JP2017531074A - 親水性置換基を有する重合性ポリシロキサン - Google Patents
親水性置換基を有する重合性ポリシロキサン Download PDFInfo
- Publication number
- JP2017531074A JP2017531074A JP2017516140A JP2017516140A JP2017531074A JP 2017531074 A JP2017531074 A JP 2017531074A JP 2017516140 A JP2017516140 A JP 2017516140A JP 2017516140 A JP2017516140 A JP 2017516140A JP 2017531074 A JP2017531074 A JP 2017531074A
- Authority
- JP
- Japan
- Prior art keywords
- group
- pyrrolidone
- methylene
- hydrophilic
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 polysiloxane Polymers 0.000 title claims abstract description 191
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 187
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- 239000000203 mixture Substances 0.000 claims abstract description 74
- 239000000017 hydrogel Substances 0.000 claims abstract description 62
- 229920001477 hydrophilic polymer Polymers 0.000 claims abstract description 60
- 229920000642 polymer Polymers 0.000 claims abstract description 54
- 238000009472 formulation Methods 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 239000000178 monomer Substances 0.000 claims description 117
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 81
- 229920002554 vinyl polymer Polymers 0.000 claims description 81
- 239000000463 material Substances 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 230000005855 radiation Effects 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 21
- 230000035699 permeability Effects 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 239000004971 Cross linker Substances 0.000 claims description 17
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- 239000003999 initiator Substances 0.000 claims description 16
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- 125000002348 vinylic group Chemical group 0.000 claims description 15
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- VDORPYPVQAFLTR-UHFFFAOYSA-N 5-methyl-3-methylidenepyrrolidin-2-one Chemical compound CC1CC(=C)C(=O)N1 VDORPYPVQAFLTR-UHFFFAOYSA-N 0.000 claims description 11
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- KYKIFKUTBWKKRE-UHFFFAOYSA-N n-ethenylpropan-2-amine Chemical compound CC(C)NC=C KYKIFKUTBWKKRE-UHFFFAOYSA-N 0.000 claims description 11
- VZPULCFQAMRUMH-UHFFFAOYSA-N 1-ethyl-3-methylidenepyrrolidin-2-one Chemical compound CCN1CCC(=C)C1=O VZPULCFQAMRUMH-UHFFFAOYSA-N 0.000 claims description 10
- CXNYYQBHNJHBNH-UHFFFAOYSA-N 1-ethyl-5-methylidenepyrrolidin-2-one Chemical compound CCN1C(=C)CCC1=O CXNYYQBHNJHBNH-UHFFFAOYSA-N 0.000 claims description 10
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- ZQXSMRAEXCEDJD-UHFFFAOYSA-N n-ethenylformamide Chemical compound C=CNC=O ZQXSMRAEXCEDJD-UHFFFAOYSA-N 0.000 claims description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 claims description 9
- AFXKUUDFKHVAGI-UHFFFAOYSA-N 1-methyl-3-methylidenepyrrolidin-2-one Chemical compound CN1CCC(=C)C1=O AFXKUUDFKHVAGI-UHFFFAOYSA-N 0.000 claims description 8
- 229920001184 polypeptide Polymers 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 8
- ZZDBHIVVDUTWJC-UHFFFAOYSA-N 1-methyl-5-methylidenepyrrolidin-2-one Chemical compound CN1C(=C)CCC1=O ZZDBHIVVDUTWJC-UHFFFAOYSA-N 0.000 claims description 7
- 239000000314 lubricant Substances 0.000 claims description 7
- 230000000379 polymerizing effect Effects 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 230000036571 hydration Effects 0.000 claims description 6
- 238000006703 hydration reaction Methods 0.000 claims description 6
- WZAPDMOCOACDGU-UHFFFAOYSA-N 1-tert-butyl-3-methylidenepyrrolidin-2-one Chemical compound CC(C)(C)N1CCC(=C)C1=O WZAPDMOCOACDGU-UHFFFAOYSA-N 0.000 claims description 5
- YNQNQJPLBDEVRW-UHFFFAOYSA-N 5-methylidene-1-propan-2-ylpyrrolidin-2-one Chemical compound CC(C)N1C(=C)CCC1=O YNQNQJPLBDEVRW-UHFFFAOYSA-N 0.000 claims description 5
- RRUNPGIXAGEPSW-UHFFFAOYSA-N 5-methylidene-1-propylpyrrolidin-2-one Chemical compound CCCN1C(=C)CCC1=O RRUNPGIXAGEPSW-UHFFFAOYSA-N 0.000 claims description 5
- 239000004471 Glycine Substances 0.000 claims description 5
- 235000001014 amino acid Nutrition 0.000 claims description 5
- 229940024606 amino acid Drugs 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- 239000004599 antimicrobial Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- KEMYALYETOKJCG-UHFFFAOYSA-N 1-butyl-3-methylidenepyrrolidin-2-one Chemical compound CCCCN1CCC(=C)C1=O KEMYALYETOKJCG-UHFFFAOYSA-N 0.000 claims description 4
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 4
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 4
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 4
- 235000004279 alanine Nutrition 0.000 claims description 4
- 229960001230 asparagine Drugs 0.000 claims description 4
- 235000009582 asparagine Nutrition 0.000 claims description 4
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 4
- 235000004554 glutamine Nutrition 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- NDKUQUPCEFPMSK-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;prop-2-enamide Chemical compound NC(=O)C=C.C=CN1CCCC1=O NDKUQUPCEFPMSK-UHFFFAOYSA-N 0.000 claims description 3
- XVGZUJYMDCFKIZ-UHFFFAOYSA-N 3-methylidene-1-propylpyrrolidin-2-one Chemical compound CCCN1CCC(=C)C1=O XVGZUJYMDCFKIZ-UHFFFAOYSA-N 0.000 claims description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 claims description 3
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 10
- 229910052710 silicon Inorganic materials 0.000 abstract description 9
- 239000002861 polymer material Substances 0.000 abstract description 8
- 125000000524 functional group Chemical group 0.000 description 33
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- 125000003396 thiol group Chemical group [H]S* 0.000 description 12
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- 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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Classifications
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- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
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- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
- B29D11/00125—Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
- B29D11/00134—Curing of the contact lens material
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00038—Production of contact lenses
- B29D11/00125—Auxiliary operations, e.g. removing oxygen from the mould, conveying moulds from a storage to the production line in an inert atmosphere
- B29D11/00192—Demoulding, e.g. separating lenses from mould halves
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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
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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
- C08F220/52—Amides or imides
- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
- C08F220/58—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide containing oxygen in addition to the carbonamido oxygen, e.g. N-methylolacrylamide, N-(meth)acryloylmorpholine
-
- 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
- C08F290/068—Polysiloxanes
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- 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
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- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
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- 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
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
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- 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
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- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
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- 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
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- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
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Abstract
Description
)、アリル、ビニル(
)、スチレニル、または他のC=C含有基が挙げられる。
(式中、R1およびR2は、互いに独立して、C1〜C8−アルキル、C1〜C4アルキル置換もしくはC1〜C4−アルコキシ置換のフェニル、フルオロ置換C1〜C18−アルキル、低分子量親水性ポリマー鎖、または−alk−(OCH2CH2)n−OE(ここで、alkはC1〜C6−アルキレン2価基であり、Eは水素もしくはC1〜C6アルキルであり、かつnは1〜50の整数である)であり、かつmは2〜500の整数である)
で示される2価基を意味する。
)はアミノ基(−NHR’)、カルボキシル、ヒドロキシル、またはチオールと約40℃〜140℃の温度で反応して結合(T1T2N−CH2−CH(OH)−CH2−E−、式中、E=NR’、COO、O、またはS)を形成する。
(式中、
υ1、υ2、およびω1は、互いに独立して、1〜500の整数であり、
ω2は、互いに独立して、1〜10の整数であり、
R3およびR4は、互いに独立して、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、
R10およびR11は、互いに独立して、置換または非置換のC1〜C10アルキレン2価基であり、
R5、R6、R7、R8、R9、R12、R13、R14、R15、R16、およびR17は、互いに独立して、C1〜C8−アルキル、C1〜C4アルキル置換もしくはC1〜C4アルコキシ置換のフェニル、またはフルオロ置換C1〜C18−アルキルであり、(ただし、好ましくはメチルである)、
L1は、
(ここで、R18は、置換または非置換のC1〜C10アルキレン2価基であり、かつR18’は、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、X1は、直接結合、チオエーテル結合(−S−)、−NR20−(ここで、R20は、置換または非置換のC1〜C10アルキルである)である)
で示される2価基、または
(ここで、R19は、置換または非置換のC1〜C10アルキレン2価基であり、かつR20は、置換または非置換のC1〜C10アルキルである)
で示される2価基であり、
L2は、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、
E1、E2、およびE3は、互いに独立して、水素、置換もしくは非置換のC1〜C8−アルキル、C1〜C8−アルコキシ、−NH2、−NHR’(ここで、R’はC1〜C10アルキルである)、ヒドロキシル、カルボキシル、ハロゲン原子(BrもしくはCl)、チオール、または
(ここで、r1およびr2は、互いに独立して、0もしくは1の整数であり、R’’は水素もしくはメチルであり、R21は、置換もしくは非置換のC1〜C10アルキレン2価基であり、X2は、
(ここで、R22およびR23は、互いに独立して、C1〜C8アルキル(好ましくはメチル)であり、かつR19は、置換もしくは非置換のC1〜C10アルキレン2価基である)
である)
である重合性基であり、ただし、E1およびE2は両方とも重合性基であるかまたはE3は重合性基であるかのいずれかであり、かつ
hPCは、(1)オキサゾリンの開環重合で得られるポリオキサゾリンセグメント
(ここで、R1は、水素、メチル基、またはエチル基であり、かつqは3〜500の整数である)、(2)アスパラギン、グルタミン、アラニン、グリシン、およびそれらの組合せからなる群から選択される少なくとも1種のアミノ酸で構成されたポリペプチドセグメント、ならびに(3)(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、ジメチルアミノエチル(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリルアミド、N−ビニル−2−ピロリドン、N−ビニル−N−メチルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、N−ビニルホルムアミド、N−ビニルアセトアミド、N−ビニルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、N−メチル−3−メチレン−2−ピロリドン、1−エチル−3−メチレン−2−ピロリドン、1−メチル−5−メチレン−2−ピロリドン、1−エチル−5−メチレン−2−ピロリドン、5−メチル−3−メチレン−2−ピロリドン、5−エチル−3−メチレン−2−ピロリドン、1−n−プロピル−3−メチレン−2−ピロリドン、1−n−プロピル−5−メチレン−2−ピロリドン、1−イソプロピル−3−メチレン−2−ピロリドン、1−イソプロピル−5−メチレン−2−ピロリドン、1−n−ブチル−3−メチレン−2−ピロリドン、1−tert−ブチル−3−メチレン−2−ピロリドン、およびそれらの混合物からなる群から選択される(好ましくは、N−ビニルピロリドン、N,N−ジメチル(メタ)アクリルアミド、(メタ)アクリルアミド、N−ビニルホルムアミド、N−ビニルアセトアミド、N−ビニルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、N−メチル−3−メチレン−2−ピロリドン、1−エチル−3−メチレン−2−ピロリドン、1−メチル−5−メチレン−2−ピロリドン、1−エチル−5−メチレン−2−ピロリドン、5−メチル−3−メチレン−2−ピロリドン、5−エチル−3−メチレン−2−ピロリドン、およびそれらの組合せからなる群から選択される)少なくとも1種の親水性ビニル系モノマーに由来する親水性モノマー単位で構成された親水性ポリマーセグメント、からなる群から選択される親水性ポリマーセグメントである)
により定義される。
式(3)
(式中、R3、R4、R5、R6、R7、R8、R9、E1、E2、υ1、およびω1は、以上に定義した通りである)
で示されるヒドロシロキサン含有ポリシロキサンと、を当業者に公知の白金触媒ヒドロシリル化反応で反応させることにより調製可能である。
(ここで、R’’、R21、X2、r1、およびr2は以上に定義した通りである)
である)
で示されるヒドロシロキサン含有ポリシロキサンは、D4対H4の所望のモル比を用いて鎖末端ブロックとしての式(4)
(式中、E1、E2、R3、R4、R5、R6、R8、およびR9は以上に定義した通りである)
で示されるジシロキサンの存在下および触媒の存在下でオクタメチルシクロテトラシロキサン(D4)と1,3,5,7−テトラメチルシクロテトラシロキサン(H4)との混合物を重合することにより調製可能である。式(4)で示されるジシロキサンは、エチレン性官能基化ビニル系モノマー(たとえば、アミノ−C2〜C6アルキル(メタ)アクリルアミド、C1〜C6アルキルアミノ−C2〜C6アルキル(メタ)アクリルアミド、(メタ)アクリル酸、N,N−2−アクリルアミドグリコール酸、ハロゲン化(メタ)アクリロイル類(CH2=CH−COXまたはCH2=CCH3−COX、X=ClまたはBr)、(メタ)アクリル酸のN−ヒドロキシスクシンイミドエステル、アズラクトン含有ビニル系モノマー(以上に記載のいずれか1つ)を用いて、反応性官能基を含有する2個の置換基を有するジシロキサン(たとえば、ジ−アミノアルキル−テトラアルキル−ジシロキサン、ジ−アルキルアミノアルキル−テトラアルキル−ジシロキサン、ジ−カルボキシアルキル−テトラアルキル−ジシロキサン、またはジ−ヒドロキシアルキル−テトラアルキル−ジシロキサン)をエチレン性官能基化することにより得ることが可能である。
CH2=CH−R18−X1−R18’−hPC−L2−E3 (5)
(式中、R18、X1、R18’、hPC、L2、およびE3は以上に定義した通りである)
で示される線状モノエン官能性親水性ポリマーは、当業者に公知の任意の方法に従って調製可能である。
CH2=CH−R18−Z1 (6)
(式中、R18は、置換または非置換のC1〜C10アルキレン2価基であり、かつZ1は、ヒドロキシル基、カルボキシル基、−NH2基、C1〜C12アルキルアミノ基、エポキシ基、ハロゲン(BrまたはCl)基、およびアゼチジニウム基からなる群から選択されて官能基である)で示されるエン含有モノマーでエチレン性官能基化することにより、調製可能である。ヘテロ二官能性ポリオキサゾリンの2つの異なる官能基の異なる反応性に基づいて式(6)で示されるエン含有モノマーをどのように選択するかは、当業者の熟知するところである。
(式中、R3、R4、R5、R6、R7、R8、R9、R18、Z1、E1、E2、υ1、およびω1は以上に定義した通りである)
で示されるポリシロキサンを得る。第2の工程では、式(7)で示されるポリシロキサンと単官能性線状親水性ポリマーまたはヘテロ二官能性線状親水性ポリマーと反応させて、式(1)で示される化学線重合性両親媒性ポリシロキサンを得る。ヘテロ二官能性線状親水性ポリマーを使用する場合、式(1)で示される得られた両親媒性ポリシロキサンとエチレン性不飽和ビニル系モノマーとをさらに反応させて、未反応末端官能基を重合性基に変換することが可能である。
)を有する親水性ポリマーを調製する。親水性ポリマーは、連鎖移動剤としてのチオールシランの存在下で従来のラジカル重合を用いて調製される。連鎖移動剤は、ポリマーの分子量の制御を可能にするだけでなく、第2の工程でさらなる鎖延長を行うためにジメトキシシラン基を提供する。第2の工程では、α,ω−ジヒドロキシポリ(ジアルキルシロキサン)(PDMS)と工程1で得られた親水性ポリマーとの間の縮合反応を行う。第3の工程では、ヒドロキシアルキル(メタ)アクリルアミド(たとえば、ヒドロキシエチルアクリルアミド)と末端メトキシシランとを反応させて架橋性アクリルアミド基を導入する。ジメトキシシランとOHとの比を制御することにより、式(2)で示される化学線重合性両親媒性ポリシロキサンを調製することが可能である。PDMSセグメント分子量は1,000〜20,000g/molの範囲内である。親水性ポリマーMWは500〜5,000g/molの範囲内である。
1. 式(1)または(2)
(式中、
υ1、υ2、およびω1は、互いに独立して、1〜500の整数であり、
ω2は、互いに独立して、1〜10の整数であり、
R3およびR4は、互いに独立して、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、
R10およびR11は、互いに独立して、置換または非置換のC1〜C10アルキレン2価基であり、
R5、R6、R7、R8、R9、R12、R13、R14、R15、R16、およびR17は、互いに独立して、C1〜C8−アルキル、C1〜C4アルキル置換もしくはC1〜C4アルコキシ置換のフェニル、またはフルオロ置換C1〜C18−アルキルであり、(ただし、好ましくはメチルである)、
L1は、
(ここで、R18は、置換または非置換のC1〜C10アルキレン2価基であり、かつR18’は、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、X1は、直接結合、チオエーテル結合(−S−)、−NR20−(ここで、R20は、置換または非置換のC1〜C10アルキルである)である)
で示される2価基、または
(ここで、R19は、置換または非置換のC1〜C10アルキレン2価基であり、かつR20は、置換または非置換のC1〜C10アルキルである)
で示される2価基であり、
L2は、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、
E1、E2、およびE3は、互いに独立して、水素、置換もしくは非置換のC1〜C8−アルキル、C1〜C8−アルコキシ、−NH2、−NHR’(ここで、R’はC1〜C10アルキルである)、ヒドロキシル、カルボキシル、ハロゲン原子(BrもしくはCl)、チオール、または
(ここで、r1およびr2は、互いに独立して、0もしくは1の整数であり、R’’は水素もしくはメチルであり、R21は、置換もしくは非置換のC1〜C10アルキレン2価基であり、X2は、
(ここで、R22およびR23は、互いに独立して、C1〜C8アルキルであり、かつR19は、置換もしくは非置換のC1〜C10アルキレン2価基である)
である)
である重合性基であり、ただし、(i)E1およびE2は両方とも重合性基であるかまたは(ii)E3は重合性基であるかのいずれかであり、かつ
hPCは、(1)オキサゾリンの開環重合で得られるポリオキサゾリンセグメント
(ここで、R1は、水素、メチル基、またはエチル基であり、かつqは3〜500の整数である)、(2)アスパラギン、グルタミン、アラニン、グリシン、およびそれらの組合せからなる群から選択される少なくとも1種のアミノ酸で構成されたポリペプチドセグメント、ならびに(3)(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、ジメチルアミノエチル(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリルアミド、N−ビニル−2−ピロリドン、N−ビニル−N−メチルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、N−ビニルホルムアミド、N−ビニルアセトアミド、N−ビニルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、N−メチル−3−メチレン−2−ピロリドン、1−エチル−3−メチレン−2−ピロリドン、1−メチル−5−メチレン−2−ピロリドン、1−エチル−5−メチレン−2−ピロリドン、5−メチル−3−メチレン−2−ピロリドン、5−エチル−3−メチレン−2−ピロリドン、1−n−プロピル−3−メチレン−2−ピロリドン、1−n−プロピル−5−メチレン−2−ピロリドン、1−イソプロピル−3−メチレン−2−ピロリドン、1−イソプロピル−5−メチレン−2−ピロリドン、1−n−ブチル−3−メチレン−2−ピロリドン、1−tert−ブチル−3−メチレン−2−ピロリドン、およびそれらの混合物からなる群から選択される少なくとも1種の親水性ビニル系モノマーに由来する親水性モノマー単位で構成された親水性ポリマーセグメント、からなる群から選択される親水性ポリマーセグメントである)
で示される化学線重合性両親媒性ポリシロキサン。
酸素透過係数の測定
レンズおよびレンズ材料の見掛けの酸素透過係数(Dkapp)、見掛けの酸素透過率(Dk/t)、固有(またはエッジ補正)酸素透過係数(Dkc)は、米国特許出願公開第2012/0026457A1号明細書(その全体が参照により本明細書に組み込まれる)の実施例1に記載の手順に従って決定される。
レンズのイオン透過係数は、米国特許第5,760,100号明細書(その全体が参照により本明細書に組み込まれる)に記載の手順に従って測定される。以下の実施例で報告したイオン透過係数の値は、基準物質としてのレンズ材料Alsaconを基準にした相対イオンフラックス拡散係数(D/Dref)である。Alsaconは、0.314×10−3mm2/分のイオンフラックス拡散係数を有する。
Claims (17)
- 式(1)または(2)
(式中、
υ1、υ2、およびω1は、互いに独立して、1〜500の整数であり、
ω2は、互いに独立して、1〜10の整数であり、
R3およびR4は、互いに独立して、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、
R10およびR11は、互いに独立して、置換または非置換のC1〜C10アルキレン2価基であり、
R5、R6、R7、R8、R9、R12、R13、R14、R15、R16、およびR17は、互いに独立して、C1〜C8−アルキル、C1〜C4アルキル置換もしくはC1〜C4アルコキシ置換のフェニル、またはフルオロ置換C1〜C18−アルキルであり、(ただし、好ましくはメチルである)、
L1は、
(ここで、R18は、置換または非置換のC1〜C10アルキレン2価基であり、かつR18’は、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、X1は、直接結合、チオエーテル結合(−S−)、−NR20−(ここで、R20は、置換または非置換のC1〜C10アルキルである)である)
で示される2価基、または
(ここで、R19は、置換または非置換のC1〜C10アルキレン2価基であり、かつR20は、置換または非置換のC1〜C10アルキルである)
で示される2価基であり、
L2は、直接結合または置換もしくは非置換のC1〜C10アルキレン2価基であり、
E1、E2、およびE3は、互いに独立して、水素、置換もしくは非置換のC1〜C8−アルキル、C1〜C8−アルコキシ、−NH2、−NHR’(ここで、R’はC1〜C10アルキルである)、ヒドロキシル、カルボキシル、Br、Cl、チオール、または
(ここで、r1およびr2は、互いに独立して、0もしくは1の整数であり、R’’は水素もしくはメチルであり、R21は、置換もしくは非置換のC1〜C10アルキレン2価基であり、X2は、
(ここで、R22およびR23は、互いに独立して、C1〜C8アルキル(好ましくはメチル)であり、かつR19は、置換もしくは非置換のC1〜C10アルキレン2価基である)
である)
である重合性基であり、ただし、(i)E1およびE2は両方とも重合性基であるかまたは(ii)E3は重合性基であるかのいずれかであり、かつ
hPCは、(1)オキサゾリンの開環重合で得られるポリオキサゾリンセグメント
(ここで、R1は、水素、メチル基、またはエチル基であり、かつqは3〜500の整数である)、(2)アスパラギン、グルタミン、アラニン、グリシン、およびそれらの組合せからなる群から選択される少なくとも1種のアミノ酸で構成されたポリペプチドセグメント、ならびに(3)(メタ)アクリルアミド、N,N−ジメチル(メタ)アクリルアミド、ジメチルアミノエチル(メタ)アクリレート、ジメチルアミノエチル(メタ)アクリルアミド、N−ビニル−2−ピロリドン、N−ビニル−N−メチルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、N−ビニルホルムアミド、N−ビニルアセトアミド、N−ビニルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、N−メチル−3−メチレン−2−ピロリドン、1−エチル−3−メチレン−2−ピロリドン、1−メチル−5−メチレン−2−ピロリドン、1−エチル−5−メチレン−2−ピロリドン、5−メチル−3−メチレン−2−ピロリドン、5−エチル−3−メチレン−2−ピロリドン、1−n−プロピル−3−メチレン−2−ピロリドン、1−n−プロピル−5−メチレン−2−ピロリドン、1−イソプロピル−3−メチレン−2−ピロリドン、1−イソプロピル−5−メチレン−2−ピロリドン、1−n−ブチル−3−メチレン−2−ピロリドン、1−tert−ブチル−3−メチレン−2−ピロリドン、およびそれらの混合物からなる群から選択される少なくとも1種の親水性ビニル系モノマーに由来する親水性モノマー単位で構成された親水性ポリマーセグメント、からなる群から選択される親水性ポリマーセグメントである)
で示される化学線重合性両親媒性ポリシロキサン。 - E1およびE2が、水素、置換もしくは非置換のC1〜C8−アルキル、C1〜C8−アルコキシ、−NH2、−NHR’(ここで、R’はC1〜C10アルキルである)、ヒドロキシル、カルボキシル、Br、Cl、またはチオールである、請求項1または2に記載の化学線重合性両親媒性ポリシロキサン。
- υ2が3〜350(好ましくは5〜200、より好ましくは10〜150)の整数である、請求項1〜4のいずれか一項に記載の化学線重合性両親媒性ポリシロキサン。
- υ1およびω1が、互いに独立して、3〜350、好ましくは5〜200、より好ましくは10〜150の整数である、請求項1〜5のいずれか一項に記載の化学線重合性両親媒性ポリシロキサン。
- hPCが、ポリオキサゾリンセグメント、次の親水性ビニル系モノマー、すなわち、N−ビニルピロリドン、N,N−ジメチル(メタ)アクリルアミド、(メタ)アクリルアミド、N−ビニルホルムアミド、N−ビニルアセトアミド、N−ビニルイソプロピルアミド、N−ビニル−N−メチルアセトアミド、N−メチル−3−メチレン−2−ピロリドン、1−エチル−3−メチレン−2−ピロリドン、1−メチル−5−メチレン−2−ピロリドン、1−エチル−5−メチレン−2−ピロリドン、5−メチル−3−メチレン−2−ピロリドン、5−エチル−3−メチレン−2−ピロリドン、およびそれらの組合せからなる群から選択される少なくとも1種の親水性ビニル系モノマーに由来する親水性モノマー単位で構成された親水性ポリマーセグメント、ならびにそれらの組合せからなる群から選択される親水性ポリマーセグメントである、請求項1〜6のいずれか一項に記載の化学線重合性両親媒性ポリシロキサン。
- hPCがポリオキサゾリンセグメントである、請求項1〜6のいずれか一項に記載の化学線重合性両親媒性ポリシロキサン。
- 式(1)で示される、請求項1〜8のいずれか一項に記載の化学線重合性両親媒性ポリシロキサン。
- υ1:ω1が約7:3〜約9.5:0.5である、請求項9に記載の化学線重合性両親媒性ポリシロキサン。
- 式(2)で示される、請求項1〜8のいずれか一項に記載の化学線重合性両親媒性ポリシロキサン。
- 請求項1〜11のいずれか一項に記載の化学線重合性両親媒性ポリシロキサンの繰返し単位を含むポリマー。
- 前記ポリマーが、少なくとも1種の親水性ビニル系モノマーの繰返し親水性単位をさらに含む化学線架橋性シリコーン含有プレポリマーである、請求項12に記載のポリマー。
- コンタクトレンズが、完全水和時に重量基準で約20%〜約75%、好ましくは約25%〜約70%、より好ましくは約30%〜約65%の含水率と、少なくとも約40barrer、好ましくは少なくとも約50barrer、より好ましくは少なくとも約60barrer、さらにより好ましくは少なくとも約70barrerの酸素透過係数(Dk)と、約0.1MPa〜約2.0MPa、好ましくは約0.2MPa〜約1.5MPa、より好ましくは約0.3MPa〜約1.2MPa、さらにより好ましくは約0.4MPa〜約1.0MPaの弾性率と、を有する、請求項1〜11のいずれか一項に記載の化学線重合性両親媒性ポリシロキサンの繰返し単位を含むシリコーンハイドロゲル材料を含むコンタクトレンズ。
- 次の工程、すなわち、コンタクトレンズを作製するために成形型内にレンズ形成配合物を導入する工程であって、前記レンズ形成配合物が、(a)水、1,2−プロピレングリコール、約400ダルトン以下の分子量を有するポリエチレングリコール、およびそれらの混合物からなる群から選択される溶媒と、(b)請求項1〜11のいずれか一項に記載の少なくとも1種の両親媒性シロキサン含有ビニル系モノマーと、(c)親水性ビニル系モノマー、親水化ポリシロキサン含有クロスリンカー、親水性クロスリンカー、光開始剤、熱開始剤、UV吸収性ビニル系モノマー、可視性ティント剤、抗微生物剤、バイオ活性剤、浸出性滑剤、浸出性涙液安定化剤、およびそれらの混合物からなる群から選択される少なくとも1種の成分と、を含む、工程と、シリコーンハイドロゲルコンタクトレンズを形成するために前記成形型内で前記レンズ形成配合物を重合する工程であって、形成されたシリコーンハイドロゲルコンタクトレンズが、完全水和時に重量基準で約20%〜約75%、好ましくは約25%〜約70%、より好ましくは約30%〜約65%の含水率と、少なくとも約40barrer、好ましくは少なくとも約50barrer、より好ましくは少なくとも約60barrer、さらにより好ましくは少なくとも約70barrerの酸素透過係数(Dk)と、約0.1MPa〜約2.0MPa、好ましくは約0.2MPa〜約1.5MPa、より好ましくは約0.3MPa〜約1.2MPa、さらにより好ましくは約0.4MPa〜約1.0MPaの弾性率と、を有する、工程と、を含む、シリコーンハイドロゲルコンタクトレンズの作製方法。
- 水または水性溶液で成形シリコーンハイドロゲルコンタクトレンズを抽出する工程をさらに含む、請求項15に記載の方法。
- 前記成形型が再使用可能な成形型であり、かつ前記レンズ形成組成物が、前記シリコーンハイドロゲルコンタクトレンズを形成するために化学線の空間制限下で化学線的に硬化(すなわち重合)される、請求項15または16に記載の方法。
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NZ728772A (en) | 2018-10-26 |
US9720139B2 (en) | 2017-08-01 |
MX2017003939A (es) | 2017-06-26 |
TW201619245A (zh) | 2016-06-01 |
EP3197940A1 (en) | 2017-08-02 |
EP3197940B1 (en) | 2023-02-15 |
KR102397773B1 (ko) | 2022-05-13 |
CA2958458C (en) | 2020-06-16 |
CN106716182A (zh) | 2017-05-24 |
RU2017114359A3 (ja) | 2019-02-13 |
TWI713468B (zh) | 2020-12-21 |
JP6438128B2 (ja) | 2018-12-12 |
BR112017005391B1 (pt) | 2021-09-14 |
CA2958458A1 (en) | 2016-03-31 |
BR112017005391A2 (pt) | 2017-12-12 |
KR20170063690A (ko) | 2017-06-08 |
US9637582B2 (en) | 2017-05-02 |
AU2015321646A1 (en) | 2017-03-09 |
US20160090432A1 (en) | 2016-03-31 |
SG11201700842RA (en) | 2017-04-27 |
CN106716182B (zh) | 2020-06-12 |
US20170176643A1 (en) | 2017-06-22 |
MY179853A (en) | 2020-11-18 |
WO2016048853A1 (en) | 2016-03-31 |
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