WO1991015536A1 - Polymere d'oxypropylene contenant un groupe de silicium reactif et production de ce polymere - Google Patents

Polymere d'oxypropylene contenant un groupe de silicium reactif et production de ce polymere Download PDF

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Publication number
WO1991015536A1
WO1991015536A1 PCT/JP1991/000461 JP9100461W WO9115536A1 WO 1991015536 A1 WO1991015536 A1 WO 1991015536A1 JP 9100461 W JP9100461 W JP 9100461W WO 9115536 A1 WO9115536 A1 WO 9115536A1
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WIPO (PCT)
Prior art keywords
group
polymer
reactive silicon
molecular weight
reactive
Prior art date
Application number
PCT/JP1991/000461
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English (en)
Japanese (ja)
Inventor
Masayuki Fujita
Michihide Homma
Hiroshi Wakabayashi
Original Assignee
Kanegafuchi Chemical Industry Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Kanegafuchi Chemical Industry Co., Ltd. filed Critical Kanegafuchi Chemical Industry Co., Ltd.
Priority to AU75756/91A priority Critical patent/AU650872B2/en
Priority to CA002056363A priority patent/CA2056363C/fr
Publication of WO1991015536A1 publication Critical patent/WO1991015536A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
    • C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon

Definitions

  • the present invention relates to a novel oxypropylene polymer containing a reactive silicon group and a method for producing the same.
  • polyoxypropylene which has a narrow molecular weight distribution (high monodispersity), and thus has a high reactivity.
  • Polyoxypropylene containing a basic group has not been known as a polymer having a wide molecular weight distribution (high polydispersity).
  • polyoxypropylene having a narrow molecular weight distribution can be obtained.
  • the present inventors have found that a polymer having a narrow chain of polyoxypropylen as a main chain and having a reactive gayene group and a urethane bond introduced at its terminal is cured. Before you The present invention was found to be low in viscosity and easy to handle, and that the cured product after curing had not only excellent tensile properties, but also chemical resistance and water spraying properties.
  • the reactive siloxane-containing oxypropylene polymer of the present invention essentially has a polymerizable polymer.
  • the production method of the present invention can be used with MwZMnforce ⁇ 1.5 or less.
  • the reactive gating group according to the present invention is not particularly limited, but typical examples thereof include those represented by the following general formula: The group represented by (1) is mentioned.
  • R 2 a are both ⁇ Ruki Le group having from 1 to 2 0 carbon atoms, the number of al-2 0 of ⁇ Li Lumpur based on carbon, the number of carbon atoms? ⁇ 2 0 ⁇ La alkyl group or a (R ') 3 S i O - shows the door the Rio Ruga Bruno filtered off key sheet group is Ru are shown in, were R 1 or R 2 is 2 or more When they are present, they can be the same or different.
  • R ' is a monovalent hydrocarbon group having 1 to 20 carbon atoms, and the three R's may be the same or different.
  • X represents a hydroxyl group or a hydrolyzable group, and when two or more Xs are present, they may be the same or different.
  • a indicates 0, 1, 2 or 3
  • b indicates 0, 1 or 2.
  • the b in X b may be different.
  • m represents 0 or an integer of 1 to 19.
  • a + ⁇ b1 shall be added.
  • the hydrolyzable group represented by X is not particularly limited, and may be any conventionally known hydrolyzable group. Specifically, it is known that a hydrogen atom, a halogen atom, an alkoxy group, an acyloxy group, a ketoxime group, an amino group, an amide group, Acid amide groups, aminooxy groups, menolecapto groups, alkenyloxy groups, and the like. Among these, a hydrogen atom, an alkoxy group, an acyloxy group, a ketoxime group, an amino group, an amide group, and an aminooxy group are included. Groups, a mercapto group and an alkenoxy group are preferred, but an alkoxy group is particularly preferred from the viewpoint of mild hydrolyzability and easy handling.
  • This hydrolyzable group or hydroxyl group can be bonded to one to three silicon atoms, and (a + ⁇ b) is preferably 1 to 5.
  • two or more hydrolyzable groups or hydroxyl groups are present in the reactive silicon group, they may be the same or different.
  • the reactive silicon group may have one or more than two silicon atoms, but the connection of the silicon atoms by siloxane coupling or the like. In the case of the provided reactive silicon group, about 20 groups are preferable.
  • a reactive silicon group represented by the following general formula (2) is preferable from the viewpoint of easy availability.
  • R 1 and R 2 in the general formula (1) include, for example, alkyl groups such as a methyl group and an ethyl group, and cycloalkyl groups.
  • Cycloalkyl groups such as xyl groups, aryl groups such as phenyl groups, aralkyl groups such as benzyl groups, R'methylol groups and phenyl groups
  • a methyl group is particularly preferred.
  • At least one, preferably 1.1 to 5 reactive silicon groups be present in one molecule of the oxypropylene polymer. If the number of reactive silicon groups contained in is less than one, the curability becomes insufficient and good rubber elasticity behavior is hardly exhibited.
  • the reactive silicon group is present at the terminal of the molecular chain, the effectiveness of the oxyprovirene polymer component contained in the finally formed cured product can be improved.
  • the increased number of mesh chains makes it easier to obtain a rubber-like cured product that exhibits high strength and high elongation (low elastic modulus).
  • the urethane bond in the present invention is a bond represented by one NHCOO—.
  • the oxyprovirene polymer constituting the polymer main chain in the polymer of the present invention is essentially
  • This phone One It consists of the return unit indicated by. This phone One —
  • the propylene polymer may be in the form of a straight line, in the form of a branch, or in a mixture thereof. Further, a small amount of other monomer units may be contained.
  • the number average molecular weight of this oxypropylene polymer one having a molecular weight of 3,000 or more can be effectively used, but preferably, the one having a linear shape is preferred.
  • the polymer having a molecular weight of 3,000 or more and the branched one is preferably 5,000 or more. More preferably, it has a number average molecular weight of 6,000 to 30,000.
  • the ratio of heavy S-average molecular weight to number-average molecular weight ( ⁇ iw ZM n) of this oxypropylene polymer is not more than 1.5, and the molecular weight distribution is extremely narrow. (Large monodispersity).
  • the value of i3 ⁇ 4wZMn is preferably less than or equal to 1.4, more preferably less than or equal to 1.3.
  • the molecular weight distribution can be measured by various methods, it is generally measured by a gel permeation chromatography (GPC) method. As described above, although the number average molecular weight is large, the molecule; a, the distribution of which is narrow, so that the polymer of the present invention has low viscosity before curing and is easy to handle, and after curing, Shows good rubber-like elastic behavior.
  • the cured product after curing has excellent strength and elongation.
  • an oxoprovirene polymer having a functional group such as a hydroxyl group at its terminal (hereinafter referred to as Y functional group) is used.
  • the propylene polymer may be reacted with a compound having an isocyanate group and a reactive silicon group that are reactive to the Y functional group. .
  • M w ZM n is 1.5 Ru
  • Mototo Ri having a number average molecular, 5 0 0 or der Ru O key sheet profile pin les down polymer 0
  • compounds having an isocyanate group and a reactive silicon group include, but are not limited to, an isocyanate-propynolate triethoxysilane. , Key-isolated-protocol-measurement xylan, key-isolated-prototype-measurement xylan, etc.
  • silane-containing silanes are not limited to these powerful and specific examples.
  • an oxypropylene copolymer having a Y functional group at the terminal is reacted with a compound having an isocyanate group and a reactive silicon group.
  • a reactive gay group can be introduced in one step without going through a complicated reaction step as in the prior art.
  • the reactive oxypropylene polymer containing a reactive silicon group of the present invention forms a three-dimensional network by exposure to the air, and is a rubber It hardens to an elastic solid.
  • a silane condensation catalyst (curing catalyst) may or may not be used.
  • a silane condensation catalyst those conventionally known can be widely used. Specific examples thereof include titanic acid esters such as tetrabutyl titanate, tetrabutyl titanate, etc .; Suzukanolevo, such as Laurate, Djibutinoles Maleate, Djibutinoresuzujiacetate, Succinooctylate, and Naphthenate Reaction products of dibutyl sulphoxide and diester phthalate; dibutyl sul diacetyl acetonate; aluminum Tri-Secire Nore Settlement, Anominator Trim Settlement Attached Jig Soproxy Numoret Minimati Seta Organic aluminum compounds such as thiocyanate; zirconium tetracetinoacetyl acetate; titantra acetic acid acetate; Chelate compounds such as; lead
  • the amount of the silane condensation catalyst used is preferably about 0.1 to 20 parts by weight based on 100 parts by weight of the oxypropylene polymer. About 10 parts by weight is more preferable.
  • the amount of the silane-condensation catalyst used is too small relative to the propylene polymer, the curing speed becomes slow; and the curing reaction does not proceed sufficiently. Is not preferred.
  • the amount of the silane-condensation catalyst used is too large relative to the oxipone pyrene polymer, local heat generation and foaming occur during curing, and a good cured product is obtained. I don't like it because it makes it difficult to obtain.
  • the reactive silicon group-containing oxyprovirene polymer of the present invention can be modified by incorporating various fillers.
  • fillers fumescent silica, settling silica, reinforcing fillers such as anhydrous ganoic acid, hydrous ganoic acid and carbon black; carbonic acid Calcium, magnesium carbonate, silicate clay, calcined clay, clay, talc, titanium oxide, bentonite, organic bentonite Fillers such as it, ferric oxide, zinc oxide, active zinc white and silica balloon; fibrous materials such as asbestos, glass male fibers and filaments Fillers can be used.
  • a filler selected from the group consisting of iron oxide, ferric oxide, zinc oxide, and silica balun is added to 100 parts by weight of the reactive silicon-containing oxypropylene polymer. Good results are obtained when used in the range of 5 to 200 parts by weight. . Of course, these fillers may be used alone or in combination of two or more.
  • the reactive gypsum group-containing oxyprovirene polymer of the present invention when used in combination with a filler, the elongation of the cured product is greatly increased. It is more effective because it can mix a large amount of filler.
  • This plasticizer is one that is commonly used.
  • esters of phthalanolic acid such as dioctyl phthalate, dibutynophthalate, butynol benzyl phthalate; adivin Aliphatic dibasic acid esters such as dioctynoleic acid, kono, isodecyl citrate and dibutyl sebacate; diethyl glycol Benzoates, pentaerythritol, and other polyesters, such as glycol esters; butyric acid oleate, acetyl acetylene resin Aliphatic esters such as methyl phosphate; triglyceryl phosphate, trioctyl phosphate, octyl diphenyl phosphate, etc.
  • Esters of phosphoric acid such as epoxidized soybean oil, and epoxies, such as epoxidized stearate benzyl.
  • Plasticizers such as polyesters of dibasic acid and divalent alcohol; Polypropylene glycols and the like.
  • Polystyrenes such as derivatives of polystyrene; poly ⁇ -methylstyrenes, polystyrenes such as polystyrenes; polybutadienes, butylenes Tadiene acrylonitrile copolymer, polyclonal plate, polyisoprene, polybutene, chlorinated paraffin, etc.
  • the plasticizer can be optionally used alone or in the form of a mixture of two or more.
  • the plasticizer S in an amount of 0 to 100 parts by weight based on 100 parts by weight of the reactive propylene group-containing oxypropylene polymer. Is obtained.
  • a phenol resin and an epoxy resin may be further used.
  • a room temperature curable composition can be obtained by appropriately adding various additives such as a system-based radical chain inhibitor, a phosphorus-based peroxide decomposer, a lubricant, and a pigment foaming agent.
  • a polycarbonate with a number average molecular weight of 15,500 was added to a flask with a stirrer (wZKin-1.38, viscosity 89%). 2) 0: (0.0447 equivalents) and 0.02 g of dibutyltin dilaurate were charged, and the solution was dissolved under nitrogen atmosphere. 8.45 g (0.0444 equivalents) of propylmethyldimethoxysilane was added dropwise at room temperature. After the completion of the dropwise addition, the mixture was reacted at 75 ° C for 1.5 hours. After measuring the IR spectrum and confirming the disappearance of the NCO absorption near 2280 cm "" 1 and the generation of C »0 absorption near 1730 cm— 1 , the reaction was terminated. Was. 213 g of a colorless and transparent polymer were obtained.
  • Polyoxypropylene glycol with a number average molecular weight of 3,000 0 4 0 g and a polyoxypropylene propylene with a number average molecular weight of 3,000 80 g of the triol was charged into a pressure-resistant glass reaction vessel in which nitrogen was replaced. After adding sodium hydroxide (40 s), the mixture was reacted at 60 for 13 hours, and then, the reaction of bromochlormethane 1 was performed at 60 for 10 hours. (The obtained polymer had an iw ZKin of 2.1 and a viscosity of 38.5 voices.) Then, 5 g of L: L was added, and the reaction was carried out for 36 hours. After the completion of the reaction, the pressure was reduced to remove the volatile substances.
  • the contents were taken out into a beaker and dissolved in hexane. After adsorption treatment with aluminum gaymate, the hexane was depressurized and removed.
  • This port Li Ma -5 0 0 8 only charged to a reaction vessel which is nitrogen S conversion, catalyst solution (H 2 P t CQ 6 ⁇ 6 H 2 0 2 5 g of Lee Seo-flop of chloroplatinic acid b After adding 0.03 g, add 12 g of dimethoxymethane, add 12 g of dimethoxymethane, and incubate at 80 for 4 hours. Reacted. After completion of the reaction, the pressure was reduced and the volatile substances were removed to obtain 550 g of a pale yellow transparent polymer.
  • Example 1 and Comparative Examples 1 and 2 were measured using a B-type viscometer (BM type rotor No. 4, 12 rpm). Measured in 23.
  • Mn number average molecular weight
  • MwZn molecular weight distribution
  • GPC uses tetrahydrofuran as a distilling solvent for a column filled with polystyrene gel (manufactured by Tosoh Ichi Co., Ltd.), and prepares an open plate. The analysis was performed at a temperature of 40 ° C. Table 11 shows the results. 4 one
  • Example 1 To 100 parts by weight of the polymer obtained in Example 1 or Comparative Example 1, 3 parts by weight of octyl acid, 0.5 part by weight of raurilamin, and water 0.6 parts by weight were kneaded, stretched in a sheet form, and then cured at room temperature for 2 days and further at 50 at 3 days.
  • the sheet strength of the cured product was punched out from a JIS No. 3 dumbbell based on JISK 6301 and a tensile test was performed to determine the strength at break (TB) and elongation at break (EB ) Are shown in Table 1-2. 5 one
  • Ebicoat 828 (a bisulfate-based epoxy resin bismuth). 50 parts by weight, Nocrack SP (Monofunol antiaging agent manufactured by Ouchi Shinko Chemical Co., Ltd.) 1 part by weight, 2, 4, 6-tris (dimethylaluminum) phenol (DMP-30) 5 parts by weight, N- ⁇
  • a No. 3 dumbbell was punched out in accordance with the sheet force of the cured product and JJIS 6301, and a tensile test was performed at a tensile speed of 500 minutes. Table 1 shows the results.
  • M 100 is the stress at 100% elongation
  • ⁇ ⁇ is the fracture.
  • Shear strength, EB indicates elongation at break
  • the reactive oxy-propylene polymer containing a reactive silicon group of the present invention has a high molecular weight even though its molecular weight is large. Since the molecular S distribution is narrow, before curing, compared to a conventional polymer having the same molecular S and a wide molecular weight distribution, the viscosity is lower and the handling is valley ⁇ 7C.
  • the polymer of the present invention has a urethane bond at a terminal, a cured product after curing has excellent strength and elongation.
  • the reactive silicon group-containing oxyprovirene polymer of the present invention has extremely high practical value.
  • the production method of the present invention is an excellent method that can introduce a reactive silicon group in one step without having a complicated reaction step as in the prior art. It is.
  • the composition containing the reactive silicon-containing oxyprovirene polymer of the present invention is particularly useful as an elastic sealant, and can be used for buildings, ships, automobiles, roads, and the like. Which sealant to use. In addition, it can adhere to a wide range of substrates, such as glass, porcelain, wood, metal, and resin moldings, alone or with the help of the primer, so that various types of substrates can be used. It can also be used as a sealing composition and an adhesive composition. Furthermore, it is also useful as a food packaging material, a casting rubber material, and a molding material.

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Silicon Polymers (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyethers (AREA)

Abstract

L'invention se rapporte à un nouveau polymère d'oxypropylène contenant un groupe de silicium réactif, dans lequel la chaîne polymère principale contient essentiellement les unités répétitives de la formule (α), dans lequel au moins un groupe de silicium réactif et au moins une liaison d'uréthane sont présents aux terminaisons de la chaîne polymère et dans lequel le rapport M^¨B7w/M^¨B7n est égal à 1,5 ou moins, et le poids moléculaire moyen en nombre est égal à 3 000 ou plus. Le procédé de production de ce polymère consiste à faire réagir un polymère d'oxypropylène, ayant un rapport M^¨B7w/M^¨B7n égal à 1,5 ou moins et un poids moléculaire moyen en nombre par unité de fonction terminale égal à 1 500 ou plus avec un composé contenant à la fois un groupe de silicium réactif et un groupe d'isocyanate.
PCT/JP1991/000461 1990-04-09 1991-04-08 Polymere d'oxypropylene contenant un groupe de silicium reactif et production de ce polymere WO1991015536A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU75756/91A AU650872B2 (en) 1990-04-09 1991-04-08 Oxypropylene polymer containing reactive silicon group and production thereof
CA002056363A CA2056363C (fr) 1990-04-09 1991-04-08 Polymere d'oxypropylene renfermant un groupe silicie reactif; methode de preparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2/94543 1990-04-09
JP9454390 1990-04-09

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US33897994A Continuation 1990-04-09 1994-11-14

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5286780A (en) * 1991-09-09 1994-02-15 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Curable composition
EP0671437A1 (fr) * 1994-03-07 1995-09-13 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Composition de résine durcissable

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0910361A2 (pt) * 2008-07-16 2015-10-06 Dow Global Technologies Inc composto de polialquileno glicol terminado por silila, método para preparar um composto de polialquileno glicol terminado por silila e composição refrigerante

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6118582B2 (fr) * 1975-12-16 1986-05-13 Kanegafuchi Chemical Ind
JPS61141761A (ja) * 1984-12-12 1986-06-28 Kanegafuchi Chem Ind Co Ltd 硬化性組成物
JPS61197631A (ja) * 1985-02-28 1986-09-01 Kanegafuchi Chem Ind Co Ltd 分子量分布の狭いポリアルキレンオキシドの製造方法

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2610305B2 (ja) * 1988-06-10 1997-05-14 鐘淵化学工業株式会社 硬化性組成物
CA2051702C (fr) * 1990-03-09 1999-06-15 Masayuki Fujita Composition durcissable

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6118582B2 (fr) * 1975-12-16 1986-05-13 Kanegafuchi Chemical Ind
JPS61141761A (ja) * 1984-12-12 1986-06-28 Kanegafuchi Chem Ind Co Ltd 硬化性組成物
JPS61197631A (ja) * 1985-02-28 1986-09-01 Kanegafuchi Chem Ind Co Ltd 分子量分布の狭いポリアルキレンオキシドの製造方法

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5286780A (en) * 1991-09-09 1994-02-15 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Curable composition
EP0671437A1 (fr) * 1994-03-07 1995-09-13 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Composition de résine durcissable
US5684094A (en) * 1994-03-07 1997-11-04 Kanegafuchi Kagaku Kogyo Kabushiki Kaisha Curable resin composition

Also Published As

Publication number Publication date
AU7575691A (en) 1991-10-30
CA2056363C (fr) 1999-06-01
AU650872B2 (en) 1994-07-07
CA2056363A1 (fr) 1991-10-10

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