CN117486724A - Ester compound and preparation method and application thereof - Google Patents
Ester compound and preparation method and application thereof Download PDFInfo
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- CN117486724A CN117486724A CN202311437073.2A CN202311437073A CN117486724A CN 117486724 A CN117486724 A CN 117486724A CN 202311437073 A CN202311437073 A CN 202311437073A CN 117486724 A CN117486724 A CN 117486724A
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- -1 Ester compound Chemical class 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000113 cyclohexyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 5
- 125000001995 cyclobutyl group Chemical class [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims abstract description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 25
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 24
- 239000003153 chemical reaction reagent Substances 0.000 claims description 11
- 238000010521 absorption reaction Methods 0.000 claims description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 150000001555 benzenes Chemical group 0.000 claims description 7
- 239000002250 absorbent Substances 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- MFGOFGRYDNHJTA-UHFFFAOYSA-N 2-amino-1-(2-fluorophenyl)ethanol Chemical compound NCC(O)C1=CC=CC=C1F MFGOFGRYDNHJTA-UHFFFAOYSA-N 0.000 claims description 4
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 4
- 230000002745 absorbent Effects 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 4
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Inorganic materials [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 claims description 4
- 150000001935 cyclohexenes Chemical class 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- 239000005022 packaging material Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000004745 nonwoven fabric Substances 0.000 claims 1
- 239000000123 paper Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 3
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 abstract 1
- 230000002159 abnormal effect Effects 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000011521 glass Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 235000009161 Espostoa lanata Nutrition 0.000 description 2
- 240000001624 Espostoa lanata Species 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001934 cyclohexanes Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid group Chemical group C(CC(=O)O)(=O)O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000004996 alkyl benzenes Chemical group 0.000 description 1
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000325 methylidene group Chemical class [H]C([H])=* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3324—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/20—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing organic materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/75—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/80—Phthalic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3324—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic
- C08G65/3326—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof cyclic aromatic
-
- 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
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Abstract
The invention relates to the technical field of novel materials, in particular to an ester compound and a preparation method and application thereof; the ester compound has a structure shown in the following formula I: wherein Y is selected fromR 1 As the outermost end groupN is an integer between 1 and 100; m is any one of substituted cyclopropane, substituted cyclobutane, substituted cyclopentane, substituted cyclohexane, substituted cyclohexene, substituted benzene ring or benzene ring; r is R 1 Selected from substituted benzene rings, C 1 ～C 10 Alkyl or C of (2) 2 ～C 10 Any one of alkenyl groups of (2); the ester compound provided by the invention has good water absorbability through the structure of the ester and the structure of a plurality of ether bonds, and the compound with the structure shown in the formula I has more excellent performance under the specific chain length.
Description
Technical Field
The invention relates to the technical field of novel materials, in particular to an ester compound and a preparation method and application thereof.
Background
The trimethylolpropane forms ester polymers and has very wide application fields. For example, the product can be applied to the fields of sanitary products, storage packages, medicaments, cosmetics and the like.
Such materials have been disclosed in the prior art as a number of related compounds.
CN03818837.6 discloses a novel (meth) acrylate related to polyalkoxylated trimethylol propane of the general formula wherein EO is O-CH 2 -CH 2 PO is in each case independently O-CH 2 -CH(CH 3 ) -or O-CH (CH) 3 )-CH 2 -n1+n2+n3 is 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59 or 60, m1+m2+m3 is 4,5,6,7,8,9, 10, 11, 12 or 13; r1, R2, R3 are independently H or CH 3 . The preparation method adopted by the method comprises the following steps: the alkoxylated trimethylolpropane is reacted with (meth) acrylic acid in the presence of at least one esterification catalyst and at least one polymerization inhibitor and optionally a water-azeotropic solvent to form an ester.
EP0506617A2 discloses a use as crosslinker in powder coatings based on polyester resins reacted with epoxide groups involving polyglycidyl compounds which are polyglycidyl esters having the following structure:
wherein R is 1 、R 2 、R 3 And R is 4 Independently of one another, hydrogen, C 1 -C 4 -alkyl or the following groups:
wherein A is a polymethylene group having 2 to 4 carbon atoms and R5 and R6 are each independently of the other hydrogen, C1-C4-alkyl, A-containing radicals or together unsubstituted or C1-C4-alkyl-substituted methylene or polymethylene groups having 2 to 7 carbon atoms, but at least two of the radicals R1 to R6 are A-containing radicals.
US4774267a discloses a compound having the structure which belongs to a prepolymer type methacrylate compound having a multifunctional group.
Therefore, the compounds provided by the method have insufficient water absorption performance, and aiming at the defects, a novel ester compound needs to be provided.
Disclosure of Invention
The invention aims to solve the technical problem that the water absorption performance of the existing compound is insufficient, and provides an ester compound, a preparation method and application thereof aiming at the defects in the prior art.
In order to solve the technical problems, the invention provides an ester compound, which is characterized in that: the ester compound has a structure shown in the following formula I:
wherein Y is selected fromR 1 As the outermost end group, n is takenAn integer having a value of 1 to 100 (e.g., 1, 10, 20, 30, 40, 50, 60, 70, 80, 90, 100, etc.);
m is any one of substituted cyclopropane, substituted cyclobutane, substituted cyclopentane, substituted cyclohexane, substituted cyclohexene, substituted benzene ring or benzene ring;
R 1 selected from substituted benzene rings, C 1 ～C 10 Alkyl or C of (2) 2 ～C 10 Any one of alkenyl groups of (a).
The ester compound provided by the invention has good water absorbability through the structure of the ester and the structure of a plurality of ether bonds, and the compound with the structure shown in the formula I has more excellent performance under the specific chain length.
In the present invention, "substituted" means that: a group may be substituted with a conventional organic group. For example: the substituted benzene ring may be an alkyl-substituted benzene ring, a benzene ring substituted with a branched group, or the like, and may be any substituted benzene ring as long as it conforms to the conventional art.
C 1 ～C 10 An alkyl group of (C) 1 、C 2 、C 3 、C 4 、C 5 、C 6 、C 7 、C 8 、C 9 Or C 10 And alkyl groups, which may be straight-chain alkyl groups or branched-chain alkyl groups.
C 2 ～C 10 Alkenyl of (2), which may be C 2 、C 3 、C 4 、C 5 、C 6 、C 7 、C 8 、C 9 Or C 10 And alkenyl groups, which may be branched alkenyl groups or branched alkenyl groups.
In some embodiments, M is any one of a substituted cyclohexane, substituted cyclohexene, substituted benzene ring, or benzene ring. When M selects these groups, it has more excellent stability.
Preferably, said R 1 Is C 1 ～C 10 Alkyl or C of (2) 2 ～C 10 Any one of alkenyl groups of (a). Compared with R 1 When other groups are selected, C is selected 1 ～C 10 Alkyl or C of (2) 2 ～C 10 The alkenyl of the formula I can ensure that the compound with the structure shown in the formula I has better water absorption and rigidity.
Preferably, n has a value of 1 to 50.
Further, in some embodiments, the M is cyclohexane, cyclohexene, or a benzene ring.
Preferably, said R 1 Is C 2 ～C 4 Alkenyl groups of (c).
Preferably, n has a value of 1 to 10. When the value of n is within the range, the compound shown in the formula I has better water absorption effect.
As a preferred embodiment, the most preferred compounds of the present invention have the structure shown in formula II below:
in a second aspect, the present invention provides a method for preparing the ester compound according to the first aspect, the method comprising:
the values of formula V, M, Y and n are in the same range as in claim 1;
(1) Reacting a compound shown in a formula III with a compound shown in a formula IV in the presence of a first alkaline reagent to obtain an intermediate compound a;
(2) And (3) reacting the intermediate compound a obtained in the step (1) with a compound shown in the formula V in the presence of a second alkaline reagent to obtain an ester compound shown in the formula I.
Preferably, the mass ratio of the compound shown in the formula III to the compound shown in the formula IV in the step (1) is 1:3.1-3.5, for example, 1:3.1, 1:3.2, 1:3.3, 1:3.4 or 1:3.5. In the present invention, the amount of the material of the reaction raw material is preferably 3 times the compound of the formula IV in a slight excess, so that the residue after the reaction is less, and the post-treatment of the reaction is facilitated.
The esterification reaction of step (1) may comprise a stirred reactor, more preferably a device with distillation means and a condenser. The distillation apparatus may be a simple distillation apparatus or a complicated distillation apparatus such as a rectifying column. During distillation, an inert gas may be introduced as a protective gas.
Preferably, the first alkaline reagent in step (1) comprises any one or a combination of at least two of potassium hydroxide, cesium hydroxide, sodium bicarbonate, sodium carbonate, or cesium carbonate. In the present invention, the condensation is generally carried out by selecting an alkaline reagent, and the alkaline reagent itself has a strong water absorption property, so that the effect of promoting the reaction is good. However, the present invention is not limited to the above-mentioned alkaline reagent, and any reagent that can promote the forward reaction in step (1) may be used. In addition, the reaction of step (1) is generally carried out by distillation to obtain the product.
Preferably, the solvent of the reaction in step (1) is water and/or dioxane.
The reaction temperature in the step (1) of the present invention is not particularly limited, and a person skilled in the art can adjust the reaction temperature according to actual reaction conditions, the reaction temperature can be 40-160 ℃, and the temperature can be constant or gradually increased in the reaction process.
Preferably, the ratio of the amount of the intermediate compound a to the compound of formula V in step (2) is 1:3.1 to 3.5, for example, 1:3.1, 1:3.2, 1:3.3, 1:3.4 or 1:3.5.
Preferably, the second alkaline agent in step (2) comprises any one or a combination of at least two of potassium hydroxide, cesium hydroxide, sodium bicarbonate, sodium carbonate or cesium carbonate.
Preferably, the solvent of the reaction in step (2) is water and/or dioxane.
The reaction temperature in the step (2) is not particularly limited, and a person skilled in the art can adjust the reaction temperature according to actual reaction conditions, the reaction temperature can be 40-160 ℃, and the temperature can be constant or gradually increased in the reaction process.
The reaction of the step (1) and the step (2) is generally carried out for 1 to 48 hours, and the reaction is kept in a reflux state in the reaction process.
In a third aspect, the present invention provides a composition having water absorbability comprising the ester compound according to the first aspect.
In a fourth aspect, the present invention provides the use of an ester compound according to the first aspect or a composition having water absorbability according to the third aspect for the preparation of a water absorbent product.
Preferably, the absorbent product comprises toilet paper, packaging material or nonwoven.
The implementation of the invention has the following beneficial effects:
the ester compound provided by the invention has good water absorbability through the structure of the ester and the structure of a plurality of ether bonds, and the compound with the structure shown in the formula I has more excellent performance under the specific chain length.
Detailed Description
For the purpose of making the objects, technical solutions and advantages of the embodiments of the present invention more apparent, the technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is apparent that the described embodiments are some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
This example prepared compound S1 of formula II by the following procedure
(1) Reflux-reacting 1mol of a compound shown in a formula III with 3.1mol of a compound shown in IVa in the presence of 4mol of potassium hydroxide at 120 ℃ for 8 hours in a mixed solvent consisting of water and dioxane to obtain an intermediate compound a1;
(2) And (3) carrying out reflux reaction on 1mol of the intermediate compound a1 obtained in the step (1) and 3.1mol of a compound shown as Va in the presence of potassium hydroxide at 120 ℃ for 8 hours in a mixed solvent consisting of water and dioxane to obtain the compound shown as the formula II.
Example 2
In this example, an ester compound s2 was prepared by the following steps
(1) Reflux-reacting 1mol of a compound shown in a formula III with 3.1mol of a compound shown in IVb in the presence of 4mol of potassium hydroxide at 120 ℃ for 8 hours in a mixed solvent consisting of water and dioxane to obtain an intermediate compound a1;
(2) And (3) carrying out reflux reaction on 1mol of the intermediate compound a2 obtained in the step (1) and 3.1mol of a compound shown as Va in the presence of potassium hydroxide at 120 ℃ for 8 hours in a mixed solvent consisting of water and dioxane to obtain a compound s2.
Example 3 and example 4
The procedure is essentially the same as in example 1, except that IVc and IVd are substituted for IVa, the compound s3 and compound s4 are prepared, and the structures of IVc and IVd and s3 and s4 are as follows:
example 5 and example 6
Substantially the same procedure as in example 1 was repeated, except that the compound represented by Va in step (2) was replaced with Vb and Vc to prepare compounds s5 and s6, wherein the structures of Vb and Vc and s5 and s6 were as follows:
comparative example 1
This comparative example is substantially the same as example 1, except that the compound Va in step (2) is replaced with Vz, and the structures of the prepared compounds s10, vz and s10 are specifically as follows:
comparative example 2
This comparative example is essentially the same as example 1, except that the compound IVa in step (1) is replaced with malonic acid to prepare compound s11, s11 having the following structure:
the material of the invention is subjected to comparison test by adopting the following UV curing ink test formula for glass processing: 10% of the compound provided in the examples and the comparative examples, 3% of an organic pigment, 25% of polyurethane acrylate, 30% of polyester acrylate resin, 10% of diatomite powder, 10% of propylene glycol methyl ether acetate, 1% of polydimethylsiloxane, 3% of a silane coupling agent KH-550% and 8% of 1-hydroxycyclohexyl phenyl ketone. The specific test results are shown in table 1 below:
the testing method comprises the following steps: hundred grid method, dividing the space between 1mm,100% attachment; using cotton balls soaked with alcohol, wiping 50 times under 300 g pressure, and having no abnormal shape; the cotton balls were soaked with saline and rubbed 50 times under 300 g pressure without any difference.
TABLE 1
| Attachment to | Water resistance | Alkali fade (second) | |
| Example 1 | 100％ | No abnormal shape | 180 |
| Example 2 | 100％ | No abnormal shape | 173 |
| Example 3 | 100％ | No abnormal shape | 193 |
| Example 4 | 100％ | No abnormal shape | 182 |
| Example 5 | 100％ | No abnormal shape | 173 |
| Example 6 | 100％ | No abnormal shape | 185 |
| Comparative example 1 | 90％ | No abnormal shape | 205 |
| Comparative example 2 | 100％ | Wrinkling | 130 |
The water absorption performance test is carried out by the compounds provided by the examples and the comparative examples, and the products provided by the examples of the invention are found to have better water absorption performance. And when the structure of the compound is changed, the water absorption performance is reduced.
Hydrophilic properties are understood to be required according to the water absorption properties.
The contrast introduces a cyclic rigid structure, balances the UV curing rate and the overall formula hydrolytic performance (a UV curing ink for organic glass processing and a preparation method thereof).
The beneficial effects of the invention are as follows: the product structure disclosed by the invention is applied to an ink formula to form a tough ink layer on the surface of glass, so that the original glass adhesion is maintained, the water resistance, the surface hardness and the scratch resistance are improved, the surface of the glass can be effectively ensured not to be scratched, and after the glass is processed, the UV light-cured ink layer can be quickly removed by using alkaline water, so that the glass cannot be influenced.
Finally, it should be noted that: the above embodiments are only for illustrating the technical solution of the present invention, and are not limiting; although the invention has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit and scope of the technical solutions of the embodiments of the present invention.
Claims (10)
1. An ester compound, characterized in that: the ester compound has a structure shown in the following formula I:
wherein Y is selected fromR 1 As the outermost end group, n is an integer between 1 and 100;
m is any one of substituted cyclopropane, substituted cyclobutane, substituted cyclopentane, substituted cyclohexane, substituted cyclohexene, substituted benzene ring or benzene ring;
R 1 selected from substituted benzene rings, C 1 ～C 10 Alkyl or C of (2) 2 ～C 10 Any one of alkenyl groups of (a).
2. The ester compound according to claim 1, wherein: the M is any one of substituted cyclohexane, substituted cyclohexene, substituted benzene ring or benzene ring;
preferably, said R 1 Is C 1 ～C 10 Alkyl or C of (2) 2 ～C 10 Any one of alkenyl groups of (2);
preferably, n has a value of 1 to 50.
3. The ester compound according to claim 1 or 2, characterized in that: m is cyclohexane, cyclohexene or benzene ring;
preferably, said R 1 Is C 2 ～C 4 Alkenyl of (c);
preferably, n has a value of 1 to 10.
4. An ester compound according to any one of claims 1 to 3, wherein: the compound has a structure shown in the following formula II:
5. the method for producing an ester compound according to any one of claims 1 to 4, characterized in that: the preparation method comprises the following steps:
m, Y and n have the same values as in claim 1;
(1) Reacting a compound shown in a formula III with a compound shown in a formula IV in the presence of a first alkaline reagent to obtain an intermediate compound a;
(2) And (3) reacting the intermediate compound a obtained in the step (1) with a compound shown in the formula V in the presence of a second alkaline reagent to obtain an ester compound shown in the formula I.
6. The method of manufacturing according to claim 5, wherein: the mass ratio of the compound shown in the formula III to the compound shown in the formula IV in the step (1) is 1:3.1-3.5;
preferably, the first alkaline reagent in step (1) comprises any one or a combination of at least two of potassium hydroxide, cesium hydroxide, sodium bicarbonate, sodium carbonate or cesium carbonate;
preferably, the solvent of the reaction in step (1) is water and/or dioxane.
7. The method of manufacturing according to claim 5 or 6, characterized in that: the ratio of the amount of the intermediate compound a to the amount of the compound represented by the formula V in the step (2) is 1:3.1-3.5;
preferably, the second alkaline reagent in step (2) comprises any one or a combination of at least two of potassium hydroxide, cesium hydroxide, sodium bicarbonate, sodium carbonate or cesium carbonate;
preferably, the solvent of the reaction in step (2) is water and/or dioxane.
8. A composition having water absorption properties, characterized in that: the water-absorbent composition comprising the ester compound according to any one of claims 1 to 4.
9. Use of the ester compound according to any one of claims 1 to 4 or the composition having water absorbability according to claim 8 for the production of an absorbent product.
10. The use according to claim 9, characterized in that: the absorbent product comprises toilet paper, packaging material or non-woven fabric.
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