CA2535961C - Random comb polymers, process for preparing them and their use - Google Patents
Random comb polymers, process for preparing them and their use Download PDFInfo
- Publication number
- CA2535961C CA2535961C CA2535961A CA2535961A CA2535961C CA 2535961 C CA2535961 C CA 2535961C CA 2535961 A CA2535961 A CA 2535961A CA 2535961 A CA2535961 A CA 2535961A CA 2535961 C CA2535961 C CA 2535961C
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- Prior art keywords
- salt
- comb polymers
- cement
- radical
- building material
- Prior art date
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- Expired - Fee Related
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 47
- 238000004519 manufacturing process Methods 0.000 title description 7
- 239000004568 cement Substances 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 30
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 11
- 239000011230 binding agent Substances 0.000 claims abstract description 9
- 239000000725 suspension Substances 0.000 claims abstract description 8
- 125000002348 vinylic group Chemical group 0.000 claims abstract description 8
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims abstract description 7
- 235000011941 Tilia x europaea Nutrition 0.000 claims abstract description 7
- 229910052925 anhydrite Inorganic materials 0.000 claims abstract description 7
- 239000004571 lime Substances 0.000 claims abstract description 7
- 238000007334 copolymerization reaction Methods 0.000 claims abstract description 6
- 238000012546 transfer Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- -1 C1-C20-alkyl radical Chemical class 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 8
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 claims description 6
- 239000011507 gypsum plaster Substances 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 5
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 239000002270 dispersing agent Substances 0.000 claims description 5
- 239000007900 aqueous suspension Substances 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 3
- 229910018828 PO3H2 Inorganic materials 0.000 claims description 3
- 239000006229 carbon black Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 229910052573 porcelain Inorganic materials 0.000 claims description 3
- 239000011435 rock Substances 0.000 claims description 3
- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 239000010954 inorganic particle Substances 0.000 claims description 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- 125000000271 carboxylic acid salt group Chemical group 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- 239000004567 concrete Substances 0.000 abstract description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 31
- 239000000203 mixture Substances 0.000 abstract description 22
- 239000004566 building material Substances 0.000 abstract description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
- 239000004033 plastic Substances 0.000 abstract description 6
- 229920003023 plastic Polymers 0.000 abstract description 6
- 239000003795 chemical substances by application Substances 0.000 abstract description 4
- 239000010440 gypsum Substances 0.000 abstract description 2
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- 239000003999 initiator Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 238000010560 atom transfer radical polymerization reaction Methods 0.000 description 6
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- 230000000694 effects Effects 0.000 description 6
- 238000010526 radical polymerization reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
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- 238000001179 sorption measurement Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- LBSPZZSGTIBOFG-UHFFFAOYSA-N bis[2-(4,5-dihydro-1h-imidazol-2-yl)propan-2-yl]diazene;dihydrochloride Chemical compound Cl.Cl.N=1CCNC=1C(C)(C)N=NC(C)(C)C1=NCCN1 LBSPZZSGTIBOFG-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920005646 polycarboxylate Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 102100026735 Coagulation factor VIII Human genes 0.000 description 2
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- 150000007942 carboxylates Chemical group 0.000 description 2
- 150000004700 cobalt complex Chemical class 0.000 description 2
- 238000010276 construction Methods 0.000 description 2
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- 239000011521 glass Substances 0.000 description 2
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- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
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- 230000008092 positive effect Effects 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical group FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SEILKFZTLVMHRR-UHFFFAOYSA-N 2-phosphonooxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOP(O)(O)=O SEILKFZTLVMHRR-UHFFFAOYSA-N 0.000 description 1
- VFXXTYGQYWRHJP-UHFFFAOYSA-N 4,4'-azobis(4-cyanopentanoic acid) Chemical compound OC(=O)CCC(C)(C#N)N=NC(C)(CCC(O)=O)C#N VFXXTYGQYWRHJP-UHFFFAOYSA-N 0.000 description 1
- VYYSFNZHWIXVCY-UHFFFAOYSA-N 4-cyanopentanoic acid Chemical compound N#C[C](C)CCC(O)=O VYYSFNZHWIXVCY-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000001112 coagulating effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- SBGKURINHGJRFN-UHFFFAOYSA-N hydroxymethanesulfinic acid Chemical class OCS(O)=O SBGKURINHGJRFN-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 229910000359 iron(II) sulfate Inorganic materials 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000006076 specific stabilizer Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/2641—Polyacrylates; Polymethacrylates
- C04B24/2647—Polyacrylates; Polymethacrylates containing polyether side chains
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B24/00—Use of organic materials as active ingredients for mortars, concrete or artificial stone, e.g. plasticisers
- C04B24/24—Macromolecular compounds
- C04B24/26—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C04B24/2664—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of ethylenically unsaturated dicarboxylic acid polymers, e.g. maleic anhydride copolymers
- C04B24/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of ethylenically unsaturated dicarboxylic acid polymers, e.g. maleic anhydride copolymers containing polyether side chains
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B2103/00—Function or property of ingredients for mortars, concrete or artificial stone
- C04B2103/0045—Polymers chosen for their physico-chemical characteristics
- C04B2103/0059—Graft (co-)polymers
- C04B2103/006—Comb polymers
-
- 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
- C08F220/10—Esters
- C08F220/26—Esters containing oxygen in addition to the carboxy oxygen
- C08F220/28—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety
- C08F220/285—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety
- C08F220/286—Esters containing oxygen in addition to the carboxy oxygen containing no aromatic rings in the alcohol moiety and containing a polyether chain in the alcohol moiety and containing polyethylene oxide in the alcohol moiety, e.g. methoxy polyethylene glycol (meth)acrylate
-
- 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
- C08F2438/00—Living radical polymerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Ceramic Engineering (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Curing Cements, Concrete, And Artificial Stone (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10337975.4 | 2003-08-19 | ||
| DE10337975A DE10337975A1 (de) | 2003-08-19 | 2003-08-19 | Statistische Kammpolymere, Verfahren zu ihrer Herstellung und deren Verwendung |
| PCT/EP2004/009230 WO2005019288A1 (de) | 2003-08-19 | 2004-08-17 | Statistische kammpolymere, verfahren zu ihrer herstellung und deren verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2535961A1 CA2535961A1 (en) | 2005-03-03 |
| CA2535961C true CA2535961C (en) | 2012-05-01 |
Family
ID=34201663
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2535961A Expired - Fee Related CA2535961C (en) | 2003-08-19 | 2004-08-17 | Random comb polymers, process for preparing them and their use |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8299192B2 (enExample) |
| EP (1) | EP1656404B1 (enExample) |
| JP (1) | JP2007502767A (enExample) |
| CN (1) | CN100415790C (enExample) |
| AT (1) | ATE368693T1 (enExample) |
| CA (1) | CA2535961C (enExample) |
| DE (2) | DE10337975A1 (enExample) |
| ES (1) | ES2287760T3 (enExample) |
| WO (1) | WO2005019288A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005008671A1 (de) * | 2005-02-25 | 2006-08-31 | Construction Research & Technology Gmbh | Phosphor-haltige Copolymere, Verfahren zu ihrer Herstellung und deren Verwendung |
| DE102005022843A1 (de) * | 2005-05-18 | 2006-11-23 | Construction Research & Technology Gmbh | Phosphor-haltige Monomere, Verfahren zu ihrer Herstellung sowie deren Verwendung |
| EP2090553A1 (de) * | 2008-02-13 | 2009-08-19 | Construction Research and Technology GmbH | Kontinuierlich betriebenes Verfahren zur Herstellung von Copolymeren |
| EP2090596A1 (de) | 2008-02-13 | 2009-08-19 | Construction Research and Technology GmbH | Copolymer mit Polyetherseitenketten und Hydroxyalkyl- und Säurebausteinen |
| US8519029B2 (en) * | 2008-06-16 | 2013-08-27 | Construction Research & Technology Gmbh | Copolymer admixture system for workability retention of cementitious compositions |
| EP2251376A1 (de) | 2009-05-15 | 2010-11-17 | Sika Technology AG | Wässrige Polymerdispersionen |
| FR2974090B1 (fr) | 2011-04-15 | 2013-05-31 | Chryso | Copolymeres a groupements gem-bisphosphones |
| EP2535362A1 (de) * | 2011-06-17 | 2012-12-19 | Sika Technology AG | Kammpolymere als Dispergiermittel für alkalisch aktivierte Bindemittel |
| WO2013039044A1 (ja) * | 2011-09-12 | 2013-03-21 | 株式会社日本触媒 | 水硬性材料添加剤用ポリカルボン酸系重合体 |
| BR112014009304A2 (pt) * | 2011-10-28 | 2017-04-11 | Rohm & Haas | composição, e, método para fabricação de uma resina funcional |
| EP2742995A1 (de) | 2012-12-11 | 2014-06-18 | Construction Research & Technology GmbH | Kontinuierliches Verfahren zur Herstellung von Copolymeren |
| WO2015057380A1 (en) * | 2013-10-18 | 2015-04-23 | W.R. Grace & Co. -Conn. | Fast response time in slump monitoring systems |
| US9624130B2 (en) | 2015-06-15 | 2017-04-18 | Gcp Applied Technologies Inc. | Optimizing polycarboxylate admixtures for cementitious compositions |
| US9546110B2 (en) | 2015-06-15 | 2017-01-17 | Gcp Applied Technologies Inc. | Superplasticizing admixture for cementitious compositions |
| CN109096452A (zh) * | 2018-06-07 | 2018-12-28 | 湖北利建建材股份有限公司 | 一种可多元调控缓释型聚羧酸减水剂及其制备方法 |
| CN111909326B (zh) * | 2020-07-06 | 2021-04-27 | 江苏奥莱特新材料股份有限公司 | 一种MOFs结构早强型聚羧酸系减水剂及其制备方法 |
| CN116284606B (zh) * | 2023-04-11 | 2025-11-28 | 湖州绿色新材股份有限公司 | 一种低分子量聚羧酸减水剂及其制备方法和应用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9316221D0 (en) | 1993-08-05 | 1993-09-22 | Zeneca Ltd | Production of polymer emulsions |
| JP2774445B2 (ja) * | 1993-12-14 | 1998-07-09 | 花王株式会社 | コンクリート混和剤 |
| GB9407129D0 (en) * | 1994-04-11 | 1994-06-01 | Zeneca Ltd | Free radical polymerisation process |
| DE19513126A1 (de) * | 1995-04-07 | 1996-10-10 | Sueddeutsche Kalkstickstoff | Copolymere auf Basis von Oxyalkylenglykol-Alkenylethern und ungesättigten Dicarbonsäure-Derivaten |
| US6117921A (en) * | 1996-08-30 | 2000-09-12 | E. I. Du Pont De Nemours And Company | Process for making printed images using pigmented ink jet compositions |
| JP3336456B2 (ja) * | 1998-12-25 | 2002-10-21 | 日本シーカ株式会社 | セメント分散剤および該分散剤を含むコンクリート組成物 |
| AR022140A1 (es) * | 1998-12-31 | 2002-09-04 | Kimberly Clark Co | Una composicion de materia, una pelicula y un articulo que comprenden dicha composicion y el proceso para hacer dicha composicion |
| DE19905488A1 (de) * | 1999-02-10 | 2000-08-17 | Sueddeutsche Kalkstickstoff | Pulverförmige Polymerzusammensetzungen auf der Basis von Polyethercarboxylaten |
| US6296698B1 (en) * | 1999-05-25 | 2001-10-02 | Showa Denko K.K. | Cement admixture and cement composition |
| JP2001002734A (ja) | 1999-06-24 | 2001-01-09 | Nippon Shokubai Co Ltd | 重合体の製造方法 |
| DE19958447A1 (de) | 1999-12-03 | 2001-06-07 | Basf Ag | Verfahren zur Herstellung von wasserlöslichen Polymerisaten, die Polyalkylenglykolether-Seitenketten enthalten |
| JP3600100B2 (ja) * | 1999-12-20 | 2004-12-08 | 花王株式会社 | コンクリート混和剤 |
| US6576576B1 (en) * | 1999-12-29 | 2003-06-10 | Kimberly-Clark Worldwide, Inc. | Multicomponent fibers |
-
2003
- 2003-08-19 DE DE10337975A patent/DE10337975A1/de not_active Withdrawn
-
2004
- 2004-08-17 EP EP04764218A patent/EP1656404B1/de not_active Expired - Lifetime
- 2004-08-17 CN CNB2004800228510A patent/CN100415790C/zh not_active Expired - Fee Related
- 2004-08-17 JP JP2006523598A patent/JP2007502767A/ja active Pending
- 2004-08-17 ES ES04764218T patent/ES2287760T3/es not_active Expired - Lifetime
- 2004-08-17 AT AT04764218T patent/ATE368693T1/de not_active IP Right Cessation
- 2004-08-17 DE DE502004004524T patent/DE502004004524D1/de not_active Expired - Lifetime
- 2004-08-17 CA CA2535961A patent/CA2535961C/en not_active Expired - Fee Related
- 2004-08-17 US US10/567,260 patent/US8299192B2/en not_active Expired - Fee Related
- 2004-08-17 WO PCT/EP2004/009230 patent/WO2005019288A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005019288A1 (de) | 2005-03-03 |
| ATE368693T1 (de) | 2007-08-15 |
| JP2007502767A (ja) | 2007-02-15 |
| DE502004004524D1 (de) | 2007-09-13 |
| CN100415790C (zh) | 2008-09-03 |
| EP1656404B1 (de) | 2007-08-01 |
| CA2535961A1 (en) | 2005-03-03 |
| CN1860144A (zh) | 2006-11-08 |
| EP1656404A1 (de) | 2006-05-17 |
| US8299192B2 (en) | 2012-10-30 |
| DE10337975A1 (de) | 2005-04-07 |
| US20070043190A1 (en) | 2007-02-22 |
| ES2287760T3 (es) | 2007-12-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20160817 |