TW202110915A - 具有全氟聚醚基之矽氧烷丙烯酸酯 - Google Patents
具有全氟聚醚基之矽氧烷丙烯酸酯 Download PDFInfo
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- TW202110915A TW202110915A TW108137986A TW108137986A TW202110915A TW 202110915 A TW202110915 A TW 202110915A TW 108137986 A TW108137986 A TW 108137986A TW 108137986 A TW108137986 A TW 108137986A TW 202110915 A TW202110915 A TW 202110915A
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- formula
- fluorine
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- compound
- acrylate
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- 239000010702 perfluoropolyether Substances 0.000 title claims abstract description 25
- -1 Siloxane acrylate Chemical class 0.000 title abstract description 43
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 67
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 63
- 239000011737 fluorine Substances 0.000 claims abstract description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 17
- 125000000962 organic group Chemical group 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 62
- 229920001296 polysiloxane Polymers 0.000 claims description 41
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 239000008199 coating composition Substances 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 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 description 7
- 229910052710 silicon Inorganic materials 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 103
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- 238000006243 chemical reaction Methods 0.000 description 21
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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- 230000000052 comparative effect Effects 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
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- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 6
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- 239000000654 additive Substances 0.000 description 6
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- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 5
- 230000003373 anti-fouling effect Effects 0.000 description 5
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- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
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- 238000006459 hydrosilylation reaction Methods 0.000 description 4
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- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- 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
- C08F222/00—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 a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/104—Esters of polyhydric alcohols or polyhydric phenols of tetraalcohols, e.g. pentaerythritol tetra(meth)acrylate
-
- 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
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/067—Polyurethanes; Polyureas
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
本發明為關於可光硬化的具有全氟聚醚基之矽氧烷丙烯酸酯(以下,稱為「含氟矽氧烷丙烯酸酯」。)。
以往,包含具有全氟烷基的聚合性單體、丙烯酸含氟烷基酯或甲基丙烯酸含氟烷基酯之聚合物,作為藉由紫外線等光照射而可硬化之氟化合物而廣為人知。作為具代表性者,以於基材表面賦予低反射性、撥水撥油性、防污性、耐磨損性、耐擦傷性等為目的而廣泛地使用下述構造式所表示的化合物。
但,近年由於環境負荷的疑慮,增強限制利用含有碳原子數8以上的長鏈全氟烷基之化合物的動向。然而,已知含有碳原子數未滿8的全氟烷基之丙烯酸化合物,與具有碳原子數8以上的長鏈全氟烷基者相較下,其表面特性顯著地惡化(非專利文獻1)。
另一方面,已知導入有包含連續之碳原子數為3以下的全氟伸烷基與醚鍵結性氧原子之全氟聚醚類的可光硬化之氟化合物。例如,提案有源自六氟環氧丙烷寡聚物之含氟丙烯酸化合物(專利文獻1)、或含有含氟聚醚二醇與甲基丙烯酸-2-異氰酸基乙酯之反應物的胺基甲酸酯丙烯酸酯(專利文獻2)。然而,由於含氟化合物的撥水撥油特性,與光聚合起始劑、非氟化丙烯酸酯及非氟化有機溶劑之相溶性較低,而可摻合成分及用途被限制。
相對於此,提案有具備環狀矽氧烷構造與胺基甲酸酯構造,且與非氟系溶劑的相溶性優異之含氟丙烯酸酯化合物(專利文獻3)。然而,考慮到將該化合物摻合於用來形成抗反射膜的組成物中,較佳為具有更低的折射率之含氟丙烯酸酯。與非氟系溶劑的相溶性及折射率存在取捨(trade‐off)的關係,為了使相溶性提升而將胺基甲酸酯構造大量導入構造中之專利文獻3所示之含氟丙烯酸酯所形成的被膜的折射率高,而損害被膜的低反射性。進而,含氟丙烯酸酯中的丙烯醯基量與折射率亦存在取捨的關係,為了使含氟丙烯酸酯的折射率降低而減少丙烯醯基的含量,則損害所形成的被膜的強度。
由於上述的背景,而期望有不損害與非氟系溶劑的相溶性,且不減少丙烯醯基,且實現更低的折射率之含氟丙烯酸酯化合物。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本特開平5-194322號公報
[專利文獻2]日本特開平11-349651號公報
[專利文獻3]日本特許第4873666號公報
[非專利文獻]
[非專利文獻1]高分子諭文集Vol.64,No.4,pp.181-190(Apr.2007)
[發明所欲解決之問題]
本發明係鑑於上述情況而完成者,其目的為提供在保持丙烯醯基的含量的同時,實現對於非氟系溶劑之良好的相溶性與低折射率之具有全氟聚醚基的含氟矽氧烷丙烯酸酯。
[解決問題之技術手段]
本發明者為了解決上述課題而精心研究的結果,發現下述含氟矽氧烷丙烯酸酯在保持丙烯醯基的含量的同時,可實現對於非氟系溶劑之良好的相溶性與低折射率,而完成本發明。
即,本發明提供:
1. 下述式(1)所表示的含氟矽氧烷丙烯酸酯,
[式中,PFPE表示數量平均分子量500~30,000之2價的全氟聚醚鏈,X分別獨立地為下述式(2)所表示的基,
{式(2)中,Y1
分別獨立地為可包含醚鍵、亦可具有環狀構造或分支構造之2價有機基,R2
分別獨立地為氫原子、氟原子、甲基或三氟甲基,G分別獨立地為碳原子數1~12的烷基或下述式(3)所表示的基,
(式(3)中,R1
為碳原子數1~12的1價烴基,Y1
如同上述。虛線表示鍵結處。)
Q為氫原子或下述式(4)所表示的基,
(式(4)中,R3
分別獨立地為碳原子數1~12的1價烴基。虛線表示鍵結處。)
e為0~2的整數,f為0~2的整數,g為1~3的整數,e+f+g為3。虛線表示鍵結處。}
Z分別獨立地為下述式所表示的2價有機基。
(式中,虛線表示鍵結處,**記號表示與前述PFPE的鍵結部位。)]
2. 如1之含氟矽氧烷丙烯酸酯,其中PFPE為下述式所表示的數量平均分子量1,000~5,000之全氟聚醚鏈,
(式中,a為a≧1之數,b為b≧1之數,a/b為1/10~10/1之數。附有a及b之括弧內的重複單位之排列可為任意。虛線表示鍵結處。)
3. 如1或2之含氟矽氧烷丙烯酸酯,其中Z為下述式所表示的2價有機基,
(式中,虛線表示鍵結處,**記號表示與前述PFPE的鍵結部位。)
4. 如1~3中任一者之含氟矽氧烷丙烯酸酯,其中Y1
為下述式所表示的2價有機基,
(式中,虛線表示鍵結處,星號(*)表示與矽原子的鍵結部位。)
5. 如1~4中任一者之含氟矽氧烷丙烯酸酯,其中G為碳原子數1~6的烷基或上述式(3)所表示的基,式(3)中的R1
為甲基、乙基或n-丙基,e為1或2,
6. 如5之含氟矽氧烷丙烯酸酯,其中G為碳原子數1~3的烷基,
7. 如1~4中任一項之含氟矽氧烷丙烯酸酯,其中e為0,
8. 一種塗布組成物,其包含如1~7中任一者之含氟矽氧烷丙烯酸酯,
9. 如8之塗布組成物,其進而包含如1~7中任一者之含氟矽氧烷丙烯酸酯以外之丙烯酸酯或胺基甲酸酯丙烯酸酯,
10. 一種具有被膜的物品,其具有由如8或9之塗布組成物的硬化物所構成之被膜。
[發明之效果]
本發明之含氟矽氧烷丙烯酸酯在丙烯醯基量與以往的含氟丙烯酸酯為同等的同時,達成與非氟系有機化合物之相溶性與低折射率兩者,而可形成利用光硬化之撥水撥油性的硬化物,其有用於抗反射膜用的樹脂、或者有用於硬塗用的添加劑。
式(1)中,PFPE為數量平均分子量500~30,000之2價的全氟聚醚鏈。較佳為1,000~5,000,較佳為具有下述構造式(5)所表示的全氟伸烷基與氧原子交互連結之構造者。另外,本發明中數量平均分子量為依據凝膠滲透層析(GPC)之標準聚苯乙烯換算值。
式(5)中,A表示碳原子數1~3的全氟伸烷基,可為相同亦可為相異,排列亦可為任意。n為1以上的數,較佳為6~60的數,更佳為10~35的數。虛線表示鍵結處(以下相同)。
全氟聚醚鏈中,從大量存在展現滑性成為彎曲點的氧原子的觀點、無阻礙鏈的彎曲運動之分支構造的觀點等而言,作為A較佳為全氟亞甲基及全氟伸乙基。
PFPE所表示之2價的全氟聚醚鏈,考量到工業上容易取得的觀點,則特佳為氧二氟亞甲基
(oxydifluoromethylenegroup)與氧四氟伸乙基
(oxytetrafluoroethylenegroup)共存之下述式(6)所表示者。
式(6)中,全氟氧亞甲基的數(a)為a≧1的數,全氟氧伸乙基的數(b)為b≧1的數。全氟氧亞甲基的數(a)與全氟氧伸乙基的數(b)之比(a/b),並非特別限定者,但較佳為1/10~10/1的數,更佳為3/10~10/3的數。附有a及b之括弧內的重複單位之排列可為任意。
R2
分別獨立地為氫原子、氟原子、甲基或三氟甲基,較佳為氫原子、甲基,特佳為氫原子。
Y1
分別獨立地為可包含醚鍵(但,在與氧原子之鍵結末端包含O,產生-O-O-鍵結者除外)、亦可具有環狀構造或分支構造之2價有機基。作為Y1
,例如舉例有碳原子數2~20、較佳為2~10的伸烷基等,但較佳為以下的構造式所表示者。
作為G的烷基,例如舉例有甲基、乙基、n-丙基、i-丙基、n-丁基、s-丁基、t-丁基、n-戊基、n-己基、環己基等。G較佳為碳原子數1~6,更佳為碳原子數1~4,進而佳為碳原子數1~3的烷基,特佳為甲基、乙基、n-丙基。
式(3)中,R1
為碳原子數1~12的1價烴基,具體而言例如舉例有甲基、乙基、n-丙基、i-丙基、n-丁基、s-丁基、t-丁基、n-戊基、n-己基、環己基等烷基、苯基等芳基等。作為R1
較佳為碳原子數1~3的烷基,更佳為甲基、乙基、n-丙基。
R3
分別獨立地為碳原子數1~12的1價烴基,具體而言,可舉例為與R1
所例示之相同者。作為R3
較佳為碳原子數1~3的烷基,更佳為甲基、乙基、n-丙基。
e為0~2的整數,但較佳為0,f為0~2的整數,g為1~3的整數,e+f+g為3。
[製造方法]
本發明之含氟矽氧烷丙烯酸酯,例如可利用以下的方法製造。
[1]氫矽氧烷的合成
首先,使下述式(7)所表示之於兩末端具有烷氧基矽基之全氟聚醚,與下述式(8a)及/或(8b)所表示的具有Si-H鍵之化合物進行共水解縮合,藉此可製造下述式(9)所表示的具有全氟聚醚基之氫矽氧烷。
式中,R4
、R5
分別獨立地為碳原子數1~12,較佳為1~6,更佳為1~4的烷基,R6
為碳原子數1~12,較佳為1~6,更佳為1~4的烷基。w分別獨立地為0~2的整數,PFPE及Z如同上述(以下相同)。
作為R4
、R5
、R6
,例如舉例有甲基、乙基、n-丙基、i-丙基、n-丁基、s-丁基、t-丁基、n-戊基、n-己基、環己基等烷基,較佳為甲基、乙基、n-丙基、n-丁基。
共水解中,為了防止化合物(7)彼此的交聯,相對於化合物(7)之化合物(8a)及/或(8b)的摻合量,較佳為相對於化合物(7)的烷氧基1當量,使用以矽換算計2當量以上的化合物(8a)及/或(8b)進行共水解,之後,藉由減壓餾除未反應的化合物(8a)及/或(8b)而去除,較佳為相對於化合物(7)的烷氧基1當量,在化合物(8a)及/或(8b)以矽換算計為2~10當量,尤其2~6當量的存在下使其反應。另外,併用化合物(8a)與化合物(8b)時,化合物(8a)與化合物(8b)的添加量(質量比)較佳為(8a)/(8b)=50/1~1/50的比例。
實施共水解時,較佳為使用水解觸媒。作為所使用的水解觸媒,可使用以往習知的觸媒,例如,舉例有鹽酸、硝酸、硫酸、鹵化氫、羧酸、磺酸等酸;酸性或弱酸性之無機鹽;離子交換樹脂等固體酸;氨、氫氧化鈉等無機鹼類;三丁胺、1,5-二氮雜雙環[4.3.0]壬烯-5(DBN)、1,8-二氮雜雙環[5.4.0]十一烯-7(DBU)等有機鹼類;有機錫化合物、有機鈦化合物、有機鋯化合物、有機鋁化合物等有機金屬化合物等,該等可單獨使用1種亦可併用2種以上之複數種。
本發明中特佳為選自鹽酸、硝酸、硫酸、甲烷磺酸等酸;有機錫化合物、有機鈦化合物及有機鋁系化合物之有機金屬化合物。作為有機金屬化合物,具體而言舉例有二月桂酸二丁基錫、二辛酸二丁基錫(dibutyl tin octoate)、二乙酸二丁基錫(dibutyl tin diacetate)、二月桂酸二辛基錫、二辛酸二辛基錫、二乙酸二辛基錫、雙乙醯乙酸二丁基錫、雙乙醯月桂酸二辛基錫、鈦酸四丁酯、鈦酸四壬酯、四乙二醇甲基醚鈦酸酯、四乙二醇乙基醚鈦酸酯、雙(乙醯丙酮基)二丙基鈦酸酯、乙醯丙酮鋁、雙(乙基乙醯乙酸酯基)單正丁酸鋁、乙基乙醯乙酸酯基二正丁酸鋁、三(乙基乙醯乙酸酯)鋁(aluminum tris(ethylacetoacetate))、該等之水解物等。該等之中,從反應性的觀點而言,較佳為鹽酸、硝酸、甲烷磺酸等酸;鈦酸四丁酯、乙基乙醯乙酸酯基二正丁酸鋁、雙(乙基乙醯乙酸酯基)單正丁酸鋁及該等之水解物,特佳為甲烷磺酸。
水解觸媒的量,並無特別限定,但相對於式(7)的化合物的矽原子上之烷氧基1莫耳較佳為0.001~15莫耳%,特佳為0.001~10莫耳%。
上述共水解・縮合反應可在有機溶媒的存在下進行。作為有機溶媒,只要是可與上述各原料化合物相溶者即可,並無特別限制,作為其具體例舉例有甲苯、二甲苯等芳香族烴類;己烷、辛烷等烴類;甲基乙基酮、甲基異丁基酮等酮類;乙酸乙酯、乙酸異丁酯等酯類;甲醇、乙醇、異丙醇、丁醇、異丁醇、t-丁醇等醇類;氟系溶媒等。
作為氟系溶媒,例如舉例有1,3-雙(三氟甲基)苯、三氟甲苯等含氟芳香族烴類;全氟己烷、全氟甲基環己烷等碳原子數3~12的全氟碳化合物類;1,1,2,2,3,3,4-七氟環戊烷、1,1,1,2,2,3,3,4,4,5,5,6,6-十三氟辛烷等氫氟碳化合物類;C3
F7
OCH3
、C4
F9
OCH3
、C4
F9
OC2
H5
、C2
F5
CF(OCH3
)C3
F7
等氫氟醚類;Fomblin、Galden(SOLVAY製)、Demnum(大金工業股份有限公司製)、Krytox(Chemours製)等聚(全氟伸烷基醚)類等。
於上述反應中較佳為添加水。水解時所使用的水之添加量較佳為用來水解原料的全部烷氧基之必需量的1倍量~5倍量,特佳為1.5倍量~3倍量。
反應條件通常較佳為-5~20℃下15~300分鐘,更佳為0~10℃下30~180分鐘。
R7
為可與Si-H基進行加成反應之烯烴基,較佳為碳原子數2~8的烯基,例如舉例有乙烯基、烯丙基、1-丙烯基、異丙烯基、1-丁烯基、異丁烯基等。該等之中較佳為乙烯基、烯丙基。Y2
為單鍵、或可包含醚鍵的2價有機基(但,在與氧原子的鍵結末端包含O,產生-O-O-鍵結者除外),亦可具有環狀構造或分支構造。作為Y2
的2價有機基,舉例有碳原子數1~18,較佳為1~8的伸烷基等,但具體而言,例如舉例有下述構造式所表示者。Q及R1
如同上述。
相對於氫矽氧烷(9)的氫矽基1當量,化合物(10a)的添加量較佳為0.2~5當量,更佳為0.5~3當量。
使用化合物(10b)時,相對於氫矽氧烷(9)的氫矽基1當量,其添加量較佳為0.1~0.8當量,更佳為0.1~0.5當量。
併用化合物(10a)及化合物(10b)時,化合物(10a)與化合物(10b)的添加量(質量比)較佳為(10a)/(10b)=50/1~0.5/1的比例。
加成反應即使不使用溶劑亦能夠實施,但亦可視需要以溶劑進行稀釋。此時稀釋溶劑較佳為不阻礙矽氫化,且可溶解反應後生成之下述化合物(11),較佳為以目的之反應溫度溶解化合物(9)、化合物(10a)、視需要之化合物(10b)者。具體而言,例如較佳為苯、甲苯、二甲苯等芳香族烴系溶劑;m-六氟化二甲苯、三氟甲苯(benzotrifluoride)等氟改質芳香族烴系溶劑;甲基全氟丁基醚、全氟(2-丁基四氫呋喃等氟改質醚系溶劑等,該等之中較佳為甲苯、二甲苯、m-六氟化二甲苯。
較佳為於矽氫化反應使用觸媒。觸媒可使用例如包含鉑、銠、鈀等鉑族金屬之化合物。該等之中較佳為包含鉑之化合物,可使用例如六氯鉑(IV)酸六水合物、鉑羰基乙烯基甲基錯合物、鉑-二乙烯基四甲基二矽氧烷錯合物、鉑-環乙烯基甲基矽氧烷錯合物、鉑-辛醛/辛醇錯合物、氯化鉑酸與烯烴、醛、乙烯基矽氧烷或乙炔醇類等之錯合物、載持於活性炭之鉑等。相對於反應系全體的質量,觸媒的摻合量較佳為所包含的鉑族金屬量成為0.1~5,000ppm的範圍,更佳為1~1,000ppm。
加成反應中,混合各成分的順序並無特別限制,但例如可採用:將包含化合物(9)、化合物(10a)與視需要之化合物(10b)與觸媒之混合物,從室溫緩緩加熱至加成反應溫度之方法;將包含化合物(9)與化合物(10a)與視需要之化合物(10b)與稀釋溶媒之混合物,加熱至作為目的之反應溫度後,添加觸媒之方法;於加熱至作為目的之反應溫度之包含化合物(10a)與視需要之化合物(10b)與觸媒之混合物,滴下化合物(9)之方法;於加熱至作為目的之反應溫度之化合物(9),滴下包含化合物(10a)與視需要之化合物(10b)與觸媒之混合物之方法等。該等之中,特佳為將包含化合物(9)與化合物(10a)與視需要之化合物(10b)與稀釋溶媒之混合物,加熱至作為目的之反應溫度後,添加觸媒之方法、或者於加熱至作為目的之反應溫度之化合物(9),滴下包含化合物(10a)與視需要之化合物(10b)與觸媒之混合物之方法。該等方法中,可視需要以溶劑稀釋各成分或混合物來使用。
使化合物(10a)及(10b)與化合物(9)進行加成反應時,理想為在進行化合物(9)與化合物(10b)之加成反應後,使用過量的化合物(10a)進行加成反應,去除未反應的化合物(10a)並純化。此時,化合物(10a)及化合物(10b)中,亦可混合使用R7
、Y2
、R1
、Q彼此相異之化合物。
加成反應通常較佳為於20~120℃進行30~300分鐘,更佳為於50~100℃進行30~120分鐘。
Q、Y1
、R1
、R5
、w如同上述,h為1~3的整數,i為0~2的整數,h+i+w=3。另外,式(2)中,對應e=w+i,f=h-g。
[3]去保護反應
Q為式(4)所表示的矽基時,藉由將其一部分或全部去保護,而轉換成氫原子,來構築與接下來要反應之包含(甲基)丙烯醯基之醯氯化合物之反應點。另外,本發明中所謂(甲基)丙烯醯基,表示丙烯醯基或甲基丙烯醯基。
去保護的條件可使用以往習知的手法,並無特別限定,可舉例:利用氟化物離子之方法、利用酸(布氏酸(Bronsted acid)、路易士酸)之方法、利用鹼(布氏鹼、路易士鹼)之方法、在中性條件下使過量的醇作用之方法、利用N-溴代丁二醯亞胺或氫化二異丁基鋁、鈀錯合物等之方法等。該等之中,較佳為利用酸(布氏酸、路易士酸)之方法、與在中性條件下使過量的醇作用之方法,特佳為在中性條件下使過量的醇作用之方法。此時,作用之醇較佳為甲醇、乙醇、丙醇、丁醇、戊醇等,特佳為甲醇、乙醇。相對於式(4)的矽基1當量,醇的添加量較佳為1~50當量。反應條件通常較佳為於50~100℃下60~1,440分鐘。
[4]酯化反應
使上述式(11)中之矽基已去保護之化合物(11’)所包含的羥基的一部分或全部、或化合物(11)的Q為氫原子之時(化合物(11”))之氫矽基的一部分或全部,與下述式(12)所表示的(甲基)丙烯醯氯反應,藉由形成酯鍵,而可得到式(1)所表示的本發明之含氟矽氧烷丙烯酸酯。
(式中,R2
如同上述。)
化合物(11’)或(11”)與化合物(12)之反應,為了中和副生成之鹽酸,藉由在鹼的存在下,以0~100℃、較佳為0~80℃的條件下,混合兩者30~180分鐘來進行。
鹼的種類並無特別限定,但例如舉例有氨、三甲基胺、三乙基胺、二異丙基胺、三丙基胺、N,N-二異丙基乙胺、三丁胺、吡啶、N,N-二甲基胺基吡啶、1,5-二氮雜雙環[4.3.0]壬烯-5(DBN)、1,8-二氮雜雙環[5.4.0]十一烯-7(DBU)等胺化合物;碳酸氫鈉、碳酸氫鉀、碳酸氫鋰、碳酸鈉、碳酸鉀、碳酸鋰、氫氧化鈉、氫氧化鋰、氫氧化鉀等無機鹼;該等之水溶液等。該等不限定為1種,亦可使用2種或2種以上之混合物。該等之中,較佳為三乙基胺、吡啶、碳酸氫鈉、碳酸氫鉀、氫氧化鈉、氫氧化鉀,特佳為三乙基胺。
相對於化合物(11’)或(11”)之化合物(12)的摻合量,相對於化合物(11’)或(11”)所具有的羥基,較佳為1~10當量,更佳為1~5當量,特佳為1~3當量。
相對於化合物(12)之鹼的摻合量,相對於自化合物(12)產生之鹽酸,較佳為1~10當量,更佳為1~5當量,特佳為1~3當量。
上述酯化反應中,各成分的混合順序並無特別限制,但例如可採用:將包含化合物(11’)或(11”)與化合物(12)與鹼之混合物,從室溫緩緩加熱至酯化反應溫度之方法;將包含化合物(11’)或(11”)與化合物(12)之混合物,加熱至目的之反應溫度後,加入鹼之方法;將包含化合物(11’)或(11”)與鹼之混合物,加熱至目的之反應溫度後,加入化合物(12)之方法;將包含化合物(12)與鹼之混合物,加熱至目的之反應溫度後,加入化合物(11’)或(11”)之方法;將化合物(12)加熱至目的之溫度後,滴下包含化合物(11’)或(11”)與鹼之混合物之方法等。該等之中,特佳為將包含化合物(11’)或(11”)與鹼之混合物,加熱至目的之反應溫度後,滴下化合物(12)之方法。
該等之方法中,可視需要以溶劑來稀釋使用各成分或者混合物。作為稀釋所使用之溶媒,只要是不與羥基及醯氯反應之溶劑,可無特別限制的使用,具體而言較佳為芳香族烴系溶劑(苯、甲苯、二甲苯);氟改質芳香族烴系溶劑(m-六氟化二甲苯、三氟甲苯等);氟改質醚系溶劑(甲基全氟丁基醚、全氟(2-丁基四氫呋喃)等);酮系溶劑(丙酮、甲基乙基酮、甲基異丁基酮、環戊酮、環己酮等);醚系溶劑(四氫呋喃、二***、二異丙基醚、二丁基醚等)等。該等之中,較佳為丙酮、甲基乙基酮、甲基異丁基酮、m-六氟化二甲苯。
如此所合成的含氟矽氧烷丙烯酸酯成為隔著酯鍵具有丙烯醯基的構造。藉此,從構造中減少使折射率上升的胺基甲酸酯鍵的量,其結果,而可能不減少丙烯醯基量並使折射率降低。
[塗布組成物]
本發明之含氟矽氧烷丙烯酸酯可藉由添加於塗布組成物,而於被膜表面賦予防污性、耐指紋性、撥水性、撥油性。例如,添加於硬塗組成物的情況下,相對於硬塗布組成物的基質聚合物100質量份之含氟矽氧烷丙烯酸酯的摻合量,較佳為0.01~20質量份,更佳為0.05~10質量份。若在這種範圍中,則可不損害硬塗布被膜的硬度而充分覆蓋表面。
又,本發明之含氟矽氧烷丙烯酸酯可適用於抗反射塗布組成物。此時,相對於塗布組成物的基質聚合物100質量份之含氟矽氧烷丙烯酸酯的摻合量,較佳為20~500質量份,更佳為20~300質量份。若在這種範圍中,則可提供在保持被膜的強度的同時具有低折射率之抗反射膜。
上述塗布組成物中,只要能與本發明之含氟矽氧烷丙烯酸酯混合、硬化,則可併用本發明之含氟矽氧烷丙烯酸酯以外的丙烯酸酯或胺基甲酸酯丙烯酸酯。
作為丙烯酸酯,舉例有包含:1,6-己二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、乙二醇二(甲基)丙烯酸酯、異三聚氰酸環氧乙烷改質二(甲基)丙烯酸酯、異三聚氰酸環氧乙烷改質三(甲基)丙烯酸酯、三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、丙三醇三(甲基)丙烯酸酯、三(甲基)丙烯醯氧基乙基磷酸酯、鄰苯二甲酸氫-(2,2,2-三-(甲基)丙烯醯氧基甲基)乙酯、丙三醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、雙三羥甲基丙烷四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、山梨醇六(甲基)丙烯酸酯等2~6官能的(甲基)丙烯酸酯化合物、該等之(甲基)丙烯酸酯化合物的環氧乙烷、環氧丙烷、環氧氯丙烷、脂肪酸、烷基、胺基甲酸酯改質品、於環氧樹脂加成丙烯酸而得之環氧丙烯酸酯類、於丙烯酸酯共聚合物的側鏈導入有(甲基)丙烯醯基之共聚合物等者。
作為胺基甲酸酯丙烯酸酯,舉例有使具有羥基之(甲基)丙烯酸酯與聚異氰酸酯反應而得者、使具有羥基之(甲基)丙烯酸酯與聚異氰酸酯及末端二醇之聚酯反應而得者、使過量的二異氰酸酯與多元醇而得之聚異氰酸酯,再與具有羥基之(甲基)丙烯酸酯反應而得者。該等之中,較佳為包含:使選自(甲基)丙烯酸2-羥基乙酯、甲基丙烯酸2-羥基-3-丙烯醯氧基丙酯、及季戊四醇三丙烯酸酯之具有羥基之(甲基)丙烯酸酯,與選自六亞甲基二異氰酸酯、異佛爾酮二異氰酸酯、甲苯二異氰酸酯、及二苯基甲烷二異氰酸酯之聚異氰酸酯反應而成之胺基甲酸酯丙烯酸酯類。
作為包含這種丙烯酸酯或胺基甲酸酯丙烯酸酯之塗布組成物,亦可使用市售品,例如舉例有「BEAMSET」荒川化學工業(股)製、「UBIQ」大橋化學工業(股)製、「UV COAT」歐利生電氣(股)製、「CashewUV」Cashew(股)製、「DeSolite」JSR(股)製、「SEIKABEAM」大日精化工業(股)製、「紫光」日本合成化學(股)製、「FUJIHARD」藤倉化成(股)製、「Diabeam」三菱麗陽(股)製、「Ultra Vin」武藏塗料(股)製等。
另外,於本發明之塗布組成物中,在不阻礙本發明之效果的範圍內可加入任意的添加劑。作為添加劑的具體例,舉例有非反應性矽氧油、反應性矽氧油、非反應性二氧化矽微粒子、反應性二氧化矽微粒子、非反應性中空二氧化矽微粒子、反應性中空二氧化矽微粒子等二氧化矽微粒子、矽烷偶合劑等之密著賦予劑、抗老化劑、防鏽劑、著色劑、界面活性劑、流變調整劑、紫外線吸收劑、紅外線吸收劑、螢光劑、研磨劑、香料、填充劑、填料、染顏料、調平劑、反應性稀釋劑、非反應性高分子樹脂、抗氧化劑、紫外線吸收劑、光穩定劑、消泡劑、分散劑、抗靜電劑、觸變賦予劑等。
本發明之含氟矽氧烷丙烯酸酯,藉由將其摻合至塗布組成物,而有用於對於被膜表面賦予防污、撥水撥油性、耐指紋性、低反射性。藉此,賦予具有下述特徵之被膜:難以被指紋、皮脂、汗等人體油脂、化妝品等污損,且即使在附著有髒污的情況下拭除性亦優異,眩光受抑制。因此,本發明之化合物,作為用以形成施予可能接觸人體,而被人體油脂、化妝品等污損的物品的表面之塗裝膜或保護膜而使用之硬化性組成物的添加劑而為有用。
作為這種物品,例如舉例有以光磁碟、CD、LD、DVD、藍光光碟等光碟、全像記錄等為代表之光記錄媒體;眼鏡透鏡、稜鏡、透鏡片、防護膜(pellicle film)、偏光板、光學過濾器、柱狀透鏡(lenticular lens)、菲涅耳透鏡、抗反射膜、光纖或光耦合器等光學零件・光學裝置;CRT、液晶顯示器、電漿顯示器、電致發光顯示器、背投影型顯示器、螢光顯示管(VFD)、場發射投影顯示器(Field emission projection display)、施體(donor)系顯示器等各種畫面顯示機器、尤其是PC、行動電話、行動資訊終端、遊戲機、數位相機、數位攝影機、自動現金取出存入裝置、自動提款機、自動販賣機、汽車用等導航裝置、保全系統終端等影像顯示裝置、及亦進行其操作之觸控面板(觸控感應器、觸控螢幕)式影像顯示輸入裝置;行動電話、行動資訊終端、可攜式音樂播放器、行動遊戲機、遙控控制器、控制器、鍵盤等、車輛裝置用面板開關等輸入裝置;行動電話、行動資訊終端、相機、可攜式音樂播放器、行動遊戲機等殼體表面;汽車外裝、鋼琴、高級家具、大理石等塗裝及表面;美術品展示用保護玻璃、櫥窗、展示櫃、廣告用罩、相框用蓋、手錶、汽車用擋風玻璃、列車、飛機等窗玻璃、汽車頭燈、尾燈等透明玻璃製或透明塑膠製(丙烯酸、聚碳酸酯等)構件、各種鏡子構件等。
又,本發明之含氟矽氧烷丙烯酸酯係添加於紫外線硬化型光阻液,藉由進行曝光,而可使硬化後的光阻表面與除去光阻的部分之撥液性具有明顯差異,而能夠防止光阻樹脂表面之顯影液或液晶溶液殘留、污染。
[實施例]
以下,示出實施例及比較例,具體地說明本發明,但本發明並非限制於下述實施例者。並且,1
H-NMR測定係使用ULTRA SHIELD 400 Plus(Bruker公司製)來進行。另外,下述例中,Me表示甲基。
[實施例1-1]
乾燥氮環境下,加入下述式(13)所表示的化合物1,255g、四甲基二矽氧烷665g、甲基乙基酮1,255g、甲烷磺酸20g,於具備回流裝置與攪拌裝置之5,000mL三口燒瓶中,一面攪拌一面冷卻至5℃。此處滴下離子交換水71g,在將內溫維持於0~10℃的狀態下繼續攪拌3小時。之後,加入水滑石(KYOWAAD 500SH,協和化學工業(股)製)100g,在將內溫維持於0~10℃的狀態下進行攪拌2小時,減壓餾除溶劑、過剩之四甲基二矽氧烷後,過濾分離水滑石,得到下述式(14)所表示的無色透明之液體1,130g。
(式中,a1≧1、b1≧1、a1/b1=0.76,附有a1及b1之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
乾燥氮環境下,對於化合物(14)190g,混合烯丙氧基三甲基矽烷117g、甲苯229g及氯化鉑酸/乙烯基矽氧烷錯合物之甲苯溶液4.3g(作為Pt單體含有8.3×10-5
莫耳),於80℃攪拌2小時。以1
H-NMR測定及FT-IR測定確認源自Si-H基之訊號(signal)消失後,減壓餾除溶劑與過剩之烯丙氧基三甲基矽烷,進行活性炭處理後再過濾,藉此得到下述式(15)所表示的淡黃色透明之液體230g。
(式中,a1≧1、b1≧1、a1/b1=0.76,附有a1及b1之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
乾燥氮環境下,對於化合物(15)230g,加入甲醇2,300g,藉由於67℃加熱攪拌12小時,常壓餾除副生成之三甲基甲氧基矽烷後,減壓餾除過剩之甲醇與三甲基矽烷,而得到下述式(16)所表示的淡黃色透明之液體197g。
(式中,a1≧1、b1≧1、a1/b1=0.76,附有a1及b1之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
乾燥氮環境下,對於化合物(16)101g,加入三乙基胺41g、六氟-m-二甲苯505g,一面攪拌一面升溫至60℃。此處,一面將內溫維持於55~60℃一面滴下以甲苯50g稀釋丙烯醯氯25g之混合物,繼續攪拌30分鐘。接著,在將內溫維持於55~60℃的狀態下滴下乙醇5.8g,繼續攪拌1小時。於過濾分離已析出之鹽而得到之濾液,加入水滑石(KYOWAAD 500SH,協和化學工業(股)製)5.6g與矽酸鋁(KYOWAAD 700,協和化學工業(股)製)5.6g,攪拌2小時後,進行減壓餾除,過濾分離水滑石及矽酸鋁,藉此得到淡黃色透明之液體56g。
所得到的生成物藉由1
H-NMR測定,而確認為下述式(17)所表示的含氟矽氧烷丙烯酸酯。將1
H-NMR圖譜之化學位移示於表1。
(式中,a1≧1、b1≧1、a1/b1=0.76,附有a1及b1之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
[實施例1-2]
乾燥氮環境下,加入下述式(18)所表示的化合物1,237g、四甲基二矽氧烷443g、甲基乙基酮1,237g、甲烷磺酸18g,於具備回流裝置與攪拌裝置之5,000mL三口燒瓶中,一面攪拌一面冷卻至5℃。此處滴下離子交換水48g,在將內溫維持於0~10℃的狀態下繼續攪拌3小時。之後,加入水滑石(KYOWAAD 500SH,協和化學工業(股)製)88g,在將內溫維持於0~10℃的狀態下進行2小時攪拌,減壓餾除溶劑、過剩之四甲基二矽氧烷後,過濾分離水滑石,得到下述式(19)所表示的無色透明之液體1,256g。
(式中,a2≧1、b2≧1、a2/b2=0.76,附有a2及b2之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
乾燥氮環境下,對於化合物(19)363g,混合烯丙氧基三甲基矽烷156g、甲苯436g及氯化鉑酸/乙烯基矽氧烷錯合物之甲苯溶液2.9g(作為Pt單體含有7.3×10-5
莫耳),於80℃攪拌2小時。以1
H-NMR測定及FT-IR測定確認源自Si-H基之訊號消失後,減壓餾除溶劑與過剩之烯丙氧基三甲基矽烷,進行活性炭處理後再過濾,藉此得到下述式(20)所表示的淡黃色透明之液體410g。
(式中,a2≧1、b2≧1、a2/b2=0.76,附有a2及b2之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
乾燥氮環境下,對於化合物(20)230g,加入甲醇2,300g,藉由於67℃加熱攪拌12小時,常壓餾除副生成之三甲基甲氧基矽烷後,減壓餾除過剩之甲醇與三甲基矽烷,而得到下述式(21)所表示的淡黃色透明之液體180g。
(式中,a2≧1、b2≧1、a2/b2=0.76,附有a2及b2之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
乾燥氮環境下,對於化合物(21)133g,加入三乙基胺34g、六氟-m-二甲苯663g,一面攪拌一面升溫至60℃。此處,一面將內溫維持於55~60℃一面滴下以甲苯40g稀釋丙烯醯氯20g之混合物,繼續攪拌30分鐘。接著,在將內溫維持於55~60℃的狀態下滴下乙醇1.8g,繼續攪拌1小時。於過濾分離已析出之鹽而得到之濾液,加入水滑石(協和化學工業(股)製,KYOWAAD 500SH)7.4g與矽酸鋁(協和化學工業(股)製,KYOWAAD 700)7.4g,攪拌2小時後,進行減壓餾除,過濾分離水滑石及矽酸鋁,藉此得到淡黃色透明之液體102g。
所得到的生成物藉由1
H-NMR測定,而確認為下述式(22)所表示的含氟矽氧烷丙烯酸酯。將1
H-NMR圖譜之化學位移示於表2。
(式中,a2≧1、b2≧1、a2/b2=0.76,附有a2及b2之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
[實施例1-3]
乾燥氮環境下,對於上述化合物(19)121g,混合烯丙基乙二醇(allylglycol)41g、甲苯121g及氯化鉑酸/乙烯基矽氧烷錯合物之甲苯溶液0.85g(作為Pt單體含有2.2×10-5
莫耳),於80℃攪拌2小時。以1
H-NMR測定及FT-IR測定確認源自Si-H基之訊號消失後,減壓餾除溶劑與過剩之烯丙基乙二醇,進行活性炭處理後再過濾,藉此得到下述式(23)所表示的淡黃色透明之液體122g。
(式中,a2≧1、b2≧1、a2/b2=0.76,附有a2及b2之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
乾燥氮環境下,對於化合物(23)141g,加入三乙基胺27g、六氟-m-二甲苯707g,一面攪拌一面升溫至60℃。此處,一面將內溫維持於55~60℃一面滴下以甲苯40g稀釋丙烯醯氯20g之混合物,繼續攪拌30分鐘。接著,在將內溫維持於55~60℃的狀態下滴下乙醇1.8g,繼續攪拌1小時。於過濾分離已析出之鹽而得到之濾液,加入水滑石(KYOWAAD 500SH,協和化學工業(股)製)7.9g與矽酸鋁(KYOWAAD 700,協和化學工業(股)製)7.9g,攪拌2小時後,進行減壓餾除,過濾分離水滑石及矽酸鋁,藉此得到淡黃色透明之液體112g。
所得到的生成物藉由1
H-NMR測定,而確認為下述式(24)所表示的含氟矽氧烷丙烯酸酯。將1
H-NMR圖譜之化學位移示於表3。
(式中,a2≧1、b2≧1、a2/b2=0.76,附有a2及b2之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為1,500。)
[比較例1-1]
下述式(25)所表示的含氟矽氧烷丙烯酸酯。
(式中,a3≧1、b3≧1、a3/b3=0.76,附有a3及b3之括弧內的重複單位之排列為不固定,全氟聚醚鏈的數量平均分子量為2,000。)
對於實施例1-1~1-3、比較例1-1之含氟矽氧烷丙烯酸酯,藉由下述方法進行評價。將結果示於表4。
[丙烯酸當量]
基於藉由1
H-NMR圖譜解析而得之構造,算出每1莫耳丙烯醯基之分子量。
[折射率]
於25℃使用折射率計(裝置名:RX-7000α,愛宕股份有限公司製)進行測定。
[實施例2-1~2-3、比較例2-1]
於甲基異丁基酮100質量份、4官能丙烯酸酯(A-TMMT,新中村化學工業(股)製)100質量份、2-羥基-2-甲基-1-苯基丙酮(Omnirad 1173,IGM RESINS B.V.製)2質量份中,混合含氟矽氧烷丙烯酸酯(實施例1-1~1-3、比較例1-1)1質量份,分別調製塗布組成物。
[比較例2-2]
除不含有含氟矽氧烷丙烯酸酯以外,與實施例2-1~2-3、比較例2-1相同的調製塗布組成物。
[組成物外觀]
對於實施例2-1~2-3、比較例2-1、2-2之塗布組成物,藉由目視來評價外觀。將結果示於表5。
[被膜外觀]
將實施例2-1~2-3、比較例2-1、2-2之塗布組成物,分別旋轉塗布於聚碳酸酯板上,使用輸送型紫外線照射裝置(Eyegraphics(股)製),於氮環境中照射600mJ/cm2
之紫外線並形成硬化膜,藉由目視來評價外觀。將結果示於表5。
[水接觸角、十六烷接觸角]
對於在上述被膜外觀試驗作成之硬化膜,使用接觸角計(協和界面科學(股)製)測定水接觸角、十六烷接觸角。將結果示於表5。
如表4所示,雖然實施例1-1~1-3的含氟矽氧烷丙烯酸酯與比較例1-1之物相較,丙烯酸當量(g/mol)較小(每單位質量之丙烯醯基濃度較大),但具有更低的折射率。
又,如表5所示,得知本發明之含氟矽氧烷丙烯酸酯顯示與比較例1-1之物同等的外觀、水接觸角及十六烷接觸角,並具有溶解性及防污性。
如以上所述,本發明之含氟矽氧烷丙烯酸酯由於溶解性、低折射率、防污性優異,不僅有用於對於玻璃、樹脂、膜、紙、金屬、陶器、木材等之塗布組成物、印刷物表面之保護膜用組成物、塗料添加劑,亦有用於低反射膜用添加劑。
Claims (10)
- 一種下述式(1)所表示的含氟矽氧烷丙烯酸酯, [式中,PFPE表示數量平均分子量500~30,000之2價的全氟聚醚鏈,X分別獨立地為下述式(2)所表示的基, {式(2)中,Y1 分別獨立地為可包含醚鍵、亦可具有環狀構造或分支構造之2價有機基,R2 分別獨立地為氫原子、氟原子、甲基或三氟甲基,G分別獨立地為碳原子數1~12的烷基或下述式(3)所表示的基, (式(3)中,R1 為碳原子數1~12的1價烴基,Y1 如同上述,虛線表示鍵結處) Q為氫原子或下述式(4)所表示的基, (式(4)中,R3 分別獨立地為碳原子數1~12的1價烴基,虛線表示鍵結處) e為0~2的整數,f為0~2的整數,g為1~3的整數,e+f+g為3,虛線表示鍵結處} Z分別獨立地為下述式所表示的2價有機基, (式中,虛線表示鍵結處,**記號表示與前述PFPE的鍵結部位)]。
- 如請求項1之含氟矽氧烷丙烯酸酯,其中G為碳原子數1~6的烷基或上述式(3)所表示的基,式(3)中的R1 為甲基、乙基或n-丙基,e為1或2。
- 如請求項5之含氟矽氧烷丙烯酸酯,其中G為碳原子數1~3的烷基。
- 如請求項1之含氟矽氧烷丙烯酸酯,其中e為0。
- 一種塗布組成物,其包含如請求項1之含氟矽氧烷丙烯酸酯。
- 如請求項8之塗布組成物,其進而包含如請求項1之含氟矽氧烷丙烯酸酯以外之丙烯酸酯或胺基甲酸酯丙烯酸酯。
- 一種具有被膜的物品,其具有由如請求項8之塗布組成物的硬化物所構成之被膜。
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