CN106632947A - Synthesis method of isocyanate curing agent - Google Patents
Synthesis method of isocyanate curing agent Download PDFInfo
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- CN106632947A CN106632947A CN201611244525.5A CN201611244525A CN106632947A CN 106632947 A CN106632947 A CN 106632947A CN 201611244525 A CN201611244525 A CN 201611244525A CN 106632947 A CN106632947 A CN 106632947A
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- Prior art keywords
- maleate
- curing agent
- isocyanate
- isocyanate curing
- performed polymer
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- 0 CC[C@@]1[C@]2(*C2)C[C@@]2[C@@]1C2 Chemical compound CC[C@@]1[C@]2(*C2)C[C@@]2[C@@]1C2 0.000 description 4
Classifications
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
-
- 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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Abstract
The invention belongs to the field of chemical processing, and particularly relates to a synthesis method of an isocyanate curing agent. The synthesis method comprises the following steps: (1) synthesis of an organic silicon modified polyaspartate prepolymer: taking amino siloxane, dropwise adding maleate in equal molar weight with the amino siloxane, and carrying out heat preservation treatment after dropwise adding is completed, thus obtaining the polyaspartate prepolymer; (2) synthesis of the isocyanate curing agent: dropwise adding the polyaspartate prepolymer into an isocyanate tripolymer which is equivalently in equal molar weight with the polyaspartate prepolymer, and carrying out heat preservation after the dropwise adding is completed, thus obtaining the organic silicon modified isocyanate curing agent. In the technology, the rising of reaction temperature is not vigorous, the speed is controllable, and synthetic isocyanate is low in viscosity and can be directly applied to the industry of two-component polyurethane coating; silicon oxygen bonds and aspartate structures are introduced to polyurethane, so that the adhesion of a polyurethane coating film can be effectively increased, and the properties of high temperature resistance, aging resistance, salt fog resistance and the like are increased; the market prospect and the economic value are huge.
Description
Technical field
The invention belongs to chemical industry manufacture field, and in particular to a kind of synthetic method of isocyanate curing agent.
Background technology
Polyurethane coating is a kind of widely used protective coating, also there is non-refractory, adhesive force bad, ageing-resistant
Property poor, salt fog resistance difference the shortcomings of.
Silane can react with many inorganic and organic materials, be a very multi-functional product, and organosilan is used as idol
Connection agent, cross-linking agent and surface modifier, with its distinctive performance many fields are widely used in, and from adhesive, are expected to painting
Foundry binders etc..
Organosilan as coupling agent, it can with the silanol groups of fiberglass surfacing or other inorganic filler surfaces point
Son effect forms covalent bond；Additionally, silicone coupling agents are also bonded containing a kind of other different functional group with polymerizable molecular, with
Good interface cohesion is obtained, further increases inorganic phase and organic alternate cross-link intensity.The silicon produced under existing technology
If oxygen alkane coupling agent in polyurethane coating sector application subject matter is added as aminopropyl triethoxysilane, because primary amine is lived
Property by force, operable time too fast with isocyanates reaction it is too short；And if add epoxide group coupling agent, due to epoxide group not
React with isocyanates, the effect of coupling is again less obvious；If the isocyanates siloxanes of addition single functionality, the crosslinking of paint film
Intensity is not enough, it may appear that the tacky phenomenon of paint film.
The content of the invention
For this purpose, the technical problem to be solved is to overcome prior art that the tacky foundation stone bottle of paint film occurs
Neck, so as to proposing a kind of adhesive force for effectively improving polyurethane coating film, improving high temperature resistant, ageing-resistant, salt spray resistance Carbimide.
The synthetic method of ester firming agent.
To solve above-mentioned technical problem, the invention discloses a kind of synthetic method of isocyanate curing agent, the synthesis
Method and step is as follows：
1) synthesis of organic-silicon-modified polyaspartic ester performed polymer：Take amino silicone, Deca and the amino silicone
The maleate of oxygen alkane equimolar amountss, isothermal holding after dripping obtains polyaspartic ester performed polymer；
2) synthesis of isocyanate curing agent：By step 1) obtained by performed polymer, be added drop-wise to equivalent to described performed polymer etc.
The isocyanate trimer of mole, isothermal holding after dripping off obtains organic-silicon-modified isocyanate curing agent.
Preferably, the maleate is dimethyl maleate, ethyl maleate., dipropyl maleate, maleic acid two
One or more in isopropyl ester, dibutyl maleate, diisobutyl maleate, diisooctyl maleate.
Preferably, step 1) described in amino silicone be aminopropyl trimethoxysilane or aminopropyl-triethoxy silicon
Alkane.
Preferably, step 2) described in isocyanate trimer be HDI trimer, TDI trimers, MDI trimers,
At least one in HMDI trimers, IPDI trimers.
Preferably, the content of NCO is 19.5%-23% in the hexamethylene diisocyanate trimer.
Preferably, step 1) in, during Deca maleate, temperature is kept for less than 50 DEG C, and while logical nitrogen enters
Row protection.
Preferably, the step 2) in, in the operating process of isocyanate trimer described in Deca, temperature is maintained at 30 DEG C
Below.
Preferably, the step 1) in, the temperature of isothermal holding is 50-120 DEG C, when a length of 24-72 hours.
Be more highly preferred to, the step 2) in, the temperature of isothermal holding is 30-80 DEG C, when a length of 2-8 hours.
The above-mentioned technical proposal of the present invention has compared to existing technology advantages below：The reaction temperature of technique of the present invention
Rise not acutely, speed is controllable, and the polyisocyanate viscosity being synthesized is low, can directly apply and be applied with the polyurethane of bi-component
In material industry；Siliconoxygen bond and aspartic acid ester structure are incorporated in polyurethane, the attachment of polyurethane coating film can be effectively improved
The performances such as power, raising high temperature resistant, ageing-resistant, salt spray resistance；With great market prospect and economic worth.
Specific embodiment
Embodiment 1 is present embodiment discloses a kind of synthetic method of isocyanate curing agent, and methods described step is as follows：
1) it is 8.6% to prepare NCO% (NCO% refers to isocyanate group content i.e. NCO content in polyisocyanate)
Organic-silicon-modified isocyanates.
Aminopropyl triethoxysilane is put in 250ml four-hole boiling flasks
110.5g, in 250ml constant pressure droppers ethyl maleate. is added86g, at normal temperatures Deca Malaysia
Diethyl phthalate, control temperature Deca and logical nitrogen protection below 45 DEG C.70 DEG C are warming up to after dripping, 48 hours are incubated
Discharging, obtains the siloxanes performed polymer with secondary amino group
(reaction descriptions：The ethyl maleate. additive reaction life of the aminopropyl triethoxysilane of one molecule and a molecule
Into aspartate).
2) performed polymer 39.3g is added to into 250ml constant pressure droppers, by the Carbimide. of hexa-methylene two of NCO%=21.7%
Ester trimer58g is added in the four-hole boiling flask of 250ml, the Deca performed polymer below 20 DEG C.
It is warming up to 30 DEG C of insulations after dripping off to discharge for 3 hours；Obtain the organic-silicon-modified isocyanates of NCO%=8.6%
Firming agent.(the siloxanes aspartate performed polymer of the molecule of reaction descriptions one and the trimerization precursor reactant of a molecule, NH:NCO=
1:3.The one of NCO in trimer is reacted away, two NCO are left.The two NCO stay the solidification as polyurethane
Agent is used.)
Embodiment 2 is present embodiment discloses a kind of synthetic method of isocyanate curing agent, and methods described step is as follows：
1) it is 12% have to prepare NCO% (NCO% refers to isocyanate group content i.e. NCO content in polyisocyanate)
Machine Si modification isocyanates.
Aminopropyl trimethoxysilane 89.5g is put in 250ml four-hole boiling flasks, in 250ml constant pressure droppers horse is added
Carry out diethyl phthalate 86g, at normal temperatures Deca ethyl maleate., control temperature Deca and logical nitrogen protection below 50 DEG C.
70 DEG C are warming up to after dripping, 48 hours are incubated and are discharged, obtain the siloxanes performed polymer with secondary amino group.
2) performed polymer 35.1g is added to into 250ml constant pressure droppers, by the Carbimide. of hexa-methylene two of NCO%=21.7%
Ester trimer 87.4g is added in the four-hole boiling flask of 250ml, the Deca performed polymer below 20 DEG C.
It is warming up to 30 DEG C of insulations after dripping off to discharge for 3 hours；The organic-silicon-modified isocyanates for obtaining NCO%=12% are consolidated
Agent.
Embodiment 3 is present embodiment discloses a kind of synthetic method of isocyanate curing agent, and methods described step is as follows：
1) it is 8.5% to prepare NCO% (NCO% refers to isocyanate group content i.e. NCO content in polyisocyanate)
Organic-silicon-modified isocyanates.
Aminopropyl trimethoxysilane 89.5g is put in 250ml four-hole boiling flasks, in 250ml constant pressure droppers horse is added
Carry out dibutyl phthalate 114g, at normal temperatures Deca dibutyl maleate, control temperature Deca and logical nitrogen protection below 50 DEG C.
70 DEG C are warming up to after dripping, 48 hours are incubated and are discharged, obtain the siloxanes performed polymer with secondary amino group.
2) performed polymer 101g is added to into 250ml constant pressure droppers, by the hexamethylene diisocyanate of NCO%=21.7%
Trimer 145g is added in the four-hole boiling flask of 250ml, the Deca performed polymer below 20 DEG C.
It is warming up to 30 DEG C of insulations after dripping off to discharge for 3 hours；Obtain the organic-silicon-modified isocyanates of NCO%=8.5%
Firming agent.
Embodiment 4 is present embodiment discloses a kind of synthetic method of isocyanate curing agent, and methods described step is as follows：
1) it is 8.5% to prepare NCO% (NCO% refers to isocyanate group content i.e. NCO content in polyisocyanate)
Organic-silicon-modified isocyanates.
Aminopropyl trimethoxysilane 89.5g is put in 250ml four-hole boiling flasks, in 250ml constant pressure droppers horse is added
Carry out dibutyl phthalate 114g, at normal temperatures Deca dibutyl maleate, control temperature Deca and logical nitrogen protection below 50 DEG C.
50 DEG C are warming up to after dripping, 72 hours are incubated and are discharged, obtain the siloxanes performed polymer with secondary amino group.
2) performed polymer 101g is added to into 250ml constant pressure droppers, the TDI trimers of NCO%=19.5% is (pre- with described
Aggressiveness equimolar amountss) four-hole boiling flask of 250ml is added to, below 20 DEG C Deca performed polymer.
It is warming up to 80 DEG C of insulations after dripping off to discharge for 2 hours；Obtain the organic-silicon-modified isocyanates of NCO%=8.5%
Firming agent.
Embodiment 5 is present embodiment discloses a kind of synthetic method of isocyanate curing agent, and methods described step is as follows：
1) it is 8.5% to prepare NCO% (NCO% refers to isocyanate group content i.e. NCO content in polyisocyanate)
Organic-silicon-modified isocyanates.
Aminopropyl trimethoxysilane 89.5g is put in 250ml four-hole boiling flasks, in 250ml constant pressure droppers horse is added
Carry out dibutyl phthalate 114g, at normal temperatures Deca dibutyl maleate, control temperature Deca and logical nitrogen protection below 50 DEG C.
120 DEG C are warming up to after dripping, 24 hours are incubated and are discharged, obtain the siloxanes performed polymer with secondary amino group.
2) performed polymer 101g is added to into 250ml constant pressure droppers, by the MDI trimers of NCO%=23% (with the pre-polymerization
Body equimolar amountss) four-hole boiling flask of 250ml is added to, below 20 DEG C Deca performed polymer.
It is warming up to 30 DEG C of insulations after dripping off to discharge for 8 hours；Obtain the organic-silicon-modified isocyanates of NCO%=8.5%
Firming agent.
Experimental example improves adhesive force and salt tolerant fog effect of the resin in base material
The use of the polyaspartic ester that amine equivalent is 276 is matrix resin and the firming agent of embodiment 1 and hexa-methylene two
Isocyanate trimer firming agent by different proportion mix, spray plate, 100 microns of thickness, conserve 2 weeks test adhesive force contrast and
Salt spray resistance adhesive force contrast afterwards in 1400 hours is following (shown in table 1)：
Table 1
| Hexamethylene diisocyanate trimer/embodiment 1 | 3/1 | 5/1 | 7/1 | 10 |
| Pull open method adhesive force Mpa | 11.4 | 11.1 | 10.9 | 11.6 |
| Salt fog postadhesion power Mpa | 16.4 | 13.4 | 12.5 | 9.8 |
Obviously, above-described embodiment is only intended to clearly illustrate example, and not to the restriction of embodiment.It is right
For those of ordinary skill in the art, can also make on the basis of the above description other multi-forms change or
Change.There is no need to be exhaustive to all of embodiment.And the obvious change thus extended out or
Among changing still in the protection domain of the invention.
Claims (9)
1. a kind of synthetic method of isocyanate curing agent, it is characterised in that the synthetic method step is as follows：
1) synthesis of organic-silicon-modified polyaspartic ester performed polymer：Take amino silicone, Deca and the amino silicone
The maleate of equimolar amountss, isothermal holding after dripping obtains polyaspartic ester performed polymer；
2) synthesis of isocyanate curing agent：By step 1) obtained by performed polymer, be added drop-wise to equivalent to the performed polymer equimolar
The isocyanate trimer of amount, isothermal holding after dripping off obtains organic-silicon-modified isocyanate curing agent.
2. the method for claim 1, it is characterised in that the maleate is dimethyl maleate, maleic acid diethyl
In ester, dipropyl maleate, isopropyl maleate, dibutyl maleate, diisobutyl maleate, diisooctyl maleate
One or more.
3. the method for claim 1, it is characterised in that step 1) described in amino silicone be aminopropyl trimethoxy
Silane or aminopropyl triethoxysilane.
4. the method for claim 1, it is characterised in that step 2) described in isocyanate trimer be HDI trimerizations
At least one in body, TDI trimers, MDI trimers, HMDI trimers, IPDI trimers.
5. the method as described in any one of claim 1-4, it is characterised in that in the hexamethylene diisocyanate trimer
The content of NCO is 19.5%-23%.
6. the method as described in any one of claim 1-4, it is characterised in that step 1) in, during Deca maleate, temperature
Degree is kept for less than 50 DEG C, and while logical nitrogen is protected.
7. the method as described in any one of claim 1-4, it is characterised in that the step 2) in, isocyanates described in Deca
In the operating process of trimer, temperature is maintained at less than 30 DEG C.
8. the method as described in any one of claim 1-4, it is characterised in that the step 1) in, the temperature of isothermal holding is
50-120 DEG C, when a length of 24-72 hours.
9. the method as described in any one of claim 1-4, it is characterised in that the step 2) in, the temperature of isothermal holding is
30-80 DEG C, when a length of 2-8 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611244525.5A CN106632947A (en) | 2016-12-29 | 2016-12-29 | Synthesis method of isocyanate curing agent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201611244525.5A CN106632947A (en) | 2016-12-29 | 2016-12-29 | Synthesis method of isocyanate curing agent |
Publications (1)
| Publication Number | Publication Date |
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| CN106632947A true CN106632947A (en) | 2017-05-10 |
Family
ID=58835597
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| CN201611244525.5A Pending CN106632947A (en) | 2016-12-29 | 2016-12-29 | Synthesis method of isocyanate curing agent |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108913007A (en) * | 2018-05-08 | 2018-11-30 | 深圳飞扬骏研新材料股份有限公司 | A kind of greasy dirt mattess oil rub resistance primer resin and its synthetic method |
| CN109852221A (en) * | 2019-01-08 | 2019-06-07 | 中海油常州涂料化工研究院有限公司 | A kind of low VOC and high performance dual-component aqueous polyurethane woodwork coating and preparation method thereof |
| CN109851738A (en) * | 2018-12-04 | 2019-06-07 | 广州市金铂尔化工有限公司 | A kind of preparation method of fluorinated silicone modified urea-based compound |
| CN110862765A (en) * | 2019-12-05 | 2020-03-06 | 湖南航天三丰科工有限公司 | Coating for surface of silicon rubber substrate and preparation method thereof |
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| JP7440500B2 (en) | 2018-10-19 | 2024-02-28 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハー | Aspartate functional polysiloxanes, their preparation and their uses |
| CN113195579B (en) * | 2018-10-19 | 2023-05-02 | 迈图高新材料有限责任公司 | Aspartate-functional polysiloxanes, their preparation and their use |
| JP2022505063A (en) * | 2018-10-19 | 2022-01-14 | モメンティブ パフォーマンス マテリアルズ ゲーエムベーハー | Aspartic acid ester functional polysiloxanes, their preparation and their use |
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| CN109852221A (en) * | 2019-01-08 | 2019-06-07 | 中海油常州涂料化工研究院有限公司 | A kind of low VOC and high performance dual-component aqueous polyurethane woodwork coating and preparation method thereof |
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| CN111363460B (en) * | 2020-03-18 | 2021-11-26 | 深圳飞扬骏研新材料股份有限公司 | Environment-friendly baking-free finishing varnish for spraying, preparation method and curing material |
| CN111363460A (en) * | 2020-03-18 | 2020-07-03 | 深圳飞扬骏研新材料股份有限公司 | Environment-friendly baking-free finishing varnish for spraying, preparation method and curing material |
| CN111793420A (en) * | 2020-06-22 | 2020-10-20 | 四川君尚亚克力制造有限公司 | Modified polyaspartic acid ester polyurea coating and preparation method thereof |
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| CN112250868A (en) * | 2020-10-26 | 2021-01-22 | 深圳飞扬兴业科技有限公司 | Polysiloxane-asparagus resin/polyaspartic polyurea and preparation method thereof |
| CN114409869A (en) * | 2022-01-12 | 2022-04-29 | 万华化学集团股份有限公司 | Multi-curing isocyanate prepolymer and preparation method and application thereof |
| CN114409869B (en) * | 2022-01-12 | 2023-07-11 | 万华化学集团股份有限公司 | Multi-curing isocyanate prepolymer and preparation method and application thereof |
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