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| Hao Wanata Ut Til at Ha Mammut |HAO WANATA UT US010023760B2TIL AT HA MAMMUT (12 ) United States Patent ( 10 ) Patent No. : US 10 , 023 ,760 B2 Yamauchi et al. ( 45 ) Date of Patent : Jul. 17 , 2018 (54 ) SEMICARBAZIDE COMPOSITION , ( 56 ) References Cited METHOD FOR PRODUCING SEMICARBAZIDE COMPOSITION , U . S . PATENT DOCUMENTS AQUEOUS POLYMER COMPOSITION AND 5 , 098 ,466 A * 3 / 1992 Anderson .. A01N 47/ 34 COMPOSITE 504 / 235 5 ,472 ,996 A 12 / 1995 Hayashi et al . @( 71 ) Applicant: ASAHI KASEI CHEMICALS 5 ,714 ,615 A * 2 / 1998 Powers . .. .. .. .. .. .. A61K 31 / 44 546 / 291 CORPORATION , Tokyo ( JP ) 5 , 880 ,312 A 3 / 1999 Nakabayashi et al. 6 , 893 ,683 B15 / 2005 Hesselmans et al. (72 ) Inventors : Toyoaki Yamauchi, Tokyo ( JP ) ; 2001/ 0018170 A1 * 8 /2001 Oyamada . .. .. .. .. GO3C 1 /49809 TakayukiMiyazaki , Tokyo ( JP ) ; 430 /620 Takahiro Itamochi, Tokyo ( JP ) 2006 / 0287260 Al 12/ 2006 Manoharan et al . 2009 /0099298 AL 4 /2009 Yukawa ( 73 ) Assignee : ASAHI KASEI CHEMICALS CORPORATION , Tokyo ( JP ) FOREIGN PATENT DOCUMENTS CN 101407688 A 4 / 2009 ( * ) Notice : Subject to any disclaimer, the term of this GB 2453669 A 4 / 2009 patent is extended or adjusted under 35 46 - 20053 Y1 6 / 1971 57 - 3850 A 1 / 1982 U . S . C . 154 (b ) by 321 days . 57 - 3857 A 1 / 1982 58 - 96643 A 6 / 1983 (21 ) Appl. No. : 14 /443 , 288 4 - 249587 A 9 / 1992 6 - 287457 A 10 / 1994 ( 22 ) PCT Filed : Nov . 15 , 2013 10 - 298158 A 11/ 1998 2001 - 164126 A 6 / 2001 2003 -510431 A 3 / 2003 ( 86 ) PCT No. : PCT/ JP2013/ 080908 2005- 29515 A 2 /2005 2005 - 42023 A 2 / 2005 § 371 (c )( 1 ), 2005 - 350580 A 12 / 2005 ( 2 ) Date : May 15 , 2015 4033518 B2 11 / 2007 2008 -504840 A 2 / 2008 ( 87 ) PCT Pub . No. : WO2014 / 077363 WO 96 /01252 AL 1 / 1996 PCT Pub . Date : May 22 , 2014 EEEEEEEEEEEEEES OTHER PUBLICATIONS (65 ) Prior Publication Data Supplementary European Search Report for European Application US 2015 /0291831 A1 Oct. 15 , 2015 No . 13855684 . 0 , dated Nov . 4 , 2015 . International Preliminary Report on Patentability and English trans Foreign Application Priority Data lation of the Written Opinion of the International Searching Author ( 30 ) ity ( Forms PCT /IB /338 , PCT/ IB /373 and PCT /ISA / 237 ) , dated May 2012 - 252603 28 , 2015 , for International Application No. PCT / JP2013 /080908 . Nov. 16 , 2012 ( JP ) .. .. .. .. .. * - -- * International Search Report ( Form PCT/ ISA / 210 ) , dated Feb . 10 , Nov . 30 , 2012 ( JP ) .. .. 2012 - 263202 2014 , for International Application No . PCT / JP2013 /080908 . (51 ) Int. Cl. C09D 133 / 26 ( 2006 .01 ) * cited by examiner C07C 281 / 06 ( 2006 .01 ) Primary Examiner — Megan McCulley C08G 18 / 75 ( 2006 .01 ) ( 74 ) Attorney, Agent, or Firm — Birch , Stewart, Kolasch C08G 18 / 32 ( 2006 .01 ) & Birch , LLP C08F 220 / 18 ( 2006 .01 ) C09D 133 / 08 ( 2006 . 01 ) (57 ) ABSTRACT C09D 163/ 00 ( 2006 . 01 ) Provided is a semicarbazide composition comprising : a C08G 59 / 40 ( 2006 .01 ) semicarbazide compound ( A ) having an amino group and a (52 ) U .S . CI. semicarbazide group ; a semicarbazide compound ( B - 1 ) hav CPC .. .. .. .. .. C09D 133 /26 ( 2013 . 01 ) ; C07C 281/ 06 ing a structure with a semicarbazide group substituted for ( 2013 .01 ) ; C08F 220 / 18 ( 2013 . 01 ) ; C08G the amino group of the semicarbazide compound ( A ); a 18 /3231 (2013 . 01 ) ; C08G 18 / 755 ( 2013 . 01 ) ; semicarbazide compound ( B - 2 ) as a dimer of the semicar CO8G 59/ 4014 ( 2013 . 01 ) ; C09D 133/ 08 bazide compound ( B - 1 ) ; and a semicarbazide compound ( 2013. 01 ) ; C09D 163 / 00 (2013 .01 ) ; C07C ( B - 3 ) as a trimer of the semicarbazide compound ( B - 1 ) ; the 2601/ 14 ( 2017 . 05 ) semicarbazide composition having an analysis area ratio ( a ) ( 58 ) Field of Classification Search of 0 . 008 % or more and 2 % or less . ??? .. .. .. CO9D 133 / 26 See application file for complete search history . 2 Claims , 5 Drawing Sheets U . S . Patent Jul. 17 , 2018 Sheet 1 of 5 US 10 ,023 , 760 B2 minmin 7 108L9 1980 ' 90 6 oemaporaneanprosessengeramenyanawwwy ) 638. 5 722. 5 p (B-2) 585. 5 mm 54614 . 5 480. 5 417. 5 374 . 5 -- T 55 152 . 4 4 785. 3 totiA wwww wwwwwwwwwwwwwwwwwww 540 .11 W (A) VWD1AWavelength=200nm 978. 10 at Fig.1 n a mpanan bercer o MAU1 800 600 400 8 0 U . S . Patent Jul. 17 , 2018 Sheet 2 of 5 US 10 ,023 ,760 B2 minmin 7 (B-3) SLE9 6 636. 5 719. 5 (B-2) 582 . 5 -- - 544. 5 - 477 . 5 414. 5 - 371 . 5 - 55 152 . 4 made 4 w (B-1) 794. 3 - - ww.1 3 mothers 2 539 * WWD1AWavelength=200nm 976. 0 Fig.2 Oye MAU1 800 6001 400 200 LO U . S . Patent Jul. 17 , 2018 Sheet 3 of 5 US 10 ,023 ,760 B2 ??? www.namashamband ulu? wwwwww 179 . 26 084. 16 9 642. 5 - 725. 5 - 689°5550. 5 484 . 5 421 . 5 378 . 5 9 160 . 4 . con w 804 . 3 vocem mam " MAI wwwwwwwwww E www www. w wwwwwwwww N 564. 1 WWD1AWavelength=200nm 0660 Fig.3 MAU1 800 600 400 2001 U . S . Patent Jul. 17 , 2018 Sheet 4 of 5 US 10 ,023 , 760 B2 ??? -* SE 179 . 16 0830 . 6 . 5 723. 5 - ast PEP9u! )2-B( 00000 481. 5 - victo418 . 5 375. 5 - ALL A 152 . 4 with memuashrewsen (B-1) 793 . 3 moramo how . 5 . 11 WWD1AWavelength=200nm 974. 0 $ y ad Fig.4 1 1 1 1 I I MAU1 008 600 400 200 o U . S . Patent Jul. 17 , 2018 Sheet 5 of 5 US 10 ,023 ,760 B2 u!WUW L 1811 . 6 085. 6 $ 9 721. 5 6 . 5 Sony 482. 5 417. 5 374 . 5 - 5 Tuy 151 . 4 momento un 4 Ww w wwwwwwwwww mediawww WWD1AWavelength=200nm wwwwwwwwwwwwwwwwww. Fig.5 motwww. to MAU1 +008 009 400 200 O US 10 ,023 , 760 B2 SEMICARBAZIDE COMPOSITION , carbonyl group - containing copolymer deteriorate with time METHOD FOR PRODUCING as described above , the composition cannot exhibit adequate SEMICARBAZIDE COMPOSITION , cross - linking performance when applied to a substrate sur AQUEOUS POLYMER COMPOSITION AND face . Furthermore , use of dicarboxylic acid dihydrazide COMPOSITE 5 having low compatibility with a carbonyl group - containing copolymer as cross - linking agent causes a problem that the TECHNICAL FIELD produced coating film by application has markedly inferior water resistance . The present invention relates to a semicarbazide compo In Patent Literature 7 and 8 , at least one selected from the sition , the method for producing a semicarbazide composi - 10 group consisting of a semicarbazide derivative and a termi tion , and an aqueous polymer composition and a composite . nal -blocked product thereof obtained by a reaction between a polyisocyanate having 3 to 20 isocyanate groups and BACKGROUND ART hydrazine or a derivative thereof , or a mixture of a non In recent years , aqueous polymer compositions have 15 terminal- blocked product and a terminal -blocked product attracted attention as material for converting to a waterborne thereof; and a semicarbazide mixture including at least one system from an organic solvent system in the coating field . selected from the group consisting of the semicarbazide Waterborne paints produced from aqueous polymer compo derivative and a terminal- blocked product thereof, and at sitions , however, still have not exhibited sufficient physical least one selected from the group consisting of a hydrophilic properties such as water resistance , stain resistance , and 20 group - containing compound and a terminal- blocked product hardness in comparison with organic solvent- based paints . thereof is proposed as a cross - linking agent. The semicar In the description here, an aqueous polymer composition bazide mixture , however , includes a large amount of com indicates the polymer dissolved and /or dispersed in water . pounds with terminal amino groups as by - products , having In this field , in order to improve physical properties of a a disadvantage of yellowing easily caused by a basic sub coating film , a functional group is generally introduced in 25 stance . the polymer of aqueous polymer composition to make In Patent Literature 9 , in addition to the auto - oxidation in cross - linkable , so that a coating film composed of a cross- a mixed system of an alkyd type emulsion and a styrene linked product of polymer (hereinafter referred to as cross acrylic emulsion containing large amounts of carboxylic linked coating film ) can be formed . acid , a styrene- acrylic emulsion ring -opening epoxy group is As an aqueous polymer composition to form a cross - 30 supported as a second cross - linking agent for combination linked coating film , the demand for cold -curing , a cold - use of the cross - linking reaction with dicarboxylic acid curing , one- pack type which is a mixture of a cross - linking dihydrazide. The water resistance of the coating film of agent and a polymer, capable of forming a cross - linked acrylic emulsion containing large amounts of carboxylic coating film in association with evaporation of an aqueous acid , however , is not satisfactory . medium without heating when applied is highly demanded . 35 In Patent Literature 10 , in order to improve the water In response to the demand , a hydrazone cross - linked water resistance of a coating film for exhibiting the stain resis borne polymer dispersions with use of a dehydration con tance , use of isophorone disemicarbazide as cross - linking densation reaction between a carbonyl group and a hydraz agent in a waterborne polymer dispersion formed of copo ide group have attracted attention in recent years . lymer which contains a carbonyl group having a high Tg In the description here , “ cold - curing , one -pack type ” 40 (glass transition temperature ) is disclosed . The combination indicates a paint which forms a coating film at 25° C . , having of a polymer having a high Tg and isophorone disemicar storage stability . In determination of storage stability , for bazide , however , has a disadvantage of incapability of film example , when a coating film formed from a paint applied formation even with use of a coalescing agent , due to to a substrate after storage at 50° C .
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