Silicon polymer production method using non-transition-metal-catalyst method of hydrosilylation

Abstract

The present invention relates to a silicon polymer production method using a non-transition-metal-catalyst method of hydrosilylation, and more specifically relates to a production method for a silicon polymer using a non-transition-metal-catalyst method of hydrosilylation, wherein an environmentally friendly silicon polymer is produced by using hydrosilylation using a non-transition metal as a catalyst, thereby avoiding the use of platinum, palladium and rhodium or other expensive platinum group catalysts and so achieving outstanding economic viability and making it possible to prevent residues of heavy metals.

Claims

1. A method for preparing an environmentally friendly silicon polymer, wherein a divinyl compound and a dihydrosilane compound represented by Chemical Formula 3 or Chemical Formula 13 are subjected to a hydrosilylation reaction in the presence of an organoboron catalyst: ##STR00021## (in Chemical Formula 3, R.sub.7 and R.sub.8 are each independently selected from the group consisting of hydrogen, (C1-C10) alkyl, OR.sub.9, N(R.sub.10)(R.sub.11), P(R.sub.12)(R.sub.13)(R.sub.14), and -D-Si(R.sub.15)(R.sub.16)(R.sub.17), not simultaneously hydrogen, the D) is selected from the group consisting of oxygen, (C1-C20) alkylene, (C3-C20) cycloalkylene, (C6-C20) arylene, (C3-C20) heterocycloalkylene, and (C4-C20) heteroarylene, the R.sub.15 to R.sub.17 are each independently selected from the group consisting of hydrogen, (C1-C10) alkyl, (C2-C20) alkenyl, (C3-C20) cycloalkyl, (C6-C20) aryl, (C3-C20) heterocycloalkyl, (C4-C20) heteroaryl, OR.sub.19, N(R.sub.20)(R.sub.21), and P(R.sub.22)(R.sub.23)(R.sub.24), the R.sub.9 to R.sub.14 and R.sub.19 to R.sub.24 are each independently hydrogen or (C1-C5) alkyl, and the alkyl, alkylene, alkenylene, cycloalkylene, and arylene are substitutable with at least one selected from the group consisting of (C1-C7) alkyl, halogen, nitro, cyano, hydroxyl, amino, (C6-C20) aryl, (C2-C7) alkenyl, and (C3-C20) cycloalkyl) ##STR00022##

2. The method of claim 1, wherein the divinyl compound is represented by Chemical Formula 1 below: ##STR00023## (in Chemical Formula 1 above, R.sub.1 to R.sub.6 are each independently selected from the group consisting of hydrogen and (C1-C10) alkyl, the A is selected from the group consisting of a chemical bond, oxygen, sulfur, carbonyl, (C1-C20) alkylene, (C2-C20) alkenylene, (C3-C20) cycloalkylene, (C6-C20) arylene, (C3-C20) heterocycloalkylene, (C4-C20) heteroarylene and (R.sub.2SiO).sub.n, the Rs in the (R.sub.2SiO).sub.n are each independently selected from hydrogen or (C1-C10) alkyl, n is selected from 10 to 10,000, and the alkyl, alkylene, alkenylene, cycloalkylene, arylene, heterocycloalkylene and heteroarylene are substitutable with at least one selected from the group consisting of (C1-C7) alkyl, halogen, nitro, cyano, hydroxy, amino, (C6-C20) aryl, (C2-C7) alkenyl, (C3-C20) cycloalkyl, (C3-C20) heterocycloalkyl and (C4-C20) heteroaryl).

3. The method of claim 2, wherein the divinyl compound is represented by Chemical Formula 2 below: ##STR00024## (in Chemical Formula 2 above, R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are each independently selected from the group consisting of hydrogen and (C1-C5) alkyl, the A is selected from the group consisting of (C1-C10) alkylene, (C2-C10) alkenylene, (C3-C10) cycloalkylene, (C6-C10) arylene and (R.sub.2SiO).sub.p, the Rs in the (R.sub.2SiO).sub.p are each independently selected from hydrogen or (C1-C10) alkyl, p is selected from 10 to 5,000, and the alkyl, alkylene, alkenylene, and cycloalkylene and arylene are substitutable with at least one selected from the group consisting of (C1-C7) alkyl, halogen, nitro, cyano, hydroxy, amino, ((C6-C20) aryl, (C2-C7) alkenyl and (C3-C20) cycloalkyl).

4. The method of claim 1, wherein an unsaturated group of the dinvinyl compound and a SiH group of the dihydrosilane compound are included at a molar ratio of 40:60 to 60:40, and the organoboron catalyst is included at an amount of 0.01 to 10 mol % based on the divinyl compound.

5. The method of claim 1, wherein the organoboron catalyst is represented by Chemical Formula 5 below: ##STR00025## (in Chemical Formula 5, R.sub.30 and R.sub.31 are each independently selected from the group consisting of halogen, (C1-C10) alkyl, (C3-C10) cycloalkyl and (C6-C10) aryl, the R.sub.32 is each independently selected from the group consisting of hydrogen, halogen, (C1-C10) alkyl, and (C6-C10) aryl, the alkyl, cycloalkyl, and aryl are substitutable with any one selected from (C1-C7) alkyl or halogen, and the n is an integer selected from 0 to 5).

6. The method of claim 5, wherein the organoboron catalyst is represented by Chemical Formula 6 below: ##STR00026## (in Chemical Formula 6 above, R.sub.30 is selected from the group consisting of halogen, (C1-C10) alkyl, (C3-C10) cycloalkyl, and (C6-C10) aryl, the R.sub.32 to R.sub.331 are each independently selected from the group consisting of hydrogen, halogen, (C1-C10) alkyl, and (C6-C0) aryl, the alkyl, cycloalkyl, and aryl are substitutable with at least one selected from (C1-C7) alkyl or halogen, and the n is an integer selected from 0 to 5, not simultaneously 0).

7. The method of claim 6, wherein the organoboron catalyst is represented by Chemical Formula 7 below: ##STR00027## (in Chemical Formula 7 above, the R.sub.32, R.sub.330, and R.sub.331 are each independently selected from the group consisting of hydrogen, halogen, (C1-C10) alkyl, and (C6-C10) aryl, the alkyl, cycloalkyl, and aryl are substitutable with at least one selected from the group consisting of (C1-C7) alkyl or halogen, and the n is an integer selected from 0 to 5, not simultaneously 0).

8. The method of claim 1, wherein the method comprises: mixing a catalyst solution including the organoboron catalyst, the dihydrosilane compound, and the divinyl compound, and reacting the resultant mixture at 20 to 40 C. for 12 to 48 hours.

Description

DESCRIPTION OF DRAWINGS

(1) FIG. 1 is a .sup.1H NMR (600 MHz, CDCl.sub.3) measurement result of a silicon polymer prepared according to Example 1 of the present invention.

(2) FIG. 2 is a .sup.13C NMR (150 MHz, CDCl.sub.3) measurement result of the silicon polymer prepared according to Example 1 of the present invention.

(3) FIG. 3 is an FT-IR measurement result of the silicon polymer prepared according to Example 1 of the present invention.

BEST MODE

(4) Hereinafter, preferred embodiments and a method of measuring physical properties for a method for preparing a silicon polymer using a non-transition-metal-catalyst method of hydrosilylation according to the present invention will be described in detail. The present invention can be better understood by the following examples, which are provided for the purpose of illustrating the present invention and which are not intended to limit the scope of protection limited by the appended claims.

(5) The inventors of the present invention have conducted studies in order to develop a silicon polymer not using expensive platinum group catalysts, and as a result, the inventors discovered that it is possible to provide a method for preparing an environmentally friendly silicon polymer with excellent economic feasibility, no residual heavy metal, improved yield of hydrosilylation reaction, and excellent reactivity because of not using platinum group catalysts, by preparation by reacting a divinyl compound and a dihydrosilane compound under the presence of an organoboron catalyst in hydrosilylation, thereby completing the present invention.

(6) Hereinafter, an embodiment of the present invention will be described in more detail.

(7) The preparation method of the environmentally friendly silicon polymer according to an embodiment of the present invention includes subjecting a divinyl compound and a dihydrosilane compound to hydrosilylation under the presence of an organoboron catalyst.

(8) The divinyl compound according to an embodiment of the present invention is a compound including at least two ethylene unsaturated groups and forms a crosslinked structure by cleaves the SiH bond of the dihydrosilane compound and binding to a double bond of the divinyl compound under the presence of an organic boron catalyst.

(9) The divinyl compound is not limited as long as it is a publicly disclosed compound in the art, and it can be represented by, for example, Chemical Formula 1 below.

(10) ##STR00008##

(11) (in Chemical Formula 1 above, R.sub.1 to R.sub.6 are each independently selected from hydrogen and (C1-C10) alkyl,

(12) the A is selected from a chemical bond, oxygen, sulfur, carbonyl, (C1-C20) alkylene, (C2-C20) alkenylene, (C3-C20) cycloalkylene, (C6-C20) arylene, (C3-C20) heterocycloalkylene, (C4-C20) heteroarylene, and (R.sub.2SiO).sub.n,

(13) the Rs are each independently selected from hydrogen or (C1-C10) alkyl, p is selected from 10 to 10,000, and

(14) the alkyl, alkylene, alkenylene, cycloalkylene, arylene, heterocycloalkylene, and heteroarylene are substitutable with at least one selected from among (C1-C7) alkyl, halogen, nitro, cyano, hydroxyl, amino, (C6-C20) aryl, (C2-C7) alkenyl, (C3-C20) cycloalkyl, (C3-C20) heterocycloalkyl, and (C4-C20) heteroaryl).

(15) The term alkyl as described in the present invention refers to a monovalent linear or branched saturated hydrocarbon radical consisting of carbon and hydrogen atoms, unless otherwise stated, and the term alkylene refers to a divalent linear or branched saturated hydrocarbon radical consisting of carbon and hydrogen atoms. Specific examples include, but are not limited to, methylene, ethylene, trimethylene, propylene, tetramethylene, pentamethylene, etc.

(16) The term (C2-C20) alkenylene as described in the present invention refers to a divalent linear or branched unsaturated hydrocarbon radical containing one or more double bonds, unless otherwise stated. Specific examples include, but are not limited to, ethenylene, prophenylene, butenyl, and pentenylene, etc.

(17) The term (C3-C20) cycloalkylene as described in the present invention refers to, unless otherwise stated, a divalent cyclic saturated hydrocarbon radical including a saturated monocyclic or saturated bicyclic ring structure of the number of carbon atoms of 3 to 20.

(18) The term (C6-C20) cycloalkylene as described in the present invention refers to a divalent organic radical induced from aromatic hydrocarbons by the removal or two hydrogen atoms and includes a single or fused ring system including 4 to 7, preferably, 5 to 6 ring atoms in each ring. Specific examples include phenylene, naphthalene, biphenylene, etc., but not limited thereto.

(19) The term heterocycloalkylene as described in the present invention refers to, unless otherwise stated, a divalent cycloalkylene radical including 1 to 3 hetero atoms selected from N, O, S as a saturated cyclic hydrocarbon skeleton atom, and the rest of saturated monocyclic or bicyclic ring skeleton atoms are carbon.

(20) The term (C4-C20) heteroarylene as described in the present invention refers to, unless otherwise stated, a divalent aryl radical including 1 to 3 heteroatoms selected from N, O, S as aromatic ring skeleton atoms, and the rest of aromatic ring skeleton atoms are carbon.

(21) Preferably, the divinyl compound can be represented by Chemical Formula 2 below.

(22) ##STR00009##

(23) (in Chemical Formula 2 above, R.sub.1, R.sub.2, R.sub.3, and R.sub.4 are each independently selected from hydrogen and (C1-C5) alkyl,

(24) the A is selected from (C1-C10) alkylene, (C2-C10) alkenylene, (C3-C10) cycloalkylene, (C6-C10) arylene, and (R.sub.2SiO).sub.p,

(25) the Rs are each independently selected from hydrogen or (C1-C10) alkyl, p is selected from 10 to 10,000, and

(26) the alkyl, alkylene, alkenylene, and cycloalkylene, and arylene are substitutable with at least one selected from among (C1-C7) alkyl, halogen, nitro, cyano, hydroxy, amino, (C6-C20) aryl, (C2-C7) alkenyl, and (C3-C20) cycloalkyl).

(27) The divinyl compound according to an embodiment of the present invention may specifically be 1,4-diisopropenylbenzene, but not limited thereto.

(28) The dihydrosilane compound according to an embodiment of the present invention is a compound including at least two or more SiH groups, and binds with the double bond of the divinyl compound while cleaving the SiH bond under the presence of an organic boron catalyst, in order to form a crosslinked structure.

(29) The dihydrosilane compound according to an embodiment of the present invention is not limited as long as it is a publicly disclosed dihydrosilane compound in the art, and more specifically it can be represented by Chemical Formula 3 below.

(30) ##STR00010##

(31) (in Chemical Formula 3 above, R.sub.7 and R.sub.8 are each independently selected from among hydrogen and (C1-C10) alkyl, (C2-C20) alkenyl, (C3-C20) cycloalkyl, (C6-C20) aryl, (C3-C20) heterocycloalkyl, (C4-C20) heteroaryl, OR.sub.9, N(R.sub.10)(R.sub.11), P(R.sub.12)(R.sub.13)(R.sub.14), and D-Si(R.sub.15)(R.sub.16)(R.sub.17), not simultaneously hydrogen,

(32) the D is selected from oxygen, (C1-C20) alkylene, (C2-C20) alkenylene, (C3-C20) cycloalkylene, and (C6-C20) arylene,

(33) the R.sub.15 to R.sub.17 are each independently selected from among hydrogen, (C1-C10) alkyl, (C2-C20) alkenyl, (C3-C20) cycloalkyl, (C6-C20) aryl, (C3-C20) heterocycloalkyl, (C4-C20) heteroaryl, OR.sub.19, N(R.sub.20)(R.sub.21), and P(R.sub.22)(R.sub.23)(R.sub.24),

(34) the R.sub.9 to R.sub.14 and R.sub.19 and R.sub.24 are each independently hydrogen or (C1-C10) alkyl, and

(35) the alkylene, alkenylene, cycloalkylene, arylene, heterocycloalkylene and heteroarylene are substitutable with at least one selected from among (C1-C7) alkyl, halogen, nitro, cyano, hydroxy, amino, (C6-C20) aryl, (C2-C7) alkenyl, (C3-C20) cycloalkyl, (C3-C20) heterocycloalkyl and (C4-C20) heteroaryl).

(36) More specifically, for the dihydrosilane compound according to an embodiment of the present invention, in Chemical Formula 3, R.sub.7 to R.sub.10 are each independently selected from hydrogen and (C1-C10) alkyl, not simultaneously hydrogen,

(37) the B is selected from (C1-C20) alkylene, (C2-C20) alkenylene, (C3-C20) cycloalkylene, and (C6-C20) arylene,

(38) the alkyl, alkylene, alkenylene, cycloalkylene, and arylene are substitutable with at least one selected from among (C1-C7) alkyl, halogen, nitro, cyano, hydroxy, amino, (C6-C20) aryl, (C2-C7) alkenyl, and (C3-C20) cycloalkyl, but not limited thereto.

(39) According to an embodiment of the present invention, in the dihydrosilane compound in Chemical Formula 3 above, R.sub.7 and R.sub.8 are each independently selected from hydrogen, (C1-C10) alkyl, OR.sub.9, N(R.sub.10)(R.sub.11), P(R.sub.12)(R.sub.3)(R.sub.4), and -D-Si(R.sub.5)(R.sub.16)(R.sub.17), not simultaneously hydrogen,

(40) the D is selected from oxygen, (C1-C20) alkylene, (C2-C20) alkenylene, (C3-C20) cycloalkylene, and (C6-C20) arylene,

(41) the R.sub.15 to R.sub.17 are each independently selected from hydrogen, (C1-C10) alkyl, (C2-C20) alkenyl, (C3-C20) cycloalkyl, (C6-C20) aryl, (C3-C20) heterocycloalkyl, (C4-C20) heteroaryl, OR.sub.19, N(R.sub.20)(R.sub.21), and P(R.sub.22)(R.sub.23)(R.sub.24),

(42) the R.sub.9 to R.sub.14, and R.sub.19 to R.sub.24 are each independently hydrogen or (C1-C5) alkyl, and

(43) the alkyl, alkylene, alkenylene, cycloalkylene, and arylene are substitutable with at least one selected from (C1-C7) alkyl, halogen, nitro, cyano, hydroxy, amino, (C6-C20) aryl, (C2-C7) alkenyl, and (C3-C20) cycloalkyl.

(44) More specifically, the dihydrosilane compound according to an embodiment of the present invention may be

(45) ##STR00011##
but not limited thereto.

(46) According to an embodiment of the present invention, the contents of the divinyl compound and the dihydrosilane compound are not limited, but the molar ratio of the unsaturated group of the divinyl compound to the SiH group of the dihydrosilane compound is preferably 40:60 to 60:40 to be mixed, and more preferably, when the molar ratio of the unsaturated group of the divinyl compound and the SiH group of the dihydrosilane compound is 45:55 to 55: 45 to be mixed, it is possible to form a uniform silicon polymer network structure, and therefore, it is effective.

(47) According to an embodiment of the present invention, the compound represented by Chemical Formula 4 may be further included.

(48) ##STR00012##

(49) (in Chemical Formula 4 above, X is Si(R.sub.51)(R.sub.52), the m is an integer selected from 0 to 100,

(50) the R.sub.41 to R.sub.43 and R.sub.51 to R.sub.52 are each independently selected from hydrogen, (C1-C10) alkyl, (C2-C20) alkenyl, (C3-C20) cycloalkyl, (C6-C20) aryl, (C3-C20) heterocycloalkyl, (C4-C20) heteroaryl, OR.sub.61, N(R.sub.62)(R.sub.63), and P(R.sub.64)(R.sub.65)(R.sub.66), not simultaneously hydrogen,

(51) the R.sub.61 to R.sub.66 are each independently hydrogen or (C1-C10) alkyl,

(52) the C is selected from a chemical bond, oxygen, sulfur, (C1-C20) alkylene, (C2-C20) alkenylene, (C3-C20) cycloalkylene, (C6-C20) arylene, (C3-C20) heterocycloalkylene, and (C4-C20) heteroarylene, and

(53) the alkyl, alkylene, alkenylene, cycloalkylene, and arylene are substitutable with at least one selected from (C1-C7) alkyl, halogen, nitro, cyano, hydroxy, amino, (C6-C20) aryl, (C2-C7) alkenyl, and (C3-C20) cycloalkyl).

(54) In order to obtain a polymer having a high molecular weight by conventional step growth polymerization, it is crucial to introduce two monomers such that each reaction group in the two monomers has a molar ratio of 1:1. When compounds satisfying Chemical Formula 4 above are used, it is possible to always maintain the molar ratio between the reaction groups to be 1:1 because the two reaction groups are simultaneously included in one molecule. Therefore, it is more advantageous to obtain a resultant with a high molecular weight.

(55) The organoboron catalyst according to an embodiment of the present invention can replace conventional platinum group metal-containing catalysts by catalyzing a hydrosilylation reaction.

(56) Platinum group metal catalysts including ruthenium, rhodium, palladium, osmium, iridium, and platinum, which promote the conventional hydrosilylation reaction, are expensive and remain in the resin after polymerization. Therefore, there are problems such as elution of heavy metal, etc. depending on the applied products in order to conduct studies to solve these problems, by applying an organoboron catalyst, economic feasibility is improved compared to platinum group metal catalysts, and by preventing residual heavy metal and improving the yield of hydrosilylation reaction, it was found that the reactivity was also excellent.

(57) The organoboron catalyst according to an embodiment of the present invention can be represented by Chemical Formula 5, but not limited thereto.

(58) ##STR00013##

(59) (in Chemical Formula 5 above, R.sub.30 and R.sub.31 are selected from halogen, (C1-C10) alkyl, (C3-C10) cycloalkyl, and (C6-C10) aryl,

(60) the R.sub.32 is each independently selected from hydrogen, halogen, (C1-C10) alkyl, and (C6-C10) aryl,

(61) the alkyl, cycloalkyl, and aryl are substitutable with any one selected from (C1-C7) alkyl or halogen, and the n is an integer selected from 0 to 5, not simultaneously 0).

(62) The organoboron catalyst according to an embodiment of the present invention can be represented by Chemical Formula 6, but not limited thereto.

(63) ##STR00014##

(64) (in Chemical Formula 6, R.sub.30 is selected from halogen, (C1-C10) alkyl, (C3-C10) cycloalkyl, and (C6-C10) aryl,

(65) the R.sub.32 and R.sub.331 are each independently selected from hydrogen, halogen, (C1-C10) alkyl, and (C6-C10) aryl, and

(66) the alkyl, cycloalkyl, and aryl are substitutable with at least one selected from (C1-C7) alkyl or halogen, and the n is an integer selected from 0 to 5, not simultaneously 0).

(67) According to an embodiment of the present invention, the organoboron catalyst can be represented by Chemical Formula 7, but not limited thereto.

(68) ##STR00015##

(69) (in Chemical Formula 7 above, the R.sub.32, R.sub.330, and R.sub.331 are each independently selected from among hydrogen, halogen, (C1-C10) alkyl, and (C6-C10) aryl,

(70) the alkyl, cycloalkyl, and aryl are substitutable with any one selected from (C1-C7) alkyl or halogen, and the n is an integer selected from 0 to 5, not simultaneously 0).

(71) More specifically, the organoboron catalyst can be selected from the compounds disclosed below, but not limited thereto.

(72) ##STR00016## ##STR00017##

(73) By including such an organic boron catalyst, it is possible to improve the economic efficiency and the heavy metal residue accompanying reduction of the raw material cost as compared with the case of using the existing platinum group metal catalyst, and at the same time, and the reactivity can be remarkably improved.

(74) The amount of the organoboron catalyst according to an embodiment of the present invention is not limited as long as it can accelerate hydrosilylation. For example, the amount of the organoboron catalyst can be 0.01 to 10 mol % based on the amount of the divinyl compound, and preferably, be 0.1 to 5 mol %, and more preferably, 1 to 5 mol %. When the organoboron catalyst is included in the amount described above, it is effective because the reactivity of hydrosilylation and the reaction yield thereof can be significantly improved.

(75) When the amount of the organoboron catalyst is below 0.01 mol %, hydrosilylation is not sufficiently accelerated so that the mechanical property and molecular weight of silicon polymers may be reduced, and when the amount thereof is above 10 mol %, the reactivity and the improvement of the yield are no longer enhanced, thereby causing a problem of an increase in unnecessary costs.

(76) According to an embodiment of the present invention, the environmentally friendly silicon polymer can be prepared by reacting a catalyst solution including the organoboron catalyst and a mixture of the dihydrosilane compound, and the divinyl compound. The reaction temperature and reaction time can be selected within a range where hydrosilylation is accelerated and the properties of the prepared environmentally friendly silicon polymer are not deteriorated. For example, the polymer can be prepared by reacting at 20 to 40 C. for 12 to 48 hours, and more preferably, at 25 to 35 C. for 20 to 30 hours, but not limited thereto.

(77) The catalyst solution can be prepared by mixing an organoboron catalyst and an organic solvent to improve reactivity and reaction yield. The organic solvent is not limited as long as the solvent is publicly disclosed, and for example, it can include chlorinated hydrocarbons, esters, ketones, alcohol aliphatic hydrocarbons, and aromatic hydrocarbons, but not limited thereto. The organic solvent can be more preferably chlorinated carbon, and specifically, methyl chloride, methylene chloride, and chloroform, as an example. Among these, using chloroform is most effective, but the present invention is not limited thereto.

(78) According to another embodiment of the present invention, the present invention can provide an environmentally friendly silicon polymer prepared according to the preparation method of the environmentally friendly silicon polymer described above.

(79) More specifically, the preparation method of the environmentally friendly silicon polymer according to an embodiment of the present invention does not include a platinum group catalyst, and the number average molecular weight can be, for example, 500 to 1,000,000 g/mol, but not limited thereto.

(80) The environmentally friendly silicon polymer according to an embodiment of the present invention can further include an additive selected from the group consisting of an antimicrobial agent, a heat stabilizer, an antioxidant, a release agent, a photostabilizer, an inorganic additive, a surfactant, a coupling agent, a plasticizer, a compatibilizer, a lubricant, an antistatic agent, a colorant, a pigment, a dye, a flame retardant, a flame resistant, an anti-drop agent, a weatherproof agent, an ultraviolet ray absorbent, an ultraviolent ray blocker, and a mixture thereof.

(81) For the environmentally friendly silicon polymer prepared according to the preparation method above, the types of the divinyl compound and the dihydrosilane compound can be changed according to the intended use, and accordingly, the molecular weight and chemical structure can be determined.

(82) For example, the environmentally friendly silicon polymer as shown in Chemical Formula 8 below can be provided by applying the divinyl compound, the dihydrosilane compound, and the organoboron catalyst according to an embodiment of the present invention.

(83) ##STR00018##

(84) in Chemical Formula 8 above, o can be selected from 10 to 1,000).

(85) The environmentally friendly silicon polymer prepared according to the preparation method of the present invention has a number average molecular weight of, for example, 5,000 to 200,000 g/mol, and more preferably, 10,000 to 100,000 g/mol, but not limited thereto.

(86) The environmentally friendly silicon polymer thus prepared has a high yield for hydrosilylation, excellent reactivity, and there is an advantage in that an environmentally friendly silicon polymer can be prepared. In addition, since heating is not necessary, there is an advantage in that the production costs and energy costs related thereto can be reduced. Due to the effects described above, there is an advantage in that the environmentally friendly silicon polymer according to the present invention can be widely applied in various technological fields such as sealants, adhesives, silicone-based coating products, etc.

(87) Hereinafter, the present invention will be described in more detail with reference to the following examples. However, the present invention is not limited to the following examples.

EXAMPLE 1

(88) As shown in Table 1 below, under the nitrogen atmosphere, the dihydrosilane compound

(89) ##STR00019##
and the divinyl compound

(90) ##STR00020##
were sequentially inserted into a mixture solution of the organoboron catalyst (B(C.sub.6F.sub.5).sub.3, 5 mol %, 0.05 mmol) and 0.4 mL of an organic solvent (chloroform). Afterwards, the mixture was stirred at room temperature for 24 hours and reacted. At the completion of the reaction, 10 mL of methanol was added to separate the formed precipitate, and the separated precipitate was dissolved in 3 mL of chloroform, then 10 mL of methanol was added to perform reprecipitation twice, in order to prepare 190 mg (reaction yield: 54%) of the final product. The number average molecular weight of the final product was measured using gel permeation chromatography (GPC) using a reference material for polystyrene, and the result thereof is shown in Table 1 below. In addition, the structure thereof was analyzed using .sup.1H NMR, .sup.13C NMR, and FT-IR, and each measurement result was shown in FIGS. 1 to 3.

EXAMPLES 2-4

(91) As shown in Table 1 below, the final product was prepared in the same manner as in Example 1, except that the amount of the organoboron catalyst was changed. The physical properties of the final product were measured and shown in Table 1 below.

EXAMPLES 5-8

(92) As shown in Table 1 below, the final product was prepared in the same manner as in Example 1, except that the amount of the dihydrosilane product was changed. The physical properties of the final product were measured and shown in Table 1 below.

COMPARATIVE EXAMPLE 1

(93) As shown in Table 1 below, the final product was prepared in the same manner as in Example 1, except that a platinum group metal catalyst (Karstedt's catalyst, Platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane). The physical properties of the final product were measured and shown in Table 1 below.

COMPARATIVE EXAMPLE 2

(94) As shown in Table 1 below, the final product was prepared in the same manner as in Example 1, except that a platinum group metal catalyst (Speier's catalyst, chloroplatinic acid hydrate). The physical properties of the final product were measured and shown in Table 1 below.

(95) TABLE-US-00001 TABLE 1 Platinum Divinyl Dihydrosilane Organoboron group metal Reaction Reaction Number average Molecular compound compound catalyst catalyst hour yield molecular weight weight (mmol0 (mmol) (mol %) (mol %) (hr) (%) (Mn) distribution Example 1 1.0 1.0 5 0 24 54 14,100 1.90 Example 2 1.0 1.0 1 0 24 54 11,700 2.00 Example 3 1.0 1.0 3 0 24 54 13,400 2.01 Example 4 1.0 1.0 10 0 24 50 14,100 1.88 Example 5 1.0 0.9 5 0 24 28 7,500 1.88 Example 6 1.0 0.98 5 0 24 49 13,300 1.89 Example 7 1.0 1.05 5 0 24 54 8,900 1.77 Example 8 1.0 1.1 5 0 24 49 6,400 1.61 Comparative 1.0 1.0 0 5 24 <5 <500 Example 1 Comparative 1.0 1.0 0 5 24 <5 <500 Example 2

(96) Although the preferred embodiments of the present invention have been described above, it is apparent that the present invention can use various changes and equivalents, and that the embodiments can be appropriately modified and applied in a similar manner. Accordingly, the above description does not limit the scope of the present invention, which is determined by the limitations of the following claims.