JP2024009446A - 成形用ハードコートフィルム及びそれを用いた成形品、並びにインサート成形品の製造方法 - Google Patents
成形用ハードコートフィルム及びそれを用いた成形品、並びにインサート成形品の製造方法 Download PDFInfo
- Publication number
- JP2024009446A JP2024009446A JP2022110973A JP2022110973A JP2024009446A JP 2024009446 A JP2024009446 A JP 2024009446A JP 2022110973 A JP2022110973 A JP 2022110973A JP 2022110973 A JP2022110973 A JP 2022110973A JP 2024009446 A JP2024009446 A JP 2024009446A
- Authority
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- Japan
- Prior art keywords
- molding
- hard coat
- coat film
- film
- base material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000465 moulding Methods 0.000 title claims abstract description 66
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 48
- 239000000463 material Substances 0.000 claims abstract description 33
- 239000011342 resin composition Substances 0.000 claims abstract description 21
- 239000005058 Isophorone diisocyanate Substances 0.000 claims abstract description 16
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000002131 composite material Substances 0.000 claims abstract description 13
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims abstract description 12
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 6
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 claims abstract description 6
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- 238000010521 absorption reaction Methods 0.000 description 12
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 11
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- -1 alkyl radicals Chemical class 0.000 description 5
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- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
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- 150000003254 radicals Chemical group 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical group NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 2
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 2
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 2
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- 238000005034 decoration Methods 0.000 description 2
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- 239000010419 fine particle Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 238000010422 painting Methods 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
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- 238000007639 printing Methods 0.000 description 2
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- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
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- 239000004420 Iupilon Substances 0.000 description 1
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 1
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- 125000002723 alicyclic group Chemical group 0.000 description 1
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- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
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- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C45/00—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor
- B29C45/14—Injection moulding, i.e. forcing the required volume of moulding material through a nozzle into a closed mould; Apparatus therefor incorporating preformed parts or layers, e.g. injection moulding around inserts or for coating articles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/16—Layered products comprising a layer of synthetic resin specially treated, e.g. irradiated
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
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Abstract
Description
撹拌機、還流冷却器、滴下漏斗、及び温度計を取り付けた四つ口フラスコに、エチレングリコール200重量部とIPDI(NCO基37.5%)825重量部と触媒とMEKとを固形分50%になるように仕込み、80℃で6時間攪拌・反応させ、赤外吸収分析でイソシアネート基のピークが所定の量になった時点で反応を終了させた。次にPETA(水酸基価120mgKOH/g)438重量部を添加し、70℃で6時間攪拌・反応させた後、赤外吸収分析でイソシアネート基の消滅したことを確認し、MEKにより固形分を50%に調整して、Mw6,200で6官能のウレアク1を得た。
撹拌機、還流冷却器、滴下漏斗、及び温度計を取り付けた四つ口フラスコに、エチレングリコール200重量部とIPDI(NCO基37.5%)930重量部と触媒とMEKとを固形分50%になるように仕込み、80℃で6時間攪拌・反応させ、赤外吸収分析でイソシアネート基のピークが所定の量になった時点で反応を終了させた。次にPETA(水酸基価120mgKOH/g)886重量部を添加し、70℃で6時間攪拌・反応させた後、赤外吸収分析でイソシアネート基の消滅したことを確認し、MEKにより固形分を50%に調整して、Mw3,200で6官能のウレアク2を得た。
撹拌機、還流冷却器、滴下漏斗、及び温度計を取り付けた四つ口フラスコに、エチレングリコール200重量部とIPDI(NCO基37.5%)895重量部と触媒とMEKとを固形分50%になるように仕込み、80℃で6時間攪拌・反応させ、赤外吸収分析でイソシアネート基のピークが所定の量になった時点で反応を終了させた。次にPETA(水酸基価120mgKOH/g)743重量部を添加し、70℃で6時間攪拌・反応させた後、赤外吸収分析でイソシアネート基の消滅したことを確認し、MEKにより固形分を50%に調整して、Mw3,800で6官能のウレアク3を得た。
撹拌機、還流冷却器、滴下漏斗、及び温度計を取り付けた四つ口フラスコに、エチレングリコール200重量部とIPDI(NCO基37.5%)808重量部と触媒とMEKとを固形分50%になるように仕込み、80℃で6時間攪拌・反応させ、赤外吸収分析でイソシアネート基のピークが所定の量になった時点で反応を終了させた。次にPETA(水酸基価120mgKOH/g)371重量部を添加し、70℃で6時間攪拌・反応させた後、赤外吸収分析でイソシアネート基の消滅したことを確認し、MEKにより固形分を50%に調整して、Mw7,800で6官能のウレアク4を得た。
撹拌機、還流冷却器、滴下漏斗、及び温度計を取り付けた四つ口フラスコに、エチレングリコール200重量部とIPDI(NCO基37.5%)790重量部と触媒とMEKとを固形分50%になるように仕込み、80℃で6時間攪拌・反応させ、赤外吸収分析でイソシアネート基のピークが所定の量になった時点で反応を終了させた。次にPETA(水酸基価120mgKOH/g)295重量部を添加し、70℃で6時間攪拌・反応させた後、赤外吸収分析でイソシアネート基の消滅したことを確認し、MEKにより固形分を50%に調整して、Mw9,800で6官能のウレアク5を得た。
ウレアクA:PETA-IPDI-(エチレングリコール-IPDI)n-PETA骨格、
6官能、固形分50%、Mw 1,800
ウレアクB:PETA-IPDI-(エチレングリコール-IPDI)n-PETA骨格、
6官能、固形分50%、Mw 13,000
ウレアクC:PETA-IPDI-ポリエチレングリコール-IPDI-PETA骨格、 6官能、固形分50%、Mw6,000
前記(A)として上記で調整したウレアク1~5を、(b1)としてTinuvin249(商品名:BASFジャパン社製)を、(b2)としてTinuvin477(商品名:BASFジャパン社製)を、(C)としてOmnirad2959及び127D(商品名:IGM Resins社製)を、架橋剤としてDPHAを、レベリング剤としてX-71-1203M(商品名:信越化学工業社製、アクリロイル基含有フッ素系シリコーン化合物)を、表1記載の配合で均一に溶解・分散するまで撹拌し、更に固形分が30%となるようにPGMを加えて希釈撹拌し、実施配合例1~9のHC樹脂組成物を得た。
上記の実施配合例で用いた材料の他、オリゴマーとして上記ウレアクA~Cを、表2記載の配合で均一に溶解・分散するまで撹拌し、更に固形分が30%となるようにPGMを加えて希釈撹拌し、比較配合例1~3のHC樹脂組成物を得た。
実施配合例及び比較配合例で作成したHC樹脂組成物を、ユーピロンフィルム(商品名:DF02PUL、三菱ガス化学社製、厚み125μm、PMMA/PC積層フィルム)を用い、PMMA面側に乾燥膜厚で3μmとなるように光硬化性樹脂を塗布し、恒温槽で80℃×1分乾燥後、高圧水銀ランプで出力1300mW/cm2、積算光量が200mJとなる様に窒素雰囲気化で紫外線照射し、評価用HCフィルムを調製した。
剥離無し:100/100、剥離有り:0/100~99/100
計算式:50mmを基準として何mm伸びたかで計算。
伸びた長さ(mm)/50mm×100=伸び率%
表2
実施配合例1、4、7の樹脂組成物を用い、表3に記載した基材上に、乾燥膜厚で3μmとなるように光硬化性樹脂を塗布し、恒温槽で80℃×1分乾燥後、高圧水銀ランプで出力1300mW/cm2、積算光量が200mJとなる様に紫外線照射し、実施例1~3、及び比較例1~8の成形用フィルムを調製した。(
(※1:ウェーブロックアドバンストテクノロジー社
実施例1のHCフィルムを用い、射出成形の樹脂として黒色のABSを用いて実際にインサート成形を行った。
Claims (7)
- ポリカーボネート基材及びアクリル基材の複合基材上に光硬化性樹脂組成物の硬化層を有することを特徴とするハードコートフィルムであって、前記光硬化性樹脂組成物が、エチレングリコールとイソホロンジイソシアネートを反応させたジイソシアネートに、ペンタエリスリトールトリアクリレートを更に反応させた構造を有するウレタンアクリレート(A)と、光安定剤(B)と、光重合開始剤(C)と、を含み、前記(A)の重量平均分子量が2,000~12,000であり、前記複合基材のUVB(0.55W/m2)、60℃、1000時間照射前後のΔEが1.0以下であることを特徴とする成形用ハードコートフィルム。
- 前記(B)として、ラジカル捕捉剤(b1)及び紫外線吸収剤(b2)を含むことを特徴とする請求項1記載の成形用ハードコートフィルム。
- 前記成形用ハードコートフィルムがインサート成形用又はアウトモールド成形用であることを特徴する請求項1又は2いずれか記載の成形用ハードコートフィルム。
- 自動車の外装用途であることを特徴とする請求項1又は2いずれか記載の成形用ハードコートフィルム。
- 請求項1記載の成形用ハードコートフィルムを、金型を用いて賦形後、光硬化性樹脂硬化層とは反対側から溶融樹脂を射出して樹脂成形品を形成することを特徴とするインサート成形品の製造方法。
- 前記溶融樹脂が着色されていることを特徴とする請求項5記載のインサート成形品の製造方法。
- 請求項1又は2いずれか記載の成形用ハードコートフィルムを用いたインサート成形品又はアウトモールド成形品。
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