DE69911065T2 - Alkoxyacrylamide photochrome beschichtungszusammensetzung und photochrome gegenstände - Google Patents
Alkoxyacrylamide photochrome beschichtungszusammensetzung und photochrome gegenstände Download PDFInfo
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- DE69911065T2 DE69911065T2 DE69911065T DE69911065T DE69911065T2 DE 69911065 T2 DE69911065 T2 DE 69911065T2 DE 69911065 T DE69911065 T DE 69911065T DE 69911065 T DE69911065 T DE 69911065T DE 69911065 T2 DE69911065 T2 DE 69911065T2
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- photochromic
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- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
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- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
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- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical compound OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
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- FTWUXYZHDFCGSV-UHFFFAOYSA-N n,n'-diphenyloxamide Chemical class C=1C=CC=CC=1NC(=O)C(=O)NC1=CC=CC=C1 FTWUXYZHDFCGSV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31507—Of polycarbonate
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31645—Next to addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31678—Of metal
- Y10T428/31692—Next to addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31859—Next to an aldehyde or ketone condensation product
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/3188—Next to cellulosic
- Y10T428/31895—Paper or wood
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Paints Or Removers (AREA)
- Laminated Bodies (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Eyeglasses (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/211,249 US6060001A (en) | 1998-12-14 | 1998-12-14 | Alkoxyacrylamide photochromic coatings compositions and photochromic articles |
| US211249 | 1998-12-14 | ||
| PCT/US1999/029389 WO2000036047A1 (en) | 1998-12-14 | 1999-12-10 | Alkoxyacrylamide photochromic coating composition and photochromic articles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69911065D1 DE69911065D1 (de) | 2003-10-09 |
| DE69911065T2 true DE69911065T2 (de) | 2004-07-08 |
Family
ID=22786130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69911065T Expired - Lifetime DE69911065T2 (de) | 1998-12-14 | 1999-12-10 | Alkoxyacrylamide photochrome beschichtungszusammensetzung und photochrome gegenstände |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6060001A (cg-RX-API-DMAC7.html) |
| EP (1) | EP1147161B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP4451988B2 (cg-RX-API-DMAC7.html) |
| AU (1) | AU744068B2 (cg-RX-API-DMAC7.html) |
| BR (1) | BR9917067B1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE69911065T2 (cg-RX-API-DMAC7.html) |
| TW (1) | TW459028B (cg-RX-API-DMAC7.html) |
| WO (1) | WO2000036047A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (92)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6268055B1 (en) * | 1997-12-08 | 2001-07-31 | Ppg Industries Ohio, Inc. | Photochromic epoxy resin coating composition and articles having such a coating |
| US6432544B1 (en) * | 1998-12-18 | 2002-08-13 | Ppg Industries Ohio, Inc. | Aminoplast resin photochromic coating composition and photochromic articles |
| US6506488B1 (en) | 1998-12-18 | 2003-01-14 | Ppg Industries Ohio, Inc. | Aminoplast resin photochromic coating composition and photochromic articles |
| WO2001002449A2 (en) | 1999-07-02 | 2001-01-11 | Ppg Industries Ohio, Inc. | Poly(meth)acrylic photochromic coating |
| US6531076B2 (en) | 2000-02-04 | 2003-03-11 | Ppg Industries Ohio, Inc. | Photochromic organic resin composition |
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| US6547390B1 (en) * | 2000-09-11 | 2003-04-15 | Exxene Corporation | Top stabilized photochromic lens system |
| JP4726172B2 (ja) * | 2001-09-14 | 2011-07-20 | 四国化成工業株式会社 | 熱硬化性樹脂組成物 |
| US8017720B2 (en) * | 2005-12-16 | 2011-09-13 | Ppg Industries Ohio, Inc. | Sulfur-containing oligomers and high index polyurethanes prepared therefrom |
| US20030096935A1 (en) * | 2001-11-16 | 2003-05-22 | Nagpal Vidhu J. | Impact resistant polyureaurethane and method of preparation |
| US20060241273A1 (en) * | 2001-11-16 | 2006-10-26 | Bojkova Nina V | High impact poly (urethane urea) polysulfides |
| US20070142604A1 (en) * | 2005-12-16 | 2007-06-21 | Nina Bojkova | Polyurethanes and sulfur-containing polyurethanes and methods of preparation |
| US7452611B2 (en) * | 2001-12-27 | 2008-11-18 | Transitions Optical, Inc. | Photochromic optical article |
| US7410691B2 (en) * | 2001-12-27 | 2008-08-12 | Ppg Industries Ohio, Inc. | Photochromic optical article |
| US20040021133A1 (en) * | 2002-07-31 | 2004-02-05 | Nagpal Vidhu J. | High refractive index polymerizable composition |
| JP4481172B2 (ja) | 2002-12-05 | 2010-06-16 | 株式会社トクヤマ | コーティング組成物および光学物品 |
| US7009032B2 (en) * | 2002-12-20 | 2006-03-07 | Ppg Industries Ohio, Inc. | Sulfide-containing polythiols |
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| US7189456B2 (en) * | 2004-03-04 | 2007-03-13 | Transitions Optical, Inc. | Photochromic optical article |
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| US7811480B2 (en) * | 2004-03-04 | 2010-10-12 | Transitions Optical, Inc. | Photochromic optical article |
| US8153344B2 (en) * | 2004-07-16 | 2012-04-10 | Ppg Industries Ohio, Inc. | Methods for producing photosensitive microparticles, aqueous compositions thereof and articles prepared therewith |
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| US20060093844A1 (en) * | 2004-10-29 | 2006-05-04 | Conklin Jeanine A | Photochromic coating compositions, methods of making coated articles and articles thereof |
| JP4762984B2 (ja) * | 2005-06-07 | 2011-08-31 | 株式会社トクヤマ | 被覆層を有するプラスチックレンズの製造方法およびレンズ保持台 |
| US7666331B2 (en) * | 2005-08-31 | 2010-02-23 | Transitions Optical, Inc. | Photochromic article |
| US7258437B2 (en) | 2005-09-07 | 2007-08-21 | Transitions Optical, Inc. | Photochromic multifocal optical article |
| US7553925B2 (en) | 2006-05-05 | 2009-06-30 | Ppg Industries Ohio, Inc. | Thioether functional oligomeric polythiols and articles prepared therefrom |
| US20070278461A1 (en) * | 2006-05-31 | 2007-12-06 | Transitions Optical, Inc. | Photochromic materials comprising haloalkyl groups |
| US7481955B2 (en) * | 2006-05-31 | 2009-01-27 | Transitions Optical, Inc. | Photochromic materials comprising metallocenyl groups |
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| US7906214B2 (en) | 2007-01-26 | 2011-03-15 | Transitions Optical, Inc. | Optical elements comprising compatiblizing coatings and methods of making the same |
| EP2116310B1 (en) | 2007-02-02 | 2015-05-20 | Tokuyama Corporation | Method for manufacturing lens having coated layer |
| US7907346B2 (en) | 2007-03-16 | 2011-03-15 | Transitions Optical, Inc. | Photochromic materials and photochromic compositions and articles including the same |
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| US20090326186A1 (en) * | 2008-06-27 | 2009-12-31 | Transitions Optical, Inc. | Mesogen containing compounds |
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| US8431039B2 (en) | 2008-06-27 | 2013-04-30 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US8613868B2 (en) | 2008-06-27 | 2013-12-24 | Transitions Optical, Inc | Mesogenic stabilizers |
| US7910020B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Liquid crystal compositions comprising mesogen containing compounds |
| US8349210B2 (en) | 2008-06-27 | 2013-01-08 | Transitions Optical, Inc. | Mesogenic stabilizers |
| US7910019B2 (en) * | 2008-06-27 | 2011-03-22 | Transitions Optical, Inc. | Mesogen containing compounds |
| US8628685B2 (en) | 2008-06-27 | 2014-01-14 | Transitions Optical, Inc | Mesogen-containing compounds |
| US7911676B2 (en) | 2008-12-16 | 2011-03-22 | Transitions Optical, Inc. | Photochromic optical articles prepared with reversible thermochromic materials |
| US20100232003A1 (en) | 2009-03-13 | 2010-09-16 | Transitions Optical, Inc. | Vision enhancing optical articles |
| US9475901B2 (en) | 2009-12-08 | 2016-10-25 | Transitions Optical, Inc. | Photoalignment materials having improved adhesion |
| US9034219B2 (en) | 2010-12-16 | 2015-05-19 | Transitions Optical, Inc. | Photochromic compounds and compositions |
| US8920928B2 (en) | 2010-12-16 | 2014-12-30 | Transitions Optical, Inc. | Photochromic compounds and compositions |
| US8641933B2 (en) | 2011-09-23 | 2014-02-04 | Ppg Industries Ohio, Inc | Composite crystal colloidal array with photochromic member |
| US9568643B2 (en) | 2012-12-13 | 2017-02-14 | Ppg Industries Ohio, Inc. | Polyurethane urea-containing compositions and optical articles and methods for preparing them |
| US9311545B2 (en) | 2013-09-18 | 2016-04-12 | Blackberry Limited | Multicolor biometric scanning user interface |
| US9418273B2 (en) | 2013-09-18 | 2016-08-16 | Blackberry Limited | Structure for multicolor biometric scanning user interface |
| WO2015077181A1 (en) | 2013-11-20 | 2015-05-28 | Transitions Optical, Inc. | Method of coating a lens and lens support |
| WO2016053662A1 (en) | 2014-09-30 | 2016-04-07 | Transitions Optical, Inc. | Ultraviolet light absorbers |
| EP3345052B1 (en) | 2015-09-03 | 2020-11-04 | Transitions Optical, Inc. | Multilayer photochromic articles |
| US11168223B2 (en) | 2017-09-28 | 2021-11-09 | Sdc Technologies, Inc. | Photochromic article |
| US10866455B2 (en) | 2017-10-19 | 2020-12-15 | Ppg Industries Ohio, Inc. | Display devices including photochromic-dichroic compounds and dichroic compounds |
| US12222587B2 (en) | 2018-03-22 | 2025-02-11 | Tokuyama Corporation | Method of producing a plastic lens having a coating layer |
| CN121241281A (zh) | 2023-06-09 | 2025-12-30 | 全视线光学有限公司 | 光致变色镜片 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3361706A (en) * | 1964-03-06 | 1968-01-02 | American Cyanamid Co | Control of the photochromic return rate of (arylazo) thioformic arylhydrazidates |
| US4720356A (en) * | 1982-03-22 | 1988-01-19 | American Optical Corporation | Photochromic composition resistant to fatigue |
| DE3602215A1 (de) * | 1986-01-25 | 1987-07-30 | Hoechst Ag | Photopolymerisierbares gemisch und dieses enthaltendes photopolymerisierbares aufzeichnungsmaterial |
| US4873029A (en) * | 1987-10-30 | 1989-10-10 | Blum Ronald D | Method for manufacturing lenses |
| US4931220A (en) * | 1987-11-24 | 1990-06-05 | Ppg Industries, Inc. | Organic photochromic pigment particulates |
| ES2143511T3 (es) * | 1992-09-25 | 2000-05-16 | Ppg Ind Ohio Inc | Composiciones fotocromaticas con resistencia a la fatiga, mejorada. |
| JP2755537B2 (ja) * | 1992-11-27 | 1998-05-20 | 株式会社トクヤマ | 重合性組成物 |
| JPH07258585A (ja) * | 1994-03-18 | 1995-10-09 | Nippon Paint Co Ltd | 水性塗料組成物及び色彩可変塗膜 |
| US5618586A (en) * | 1994-03-29 | 1997-04-08 | Ppg Industries, Inc. | N-alkoxymethyl (meth)acrylamide functional polymers and their use in self-crosslinkable coating compositions |
| US5645767A (en) * | 1994-11-03 | 1997-07-08 | Transitions Optical, Inc. | Photochromic indeno-fused naphthopyrans |
| US5658501A (en) * | 1995-06-14 | 1997-08-19 | Transitions Optical, Inc. | Substituted naphthopyrans |
| US5770115A (en) * | 1996-04-19 | 1998-06-23 | Ppg Industries, Inc. | Photochromic naphthopyran compositions of improved fatigue resistance |
| AU718471B2 (en) * | 1997-02-21 | 2000-04-13 | Ppg Industries Ohio, Inc. | Photochromic polyurethane coating and articles having such a coating |
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1998
- 1998-12-14 US US09/211,249 patent/US6060001A/en not_active Expired - Lifetime
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- 1999-12-10 EP EP99966127A patent/EP1147161B1/en not_active Expired - Lifetime
- 1999-12-10 DE DE69911065T patent/DE69911065T2/de not_active Expired - Lifetime
- 1999-12-10 BR BRPI9917067-1A patent/BR9917067B1/pt not_active IP Right Cessation
- 1999-12-10 JP JP2000588300A patent/JP4451988B2/ja not_active Expired - Lifetime
- 1999-12-10 AU AU21744/00A patent/AU744068B2/en not_active Expired
- 1999-12-10 WO PCT/US1999/029389 patent/WO2000036047A1/en not_active Ceased
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2000
- 2000-01-21 TW TW088121895A patent/TW459028B/zh active
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|---|---|
| TW459028B (en) | 2001-10-11 |
| BR9917067B1 (pt) | 2009-05-05 |
| DE69911065D1 (de) | 2003-10-09 |
| EP1147161A1 (en) | 2001-10-24 |
| WO2000036047A1 (en) | 2000-06-22 |
| EP1147161B1 (en) | 2003-09-03 |
| JP2002532743A (ja) | 2002-10-02 |
| AU744068B2 (en) | 2002-02-14 |
| US6060001A (en) | 2000-05-09 |
| BR9917067A (pt) | 2002-05-14 |
| AU2174400A (en) | 2000-07-03 |
| JP4451988B2 (ja) | 2010-04-14 |
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