TWI389965B - 聚合性組合物,彼等之製法及得自其之複合物件 - Google Patents
聚合性組合物,彼等之製法及得自其之複合物件 Download PDFInfo
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- TWI389965B TWI389965B TW094111517A TW94111517A TWI389965B TW I389965 B TWI389965 B TW I389965B TW 094111517 A TW094111517 A TW 094111517A TW 94111517 A TW94111517 A TW 94111517A TW I389965 B TWI389965 B TW I389965B
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- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
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- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 1
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- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/22—Esters containing halogen
- C08F220/24—Esters containing halogen containing perhaloalkyl radicals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/323—Polymers modified by chemical after-treatment with inorganic compounds containing halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
- C08G65/223—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens
- C08G65/226—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring containing halogens containing fluorine
-
- C—CHEMISTRY; METALLURGY
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
- C08G65/328—Polymers modified by chemical after-treatment with inorganic compounds containing other elements
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
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Description
經氟化聚醚(例如,全氟聚醚)具有有用性能,包括低折射率、防污性、潤滑性及高排水性。因此,已用經氟化聚醚併入各種保護性塗層,以提供一或多種低折射率、清潔性、耐久性及抗劃性。
已併入塗層的很多經氟化聚醚趨向於擴散到塗層表面,並可能由重複清洗保護性塗層表面經時間耗盡。
現已用具有反應性基團的經氟化聚醚併入塗層,以解決擴散問題,但,很多此等方法費力及/或不可行。
因此,仍需要允許經氟化聚醚併入保護性塗層之物质及方法,以使經氟化聚醚不會傾向於經時間耗盡。
一方面,本發明係關於一種可聚合組合物,該組合物包括至少一種由下式所描述之化合物(F(Rf
O)x
QZ1
R1
NR2
CH2
CH2
C(=O)Z2
)y
M(Z3
C(C=O)CR3
=CH2
)z
或X[((Rf
O)x
QZ1
R1
NR2
CH2
CH2
C(=O)Z2
)y
M(Z3
C(=O)CR3
=CH2
)z
]b
其中各Rf
獨立代表具有1至6個碳原子之經氟化伸烷基;各x獨立代表大於或等於2之整數;各Q獨立代表-CF2
-、-CF(CF3
)-、-CF2
CF2
-、-CF2
CF2
CF2
-、-CF2
CF(CF3
)-、-CF(CF3
)CF2
-、-CF2
CF2
CH2
-、-CF2
CH2
-、-CF2
CF2
C(=O)-、-CF2
C(=O)-、-CF(CF3
)C(=O)-、-CF(CF3
)CH2
-、具有1至6個碳原子之伸烷基或具有1至6個碳原子之雜伸烷基;各Z1
、Z2
和Z3
獨立代表-S-、-O-、-NH-或-NR2
-;各R1
獨立代表伸烷基、伸芳烷基或雜伸烷基;各R2
獨立代表H、具有1至6個碳原子之烷基、-CH2
CH2
C(=O)Z2
M(Z3
C(=O)CR3
=CH2
)z
或-R1
Z1
Q(ORf
)x
F;各R3
獨立代表H、F或甲基;各y和z獨立代表大於或等於1之整數;各M獨立代表具有y+z價之多價有機基團;X代表具有b價之多價有機基團;且b代表大於或等於2之整數。
另一方面,本發明係關於一種可聚合組合物,該組合物包括至少一種可由反應性經氟化聚醚與聚(甲基)丙烯醯基化合物之邁克爾類型加成反應(Michael-type addition)製備之化合物。
在一些具體實施例中,本發明之可聚合組合物進一步包括至少一種游離基可聚合單體。
另一方面,本發明提供一種製造可聚合組合物之方法,其包括:使反應性經氟化聚醚;和聚(甲基)丙烯醯基化合物在足以生成其邁克爾類型加合物(Michael-type addition)之條件下反應,其中該可聚合化合物具有至少一丙烯醯基。根據本發明之方法一般相對容易進行,並可用於自市售起始物質製備廣範圍具有經氟化聚醚部分之可聚合化合物。
在一些具體實施例中,根據本發明之可聚合組合物係塗覆於基材上,並至少經部分聚合以形成保護性塗層。
因此,另一方面,本發明提供一種複合物件,該物件包括其上具有防污組合物之基材,該防污組合物可藉由使一種可聚合組合物至少部分聚合而製備,該可聚合組合物包括至少一種由下式所描述之化合物(F(Rf
O)x
QZ1
R1
NR2
CH2
CH2
C(=O)Z2
)y
M(Z3
C(C=O)CR3
=CH2
)z
或X[((Rf
O)x
QZ1
R1
NR2
CH2
CH2
C(=O)Z2
)y
M(Z3
C(=O)CR3
=CH2
)z
]b
其中各Rf
獨立代表具有1至6個碳原子之經氟化伸烷基;各x獨立代表大於或等於2之整數;各Q獨立代表-CF2
-、-CF(CF3
)-、-CF2
CF2
-、-CF2
CF2
CF2
-、-CF2
CF(CF3
)-、-CF(CF3
)CF2
-、-CF2
CF2
CH2
-、-CF2
CH2
-、-CF2
CF2
C(=O)-、-CF2
C(=O)-、-CF(CF3
)C(=O)-、-CF(CF3
)CH2
-、具有1至6個碳原子之伸烷基或具有1至6個碳原子之雜伸烷基;各Z1
、Z2
和Z3
獨立代表-S-、-O-、-NH-或-NR2
-;各R1
獨立代表伸烷基、伸芳烷基或雜伸烷基;各R2
獨立代表H、具有1至6個碳原子之烷基、-CH2
CH2
C(=O)Z2
M(Z3
C(=O)CR3
=CH2
)z
或-R1
Z1
Q(ORf
)x
F;各R3
獨立代表H、F或甲基;各y和z獨立代表大於或等於1之整數;各M獨立代表具有y+z價之多價有機基團;X代表具有b價之多價有機基團;且b代表大於或等於2之整數。
另一方面,本發明提供一種複合物件,該物件包括其至少部分上具有防污組合物之基材,該防污組合物可藉由使一種可聚合組合物至少部分聚合而製備,該可聚合組合物包括一種可由反應性經氟化聚醚與聚(甲基)丙烯醯基化合物之邁克爾類型加成反應製備之化合物。
在一具體實施例中,根據本發明之複合物件包括一種資訊顯示保護器,該保護器包括具有相反第一和第二表面之柔韌性薄膜,其中一接著層係支撐於該第一表面上,其中一硬膜層係支撐於該第二表面上,且其中該防污組合物層係支撐於該硬膜層上。
藉由經氟化聚醚部分化學併入聚合性保護塗層,一般減少或消除經氟化聚醚自保護性塗層經時間消耗。
進一步發現,可製備與普通游離基可聚合單體相容的根據本發明之邁克爾類型加成產物,以使寬產物調配範圍成為可能。
在本文中:"雜伸烷基"包括經取代和未經取代二者的雜伸烷基;"(甲基)丙烯醯基"包括丙烯醯基和甲基丙烯醯基二者;"聚(甲基)丙烯醯基化合物"包括具有複數個(甲基)丙烯醯基之化合物;"反應性經氟化聚醚"指具有至少一個-NH2
或-NR2
H基之經氟化聚醚,其中R2
係如本文所界定者;而"邁克爾類型加成反應"指如下一般性顯示之加成反應:
其中A和E代表單價殘基。
根據本發明之可聚合組合物包括至少一種化合物,且該化合物具有一或多個結合到一或多個可聚合(甲基)丙烯醯基之經氟化聚醚部分。概括而言,此類化合物一般可由反應性經氟化聚醚到具有複數個(甲基)丙烯醯基化合物之邁克爾類型加成反應而製備,其複數個(甲基)丙烯醯基之至少一個為丙烯醯基。
與邁克爾類型加成反應有關,在丙烯醯基和甲基丙烯醯基之間一般有不同反應性。利用丙烯醯基一般容易發生邁克爾類型加成反應(例如,視需要利用溫和加熱,雖然不是必需,僅僅使反應性經氟化聚醚與具有丙烯醯基之化合物組合即引起自發邁克爾類型加成反應),但如果完全在甲基丙烯醯基之例,僅艱難進行。因此,聚(甲基)丙烯醯基化合物一般具有至少一個丙烯醯基(例如,作為丙烯醯氧基或丙烯醯胺基官能之部分),雖然聚(甲基)丙烯醯基化合物亦可具有額外(甲基)丙烯醯基(例如,作為甲基丙烯酸酯或甲基丙烯醯胺基官能之部分)。
可加入酸或鹼催化劑,以促進反應性經氟化聚醚與聚(甲基)丙烯醯基化合物之反應。例如,所用酸催化劑包括(例如)路易絲(Lewis)酸(例如,AlCl3
,MgCl2
)和布朗(Bronsted)酸。所用鹼催化劑包括(例如)非親核性三級胺(例如,N,N,N',N'-四甲基-1,8-萘二胺;1,8-二氮雜雙環[5.4.0]十一碳-7-烯;1,5-二氮雜雙環[4.3.0]壬-5-烯)。所用聚(甲基)丙烯醯基化合物包括(例如)(甲基)丙烯酸酯單體,其係選自由(a)含二(甲基)丙烯醯基之化合物,如1,3-丁二醇二丙烯酸酯、1,4-丁二醇二丙烯酸酯、1,6-己二醇二丙烯酸酯、1,6-己二醇單丙烯酸單甲基丙烯酸酯、乙二醇二丙烯酸酯、烷氧基化脂系二丙烯酸酯、烷氧基化環己烷二甲醇二丙烯酸酯、烷氧基化己二醇二丙烯酸酯、烷氧基化新戊二醇二丙烯酸酯、經己內酯改質的新戊二醇羥基新戊酸二丙烯酸酯、經己內酯改質的新戊二醇羥基新戊酸二丙烯酸酯、環己烷二甲醇二丙烯酸酯、二乙二醇二丙烯酸酯、二丙二醇二丙烯酸酯、乙氧基化(10)雙酚二丙烯酸酯、乙氧基化(3)雙酚二丙烯酸酯、乙氧基化(30)雙酚二丙烯酸酯、乙氧基化(4)雙酚二丙烯酸酯、經羥基新戊醛改質的三羥甲基丙烷二丙烯酸酯、新戊二醇二丙烯酸酯、聚乙二醇(200)二丙烯酸酯、聚乙二醇(400)二丙烯酸酯、聚乙二醇(600)二丙烯酸酯、丙氧基化新戊二醇二丙烯酸酯、四乙二醇二丙烯酸酯、三環癸烷二甲醇二丙烯酸酯、三乙二醇二丙烯酸酯、三丙二醇二丙烯酸酯;(b)含三(甲基)丙烯醯基之化合物,如甘油三丙烯酸酯、乙氧基化三丙烯酸酯(例如,乙氧基化(3)三羥甲基丙烷三丙烯酸酯、乙氧基化(6)三羥甲基丙烷三丙烯酸酯、乙氧基化(9)三羥甲基丙烷三丙烯酸酯、乙氧基化(20)三羥甲基丙烷三丙烯酸酯)、四級戊四醇三丙烯酸酯、丙氧基化三丙烯酸酯(例如,丙氧基化(3)甘油基三丙烯酸酯、丙氧基化(5.5)甘油基三丙烯酸酯、丙氧基化(3)三羥甲基丙烷三丙烯酸酯、丙氧基化(6)三羥甲基丙烷三丙烯酸酯)、三羥甲基丙烷三丙烯酸酯、叁(2-羥乙基)異氰脲酸三丙烯酸酯;(c)含更高官能性(甲基)丙烯醯基之化合物,如二(三羥甲基丙烷)四丙烯酸酯、二(四級戊四醇)五丙烯酸酯、乙氧基化(4)四級戊四醇四丙烯酸酯、四級戊四醇四丙烯酸酯、經己內酯改質的二(四級戊四醇)六丙烯酸酯;(d)寡聚性(甲基)丙烯醯基化合物,例如,脲烷丙烯酸酯、聚酯丙烯酸酯、環氧丙烯酸酯;前述之聚丙烯醯胺類似物及其組合所組成之群組。此等化合物可自廠家獲得,例如,賓夕法尼亞州,伊斯坦,薩托默公司(Sartomer Company,Exton,Pennsylvania);喬治亞州,土麥那,UCB化學公司(UCB Chemical Corporation,Smyrna,Georgia);及威斯康辛州,密爾瓦基,阿瑞化學公司(Aldrich Chemical Company,Milwaukee,Wisconsin)。額外有用(甲基)丙烯酸酯物質包括含乙內醯脲部分之聚(甲基)丙烯酸酯,如美國專利第4,262,072號中所述(文德令(Wendling)等人)。
所用(甲基)丙烯醯基化合物亦包括(例如)遊離基可聚合(甲基)丙烯酸酯寡聚物及具有懸垂(甲基)丙烯醯基之聚合物,其中至少一個為(甲基)丙烯醯基為丙烯醯基。
所用(甲基)丙烯酸酯寡聚物包括(甲基)丙烯酸化聚醚及聚酯寡聚物。所用丙烯酸化聚醚寡聚物之實例包括聚乙二醇二丙烯酸酯,例如自薩托默公司在商品名"SR259"和"SR344"下獲得。丙烯酸化聚酯寡聚物(例如)自UCB化學公司在商品名"EBECRYL 657"和"EBECRYL 830"下獲得。
其他有用(甲基)丙烯酸酯寡聚物包括(甲基)丙烯酸化環氧樹脂,例如,環氧官能材料之二丙烯酸化酯(例如,雙酚A環氧官能材料之二丙烯酸化酯)和(甲基)丙烯酸化胺基甲酸酯。所用(甲基)丙烯酸化環氧樹脂包括(例如)自UCB化學公司在商品名"EBECRYL 3500"、"EBECRYL 3600"、"EBECRYL 3700"和"EBECRYL 3720"下獲得的丙烯酸化環氧樹脂。所用(甲基)丙烯酸化胺基甲酸酯包括(例如)自UCB化學公司在商品名"EBECRYL 270"、"EBECRYL 1290"、"EBECRYL 8301"和"EBECRYL 8804"下獲得的丙烯酸化胺基甲酸酯。
在本發明一具體實施例中,邁克爾類型加成反應化合物為由下式所描述者(F(Rf
O)x
QZ1
Rl
NR2
CH2
CH2
C(=O)Z2
)y
M(Z3
C(C=O)CR3
=CH2
)z
或X[((Rf
O)x
QZ1
R1
NR2
CH2
CH2
C(=O)Z2
)y
M(Z3
C(=O)CR3
=CH2
)z
]b
各Rf
獨立代表具有1至6個碳原子之經氟化伸烷基。例如,Rf
可為部分氟化基團,如-CF2
CF2
CH2
-、-CH2
CF2
CH2
-,或為具有1至6個碳原子之全氟化伸烷基,如-CF2
-、-CF(CF3
)-、-CF2
CF2
-、-CF2
CF2
CF2
-、-CF(CF3
)CF2
-、-CF2
CF(CF3
)-或-(CF2
)6
。由於各Rf
係獨立選擇,因此,例如,-(Rf
O)x
-可代表-(CF(CF3
)CF2
O)8
-、-(CF2
CF2
O)3
(CF(CF3
)CF2
O)1 2
-、-(CF2
CF2
O)2
(CF(CF3
)CF2
O)9 8
(CF2
CF2
O)-等。
各X獨立代表大於或等於2之整數。例如X可大於3或大於4。
各Q獨立代表-CF2
-、-CF(CF3
)-、-CF2
CF2
-、-CF2
CF2
CF2
-、-CF2
CF(CF3
)-、-CF(CF3
)CF2
-、-CF2
CF2
CH2
-、-CF2
CH2
-、-CF2
CF2
C(=O)-、-CF2C(=O)-、-CF(CF3
)C(=O)-、-CF(CF3
)CH2
-、具有1至6個碳原子之伸烷基或具有1至6個碳原子之雜伸烷基;各Z1
、Z2
和Z3
獨立代表-S-、-O-、-NH-或-NR2
-;各R1
獨立代表伸烷基、伸芳烷基或雜伸烷基;例如,各R1
可代表具有1或2個碳原子至6、8、10、12或甚至18個碳原子之伸烷基、伸芳烷基或雜伸烷基,並可具有至少1、2、3或4個懸鏈狀視需要取代的雜原子(例如,-S-、-O-、-NH-、-N(R2
)-)。實例包括:-CH2
CH2
OCH2
CH2
OCH2
CH2
-、-CH2
NHCH2
CH2
CH2
NHCH2
-、-CHBCH2
NHC
H2
CH2
NHCH2
CH2
-、-CH2
CH2
NHCH2
CH2
N(CH2
CH3
)CH2
CH2
-、-CH2
CH2
CH2
-、-CH2
CH2
-及-CH2
。
各R2
獨立代表H、具有1至6個碳原子之烷基、-CH2
CH2
C(=O)Z2
M(Z3
C(=O)CR3
=CH2
)z
或-R1
Z1
Q(ORf
)xF。
各R3
獨立代表H、F或甲基;各y和z獨立代表大於或等於1之整數。例如y和/或z可為1、2或3。
各M獨立代表具有y+z之價之多價有機基團。在一具體實施例中,M可為具有至少3之價之多價有機基團。多價基團M之實例包括2,2-雙(基甲基)丁-1-基、伸乙基、2,2-雙(基甲基)-丙-1,3-二基、2,2,6,6-肆(基甲基)-4-氧雜庚-1,7-二基、丁-1,3-二基、己-1,6-二基及1,4-雙(基甲基)環己烷。
各X獨立代表具有b之價之多價有機基團,且b代表大於或等於2之整數。例如,X可為包含至少3個全氟伸烷氧基之全氟伸烷二氧基。
各b獨立代表大於或等於2之整數。
例如,反應性氟化聚醚可藉由對應經氟化聚醚酯(包括經氟化聚醚多酯)或對應氟化聚醚醯鹵(包括經氟化聚醚多醯鹵)(一般為醯氟)與親核化合物之反應而製備,親核化合物如作為二(一級)、二(二級)或混合一和二級二胺之烷二胺及較高級聚胺(例如,三乙四胺)。在此例中,一般應調節化學計量,以使所得反應性氟化聚醚加合物平均每反應性氟化聚醚分子具有至少一個親核基。
因此,在一具體實施例中,所用反應性氟化聚醚為由下式所描述者F(Rf
O)x
QZ1
R1
NR2
H或X(Rf
O)x
QZ1
R1
NR2
H其中各Rf
、x、Q、Z1
、R1
、R2
和X係如上所界定者。
在一具體實施例中,根據本發明之可聚合組合物可利用或不利用催化劑自反應性氟化聚醚藉由到多官能丙烯酸酯之邁克爾類型加成反應而製備。
在另一具體實施例中,根據本發明之可聚合組合物可藉由經氟化聚醚醯鹵和所完成的邁克爾類型加合物之反應而製備,該邁克爾類型加合物具有可聚合部分及游離羥基,例如,由胺基醇(例如,N-甲基乙醇胺)與聚丙烯酸酯(例如,三羥甲基丙烷三丙烯酸酯)之反應獲得之物質。
對熟諳此藝者很明顯,可用反應性經氟化聚醚之混合物製備根據本發明之可聚合組合物。類似地,對熟諳此藝者很明顯,一般可作為加合物之混合物(例如,統計混合物)製備根據本發明之可聚合組合物,加合物可"原樣"使用,或進一步純化,例如,使用習知方法。
關於製備反應性氟化聚醚的物質和步驟之額外細節可發現於,例如,美國專利第3,242,218號(米勒(Miller))、第3,322,826號(莫爾(Moore))、第3,250,808號(莫爾等人)、第3,274,239號(賽曼(Selman))、第3,293,306號(裏伯魯(Le Bleu)等人)、第3,810,874號(米齊(Mitsch)等人)、第3,544,537號(布瑞斯(Brace))、第3,553,179號(巴特萊(Bartlett))、第3,864,318號(卡泊雷克(Caporiccio)等人)、第4,321,404號(威廉斯(Williams)等人)、第4,647,413號(薩沃(Savu))、第4,818,801號(賴斯(Rice)等人)、第4,472,480號(奧森(Olson))、第4,567,073號(拉森(Larson)等人)、第4,830,910號(拉森)及第5,306,758號(比利萊特(Pellerite)。
根據本發明之可聚合組合物可進一步包括至少一種額外游離基可聚合單體。除前述聚(甲基)丙烯醯基化合物單體、寡聚物及聚合物外,所用游離基可聚合單體包括,例如,苯乙烯和經取代苯乙烯(例如,1,4-二乙烯基苯、α-甲基苯乙烯);乙烯基酯(例如,乙酸乙烯酯);乙烯基醚(例如,丁基乙烯基醚);N-乙烯基化合物(例如,N-乙烯基-2-吡咯啶酮、N-乙烯基己內醯胺);丙烯醯胺和經取代丙烯醯胺(例如,N,N-二烷基丙烯醯胺);單官能(甲基)丙烯酸酯(例如,(甲基)丙烯酸異辛酯、乙氧基化(甲基)丙烯酸壬基酚酯、(甲基)丙烯酸異壬酯、(甲基)丙烯酸二乙二醇酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸2-(2-乙氧基乙氧基)乙酯、(甲基)丙烯酸2-乙基己酯、(甲基)丙烯酸月桂酯、丁二醇單(甲基)丙烯酸酯、(甲基)丙烯酸β-羧乙酯、(甲基)丙烯酸異丁酯、(甲基)丙烯酸2-羥乙酯、(甲基)丙烯腈、馬來酸酐、衣康酸、(甲基)丙烯酸異癸酯、(甲基)丙烯酸十二烷酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸甲酯、(甲基)丙烯酸己酯、(甲基)丙烯酸、(甲基)丙烯酸硬脂酯、羥基官能聚己內酯(甲基)丙烯酸酯、(甲基)丙烯酸羥丙酯、(甲基)丙烯酸羥異丙酯、(甲基)丙烯酸羥丁酯、(甲基)丙烯酸四氫糠酯、(甲基)丙烯酸環己酯、(甲基)丙烯酸正己酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸異癸酯、(甲基)丙烯酸2-甲氧基乙酯、(甲基)丙烯酸2-(2-乙氧基乙氧基)乙酯、(甲基)丙烯酸月桂酯、(甲基)丙烯酸2-苯氧基乙酯、(甲基)丙烯酸異氰酸乙酯、(甲基)丙烯酸縮水甘油酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸十三烷酯、己內酯(甲基)丙烯酸酯、(甲基)丙烯酸羥異丁酯及(甲基)丙烯酸四氫糠酯);及其組合。此等化合物可自廠家獲得,例如,賓夕法尼亞州,伊斯坦,薩托默公司;喬治亞州,土麥那,UCB化學公司;及威斯康辛州,密爾瓦基,阿瑞化學公司。
根據本發明之可聚合組合物亦可包括額外可聚合物質,例如,環氧樹脂、聚異氰酸酯及酚醛樹脂。
經氟化(甲基)丙烯酸酯化合物亦可包含於本發明之可聚合組合物中。適合經氟化(甲基)丙烯酸酯化合物之實例包括丙烯酸1H,1H-2,2,3,3,4,4,4-七氟丁酯,自密蘇里州,聖-路易士,西格馬-阿瑞公司(Sigma-Aldrich,Saint Louis,Missouri)獲得;丙烯酸1H,1H,2H,2H-全氟癸酯及/或丙烯酸ω-氫-2,2,3,3,4,4,5,5-八氟戊酯,二者均自新罕布夏,溫德姆,蘭開斯特合成公司(Lancaster Synthesis,Windham,New Hampshire)獲得;由美國專利第6,664,354號(薩沃等人)之實例2A和2B之步驟製造之C4
F9
SO2
N(CH3
)CH2
CH2
OC(=O)CH=CH2
;和美國專利第4,968,116號(胡姆-洛(Hulme-Lowe)等人)及第5,239,026號(巴比拉德(Babirad)等人)提及的經氟化(甲基)丙烯醯基化合物,包括丙烯酸(全氟環己基)甲酯。
可聚合組合物中可存在一定量邁克爾類型加成反應產物。例如,在其中清潔能力、耐久性及抗劃性理想之彼等應用中,以可聚合組合物之總重量計,邁克爾類型加成反應產物之量可小於或等於20重量%,例如,小於或等於10重量%或甚至小於或等於5重量%。在其中低折射率理想之應用中,可聚合組合物中的邁克爾類型加成反應產物之量可至少為50、60、70或甚至80重量%,至多至少95重量%。
為促進熟化,根據本發明之可聚合組合物可進一步包括至少一種游離基熱起始劑及/或光起始劑。如果此起始劑及/或光起始劑存在,以可聚合組合物之總重量計,其一般占可聚合組合物小於10重量%,更一般小於5重量%。游離基熟化技術為此項技藝上所熟悉,並包括(例如)熱熟化方法以及輻射熟化方法(如,電子束或紫外輻射)。關於游離基熱及光聚合技術之額外細節可發現於,例如,美國專利第4,654,233號(格蘭特(Grant)等人)、第4,855,184號(克侖(Klun)等人)及第6,224,949號(萊特(Wright)等人)。此外,敏化劑,如,自密西西比,帕斯卡古拉,第一化學公司(First Chemical Corporation,Pascagoula,Mississippi)購得的2-異丙基噻噸酮,可與光起始劑組合使用,例如"IRGACURE 369"。
所用游離基熱起始劑包括(例如)偶氮、過氧化物、過硫酸鹽及氧化還原起始劑及其組合。
適合偶氮起始劑包括,例如,2,2'-偶氮雙(4-甲氧基-2,4-二甲基戊腈)(在商品名"VAZO 33"下獲得)、2,2'-偶氮雙(2-脒基丙烷)二鹽酸鹽(在商品名"VAZO 50"下獲得)、2,2'-偶氮雙(2,4-二甲基戊腈)(在商品名"VAZO 52"下獲得)、2,2'-偶氮雙(異丁腈)(在商品名"VAZO 64"下獲得)、2,2'-偶氮-2-甲基丁腈)(在商品名"VAZO 67"下獲得)及1,1'-偶氮雙(1-環己烷甲腈)(在商品名"VAZO 88"下獲得),所有此等均自德拉瓦州,維明頓,E.I.杜邦-耐默斯公司獲得(E.I.du Pont de Nemours and Company,Wilmington,Delaware);及2,2'-偶氮雙(異丁酸甲酯),在商品名"V-601"自日本,大阪,瓦克純化學工業有限公司獲得(Wako Pure Chemical Industries,Ltd.,Osaka,Japan)。
適合過氧化物起始劑包括(例如)過氧化苯甲醯、過氧化物乙醯、過氧化月桂醯、過氧化十二烷醯、過氧二碳酸二(十六烷酯)、過氧二碳酸二(4-第三丁基環己酯)(自伊利諾斯州,芝加哥,亞克蘇化學公司(Akzo Chemicals,Chicago,Illinois)在商品名(PERKADOX 16)下獲得)、過氧二碳酸二(2-乙基己酯)、過新戊酸第三丁酯(自紐約,布法羅,亞托化學北美公司,有機過氧化物分公司(Lucidol Division,Atochem North America,Buffalo,New York)在商品名"LUPERSOL 11"下獲得)、2-乙基過己酸第三丁酯(自亞克蘇化學公司在商品名"TRIGONOX 21-C50"下獲得)及二枯基過氧化物。
適合過硫酸鹽起始劑包括(例如)過硫酸鉀、過硫酸鈉及過硫酸銨。
適合氧化還原(氧化-還原)起始劑包括,例如,過硫酸鹽起始劑與還原劑之組合,包括,例如偏亞硫酸氫鈉及亞硫酸氫鈉;以有機過氧化物和三級胺為基礎的系統(例如,過氧化苯甲醯與二甲基苯胺);及以有機氫過氧化物和過渡金屬為基礎的系統(例如,枯烯氫過氧化物與環烷酸鈷)。
所用游離基光起始劑包括(例如)已知用於丙烯酸酯聚合物UV熟化所用者。此等起始劑包括,二苯酮及其衍生物(包括丙烯酸化的二苯酮);苯偶姻,α-甲基苯偶姻,α-苯基苯偶姻,α-烯丙基苯偶姻,α-苄基苯偶姻;苯偶姻醚,如苯偶醯二甲基縮酮(自紐約,塔利頓,西巴特種化學品公司(Ciba Specialty Chemicals Corporation of Tarrytown,New York)在商品名"IRGACURE 651"下獲得),苯偶姻甲醚,苯偶姻乙醚,苯偶姻正丁醚;乙醯苯及其衍生物,如2-羥基-2-甲基-1-苯基-1-丙酮(自西巴特種化學品公司在商品名"DAROCUR 1173"下獲得)及1-羥基環己基苯基酮(亦自西巴特種化學品公司在商品名"IRGACURE 184"下獲得);2-甲基-1-[4-(甲基硫基)苯基]-2-(4-嗎啉基)-1-丙酮,在商品名"IRGACURE 907"下獲得,亦自西巴特種化學品公司;2-苄基-2-(二甲胺基)-1-[4-(4-嗎啉基)苯基]-1-丁酮,自西巴特種化學品公司在商品名"IRGACURE 369"下獲得;芳族酮(如,二苯酮)及其衍生物和蔥醌及其衍生物;鎓鹽,如重氮鹽、碘鎓鹽、硫鎓鹽;鈦錯合物,例如,在商品名"CGI 784 DC"下獲得者,亦自西巴特種化學品公司;鈾醯鹽;鹵代甲基硝基苯;及單-和雙-醯基膦,如自西巴特種化學品公司在商品名"IRGACURE 1700"、"IRGACURE 1800"、"IRGACURE 1850"、"IRGACURE 819"、"IRGACURE 2005"、"IRGACURE 2010"、"IRGACURE 2020"及"DAROCUR 4265"下獲得者。例如,亦可使用二或多種光起始劑之組合,以同時達到優良表面及完全熟化。
根據本發明之可聚合組合物可視需要包含一或多種額外成分,如抗氧化劑、光穩定劑、填料、香料、著色劑、抗靜電劑、無機奈米顆粒及/或溶劑。
可使根據本發明之可聚合組合物塗覆於基材上,且至少部分熟化,以提供如圖1中所示的複合物件。現在參考圖1,典型複合物件10包括具有在其上佈置的至少部分經聚合可聚合塗層12之基材14。在一些具體實施例中,經聚合塗層可形成提供至少一種抗損傷、抗塗畫、防污、黏著性釋放、低折射率及排水性之保護性塗層。
適合基材包括,例如,玻璃(例如,窗和光學元件,如透鏡及鏡子)、陶瓷(例如,瓷磚)、水泥、石、塗漆的表面(例如,汽車體面板、船表面)、金屬(例如,建築柱)、紙(例如,黏著性釋放襯墊)、卡紙板(例如,食品容器)、熱固材料、熱塑膠(例如,聚碳酸酯、丙烯酸樹脂、聚烯烴、聚胺基甲酸酯、聚酯、聚醯胺、聚醯亞胺、酚醛樹脂、二乙酸纖維素、三乙酸纖維素、聚苯乙烯及苯乙烯-丙烯腈共聚物)及其組合。基材可為薄膜、片材,或可具有一些其他形式。基材可包括其上視需要具有陶瓷硬膜的透明或半透明顯示元件。
可聚合組合物可由習知技術塗覆於基材上,如噴、刀塗、凹槽塗覆、反輥塗覆、凹版塗覆、浸塗、棒塗、泛塗或旋塗。一般便可聚合組合物作為相對較薄層塗覆到基材,產生具有40奈米至60奈米範圍厚度之經乾燥熟化層,雖然亦可使用更薄和更厚(例如,具有至高100微米或更厚之厚度)層。下一步,一般至少部分移除任何選用的溶劑(例如,強迫通風烘箱),然後使可聚合組合物至少部分聚合(即,熟化),以形成可耐久塗層,例如,如上所述。
例如,根據本發明之複合物件包括眼鏡片、鏡、窗、黏著劑性釋放襯墊及抗塗畫薄膜。
此外,根據本發明之複合物件可包括資訊顯示保護器。以圖說明,圖2顯示一典型資訊顯示保護器,一般性標為230。柔韌性透明薄膜233之第一主表面202支撐黏著層234,該層接觸到選用的保護性襯墊232。可視需要使黏著劑234之外表面204微結構化,例如,如圖所繪。在施加到顯示幕時,微結構化一般幫助氣泡自下面的資訊顯示器保護器230逸出,由此幫助在資訊顯示保護器230和顯示幕(未顯示)之間提供優良光學偶合。硬膜層236支撐於薄膜233之第二主表面206上。硬膜層236視需要具有粗化向外表面237,例如,如圖所繪,這用於對資訊顯示保護器230所接著的顯示幕提供眩光保護,並使其易於用觸筆寫於資訊顯示保護器230上。根據本發明之防污塗料組合物238支撐於硬膜236之上表面237上,且一般足夠薄,以在觀察表面231上複製硬膜236之粗化上表面237。
關於陶瓷硬膜、基材和顯示元件之額外細節可發現於(例如)美國專利第6,660,389號(琉(Liu)等人)及美國專利公開案第2003/0068486號(安尼(Arney)等人)。
本發明的目的及優勢進一步由以下非限制實例說明,但,此等實例中所引用的特定材料及其量以及其他條件和細節不應不適當限制本發明。
在實例中,除非另外注解,實例和說明書中其餘部分中的所有份、百分比、比等均以重量計。此外,除非另外注解,實例中所用的所有反應劑均可獲得,或自一般化學供應商獲得,例如,密蘇里州,聖-路易士,西格馬-阿瑞公司,或可藉由習知方法合成。
貫穿實例使用以下縮略符號:
此外,以下使用:mm=毫米,g=克,mg=毫克,mol=莫耳,mmol=毫莫耳,meq=毫當量,且mL=毫升。
在表2中,"NM"指未檢測。
將欲經檢驗的樣品(S1基材:30.5釐米×22.9釐米;S2基材:30.5釐米×15.2釐米)固定於能夠以35釐米/秒之速率振盪的機械裝置上,將此乾酪布折疊成十二層,並由橡膠襯墊固定到觸筆。將樣品固定,以使乾酪布以垂直於樣品塗覆方向之方向移動。觸筆具有具1.25英寸(3.2釐米)直徑之平、圓柱形幾何形狀。將該裝置用結合不同重量的平臺裝配,以增加由垂直於薄膜表面的觸筆所產生的力。乾酪布自賓夕法尼亞州,哈斯費德,薩默光學EMS包裝公司,EMS阿奎悉申公司分部(Summers Optical,EMS Packaging,a subdivision of EMS Acquisition Corp.,Hatsfield,Pennsylvania)在商品名"MIL SPEC CCC-C-440 PRODUCT# S12905"下獲得。"擦"係界定為單次10釐米移動。對各樣品報告對觸筆施加的重量(克)及對檢驗條件所用的"擦"數。
對樣品之表面塗層施加墨水標記,且毛氈筆(felt marker)在商品名"SANFORD SHARPIE,FINE POINT PERMANENT MARKER,NO.30001"下購得。觀察墨水標記,並確定墨水標記在施加到表面時起珠("是")與否("否")。
在適度手壓下用薄紙(tissue)擦墨水標記,所用薄紙自喬治亞州,羅斯維爾,親伯裏-克拉克公司(Kimberly Clark Corporation,Roswell,Georgia)在商品名"SURPASS FACIAL TISSUE"下獲得。觀察墨水標記,並確定墨水標記是否用薄紙由擦移除("是"或"否")。
在擦50、100、150、200、300和500次後記錄表面性能。
將具有2.5釐米×4釐米適合尺寸的經塗覆薄膜樣品切割並用雙面膠黏帶固定於標準顯微鏡載玻片上。用所接收的試劑級十六烷(威斯康辛州,密爾瓦基,阿瑞化學公司)進行接觸角檢測,去離子水通過自米利浦公司(Millipore Corporation)(麻塞諸塞州,比爾裏卡(Billerica,Massachusetts))獲得的過濾系統"MIILI-Q"過濾,視接觸角分析儀自AST產品公司(AST Products)(麻塞諸塞州,比爾裏卡)在商品名"VCA-2500XE"下獲得。報告值為對各滴相反側檢測的至少三滴之檢測平均值。對於靜態檢測,滴體積為5微升,而對於前進及後退檢測,滴體積為1-3微升。
將可聚合組合物用注射泵塗覆於基材S1或S2上,以使溶液計量進入模,以提供40-60奈米之乾燥厚度(nm)。溶劑利用在65℃加熱於習知氣浮烘箱中移除,然後將其以3米/分之線速度送過熟化室,熟化室具有小於50百萬分比(ppm)氧,並包含自馬里蘭州,蓋瑟斯堡,聯合UV系統公司(Fusion UV Systems,Gaithersburg,Maryland)獲得的在完全功率操作的600瓦H-型燈泡。
將可聚合組合物用塗覆滑塊(coating block)以127微米濕厚塗覆於基材S1或S2上。溶劑在120℃溫度操作的烘箱中經10分鐘移除。下一步,利用自馬里蘭州,蓋瑟斯堡,聯合UV系統公司獲得的在完全功率操作的600瓦(600焦耳/秒)"D-型"燈泡,使塗層在氮氣下以35英尺/分(11米/分)之線速度熟化。
製備HFPOC(=O)NHCH 2 CH 2 CH 2 NHCH 3 (FC-1/AM-1)
二者均在室溫,用291.24克(0.2405莫耳)之FC-1和21.2克(0.2405莫耳)AM-1填充一個1升圓底燒瓶,產生混濁溶液。使燒瓶內形成渦旋,並使混合物之溫度升到45℃,以得到水白色液體,將其於55℃加熱過夜。然後將產物置於75℃和28英寸Hg真空的旋轉式蒸發器上,以移除甲醇,產生301.88克黏性徵黃液體(即,FC-1/AM-1),名義分子量=1267.15克/莫耳。
製備HFPOC(=O)NHCH 2 CH 2 NHCH 2 CH 3 (FC-1/AM-2)
根據製備FC-1/AM-1之步驟,但用AM-2代替AM-1,使50克(41.29毫莫耳)FC-1與3.64克(41.29毫莫耳)AM-2化合,以提供FC-1/AM-2,名義分子量=1267.15克/莫耳。
製備HFPOC(=O)NHCH 2 CH 2 NHCH 2 CH 2 OH(FC-1/AM-3)
根據製備FC-1/AM-1之步驟,但用AM-3代替AM-1,使300克(0.2477莫耳)FC-1與25.8克(0.2477莫耳)AM-3反應,以提供312.0克FC-1/AM-3,名義分子量=1283.15克/莫耳。
製備HFPOC(=O)NH(CH 2 CH 2 NH) 4 CH 2 CH 2 NHC(=O)HFPO(FC-1/AM-4)
根據製備FC-1/AM-1之步驟,但用AM-4代替AM-1,使50克(41.29毫莫耳)FC-1與4.80克(20.64毫莫耳)AM-4化合,並且濃縮,以提供FC-1/AM-4,名義分子量2590.4,名義當量=647.6克/莫耳。
製備HFPOC(O)N(H)CH 2 CH 2 NH 2 (FC-1/AM-5)
將9.92克(165毫莫耳)之AM-5加入一配有磁力攪拌棒之100毫升圓底燒瓶。下一步,在室溫經約1小時加入20克(16.5毫莫耳)之FC-1。在攪拌額外1小時後,在高達130℃之溫度於2.5毫米壓力移除揮發物,以提供FC-1/AM-5,名義分子量=1239.1克/莫耳。
製備HFPOC(=O)NHCH 2 CH 2 CH 2 NH 2 (FC-1/AM-7)
在室溫將6.12克(82.6毫莫耳)之AM-7和20克(16.5毫莫耳)FC-1加入一配有磁力攪拌棒之50毫升圓底燒瓶。下一步,在室溫將混合物攪拌約30分鐘。最後,在高達150℃之溫度於4.0毫米壓力移除揮發物,以提供FC-1/AM-7,名義分子量=1253.1克/莫耳。
CH 3 NHCH 2 CH 2 CH 2 NHC(=O)-CF 2 O(CF 2 CF 2 O)b(CF 2 O) c CF 2 O-C(=O)NHCH 2 CH 2 CH 2 NHCH 3 (FC-2/AM-1)之製備
根據製備FC-1/AM-1之步驟,但用FC-2代替FC-1,使20克(20毫當量)FC-2與1.76克(20毫當量)AM-1化合,並且濃縮,以提供FC-2/AM-1,名義分子量2112.3,名義當量=1056.15克/莫耳。
製備1:1莫耳比之AM-6與AC-1之加合物(AM-6/AC-1)
將7.51克(0.1莫耳)之AM-6和1.8毫克吩噻嗪加入一配有磁力攪拌棒之100毫升燒瓶。下一步,在23℃,通過壓力平衡漏斗加入29.61克(0.1莫耳)AC-1。使反應溫度升到51℃,然後降回到室溫,以提供AM-6/AC-1,名義分子量=371.1克/莫耳。
本實例描述製備約1:1莫耳比之FC-1/AM-1與AC-1之加合物(FC-1/AM-1/AC-1)。
用4.48克(15.13毫莫耳)之AC-1、4.45克四氫呋喃(THF)和1.6毫克吩噻嗪填充一250毫升圓底燒瓶,並在油浴中於55℃加熱。下一步,在100毫升瓶中使20克(15.78毫莫耳)FC-1/AM-1溶於32克THF。將該溶液放入利用壓力平衡側臂之60毫升滴液漏斗。用~3毫升THF清洗該瓶,亦將其加到該滴液漏斗,並在空氣氣氛下,經38分鐘將漏斗之內容物加入AC-1/THF/吩噻嗪混合物。反應起初混濁,但在約30分鐘後清澈。在加入完成後20分鐘,將反應燒瓶置於45-55℃和28英寸Hg真空的旋轉式蒸發器上,以產生24.38克清澈、黏性黃色液體,由1
H和1 3
C NMR及HPLC/質譜分析其特徵。由HPLC/質譜測定,所得物質(即,FC-1/AM-1/AC-1)具有以下近似莫耳產物分佈:20% AC-140%具有下式之單加合物
40%二加合物。
本實例描述製備約1:1莫耳比之FC-1/AM-1與AC-2之加合物(FC-1/AM-1/AC-2)。
根據實例1之步驟,但用AC-2代替AC-1,將於約35克THF中的20克(15.78毫莫耳)之FC-1/AM-1加入於約4.5克THF中的4.51克(15.13毫莫耳)之AC-2與1.6毫克吩噻嗪,並且濃縮,以提供FC-1/AM-1/AC-2。
本實例描述製備約1:1莫耳比之FC-1/AM-1與AC-4之加合物(FC-1/AM-1/AC-4)。
根據實例1之步驟,但用AC-4代替AC-1,將於約35克THF中的20克(15.78毫莫耳)之FC-1/AM-1加入於約6.8克THF中的6.56克(15.33毫莫耳)之AC-4與2.0毫克吩噻嗪,並且濃縮,以提供FC-1/AM-1/AC-4。
本實例描述製備約1:1莫耳比之FC-1/AM-1與AC-5之加合物(FC-1/AM-1/AC-5)。
根據實例1之步驟,但用AC-5代替AC-1,將於約40克THF中的20克(15.78毫莫耳)之FC-1/AM-1加入於約8.41克THF中的8.14克(15.48毫莫耳)之AC-5與1.6毫克吩噻嗪,並且濃縮,以提供FC-1/AM-1/AC-5。
本實例描述製備約1:3莫耳比之FC-1/AM-1與AC-6之加合物(FC-1/AM-1/AC-6)。
根據實例1之步驟,但用AC-6代替AC-1,將於約15克THF中的5.00克(3.95毫莫耳)之FC-1/AM-1加入於約2.5克THF中的2.35克(11.84毫莫耳)之AC-6與0.3毫克吩噻嗪,以在濃縮時提供FC-1/AM-1/AC-6。
本實例描述製備約1:1莫耳比之FC-1/AM-2與AC-1之加合物(FC-1/AM-2/AC-1)。
根據實例1之步驟,但用AM-2代替AM-1,將於約35克THF中的20克(15.78毫莫耳)之FC-1/AM-2加入於約4.5克THF中的4.48克(15.14毫莫耳)之AC-1與1.6毫克吩噻嗪,以在濃縮時提供FC-1/AM-2/AC-1。
本實例描述製備1:1莫耳比之FC-1/AM-2與AC-3之加合物(FC-1/AM-2/AC-3)。
根據實例7之步驟,但用AC-3代替AC-1,將於約35克THF中的19.5克(15.4毫莫耳)之FC-1/AM-2加入於約8克THF中的7.81克(15.4毫莫耳)之AC-3與2.1毫克吩噻嗪,以在濃縮時提供FC-1/AM-2/AC-3。
本實例描述製備1:1莫耳比之FC-1/AM-2與AC-4之加合物(FC-1/AM-2/AC-4)。
根據實例7之步驟,但用AC-4代替AC-1,將於約35克THF中的20克(15.78毫莫耳)之FC-1/AM-2加入於約6.6克THF中的6.56克(15.33毫莫耳)之AC-4與1.2毫克吩噻嗪,以在濃縮時提供FC-1/AM-2/AC-4。
本實例描述製備約1:1莫耳比之FC-1/AM-2與AC-5之加合物(FC-1/AM-2/AC-5)。
根據實例7之步驟,但用AC-5代替AC-1,將於約35克THF中的20克(15.78毫莫耳)之FC-1/AM-2加入於約8.2克THF中的8.14克(15.48毫莫耳)之AC-5與1.2毫克吩噻嗪,以在濃縮時提供FC-1/AM-2/AC-5。
本實例描述製備約1:1莫耳比之FC-1/AM-3與AC-1之加合物(FC-1/AM-3/AC-1)。
根據實例1之步驟,但用AM-3代替AM-1,使20克(15.6毫莫耳)之FC-1/AM-3與4.43克(14.97毫莫耳)之AC-1反應,以產生24.37克產物(FC-1/AM-3/AC-1),以莫耳計,該產物為約三分之二之胺單加合物
及約三分之一可相信為以上化合物和AC-1之羥基單加合物之物質。
本實例描述製備約1:1莫耳比之FC-1/AM-3與AC-2之加合物(FC-1/AM-3/AC-2)。
根據實例10之步驟,但用AC-2代替AC-1,將於約35克THF中的20克(15.6毫莫耳)之FC-1/AM-3加入於約4.4克THF中的4.46克(14.97毫莫耳)之AC-2與1.8毫克吩噻嗪,以在濃縮時提供FC-1/AM-3/AC-2。
本實例描述製備約1:1莫耳比之FC-1/AM-3與AC-4之加合物(FC-1/AM-3/AC-3)。
根據實例10之步驟,但用AC-3代替AC-1,將於約35克THF中的20克(15.59毫莫耳)之FC-1/AM-3加入於約6.5克THF中的6.48克(15.14毫莫耳)之AC-4,以在濃縮時提供FC-1/AM-3/AC-4。
本實例描述製備約1:4莫耳比(1:1當量)之FC-1/AM-4與AC-1之加合物(FC-1/AM-4/AC-1)。
根據實例1之步驟,但用AM-4代替AM-1,將於約40克THF中的20克(30.88毫當量)之FC-1/AM-4加入於約8.8克THF中的8.77克(29.62毫當量)之AC-1與1.6毫克吩噻嗪,以在濃縮時提供FC-1/AM-4/AC-1。
本實例描述製備約1:2莫耳比之FC-1/AM-5與AC-1(FC-1/AM-5/AC-1)。
根據實例1之步驟,但用AM-5代替AM-1,將於約9.9克THF和10.1克FS中的5.0克(4.04毫莫耳)之FC-1/AM-5加入於約5.6克THF和5.8克FS中的2.39克(8.07毫莫耳)之AC-1與0.4毫克吩噻嗪,以在濃縮時提供FC-1/AM-5/AC-1。
本實例描述製備約1:2莫耳比之FC-1/AM-7與AC-1(FC-1/AM-7/AC-1)。
根據實例1之步驟,但用AM-7代替AM-1,將於約6克THF和6克FS中的5.0克(3.99毫莫耳)之FC-1/AM-7加入於約6克THF和6克FS中的2.36克(7.98毫莫耳)之AC-1與0.4毫克吩噻嗪,以在濃縮時提供FC-1/AM-7/AC-1。
本實例描述製備約1:2莫耳比(1:1當量)之FC-2/AM-1與AC-1之加合物(FC-2/AM-1/AC-1)。
根據實例1之步驟,但用FC-2代替FC-1,將於約25克THF中的10克(9.47毫當量)之FC-2/AM-1加入於約3克THF中的2.80克(9.46毫當量)之AC-1與0.6毫克吩噻嗪,以在濃縮時提供FC-2/AM-1/AC-1。
本實例描述製備約1:1莫耳比之FC-3和AM-6/AC-1之加合物(FC-3/AM-6/AC-1)。
將3.32克(8.97毫莫耳)之AM-6/AC-1、1.17克(8.97毫莫耳)之N,N-二異丙基-N-乙胺、0.7毫克吩噻嗪、7.25克乙酸乙酯和8.21克FS加入一個配有磁力攪拌棒之100毫升燒瓶,並加熱到40℃,歷經30分鐘自壓力平衡漏斗加入10.0克(8.97毫莫耳)之FC-3、18.62克FS和17.92克乙酸乙酯之混合物。攪拌過夜後,反應用等體積去離子水清洗兩次,經無水硫酸鎂乾燥,過濾,並由旋轉式蒸發濃縮。
利用表1中所報告的物質和量,用可聚合組合物塗覆基材。所有可聚合組分均稀釋到總固體之10重量%總固體。利用10%固體光起始劑溶液(於甲基乙基酮中),將2重量%之光起始劑PI-1或1重量%之PI-2包括於可聚合組合物中。在稀釋到最終重量百分比總固體前加入光起始劑。對含PI-1之調配物使用甲基異丁基酮或對含PI-2之調配物使用甲基乙基酮,將彼等稀釋到最終重量百分比總固體。各塗料溶液用下述塗覆方法1或塗覆方法2塗覆於塗覆基材上。
用接觸角測量步驟評估塗層,以用水(靜態、前進及後退)與十六烷(靜態、前進及後退)測定接觸角。此等分析之結果報告於表2中(以下)。
使60奈米名義塗層厚度的一些經塗覆烏澤薄膜經過至多500摩擦的乾酪布耐久性檢驗。結果報告於表3中(以下),其中"Y"意味是,"N"表示否。
熟諳此藝者可在不脫離本發明之範圍和主旨下對本發明進行不同改進和替代,且應懂得,不應不適當限制本發明於本文所述的說明性具體實施例。
10...複合物件
12...經聚合可聚合塗層
14...基材
202...第一主表面
204...黏著層
206...第二主表面
230...資訊顯示保護器
231...觀察表面
232...保護性襯墊
233...柔韌性透明薄膜233
234...觀察表面
236...硬膜層
237...粗化向外表面
238...防污塗料組合物
圖1為根據本發明一典型具體實施例之複合物件之示意側視圖。
圖2為根據本發明一典型具體實施例之資訊顯示保護器之示意側視圖。
10...複合物件
12...經聚合可聚合塗層
14...基材
Claims (28)
- 一種可聚合組合物,其包括至少一種由下式所描述之化合物(F(Rf O)x QZ1 R1 NR2 CH2 CH2 C(=O)Z2 )y M(Z3 C(C=O)CR3 =CH2 )z 或X[((Rf O)z QZ1 R1 NR2 CH2 CH2 C(=O)Z2 )y M(Z3 C(=O)CR3 =CH2 )z ]b 其中各Rf 獨立代表具有1至6個碳原子之經氟化伸烷基;各x獨立代表大於或等於2之整數;各Q獨立代表-CF2 -、-CF(CF3 )-、-CF2 CF2 -、-CF2 CF2 CF2 -、-CF2 CF(CF3 )-、-CF(CF3 )CF2 -、-CF2 CF2 CH2 -、-CF2 CH2 -、-CF2 CF2 C(=O)-、-CF2 C(=O)-、-CF(CF3 )C(=O)-、-CF(CF3 )CH2 -、具有1至6個碳原子之伸烷基或具有1至6個碳原子之雜伸烷基;各Z1 、Z2 和Z3 獨立代表-S-、-O-、-NH-或-NR2 -;各R1 獨立代表伸烷基、伸芳烷基或雜伸烷基;各R2 獨立代表H、具有1至6個碳原子之烷基、-CH2 CH2 C(=O)Z2 M(Z3 C(=O)CR3 =CH2 )z 或-R1 Z1 Q(ORf )x F;各R3 獨立代表H、F或甲基;各y和z獨立代表大於或等於1之整數;各M係選自由2,2-雙(基甲基)丁-1-基、伸乙基、2,2-雙(基甲基)-丙-1,3-二基、2,2,6,6-肆(基甲基)-4-氧雜庚-1,7-二基、丁-1,3-二基、己-1,6-二基及1,4-雙(基甲基)環己烷所組成之群組; X為全氟伸烷二氧基;且b代表大於或等於2之整數。
- 如請求項1之可聚合組合物,其中該各Rf 係獨立選自-CF2 -、-CF(CF3 )-、-CF2 CF2 -、-CF2 CF2 CF2 -、-CF(CF3 )CF2 -或-CF2 CFCH2 -。
- 如請求項1之可聚合組合物,其中該各Rf 係經全氟化。
- 如請求項1之可聚合組合物,其中該各R1 獨立具有1至6個碳原子。
- 如請求項1之可聚合組合物,其中該各x係獨立大於或等於3。
- 如請求項1之可聚合組合物,其中該各y獨立為1、2或3。
- 如請求項1之可聚合組合物,其中該各Z3 獨立為-O-。
- 如請求項1之可聚合組合物,其中該各Z2 獨立代表-O-。
- 如請求項1之可聚合組合物,其中該各M獨立為具有至少3價之多價有機基團。
- 如請求項1之可聚合組合物,其進一步包括至少一種額外游離基可聚合單體。
- 一種製造如請求項1之可聚合組合物之方法,其包括使反應性經氟化聚醚,其中該反應性經氟化聚醚係由下式所描述者:F(Rf O)x QZ1 R1 NR2 H或X(Rf O)x QZ1 R1 NR2 H 其中各Rf 獨立代表具有1至6個碳原子之經氟化伸烷基;各x獨立代表大於或等於2之整數;各Q獨立代表-CF2 -、-CF(CF3 )-、-CF2 CF2 -、-CF2 CF2 CF2 -、-CF2 CF(CF3 )-、-CF(CF3 )CF2 -、-CF2 CF2 CH2 -、-CF2 CH2 -、-CF2 CF2 C(=O)-、-CF2 C(=O)-、-CF(CF3 )C(=O)-、-CF(CF3 )CH2 -、具有1至6個碳原子之伸烷基或具有1至6個碳原子之雜伸烷基;Z1 代表-S-、-O-、-NH-或-NR2 -;R1 獨立代表伸烷基、伸芳烷基或雜伸烷基;R2 獨立代表H或具有1至6個碳原子之烷基;及X代表多價有機基團;和包括複數個(甲基)丙烯醯基之聚(甲基)丙烯醯基化合物在足以生成其邁克爾類型加合物之條件下化合,其中該邁克爾類型加合物具有至少一個(甲基)丙烯醯基。
- 如請求項11之方法,其中該R1 具有1至6個碳原子。
- 如請求項11之方法,其中該x係大於或等於3。
- 如請求項11之方法,其中該Z1 代表-NR2 -。
- 如請求項11之方法,其中該Z1 代表-NH-。
- 如請求項11之方法,其進一步包括使該邁克爾類型加合物和至少一種額外可聚合單體化合。
- 如請求項16之方法,其進一步包括使該邁克爾類型加合物和至少一種額外可聚合單體至少部分聚合。
- 如請求項16之方法,其進一步包括使該邁克爾類型加合物和至少一種額外可聚合單體之組合施加到基材。
- 如請求項18之方法,其進一步包括使該邁克爾類型加合物和至少一種額外可聚合單體至少部分聚合,以提供經聚合的混合物。
- 如請求項11之方法,其進一步使該邁克爾類型加合物、至少一種額外可聚合單體及至少一種遊離基光起始劑化合。
- 如請求項20之方法,其進一步包括使該邁克爾類型加合物和至少一種額外可聚合單體至少部分聚合。
- 如請求項20之方法,其進一步包括使該至少部分經聚合的邁克爾類型加合物和至少一種額外可聚合單體施加到基材。
- 如請求項22之方法,其進一步包括使該可聚合混合物至少部分聚合。
- 一種複合物件,其包括其至少部分上具有防污組合物之基材,該防污組合物可藉由使一種可聚合組合物至少部分聚合而製備,該可聚合組合物包括至少一種由下式所描述之化合物(F(Rf O)x QZ1 R1 NR2 CH2 CH2 C(=O)Z2 )y M(Z3 C(C=O)CR3 =CH2 )z 或X[((Rf O)x QZ1 R1 NR2 CH2 CH2 C(=O)Z2 )y M(Z3 C(=O)CR3 =CH2 )z ]b 其中各Rf 獨立代表具有1至6個碳原子之經氟化伸烷基; 各x獨立代表大於或等於2之整數;各Q獨立代表-CF2 -、-CF(CF3 )-、-CF2 CF2 -、-CF2 CF2 CF2 -、-CF2 CF(CF3 )-、-CF(CF3 )CF2 -、-CF2 CF2 CH2 -、-CF2 CH2 -、-CF2 CF2 C(=O)-、-CF2 C(=O)-、-CF(CF3 )C(=O)-、-CF(CF3 )CH2 -、具有1至6個碳原子之伸烷基或具有1至6個碳原子之雜伸烷基;各Z1 、Z2 和Z3 獨立代表-S-、-O-、-NH-或-NR2 -;各R1 獨立代表伸烷基、伸芳烷基或雜伸烷基;各R2 獨立代表H、具有1至6個碳原子之烷基、-CH2 CH2 C(=O)Z2 M(Z3 C(=O)CR3 =CH2 )z 或-R1 Z1 Q(ORf )x F;各R3 獨立代表H、F或甲基;各y和z獨立代表大於或等於1之整數;各M係選自由2,2-雙(基甲基)丁-1-基、伸乙基、2,2-雙(基甲基)-丙-1,3-二基、2,2,6,6-肆(基甲基)-4-氧雜庚-1,7-二基、丁-1,3-二基、己-1,6-二基及1,4-雙(基甲基)環己烷所組成之群組;X為全氟伸烷二氧基;且b代表大於或等於2之整數。
- 如請求項24之複合物件,其中該防污組合物進一步包括至少一種額外的游離基可聚合單體。
- 如請求項25之複合物件,其中該防污組合物係支撐於硬膜上。
- 如請求項25之複合物件,其中該複合物件包括一種資訊顯示保護器。
- 如請求項27之複合物件,其中該資訊顯示保護器包括具有第一和第二相反主表面之柔韌性透明薄膜,其中一接著層係支撐於該第一表面上,其中一硬膜層係支撐於該第二表面上,且其中該防污組合物層係支撐於該硬膜層上。
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2004
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2005
- 2005-03-14 JP JP2007511359A patent/JP5038129B2/ja not_active Expired - Fee Related
- 2005-03-14 KR KR1020067025639A patent/KR101187124B1/ko active IP Right Grant
- 2005-03-14 WO PCT/US2005/008572 patent/WO2005113642A1/en active Application Filing
- 2005-03-14 DE DE602005010683T patent/DE602005010683D1/de active Active
- 2005-03-14 EP EP05729213A patent/EP1742985B1/en not_active Not-in-force
- 2005-03-14 AT AT05729213T patent/ATE412685T1/de not_active IP Right Cessation
- 2005-03-14 CN CNB2005800145739A patent/CN100549064C/zh not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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DE602005010683D1 (de) | 2008-12-11 |
KR20070010078A (ko) | 2007-01-19 |
WO2005113642A1 (en) | 2005-12-01 |
KR101187124B1 (ko) | 2012-09-28 |
JP5038129B2 (ja) | 2012-10-03 |
EP1742985B1 (en) | 2008-10-29 |
EP1742985A1 (en) | 2007-01-17 |
CN1950427A (zh) | 2007-04-18 |
CN100549064C (zh) | 2009-10-14 |
JP2007536393A (ja) | 2007-12-13 |
ATE412685T1 (de) | 2008-11-15 |
TW200611935A (en) | 2006-04-16 |
US7342080B2 (en) | 2008-03-11 |
US20050250921A1 (en) | 2005-11-10 |
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