JPS6189229A - Siloxane-containing copolymer - Google Patents

Abstract

PURPOSE:To provide the titled copolymer giving highly weatherable sealing material free from joint staining capable of post-coating, constituted by polysiloxane-polyoxyalkylene block copolymer reactive at its molecular ends. CONSTITUTION:The objective copolymer constituted by siloxane-contg. copolymer of formula (Y is reactive monovalent group selected from H, -Q<2>(R2<1> SiO)mSiR2<1>R<2>, and -Q<3>SiR2<3>X3-a; Q<1> is 2-4C divalent hydrocarbon group; Q<2> is 2-6C divalent hydrocarbon group; R<1> is monovalent hydrocarbon; R<2> is 2-6C monovalent hydrocarbon group containing aliphatic unsaturated bond; R<3> is 2-6C divalent hydrocarbon group; R<3> is 1-6C monovalent hydrocarbon group; X is hydrolyzable group; m, n, and p are each integer >=1; a is 0-2). This copolymer can be obtained by blending (A) polyoxyalkylene dithiol of formula HS(Q<1>O)nQ<1>SH and (B) unsaturated hydrocarbon group-contg. polysiloxane followed by reaction under photoirradiation.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a novel copolymer containing siloxane,
More specifically, polysiloxane with reactivity at the molecular end.
This invention relates to polyoxyalkylene block copolymers.

[Conventional technology and problems]

Room-temperature-curable polyorganosiloxane compositions that cure with moisture in the air to give rubber-like elastic bodies are generally well known, and products with various curing mechanisms are commercially available.

Among these, room temperature-curable polyorganosiloxane compositions having adhesive properties are widely used as elastic adhesives. In particular, its heat resistance, cold resistance,
It is widely prized as a sealing material for construction because of its excellent durability such as weather resistance and ozone resistance, good workability, and excellent adhesive properties.

Room-temperature-curing polyorganosiloxane compositions used as sealants for buildings have been more than satisfactory in terms of sealing performance, but as the design of buildings has become more important in recent years, problems from a design perspective have arisen. (One problem that has come to mind is the problem of contamination of the joints, and the other major problem is the problem of paintability.The former is caused by the diffusion of unreacted silicone polymer around the joints where the silicone sealant has been applied. However, water-repellent contamination, dust adsorption, etc. occur, and the area around the joints gets dirty.The latter means that paints or thinners do not get on top of the silicone sealant, making it impossible to apply post-painting. All of these are due to the basic properties of polyorganosiloxane, such as low surface tension, water repellency, and mold release properties.

Several methods are being considered to solve these problems. One method is to use organically modified silicone polymers or silane modified organic polymers, and various polymers have been investigated. For example, JP-A-5
Publication No. 2-73998 discloses a polyether silylated at both ends, which is obtained by addition-reacting a polyether having unsaturated hydrocarbon groups at both ends and a hydrogen silane having a hydrolyzable group. Similarly, silylated polyesters, polyurethanes, vinyl polymers, polysulfides, and the like are known. Sealing materials using these materials have already been applied. In addition, instead of the above-mentioned hydrogen silane, hydrogen polysiloxane having a hydrolyzable group may be added to increase the amount of siloxane (JP-A-57-115456), or a siloxane obtained by partially hydrolyzing and condensing them may be used. Organic copolymers have also been disclosed (Japanese Unexamined Patent Publication No. 125152/1983).

However, sealants using polymers obtained by these methods have little joint contamination and can be painted afterward, but on the other hand, they have a basically small siloxane segment ratio and are inferior to silicone in terms of durability and weather resistance. It cannot be denied that it is considerably inferior when compared to sealants.

[Means for solving problems]

In light of these circumstances, the inventors of the present invention have conducted intensive studies on polymers that do not cause the problem of joint contamination, can be post-painted, and provide a sealing material with good weather resistance. The present invention has been accomplished by obtaining a crosslinkable polysiloxane-polyoxyalkylene copolymer and its intermediates which have anti-staining properties and post-paintability by modifying their surface properties.

Furthermore, since these intermediates similarly have reactivity at the molecular ends, they can open the way to various modified polymers.

That is, the present invention provides a compound having the general formula (wherein Y may be the same or different from each other and is selected from the group consisting of a hydrogen atom, -Q"(R'zSiO)-SiR'zR", and -Q3SiR3a Xl-a) The selected reactive monovalent group, Ql is the same or different divalent hydrocarbon group having 2 to 4 carbon atoms, and Q2 is 2 to 6 carbon atoms.
R1 is the same or different substituted or unsubstituted monovalent hydrocarbon group, R2 is a monovalent hydrocarbon group having 2 to 6 carbon atoms containing an aliphatic unsaturated bond, Q3 is A divalent hydrocarbon group having 2 to 6 carbon atoms, R3 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, X is a hydrolyzable group, m, n, and p are each an integer of 1 or more, a is O It relates to a siloxane-containing copolymer represented by (an integer of 2 to 2).

The copolymer of the present invention is a novel polymer that has not yet been described in the literature, and has a common structure except for Y at the molecular terminal.

In the copolymer of the present invention, Ql is an alkylene group of the polyoxyalkylene moiety, and also connects the polyoxyalkylene moiety with a thiosulfur atom, and Ql is an ethylene group, propylene group, trimethylene group, butylene group, or tetramethylene group. For example, ethylene groups, propylene groups, and combinations thereof are preferred because they are easy to synthesize and provide a copolymer with the surface properties targeted by the present invention.

Ql connects the polysiloxane moiety and the thiosulfur atom.
・) Examples include ethylene group, trimethylene group, tetramethylene group, pentamethylene group, hexamethylene group, etc., but ethylene group and trimethylene group are preferable because of easy synthesis, and ethylene group is particularly preferable.

R1 is an organic group bonded to the silicon atom of the polysiloxane moiety, and is an alkyl group such as a methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, octyl group, decyl group, dodecyl group, or octadecyl group; vinyl group,
2. Alkenyl groups such as allyl group; aryl groups such as phenyl group; aralkyl groups such as benzyl group, β-phenylethyl group, β-phenylpropyl group; and β-cyanoethyl group, γ-chloropropyl group. 3. Substituted hydrocarbon groups such as 3-trifluoropropyl group and chlorophenyl group are exemplified, and provide a copolymer with excellent weather resistance, and the resulting crosslinked polymer has excellent weather resistance and mechanical properties. Methyl groups are preferred in order to maintain fluidity in an uncrosslinked state while maintaining the necessary degree of polymerization and therefore good workability. To obtain excellent cold resistance, some phenyl groups,
To obtain oil resistance, other substituted or unsubstituted monovalent hydrocarbon groups, such as a 1°1,1-trifluoropropyl group, can be used depending on the required properties.

In the copolymer of the present invention, Y is a reactive group at the end of the molecule, and is a hydrogen atom, -Q''(R'□5in), 5tR1
□R", -QSiR', is either 1.

Among these, in order to obtain a crosslinkable polymer that exhibits rubber-like elasticity,
Both terminal Y's of the molecule are -Q3SiR-x2-. A copolymer of is used as the base polymer. Further, as an intermediate for obtaining such a copolymer, a polymer in which both Y terminals are hydrogen atoms is used. Y at both ends
are both Q''(R'zSiO) and SiR'zR'', and one Y is a hydrogen atom and the other is 10''
The polymers (R'zSiO)l and 1SiR12R1 can be generated as a by-product when obtaining the above intermediate, or can be synthesized for their own purposes, but they can be obtained by combining various block copolymers and graft copolymers. It is useful as a prepolymer for obtaining. Further, it is also possible to use the intermediate in which these by-product polymers are still present as a raw material for a crosslinkable polymer.

m is the degree of polymerization of the polysiloxane moiety and n is the degree of polymerization of the polyoxyalkylene moiety, and both can be any integer of 1 or more, and are selected depending on the physical properties required for the copolymer. From the mechanical properties of the copolymer and crosslinked polymer, m is preferably in the range of 5 to 2, Q00,
The number n is more preferably 10 to 1,000. Considering the ease of synthesis of the raw materials, the ease of reaction, and the properties of the obtained copolymer, n is preferably in the range of 1 to 100, and more preferably 2 to 40.

p is the number of repetitions of both segments and is an integer of 1 or more. Physical properties of the copolymer, especially when used as a base polymer of a crosslinked polymer and its intermediate, from the viewpoint of ease of handling and mechanical properties of the crosslinked polymer, the viscosity of the copolymer at 25°C is 100 to 100, Q00 cP. It is preferable that the number is such that The polymerization degree ratio of the siloxane part and the polyoxyalkylene part, that is, m+1/n+1, is 0.2 to 40 from the viewpoint of weather resistance and surface properties of the resulting copolymer.
A range of is preferred.

Hz contains an aliphatic unsaturated bond, and port 3 is obtained by hydrosilylation reaction of R2. R2 is a vinyl group,
Allyl group, butenyl group, pentenyl group, hexenyl group;
Examples of R3 include ethylene group, trimethylene group, tetramethylene group, pentamethylene group, and hexamethylene group.
It is preferable that 2 is a vinyl group or an allyl group, and R3 is an ethylene group or a trimethylene group, and an ethylene group is particularly preferable.

Examples of R3 include the same substituted or unsubstituted monovalent hydrocarbon group as R1, but a methyl group is preferred because of its ease of synthesis.

X is a hydrolyzable group bonded to a silicon atom; an alkoxy group such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group; a β-methoxyethoxy group, a β-ethoxyethoxy group, a β-butoxyethoxy group; alkoxyalkoxy group; enoxy group such as isopropenyloxy group; ketoximato group such as dimethylketooximado group, methylethylketooximado group; amino group such as diethylamino group, dibutylamino group; aminoxy group such as diethylaminoxy group Examples include a group; a carboxy group such as an acetoxy group or an octanoyloxy group; and an amide group such as an N-methylacetamide group. Among these, lower alkoxy groups having 1 to 4 carbon atoms are preferred because they are easy to synthesize and do not corrode the base material when used as a sealing material. A methoxy group is more preferable because a fast reaction rate can be obtained, and a ketooximado group is also preferable because it is easy to synthesize, has a good balance between curing speed and adhesion, and has no irritating odor.

a Lt is an integer from O to 2. When using this siloxane-containing copolymer as a base polymer to obtain a rubber-like elastic body by reaction with moisture in the air, it is necessary that a be less than 2 on average.

On the other hand, when used for modifying other polymers, a may be 2.

Examples of such siloxane-containing copolymers include the following. The following abbreviations will be used below to simplify the description.

Me: methyl i Et: ethyl group Vi: vinyl group P
h: phenyl group EO nioxyethylene position PO nioxypropylene unit ligL; lit (MezSiOJ zosiMez
Among the siloxane-containing copolymers of the present invention, those in which Y is a hydrogen atom and -Q"(R'2SiO), SiR'zR" are synthesized as follows.

That is, the general formula HS(Q'0)fiQ'SH (wherein,
Ql, n are as described above) and a polyoxyalkylene dithiol represented by the general formula R''(R', SiO)M Si
Unsaturated hydrocarbon group-containing polysiloxanes represented by R', R'' (where RISRl and m are as described above) are mixed in the presence or absence of a catalyst, and heated at room temperature or heated. or under irradiation with light such as ultraviolet light.

Examples of polyoxyalkylene dithiols include the following.

R5ECHzCHzO) XCHzCHzS11H5
(CHzCH(CHz)0) y CHzCH(
CHi)SHHS (CH2CH20), (C
1hCfl(CHi)0), C)IzCHz
SHH5((CHg) +0) z (CII
Z) aSH (In the formula,
, ω-divinylpolydimethylsiloxane and α,ω-diallylpolydimethylsiloxane are common.

The blending ratio of the polyoxyalkylene dithiol and the unsaturated hydrocarbon group-containing polysiloxane can be selected arbitrarily as the molar ratio of the mercapto group to R2, but it is preferably between 374 and 4/3. Theoretically, when the molar ratio is 171, one Y in the molecule is a hydrogen atom and the other Y is -G''(
R'□5in), Si; R'2R" copolymer was obtained with the highest yield, and the molar
) If the ratio increases, both Ys are hydrogen atoms, and if the molar ratio decreases, both Ys become -Q''(R'□5
in).

A large amount of SiR', R'' can be obtained. However, if the molar ratio is less than 374 or more than 4/3, the degree of polymerization required for use as a base polymer for rubber-like elastic bodies cannot be obtained. In addition, the reaction is carried out in two stages.After the first stage is carried out within the above molar ratio range to obtain a sufficient degree of polymerization, one of the raw materials is added, for example, the remaining R
By adding polyoxyalkylene dithiol containing an equimolar amount of mercapto group to 2 and carrying out the second stage reaction,
It is also possible to obtain only a terminal diol copolymer having only a hydrogen atom as the terminal Y.

As a catalyst for this reaction, any catalyst commonly used for the reaction between a vinyl group and a mercapto group can be used, and examples thereof include diisobutyl peroxide, 2.2-bis(t-butylperoxy)butane, and 2.2-bis(t-butylperoxy)butane. (L-butylperoxy)octane, dicumyl peroxide, 1.1-bis(t-butylperoxy)cyclohexane, 1.1-bis(t-butylperoxy)-3,3,5-)limethyl Cyclohexane, α,α-bis(t-butylbaroxyisobrorobyl)benzene, t-butylperoxyisobutyrate, t-butylperoxypivalate, t-
Butylperoxy-2-ethylhexanoate, 1-butylperoxy-3,5,5-)limethylhexanoate, t-butylperoxyneodecanoate, t-butylperoxylaurate, t- Butyl peroxymaleate, cumylperoxyneodecanoate, t-butylperoxyisobrobyl carbonate, diisopropylberoxydicarbonate, di(methoxyisopropyl)peroxydicarbonate, di(2-ethoxyethyl)peroxydicarbonate Oxydicarbonate, di(3-methyl-3-methoxybutyl) peroxydicarbonate, di(2-ethylhexyl) peroxydicarbonate, dimyristyl peroxydicarbonate, t-butyl peroxybenzoate, 2,5-dimethyl -2,5-di(benzoylperoxy)hexane, acetyl peroxide, octanoyl peroxide, 3,3,5-1-limethylhexanoyl peroxide, decanoyl peroxide, lauroyl peroxide, succinic acid peroxide , benzoyl peroxide, 2,4-dichlorobenzoyl peroxide, totle oil peroxide,
Organic peroxides such as methyl ethyl ketone peroxide, cyclohexanone peroxide, benzoylcyclohexylsulfonyl peroxide; nitrile compounds such as azobisisobutyronitrile; alkali metal alcoholades such as sodium methoxide; tetramethylammonium hydroxide, tetrahydroxide propylammonium,
Quaternary ammonium compounds such as tetrabutylammonium hydroxide and tetrabutylammonium fluoride, and ion exchange resins with these quaternary ammonium structures; triethylamine, dimethylaminoethanol, triethanolamine, triethylenediamine, N,N-dimethyl Tertiary amines such as aniline, diazabicycloundecene-7; Guanidines such as 1,1,3,3-tetramethylguanidine; ((CH3)2N)zC=N(CHz)zsi(O
Examples include amino group-containing silanes such as CR+)z; Lewis acids such as zinc chloride, tin chloride, aluminum chloride, titanium chloride, boron fluoride, and complex compounds thereof.

The amount of these catalysts used is preferably in the range of 0, Q01 to 30% by weight based on the sum of the weights of polyoxyalkylene dithiol and unsaturated group-containing polysiloxane, and 0, Q5.
-20% by weight is more preferable. If it is less than 0.001% by weight, the effect of the catalyst will not be sufficient (and if it is used in excess of 30% by weight, no further effect can be expected).

This reaction can be carried out without a solvent, but in order to make the starting materials compatible (or when their viscosity is high), to facilitate stirring and mixing and to make the reaction proceed uniformly, The reaction may be carried out by dissolving it in an inert organic solvent. Examples of organic solvents used include aromatic hydrocarbons such as benzene, toluene, and xylene; aliphatic hydrocarbons such as hexane, octane, and cyclohexane; Ethers such as butyl ether; ketones such as methyl ethyl ketone and methyl isobutyl ketone; trichlorethylene,
Examples include halogenated hydrocarbons such as 1,1.1-) dichloroethane.

Among the siloxane-containing copolymers of the present invention, Y is -Q3S
, iR3, can do. Examples of the aliphatic unsaturated hydrocarbon group include a vinyl group, an allyl group, a butenyl group, a pentenyl group, and a hexenyl group. A vinyl group is preferred because the raw material silane can be easily synthesized, handling and addition reactions can be easily carried out, and the desired product can be obtained in good yield. Examples of R'' and
Examples include (β-methoxyethoxy)silane, trimethoxysilane, vinylmethyldimethoxysilane, vinyldimethylmethoxysilane, vinyltri(methylethylketoximato)silane, vinyltriacetoxysilane, vinylt'J(N-methylacetamido)silane, etc. be done.

Vinyltrimethoxysilane,
Vinylmethyldimethoxysilane, vinyltri(β-methoxyethoxy)silane, vinyltri(methylethylketoximato)silane, and the like are preferred.

The blending ratio of the siloxane-containing copolymer of terminal dithiol and silane is such that the ratio of the mercapto group of the former to the R2 of the latter is 1.
/1 or less, but a normal value of 1/1.1 to 1/10 is preferable in order to make the reaction proceed smoothly.
More preferably 1/1.5 to 115.

The siloxane-containing copolymer of terminal dithiol is a mixed by-product, that is, one or both of Y is Q''(R' zs
to) m StR' zR2 may be reacted with the above-mentioned silane in the presence of the copolymer.

The reaction is carried out under the same conditions as the first stage reaction, that is, the reaction of the polyoxydialkylene dithyl ol and the unsaturated hydrocarbon group-containing polysiloxane.

After the reaction is complete, excess unsaturated group-containing silane can be recovered by stripping and reused.

〔Effect of the invention〕

Among the siloxane-containing copolymers obtained by the present invention, those in which Y at both ends are -Q3SiR3@X3-a are polysiloxane-polyoxyalkylene copolymers in which a silyl group having a hydroxyl group or a hydrolyzable group exists at the end. It is a polymer. Those with hydrolyzable groups react with moisture in the air at room temperature to provide a rubber-like elastic body that has good weather resistance, does not cause joint staining, and can be post-coated.

In addition, among the siloxane-containing copolymers obtained by the present invention, those in which Y at both ends are hydrogen atoms can be used as intermediates for synthesizing the above-mentioned copolymer of Y10'5iR3a X3-11. Useful. Furthermore, Y is a hydrogen atom and/or
or -Q''(R'□5iO)+++SiR'□R2, the copolymers are useful as modifiers for other polymers.

[Examples] Hereinafter, the present invention will be explained with reference to Examples, but the present invention is not limited to these Examples.

In the examples, parts represent parts by weight. Physical property values such as viscosity are 2
This is the value at 5°C.

Example 1 ViMezSi was placed in a reaction vessel equipped with a stirrer, a thermometer, a cooling tube with a silica gel-filled absorption tube, and a nitrogen introduction tube.
O(MezSiO), SiMe, 63 parts of Vi, 39 parts of ethylene glycol bis(2-mercaptoethyl) ether, 200 parts of toluene, 25 parts of triethylenediamine
The mixture was heated at 90° C. for 12 hours while stirring in a nitrogen stream. Then, toluene, triethylenediamine 1, and excess ethylene glycol bis(2-mercaptoethyl) ether were distilled off under reduced pressure to obtain 93 parts of a pale yellow, transparent liquid reaction product.

Potentiometric titration method (JIS K2276
) analysis of mercapto groups, NMR analysis, IR analysis, and elemental analysis were performed. The results are as follows, and were in good agreement with the theoretical values of the compound represented by the following structural formula (theoretical values are shown in parentheses).

Mercapto group: 6.52χ C,C: Not detected 3.8 By NMR (SCHz) / (Si(Cth)z)
Ratio 0.15 Example 2 Using the same apparatus as in Example 1, the same reaction as in Example 1 was carried out by changing the degree of polymerization of siloxane, the catalyst, and the mixing ratio of raw materials. The following siloxanes were used.

VSi-1: ViMezSiOSiMezViVSi-
2: ViMezSiO (MezSiO) zqSiMe
zViVSi-3: ViMe2SiO(Me, 5iO)
+t, SiMezVi The raw materials and reaction conditions used, as well as the yield, physical property values, and analysis results of the reaction products are shown in Table 1.

Example 3 Using the same apparatus as in Example 1, reactions were carried out in the same manner as in Example 1 using various raw materials and blending ratios to obtain various copolymers. That is, in Experiments 31 and 32, VSi-2 used in Example 2 was used as the siloxane, and by lowering the ratio of mercapto groups to vinyl groups bonded to silicon atoms, in Experiment 31, copolymers with various terminal groups were prepared. In Experiment 32, a copolymer having vinyl groups at both ends was obtained.

Experiments 33 and 34 introduced a different polyether moiety than in Examples 1 and 2. In Experiments 35 and 36, by using the following siloxanes, in Experiment 35, a siloxane moiety with a phenyl group bonded to a silicon atom was introduced, and in Experiment 36, a siloxane moiety with a trimethylene chain was introduced in the connecting part between the siloxane chain and the polyether chain. A polymer was obtained.

VSi-4: ViMe, SiO (MezSiO) 7 (
PhzSiO) SiMe2ViASi-1:CHz=
CHCHzMezSiOSiMezCHzCH=CHz
Table 2 shows the raw materials and reaction conditions used, as well as the yield, physical property values, and analysis results of the reaction products.

Example 4 270 parts of the reaction product obtained in Experiment 22 of Example 2, 200 parts of toluene, 10 parts of triethylenediamine, and 60 parts of vinyltrimethoxysilane were charged into the same apparatus as in Example 1, and stirred in a nitrogen stream. While heating, heating was performed at 90° C. for 12 hours.

Then, toluene, triethylenediamine, and excess vinyltrimethoxysilane were distilled off under reduced pressure to obtain 289 parts of a pale yellow, transparent liquid.

Neither mercapto groups nor C=C bonds were detected in this product, and the elemental analysis results were in good agreement with the theoretical values of the following formula.

Viscosity (25°C): 75 cP Example 5 Using the same apparatus as in Example 1, the same reaction as in Example 4 was carried out except that the silane shown in Table 2 was used instead of vinyltrimethoxysilane, and each A liquid reaction product was obtained. Table 3 shows the yield, physical property values, and analysis results of those reaction products.

The composition formula of the product obtained in each experiment is as follows.

Experiment 51: Experiment 52: Experiment 53: Experiment 54: Example 6 Into the same apparatus as in Example 1, 180 parts of the reaction product obtained in Experiment 31 of Example 3, ethylene glycol bis(2-
20 parts of mercaptoethyl ether, 5 parts of triethylenediamine, and 200 parts of xylene were charged, and the mixture was heated at 120° C. for 4 hours while stirring in a nitrogen stream. Then, xylene, triethylene diamine, and excess ethylene glycol bis(2-mercaptoethyl) ether were distilled off under reduced pressure to obtain 182 parts of a pale yellow transparent liquid.

No vinyl groups were detected in this product, and the amount of malecapto groups was 0.32%. The viscosity at 25° C. was 740 cP.

[Brief explanation of drawings]

FIG. 1 is an infrared spectroscopy chart of the product obtained in Experiment 22 of Example 2, and FIG. 2 is an infrared spectroscopy chart of the product obtained in Experiment 24 of Example 2.

Claims (1)

[Claims] 1. General formula Y-S-(Q^1O)-_n-Q^1-[S-Q^2(
R^1_2SiO)-_mR^1_2Si-Q^2--
S-(Q^1O)-_nQ^1]-_pS-Y (in the formula,
Y may be the same or different, and may be a hydrogen atom, -
Q^2(R^1_2SiO)_mSiR^1_2R^2
, and -Q^3SiR^3_aX_3_-_a, Q^1 is a divalent hydrocarbon group having 2 to 4 carbon atoms that is the same or different from each other, Q^2
is a divalent hydrocarbon group having 2 to 6 carbon atoms, R^1 is a substituted or unsubstituted monovalent hydrocarbon group that is the same or different from each other, R
^2 is a monovalent hydrocarbon group having 2 to 6 carbon atoms containing an aliphatic unsaturated bond, Q^3 is a divalent hydrocarbon group having 2 to 6 carbon atoms,
R^3 is a monovalent hydrocarbon group having 1 to 6 carbon atoms, X is a hydrolyzable group, m, n, and p are each an integer of 1 or more, and a is 0 to
is an integer of 2) A siloxane-containing copolymer represented by: 2. The siloxane-containing copolymer according to claim 1, wherein each of the two Y's is a hydrogen atom. 3. One of Y is a hydrogen atom and the other is -Q^2(R^1
The siloxane-containing copolymer according to claim 1, which is _2SiO)_mSiR^1_2R^2. 4. Both Y are −Q^2(R^1_2SiO)
The siloxane-containing copolymer according to claim 1, which is __mSiR^1_2R^2. 5. The siloxane-containing copolymer according to claim 3 or 4, wherein R^2 is a vinyl group. 6. Both Y are -Q^3SiR^3_aX_3
The siloxane-containing copolymer according to claim 1, which is ___a. 7. The siloxane-containing copolymer according to claim 6, wherein X is an alkoxy group having 1 to 4 carbon atoms. 8. The siloxane-containing copolymer according to claim 7, wherein X is a methoxy group. 9. The siloxane-containing copolymer according to claim 6, wherein X is a ketoximato group. 10. The siloxane-containing copolymer according to claim 1, wherein Q^1 is one or both of an ethylene group and a propylene group. 11. The siloxane-containing copolymer according to claim 1, wherein Q^2 is an ethylene group. 12. The siloxane-containing copolymer according to claim 1, wherein R^1 is a methyl group. 13. Claim 1 in which m is 10 to 1,000
The siloxane-containing copolymer described in . 14. The siloxane-containing copolymer according to claim 1, wherein n is 2 to 40. 15. The siloxane-containing copolymer according to claim 1, wherein m+1/n+1 is 0.2 to 40. 16. The siloxane-containing copolymer according to claim 1, wherein Q^3 is an ethylene group. 17. The siloxane-containing copolymer according to claim 1, wherein R^3 is a methyl group.