Acrylic resin composition

Inactive Publication Date: 2005-11-03
SUMITOMO CHEM CO LTD
3 Cites 5 Cited by

AI-Extracted Technical Summary

Problems solved by technology

Such an optical laminated film tends to generate curl and the like due to large dimension change by expansion and shrinkage under heating or moistening and heating conditions, consequently, there are problems such as occurrence of foaming in an adhesive layer of the resulted optical laminate, generation of peeling between an adhesive layer and a glass base material, and the like.
Under heating or moistening and heating conditions, distribution of remaining stress acting on an optical laminated film becomes non-uni...
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Method used

[0105] The optical laminated film can be produced in comparatively short time by compounding a cross-linking catalyst together with a cross-linking agent to the adhesive. In the optical laminate containing the optical laminated film, floating and peeling between an optical film and an adhesive layer and foaming in the adhesive layer tend to lower, further, a re-working property tends to be improved, preferably.
[0121] The acrylic resin composition of the present invention can be provided the optical laminated film used for a liquid crystal cell in which light leakage is suppressed and durability is excellent.
[0125] In such an optical laminate, the adhesive layer absorbs and relaxes stress derived from the dimension change of the optical film and glass base ...
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Benefits of technology

[0005] An object of the present invention is to provide an acrylic resin composition capable of producing an opti...
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Abstract

An acrylic resin composition comprising the following acrylic resins (1) and (2): acrylic resin (1): an acrylic resin containing a structural unit derived from a monomer (a) (structural unit (a)) and a structural unit derived from a monomer (b) (structural unit (b)); acrylic resin (2): an acrylic resin having a molecular weight of 1,100,000 to 1,500,000, and containing the structural unit (a) as the main component and a structural unit derived from a monomer (c) (structural unit (c)) and substantially not containing the structural unit (b);
(a): a (meth)acrylate of the formula (A)
(wherein, R1 represents a hydrogen atom or methyl group, R2 represents an alkyl group having 1 to 14 carbon atoms or an aralkyl group having 1 to 14 carbon atoms, and a hydrogen atom in the alkyl group R2 or a hydrogen atom in the aralkyl group R2 may be substituted with an alkoxy group having 1 to 10 carbon atoms.),
(b): a monomer containing an olefinic double bond in the molecule and at least one 5- or more-membered heterocyclic group in the molecule, (c): a monomer not containing 5- or more-membered heterocyclic group and containing one olefinic double bond and at least one polar functional group selected from the group consisting of a carboxyl group, hydroxyl group, amide group, amino group, epoxy group, oxetanyl group, aldehyde group and isocyanate group in the molecule.

Application Domain

Technology Topic

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  • Acrylic resin composition
  • Acrylic resin composition
  • Acrylic resin composition

Examples

  • Experimental program(2)

Example

Polymerization Example 1-5
[0138] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 183 parts of ethyl acetate, and 60.0 parts of n-butyl acrylate and 8.9 parts of n-butyl methacrylate as a monomer (a), 6.9 parts of N-vinylpyrrolidone as a monomer (b), 6.4 parts of isobornyl acrylate as a monomer (d), and 0.49 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 30 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 84,800.
Polymerization Example 1-6
[0139] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 159 parts of ethyl acetate, and 45.0 parts of n-butyl acrylate and 23.4 parts of n-butyl methacrylate as a monomer (a), 3.0 parts of N-vinylpyrrolidone as a monomer (b), 0.4 parts of acrylic acid as a monomer (c), and 0.43 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 42 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 70,100.
Polymerization Example 1-7
[0140] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 178 parts of ethyl acetate, and 40.0 parts of n-butyl acrylate, 26.6 parts of n-butyl methacrylate and 5.4 parts of methyl methacrylate as a monomer (a), 6.9 parts of N-vinylpyrrolidone as a monomer (b) and 1.58 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 16 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 37,300.
Polymerization Example 1-8
[0141] The reaction was completed in the same manner as in Polymerization Example 1-7 except that 176 parts of ethyl acetate and 0.79 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 25 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 66,900.
Polymerization Example 1-9
[0142] The reaction was completed in the same manner as in Polymerization Example 1-7 except that 175 parts of ethyl acetate and 0.47 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 31 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 91,600.
Polymerization Example 1-10
[0143] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 153 parts of ethyl acetate, and 55.0 parts of n-butyl acrylate, 36.6 parts of n-butyl methacrylate and 7.4 parts of methyl acrylate as a monomer (a), 9.5 parts of N-vinylpyrrolidone as a monomer (b) and 0.33 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 50 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 178,000.
Polymerization Example 1-11
[0144] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 128 parts of ethyl acetate, and 70.0 parts of n-butyl acrylate, 46.6 parts of n-butyl methacrylate and 9.4 parts of methyl methacrylate as a monomer (a), 12.1 parts of N-vinylpyrrolidone as a monomer (b) and 0.28 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 106 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 251,000.
Polymerization Example 1-12
[0145] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 95 parts of ethyl acetate, and 80.0 parts of n-butyl acrylate, 53.3 parts of n-butyl methacrylate and 10.8 parts of methyl acrylate as a monomer (a), 13.9 parts of N-vinylpyrrolidone as a monomer (b) and 0.16 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 310 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 392,000.
Polymerization Example 1-13
[0146] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 178 parts of ethyl acetate, and 80.0 parts of n-butyl acrylate as a monomer (a) and 0.48 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 27 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 78,600.
Polymerization Example 1-14
[0147] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 162 parts of ethyl acetate, and 60.0 parts of n-butyl acrylate, 8.3 parts of iso-butyl methacrylate and 5.0 parts of methyl acrylate as a monomer (a) and 0.44 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 25 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 75,500.
Polymerization Example 1-15
[0148] The reaction was completed in the same manner as in Polymerization Example 1-1 except that 179 parts of ethyl acetate, and 80.0 parts of n-butyl acrylate as a monomer (a), 0.45 parts of acrylic acid as a monomer (c), and 0.48 parts of AIBN were used. The content of non-volatile components in the resulted acrylic resin solution was regulated to 30%, to find a viscosity of 20 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 82,400.
Production Example of Acrylic Resin (2)
Polymerization Example 2-1
[0149] Into the same reactor as in Polymerization Example 1-1 was charged 206 parts of acetone, and 210 parts of butyl acrylate as a monomer (a) and 1.2 parts of acrylic acid as a monomer (c), air in the apparatus was purged with a nitrogen gas to make no-oxygen atmosphere, then, the inner temperature was raised to 55° C. 0.148 parts of 2,2′-azobis(2,4-dimethylvaleronitrile) as an initiator was dissolved in 5 parts of acetone and the prepared solution was all added to the reactor. In this point, the concentration of monomers was 50%. After adding the initiator, the inner temperature was raised at up to approximately 70° C. for 30 minutes and lowered at 55° C. during 30 minutes. Then, while keeping the inner temperature at 54 to 56° C., acetone was added over 8 hours so that the total concentration of the charged monomers was 35%. After completion of adding, while keeping the inner temperature at 54 to 56° C. for further 3 hours to complete the reaction, the monomer concentration was adjusted to 20%. The content of non-volatile components in the resulted acrylic resin solution 19.9%, and the viscosity was 1950 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 780,000.
Polymerization Example 2-2
[0150] The reaction was completed in the same manner as in Polymerization Example 2-1 except that 168 parts of acetone and 0.085 part of 2,2′-azobis(2,4-dimethylvaleronitrile) were used. The content of non-volatile components in the resulted acrylic resin solution was 19.6%, to find a viscosity of 6450 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 1,040,000.
Polymerization Example 2-3
[0151] The reaction was completed in the same manner as in Polymerization Example 2-2 except that the inner temperature was keeping at 50° C. The content of non-volatile components in the resulted acrylic resin solution was 18.8%, to find a viscosity of 4400 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 1,150,000.
Polymerization Example 2-4
[0152] The reaction was completed in the same manner as in Polymerization Example 2-1 except that 0.042 part of 2,2′-azobis(2,4-dimethylvaleronitrile) was used. The content of non-volatile components in the resulted acrylic resin solution was 20.1%, to find a viscosity of 14300 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 1,380,000.
Polymerization Example 2-5
[0153] The reaction was completed in the same manner as in Polymerization Example 2-1 except that 0.031 part of 2,2′-azobis(2,4-dimethylvaleronitrile) was used. The content of non-volatile components in the resulted acrylic resin solution was 19.3%, to find a viscosity of 9900 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 1,450,000.
Polymerization Example 2-6
[0154] The reaction was completed in the same manner as in Polymerization Example 2-1 except that 0.021 part of 2,2′-azobis(2,4-dimethylvaleronitrile) was used. The content of non-volatile components in the resulted acrylic resin solution was 19.7%, to find a viscosity of 18400 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 1,570,000.
Polymerization Example 2-7
[0155] The reaction was completed in the same manner as in Polymerization Example 2-3 except that 176 parts of acetone, and 9.7 parts of vinylpyrrolidone as a monomer (b), 1.3 parts of acrylic acid as a monomer (c), and 0.022 part of 2,2′-azobis(2,4-dimethylvaleronitrile) were used. The content of non-volatile components in the resulted acrylic resin solution was 19.4%, to find a viscosity of 1280 mPa.s. The weight-average molecular weight based on polystyrene calibration standard by GPC was approximately 600,000.
Acrylic Resin Composition and Production Example of Adhesive Containing the Same Composition
Example 1
[0156] The acrylic resin solution obtained in Polymerization Example 1-1 was used as a solution of an acrylic resin (1), the acrylic resin solution obtained in Polymerization Example 2-3 was used as a solution of an acrylic resin (2), and they were mixed so that the content of non-volatile components in the acrylic resin (1) was 70 parts and the content of non-volatile components in the acrylic resin (2) was 30 parts, to obtain an ethyl acetate solution of acrylic resin composition having a non-volatile component content of 20.0%. To 100 parts of non-volatile components in the resulted solution was mixed 1.0 part of non-volatile components of a polyisocyanate-based compound (trade name: Takenate D-160N, manufactured by Mitsui-Takeda Chemical Inc.) and 0.4 part of a silane-based compound (trade name: KBM-403, manufactured by Shin-Etsu Silicones) as a cross-linking agent, to obtain an adhesive of the present invention.
Production Examples of Optical Laminated Film, and Optical Laminate
[0157] Thus obtained adhesive was applied, using an applicator, on a releasing-treated surface of a polyethylene terephthalate film (manufactured by LINTEC Corporation, trade name: PET 3811) which had been subjected to releasing treatment so that the thickness after drying was 25 μm, the dried at 90° C. for 1 minute, to obtain an adhesive in the form of sheet. Then, a polarizing film (film having a three-layer structure obtained by adsorbing iodine into polyvinyl alcohol and stretching to obtain a stretched film and sandwiching said stretched film on both surfaces thereof by triacetylcellulose-based protective films) was used as an optical film, and a surface having the adhesive obtained above was applied on this optical film by a laminator, then, aged under a temperature of 23° C. and a humidity of 65% for 7 days, to obtain an optical laminated film having an adhesive layer. Subsequently, this optical laminated film was adhered on both surfaces of a glass base plate for liquid crystal cell (manufactured by Corning, 1737) so as to give Cross Nicol condition. This was preserved under 80° C. and dry condition for 96 hours (condition 1) and durability and light leakage of the optical laminate after preservation were observed visually. This was also preserved under 60° C. and 90% RH for 96 hours (condition 2) and durability of the optical laminate was observed visually. The results are classified as described below and shown in Table 1.
Light Leakage Property of Optical Laminate
[0158] Evaluation of state of generation of light leakage was conducted according to the following four stages. [0159] ⊚: no light leakage [0160] ◯: little light leakage [0161] Δ: slight light leakage [0162] ×: remarkable light leakage
Durability of Optical Laminate
[0163] Evaluation of durability was conducted according to the following four stages. [0164] ⊚: no change in appearance such as floating, peeling, foaming and the like [0165] ◯: little change in appearance such as floating, peeling, foaming and the like [0166] Δ: slight change in appearance such as floating, peeling, foaming and the like [0167] ×: remarkable change in appearance such as floating, peeling, foaming and the like
Re-Working Property
[0168] Evaluation of the re-working property was conducted as described below. First, the above-mentioned optical laminate was processed into a specimen of 25 mm×150 mm. Then, this specimen was pasted on a glass base plate for liquid crystal cell (manufactured by Corning, 1737) using a pasting apparatus (“Lamipacker”, manufactured by Fuji Plastic Machine K.K.), and treated in an autoclave under 50° C., 5 kg/cm2 (490.3 kPa) for 20 minutes, subsequently, heated in an oven under 70° C. for 2 hours, preserved in an oven under 70° C. for 24 hours. The optical laminate for peeling test was peeled toward 180° direction at a rate of 300 mm/min in an atmosphere of 23° C. and 50% RH, and the state of the surface of the glass plate classified according to the following conditions was observed and shown in Table 1-3.
[0169] Evaluation of the re-working property was conducted by observing the state of the surface of the glass plate according to the following four stages. [0170] ⊚: no fogging and past remaining on the surface of glass plate [0171] ◯: little fogging and the like on the surface of glass plate [0172] Δ: fogging and the like on the surface of glass plate [0173] ×: paste remaining on the surface of glass plate

Example

Examples 2 to 14 and Comparative Examples 1 to 7
[0174] An acrylic resin composition, adhesive, optical laminated film and optical laminate were produced according to Example 1 using the acrylic resins (1) and (2) at weight ratios shown in Tables 1-3. Evaluation of the resulted optical laminate was conducted in the same manner as in Example 1, and the results are shown in Tables 1-3 together with that of Example 1. TABLE 1 Example 1 2 3 4 5 6 7 Acrylic Polymerization example 1-1 1-2 1-3 1-4 1-5 1-6 1-7 resin (1) Non-volatile component 30 30 30 30 30 30 30 content (part by weight) (a)*1 91.0 89.0 95.5 86.4 83.8 95.2 91.2 (part by weight) (b)*1 9.0 11.0 4.5 13.6 8.4 4.2 8.8 (part by weight) (c)*1 0 0 0 0 0 0.6 0 (part by weight) (d)*1 0 0 0 0 7.8 0 0 (part by weight) Molecular weight (×103) 126 88.3 93 96.9 84.8 70.1 37.3 Acrylic Polymerization example 2-3 2-3 2-3 2-3 2-3 2-3 2-3 resin Non-volatile component 70 70 70 70 70 70 70 (2)*3 content (part by weight) (a)*2 99.4 99.4 99.4 99.4 99.4 99.4 99.4 (part by weight) (b)*1 0 0 0 0 0 0 0 (part by weight) (c)*1 0.6 0.6 0.6 0.6 0.6 0.6 0.6 (part by weight) Molecular weight (×106) 1.15 1.15 1.15 1.15 1.15 1.15 1.15 Condition 1 Durability ⊚ ⊚ ⊚ ⊚ ⊚ ⊚ ⊚ Light leakage property ⊚ ⊚ ◯ ⊚ ⊚ ◯ ⊚ Condition 2 Durability ◯ ◯ ⊚ ◯ ◯ ⊚ ⊚ reworking Paste remaining property ◯ ◯ ⊚ ◯ ◯ ⊚ ◯ property
*1Parts by weight of structural units (a) + (b) + (c) + (d) = 100 (parts by weight)
[0175] TABLE 2 Example 8 9 10 11 12 13 14 Acrylic Polymerization example 1-8 1-9 1-10 1-11 1-12 1-8 1-8 resin (1) Non-volatile component 30 30 30 30 30 30 30 content (part by weight) (a)*1 91.2 91.2 91.2 91.2 91.2 91.2 91.2 (part by weight) (b)*1 8.8 8.8 8.8 8.8 8.8 8.8 8.8 (part by weight) (c)*1 0 0 0 0 0 0 0 (part by weight) (d)*1 0 0 0 0 0 0 0 (part by weight) Molecular weight (×103) 66.9 91.6 17.8 251 392 66.9 66.9 Acrylic Polymerization example 2-3 2-3 2-3 2-3 2-3 2-4 2-5 resin Non-volatile component 70 70 70 70 70 70 70 (2)*3 content (part by weight) (a)*2 99.4 99.4 99.4 99.4 99.4 99.4 99.4 (part by weight) (b)*1 0 0 0 0 0 0 0 (part by weight) (c)*1 0.6 0.6 0.6 0.6 0.6 0.6 0.6 (part by weight) Molecular weight (×106) 1.15 1.15 1.15 1.15 1.15 1.38 1.45 Condition 1 Durability ⊚ ⊚ ⊚ ⊚ ⊚ ⊚ ⊚ Light leakage property ⊚ ⊚ ⊚ ⊚ ⊚ ◯ ◯ Condition 2 Durability ⊚ ⊚ ⊚ ⊚ ⊚ ⊚ ⊚ reworking Paste remaining property ◯ ◯ ◯ ◯ ⊚ ⊚ ⊚ property
*1Parts by weight of structural units (a) + (b) + (c) + (d) = 100 (parts by weight)
[0176] TABLE 3 Comparative Example 1 2 3 4 5 6 7 Acrylic Polymerization example 1-13 1-14 1-15 1-8 1-8 1-8 — resin (1) Non-volatile component 30 30 30 30 30 30 — content (part by weight) (a)*1 100 100 99.4 91.2 91.2 91.2 — (part by weight) (b)*1 0 0 0 8.8 8.8 8.8 — (part by weight) (c)*1 0 0 0.6 0 0 0.6 — (part by weight) (d)*1 0 0 0 0 0 0 — (part by weight) Molecular weight (×103) 78.6 75.5 82.4 66.9 66.9 66.9 — Acrylic Polymerization example 2-3 2-3 2-3 2-1 2-2 2-6 2-7 resin Non-volatile component 70 70 70 70 70 70 70 (2)*3 content (part by weight) (a)*2 99.4 99.4 99.4 99.4 99.4 99.4 95 (part by weight) (b)*1 0 0 0 0 0 0 4.4 (part by weight) (c)*1 0.6 0.6 0.6 0.6 0.6 0.6 0.6 (part by weight) Molecular weight (×106) 1.15 1.15 1.15 0.78 1.04 1.57 0.6 Condition 1 Durability ⊚ ⊚ ⊚ X ◯ ⊚ X Light leakage property X X X ⊚ ⊚ Δ ◯ Condition 2 Durability ⊚ ◯ ⊚ X X ⊚ X reworking Paste remaining property ◯ ◯ ◯ X X Δ X property
*1Parts by weight of structural units (a) + (b) + (c) + (d) = 100 (parts by weight)
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PUM

PropertyMeasurementUnit
Percent by mass0.1 ~ 40.0mass fraction
Percent by mass100.0mass fraction
Percent by mass60.0 ~ 99.9mass fraction
tensileMPa
Particle sizePa
strength10

Description & Claims & Application Information

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