JP2015524082A5 - - Google Patents

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Publication number: JP2015524082A5
Authority: JP; Japan
Prior art keywords: copolymer; group; polymer; ophthalmic device; meth
Prior art date: 2013-05-24
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

Application number

JP2015514217A

Other languages

English (en)

Japanese (ja)

Other versions

JP2015524082A (ja

JP6290189B2 (ja

Filing date

2013-05-24

Publication date

2016-07-14

2013-03-15 Priority claimed from US13/840,919 external-priority patent/US10073192B2/en

2013-05-22 Priority claimed from US13/899,676 external-priority patent/US9297929B2/en

2013-05-22 Priority claimed from US13/899,694 external-priority patent/US9244196B2/en

2013-05-24 Application filed filed Critical

2013-05-24 Priority claimed from PCT/US2013/042628 external-priority patent/WO2013177506A2/en

2015-08-20 Publication of JP2015524082A publication Critical patent/JP2015524082A/ja

2016-07-14 Publication of JP2015524082A5 publication Critical patent/JP2015524082A5/ja

2018-03-07 Application granted granted Critical

2018-03-07 Publication of JP6290189B2 publication Critical patent/JP6290189B2/ja

Status Expired - Fee Related legal-status Critical Current

2033-05-24 Anticipated expiration legal-status Critical

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229920001577 copolymer Polymers 0.000 claims description 46
229920000642 polymer Polymers 0.000 claims description 42
238000006116 polymerization reaction Methods 0.000 claims description 11
150000002632 lipids Chemical class 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
229920001296 polysiloxane Polymers 0.000 claims description 7
239000003431 cross linking reagent Substances 0.000 claims description 6
239000000203 mixture Substances 0.000 description 41
238000000034 method Methods 0.000 description 20
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 17
239000000178 monomer Substances 0.000 description 13
-1 cyano, silyl Chemical group 0.000 description 10
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
239000003889 eye drop Substances 0.000 description 8
229920001515 polyalkylene glycol Polymers 0.000 description 6
239000004971 Cross linker Substances 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
125000000129 anionic group Chemical group 0.000 description 4
229920006037 cross link polymer Polymers 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 3
125000002947 alkylene group Chemical group 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
229920000831 ionic polymer Polymers 0.000 description 3
239000000463 material Substances 0.000 description 3
HMYBDZFSXBJDGL-UHFFFAOYSA-N 1,3-bis(ethenyl)imidazolidin-2-one Chemical compound C=CN1CCN(C=C)C1=O HMYBDZFSXBJDGL-UHFFFAOYSA-N 0.000 description 2
BJELTSYBAHKXRW-UHFFFAOYSA-N 2,4,6-triallyloxy-1,3,5-triazine Chemical compound C=CCOC1=NC(OCC=C)=NC(OCC=C)=N1 BJELTSYBAHKXRW-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
XRUKRHLZDVJJSX-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical class N#CC(C)CCC(O)=O XRUKRHLZDVJJSX-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
125000004423 acyloxy group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
239000000017 hydrogel Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
229920001480 hydrophilic copolymer Polymers 0.000 description 2
229920001477 hydrophilic polymer Polymers 0.000 description 2
WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000004929 pyrrolidonyl group Chemical group N1(C(CCC1)=O)* 0.000 description 2
229920000208 temperature-responsive polymer Polymers 0.000 description 2
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
ABYZXVFUYMAIGL-UHFFFAOYSA-N 3-(2-methylbutyl)aziridin-2-one Chemical compound CCC(C)CC1NC1=O ABYZXVFUYMAIGL-UHFFFAOYSA-N 0.000 description 1
PWXIKGAMKWRXHD-UHFFFAOYSA-N 3-butylaziridin-2-one Chemical group CCCCC1NC1=O PWXIKGAMKWRXHD-UHFFFAOYSA-N 0.000 description 1
JRDBJIDIYUPWNR-UHFFFAOYSA-N 3-pentan-2-ylaziridin-2-one Chemical group CCCC(C)C1NC1=O JRDBJIDIYUPWNR-UHFFFAOYSA-N 0.000 description 1
101710141544 Allatotropin-related peptide Proteins 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
CVCDIGOEHQSPNM-UHFFFAOYSA-N CNC(C)=O.C(CC)S(=O)(=O)O Chemical compound CNC(C)=O.C(CC)S(=O)(=O)O CVCDIGOEHQSPNM-UHFFFAOYSA-N 0.000 description 1
VKTUOEHEJNQDBY-UHFFFAOYSA-N C[N+](C)(C)CC(O)=P(CCC([O-])=O)=O Chemical compound C[N+](C)(C)CC(O)=P(CCC([O-])=O)=O VKTUOEHEJNQDBY-UHFFFAOYSA-N 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical class CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
125000005333 aroyloxy group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
238000010560 atom transfer radical polymerization reaction Methods 0.000 description 1
125000000656 azaniumyl group Chemical group [H][N+]([H])([H])[*] 0.000 description 1
125000005620 boronic acid group Chemical group 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000536 complexating effect Effects 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003792 electrolyte Substances 0.000 description 1
UYMKPFRHYYNDTL-UHFFFAOYSA-N ethenamine Chemical compound NC=C UYMKPFRHYYNDTL-UHFFFAOYSA-N 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
IXHFNEAFAWRVCF-UHFFFAOYSA-N n,2-dimethylpropanamide Chemical compound CNC(=O)C(C)C IXHFNEAFAWRVCF-UHFFFAOYSA-N 0.000 description 1
229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
ZTUGCJNAJJDKDC-UHFFFAOYSA-N n-(3-hydroxypropyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCCCO ZTUGCJNAJJDKDC-UHFFFAOYSA-N 0.000 description 1
RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 1
LFKORVQXDHAIFK-UHFFFAOYSA-N n-[2-[2-(prop-2-enoylamino)ethoxy]ethyl]prop-2-enamide Chemical compound C=CC(=O)NCCOCCNC(=O)C=C LFKORVQXDHAIFK-UHFFFAOYSA-N 0.000 description 1
QJQAMHYHNCADNR-UHFFFAOYSA-N n-methylpropanamide Chemical compound CCC(=O)NC QJQAMHYHNCADNR-UHFFFAOYSA-N 0.000 description 1
CHDKQNHKDMEASZ-UHFFFAOYSA-N n-prop-2-enoylprop-2-enamide Chemical compound C=CC(=O)NC(=O)C=C CHDKQNHKDMEASZ-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
125000004928 piperidonyl group Chemical group 0.000 description 1
229920003213 poly(N-isopropyl acrylamide) Polymers 0.000 description 1
239000012985 polymerization agent Substances 0.000 description 1
XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-M propane-1-sulfonate Chemical compound CCCS([O-])(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-M 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000243 solution Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1

JP2015514217A 2012-05-25 2013-05-24 ポリマー及びナノゲル材料並びにその製造方法及び使用方法 Expired - Fee Related JP6290189B2 (ja)

Applications Claiming Priority (13)

Application Number	Priority Date	Filing Date	Title
US201261651767P	2012-05-25	2012-05-25
US61/651,767		2012-05-25
US201361771961P	2013-03-04	2013-03-04
US201361771959P	2013-03-04	2013-03-04
US61/771,961		2013-03-04
US61/771,959		2013-03-04
US13/840,919 US10073192B2 (en)	2012-05-25	2013-03-15	Polymers and nanogel materials and methods for making and using the same
US13/840,919		2013-03-15
US13/899,694		2013-05-22
US13/899,676		2013-05-22
US13/899,676 US9297929B2 (en)	2012-05-25	2013-05-22	Contact lenses comprising water soluble N-(2 hydroxyalkyl) (meth)acrylamide polymers or copolymers
US13/899,694 US9244196B2 (en)	2012-05-25	2013-05-22	Polymers and nanogel materials and methods for making and using the same
PCT/US2013/042628 WO2013177506A2 (en)	2012-05-25	2013-05-24	Polymers and nanogel materials and methods for making and using the same

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2018014560A Division JP2018092178A (ja)	2012-05-25	2018-01-31	ポリマー及びナノゲル材料並びにその製造方法及び使用方法

Publications (3)

Publication Number	Publication Date
JP2015524082A JP2015524082A (ja)	2015-08-20
JP2015524082A5 true JP2015524082A5 (2)	2016-07-14
JP6290189B2 JP6290189B2 (ja)	2018-03-07

Family

ID=49624375

Family Applications (4)

Application Number	Title	Priority Date	Filing Date
JP2015514217A Expired - Fee Related JP6290189B2 (ja)	2012-05-25	2013-05-24	ポリマー及びナノゲル材料並びにその製造方法及び使用方法
JP2015514219A Pending JP2015526745A (ja)	2012-05-25	2013-05-24	水溶性ｎ−（２ヒドロキシアルキル）（メタ）アクリルアミドポリマー又はコポリマーを含むコンタクトレンズ
JP2017218977A Active JP6526768B2 (ja)	2012-05-25	2017-11-14	水溶性ｎ−（２ヒドロキシアルキル）（メタ）アクリルアミドポリマー又はコポリマーを含むコンタクトレンズ
JP2018014560A Pending JP2018092178A (ja)	2012-05-25	2018-01-31	ポリマー及びナノゲル材料並びにその製造方法及び使用方法

Family Applications After (3)

Application Number	Title	Priority Date	Filing Date
JP2015514219A Pending JP2015526745A (ja)	2012-05-25	2013-05-24	水溶性ｎ−（２ヒドロキシアルキル）（メタ）アクリルアミドポリマー又はコポリマーを含むコンタクトレンズ
JP2017218977A Active JP6526768B2 (ja)	2012-05-25	2017-11-14	水溶性ｎ−（２ヒドロキシアルキル）（メタ）アクリルアミドポリマー又はコポリマーを含むコンタクトレンズ
JP2018014560A Pending JP2018092178A (ja)	2012-05-25	2018-01-31	ポリマー及びナノゲル材料並びにその製造方法及び使用方法

Country Status (13)

Country	Link
EP (6)	EP3401342A1 (2)
JP (4)	JP6290189B2 (2)
KR (2)	KR20150023485A (2)
CN (3)	CN104350076B (2)
AU (1)	AU2013266146A1 (2)
BR (2)	BR112014029253A2 (2)
CA (2)	CA2874718A1 (2)
HK (4)	HK1208482A1 (2)
IN (1)	IN2014DN09503A (2)
RU (2)	RU2640593C2 (2)
SG (2)	SG11201407374YA (2)
TW (2)	TWI598387B (2)
WO (3)	WO2013177523A2 (2)

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CN109734845A (zh) *	2018-12-03	2019-05-10	华东理工大学	一种基于聚电解质为模板的纳米凝胶的制备方法
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JP7492966B2 (ja)	2019-01-29	2024-05-30	ボシュ・アンド・ロム・インコーポレイテッド	コンタクトレンズのための包装溶液
CN110359276A (zh) *	2019-07-30	2019-10-22	北京化工大学常州先进材料研究院	聚异丙基丙烯酰胺分子刷聚癸二酸甘油酯基纤维膜及其制备方法和应用
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- 2013-05-24 CA CA2874718A patent/CA2874718A1/en not_active Abandoned
- 2013-05-24 IN IN9503DEN2014 patent/IN2014DN09503A/en unknown
- 2013-05-24 WO PCT/US2013/042658 patent/WO2013177523A2/en not_active Ceased
- 2013-05-24 RU RU2014152725A patent/RU2640593C2/ru not_active IP Right Cessation
- 2013-05-24 WO PCT/US2013/042628 patent/WO2013177506A2/en not_active Ceased
- 2013-05-24 HK HK15109232.2A patent/HK1208482A1/xx unknown
- 2013-05-24 EP EP18176232.9A patent/EP3401342A1/en not_active Withdrawn
- 2013-05-24 EP EP17198865.2A patent/EP3296334B9/en not_active Revoked
- 2013-05-24 CN CN201380027513.5A patent/CN104350076B/zh not_active Expired - Fee Related
- 2013-05-24 BR BR112014029253A patent/BR112014029253A2/pt not_active Application Discontinuation
- 2013-05-24 JP JP2015514217A patent/JP6290189B2/ja not_active Expired - Fee Related
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- 2013-05-24 HK HK15105318.7A patent/HK1204794A1/xx unknown
- 2013-05-24 CN CN201710281355.6A patent/CN107254026A/zh active Pending
- 2013-05-24 EP EP13728602.7A patent/EP2855546B1/en not_active Revoked
- 2013-05-24 HK HK15109726.5A patent/HK1209142A1/xx unknown
- 2013-05-24 CA CA2874664A patent/CA2874664A1/en not_active Abandoned
- 2013-05-24 SG SG11201407374YA patent/SG11201407374YA/en unknown
- 2013-05-24 TW TW102118452A patent/TWI598387B/zh not_active IP Right Cessation
- 2013-05-24 RU RU2014152715A patent/RU2014152715A/ru unknown
- 2013-05-24 KR KR20147036331A patent/KR20150023485A/ko not_active Withdrawn
- 2013-05-24 EP EP13729150.6A patent/EP2855547A2/en not_active Withdrawn
- 2013-05-24 SG SG11201407394TA patent/SG11201407394TA/en unknown
- 2013-05-24 TW TW102118348A patent/TWI582118B/zh active
- 2013-05-24 JP JP2015514219A patent/JP2015526745A/ja active Pending
- 2013-05-24 WO PCT/US2013/042644 patent/WO2013177513A1/en not_active Ceased
- 2013-05-24 EP EP13727758.8A patent/EP2855545B1/en not_active Revoked
- 2013-05-24 KR KR20147036157A patent/KR20150023464A/ko not_active Abandoned
- 2013-05-24 AU AU2013266146A patent/AU2013266146A1/en not_active Abandoned
- 2013-05-24 EP EP24204932.8A patent/EP4502052A3/en not_active Withdrawn
- 2013-05-24 BR BR112014029270A patent/BR112014029270A2/pt not_active Application Discontinuation
2017
- 2017-11-14 JP JP2017218977A patent/JP6526768B2/ja active Active
2018
- 2018-01-31 JP JP2018014560A patent/JP2018092178A/ja active Pending
- 2018-08-10 HK HK18110268.4A patent/HK1251003A1/en unknown

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