KR20070036693A - Flame retardant silicone composition - Google Patents

Abstract

According to the invention, it is possible to provide light curing, in particular UV curing, and to provide a transparent flame retardant silicone composition.

The flame retardant silicone composition

(A) an organopolysiloxane represented by the following general formula (1) and having two or more siloxy groups in one molecule, having a hydroxyl group, a silalkylene silanol group, or two or more hydrolyzable groups,

(B) an organosilicon compound having an acryloyloxy group and / or a methacryloyloxy group and a hydrolyzable group,

(C) condensation catalyst,

(D) a photopolymerization initiator, and

(E) Phosphoric acid ester compound represented by the following general formula (3)

It is characterized by containing.

Wherein R is a hydroxyl group, a silalkylenesilanol group or a hydrolyzable group, R ¹ is a methyl group or a phenyl group, a and b are independently positive, provided that a + b is a number from 1.9 to 2.4.

In the formula, R ⁶ is a monovalent hydrocarbon group.

In the formula, R ⁶ is a monovalent hydrocarbon group, and Q is a divalent hydrocarbon group.

Flame retardant silicone composition, organopolysiloxane, organosilicon compound, phosphate ester compound

Description

Flame Retardant Silicone Composition

[Patent Document 1] US Patent No. 4475346

[Patent Document 2] Specification of British Patent No. 1323869

[Patent Document 3] US Patent No. 4201808

[Patent Document 4] US Patent No. 4482454

[Patent Document 5] British Patent No. 2023 287

[Patent Document 6] US Patent No. 4528081

[Patent Document 7] US Patent No. 4699802

The present invention relates to a flame retardant silicone composition capable of photocuring.

Conventionally, the ultraviolet-ray (henceforth "UV") curable silicone composition which has a methacryloyloxy group is known. UV curable silicone compositions comprising, for example, at least 50% of certain types of silicone resins, at least 10% of fumed silica fillers, and photoinitiators (US Pat. No. 4675346); An organopolysiloxane having an acryloyloxy group or a methacryloyloxy group, a composition for producing a plate such as printing, comprising a photosensitive agent and a solvent (British Patent No. 1323869); UV curable compositions comprising organopolysiloxanes having one or more acryloyloxy groups and / or methacryloyloxy groups, low molecular weight polyacrylic crosslinkers and photosensitizers on average per molecule and suitable for exfoliating coatings (US Pat. No. 4201808) Specification and US Pat. No. 4,448,454 specification); There are proposed compositions for protective coating on paper (British Patent No. 2039287) prepared by the reaction of methacryloyloxypropyltrimethoxysilane and low molecular weight hydroxy terminated polyorganosiloxane.

Ultraviolet / moisture double curable silicone compositions are also known. For example, a dual curable silicone containing a silicone moisture curing catalyst and containing a polyorganosiloxane sealed with an acrylic functional dialkoxysilyl group or a diaryloxysilyl group, a silicone oil sealed with a trimethylsilyl group, and a photosensitizer ( US Pat. No. 4,452,801 and US Pat. No. 4,980,980 specifications).

When flame retardancy is requested | required in the fields of these plate manufacture, coating, etc., it is not common to respond with the conventional UV curable silicone composition, and it is common to ensure flame retardance by component parts other than a silicone hardened | cured material. However, with recent reconsideration of environmental problems, there is a demand for silicone compositions having good curability and further excellent flame retardancy because the demand for flame retardancy is also becoming severe. Among them, development of a transparent and flame retardant material capable of photocuring, in particular UV curing, has been difficult.

It is therefore an object of the present invention to provide a transparent flame retardant silicone composition capable of photocuring, in particular UV curing, and transparent.

MEANS TO SOLVE THE PROBLEM As a result of earnestly examining in order to solve the said subject, the present inventors discovered that favorable flame retardance, especially the flame retardance of UL94V-0, V-1, V-2 level is achieved by the following composition, It was completed.

That is, the present invention

(A) an organopolysiloxane represented by the following formula (1) and having a total of two or more in one molecule of one or a combination of two or more kinds of siloxy groups having a hydroxyl group, a silalkylene silanol group, or two or more hydrolyzable groups : 100 parts by mass,

(B) an organosilicon compound represented by the following formula (2): 0.1 to 30 parts by mass,

(C) condensation catalyst: effective amount,

(D) photoinitiator: effective amount, and

(E) It is an object to provide a flame-retardant silicone composition containing 0.1 to 30 parts by mass of a phosphate ester compound represented by the following general formula (3) or (4).

<Formula 1>

Wherein R is a hydroxyl group, silalkylenesilanol group or a hydrolyzable group, R ¹ is a methyl group or a phenyl group, a and b are independently positive, provided that a + b is a number from 1.9 to 2.4.

Wherein R ² is independently a hydrogen atom, a phenyl group or a halogenated phenyl group, R ³ is independently a hydrogen atom or a methyl group, R ⁴ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X is a hydrolyzable group, Z ¹ is independently a chemical formula -R ^5- , -R ⁵ O- or -R ⁵ (CH ₃ ) ₂ SiO- (wherein R ⁵ is independently substituted or unsubstituted carbon atoms 1 To a divalent hydrocarbon group of 10 to 10, Z ² is an oxygen atom or a substituted or unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, and m and n are each independently an integer of 0 to 2.

<Formula 3>

In formula, R <^6> is a substituted or unsubstituted monovalent hydrocarbon group independently.

<Formula 4>

In the formula, R ⁶ is independently a substituted or unsubstituted monovalent hydrocarbon group, and Q is a substituted or unsubstituted divalent hydrocarbon group.

Best Mode for Carrying Out the Invention

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated in detail.

<(A) organopolysiloxane>

Component (A) of the present invention is represented by the above formula (1), a hydroxyl group, a silalkylene silanol group, or a siloxy group having two or more, preferably two to three hydrolyzable groups, one kind or two or more kinds Organopolysiloxanes containing two or more, preferably 4 to 6, in total in one molecule.

(A) The structure of the organopolysiloxane of the component is not particularly limited, a straight chain one may have, RSiO _3/2 units, R ¹ SiO _3/2 units (wherein, R and R ¹ are as described above) or It may be a branched phase comprising SiO _4/2 units, or a combination thereof.

The viscosity at 25 ° C. of the organopolysiloxane of component (A) is preferably 50 to 100,000 mm ² / s, more preferably 100 to 10,000 mm ² / s. When the viscosity meets the above range, the cured product has better flame retardancy and sufficient hardness, and the composition also has adequate fluidity.

The organopolysiloxane of component (A) is 2 mol% or more, especially 10-40 mol with respect to the sum total of R in the said General formula (1) and all R <^1> (that is, all organic groups couple | bonded with Si of a siloxane skeleton). It is preferable to contain%.

The said silalkylene silanol group is group represented by following General formula (1a) normally.

In the formula, R ^p is independently an alkyl group, R ^q is an alkylene group, r is 1 to 10, preferably an integer of 1 to 6.

In said Formula (1a), R <^p> is a C1-C6 alkyl group normally. As the specific example, a methyl group, an ethyl group, a propyl group, etc. are mentioned, Preferably it is a methyl group.

In Formula 1a, R ^q is usually a methylene group or an alkylene group having 2 to 6 carbon atoms. Specific examples thereof include an ethylene group, a propylene group, trimethylene group, tetramethylene group, and the like, and preferably an ethylene group.

로 표시되는 실에틸렌실라놀기가 바람직하다.As a silalkylene silanol group represented by the said General formula (1a),

The silethylene silanol group represented by is preferable.

As said hydrolysable group, alkoxy groups, such as a methoxy group, an ethoxy group, a propoxy group, butoxy group, etc. are mentioned, For example, Preferably it is a methoxy group.

As the siloxy group having the hydrolyzable group, a trimethoxysiloxy group is preferable.

As said silalkylene silanol group represented by R in the said General formula (1), a silethylene silanol group is preferable and a methoxy group is preferable as a hydrolysable group. As R, a hydroxyl group and a methoxy group are especially preferable.

In said Formula (1), R <^1> is a methyl group or a phenyl group.

In Formula 1, a and b are defined so that the organopolysiloxane of component (A) has two or more R in one molecule, but need to be positively independently, provided that a + b will satisfy the range of 1.9 to 2.4. There is a need.

The organopolysiloxane of the component (A) is, for example

(Wherein Me represents a methyl group).

The organopolysiloxane of (A) component may be used individually by 1 type, and may use 2 or more types together.

<(B) organosilicon compound>

(B) component of this invention is a component which acts as a crosslinking agent, and is an organosilicon compound represented by the said General formula (2).

In said Formula (2), R <^2> is a hydrogen atom, a phenyl group, or a halogenated phenyl group, Preferably it is a hydrogen atom.

In said Formula (2), R <^3> is a hydrogen atom or a methyl group.

As said monovalent hydrocarbon group represented by R <^4> in the said General formula (2), a methyl group, an ethyl group, a propyl group, isopropyl group, a butyl group, isobutyl group, tert- butyl group, a pentyl group, hexyl group, cyclohex Alkyl groups, such as a real group, an octyl group, and a decyl group; Alkenyl groups such as vinyl group and allyl group; Chloromethyl group, 2-chloroethyl group, 2-bromoethyl group, 1, which substituted some or all of these hydrogen atoms with halogen atoms, such as an aryl group, such as a phenyl group and a tolyl group, and an aralkyl group, such as a benzyl group and a phenylethyl group, And halogenated alkyl groups such as 1-dichloropropyl group, 3-chloropropyl group, 3,3,3-trifluoropropyl group, and the like, and preferably substituted or unsubstituted monovalent hydrocarbons having 1 to 3 carbon atoms. Group, More preferably, it is a methyl group.

As said hydrolysable group represented by X in the said Formula (2), a hydrocarbyloxy group etc. are mentioned, for example, Preferably a methoxy group, an ethoxy group, a propoxy group, butoxy group, a methoxyethoxy group, etc. are mentioned. Lower alkoxy having 1 to 6 carbon atoms, particularly 1 to 4 carbon atoms, such as an alkenyloxy group such as an alkoxy group, vinyloxy group, allyloxy group, propenyloxy group, isopropenyloxy group, butenyloxy group Groups, lower alkenyloxy groups, etc., More preferably, they are a methoxy group, an ethoxy group, and isopropenyloxy group.

In the formula (2), the group represented by Z ¹ is represented by the formula -R ^5- , -R ⁵ O- or -R ⁵ (CH ₃ ) ₂ SiO- (wherein R ⁵ is as described above), preferably Preferably a group represented by the formula -R ⁵ O-. As a divalent hydrocarbon group represented by R <^5> , some of these hydrogen atoms, such as alkylene groups, such as a methylene group, ethylene group, trimethylene group, a propylene group, tetramethylene group, and arylene groups, such as a phenylene group, or Halogen-substituted alkylene groups such as chloromethylene group, dichloromethylene group, and chloroethylene group, all of which are substituted with halogen atoms; and among these, substituted or unsubstituted divalent hydrocarbon groups having 1 to 3 carbon atoms are preferable, Ethylene group and trimethylene group are especially preferable.

As said divalent hydrocarbon group represented by Z <^2> in the said General formula (2), although it is the same as what was demonstrated as the divalent hydrocarbon group represented by said R <^5> , an ethylene group is especially preferable.

In Formula 2, m and n are each independently an integer of 0 to 2, m is 2, n is preferably 0 or 1.

As a specific example of the organosilicon compound of (B) component, the thing of the following structures is mentioned.

In formula, Me represents a methyl group and is the same below.

The compounding quantity of the organosilicon compound of (B) component needs to be 0.1-30 mass parts with respect to 100 mass parts of (A) component, Preferably it is 1-20 mass parts, More preferably, it is 5-20 mass parts. . When the said compounding quantity is less than 0.1 mass part, crosslinking density may become low too much, and may adversely affect the heat resistance of hardened | cured material, or when a composition exceeds 30 mass parts, the composition may not fully harden or heat resistance of hardened | cured material. May adversely affect

The organosilicon compound of (B) component may be used individually by 1 type, and may use 2 or more types together.

<(C) Condensation Catalyst>

Component (C) of the present invention is a condensation catalyst that promotes hydrolysis and condensation of the hydroxyl group (including the hydroxyl group in the silalkylenesilanol group) or the hydrolyzable group in the component (A).

As a condensation catalyst of (C) component, basic compounds, such as organometallic compounds, such as titanium, tin, and a zirconium, and the nitrogen containing compound which has a guanidyl group, etc. are mentioned, Preferably tetraisopropoxy citata is mentioned. Basic compounds such as organometallic compounds such as nate, tetrabutoxy titanate, dibutyl tin dioctate and dibutyl tin dilaurate, and tetramethylguanidine derivatives, more preferably tetramethylguanidylpropyl trimethoxysilane, Tetraisopropoxy citrate and tetrabutoxy titanate. Details are also described in US Pat. No. 4,111,890.

Although the compounding quantity of the condensation catalyst of (C) component should just be an effective amount required to harden a composition, it is 0.1-3 mass parts normally with respect to 100 mass parts of (A) component, Preferably it is 0.5-1.5 mass parts.

The condensation catalyst of (C) component may be used individually by 1 type, and may use 2 or more types together.

<(D) Photoinitiator>

Component (D) of the present invention is a photopolymerization initiator for efficiently initiating a photopolymerization reaction.

As a photoinitiator of (D) component, For example, benzoin and substituted benzoin (for example, alkylester substituted benzoin etc.), Michler's ketone, acetophenone, diethoxy acetophenone (DEAP), etc. Known for promoting photopolymerization reaction of acryloyl group and methacryloyl group, such as substituted acetophenone, benzophenone, and substituted benzophenone, xanthone, and substituted xanthone, such as dialkoxy acetophenone.

Specifically, diethoxy acetophenone, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, diethoxyxanthone, chloro thioxanthone, azobisisobutyronitrile, N-methyl diethanolamine benzophenone, and Visible light polymerization initiators, such as an ultraviolet-ray polymerization initiator, such as these mixtures, a camphorquinone peroxy ester initiator, a bifluorene carboxylic acid peroxy ester, and a mixture thereof, are mentioned, Especially, diethoxy acetophenone is preferable.

Commercially available photopolymerization initiators include initiators available under the trade names IRGACURE and DAROCURE from Ciba Specialty Chemicals, in particular Irgacure 184 (1-hydroxy). Cyclohexylphenyl ketone), 907 (2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one), 369 (2-benzyl-2-N, N-dimethylamino -1- (4-morpholinophenyl) -1-butanone), 500 (combination of 1-hydroxycyclohexylphenyl ketone and benzophenone), 651 (2,2-dimethoxy-2-phenylacetophenone) , 1700 (combination of bis (2,6-dimethoxybenzoyl-2,4,4-trimethylphenyl) phosphineoxide and 2-hydroxy-2-methyl-1-phenyl-propan-1-one) and 819 ( Bis (2,4,6-trimethylbenzoyl) phenylphosphineoxide); Darocure 1173 (2-hydroxy-2-methyl-1-phenyl-1-propane) and 4265 (2,4,6-trimethylbenzoyldiphenylphosphine oxide and 2-hydroxy-2-methyl-1-phenyl UV polymerization initiators, such as a combination of -propan-1-one; And d1-camphorquinone and Irgacure 784DC (bis (η ⁵ -2,4-cyclopentadien-1-yl) -bis [2,6-difluoro-3- (1H-pyrrol-1-yl) And visible light (blue) photopolymerization initiators such as phenyl] titanium).

Although the compounding quantity of the photoinitiator of (D) component will not be specifically limited if it is an effective amount required in order to start photopolymerization reaction efficiently, Usually, it is 0.1-3 mass parts with respect to 100 mass parts of (A) component, Preferably it is 0.5- 2.5 parts by mass.

The photoinitiator of (D) component may be used individually by 1 type, and may use 2 or more types together.

<(E) Phosphate Ester Compounds>

Component (E) of the present invention is a phosphate ester compound represented by the above formula (3) or (4), which acts as a flame retardant to impart flame retardancy to the cured product.

In the formulas (3) and (4), the monovalent hydrocarbon group represented by R ⁶ usually has 1 to 12 carbon atoms, specifically, the following formula

In the formula, ⁱ Pr represents an isopropyl group (hereinafter, the same), n is an integer of 1 to 5, and the like. However, since the flame retardancy of the cured product becomes particularly good, a substituted or unsubstituted Phenyl groups are preferred.

In the above formula (4), the divalent hydrocarbon group represented by Q has usually 1 to 12 carbon atoms, specifically, the following formula

The group etc. which are represented by are mentioned.

As a specific example of the phosphate ester compound of (E) component, the following general formula

Wherein n is an integer from 1 to 5

The thing represented by is mentioned.

The compounding quantity of the phosphate ester compound of (E) component needs to be 0.1-30 mass parts with respect to 100 mass parts of (A) component, Preferably it is 1-15 mass parts, More preferably, it is 10-15 mass parts. If the blending amount is less than 0.1 part by mass, the flame retardancy of the cured product may be remarkably inferior, and if it exceeds 30 parts by mass, the physical properties (hardness, elongation, tensile strength) of the cured product may be impaired.

The phosphate ester compound of (E) component may be used individually by 1 type, and may use 2 or more types together.

<Optional ingredient>

You may mix | blend another component with the composition of this invention in addition to the said (A)-(E) component within the range which does not impair the effect of this invention. Specifically, the following are mentioned.

Inorganic Filling Materials

For example, inorganic fillers can be added. This is a component that adds structural characteristics (ie, physical properties of the cured product) to the cured product and at the same time provides flow characteristics to the uncured composition. As the inorganic filler, for example, reinforcing silicas such as fumed silica can be used. The silica may be used in an untreated state (i.e., hydrophilic) or may be used after performing a surface hydrophobization treatment (i.e., hydrophobicity), but is preferably surface hydrophobization treatment.

Preferred hydrophobic silicas subjected to surface hydrophobization treatment include, for example, hexamethyldisilazane treated silica commercially available from Walker-Chemie under the trade name HDK-2000; Polydimethyl siloxane treatments commercially available from Cabot Corporation under the tradename CAB-O-SIL N70-TS, or from Degusa Corporation under the tradename AEROSIL R202. Silica; Trimethoxyoctylsilane-treated silica commercially available from Degussa under the trade name Aerosil R805; And trialkoxyalkylsilane-treated silicas such as 3-dimethyldichlorosilane-treated silica, which are commercially available from Degussa under the trade names Aerosil R972, R974 and R976.

Although the compounding quantity of an inorganic filler is 0-100 mass parts with respect to 100 mass parts of (A) component, in consideration of the characteristic of the silica to mix | blend, the desired characteristic of a composition, and a hardened | cured material, the composition has a suitable permeability level and UV curability It is to be noted that the compounding is carried out in the inside, and in the case of blending, it is preferable to blend 5 parts by mass or more, in particular 8 to 15 parts by mass.

Other optional ingredients

As other optional components, in order to adjust the hardness of hardened | cured material, it does not contain the organopolysiloxane which contains only one siloxy group in total, and / or alkenyl group which has an alkenyl group, a hydroxyl group, or two or more hydrolysable groups in one molecule. Organopolysiloxane may be blended. Moreover, flame retardant adjuvant, such as carbon black, iron oxide, cerium oxide, titanium oxide, a calcium carbonate, aluminum hydroxide, titanic acid ester, can also be mix | blended. In addition, silane coupling agents, such as isocyanate propyl triethoxysilane, can also be mix | blended.

<Production of composition>

The composition of this invention can be manufactured by mixing the said (A)-(E) component and arbitrary components uniformly. The composition can be cured by light irradiation, in particular UV radiation, or by moisture in the air to obtain a cured silicone rubber or cured silicone gel having excellent flame retardancy.

<Example>

Hereinafter, although an Example and a comparative example are given and this invention is demonstrated concretely, this invention is not limited to the following Example.

<Examples 1-6, Comparative Examples 1-5>

Each component was uniformly mixed with the kind and the blending amount shown in Table 1 below to prepare a silicone composition. The composition was introduced into a mold such that the thickness after curing was 1.5 mm, and the irradiation conditions of a high pressure mercury lamp (80 W / cm), a distance of 10 cm, and a speed of 1 m / min were carried out using a conveyor UV irradiation device (manufactured by Nippon Denchi Co., Ltd.). After irradiating with ultraviolet rays three times repeatedly, it was left to cure at 23 degreeC and 55% RH for 5 days, and it hardened | cured. The hardness and flame retardance of the obtained sheet-like hardened | cured material were measured and evaluated by the following method. The results are shown in Table 1.

<Measurement and evaluation method>

1. Hardness

The hardness of hardened | cured material was measured by the durometer type A (made by Shimadzu Corporation) of JISK6253 regulation.

2. Flame retardant

The sheet-like cured product was cut into a single sheet of 125 mm x 13 mm. Using the obtained single hardened | cured material, the combustion test was done according to UL94V-0, V-1, V-2 vertical combustion test by UNDERWRITERS LABORATORIES INC .. This test was performed 5 times for each cured product, and the average was evaluated. This test was repeated twice. The result (average value) is shown in Table 1.

* (A-1), (A-2), (A-3), (B), (E-1), (E-2), and (E-3) component and inorganic filler of Table 1 are as follows. same.

Component (A-1): Methylphenylpolysiloxane having a viscosity of 3000 mm ² / s at room temperature (25 ° C) in which both ends of the molecular chain are sealed with dimethylsilanol groups (phenyl group for all organic groups bonded to silicon atoms of the siloxane skeleton) Content 10 mol%)

(A-2) Component: The both ends of the molecular chain are represented by the following formula

Methylphenylpolysiloxane having a viscosity of 3000 mm ² / s at room temperature (25 ° C.) sealed with silethylenesilanol group represented by (phenyl mole content of 10 mol% based on total organic groups bonded to silicon atoms of the siloxane skeleton)

Component (A-3): methylphenylpolysiloxane having a viscosity of 900 mm ² / s at room temperature (25 ° C) in which both ends of the molecular chain are sealed with a trimethoxysiloxy group (all organic groups bonded to silicon atoms of the siloxane skeleton) Phenyl group content 10 mol%)

(B) component: the organosilicon compound represented by a following formula

(E) component: the phosphate ester compound represented by a following formula

-(E-1) component-

(E-2) Component-

(E-3) Component-

ㆍ Inorganic filler: Hydrophobic silica (trade name: R-972, manufactured by Nippon Aerosil Co., Ltd.)

"X" in flame retardancy evaluation indicates that none of the criteria of UL94V-0, V-1, and V-2 is satisfied.

The silicone composition of the present invention is useful for producing a transparent cured product having excellent flame retardancy, and is one capable of light curing, in particular UV curing. Therefore, application to the coating of the board | substrate which is transparent and flame-retardant which especially the electrical and electronic field is required is expected.

Claims (3)

(A) an organopolysiloxane represented by the following general formula (1) and having a total of two or more in one molecule of one or a combination of two or more kinds of siloxy groups having a hydroxyl group, a silalkylene silanol group, or two or more hydrolyzable groups : 100 parts by mass, (B) an organosilicon compound represented by the following formula (2): 0.1 to 30 parts by mass, (C) condensation catalyst: effective amount, (D) photoinitiator: effective amount, and (E) Phosphoric acid ester compound represented by the following general formula (3) or (4): Flame retardant silicone composition containing 0.1 to 30 parts by mass. <Formula 1>

Wherein R is a hydroxyl group, a silalkylenesilanol group or a hydrolyzable group, R ¹ is a methyl group or a phenyl group, a and b are independently positive, provided that a + b is a number from 1.9 to 2.4. <Formula 2>

Wherein R ² is independently a hydrogen atom, a phenyl group or a halogenated phenyl group, R ³ is independently a hydrogen atom or a methyl group, R ⁴ is independently a substituted or unsubstituted monovalent hydrocarbon group having 1 to 10 carbon atoms, X is a hydrolyzable group, Z ¹ is independently a chemical formula -R ^5- , -R ⁵ O- or -R ⁵ (CH ₃ ) ₂ SiO- (wherein R ⁵ is independently substituted or unsubstituted carbon atoms 1 To a divalent hydrocarbon group of 10 to 10, Z ² is an oxygen atom or a substituted or unsubstituted divalent hydrocarbon group having 1 to 10 carbon atoms, and m and n are each independently an integer of 0 to 2. <Formula 3>

In formula, R <^6> is a substituted or unsubstituted monovalent hydrocarbon group independently. <Formula 4>

In the formula, R ⁶ is independently a substituted or unsubstituted monovalent hydrocarbon group, and Q is a substituted or unsubstituted divalent hydrocarbon group. The composition according to claim 1, wherein the organopolysiloxane as the component (A) contains 2 mol% or more of phenyl groups based on the total of all R and all R ¹ . The composition according to claim 1 or 2, wherein R ⁶ in the (E) phosphate ester compound is a substituted or unsubstituted aryl group.