KR101898466B1 - 폴리메타크릴산 무수물 텔로머 - Google Patents
폴리메타크릴산 무수물 텔로머 Download PDFInfo
- Publication number
- KR101898466B1 KR101898466B1 KR1020147012731A KR20147012731A KR101898466B1 KR 101898466 B1 KR101898466 B1 KR 101898466B1 KR 1020147012731 A KR1020147012731 A KR 1020147012731A KR 20147012731 A KR20147012731 A KR 20147012731A KR 101898466 B1 KR101898466 B1 KR 101898466B1
- Authority
- KR
- South Korea
- Prior art keywords
- hypophosphite
- methacrylic
- telomer
- anhydride
- telomers
- 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.)
- Active
Links
- 229920002845 Poly(methacrylic acid) Polymers 0.000 title description 31
- 150000008065 acid anhydrides Chemical class 0.000 title 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims abstract description 81
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical class CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000003839 salts Chemical group 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000004437 phosphorous atom Chemical group 0.000 claims abstract description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 5
- 229920000642 polymer Polymers 0.000 claims description 67
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 26
- 238000010438 heat treatment Methods 0.000 claims description 16
- 229920001577 copolymer Polymers 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 13
- 239000000178 monomer Substances 0.000 claims description 12
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 11
- -1 hypophosphite compound Chemical class 0.000 claims description 10
- 230000002378 acidificating effect Effects 0.000 claims description 9
- 239000000376 reactant Substances 0.000 claims description 5
- 238000001694 spray drying Methods 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000008365 aqueous carrier Substances 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 239000008188 pellet Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract description 4
- 150000008064 anhydrides Chemical group 0.000 description 29
- 230000000052 comparative effect Effects 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- 230000004580 weight loss Effects 0.000 description 10
- 229920002125 Sokalan® Polymers 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 8
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000003545 alkoxy group Chemical group 0.000 description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 6
- 238000005102 attenuated total reflection Methods 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 4
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 125000005702 oxyalkylene group Chemical group 0.000 description 4
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 4
- 238000002411 thermogravimetry Methods 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 229920005862 polyol Polymers 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 229920001187 thermosetting polymer Polymers 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FWMFMCKIDWLKIH-UHFFFAOYSA-N C(C(=C)C)(=O)O.[PH2](=O)O Chemical compound C(C(=C)C)(=O)O.[PH2](=O)O FWMFMCKIDWLKIH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 238000003763 carbonization Methods 0.000 description 2
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 238000012711 chain transfer polymerization Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 229910003460 diamond Inorganic materials 0.000 description 2
- 239000010432 diamond Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000006254 rheological additive Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N chembl421 Chemical compound C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000008235 industrial water Substances 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000010606 normalization Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000013618 particulate matter Substances 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 102000055501 telomere Human genes 0.000 description 1
- 108091035539 telomere Proteins 0.000 description 1
- 210000003411 telomere Anatomy 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Classifications
-
- 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
- C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/08—Anhydrides
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerisation Methods In General (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161558771P | 2011-11-11 | 2011-11-11 | |
| US61/558,771 | 2011-11-11 | ||
| PCT/US2012/063674 WO2013070581A1 (en) | 2011-11-11 | 2012-11-06 | Polymethacrylic acid anhydride telomers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20140088875A KR20140088875A (ko) | 2014-07-11 |
| KR101898466B1 true KR101898466B1 (ko) | 2018-09-13 |
Family
ID=47178992
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020147012731A Active KR101898466B1 (ko) | 2011-11-11 | 2012-11-06 | 폴리메타크릴산 무수물 텔로머 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US9045575B2 (enExample) |
| EP (1) | EP2748214A1 (enExample) |
| JP (1) | JP6165756B2 (enExample) |
| KR (1) | KR101898466B1 (enExample) |
| CN (1) | CN104169315B (enExample) |
| BR (1) | BR112014010919A2 (enExample) |
| MX (1) | MX342237B (enExample) |
| WO (1) | WO2013070581A1 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9499642B2 (en) | 2011-11-11 | 2016-11-22 | Rohm And Haas Company | Small particle size hypophosphite telomers of unsaturated carboxylic acids |
| JP6600132B2 (ja) * | 2013-11-22 | 2019-10-30 | ローム アンド ハース カンパニー | （メタ）アクリルプロペンコポリマー及びその作製方法 |
| WO2016105948A1 (en) | 2014-12-22 | 2016-06-30 | Dow Global Technologies Llc | Amphiphilic comb polymers containing methacrylic anhydride |
| EP3237497B1 (en) | 2014-12-22 | 2019-06-12 | Dow Global Technologies LLC | Polymethacrylic imide-acid polymers and methods of making and using |
| US20170369371A1 (en) * | 2014-12-22 | 2017-12-28 | Dow Global Technologies Llc | Derivatized polyimides and methods of making and using |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL100455C (enExample) | 1955-12-27 | |||
| DE2509237A1 (de) | 1974-03-25 | 1975-10-09 | Rohm & Haas | Verfahren zum haerten von polymeren und haertbare polymerenzusammensetzungen |
| GB1595688A (en) | 1978-05-26 | 1981-08-12 | Ciba Geigy Uk Ltd | Treatment of aqueous systems |
| US4742123A (en) | 1981-10-07 | 1988-05-03 | Rohm And Haas Co. | Thermoplastic non-crosslinked polymers, imide polymers, and process for preparation |
| US4797711A (en) | 1986-09-10 | 1989-01-10 | Dainippon Screen Mfg., Co., Ltd. | Image scanning apparatus |
| CA1321851C (en) | 1988-01-11 | 1993-08-31 | Kathleen Anne Hughes | Process for preparing functionalized polymeric compositions |
| US5216099A (en) | 1989-06-26 | 1993-06-01 | Rohm And Haas Company | Low molecular weight water soluble phosphinate and phosphonate containing polymers |
| US5256746A (en) | 1991-04-25 | 1993-10-26 | Rohm And Haas Company | Low molecular weight monoalkyl substituted phosphinate and phosphonate copolymers |
| GB9111704D0 (en) | 1991-05-31 | 1991-07-24 | Ciba Geigy | Telomers |
| ATE163657T1 (de) | 1992-05-29 | 1998-03-15 | Rohm & Haas | Verfahren zur herstellung vernetzter copolymere von methacrylsäureanhydrid |
| US5294686A (en) | 1993-03-29 | 1994-03-15 | Rohm And Haas Company | Process for efficient utilization of chain transfer agent |
| CN1104222A (zh) * | 1993-12-24 | 1995-06-28 | 化学工业部天津化工研究院 | 膦羧酸共聚化合物 |
| US5614017A (en) | 1996-03-26 | 1997-03-25 | Arco Chemical Technology, L.P. | Cement additives |
| US6384111B1 (en) | 1996-12-20 | 2002-05-07 | Basf Aktiengesellschaft | Polymers containing carboxyl groups and polyalkylene ether side- chains as additives in mineral building materials |
| GB9703951D0 (en) * | 1997-02-26 | 1997-04-16 | Albright & Wilson Uk Ltd | Novel phosphino derivatives |
| CN1169853C (zh) | 1999-08-23 | 2004-10-06 | 花王株式会社 | (甲基)丙烯酸系聚合物的制造方法 |
| TWI239340B (en) * | 2001-12-06 | 2005-09-11 | Nippon Catalytic Chem Ind | Process for production of water-soluble (meth)acrylic polymers, water-soluble (meth)acrylic polymers, and use thereof |
| EP1348729A1 (de) | 2002-03-25 | 2003-10-01 | Sika Schweiz AG | Polymere in festem Aggregatzustand |
| US7632916B2 (en) | 2002-08-02 | 2009-12-15 | 3M Innovative Properties Company | Process to modify polymeric materials and resulting compositions |
| JP4255709B2 (ja) | 2003-02-10 | 2009-04-15 | 株式会社リコー | 画像形成装置及びその転写材ジャム検出方法 |
| DE102005053019A1 (de) | 2005-11-07 | 2007-05-10 | Basf Ag | Kammpolymere und deren Verwendung als Additive für Zubereitungen mineralischer Bindemittel |
| FR2900930B1 (fr) | 2006-05-12 | 2008-08-08 | Coatex Sas | Procede de fabrication de polymeres peigne par sechage puis fonctionnalisation de la chaine principale (meth)acrylique, polymeres obtenus et leurs utilisations |
| EP1916265A1 (de) | 2006-10-26 | 2008-04-30 | Sika Technology AG | Verfahren zur Herstellung von Amid- und Estergruppen aufweisenden Polymeren im festen Aggregatszustand |
| US20100069532A1 (en) | 2006-12-08 | 2010-03-18 | Basf Se | Process for preparing polymerizable carboxylic esters with alkoxy groups |
| US8604122B2 (en) | 2006-12-20 | 2013-12-10 | Rohm And Haas Company | Curable aqueous compositions |
| EP1942141A1 (en) * | 2006-12-22 | 2008-07-09 | Rohm and Haas France SAS | Curable composition |
| EP1942142B1 (en) | 2006-12-22 | 2010-02-17 | Rohm and Haas Company | Curable composition |
| JP5065190B2 (ja) * | 2007-09-04 | 2012-10-31 | ローム アンド ハース カンパニー | 低腐食性硬化性組成物 |
| JP4975714B2 (ja) | 2007-11-28 | 2012-07-11 | ローム アンド ハース カンパニー | ポリマーの製造法 |
| EP2072531A1 (de) | 2007-12-21 | 2009-06-24 | Sika Technology AG | Polymere mit Saccharidseitenketten und deren Verwendung als Dispergiermittel |
| FR2926558B1 (fr) | 2008-01-17 | 2010-03-05 | Coatex Sas | Amelioration d'un procede de fabrication de polymeres peignes par ajout d'un antioxydant, polymeres obtenus et leurs applications |
| CN101952326A (zh) | 2008-01-22 | 2011-01-19 | 陶氏环球技术公司 | 疏水性涂料 |
| US9499642B2 (en) | 2011-11-11 | 2016-11-22 | Rohm And Haas Company | Small particle size hypophosphite telomers of unsaturated carboxylic acids |
-
2012
- 2012-11-06 US US14/356,969 patent/US9045575B2/en active Active
- 2012-11-06 CN CN201280055115.XA patent/CN104169315B/zh active Active
- 2012-11-06 WO PCT/US2012/063674 patent/WO2013070581A1/en not_active Ceased
- 2012-11-06 EP EP12787309.9A patent/EP2748214A1/en not_active Withdrawn
- 2012-11-06 MX MX2014005588A patent/MX342237B/es active IP Right Grant
- 2012-11-06 KR KR1020147012731A patent/KR101898466B1/ko active Active
- 2012-11-06 JP JP2014541152A patent/JP6165756B2/ja active Active
- 2012-11-06 BR BR112014010919A patent/BR112014010919A2/pt not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2013070581A1 (en) | 2013-05-16 |
| MX2014005588A (es) | 2014-07-30 |
| BR112014010919A2 (pt) | 2017-05-16 |
| JP2014533317A (ja) | 2014-12-11 |
| US20140323743A1 (en) | 2014-10-30 |
| CN104169315B (zh) | 2017-03-22 |
| CN104169315A (zh) | 2014-11-26 |
| EP2748214A1 (en) | 2014-07-02 |
| KR20140088875A (ko) | 2014-07-11 |
| MX342237B (es) | 2016-09-21 |
| JP6165756B2 (ja) | 2017-07-19 |
| US9045575B2 (en) | 2015-06-02 |
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