KR101214711B1 - 폴리우레아 및 인-함유 폴리올을 포함하는 코팅 조성물 - Google Patents
폴리우레아 및 인-함유 폴리올을 포함하는 코팅 조성물 Download PDFInfo
- Publication number
- KR101214711B1 KR101214711B1 KR1020107028406A KR20107028406A KR101214711B1 KR 101214711 B1 KR101214711 B1 KR 101214711B1 KR 1020107028406 A KR1020107028406 A KR 1020107028406A KR 20107028406 A KR20107028406 A KR 20107028406A KR 101214711 B1 KR101214711 B1 KR 101214711B1
- Authority
- KR
- South Korea
- Prior art keywords
- isocyanate
- phosphorus
- composition
- component
- coating composition
- 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.)
- Expired - Fee Related
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- 239000008199 coating composition Substances 0.000 title claims abstract description 93
- 229920005862 polyol Polymers 0.000 title claims abstract description 66
- 150000003077 polyols Chemical class 0.000 title claims abstract description 65
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 63
- 239000011574 phosphorus Substances 0.000 title claims abstract description 63
- 229920002396 Polyurea Polymers 0.000 title claims abstract description 34
- 239000012948 isocyanate Substances 0.000 claims abstract description 146
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 142
- 150000001412 amines Chemical class 0.000 claims abstract description 63
- 239000011541 reaction mixture Substances 0.000 claims abstract description 60
- 239000000463 material Substances 0.000 claims abstract description 38
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- 239000002253 acid Substances 0.000 claims description 34
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- 239000003063 flame retardant Substances 0.000 claims description 28
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 25
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- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 16
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- 239000010439 graphite Substances 0.000 claims description 9
- 229910002804 graphite Inorganic materials 0.000 claims description 9
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 9
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- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 8
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
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- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 claims description 4
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 claims description 4
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- 239000005696 Diammonium phosphate Substances 0.000 claims description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 2
- PQYJRMFWJJONBO-UHFFFAOYSA-N Tris(2,3-dibromopropyl) phosphate Chemical compound BrCC(Br)COP(=O)(OCC(Br)CBr)OCC(Br)CBr PQYJRMFWJJONBO-UHFFFAOYSA-N 0.000 claims description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 2
- 229910000410 antimony oxide Inorganic materials 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- IUTYMBRQELGIRS-UHFFFAOYSA-N boric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OB(O)O.NC1=NC(N)=NC(N)=N1 IUTYMBRQELGIRS-UHFFFAOYSA-N 0.000 claims description 2
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 claims description 2
- 229910000388 diammonium phosphate Inorganic materials 0.000 claims description 2
- 235000019838 diammonium phosphate Nutrition 0.000 claims description 2
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 235000011180 diphosphates Nutrition 0.000 claims description 2
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 claims description 2
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical class [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 claims description 2
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 claims description 2
- XFZRQAZGUOTJCS-UHFFFAOYSA-N phosphoric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OP(O)(O)=O.NC1=NC(N)=NC(N)=N1 XFZRQAZGUOTJCS-UHFFFAOYSA-N 0.000 claims description 2
- 229920000909 polytetrahydrofuran Polymers 0.000 claims description 2
- 239000011527 polyurethane coating Substances 0.000 claims description 2
- 150000004684 trihydrates Chemical class 0.000 claims description 2
- DHNUXDYAOVSGII-UHFFFAOYSA-N tris(1,3-dichloropropyl) phosphate Chemical compound ClCCC(Cl)OP(=O)(OC(Cl)CCCl)OC(Cl)CCCl DHNUXDYAOVSGII-UHFFFAOYSA-N 0.000 claims description 2
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 claims description 2
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical group 0.000 claims 1
- 238000000576 coating method Methods 0.000 description 55
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- 239000003086 colorant Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
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- QQWAKSKPSOFJFF-UHFFFAOYSA-N oxiran-2-ylmethyl 2,2-dimethyloctanoate Chemical compound CCCCCCC(C)(C)C(=O)OCC1CO1 QQWAKSKPSOFJFF-UHFFFAOYSA-N 0.000 description 5
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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 4
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/721—Two or more polyisocyanates not provided for in one single group C08G18/73 - C08G18/80
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/40—High-molecular-weight compounds
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Abstract
(a) 인-함유 폴리올을 포함하는 물질과 아이소시아네이트를 포함하는 반응 혼합물로부터 형성된 아이소시아네이트 작용성 예비중합체를 포함하는 아이소시아네이트를 포함하는 제 1 성분, 및
(b) 아민을 포함하는 제 2 성분
을 포함하는 반응 혼합물로부터 형성된 폴리우레아를 포함하는 코팅 조성물에 관한 것이다.
Description
Claims (37)
- (a) 아이소시아네이트를 포함하는 제 1 성분으로서, 상기 아이소시아네이트가, 인-함유 폴리올을 포함하는 물질과 아이소시아네이트 둘 다를 포함하는 반응 혼합물로부터 형성된 아이소시아네이트 작용성 예비중합체를 포함하는, 제 1 성분, 및
(b) 아민을 포함하는 제 2 성분
을 포함하는 반응 혼합물로부터 형성된 폴리우레아를 포함하고,
아민 기의 당량에 대한 아이소시아네이트 기의 당량의 비가 1보다 크고, 상기 아이소시아네이트 및 상기 아민을 1:1의 부피 혼합 비로 기재에 적용할 수 있는, 코팅 조성물. - 제 1 항에 있어서,
상기 물질이 난연재인, 코팅 조성물. - 삭제
- 제 1 항에 있어서,
상기 인-함유 폴리올이 폴리포스페이트 다이올, 포스파이트 다이올 및/또는 이들의 블렌드를 포함하는, 코팅 조성물. - 제 1 항에 있어서,
상기 제 1 성분이 추가로 비-예비중합체 아이소시아네이트를 포함하는, 코팅 조성물. - 제 1 항에 있어서,
상기 반응 혼합물이 추가로, 폴리올, 폴리티올 및/또는 폴리아민 중 하나 이상을 포함하는, 코팅 조성물. - 제 6 항에 있어서,
상기 폴리올이 부탄다이올, 폴리테트라메틸렌 에터 글리콜 또는 이들의 혼합물을 포함하는, 코팅 조성물. - 제 1 항에 있어서,
상기 제 1 성분, 상기 제 2 성분 또는 이 둘 모두에 첨가된 난연재를 추가로 포함하는, 코팅 조성물. - 제 8 항에 있어서,
상기 난연재가, 할로겐화된 포스페이트, 무-할로겐 포스페이트, 트리스(2-클로로프로필) 포스페이트, 트리스(2,3-다이브로모프로필) 포스페이트, 트리스(1,3-다이클로로프로필) 포스페이트, 다이암모늄 포스페이트, 분말 또는 발연(fumed) 실리카, 층상 실리케이트, 알루미늄 하이드록사이드, 브롬화된 난연제, 할로겐화된 방향족 화합물, 안티몬 옥사이드, 알루미나 삼수화물, 금속 보레이트, 아연 보레이트, 바륨 메타보레이트 오수화물, 포스페이트 에스터, 폴리비닐 클로라이드, 멜라민 시아누레이트, 멜라민 포스페이트, 폴리멜라민 포스페이트, 멜라민 파이로포스페이트, 폴리멜라민 파이로포스페이트, 멜라민 보레이트, 다른 멜라민 유도체 또는 이들의 조합을 포함하는, 코팅 조성물. - 제 8 항에 있어서,
상기 난연재가 흑연을 포함하는, 코팅 조성물. - 제 1 항에 있어서,
하이드록실 기의 당량에 대한 아이소시아네이트 기의 당량의 비가 1보다 큰, 코팅 조성물. - 제 1 항에 있어서,
상기 인-함유 폴리올이, 출발 인-함유 폴리올과 에폭시 작용성 화합물의 반응 생성물인, 코팅 조성물. - 제 12 항에 있어서,
상기 에폭시 작용성 화합물이, 에틸렌 옥사이드, 프로필렌 옥사이드, 1,2-에폭시부탄, 부틸 글리시딜 에터, 네오데칸산 글리시딜 에스터 또는 이들의 조합을 포함하는, 코팅 조성물. - 제 1 항에 있어서,
상기 인-함유 폴리올이, 인-함유 산 및 에폭시 작용성 화합물의 반응 생성물 또는 인-함유 산, 에폭시 작용성 화합물 및 출발 인-함유 폴리올의 반응 생성물인, 코팅 조성물. - (a) (i) 아이소시아네이트를 포함하는 제 1 성분으로서, 상기 아이소시아네이트가, 인-함유 폴리올을 포함하는 물질과 아이소시아네이트 둘 다를 포함하는 반응 혼합물로부터 형성된 아이소시아네이트 작용성 예비중합체를 포함하는, 제 1 성분, 및
(ii) 아민을 포함하는 제 2 성분
을 포함하는 반응 혼합물로부터 형성된 폴리우레아, 및
(b) 폴리우레탄
을 포함하는 코팅 조성물. - 제 15 항에 있어서,
상기 물질이 난연재인, 코팅 조성물. - 제 15 항에 있어서,
아민 기의 당량에 대한 아이소이아네이트 기의 당량의 비가 1보다 크고, 상기 아이소시아네이트 및 상기 아민을 1:1의 부피 혼합 비로 기재에 적용할 수 있는, 코팅 조성물. - 제 15 항에 있어서,
상기 폴리우레탄이 동일 반응계에서 형성되는, 코팅 조성물. - 제 15 항에 있어서,
상기 폴리우레탄이 상기 제 1 성분, 상기 제 2 성분 또는 이 둘 모두에 첨가된, 코팅 조성물. - 제 15 항에 있어서,
상기 제 1 성분, 상기 제 2 성분 또는 이 둘 모두에 첨가된 난연재를 추가로 포함하는, 코팅 조성물. - 제 20 항에 있어서,
상기 난연재가 흑연을 포함하는, 코팅 조성물. - 제 15 항에 있어서,
상기 인-함유 폴리올이, 출발 인-함유 폴리올과 에폭시 작용성 화합물의 반응 생성물인, 코팅 조성물. - 제 22 항에 있어서,
상기 에폭시 작용성 화합물이 에틸렌 옥사이드, 프로필렌 옥사이드, 1,2-에폭시부탄, 부틸 글리시딜 에터, 네오데칸산 글리시딜 에스터, 또는 이들의 혼합물을 포함하는, 코팅 조성물. - 제 15 항에 있어서,
상기 인-함유 폴리올이, 인-함유 산 및 에폭시 작용성 화합물의 반응 생성물 또는 인-함유 산, 에폭시 작용성 화합물 및 출발 인-함유 폴리올의 반응 생성물인, 코팅 조성물. - 기재,
상기 기재의 적어도 일부 위에 적용되는 제 1 조성물로부터 침착된 제 1 층, 및
상기 제 1 층의 적어도 일부 위에 적용되는 제 2 조성물로부터 침착된 제 2 층
을 포함하는 코팅된 물품으로서,
상기 제 1 조성물 및 상기 제 2 조성물 중 적어도 하나가 제 1 항에 따른 코팅 조성물을 포함하는, 코팅된 물품. - 기재,
상기 기재의 적어도 일부 위에 적용되는 제 1 조성물로부터 침착된 제 1 층, 및
상기 제 1 층의 적어도 일부 위에 적용되는 제 2 조성물로부터 침착된 제 2 층
을 포함하는 코팅된 물품으로서,
상기 제 1 조성물 및 상기 제 2 조성물 중 적어도 하나가 제 15 항에 따른 코팅 조성물을 포함하는, 코팅된 물품. - 기재, 및
상기 기재의 적어도 일부 상에 침착되는, 제 1 항에 따른 코팅 조성물로 형성된 코팅층
을 포함하는 코팅된 물품. - 기재, 및
상기 기재의 적어도 일부 상에 침착되는, 제 15 항에 따른 코팅 조성물로 형성된 코팅층
을 포함하는 코팅된 물품. - 제 27 항에 있어서,
제 2 층 형성을 위해 상기 코팅층 위에 적용된 제 1 항에 따른 코팅 조성물을 포함하는 제 2 층을 추가로 포함하되, 상기 제 2 층이 상기 코팅층의 표면 텍스쳐보다 큰 표면 텍스쳐를 갖는, 코팅된 물품. - 제 28 항에 있어서,
제 2 층 형성을 위해 상기 코팅층 위에 적용된 제 15 항에 따른 코팅 조성물을 포함하는 제 2 층을 추가로 포함하되, 상기 제 2 층이 상기 코팅층의 표면 텍스쳐보다 큰 표면 텍스쳐를 갖는, 코팅된 물품. - 기재를 제공하는 단계; 및
제 1 조성물로부터 침착되는 제 1 층을 적용하고, 상기 제 1 층의 적어도 일부 위에 제 2 조성물로부터 침착되는 제 2 층을 적용하는 단계
를 포함하되, 상기 제 1 조성물 및 상기 제 2 조성물 중 적어도 하나가 제 1 항에 따른 코팅 조성물을 포함하는, 코팅된 물품을 형성하는 방법. - 기재를 제공하는 단계; 및
제 1 조성물로부터 침착되는 제 1 층을 적용하고, 상기 제 1 층의 적어도 일부 위에 제 2 조성물로부터 침착되는 제 2 층을 적용하는 단계
를 포함하되, 상기 제 1 조성물 및 상기 제 2 조성물 중 적어도 하나가 제 15 항에 따른 코팅 조성물을 포함하는, 코팅된 물품을 형성하는 방법. - (a) 아이소시아네이트 작용성 예비중합체 및 비-예비중합체 아이소시아네이트를 포함하는 제 1 성분으로서, 상기 아이소시아네이트 작용성 예비중합체가 상기 비-예비중합체 아이소시아네이트와 실질적으로 혼화성이고, 인-함유 폴리올을 포함하는 물질과 아이소시아네이트 둘 다를 포함하는 반응 혼합물로부터 형성되는, 제 1 성분, 및
(b) 아민을 포함하는 제 2 성분
을 포함하는 반응 혼합물로부터 형성된 폴리우레아를 포함하는 코팅 조성물. - 제 33 항에 있어서,
상기 제 1 성분, 상기 제 2 성분 또는 이 둘 모두에 첨가된 난연재를 추가로 포함하는, 코팅 조성물. - 제 33 항에 있어서,
상기 인-함유 폴리올이, 출발 인-함유 폴리올과 에폭시 작용성 화합물의 반응 생성물인, 코팅 조성물. - 제 35 항에 있어서,
상기 에폭시 작용성 화합물이 에틸렌 옥사이드, 프로필렌 옥사이드, 1,2-에폭시부탄, 부틸 글리시딜 에터, 네오데칸산 글리시딜 에스터 또는 이들의 조합을 포함하는, 코팅 조성물. - 제 33 항에 있어서,
상기 인-함유 폴리올이, 인-함유 산 및 에폭시 작용성 화합물의 반응 생성물 또는 인-함유 산, 에폭시 작용성 화합물 및 출발 인-함유 폴리올의 반응 생성물인, 코팅 조성물.
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US12/122,980 | 2008-05-19 | ||
US12/122,980 US8129492B1 (en) | 2006-07-27 | 2008-05-19 | Coating compositions comprising polyurea and a phosphorous-containing polyol |
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KR20110009251A KR20110009251A (ko) | 2011-01-27 |
KR101214711B1 true KR101214711B1 (ko) | 2012-12-21 |
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US (1) | US8129492B1 (ko) |
EP (1) | EP2283054B1 (ko) |
KR (1) | KR101214711B1 (ko) |
CN (1) | CN102066448B (ko) |
AU (1) | AU2009249344B2 (ko) |
BR (1) | BRPI0908652A2 (ko) |
CA (1) | CA2724485C (ko) |
ES (1) | ES2526965T3 (ko) |
IL (1) | IL209297A0 (ko) |
MX (1) | MX2010012552A (ko) |
RU (1) | RU2478658C2 (ko) |
WO (1) | WO2009142999A1 (ko) |
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-
2008
- 2008-05-19 US US12/122,980 patent/US8129492B1/en active Active
-
2009
- 2009-05-15 AU AU2009249344A patent/AU2009249344B2/en not_active Ceased
- 2009-05-15 BR BRPI0908652A patent/BRPI0908652A2/pt not_active IP Right Cessation
- 2009-05-15 EP EP09751228.9A patent/EP2283054B1/en not_active Not-in-force
- 2009-05-15 KR KR1020107028406A patent/KR101214711B1/ko not_active Expired - Fee Related
- 2009-05-15 CA CA2724485A patent/CA2724485C/en not_active Expired - Fee Related
- 2009-05-15 CN CN2009801234422A patent/CN102066448B/zh not_active Expired - Fee Related
- 2009-05-15 MX MX2010012552A patent/MX2010012552A/es active IP Right Grant
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AU2009249344B2 (en) | 2012-02-02 |
US20120037034A1 (en) | 2012-02-16 |
ES2526965T3 (es) | 2015-01-19 |
BRPI0908652A2 (pt) | 2015-10-06 |
CN102066448B (zh) | 2013-04-03 |
MX2010012552A (es) | 2010-12-07 |
RU2478658C2 (ru) | 2013-04-10 |
EP2283054A1 (en) | 2011-02-16 |
CA2724485C (en) | 2013-08-13 |
EP2283054B1 (en) | 2014-10-08 |
CN102066448A (zh) | 2011-05-18 |
CA2724485A1 (en) | 2009-11-26 |
AU2009249344A1 (en) | 2009-11-26 |
US8129492B1 (en) | 2012-03-06 |
IL209297A0 (en) | 2011-01-31 |
KR20110009251A (ko) | 2011-01-27 |
RU2010151897A (ru) | 2012-06-27 |
WO2009142999A1 (en) | 2009-11-26 |
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