CN1100838C - Organosilicon modified polyurethane paint - Google Patents
Organosilicon modified polyurethane paint Download PDFInfo
- Publication number
- CN1100838C CN1100838C CN99102825A CN99102825A CN1100838C CN 1100838 C CN1100838 C CN 1100838C CN 99102825 A CN99102825 A CN 99102825A CN 99102825 A CN99102825 A CN 99102825A CN 1100838 C CN1100838 C CN 1100838C
- Authority
- CN
- China
- Prior art keywords
- siloxane
- composition
- polyurethane prepolymer
- hydrogen
- polyurethane
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
Abstract
The present invention relates to organosilicon modified polyurethane paint which is composed of a polyurethane prepolymer, ammonia alkylsilane or siloxane, organopolysiloxane adhesion promoter, siloxane with hydrogen, organic solvent, etc. The paint can be solidified into a film at 150 to 200 DEG C under the existence of a chloroplatinic acid catalyst, and a solidified coating film has the advantages of smoothness, and heat and wear resistance, and has fine attaching performance to silicon rubber of which the surface is not processed.
Description
The invention relates to an organic silicon modified polyurethane coating.
Polyurethane coatings have good overall properties and excellent adhesion to many substrates but do not adhere to silicone rubbers having low surface free energy, and patent documents JP0853607 and u.s.5677007 have reported that polyurethane is used as a coating for silicone rubber keys, but the silicone rubber surface must be treated with plasma or ultraviolet light irradiation before coating and then primed with silane coupling agents such as KBP40 and KBM403 to obtain good adhesion. German patent DE19539653 reports a reactive polyurethane tackifier suitable for the adhesion of silicone rubber to plastics, mainly as a dental prosthesis and a surgical implant sealant.
The invention aims to realize that the amino alkyl silane or siloxane is used as a modifier of polyurethane, and the vinyl-containing organopolysiloxane tackifier is added to prepare the organic silicon modified polyurethane coating, which can generate a crosslinking reaction with the hydrogen-containing siloxane in the presence of a chloroplatinic acid catalyst and is cured to form a film. The coating after film formation has good adhesion to silicone rubber without any surface treatment.
In order to realize the purpose of the invention, the invention adopts the following technical scheme: the organic silicon modified polyurethane coating composition comprises: (A) the polyurethane prepolymer, (B) amino alkyl silane or siloxane, (C) organopolysiloxane tackifier, (D) hydrogen-containing siloxane, (E) organic solvent, and (F) chloroplatinic acid catalyst, wherein the weight parts of (A), (B), (C) and (D) are as follows: (A) 1 part of a copolymer consisting of (A) and (B), and the A/B weight ratio is from 2.1 to 5.6/1; (C)0.5 part; (D)0 to 0.1 portion of (A) + (B) + (C) + (D) accounting for 10 to 30 weight percent of the total weight; (E) accounts for 70-90 wt% of the total amount, and the amount of (F) used is 2-100ppm (calculated as platinum).
In the composition, the polyurethane prepolymer is prepared by reacting polyether polyol or polyester polyol, diisocyanate, a chain extender-low molecular weight diol at the temperature of 40-80 ℃, phosphoric acid is used as a polymerization inhibitor, dibutyltin dilaurate is used as a catalyst, and a mixed solvent consisting of toluene, butanone and cyclohexanone is used as a diluent.
In the composition, the amino alkyl silane or siloxane is used as a modifier of polyurethane, and the reaction of the amino alkyl silane or siloxane and a polyurethane prepolymer is carried out at the temperature of 20-40 ℃ to generate a silicon-containing substituentOrThe copolymer of (1); wherein n is more than 10.
In the composition of the invention, the organopolysiloxane tackifier is polysiloxane containing vinyl, and can generate crosslinking reaction with hydrogen-containing siloxane in the presence of chloroplatinic acid catalyst.
In the composition of the present invention, the hydrogen-containing siloxane refers to a siloxane oligomer having Si-H bonds.
In the composition of the present invention, the organic solvent is a mixed solvent composed of toluene, butanone and cyclohexanone.
In the composition, the organosilicon modified polyurethane coating has good heat resistance and can be baked and cured at the temperature of 150-200 ℃, and the formed coating has firm bonding force and good wear resistance to silicon rubber.
The present invention will be described in detail below.
The organic silicon modified polyurethane coating comprises (A) polyurethane prepolymer, (B) amino alkyl silane or siloxane, (C) organic polysiloxane tackifier, (D) hydrogen-containing siloxane, (E) organic solvent, (F) chloroplatinic acid catalyst and the like. The organic silicon modified polyurethane coating can be baked at the temperature of 150-200 ℃ for 10-30 minutes to be cured into a film, and has good adhesive force on the surface of a silicon rubber product. The cured coating is smooth, heat-resistant and wear-resistant, and when the silicon rubber product is stretched or compressed, the coating does not crack or wrinkle. (A) The polyurethane prepolymer is composed of the following materials:
(1) polyether polyols and/or polyester polyols
Polyether polyols such as: polypropylene oxide glycol
Polyethylene oxide glycol
THF-homopolyether glycols
Polyethylene oxide propylene oxide copolyether glycol
And trihydroxy polyetherAnd tetrahydroxy polyethers
Polyester polyols such as: polyethylene glycol adipate glycolPolyethylene glycol propylene glycol adipate glycol
Poly (1, 4-butylene adipate) glycol
Castor oilPoly-caprolactone diolAnd the like. (2) Polyisocyanate toluene diisocyanate
(2, 4-body) or(2, 6-isomer) 4, 4-diphenylmethane diisocyanate
Or
(isomers) 1, 3-diisocyanatesHexamethylene diisocyanate
Polyphenyl polyisocyanatesAnd (3) chain extender glycol-based chain extenders such as: ethylene glycol HO- (CH)2)2-OH propylene glycol
1, 4-butanediol HO- (CH)2)4-OH hexanediol HO- (CH)2)6-OH
Diethylene glycol HO- (CH)2)2-O-(CH2)2OH and the like
Diamine chain extenders such as: ethylene diamine H2N-(CH2)2-NH2
4.4-methylene-bis (o-chloroaniline)
1, 4-diaminobutane H2N-(CH2)4-NH2
1, 6-diaminohexane H2N-(CH2)6-NH2Etc. of
(B) Aminoalkyl silanes or siloxanes are a class of organosilicon compounds which react with the isocyanate in the polyurethane prepolymer such as:
aminopropyltrimethoxysilane H2N-(CH2)3Si(OCH3)5、
Aminopropyltriethoxysilane H2N(CH2)3Si(OC2H5)3、
Aminopropylmethyldimethoxysilane H2N(CH2)3Si(CH3)(OCH3)2、
Aminopropyl methyldiethoxysilane H2N(CH)Si(CH)(OCH)、
Aminoethylaminopropyltrimethoxysilane H2N(CH2)2NH(CH2)3Si(OCH3)3、
Aminoethylaminopropyltriethoxysilane H2N(CH2)2NH(CH2)3Si(OC2H5)3、
Aminoethylaminopropylmethyldimethoxysilane H2N(CH2)2NH(CH2)3Si(CH3)(OCH3)2、
Aminoethylaminopropylmethyldiethoxysilane H2N(CH2)2NH(CH2)3Si(CH3)(OC2H5)2、
Siloxane oligomers containing aminopropyl or aminoethylaminopropyl groups, and the like.
(C) The organopolysiloxane tackifier is polysiloxane containing vinyl, can generate a crosslinking reaction with hydrogen-containing siloxane in the presence of a platinum catalyst, is cured to form a film, has good adhesion performance on the surface of a silicon rubber product, and can be used as screen printing ink of the silicon rubber product, such as: SILMARK addition type liquid silicone rubber manufactured by Japan shin-Etsu chemical company, Toshiba-3221 single-component addition type liquid silicone rubber manufactured by Japan Toshiba organosilicon company and the like belong to the category of organosiloxane tackifier.
(D) The hydrogen-containing siloxane refers to an organosiloxane oligomer containing Si-H bonds in the molecular structure, such as:
trimethylsilyl-terminated polymethylhydrosiloxane
Dimethyl hydrogen silicon base end-capped polydimethylsiloxane
Trimethylsilyl-terminated polymethylhydrogensiloxane
Dimethyl hydrogen silicon base end-capped polymethyl hydrogen dimethyl siloxane
And MQ silicone resin containing Si-H bonds. The hydrogen-containing siloxane is used as a cross-linking agent and can perform addition reaction with polysiloxane containing vinyl under the action of a platinum catalyst.
(E) The organic solvent is used to dilute the polyurethane prepolymer, aminoalkyl siloxane, organopolysiloxane tackifier, etc. to control the viscosity of the material. Commonly used organic solvents are ketones, ethers, esters, amides, hydrocarbons, halogenated hydrocarbons and mixtures thereof.
(F) Chloroplatinic acid H2PtCl6Is used as
Andthe catalyst for addition reaction is usually isopropanol solution of chloroplatinic acid, diethyl chloroplatinate phthalate conjugate and high-activity chloroplatinate vinylsiloxane complex, and the dosage is 1-100 ppm (calculated as platinum).
The preparation method of the organic silicon modified polyurethane coating comprises the following steps:
(A) preparation of polyurethane prepolymer
And (3) reacting the polyether polyol and/or the polyester polyol with excessive diisocyanate at the temperature of 40-80 ℃ for 1-3 hours, adding a chain extender, and reacting for 1-3 hours to further increase the molecular weight of the prepolymer, wherein a micro-catalyst is added in the reaction process to ensure that the reaction is more complete. The catalysts are of various types, such as acids, bases, acid chlorides, amines and certain metal compounds, which promote the chemical reaction of isocyanates with alcoholic hydroxyl groups, but the most useful catalysts are tertiary amines and certain organometallic compounds, such as dibutyltin dilaurate, stannous octoate, triethylamine, etc. In order to facilitate the operation, the polyurethane prepolymer can be diluted by an organic solvent, so that the solid content of the polyurethane prepolymer is 8-80%, and the free isocyanate content (-NCO%) in the prepolymer is generally controlled to be 2-13%.
(B) Copolymerization of polyurethane prepolymer and aminoalkyl silane or siloxane
The residual isocyanate in the polyurethane prepolymer can continue to react with the compound containing active hydrogen and has the following activity sequence;
aliphatic amine-NH2arylamine-NH2primary-OH>water>secondary-OH>tertiary-OH>phenol-OH>COOH.
As can be seen from the above active sequence, the aminoalkyl silane or siloxane is a high-activity polyurethane modifier. At normal temperature, the-NH group in the amino alkyl silane or siloxane can react with isocyanate in the polyurethane prepolymer to generate silicon-containing substituent
. After silica chain links are introduced into the molecular structure of the polyurethane, the heat resistance is improved, and the affinity of the polyurethane to an organic silicon material is improved.
(C) The preparation of the organic silicon modified polyurethane coating which can be firmly bonded with the surface of a silicon rubber product is carried out by blending a polyurethane prepolymer with the solid content of 8-30%, an amino alkyl silane or siloxane copolymer solution (I) and an organopolysiloxane tackifier solution (II) containing hydrogen-containing siloxane with the solid content of 8-30%, wherein the mixing weight ratio of the (I) and the (II) is 4: 1-2: 1, and the organic solvent is a mixture of butanone, cyclohexanone, toluene and kerosene.
(D) Construction and curing of organosilicon modified polyurethane coating
The organic silicon modified polyurethane coating has good leveling property, can be coated on the surface of a silicon rubber product by adopting methods such as spraying, brushing, rolling and the like, and is added with 1-100 ppm of chloroplatinic acid isopropanol solution (calculated by platinum) before coating. The coated silicon rubber product is placed for 10-20 minutes at room temperature, and is baked for 10-30 minutes at the high temperature of 150-200 ℃ after the organic solvent naturally volatilizes, so that the silicon rubber product is cured to form a film, has firm bonding force with the silicon rubber, and is smooth and wear-resistant in film coating.
Example one
104 g of polypropylene oxide diol with the molecular weight of 2000, 114 g of polypropylene oxide diol with the molecular weight of 400, 68 g of polypropylene oxide triol with the molecular weight of 3000, 26 g of polypropylene oxide triol with the molecular weight of 300 and 0.2 g of phosphoric acid are added into a four-neck flask with a thermometer, a stirrer, a condenser and a dropping funnel, the materials are heated to 45-50 ℃ under stirring, 229 g of toluene diisocyanate is dropwise added into the dropping funnel for 30 minutes, then the materials are heated to 75-80 ℃ for reaction for 1 hour, 0.46 g of dibutyltin dilaurate is added, and the reaction is continued for 2.5 hours at 75-80 ℃. Cooling the reaction material to 55 ℃, dropwise adding 16 g of 1, 4-butanediol, 42 g of diethylene glycol and 100 g of mixed solvent consisting of toluene, butanone and cyclohexanone, controlling the reaction temperature below 75 ℃, feeding for 30 minutes, and continuing to react for 1 hour after the feeding is finished. Then, 42 g of castor oil and 100 g of the above-mentioned mixed solvent were added thereto, and the reaction was carried out at 75 ℃ for 2 hours. Then the temperature of the materials is reduced to below 50 ℃, 440 g of mixed solvent is added, and the mixture is stirred for 15 minutes to obtain the polyurethane prepolymer I with 50 percent of solid content.
Example two
Adding 48 g of 27.5 g of polypropylene oxide diol with the molecular weight of 1000, 27.5 g of polypropylene oxide triol with the molecular weight of 3000, 10 g of polypropylene oxide triol with the molecular weight of 3000 and 0.1 g of phosphoric acid into a four-mouth bottle with a thermometer, a stirrer, a condenser and a dropping funnel, heating the materials to about 40 ℃ under stirring, dropwise adding 30 g of toluene diisocyanate into the dropping funnel for 30 minutes, heating the materials to 75-80 ℃ for reaction for 1 hour, heating 0.2 g of dibutyltin dilaurate, and continuing the reaction for 2.5 hours at 75-80 ℃. The reaction mass was cooled to 55 ℃ and 2 g of diethylene glycol, 1 g of 1.4-butanediol and 18 g of a mixed solvent consisting of toluene, butanone and cyclohexanone were added dropwise over 30 minutes. After the materials are added, slowly raising the temperature to 75 ℃, continuing the reaction for 1 hour, then reducing the temperature of the materials to below 50 ℃, heating 100 g of mixed solvent, and stirring for 15 minutes to obtain the polyurethane prepolymer II with the solid content of 50%.
Example three
20.5 g of a polypropylene oxide diol having a molecular weight of 2000, 20 g of a polypropylene oxide diol having a molecular weight of 400, 12.5 g of a polypropylene oxide triol having a molecular weight of 3000, 4 g of a polypropylene oxide triol having a molecular weight of 300 and 0.1 g of phosphoric acid were placed in a four-neck flask equipped with a thermometer, a stirrer, a condenser and a dropping funnel, and the materials were heated to about 45 ℃ with stirring, and 50 g of toluene diisocyanate was dropped from the dropping funnel for 30 minutes. And then heating the materials to 75-80 ℃ to react for 1 hour, adding 0.2 g of dibutyltin dilaurate, and continuing to react for 2.5 hours at 75-80 ℃. Cooling the materials to 55 ℃, dropwise adding 3 g of 1.4-butanediol, 7.5 g of diethylene glycol and 30 g of mixed solvent consisting of toluene, butanone and cyclohexanone for 30 minutes, slowly heating to 75 ℃ after the materials are added, continuously reacting for 1 hour, dropwise adding 8 g of castor oil and 10 g of the mixed solvent, reacting for 2 hours at 75 ℃, cooling the materials to below 50 ℃, adding 85 g of the mixed solvent, and stirring for 15 minutes to obtain the polyurethane prepolymer III with the solid content of 50%.
Example four
Adding 15 g of polyurethane prepolymer I and 17 g of mixed solvent consisting of toluene, butanone and cyclohexanone into a four-mouth bottle with a thermometer, a stirrer, a condenser and a dropping funnel, stirring the materials uniformly at room temperature, slowly dropwise adding 3.5 g of aminoethyl aminopropyl dimethoxysilane and 17 g of mixed solvent into the dropping funnel for 30 minutes, adding the materials, and continuously stirring for 1 hour to obtain the copolymer of the polyurethane prepolymerI containing silicon substituent and the aminoethyl aminopropyl methyldimethoxysilane.
Example five
30 g of polyurethane prepolymer II and 74 g of a mixed solvent consisting of toluene, butanone and cyclohexanone are added into a four-neck flask provided with a thermometer, a stirrer, a condenser and a dropping funnel, the materials are stirred uniformly at room temperature, and 2.7 g of aminoethyl aminopropyl methyl dimethoxysilane and 74 g of the mixed solvent are slowly dropped into the dropping funnel for 30 minutes. After the addition of the materials, stirring is continued for 30 minutes to obtain a copolymer of the polyurethane prepolymer II containing the silicon substituent group and the aminoethyl aminopropyl methyl dimethoxy silane, wherein the solid content of the copolymer is about 10 percent.
Example six
7.5 g of polyurethane prepolymer III and 22 g of mixed solvent consisting of toluene, butanone and cyclohexanone are added into a four-mouth bottle provided with a thermometer, a stirrer, a condenser and a dropping funnel, the materials are stirred uniformly at room temperature, and 1.7 g of aminoethyl aminopropyl methyl dimethoxysilane and 22 g of mixed solvent are slowly dropped into the dropping funnel for 30 minutes. After the addition of the materials, the mixture was stirred for 30 minutes to obtain a copolymer of a silicon-containing substituent group-containing polyurethane prepolymer III having a solid content of 10% and aminoethyl aminopropyl methyldimethoxysilane.
Example seven
41 g of a polypropylene oxide diol having a molecular weight of 2000, 36 g of a polypropylene oxide diol having a molecular weight of 400, 13 g of a polypropylene oxide triol having a molecular weight of 3000, 2 g of a polypropylene oxide triol having a molecular weight of 300 and0.1 g of phosphoric acid were placed in a four-necked flask equipped with a thermometer, stirrer, condenser and dropping funnel. The batch was heated to 45 ℃ with stirring and 83 g of toluene diisocyanate were added dropwise from a dropping funnel over a period of 30 minutes. And then heating the materials to 75-80 ℃ for reaction for 1 hour, adding 0.2 g of dibutyltin dilaurate, reacting at 75-80 ℃ for 2.5 hours, cooling the temperature of the reaction materials to 55 ℃, and dropwise adding 6 g of 1.4-butanediol, 13 g of diethylene glycol and 30 g of mixed solvent consisting of toluene, butanone and cyclohexanone for 30 minutes. After the materials are added, the temperature of the materials is raised to 75 ℃, the reaction is continued for 1 hour, 15.8 g of castor oil and 30 g of mixed solvent are added, the reaction is carried out for 2 hours at the temperature of 75 ℃, then the temperature of the materials is reduced to below 50 ℃, 150 g of mixed solvent is added, and the stirring is carried out for 15 minutes, so as to obtain the polyurethane prepolymer IV with the solid content of 50%.
Example eight
7.5 g of polyurethane prepolymer IV and 22 g of mixed solvent consisting of methyl, butanone and cyclohexanone are added into a four-mouth bottle provided with a thermometer, a stirrer, a condenser and a dropping funnel, the materials are stirred uniformly at room temperature, 1.7 g of aminopropyltrimethoxysilane and 22 g of mixed solvent are slowly dropped into the dropping funnel for 30 minutes, and the mixture is continuously stirred for 30 minutes after the materials are added, so that the copolymer of the polyurethane prepolymer IV and the aminopropyltrimethoxysilane with the solid content of 10 percent is obtained.
Example nine
A solution with a concentration of 20% was prepared by dissolving a Silmark addition type liquid silicone rubber produced by Nippon Beacon chemical company in a mixed solvent composed of toluene, methyl ethyl ketone and cyclohexanone. 10 g of the copolymer from example 6 and 2.5 g of the above 20% strength Silmak solution and 0.1 g of a hydrosiloxane having a hydrogen content of 1.6% and 20ppm of H are weighed out2PtCl6The isopropanol solution (calculated by platinum) can be used as the wear-resistant coating of the silicon rubber product after being uniformly mixed.
Example ten
Toshiba-3221 single-component addition type liquid silicone rubber manufactured by Toshiba organosilicon company of Japan is dissolved in a mixed solvent composed of toluene, butanone and cyclohexanone to prepare a solution with a concentration of 20%. 10 g of the copolymer of example six and 2.5 g of the aforementioned 20% strength solution of Toshiba-3221 and 20ppm of H are weighed out2PtCl6The isopropanol solution (calculated by platinum) can be used as the wear-resistant coating of the silicon rubber product after being uniformly mixed.
Claims (6)
1. An organosilicon modified polyurethane coating composition, comprising:
(A) the polyurethane prepolymer, (B) amino alkyl silane or siloxane, (C) organopolysiloxane tackifier, (D) hydrogen-containing siloxane, (E) organic solvent, and (F) chloroplatinic acid catalyst, wherein the weight parts of (A), (B), (C) and (D) are as follows: (A) 1 part of a copolymer consisting of (A) and (B), and the A/B weight ratio is from 2.1 to 5.6/1; (C)0.5 part; (D)0 to 0.1 portion of (A) + (B) + (C) + (D) accounting for 10 to 30 weight percent of the total weight; (E) accounts for 70-90 wt% of the total amount, and the amount of (F) used is 2-100ppm (calculated as platinum).
2. The composition as defined in claim 1, wherein the polyurethane prepolymer is prepared by reacting polyether polyol or polyester polyol, diisocyanate, chain extender-low molecular weight diol at a temperature of 40-80 ℃, phosphoric acid is used as a polymerization inhibitor, dibutyltin dilaurate is used as a catalyst, and a mixed solvent of toluene, butanone and cyclohexanone is used as a diluent.
3. The composition as claimed in claim 1, wherein the aminoalkylsilane or siloxane is used as modifier of polyurethane, and the reaction of aminoalkylsilane or siloxane with polyurethane prepolymer is carried out at 20-40 deg.C to generate silicon-containing substituent
Or
The copolymer of (1); wherein n is more than 10.
4. The composition of claim 1, wherein the organopolysiloxane adhesion promoter is a vinyl-containing polysiloxane that undergoes a crosslinking reaction with a hydrogen-containing siloxane in the presence of a chloroplatinic acid catalyst.
5. The composition as set forth in claim 1, wherein the hydrogen-containing siloxane means a siloxane oligomer having Si-H bonds.
6. The composition as set forth in claim 1, wherein the organic solvent is a mixed solvent consisting of toluene, butanone and cyclohexanone.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN99102825A CN1100838C (en) | 1999-03-05 | 1999-03-05 | Organosilicon modified polyurethane paint |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN99102825A CN1100838C (en) | 1999-03-05 | 1999-03-05 | Organosilicon modified polyurethane paint |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1239127A CN1239127A (en) | 1999-12-22 |
| CN1100838C true CN1100838C (en) | 2003-02-05 |
Family
ID=5270996
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99102825A Expired - Fee Related CN1100838C (en) | 1999-03-05 | 1999-03-05 | Organosilicon modified polyurethane paint |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1100838C (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101376791B (en) * | 2007-08-31 | 2011-04-20 | 比亚迪股份有限公司 | Organosilicon coating and preparation thereof |
| WO2016057599A1 (en) * | 2014-10-07 | 2016-04-14 | Nbd Nanotechnologies, Inc. | Synthetic blend f-poss compositions formed from multiple feedstock materials |
| US10442823B2 (en) | 2014-10-07 | 2019-10-15 | Nbd Nanotechnologies, Inc. | Functionalized F-POSS monomer compositions and uses thereof |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100969496B1 (en) * | 2002-06-05 | 2010-07-13 | 다우 코닝 코포레이션 | Polysiloxane film and process for producing the same |
| CN1326966C (en) * | 2004-09-21 | 2007-07-18 | 济南大学 | Organic silicon modified polyurethane gap-filling rubber for cement road |
| CN101096004B (en) * | 2006-06-27 | 2010-12-01 | 深圳市海川实业股份有限公司 | Method for preparing polyurethane dispersants |
| CN101781515A (en) * | 2010-03-18 | 2010-07-21 | 上海集宝材料科技有限公司 | Aqueous double-component polyurethane rubber coating, preparation thereof and use thereof |
| CN103805041B (en) * | 2012-11-08 | 2016-06-22 | 东莞劲胜精密组件股份有限公司 | Composite high-performance coating |
| CN109504282A (en) * | 2018-12-05 | 2019-03-22 | 湖南松井新材料股份有限公司 | A kind of anti-pollution type hand-feeling coating and its preparation method and application |
| CN111074263B (en) * | 2019-12-23 | 2022-02-01 | 三达奥克化学股份有限公司 | Environment-friendly sealant used after phosphorization of wear-resistant rail transit parts and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0291172A (en) * | 1988-09-27 | 1990-03-30 | Toyoda Gosei Co Ltd | Coating composition |
| EP0430421A2 (en) * | 1989-11-30 | 1991-06-05 | Gencorp Inc. | Polyurethane/silicone compositions |
| JPH04293982A (en) * | 1991-03-25 | 1992-10-19 | Toyoda Gosei Co Ltd | Coating composition |
| EP0679705A1 (en) * | 1994-04-26 | 1995-11-02 | Gencorp Inc. | Polyurethane compositions, their preparation and use |
| JPH1120107A (en) * | 1997-07-07 | 1999-01-26 | Teijin Ltd | Film having property of easy adhesion to silicone and manufacture thereof |
-
1999
- 1999-03-05 CN CN99102825A patent/CN1100838C/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0291172A (en) * | 1988-09-27 | 1990-03-30 | Toyoda Gosei Co Ltd | Coating composition |
| EP0430421A2 (en) * | 1989-11-30 | 1991-06-05 | Gencorp Inc. | Polyurethane/silicone compositions |
| JPH04293982A (en) * | 1991-03-25 | 1992-10-19 | Toyoda Gosei Co Ltd | Coating composition |
| EP0679705A1 (en) * | 1994-04-26 | 1995-11-02 | Gencorp Inc. | Polyurethane compositions, their preparation and use |
| JPH1120107A (en) * | 1997-07-07 | 1999-01-26 | Teijin Ltd | Film having property of easy adhesion to silicone and manufacture thereof |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101376791B (en) * | 2007-08-31 | 2011-04-20 | 比亚迪股份有限公司 | Organosilicon coating and preparation thereof |
| WO2016057599A1 (en) * | 2014-10-07 | 2016-04-14 | Nbd Nanotechnologies, Inc. | Synthetic blend f-poss compositions formed from multiple feedstock materials |
| US9409933B2 (en) | 2014-10-07 | 2016-08-09 | Nbd Nanotechnologies, Inc. | Synthetic blend F-POSS compositions formed from multiple feedstock materials |
| US10208070B2 (en) | 2014-10-07 | 2019-02-19 | Nbd Nanotechnologies, Inc. | Synthetic blend F-POSS compositions formed from multiple feedstock materials |
| US10442823B2 (en) | 2014-10-07 | 2019-10-15 | Nbd Nanotechnologies, Inc. | Functionalized F-POSS monomer compositions and uses thereof |
| US10584137B2 (en) | 2014-10-07 | 2020-03-10 | Nbd Nanotechnologies, Inc. | Synthetic blend F-POSS compositions formed from multiple feedstock materials |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1239127A (en) | 1999-12-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1266184C (en) | Cross-linkable polymer blends containing alkoxysilane-terminated polymers | |
| EP2102261B1 (en) | Silicone-containing composition | |
| CN1288192C (en) | Organopoly siloxane/polyurea/polyurethane block copolymers | |
| CN1138808C (en) | Process for producing prepolymers which cure to improved sealants, and products formed thereby | |
| US11226559B2 (en) | Blocking groups for light polymerizable resins useful in additive manufacturing | |
| JP5511381B2 (en) | Solid polymer substrate having an adhesive resin component derived from a curable silylated polyurethane composition | |
| CN1146609C (en) | Polyrethane prepolymers having alkoxysilane end groups, method for the production thereof and their use for the production of sealants | |
| CN1572817A (en) | Organopolysiloxane/polyurea/polyurethane block copolymers | |
| JP3661755B2 (en) | Coating agent and silicone rubber member | |
| CN1100838C (en) | Organosilicon modified polyurethane paint | |
| CN1764685A (en) | Organopolysiloxane/polyurea/polyurethane block copolymers | |
| CN112143442B (en) | Water-resistant high-temperature-resistant mixed acrylate flexible ultraviolet curing adhesive and preparation method thereof | |
| CN110922600B (en) | Hydroxyalkyl organosilicon compounds, and preparation method and application thereof | |
| CA2477945A1 (en) | Hydrosilylation cure of silicone resin containing colloidal silica and a process for producing the same | |
| EP0690101B1 (en) | Functional polyorganosiloxane emulsions from silanes having two hydrolysable functional groups and photocurable compositions therefrom | |
| CN101048438A (en) | In-situ chain extended RTV-curing polyether | |
| KR101407617B1 (en) | Thermoset coating composition having self-healing capacity, coating film, and preparation method of coating film | |
| KR20120099451A (en) | Compositions comprising siloxane copolymers | |
| JP3814743B2 (en) | Aqueous resin composition and aqueous curable resin composition containing the same | |
| JP7290043B2 (en) | Urethane resin composition | |
| JP2004269807A (en) | Thixotropic ordinary temperature-curable composition and process for producing the same | |
| JPH07216229A (en) | Orghanopolysiloxane composition and rubber part | |
| TW202411369A (en) | Light- and moisture-curable resin compositions, cured products, uses of light- and moisture-curable resin compositions, and end-face protection methods | |
| US20220220247A1 (en) | Composition Comprising Silylated Polymer | |
| JP2003040650A (en) | Color-coated article |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| ASS | Succession or assignment of patent right |
Owner name: SILITECH CORP. Free format text: FORMER OWNER: XULI CO., LTD. Effective date: 20030307 |
|
| C41 | Transfer of patent application or patent right or utility model | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20030307 Patentee after: Honghui Industry Co., Ltd. Patentee before: Xuli Co., Ltd. |
|
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20030205 Termination date: 20140305 |