Lubricating agent

Abstract

The present invention is a lubricating agent containing a compound represented by the following formula 1: ##STR00001## wherein R.sup.1 and R.sup.2 each represent a hydrocarbon group with 6 or more and 24 or less carbons; A.sup.1O and A.sup.2O each represent an alkyleneoxy group with 2 or more and 4 or less carbons; x1 and x2 are average numbers of added moles, and each represent a number of 0 or more and 10 or less; and M is a cationic ion.

Claims

1. A method comprising: adhering (A) a compound represented by the following formula 1 and water to a textile product to form a liquid sliding surface against water on the textile product, ##STR00008## wherein: R.sup.1 and R.sup.2 each represent a branched-chain alkyl group with 10 or more and 12 or less carbons; A.sup.1O and A.sup.2O each represent an alkyleneoxy group with 2 or more and 4 or less carbons; x1 and x2 are average numbers of added moles, and each represent a number of 0 or more and 10 or less; and M is a cationic ion.

2. The method according to claim 1, wherein x1 and x2 in the formula 1 each represent 0.

3. The method according to claim 1, herein R.sup.1 and R.sup.2 in the formula 1 each represent a branched-chain alkyl group derived from a Guerbet alcohol with 10 or more and 12 or less carbons.

4. The method according to claim 1, wherein the textile product is treated with a treatment liquid comprising the compound represented by formula 1 and water.

5. The method according to claim 1, wherein the textile product comprises a cotton fiber.

6. The method according to claim 1, wherein (B) a surfactant, which is not a compound of formula 1, is further adhered to the textile product together with the compound represented by formula 1 and water.

7. The method according to claim 1, wherein the textile product comprises a fiber selected from natural fibers, synthetic fibers and semi-synthetic fibers.

8. The method according to claim 1, wherein the textile product comprises a hydrophobic fiber.

9. The method according to claim 1, wherein the textile product comprises a fiber selected from protein fibers, polyamide fibers, polyester fibers, polyacrylonitrile fibers, polyvinyl alcohol fibers, polyvinyl chloride fibers, polyvinylidene chloride fibers, polyolefin fibers, polyurethane fibers, polyvinyl chloride/polyvinyl alcohol copolymer fibers, polyalkylene paraoxybenzoate fibers, and polyfluoroethylene fibers.

10. The method according to claim 1, wherein the textile product comprises a hydrophilic fiber.

11. The method according to claim 1, wherein the textile product comprises a fiber selected from seed hair fibers, bast fibers, vein fibers, palm fibers, juncus, straw, aminal hair fibers, silk fibers, feathers, and cellulose fibers.

12. The method according to claim 1, wherein the textile product comprises at least 5 mass % cotton fiber.

13. The method according to claim 1, wherein the textile product comprises at least 10 mass % cotton fiber.

14. The method according to claim 1, wherein the textile product comprises at least 20 mass % cotton fiber.

15. The method according to claim 1, wherein the textile product comprises 100 mass % cotton fiber.

Description

EXAMPLES

(1) <Lubricity evaluation 1>

(2) A textile product was treated with a water bath using each of the following lubricating agents 1 to 3 and comparative lubricating agent 1, and the water content after dehydration was measured by the method described later and used as an indicator of lubricity (liquid sliding ability against water) impartation. Lubricating agent 1: sodium bis-(2-propylheptyl) sulfosuccinate Lubricating agent 2: sodium bis-(2-butyloctyl) sulfosuccinate Lubricating agent 3: a sodium dialkyl sulfosuccinate obtained by sulfonating a maleic acid diester obtained by using the raw materials of isodecyl alcohol (manufactured by KH Neochem Co., Ltd., decanol) and maleic anhydride Comparative lubricating agent 1: dioctadecyl ammonium chloride
(1) Pretreatment of Towel for Evaluation

(3) Towels treated beforehand in the following manner to remove starching agents and impurities were used for evaluation.

(4) With a fully automatic washing machine (manufactured by Panasonic Corporation, model number: NA-F60PB3), a series of steps of a washing process (the water amount 50 L, washing for 10 minutes->tub rinsing twice->dehydration for 9 minutes) was repeated three times on 24 commercial cotton towels (manufactured by Yoshikawa Towel Co., Ltd., TW220, white) by adding 52.22 g of a 10% diluted solution of a nonionic surfactant (manufactured by Kao Corporation, EMULGEN 108) as a detergent and using Wakayama city tap water as water. Subsequently, the series of steps of the washing process was repeated twice with water alone. After that, the towels were left at a room temperature (25? C.) for 24 hours and thus naturally dried.

(5) (2) Method for Treating Towel

(6) In a portable washing machine (manufactured in the name of National, model number: NA-35), a predetermined amount of ion exchange water (bath ratio 25 kilograms per kilogram of the towels) was placed, and an aqueous calcium chloride solution (equivalent to 4000?DH) was added such that a treatment liquid to be obtained had any hardness shown in Table 1, and while stirring the mixture, a 5 mass % water dispersion of any of the lubricating agents shown in Table 1 was added such that the treating amount was as shown in Table 1 and stirred for 1 minute to prepare the treatment liquid, in which three of the cotton towels pretreated in the above (1) (about 210 g in total) were thereafter placed and treated for 5 minutes under stirring.

(7) (3) Measurement of the Water Content after Dehydration

(8) The three cotton towels treated in (2) were dehydrated for 5 minutes in a dehydration tub of a twin tub washing machine (manufactured by TOSHIBA CORPORATION, model number: VH-52G (H)), and the water content after dehydration was measured. The results are shown in Table 1.

(9) TABLE-US-00001 TABLE 1 Comparative Comparative Comparative Example 1-1 Example 1-2 Example 1-3 Example 1-4 Example 1-5 Example 1-6 example 1-1 example 1-2 example 1-3 Test number a b c a b c a b c a b c a b c a b c a b c a b c a b c Lubricating Type Lubricating Lubricating Lubricating Lubricating Lubricating Lubricating Comparative Comparative agent agent 1 agent 1 agent 2 agent 2 agent 3 agent 3 lubricating agent 1 lubricating agent 1 Treating 0.1 0.3 0.1 0.3 0.1 0.3 0.1 0.3 amount [% o.w.f.] Hardness of treatment 0 4 20 0 4 20 0 4 20 0 4 20 0 4 20 0 4 20 0 4 20 0 4 20 0 4 20 liquid [? DH] Water content after 49 46 46 49 47 47 56 54 48 52 49 47 54 53 51 52 53 52 62 60 60 56 58 59 53 57 57 dehydration [mass %] Dehydration promoting 21% 23% 23% 21% 22% 22% 10% 10% 20% 16% 18% 22% 13% 12% 15% 16% 12% 13% 10% 3% 2% 15% 5% 5% rate

(10) It is understood that the water content after dehydration can be reduced in examples 1-1 to 1-4 in which the lubricating agent of the present invention was used. Particularly, in examples 1-1 and 1-2, the dehydration promoting rate is 20% or more at any hardness, which indicates excellent lubricity against water and less susceptibility to the hardness of water.

(11) Note that the dehydration promoting rate (%) is calculated by the following formula from the water content W after the treatment with any of the treatment liquids having a predetermined hardness and dehydration and the water content W.sub.0 after the treatment with a treatment liquid having the same hardness and with no lubricating agents and dehydration. In the present example, W.sub.0 is selected from any of a, b and c of comparative example 1-1.
Dehydration Promoting Rate (%)=100?[W.sub.0?W]/W.sub.0

(12) From the results in Table 1, the lubricating agent of the present invention is judged to be more effective in promoting the separation of water during dehydration than the lubricating agent used in comparative examples.

(13) (4) Measurement 2 of the Water Content after Dehydration

(14) The three cotton towels treated in (2) were dehydrated for 2 minutes in the dehydration tub of the twin tub washing machine (manufactured by TOSHIBA CORPORATION, model number: VH-52G (H)), and the water content after dehydration was measured to calculate the dehydration promoting rate in the same manner as described above. In the present example, W.sub.0 in the calculation formula of the dehydration promoting rate is selected from any of a, b and c of comparative example 2-1. The results are shown in Table 2.

(15) TABLE-US-00002 TABLE 2 Comparative Example 2-1 Example 2-2 example 2-1 Test number a b c a b c a b c Lubricating Type Lubricating agent 1 Lubricating agent 3 agent Treating amount 0.3 0.3 [% o.w.f.] Hardness of treatment 0 4 20 0 4 20 0 4 20 liquid [? DH] Water content after 59 58 57 58 59 57 67 66 66 dehydration [mass %] Dehydration promoting rate 12% 12% 14% 13% 11% 14%

(16) It is understood that the water content after dehydration can be reduced in examples 2-1 to 2-2 in which the lubricating agent of the present invention was used. Even with dehydration shorter than usual for 2 minutes, the dehydration promoting rate is 10% or more at any hardness, which indicates excellent lubricity against water and less susceptibility to the hardness.

(17) The lubricating agent compositions in Tables 3a and 3b were prepared by using lubricating agent 1 and the components listed below, and the textile product was treated with a water bath using each of them and the water content after dehydration was measured in the same manner as in example 1 or the like and used as an indicator of lubricity impartation. In the treatment of towels in the above (2) in the present example, the lubricating agent compositions were used such that the total amounts of components (A) and (B) were the treating amounts in Tables 3a and 3b (provided that, for comparative examples 3-9 and 3-10, the amount of PG is shown in parentheses). Further, the water content was measured by the method in the above (3) after dehydration for 5 minutes and by the method in the above (4) after dehydration for 2 minutes. Further, the dehydration enhancing rates (%) were calculated by the following formula, where W represents the water content after the treatment with any of the treatment liquids having a predetermined hardness and dehydration, and W.sub.B represents the water content after the treatment with the treatment liquid having the same hardness obtained from the reference composition containing the same component (B) as that contained in the composition for which W was evaluated and dehydration. Note that the dehydration enhancing rates were not calculated for the compositions not containing component (B).
Dehydration enhancing rate (%)=100?[W.sub.B?W]/W.sub.B
<Component (B)> B-1: sodium internal olefin sulfonate with 18 carbons B-2: sodium dodecyl benzene sulfonate B-3: a sodium polyoxyethylene/polyoxypropylene lauryl ether sulfate (a compound with an average number of added moles of ethylene oxide of 1.5 and an average number of added moles of propylene oxide of 0.4 in which the polyoxyethylene group and the polyoxypropylene group are bonded to the lauryl group in blocks in this order) B-4: sodium lauryl sulfate B-5: sodium myristyl sulfate B-6: sodium palmityl sulfate B-7: a polyoxyethylene lauryl ether (with an average number of added moles of ethylene oxide of 6) B-8: a polyoxyethylene lauryl ether (with an average number of added moles of ethylene oxide of 21) B-9: a polyoxyethylene lauryl ether (with an average number of added moles of ethylene oxide of 4) B-10: lauryl betaine, lauryl dimethyl aminoacetic acid betaine B-11: 2-cocoyl-N-carboxymethyl-N-hydroxyethyl imidazolinium betaine
<Other Components> BDG: butyl diglycol PG: propylene glycol

(18) TABLE-US-00003 TABLE 3a Example 3-1 3-2 3-3 3-4 3-5 3-6 3-7 3-8 3-9 3-10 3-11 3-12 3-13 3-14 3-15 3-16 3-17 Lubricating Formulation (A) Lubricating agent 1 7.7 6.5 7.7 7.7 7.7 8.7 1.7 2.5 3 7.7 7.7 7.6 8.1 2.3 2.5 13.0 13.0 agent component (B) B-1 7.7 composition (mass %) B-2 9.8 7.7 7.7 7.7 5.8 3.3 2.5 2 B-3 7.7 7.7 B-7 7.6 B-8 8.1 B-10 2.3 B-11 2.5 BDG 1.9 PG 30.9 30.9 30.9 30.9 30.9 30.9 30.9 30.9 31.5 27.2 44.2 44.2 Water Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Balance Total 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 (B)/(A) (mass ratio) 1 1.5 1 1 1 0.67 2 1 0.67 1 1 1 1 1 1 0 0 Treating amount [% o.w.f.] 0.3 0.3 0.1 0.2 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 Hardness of treatment liquid [? DH] 4 4 4 4 4 4 4 4 4 4 20 4 4 4 4 4 20 Dehydration for Water content after 59 63 67 64 62 61 66 63 63 60 59 61 63 67 66 59 60 2 minutes dehydration [mass %] Dehydration enhancing 8 7 1 6 9 10 3 7 7 12 12 10 10 0 6 rate [%] Dehydration for Water content after 54 55 59 55 53 54 57 55 54 54 52 55 56 59 58 53 53 5 minutes dehydration [mass %] Dehydration enhancing 0 5 0 5 9 7 2 5 7 10 9 5 11 2 3 rate [%]

(19) TABLE-US-00004 TABLE 3b Comparative example 3-1 3-2 3-3 3-4 3-5 3-6 3-7 3-8 3-9 3-10 3-11 3-12 Lubricating Formulation (A) Lubricating agent 1 agent component (B) B-1 20 composition (mass %) B-2 20 B-3 20 20 B-7 20 B-8 19.6 B-10 31 B-11 40 BDG 5.0 PG 10 10 10 10 10 11.8 100 100 Water Balance Balance Balance Balance Balance Balance Balance Balance 100 100 Total 100 100 100 100 100 100 100 100 100 100 100 100 (B)/(A) (mass ratio) Treating amount [% o.w.f.] 0.3 0.3 0.3 0.3 0.3 0.3 0.3 0.3 (2.0) (2.0) Hardness of treatment liquid [? DH] 4 4 4 20 4 4 4 4 4 20 4 20 Dehydration for Water content after 64 68 68 67 68 70 67 70 67 66 67 68 2 minutes dehydration [mass %] Dehydration enhancing rate [%] (Reference) (Reference) (Reference) (Reference) (Reference) (Reference) (Reference) (Reference) Dehydration for Water content after 54 58 60 57 58 63 60 60 60 60 62 58 5 minutes dehydration [mass %] Dehydration enhancing rate [%] (Reference) (Reference) (Reference) (Reference) (Reference) (Reference) (Reference) (Reference)

(20) It is understood that the water contents after dehydration can be reduced in examples 3-1 to 3-17 in which the lubricating agent of the present invention was used. The dehydration rates are enhanced with any component (B), and particularly, the results of examples 3-2 and 3-9 show less susceptibility to the mass ratio (B)/(A).

(21) <Lubricity Evaluation 2>

(22) Treatment liquids were prepared by the method described later and each substrate was treated with certain treatment liquids prepared, and the dynamic contact angle of water was measured on the treated substrate and used as an indicator of lubricity (the ability to form a liquid sliding surface against water). The lubricating agents and component (B) used in the present evaluation are the same as those used in lubricity evaluation 1. Further, the following substrates 1 to 4 with a size of 1.0 mm?25 mm?70 mm and substrate 5 with a size of 2.0 mm?10 mm?70 mm were used. Substrate 1: a polypropylene substrate (Standard Test Piece, Inc., PP-N-AN) Substrate 2: a polyethylene terephthalate substrate (Standard Test Piece, Inc., SUNLOID PET PIECE) Substrate 3: a glass substrate (Matsunami Glass Ind., Ltd., S2112) Substrate 4: a SUS substrate (Standard Test Piece, Inc., SUS430) Substrate 5: a chloroprene rubber substrate (Nippon Testpanel Co., Ltd., CR)
(1) Preparation of Treatment Liquid

(23) Any lubricating agent and as necessary any component (B) shown in Tables 4 to 9 were mixed with water having a predetermined hardness at any treating concentrations shown in the tables, thereby preparing each of the treatment liquids having any hardness shown in the tables.

(24) (2) Washing of Substrate

(25) Each substrate shown in Tables 4 to 8 was immersed in 300 mL of a washing liquid (manufactured by FUJIFILM Wako Pure Chemical Corporation in which Contaminon? L was used at a concentration of 2%) and subjected to an ultrasonic treatment for 15 minutes. The substrate was rinsed with 25 mL of ion exchange water, and thereafter immersed in ethanol and subjected to an ultrasonic treatment for 30 minutes. The substrate was rinsed with 25 mL of ion exchange water and thereafter dried by being left to stand overnight (for 12 hours) under an environment at a humidity of 40 to 50% RH, and used as an untreated substrate. Note that the model number UT-604 manufactured by SHARP CORPORATION was used for the ultrasonic treatment.

(26) (3) Treatment of Substrate

(27) 100 mL of the treatment liquid prepared in (1) was placed in a PP wide-mouth bottle (manufactured by AS ONE Corporation, product number 100 mL), in which the untreated substrate washed in (2) was immersed and treated for 15 minutes at 25? C. while shaken with the model number BR-21FH manufactured by TAITEC CORPORATION at 200 rpm. After that, the substrate was immersed in 100 mL of water having the same hardness as that of the treatment liquid for 30 seconds, and thereafter dried by being left to stand overnight (for 12 hours) under the conditions of a temperature of 23? C. and a humidity of 40 to 50%.

(28) (4) Method for Measuring Dynamic Contact Angle

(29) With a fully automatic contact angle meter (manufactured by Kyowa Interface Science Co., Ltd., DropMaster), 4 ?L of ion exchange water was added dropwise to each substrate and the inclination was started 10 seconds later, and increasing the angle of inclination at a rate of 2?/s, the angle of inclination and the contact angle were measured by a slip-down method to determine the roll-off angle and the contact angle hysteresis. The results are shown in each table. Note that the angle of inclination at which the droplet begins to slip down is referred to as the roll-off angle [? ]. Further, the difference between the advancing contact angle and the receding contact angle at the start of rolling off is referred to as the contact angle hysteresis [? ]. The roll-off angle shown in each table is the additive average of three roll-off angle measurements taken at three different locations on each substrate. The contact angle hysteresis shown in each table is the additive average of three contact angle hysteresis measurements corresponding to the roll-off angle measurements at the three locations.

(30) TABLE-US-00005 TABLE 4 Example 4-1 4-2 4-3 4-4 4-5 4-6 4-7 4-8 Lubricating Type Lubricating Lubricating Lubricating Lubricating Lubricating Lubricating Lubricating Lubricating agent agent 1 agent 1 agent 1 agent 1 agent 1 agent 1 agent 1 agent 1 Treating 120 60 96 500 1000 60 96 120 concentration (ppm) Hardness of treatment 4 4 4 4 4 20 20 20 liquid [? DH] Roll-off Substrate 1 37 57 38 40 35 37 41 35 angle [?] Substrate 2 33 58 52 27 19 29 31 26 Substrate 3 27 13 16 11 28 8 24 22 Substrate 4 35 38 36 34 31 36 32 34 Substrate 5 43 55 51 Contact Substrate 1 29 25 27 26 27 27 angle Substrate 2 24 36 35 23 13 26 30 18 hysteresis Substrate 3 19 9 17 8 16 13 16 12 [?] Substrate 4 29 25 27 25 23 26 20 23 Substrate 5 32 31 29 Example Comparative example 4-9 4-10 4-1 4-2 Lubricating Type Lubricating Lubricating agent agent 1 agent 1 Treating 500 1000 concentration (ppm) Hardness of treatment 20 20 4 20 liquid [? DH] Roll-off Substrate 1 32 29 >80 >80 angle [?] Substrate 2 27 23 >80 >80 Substrate 3 22 28 >80 >80 Substrate 4 36 35 >80 >80 Substrate 5 42 36 >80 >80 Contact Substrate 1 32 22 angle Substrate 2 24 18 hysteresis Substrate 3 16 22 [?] Substrate 4 25 21 Substrate 5 27 21

(31) It is understood that lubricity against water can be imparted to the target surfaces in examples 4-1 to 4-10 in which the surfaces were treated with the lubricating agent of the present invention. The excellent lubricity against water on any target surface in the examples indicates less susceptibility to the type of target surface. Note that >80 in the tables means more than 80 (the same applies hereinafter).

(32) TABLE-US-00006 TABLE 5 Example 5-1 5-2 5-3 5-4 5-5 5-6 Lubricating Type Lubricating Lubricating Lubricating Lubricating Lubricating Lubricating agent agent 1 agent 1 agent 1 agent 1 agent 1 agent 1 Treating 120 120 120 120 60 60 concentration (ppm) Hardness of treatment 4 8 12 20 1 2 liquid [? DH] Roll-off Substrate 2 33 41 30 26 52 59 angle [?] Contact angle Substrate 2 24 32 28 18 34 37 hysteresis [?] Example 5-7 5-8 5-9 5-10 Lubricating Type Lubricating Lubricating Lubricating Lubricating agent agent 1 agent 1 agent 1 agent 1 Treating 60 60 60 60 concentration (ppm) Hardness of treatment 4 8 12 20 liquid [? DH] Roll-off Substrate 2 58 41 44 29 angle [?] Contact angle Substrate 2 36 33 34 26 hysteresis [?]

(33) It is understood that the liquid sliding ability against water can be imparted to the target surface in examples 5-1 to 5-10 in which the surface was treated with the lubricating agent of the present invention. The excellent lubricity against water at any hardness in the examples indicates less susceptibility to the hardness.

(34) TABLE-US-00007 TABLE 6 Example Comparative example 6-1 6-2 6-3 6-4 6-5 6-6 6-7 6-1 6-2 6-3 6-4 6-5 6-6 6-7 Treatment Treating (A) Lubricating 120 96 96 96 96 96 96 liquid concentration agent 1 (ppm) (B) B-2 24 120 B-4 24 120 B-5 24 120 B-6 24 120 B-9 24 120 B-7 24 120 Total of 120 120 120 120 120 120 120 0 120 120 120 120 120 120 (A) and (B) Hardness of treatment 4 4 4 4 4 4 4 4 4 4 4 4 4 4 liquid [? DH] Roll-off angle [?] Substrate 1 37 57 36 38 35 36 >80 >80 >80 >80 >80 >80 >80 Substrate 2 33 42 47 28 40 26 23 >80 >80 >80 >80 >80 >80 >80 Contact angle Substrate 1 29 25 34 28 17 hysteresis [?] Substrate 2 24 28 33 23 29 18 11

(35) It is understood that lubricity against water can be imparted to the target surfaces in examples 6-1 to 6-7 in which the surfaces were treated with the lubricating agent of the present invention. It is understood from the results of examples 6-2 to 6-7 that the combined use of components (A) and (B) does not inhibit the lubricity against water of component (A).

(36) TABLE-US-00008 TABLE 7 Comparative Example example 7-1 7-2 7-3 7-4 7-5 7-6 7-7 7-1 Treatment Treating (A) Lubricating 120 96 96 96 96 96 96 liquid concentration agent 1 (ppm) (B) B-2 24 B-4 24 B-5 24 B-6 24 B-9 24 B-7 24 Total of 120 120 120 120 120 120 120 0 (A) and (B) Hardness of treatment 20 20 20 20 20 20 20 20 liquid [? DH] Roll-off angle [?] Substrate 1 35 51 47 54 49 24 56 >80 Substrate 2 26 33 39 43 44 20 22 >80 Contact angle Substrate 1 27 16 32 8 16 hysteresis [?] Substrate 2 18 21 29 30 30 17 18

(37) It is understood that lubricity against water can be imparted to the target surfaces in examples 7-1 to 7-7 in which the surfaces were treated with the lubricating agent of the present invention. It is understood from the results of examples 7-2 to 7-7 that the combined use of components (A) and (B) does not inhibit the lubricity against water of component (A).

(38) TABLE-US-00009 TABLE 8 Comparative Example example 8-1 8-2 8-3 8-1 8-2 Lubricating agent Type Lubricating Lubricating Lubricating agent 1 agent 3 agent 3 Treating 120 120 120 concentration (ppm) Hardness of treatment liquid [? DH] 4 4 20 4 20 Roll-off angle [?] Substrate 1 37 61 27 >80 >80 Substrate 2 33 14 40 >80 >80 Substrate 3 27 11 27 >80 >80 Contact angle Substrate 1 29 hysteresis [?] Substrate 2 24 10 26 Substrate 3 19 10 23

(39) It is understood that lubricity against water can be imparted to the target surfaces in examples 8-1 to 8-3 in which the surfaces were treated with the lubricating agent of the present invention. The excellent lubricity against water on any target surface indicates less susceptibility to the material of target surface.

(40) TABLE-US-00010 TABLE 9 Comparative Example example 9-1 9-2 9-3 9-4 9-5 9-6 9-7 9-8 9-9 10-1 10-2 Treatment Treating (A) Lubricating 120 96 72 48 120 96 72 48 24 liquid concentration agent 1 (ppm) (B) B-7 24 48 72 24 48 72 96 120 120 Total of 120 120 120 120 120 120 120 120 120 120 120 (A) and (B) Hardness of treatment 4 4 4 4 20 20 20 20 20 4 20 liquid [? DH] Static contact Substrate 2 22 14 ND*.sup.1 ND*.sup.1 24 ND*.sup.1 ND*.sup.1 ND*.sup.1 ND*.sup.1 45 58 angle [?] Roll-off angle [?] Substrate 2 20 7 ND*.sup.2 ND*.sup.2 18 ND*.sup.2 ND*.sup.2 ND*.sup.2 ND*.sup.2 >80 >80 Contact angle Substrate 2 19 5 ND*.sup.3 ND*.sup.3 11 ND*.sup.3 ND*.sup.3 ND*.sup.3 ND*.sup.3 hysteresis [?] *.sup.1spread wetly to the extent that the static contact angle cannot be measured *.sup.2spread wetly to the extent that the roll-off angle cannot be measured *.sup.3the roll-off angle cannot be measured, and consequently, the hysteresis cannot be measured either

(41) It is understood that the target surface is highly hydrophilized and excellent in lubricity against water in examples 9-1 to 9-9 in which the surface was treated with the lubricating agent of the present invention.

(42) <Dewaterability Evaluation>

(43) Substrates 2 and 3 used in lubricity evaluation 2 were washed and treated in the same manner as in (2) and (3) in lubricity evaluation 2. Ion exchange water was sprayed with a sprayer to each substrate after the treatment, and the amount of water adhering to the substrate immediately after the spraying (initial adhesion amount) (g) and the amount of water adhering to the substrate 10 seconds later (residual amount) (g) were measured to evaluate the dewaterability on the basis of the discharge rate determined by the following formula from those amounts.
Discharge rate (%)=100?[1?(residual amount)/(initial adhesion amount)]

(44) Note that a sprayer manufactured by Maruemu Corporation (300 mL in volume, No. 6) was pushed three times to spray ion exchange water to the substrate. Further, the residual amount and the initial adhesion amount were determined in the following manner.
(Residual amount)=(total mass of substrate 10 seconds later)?(mass of substrate before spraying)
(Initial adhesion amount)=(residual amount)+(amount of water dropping off for 10 seconds)

(45) TABLE-US-00011 TABLE 10 Comparative Example example 10-1 10-2 10-1 10-2 Lubricating Type Lubricating Lubricating agent agent 1 agent 1 Treating 120 120 concentration (ppm) Hardness of treatment 4 20 4 20 liquid [?DH] Dewaterability Substrate 2 92 85 56 1 (discharge Substrate 3 87 96 52 30 rate) [%]

(46) It is understood that the dewaterability of each target surface can be enhanced in examples 10-1 to 10-2 in which the surfaces were treated with the lubricating agent of the present invention. The discharge rates of 80% or more on both target surfaces indicate less susceptibility to the material of target surface.

(47) <Evaluation of Spotty Adsorptivity>

(48) The pretreatment of towels, the treatment of towels with lubricating agents and dehydration were carried out in the same manner as in example 1-1 except that 24 towels were treated simultaneously under any conditions shown in Table 11. After dehydrated, the towels were naturally dried.

(49) After drying, five towels were selected at random, from each of which five towel pieces with a size of 10 cm?10 cm were cut, and the amount of lubricating agent adsorbed to the cut fabric was determined in the following manner. The standard deviation of the adsorption amounts of a total of 25 towel pieces was determined. The standard deviation for 25 towel pieces is shown in Table 11.

(50) (Measurement of Adsorption Amount)

(51) 80 mL of methanol was placed in a screw bottle manufactured by Maruemu Corporation (100 mL in volume, No. 8), in which the towel pieces were immersed and subjected to an ultrasonic treatment with the model number UT-604 manufactured by SHARP CORPORATION for 30 minutes. The obtained extracted liquid was appropriately diluted, and filtered with the disposable membrane filter unit DISMIC 13HP with a hole diameter of 0.2 ?m manufactured by ADVANTEC CORPORATION, and thereafter subjected to LC/MS. Note that the model number LCMS-2020 manufactured by SHIMADZU CORPORATION was used for the LC/MS. The LC/MS was performed under the following conditions.

(52) (Chromatography Separation)

(53) Column: UK-C18 HT manufactured by IMTAKT CORPORATION, 2 mm in inner diameter?50 mm in length, 3 ?m in particle size Column temperature: 40? C. Eluent A: 10 mM ammonium acetate-containing water Eluent B: 10 mM ammonium acetate-containing methanol Flow rate: 0.3 mL/min Gradient: eluent B 0% (0 to 5 minutes)->100% (5 to 15 minutes)->100% (15 to 25 minutes)->0% (25.01 to 30 minutes) Injection volume: 1 ?L
(Mass Analysis) Ionization method: electrospray ionization (ESI)
Analysis Mode: lubricating agent 1: negative, SIM (m/z=477.1) comparative lubricating agent 1: positive, SIM (m/z=550.6)

(54) TABLE-US-00012 TABLE 11 Test group I Test group II Com- Com- Ex- parative Ex- parative ample example ample example 11-1 11-1 11-2 11-2 Lubricating Type Lubri- Com- Lubri- Com- agent cating parative cating parative agent 1 lubri- agent 1 lubri- cating cating agent 1 agent 1 Treating 0.1 0.1 0.3 0.3 amount [% o.w.f.] Hardness of treatment 4 4 4 4 liquid [?DH] Spotty Standard 33.7 39.9 12.0 18.5 adsorption deviation of evaluation adsorption amounts

(55) In examples 11-1 and 11-2 in which towels were treated with the lubricating agent of the present invention, the maximum values of the standard deviation for the towels are smaller compared with those in comparative examples 11-1 and 11-2, respectively, indicating that spotty adsorption occurs less.