JP4529016B2 - ヒドラジンベースのジウレア誘導体の針状結晶及び塗料組成物及び接着剤組成物におけるレオロジー調節剤としてのその使用 - Google Patents
ヒドラジンベースのジウレア誘導体の針状結晶及び塗料組成物及び接着剤組成物におけるレオロジー調節剤としてのその使用 Download PDFInfo
- Publication number
- JP4529016B2 JP4529016B2 JP2003540132A JP2003540132A JP4529016B2 JP 4529016 B2 JP4529016 B2 JP 4529016B2 JP 2003540132 A JP2003540132 A JP 2003540132A JP 2003540132 A JP2003540132 A JP 2003540132A JP 4529016 B2 JP4529016 B2 JP 4529016B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrazine
- diurea
- formaldehyde
- crystals
- paint
- 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
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 title claims description 156
- 239000000203 mixture Substances 0.000 title claims description 64
- XMKLTEGSALONPH-UHFFFAOYSA-N 1,2,4,5-tetrazinane-3,6-dione Chemical class O=C1NNC(=O)NN1 XMKLTEGSALONPH-UHFFFAOYSA-N 0.000 title claims description 53
- 239000003973 paint Substances 0.000 title claims description 36
- 239000013078 crystal Substances 0.000 title claims description 32
- 239000000853 adhesive Substances 0.000 title claims description 28
- 230000001070 adhesive effect Effects 0.000 title claims description 28
- 239000006254 rheological additive Substances 0.000 title claims description 8
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 78
- 229920005989 resin Polymers 0.000 claims description 37
- 239000011347 resin Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 methoxybenzyl Chemical group 0.000 claims description 21
- 238000001723 curing Methods 0.000 claims description 12
- 150000002430 hydrocarbons Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000012948 isocyanate Substances 0.000 claims description 11
- 150000002513 isocyanates Chemical class 0.000 claims description 10
- 239000003630 growth substance Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000011342 resin composition Substances 0.000 claims description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006232 ethoxy propyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 238000001556 precipitation Methods 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 description 16
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 10
- 239000002245 particle Substances 0.000 description 10
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 9
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 9
- 230000009974 thixotropic effect Effects 0.000 description 9
- 239000008199 coating composition Substances 0.000 description 8
- 238000004220 aggregation Methods 0.000 description 7
- 230000002776 aggregation Effects 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 229920005862 polyol Polymers 0.000 description 7
- 238000000518 rheometry Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 4
- 239000004922 lacquer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QWDQYHPOSSHSAW-UHFFFAOYSA-N 1-isocyanatooctadecane Chemical compound CCCCCCCCCCCCCCCCCCN=C=O QWDQYHPOSSHSAW-UHFFFAOYSA-N 0.000 description 3
- 239000004971 Cross linker Substances 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000007665 sagging Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VBWBRZHAGLZNST-UHFFFAOYSA-N 1,3-bis(2-chloroethyl)urea Chemical group ClCCNC(=O)NCCCl VBWBRZHAGLZNST-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 238000007689 inspection Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- DDHUNHGZUHZNKB-UHFFFAOYSA-N 2,2-dimethylpropane-1,3-diamine Chemical compound NCC(C)(C)CN DDHUNHGZUHZNKB-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 235000002566 Capsicum Nutrition 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000006002 Pepper Substances 0.000 description 1
- 235000016761 Piper aduncum Nutrition 0.000 description 1
- 235000017804 Piper guineense Nutrition 0.000 description 1
- 244000203593 Piper nigrum Species 0.000 description 1
- 235000008184 Piper nigrum Nutrition 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 238000007590 electrostatic spraying Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000004626 scanning electron microscopy Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- 239000005028 tinplate Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/04—Thixotropic paints
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01204060 | 2001-10-26 | ||
| PCT/EP2002/011715 WO2003037849A2 (en) | 2001-10-26 | 2002-10-18 | Acicular crystals of hydrazine-based diurea derivatives and their use as rheology modifiers in coating and adhesive compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005515170A JP2005515170A (ja) | 2005-05-26 |
| JP2005515170A5 JP2005515170A5 (enExample) | 2006-01-05 |
| JP4529016B2 true JP4529016B2 (ja) | 2010-08-25 |
Family
ID=8181130
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003540132A Expired - Fee Related JP4529016B2 (ja) | 2001-10-26 | 2002-10-18 | ヒドラジンベースのジウレア誘導体の針状結晶及び塗料組成物及び接着剤組成物におけるレオロジー調節剤としてのその使用 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1641747B1 (enExample) |
| JP (1) | JP4529016B2 (enExample) |
| AU (1) | AU2002350573A1 (enExample) |
| DE (1) | DE60237243D1 (enExample) |
| WO (1) | WO2003037849A2 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5336043B2 (ja) * | 2003-07-08 | 2013-11-06 | ヌプレクス レジンズ ビー．ブイ． | 炭素において置換されたメチルアミン誘導体およびレオロジー制御剤としてのその使用方法 |
| BRPI0606710A2 (pt) * | 2005-01-11 | 2017-07-11 | Nuplex Resins Bv | Composto de poliuréia, uso do mesmo, composições de agente de controle de deformação e de revestimento, revestimento, processo para a preparação de um composto de poliuréia, e, produto de poliuréia intermediário |
| US7799858B2 (en) | 2005-01-11 | 2010-09-21 | Nuplex Resins B.V. | Commixtures for use in rheology modification |
| US7632882B2 (en) | 2005-01-13 | 2009-12-15 | E.I. Du Pont De Nemours And Company | Rheology control agents for coating compositions |
| US7652121B2 (en) | 2005-01-13 | 2010-01-26 | E.I. Du Pont De Nemours And Company | Rheology control agents for coating compositions |
| US7741510B2 (en) | 2005-01-13 | 2010-06-22 | E. I. Du Pont De Nemours And Company | Rheology control agents |
| EP2463340A1 (de) * | 2010-12-09 | 2012-06-13 | Sika Technology AG | Thixotrope Polyharnstoffaddukte |
| JP6295706B2 (ja) * | 2014-02-19 | 2018-03-20 | 東ソー株式会社 | ポリオール組成物 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3598871A (en) * | 1969-08-06 | 1971-08-10 | American Cyanamid Co | Manufacture of 1,6-dialkylbiureas |
| SU384331A1 (ru) * | 1971-05-10 | 1976-12-05 | Способ получени 1-замещенных карбамоил-4(2-оксиарил)-семинарбазидов | |
| US3893956A (en) * | 1972-12-11 | 1975-07-08 | August Merckens Nachfolger Kom | Thixotropic coating agents based on urea adduct of polyamine and diisocyanates |
| JPS61185577A (ja) * | 1985-02-13 | 1986-08-19 | Toyo Linoleum Mfg Co Ltd:The | 溶剤型接着剤 |
| NL8500476A (nl) * | 1985-02-20 | 1986-09-16 | Akzo Nv | Thixotrope bekledingssamenstelling. |
| JPH0255255A (ja) * | 1988-08-19 | 1990-02-23 | Tokuyama Soda Co Ltd | 石膏組成物 |
| JPH07126588A (ja) * | 1993-10-28 | 1995-05-16 | Cemedine Co Ltd | 揺変性組成物 |
| JP3336596B2 (ja) * | 1993-12-17 | 2002-10-21 | 日本製紙株式会社 | 感熱記録体 |
| JP3121795B2 (ja) * | 1998-09-03 | 2001-01-09 | 大塚化学株式会社 | 鋳型用樹脂被覆砂用熱硬化性樹脂組成物 |
| US6127514A (en) * | 1998-11-23 | 2000-10-03 | Bayer Corporation | One-component thermoset coating compositions |
| WO2000037520A1 (en) * | 1998-12-22 | 2000-06-29 | Akzo Nobel N.V. | Thixotropic amino formaldehyde resin |
| JP2000344998A (ja) * | 1999-06-03 | 2000-12-12 | Otsuka Chem Co Ltd | ポリアセタール樹脂組成物 |
-
2002
- 2002-10-18 WO PCT/EP2002/011715 patent/WO2003037849A2/en not_active Ceased
- 2002-10-18 JP JP2003540132A patent/JP4529016B2/ja not_active Expired - Fee Related
- 2002-10-18 DE DE60237243T patent/DE60237243D1/de not_active Expired - Lifetime
- 2002-10-18 EP EP02785250A patent/EP1641747B1/en not_active Expired - Lifetime
- 2002-10-18 AU AU2002350573A patent/AU2002350573A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005515170A (ja) | 2005-05-26 |
| WO2003037849A2 (en) | 2003-05-08 |
| EP1641747B1 (en) | 2010-08-04 |
| EP1641747A2 (en) | 2006-04-05 |
| WO2003037849A3 (en) | 2007-12-06 |
| DE60237243D1 (de) | 2010-09-16 |
| AU2002350573A1 (en) | 2003-05-12 |
| AU2002350573A8 (en) | 2008-02-28 |
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