CS205116B2 - Method of preparing silicone copolymers grafted by hydrophylic monomers - Google Patents

Method of preparing silicone copolymers grafted by hydrophylic monomers Download PDF

Info

Publication number: CS205116B2
Authority: CS; Czechoslovakia
Prior art keywords: grafting; silicone; copolymers; hydrophilic; contact lens
Prior art date: 1977-03-31

Application number

CS782085A

Other languages

Czech (cs)

English (en)

Inventor

Georges Wajs

Original Assignee

Essilor Int

Priority date (The priority date 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 date listed.)

1977-03-31

Filing date

1978-03-31

Publication date

1981-04-30

1978-03-31 Application filed by Essilor Int filed Critical Essilor Int

1981-04-30 Publication of CS205116B2 publication Critical patent/CS205116B2/cs

Links

229920001296 polysiloxane Polymers 0.000 title claims abstract description 34
238000000034 method Methods 0.000 title claims abstract description 30
239000000178 monomer Substances 0.000 title claims abstract description 23
230000005855 radiation Effects 0.000 claims abstract description 23
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
239000001301 oxygen Substances 0.000 claims abstract description 8
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
238000002360 preparation method Methods 0.000 claims abstract description 4
238000004519 manufacturing process Methods 0.000 claims description 13
229920001577 copolymer Polymers 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 4
150000001875 compounds Chemical class 0.000 abstract description 10
229920000578 graft copolymer Polymers 0.000 abstract description 5
229920002050 silicone resin Polymers 0.000 abstract 2
238000009281 ultraviolet germicidal irradiation Methods 0.000 abstract 1
229920005573 silicon-containing polymer Polymers 0.000 description 24
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 11
239000000203 mixture Substances 0.000 description 10
WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 9
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 9
229910052753 mercury Inorganic materials 0.000 description 9
239000000463 material Substances 0.000 description 7
229920000036 polyvinylpyrrolidone Polymers 0.000 description 7
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 7
239000001267 polyvinylpyrrolidone Substances 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
229910052697 platinum Inorganic materials 0.000 description 5
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
239000002253 acid Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
229910004298 SiO 2 Inorganic materials 0.000 description 3
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
230000005587 bubbling Effects 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000007334 copolymerization reaction Methods 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
238000006116 polymerization reaction Methods 0.000 description 3
239000004215 Carbon black (E152) Substances 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
230000002411 adverse Effects 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
150000002433 hydrophilic molecules Chemical class 0.000 description 2
230000005865 ionizing radiation Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229920001558 organosilicon polymer Polymers 0.000 description 2
-1 polysiloxanes Polymers 0.000 description 2
239000010453 quartz Substances 0.000 description 2
238000004383 yellowing Methods 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 1
JSOWQCTXCCXWCJ-UHFFFAOYSA-N 1-ethylpyrrolidin-2-one;prop-2-enoic acid Chemical compound OC(=O)C=C.CCN1CCCC1=O JSOWQCTXCCXWCJ-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000654 additive Substances 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000003321 amplification Effects 0.000 description 1
229940045985 antineoplastic platinum compound Drugs 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
210000004087 cornea Anatomy 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
230000006866 deterioration Effects 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
230000002209 hydrophobic effect Effects 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
230000001678 irradiating effect Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000000465 moulding Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000003199 nucleic acid amplification method Methods 0.000 description 1
150000003057 platinum Chemical class 0.000 description 1
150000003058 platinum compounds Chemical class 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000009877 rendering Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000007858 starting material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000000007 visual effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/16—Chemical modification with polymerisable compounds
- C08J7/18—Chemical modification with polymerisable compounds using wave energy or particle radiation
- 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
- B29D11/00134—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
- B29D11/00865—Applying coatings; tinting; colouring
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes

Landscapes

Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Physics & Mathematics (AREA)
Mechanical Engineering (AREA)
Ophthalmology & Optometry (AREA)
Manufacturing & Machinery (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
Polymers & Plastics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Toxicology (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Eyeglasses (AREA)
Treatments Of Macromolecular Shaped Articles (AREA)
Silicon Polymers (AREA)
Graft Or Block Polymers (AREA)
Macromonomer-Based Addition Polymer (AREA)

CS782085A 1977-03-31 1978-03-31 Method of preparing silicone copolymers grafted by hydrophylic monomers CS205116B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7709766A FR2385763A1 (fr)	1977-03-31	1977-03-31	Procede de preparation de copolymeres greffes de silicones

Publications (1)

Publication Number	Publication Date
CS205116B2 true CS205116B2 (en)	1981-04-30

Family

ID=9188842

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS782085A CS205116B2 (en)	1977-03-31	1978-03-31	Method of preparing silicone copolymers grafted by hydrophylic monomers

Country Status (15)

Country	Link
US (1)	US4229273A (de)
JP (1)	JPS53121874A (de)
AT (1)	AT380962B (de)
BE (1)	BE865071A (de)
BR (1)	BR7801971A (de)
CH (1)	CH630103A5 (de)
CS (1)	CS205116B2 (de)
DD (1)	DD137238A5 (de)
DE (1)	DE2813558C2 (de)
ES (1)	ES468279A1 (de)
FR (1)	FR2385763A1 (de)
GB (1)	GB1598754A (de)
HU (1)	HU180453B (de)
NL (1)	NL7803234A (de)
SU (1)	SU973027A3 (de)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3004685C2 (de) *	1980-02-08	1986-07-31	Titmus Eurocon Kontaktlinsen GmbH, 8750 Aschaffenburg	Verfahren zur Hydrophilierung von Kontaktlinsen aus Siliconkautschuk
EP0220919A3 (de) *	1985-10-21	1989-04-12	Shin-Etsu Chemical Co., Ltd.	Kontaktlinse
US4983702A (en) *	1988-09-28	1991-01-08	Ciba-Geigy Corporation	Crosslinked siloxane-urethane polymer contact lens
US4968532A (en) *	1989-01-13	1990-11-06	Ciba-Geigy Corporation	Process for graft copolymerization on surfaces of preformed substrates to modify surface properties
US4978481A (en) *	1989-01-13	1990-12-18	Ciba-Geigy Corporation	Process for the encapsulation of preformed substrates by graft copolymerization
US5274028A (en) *	1990-12-06	1993-12-28	Baxter International Inc.	Polyvinyl pyrrolidone-grafted coatings on preformed polymers
US7468398B2 (en)	1994-09-06	2008-12-23	Ciba Vision Corporation	Extended wear ophthalmic lens
US5760100B1 (en)	1994-09-06	2000-11-14	Ciba Vision Corp	Extended wear ophthalmic lens
EP0814116A1 (de) *	1996-06-19	1997-12-29	Hüls Aktiengesellschaft	Hydrophile Beschichtung von Oberflächen polymerer Substrate
US6132561A (en) *	1997-10-13	2000-10-17	Mincher; Bruce J.	Process for the solvent extraction for the radiolysis and dehalogenation of halogenated organic compounds in soils, sludges, sediments and slurries
JP5242876B2 (ja) *	2000-03-24	2013-07-24	ノバルティスアーゲー	架橋結合性または重合性プレポリマー
DK1385423T3 (da) *	2001-04-27	2008-03-25	Eyesense Ag	Udstyr til måling af glukosekoncentrationer i blod
US7438411B2 (en) *	2005-05-07	2008-10-21	Nanospectra Biosciences, Inc.	Plasmon resonant based eye protection
US8524800B2 (en) *	2006-12-13	2013-09-03	Novartis Ag	Actinically curable silicone hydrogel copolymers and uses thereof
BRPI0809151A2 (pt) *	2007-03-22	2014-09-16	Novartis Ag	Prepolímeros contendo silicone com cadeias poliméricas hidrófilas pendentes
CN101641206B (zh) *	2007-03-22	2013-03-20	诺瓦提斯公司	具有含悬挂的聚硅氧烷的聚合物链的预聚物
US8044111B2 (en)	2007-11-30	2011-10-25	Novartis Ag	Actinically-crosslinkable silicone-containing block copolymers
US8506856B2 (en) *	2007-12-10	2013-08-13	Novartis Ag	Method for making silicone hydrogel contact lenses
BR112012005626A2 (pt) *	2009-09-15	2016-08-02	Novartis Ag	pré-polímeros adequados para tornar lentes de contato de absorção de ultravioleta
KR101637254B1 (ko)	2010-07-30	2016-07-07	노파르티스 아게	양친매성 폴리실록산 예비중합체 및 그의 용도

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1526934A (fr) *	1966-12-01	1968-05-31	Commissariat Energie Atomique	Procédé de préparation des silicones hydrophiles par greffage radiochimique
US3959102A (en) *	1973-08-06	1976-05-25	Essilor International (Compagnie Generale D'optique S.A.)	Method for preparing a crosslinked graft copolymer of silicone and polyvinylpyrrolidone for use as a contact lens, and a contact lens produced thereby
GB1480880A (en) *	1974-05-06	1977-07-27	Bausch & Lomb	Shaped body of a simultaneously interpenetrating network polymer and method of preparing same

1977
- 1977-03-31 FR FR7709766A patent/FR2385763A1/fr active Granted
1978
- 1978-03-16 AT AT0187578A patent/AT380962B/de not_active IP Right Cessation
- 1978-03-20 BE BE186075A patent/BE865071A/xx not_active IP Right Cessation
- 1978-03-28 HU HU78EI786A patent/HU180453B/hu unknown
- 1978-03-28 ES ES468279A patent/ES468279A1/es not_active Expired
- 1978-03-28 NL NL7803234A patent/NL7803234A/xx not_active Application Discontinuation
- 1978-03-28 CH CH326778A patent/CH630103A5/fr not_active IP Right Cessation
- 1978-03-29 DE DE2813558A patent/DE2813558C2/de not_active Expired
- 1978-03-29 JP JP3650178A patent/JPS53121874A/ja active Pending
- 1978-03-30 BR BR7801971A patent/BR7801971A/pt unknown
- 1978-03-30 DD DD78204484A patent/DD137238A5/de unknown
- 1978-03-30 GB GB12495/78A patent/GB1598754A/en not_active Expired
- 1978-03-31 CS CS782085A patent/CS205116B2/cs unknown
- 1978-03-31 SU SU782599202A patent/SU973027A3/ru active
1979
- 1979-05-23 US US06/041,734 patent/US4229273A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
HU180453B (en)	1983-03-28
FR2385763B1 (de)	1980-12-05
DE2813558C2 (de)	1983-01-05
ES468279A1 (es)	1978-11-16
ATA187578A (de)	1985-12-15
DE2813558A1 (de)	1978-10-12
CH630103A5 (fr)	1982-05-28
SU973027A3 (ru)	1982-11-07
DD137238A5 (de)	1979-08-22
JPS53121874A (en)	1978-10-24
AT380962B (de)	1986-08-11
US4229273A (en)	1980-10-21
FR2385763A1 (fr)	1978-10-27
BE865071A (fr)	1978-07-17
BR7801971A (pt)	1978-12-26
GB1598754A (en)	1981-09-23
NL7803234A (nl)	1978-10-03

Publication	Publication Date	Title
CS205116B2 (en)	1981-04-30	Method of preparing silicone copolymers grafted by hydrophylic monomers
US3959102A (en)	1976-05-25	Method for preparing a crosslinked graft copolymer of silicone and polyvinylpyrrolidone for use as a contact lens, and a contact lens produced thereby
TWI712649B (zh)	2020-12-11	具有耐用的潤滑塗層於其上的軟性矽酮醫療器材
JP2551580B2 (ja)	1996-11-06	コンタクトレンズの親水化方法
AU2002323660B2 (en)	2007-11-08	Biomedical devices containing internal wetting agents
EP0643083B1 (de)	1997-05-14	Hydrophiles, durchsichtiges Material mit hoher Sauerstoffdurchlässigkeit auf der Basis von interpenetrierenden Polymernetzwerken, Verfahren zur Herstellung und Herstellung von weichen hochsauerstoffdurchlässigen Kontaktlinsen
ES2390246T3 (es)	2012-11-08	Procedimiento para fabricar monómeros de siloxanilo hidrófilos catiónicos
JP2005534737A (ja)	2005-11-17	改良されたバイオ医療品組成物
GB1579469A (en)	1980-11-19	Contact lens
EP1036102A1 (de)	2000-09-20	Verfahren zur herstellung von transparentpolymeren mit einer proteinhinterlegungbeständigkeit, polymere erhältlich mit diesem verfahren und kontaktlinse und intraokularimplantate daraus erhältlich
KR20020040661A (ko)	2002-05-30	안용(眼用)렌즈 재료 및 그 제조방법
JPH08510781A (ja)	1996-11-12	シリコーンポリマーの親水性を向上させる方法
IE873384L (en)	1988-06-15	Contact lens fabricated from an oxirane containing¹hydrophobic polymer
US5529727A (en)	1996-06-25	Method of treating contact lenses
KR20200062341A (ko)	2020-06-03	실리콘 고무 표면의 친수성 개질 방법 및 응용 방법
US4062627A (en)	1977-12-13	Flexible contact lens
JPH0570546A (ja)	1993-03-23	ポリシロキサン−尿素スチレン系マクロマー及びその架橋重合体
JPH07266443A (ja)	1995-10-17	ソフトコンタクトレンズの製造方法
JP5051808B2 (ja)	2012-10-17	プラスチック成形品、およびそれからなるコンタクトレンズ
CS208106B2 (en)	1981-08-31	Flexible contact lens and method of making the same
JP2003215509A (ja)	2003-07-30	親水化表面を有するシリコーンハイドロゲルからなるソフトコンタクトレンズの製造方法及びソフトコンタクトレンズ
JP2844772B2 (ja)	1999-01-06	ソフトコンタクトレンズ
JPS6370221A (ja)	1988-03-30	眼用レンズの製造方法
JPS63257720A (ja)	1988-10-25	酸素透過性硬質コンタクトレンズ
EP0116638A1 (de)	1984-08-29	Prothesen, kontaktlinsen und polymere dafür