KR100736992B1 - 고충격 폴리(우레탄 우레아) 폴리설파이드 - Google Patents
고충격 폴리(우레탄 우레아) 폴리설파이드 Download PDFInfo
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- KR100736992B1 KR100736992B1 KR1020057011657A KR20057011657A KR100736992B1 KR 100736992 B1 KR100736992 B1 KR 100736992B1 KR 1020057011657 A KR1020057011657 A KR 1020057011657A KR 20057011657 A KR20057011657 A KR 20057011657A KR 100736992 B1 KR100736992 B1 KR 100736992B1
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- sulfur
- limiting embodiment
- polyureaurethane
- mixtures
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- 239000005077 polysulfide Substances 0.000 title claims description 4
- 229920001021 polysulfide Polymers 0.000 title claims description 4
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- 229920003226 polyurethane urea Polymers 0.000 title 1
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 65
- 238000000034 method Methods 0.000 claims abstract description 61
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- 239000011593 sulfur Substances 0.000 claims abstract description 57
- 229920000162 poly(ureaurethane) Polymers 0.000 claims abstract description 53
- 239000000203 mixture Substances 0.000 claims description 129
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- 150000001412 amines Chemical class 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
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- 125000001931 aliphatic group Chemical group 0.000 claims description 21
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- 239000000047 product Substances 0.000 claims description 20
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- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical group CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 5
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- RQEOBXYYEPMCPJ-UHFFFAOYSA-N 4,6-diethyl-2-methylbenzene-1,3-diamine Chemical compound CCC1=CC(CC)=C(N)C(C)=C1N RQEOBXYYEPMCPJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- VIOMIGLBMQVNLY-UHFFFAOYSA-N 4-[(4-amino-2-chloro-3,5-diethylphenyl)methyl]-3-chloro-2,6-diethylaniline Chemical group CCC1=C(N)C(CC)=CC(CC=2C(=C(CC)C(N)=C(CC)C=2)Cl)=C1Cl VIOMIGLBMQVNLY-UHFFFAOYSA-N 0.000 claims description 2
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical group C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 claims description 2
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical class N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims 8
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Abstract
Description
Claims (98)
- (a) OH-함유 물질, SH-함유 물질 및 이들의 혼합물로부터 선택되는 하나 이상의 수소-함유 물질 및 폴리아이소(티오)사이아네이트로부터 수득되는 폴리우레탄 예비중합체;(b) 하나 이상의 에피설파이드-함유 물질; 및(c) 아민-함유 경화제의 반응 생성물을 포함하고,적어도 부분적으로 경화될 때 1.57 이상의 굴절률, 35 이상의 아베 수(Abbe number) 및 1.3g/cm3 미만의 밀도를 갖는 황-함유 폴리우레아우레탄.
- 삭제
- 삭제
- 삭제
- 삭제
- 삭제
- 제 1 항에 있어서,2J 이상의 충격 강도를 추가로 포함하는 황-함유 폴리우레아우레탄.
- 삭제
- 삭제
- 제 1 항에 있어서,상기 폴리아이소(티오)사이아네이트가 폴리아이소사이아네이트, 폴리아이소티오사이아네이트 및 이들의 혼합물로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 10 항에 있어서,상기 폴리아이소(티오)사이아네이트가 지방족 폴리아이소사이아네이트, 지환족 폴리아이소사이아네이트, 방향족 폴리아이소사이아네이트, 및 이들의 혼합물로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 11 항에 있어서,상기 폴리아이소(티오)사이아네이트가 지방족 다이아이소사이아네이트, 지환족 다이아이소사이아네이트, 방향족 다이아이소사이아네이트, 이들의 환상 이량체 및 환상 삼량체, 및 이들의 혼합물로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 11 항에 있어서,상기 폴리아이소(티오)사이아네이트가 다이사이클로헥실메테인 다이아이소사이아네이트 및 그의 이성질체 혼합물로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 11 항에 있어서,상기 폴리아이소(티오)사이아네이트가 4,4'-메틸렌비스(사이클로헥실 아이소사이아네이트)의 트랜스,트랜스 이성질체로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 11 항에 있어서,상기 폴리아이소(티오)사이아네이트가 3-아이소사이아네이토-메틸-3,5,5-트라이메틸 사이클로헥실 아이소사이아네이트; 메타-테트라메틸자일렌 다이아이소사이아네이트(1,3-비스(1-아이소사이아네이토-1-메틸에틸)-벤젠) 및 이들의 혼합물로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 1 항에 있어서,상기 수소-함유 물질이 폴리올, 폴리 티올, 및 하이드록실 작용기와 티올 작용기를 둘 다 갖는 물질로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 16 항에 있어서,상기 수소-함유 물질이 폴리에스터 폴리올, 폴리카프로락톤 폴리올, 폴리에터 폴리올, 폴리카본에이트 폴리올 및 이들의 혼합물로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 1 항에 있어서,상기 수소-함유 물질이 200 내지 32,000의 중량 평균 분자량을 갖는 황-함유 폴리우레아우레탄.
- 제 18 항에 있어서,상기 수소-함유 물질이 약 2,000 내지 15,000의 중량 평균 분자량을 갖는 황-함유 폴리우레아우레탄.
- 제 1 항에 있어서,상기 수소-함유 물질이 폴리에터 폴리올로부터 유도된 블록 잔기를 포함하는 황-함유 폴리우레아우레탄.
- 제 20 항에 있어서,상기 폴리에터 폴리올이 하기 화학식 XXXI'으로 나타내어지는 황-함유 폴리우레아우레탄:화학식 XXXI'H-(O-CRRCRR-Yn)a-(CRRCRR-Yn-O)b-(CRRCRR-Yn-O)c-H상기 식에서,R은 수소 또는 C1-C6 알킬일 수 있고;Y는 CH2일 수 있고;n은 0 내지 6의 정수일 수 있으며;a, b 및 c는 각각 0 내지 300의 정수일 수 있으며, 폴리올의 중량 평균 분자량이 32,000을 초과하지 않도록 선택된다.
- 제 16 항에 있어서,상기 폴리티올이 지방족 폴리티올, 지환족 폴리티올, 방향족 폴리티올, 중합체 폴리티올, 에터 결합을 함유하는 폴리티올, 설파이드 결합을 함유하는 폴리티올, 폴리설파이드 결합을 함유하는 폴리티올로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 1 항에 있어서,상기 예비중합체가 2.0 이상 5.5 미만의 NCO/OH 당량 비를 갖는 황-함유 폴리우레아우레탄.
- 제 25 항에 있어서,상기 아민-함유 경화제가 4,4'-메틸렌비스(3-클로로-2,6-다이에틸아닐린)인 황-함유 폴리우레아우레탄.
- 제 1 항에 있어서,상기 아민-함유 경화제가 2,4-다이아미노-3,5-다이에틸-톨루엔; 2,6-다이아미노-3,5-다이에틸-톨루엔 및 이들의 혼합물로부터 선택되는 황-함유 폴리우레아우레탄.
- 제 1 항에 있어서,상기 아민-함유 경화제가 1.0 NCO/0.60 NH2 내지 1.0 NCO/1.20 NH2의 NCO/NH2 당량 비로 존재하는 황-함유 폴리우레아우레탄.
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- (a) 폴리올, 폴리 티올, 및 하이드록실 작용기와 티올 작용기를 둘 다 갖는 물질로부터 선택되는 하나 이상의 수소-함유 물질과 폴리아이소(티오)사이아네이트를 반응시켜 폴리우레탄 예비중합체를 형성하는 단계;(b) 상기 예비중합체를 하나 이상의 에피설파이드-함유 물질과 반응시키는 단계; 및(c) 아민-함유 경화제와 단계 (b)로부터의 혼합물을 반응시키는 단계를 포함하고,적어도 부분적으로 경화될 때 1.57 이상의 굴절률, 35 이상의 아베 수 및 1.3g/cm3 미만의 밀도를 갖는 황-함유 폴리우레아우레탄의 제조 방법.
- 제 75 항에 있어서,상기 황-함유 폴리우레아우레탄이 2J 이상의 충격 강도를 추가로 갖는 제조 방법.
- 제 75 항 또는 제 76 항에 있어서,상기 폴리아이소(티오)사이아네이트, 하나 이상의 수소-함유 물질, 에피설파이드-함유 물질, 아민-함유 경화제, 예비중합체의 NCO/OH 당량비, 및 NCO/NH2 당량비가 제 10 항 내지 제 28 항 중 어느 한 항에 정의된 바와 같은 제조 방법.
- 제 1 항, 제 7항 및 제 10 항 내지 제 28 항 중 어느 한 항에 따른 황-함유 폴리우레아우레탄을 포함하는 광학 제품.
- 제 78 항에 있어서,광변색성인 광학 제품.
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Applications Claiming Priority (4)
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US10/725,023 US20040138401A1 (en) | 2002-11-05 | 2003-12-02 | High impact poly (urethane urea) polysulfides |
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Families Citing this family (82)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20050282991A1 (en) * | 2001-11-16 | 2005-12-22 | Bojkova Nina V | High impact poly (urethane urea) polysulfides |
US8017720B2 (en) * | 2005-12-16 | 2011-09-13 | Ppg Industries Ohio, Inc. | Sulfur-containing oligomers and high index polyurethanes prepared therefrom |
US20070142606A1 (en) * | 2005-12-16 | 2007-06-21 | Bojkova Nina V | Polyurethane (ureas) and sulfur-containing polyurethane (ureas) methods of preparation |
US20070142604A1 (en) * | 2005-12-16 | 2007-06-21 | Nina Bojkova | Polyurethanes and sulfur-containing polyurethanes and methods of preparation |
US20070142602A1 (en) * | 2005-12-16 | 2007-06-21 | Rukavina Thomas G | Polyurethanes and sulfur-containing polyurethanes and methods of preparation |
US20070142603A1 (en) * | 2005-12-16 | 2007-06-21 | Rukavina Thomas G | Polyurethane(urea) and sulfur-containing polyurethane(urea) and methods of preparation |
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 |
US20040021133A1 (en) * | 2002-07-31 | 2004-02-05 | Nagpal Vidhu J. | High refractive index polymerizable composition |
US7009032B2 (en) * | 2002-12-20 | 2006-03-07 | Ppg Industries Ohio, Inc. | Sulfide-containing polythiols |
EP1775315B1 (en) * | 2004-06-23 | 2012-02-22 | Mitsubishi Gas Chemical Company, Inc. | Polymerizable composition |
JP4595706B2 (ja) * | 2004-06-23 | 2010-12-08 | 三菱瓦斯化学株式会社 | 重合性組成物 |
US20070251421A1 (en) * | 2004-09-01 | 2007-11-01 | Rukavina Thomas G | Powder coatings prepared from polyurethanes and poly(ureaurethane)s, coated articles and methods of making the same |
US8927675B2 (en) | 2004-09-01 | 2015-01-06 | Ppg Industries Ohio, Inc. | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
US9598527B2 (en) * | 2004-09-01 | 2017-03-21 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US9464169B2 (en) | 2004-09-01 | 2016-10-11 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US8207286B2 (en) | 2004-09-01 | 2012-06-26 | Ppg Industries Ohio, Inc | Methods for preparing polyurethanes |
US8734951B2 (en) * | 2004-09-01 | 2014-05-27 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US11149107B2 (en) | 2004-09-01 | 2021-10-19 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US8889815B2 (en) * | 2004-09-01 | 2014-11-18 | Ppg Industries Ohio, Inc. | Reinforced polyurethanes and poly(ureaurethane)s, methods of making the same and articles prepared therefrom |
US20070148471A1 (en) * | 2004-09-01 | 2007-06-28 | Rukavina Thomas G | Impact resistant polyurethane and poly(ureaurethane) articles and methods of making the same |
US11248083B2 (en) | 2004-09-01 | 2022-02-15 | Ppg Industries Ohio, Inc. | Aircraft windows |
US8399094B2 (en) * | 2004-09-01 | 2013-03-19 | Ppg Industries Ohio, Inc. | Multilayer laminated articles including polyurethane and/or poly(ureaurethane) layers and methods of making the same |
US20070173601A1 (en) * | 2004-09-01 | 2007-07-26 | Rukavina Thomas G | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US20090280709A1 (en) | 2004-09-01 | 2009-11-12 | Ppg Industries Ohio, Inc. | Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same |
US11591436B2 (en) | 2004-09-01 | 2023-02-28 | Ppg Industries Ohio, Inc. | Polyurethane article and methods of making the same |
US20090280329A1 (en) | 2004-09-01 | 2009-11-12 | Ppg Industries Ohio, Inc. | Polyurethanes, Articles and Coatings Prepared Therefrom and Methods of Making the Same |
US8604153B2 (en) * | 2004-09-01 | 2013-12-10 | Ppg Industries Ohio, Inc. | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
US20070167601A1 (en) * | 2004-09-01 | 2007-07-19 | Rukavina Thomas G | Polyurethanes prepared from polycarbonate polyols, articles and coatings prepared therefrom and methods of making the same |
US8399559B2 (en) * | 2004-09-01 | 2013-03-19 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US8933166B2 (en) * | 2004-09-01 | 2015-01-13 | Ppg Industries Ohio, Inc. | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
US20070149749A1 (en) * | 2004-09-01 | 2007-06-28 | Rukavina Thomas G | Polyurethanes prepared from polycarbonate polyols, articles and coatings prepared therefrom and methods of making the same |
US20070225468A1 (en) * | 2004-09-01 | 2007-09-27 | Rukavina Thomas G | Polyurethanes prepared from polyester polyols and/or polycaprolactone polyols, articles and coatings prepared therefrom and methods of making the same |
US8859680B2 (en) * | 2004-09-01 | 2014-10-14 | Ppg Industries Ohio, Inc | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
US20070167600A1 (en) * | 2004-09-01 | 2007-07-19 | Rukavina Thomas G | Polyurethanes prepared from polycaprolactone polyols, articles and coatings prepared therefrom and methods of making the same |
US11008418B2 (en) | 2004-09-01 | 2021-05-18 | Ppg Industries Ohio, Inc. | Polyurethanes, articles and coatings prepared therefrom and methods of making the same |
US8653220B2 (en) * | 2004-09-01 | 2014-02-18 | Ppg Industries Ohio, Inc. | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
US8349986B2 (en) * | 2004-09-01 | 2013-01-08 | Ppg Industries Ohio, Inc. | Poly(ureaurethane)s, articles and coatings prepared therefrom and methods of making the same |
EP2236536B1 (en) * | 2005-12-16 | 2012-11-28 | PPG Industries Ohio, Inc. | Polyurethane (ureas) and methods of preparation |
CN102030880A (zh) * | 2006-05-05 | 2011-04-27 | Ppg工业俄亥俄公司 | 由硫醚官能的低聚多硫醇制备的组合物和制品 |
US8623989B1 (en) * | 2006-05-05 | 2014-01-07 | PRC De Soto International, Inc. | Polyurea/polythiourea coatings |
EP2065415B1 (en) * | 2006-08-31 | 2019-03-06 | Hoya Corporation | Method for producing polythiourethane resin |
US7986450B2 (en) * | 2006-09-22 | 2011-07-26 | E Ink Corporation | Electro-optic display and materials for use therein |
US7879955B2 (en) * | 2007-05-01 | 2011-02-01 | Rao Chandra B | Compositions including a polythioether |
US20090081463A1 (en) * | 2007-09-21 | 2009-03-26 | Ppg Industries Ohio, Inc. | Tinted article having a high refractive index |
JP4941942B2 (ja) * | 2008-01-30 | 2012-05-30 | 日立化成工業株式会社 | 含硫黄多分岐化合物及び不飽和基含有多分岐化合物 |
AU2011286681B2 (en) * | 2010-08-06 | 2014-01-16 | Tokuyama Corporation | Photochromic composition |
US8848288B2 (en) | 2011-03-04 | 2014-09-30 | Ppg Industries Ohio, Inc. | Composite optical articles |
KR101570920B1 (ko) | 2011-06-23 | 2015-11-20 | 미쓰이 가가쿠 가부시키가이샤 | 중합성 조성물 |
JP5888895B2 (ja) * | 2011-08-02 | 2016-03-22 | 株式会社トクヤマ | フォトクロミック積層体、及びその製造方法 |
WO2013099640A1 (ja) * | 2011-12-26 | 2013-07-04 | 株式会社トクヤマ | フォトクロミック組成物 |
US9568643B2 (en) | 2012-12-13 | 2017-02-14 | Ppg Industries Ohio, Inc. | Polyurethane urea-containing compositions and optical articles and methods for preparing them |
TWI543995B (zh) * | 2013-07-08 | 2016-08-01 | 旭化成化學股份有限公司 | 經改質之樹脂及樹脂組成物 |
CN108690180B (zh) * | 2013-12-10 | 2021-07-23 | Ppg工业俄亥俄公司 | 含聚氨酯脲的组合物和光学制品及其制备方法 |
US10344116B2 (en) | 2014-07-08 | 2019-07-09 | Mitsui Chemicals, Inc. | Polymerizable composition for optical material and use thereof |
CN106471030B (zh) * | 2014-07-08 | 2019-11-08 | 三井化学株式会社 | 光学材料用聚合性组合物及其用途 |
HUE053430T2 (hu) * | 2015-03-10 | 2021-07-28 | Tokuyama Corp | Eljárás fotokróm keményített test elõállítására |
EP3417031B1 (en) * | 2016-02-16 | 2020-04-15 | Suzhou Rainbow Materials Co., Ltd. | Polythiourethane matrix containing nanocrystals |
JP2018070865A (ja) | 2016-10-25 | 2018-05-10 | 三井化学株式会社 | 光学材料用重合性組成物、該組成物から得られた光学材料及びその製造方法 |
CN107540811B (zh) * | 2017-08-08 | 2020-06-09 | 海泉风雷新能源发电股份有限公司 | 一种三聚氰胺接枝改性的聚氨酯塑料及其制备方法 |
CN111788245B (zh) * | 2018-03-16 | 2022-05-03 | 三井化学株式会社 | 光学材料用聚合性组合物、光学材料用聚合性组合物的制造方法及光学物品的制造方法 |
JP7332251B2 (ja) | 2018-06-28 | 2023-08-23 | ホヤ レンズ タイランド リミテッド | 光学部材用重合性組成物 |
US11866648B2 (en) * | 2019-01-30 | 2024-01-09 | Mitsui Chemicals, Inc. | Process for producing polymerizable composition for optical materials |
FR3109313B1 (fr) | 2020-04-15 | 2022-11-25 | Oreal | Procede de traitement de matieres keratiniques mettant en oeuvre un polymere acrylique d’anhydride en dispersion huileuse et d’un compose hydroxyle et/ou thiole |
WO2022136110A1 (fr) | 2020-12-23 | 2022-06-30 | L'oreal | Composition cosmétique comprenant des particules polymériques à base de fonctions acétoacétates |
JP2024502278A (ja) | 2020-12-23 | 2024-01-18 | ロレアル | アセトアセテート官能基(functions)系のコポリマーを含む化粧用組成物 |
FR3117794B1 (fr) | 2020-12-23 | 2023-07-28 | Oreal | Dispersion aqueuse d’un copolymère spécifique et ses applications cosmétiques |
WO2022136114A1 (fr) | 2020-12-23 | 2022-06-30 | L'oreal | Dispersion aqueuse d'un copolymère spécifique et ses applications cosmétiques |
FR3117852B1 (fr) | 2020-12-23 | 2023-06-23 | Oreal | Composition cosmétique comprenant un copolymère à base de fonctions acétoacétates |
FR3117856B1 (fr) | 2020-12-23 | 2024-05-10 | Oreal | Composition cosmétique comprenant un copolymère séquencé à base de fonctions acétoacétates |
FR3117854B1 (fr) | 2020-12-23 | 2024-03-15 | Oreal | Composition cosmétique comprenant des particules polymériques à base de fonctions acétoacétates |
FR3130573A1 (fr) | 2021-12-17 | 2023-06-23 | L'oreal | Composition cosmetique comprenant un copolymère à motifs alkyl-azlactone et ses utilisations |
FR3130611A1 (fr) | 2021-12-20 | 2023-06-23 | L'oreal | Copolymère polyhydroxyalcanoate à groupe acétoacétate, composition le contenant et son utilisation en cosmétique |
WO2023167262A1 (ja) * | 2022-03-01 | 2023-09-07 | 三井化学株式会社 | 樹脂、成形体、光学材料、レンズ、2,5-ビス(イソシアナトメチル)フラン及び重合性組成物 |
FR3142898A1 (fr) | 2022-12-13 | 2024-06-14 | L'oreal | Procédé de traitement des matières kératiniques mettant en œuvre au moins un composé polysaccharide à fonctions acétoacétates |
FR3142894A1 (fr) | 2022-12-13 | 2024-06-14 | L'oreal | Procédé de traitement des fibres kératiniques mettant en œuvre un composé issu de la condensation de poly(thi)ol, et d’acétoacétate, et un agent réticulant |
FR3142893A1 (fr) | 2022-12-13 | 2024-06-14 | L'oreal | Procédé de traitement des matières kératiniques mettant en œuvre un composé issu de la condensation de poly(thi)ol et d’acétoacétate et un agent réticulant |
FR3143997A1 (fr) | 2022-12-27 | 2024-06-28 | L'oreal | Procédé de traitement des matières kératiniques mettant en œuvre au moins un composé alcoxysilane à fonctions acétoacétates et au moins un agent réticulant |
FR3143985A1 (fr) | 2022-12-27 | 2024-06-28 | L'oreal | Procédé de traitement des matières kératiniques mettant en œuvre au moins une huile à fonctions acétoacétates et au moins un agent réticulant |
FR3144134A1 (fr) | 2022-12-27 | 2024-06-28 | L'oreal | Procédé de traitement des fibres kératiniques mettant en œuvre au moins une huile à fonctions acétoacétates |
FR3144001A1 (fr) | 2022-12-27 | 2024-06-28 | L'oreal | Procédé de traitement des fibres kératiniques mettant en œuvre au moins un (co)polymère d’alcool polyvinylique (PVA) à fonctions acétoacétates |
FR3144000A1 (fr) | 2022-12-27 | 2024-06-28 | L'oreal | Procédé de traitement des matières kératiniques mettant en œuvre au moins un (co)polymère d’alcool polyvinylique (PVA) à fonctions acétoacétates et au moins un agent réticulant |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000014137A1 (en) * | 1998-09-02 | 2000-03-16 | Simula, Inc. | Impact resistant polyurethane and method of manufacture thereof |
WO2001036508A1 (en) * | 1999-11-18 | 2001-05-25 | Ppg Industries Ohio, Inc. | Method of preparing an optical polymerizate |
WO2003042270A1 (en) * | 2001-11-14 | 2003-05-22 | Essilor International Compagnie Generale D'optique | High refractive index and high impact resistant polythiourethane/urea material, method of manufacturing same and its use in the optical field |
WO2003044070A1 (en) * | 2001-11-16 | 2003-05-30 | Ppg Industries Ohio, Inc. | High impact poly(urethane urea) polysulfides |
EP1384736A1 (en) * | 2001-03-21 | 2004-01-28 | Hoya Corporation | Transparent molded objects, optical member, plastic lens, and processes for producing these |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2644007A (en) * | 1951-10-08 | 1953-06-30 | Du Pont | Preparation of polyamine hydrochlorides and polyisocyanates |
US2680127A (en) * | 1952-01-02 | 1954-06-01 | Monsanto Chemicals | Method of making organic isocyanates |
US2965650A (en) * | 1955-06-08 | 1960-12-20 | Du Pont | Keto-substituted dithiacycloparaffins of 7 to 9 annular atoms and their preparation |
US3361706A (en) * | 1964-03-06 | 1968-01-02 | American Cyanamid Co | Control of the photochromic return rate of (arylazo) thioformic arylhydrazidates |
US3567605A (en) * | 1966-03-30 | 1971-03-02 | Ralph S Becker | Photochemical process |
GB1186987A (en) * | 1967-08-30 | 1970-04-08 | Fuji Photo Film Co Ltd | Photochromic Compounds |
JPS4948631B1 (ko) * | 1968-10-28 | 1974-12-23 | ||
US4166043A (en) * | 1974-12-23 | 1979-08-28 | American Optical Corporation | Stabilized photochromic materials |
US4367170A (en) * | 1975-01-24 | 1983-01-04 | American Optical Corporation | Stabilized photochromic materials |
US4160853A (en) * | 1976-04-28 | 1979-07-10 | Ppg Industries, Inc. | Catalyst for making polycarbonate diols for use in polycarbonate urethanes |
US4215010A (en) * | 1978-09-08 | 1980-07-29 | American Optical Corporation | Photochromic compounds |
US4342668A (en) * | 1978-09-08 | 1982-08-03 | American Optical Corporation | Photochromic compounds |
US4637698A (en) * | 1983-11-04 | 1987-01-20 | Ppg Industries, Inc. | Photochromic compound and articles containing the same |
US4880667A (en) * | 1985-09-24 | 1989-11-14 | Ppg Industries, Inc. | Photochromic plastic article and method for preparing same |
GB8611837D0 (en) * | 1986-05-15 | 1986-06-25 | Plessey Co Plc | Photochromic spiropyran compounds |
GB8614680D0 (en) * | 1986-06-17 | 1986-07-23 | Plessey Co Plc | Photoreactive lenses |
US4816584A (en) * | 1986-11-12 | 1989-03-28 | Ppg Industries, Inc. | Photochromic spiro(indoline)benzoxazines |
US4931219A (en) * | 1987-07-27 | 1990-06-05 | Ppg Industries, Inc. | Photochromic compound and articles containing the same |
US4931220A (en) * | 1987-11-24 | 1990-06-05 | Ppg Industries, Inc. | Organic photochromic pigment particulates |
US5191055A (en) * | 1988-12-22 | 1993-03-02 | Mitsui Toatsu Chemicals, Inc. | Mercapto compound, a high refractive index resin and lens and a process for preparing them |
US5066818A (en) * | 1990-03-07 | 1991-11-19 | Ppg Industries, Inc. | Photochromic naphthopyran compounds |
JP2811353B2 (ja) * | 1990-07-06 | 1998-10-15 | ゼリア新薬工業株式会社 | 炎症性腸疾患予防・治療剤 |
US5225472A (en) * | 1992-05-19 | 1993-07-06 | Courtaulds Aerospace, Inc. | Low viscosity polythiol and method therefor |
US5274132A (en) * | 1992-09-30 | 1993-12-28 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
US5405958A (en) * | 1992-12-21 | 1995-04-11 | Transitions Optical, Inc. | Photochromic spiro(indoline)naphthoxazine compounds |
WO1994020869A1 (en) * | 1993-03-12 | 1994-09-15 | Ppg Industries, Inc. | Novel benzopyrans |
US5384077A (en) * | 1993-06-21 | 1995-01-24 | Transitions Optical, Inc. | Photochromic naphthopyran compounds |
US5466398A (en) * | 1993-06-21 | 1995-11-14 | Transitions Optical, Inc. | Photochromic substituted naphthopyran compounds |
US5693738A (en) * | 1994-04-08 | 1997-12-02 | Mitsui Toatsu Chemicals, Inc. | Composition for urethane-base plastic lens, urethane-base plastic lens obtained from the composition, and process for the production of the plastic lens |
US5908876A (en) * | 1996-04-19 | 1999-06-01 | Mitsui Chemicals, Inc. | Optical resin composition comprising a thiourethane prepolymer and use thereof |
US6509418B1 (en) * | 1997-02-19 | 2003-01-21 | Prc-Desoto International, Inc. | Sealants and potting formulations including mercapto-terminated polymers produced by the reaction of a polythiol and polyvinyl ether monomer |
EP0963390B1 (en) * | 1997-02-21 | 2003-05-02 | PPG Industries Ohio, Inc. | Photochromic polyurethane coating and articles having such a coating |
JP2001131257A (ja) * | 1999-11-09 | 2001-05-15 | Mitsubishi Gas Chem Co Inc | 樹脂用組成物 |
US6486269B2 (en) | 2000-03-09 | 2002-11-26 | Pbt Brands, Inc. | Curable polythiol-cyclopolyene sealant compounds |
US6960640B2 (en) * | 2001-08-30 | 2005-11-01 | Mitsubishi Gas Chemical Co., Ltd. | Composition for optical material |
-
2003
- 2003-12-02 US US10/725,023 patent/US20040138401A1/en not_active Abandoned
- 2003-12-03 MX MXPA05006213A patent/MXPA05006213A/es active IP Right Grant
- 2003-12-03 EP EP03814645.2A patent/EP1581574B1/en not_active Expired - Lifetime
- 2003-12-03 AU AU2003297632A patent/AU2003297632A1/en not_active Abandoned
- 2003-12-03 CA CA002502710A patent/CA2502710A1/en not_active Abandoned
- 2003-12-03 BR BR0316910-3A patent/BR0316910A/pt not_active IP Right Cessation
- 2003-12-03 JP JP2005508552A patent/JP4109287B2/ja not_active Expired - Fee Related
- 2003-12-03 DE DE60314448T patent/DE60314448T2/de not_active Expired - Lifetime
- 2003-12-03 ES ES03808428T patent/ES2288638T3/es not_active Expired - Lifetime
- 2003-12-03 KR KR1020057011657A patent/KR100736992B1/ko active IP Right Grant
- 2003-12-03 EP EP11001940A patent/EP2325233A3/en not_active Withdrawn
- 2003-12-03 SG SG2005037163A patent/SG113724A1/en unknown
- 2003-12-03 AU AU2003303554A patent/AU2003303554B2/en not_active Ceased
- 2003-12-03 IN IN1409KO2005 patent/IN222382B/en unknown
- 2003-12-03 WO PCT/US2003/038436 patent/WO2004060951A1/en active Application Filing
- 2003-12-03 MX MXPA05006212A patent/MXPA05006212A/es active IP Right Grant
- 2003-12-03 BR BR0316909-0A patent/BR0316909A/pt not_active IP Right Cessation
- 2003-12-03 WO PCT/US2003/038319 patent/WO2004060971A2/en active IP Right Grant
- 2003-12-03 CA CA002500379A patent/CA2500379A1/en not_active Abandoned
- 2003-12-03 KR KR1020057011255A patent/KR100685534B1/ko not_active IP Right Cessation
- 2003-12-03 EP EP03808428A patent/EP1572778B1/en not_active Expired - Fee Related
- 2003-12-03 JP JP2005508549A patent/JP4431539B2/ja not_active Expired - Fee Related
- 2003-12-16 MY MYPI20034833A patent/MY148490A/en unknown
- 2003-12-17 TW TW092135768A patent/TWI268944B/zh not_active IP Right Cessation
-
2006
- 2006-05-16 HK HK06105636A patent/HK1088620A1/xx not_active IP Right Cessation
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000014137A1 (en) * | 1998-09-02 | 2000-03-16 | Simula, Inc. | Impact resistant polyurethane and method of manufacture thereof |
WO2001036508A1 (en) * | 1999-11-18 | 2001-05-25 | Ppg Industries Ohio, Inc. | Method of preparing an optical polymerizate |
WO2001036507A1 (en) * | 1999-11-18 | 2001-05-25 | Ppg Industries Ohio, Inc. | Method of preparing an optical polymerizate |
EP1384736A1 (en) * | 2001-03-21 | 2004-01-28 | Hoya Corporation | Transparent molded objects, optical member, plastic lens, and processes for producing these |
WO2003042270A1 (en) * | 2001-11-14 | 2003-05-22 | Essilor International Compagnie Generale D'optique | High refractive index and high impact resistant polythiourethane/urea material, method of manufacturing same and its use in the optical field |
WO2003044070A1 (en) * | 2001-11-16 | 2003-05-30 | Ppg Industries Ohio, Inc. | High impact poly(urethane urea) polysulfides |
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