JP5826282B2 - リン含有酸基及びアルコキシシラン基を含むフッ素化組成物 - Google Patents
リン含有酸基及びアルコキシシラン基を含むフッ素化組成物 Download PDFInfo
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- JP5826282B2 JP5826282B2 JP2013537686A JP2013537686A JP5826282B2 JP 5826282 B2 JP5826282 B2 JP 5826282B2 JP 2013537686 A JP2013537686 A JP 2013537686A JP 2013537686 A JP2013537686 A JP 2013537686A JP 5826282 B2 JP5826282 B2 JP 5826282B2
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- 239000000203 mixture Substances 0.000 title claims description 65
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- 229910052698 phosphorus Inorganic materials 0.000 title claims description 15
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- 239000011574 phosphorus Substances 0.000 title claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 29
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 24
- 125000002947 alkylene group Chemical group 0.000 claims description 20
- 229910052751 metal Inorganic materials 0.000 claims description 19
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- 238000005260 corrosion Methods 0.000 claims description 13
- 230000007797 corrosion Effects 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
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- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
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- 239000006184 cosolvent Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229910001092 metal group alloy Inorganic materials 0.000 description 2
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- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 2
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- 230000003068 static effect Effects 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- OKIYQFLILPKULA-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-methoxybutane Chemical compound COC(F)(F)C(F)(F)C(F)(F)C(F)(F)F OKIYQFLILPKULA-UHFFFAOYSA-N 0.000 description 1
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- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
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- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 1
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- 125000000913 palmityl 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])C([H])([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
- 125000005003 perfluorobutyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)C(F)(F)* 0.000 description 1
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- 125000003226 pyrazolyl group Chemical group 0.000 description 1
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- SXHLENDCVBIJFO-UHFFFAOYSA-M sodium;2-[2-(2-dodecoxyethoxy)ethoxy]ethyl sulfate Chemical compound [Na+].CCCCCCCCCCCCOCCOCCOCCOS([O-])(=O)=O SXHLENDCVBIJFO-UHFFFAOYSA-M 0.000 description 1
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- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl 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])C([H])([H])C([H])([H])C([H])([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
- 239000010959 steel Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229940035024 thioglycerol Drugs 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
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- C09D143/00—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 containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
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- 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
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- 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
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Description
によって表される少なくとも1個の二価単位と、
ペンダントZ基を含む第2の二価単位又はチオエーテル結合及び末端Z基を含む一価単位のうち少なくとも1個(各Z基は、独立して−P(O)(OY)2及び
−O−P(O)(OY)2からなる群から選択される)とを含む組成物について記載している。Rfは、ペルフルオロポリエーテル基である。Qは、結合、−C(O)−N(R1)−、及び−C(O)−O−からなる群から選択される。R’’、R’’’、R及びR1は、それぞれ独立して水素及び1〜4個の炭素原子を有するアルキルからなる群から選択される。Xは、アルキレン、アリールアルキレン及びアルキルアリーレンからなる群から選択され、前記アルキレン、アリールアルキレン及びアルキルアリーレンは、それぞれ所望により少なくとも1個のエーテル結合によって割り込まれる。Yは、水素、アルキル、トリアルキルシリル及び対カチオンからなる群から選択される。これらの組成物を用いる表面の処理方法及び、これらの組成物と接触する表面を有する物品が提供される。これらの組成物の製造方法もまた提供される。
特に規定しない限り、「アルキル基」及び接頭語「アルキ−」は、直鎖及び分岐鎖、並びに30個以下の炭素(いくつかの実施形態では、25、20、15、12、10、8、7、6又は5個以下の炭素)を有する環状基の両方を含む。環状基は、単環式又は多環式であってよく、いくつかの実施形態では、3〜10個の環炭素原子を有する。
「アルキレン」は、上記で定義した「アルキル」基の二価形態である。
「アリールアルキレン」は、アリール基が結合している「アルキレン」部分を指す。
用語「アリール」は、本明細書で使用するとき、炭素環式芳香環、又は例えば、1、2又は3個の環を有し、かつ環内に少なくとも1個のヘテロ原子(例えば、O、S又はN)を含有する場合のある環構造を含む。アリール基の例としては、フェニル、ナフチル、ビフェニル、フルオレニル、並びに、フリル、チエニル、ピリジル、キノリニル、イソキノリニル、インドリル、イソインドリル、トリアゾリル、ピロリル、テトラゾリル、イミダゾリル、ピラゾリル、オキサゾリル、及びチアゾリルが挙げられる。
「アリーレン」は、上記で定義した「アリール」基の二価形態である。
「アルキルアリーレン」は、アルキル基が結合している「アリーレン」部分を指す。
「アルコキシシラン」は、基−Si(OR)3(式中、Rは、独立して、水素又は1〜4個の炭素原子を有するアルキル基である)を指す。
式中、Rf aは、1〜10個(いくつかの実施形態では、1〜6、1〜4、2〜4、又は3個)の炭素原子を有するペルフルオロアルキルであり、各Rf bは、独立して1〜4個(すなわち、1、2、3、又は4個)の炭素原子を有するペルフルオロアルキレンであり、Rf cは、1〜6個(いくつかの実施形態では、1〜4個又は2〜4個)の炭素原子を有するペルフルオロアルキレンであり、zは、2〜50(いくつかの実施形態では、2〜25、2〜20、3〜20、3〜15、5〜15、6〜10、又は6〜8)の整数である。
Rf−Q−X−O−C(O)−C(R)=CH2,
(式中、Rf、Q、R、及びXは、式Iの二価単位について上で定義した通りである)。いくつかの実施形態では、化合物は、Rf−C(O)−N(R1)−X−O−C(O)−C(R)=CH2(式中、R1は、式Iの化合物について上で定義した通りである)。
(式中、RF 1は、ペルフルオロアルキル基であり、X1は、結合又は−SO2N(R)−等の二価結合基である)。
(式中、R’’及びR’’’は、それぞれ独立して、水素又は1〜4個の炭素原子を有するアルキルである)。いくつかの実施形態では、各R’’は独立して水素又はメチルである。いくつかの実施形態では、R’’’は、メチル又はエチルである。
(RO)2−P(O)−V−(O)n[C(R)−CH2]−又は
(RO)2−P(O)−O−V−O−C(O)−[C(R)CH2]−
(YO)2−P(O)−V−C(R)=CH2又は
(YO)2−P(O)−O−V−O−C(O)−C(R)=CH2、
(式中、R及びVは、既に記載した通りである)。これらの式のいくつかの第2の成分は、例えば、商業的供給元から入手することが可能であり(例えば、エチレングリコールメタクリレートホスフェートHEMA−P)又は既知の合成法を用いて調製することもできる。ハイドロフルオロエーテル等の有機溶媒との相溶性を改善するために、ペンダントリン−酸含有基を提供する出発成分のフリーラジカル重合性基は、好ましくは、ビニル基ではなく(メタ)アクリレート基である。
(式中、
Lは、CO2(CH2)n(式中、n=2〜6である)又はフェニルであり、
Yは、独立して、1〜4個の炭素原子を有するアルキル基である)。
−S−W−Si(OR)3
(式中、Wは、アルキレン、アリールアルキレン、及びアリーレンからなる群より選択される二価又は三価の結合基であり、前記アルキレンは、所望により、少なくとも1個のエーテル結合、エステル結合、又はアミド結合によって割り込まれ、Rは、H又は1〜4個の炭素原子を有するアルキル基である)。典型的に、Wは、1〜4個の炭素原子を有するアルキレン基である。
(式中、aは1〜3の整数であり、Rf 1は、直鎖、分岐鎖、環状又はこれらの組み合わせであり、所望により少なくとも1個のエーテル結合(すなわち、−O−)により割り込まれる一価、二価又は三価のペルフルオロアルキルであり、Rhは、直鎖、分岐鎖、環状又はこれらの組み合わせであり、所望により少なくとも1個のヘテロ原子(例えば、N、O又はS)を含有するアルキル基である)。例えば、ヒドロフルオロエーテルは、メチルペルフルオロブチルエーテル又はエチルペルフルオロブチルエーテルであってよい。
磁気棒、凝縮器を備える2つ口のオーブンで乾燥させた250mLのフラスコを油浴に浸漬し、HFPO−CONHCH2CH2−O−CO−C(CH3)=CH2(20g、米国特許公開第20050137355A1(Buckaninら)に記載の通り調製)、HEMA−P(2g、Esstech,Inc.,Essington PAから入手)、SH−(CH2)3−CH3(1g)、2,2’,−アゾビス(2−メチルブチロニトリル)、熱フリーラジカル開始剤(100mg、E.I.du Pont de Nemours & Co.,Wilmington DEから商品名「VAZO(登録商標)−67」として入手)、ハイドロフルオロエーテル溶媒(40g、3M Company,St.Paul,MNから商品名「Novec(商標)7200 Engineered Fluid」として市販)を入れた。N2を用いて10分間溶液を脱気し、次いで、蓋をし、70℃で16時間撹拌した。反応混合物を冷却し、濾紙(Whatman,Inc.,Piscataway,NJから商品名WHATMAN GRADE 40として入手可能)を用いて濾過し、コーティング用に「Novec(商標)7200 Engineered Fluid」で所望の濃度(10重量%)に希釈した。
N2入口及び凝縮器を備えるオーブンで乾燥させた250mLの三角フラスコを油浴に浸漬し、HFPO−CONHCH2CH2−O−CO−C(CH3)=CH2(20g)、HEMA−P(2g)、SH−(CH2)3−Si(OCH3)3(1g)、VAZO−67(100mg)、及び「Novec(商標)7200 Engineered Fluid」(40g)を入れた。N2を用いて10分間溶液を脱気し、次いで、蓋をし、70℃(油浴温度)で16時間撹拌した。反応混合物を冷却し、濾紙(WHATMAN GRADE 40)を用いて濾過し、コーティング用に「Novec(商標)7200 Engineered Fluid」で所望の濃度(10重量%)に希釈した。
N2入口及び凝縮器を備えるオーブンで乾燥させた250mLの三角フラスコを油浴に浸漬し、HFPO−CONHCH2CH2−O−CO−C(CH3)=CH2(20g)、HEMA−P(2g)、A−174(2g、Momentive Performance Materials,Wilton,CTから商品名SILQUEST A−174 SILANEとして入手)SH−(CH2)3−Si(OCH3)3(1g)、VAZO−67(100mg)、及び「Novec(商標)7200 Engineered Fluid」(40g)を入れた。N2を用いて10分間溶液を脱気し、次いで、蓋をし、70℃(油浴温度)で16時間撹拌した。反応混合物を冷却し、濾紙(WHATMAN GRADE 40)を用いて濾過し、コーティング用に「Novec(商標)7200 Engineered Fluid」で所望の濃度(10重量%)に希釈した。
第1、第2、及び第3の単位のモル百分率は、48/36/34であった。
コーティングされた板を、以下の表に記載の通り水(室温で48時間又は90℃で3時間)、3.5重量% NaCl水溶液に48時間浸漬することにより、上記の通りコーティングした銅板を、その腐食耐性について試験した。
接触角を、VCA−2500XEビデオ接触角装置を用いて測定した。結果を表に示す。報告された値は、少なくとも3滴の左側と右側の測定値の平均である。液滴体積は、静的測定の場合5マイクロリットルであった。
Claims (5)
- ペンダントペルフルオロポリエーテル又はペルフルオロアルキル基を含む少なくとも1個の第1の二価単位と、
ペンダントリン含有酸基を含む少なくとも1個の第2の二価単位であって、
(RO)2−P(O)−V−(O)n[C(R)−CH2]−、
(RO)2−P(O)−O−V−O−C(O)−[C(R)CH2]−、又は
これらの組合せ
(式中、Rは、独立して、水素及び1〜4個の炭素原子を有するアルキルからなる群より選択され、
Vは、独立して、所望により少なくとも1個のエーテル結合又はアミン結合により割り込まれるアルキレンであり、
n=0又は1である)から選択される第2の二価単位と、
末端又はペンダントアルコキシシラン基を含む少なくとも1個の第3の単位と、を含むポリマーを含有する組成物であって、
前記第1の二価単位が、
(式中、
Rfは、独立して、ペルフルオロポリエーテル基であり、
Qは、独立して、結合、−C(O)−N(R1)−(R 1 は、水素又は1〜4個の炭素原子を有するアルキルである)、及び−C(O)−O−からなる群より選択され、
Rは、独立して、水素又は1〜4個の炭素原子を有するアルキルであり、
Xは、独立して、アルキレン、アリールアルキレン、及びアルキルアリーレンからなる群から選択され、前記アルキレン、アリールアルキレン、及びアルキルアリーレンは、それぞれ所望により少なくとも1個のヘテロ原子により割り込まれる)、
又は
(式中、
RF 1は、3〜12個の炭素原子を有するペルフルオロアルキル基であり、
pは、2〜11の整数であり、
X1は、結合又は−SO 2 N(R)−(当該Rは、水素又は1〜4個の炭素原子を有するアルキルである)であり、
Rは、独立して、水素又は1〜4個の炭素原子を有するアルキル基である)から選択される二価単位であり、
前記第3の単位が、
(式中、
Rは、H又は1〜4個の炭素原子を有するアルキル基であり、
Lは、CO2(CH2)n(式中、n=2〜6である)又はフェニルであり、
Yは、独立して、1〜4個の炭素原子を有するアルキル基である)の式を有する、組成物。 - アクリル骨格鎖を含む、請求項1に記載の組成物。
- 金属表面を含む物品と、
金属含有表面上に配置されている、請求項1又は2に記載の組成物と、を含む、腐食保護された物品。 - ペンダントペルフルオロポリエーテル又はペルフルオロアルキル基を含む少なくとも1個の第1の二価単位と、
ペンダントリン含有酸基を含む少なくとも1個の第2の二価単位と、
末端又はペンダントアルコキシシラン基を含む少なくとも1個の第3の単位であって、
式:
−S−W−Si(OR)3
(式中、Rは、独立して、H又は1〜4個の炭素原子を有するアルキル基であり、Wは、1〜4個の炭素原子を有するアルキレン基である)を有する第3の単位と、を含むポリマーを含有する組成物であって、
前記第1の単位が、
(式中、
Rfは、独立して、ペルフルオロポリエーテル基であり、
Qは、独立して、結合、−C(O)−N(R1)−(R 1 は、水素又は1〜4個の炭素原子を有するアルキルである)、及び−C(O)−O−からなる群より選択され、
Rは、独立して、水素又は1〜4個の炭素原子を有するアルキルであり、
Xは、独立して、アルキレン、アリールアルキレン、及びアルキルアリーレンからなる群から選択され、前記アルキレン、アリールアルキレン、及びアルキルアリーレンは、それぞれ所望により少なくとも1個のヘテロ原子により割り込まれる)、
又は
(式中、
RF 1は、3〜12個の炭素原子を有するペルフルオロアルキル基であり、
pは、2〜11の整数であり、
X1は、結合又は−SO 2 N(R)−(当該Rは、水素又は1〜4個の炭素原子を有するアルキルである)であり、
Rは、独立して、水素又は1〜4個の炭素原子を有するアルキル基である)から選択される二価単位であり、
前記第2の二価単位が、
(RO) 2 −P(O)−V−(O) n [C(R)−CH 2 ]−、
(RO) 2 −P(O)−O−V−O−C(O)−[C(R)CH 2 ]−、又は
これらの組合せ
(式中、Rは、独立して、水素及び1〜4個の炭素原子を有するアルキルからなる群より選択され、
Vは、独立して、所望により少なくとも1個のエーテル結合又はアミン結合により割り込まれるアルキレンであり、
n=0又は1である)から選択される、組成物。 - 金属表面を含む物品と、
金属含有表面上に配置されている、請求項4に記載の組成物と、を含む、腐食保護された物品。
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US61/410,280 | 2010-11-04 | ||
PCT/US2011/056988 WO2012061021A1 (en) | 2010-11-04 | 2011-10-20 | Fluorinated composition comprising phosphorus containing acid group and alkoxy silane group |
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KR101611006B1 (ko) * | 2013-08-13 | 2016-04-08 | 제일모직주식회사 | 광경화 조성물 및 이를 사용하여 제조된 봉지화된 장치 |
US10093822B2 (en) | 2014-08-19 | 2018-10-09 | 3M Innovative Properties Company | Amphiphilic polymers, coating compositions, and methods |
KR101947421B1 (ko) * | 2014-10-20 | 2019-02-14 | (주)엘지하우시스 | 표면코팅용 수성 조성물 및 이를 적용한 자동차용 시트 |
EP3233942B1 (en) * | 2014-12-18 | 2020-04-01 | 3M Innovative Properties Company | Fluorinated polymers comprising phosphonic moieties |
EP3070133B1 (fr) * | 2015-03-18 | 2019-02-20 | The Swatch Group Research and Development Ltd. | Pièce d'horlogerie ou de bijouterie comprenant une surface recouverte d'un agent épilame et procédé d'épilamage d'un tel substrat |
JP6488890B2 (ja) * | 2015-06-03 | 2019-03-27 | 信越化学工業株式会社 | フルオロオキシアルキレン基含有ポリマー変性ホスホン酸誘導体、該誘導体を含む表面処理剤、該表面処理剤で処理された物品及び光学物品 |
WO2017061235A1 (ja) * | 2015-10-09 | 2017-04-13 | 信越化学工業株式会社 | フルオロオキシアルキレン基含有ポリマー変性ホスホン酸誘導体及び該誘導体を含む表面処理剤、該表面処理剤を用いた表面処理方法 |
EP3290451B1 (fr) * | 2016-09-01 | 2021-08-18 | The Swatch Group Research and Development Ltd. | Substrat comprenant une surface recouverte d'un agent épilame et procédé d'épilamage d'un tel substrat |
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JP2014500896A (ja) | 2014-01-16 |
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US20130216837A1 (en) | 2013-08-22 |
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