JP6157470B2 - 乳化重合、色素分散、およびuvコーティングのための、新規な反応性界面活性剤 - Google Patents
乳化重合、色素分散、およびuvコーティングのための、新規な反応性界面活性剤 Download PDFInfo
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- JP6157470B2 JP6157470B2 JP2014528561A JP2014528561A JP6157470B2 JP 6157470 B2 JP6157470 B2 JP 6157470B2 JP 2014528561 A JP2014528561 A JP 2014528561A JP 2014528561 A JP2014528561 A JP 2014528561A JP 6157470 B2 JP6157470 B2 JP 6157470B2
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- polymerization
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- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000004815 dispersion polymer Substances 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010556 emulsion polymerization method Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 235000010350 erythorbic acid Nutrition 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-M ethenesulfonate Chemical compound [O-]S(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-M 0.000 description 1
- BNKAXGCRDYRABM-UHFFFAOYSA-N ethenyl dihydrogen phosphate Chemical compound OP(O)(=O)OC=C BNKAXGCRDYRABM-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000007046 ethoxylation reaction Methods 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 description 1
- VBMVTYDPPZVILR-UHFFFAOYSA-N iron(2+);oxygen(2-) Chemical class [O-2].[Fe+2] VBMVTYDPPZVILR-UHFFFAOYSA-N 0.000 description 1
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 229940026239 isoascorbic acid Drugs 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- CTIQLGJVGNGFEW-UHFFFAOYSA-L naphthol yellow S Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C([O-])=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 CTIQLGJVGNGFEW-UHFFFAOYSA-L 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 150000002978 peroxides Chemical class 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
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- GVKCHTBDSMQENH-UHFFFAOYSA-L phloxine B Chemical compound [Na+].[Na+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(Br)C(=O)C(Br)=C2OC2=C(Br)C([O-])=C(Br)C=C21 GVKCHTBDSMQENH-UHFFFAOYSA-L 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- MZZAMHUKGIYTJW-UHFFFAOYSA-N propyl 2-methylprop-2-eneperoxoate Chemical compound CCCOOC(=O)C(C)=C MZZAMHUKGIYTJW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- FZUOVNMHEAPVBW-UHFFFAOYSA-L quinoline yellow ws Chemical compound [Na+].[Na+].O=C1C2=CC=CC=C2C(=O)C1C1=NC2=C(S([O-])(=O)=O)C=C(S(=O)(=O)[O-])C=C2C=C1 FZUOVNMHEAPVBW-UHFFFAOYSA-L 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 1
- SZHIIIPPJJXYRY-UHFFFAOYSA-M sodium;2-methylprop-2-ene-1-sulfonate Chemical compound [Na+].CC(=C)CS([O-])(=O)=O SZHIIIPPJJXYRY-UHFFFAOYSA-M 0.000 description 1
- KQFAFFYKLIBKDE-UHFFFAOYSA-M sodium;ethanesulfonate Chemical compound [Na+].CCS([O-])(=O)=O KQFAFFYKLIBKDE-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
- C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/14—Unsaturated oxiranes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/334—Polymers modified by chemical after-treatment with organic compounds containing sulfur
- C08G65/3344—Polymers modified by chemical after-treatment with organic compounds containing sulfur containing oxygen in addition to sulfur
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/335—Polymers modified by chemical after-treatment with organic compounds containing phosphorus
- C08G65/3353—Polymers modified by chemical after-treatment with organic compounds containing phosphorus containing oxygen in addition to phosphorus
- C08G65/3355—Polymers modified by chemical after-treatment with organic compounds containing phosphorus containing oxygen in addition to phosphorus having phosphorus bound to carbon and oxygen
-
- 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
- C09D171/00—Coating compositions based on polyethers obtained by reactions forming an ether link in the main chain; Coating compositions based on derivatives of such polymers
- C09D171/02—Polyalkylene oxides
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Polyethers (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Description
高分子量のポリマーを高重合速度で形成し得る。対照的に、バルク重合および溶液を用いないラジカル重合では、分子量と重合速度(rate)との間に交換関係がある。
ここで、
R=CH3 、またはCH 2 CH 3 であり;
n=1、2、または3であり;
xは2−10であり;
yは0−200であり;
zは4−200であり;
より好ましくは約5から60であり;
最も好ましくは約5から40であり;
ZーはSO3 −またはPO3 2−のいずれかであってもよく;
M+はNa+、K+、NH4 +、またはアルカノールアミンである。
ここで、R=CH 3 、またはCH 2 CH 3 であり;
n=1、2、または3であり;
xは2−10であり;
yは0−200であり;
zは4−200であり;
より好ましくは約5から60であり;
最も好ましくは約5から40である。
ここで、
R1はC10−24アルカリール(alkaryl)、アルケニル、またはシクロアルキルであり;
R2=CH3、CH2CH3、C6H5、またはC14H29であり;
xは2−10であり;
yは0−200であり;
zは4−200であり;
より好ましくは約5から60であり;
最も好ましくは約5から40であり;
Z − はSO3 −またはPO3 2−のいずれかであってもよく;
M+はNa+、K+、NH 4 +、またはアルカノールアミンである。
ここで、
R1はC10−24アルカリール、アルケニル、またはシクロアルキルであり;
R2=CH3、CH2CH3、C6H5、またはC14H29であり;
xは2−10であり;
yは0−200であり;
zは4−200であり;
より好ましくは約5から60であり;
最も好ましくは約5から40である。
ここで、
R=CH 3 、またはCH 2 CH 3 であり;
n=1、2、または3であり;
xは2−10であり;
yは0−200であり;
zは4−200であり;
より好ましくは約5から60であり;
最も好ましくは約5から40であり;
Z − はSO3 −またはPO3 2−のいずれかであってもよく;
M+はNa+、K+、NH4 +、またはアルカノールアミンであり;
ここで、
R=CH 3 、またはCH 2 CH 3 であり;
n=1、2、または3であり;
xは2−10であり;
yは0−200であり;
zは4−200であり;
より好ましくは約5から60であり;
最も好ましくは約5から40であり;
ここで、
R1はC10−24アルカリール、アルケニル、またはシクロアルキルであり;
R2=CH3、CH2CH3、C6H5、またはC14H29であり;
xは2−10であり;
yは0−200であり;
zは4−200であり;
より好ましくは約5から60であり;
最も好ましくは約5から40であり;
Z − はSO3 −またはPO3 2−のいずれかであってもよく;
M+はNa+、K+、NH 4 +、またはアルカノールアミンであり;および
ここで、
R1はC10−24アルカリール、アルケニル、またはシクロアルキルであり;
R2=CH3、CH2CH3、C6H5、またはC14H29であり;
xは2−10であり;
yは0−200であり;
zは4−200であり;
より好ましくは約5から60であり;
最も好ましくは約5から40である。
ここで、R = CH3またはCH2CH3であり、n = 1、2、3であり;xは2-10であり、yは0-200であり、zは4-200であり、より好ましくは約5から60であり、最も好ましくは約5から40であり;ZはSO3 -またはPO3 2-のいずれかであってもよく、M+はNa+、K+、NH4 +、またはアルカノールアミンである。
ここで、R = CH3またはCH2CH3であり、n =1、2、3であり;xは2-10であり、yは0-200であり、zは4-200であり、より好ましくは約5から60であり、最も好ましくは約5から40である。
ここで、R1はC10-24アルキル、アルカリール、アルケニル、またはシクロアルキルであり、R2 = CH3、CH2CH3、C6H5、またはC14H29であり;xは2-10であり、yは0-200であり、zは4-200であり、より好ましくは約5から60であり、最も好ましくは約5から40である。ZはSO3 -またはPO3 2-のいずれかであってもよく、M+はNa+、K+、NH 4 +、またはアルカノールアミンであり;
ここで、R1はC10-24アルキル、アルカリール、アルケニル、またはシクロアルキルであり、R2 = CH3、CH2CH3、C6H5、またはC14H29であり;xは2-10であり、yは0-200であり、zは4-200であり、より好ましくは約5から60であり、最も好ましくは約5から40である。
成 分 %-重量ベース(Wet Basis)
モノマー 30 − 50
界面活性剤 1 − 3
保護コロイド 0 − 3
開始剤 1 − 3
重合調整剤 0 − 1
緩衝剤 0 − 1
水 50 − 70
界面活性剤の製造
ジスチレン化フェノール(DSP)(694 g、1当量)を、アリルグリシジルエーテル(AGE)(494 g、2当量)および水酸化カリウムKOH(2.3 g)と共に、ステンレススチール製オートクレーブに加え、このオートクレーブを密封して105℃に加熱した。全てのAGEが消費された時点で、反応塊を冷却し、生成物を排出した。これはAGE 2 DSP付加物である。
ジスチレン化フェノール(DSP)(1388 g、2当量)を、アリルグリシジルエーテル(AGE)(988 g、4当量)および水酸化カリウムKOH(4.6 g)と共に、ステンレススチール製オートクレーブに加え、このオートクレーブを密封して105℃に加熱した。全てのAGEが消費された時点で、反応塊を冷却し、生成物を排出した。これはAGE 2 DSP付加物である。
ジスチレン化フェノール(DSP)(347 g、0.5当量)を、アリルグリシジルエーテル(AGE)(247 g、1当量)および水酸化カリウムKOH(1.15 g)と共に、ステンレススチール製オートクレーブに加え、このオートクレーブを密封して105℃に加熱した。全てのAGEが消費された時点で、反応塊を冷却し、生成物を排出した。これはAGE 2 DSP付加物である。
ジスチレン化フェノール(DSP)(2776 g、4当量)を、アリルグリシジルエーテル(AGE)(1976 g、8当量)および水酸化カリウムKOH(9.2 g)と共に、ステンレススチール製オートクレーブに加え、このオートクレーブを密封して105℃に加熱した。全てのAGEが消費された時点で、反応塊を冷却し、生成物を排出した。これはAGE 2 DSP付加物である。
実施例1を、撹拌器、温度計、および還流冷却器を備えたガラス製反応器中、スルファミン酸を用いて120℃に加熱することにより、硫酸エステル%が>90%になるまで硫酸化した。生成物はアンモニウム塩として単離した。
3モルの実施例1を、撹拌器、温度計、および還流冷却器を備えたガラス製反応器中、1モルの五酸化リン(P2O5)を用いて70℃に加熱することにより、反応が完了するまでリン酸化した。生成物のリン酸エステル、モノおよびジエステルの混合物は、水酸化アンモニウム水溶液で中和した。生成物は水溶液中、アンモニウム塩として単離した。
実施例4〜24
TSPは、トリスチレン化フェノールであり、トリスチレン化フェノールを主成分とする、モノ-、ジ-、およびトリスチレン化フェノールの混合物である。DSPは、ジスチレン化フェノールであり、ジスチレン化フェノールを主成分とする、モノ-、ジ-、およびトリスチレン化フェノールの混合物である。
ラテックスの耐透水性
全てのラテックスの実施例25〜28は、以下の処方を用いて、ジャケット型ガラス製反応器で製造した。各実施例は、ラテックス調製に使用した界面活性剤のみ異なっていた。
* ベルサチン酸ビニル(VV10 − モメンティブMomentive)
1. 温水器の循環を開始する
2. 初期および遅効性酸化剤溶液を作る(Make up initial and delayed oxidizer solutions)
3. 初期充填を形成する(Make up initial charge)
4. 示した順番でモノマー供給を形成する(Make up monomer feed in the order presented)
5. 初期充填を添加する(Add initial charge)
6. 温度を80℃に上げる
7. 初期酸化剤を添加する
8. モノマー供給を開始する
9. 遅効性酸化剤の供給を開始する
10. フィードの終点で、1時間待つ
11. 60分間にわたって、後期酸化剤および後期還元剤を開始する(Begin post oxidizer and post reducer over 60 minutes.)
12. 熱を除去し、冷却する
13. pHを調節する
14. 特性を測定する
最高 実施例25>実施例28>実施例27>実施例26 最低
実施例25〜28のラテックスをウッド・デッキ用染料に処方した。
ウッド・デッキ用染料の処方手順を以下に示す。
ウッド・デッキ用染料の性能は、水と共にスプレーした際の水滴を作る能力によって示されることがある。本来、より疎水性の高いラテックスは、優れた水滴化を提供する。ウッド・デッキ用染料に処方されたラテックスの水滴化特性を定量するため、染料をサザンイエローパイン材の板に塗布した。染料3 gを、面積3 x 5"の木材に塗布し、一晩乾燥させた(図5参照)。
最終的な染料について、簡単な臭気テストを実施した。染料を1/2パイントの缶に入れ、1時間静置した。上部の空間からサンプルを採取し、相対臭気を評価した。結果を以下に示す:
最も強い臭気 実施例29>>実施例30>実施例31=実施例32 最も弱い臭気
Claims (9)
- 以下よりなる群から選択される化合物:
ここで、
R=CH3またはCH2CH3であり;
n=1、2または3であり;
xは2−10であり;
yは0−200であり;
zは5−40であり;
Z − は、SO3 -またはPO3 2−のいずれかで;
M+は、Na+、K+、NH4 +、またはアルカノールアミンであり;
ここで、
R=CH3またはCH2CH3であり;
n=1,2または3であり;
xは2−10であり;
yは0−200であり;
zは5−40であり;
ここで、
R1はC10−24アルカリール、アルケニル、またはシクロアルキルであり;
R2=CH3、CH2CH3、C6H5、またはC14H29であり;
xは2−10であり;
yは0−200であり;
zは5−40であり;
Z − は、SO3 -またはPO3 2−のいずれかで;
M+は、Na+、K+、NH4 +、またはアルカノールアミンであり;および
ここで、
R1は、C10−24アルカリール、アルケニル、またはシクロアルキルであり;
R2=CH3、CH2CH3、C6H5、またはC14H29であり;
xは2−10であり;
yは0−200であり;
zは5−40である。 - 請求項1の1以上の化合物をその中に組み込んでいる、ポリマーラテックス。
- 請求項1の1以上の化合物をその中に組み込んでいる、コーティング組成物。
- 請求項2のラテックスを組み込んでいるコーティング組成物。
- 請求項1の化合物であって、R1が、ノニルフェニルおよびトリデシルよりなる群から選択される、化合物。
- 請求項1の1以上の化合物を取り込んでいる、UV硬化性コーティング組成物。
- 請求項1の1以上の化合物をその中に取り込んでいる、顔料分散系。
- 請求項1の1以上の化合物をその中に取り込んでいる、顔料。
- 請求項1の1以上の化合物をその中に取り込んでいる、二酸化チタン顔料。
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US61/573,084 | 2011-08-29 | ||
US13/598,437 | 2012-08-29 | ||
US13/598,437 US9051341B2 (en) | 2011-08-29 | 2012-08-29 | Reactive surfactants for emulsion polymerization, pigment dispersion, and UV coatings |
PCT/US2012/052919 WO2013033256A1 (en) | 2011-08-29 | 2012-08-29 | New reactive surfactants for emulsion polymerization, pigment dispersion, and uv coatings |
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KR (1) | KR101953811B1 (ja) |
CN (1) | CN104053697B (ja) |
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AU2016231634B2 (en) | 2018-05-17 |
US20130047892A1 (en) | 2013-02-28 |
MX356505B (es) | 2018-05-31 |
JP2014529667A (ja) | 2014-11-13 |
CA2847280C (en) | 2019-09-24 |
MX2014002413A (es) | 2014-11-26 |
WO2013033256A1 (en) | 2013-03-07 |
CA2847280A1 (en) | 2013-03-07 |
EP2751166A1 (en) | 2014-07-09 |
CN104053697A (zh) | 2014-09-17 |
KR20140117344A (ko) | 2014-10-07 |
US9051341B2 (en) | 2015-06-09 |
AU2012302039B2 (en) | 2016-06-23 |
BR112014004927A2 (pt) | 2017-04-11 |
AU2012302039A1 (en) | 2014-03-20 |
CN104053697B (zh) | 2016-11-23 |
KR101953811B1 (ko) | 2019-03-04 |
EP2751166B1 (en) | 2018-01-24 |
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AU2016231634A1 (en) | 2016-10-20 |
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