JP2013087289A - 単相シリコーンアクリレート製剤 - Google Patents
単相シリコーンアクリレート製剤 Download PDFInfo
- Publication number
- JP2013087289A JP2013087289A JP2012233020A JP2012233020A JP2013087289A JP 2013087289 A JP2013087289 A JP 2013087289A JP 2012233020 A JP2012233020 A JP 2012233020A JP 2012233020 A JP2012233020 A JP 2012233020A JP 2013087289 A JP2013087289 A JP 2013087289A
- Authority
- JP
- Japan
- Prior art keywords
- silicone
- acrylate
- sensitive adhesive
- silicon
- compatibilizer
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 185
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 150
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 147
- 238000009472 formulation Methods 0.000 title claims abstract description 49
- 239000004820 Pressure-sensitive adhesive Substances 0.000 claims abstract description 115
- 239000010703 silicon Substances 0.000 claims abstract description 88
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 88
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 87
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 66
- 238000000034 method Methods 0.000 claims abstract description 31
- 238000005191 phase separation Methods 0.000 claims abstract description 29
- 239000003999 initiator Substances 0.000 claims abstract description 22
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 16
- 239000013543 active substance Substances 0.000 claims description 65
- 239000000178 monomer Substances 0.000 claims description 63
- 238000006243 chemical reaction Methods 0.000 claims description 55
- -1 polydimethylsiloxane Polymers 0.000 claims description 52
- 229920002050 silicone resin Polymers 0.000 claims description 34
- 229920005573 silicon-containing polymer Polymers 0.000 claims description 31
- 229920005989 resin Polymers 0.000 claims description 20
- 239000011347 resin Substances 0.000 claims description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 18
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 claims description 16
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 12
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 12
- 238000006482 condensation reaction Methods 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- 229960005309 estradiol Drugs 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 claims description 7
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 5
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims description 5
- 238000011065 in-situ storage Methods 0.000 claims description 5
- 239000002480 mineral oil Substances 0.000 claims description 5
- 235000010446 mineral oil Nutrition 0.000 claims description 5
- GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 claims description 4
- 229960002896 clonidine Drugs 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 claims description 4
- 229960000991 ketoprofen Drugs 0.000 claims description 4
- 229930182833 estradiol Natural products 0.000 claims description 3
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 claims description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 229940055577 oleyl alcohol Drugs 0.000 claims description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- 239000011541 reaction mixture Substances 0.000 description 44
- 239000002904 solvent Substances 0.000 description 40
- 238000002156 mixing Methods 0.000 description 30
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000011521 glass Substances 0.000 description 23
- 238000010438 heat treatment Methods 0.000 description 22
- 238000003756 stirring Methods 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 20
- 239000003814 drug Substances 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 18
- 239000000758 substrate Substances 0.000 description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
- 239000000463 material Substances 0.000 description 16
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 15
- 239000012467 final product Substances 0.000 description 15
- 229940079593 drug Drugs 0.000 description 14
- 238000010926 purge Methods 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000013271 transdermal drug delivery Methods 0.000 description 14
- 230000001070 adhesive effect Effects 0.000 description 13
- 239000002981 blocking agent Substances 0.000 description 13
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 13
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- 210000003491 skin Anatomy 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000008096 xylene Substances 0.000 description 11
- 239000000853 adhesive Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000009833 condensation Methods 0.000 description 10
- 230000005494 condensation Effects 0.000 description 10
- 239000004971 Cross linker Substances 0.000 description 8
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 8
- 235000014443 Pyrus communis Nutrition 0.000 description 8
- 229910004283 SiO 4 Inorganic materials 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 7
- 235000019400 benzoyl peroxide Nutrition 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
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- 230000037317 transdermal delivery Effects 0.000 description 6
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 5
- 239000004342 Benzoyl peroxide Substances 0.000 description 5
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229920006026 co-polymeric resin Polymers 0.000 description 5
- 239000003431 cross linking reagent Substances 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 229960004125 ketoconazole Drugs 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
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- 229940124597 therapeutic agent Drugs 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- PWWVAXIEGOYWEE-UHFFFAOYSA-N Isophenergan Chemical compound C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1 PWWVAXIEGOYWEE-UHFFFAOYSA-N 0.000 description 2
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- UOKUUKOEIMCYAI-UHFFFAOYSA-N trimethoxysilylmethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)COC(=O)C(C)=C UOKUUKOEIMCYAI-UHFFFAOYSA-N 0.000 description 1
- 229960002431 trimipramine Drugs 0.000 description 1
- ZSCDBOWYZJWBIY-UHFFFAOYSA-N trimipramine Chemical compound C1CC2=CC=CC=C2N(CC(CN(C)C)C)C2=CC=CC=C21 ZSCDBOWYZJWBIY-UHFFFAOYSA-N 0.000 description 1
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 1
- 229960001128 triprolidine Drugs 0.000 description 1
- CBEQULMOCCWAQT-WOJGMQOQSA-N triprolidine Chemical compound C1=CC(C)=CC=C1C(\C=1N=CC=CC=1)=C/CN1CCCC1 CBEQULMOCCWAQT-WOJGMQOQSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/10—Block or graft copolymers containing polysiloxane sequences
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/192—Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4168—1,3-Diazoles having a nitrogen attached in position 2, e.g. clonidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
- A61K9/7061—Polyacrylates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or 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 of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
- C08L43/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J143/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Adhesives based on derivatives of such polymers
- C09J143/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C09J151/085—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds on to polysiloxanes
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J2301/00—Additional features of adhesives in the form of films or foils
- C09J2301/30—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J2301/302—Additional features of adhesives in the form of films or foils characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier the adhesive being pressure-sensitive, i.e. tacky at temperatures inferior to 30°C
Abstract
【解決手段】単相シリコーンアクリレート製剤はまた、(B)シリコーン官能性および(メタ)アクリレート官能性を有し、シリコン含有感圧接着剤組成物、(メタ)アクリレートおよび開始剤の反応生成物であるシリコーンアクリレートハイブリッド相溶化剤を含む。単相シリコーンアクリレート製剤の相分離を最小限にする方法は、(A)および(B)を組み合わせて単相シリコーンアクリレート製剤を形成する工程を備える。
【選択図】なし
Description
と表すことができることを認識する。
と表すことができる。
心臓作用薬、例えば、ニトログリセリン、二硝酸イソソルビドおよび一硝酸イソソルビドのような有機硝酸塩;硫酸キニジン;プロカインアミド;ベンドロフルメチアジド、クロロチアジドおよびヒドロクロロチアジドのようなチアジド;ニフェジピン;ニカルジピン;チモロールおよびプロプラノロールのような抗アドレナリン薬;ベラパミル;ジルチアゼム;カプトプリル;クロニジンおよびプラゾシン;
テストステロン、メチルテストステロンおよびフルオキシメステロンのようなアンドロゲンステロイド;
共役エストロゲン、エステル化エストロゲン、キネストロール、エストロピペート、17−βエストラジオール、吉草酸17−βエストラジオール、エクイリン、メストラノール、エストロン、エストリオール、17−βエチニルエストラジオールおよびジエチルスチルベストロールのようなエストロゲン;
プロゲステロン、19−ノルプロゲステロン、ノルエチンドロン、酢酸ノルエチンドロン、メレンゲストロール、クロルマジノン、エチステロン、酢酸メドロキシプロゲステロン、カプロン酸ヒドロキシプロゲステロン、二酢酸エチノジオール、ノルエチノドレル、17−α−ヒドロキシプロゲステロン、ジドロゲステロン、ジメチステロン、エチニルエストレノール、ノルゲストレル、デメゲストン、プロメゲストンおよび酢酸メゲストロールのようなプロゲステロン作用薬;
中枢神経系に対する作用を有する薬物、例えば、鎮静薬、催眠薬、抗不安薬、鎮痛薬および麻酔薬、例えば、クロラール、ブプレノルフィン、ナロキソン、ハロペリドール、フルフェナジン、ペントバルビタール、フェノバルビタール、セコバルビタール、コデイン、リドカイン、テトラカイン、ジクロニン、ジブカイン、コカイン、プロカイン、メピバカイン、ブピバカイン、エチドカイン、プリロカイン、ベンゾカイン、フェンタニル、およびニコチン;
ビタミン(例えばナイアシンアミド)、必須アミノ酸および必須脂肪のような栄養剤;
抗炎症剤、例えば、ヒドロコルチゾン、コルチゾン、デキサメタゾン、フルオシノロン、トリアムシノロン、メドリゾン、プレドニゾロン、フルランドレノリド、プレドニゾン、ハルシノニド、メチルプレドニゾロン、フルドロコルチゾン、コルチコステロン、パラメタゾン、ベタメタゾン、イブプロフェン、ナプロキセン、フェノプロフェン、フェンブフェン、フルルビプロフェン、アセトアミノフェン、インドプロフェン、ケトプロフェン、スプロフェン、インドメタシン、ピロキシカム、アスピリン、サリチル酸、ジフルニサル、サリチル酸メチル、フェニルブタゾン、スリンダック、メフェナム酸、メクロフェナム酸ナトリウム、ナプロキセン等;
カンファー、メントール、トウガラシ抽出物、乳香、緑茶、ジュニパー茶およびカフェインのような外部鎮痛薬;
ジフェンヒドラミン、ジメンヒドリネート、ペルフェナジン、トリプロリジン、ピリラミン、クロルシクリジン、プロメタジン、カルビノキサミン、トリペレナミン、ブロムフェニラミン、ヒドロキシジン、シクリジン、メクリジン、テルレナジンおよびクロルフェニラミンのような抗ヒスタミン;
テオフィリンのような呼吸器作用薬およびβ−アドレナリン作動薬、例えばアルブテロール、テルブタリン、メタプロテレノール、リトドリン、カルブテロール、フェノテロール、キンテレノール、リミテロール、ソルメファモール、ソテレノール、およびトレトキノール;
ドーパミン、ノルエピネフリン、フェニルプロパノールアミン、フェニレフリン、プソイドエフェドリン、アンフェタミン、プロピルヘキセドリンおよびエピネフリンのような交感神経作用薬;
ピロカルピン等のような縮瞳薬;
コリン、アセチルコリン、メタコリン、カルバコール、ベタネコール、ピロカルピン、ムスカリンおよびアレコリンのようなコリン作動薬;
抗ムスカリン性またはムスカリン性抗コリン剤、例えばアトロピン、スコポラミン、ホマトロピン、メトスコポラミン、ホマトロピンメチルブロミド、メタンテリン、シクロペントレート、トロピカミド、プロパンテリン、アニソトロピン、ジシクロミン、およびユーカトロピン;
アトロピン、シクロペントレート、ホマトロピン、スコポラミン、トロピカミド、ユーカトロピンおよびヒドロキシアンフェタミンのような散瞳薬;
3−(2−アミノプロピル)インドール、3−(2−アミノブチル)インドール等のような精神賦活剤;
抗感染剤、例えばペニシリン、テトラシクリン、クロランフェニコール、スルファセタミド、スルファジアジン、スルファメトキサゾールおよびスルフィソキサゾールを含む抗生物質;イドクスウリジンを含む抗ウィルス剤;エリスロマイシンおよびクラリスロマイシンのような抗菌剤;ケトコナゾールのような抗真菌剤;ならびニトロフラゾン、シクロピロクス、テルバフィン、ウィッチヘーゼル等を含む他の抗感染剤;
外皮用薬、例えばレチノイド;ビタミンCおよびE;過酸化ベンゾイル(BPO)(一般的には過酸化ジベンゾイルとも称される);ならびにダプソン;
天然および合成プロスタグランジンのような体液性剤、例えばPGEl、PGE2−α、PGF2−αおよびPGEl類似体ミソプロストール;
アトロピン、メタンテリン、パパベリン、シンナメドリン、およびメタスコポラミンのような抗痙攣薬;
パロキセチン、フェネルジン、トラニルシプロミン、イミプラミン、アミトリプチリン、トリミプラミン、ドキセピン、デシプラミン、ノルトリプチリン、プロトリプチリン、アモキサピン、マプロチリンおよびトラゾドンのような抗うつ薬;
インスリンのような抗糖尿病薬、ならびにタモキシフェンおよびメトトレキセートのような抗癌薬;
デキストロアンフェタミン、メタンフェタミン、フェニルプロパノールアミン、フェンフルラミン、ジエチルプロピオン、マジンドールおよびフェンテルミンのような食欲抑制薬;
アンタゾリン、メタピリレン、クロルフェニラミン、ピリラミンおよびフェニラミンのような抗アレルギー薬;
レセルピン、クロルプロマジンのような精神安定剤、および抗不安ベンゾジアゼピン、例えば、アルプラゾラム、クロルジアゼポキシド、クロラゼプテート、ハラゼパム、オキサゼパム、パラゼパム、クロナゼパム、フルラゼパム、トリアゾラム、ロラゼパムおよびジアゼパム;
チオプロパゼート、クロロプロマジン、トリフルプロマジン、メソリダジン、ピペラセタジン、チオリダジン、アセトフェナジン、フルフェナジン、ペルフェナジン、トリフルオペラジン、クロロプロチキセン、チオチキセン、ハロペリドール、ブロムペリドール、ロキサピンおよびモリンドンのような抗精神病薬;
フェニルエフリン、エフェドリン、ナファゾリン、テトラヒドロゾリンのようなうっ血除去薬;
アスピリン、サリチルアミド等のような解熱薬;
ジヒドロエルゴタミンおよびピゾチリンのような抗片頭痛薬;
悪心および嘔吐の治療薬、例えばクロロプロマジン、ペルフェナジン、プロクロルペラジン、プロメタジン、トリエチルペラジン、トリフルプロマジン、およびトリメプラジン;
4−アミノキノリン、αアミノキノリン、クロロキンおよびピリメタミンのような抗マラリア薬;
ミソプロストール、オメプラゾールおよびエンプロスチルのような抗潰瘍薬;
成長ホルモン放出因子のようなペプチド;
パーキンソン病、痙縮、および急性筋痙攣の治療薬、例えば、レボドパ、カルビドパ、アマンタジン、アポモルフィン、ブロモクリプチン、セレギリン(デプレニル)、トリへキシフェニジル、ヒドロクロリド、ベンズトロピンメシレート、塩酸プロシクリジン、バクロフェン、ジアゼパムおよびダントロレン;ならびに
タモキシフェンまたはヒト絨毛性ゴナドトロピンのような抗エストロゲンまたは抗ホルモン剤が挙げられる。
ハイブリッド1は以下の方法を用いて形成する。16オンスのジャーに74.58gの2−EHAと、60.97gのMAと、214.01gのシリコン含有感圧接着剤組成物と、32.72gの酢酸エチル溶剤と、0.196gのVazo(登録商標)67とを添加して、予備反応混合物を形成する。
ハイブリッド2は以下の方法を用いて形成する。16オンスのジャーに75.93gの2−EHAと、50.55gのMAと、201.5gの後述する第1キャップ化合物と、28.5gの酢酸エチル溶剤と、0.183gのVazo(登録商標)67とを添加して、予備反応混合物を形成する。2−EHA、MA、およびVazo(登録商標)67は上述のとおりである。
ハイブリッド3は以下の方法を用いて形成する。16オンスのジャーに44.0gの2−EHAと、44.0gのMAと、140.51gの同様に後述する第2キャップ化合物と、13.9gの酢酸エチル溶剤と、0.126gのVazo(登録商標)67とを添加して、予備反応混合物を形成する。2−EHA、MA、およびVazo(登録商標)67は上述のとおりである。
ハイブリッド4は以下の方法を用いて形成する。16オンスのジャーに75.62gの2−EHAと、51.4gのMAと、198.01gの同様に後述する第3キャップ化合物と、31.02gの酢酸エチル溶剤と、0.183gのVazo(登録商標)67とを添加して、予備反応混合物を形成する。2−EHA、MA、およびVazo(登録商標)67は上述のとおりである。
ハイブリッド5は以下の方法を用いて形成する。16オンスのジャーに63.4gの2−EHAと、42.4gのMAと、150.3gの同様に後述する第4キャップ化合物と、26.6gの酢酸エチル溶剤と、0.152gのVazo(登録商標)67とを添加して、予備反応混合物を形成する。2−EHA、MA、およびVazo(登録商標)67は上述のとおりである。
ハイブリッド6は、シリコン含有PSA、2−エチルヘキシルアクリレートおよびメチルアクリレートのラジカル重合によって生成したシリコーンアクリレートハイブリッドであり、酢酸エチル中42%の固体である。より具体的には、ハイブリッド6は32.91%のシリコン含有PSAと、14.00%の2−EHAと、7.54%のメチルアクリレートと、0.03%のVazo67と、45.52%の酢酸エチルとを用いて形成する。
ハイブリッド7は以下の方法を用いて形成する。16オンスのジャーに88.5gの2−EHAと、48.0gのMAと、213.53gのハイブリッド1を形成するのに用いるシリコン含有感圧接着剤組成物と、32.72gの酢酸エチル溶剤と、0.197gのVazo(登録商標)67とを添加して、予備反応混合物を形成する。2−EHA、MA、およびVazo(登録商標)67は上述のとおりである。
ハイブリッド8は以下の方法を用いて形成する。16オンスのジャーに81.36gの2−EHAと、87.02gのMAと、213.9gのハイブリッド1を形成するのに用いるシリコン含有感圧接着剤組成物と、32.77gの酢酸エチル溶剤と、0.195gのVazo(登録商標)67とを添加して、予備反応混合物を形成する。予備反応混合物中の物質を十分に均質になるまで15分撹拌する。混合後、92.1gの予備反応混合物および263.4gの酢酸エチル溶剤を、加熱マントル、撹拌ブレード/シャフト、窒素パージ、水冷冷却器および熱電対を備えた四つ口ガラス反応器に添加する。予備反応混合物の残りの部分を別の梨型ガラス貯蔵器に添加する。次いで、加熱および混合を反応器中の混合物に対して開始する。反応温度を78℃に設定する。反応温度に達してすぐに、混合物を60分間反応させた後、さらに予備反応混合物を反応器に添加する。60分経過後、貯蔵器中の混合物がなくなるまで、貯蔵器中の混合物を定量ポンプを用いて1.27グラム/分の速度で255分間添加する。反応器中の混合物を78℃でさらに437分間反応させて、ハイブリッドを形成する。完了後、ハイブリッドを室温まで冷却した後、ハイブリッドを反応器から取り出す。最終生成物は不透明である。
ハイブリッド9は以下の方法を用いて形成する。32オンスのジャーに682.9gの2−EHAと、682.6gのMAと、2128.4gのハイブリッド1を形成するのに用いるシリコン含有感圧接着剤組成物と、353.6gの酢酸エチル溶剤とを添加して、予備反応混合物Aを形成する。32オンスのジャーに1.987gのVazo(登録商標)67および822.41gの酢酸エチル溶剤を添加して、予備反応混合物Bを形成する。2−EHA、MA、ハイブリッド1を形成するのに用いるシリコン含有感圧接着剤組成物、およびVazo(登録商標)67は上述したとおりである。AおよびB両方を十分に均質になるまで15分撹拌する。混合後、1047.0gのA、206.0gのBおよび1831.2gの酢酸エチル溶剤を、加熱ジャケット、撹拌ブレード/シャフト、窒素パージ、水冷冷却器および熱電対を備えた四つ口ガラス反応器に添加する。AおよびBの残りの部分を別の梨型ガラス貯蔵器に添加する。次いで、加熱および混合を反応器中の混合物に対して開始する。反応温度を78℃に設定する。反応温度に達してすぐに、混合物を60分間反応させた後、さらに予備反応混合物を反応器に添加する。60分経過後、貯蔵器が空になるまで、定量ポンプを用いて貯蔵器中の混合物をAについて11.38グラム/分、Bについて3.16グラム/分の速度で添加する。反応器中の混合物を78℃でさらに1200分間反応させる。次いで、79.69gのHMDZおよび2.49gのトリフルオロ酢酸を反応器に添加し、混合物を78℃でさらに240分間反応させる。406.25gの水および82.1gのイソプロピルアルコールを次に反応器に添加し、混合物を78℃でさらに60分間反応させる。最終反応の60分後、水およびイソプロピルアルコールをディーンスタークトラップ中での回収により混合物から除去する。完了後、ハイブリッドを室温まで冷却した後、反応器から取り出す。最終生成物は不透明である。
第1キャップ化合物は以下の方法を用いて形成する。約700グラムの後述するシリコーン1を150℃の強制空気炉で120分間乾燥して、酢酸エチル溶剤を除去する。次いで、360.0グラムのシリコーン1および240.0グラムのキシレンを、加熱マントル、撹拌ブレード/シャフト、窒素パージ、水冷冷却器および熱電対を備えた四つ口ガラス反応器に入れる。これら成分を十分に均質になるまで混合する。次いで、19.47グラムのHMDZを反応器に添加し、システムの加熱を行う。反応温度を115℃に設定する。目標温度に達すると、混合物を11.25時間反応させて、反応の完了を確実にする。反応の内容物を室温まで冷却した後、反応器から取り出す。次いで、反応の内容物を200℃の強制空気炉で2時間乾燥して、キシレン溶剤を除去する。314.0グラムの反応の内容物および190.0グラムの酢酸エチルを32オンスのジャーに添加し、均質になるまで混合ホイール上で一晩混合する。470.0グラムの溶液および2.89グラムのCAを16オンスのジャーに添加し、物質を混合ホイール上で一晩混合する。pH紙の色変化により示されるように、すぐにHClが発生する。翌日、35.0グラムの重炭酸ナトリウムを添加して、HClの中和を補助する。試料を一晩混合する。次いで、試料を加圧ろ過して、微粒子を除去する。最終生成物は透明である。本例において、HMDZはトリメチルシロキシ官能性をもたらすシリコン含有キャッピング剤、より具体的にはヘキサメチルジシラザンである。また、この例において、CAはシリコン含有キャッピング剤、より具体的にはGelestから市販された3−メタクリロキシプロピルジメチルクロロシランである。
第2キャップ化合物は以下の方法を用いて形成する。約500グラムの上述および後述するシリコーン1を150℃の強制空気炉で120分間乾燥して、酢酸エチル溶剤を除去する。次に、180.71グラムの乾燥シリコーンおよび120.47グラムのキシレンを、加熱マントル、撹拌ブレード/シャフト、窒素パージ、水冷冷却器および熱電対を備えた四つ口ガラス反応器に入れる。これら成分を十分に均質になるまで混合する。次いで、9.74グラムの同様に上述したHMDZを反応器に添加し、システムの加熱を行う。反応温度を115℃に設定する。目標温度に達すると、混合物を491分間反応させ、反応の完了を確実にする。反応の内容物を室温まで冷却した後、反応器から取り出す。次いで、反応の内容物を200℃の強制空気炉で1.5時間乾燥して、キシレン溶剤を除去する。174.33グラムの反応の内容物および116.30グラムの酢酸エチルを16オンスのジャーに添加し、均質になるまで混合ホイール上で一晩混合する。259.71グラムの溶液および1.58グラムの同様に上述したCAを、撹拌ブレード/シャフト、窒素パージ、水冷冷却器および熱電対を備えた三つ口フラスコに添加し、24時間混合する。pH紙の色変化により示されるように、すぐにHClが発生する。50.0グラムの重炭酸ナトリウムをフラスコに添加して、HClの中和を補助する。試料を21時間混合する。次いで、試料を加圧ろ過して、微粒子を除去する。最終生成物は透明である。
第3キャップ化合物は以下の方法を用いて形成する。約700グラムの上述および後述するシリコーン1を150℃の強制空気炉で120分間乾燥して、酢酸エチル溶剤を除去する。次に、360.0グラムの乾燥シリコーンおよび240.0グラムのキシレンを、加熱マントル、撹拌ブレード/シャフト、窒素パージ、水冷冷却器および熱電対を備えた四つ口ガラス反応器に入れる。これら成分を十分に均質になるまで混合する。次いで、23.76グラムのHMDZを反応器に添加し、システムの加熱を行う。反応温度を115℃に設定する。目標温度に達すると、混合物を11.25時間反応させ、反応の完了を確実にする。反応の内容物を室温まで冷却した後、反応器から取り出す。次いで、反応の内容物を200℃の強制空気炉で2時間乾燥して、キシレン溶剤を除去する。300.87グラムの反応の内容物および178.0グラムの酢酸エチルを32オンスのジャーに添加し、均質になるまで混合ホイール上で一晩混合する。429.0グラムの溶液および2.61グラムのCAを16オンスのジャーに添加し、物質を混合ホイール上で一晩混合する。pH紙の色変化により示されるように、すぐにHClが発生する。翌日、35.0グラムの重炭酸ナトリウムを添加して、HClの中和を補助する。試料を一晩混合する。次いで、試料を加圧ろ過して、微粒子を除去する。最終生成物は透明である。HMDZおよびCAは上述のとおりである。
第4キャップ化合物は以下の方法を用いて形成する。約700グラムの上述および後述するシリコーン1を150℃の強制空気炉で120分間乾燥して、酢酸エチル溶剤を除去する。次に、360.0グラムの乾燥シリコーンおよび240.0グラムのキシレンを、加熱マントル、撹拌ブレード/シャフト、窒素パージ、水冷冷却器および熱電対を備えた四つ口ガラス反応器に入れる。これら成分を十分に均質になるまで混合する。次いで、15.20グラムのHMDZを反応器に添加し、システムの加熱を行う。反応温度を115℃に設定する。目標温度に達すると、混合物を11.25時間反応させ、反応の完了を確実にする。反応の内容物を室温まで冷却した後、反応器から取り出す。次いで、反応の内容物を200℃の強制空気炉で2時間乾燥して、キシレン溶剤を除去する。308.0グラムの反応の内容物および185.0グラムの酢酸エチルを32オンスのジャーに添加し、均質になるまで混合ホイール上で一晩混合する。459.0グラムの溶液および2.79グラムのCAを16オンスのジャーに添加し、物質を混合ホイール上で一晩混合する。pH紙の色変化により示されるように、すぐにHClが発生する。翌日、35.0グラムの重炭酸ナトリウムを添加して、HClの中和を補助する。試料を一晩混合する。次いで、試料を加圧ろ過して、微粒子を除去する。最終生成物は透明である。HMDZおよびCAは上述のとおりである。
実施例1〜60のそれぞれは、前述のハイブリッドの1つをバイアル中に添加することにより形成する。その後、シリコーン1および/もしくは2またはアクリレート1もバイアルに添加する。1つ以上の賦形剤および/または医薬活性薬剤も実施例に応じて添加する。さらに、酢酸エチルを必要に応じて添加して、45%〜50%固体に調整する。次に、各バイアルを、プロセス回転炉を用いてブレンドし、確実に混合する。ハイブリッド、シリコーンおよびアクリレート、賦形剤、ならびに医薬活性薬剤の重量パーセントを以下の表に記載する。
Claims (10)
- 相分離に抵抗し、
A.シリコーン、アクリレートおよびこれらの組み合わせの少なくとも1つと、
B.シリコーン官能性および(メタ)アクリレート官能性を有し、(1)シリコン含有感圧接着剤組成物および(2)(メタ)アクリレートモノマーの(3)開始剤の存在下での反応生成物であるシリコーンアクリレートハイブリッド相溶化剤とを含み、
前記(1)シリコン含有感圧接着剤組成物が任意の触媒の存在下での(a)シリコーン樹脂と、(b)シリコーンポリマーと、(c)シリコン含有キャッピング剤との縮合反応生成物を含み、
ここで前記(a)シリコーン樹脂および(b)シリコーンポリマーを反応させて感圧接着剤を形成し、
前記(c)シリコン含有キャッピング剤を(a)シリコーン樹脂および(b)シリコーンポリマーの反応前、反応中または反応後に導入し、
前記(a)シリコーン樹脂および(b)シリコーンポリマーを縮合反応させて前記感圧接着剤を形成した後に、前記(c)シリコン含有キャッピング剤が該感圧接着剤と反応するか、または
前記(c)シリコン含有キャッピング剤が前記(a)シリコーン樹脂および(b)シリコーンポリマーと現場で反応し、
前記(A)のアクリレートが任意に2−エチルヘキシルアクリレートおよびメタクリレートの組み合わせを含むことを特徴とする単相シリコーンアクリレート製剤。 - 約10〜約90重量パーセントのアクリレート含有量を有する請求項1に記載の単相製剤。
- 約10〜約90重量パーセントのシリコーン含有量を有する請求項1または2に記載の単相製剤。
- 前記シリコーンアクリレートハイブリッド相溶化剤が、約50重量パーセントのシリコーン含有量および約50重量パーセントの(メタ)アクリレート含有量を有する請求項1に記載の単相製剤。
- 前記シリコーンアクリレートハイブリッド相溶化剤が、約25重量パーセントのシリコーン含有量および約75重量パーセントの(メタ)アクリレート含有量を有する請求項1に記載の単相製剤。
- 前記シリコーンアクリレートハイブリッド相溶化剤が、約75重量パーセントのシリコーン含有量および約25重量パーセントの(メタ)アクリレート含有量を有する請求項1に記載の単相製剤。
- 賦形剤をさらに含み、該賦形剤が任意にジプロピレングリコール、オレイン酸、オレイルアルコール、鉱油およびこれらの組み合わせの群から選択される請求項1〜6のいずれか1項に記載の単相製剤。
- 医薬活性薬剤をさらに含み、該医薬活性薬剤が任意にケトプロフェン、エストラジオール、クロニジンおよびこれらの組み合わせの群から選択される請求項1〜7のいずれか1項に記載の単相製剤。
- 前記(A)のシリコーンが、シラノール末端ブロックポリジメチルシロキサンおよびシリケート樹脂の縮合反応生成物であり、該ポリジメチルシロキサンおよび/またはシリケート樹脂を任意にトリメチルシロキシ官能基でキャップする請求項1〜8のいずれか1項に記載の単相製剤。
- (A)シリコーン、アクリレートおよびこれらの組み合わせの少なくとも1つと、(B)シリコーン官能性および(メタ)アクリレート官能性を有するシリコーンアクリレートハイブリッド相溶化剤とを含む単相シリコーンアクリレート製剤の相分離を最小限にする方法であって、(A)および(B)を組み合わせて単相シリコーンアクリレート製剤を形成する工程を備え、該(B)シリコーンアクリレートハイブリッド相溶化剤が(1)シリコン含有感圧接着剤組成物および(2)(メタ)アクリレートモノマーの(3)開始剤の存在下での反応生成物であり、
前記(1)シリコン含有感圧接着剤組成物が、任意の触媒の存在下での(a)シリコーン樹脂と、(b)シリコーンポリマーと、(c)シリコン含有キャッピング剤との縮合反応生成物を含み、
ここで前記(a)シリコーン樹脂および(b)シリコーンポリマーを反応させて感圧接着剤を形成し、
前記(a)シリコーン樹脂および(b)シリコーンポリマーの反応前、反応中または反応後に前記(c)シリコン含有キャッピング剤を導入し、
前記(a)シリコーン樹脂および(b)シリコーンポリマーを縮合反応させて前記感圧接着剤を形成した後に、前記(c)シリコン含有キャッピング剤が該感圧接着剤と反応するか、または
前記(c)シリコン含有キャッピング剤が前記(a)シリコーン樹脂および(b)シリコーンポリマーと現場で反応することを特徴とする方法。
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Cited By (1)
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JP2018511661A (ja) * | 2015-01-29 | 2018-04-26 | ダウ コーニング コーポレーションDow Corning Corporation | シリコーンアクリレート組成物及びその調製方法 |
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CN103342782B (zh) * | 2013-07-02 | 2014-06-25 | 广东海顺新材料科技有限公司 | 有机硅改性丙烯酸酯乳液、制备方法及其制备成的水性人造石 |
EP3256504B1 (en) * | 2015-02-09 | 2020-06-24 | Dow Silicones Corporation | Multi-phase silicone acrylic hybrid visco-elastic compositions and methods of making same |
CN111094483A (zh) * | 2017-08-31 | 2020-05-01 | 三星Sdi株式会社 | 接着膜及包括其的光学构件 |
TW202019992A (zh) * | 2018-05-16 | 2020-06-01 | 德商漢高智慧財產控股公司 | 製造聚矽氧-丙烯酸混合型壓敏性黏著劑組合物之一鍋製程 |
KR102430601B1 (ko) | 2020-03-03 | 2022-08-08 | 삼성에스디아이 주식회사 | 점착 필름, 이를 포함하는 광학 부재 및 이를 포함하는 광학표시장치 |
KR102527459B1 (ko) | 2020-05-29 | 2023-04-28 | 삼성에스디아이 주식회사 | 점착성 보호 필름, 이를 포함하는 광학 부재 및 이를 포함하는 광학표시장치 |
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JP6108759B2 (ja) | 2017-04-05 |
CN103055315A (zh) | 2013-04-24 |
EP2584016A1 (en) | 2013-04-24 |
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