TWI409089B - 預填充式注射器 - Google Patents
預填充式注射器 Download PDFInfo
- Publication number
- TWI409089B TWI409089B TW096148663A TW96148663A TWI409089B TW I409089 B TWI409089 B TW I409089B TW 096148663 A TW096148663 A TW 096148663A TW 96148663 A TW96148663 A TW 96148663A TW I409089 B TWI409089 B TW I409089B
- Authority
- TW
- Taiwan
- Prior art keywords
- dicarboxylic acid
- unit
- polyester resin
- prefilled syringe
- group
- Prior art date
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- 229940071643 prefilled syringe Drugs 0.000 title claims abstract description 36
- 229920001225 polyester resin Polymers 0.000 claims abstract description 69
- 239000004645 polyester resin Substances 0.000 claims abstract description 69
- 230000035699 permeability Effects 0.000 claims abstract description 53
- 150000002009 diols Chemical group 0.000 claims abstract description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000001301 oxygen Substances 0.000 claims abstract description 24
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 24
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims abstract description 19
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 15
- 229920005989 resin Polymers 0.000 claims abstract description 14
- 239000011347 resin Substances 0.000 claims abstract description 14
- 230000009477 glass transition Effects 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 238000005809 transesterification reaction Methods 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 4
- NECLQTPQJZSWOE-UHFFFAOYSA-N spiro[5.5]undecane Chemical compound C1CCCCC21CCCCC2 NECLQTPQJZSWOE-UHFFFAOYSA-N 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 3
- CHDRADPXNRULGA-UHFFFAOYSA-N naphthalene-1,3-dicarboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC(C(O)=O)=C21 CHDRADPXNRULGA-UHFFFAOYSA-N 0.000 claims description 2
- ABMFBCRYHDZLRD-UHFFFAOYSA-N naphthalene-1,4-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1 ABMFBCRYHDZLRD-UHFFFAOYSA-N 0.000 claims description 2
- DFFZOPXDTCDZDP-UHFFFAOYSA-N naphthalene-1,5-dicarboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1C(O)=O DFFZOPXDTCDZDP-UHFFFAOYSA-N 0.000 claims description 2
- WPUMVKJOWWJPRK-UHFFFAOYSA-N naphthalene-2,7-dicarboxylic acid Chemical compound C1=CC(C(O)=O)=CC2=CC(C(=O)O)=CC=C21 WPUMVKJOWWJPRK-UHFFFAOYSA-N 0.000 claims description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 15
- -1 polyethylene Polymers 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 9
- 238000011156 evaluation Methods 0.000 description 9
- 238000005259 measurement Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 8
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 7
- 229930003316 Vitamin D Natural products 0.000 description 7
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 7
- 239000000470 constituent Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000001179 sorption measurement Methods 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 235000019166 vitamin D Nutrition 0.000 description 7
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- 229940046008 vitamin d Drugs 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000000945 filler Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000004743 Polypropylene Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
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- 229920001155 polypropylene Polymers 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- 238000011049 filling Methods 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 4
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- 230000000052 comparative effect Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
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- 238000000465 moulding Methods 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
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- 238000006068 polycondensation reaction Methods 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000573 polyethylene Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 238000004659 sterilization and disinfection Methods 0.000 description 3
- WOZVHXUHUFLZGK-UHFFFAOYSA-N terephthalic acid dimethyl ester Natural products COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
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- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 2
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
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- 229910052787 antimony Inorganic materials 0.000 description 2
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M5/00—Devices for bringing media into the body in a subcutaneous, intra-vascular or intramuscular way; Accessories therefor, e.g. filling or cleaning devices, arm-rests
- A61M5/178—Syringes
- A61M5/31—Details
- A61M5/3129—Syringe barrels
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M5/00—Devices for bringing media into the body in a subcutaneous, intra-vascular or intramuscular way; Accessories therefor, e.g. filling or cleaning devices, arm-rests
- A61M5/178—Syringes
- A61M5/28—Syringe ampoules or carpules, i.e. ampoules or carpules provided with a needle
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Anesthesiology (AREA)
- Vascular Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Infusion, Injection, And Reservoir Apparatuses (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Description
本發明係相關於在密封狀態下，預先將藥液填充之注射器(預填充式注射器)。
先前，注射器的材料係使用玻璃。惟，玻璃若掉落則破損，而以聚碳酸酯、聚乙烯、聚丙烯、環烴聚合物等、塑膠來替代。
另一方面，先前注射器的使用方法，係在使用時將藥液往上吸至注射器之方法。惟，該方法的操作效率差，且發生藥液的填充錯誤等人為疏失，而進展至預先填充規定量的規定藥液之預填充式注射器。
預填充式注射器的材料，基於上述理由，宜為塑膠，因塑膠特有的水蒸氣透過性(透濕性)、透氧性、吸附性而限制其使用，現今尚無替代品。
例如聚碳酸酯的注射器，因其透濕性而使藥劑的水分蒸發，聚丙烯或環烴聚合物的注射器，因其透氧性而使藥液氧化，且因其吸附性而使特定的藥劑成分變薄。
聚酯樹脂係低透氧性、低吸附性。聚乙烯萘酯係兼具低透濕性，惟因其結晶性而於煮沸消毒時發生部分結晶化，故此，其尺寸發生變化而無法使用為注射器。於聚酯樹脂中尚無兼具耐煮沸消毒之耐熱性和低透濕性者。
專利文獻1中記載一種使用丁基橡膠於墊圈之低吸附性的合成樹脂製預填充式注射器，惟不具充分的高耐熱
性、低吸附性、低透濕性、低透氧性。
專利文獻1：特開2004－298220號公報
鑑於上述問題，本發明之目的係提供一種高耐熱性、低透濕性、低透氧性、低吸附性之預填充式注射器。
本發明係相關於一種預填充式注射器，其含有至少分別構成筒及接合部之樹脂，該樹脂係二醇單元中之1~30莫耳%為具有環狀縮醛骨架之二醇單元，二羧酸單元中之70莫耳%以上為具有萘骨架之二羧酸單元，滿足全部下述式(i)~(iii)之聚酯樹脂。
(i)以微差掃瞄熱量卡計測得之玻璃轉移溫度為110℃以上
(ii)透濕係數為1g．mm/m2
/日以下
(iii)透氧係數為10cc．mm/m2
/日/atm以下
本發明的預填充式注射器係高耐熱性、低透濕性、低透氧性、低吸附性，較先前的塑膠製預填充式注射器，更提升長期保存性。
以下，詳細地說明本發明。
本發明的預填充注射器，係由含有至少分別構成筒及接合部之樹脂，該樹脂係二醇單元中之1~30莫耳%為具有環狀縮醛骨架之二醇單元，二羧酸單元中之70莫耳%以上為具有萘骨架的二羧酸單元的聚酯樹脂之樹脂所構成。
使用於本發明的聚酯樹脂中的具有環狀縮醛骨架之二醇單元之比例係1~30莫耳%。含有1莫耳%以上的具有環狀縮醛骨架之二醇單元，可提高聚酯樹脂的玻璃轉移溫度，提升該聚酯樹脂之耐熱性。且結晶性降低，故不發生煮沸消毒時的部分結晶化、伴隨的尺寸變化、白化、脆化。具有環狀縮醛骨架的二醇單元之比例宜為3莫耳%以上，尤宜5莫耳%以上。另一方面，若聚酯樹脂中的具有環狀縮醛骨架的二醇單元之比例超過30莫耳%，則增加聚酯樹脂之透濕性、透氧性，較不適宜。具有環狀縮醛骨架的二醇單元之比例宜為25莫耳%以下，較宜為22莫耳%以下，更宜為20莫耳%以下，尤宜15莫耳%以下。因此，從聚酯樹脂的耐熱性、透濕性之觀點，具有環狀縮醛骨架之二醇單元之比例宜為1~25莫耳%，更宜為3~25莫耳%，尤宜5~22莫耳%。
使用於本發明的聚酯樹脂的二醇構成單元中之具有環狀縮醛骨架之二醇單元，宜為來自一般式(1)：
或一般式(2)：
表示的化合物之單元。一般式(1)和(2)中，R1
及R2
係各自獨立，表示選自由碳數為1~10之脂肪族烴基、碳數為3~10之脂環式烴基及碳數為6~10之芳香族烴基所構成群組的烴基。R1
及R2
各宜為亞甲基、伸乙基、伸丙基、伸丁基或其結構異構物。該結構異構物例如異伸丙基、異伸丁基。R3
表示選自由碳數為1~10之脂肪族烴基、碳數為3~10之脂環式烴基及碳數為6~10之芳香族烴基所構成群組的烴基。R3
宜為甲基、乙基、丙基、丁基或其結構異構物。該結構異構物例如來自異丙基、異丁基。一般式(1)及(2)之各個化合物，尤宜為3,9－雙(1,1－二甲基－2－羥乙基)－2,4,8,10－四螺[5.5]十一烷、5－羥甲基－5－乙基－2－(1,1－二甲基－2－羥乙基)－1,3－二烷等。上述具有環狀縮醛骨架之二醇單元係可由1種類構成，亦可由2種類以上構成。
具有環狀縮醛骨架的二醇單元以外之二醇構成單元，係無特別的限制，例如來自乙二醇、三甲二醇、1,4－丁二醇、1,5－戊二醇、1,6－己二醇、二乙二醇、丙二醇、新戊二醇等
脂肪族二醇類；1,3－環己烷二甲醇、1,4－環己烷二甲醇、1,2－十氫化萘二甲醇、1,3－十氫化萘二甲醇、1,4－十氫化萘二甲醇、1,5－十氫化萘二甲醇、1,6－十氫化萘二甲醇、2,7－十氫化萘二甲醇、四氫化萘二甲醇、降茨烷二甲醇、三環癸烷二甲醇、五環十二烷二甲醇等脂環式二醇類；聚乙二醇、聚丙二醇、聚丁二醇等聚醚化合物類；4,4’－(1－甲基亞乙基)雙酚、亞甲基雙酚(雙酚F)、4,4’－環亞己基雙酚(雙酚Z)、4,4’－磺醯基雙酚(雙酚S)等雙酚類；上述雙酚類的環氧化物附加物；氫輥、間苯二酚、4,4’－二羥聯苯、4,4’－二羥二苯醚、4,4’－二羥二苯基二苯基酮等芳香族二羥化合物；上述芳香族二羥化合物的環氧化物附加物等之二醇單元。考量聚酯樹脂的機械強度、耐熱性及二醇的取得容易度等，宜為來自乙二醇、三甲二醇、1,4－丁二醇、1,4－環己烷二甲醇等之二醇單元，尤宜乙二醇單元。上述具有環狀縮醛骨架的二醇單元以外之二醇構成單元，可由1種類構成，亦可由2種類以上構成。
另一方面，使用於本發明的聚酯樹脂中的具有萘骨架之二羧酸單元之比例係70莫耳%以上。含有70莫耳%以上的具有萘骨架之二羧酸單元，可提高聚酯樹脂的玻璃轉移溫度，亦即同時達到提升耐熱性、降低透濕係數、降低透氧係數。另一方面，若聚酯樹脂中的具有萘骨架之二羧酸單元之比例低於70莫耳%，則增加聚酯樹脂的透濕係數、透氧係數，且降低耐熱性，較不適當。因此，從聚酯
樹脂的耐熱性、透濕性、透氧性之觀點，具有萘骨架之二羧酸單元之比例宜為85莫耳%以上，尤宜95莫耳%以上。
使用於本發明的聚酯樹脂中的具有萘骨架之二羧酸單元，例如來自1,3－萘二羧酸、1,4－萘二羧酸、1,5－萘二羧酸、2,6－萘二羧酸及2,7－萘二羧酸等之單元。聚酯樹脂中的具有萘骨架之二羧酸單元，可由1種類構成，亦可由2種類以上構成。從耐熱性、低透濕性之觀點，最宜為來自2,6－萘二羧酸之單元。
使用於本發明的聚酯樹脂之具有萘骨架之二羧酸單元以外之二羧酸單元，無特別的限制，例如來自琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、癸烷二羧酸、十二烷二羧酸、環己烷二羧酸、十氫萘烷二羧酸、降茨烷二羧酸、三環癸烷二羧酸、五環癸烷二羧酸、3,9－雙(1,1－二甲基－2－羥乙基)－2,4,8,10－四螺[5.5]十一烷、5－羧－5－乙基－2－(1,1－二甲基－2－羧乙基)－1,3－二烷、二聚物酸等脂肪族二羧酸之單元；對苯二甲酸、間苯二甲酸、苯二甲酸、2－甲基對苯二甲酸、聯苯二羧酸、四氫化萘二羧酸等芳香族二羧酸之單元。考量聚酯樹脂的機械強度、耐熱性，宜為來自芳香族二羧酸之單元，考量二羧酸的取得容易度，宜為來自對苯二甲酸或間苯二甲酸來源之單元。聚酯樹脂中的具有萘骨架的二羧酸以外之二羧酸構成單元，可由1種類構成，亦可由2種類以上構成。
於聚酯樹脂中，為調整熔融黏彈性和分子量等，在不
危及本發明的目的之範圍，亦可含有來自丁醇、己醇、辛醇等單醇之單元或三羥甲基丙烷、甘油、1,3,5－戊三醇、季戊四醇等3價以上來自多價醇之單元、來自苯甲酸、丙酸、丁酸等單羧酸之單元、來自偏苯三酸、均苯四甲酸等多價羧酸之單元、來自乙醇酸、乳酸、羥丁酸、2－羥異丁酸、羥苯甲酸等羥酸之單元。
使用於本發明的聚酯樹脂，特別考其量高耐熱性、低透濕性、低透氧性、機械性能等，具有環狀縮醛骨架的二醇單元宜為來自3,9－雙(1,1－二甲基－2－羥乙基)－2,4,8,10－四螺[5.5]十一烷之單位，具有環狀縮醛骨架的二醇單元以外之二醇構成單元為來自二乙醇之單元，全部的二羧酸構成單元宜為2,6－萘二羧酸來源之單元。
使用於本發明的聚酯樹脂係滿足全部下述式(i)~(iii)。
(i)以微差掃瞄熱量卡計測得之玻璃轉移溫度為110℃以上；(ii)透濕係數為1g．mm/m2
/日以下；(iii)透氧係數為10cc．mm/m2
/日/atm以下
如上述般，使用於本發明的聚酯樹脂之玻璃轉移溫度，以微差掃瞄熱量卡計測得之值為110℃以上，宜為115℃以上，尤宜120℃以上。聚酯樹脂之玻璃轉移溫度在上述範圍時，本發明的預填充式注射器係可煮沸消毒。又藉由適當地選擇如上述般具有環狀縮醛骨架之二醇及具有萘骨
架之二羧酸，可使聚酯樹脂之玻璃轉移溫度為上述範圍內之值。又玻璃轉移溫度之上限值，無特別的限制，惟考量聚酯樹脂的構成單位之種類、其組成，一般為160℃。
使用於本發明的聚酯樹脂之透濕係數，在40℃、90% RH的條件下為1g．mm/m2
/日以下，宜為0.9g．mm/m2
/日以下，尤宜0.8g．mm/m2
/日以下。聚酯樹脂之透濕係數在上述範圍時，本發明的預填充式注射器可長期保存藥液。又藉由適當地選擇如上述般具有環狀縮醛骨架之二醇及具有萘骨架之二羧酸，可使聚酯樹脂之透濕係數為上述範圍內之值。
使用於本發明的聚酯樹脂之透氧係數，在23℃、65% RH的條件下為10cc．mm/m2
/日/atm以下，宜為7cc．mm/m2
/日/atm以下，尤宜5cc．mm/m2
/日/atm以下。聚酯樹脂之透濕係數在上述範圍時，可預防藥液的氧化劣化，可增加保存安定性。藉由適當地選擇如上述般具有環狀縮醛骨架之二醇及具有萘骨架之二羧酸，可使聚酯樹脂之透氧係數為上述範圍內之值。
使用於本發明的聚酯樹脂，係與其他聚酯樹脂同樣為低吸附性。例如實際上不吸附維生素D或檸檬烯。
使用於本發明的聚酯樹脂之極限黏度(IV)，可因應成形方法和用途適當地選擇，宜為使用苯酚和1,1,2,2－四氯乙烷的質量比6：4之混合溶劑，於25℃的測定值在0.5~1.5dl/g之範圍，更宜0.5~1.2dl/g，尤宜0.5~1.0dl/g。若極限黏度
在此範圍，則使用於本發明的聚酯樹脂之成形性及機械性能的平衡優異。
使用於本發明的聚酯樹脂之製法，無特別的限制，可使用先前既知的任一種聚酯之製法。例如酯交換法、直接酯化法等熔融聚合法或溶液聚合法等。直接酯化法中，二羧酸以不具有環狀縮醛骨架之二醇進行酯化後，必須低酸價化後再使具有環狀縮醛骨架之二醇反應。上述聚酯樹脂之製法中，考量原料之取得容易與否，宜為酯交換法。
使用於製造聚酯樹脂時之酯交換催化劑、酯化催化劑、縮聚催化劑等各種催化劑、抗醚化劑、熱安定劑、光安定劑等各種安定劑、聚合調整劑等，可使用先前既知的任一種，這些係可因應反應速度或聚酯樹脂的色調、安全性、熱安定性、耐候性、自體溶出性等而適當地選擇。上述各種催化劑例如鋅、鉛、鈰、鎘、錳、鈷、鋰、鈉、鉀、鈣、鎳、鎂、釩、鋁、鈦、銻、錫等金屬化合物(例如脂肪酸鹽、碳酸鹽、磷酸鹽、氫氧化物、氯化物、氧化物、醇鹽)和金屬鎂等，這些可單獨使用，亦可組合複數種而使用。酯交換法中的酯交換催化劑，因高活性、少副反應，故宜為上述中的錳化合物，縮聚催化劑宜為上述中的銻、鈦化合物。
使用於本發明的聚酯樹脂中，可添加抗氧化劑、光安定劑、紫外線吸收劑、可塑劑、增量劑、退光劑、除濕劑、抗靜電劑、抗沉澱劑、界面活性劑、流動改良劑、乾燥油、
蠟類、填充劑、著色劑、增強劑、表面平滑劑、塗平劑、硬化反應促進劑、增稠劑等各種添加劑、成形輔助劑。
其次，說明本發明的預填充式注射器。
本發明的預填充式注射器係以射出成形法來製造。本發明的預填充式注射器與一般的注射器無太大變化，至少由為填充藥液之筒、為在筒的一端連接注射針之接合部及使用時為擠押藥液之柱塞所構成，至少筒及接合部係由含有使用於本發明的上述聚酯樹脂之樹脂成形時所必需者。
從本發明的效果之觀點，含有聚酯樹脂之樹脂中，宜含有60質量%以上之上述聚酯樹脂，更宜為80質量%以上，尤宜含有100質量%。聚酯樹脂以外之樹脂，可含有例如聚丙烯、聚乙烯、聚碳酸酯、環烯聚合物等。
本發明的預填充式注射器中，筒和接合部係一體成形，亦可使個別成形物接合。接合部的前端必需密封，惟其方法係使接合部前端的樹脂於熔融狀態加熱，以鉗子等夾入使其熔敷等。
本發明的預填充式注射器，為增加柱塞和筒之黏密性，亦可使用填料。亦可使用用於本發明的聚酯樹脂為填料，惟宜為橡膠彈性材料，例如丁基橡膠、異戊橡膠、熱可塑性彈性體等。因使用填料等而柱塞和內容物不接合時，使用於柱塞的樹脂，除本發明的聚酯樹脂以外，可使用例如聚丙烯、聚乙烯、聚碳酸酯、環烯聚合物等，惟柱塞和內容物接觸時，柱塞宜使用用於本發明之聚酯樹脂。
本發明的預填充式注射器具有比玻璃製注射器更優異之耐衝擊性。
本發明的預填充式注射器之填充物，無特別之限制，惟從本發明的效果之觀點，宜為脂溶性化合物，從其化合物的助益性之觀點，宜為萜類、蛋白質等。更具體而言，萜類宜為例如維生素A、維生素D、維生素E、維生素K等脂溶性維生素、檸檬烯、薄荷醇、香茅烯(myrcene)、羅勒萜(ocimene)、波斯菊萜(cosmene)等單萜、菌綠烯醇(farnesol)醇、橙花三級醇(nerolidol)、β－安烯醇(sinensal)、丁子香烯(caryophyllene)等倍半萜、雙萜、二倍半萜(sesterterpene)、三萜、四萜等。蛋白質例如卵白蛋白、血清白蛋白、乳白蛋白等白蛋白等。以含胜肽鍵的化合物修飾之萜類亦可使用為填充物，例如Paclitaxel。本發明的預填充式注射器，當填充這些化合物時，這些化合物的吸附量變少。
以下，舉出實施例更具體地說明本發明，惟本發明不受限於這些實施例。
使用於本實施例的聚酯樹脂及預填充式注射器之評估方法如下所述。
(1)具有環狀縮醛骨架之二醇單元和具有萘骨架之二羧酸單元之比例
以1
H－NMR測定來算出聚酯樹脂中的具有環狀縮醛骨架之二醇單元和具有萘骨架之二羧酸單元之比例。測定裝置係使用日本電子(股)製JNM－AL400，於400MHz測定。溶劑係使用重三氯甲烷。
(2)玻璃轉移溫度(Tg)
使用島津製作所製DSC/TA－50WS測定聚酯樹脂之玻璃轉移溫度，將大約10mg的聚酯樹脂放入鋁製非密閉容器，氮氣(30ml/min)氣流中，以升溫速度20℃/min加熱至280℃，使熔融物急速冷卻作為測定用試驗品。於相同條件下測定該試驗品，僅發生DSC曲線的轉移前後的基線差的1/2之溫度作為玻璃轉移溫度。
(3)極限黏度(IV)
極限黏度測定的試驗品之調製，係將0.5g的聚酯樹脂加熱溶解於120g的苯酚和1,1,2,2－四氯乙烷之混合溶劑(質量比＝6：4)，過濾後冷卻至25℃而成。測定裝置係使用(股)柴山科學機械製作所製的毛細管黏度計自動測定裝置SS－300－L1，於溫度25℃進行測定。
(4)透濕係數
於熔融擠壓成形製得的厚度200 μm之薄膜作為測定用試驗品，測定聚酯樹脂之透濕度。測定條件為40℃、90% RH。測定裝置係LYSSY公司製的水蒸氣透過度計L80－4005L。由測得的透濕度，依據下式算出透濕係數。
透濕係數(g．mm/m2
/日)＝透濕度(g/m2
/日)×厚度(mm)
(5)透氧係數
於熔融擠壓成形製得的厚度200 μm之薄膜作為測定用試驗品，測定聚酯樹脂之透氧度。測定條件為23℃、65% RH。測定裝置係MOCON公司製的OX－TRAN2/21。由測得的透氧度，依據下式算出透氧係數。
透氧係數(cc．mm/m2
/日/atm)＝透氧度(cc/m2
/日/atm)×厚度(mm)
(6)水之蒸散率
將填充水且密封的預填充式注射器保存於40℃、75% RH的恆溫恆濕機中3個月。由保存前後之包含內容物的注射器之質量W1(保存前)、W2(保存後)及初期的水填充量(w1)，以下式測定蒸散率。
水的蒸散率(%)＝[(W1－W2)/w1]×100
(7)於蛋白質吸附試驗之氮增加量
將填充蛋白質水溶液的預填充式注射器保存於23℃、50% RH條件下8日。保存後的預填充式注射器，以純水清洗5次後，於氮元素分析中定量氮量(N2)。以N2和蛋白質水溶液填充前的氮元素量(N1)之差，作為在蛋白質吸附試驗之氮增加量。蛋白質水溶液係使用Sigma Aldrich Japan製的白蛋白(牛來源、粉末)，餾分V的1wt%水溶液。元素分析係使用三菱化成製總氮分析計TN－10。
(8)維生素D之保存率
將填充含有定量(M1)的維生素D溶液之預填充式注
射器保存於23℃、50% RH條件下8日。於液態色譜層析中定量保存後的內容物之維生素D量(M2)，由下式算出維生素D之保存率。
維生素D之保存率(%)＝[1－(M1－M2)/M1]×100
(9)落下試驗
使填充水之預填充式注射器，從高度1.5m連續5次自由落下。對於10個試驗品，若試驗期間無任何破損即為合格。
(10)煮沸試驗
將填充水之預填充式注射器放入沸騰水中煮沸消毒10分鐘後，觀察柱塞和筒之間是否有漏水或白化等外觀變化。均不發生者即為合格。
將表1的原料單體放入具備填充塔式精餾塔、部分冷凝器、全冷凝器、冷槽、攪拌機、加熱裝置、氮導入管之0.15公升的聚酯製造裝置，在相對於二羧酸成分0.03莫耳%的醋酸錳四水合物之存在下，於氮氣環境下升溫至215℃，進行酯交換反應。二羧酸成分的反應轉化率達90%以上後，加入相對於二羧酸成分0.02莫耳%的氧化銻(III)和0.06莫耳%的磷酸三乙酯，緩慢地進行升溫和減壓，最後，於280℃、0.1kPa以下的條件下進行縮聚。於達到適度的熔融黏度時終止反應，製得聚酯樹脂。
於具備T模頭的25mm單軸擠壓機，以240~260℃使製
得的聚酯樹脂熔融擠壓成形，製得厚度200 μm的薄膜。
使製得的聚酯樹脂及薄膜進行上述評估，其結果如表1所示。
又，表中的簡稱之意，如下所示。
NDCM：2,6－萘二羧酸二甲酯
DMT：對苯二甲酸二甲酯
EG：乙二醇
SPG：3,9－雙(1,1－二甲基－2－羥乙基)－2,4,8,10－四螺[5.5]十一烷
於合模壓力100噸的射出成形機，以240~260℃的溫度條件，使上述製得的聚酯樹脂射出成形，作成接合部一體型的筒、柱塞。使柱塞前端具有丁基橡膠製的填料，準備容量5ml的注射器。使製得的注射器進行上述的評估，其結果如表1所示。
實施例1中，除使用Primepolymer公司製的聚丙烯J－452HP取代聚酯樹脂以外，和實施例1同樣地準備注射器，並進行評估。評估結果如表2所示。
實施例1中，除使用Ticona GmbH公司製的環烯聚合物－TOPAS6013取代聚酯樹脂以外，和實施例1同樣地準備注射器，並進行評估。評估結果如表2所示。
Claims (7)
- 一種預填充式注射器，其含有至少分別構成筒及接合部之樹脂，該樹脂係二醇單元中之1~30莫耳%為具有環狀縮醛骨架之二醇單元，二羧酸單元中之70莫耳%以上為具有萘骨架之二羧酸單元，滿足全部下述式(i)至(iii)之聚酯樹脂，(i)以微差掃瞄熱量卡計測得之玻璃轉移溫度為110℃以上；(ii)透濕係數為1g˙mm/m2 /日以下；(iii)透氧係數為10cc˙mm/m2 /日/atm以下。
- 如申請專利範圍第1項之預填充式注射器，其中具有環狀縮醛骨架之二醇單元係來自以一般式(1)：
- 如申請專利範圍第1項之預填充式注射器，其中具有環狀縮醛骨架之二醇單元係來自3,9-雙(1,1-二甲基-2-羥乙基)-2,4,8,10-四螺[5.5]十一烷、或5-羥甲基-5-乙基-2-(1,1-二甲基-2-羥乙基)-1,3-二烷之二醇單元。
- 如申請專利範圍第1項之預填充式注射器，其中二羧酸單元係來自選自由1,3-萘二羧酸、1,4-萘二羧酸、1,5-萘二羧酸、2,6-萘二羧酸及2,7-萘二羧酸所構成群組之1種以上之二羧酸。
- 如申請專利範圍第1項之預填充式注射器，其中二羧酸單元係來自2,6-萘二羧酸。
- 如申請專利範圍第1項之預填充式注射器，其中聚酯樹脂之於25℃的極限黏度(IV)為0.5~1.5dl/g之範圍。
- 如申請專利範圍第1項之預填充式注射器，其中聚酯樹脂係使用酯交換法所製造之物。
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| JP2006342764 | 2006-12-20 |
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| US (1) | US8398600B2 (zh) |
| EP (1) | EP2095837B1 (zh) |
| JP (1) | JP5374159B2 (zh) |
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| US20140223862A1 (en) * | 2010-07-16 | 2014-08-14 | Safety Syringes, Inc. | Manufacturing Process For Packing Of Injectables |
| WO2013051686A1 (ja) | 2011-10-07 | 2013-04-11 | 三菱瓦斯化学株式会社 | 医療用包装容器 |
| JP6015322B2 (ja) * | 2012-10-05 | 2016-10-26 | 三菱瓦斯化学株式会社 | 医療用多層容器 |
| JP6015334B2 (ja) * | 2012-10-16 | 2016-10-26 | 三菱瓦斯化学株式会社 | 酸素吸収性紙容器 |
| JP6015344B2 (ja) * | 2012-10-25 | 2016-10-26 | 三菱瓦斯化学株式会社 | バイオ医薬の保存方法 |
| JP6015343B2 (ja) * | 2012-10-25 | 2016-10-26 | 三菱瓦斯化学株式会社 | 医療用多層容器 |
| JP6015328B2 (ja) * | 2012-10-10 | 2016-10-26 | 三菱瓦斯化学株式会社 | 酸素吸収性多層インジェクション成形体 |
| JP5966852B2 (ja) * | 2012-10-24 | 2016-08-10 | 三菱瓦斯化学株式会社 | プレフィルドシリンジ |
| CN103958604B (zh) | 2011-11-25 | 2016-05-04 | 三菱瓦斯化学株式会社 | 吸氧性树脂组合物及使用其的吸氧性成型体、以及使用它们的多层体、容器、注射成型体及医疗用容器 |
| US10780228B2 (en) | 2012-05-07 | 2020-09-22 | Medline Industries, Inc. | Prefilled container systems |
| CN104321363A (zh) * | 2012-05-11 | 2015-01-28 | 三菱瓦斯化学株式会社 | 具有环状缩醛骨架的聚酯树脂的制造方法 |
| TWI455956B (zh) | 2012-11-21 | 2014-10-11 | Ind Tech Res Inst | 非晶系共聚酯、基材、及光學膜 |
| WO2014136812A1 (ja) | 2013-03-06 | 2014-09-12 | 三菱瓦斯化学株式会社 | 酸素吸収剤組成物 |
| CN104262355A (zh) * | 2014-08-29 | 2015-01-07 | 北京化工大学常州先进材料研究院 | 含双二氧六环环缩醛结构可生物降解的烯类单体的制备方法 |
| AU2018251806B2 (en) | 2017-04-12 | 2023-05-25 | Urigen Pharmaceuticals, Inc. | Article of manufacture comprising local anesthetic, buffer, and glycosaminoglycan in syringe with improved stability |
| CN114853990A (zh) * | 2021-02-03 | 2022-08-05 | 长春人造树脂厂股份有限公司 | 耐黄变聚酯材料及其制备方法 |
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| US6284865B1 (en) * | 1999-09-20 | 2001-09-04 | E. I. Du Pont De Nemours And Company | Polymeric phosphite composition and hydrocyanation of unsaturated organic compounds and the isomerization of unsaturated nitriles |
| JP2001279085A (ja) * | 2000-01-25 | 2001-10-10 | Mitsubishi Engineering Plastics Corp | 熱可塑性樹脂組成物、熱可塑性樹脂成型品および医療用部品 |
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| US7179869B2 (en) * | 2004-03-22 | 2007-02-20 | Mitsubishi Gas Chemical Company, Inc. | Process for producing polyester resins |
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| US20030195303A1 (en) * | 2001-12-21 | 2003-10-16 | Tsuyoshi Ikeda | Polyester resin composition |
| JP2004298220A (ja) * | 2003-03-28 | 2004-10-28 | Terumo Corp | プレフィルドシリンジ |
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