JP7293518B1 - 自動車外装の成形用フィルム用ハードコート樹脂組成物 - Google Patents
自動車外装の成形用フィルム用ハードコート樹脂組成物 Download PDFInfo
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- JP7293518B1 JP7293518B1 JP2023001434A JP2023001434A JP7293518B1 JP 7293518 B1 JP7293518 B1 JP 7293518B1 JP 2023001434 A JP2023001434 A JP 2023001434A JP 2023001434 A JP2023001434 A JP 2023001434A JP 7293518 B1 JP7293518 B1 JP 7293518B1
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- molding
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- resin
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- 238000000465 moulding Methods 0.000 title claims abstract description 51
- 239000011342 resin composition Substances 0.000 title claims abstract description 23
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- 239000000758 substrate Substances 0.000 claims abstract description 18
- 239000005058 Isophorone diisocyanate Substances 0.000 claims abstract description 15
- 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 13
- 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 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 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 5
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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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- 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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- 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
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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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- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 2
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- 235000020971 citrus fruits Nutrition 0.000 description 2
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- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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- 238000004383 yellowing Methods 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
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- HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
- PCKZAVNWRLEHIP-UHFFFAOYSA-N 2-hydroxy-1-[4-[[4-(2-hydroxy-2-methylpropanoyl)phenyl]methyl]phenyl]-2-methylpropan-1-one Chemical compound C1=CC(C(=O)C(C)(O)C)=CC=C1CC1=CC=C(C(=O)C(C)(C)O)C=C1 PCKZAVNWRLEHIP-UHFFFAOYSA-N 0.000 description 1
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- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
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- 101000642347 Homo sapiens Splicing factor 45 Proteins 0.000 description 1
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- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
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- 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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- 125000003118 aryl group Chemical group 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-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
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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%
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。(
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)
- 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、反応性官能基を有するフッ素系シリコーン化合物と、を含み、前記(A)の重量平均分子量が3,500~12,000であることを特徴とする自動車外装の成形用フィルム用ハードコート樹脂組成物。
- 前記(B)として、ラジカル捕捉剤(b1)及び紫外線吸収剤(b2)を含み、(b1)の配合量が固形分全量に対し1~10重量%であり、(b2)の配合量が0.3~5重量%であることを特徴とする請求項1記載の自動車外装の成形用フィルム用ハードコート樹脂組成物。
- 前記反応性官能基を有するフッ素系シリコーン化合物の配合量が、固形分全量に対し0.1~3重量%であることを特徴とする請求項1記載の自動車外装の成形用フィルム用ハードコート樹脂組成物。
- 基材上に前記請求項1~3いずれか記載の自動車外装の成形用フィルム用ハードコート樹脂組成物の硬化層を有することを特徴とする成形用ハードコートフィルム。
- 請求項4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4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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