CA1094728A - Method of making aqueous emulsion of acrylate copolymers in the presence of a degraded starch protective colloid - Google Patents
Method of making aqueous emulsion of acrylate copolymers in the presence of a degraded starch protective colloidInfo
- Publication number
- CA1094728A CA1094728A CA294,632A CA294632A CA1094728A CA 1094728 A CA1094728 A CA 1094728A CA 294632 A CA294632 A CA 294632A CA 1094728 A CA1094728 A CA 1094728A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- polymer
- units
- acrylate
- coating composition
- 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
Links
- 229920002472 Starch Polymers 0.000 title claims abstract description 42
- 235000019698 starch Nutrition 0.000 title claims abstract description 42
- 239000008107 starch Substances 0.000 title claims abstract description 41
- 239000000084 colloidal system Substances 0.000 title claims abstract description 18
- 230000001681 protective effect Effects 0.000 title claims abstract description 14
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 239000000839 emulsion Substances 0.000 title claims description 12
- 229920001577 copolymer Polymers 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 33
- 239000000178 monomer Substances 0.000 claims abstract description 33
- 229920000642 polymer Polymers 0.000 claims abstract description 21
- 239000004908 Emulsion polymer Substances 0.000 claims abstract description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 20
- 239000000758 substrate Substances 0.000 claims abstract description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 12
- -1 alkyl methacrylates Chemical class 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 239000008199 coating composition Substances 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 7
- 125000005250 alkyl acrylate group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 239000006185 dispersion Substances 0.000 claims description 45
- 238000000576 coating method Methods 0.000 claims description 15
- 239000003995 emulsifying agent Substances 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 10
- 239000011248 coating agent Substances 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 7
- 239000007787 solid Substances 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 6
- 125000000129 anionic group Chemical group 0.000 claims description 6
- 239000008346 aqueous phase Substances 0.000 claims description 5
- 125000002091 cationic group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000002245 particle Substances 0.000 claims description 3
- ULEVTQHCVWIDPC-UHFFFAOYSA-N 2-(methylamino)ethyl prop-2-enoate Chemical compound CNCCOC(=O)C=C ULEVTQHCVWIDPC-UHFFFAOYSA-N 0.000 claims description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 claims description 2
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 claims description 2
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- CNCOEDDPFOAUMB-UHFFFAOYSA-N N-Methylolacrylamide Chemical compound OCNC(=O)C=C CNCOEDDPFOAUMB-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- ARZLUCYKIWYSHR-UHFFFAOYSA-N hydroxymethoxymethanol Chemical class OCOCO ARZLUCYKIWYSHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 description 26
- 239000003973 paint Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 238000000354 decomposition reaction Methods 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 229920001353 Dextrin Polymers 0.000 description 7
- 239000004375 Dextrin Substances 0.000 description 7
- 235000019425 dextrin Nutrition 0.000 description 7
- 229920003023 plastic Polymers 0.000 description 7
- 239000004033 plastic Substances 0.000 description 7
- 239000004160 Ammonium persulphate Substances 0.000 description 6
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 6
- 235000019395 ammonium persulphate Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000123 paper Substances 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 5
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 5
- 229940117927 ethylene oxide Drugs 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- TXPYHRFTMYVSLD-UHFFFAOYSA-N 2,3,4-tris(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=C(O)C(CC(C)C)=C1CC(C)C TXPYHRFTMYVSLD-UHFFFAOYSA-N 0.000 description 4
- 229920000945 Amylopectin Polymers 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- 229920000881 Modified starch Polymers 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 239000007857 degradation product Substances 0.000 description 4
- 235000019426 modified starch Nutrition 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 229920000180 alkyd Polymers 0.000 description 2
- 229920003086 cellulose ether Polymers 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000002649 leather substitute Substances 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 239000004408 titanium dioxide Substances 0.000 description 2
- 239000010876 untreated wood Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- 102000013142 Amylases Human genes 0.000 description 1
- 108010065511 Amylases Proteins 0.000 description 1
- 241000132092 Aster Species 0.000 description 1
- 101000952982 Conus striatus Conopressin-S Proteins 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 229920002774 Maltodextrin Polymers 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000019418 amylase Nutrition 0.000 description 1
- 229940025131 amylases Drugs 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000011362 coarse particle Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000001034 iron oxide pigment Substances 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- MOUPNEIJQCETIW-UHFFFAOYSA-N lead chromate Chemical compound [Pb+2].[O-][Cr]([O-])(=O)=O MOUPNEIJQCETIW-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- SONHXMAHPHADTF-UHFFFAOYSA-M sodium;2-methylprop-2-enoate Chemical compound [Na+].CC(=C)C([O-])=O SONHXMAHPHADTF-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H19/00—Coated paper; Coating material
- D21H19/36—Coatings with pigments
- D21H19/44—Coatings with pigments characterised by the other ingredients, e.g. the binder or dispersing agent
- D21H19/56—Macromolecular organic compounds or oligomers thereof obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D21H19/58—Polymers or oligomers of diolefins, aromatic vinyl monomers or unsaturated acids or derivatives thereof
-
- 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
- C09D133/064—Copolymers with monomers not covered by C09D133/06 containing anhydride, COOH or COOM groups, with M being metal or onium-cation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L3/00—Compositions of starch, amylose or amylopectin or of their derivatives or degradation products
- C08L3/02—Starch; Degradation products thereof, e.g. dextrin
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/91—Suspending agents
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Graft Or Block Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2659133.3 | 1976-12-28 | ||
| DE2659133A DE2659133C2 (de) | 1976-12-28 | 1976-12-28 | Verfahren zur Herstellung von blockfesten Überzügen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1094728A true CA1094728A (en) | 1981-01-27 |
Family
ID=5996814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA294,632A Expired CA1094728A (en) | 1976-12-28 | 1977-12-28 | Method of making aqueous emulsion of acrylate copolymers in the presence of a degraded starch protective colloid |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4171407A (ref) |
| BE (1) | BE862418A (ref) |
| CA (1) | CA1094728A (ref) |
| CH (1) | CH631363A5 (ref) |
| DE (1) | DE2659133C2 (ref) |
| DK (1) | DK151039C (ref) |
| FR (1) | FR2375917A1 (ref) |
| GB (1) | GB1594120A (ref) |
| NO (1) | NO148853C (ref) |
| SE (1) | SE425913B (ref) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337181A (en) * | 1980-01-17 | 1982-06-29 | The United States Of America As Represented By The Secretary Of Agriculture | Biodegradable starch-based blown films |
| DE3202061A1 (de) * | 1982-01-23 | 1983-08-04 | Röhm GmbH, 6100 Darmstadt | Papierstreichmasse |
| SE452472B (sv) * | 1984-11-26 | 1987-11-30 | Lacani Ab | Forfarande for behandling av spik for att oka dess utdragshallfasthet |
| US4876142A (en) * | 1987-04-17 | 1989-10-24 | Magic Stuff, Inc. | Fluid resistant coating composition |
| US4845144A (en) * | 1987-04-17 | 1989-07-04 | Magic Stuff, Inc. | Fluid resistant coating composition |
| GB8715736D0 (en) * | 1987-07-03 | 1987-08-12 | Harlow Chem Co Ltd | Adhesive compositions |
| GB8806692D0 (en) * | 1988-03-21 | 1988-04-20 | Cerestar Holding Bv | Acrylate polymer compositions |
| GB8816515D0 (en) * | 1988-07-12 | 1988-08-17 | Harlow Chem Co Ltd | Surface coating compositions |
| DE3902103A1 (de) * | 1989-01-25 | 1990-08-02 | Roehm Gmbh | Bindemittel fuer waessrige glanzfarben |
| US5055504A (en) * | 1989-07-11 | 1991-10-08 | Harlow Chemical Company Limited | Surface coating compositions |
| DE4122212C2 (de) * | 1991-07-04 | 1994-06-16 | Inventa Ag | Thermoplastisch verarbeitbare Masse aus Stärke und Acrylatcopolymeren |
| DE4133192A1 (de) * | 1991-10-07 | 1993-04-08 | Basf Ag | Verfahren zum ueberziehen von arzneiformen |
| DE4242193A1 (de) * | 1992-12-15 | 1994-06-16 | Basf Ag | Mikrokapseln mit einem als Verlaufmittel geeigneten Kernmaterial |
| JP3416194B2 (ja) * | 1993-04-26 | 2003-06-16 | 株式会社ジーシー | 義歯床用分離材 |
| DE19644309A1 (de) * | 1996-10-24 | 1998-04-30 | Basf Ag | Pulverförmiger Klebstoff |
| US5853050A (en) * | 1997-05-07 | 1998-12-29 | Rusmar Incorporated | Composition and method for generating a foam barrier and methods of use thereof |
| DE19756372A1 (de) * | 1997-12-18 | 1999-06-24 | Bayer Ag | Verbesserte Leimungsmittel für Papier |
| US6090884A (en) * | 1998-05-07 | 2000-07-18 | S. C. Johnson Commercial Markets, Inc. | Starch degradation/graft polymerization composition, process, and uses thereof |
| JP4879396B2 (ja) * | 1998-07-31 | 2012-02-22 | コオペラティ・アヴェベ・ユー・エイ | でんぷんの酸化 |
| US6114417A (en) * | 1998-10-16 | 2000-09-05 | Cytec Technology Corp. | Paper sizing agents and methods |
| TWI389925B (zh) * | 2004-11-09 | 2013-03-21 | 出光興產股份有限公司 | Optoelectronic semiconductors |
| SI2373745T1 (sl) * | 2008-12-03 | 2019-09-30 | Omya International Ag | Vodne gošče polnil iz finih delcev, postopek za njihovo pripravo in njihova uporaba za izdelavo papirjev, ki vsebuejo polnila |
| FI124806B (fi) * | 2008-12-18 | 2015-01-30 | Kemira Oyj | Päällystyspastakoostumus ja sillä päällystetty paperi tai kartonki |
| FR3024874B1 (fr) * | 2014-08-14 | 2016-09-02 | Roquette Freres | Copolymere de dextrine avec du styrene et un ester acrylique, son procede de fabrication et son utilisation pour le couchage papetier |
| CN108690169A (zh) * | 2018-06-11 | 2018-10-23 | 华东理工大学 | 一种表面施胶剂的制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2354210A (en) * | 1942-10-20 | 1944-07-25 | Du Pont | Polymerization of acrylic compounds |
| FR1377670A (fr) * | 1962-11-30 | 1964-11-06 | Wacker Chemie Gmbh | Procédé de préparation de dispersions de polymères cationiques stables |
| NL128898C (ref) * | 1963-02-08 | |||
| NL134017C (ref) * | 1965-10-29 | |||
| FR1536889A (fr) * | 1966-09-19 | 1968-08-16 | Minnesota Mining & Mfg | Revêtements polymères anti-adhérents |
| US3767604A (en) * | 1969-07-15 | 1973-10-23 | Penick & Ford Ltd | Compatible mixtures of modified starch and polyvinyl alcohol |
| US3770672A (en) * | 1971-02-10 | 1973-11-06 | Nihon Rika Seishi K K | Paste for gummed tape and process for producing the same from hydrolyzed starch |
| CA980475A (en) * | 1971-04-02 | 1975-12-23 | Richard Martorano | Metal decorating and aqueous coating composition comprising copolymer and aminoplast |
| US3769248A (en) * | 1971-10-06 | 1973-10-30 | Anheuser Busch | Starch derivative protective colloids in emulsion polymer systems |
| US3862071A (en) * | 1973-05-15 | 1975-01-21 | Du Pont | Aqueous Thermosetting Acrylic Enamel Containing Metallic Flake Pigment |
| GB1466064A (en) * | 1974-03-06 | 1977-03-02 | Ferguson Sons Ltd J | Production of emulsion polymers |
| US3957711A (en) * | 1974-12-20 | 1976-05-18 | Celanese Coatings & Specialties Company | Dispersion polymerization process using hydroxyalkyl acrylate as protective colloids |
| JPS5243891A (en) * | 1975-10-03 | 1977-04-06 | Japan Exlan Co Ltd | Process for preparing stable polymer emulsions |
| US4079025A (en) * | 1976-04-27 | 1978-03-14 | A. E. Staley Manufacturing Company | Copolymerized starch composition |
-
1976
- 1976-12-28 DE DE2659133A patent/DE2659133C2/de not_active Expired
-
1977
- 1977-11-30 NO NO774104A patent/NO148853C/no unknown
- 1977-12-08 CH CH1508777A patent/CH631363A5/de not_active IP Right Cessation
- 1977-12-15 US US05/860,826 patent/US4171407A/en not_active Expired - Lifetime
- 1977-12-23 DK DK578577A patent/DK151039C/da not_active IP Right Cessation
- 1977-12-27 SE SE7714806A patent/SE425913B/sv not_active IP Right Cessation
- 1977-12-27 FR FR7739293A patent/FR2375917A1/fr active Granted
- 1977-12-28 CA CA294,632A patent/CA1094728A/en not_active Expired
- 1977-12-28 BE BE183922A patent/BE862418A/xx not_active IP Right Cessation
- 1977-12-28 GB GB53959/77A patent/GB1594120A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK151039C (da) | 1988-06-06 |
| NO774104L (no) | 1978-06-29 |
| GB1594120A (en) | 1981-07-30 |
| DK151039B (da) | 1987-10-12 |
| SE425913B (sv) | 1982-11-22 |
| NO148853C (no) | 1983-12-28 |
| SE7714806L (sv) | 1978-06-29 |
| DK578577A (da) | 1978-06-29 |
| FR2375917A1 (fr) | 1978-07-28 |
| US4171407A (en) | 1979-10-16 |
| BE862418A (fr) | 1978-04-14 |
| DE2659133C2 (de) | 1978-09-21 |
| FR2375917B1 (ref) | 1982-05-07 |
| DE2659133B1 (de) | 1978-01-26 |
| CH631363A5 (en) | 1982-08-13 |
| NO148853B (no) | 1983-09-19 |
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