AU758504B2 - Protonated amines for controlled crosslinking of latex polymers - Google Patents
Protonated amines for controlled crosslinking of latex polymers Download PDFInfo
- Publication number
- AU758504B2 AU758504B2 AU38802/99A AU3880299A AU758504B2 AU 758504 B2 AU758504 B2 AU 758504B2 AU 38802/99 A AU38802/99 A AU 38802/99A AU 3880299 A AU3880299 A AU 3880299A AU 758504 B2 AU758504 B2 AU 758504B2
- Authority
- AU
- Australia
- Prior art keywords
- acid
- amine
- component
- meth
- polymer
- 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.)
- Ceased
Links
- 229920000642 polymer Polymers 0.000 title claims description 119
- 239000004816 latex Substances 0.000 title claims description 67
- 229920000126 latex Polymers 0.000 title claims description 66
- 238000004132 cross linking Methods 0.000 title claims description 43
- 150000001412 amines Chemical class 0.000 title claims description 40
- 239000000203 mixture Substances 0.000 claims description 86
- 239000000178 monomer Substances 0.000 claims description 64
- -1 acetoacetoxyethyl Chemical group 0.000 claims description 54
- 239000002253 acid Substances 0.000 claims description 45
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 27
- 238000000576 coating method Methods 0.000 claims description 24
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 24
- 229920002554 vinyl polymer Polymers 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 125000002339 acetoacetyl group Chemical group O=C([*])C([H])([H])C(=O)C([H])([H])[H] 0.000 claims description 20
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 16
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000000524 functional group Chemical group 0.000 claims description 9
- 239000011248 coating agent Substances 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 150000007524 organic acids Chemical class 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical class NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 4
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical class NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 claims description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical class NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 claims description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical class NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 3
- 235000011054 acetic acid Nutrition 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 3
- BMXFFBCPBDWECJ-UHFFFAOYSA-N 2-(diaminoamino)ethanol Chemical compound NN(N)CCO BMXFFBCPBDWECJ-UHFFFAOYSA-N 0.000 claims description 2
- HMJBXEZHJUYJQY-UHFFFAOYSA-N 4-(aminomethyl)octane-1,8-diamine Chemical compound NCCCCC(CN)CCCN HMJBXEZHJUYJQY-UHFFFAOYSA-N 0.000 claims description 2
- 229920002873 Polyethylenimine Chemical class 0.000 claims description 2
- GKXVJHDEWHKBFH-UHFFFAOYSA-N [2-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC=C1CN GKXVJHDEWHKBFH-UHFFFAOYSA-N 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 claims description 2
- MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims description 2
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical compound NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 claims description 2
- OYOFUEDXAMRQBB-UHFFFAOYSA-N cyclohexylmethanediamine Chemical compound NC(N)C1CCCCC1 OYOFUEDXAMRQBB-UHFFFAOYSA-N 0.000 claims description 2
- GPQWKLDEDGOJQH-UHFFFAOYSA-N ethane-1,1,1,2-tetramine Chemical compound NCC(N)(N)N GPQWKLDEDGOJQH-UHFFFAOYSA-N 0.000 claims description 2
- LSHROXHEILXKHM-UHFFFAOYSA-N n'-[2-[2-[2-(2-aminoethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical class NCCNCCNCCNCCNCCN LSHROXHEILXKHM-UHFFFAOYSA-N 0.000 claims description 2
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 229920000333 poly(propyleneimine) Chemical class 0.000 claims description 2
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 claims description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical class CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 claims description 2
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical class NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical class NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 1
- AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical class CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims 1
- OLIBHZVRLPRRHI-UHFFFAOYSA-N benzoic acid;carbonic acid Chemical compound OC(O)=O.OC(=O)C1=CC=CC=C1 OLIBHZVRLPRRHI-UHFFFAOYSA-N 0.000 claims 1
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 1
- 235000019253 formic acid Nutrition 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 239000002245 particle Substances 0.000 description 27
- 239000004094 surface-active agent Substances 0.000 description 22
- 239000008199 coating composition Substances 0.000 description 21
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 20
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 15
- 239000008367 deionised water Substances 0.000 description 15
- 229910002092 carbon dioxide Inorganic materials 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000654 additive Substances 0.000 description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 8
- 229920001002 functional polymer Polymers 0.000 description 8
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- WDJHALXBUFZDSR-UHFFFAOYSA-M acetoacetate Chemical compound CC(=O)CC([O-])=O WDJHALXBUFZDSR-UHFFFAOYSA-M 0.000 description 5
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000019394 potassium persulphate Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
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- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
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- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
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- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- CWERGRDVMFNCDR-UHFFFAOYSA-M thioglycolate(1-) Chemical compound [O-]C(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-M 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
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- 150000003623 transition metal compounds Chemical class 0.000 description 1
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Classifications
-
- 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
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09D133/062—Copolymers with monomers not covered by C09D133/06
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
- C08L101/02—Compositions of unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical
- C08L33/062—Copolymers with monomers not covered by C08L33/06
-
- 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
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
- C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/36—Nitrogen-containing compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/078924 | 1998-05-14 | ||
| US09/078,924 US6262169B1 (en) | 1998-05-14 | 1998-05-14 | Protonated amines for controlled crosslinking of latex polymers |
| PCT/US1999/009750 WO1999058608A1 (en) | 1998-05-14 | 1999-05-05 | Protonated amines for controlled crosslinking of latex polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU3880299A AU3880299A (en) | 1999-11-29 |
| AU758504B2 true AU758504B2 (en) | 2003-03-20 |
Family
ID=22147053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU38802/99A Ceased AU758504B2 (en) | 1998-05-14 | 1999-05-05 | Protonated amines for controlled crosslinking of latex polymers |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6262169B1 (enExample) |
| EP (1) | EP1084193A1 (enExample) |
| JP (1) | JP2002514673A (enExample) |
| KR (1) | KR20010043556A (enExample) |
| CN (1) | CN1309683A (enExample) |
| AU (1) | AU758504B2 (enExample) |
| BR (1) | BR9910473A (enExample) |
| CA (1) | CA2331673A1 (enExample) |
| MY (1) | MY117044A (enExample) |
| WO (1) | WO1999058608A1 (enExample) |
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| JP3591808B2 (ja) * | 1998-03-17 | 2004-11-24 | 株式会社東芝 | 画像入力装置および方法および記録媒体 |
| US6869996B1 (en) | 1999-06-08 | 2005-03-22 | The Sherwin-Williams Company | Waterborne coating having improved chemical resistance |
| US20020103278A1 (en) * | 2000-09-15 | 2002-08-01 | Krajnik John M. | Waterborne coating composition |
| DE10133727A1 (de) * | 2001-07-11 | 2003-01-23 | Borchers Gmbh | Verwendung von Mischungen spezieller organischer Verbindungen als Hautverhinderungsmittel in lufttrocknenden Lacken |
| US6673854B2 (en) * | 2001-10-05 | 2004-01-06 | National Starch And Chemical Investment Holding Corporation | Vinyl acetate/ethylene emulsion stabilized with a phosphate surfactant |
| US6770864B2 (en) * | 2001-12-22 | 2004-08-03 | Yong Yan | Light beam operated personal interfaces to computers |
| US20040003892A1 (en) * | 2002-07-08 | 2004-01-08 | Lehman Nicholas C. | One part woodworking adhesive composition |
| KR100863501B1 (ko) * | 2002-10-07 | 2008-10-15 | 주식회사 코오롱 | 광디바이스용 보호막 형성 재료로 유용한 감광성 수지조성물 |
| US6992156B2 (en) | 2002-12-31 | 2006-01-31 | The Goodyear Tire & Rubber Company | Controlled polymerization |
| US7528204B2 (en) * | 2004-05-17 | 2009-05-05 | The Goodyear Tire & Rubber Company | Hydrogenation and epoxidation of polymers made by controlled polymerization |
| JP5311824B2 (ja) * | 2004-05-19 | 2013-10-09 | フレクスコン カンパニー インク | 基材にカーボンナノチューブインク又は油性インクを印刷する方法 |
| US20050260240A1 (en) * | 2004-05-20 | 2005-11-24 | Isp Investments Inc. | Rain-fast bioactive compositions |
| EP1799782B1 (en) * | 2004-10-08 | 2012-12-12 | The Sherwin-Williams Company | Self crosslinking waterborne coatings |
| NL1031208C2 (nl) * | 2006-02-22 | 2007-08-24 | Univ Eindhoven Tech | Waterige dispersie en werkwijze voor het aanbrengen op een substraat van een coating op basis van een dergelijke dispersie. |
| US8222304B2 (en) | 2006-03-23 | 2012-07-17 | Rhodia Operations | Process for the treatment of a hydrophobic surface by an aqueous phase |
| DE102006039941A1 (de) * | 2006-08-25 | 2008-02-28 | Wacker Chemie Ag | Verfahren zur Behandlung von cellulosehaltigen Fasern oder Flächengebilde enthaltend cellulosehaltige Fasern |
| US8921477B2 (en) * | 2008-10-13 | 2014-12-30 | Eastern Michigan University | Conventional latex / nanolatex blends |
| EP2374836A1 (en) * | 2010-04-07 | 2011-10-12 | Nuplex Resins B.V. | Crosslinkable composition crosslinkable with a latent base catalyst. |
| US8809446B2 (en) * | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Substituted 3-oxopentanoates and their uses in coating compositions |
| US9029451B2 (en) | 2010-12-15 | 2015-05-12 | Eastman Chemical Company | Waterborne coating compositions that include 2,2,4-trimethyl-3-oxopentanoate esters as reactive coalescents |
| US8809447B2 (en) | 2010-12-15 | 2014-08-19 | Eastman Chemical Company | Acetoacetate-functional monomers and their uses in coating compositions |
| EP2764036B9 (en) | 2011-10-07 | 2017-04-05 | Nuplex Resins B.V. | A crosslinkable composition comprising a latent base catalyst and latent base catalyst compositions |
| CN105985724A (zh) | 2011-10-07 | 2016-10-05 | 树脂核动力工业有限公司 | 可交联组合物 |
| CN102504090A (zh) * | 2011-10-12 | 2012-06-20 | 辽宁恒星精细化工有限公司 | 一种纺织品涂料印花用粘合剂及其制备方法 |
| JP6059088B2 (ja) * | 2012-06-14 | 2017-01-11 | 日東電工株式会社 | 耐水性有機薄膜、耐水性有機薄膜の製造方法、及び、耐水性有機薄膜を有する画像表示装置 |
| US11535762B2 (en) | 2012-09-18 | 2022-12-27 | Ennis Flint | Fast drying aqueous amine free coating composition(s) |
| JP2014125512A (ja) * | 2012-12-25 | 2014-07-07 | Henkel Japan Ltd | 水性アミンエマルション |
| EP2945994B1 (en) | 2013-01-18 | 2018-07-11 | Basf Se | Acrylic dispersion-based coating compositions |
| US9822275B2 (en) | 2013-03-15 | 2017-11-21 | Valspar Sourcing, Inc. | Water-based compositions that resist dirt pick-up |
| US9120936B2 (en) | 2013-03-15 | 2015-09-01 | Valspar Sourcing, Inc. | Water-based compositions that resist dirt pick-up |
| US10196537B2 (en) | 2013-03-15 | 2019-02-05 | The Sherwin-Williams Company | Dirt pick-up resistant composition |
| US10221322B2 (en) | 2013-03-15 | 2019-03-05 | The Sherwin-Williams Company | Dirt pick-up resistant composition |
| ES2669524T3 (es) | 2013-04-08 | 2018-05-28 | Allnex Netherlands B.V. | Composición reticulable por reacción de adición de Michael Real (RMA) |
| WO2015022186A1 (de) | 2013-08-13 | 2015-02-19 | Basf Se | Verwendung von polypropylenimin als härter für epoxidharze |
| EP3191553A4 (en) | 2014-09-12 | 2018-08-22 | Valspar Sourcing, Inc. | Water-based coating compositions that resist dirt pickup |
| JP6713796B2 (ja) * | 2015-03-28 | 2020-06-24 | 株式会社日本触媒 | 塗料用水性樹脂組成物 |
| CN107667146B (zh) | 2015-04-17 | 2021-01-01 | 欧尼克斯荷兰有限公司 | 制造可交联组合物的方法 |
| EP3283585B1 (en) | 2015-04-17 | 2023-11-15 | Allnex Netherlands B.V. | Adhesion promotor for real michael addition crosslinkable compositions |
| EP3283588B1 (en) | 2015-04-17 | 2025-06-18 | Allnex Netherlands B.V. | A method for curing a rma crosslinkable resin coating, rma crosslinkable compositions and resins for use therein |
| CN107660227B (zh) | 2015-04-17 | 2021-07-16 | 欧尼克斯荷兰有限公司 | 地板涂料组合物 |
| CN105154054B (zh) * | 2015-08-07 | 2017-12-22 | 中国石油化工股份有限公司胜利油田分公司勘探开发研究院 | 一种三元胺参与合成的交联型聚合物驱油剂及其制备方法 |
| US10717800B2 (en) | 2015-09-17 | 2020-07-21 | Ennis Paint, Inc. | Controlled crosslinking of latex polymers with polyfunctional amines |
| US10450475B2 (en) | 2015-11-17 | 2019-10-22 | Ennis Paint, Inc. | Traffic marking compositions containing polyfunctional amines |
| BR112019024332A2 (pt) * | 2017-05-29 | 2020-06-16 | Dow Global Technologies Llc | Processo para preparar um polímero funcional de acetoacetil |
| US10876014B2 (en) * | 2017-09-22 | 2020-12-29 | Natoco Co., Ltd. | Coating composition, coating material, cured film, article having cured film, and method for producing article having cured film |
| MX2020012514A (es) | 2018-05-29 | 2021-02-16 | Swimc Llc | Composiciones a base de agua con retencion de brillo a largo plazo. |
| EP3663326A1 (en) | 2018-12-04 | 2020-06-10 | Allnex Netherlands B.V. | Rma crosslinkable polymer |
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| GB2213157A (en) * | 1987-12-29 | 1989-08-09 | Nippon Synthetic Chem Ind | Adhesive containing acetoacetyl group-containing acrylic copolymer |
| EP0778317A2 (en) * | 1995-12-04 | 1997-06-11 | Rohm And Haas Company | Waterborne crosslinkable compositions |
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| DE3661834D1 (en) | 1985-03-29 | 1989-02-23 | Akzo Nv | A liquid coating composition and a process for coating a substrate with such coating composition |
| DE3642485A1 (de) | 1986-12-12 | 1988-06-23 | Basf Ag | Klebstoffe fuer verklebungen mit erhoehter waermestandfestigkeit |
| US5391624A (en) | 1992-02-10 | 1995-02-21 | S. C. Johnson & Son, Inc. | Thermosettable compositions |
| AT396934B (de) | 1992-02-14 | 1993-12-27 | Vianova Kunstharz Ag | Verfahren zur herstellung von wässrigen, selbstvernetzenden polymerdispersionen und ihre verwendung als bindemittel für lagerstabile einkomponentenlacke |
| ZA947536B (en) | 1993-09-29 | 1995-05-26 | Ici Australia Operations | Crosslinkable aqueous coating compositions |
| JP3454564B2 (ja) * | 1994-03-01 | 2003-10-06 | ダイセル化学工業株式会社 | 水性エマルジョン組成物およびその製造方法 |
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| WO1996016998A1 (de) | 1994-11-29 | 1996-06-06 | Vianova Resins Aktiengesellschaft | Verfahren zur zweistufigen herstellung von wässrigen, selbstvernetzenden copolymerisatdispersionen und deren verwendung für lacke |
| US5451653A (en) | 1994-12-28 | 1995-09-19 | Air Products And Chemicals, Inc. | Curable crosslinking system with monobenzaldimine as crosslinker |
| JPH08218026A (ja) * | 1995-02-17 | 1996-08-27 | Toyo Ink Mfg Co Ltd | 水性印刷インキ組成物 |
| JPH08311407A (ja) | 1995-05-24 | 1996-11-26 | Rohm & Haas Co | アセトアセテート官能性ポリマー及び多官能性アミンを含有する水性組成物 |
| US6005035A (en) | 1997-09-18 | 1999-12-21 | Eastman Chemical Company | Stable waterborne polymer compositions containing poly(alkylenimines) |
-
1998
- 1998-05-14 US US09/078,924 patent/US6262169B1/en not_active Expired - Lifetime
-
1999
- 1999-05-05 JP JP2000548405A patent/JP2002514673A/ja active Pending
- 1999-05-05 CN CN99808551A patent/CN1309683A/zh active Pending
- 1999-05-05 BR BR9910473-3A patent/BR9910473A/pt not_active Application Discontinuation
- 1999-05-05 EP EP99921650A patent/EP1084193A1/en not_active Withdrawn
- 1999-05-05 MY MYPI99001785A patent/MY117044A/en unknown
- 1999-05-05 CA CA002331673A patent/CA2331673A1/en not_active Abandoned
- 1999-05-05 KR KR1020007012676A patent/KR20010043556A/ko not_active Withdrawn
- 1999-05-05 AU AU38802/99A patent/AU758504B2/en not_active Ceased
- 1999-05-05 WO PCT/US1999/009750 patent/WO1999058608A1/en not_active Ceased
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2213157A (en) * | 1987-12-29 | 1989-08-09 | Nippon Synthetic Chem Ind | Adhesive containing acetoacetyl group-containing acrylic copolymer |
| EP0778317A2 (en) * | 1995-12-04 | 1997-06-11 | Rohm And Haas Company | Waterborne crosslinkable compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2331673A1 (en) | 1999-11-18 |
| CN1309683A (zh) | 2001-08-22 |
| JP2002514673A (ja) | 2002-05-21 |
| BR9910473A (pt) | 2001-01-09 |
| KR20010043556A (ko) | 2001-05-25 |
| US6262169B1 (en) | 2001-07-17 |
| EP1084193A1 (en) | 2001-03-21 |
| WO1999058608A1 (en) | 1999-11-18 |
| MY117044A (en) | 2004-04-30 |
| AU3880299A (en) | 1999-11-29 |
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