JP2012136676A - 硬化性組成物および該組成物の硬化層を有する物品 - Google Patents
硬化性組成物および該組成物の硬化層を有する物品 Download PDFInfo
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- JP2012136676A JP2012136676A JP2010291658A JP2010291658A JP2012136676A JP 2012136676 A JP2012136676 A JP 2012136676A JP 2010291658 A JP2010291658 A JP 2010291658A JP 2010291658 A JP2010291658 A JP 2010291658A JP 2012136676 A JP2012136676 A JP 2012136676A
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- 239000000412 dendrimer Substances 0.000 claims abstract description 37
- 229920000736 dendritic polymer Polymers 0.000 claims abstract description 37
- 239000012948 isocyanate Substances 0.000 claims abstract description 28
- 239000000178 monomer Substances 0.000 claims description 58
- 239000003795 chemical substances by application Substances 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 31
- 125000000962 organic group Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 20
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
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- 239000000654 additive Substances 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000002131 composite material Substances 0.000 description 3
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- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
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- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
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- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
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- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 238000009423 ventilation Methods 0.000 description 1
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- 125000005023 xylyl group Chemical group 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/14—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
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- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
- C09D133/066—Copolymers with monomers not covered by C09D133/06 containing -OH groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2312/00—Crosslinking
- C08L2312/08—Crosslinking by silane
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
【解決手段】特定のカルボシロキサンデンドリマー構造を有する基および水酸基を含有する共重合体(A)およびイソシアネート化合物(B)を含有する硬化性組成物、および該硬化性組成物を硬化させてなる硬化層を有する物品。
【選択図】なし
Description
から、iは2以上であることが好ましく、iが2または3である、第2世代型および第3世代型のカルボシロキサンデンドリマー構造は、本発明の特に好適な実施形態に包含される。
イソブトキシメトキシアクリルアミド,イソブトキシメトキシメタクリルアミド,N,N−ジメチルアクリルアミド,N,N−ジメチルメタクリルアミド等のアミド基含有ビニル系単量体;アクリル酸,メタクリル酸,イタコン酸,クロトン酸,フマル酸,マレイン酸等のカルボン酸含有ビニル系単量体;テトラヒドロフルフリルアクリレート,テトラヒドロフルフリルメタクリレート,ブトキシエチルアクリレート,ブトキシエチルメタクリレート,エトキシジエチレングリコールアクリレート,エトキシジエチレングリコールメタクリレート,セチルビニルエーテル,2ーエチルヘキシルビニルエーテル等のエーテル結合含有ビニル系単量体;片末端にアクリル基若しくはメタクリル基を含有するポリジメチルシロキサン,片末端にアルケニルアリール基を含有するポリジメチルシロキサンなどの不飽和基含有シリコ−ン化合物;ブタジエン;塩化ビニル;塩化ビニリデン;アクリロニトリル,メタクリロニトリル;フマル酸ジブチル;無水マレイン酸;ドデシル無水コハク酸;アクリルグリシジルエーテル,メタクリルグリシジルエーテル,3,4−エポキシシクロヘキシルメチルアクリレート,3,4−エポキシシクロヘキシルメチルメタクリレート:アクリル酸,メタクリル酸,イタコン酸,クロトン酸,フマル酸,マレイン酸等のラジカル重合性不飽和カルボン酸のアルカリ金属塩,アンモニウム塩,有機アミン塩,スチレンスルホン酸のようなスルホン酸基を有するラジカル重合性不飽和単量体及びそれらのアルカリ金属塩,アンモニウム塩,有機アミン塩;3−メタクリルオキシプロピルトリメチルアンモニウムクロライドのようなアクリル酸若しくはメタクリル酸から誘導される4級アンモニウム塩,メタクリル酸ジエチルアミンエステルのような3級アミン基を有するアルコールのメタクリル酸エステル及びそれらの4級アンモニウム塩が例示される。C1−6低級アルキル基を有する低級アクリレート又はメタクリレートが好ましい。
基および水酸基が主鎖に所定の比率で導入されているため、主剤として用いた場合、硬化層の硬度、均一性、透明性、耐溶剤性、耐汚染性、撥水性に優れ、また、溶媒中での合成の際に、白濁せず、透明な状態であり、コーティング剤用添加剤の経日安定性と、任意のコーティング剤に対する配合安定性に特に優れる点で有用である。
ることが好ましい。硬化温度が高い程、硬化時間は短くでき、硬化触媒を併用することでさらに硬化時間を短縮できる。また、架橋反応を促進させるためには塗布乾燥後の硬化層を30〜120℃の温度で1〜7日間養生処理することもできる。
ンデンドリマー構造と水酸基を有する共重合体を主剤とするものであり、透明な樹脂溶液とすることができる。また、本発明の共重合体を主剤としてイソシアネート化合物と反応させて得られた硬化性組成物は、カルボシロキサンデンドリマー構造の効果により、高い透明性、硬度および耐汚染性を示す。このため、本発明の硬化性組成物は、各種物品に塗布することにより、表面保護剤として耐汚染性を付与することができ、油汚れ、空気中の埃や塵、排ガス、雨水に混入した汚れなどの幅広い汚れの種類に対して用いることができる。また、本発明に係る硬化性組成物を硬化させてなる硬化層を有する物品は、高硬度かつ機能性の塗膜を有するため高機能素材として極めて有用である。
Claims (11)
- 分子中に下記式(1)で示されるカルボシロキサンデンドリマー構造を有する基および水酸基を含有する共重合体(A) ならびに
イソシアネート化合物およびメラミン化合物からなる群から選択される1種類以上の硬化剤(B)を含有する硬化性組成物。
Zは、2価の有機基であり、
pは、0又は1であり、
R1及びR2は、それぞれ独立して、炭素原子数1〜10のアルキル基、アリール基又はアラルキル基であり、
L1は、i=1とした場合の下記構造式(2)で示されるシリルアルキル基
Z及びpは、前記と同じであり、
R1及びR2は、前記と同じであり、
iは、前記シリルアルキル基の総階層数を示す1〜10の整数であり、
Li+1は、水素原子、炭素原子数1〜10のアルキル基、アリール基、アラルキル基及び前記シリルアルキル基からなる群から選択される基であり、但し、i=c(cは前記シリルアルキル基の階層を示す1〜10の整数である)の場合は、Li+1は水素原子、炭素原子数1〜10のアルキル基、アリール基又はアラルキル基であり、i<cの場合は前記シリルアルキル基であり、
aiは0〜3の整数である)である} - 上記式(1´)で示されるラジカル重合可能な不飽和単量体において、ラジカル重合可能な不飽和含有基Yが、
一般式:
一般式:
- 前記共重合体(A)が、更に、少なくとも1種以上の(a3)分子中に水酸基を含有しない不飽和単量体 を共重合させてなる共重合体である、請求項2に記載の硬化性組成物。
- 前記共重合体(A)がその構成単位として、前記の不飽和単量体(a1)、(a2)および任意で(a3)を共重合させてなる共重合体であり、
当該共重合体を構成する不飽和単量体(a1)〜(a3)の質量の和が100質量部であるとき、その質量比が、
(a1):(a2):(a3)=0.5〜50.0:0.5〜50.0:0〜99.0
の範囲にあることを特徴とする、請求項2〜4のいずれか1項に記載の硬化性組成物。 - 前記共重合体(A)を構成する不飽和単量体(a1)が、アクリル酸ヒドロキシエチル,メタクリル酸ヒドロキシエチル,アクリル酸ヒドロキシプロピルおよびメタクリル酸ヒドロキシプロピルからなる群から選択される1種類以上の水酸基を含有する不飽和単量体である、請求項1〜5のいずれか1項に記載の硬化性組成物。
- 前記硬化剤が、1種類以上のイソシアネート化合物(B1)である請求項1に記載の硬化性組成物。
- 前記硬化剤が、1種類以上のポリイソシアネート化合物(B1−2)である請求項1または請求項7に記載の硬化性組成物。
- 前記共重合体(A)中の水酸基1当量に対し、前記硬化剤(B)中のNCO基の物質量が0.1〜2.0の範囲内にある請求項1〜8に記載の硬化性組成物。
- 請求項1〜9のいずれか1項に記載の硬化性組成物を硬化させてなる、厚さ0.1〜10μmの硬化層を有する物品。
- 板状またはシート状部材であるである、請求項10に記載の物品。
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