KR102022410B1 - Silane compound having urea group and method for preparing the same - Google Patents
Silane compound having urea group and method for preparing the same Download PDFInfo
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- KR102022410B1 KR102022410B1 KR1020150151628A KR20150151628A KR102022410B1 KR 102022410 B1 KR102022410 B1 KR 102022410B1 KR 1020150151628 A KR1020150151628 A KR 1020150151628A KR 20150151628 A KR20150151628 A KR 20150151628A KR 102022410 B1 KR102022410 B1 KR 102022410B1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/10—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
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Abstract
The present application relates to a compound of Formula 1 and a method for preparing the same.
Description
The present application relates to a silane compound having a urea group and a preparation method thereof.
Among the UV curable adhesives, the radical curable adhesives are very vulnerable to moisture because the adhesion with the polarizer is mainly made of hydrogen bonds. Accordingly, the adhesive force may vary depending on the type of the substrate, the moisture content of the polarizing element, the change in humidity, and the like, thus making it difficult to secure stable physical properties. In addition, when the additive to help increase the adhesive strength to the adhesive composition is accompanied by a drop in glass transition temperature, there is a problem that the durability is weakened.
Accordingly, there is a need for the development of materials to improve adhesion and durability.
The present application provides a silane compound having a urea group and a method for preparing the same.
An exemplary embodiment of the present application provides a compound of Formula 1 below.
[Formula 1]
In Chemical Formula 1,
X1 and Y1 are the same as or different from each other, and each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, or
R1 to R3 are the same as or different from each other, hydrogen, hydroxy, substituted or unsubstituted alkoxy, substituted or unsubstituted aryloxy, or
L1, L2, L3, L4, L5, L12 and L13 are the same as or different from each other, and each independently substituted or unsubstituted alkylene, substituted or unsubstituted arylene, substituted or unsubstituted alkylarylene, or substituted Or unsubstituted arylalkylene,
X2, Y2, X5 and Y5 are the same as or different from X1 or Y1, and are as defined in X1 and Y1,
R5, R6, R7, R21 and R22 are each independently the same as or different from R1 to R4, and are as defined in R1 to R4,
R4 and R13 are the same as or different from each other, and each independently hydrogen, substituted or unsubstituted alkyl, or substituted or unsubstituted aryl,
Z1, Z2, Z5 and Z6 are the same as or different from each other, and each independently O, NR or S, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl,
However, X1
According to another exemplary embodiment of the present application, Chemical Formula 1 may be represented by the following Chemical Formula 1-1 or 1-2.
[Formula 1-1]
[Formula 1-2]
In Chemical Formulas 1-1 and 1-2, the substituents are as defined in Chemical Formula 1.
Another exemplary embodiment of the present application provides a method of preparing the compound of Formula 1, which includes reacting a compound having an isocyanate functional group with a silane compound including an amine.
Since the compound according to the exemplary embodiments of the present application has a silane group and at the same time includes a urea group and a (meth) acrylate functional group, the polarizing element is excellent in reactivity with the hydroxyl group of the polarizing element by a urea group compared to a material having only an alkyl silane group. It is easy to form a covalent bond with, it is possible to secure excellent adhesion. This makes the distance between the hydroxy group and the silane group of the polarizing element physically close by the electron cloud of the non-shared electron pair of urea group, which makes the formation of covalent bonds more advantageous than the case where no urea group is included. In addition, in general, when adding a monomer to help increase the adhesion, accompanied by a drop in glass transition temperature, although the compound of Formula 1 is added to the adhesive composition there is no increase or decrease in the glass transition temperature adhesive layer excellent in durability Can be provided.
1 and 2 show the synthesis confirmation data of the compound prepared in Synthesis Example 1.
An exemplary embodiment of the present application provides the compound of Formula 1, 1-1 or 1-2 described above.
In this specification, "substituted or unsubstituted" means substituted with alkyl, aryl, hydroxy, alkoxy or aryloxy or has no further substituent.
In the present specification, alkyl includes linear or branched alkyl, for example, alkyl having 1 to 20 carbon atoms, specifically 1 to 6 carbon atoms, such as methyl, ethyl, propyl, and the like.
In the present specification, alkoxy includes linear or branched alkoxy, for example, alkoxy having 1 to 20 carbon atoms, specifically 1 to 6 carbon atoms, such as methoxy, ethoxy, propoxy and the like.
In the present specification, aryl includes monocyclic or polycyclic aryl, and for example, aryl having 6 to 20 carbon atoms, specifically 6 to 12 carbon atoms, such as phenyl, biphenyl, naphthyl and anthryl.
In the present specification, aryloxy is an oxy group having a monocyclic or polycyclic aryl, for example, having an aryl group having 6 to 20 carbon atoms, specifically 6 to 12 carbon atoms, such as phenyl, biphenyl, naphthyl and anthryl. Can be.
In the present specification, alkylene includes linear or branched alkylene, for example, alkylene having 1 to 20 carbon atoms, specifically 1 to 6 carbon atoms, such as methylene, ethylene, propylene, and the like.
In the present specification, arylene includes monocyclic or polycyclic arylene, and for example, arylene having 6 to 20 carbon atoms, specifically 6 to 12 carbon atoms, such as phenylene, biphenylene, naphthylene, anthylene, etc. have.
In the present specification, the alkylarylene includes monocyclic or polycyclic arylene substituted with linear or branched alkyl, and for example, 6 to 20 carbon atoms substituted with alkyl having 1 to 20 carbon atoms, specifically 1 to 6 carbon atoms, Specifically, arylene has 6 to 12 carbon atoms.
In the present specification, arylalkylene includes linear or branched alkylene substituted with monocyclic or polycyclic aryl, and for example, 6 to 20 carbon atoms, specifically 1 to 20 carbon atoms substituted with aryl having 6 to 12 carbon atoms. Specifically, there is alkylene having 1 to 6 carbon atoms.
According to another exemplary embodiment of the present application, Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3.
[Formula 2]
In Chemical Formula 2,
R1 to R7, L1 to L5, Y1, Y2, Z1 and Z2 are as defined in Formula 1, n is an integer of 0 to 3,
L6, L7 and L8 are the same as or different from each other, and are each independently substituted or unsubstituted alkylene, substituted or unsubstituted arylene, substituted or unsubstituted alkylarylene, or substituted or unsubstituted arylalkylene ,
Z3 is O, NR or S, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl,
R8 to R10 are the same as or different from each other, and each independently hydrogen, a hydroxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group,
X3 and Y3 are the same as or different from each other, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
[Formula 3]
In Chemical Formula 3,
R1 to R7, L1 to L5, Y1, X2, Z1 and Z2 are as defined in Formula 1, m is an integer of 0 to 3,
L9, L10 and L11 are the same as or different from each other, and are each independently substituted or unsubstituted alkylene, substituted or unsubstituted arylene, substituted or unsubstituted alkylarylene, or substituted or unsubstituted arylalkylene. ,
Z 4 is O, NR or S, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl,
R11 to R13 are the same as or different from each other, and each independently hydrogen, a hydroxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group,
X4 and Y4 are the same as or different from each other, and are each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl.
According to another exemplary embodiment of the present application, Chemical Formula 2 may be represented by the following Chemical Formula 4 or 5.
[Formula 4]
[Formula 5]
In Chemical Formulas 4 and 5, the substituents are as defined in Chemical Formula 2.
According to another exemplary embodiment of the present application, Chemical Formula 3 may be represented by the following Chemical Formula 6 or 7.
[Formula 6]
[Formula 7]
In Formulas 6 and 7, R14 to R16 are the same as or different from each other, and are each independently hydrogen, a hydroxy group, a substituted or unsubstituted alkoxy group, or a substituted or unsubstituted aryloxy group.
According to yet an embodiment of the present application, Formula 1 may be represented by the following formula (8).
[Formula 8]
In Chemical Formula 8, the substituent is as defined in Chemical Formula 1.
According to another exemplary embodiment of the present application, Chemical Formula 8 may be represented by the following Chemical Formula 9 or 10.
[Formula 9]
[Formula 10]
In Chemical Formulas 9 and 10,
n and m are the same as or different from each other, and each independently an integer of 0 to 3,
L6, L7, L8, L9, L10 and L11 are the same as or different from each other, and each independently substituted or unsubstituted alkylene, substituted or unsubstituted arylene, substituted or unsubstituted alkylarylene, or substituted or unsubstituted Ring arylalkylene,
Z3 and Z4 are the same as or different from each other, and each independently O, NR or S, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl,
R8 to R13 are the same as or different from each other, and each independently hydrogen, a hydroxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group,
X3, Y3, X4 and Y4 are the same as or different from each other, and each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl,
Other substituents are as defined in formula (1).
According to another exemplary embodiment of the present application, Chemical Formula 8 may be represented by the following Chemical Formula 11 or 12.
[Formula 11]
[Formula 12]
In Chemical Formulas 11 and 12,
n and m are the same as or different from each other, and each independently an integer of 0 to 3,
L6, L7, L8, L9, L10 and L11 are the same as or different from each other, and each independently substituted or unsubstituted alkylene, substituted or unsubstituted arylene, substituted or unsubstituted alkylarylene, or substituted or unsubstituted Ring arylalkylene,
Z3 and Z4 are the same as or different from each other, and each independently O, NR or S, R is hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl,
R8 to R13 are the same as or different from each other, and each independently hydrogen, a hydroxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aryloxy group,
X3, Y3, X4 and Y4 are the same as or different from each other, and each independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl,
Other substituents are as defined in formula (1).
According to yet an embodiment of the present application, in the above formulas 1 to 12, X1 to X5 and Y1 to Y5 are hydrogen.
According to yet an embodiment of the present application, in the general formula 1, 1-1, 2 to 7, at least one of R1 to R3 is alkoxy.
According to yet an embodiment of the present application, in the general formula 1, 1-1, 2 to 7, R1 to R3 is alkoxy.
According to yet an embodiment of the present application, in the general formula 1, 1-1, 2 to 7, R1 is hydroxy, R2 and R3 is alkoxy.
According to yet an embodiment of the present application, in the general formula 1, 1-1, 2 to 12, at least one of R5 to R7 is alkoxy.
According to yet an embodiment of the present application, in the general formula 1, 1-1, 2 to 12, R5 to R7 is alkoxy.
According to yet an embodiment of the present application, in the general formula 1, 1-1, 2 to 12, R5 is hydroxy, R6 and R7 is alkoxy.
According to yet an embodiment of the present application, in the general formula (2), 5, 9 and 11, at least one of R8 to R10 is alkoxy.
According to yet an embodiment of the present application, in the formula 2, 5, 9 and 11, R8 to R10 is alkoxy.
According to yet an embodiment of the present application, in the general formula (2), 5, 9 and 11, R8 is hydroxy, R9 and R10 is alkoxy.
According to yet an embodiment of the present application, in the general formula 3, 6, 7, 10 and 12, at least one of R11 to R13 is alkoxy.
According to yet an embodiment of the present application, in the general formula 3, 6, 7, 10 and 12, R11 to R13 is alkoxy.
According to yet an embodiment of the present application, in the general formula 3, 6, 7, 10 and 12, R11 is hydroxy, R12 and R13 is alkoxy.
According to yet an embodiment of the present application, in the general formula (7), at least one of R14 to R16 is alkoxy.
According to yet an embodiment of the present application, in the general formula 7 R14 to R16 is alkoxy.
According to yet an embodiment of the present application, in the general formula 7, R14 is hydroxy, R15 and R16 is alkoxy.
According to yet an embodiment of the present application, in the above formulas 1 to 12, Z1 to Z6 is O.
According to another exemplary embodiment of the present application, in the above Chemical Formulas 1 to 12, L1 to L13 are alkylene having 1 to 20 carbon atoms, such as 1 to 6 carbon atoms.
According to yet an embodiment of the present application, R4 and R13 is hydrogen or methyl.
According to yet an embodiment of the present application, R4 and R13 is hydrogen.
According to yet an embodiment of the present application, the compound of Formula 1 may be selected from the following structural formulas.
Another exemplary embodiment of the present application provides a method of preparing the compound of Formula 1, which includes reacting a compound having an isocyanate functional group with a silane compound including an amine.
Examples of the silane compound containing an amine include N-2- (aminoethyl) -3-aminopropyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltrimeth Methoxysilane, 3-ureidopropyltrialkoxysilane, 3-mercaptopropyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, and the like, but are not limited thereto. .
Examples of the compound having an isocyanate functional group include 2-isocyanatoethyl acrylate, 2-isocytate ethyl methacrylate, and the like, but are not limited thereto.
The production process proceeds by the reaction of forming a urea (urea) by the reaction of an isocyanate functional group and an amine, and is easily synthesized by strong reactivity. The above reaction is a strong exothermic reaction to maintain the temperature of the reactor at -10 ~ 40, preferably -2 ~ 25.
On the other hand, the content ratio of the silane compound containing an amine, such as 3-aminopropyltriethoxysilane and the compound having an isocyanate functional group, such as 2-isocyanatoethyl acrylate, proceeds at a molar ratio of 1: 1, or isocyanate functional group. It is preferable to proceed in a molar ratio of 1.1: 1 so that all of the compounds having The compound having an isocyanate functional group may be added dropwise to the silane compound containing the amine, and the dropping rate may be adjusted as necessary. During or after the dropwise addition of the compound having an isocyanate functional group, stirring may be performed, and stirring may be performed, for example, for 2 hours to 75 hours, more preferably for 4 hours to 24 hours. By determining the consumption of isocyanate and the production of urea through IR, it is possible to determine whether the reaction is terminated, and the structure of the composite can be analyzed through NMR analysis.
In the reaction, a solvent may be additionally used, and the type of the solvent is not particularly limited, and for example, THF (tetrahydrofuran), EA (ethyl acetate), AN (acetonitrile), or the like may be used.
Hereinafter, the present invention will be described in more detail. However, the following examples are only intended to illustrate the present invention, but are not intended to limit the scope of the present invention.
Synthesis Example One
3-aminopropyltriethoxysilane (KBE903, Shinetsu) and 2-isocyanatoethyl acrylate (Karenz AOI, Showadenko) were prepared in a molar ratio of 1.1: 1. The temperature of the reactor was set to −2 ° C., and 2-isocyateethyl acrylate was added dropwise to 3-aminopropyltriethoxysilane using a dropping funnel. At this time, the mixture was stirred at a speed of 200 rpm. After dropping, the mixture was stirred for 12 hours. IR was used to determine whether the compound synthesis reaction was terminated. Specifically, an isocyanate peak was observed at 2260cm-1 at the beginning of the reaction, and it was confirmed that the 2260cm-1 peak disappeared as the reaction proceeded, and urea production peaks were confirmed at 1560cm-1 and 1630cm-1. IR was used Excalibur 3100 (Varian) equipped with a diamond accessory (checked in reflection mode). NMR results of the synthesized compound are shown in FIGS. 1 and 2. The compound prepared in Synthesis Example 1 is referred to below as urea silane (US-1).
Synthesis Example 2
N-2- (aminoethyl) -3-aminopropylmethyltrimethoxysilane (KBE603, Shinetsu) and 2-isocyanatoethyl acrylate (Karenz AOI, Showadenko) were prepared in a molar ratio of 1.1: 1. . The temperature of the reactor was set at −2 ° C., and 2-isocyateethyl acrylate was added dropwise to N-2- (aminoethyl) -3-aminopropylmethyltrimethoxysilane dropwise using a dropping funnel. . At this time, the mixture was stirred at a speed of 200 rpm. After dropping, the mixture was stirred for 12 hours. In the same manner as in Synthesis Example 1, it was confirmed whether the compound synthesis reaction was terminated using IR. The compound prepared in Synthesis Example 2 is referred to below as urea silane (US-2).
Synthesis Example 3
3-ureidopropyltrialkoxysilane (KBE585, Shinetsu Co., Ltd.) and 2-isocyanatoethyl acrylate (Karenz AOI, Showadenko Co., Ltd.) were prepared in a molar ratio of 1.1: 1. The temperature of the reactor was set at −2 ° C., and 2-isocyateethyl acrylate was added dropwise to 3-ureidopropyltrialkoxysilane using a dropping funnel. At this time, the mixture was stirred at a speed of 200 rpm. After dropping, the mixture was stirred for 12 hours. The compound prepared in Synthesis Example 2 is referred to below as urea silane (US-3).
Synthesis Example 4
3-mercaptopropylmethyltrimethoxysilane (Mercaptopropylmethyltrimethoxysilane, KBE803, Shinetsu Co., Ltd.) and 2-isocyanatoethyl acrylate (Karenz AOI, Showadenko Co., Ltd.) were prepared in a molar ratio of 1.1: 1. The temperature of the reactor was set at −2 ° C., and 2-isocytateethyl acrylate was added dropwise to 33-mercaptopropylmethyltrimethoxysilane dropwise using a dropping funnel. At this time, the mixture was stirred at a speed of 200 rpm. After dropping, the mixture was stirred for 12 hours. The compound prepared in Synthesis Example 3 is referred to below as urea silane (US-4).
Urea Silane Hydroxide
2/3 of water and 100 ppm of triethylamine were added to US-1 at a molar ratio to pH 10-11 and stirred for 4 days. The material thus produced is referred to as US-1-H.
Example
Composition A
95 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 5 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition 3 parts by weight of irgacure-819 (Ciba). It added and manufactured the adhesive composition A for polarizing plates.
Composition B
95 parts by weight of N- (butoxymethyl) acrylamide and 5 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition, to which 3 parts by weight of irgacure-819 (Ciba), a radical initiator, was added. Adhesive Composition B was prepared.
Composition C
90 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 10 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition 3 parts by weight of irgacure-819 (Ciba). It added and manufactured the adhesive composition C for polarizing plates.
Composition D
90 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 10 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition, 1 part by weight of irgacure-819 (Ciba), a radical initiator. , 2 parts by weight of a photobase generator irgacure 907 (Ciba) was added to prepare an adhesive composition D for a polarizing plate.
Composition E
90 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 10 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition, 3 parts by weight of irgacure-819 (Ciba). , 0.5 parts by weight of the photobase generator WPBG 266 (Wako Pure Chemical Industries, Ltd.) and 0.5 parts by weight of 2-isopropylthioxanthone were added to prepare an adhesive composition E for a polarizing plate.
Composition F
90 parts by weight of N- (butoxymethyl) acrylamide and 10 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition, to which 3 parts by weight of irgacure-819 (Ciba), a radical initiator, was added. Adhesive composition F was prepared.
Composition G
90 parts by weight of N- (butoxymethyl) acrylamide and 10 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition, 1 part by weight of irgacure-819 (Ciba), a radical initiator, and photobase generation. 2 parts by weight of irgacure 907 (Ciba) was added to prepare an adhesive composition G for a polarizing plate.
Composition H
90 parts by weight of N- (butoxymethyl) acrylamide and 10 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition, 3 parts by weight of irgacure-819 (Ciba), a radical initiator, and photobase generation. 0.5 weight part of WPBG 266 (Wako Pure Chemical Industries, Ltd.) and 0.5 weight part of 2-isopropyl thioxanthones were added, and the adhesive composition H for polarizing plates was manufactured.
Composition I
50 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 50 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition, 3 parts by weight of irgacure-819 (Ciba). It added and manufactured the adhesive composition I for polarizing plates.
Composition J
80 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 20 parts by weight of urea silane (US-1) were added to 100 parts by weight of the resin composition 3 parts by weight of irgacure-819 (Ciba). It added and manufactured the adhesive composition J for polarizing plates.
Composition K
A radical initiator was added to 100 parts by weight of the resin composition prepared by adding 60% by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical), 20% by weight of 4-hydroxy butyl acrylate, and 20% by weight of urea silane (US-1). 3 parts by weight of phosphorus irgacure-819 (Ciba) was added to prepare an adhesive composition K for a polarizing plate.
Composition L
To 100 parts by weight of a resin composition prepared by adding 60% by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical), 20% by weight of N- (butoxylmethyl) acrylamide, and 20% by weight of urea silane (US-1) 3 parts by weight of a radical initiator irgacure-819 (Ciba) was added to prepare an adhesive composition L for a polarizing plate.
Composition M
Phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) 72.7% by weight, urea silane (US-1) 18.2% by weight, tri (acryloyloxy ethyl) phosphate was added to 100 parts by weight of the resin composition prepared 3 parts by weight of a radical initiator irgacure-819 (Ciba) was added to prepare an adhesive composition M for a polarizing plate.
Composition N
80 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 20 parts by weight of urea silane (US-2) were added to 100 parts by weight of the resin composition, 3 parts by weight of irgacure-819 (Ciba). It added and prepared adhesive composition N for polarizing plates.
Composition O
80 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 20 parts by weight of urea silane (US-3) were added to 100 parts by weight of the resin composition, 3 parts by weight of irgacure-819 (Ciba). It added and manufactured the adhesive composition O for polarizing plates.
Composition P
80 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 20 parts by weight of urea silane (US-4) were added to 100 parts by weight of the resin composition 3 parts by weight of irgacure-819 (Ciba). It added and manufactured the adhesive composition P for polarizing plates.
Composition Q
80 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 20 parts by weight of urea silane (US-1-H) were added to 100 parts by weight of the resin composition irgacure-819 (Ciba) 3 A weight part was added to prepare an adhesive composition Q for a polarizing plate.
Composition R
5 parts by weight of vinylimidazole, 100 parts by weight of a resin composition prepared by adding 80% by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 20% by weight of urea silane (US-1), irgacure- as a radical initiator 3 weight part of 819 (Ciba company) was added, and the adhesive composition R for polarizing plates was manufactured.
Composition S
80 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 20 parts by weight of urea silane (US-1) were added to 100 parts by weight of acetic acid and 100 parts of acetic acid, a radical initiator irgacure-819 (Ciba) 3 weight part was added and the adhesive composition S for polarizing plates was manufactured.
Composition T
80 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical), 20 parts by weight of urea silane (US-1) to 5 parts by weight of CPI 100P (Sanapro), a photoacid generator, 3 parts by weight of a radical initiator irgacure-819 (Ciba) was added to prepare an adhesive composition T for a polarizing plate.
Composition U
80 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) and 20 parts by weight of urea silane (US-1) were added to 100 parts by weight of 3,4-epoxycyclohexylmethyl-3,4 '. -5 parts by weight of epoxy cyclohexane carboxylate (Celloxide 2021P from Dicel), 5 parts by weight of CPI 100P (Sanapro), a photoacid generator, and 3 parts by weight of irgacure-819 (Ciba), a radical initiator, to prepare an adhesive composition U for a polarizing plate. Prepared.
Composition V
To 100 parts by weight of phenoxyl benzyl acrylate (Miramer M1122, Miwon Specialty Chemical) 3 parts by weight of a radical initiator irgacure-819 (Ciba) was added to prepare an adhesive composition V for a polarizing plate.
Composition W
To 100 parts by weight of N- (butoxymethyl) acrylamide, 3 parts by weight of irgacure-819 (Ciba), which is a radical initiator, was added to prepare an adhesive composition W for a polarizing plate.
Experimental Example 1-adhesion evaluation
The adhesion to the polarizer of the composition was measured and shown in the following [Table 1]. Specifically, the composition is applied to the polarizer (PVA device) with a thickness of 2 ~ 3㎛, laminated on the polarizer (PVA device) and passed through the laminator, and then 200mJ / cm 2 using an ultraviolet light irradiation device (Metal halide lamp) UV irradiation was carried out to prepare a peel force sample consisting of a polarizer / adhesive / polarizer. The prepared sample was cut to a width of 20 mm and a length of 100 mm, and the peel force was measured at a speed of 300 m / min and 90 degrees with a Texture Analyzer (TA-XT Plus, Stable Micro Systems). At this time, peeling force was displayed. If peeling force is 2.5N / 2cm or more, if it is 2.0-2.5N / 2cm, if it is 1.5-2.0N / 2cm, if it is 1.5N / 2cm or less, it represented by X.
Claims (9)
[Formula 2]
In Chemical Formula 2,
Y 1 is hydrogen, alkyl having 1 to 20 carbon atoms, or
R1 to R3 are the same as or different from each other, and each independently hydrogen, hydroxy, alkoxy having 1 to 20 carbon atoms, or
L1, L2, L3, L4, L5, L12 and L13 are the same as or different from each other, and are each independently alkylene having 1 to 20 carbon atoms,
X2, Y2, X5 and Y5 are the same as or different from Y1, same as the definition of Y1,
R5, R6, R7, R21 and R22 are each independently the same as or different from R1 to R3, and are as defined in R1 to R3,
R4 and R13 are the same as or different from each other, and each independently hydrogen or alkyl having 1 to 20 carbon atoms,
Z1, Z2, Z5 and Z6 are the same as or different from each other, and are each independently O or S,
n is an integer from 0 to 3,
L6, L7 and L8 are the same as or different from each other, and are each independently alkylene having 1 to 20 carbon atoms,
Z3 is O or S,
R8 to R10 are the same as or different from each other, and each independently hydrogen, a hydroxy group, or an alkoxy group having 1 to 20 carbon atoms,
X3 and Y3 are the same as or different from each other, and each independently hydrogen or alkyl having 1 to 20 carbon atoms,
[Formula 3]
In Chemical Formula 3,
R1 to R7, L1 to L5, Y1, X2, Z1 and Z2 are as defined in Formula 2, m is an integer of 0 to 3,
L9, L10 and L11 are the same as or different from each other, and are each independently alkylene having 1 to 20 carbon atoms,
Z4 is O or S,
R11 to R13 are the same as or different from each other, and each independently hydrogen, a hydroxy group, or an alkoxy group having 1 to 20 carbon atoms,
X4 and Y4 are the same as or different from each other, and each independently hydrogen or alkyl having 1 to 20 carbon atoms,
[Formula 8]
In Chemical Formula 8, the substituent is as defined in Chemical Formula 2.
[Formula 4]
[Formula 5]
In Chemical Formulas 4 and 5, the substituents are as defined in Chemical Formula 2.
[Formula 6]
[Formula 7]
In Chemical Formulas 6 and 7, R14 to R16 are the same as or different from each other, and each independently hydrogen, a hydroxy group, or an alkoxy group having 1 to 20 carbon atoms,
L3 'to L5' is the same as the definition of L3 to L5 in Formula 3,
Z2 'is the same as the definition of Z2 in Chemical Formula 3,
X2 'is as defined in X2 of Formula 3,
Other substituents are as defined in formula (3).
[Formula 9]
[Formula 10]
In Chemical Formulas 9 and 10,
n and m are the same as or different from each other, and each independently an integer of 0 to 3,
L6, L7, L8, L9, L10 and L11 are the same as or different from each other, and are each independently alkylene having 1 to 20 carbon atoms,
Z3 and Z4 are the same as or different from each other, and each independently O or S,
R8 to R13 are the same as or different from each other, and each independently hydrogen, a hydroxy group, or an alkoxy group having 1 to 20 carbon atoms,
X3, Y3, X4 and Y4 are the same as or different from each other, and each independently hydrogen or alkyl having 1 to 20 carbon atoms,
Other substituents are as defined in formula (2).
[Formula 11]
[Formula 12]
In Chemical Formulas 11 and 12,
n and m are the same as or different from each other, and each independently an integer of 0 to 3,
L6, L7, L8, L9, L10 and L11 are the same as or different from each other, and are each independently alkylene having 1 to 20 carbon atoms,
Z3 and Z4 are the same as or different from each other, and each independently O or S,
R8 to R13 are the same as or different from each other, and each independently hydrogen, a hydroxy group, or an alkoxy group having 1 to 20 carbon atoms,
X3, Y3, X4 and Y4 are the same as or different from each other, and each independently hydrogen or alkyl having 1 to 20 carbon atoms,
Other substituents are as defined in formula (2).
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