CN107151326A - A kind of method of the organic siliconresin constituent prepared containing amino - Google Patents
A kind of method of the organic siliconresin constituent prepared containing amino Download PDFInfo
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- CN107151326A CN107151326A CN201710302107.5A CN201710302107A CN107151326A CN 107151326 A CN107151326 A CN 107151326A CN 201710302107 A CN201710302107 A CN 201710302107A CN 107151326 A CN107151326 A CN 107151326A
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- organic siliconresin
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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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/18—Fireproof paints including high temperature resistant paints
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- Polymers & Plastics (AREA)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
Abstract
The present invention provides a kind of method of the organic siliconresin constituent prepared containing amino, and organic siliconresin constituent unit composition is:R1 a(R2O)bXcSiO(4‑a‑b‑c)/2(Ia).It is R that this method, which includes heating unit composition,1 a(R2O)b+cSiO(4‑a‑b‑c)/2(Ib) the organic siliconresin containing silicone hydroxyl or silane epoxide, aminated compounds X H (Ic), the catalyst reaction of hydroxyl is prepared.Wherein, the group that X connects for the SiOC keys of formula (Ia):‑O‑Z‑NH2;This method synthesis technique is simple, is not required to press device, and non-corrosiveness accessory substance is produced, and can prepare the compound containing amido organosilicon of high amino content.The organic siliconresin constituent is particularly suitable for the curing agent of epoxy resin, can normal temperature or low-temperature bake and epoxy resin cure, due to the importing of organosilicon chain link, there is excellent heat resistance, weatherability, red hardness with the film forming matter of epoxy resin, available for heat-resisting paint either heat-resistant high-performance composite.
Description
Technical field
The present invention relates to a kind of organic siliconresin constituent containing amino, more particularly to its preparation method and constituent.
Background technology
The film forming matter of organic heat proof material in the market mainly has the tree such as polytetrafluoroethylene (PTFE), organosilicon modified polyester
Fat, but the baking temperature of these film forming matters is higher, generally requires more than 200 DEG C, particularly polytetrafluoroethylene (PTFE) is needed 380
More than DEG C, construction environment, the scope of construction substrate significantly limit.The organo-silicon compound of amido-containing group have a variety of use
On the way, it can especially solidify with epoxy resin in room temperature or low-temperature bake, film forming matter has excellent heat resistance, weatherability, heat hard
Degree, thus can be applicable to room temperature or low-temperature bake solidification heat-resisting paint, non-viscous paint, decorative paint, outdoor weather resistance coating,
Available for the high performance composite such as heat-resisting die.
Hydroxy silicon oil or cyclosiloxane prepare amido silicon oil with the silane coupler hydrolytic condensation with amino group, are one
The method of the organo-silicon compound of the synthesis amido-containing group of quasi-tradition.The active group of amido silicon oil can be with natural fiber, change
Fine and blend fabric is combined well, can be widely used in the fields such as textile finishing, printing and dyeing as soft finishing agent etc..In for example
State Patent document number CN201210114477.3 discloses a kind of synthetic method of hydrophilic amino silicone oil, using low viscosity
The one or two of hydroxy silicon oil and cyclosiloxane are with the amino coupling agent of the chain link containing polyethers under conditions of alcohol or ester are solvent
Condensation reaction is carried out to be made.But the amino content of the amido silicon oil of such method synthesis is not high, it is impossible to be used as epoxy resin
Curing agent use.
Chinese patent literature CN201210114477.3 discloses a kind of method for preparing amino silicone, its preparation side
Method is to be reacted the siloxanes of unsaturated aminated compounds and siliceous hydrogen under conditions of the presence of catalyst platinum dioxide, should
Method high catalytic efficiency, adds the selectivity of γ-addition compound product, and catalyst is easily isolated, recyclable to recycle.But should
Method technique is more complicated, and the catalyst used and unsaturated amine are costly.
Chinese patent literature CN201310318551.8 discloses a kind of organic oximido compound containing amine propyl group
Preparation method, this method is mixed chloropropyl chlorosilane with organic amine, and is reacted in pressure reacting container, and is obtained
The amino silane containing amine propyl group is obtained, then with organic oxime react obtaining the organic oximino silane of amine propyl group.But the method is related to
And to stress reaction, and have hydrochloric acid as accessory substance, add the cost of equipment corrosion and post processing.
The content of the invention
In order to solve the above-mentioned technical problem, present invention employs following technical proposals:It is a kind of to prepare containing the organic of amino
The method of silicon resin component, comprises the following steps:
Step one:Prepare the organosilicon containing silicone hydroxyl or silane epoxide that the unit by (Ib) of 30 to 99 parts by weight is constituted
The amino-compound X-H (Ic) and the catalyst of 0.001-1 parts by weight of resin, the hydroxyl of 1 to 70 parts by weight;
Step 2:The material prepared in step one is added in reactor, leads to nitrogen and heating stirring;
Step 3:Mixture in reactor is heated to 125 ± 5 DEG C, methanol distillate is drawn;
Step 4:Methanol distillate is cooled to≤65 DEG C, 160-180 DEG C is then to slowly warm up to, finally evaporate temperature to≤
50 DEG C, it is filtrated to get organo-silicon compound of the pale yellow transparent containing amino.
In above-mentioned steps, the unit group of the organic siliconresin containing silicone hydroxyl or silane epoxide in the step one turns into R1a
(R2O)b+cSiO(4-a-b-c)/2(Ib)。
In above-mentioned steps, the unit group of the amine compound of hydroxyl turns into HO-X-NH2 (Ic) in the step one.
In above-mentioned steps, the unit composition of organo-silicon compound of the pale yellow transparent drawn in the step 4 containing amino
For:R1a(R2O)bXcSiO(4-a-b-c)/2(Ia).
In above-mentioned steps, unit composition R1a (R2O) b+ of the organic siliconresin containing silicone hydroxyl or silane epoxide
In cSiO (4-a-b-c)/2 (Ib), the silane epoxide of silicone hydroxyl or 4-20 parts by weight with 2 to 10 parts by weight;Wherein a and b
Summation between 0 to 4;B is more than 0;Condition be a+b+c≤4, R1 be selected from aromatic radical, alkyl or alkenyl, its can by O, S,
N or P intervals, R2 is selected from hydrogen or alkyl.
In above-mentioned steps, in the unit composition HO-X-NH2 of the amine compound of described hydroxyl, X for divalence, not
Aromatic radical, alkyl or alkenyl substitution or be substituted, it can be by O, S, N or P interval.
In above-mentioned steps, described catalyst includes but is not limited to metallic salt, preferably dibutyl tin dilaurate, only son
Base tin oxide, butyl titanate, tetraisopropyl titanate, or combinations of the above.
In above-mentioned steps, in preparation process, the unit composition R1a of the organic siliconresin containing silicone hydroxyl or silane epoxide
(R2O) all or part of R2O groups are constituted by the unit of the amine compound of hydroxyl in b+cSiO (4-a-b-c)/2 (Ib)
X group in HO-X-NH2 (Ic) is replaced, and eliminates corresponding R2OH molecules.
In above-mentioned steps, described organo-silicon compound are preferably made up of the unit of 1 to 100 formula (Ia) or (Ib), special
Wei not 1 to 10 unit.Especially, summation a+b+c=4 in (Ia) or (Ib);In other words, organo-silicon compound are silane.
In above-mentioned steps, it is siliconated that the unit by R1a (R2O) bXcSiO (4-a-b-c)/2 (Ia) is constituted
Compound preferably comprises 1 to 50, specifically for 2-10 X group.
After adopting the above technical scheme, the present invention has the advantages that compared with prior art:Pass through above-mentioned side
Organic siliconresin constituent technique of the method synthesis containing amino is simple, is not required to press device, and non-corrosiveness accessory substance is produced, can prepared
The organo-silicon compound of high amino content, and the organo-silicon compound of the amido-containing group at preparation serve many purposes, especially
It is can to solidify with epoxy resin in room temperature or low-temperature bake, and film forming matter has excellent heat resistance, weatherability, red hardness, because
This can be applicable to heat-resisting paint, non-viscous paint, decorative paint, the outdoor weather resistance coating of room temperature or low-temperature bake solidification, it is also possible to
In the high performance composite such as heat-resisting die.
Embodiment
With reference to embodiment, the invention will be further described.
First embodiment
DC-3074 (DOW CORNING silicone intermediate, silicon are put into the reactor for being provided with stirring, nitrogen and thermometer
Methoxyl content is about 18%) 900g, 6- amino -1- hexanols 510.36g, dibutyl tin laurate 0.8g, it is heated to 125 ±
5 DEG C, start to be collected into methanol distillate, holding evaporates temperature≤65 DEG C, 160-180 DEG C is to slowly warm up to, until evaporating temperature≤50
DEG C stop reaction.Organo-silicon compound of the pale yellow transparent containing amino are filtrated to get, viscosity is 2500cps at room temperature.
By the organo-silicon compound and bisphenol A type epoxy resin NPEL-128, (South Asia liquid epoxies, epoxide equivalent is
180-190) press 0.8:1 ratio is well mixed, plus a small amount of solvent and auxiliary agent are made into two component epoxy coating and be sprayed on aluminium sheet,
The film forming after 80 DEG C are toasted 2h.This film is 4H in the hardness of room temperature, and 180 DEG C of red hardness is 2H, other physical properties of film
As shown in table 1.
Second embodiment
Put into the reactor for being provided with stirring, nitrogen and thermometerIC 232 is (in watt gram organosilicon
Mesosome, silicon methoxyl content is about 15%) 900g, 6- amino -1- hexanols 425.3g, Mono-n-butyltin 0.8g, is heated to 125
± 5 DEG C, start to be collected into methanol distillate, holding evaporates temperature≤65 DEG C, is to slowly warm up to 160-180 DEG C, until evaporate temperature≤
50 DEG C are stopped reaction.Organo-silicon compound of the pale yellow transparent containing amino are filtrated to get, viscosity is 1600cps at room temperature.
By the organo-silicon compound and bisphenol A type epoxy resin NPEL-128, (South Asia liquid epoxies, epoxide equivalent is
180-190) press 0.7:1 ratio is well mixed, plus a small amount of solvent and auxiliary agent are made into two component epoxy coating and be sprayed on aluminium sheet,
The film forming after 80 DEG C are toasted 2h.This film is 4H in the hardness of room temperature, and 180 DEG C of red hardness is H, other physical properties of film
As shown in table 1.
3rd embodiment
1,3- dimethoxy -1,1,3,3- tetramethyls two are put into the reactor for being provided with stirring, nitrogen and thermometer
Siloxanes 800g, 1,3- diaminourea -2- hydroxy propanes 741.80g, dibutyl tin laurate 1.0g, are heated to 125 ± 5 DEG C,
Start to be collected into methanol distillate, holding evaporates temperature≤65 DEG C, is to slowly warm up to 160-180 DEG C, stop until evaporating temperature≤50 DEG C
Reaction.Organo-silicon compound of the pale yellow transparent containing amino are filtrated to get, viscosity is 1500cps at room temperature.
By the organo-silicon compound and bisphenol A type epoxy resin NPEL-128, (South Asia liquid epoxies, epoxide equivalent is
180-190) press 0.2:1 ratio is well mixed, plus a small amount of solvent and auxiliary agent are made into two component epoxy coating and be sprayed on aluminium sheet,
The film forming after 80 DEG C are toasted 2h.This film is 3H in the hardness of room temperature, and 180 DEG C of red hardness is F, other physical properties of film
As shown in table 1.
Fourth embodiment
Put into the reactor for being provided with stirring, nitrogen and thermometer tetraethyl orthosilicate 800g, 6- amino -1- oneself
Alcohol 843.78g, dibutyl tin laurate 1.0g, are heated to 125 ± 5 DEG C, start that methanol distillate can be collected into, keep evaporating
Temperature≤65 DEG C, be to slowly warm up to 160-180 DEG C, until evaporate temperature≤50 DEG C stop reaction.Pale yellow transparent is filtrated to get containing amino
Organo-silicon compound, viscosity is 500cps at room temperature.
By the organo-silicon compound and bisphenol A type epoxy resin NPEL-128, (South Asia liquid epoxies, epoxide equivalent is
180-190) press 0.4:1 ratio is well mixed, plus a small amount of solvent and auxiliary agent are made into two component epoxy coating and be sprayed on aluminium sheet,
The film forming after 80 DEG C are toasted 2h.This film is 3H in the hardness of room temperature, and 180 DEG C of red hardness is HB, other physical properties of film
As shown in table 1.
5th embodiment
Put into the reactor for being provided with stirring, nitrogen and thermometerSY 300 is (in watt gram organosilicon
Mesosome, silicone hydroxyl content is about 3.5-5.5%) 500g, diglycolamine 139.16g, butyl titanate 0.6g, be heated to 125 ± 5
DEG C, start to be collected into methanol distillate, holding evaporates temperature≤65 DEG C, is to slowly warm up to 160-180 DEG C, until evaporating temperature≤50 DEG C
Stop reaction.Organo-silicon compound of the pale yellow transparent containing amino are filtrated to get, viscosity is 800cps at room temperature.
The organo-silicon compound and hydrogenated epoxy resin EPONEX 1510 (are stepped into figure epoxy resin, epoxide equivalent is 210-
215) 1 is pressed:1 ratio is well mixed, plus a small amount of solvent and auxiliary agent are made into two component epoxy coating and be sprayed on aluminium sheet, by 80
DEG C baking 2h after film forming.This film is 2H in the hardness of room temperature, and 180 DEG C of red hardness is HB, other physical properties such as institute of table 1 of film
Show.
Sixth embodiment
1,2- dimethoxy -1,1,2,2- tetramethyls two are put into the reactor for being provided with stirring, nitrogen and thermometer
Silane 800g, 1,3- diaminourea -2- hydroxy propanes 808.34g, tetraisopropyl titanate 1.0g, are heated to 125 ± 5 DEG C, starting can
To be collected into methanol distillate, holding evaporates temperature≤65 DEG C, is to slowly warm up to 160-180 DEG C, and reaction is stopped until evaporating temperature≤50 DEG C.Cross
Filter obtains organo-silicon compound of the pale yellow transparent containing amino, and viscosity is 1400cps at room temperature.
By the organo-silicon compound and bisphenol A type epoxy resin NPEL-128, (South Asia liquid epoxies, epoxide equivalent is
180-190) press 0.2:1 ratio is well mixed, plus a small amount of solvent and auxiliary agent are made into two component epoxy coating and be sprayed on aluminium sheet,
The film forming after 80 DEG C are toasted 2h.This film is 3H in the hardness of room temperature, and 180 DEG C of red hardness is F, other physical properties of film
As shown in table 1.
Table 1
Although the present invention is disclosed as above with several preferred embodiments, it is not limited to the present invention, any this area
Technical staff, without departing from the spirit and scope of the present invention, arbitrarily changes and retouches when that can make, therefore the protection of the present invention
Scope is when being defined that the claim depending on enclosing is defined.
Claims (10)
1. a kind of method of the organic siliconresin constituent prepared containing amino, it is characterised in that:Comprise the following steps:
Step one:Prepare the organosilicon tree containing silicone hydroxyl or silane epoxide that the unit by (Ib) of 30 to 99 parts by weight is constituted
The amino-compound X-H (Ic) and the catalyst of 0.001-1 parts by weight of fat, the hydroxyl of 1 to 70 parts by weight;
Step 2:The material prepared in step one is added in reactor, leads to nitrogen and heating stirring;
Step 3:Mixture in reactor is heated to 125 ± 5 DEG C, methanol distillate is drawn;
Step 4:Methanol distillate is cooled to≤65 DEG C, 160-180 DEG C is then to slowly warm up to, temperature is finally evaporated to≤50 DEG C,
It is filtrated to get organo-silicon compound of the pale yellow transparent containing amino.
2. a kind of method of organic siliconresin constituent prepared containing amino according to claim 1, it is characterised in that:
The unit group of organic siliconresin containing silicone hydroxyl or silane epoxide in the step one turns into R1 a(R2O)b+cSiO(4-a-b-c)/2
(Ib)。
3. a kind of method of organic siliconresin constituent prepared containing amino according to claim 1, it is characterised in that:
The unit group of the amine compound of hydroxyl turns into HO-X-NH2 (Ic) in the step one.
4. a kind of method of organic siliconresin constituent prepared containing amino according to claim 1, it is characterised in that:
The unit group of organo-silicon compound of the pale yellow transparent drawn in the step 4 containing amino turns into:R1 a(R2O)bXcSiO(4-a-b-c)/2(Ia)。
5. a kind of method of organic siliconresin constituent prepared containing amino according to claim 2, it is characterised in that:
The unit composition R of the described organic siliconresin containing silicone hydroxyl or silane epoxide1 a(R2O)b+cSiO(4-a-b-c)/2(Ib) in, with 2
To the silicone hydroxyl or the silane epoxide of 4-20 parts by weight of 10 parts by weight;
Wherein a and b summation is between 0 to 4;
B is more than 0;
Condition is a+b+c≤4,
R1 be selected from aromatic radical, alkyl or alkenyl, its can by O, S, N or P interval,
R2 is selected from hydrogen or alkyl.
6. a kind of method of organic siliconresin constituent prepared containing amino according to claim 3, it is characterised in that:
In the unit composition HO-X-NH2 of the amine compound of described hydroxyl, X is fragrance that is divalence, unsubstituted or being substituted
Base, alkyl or alkenyl, it can be by O, S, N or P interval.
7. a kind of method of organic siliconresin constituent prepared containing amino according to claim 1, it is characterised in that:
Described catalyst includes but is not limited to metallic salt, preferably dibutyl tin dilaurate, Mono-n-butyltin, the fourth of metatitanic acid four
Ester, tetraisopropyl titanate, or combinations of the above.
8. a kind of method of organic siliconresin constituent prepared containing amino according to claim 1, it is characterised in that:
In preparation process, the unit composition R of the organic siliconresin containing silicone hydroxyl or silane epoxide1 a(R2O)b+cSiO(4-a-b-c)/2(Ib)
In all or part of R2O groups the X group in HO-X-NH2 (Ic) constituted by the unit of the amine compound of hydroxyl put
Change, and eliminate corresponding R2OH molecules.
9. a kind of method of organic siliconresin constituent prepared containing amino according to claim 1, it is characterised in that:
Described organo-silicon compound are preferably made up of the unit of 1 to 100 formula (Ia) or (Ib), specifically for 1 to 10 unit, especially
Summation a+b+c=4 in ground, (Ia) or (Ib);In other words, organo-silicon compound are silane.
10. a kind of method of organic siliconresin constituent prepared containing amino according to claim 4, its feature exists
In:It is described by R1 a(R2O)bXcSiO(4-a-b-c)/2(Ia) organo-silicon compound of unit composition preferably comprise 1 to 50, spy
Wei not 2-10 X group, the group that wherein X connects for the SiOC- keys of formula (Ia):-O-Z-NH2.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107880270A (en) * | 2017-11-21 | 2018-04-06 | 广东拓普合成科技股份有限公司 | A kind of preparation method of the water-based isocyanate type curing agent containing silicone segments |
CN113881318A (en) * | 2021-11-09 | 2022-01-04 | 嘉兴学院 | Normal-temperature curing anti-icing coating and preparation method thereof |
CN116589899A (en) * | 2022-10-25 | 2023-08-15 | 安徽博斯科新材料科技有限公司 | Hydrogenated epoxy-amino alkoxy polysiloxane coating and application thereof |
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EP1359182A1 (en) * | 2002-05-03 | 2003-11-05 | SigmaKalon Group B.V. | Organo-functional polysiloxanes |
CN1662581A (en) * | 2002-05-03 | 2005-08-31 | 式玛卡龙服务股份有限公司 | Amino-functional polysiloxanes and their use in coatings |
CN1814654A (en) * | 2005-02-04 | 2006-08-09 | 信越化学工业株式会社 | Method for preparing organic polysiloxane containing amino |
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Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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EP1359182A1 (en) * | 2002-05-03 | 2003-11-05 | SigmaKalon Group B.V. | Organo-functional polysiloxanes |
CN1662581A (en) * | 2002-05-03 | 2005-08-31 | 式玛卡龙服务股份有限公司 | Amino-functional polysiloxanes and their use in coatings |
CN1814654A (en) * | 2005-02-04 | 2006-08-09 | 信越化学工业株式会社 | Method for preparing organic polysiloxane containing amino |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN107880270A (en) * | 2017-11-21 | 2018-04-06 | 广东拓普合成科技股份有限公司 | A kind of preparation method of the water-based isocyanate type curing agent containing silicone segments |
CN107880270B (en) * | 2017-11-21 | 2021-07-09 | 广东拓普合成科技股份有限公司 | Preparation method of water-based isocyanate curing agent containing organic silicon chain segment |
CN113881318A (en) * | 2021-11-09 | 2022-01-04 | 嘉兴学院 | Normal-temperature curing anti-icing coating and preparation method thereof |
CN116589899A (en) * | 2022-10-25 | 2023-08-15 | 安徽博斯科新材料科技有限公司 | Hydrogenated epoxy-amino alkoxy polysiloxane coating and application thereof |
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Application publication date: 20170912 |