Mixtures, their preparation, and uses

Abstract

The current invention is directed towards mixtures, comprising (A) in the range of from 15 to 85% by weight of at least one compound of the general formula (I) (B) in the range of from 85 to 15% by weight of at least one compound of the general formula (II), wherein the integers are defined as follows: R.sup.1 is C.sub.3-C.sub.4-alkyl, linear or branched, R.sup.2 is C.sub.5-C.sub.6-alkyl, linear or branched, G.sup.1, G.sup.2 are different or identical and selected from monosaccharides with 4 to 6 carbon atoms, x, y are numbers in the range of from 1.1 to 4, R.sup.3 is C.sub.3-C.sub.9-alkyl, linear or branched, the percentages referring to the total mixture. ##STR00001##

Claims

1. A mixture, comprising: (A) from 15 to 85% by weight of at least one compound of formula (I): ##STR00008## and (B) from 85 to 15% by weight of at least one compound of formula (II);
R.sup.3—CH.sub.2—O-(G.sup.2).sub.y-H  (II), wherein: R.sup.1 is C.sub.3-C.sub.4-alkyl, linear or branched, R.sup.2 is C.sub.5-C.sub.6-alkyl, linear or branched, G.sup.1, G.sup.2 are each independently monosaccharides with 4 to 6 carbon atoms, x, y are 1.4, R.sup.3 is C.sub.3-C.sub.9-alkyl, linear or branched, wherein the percentages of compound (A) and compound (B) refer to the total mixture, and compound (A) is different from compound (B).

2. The mixture of claim 1, wherein G.sup.1 and G.sup.2 are selected from the group consisting of glucose, arabinose, and xylose.

3. The mixture of claim 1, wherein R.sup.3 is selected from the group consisting of CH(C.sub.2H.sub.5)—(CH.sub.2).sub.3—CH.sub.3, n-heptyl, and n-nonyl.

4. The mixture according to claim 1, comprising at least two of the compounds (A).

5. The mixture of claim 1, wherein in one compound (A), R.sup.1 is isopropyl and R.sup.2 is CH.sub.2—CH.sub.2—CH(CH.sub.3).sub.2.

6. The mixture of claim 1, wherein in one compound (A), R.sup.1 is n-C.sub.3H.sub.7 and R.sup.2 is n-C.sub.5H.sub.11.

7. A process for making the mixture of claim 1, comprising mixing at least one compound (A) with at least one compound (B).

8. A process for cleaning a hard surface or fiber, comprising contacting the mixture of claim 1 with the hard surface or fiber.

9. The process of claim 8, further comprising a degreasing.

10. An aqueous formulation, comprising: from 35 to 80% by weight of the mixture of claim 1; and water.

11. The aqueous formulation of claim 10, further comprising a by-product, stemming from the synthesis of compound (A) or compound (B).

12. The mixture of claim 1, which is a clear mixture.

13. The aqueous formulation of claim 10, which is a clear aqueous formulation.

14. The mixture of claim 1, which is a clear mixture as determined by a Hazen number for a clear liquid and measured according to DIN EN ISO 6271-1 or 6271-2.

15. A mixture, comprising: (A) from 15 to 85% by weight of at least one compound of formula (I): ##STR00009## and (B) from 85 to 15% by weight of at least one compound of formula (II):
R.sup.3—CH.sub.2—O-(G.sup.2).sub.y-H  (II), wherein: R.sup.1 is C.sub.3-C.sub.4-alkyl, linear or branched, R.sup.2 is C.sub.5-C.sub.6-alkyl, linear or branched, G.sup.1, G.sup.2 are each independently monosaccharides with 4 to 6 carbon atoms, x, y are numbers in the range of from 1.1 to 4, R.sup.3 is a branched C.sub.3-C.sub.6-alkyl or a linear C.sub.3-C.sub.4 alkyl, wherein the percentages of compound (A) and compound (B) refer to the total mixture, and compound (A) is different from compound (B).

16. The mixture of claim 15, wherein R.sup.3 is a branched C.sub.3-C.sub.6-alkyl.

17. An aqueous formulation, comprising: from 35 to 80% by weight of the mixture of claim 15; and water.

18. The mixture of claim 15, wherein in molecules with x or y, respectively, being 2 or more, the sugar molecules are linked in 1,4-position(s).

Description

WORKING EXAMPLES

(1) General Remarks

(2) Percentages are % by weight (wt %) unless expressly noted otherwise.

(3) In the context of the present invention, room temperature and ambient temperature both refer to 20° C. unless expressly noted otherwise.

(4) Hazen numbers were determined using solutions of the respective compound of general formula (I) or (II) in 10% by weight solutions, with mixtures of 90% by weight of water and 10% by weight of isopropanol as solvent. Only if a turbid mixture was formed, a mixture of 80% by weight of water and 20% by weight of isopropanol was used. A round vessel (11 mm diameter) was used as cuvette. The colour was then determined with a spectrophotometer Dr. Lange Lico 200 according to the user's manual.

(5) (A.2) was synthesized as follows:

(6) As alcohol (III.1), the following compound was used:

(7) ##STR00006##

(8) It was obtained by a Guerbet reaction of iso-amyl alcohol. It had an impurity of 10 mol-% of (III.1a)

(9) ##STR00007##

(10) It was thus a 9:1 mixture of isomers hereinafter also being referred to as “alcohol mixture (III.1)”.

(11) A jacketed 4 l glass reactor equipped with a condenser with a Dean-Stark trap, a three stage agitator, a distillation receiver and a dropping funnel was charged with 703.6 g (2.4 moles) of glucose monohydrate and 1250 g of alcohol mixture (III.1). The resultant slurry was dried at 75° C. at a pressure of 30 mbar for a period of 30 minutes under stirring. Then, the pressure was adjusted to ambient pressure, and the slurry was heated to 90° C. An amount of 2.14 g of concentrated sulfuric acid (96% by weight), dissolved in 100 g of alcohol mixture (III.1), was added and heating was continued until a temperature of 106° C. was reached. The pressure was set to 30 mbar, and, under stirring, the water formed was distilled off at the Dean-Stark trap equipped with cold traps. After 5.5 hours, no more water was formed, and the amount of water to be formed theoretically was in the cold traps.

(12) The reaction was then quenched by neutralizing the catalyst with 2.6 g of 50% by weight aqueous NaOH. The pH value, measured in a 10% solution in isopropanol/water (1:10), was at least 9.5. The reaction mixture was then transferred into a round flask, excess alcohol mixture (III.1) was distilled off at 140° C./1 mbar. During the removal of the excess alcohol mixture (III.1), the temperature was step-wise raised to 180° C. within 2 hours. When no more alcohol would distil off, the liquid reaction mixture was stirred into water (room temperature) in order to adjust the solids content to 60% and cooled to ambient temperature, hereby forming an aqueous paste. The compound (A.2) had a degree of polymerization (number average) of 1.3 and a residual alcohol content of 0.04 g, and the paste so obtained had a water content of 40.8%. The pH value was 4.1, the colour number (Gardner) was 16.3.

(13) In order to improve the colour, 800 g of the above aqueous paste were transferred into a 4 l vessel and reacted with 38.5 g of 35% by weight aqueous H.sub.2O.sub.2 which was added in a way that the total peroxide content was in the range of from 300 to 1,500 ppm, determined with Merckoquant peroxide test sticks. The pH value was maintained in the range from 7.5 to 8. Finally, the pH value was adjusted to 11.5 with 50% by weight aqueous NaOH. The colour number (Gardner) had dropped to 2.9, and the water content had raised to 45.9%. All measurements with respect to pH value and peroxide content were performed on a 10% by volume diluted paste. For dilution, a 15% by volume aqueous solution of isopropanol was used.

(14) The following alkyl polyglucosides were used:

(15) (A.1): 2-n-propyl heptyl glucoside: G.sup.1=glucose, x=1.4, R.sup.1=n-C.sub.3H.sub.7, R.sup.2=n-C.sub.5H.sub.11

(16) (A.2): 2-isopropyl 5-methylhexyl glucoside, G.sup.1=glucose, x=1.3, R.sup.1=iso-C.sub.3H.sub.7, R.sup.2=iso-C.sub.5H.sub.11

(17) (B.1): 2-ethylhexyl glucoside, G.sup.2=glucose, y=1.4, R.sup.3=CH(C.sub.2H.sub.5)—(CH.sub.2).sub.2CH.sub.3

(18) (B.2): n-hexyl glucoside, G.sup.2=glucose, y=1.4, R.sup.3=n-C.sub.5H.sub.11

(19) (B.3): isoamyl glucoside, G.sup.2=glucose, y=1.4, R.sup.3=(CH.sub.2).sub.2CH(CH.sub.3).sub.2

(20) (B.4): n-butyl glucoside, G.sup.2=glucose, y=1.4, R.sup.3=n-C.sub.3H.sub.7

(21) The values of x and y were calculated based on the glucoside distribution determined by high temperature gas chromatography (HTGC), e.g. 400° C., in accordance with K. Hill et al., Alkyl Polyglycosides, VCH Weinheim, New York, Basel, Cambridge, Tokyo, 1997, in particular pages 28 ff., with Duran glass as capillary material.

(22) I. Formation of Mixtures According to the Invention and of Comparative Mixtures

(23) The respective compounds (A) and (B) were each dissolved in water to form 50% by weight of aqueous solutions. One solution of a compound (A) and one of a compound (B) were combined in the desired mass ratio in a beaker with magnetic stirring. Depending on the ratio of the compounds (A) and (B), mixture according to the invention or comparative mixtures were obtained according to table 1 as clear aqueous solutions.

(24) Samples of the respective mixtures were stored at ambient temperature for twelve weeks and then evaluated visually.

(25) As additional comparison, 50% by weigh aqueous solutions with pure (A.1) and pure (A.2) each were stored at ambient temperature for twelve weeks and then evaluated visually. Both the solutions were turbid.

(26) The results are summarized in table 1.

(27) TABLE-US-00001 TABLE 1 mixtures according to the invention, comparative mixtures and their storage behaviour Name (A) (B) mass ratio (A):(B) Stability (20° C.) C-(M-1.1-8/1) (A.1) (B.1) 8:1 turbid (M-1.1-2/1) (A.1) (B.1) 2:1 clear (M-1.1-1/1) (A.1) (B.1) 1:1 clear C-(M-1.2-4/1) (A.1) (B.2) 8:1 turbid (M-1.2-4/1) (A.1) (B.2) 4:1 clear (M-1.2-2/1) (A.1) (B.1) 2:1 clear (M-1.2-1/1) (A.1) (B.1) 1:1 clear C-(M-1.3-8/1) (A.1) (B.3) 8:1 turbid (M-1.3-4/1) (A.1) (B.3) 4:1 clear (M-1.3-2/1) (A.1) (B.3) 2:1 clear (M-1.3-1/1) (A.1) (B.3) 1:1 clear C-(M-1.4-8/1) (A.1) (B.4) 8:1 turbid (M-1.4-4/1) (A.1) (B.4) 4:1 clear (M-1.4-2/1) (A.1) (B.4) 2:1 clear (M-1.4-1/1) (A.1) (B.4) 1:1 clear C-(M-2.1-8/1) (A.2) (B.1) 8:1 turbid (M-2.1-2/1) (A.2) (B.1) 2:1 clear (M-2.1-1/1) (A.2) (B.1) 1:1 clear C-(M-2.2-4/1) (A.2) (B.2) 8:1 turbid (M-2.2-4/1) (A.2) (B.2) 4:1 clear (M-2.2-2/1) (A.2) (B.2) 2:1 clear (M-2.2-1/1) (A.2) (B.2) 1:1 clear C-(M-2.3-8/1) (A.2) (B.3) 8:1 turbid (M-2.3-4/1) (A.2) (B.3) 4:1 clear (M-2.3-2/1) (A.2) (B.3) 2:1 clear (M-2.3-1/1) (A.2) (B.3) 1:1 clear C-(M-2.4-8/1) (A.2) (B.4) 8:1 turbid (M-2.4-4/1) (A.2) (B.4) 4:1 clear (M-2.4-2/1) (A.2) (B.4) 2:1 clear (M-2.4-1/1) (A.2) (B.4) 1:1 clear

(28) II. Cleaning Properties of Mixtures According to the Invention and of Comparative Mixtures

(29) Test Soil:

(30) 36 wt % white spirit (boiling range 80/110°);

(31) 17 wt % triglyceride (commercially available Myritol® 318);

(32) 40 wt % mineral oil (commercially available Nytex® 801),

(33) 7 wt % carbon black.

(34) For preparing the test soil, a beaker was charged with the white spirit. The triglyceride and the mineral oil were added under stirring (500 rpm) until a clear solution had formed. The carbon black was then slowly added. The dispersion so obtained was then stirred for 30 minutes with an IKA Ultra-Turrax® T25 digital—basic. Thereafter, the dispersion was then stirred with a magnetic stirrer for 21 days at ambient temperature and then for 30 minutes with the Ultra-Turrax specified above. The dispersion so obtained was then stored in a closed glass bottle for additional 14 days under ambient conditions while being continuously stirred on a magnetic stirring device. The test soil so obtained was then ready for use.

(35) As test substrates, white PVC stripes (37.Math.423.Math.1.2 mm) (commercially available from Gerrits, PVC-Tanzteppich® 5410 Vario white) were used.

(36) As test cleaners, the amounts of mixture according to the invention or of comparative mixture according to tables 1 and 2 were dissolved in 50 ml of water. The pH value was adjusted to 7 with 0.1 M NaOH or 0.1 M acetic acid, if necessary. Then, the total mass of each of the test cleaners was adjusted to the total mass of 100 g (±0.2) g by addition of distilled water.

(37) The tests were Gardner tests performed in an automatic test robot. It contained a sponge (viscose, commercially available as Spontex® Z14700), cross section 9.Math.4 cm. Per run, 5 test stripes were first soiled with 0.28 (±0.2) g of test soil by brush and then dried at ambient temperature for one hour. Then they were treated with the humid sponge, soaked with 20 ml of test cleaner, swaying ten times with a weight of 300 g and a swaying velocity 10 m/s, followed by rinsing twice with distilled water and drying at ambient temperature for 4 hours. For each test stripe, a new sponge was used. The soiling and de-soiling were each recorded with a digital camera.

(38) TABLE-US-00002 TABLE 2 Test cleaners and their performance Soil Standard Mixture Ratio solids removal deviation Name tested (A), (B) (A)/(B) content [%] [%] C-TC.1 — (A.1) 100:0  1.0 83.3 3.4 C-TC.2 — (A.1) 100:0  2.0 87.0 4.6 TC.3 (M-1.1-2/1) (A.1), 2:1 1.0 83.3 5.0 (B.1) TC.4 (M-1.1-2/1) (A.1), 2:1 2.0 81.3 4.6 (B.1) TC.5 (M-1.1-1/1) (A.1), 1:1 1.0 78.0 4.3 (B.1) TC.6 (M-1.1-1/1) (A.1), 1:1 2.0 75.1 5.2 (B.1) C-TC.7 — (B.1)  0:100 0.5 28.6 1.5 C-TC.8 — (B.1)  0:100 1.0 43.5 1.8 C-TC.9 — (B.1)  0:100 2.0 54.8 2.4

(39) The solids content refers to the test cleaner and is expressed in g solids/100 g.

(40) The standard deviation refers to the 5 PVC stripes tested per run with the same cleaner and the same soil.