight.

Claim 8

Dependent Claim 31 words

A method as defined in claim 4, wherein the amount of the monoglycoside present in the alkyl polyglycoside composition after separation of monoglycoside therefrom is less than about 20% by weight.

Claim 9

Dependent Claim 66 words

A method as defined in claim 1 wherein said alkyl monoglycoside is removed by molecularly distilling said alkyl glycoside reaction mixture having a Flory distribution at a temperature above about 200° C. and a pressure of about 0.1 mbar and lower for a time sufficient to remove the alkyl monoglycoside in an amount to provide a polyglycoside residue with an average DP of at least 1.8.

Claim 10

Dependent Claim 35 words

A method as defined in claim 8 wherein the vaporizing and condensing surfaces in said molecular distillation is in the range of about 0.1 to about 10 times the mean free path of distilling molecules.

Claim 11

Dependent Claim 22 words

A method as defined in claim 8 in which said distillation temperature is in the range of about 220° to 260° C.

Claim 12

Dependent Claim 18 words

A method as defined in claim 10 wherein said distillation temperature is about 240° to about 250° C.

Claim 13

Dependent Claim 51 words

A method as defined in claim 8 wherein at least about half of the alkyl monoglycoside in said alkyl glycoside reaction mixture having a Flory distribution is removed providing a retained polyglycoside composition having a monoglycoside content less than about 30% by weight based on the total retained polyglycoside residue composition.

Claim 14

Dependent Claim 23 words

A method as defined in claim 12 wherein said monoglycoside content in said retained polyglycoside composition is less than about 25% by weight.

Claim 15

Independent Claim 176 words

A method of producing an alkyl polyglycoside composition having enhanced surfactant properties and a purified alkyl monoglycoside composition, in which the alkyl group contains from about 8 to about 20 carbon atoms comprising (a) providing a reaction mixture of alkyl monoglycoside and alkyl polyglycoside having an essentially Flory distribution resulting from the reaction of an alkyl alcohol and a saccharide in the presence of an acid catalyst; (b) molecularly distilling said reaction mixture at a pressure of 0.1 mbar or lower and a temperature above 200° C. so as to separate at least about half of the monoglycoside from the polyglycoside; and (c) recovering from the molecular distillation (i) a highly concentrated, purified alkyl monoglycoside stream essentially free from polyglycoside and (ii) an alkyl polyglycoside composition containing polyglycosides having DPs of 2 and higher and having an HLB in the range of about 10 to about 16 and an average DP at least about 1.8 and at least about 0.2 units higher than the average DP of the reaction mixture before separation of the alkyl monoglycoside.

Claim 16

Independent Claim 176 words

A method of producing an alkyl polyglycoside composition having enhanced surfactant properties and a purified alkyl monoglycoside composition, in which the alkyl group contains from about 8 to about 20 carbon atoms comprising (a) providing a reaction mixture of alkyl monoglycoside and alkyl polyglycoside having an essentially Flory distribution resulting from the reaction of an alkyl alcohol and a saccharide in the presence of an acid catalyst; (b) molecularly distilling said reaction mixture at a pressure of 0.1 mbar or lower and a temperature above 200° C. so as to separate at least about half of the monoglycoside from the polyglycoside; and (c) recovering from the molecular distillation (i) a highly concentrated, purified alkyl monoglycoside stream essentially free from polyglycoside and (ii) an alkyl polyglycoside composition containing polyglycosides having DPs of 2 and higher and having an HLB in the range of about 10 to about 16 and an average DP at least about 1.8 and at least about 0.2 units higher than the average DP of the reaction mixture before separation of the alkyl monoglycoside.

Claim 17

Dependent Claim 22 words

A method as defined in claim 14 wherein the distillation temperature is in the range of about 220° to about 260° C.

Claim 18

Dependent Claim 21 words

A pressure as defined in claim 15 wherein said temperature is in the range of about 240° to about 250° C.

Claim 19

Dependent Claim 48 words

A method as defined in claim 15 wherein said original reaction mixture before the molecular distillation has an average DP of about 1.3 to about 1.7 and said alkyl polyglycoside composition recovered after the molecular distillation has an average DP within the trapezoidal area ABCDE of FIG. 4.

Claim 20

Dependent Claim 11 words

The retained alkyl polyglycoside composition of the process of claim 1.

Claim 21

Dependent Claim 13 words

The alkyl polyglycoside residue after the molecular distillation process defined in claim 14.

Claim 22

Dependent Claim 13 words

The alkyl polyglycoside residue after the molecular distillation process defined in claim 17.

Claim 23

Dependent Claim 103 words

An alkyl polyglycoside composition having increased surfactant properties and an HLB in the range of about 10 to about 16 and having a non-Flory distribution of glycosides, comprising a mixture of an alkyl monoglycoside and a mixture of alkyl polyglycosides having varying degrees of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with the polyglycoside having a degree of polymerization of 3, predominate in relation to the amount of monoglycoside, said composition having an average degree of polymerization of about 1.8 to about 3.

Claim 24

Dependent Claim 103 words

An alkyl polyglycoside composition having increased surfactant properties and an HLB in the range of about 10 to about 16 and having a non-Flory distribution of glycosides, comprising a mixture of an alkyl monoglycoside and a mixture of alkyl polyglycosides having varying degrees of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with the polyglycoside having a degree of polymerization of 3, predominate in relation to the amount of monoglycoside, said composition having an average degree of polymerization of about 1.8 to about 3.

Claim 25

Dependent Claim 22 words

An alkyl polyglycoside composition as defined in claim 21 in which the alkyl monoglycoside content is less than about 30% by weight.

Claim 26

Dependent Claim 23 words

An alkyl polyglycoside composition as defined in claim 22 in which the amount of alkyl monoglycoside is less than about 25% by weight.

Claim 27

Dependent Claim 29 words

An alkyl polyglycoside composition as defined in claim 21 in which the amount of polyglycoside having a degree of polymerization above 4 is less than about 20% by weight.

Claim 28

Dependent Claim 23 words

An alkyl polyglycoside composition as defined in claim 21 in which the alkyl group contains from about 8 to about 18 carbon atoms.

Claim 29

Dependent Claim 27 words

An alkyl polyglycoside composition as defined in claim 25 in which the average carbon chain length of the alkyl group is from about 9 to about 13.

Claim 30

Dependent Claim 19 words

An alkyl polyglycoside composition as defined in claim 21 and falling within the trapezoid area ABCDE of FIG. 4.

Claim 31

Dependent Claim 45 words

An alkyl polyglycoside composition as defined in claim 27 derived from the removal of at least about half of the alkyl monoglycoside from a mixture of alkyl monoglycoside and alkyl polyglycoside having a Flory distribution and an average DP of about 1.3 to about 1.7.

Claim 32

Independent Claim 93 words

A method of preparing an alkyl polyglycoside with mole ratios of anhydroglucose to bound alkyl groups of 1.5 or lower in which the alkyl group contains from about 6 to about 20 carbon atoms comprising reacting an alkyl monoglycoside fraction essentially free of polyglycoside with an alkyl alcohol in which the alkyl group contains from about 6 to about 20 carbon atoms in the presence of an acid catalyst for a time sufficient to provide an alkyl polyglycoside having a mole ratio of anhydroglucose to alkyl group of about 1.1 to about 1.5.

Claim 33

Independent Claim 93 words

A method of preparing an alkyl polyglycoside with mole ratios of anhydroglucose to bound alkyl groups of 1.5 or lower in which the alkyl group contains from about 6 to about 20 carbon atoms comprising reacting an alkyl monoglycoside fraction essentially free of polyglycoside with an alkyl alcohol in which the alkyl group contains from about 6 to about 20 carbon atoms in the presence of an acid catalyst for a time sufficient to provide an alkyl polyglycoside having a mole ratio of anhydroglucose to alkyl group of about 1.1 to about 1.5.

Claim 34

Dependent Claim 19 words

A process as defined in claim 29 wherein said alkyl monoglycoside is the monoglycoside fraction (a) of claim 1.

Claim 35

Dependent Claim 23 words

A process as defined in claim 29, wherein the alkyl group in said monoglycoside contains from about 8 to about 16 carbon atoms.

Claim 36

Dependent Claim 28 words

A process as defined in claim 31 wherein said alkyl alcohol is employed at a level to provide less than about 4 moles alkyl group to anhydroglucose unit.

Claim 37

Dependent Claim 28 words

A process as defined in claim 32 wherein said alcohol is employed at a level to provide about 1.5 to about 3 moles alkyl group per anhydroglucose unit.

Claim 38

Dependent Claim 26 words

A process as defined in claim 32 wherein said acid catalyst is present in an amount of about to about 10 milliequivalents per mole of anhydroglucose.

Claim 39

Dependent Claim 26 words

A process as defined in claim 34 wherein said catalyst is present in an amount of about 5 to about 8 milliequivalents per mole of anhydroglucose.

Claim 40

Dependent Claim 25 words

A process as defined in claim 29 wherein said monoglycoside and said alcohol is heated at a temperature of about 80° to about 140° C.

Claim 41

Dependent Claim 31 words

A process as defined in claim 36 wherein said acid catalyst is an alkyl benzene sulfonic acid in which the alkyl group contains from about 8 to about 20 carbon atoms.

Claim 42

Dependent Claim 24 words

An alkylpolyglycoside having a mole ratio of anhydroglucose to bound alkyl groups of about 1.5 or lower prepared by the process of claim 29.

Claim 43

Dependent Claim 24 words

An alkyl polyglycoside as defined in claim 38 having a mole ratio of anhydroglucose to bound alkyl group of about 1.1 to about 1.5.

Claim 44

Dependent Claim 21 words

A surfactant composition comprising from about 0.5 to about 99% by weight of the alkyl polyglycoside composition defined in claim 21.

Claim 45

Dependent Claim 16 words

A surfactant composition as defined in claim 40 and further comprising a solvent and an adjuvant.

Claim 46

Dependent Claim 37 words

A surfactant as defined in claim 41 wherein said solvent is present in an amount of about 0.5 to about 99.5% by weight and said adjuvant is present in an amount up to about 99.5% by weight.

Claim 47

Dependent Claim 11 words

A hard surface cleaner containing the surfactant composition of claim 40.

Claim 48

Dependent Claim 10 words

A laundry detergent containing the surfactant composition of claim 40.

Claim 49

Dependent Claim 11 words

A liquid hand soap containing the surfactant composition of claim 40.

Claim 50

Dependent Claim 10 words

A hair shampoo containing the surfactant composition of claim 40.

Annuity Stage	Window Opens	Payment Deadline	Surcharge Period Until	Estimated Fee	Status
3.5 Years (Year 4)	1996-11-29	1997-05-31	1997-11-30	$2000.00	Window Closed / Lapsed
7.5 Years (Year 8)	2000-11-29	2001-05-31	2001-11-30	$3760.00	Window Closed / Lapsed
11.5 Years (Year 12)	2004-11-29	2005-05-31	2005-11-30	$7700.00	Window Closed / Lapsed

Preparation of alkylpolyglycosides

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