Antistatic release agent and antistatic release film

Abstract

The invention relates to an antistatic release agent comprising: a release component that contains a condensation-curing type organopolysiloxane, a conductive component that contains a complex of a -conjugated electrically conductive polymer and a polyanion and an organic solvent, wherein the amount of the conductive component relative to 100 parts by mass of the release component is 1 to 300 parts by mass, at least one amine-type compound selected from the group consisting of a secondary amine, a tertiary amine or a quaternary ammonium salt is coordinated to or bonded to portion of anion groups in the polyanion as an ion pair, and the amine-type compound has one or more substituent selected from the group consisting of an alkyl group having 4 or more carbon atoms, an aryl group, an aralkyl group, an alkylene group, an arylene group, an aralkylene group and an oxyalkylene group.

Claims

1. An antistatic release agent comprising: a release component that contains a condensation-curing type organopolysiloxane; a conductive component that contains a complex of a -conjugated electrically conductive polymer and a polyanion; and an organic solvent; wherein the amount of the conductive component relative to 100 parts by mass of the release component is 1 to 300 parts by mass, at least one amine compound selected from the group consisting of a secondary amine, a tertiary amine or a quaternary ammonium salt is coordinated to or bonded to a portion of anion groups in the polyanion as an ion pair, the amine compound has one or more substituent selected from the group consisting of an alkyl group having 4 or more carbon atoms, an aryl group, an aralkyl group, an alkylene group, an arylene group, an aralkylene group and an oxyalkylene group, and the amount of the portion of anion groups relative to the total anion groups in the polyanion is 30 to 90 mol %.

2. An antistatic release film comprising: a base composed of a plastic film or paper; and a release agent layer formed on at least one surface of the base; wherein the release agent layer is formed from an antistatic release agent of claim 1.

3. The antistatic release agent according to claim 1, wherein the release component is a silicone material containing at least one composition selected from the group consisting of compositions (A) to (C), wherein the composition (A) includes components (A-1) to (A-3), the component (A-1) is an organopolysiloxane having at least two hydroxyl groups within one molecule thereof, the component (A-2) is an organopolysiloxane having at least three SiH groups within one molecule thereof, and the component (A-3) is a condensation catalyst; the composition (B) includes components (B-1) to (B-3), the component (B-1) is an organopolysiloxane having at least two hydroxyl groups within one molecule thereof, the component (B-2) is an organopolysiloxane having at least three hydrolyzable groups within one molecule thereof, and the component (B-3) is a condensation catalyst; and the composition (C) includes components (C-1) and (C-2), the component (C-1) is an organopolysiloxane having at least three hydrolyzable groups within one molecule thereof, and the component (C-2) is a condensation catalyst.

4. The antistatic release agent according to claim 3, wherein the release component is a silicone material containing the composition (A).

5. The antistatic release agent according to claim 4, wherein the component (A-1) is an organopolysiloxane which has at least two hydroxyl groups within one molecule thereof, and is represented by any one of formulae (1-1) to (1-3) shown below; ##STR00006## wherein Me represents a methyl group; Ph represents a phenyl group; R represents a hydroxyl group, a monovalent hydrocarbon group having 1 to 20 carbon atoms or a siloxane residue represented by general formula (2-1) or (2-2); R.sup.l represents an oxygen atom or an alkylene group having 1 to 6 carbon atoms; 1 represents an integer of 0 to 1,000; 1 represents an integer of 50 to 9,000; 2 represents an integer of 0 to 900; 2 represents an integer of 0 to 9,000; and represents an integer of 1 to 3,000.

6. The antistatic release agent according to claim 4, wherein the component (A-2) is an organohydrogenpolysiloxane which has at least three SiH groups within one molecule thereof and is represented by any one of formulae (3-1) to (3-5) shown below; ##STR00007## wherein Me represents a methyl group; Y represents a group represented by general formula (4-1); Z represents a group represented by general formula (4-2); a and e each independently represents an integer of 3 to 500; c represents an integer of 1 to 500; and b, d, f, g, h, i, j, k, m, n, o, p and q each independently represents an integer of 0 to 500.

7. The antistatic release agent according to claim 4, wherein the component (A-1) is an organopolysiloxane which has at least two hydroxyl groups within one molecule thereof, has 50 to 100,000 mPa.Math.s of a viscosity of 30% by mass toluene solution, determined using a rotating viscometer at 25 C., and has dimethylhydroxysiliy groups at the both terminals of main chain of the molecular chain and has a main skeleton containing 90 to 100 mol % of dimethylsiloxane unit and 0 to 10 mol % of diphenylsiloxane unit.

8. The antistatic release agent according to claim 4, wherein the component (A-2) is an organopolysiloxane which has at least three SiH groups within one molecule thereof, has trimethylsilyl groups at the both terminals of main chain of molecular chain, has a main skeleton containing 10 to 100 mol % of MeHSiO.sub.2/2 unit relative to the total mole number of the structural units constituting the main skeleton, and has 2 to 1,000 mPa.Math.s of an absolute viscosity determined using a rotating viscometer at 25 C.

9. The antistatic release agent according to claim 3, wherein the release component is a silicone material containing the composition (B).

10. The antistatic release agent according to claim 9, wherein the component (B-1) is an organopolysiloxane which has at least two hydroxyl groups within one molecule thereof, and is represented by any one of formulae (1-1) to (1-3) shown below; ##STR00008## wherein Me represents a methyl group; Ph represents a phenyl group; R represents a hydroxyl group, a monovalent hydrocarbon group having 1 to 20 carbon atoms or a siloxane residue represented by general formula (2-1) or (2-2); R.sup.1 represents an oxygen atom or an alkylene group having 1 to 6 carbon atoms; 1 represents an integer of 0 to 1,000; 1 represents an integer of 50 to 9,000; 2 represents an integer of 0 to 900; 2 represents an integer of 50 to 9,000; and represents an integer of 1 to 3,000.

11. The antistatic release agent according to claim 9, wherein the component (B-2) is an organopolysiloxane which has at least three hydrolyzable groups within one molecule thereof and is represented by any one of formulae (5-1) to (5-4) shown below; ##STR00009## wherein r represents an integer of 1 to 200; s represents an integer of 1 to 200; and n represents an integer of 1 to 10.

12. The antistatic release agent according to claim 9, wherein the component (B-1) is an organopolysiloxane which has at least two hydroxyl groups within one molecule thereof, has 50 to 100,000 mPa.Math.s of a viscosity of 30% by mass toluene solution, determined using a rotating viscometer at 25 C., and has dimethylhydroxysiliy groups at the both terminals of main chain of the molecular chain, and has a main skeleton containing 90 to 100 mol % of dimethylsiloxane unit and 0 to 10 mol % of diphenylsiloxane unit.

13. The antistatic release agent according to claim 9, wherein the component (B-2) is an organopolysiloxane which has at least three hydrolyzable groups within one molecule thereof, and is a partial hydrolysis condensate of MeSi(OMe).sub.3, and has 1 to 100mPa.Math.s of an absolute viscosity determined using a rotating viscometer at 25 C.

14. The antistatic release agent according to claim 3, wherein the release component is a silicone material containing the composition (C).

15. The antistatic release agent according to claim 14, wherein the component (C-1) is an organopolysiloxane which has at least three hydrolyzable groups within one molecule thereof and is represented by any one of formulae (5-1) to (5-4) shown below; ##STR00010## wherein r represents an integer of 1 to 200; s represents an integer of 1 to 200; and n represents an integer of 1 to 10.

16. The antistatic release agent according to claim 14, wherein the component (C-1) is an organopolysiloxane which has at least three hydrolyzable groups within one molecule thereof, and is a partial hydrolysis condensate of MeSi(OMe).sub.3, and has 1 to 100mPa.Math.s of an absolute viscosity determined using a rotating viscometer at 25 C.

Description

EXAMPLES

(1) Although the following indicates examples and comparative examples of the present invention, the present invention is not limited to the following examples. In the following examples, parts means parts by mass, and % means % by mass.

Production Example 1

(2) 206 g of sodium styrene sulfonate were dissolved in 1000 ml of ion exchange water followed by adding thereto, a solution of 1.14 g of ammonium persulfate preliminarily dissolved in 10 ml of water in a dropwise manner over 20 minutes while stirring at 80 C., and further stirring the solution for 12 hours.

(3) 1000 ml of sulfuric acid diluted to 10% by mass was added to the resulting sodium styrene sulfonate-containing solution. Subsequently, about 1,000 ml of polystyrene sulfonate-containing solution were removed using ultrafiltration. Moreover, 2,000 ml of ion exchange water were added to the residual liquid, and about 2,000 ml of solution were removed using ultrafiltration. The aforementioned ultrafiltration procedure was repeated three times. Subsequently, 2,000 mL of ion exchange water were added to the obtained filtrate, and about 2,000 mL of solution were removed using ultrafiltration. The aforementioned ultrafiltration procedure was repeated three times and the water in the resulting solution was removed under reduced pressure to obtain polystyrene sulfonate in the form of a colorless solid. The mass average molecular mass of this polystyrene sulfonate was about 300,000.

Production Example 2

(4) 14.2 g of 3,4-ethylenedioxythiophene and a solution obtained by dissolving 36.7 g of the polystyrene sulfonate obtained in Production Example 1 in 2,000 ml of ion exchange water were mixed at 20 C.

(5) While holding at 20 C., an oxidation catalyst solution obtained by dissolving 29.64 g of ammonium persulfate and 8.0 g of ferric sulfate in 200 ml of ion exchange water were slowly added to the resulting mixed solution while stirring. The reaction was allowed to proceed for 3 hours.

(6) 2,000 ml of ion exchange water were added to the resulting reaction liquid and about 2,000 ml of the solution were removed using ultrafiltration. This procedure was repeated three times.

(7) Next, 200 ml of dilute sulfuric acid having a concentration of 10% by mass and 2,000 ml of ion exchange water were added to the treated liquid on which the aforementioned ultrafiltration was carried out, and about 2,000 ml of the treated liquid were removed using ultrafiltration. Subsequently, 2,000 ml of ion exchange water were further added to the solution, and about 2000 ml of liquid were removed using ultrafiltration. This procedure was repeated three times.

(8) Moreover, 2,000 ml of ion exchange water were added to the resulting treated liquid and about 2,000 ml of the treated liquid were removed by ultrafiltration. This procedure was repeated five times to obtain an aqueous dispersion of about 1.2% by mass of polystyrene sulfonate-doped poly(3,4-ethylenedioxythiophene) (hereinafter, referred to as PEDOT-PSS aqueous dispersion).

Production Example 3

(9) 1,000 g of the PEDOT-PSS aqueous dispersion was freeze-dried to obtain 12 g of powder of PEDOT-PSS. To the obtained 12.0 g of powder of PEDOT-PSS, 2,882 g of isopropanol and 10.6 g of trioctylamine were added and mixed to obtain an isopropanol dispersion of PEDOT-PSS (1) having a concentration of 0.4%.

Production Example 4

(10) The isopropanol dispersion of PEDOT-PSS (2) having a concentration of 0.4% was prepared in the same manner as in the Production Example 3 except that 4.2 g of triethylamine was used instead of 10.6 g of trioctylamine.

Production Example 5

(11) The isopropanol dispersion of PEDOT-PSS (3) having a concentration of 0.4% was prepared in the same manner as in the Production Example 3 except that 3.0 g of tripropylamine was used instead of 10.6 g of trioctylamine.

Production Example 6

(12) The isopropanol dispersion of PEDOT-PSS (4) having a concentration of 0.4% was prepared in the same manner as in the Production Example 3 except that 3.0 g of mono-n-hexylamine was used instead of 10.6 g of trioctylamine.

Production Example 7

(13) The isopropanol dispersion of PEDOT-PSS (5) having a concentration of 0.4% was prepared in the same manner as in the Production Example 3 except that 1.8 g of Ethomeen C25 (trade name, Lion Akzo Co., Ltd.) was used instead of 10.6 g of trioctylamine.

(14) <Preparation of Release Agent>

(15) A condensation-curing type organopolysiloxane used in the following examples will be explained as follows.

(16) Condensation-Curing Type Organopolysiloxane C

(17) Active ingredient: 20%; a mixture of an organic resin derivative and an alkoxy group-containing organopolysiloxane oil; in the condensation-curing type organopolysiloxane C, the amount of the organic resin derivative: 14% by mass; the amount of the alkoxy group-containing organopolysiloxane oil: 6% by mass; the amount of toluene: 55% by mass; and the amount of butanol: 25% by mass

(18) In the present specification, the term active ingredient refers to the component contained in the release component (excluding solvent).

(19) The organic resin derivative is a compound in which portion of hydroxyl groups of cellulose has been etherified by an ethyl group.

(20) The alkoxy group-containing organopolysiloxane oil is methylmethoxypolysiloxane which is a partial hydrolysis condensate of MeSi(OMe).sub.3 and has 10 mPa.Math.s of viscosity. The compound has at least three OMe groups in one molecule.

(21) Condensation-Curing Type Organopolysiloxane B1

(22) Active ingredient: 50%; a mixture of a silanol group-containing organopolysiloxane oil and an alkoxy group-containing organopolysiloxane oil; in the condensation-curing type organopolysiloxane B1, the amount of the silanol group-containing organopolysiloxane oil: 45% by mass; the amount of the alkoxy group-containing organopolysiloxane oil: 5% by mass; and the amount of toluene: 50% by mass

(23) The silanol group-containing organopolysiloxane oil is a organopolysiloxane which has 800 mPa.Math.s of a viscosity of 30% by mass toluene solution, determined using a rotating viscometer at 25 C., and has dimethylhydroxysiliy groups at the both terminals of main chain of the molecular chain, and has a main skeleton excluding the both units at the terminals, composed of 90 mol % of dimethylsiloxane unit and 10 mol % of diphenylsiloxane unit.

(24) The alkoxy group-containing organopolysiloxane oil is a methylmethoxypolysiloxane which is a partial hydrolysis condensate of MeSi(OMe).sub.3 and has 10 mPa.Math.s of viscosity. The compound has at least three OMe groups in one molecule.

(25) Condensation-Curing Type Organopolysiloxane B2

(26) Active ingredient: 30%; a mixture of a silanol group-containing organopolysiloxane gum and an alkoxy group-containing organopolysiloxane oil; in the condensation-curing type organopolysiloxane B2, the amount of the silanol group-containing organopolysiloxane gum: 24% by mass; the amount of the alkoxy group-containing organopolysiloxane oil: 6% by mass; and the amount of toluene: 70% by mass

(27) The silanol group-containing organopolysiloxane gum is an organopolysiloxane which has 15,000 mPa.Math.s of a viscosity of 30% by mass toluene solution, determined using a rotating viscometer at 25 C., and has dimethylhydroxysiliy groups at the both terminals of main chain of the molecular chain, and has a main skeleton composed of 100 mol % of dimethylsiloxane unit.

(28) The alkoxy group-containing organopolysiloxane oil is a methylmethoxypolysiloxane which is a partial hydrolysis condensate of MeSi(OMe).sub.3 and has a viscosity of 10 mPa.Math.s. The compound has at least three OMe group in one molecule.

(29) Condensation-Curing Type Organopolysiloxane A

(30) Active ingredient: 30%; a mixture of a silanol group-containing organopolysiloxane gum and an SiH group-containing organopolysiloxane oil; in the condensation-curing type organopolysiloxane A, the amount of the silanol group-containing organopolysiloxane gum: 29% by mass; the amount of the SiH group-containing organopolysiloxane oil: 1% by mass; and the amount of toluene: 70% by mass

(31) The silanol group-containing organopolysiloxane gum is an organopolysiloxane which has 1,5000 mPa.Math.s of a viscosity of 30% by mass toluene solution determined using a rotating viscometer at 25 C., and has dimethylhydroxysiliy groups at the both terminals of main chain of the molecular chain, and has a main skeleton composed of 100 mol % of dimethylsiloxane unit.

(32) The SiH group-containing organopolysiloxane oil is an organopolysiloxane which has trimethysiliy groups at the both terminals of main chain of the molecular chain, has a main skeleton composed of 100 mol % of MeHSiO.sub.2/2 unit relative to the total mole number of the structural units constituting the main skeleton, and has an absolute viscosity of 25 mPa.Math.s, determined using a rotating viscometer at 25 C.

(33) The viscosity was determined using TVB-10 type viscometer (manufactured by Told Sangyo Co., Ltd.).

Example 1

(34) 10.9 g of condensation-curing type organopolysiloxane C, 2.74 g of condensation-curing type organopolysiloxane B1 as condensation-curing type organopolysiloxanes and 0.5 g of dioctyl tin diacetate as a condensation catalyst were added to 30 g of isopropanol dispersion of PEDOT-PSS (1) obtained in Production Example 3. Then, the mixture was diluted with 45.86 g of methyl ethyl ketone and 10.0 g of diacetone alcohol, thereby obtaining a release agent (moisture content: 0.01%).

Example 2

(35) 10.0 g of condensation-curing type organopolysiloxane 2 as a condensation-curing type organopolysiloxane and 0.4 g of dioctyl tin diacetate as a condensation catalyst were added to 30 g of isopropanol dispersion of PEDOT-PSS (1) obtained in Production Example 3. Then, the mixture was diluted with 59.6 g of methyl ethyl ketone, thereby obtaining a release agent.

Example 3

(36) A release agent was obtained in the same manner as in the Example 2, except that the condensation-curing type organopolysiloxane A was used as a condensation-curing type organopolysiloxane.

Example 4

(37) 0.3 g of dimethylsulfoxide was added to 100 g of the release agent of Example 1, thereby obtaining a release agent containing a conductive improver.

Example 5

(38) A release agent containing a conductive improver was prepared in the same manner as in Example 4, except that ethylene glycol instead of dimethylsulfoxide was added to 100 g of the release agent of Example 1.

Example 6

(39) A release agent containing a conductive improver was prepared in the same manner as in Example 5, except that 2-hydroxyethylacrylamide instead of dimethylsulfoxide was added to 100 g of the release agent of Example 1.

Example 7

(40) A release agent containing a conductive improver was prepared by adding 0.3 g of ethyl lactate instead of dimethyl sulfoxide to 100 g of the release agent of Example 1.

Example 8

(41) 0.456 g of condensation-curing type organopolysiloxane B1 as a condensation-curing type organopolysiloxane and 0.018 g of dioctyl tin diacetate as a condensation catalyst were added to 170 g of isopropanol dispersion of PEDOT-PSS (1) obtained in Production Example 3. Then, the mixture was diluted with 45.86 g of methyl ethyl ketone and 10.0 g of diacetone alcohol, thereby obtaining a release agent.

Example 9

(42) A release agent was obtained in the same manner as in the Example 8, except that the amount of isopropanol dispersion of PEDOT-PSS (1) was changed to 120 g.

Example 10

(43) A release agent was obtained in the same manner as in the Example 8, except that the amount of isopropanol dispersion of PEDOT-PSS (1) was changed to 60 g.

Example 11

(44) A release agent was obtained in the same manner as in the Example 1, except that the amount of the condensation-curing type organopolysiloxane C was changed to 0.568 g, the amount of the condensation-curing type organopolysiloxane B1 was changed to 0.143 g, and the amount of dioctyl tin diacetate was changed to 0.028 g.

Example 12

(45) A release agent was obtained in the same manner as in the Example 1, except that the amount of the condensation-curing type organopolysiloxane C was changed to 1.09 g, the amount of the condensation-curing type organopolysiloxane B1 was changed to 0.247 g, and the amount of dioctyl tin diacetate was changed to 0.054 g.

Example 13

(46) A release agent was obtained in the same manner as in the Example 1, except that the amount of the condensation-curing type organopolysiloxane C was changed to 2.18 g, the amount of the condensation-curing type organopolysiloxane B1 was changed to 0.548 g, and the amount of dioctyl tin diacetate was changed to 0.108 g.

Example 14

(47) A release agent was obtained in the same manner as in the Example 1, except that the amount of the condensation-curing type organopolysiloxane C was changed to 4.36 g, the amount of the condensation-curing type organopolysiloxane B1 was changed to 1.096 g, and the amount of dioctyl tin diacetate was changed to 0.216 g.

Example 15

(48) A release agent was obtained in the same manner as in the Example 1, except that the amount of the isopropanol dispersion of PEDOT-PSS (1) in Example 2 was changed to 20 g.

Example 16

(49) A release agent was obtained in the same manner as in the Example 1, except that the amount of the isopropanol dispersion of PEDOT-PSS (1) in Example 2 was changed to 15 g.

Example 17

(50) A release agent was obtained in the same manner as in the Example 1, except that the amount of the isopropanol dispersion of PEDOT-PSS (1) in Example 2 was changed to 10 g.

Example 18

(51) 10.9 g of condensation-curing type organopolysiloxane C and 2.74 g of condensation-curing type organopolysiloxane B1 as condensation-curing type organopolysiloxanes and 0.5 g of dioctyl tin diacetate as a condensation catalyst were added to 30 g of isopropanol dispersion of PEDOT-PSS (5) obtained in Production Example 7. Then, the mixture was diluted with 45.86 g of methyl ethyl ketone and 10.0 g of diacetone alcohol, thereby obtaining a release agent.

Example 19

(52) 3 g of the compound represented by chemical formula III shown below as a condensation-curing type organopolysiloxane and 0.5 g of dioctyl tin diacetate as a condensation catalyst were added to 30 g of isopropanol dispersion of PEDOT-PSS (1) obtained in Production Example 3. Then, the mixture was diluted with 45.86 g of methyl ethyl ketone and 10.0 g of diacetone alcohol, thereby obtaining a release agent.

(53) ##STR00005##

Comparative Example 1

(54) 10.9 g of condensation-curing type organopolysiloxane C and 2.74 g of condensation-curing type organopolysiloxane B1 as condensation-curing type organopolysiloxanes and 0.5 g of dioctyl tin diacetate as a condensation catalyst were weighed. Then, 45.86 g of methyl ethyl ketone and 10.0 g of diacetone alcohol were added so as to adjust the solid content to 3% by mass, thereby obtaining a release agent.

Comparative Example 2

(55) 10 g of condensation-curing type organopolysiloxane B2 and 0.4 g of dioctyl tin diacetate were weighed. Then 59.6 g of methyl ethyl ketone was added, thereby obtaining a release agent.

Comparative Example 3

(56) A release agent was prepared in the same manner as in Comparative Example 2, except that the condensation-curing type organopolysiloxane A was used instead of the condensation-curing type organopolysiloxane B2.

Comparative Example 4

(57) A release agent was prepared in the same manner as in Example 1, except that the amount of the isopropanol dispersion of PEDOT-PSS in Example 8 was changed to 190 g.

Comparative Example 5

(58) A release agent was prepared in the same manner as in Example 1, except that the amount of the isopropanol dispersion of PEDOT-PSS in Example 2 was changed to 5 g.

Comparative Example 6

(59) A release agent was prepared in the same manner as in Example 1, except that isopropanol dispersion of PEDOT-PSS (2) was used instead of isopropanol dispersion of PEDOT-PSS (1).

Comparative Example 7

(60) A release agent was prepared in the same manner as in Example 1, except that isopropanol dispersion of PEDOT-PSS (3) was used instead of isopropanol dispersion of PEDOT-PSS (1).

Comparative Example 8

(61) A release agent was prepared in the same manner as in Example 1, except that isopropanol dispersion of PEDOT-PSS (4) was used instead of isopropanol dispersion of PEDOT-PSS (1).

(62) <Evaluation>

(63) With respect to each release agent, curable properties, force required peeling (hereinafter, referred to as peel strength), residual adhesion ratio, and surface resistivity were evaluated and measured by the following method. The results are shown in Table 1.

(64) [Curing Properties]

(65) The obtained release agent was applied to a PET film having a thickness of 38 m using barcoater, and heated at 120 C. for 1 minute in a hot air drier to form a release agent layer. The release agent layer was rubbed with a finger ten times, and the existence or non-existence of cloud or defect was visually observed, and evaluated in accordance with following criteria. A: cloud and rub-off were not observed. B: cloud and rub-off were observed.
[Peel Strength]

(66) A release agent layer was formed in the same manner as in the [curing properties], and polyester adhesion tape (product name: nitto-31B, manufactured by Nitto Denko Corporation) was laminated on the surface of the release agent layer, and a load of 1976Pa was applied to the adhesion tape so as to adhere the polyester adhesion tape to the release agent layer. Using a tensile testing machine, the polyester adhesion tape was peeled from the release agent layer such that the angle between the polyester adhesion tape and the release agent layer became 180 (peeling speed: 0.3 m/min), and then, peel strength was measured. As the peel strength is smaller, the adhesion sheet can be easily peeled after the adhesion sheet is adhered to the release agent layer. That is, the adhesive sheet becomes a film having easy-peeling properties.

(67) [Residual Adhesion Ratio (Subsequent Adhesion Ratio)]

(68) A polyester adhesion tape was laminated on the release agent layer in the same manner as in the measurement of peel strength. Then, the laminated structure was left at room temperature for 20 hours, or the laminated structure was subjected to heat treatment at 85 C. for 20 hours. Next, the polyester adhesion tape was peeled from the release agent layer. The peeled polyester adhesion tape was adhered to a stainless panel. Thereafter, using a tensile testing machine, the polyester adhesion tape was peeled from the stainless panel and then, peel strength X was measured.

(69) A polyester adhesion tape that had not been adhered to a release agent layer was adhered to a stainless board, and using a tensile testing machine, the polyester adhesion tape was peeled from the stainless board and then, peel strength Y was measured.

(70) In accordance with the formula (peel strength X/peel strength Y)100(%), residual adhesion ratio was calculated.

(71) As the residual adhesion ratio becomes larger, the release properties the release agent layer becomes excellent, and deterioration of adhesion properties of polyester adhesion sheet which had been adhered to the release agent layer can be suppressed.

(72) [Surface Resistivity]

(73) Using Hiresta MCP-HT450 manufactured by Mitsubishi Chemical Corporation and a probe MCP-HTP12, surface resistivity was measured under applied voltage of 10V. The result OVER in Table means that surface resistivity was too high to measure it. The expression / means /sq..

(74) TABLE-US-00001 TABLE 1 Room temperature, Amount 20 hours 85 C., 20 hours of Residual Residual Conductive Peel adhesion adhesion Surface component Condensation-curing Curing strength ratio Peel strength ratio resistivity (parts) type organopolysiloxane properties (N/25 mm) (%) (N/25 mm) (%) (/) Example 1 3.4 Composition (B) A 0.04 90 0.09 83 .sup.1 10.sup.10 Example 2 4.0 Composition (B) A 0.03 73 0.06 62 1 10.sup.8 Example 3 4.0 Composition (A) A 0.04 67 0.05 61 1 10.sup.8 Example 4 3.4 Composition (B) A 0.05 90 0.15 80 2 10.sup.8 Example 5 3.4 Composition (B) A 0.05 89 0.16 79 3 10.sup.9 Example 6 3.4 Composition (B) A 0.05 90 0.15 80 3 10.sup.8 Example 7 3.4 Composition (B) A 0.05 88 0.14 81 2 10.sup.8 Example 8 298.3 Composition (B) A 5.14 79 5.32 59 5 10.sup.5 Example 9 210.5 Composition (B) A 3.43 78 3.86 61 3 10.sup.5 Example 10 105.3 Composition (B) A 2.83 82 2.90 65 2 10.sup.6 Example 11 64.8 Composition (B) A 2.50 86 2.50 68 3 10.sup.7 Example 12 33.8 Composition (B) A 1.50 87 1.50 70 4 10.sup.7 Example 13 16.9 Composition (B) A 0.40 96 1.00 80 3 10.sup.8 Example 14 8.5 Composition (B) A 0.06 91 0.25 82 2 10.sup.9 Example 15 2.6 Composition (B) A 0.03 87 0.05 76 3 10.sup.7 Example 16 2.0 Composition (B) A 0.03 87 0.05 76 3 10.sup.8 Example 17 1.3 Composition (B) A 0.03 87 0.05 76 .sup.7 10.sup.10 Example 18 3.4 Composition (B) A 0.06 90 0.19 79 3 10.sup.9 Example 19 3.4 Composition (C) A 5.34 87 7.40 76.5 2 10.sup.7 Comparative 0.0 Composition (B) A 0.04 90 0.09 84 OVER Example 1 Comparative 0.0 Composition (B) A 0.04 73 0.06 62 OVER Example 2 Comparative 0.0 Composition (A) A 0.04 76 0.05 62 OVER Example 3 Comparative 333.3 Composition (B) A 10.19 56 6.90 22.8 5 10.sup.5 Example 4 Comparative 0.7 Composition (B) A 0.04 87 0.05 76 OVER Example 5 Comparative 3.4 Composition (B) A 0.06 89 0.17 79 OVER Example 6 Comparative 3.4 Composition (B) A 0.05 87 0.2 76 OVER Example 7 Comparative 3.4 Composition (B) A 0.06 93 0.16 83 OVER Example 8

(75) With respect to the release agents according to Examples 1 to 19, peel strength was low, and surface resistivity was low. With respect to Comparative Examples 1 to 3 which did not contain the conductive component and Comparative Example 5 in which the amount of conductive component was too small, surface resistivity was too high to measure the value.

(76) With respect to Comparative example 4 in which the amount of the conductive component was too large and the amount of the release component was relatively too small, surface resistivity was high.

(77) With respect to Comparative Examples 6 and 7 in which the substituent of the amine compound coordinated to or bonded to the surplus sulfonate groups within a polystyrene sulfonate had less than 4 of carbon atoms, the liquid was not stable, the conductive complex was incompatible with a silicon resin and therefore, uniform film could not be formed. As a result, surface resistivity could not be measured.

(78) With respect to Comparative Example 8 in which the number of the substituent of the amine compound coordinated to or bonded to the surplus sulfonate groups within polystylene sulfonate was 1 (that is, the amine compound was a primary amine), the liquid was not stable, the conductive complex was incompatible with a silicon resin and therefore, uniform film could not be formed. As a result, surface resistivity could not be measured.

INDUSTRIAL APPLICABILITY

(79) The antistatic release agent and antistatic release film are superior in both antistatic properties and release properties, and useful in industrial prospective.