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CN114316240B - Cationic curable composition - Google Patents

Cationic curable composition Download PDF

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Publication number
CN114316240B
CN114316240B CN202011029144.1A CN202011029144A CN114316240B CN 114316240 B CN114316240 B CN 114316240B CN 202011029144 A CN202011029144 A CN 202011029144A CN 114316240 B CN114316240 B CN 114316240B
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alkyl
curable composition
compound
cyclic ether
optionally
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CN114316240A (en
Inventor
严春霞
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Changzhou Zhengjie Intelligent Manufacturing Technology Co ltd
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Changzhou Zhengjie Intelligent Manufacturing Technology Co ltd
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Priority to CN202011029144.1A priority Critical patent/CN114316240B/en
Priority to PCT/CN2021/118557 priority patent/WO2022063004A1/en
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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
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
    • 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
    • C08G65/04—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 from cyclic ethers only
    • C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
    • C08G65/16—Cyclic ethers having four or more ring atoms
    • C08G65/18—Oxetanes
    • 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
    • C08G65/04—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 from cyclic ethers only
    • C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
    • 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
    • C09D1/00—Coating compositions, e.g. paints, varnishes or lacquers, based on inorganic substances
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Inorganic Chemistry (AREA)
  • Epoxy Resins (AREA)
  • Polyethers (AREA)

Abstract

A cationically curable composition comprising a cationically polymerizable compound, a super acid and water is disclosed. The composition can solve the problems that the existing strong acid curing is difficult to implement, and the photo-curing composition has high viscosity, is easy to yellow and has limited application fields.

Description

Cationic curable composition
Technical Field
The application belongs to the technical field of chemical and photoelectric crossing, and particularly relates to a cationic curable composition.
Background
Cationic polymerization is mainly carried out by using a catalyst to promote the start of chains, and all used initiators are electrophiles, mainly protonic acids, lewis acids and the like. As one of protonic acid, super strong acid has strong acidity, large dissociation constant, high activity and high initiation speed, but the generated counter anion has weak nucleophilicity, is difficult to form covalent bond with the active center of a growing chain to terminate the reaction, has limited monomer selectivity and greatly limits the application of the super strong acid.
In recent years, cationic photopolymerization develops rapidly, and has the advantages of no influence of oxygen, small volume shrinkage and the like. However, the cationic free radical is unstable, the photopolymerization condition is more severe, the polymerization is greatly influenced by trace water, air and impurities, the experimental repeatability is poor, and the development of the cationic free radical is limited to a great extent; meanwhile, in order to improve the initiation efficiency, it is often necessary to increase the absorption wavelength of the initiator, so that yellowing is easy to occur after the composition is applied, and the viscosity adjustment of the composition is limited, and the application field is limited.
Disclosure of Invention
Aiming at the defects of the prior art, the application mainly aims to provide a cationic curable composition to solve the problems that the existing strong acid curing is difficult to implement, and the photo-curing composition has high viscosity, is easy to yellow and has limited application prospect.
In order to achieve the above object, there is provided a cationic curable composition comprising the following components:
(A) A cationically polymerizable compound;
(B) Super acid;
(C) And (3) water.
As component (A), the cationically polymerizable compound is one or more of a cyclic ether compound and a vinyl ether compound, preferably a cyclic ether compound.
Further, the cyclic ether compound is one or more of an epoxy compound and an oxetane compound.
As the epoxy compound, an alicyclic epoxy compound and/or a non-alicyclic epoxy compound may be mentioned. From the viewpoint of further improving the curing speed, it is preferable to use a polyfunctional alicyclic epoxy compound having 2 or more alicyclic epoxy groups in the molecule and/or an alicyclic epoxy compound having 1 alicyclic epoxy group in the molecule and an unsaturated double bond group such as a vinyl group; preference is given to epoxy compounds having an epoxycyclohexyl group, such as 3, 4-epoxycyclohexylmethyl-3 ',4' -epoxycyclohexylcarboxylate, epsilon-caprolactone-modified-3, 4-epoxycyclohexylmethyl-3 ',4' -epoxycyclohexylcarboxylate, bis ((3, 4-epoxycyclohexyl) methyl) adipate, epoxycyclohexane, 2- (3, 4-epoxycyclohexane) ethyltrimethoxysilane, 3, 4-epoxycyclohexylmethacrylate, 1, 2-epoxy-4-vinylcyclohexane, 3, 4-epoxycyclohexylcarboxylate, polymerized products of 3, 4-epoxycyclohexylmethyl-3 ',4' -epoxycyclohexylcarboxylate and caprolactone, 4-methyl-1, 2-epoxycyclohexane, 2-bis (3, 3' -epoxycyclohexyl) propane, 2- (3, 4-epoxycyclohexane) ethyltrimethoxysilane and the like. From the viewpoint of the storage stability of the composition, non-alicyclic epoxy compounds such as diglycidyl ether of bisphenol a, diglycidyl or triglycidyl ether of alkoxylated bisphenol a, novolak epoxide and the like can be preferably used.
The oxetane compound is not particularly limited in its kind, and may be monofunctional or may be di-or polyfunctional. Theoretically, all of the oxetanes used in the field of cationic curable compositions are applicable. Illustratively, oxetanes such as those described in chinese patent application publication No. CN107619399A, CN107621752A, CN109305947A, CN109400551a may be used, the relevant disclosure of which is incorporated herein.
Further, the above-mentioned cyclic ether compound is preferably a combination of one or more hydroxyl-functional cyclic ether compounds compatible with water and a cyclic ether compound having no hydroxyl functional group, and the hydroxyl-functional cyclic ether compound is preferably a hydroxyl-containing oxetane compound.
Preferably, as the hydroxyl group-containing oxetane compound, at least one compound having a structure represented by the following general formula I:
wherein,,
R 1 represents hydrogen or C 1 -C 6 Alkyl of (a);
R 2 represents C 1 -C 80 Linear or branched m+n-valent alkyl or alkenyl groups, optionally (optionally), one or more of the alkyl or alkenyl groups-CH 2 Can be each independently replaced by-O-, -COO-, -OCO-, 1, 4-phenylene,Substituted, provided that-O-is not directly attached, and optionally, R 2 May also contain at least one epoxy group;
n represents an integer of 1 to 6;
m represents an integer of 1 to 6.
As a preferred embodiment, in the above structure of formula I:
R 1 represents hydrogen or C 1 -C 4 Alkyl of (a);
R 2 represents C 1 -C 60 Linear or branched m+n-valent alkyl or alkenyl groups of (a) optionally, -CH of one or more of the alkyl or alkenyl groups 2 Can be each independently replaced by-O-, -COO-, -OCO-, 1, 4-phenylene,Substituted, provided that-O-is not directly attached, and optionally, R 2 An epoxy group is attached to at least one end;
n represents 1,2, 3 or 4;
m represents 1,2, 3 or 4.
Illustratively, the oxetane compound may be selected from compounds having the following structure:
the content of the cationically polymerizable compound of component (a) in the total amount of 100 parts by mass is 30 to 95 parts by mass, preferably 60 to 90 parts by mass.
As component (B), the superacid is preferably M - 、ClO 4 - 、CN - 、HSO 4 - 、NO 3 - 、CF 3 COO - 、(BM 4 ) - 、(SbM 6 ) - 、(AsM 6 ) - 、(PM 6 ) - 、Al[OC(CF 3 ) 3 ] 4 - 、HSO 3 - 、FSO 3 - 、CF 3 SO 3 - 、B(C 6 M 5 ) 4 - Or [ (Rf) b PF 6-b ] - At least one of the acids being anionic, wherein M represents halogen (e.g., fluorine, chlorine, bromine, iodine), b represents an integer of 1 to 5, rf may be the same or different and each independently represents an alkyl group having 80% or more of the hydrogen atoms replaced with fluorine atoms.
Further preferably, the anion of the super acid is selected from BF 4 - 、ClO 4 - 、FSO 3 - 、PF 6 - 、AsF 6 - 、SbF 6 - 、CF 3 SO 3 - 、B(C 6 H 5 ) 4 - 、B(C 6 F 5 ) 4 - . Illustratively, the super acid may be hexafluorophosphoric acid, hexafluoroantimonic acid, tetrafluorophenyl boric acid, hexafluoroarsinic acid, and the like.
The content of the superacid of the component (B) is 0.1 to 10 parts by mass, preferably 0.5 to 5 parts by mass, in the total amount of 100 parts by mass of the cationic curable composition.
As component (C), water is used as a diluent for controlling the viscosity and ensuring a certain stability of the composition. The water is not particularly limited, and deionized water is preferable.
The content of water of component (C) in the total amount of 100 parts by mass of the cationic curable composition is 1 to 99 parts by mass, preferably 5 to 40 parts by mass.
Further, organic and/or inorganic additives commonly used in the art, including but not limited to solvents, fillers, leveling agents, dispersants, defoamers, pigments, dyes, surfactants, solvents, etc., may also be optionally added to the curable composition of the present application depending on the product application requirements, as is conventional technology readily understood and ascertained by those skilled in the art.
Furthermore, the components of the application can be directly applied after being mixed, can be stored for a certain time and can be applied after being mixed, or partial components can be prepared into prepreg firstly and are further mixed during application.
The cationic curable composition of the present application has higher enhanced reactivity, lower viscosity and excellent yellowing resistance. The components in the formula form a single-phase mixture, so that the rheological property is strong, and the composition can be suitable for various application scenes.
Detailed Description
The present application will be described in further detail with reference to specific examples, which should not be construed as limiting the scope of the application.
1. Evaluation of essential Properties of curable compositions
The components were uniformly mixed according to the formulations shown in table 1 to obtain curable compositions. The amounts indicated in the examples are parts by weight.
TABLE 1
1. Viscosity of the mixture
The curable composition was tested for viscosity at 25℃using a viscometer (DV-1).
2. Curing time
The curable composition was applied to a tin plate substrate using a 15 μm bar to form a coating about 10 μm thick. The sample was then placed in an 80 ℃ oven and the minimum time required for the coating to touch the surface was recorded. The shorter the time, the faster the cure speed.
3. Hardness of
The hardness of the cured films was tested with reference to GB T6739-1996.
4. Adhesion force
Referring to GB 1720-1979, the adhesion of cured films was tested.
The evaluation results are recorded in table 2.
TABLE 2
The evaluation results show that: the cationic curable composition of the application has low viscosity, strong rheological property and good operability; the coating layer after application had a short curing time, examples 6, 9 and 10 were only 30s, and the cured film was high in hardness and adhesion, exhibiting excellent curing properties.
2. Comparison of yellowing Properties of aqueous Strong acid curing and cationic photo curing
The curable compositions of examples 11-13 and comparative examples 1-3 were formulated according to the formulations shown in Table 3, and then the compositions were manually applied to tin substrates through 30 μm applicator bars, respectively, and the coating thickness after drying was about 20. Mu.m.
The samples of examples 11-13 were cured into films by heating at 80℃for 1min, and the samples of comparative examples 1-3 were given 2000mj/cm by a high pressure mercury lamp (model: RW-UVATP 201-20) 2 Is cured into a film by ultraviolet radiation. The yellowing Δb values before and after curing were tested using a alicylic color difference meter (model: ci 7600).
TABLE 3 Table 3
Remarks: cationic initiator 6990 is a mixed triarylsulfonium hexafluorophosphate salt, commercially available from Strong electronics New Material Co., ltd.
The test results show that the cationic curable compositions of the present application have significant advantages in terms of resistance to yellowing, the yellowing Δb value being lower by an integer of one order of magnitude, compared to photocurable waterborne coatings.
3. Coloring system curability contrast
The curable compositions of examples 14-16 and comparative examples 4-6 were formulated according to the formulations shown in Table 4, and then the compositions were manually applied to tin substrates via 30 μm applicator bars, respectively, and dried to a coating thickness of about 20 μm.
The samples of examples 14-16 were heated at 80℃for 1min, and the samples of comparative examples 4-6 were given 2000mJ/cm by a high pressure mercury lamp (model: RW-UVATP 201-20) 2 Is a radiation source for ultraviolet radiation. Cured film formation was evaluated by finger touch.
TABLE 4 Table 4
Remarks: pigment blue 60, tin-free ocean chemical industry, inc.
The test results show that the coloring system has a great effect on the photocuring film forming property, and when the concentration of the coloring agent is high (such as comparative examples 5 and 6), the coating of the composition cannot be cured into a film; the application of the curable composition of the application is not affected, can form a film smoothly, and has obvious advantages compared with the photo-curing water-based paint.
The above description is not intended to limit the application to the particular embodiments disclosed, but on the contrary, the intention is to cover all modifications, alternative constructions, and alternatives falling within the spirit and principles of the application.

Claims (3)

1. A cationic curable composition comprising the following components:
(A) A cationically polymerizable compound, the cationically polymerizable compound being a cyclic ether compound;
(B) Super acid, said super acid is M - 、ClO 4 - 、CN - 、HSO 4 - 、NO 3 - 、CF 3 COO - 、(BM 4 ) - 、(SbM 6 ) - 、(AsM 6 ) - 、(PM 6 ) - 、Al[OC(CF 3 ) 3 ] 4 - 、HSO 3 - 、FSO 3 - 、CF 3 SO 3 - 、B(C 6 M 5 ) 4 - Or [ (Rf) b PF 6-b ] - At least one kind of acid which is anionic, wherein M represents halogen, b represents an integer of 1-5, rf, which may be the same or different, each independently represents an alkyl group in which 80% or more of hydrogen atoms are replaced with fluorine atoms;
(C) Water;
the cyclic ether compound is a combination of one or more water-compatible hydroxy-functionalized cyclic ether compounds and a cyclic ether compound that does not contain a hydroxy-functional group, the hydroxy-functionalized cyclic ether compound being a hydroxy-containing oxetane compound;
as the hydroxyl group-containing oxetane compound, at least one of compounds having a structure represented by the following general formula I is contained:
wherein,,
R 1 represents hydrogen or C 1 -C 6 Alkyl of (a);
R 2 represents C 1 -C 80 Linear or branched m+n-valent alkyl or alkenyl groups of (a) optionally, -CH of one or more of the alkyl or alkenyl groups 2 Can be each independently replaced by-O-, -COO-, -OCO-, 1, 4-phenylene,Substituted, provided that-O-is not directly attached, and optionally, R 2 May also contain at least one epoxy group;
n represents an integer of 1 to 6;
m represents an integer of 1 to 6.
2. The cationic curable composition according to claim 1, wherein in the structure of formula I:
R 1 represents hydrogen or C 1 -C 4 Alkyl of (a);
R 2 represents C 1 -C 60 Linear or branched m+n-valent alkyl or alkenyl groups of (a) optionally, -CH of one or more of the alkyl or alkenyl groups 2 Can be each independently replaced by-O-, -COO-, -OCO-, 1, 4-phenylene,Substituted, provided that-O-is not directly attached, and optionally, R 2 An epoxy group is attached to at least one end;
n represents 1,2, 3 or 4;
m represents 1,2, 3 or 4.
3. The cationic curable composition according to claim 1, wherein: the anion of the super acid is selected from BF 4 - 、ClO 4 - 、FSO 3 - 、PF 6 - 、AsF 6 - 、SbF 6 - 、CF 3 SO 3 - 、B(C 6 H 5 ) 4 - 、B(C 6 F 5 ) 4 - 。
CN202011029144.1A 2020-09-27 2020-09-27 Cationic curable composition Active CN114316240B (en)

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CN119661478B (en) * 2025-02-19 2025-09-16 广东工业大学 Active hybrid monomer, preparation method thereof, hybrid curing solder resist ink containing monomer and application of monomer

Citations (4)

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Publication number Priority date Publication date Assignee Title
CN1344302A (en) * 1998-12-11 2002-04-10 太阳化学公司 Radiation curable water based cationic inks and coatings
CN103354829A (en) * 2010-12-23 2013-10-16 好利获得股份公司 Bicomponent reactive ink for ink jet printing
CN105143375A (en) * 2013-03-15 2015-12-09 汉高知识产权控股有限责任公司 Two-part, cyanoacrylate/cationically curable adhesive systems
CN105873974A (en) * 2013-08-27 2016-08-17 汉高股份有限及两合公司 Curable composition and its use for electronic devices

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Publication number Priority date Publication date Assignee Title
TWI428389B (en) * 2007-10-31 2014-03-01 Dainippon Ink & Chemicals Activated energy ray curable composition and process for producing the same
KR20150052347A (en) * 2012-06-19 2015-05-13 나토코 가부시키가이샤 An active energy ray curable composition, and cured product and use thereof
CN104447635B (en) * 2014-10-31 2017-09-15 常州强力电子新材料股份有限公司 A kind of ester compounds of oxetane group-containing and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1344302A (en) * 1998-12-11 2002-04-10 太阳化学公司 Radiation curable water based cationic inks and coatings
CN103354829A (en) * 2010-12-23 2013-10-16 好利获得股份公司 Bicomponent reactive ink for ink jet printing
CN105143375A (en) * 2013-03-15 2015-12-09 汉高知识产权控股有限责任公司 Two-part, cyanoacrylate/cationically curable adhesive systems
CN105873974A (en) * 2013-08-27 2016-08-17 汉高股份有限及两合公司 Curable composition and its use for electronic devices

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