TWI385199B - A method for producing a polymer powdery matter having a cold water solubility, and a polymer powder particle having a cold water solubility - Google Patents
A method for producing a polymer powdery matter having a cold water solubility, and a polymer powder particle having a cold water solubility Download PDFInfo
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- TWI385199B TWI385199B TW094134035A TW94134035A TWI385199B TW I385199 B TWI385199 B TW I385199B TW 094134035 A TW094134035 A TW 094134035A TW 94134035 A TW94134035 A TW 94134035A TW I385199 B TWI385199 B TW I385199B
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- Prior art keywords
- powder
- water
- soluble polymer
- cold water
- polymer powder
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- 239000002245 particle Substances 0.000 title claims description 41
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title description 48
- 229920000642 polymer Polymers 0.000 title description 7
- 239000000843 powder Substances 0.000 claims description 94
- 229920003169 water-soluble polymer Polymers 0.000 claims description 51
- 239000000080 wetting agent Substances 0.000 claims description 22
- 238000003756 stirring Methods 0.000 claims description 20
- -1 hydroxyethyl hydroxypropyl Chemical group 0.000 claims description 14
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 14
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 14
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 14
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 14
- 239000008187 granular material Substances 0.000 claims description 13
- 239000007788 liquid Substances 0.000 claims description 8
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 claims description 7
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- 239000001863 hydroxypropyl cellulose Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 229920001479 Hydroxyethyl methyl cellulose Polymers 0.000 claims description 5
- 229920000609 methyl cellulose Polymers 0.000 claims description 5
- 239000001923 methylcellulose Substances 0.000 claims description 5
- 235000010981 methylcellulose Nutrition 0.000 claims description 5
- 239000003945 anionic surfactant Substances 0.000 claims description 4
- 239000003093 cationic surfactant Substances 0.000 claims description 4
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims description 3
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 claims description 3
- 235000010948 carboxy methyl cellulose Nutrition 0.000 claims description 3
- 239000008112 carboxymethyl-cellulose Substances 0.000 claims description 3
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims description 3
- 229920013819 hydroxyethyl ethylcellulose Polymers 0.000 claims description 3
- 239000002736 nonionic surfactant Substances 0.000 claims description 3
- 238000005507 spraying Methods 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims 1
- 229920003086 cellulose ether Polymers 0.000 description 23
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 15
- 238000000034 method Methods 0.000 description 12
- 238000001035 drying Methods 0.000 description 9
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 8
- 238000005054 agglomeration Methods 0.000 description 8
- 230000002776 aggregation Effects 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 7
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 239000003906 humectant Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 239000012530 fluid Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003431 cross linking reagent Substances 0.000 description 3
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 3
- 239000004014 plasticizer Substances 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 2
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- 102100026816 DNA-dependent metalloprotease SPRTN Human genes 0.000 description 2
- 101710175461 DNA-dependent metalloprotease SPRTN Proteins 0.000 description 2
- ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011362 coarse particle Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000006266 etherification reaction Methods 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- ANBBCZAIOXDZPV-UHFFFAOYSA-N 1,1,1-trimethoxy-2-methyldecane Chemical compound CC(C(OC)(OC)OC)CCCCCCCC ANBBCZAIOXDZPV-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 1
- GCZWJRLXIPVNLU-UHFFFAOYSA-N 2,2-dimethoxy-3-methylundecane Chemical compound CC(C(OC)(OC)C)CCCCCCCC GCZWJRLXIPVNLU-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 241000237858 Gastropoda Species 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- LWZFANDGMFTDAV-BURFUSLBSA-N [(2r)-2-[(2r,3r,4s)-3,4-dihydroxyoxolan-2-yl]-2-hydroxyethyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O LWZFANDGMFTDAV-BURFUSLBSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 229960000878 docusate sodium Drugs 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000005183 environmental health Effects 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 239000011361 granulated particle Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 229950006451 sorbitan laurate Drugs 0.000 description 1
- 235000011067 sorbitan monolaureate Nutrition 0.000 description 1
- 229950011392 sorbitan stearate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- KUCOHFSKRZZVRO-UHFFFAOYSA-N terephthalaldehyde Chemical compound O=CC1=CC=C(C=O)C=C1 KUCOHFSKRZZVRO-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/12—Powdering or granulating
- C08J3/122—Pulverisation by spraying
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F27/00—Mixers with rotary stirring devices in fixed receptacles; Kneaders
- B01F27/05—Stirrers
- B01F27/11—Stirrers characterised by the configuration of the stirrers
- B01F27/112—Stirrers characterised by the configuration of the stirrers with arms, paddles, vanes or blades
- B01F27/1121—Stirrers characterised by the configuration of the stirrers with arms, paddles, vanes or blades pin-shaped
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F27/00—Mixers with rotary stirring devices in fixed receptacles; Kneaders
- B01F27/60—Mixers with rotary stirring devices in fixed receptacles; Kneaders with stirrers rotating about a horizontal or inclined axis
- B01F27/62—Mixers with rotary stirring devices in fixed receptacles; Kneaders with stirrers rotating about a horizontal or inclined axis comprising liquid feeding, e.g. spraying means
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F27/00—Mixers with rotary stirring devices in fixed receptacles; Kneaders
- B01F27/60—Mixers with rotary stirring devices in fixed receptacles; Kneaders with stirrers rotating about a horizontal or inclined axis
- B01F27/70—Mixers with rotary stirring devices in fixed receptacles; Kneaders with stirrers rotating about a horizontal or inclined axis with paddles, blades or arms
- B01F27/701—Mixers with rotary stirring devices in fixed receptacles; Kneaders with stirrers rotating about a horizontal or inclined axis with paddles, blades or arms comprising two or more shafts, e.g. in consecutive mixing chambers
- B01F27/704—Mixers with rotary stirring devices in fixed receptacles; Kneaders with stirrers rotating about a horizontal or inclined axis with paddles, blades or arms comprising two or more shafts, e.g. in consecutive mixing chambers with stirrers facing each other, i.e. supported by opposite walls of the receptacle
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B7/00—Mixing; Kneading
- B29B7/02—Mixing; Kneading non-continuous, with mechanical mixing or kneading devices, i.e. batch type
- B29B7/06—Mixing; Kneading non-continuous, with mechanical mixing or kneading devices, i.e. batch type with movable mixing or kneading devices
- B29B7/10—Mixing; Kneading non-continuous, with mechanical mixing or kneading devices, i.e. batch type with movable mixing or kneading devices rotary
- B29B7/18—Mixing; Kneading non-continuous, with mechanical mixing or kneading devices, i.e. batch type with movable mixing or kneading devices rotary with more than one shaft
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29B—PREPARATION OR PRETREATMENT OF THE MATERIAL TO BE SHAPED; MAKING GRANULES OR PREFORMS; RECOVERY OF PLASTICS OR OTHER CONSTITUENTS OF WASTE MATERIAL CONTAINING PLASTICS
- B29B7/00—Mixing; Kneading
- B29B7/80—Component parts, details or accessories; Auxiliary operations
- B29B7/88—Adding charges, i.e. additives
- B29B7/94—Liquid charges
- B29B7/945—Liquid charges involving coating particles
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/05—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media from solid polymers
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
- C08L1/02—Cellulose; Modified cellulose
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F27/00—Mixers with rotary stirring devices in fixed receptacles; Kneaders
- B01F27/05—Stirrers
- B01F27/11—Stirrers characterised by the configuration of the stirrers
- B01F27/112—Stirrers characterised by the configuration of the stirrers with arms, paddles, vanes or blades
- B01F27/1122—Stirrers characterised by the configuration of the stirrers with arms, paddles, vanes or blades anchor-shaped
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2301/02—Cellulose; Modified cellulose
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Dispersion Chemistry (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Medicinal Preparation (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Description
本發明係有關水濕潤性良好，未形成結塊，快速溶解之冷水溶解性之高分子粉粒物及其製造方法。
先行技術中，水溶性高分子係用於化粧用或使用水泥類之建材用等各種用途。特別可用於水溶性高分子之水溶性纖維素醚係以紙漿等為原料，藉由鹼性溶液之鹼纖維素化反應後，進行醚化反應，於含熱水或水之有機溶劑中洗淨後，脫液過濾後所得之純化過後的水溶性纖維素醚經熱風乾燥後粉碎製造。
惟，上述步驟所得之水溶性纖維素醚等之水溶性高分子粉粒物具有下述問題。
所得之水溶性纖維素醚等之水溶性高分子之粒徑不均，且纖維狀微粉末較多，因此，溶解時產生結塊，且溶解性不良，需要長時間溶解。放水溶性高分子之一種的甲基纖維素、羥丙基甲基纖維素、羥乙基甲基纖維素等利用不溶於90℃以上熱水之性質，將上述纖維素醚分散於預先準備之熱水中，再緩緩冷卻進行溶解等煩雜之方法。其他聚環氧乙烷、聚丙烯酸鈉等水溶性高分子則採用高速攪拌裝置內使不會產生結塊的狀態下，分散於水中後藉由攪拌溶解等煩雜之方法。
因上述問題而於特公昭48－6622號公報(專利文獻1)中被揭示做為防止於冷水中產生結塊之方法之於水溶性高分子之一的水溶性纖維素醚粉中至少添加1種選自0.01~15質量份之醚系、酯系及胺系之可塑劑，均勻混合後，乾燥之後，將此進行粉碎呈粗粒狀之方法。惟，此法所得之粗粒時，其可塑劑與濕潤劑混合後，將呈粒狀至塊狀物進行乾燥後為進行粉碎，以混合與乾燥步驟特地混合，精密化者藉由粉碎後再度呈具有纖維狀部份之粗粒，於表面具有纖維質之細粉體至顆粒體，導致冷水中出現結塊。為防止此現象產生，添加可塑劑後於混合粉體時置入大量水，提高外觀之容積密度後，乾燥後進行粉碎之，惟，所得顆粒之容積密度太高，導致溶解時間太長之問題產生。
特開平6－166026號公報(專利文獻2)被揭示有利用特定之造粒裝置後，乾燥所造粒之粒子後，可製造出減少纖維狀物，幾乎接近均勻之球形，粒度亦呈幾乎一定之球狀顆粒體之造粒方法，惟，無法調製可防止於冷水中產生粉之顆粒。此乃水溶性纖維素醚之濕潤性不良，往所調製顆粒內之水滲透不足所致。
另外，於特公昭42－6674號公報(專利文獻3)被揭示有水溶性纖維素醚時，於其粉體表面使二醛等交聯劑作用後，使於冷水中所仍不產生結塊，分散粉體後，使交聯構造添加鹼成份後破壞之後，提前出現溶解性之動作，又，特開2000－63565號公報(專利文獻4)被揭示有水溶性之纖維素醚中添加交聯劑、酸、濕潤劑後，取得30篩網編號通過量為30質量%以下，200篩網編號殘留量為30質量%以下之粒狀物，未起粉狀、水濕潤性佳，冷水中未出現結塊，可於短時間下溶解之。惟，甲醛、丁醛、甘油醛等單醛、乙二醛、乙醛、對苯二甲醛等二醛等出現變異原性，藉由此變異原性造成環境衛生上的問題疑慮。另外，四甲氧基矽烷、甲基三甲氧基矽烷、二甲基二甲氧基矽烷等烷基烷氧基矽烷類等高價矽化合物之交聯劑添加後，互溶性變差，產生無法用於化粧劑、懸浮聚合劑用等問題。
[專利文獻1]特公昭48－6622號公報[專利文獻2]特開平6－166026號公報[專利文獻3]特公昭42－6674號公報[專利文獻4]特開2000－63565號公報
本發明鑑於上述問題所完成者，本發明之目的係提供一種防止產生結塊之改善冷水溶解性之水溶性纖維素醚等水溶解性高分子粉粒物之製造方法及藉此所得之冷水溶解性之高分子粉粒物。
本發明者為達成該目的而進行精密研討後結果發現，使水溶性纖維素醚等水溶性高分子粉粒物產生流動下，將濕潤劑之溶液或粉體滴下，進行噴霧或混合處理後，此處理物未強制乾燥及粉碎，直接供使用時，可得到對冷水之速溶性優之水溶解性高分子粉粒物，遂完成本發明。
又，本發明者預先於特願2003－113742號中揭示使非離子性纖維素醚之粉體產生流動下，將含有濕潤劑之粉體結合液滴下或噴霧，造粒後、乾燥，未經粉碎得到造粒物為特徵之非離子性纖維素醚之製造方法，惟，此方法在混合與乾燥兩步驟中，必須粒子調整為適當之粒徑，特別是必須乾燥步驟之製造方法，因此，乾燥所需之製造階段的設備，使用成本高，本發明係對此進行改良者。
因此，本發明提供下述水溶解性高分子粉粒物的製造方法及藉此所得具冷水溶解性之高分子粉粒物。
申請項1：使水溶性高分子粉粒物流動之同時，滴入含有濕潤劑之液體或濕潤劑粉體，進行噴霧或混合處理，對於此處理粉粒物未進行強制乾燥及粉碎者為特徵之冷水溶解性高分子粉粒物之製造方法。
申請項2：濕潤劑為選自非離子系界面活性劑、陰離子系界面活性劑、陽離子系界面活性劑者為其特徵之申請項1之水溶解性高分子粉粒物之製造方法。
申請項3：原料粉粒物及目的粉粒物分別通過第14修訂日本藥局方B－1061所載之篩網編號140(開孔106μm)之網篩通過量為30質量%以上之粉體之申請項1或2之水溶解性高分子粉粒物的製造方法。
申請項4：原料粉粒物及目的粉粒物分別通過第14修訂日本藥局方B－1061所載篩網編號140(開孔106μm)之網篩通過量為未達30質量%、同篩網編號30(開孔500μm)之網篩上殘留量為10質量%以下之粉狀物之申請項1或2之水溶解性高分子粉粒物之製造方法。
申請項5：水溶性高分子為甲基纖維素、羥乙基纖維素、羥丙基甲基纖維素、羥乙基甲基纖維素、羥乙基乙基纖維素、羥乙基羥丙基纖維素、羥丙基纖維素、羥丁基纖維素或羧甲基纖維素者為其特徵之申請項1~申請項4中任一項之水溶解性高分子粉粒物之製造方法。
申請項6：將流動水溶性高分子粉粒物之攪拌機之攪拌翼旋轉軸1支以上被水平設備，使至少1支旋轉軸每分鐘1,500旋轉以上旋轉，使水溶性高分子粉粒物為流動為其特徵之申請項1~5中任一項之水溶解性高分子粉粒物之製造方法。
申請項7：藉由申請項1~6中任一項製造方法取得具冷水溶解性之高分子粉粒物。
藉由本發明可由粉或粒狀之水溶性高分子類取得水濕潤性良好、未形成結塊、快速溶解之水溶解性高分子粉體或未進行強制乾燥操作粒狀物之理想製造。
本發明冷水溶解性高分子粉粒物之製造方法係使水溶性高分子粉粒物流動下，將含濕潤劑之液體或粉體滴下或噴霧或混合處者。
本發明所使用之水溶性高分子粉粒物，例如：甲基纖維素、羥乙基纖維素、羥丙基甲基纖維素、羥乙基甲基纖維素、羥乙基乙基纖維素、羥乙基羥丙基纖維素、羥丙基纖維素、羥丁基纖維素、羧甲基纖維素，等水溶性纖維素醚、聚丙烯酸鈉、聚環氧乙烷或其衍生物、聚乙烯醇等粉體。
又，濕潤劑亦可使用乙二醇、丙二醇、甘油等，而以具有易滲透水之性質的界面活性劑類較佳，滿足此性質之界面活性劑並未特別限定，可選自非離子系界面活性劑，陰離子系界面活性劑、陽離子系界面活性劑。
非離子系界面活性劑例如：聚環氧乙烷油醚、聚環氧乙烷月桂醚、聚環氧乙烷硬脂醚等聚環氧乙烷之高級脂肪酸醚、聚環氧乙烷單油酸酯、聚環氧乙烷月桂酸酯、聚環氧乙烷硬脂酸酯等之聚環氧乙烷之高級脂肪酸酯、山梨糖醇酐硬脂酸酯等山梨糖醇酐之脂肪酸酯、聚環氧乙烷山梨糖醇酐月桂酸酯等聚環氧乙烷山梨糖醇酐醚之脂肪酸酯、聚環氧乙烷與聚環氧丙烷之共聚物例。特別以山梨糖醇酐辛酸酯、山梨糖醇酐己酸酯等之HLB＝10以上之界面活性劑顯示良好之濕潤性，為較佳者。
陰離子系界面活性劑例如：磺基琥珀酸二辛鈉等之磺基琥珀酸酯或其鹽、月桂苯磺酸鈉等之烷基苯磺酸鹽、月桂基硫酸鈉等脂肪酸硫酸酯鹽等例。特別以磺基琥珀酸酯或其鹽較佳，其中又以磺基琥珀酸二辛基鈉具有提高水溶性纖維素醚中之羥丙基甲基纖維素之濕潤效果之性能優異，溶解後之水溶液透明性也優異。
陽離子系界面活性劑例者如：十八烷基三甲基氯化銨等。
濕潤劑特別以1種或2種以上選自磺基琥珀酸二辛鈉之30~80質量%水溶液，山梨糖醇酐脂肪酸辛酸酯、山梨糖醇酐己酸酯、聚環氧乙烷山梨糖醇酐脂肪酸酯類、聚環氧乙烷與聚環氧丙烷之共聚物者為更佳者。
濕潤劑之添加量對於每100質量份水溶性高分子時為0.1~3質量份，特別以0.5~1質量份為較佳。當未達0.1質量份則無法改善對水之濕潤性，反之，超過3質量份時亦只能發揮所添加其濕潤劑之效果。
本發明所使用之水溶性高分子係以一般工業之製造方法被製造之。特別是，纖維素醚之粉體藉由如公知之方法所調製之。亦即，以紙漿用於原料後，經由乙醯化反應及醚化反應，以熱水或冷水有機溶劑下之洗淨與必要時進行中和處理，藉由脫液過濾、乾燥後，取得水溶性纖維素醚。之後，將水溶性纖維素醚藉由如：撞擊型粉碎裝置，進行粉碎後，取得最終之水溶性纖維素醚之粉粒物。又，此粉粒物之粒度(原料水溶性高分子粉粒物之粒度)相同於使後述之含有濕潤劑之液體或濕潤劑粉體進行滴入，噴霧或混合處理後之粒度(所處理之目的冷水溶解性高分子粉粒物之粒度)。
所水溶性纖維素醚之粉末係做成2質量%之水溶液，以旋轉式黏度計或毛細管型黏度計測定20℃之黏度後被調製之。藉由此時之黏度管理後，本發明界面活性劑處理後之黏度亦具可管理之便利性。
以上方法所得之水溶性纖維素醚粉粒物係以信越化學工業(股份)製之商品名motolose Dwchemical公司製之商品名motolose Aqualone公司製之商品名Benecell及natolozol、SE－TYLOSE公司製之商品名thilose、worf公司之商品名Warocell，日本曹達(股份)製之商品名日曹HPC等被販賣之。
其次，添加所得之水溶性高分子粉粒物與界面活性劑之濕潤劑或其溶液之方法係水溶性高分子粉粒物未經粉碎，將此置入可流動之攪拌裝置或流動層裝置，使該粉粒物流動下，將必要之水及濕潤劑以噴霧器等滴下或噴霧，或添加、混合、均勻供給粉粒物，得到所期待之改善冷水溶解性之粉粒物。此時，所得目的之冷水溶性高分子粉粒物未經其後之乾燥(強制乾燥)及粉碎，直接使用。其中未進行乾燥係指加溫、減壓等後未強制強燥粉粒物之意，粉碎物於室溫下放置後，自然乾燥者除外。亦即，上述所得目的粒粉物係將此於室溫下進行放置者，藉此，粉粒物中之水份蒸發後減少水份之狀態被許可者。
添加之水量係混合時，調整界面活性劑等之濕潤劑可滴下或可噴霧程度之低黏性之必要最低量為宜，必須是滴下、噴霧、或混合後自然乾燥，水溶性高分子粉粒物彼此不會附著的程度。因此，水添加量對於之水溶性高分子100質量份時以0~40質量份較佳，特別以0~30質量份更佳。水之添加超出上述範圍時，未乾燥時則粒子彼此附著，保存中粒子可能成為塊狀。
濕潤劑水溶液(粉體結合液)之供給速度以1~500g/min，特別以2~20g/min者佳，當供給速度太慢，則所得目的物過於費時，恐生產性不良。反之，太快，則均勻之濕潤劑未附著水溶性高分子之粉體，恐無法改善對水之濕潤性。
本發明之實施例之理想攪拌裝置，例如圖1所示之裝置。此裝置1係具有處理槽2，由此處理槽2之一側部份高度方向大致中央部，其第1旋轉軸3沿著水平方向以可旋轉試插入處理槽2之內部，此第1旋轉軸3之外圍部突設多數攪拌旋轉翼4，藉由無圖示之馬達等驅動裝置使第1旋轉軸3旋轉，與此成一體使攪拌旋轉翼4同方向旋轉。又，與上述第1旋轉軸3之處理槽內突出方向相向之處理槽2之另一側部配設同樣藉由馬達等驅動裝置(無圖示)與上述第1旋轉軸3相反方向旋轉之第2旋轉軸5，往此第2旋轉軸5之處理槽2內之突出尖端部，沿著該處理槽2之另側部內壁及上部內壁、底部內壁設置螺帶狀、或籠狀攪拌翼6，此第2旋轉軸5旋轉時，與此成一體使上述第1旋轉軸3之攪拌旋轉翼4之旋轉方向形成反方向旋轉者。又，圖中7係供應含有濕潤劑之液體或濕潤劑粉體之流體噴嘴。又，水溶性高分子粉粒物係由處理槽2上部所形成之投入口8供應。
此時，該粉粒物之流動速度係如圖1所示之Dulton(股份)之Spartan liusa，使1支攪拌旋轉翼水平設置於處理槽之中心部，直徑250mm之12L容器中置入0.5kg之水溶性纖維素醚等水溶性高分子粉粒物時之旋轉翼速度較佳為1,500~10,000rpm，特別佳為2,000~7,000rpm。當此速度太慢則恐無法均勻附著濕潤劑。反之，太快時，旋轉翼之磨損快速，恐損傷裝置。
如圖1所示，針對攪拌旋轉翼使反向旋轉之螺帶狀或籠型攪拌翼呈水平設置於攪拌旋轉翼外部，使用具旋轉機序之構造攪拌裝置者宜。亦即，針對高速下攪拌之旋轉翼所產生之粉粒物流動，作成反方向之流動後，流體旋攪槽內無對流現象可均勻攪拌，因此，針對此攪拌旋轉翼設置反向旋轉之螺帶狀或籠型攪拌翼者宜。做為此攪拌翼之旋轉速度以10~1,000rpm，特別是20~100rpm為較佳。當此速度太慢時，則將無法抑制此粉粒物之停滯，反之，太快則相互粉粒物間引起撞擊，產生粉碎作用而不理想。
針對粉粒物供給濕潤劑液時之溫度以5~50℃者宜，若溫度太低時，則濕潤劑之黏性太高，將無法均勻附著，反之溫度太高則含濕潤劑之水溶液蒸發後，恐無法均勻附著。
所得冷水溶解性高分子之粉粒物粒度只要投入冷水後不易形成結塊，可溶解之程度即可，並未特別限定，粉體以通過第14修訂日本藥局方B－1061記載之篩網編號140(開孔106μm)之網篩通過量為30質量%以上，較佳為70質量%以上，更佳為90質量%以上，粒狀物時以通過第14修訂日本藥局方B－1061記載之篩網編號140(開孔106μm)之網篩通過量為30質量%以下，同篩網號30(開孔500μm)之網篩殘留量為10質量%以下。
本發明所得之冷水溶性纖維素醚等之冷水溶性高分子粉粒物不致出現先行技術中之粉粒物於冷水中產生結塊、需耗費長時間溶解，可於冷水中溶解。亦即，甲基纖維素、羥丙基甲基纖維素、羥乙基甲基纖維素等粉粒物以往不溶於熱水，因此，將該纖維素醚粉分散於預先準備之熱水中後，使緩慢冷卻，溶解等方法進行溶解，但是本發明之冷水溶解性之高分子粉粒物即使未採用此煩雜方法，仍可於超過0℃之室溫以下之冷水或於5~70℃之水溫迅速溶解。
以下，以實施例及比較例進行本發明之具體說明，惟，本發明並未受限於實施例。
如圖1所示，攪拌槽之中心部裝置水平旋轉之第1旋轉軸之攪拌旋轉翼及設置其旋轉翼周圍反方向旋轉之螺帶式攪拌翼之Dulton(股份)製，RMO－2H(有效容積2L)Spartan liuser混合造粒裝置(攪拌裝置)中投入0.5kg之信越化學工業(股份)製之羥丙基甲基纖維素(商品名：metolose 60SH－10000)之粉體(通過第14修訂日本藥局方B－106記載之篩網編號30(開孔500μm)之網篩殘留量為0%，篩網編號140(開孔106μm)之網篩通過量為82質量%、平均粒徑64μm)，以每分鐘4,700旋轉使旋轉翼轉動，使此旋轉翼之周圍之螺帶式攪拌翼以每分鐘25旋轉進行反方向旋轉，使粉體流動。以日本油脂(股份)製之磺基琥珀酸二辛基鈉(商品名：Rabisol A－80)做為濕潤劑取2.5g，分散於20g之水中，以0.03MPa插入裝置中，同時，以空氣壓力0.15MPa，以2流體噴嘴進行噴霧添加5分鐘後，流動攪拌1分鐘。
所得之羥丙基甲基纖維素粉體，其通過第14修訂日本藥局方B－1060記載之篩網編號140(開孔106μm)之網篩通過量為77質量%，平均粒徑為70μm。
將245ml之25℃純水置入每分鐘700轉之攪拌翼300mL之高筒燒杯中，再置入所得之羥丙基甲基纖維素粉5g，攪拌30分鐘後，取得無結塊均勻之黏稠溶液。
使實施例1之羥丙基甲基纖維素粉做成日本曹達(股份)製羥丙基纖維素M，使濕潤劑做成0.25g日本油脂(股份)製山梨聚糖單辛酸酯(商品名：Ceramisol C08)，做成10g分散此之水之外，與實施例1同法進行冷水溶解性改善處理。
更與實施例1同法進行過篩，取得通過第14修訂日本藥局方B－1061記載之篩網編號140(開孔106μm)之網篩通過量為66質量%，平均粒徑72μm之水溶性高分子粉。針對所得粉體，與實施例1同法測定溶解所需時間後，確定於30分鐘內溶解。
使粉狀的羥丙基甲基纖維素為信越化學工業(股份)製之粒狀羥丙基甲基纖維素60SH－10000G(通過第14修訂日本藥局方B－1061記載之篩網編號30(開孔500μm)之網篩通過量為12質量%、平均粒徑為190μm)，濕潤劑為0.25g之日本油脂(股份)製之山梨聚糖單辛酸酯(商品名：Ceramisol C08)，做成10g分散此之水，除外，與實施例1同法進行冷水溶解性改善處理。更與實施例1同法進行過篩，取得通過第14修訂日本藥局方B－1060記載之篩網編號30(開孔500μm)之網篩上殘量為9.8質量%，篩網編號140(開孔106μm)之網篩通量量12質量%，平均粒徑185μm之羥丙基甲基纖維素粒子。與實施例1同法測定所得粒子其溶解所需時間，結果確定於60分鐘內溶解。
實施例1所使用之羥丙基甲基纖維素未藉由Dulton(股份)製，RMO－2H(有效容積2L)spartanleuza混合造粒裝置進行處理，與實施例1同法評定溶解性，結果出現水中產生結塊，即使經過15小時仍未消失結塊狀物。
1．．．攪拌裝置
2．．．處理槽
3．．．第1旋轉軸
4．．．攪拌旋轉翼
5．．．第2旋轉軸
6．．．攪拌翼
7．．．流體噴嘴
8．．．投入口
[圖1]代表用於本發明實施例之攪拌裝置一例之概略截面圖。
Claims (6)
- 一種冷水溶解性高分子粉粒物的製造方法，其特徵係使水溶性高分子粉粒物流動之攪拌機的攪拌翼旋轉軸之1支以上被設置成水平狀，使至少1支之旋轉軸以每分鐘1,500旋轉以上進行旋轉，使水溶性高分子粉粒物流動之同時，滴入含有濕潤劑之液體或濕潤劑粉體，進行噴霧或混合處理，對於此處理粉粒物未進行強制乾燥及粉碎。
- 如申請專利範圍第1項之冷水溶解性高分子粉粒物的製造方法，其中該濕潤劑為選自非離子系界面活性劑、陰離子系界面活性劑、陽離子系界面活性劑者。
- 如申請專利範圍第1項或第2項之冷水溶解性高分子粉粒物的製造方法，其中該原料粉粒物及目的粉粒物分別通過第14修訂日本藥局方B-1061記載之篩網編號140(開孔106μm)之網篩通過量為30質量%以上之粉體。
- 如申請專利範圍第1項或第2項之冷水溶解性高分子粉粒物的製造方法，其中該原料粉粒物及目的粉粒物分別通過第14修訂日本藥局方B-1061記載之篩網編號140(開孔106μm)之網篩通過量為未達30質量%、同篩網編號30(開孔500μm)之網篩上殘留量為10質量%以下之粉狀物。
- 如申請專利範圍第1項或第2項之冷水溶解性高分子粉粒物的製造方法，其中該水溶性高分子為甲基纖維素 、羥乙基纖維素、羥丙基甲基纖維素、羥乙基甲基纖維素、羥乙基乙基纖維素、羥乙基羥丙基纖維素、羥丙基纖維素、羥丁基纖維素或羧甲基纖維素。
- 一種冷水溶解性之高分子粉粒物，其特徵係藉由申請專利範圍第1項至第5項中任一項之製造方法所得。
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| CN104703580A (zh) * | 2012-10-11 | 2015-06-10 | 陶氏环球技术有限公司 | 用于个人护理组合物的不含乙二醛的纤维素衍生物 |
| JP6015616B2 (ja) * | 2012-10-18 | 2016-10-26 | 信越化学工業株式会社 | セルロースエーテル粉粒体の製造方法 |
| EP2937363B1 (en) | 2014-04-22 | 2019-02-27 | Shin-Etsu Chemical Co., Ltd | Method for producing cellulose ether |
| MX2016013830A (es) * | 2015-10-27 | 2017-05-10 | Shinetsu Chemical Co | Eter de celulosa porosa no ionico soluble en agua que tiene excelente solubilidad y metodo para producir el mismo. |
| KR102687046B1 (ko) * | 2016-07-13 | 2024-07-23 | 롯데정밀화학 주식회사 | 셀룰로오스 에테르의 제조방법, 상기 방법에 의해 제조된 셀룰로오스 에테르 및 이를 포함하는 건축 마감재 |
| KR102724684B1 (ko) | 2019-01-21 | 2024-10-31 | 롯데정밀화학 주식회사 | 가교 결합된 셀룰로오스 에테르, 이의 제조방법 및 이를 포함하는 분산제 |
| CN110370485A (zh) * | 2019-07-18 | 2019-10-25 | 南京汇科高分子材料有限公司 | 一种用于生产汽车顶棚用聚氨酯组合料混拌机 |
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| KR20060051803A (ko) | 2006-05-19 |
| CN1814656A (zh) | 2006-08-09 |
| TW200621857A (en) | 2006-07-01 |
| EP1642922B2 (en) | 2015-02-25 |
| EP1642922B1 (en) | 2011-11-09 |
| US7452928B2 (en) | 2008-11-18 |
| CN1814656B (zh) | 2011-12-21 |
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| US20060069193A1 (en) | 2006-03-30 |
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