CN1061060C - 基于聚丙烯树脂的多孔拉伸制品及其制备方法 - Google Patents
基于聚丙烯树脂的多孔拉伸制品及其制备方法 Download PDFInfo
- Publication number
- CN1061060C CN1061060C CN94105139A CN94105139A CN1061060C CN 1061060 C CN1061060 C CN 1061060C CN 94105139 A CN94105139 A CN 94105139A CN 94105139 A CN94105139 A CN 94105139A CN 1061060 C CN1061060 C CN 1061060C
- Authority
- CN
- China
- Prior art keywords
- acid
- straight
- polyacrylic resin
- amide compound
- amino
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims abstract description 80
- 238000002360 preparation method Methods 0.000 title claims description 11
- 229920005673 polypropylene based resin Polymers 0.000 title abstract 6
- -1 amide compound Chemical class 0.000 claims abstract description 86
- 239000004925 Acrylic resin Substances 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 238000002425 crystallisation Methods 0.000 claims description 18
- 230000008025 crystallization Effects 0.000 claims description 17
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 150000004984 aromatic diamines Chemical group 0.000 claims description 6
- 229920000178 Acrylic resin Polymers 0.000 claims description 5
- BVXGBMBOZMRULW-UHFFFAOYSA-N 1-n,4-n-dicyclohexylbenzene-1,4-dicarboxamide Chemical compound C=1C=C(C(=O)NC2CCCCC2)C=CC=1C(=O)NC1CCCCC1 BVXGBMBOZMRULW-UHFFFAOYSA-N 0.000 claims description 3
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000004427 diamine group Chemical group 0.000 claims description 3
- 125000001142 dicarboxylic acid group Chemical group 0.000 claims description 3
- KBQKHBYOZSOBQD-UHFFFAOYSA-N C(=O)=C1C(CCC(C1)N)N Chemical compound C(=O)=C1C(CCC(C1)N)N KBQKHBYOZSOBQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 229950001902 dimevamide Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims 1
- 239000000155 melt Substances 0.000 abstract description 3
- 239000013078 crystal Substances 0.000 abstract 2
- 239000011342 resin composition Substances 0.000 abstract 2
- 238000002844 melting Methods 0.000 abstract 1
- 230000008018 melting Effects 0.000 abstract 1
- 239000004743 Polypropylene Substances 0.000 description 30
- 239000002253 acid Substances 0.000 description 26
- 239000000047 product Substances 0.000 description 17
- 125000002723 alicyclic group Chemical group 0.000 description 14
- 229920001155 polypropylene Polymers 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 150000004985 diamines Chemical group 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 description 10
- 240000008415 Lactuca sativa Species 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 235000012045 salad Nutrition 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- 230000000875 corresponding effect Effects 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000011148 porous material Substances 0.000 description 7
- 150000001263 acyl chlorides Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical group CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 229940059260 amidate Drugs 0.000 description 5
- NPUKDXXFDDZOKR-LLVKDONJSA-N etomidate Chemical compound CCOC(=O)C1=CN=CN1[C@H](C)C1=CC=CC=C1 NPUKDXXFDDZOKR-LLVKDONJSA-N 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 4
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- YWIQQKOKNPPGDO-UHFFFAOYSA-N 2,3-didehydrophenylalanine zwitterion Chemical group OC(=O)C(N)=CC1=CC=CC=C1 YWIQQKOKNPPGDO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- YVNRUPSDZZZUQJ-UHFFFAOYSA-N [O].NC1=CC=CC=C1 Chemical compound [O].NC1=CC=CC=C1 YVNRUPSDZZZUQJ-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 3
- LRTFPLFDLJYEKT-UHFFFAOYSA-N para-isopropylaniline Chemical group CC(C)C1=CC=C(N)C=C1 LRTFPLFDLJYEKT-UHFFFAOYSA-N 0.000 description 3
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- FHBXQJDYHHJCIF-UHFFFAOYSA-N (2,3-diaminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1N FHBXQJDYHHJCIF-UHFFFAOYSA-N 0.000 description 2
- WOXWUZCRWJWTRT-UHFFFAOYSA-N 1-amino-1-cyclohexanecarboxylic acid Chemical compound OC(=O)C1(N)CCCCC1 WOXWUZCRWJWTRT-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 description 2
- MMEDJBFVJUFIDD-UHFFFAOYSA-N 2-[2-(carboxymethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CC(O)=O MMEDJBFVJUFIDD-UHFFFAOYSA-N 0.000 description 2
- YDUMDNFZGQAOJB-UHFFFAOYSA-N 2-methylcyclopentane-1-carboxylic acid Chemical compound CC1CCCC1C(O)=O YDUMDNFZGQAOJB-UHFFFAOYSA-N 0.000 description 2
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 2
- ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical group OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 2
- OQEBBZSWEGYTPG-UHFFFAOYSA-N 3-aminobutanoic acid Chemical compound CC(N)CC(O)=O OQEBBZSWEGYTPG-UHFFFAOYSA-N 0.000 description 2
- FPRSHRPBZCFRSF-UHFFFAOYSA-N 4-(cyclohexanecarbonylamino)-n-cyclohexylbenzamide Chemical compound C1CCCCC1C(=O)NC(C=C1)=CC=C1C(=O)NC1CCCCC1 FPRSHRPBZCFRSF-UHFFFAOYSA-N 0.000 description 2
- KOGDFDWINXIWHI-OWOJBTEDSA-N 4-[(e)-2-(4-aminophenyl)ethenyl]aniline Chemical compound C1=CC(N)=CC=C1\C=C\C1=CC=C(N)C=C1 KOGDFDWINXIWHI-OWOJBTEDSA-N 0.000 description 2
- XRSQZFJLEPBPOZ-UHFFFAOYSA-N 4-amino-2-methylbenzoic acid Chemical compound CC1=CC(N)=CC=C1C(O)=O XRSQZFJLEPBPOZ-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JWKLWGCHIHZXPM-UHFFFAOYSA-N C1(=CC=CC=C1)C(=O)O.C(=O)(NC(=O)OCC)NC(=O)OCC Chemical compound C1(=CC=CC=C1)C(=O)O.C(=O)(NC(=O)OCC)NC(=O)OCC JWKLWGCHIHZXPM-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- WNNNWFKQCKFSDK-UHFFFAOYSA-N allylglycine Chemical compound OC(=O)C(N)CC=C WNNNWFKQCKFSDK-UHFFFAOYSA-N 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- LJOODBDWMQKMFB-UHFFFAOYSA-N cyclohexylacetic acid Chemical compound OC(=O)CC1CCCCC1 LJOODBDWMQKMFB-UHFFFAOYSA-N 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000004700 high-density polyethylene Substances 0.000 description 2
- 229920001519 homopolymer Polymers 0.000 description 2
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- KUDRVFHSKWNDDA-UHFFFAOYSA-N n-(4-benzamidocyclohexyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(CC1)CCC1NC(=O)C1=CC=CC=C1 KUDRVFHSKWNDDA-UHFFFAOYSA-N 0.000 description 2
- BIHJEIFLAWVSQP-UHFFFAOYSA-N n-(anilinodisulfanyl)aniline Chemical compound C=1C=CC=CC=1NSSNC1=CC=CC=C1 BIHJEIFLAWVSQP-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- UDEWPOVQBGFNGE-UHFFFAOYSA-N propyl benzoate Chemical compound CCCOC(=O)C1=CC=CC=C1 UDEWPOVQBGFNGE-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- UQFHJDVUQSAVOQ-UHFFFAOYSA-N (2-aminophenyl) acetate Chemical group CC(=O)OC1=CC=CC=C1N UQFHJDVUQSAVOQ-UHFFFAOYSA-N 0.000 description 1
- NQBWNECTZUOWID-UHFFFAOYSA-N (E)-cinnamyl (E)-cinnamate Natural products C=1C=CC=CC=1C=CC(=O)OCC=CC1=CC=CC=C1 NQBWNECTZUOWID-UHFFFAOYSA-N 0.000 description 1
- ASJYWWLGWAQXDB-UHFFFAOYSA-N 1,1,1,2,2,2-hexachloroethane;triphenylphosphane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ASJYWWLGWAQXDB-UHFFFAOYSA-N 0.000 description 1
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- VFFRLRQQWXGEBX-UHFFFAOYSA-N 1-aminonaphthalene-2-carboxylic acid Chemical compound C1=CC=C2C(N)=C(C(O)=O)C=CC2=C1 VFFRLRQQWXGEBX-UHFFFAOYSA-N 0.000 description 1
- UJAHMMDIDKVNLK-UHFFFAOYSA-N 1-cyclohexylpropan-1-amine Chemical compound CCC(N)C1CCCCC1 UJAHMMDIDKVNLK-UHFFFAOYSA-N 0.000 description 1
- GULLOFXXKJRCMW-UHFFFAOYSA-N 1-methylcycloheptane-1-carboxylic acid Chemical compound OC(=O)C1(C)CCCCCC1 GULLOFXXKJRCMW-UHFFFAOYSA-N 0.000 description 1
- REHQLKUNRPCYEW-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(C)CCCCC1 REHQLKUNRPCYEW-UHFFFAOYSA-N 0.000 description 1
- MNIBBVOEXUQHFF-UHFFFAOYSA-N 1-methylcyclopentanecarboxylic acid Chemical compound OC(=O)C1(C)CCCC1 MNIBBVOEXUQHFF-UHFFFAOYSA-N 0.000 description 1
- QXXHHHWXFHPNOS-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCCC1 QXXHHHWXFHPNOS-UHFFFAOYSA-N 0.000 description 1
- RHPCYZLXNNRRMB-UHFFFAOYSA-N 1-phenylcyclopentane-1-carboxylic acid Chemical compound C=1C=CC=CC=1C1(C(=O)O)CCCC1 RHPCYZLXNNRRMB-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
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- B29C55/005—Shaping by stretching, e.g. drawing through a die; Apparatus therefor characterised by the choice of materials
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Abstract
公开了一种制备基于聚丙烯的树脂的多孔位伸制品的方法,该方法包括在15-140℃,使基于聚丙烯的树脂组合物的熔体结晶,以形成含β型结晶的固化产物,并将所得固化产物在高于20℃,但低于所述固化产物中β型结晶的熔点的温度拉伸,基于聚丙烯的树脂组合物包括基于聚丙烯的树脂和0.0001-5重量份(每100重量份基于聚丙烯的树脂)至少一种特定的酰胺化合物。本发明还公开了通过该方法制得的多孔位伸制品。
Description
本发明涉及基于β-结晶聚丙烯树脂的多孔拉伸制品的制备方法,以及由该方法生产的基于聚丙烯树脂的拉伸制品。
已知多种制备基于聚丙烯的多孔材料的方法。例如,已知下列方法:
方法(1):该方法包括使无机物和/或不相容树脂与聚丙烯混合,将混合物挤压成膜并对该膜取向或拉伸以得到多孔膜(日本未审查专利申请(公开)第116561/1975号等),和
方法(2):该方法包括使无机物或有机液体与聚丙烯混合,用溶剂或碱提取该混合物,将混合物挤压成膜,并将膜拉伸以得到多孔膜(日本未审查专利申请第59072/1983号等)。
方法(1)的缺点在于无机物溢出和所得到膜的断裂伸长减小,而方法(2)的缺点在于需要烦锁的工艺,例如耗时的提取步骤。
还有一种已知的生产多孔膜的方法(3),该方法使用结晶形式(β-型结晶),仅限于聚丙烯(日本审查专利申请(公布)第40411/1980等)。但该方法在实际条件下难以形成足够量的β-型结晶,不能给出具有令人满意的多孔率的多孔膜。
迄今提出的制备β-型结晶聚丙烯的方法包括:例如在一定温度梯度下将聚丙烯熔体结晶的方法,或使用少量β-成核剂(γ-喹吖酮)的方法(POLYMER LETTERS,6,539-546,(1968)),前一方法的缺点在于需长时间,而仅得到少量产物。后一方法的缺点是要求特别设计的装置,和使成核剂与聚丙烯混合的工序,其进一步的问题是实用性小,因为为了在未取向的产物中形成一定增加量的β-型结晶,需进行高温结晶步骤,因此需长时间模塑。此外,该方法的进一步问题是产物为红色。本发明者提出多种新的成核剂以增加β-型结晶含量,避免上述问题(美国专利申请系列号,第08/003659号)。
本发明的一个目的是改进上述方法(3),从而提供在实际条件下制备具有满意性能的基于聚丙烯的多孔材料的新的有用的方法。
为克服常规技术的缺点,本发明者进行了广泛研究,发现可通过下列方法得到预期的拉伸多孔制品,该方法是在特定温度下,使包含特定结构的预定量的酰胺化合物成核剂的聚丙烯熔体结晶,并将所得产物在特定温度下拉伸。本发明者基于这个发现完成了本发明。
本发明提供一种制备基于β-结晶聚丙烯树脂的多孔拉伸制品的方法,该方法包括在15-140℃,使基于聚丙烯的树脂组合物的熔体结晶,以形成含β-型结晶的固化产物,并将所得固化产物在高于20℃,但低于所述固化产物中β型结晶的熔点的温度拉伸,基于聚丙烯的树脂组合物包括基于聚丙烯的树脂和0.0001-5重量份(每100重量份基于聚丙烯的树脂)至少一种选自下列一组的酰胺化合物:
(1)下式的酰胺化合物
R2-NHCO-R1-CONH-R3 (1)其中R1是C1-24饱和或不饱和脂族二羧酸残基、C4-28饱和或不饱和脂环族二羧酸残基或C6-28芳族二羧酸残基;R2和R3彼此相同或不同,各代C3-18环烷基、C3-12环烯基或式
,其中R4是氢原子、C1-12直链或支链烷基、C2-12直链或支链烯基、C6-10环烷基或苯基;R5是C1-12直链或支链烷基或C2-12直链或支链烯基;R6和R7各自代表C1-4直链或支链烯基;
(2)下式的酰胺化合物:
R9-CONH-R8-NHCO-R10 (2)其中R8是C1-24饱和或不饱和脂族二胺残基、C4-28脂环族二胺残基、C4-14杂环族二胺残基或C6-28芳族二胺残基;R9和R10彼此相同或不同,各自代表C3-12环烷基、C3-12环烯基或
,其中R11是氢原子、C1-12直链或支链烷基、C2-12直链或支链烯基、C6-10环烷基或苯基;R12是C1-12直链或支链烷基、C2-12链烯基、C6-10环烷基或苯基;R13和R14各自代表C1-4直链或支链烯基;和
(3)下式的酰胺化合物:
R16-CONH-R15-CONH-R17 (3)其中R15是C1-28饱和或不饱和脂族氨基酸残基、C6-12饱和或不饱和脂环族氨基酸残基或C6-14芳族氨基酸残基;R16和R17彼此相同或不同,R16的意义与式(2)中R9或R10的相同,R17的意义与式(1)中R2或R3的相同。
用在本发明中的基于聚丙烯的树脂是一种主要由聚丙烯组成的聚合物。该聚合物的实例是聚丙烯均聚物、以丙烯为主要共聚单体,与至少一种选自乙烯和至少一种1-烯烃的共聚单体的共聚物(包括无规共聚物和嵌段共聚物),乙丙共聚物还可包含其它共聚单体(例如可进一步包含5-亚乙基-2-壬烯、5-亚甲基-2-壬烯或1,4-己二烯),丙烯-苯乙烯共聚物等。聚丙烯和少量热塑性树脂例如高密度聚乙烯、聚丁烯-1或聚-4-甲基戊烯-1的混合物也可以使用。
基于聚丙烯的树脂的熔体流动速率(以后简单表示为“MFR”,按JISK 6758-1981测定)可根据要使用的模塑方法适当选择,从所得拉伸制品的可加工性和机械性能以及其它性能的角度考虑通常大约为0.1-100g/10分钟,优选0.5-50g/分钟。
在本发明中,使用上式(1)、(2)和(3)的酰胺化合物。式(Ⅰ)的酰胺化合物
式(1)的酰胺化合物是已知的,或者可通过常规方法容易地制备,例如,通过使式(1a)HOOC-R1-COOH的脂族、脂环族或芳族二羧酸与式R2-NH2,或R3-NH2的脂环族或芳族一元胺进行酰胺化反应。(其中R1、R2和R3定义同上)。
作为式(Ⅰa)的二羧酸,可以提到的脂族、脂环族或芳族相应于R1的二羧酸。因此,R1是由下列脂族、脂环族和芳族二羧酸脱去两个羧基形成的残基。
脂族二羧酸具体包括C3-26优选C3-14饱和或不饱和脂族二羧酸,例如马来酸、二苯基马来酸、琥珀酸、苯基琥珀酸、二苯基琥珀酸、戊二酸、3,3-二甲基戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸、1 12-十二双酸、1,14-十四双酸、1,18-十八双酸等。
脂环族二羧酸的具体实例包括:C6-30,优选C8-12饱和或不饱和脂环族二羧酸,例如1,2-环己烷二羧酸、1,4-环己烷二羧酸、1,4-环己烷二乙酸等。
芳族二羧酸的具体实例包括:C8-30、优选C8-22芳族二羧酸例如对苯二乙酸、对苯二乙酸、邻苯二甲酸、4-叔丁基邻苯二甲酸、间苯二甲酸、5-叔丁基间苯二甲酸、对苯二甲酸、1,8-萘二甲酸、1,4-萘二甲酸、2,6-萘二甲酸、2,7-萘二甲酸、联苯甲酸、3,3′-联苯二甲酸、4,4′-联苯二甲酸、4,4′-联萘二甲酸、双(3-羧基苯基)甲烷、双(4-羧基苯基)甲烷、2,2-双(3-羧基苯基)丙烷、2,2-双(4-羧基苯基)丙烷、3,3′-磺酰基二苯甲酸、4,4′-磺酰基二苯甲酸、3,3′-氧代二苯甲酸、4,4′-氧代二苯甲酸、3,3′-羰基二苯甲酸、4,4′-羰基二苯甲酸、3,3′-硫代二苯甲酸、4,4′-硫代二苯甲酸、4,4′-(对苯二氧代)二苯甲酸、4,4′-间苯二酰二苯甲酸、4,4′-对苯二酰二苯甲酸、二硫代水杨酸等。
另一方面,使用的一元胺为脂环族或芳族相应于R2或R3的一元胺(即R2-NH2或R2-NH2)。
脂环族一元胺具体包括:C3-18环烷基胺、C3-12环烯基胺、H2 (其中R5定义如上)、
(其中R7定义如上)等,具体包括:环丙胺、环丁胺、环戊胺、环己胺、2-甲基环己胺、3-甲基环己胺、4-甲基-环己胺、2-乙基环己胺、4-乙基-环己胺、2-丙基环己胺、2-异丙基环己胺、4-丙基环己胺、4-异丙基环己胺、2-叔丁基环己胺、4-正丁基环己胺、4-异丁基环己胺、4-仲丁基环己胺、4-叔丁基环己胺、4-正戊基环己胺、4-异戊基环己胺、4-仲戊基环己胺、4-叔戊基环己胺、4-己基环己胺、4-庚基环己胺、4-辛基环己胺、4-壬基环己胺、4-癸基环己胺、4-十一烷基环己胺、4-十二烷基环己胺、4-环己基环己胺、4-苯基环己胺、环庚胺、环十二烷胺、环己基甲胺、α-环己基乙胺、β-环己基乙胺、α-环己基丙胺、β-环己基丙胺、γ-环己基丙胺等。
芳族一元胺具体包括:
(其中R4定义如上),H2N-
(其中R6定义如上)等,具体包括:苯胺、邻甲苯胺、间甲苯胺、对甲苯胺、邻乙苯胺、对乙苯胺、邻丙苯胺、间丙苯胺、对丙苯胺、邻枯胺、间枯胺、对枯胺、邻叔丁基苯胺、对正丁基苯胺、对异丁基苯胺、对仲丁基苯胺、对叔丁基苯胺、对正戊基苯胺、对异戊基苯胺、对仲戊基苯胺、对叔戊基苯胺、对己基苯胺、对庚基苯胺、对辛基苯胺、对壬基苯胺、对癸基苯胺、对十一烷基苯胺、对十二烷基苯胺、对环己基苯胺、邻氨基联苯、间氨基联苯、对氨基联苯、对氨基苯乙烯、苄胺、α-苯基乙胺、β-苯基乙胺、α-苯基丙胺、β-苯基丙胺和γ-苯基丙胺等。
在式(1)的酰胺化合物中,特别优选的包括:N,N′-二苯基己二酰二胺、N,N′-二环己基对苯二甲酰胺或N,N′-二环己基-2,6-萘二甲酰胺。式(2)的酰胺化合物
式(2)的酰胺化合物可通过使式(2a)的脂族、脂环族、杂环族或芳族二胺与式R9-COOH或R10-COOH(其中R9和R10定义如上)的脂环族或芳族一元羧酸按常规方式进行酰胺化反应而容易地制得。式(2a)为:
H2N-R8-NH2 (2a)其中R8定义如上。
酰胺化反应可按各种常规方式进行,但通常是按下面所述方法之一进行的:
(1)在惰性溶剂中,在约60-200℃的温度下,使上述二胺与一元羧酸反应2-8小时。一元羧酸的用量通常为每当量二胺约2-10当量。在该方法中,优选使用活化剂来加速反应。可使用的活化剂包括:五氧化二磷、多磷酸、五氧化二磷-甲磺酸、亚磷酸酯(例如亚磷酸三苯酯)-吡啶、亚磷酸酸-金属盐(例如氯化锂)、三苯膦-六氯乙烷等。活化剂的用量通常为与二胺等摩尔。
(ⅱ)在惰性溶剂中,在约0-100℃的温度下,使上述二胺与所述一元羧酸的酰氯反应约1-5小时。一元羧酸的酰氯的用量为每当量二胺约2-3当量。
(ⅲ)在惰性溶剂中,在催化剂存在下,在约0-150℃,使上述二胺与所述一元羧酸的酯-特别是C1-3烷基酯反应3-10小时。一元羧酸酯的用量通常为每当量二胺约2-20当量。所述催化剂可以是酯-酰胺互换反应中常用的酸性或碱性催化剂,优选碱性催化剂。因此,可以提到的是:锂、钠、钾;碱金属氢化物例如氢化锂、氢化钠、氢化钾等;碱金属氢氧化物例如氢氧化锂、氢氧化钠、氢氧化钾;金属醇盐例如甲醇钠、乙醇钠、叔丁醇钾等;碱金属氨化物例如氨基化钠、二丙基氨基化锂等。
当式(2)中的R9和R10彼此不同时,使用两种相应的一元羧酸的基本上等摩尔的混合物(或两种相应的一元酰氯或两种相应的一元羧酸酯的基本上等摩尔的混合物)。
可用于方法(ⅰ)、(ⅱ)和(ⅲ)的惰性溶剂包括:苯、甲苯、二甲苯、氯仿、氯苯、二氯苯、四氢呋喃、二噁烷、乙腈、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺和N-甲基吡咯烷酮。
由上述方法得到的化合物通过常规方法例如色谙法、再沉淀、重结晶、分级结晶等进行分离和纯化。
在上述方法(ⅰ)、(ⅱ)和(ⅲ)中,式(2a)的二胺为脂族、脂环族、杂环族或芳族相应于R8的二胺。因此,R8是下列脂族、脂环族、杂环族和芳族二胺脱去两个氨基而形成的残基。
因此,脂族二胺包括C1-24、优选C1-12脂族二胺例如1,2-二氨基乙烷,1,2-二氨基丙烷、1,3-二氨基丙烷、1,4-二氨基丁烷、1,3-二氨基戊烷、1,5-二氨基戊烷、1,6-二氨基己烷、1,8-二氨基辛烷、1,10-二氨基癸烷、1,11-二氨基十一烷等。
脂环族二胺包括C4-28、优选C6-15脂环族二胺例如1,2-二氨基环己烷、1,4-二氨基环己烷、4,4′-二氨基二环己基、4,4′-二氨基-3,3′-二甲基二环己基、4,4′-二氨基二环己基甲烷、4,4′-二氨基-3,3′-二甲基二环己基甲烷、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷,另外还包括异佛尔酮二胺、_烯二胺等。
杂环族二胺包括:在环结构中含1或2个氮或硫原子,且有4-14个碳原子的5或6元杂环二胺,例如2,3-二氨基吡啶、2,6-二氨基吡啶、3,4-二氨基吡啶、邻联甲苯胺砜(o-tolidnesulfone)等。
芳族二胺包括那些含6-28个,优选6-15个碳原子的芳族二胺,例如邻苯二胺、间苯二胺、对苯二胺、2,3-二氨基甲苯、2,4-二氨基甲苯、2,6-二氨基甲苯、3,4-二氨基甲苯、4,6-二甲基间苯二胺、2,5-二甲基对苯二胺、4,5-二甲基邻苯二胺、邻二甲苯二胺、间二甲苯二胺、对二甲苯二胺、2,4-二氨基米、1,5-二氨基萘、1,8-二氨基萘、2,3-二氨基萘、2,7-二氯基萘、9,10-二氯基菲、3,3′,5,5′-四甲基联苯胺、3,3′-二甲基-4,4′-二氨基联苯、3,3′-二甲氧基-4,4′-二氨基联苯、4,4′-二氨基二苯甲烷、3,3′-二氨基二苯甲烷、3,4′-二氨基二苯甲烷、4,4′-亚甲基二邻甲苯胺、4,4′-亚甲基二-2,6-二甲代苯胺、4,4′-亚甲基二-2,6-二乙苯胺、4,4′-二氨基-1,2-二苯乙烷、4,4′-二氨基-2,2′-二甲基联苄、4,4′-二氨基芪、3,4′-二氨基-2,2-二苯基丙烷、4,4′-二氨基-2,2-二苯基丙烷、4,4′-二氨基二苯醚、3,4′-二氨基二苯醚、4,4′-硫代双苯胺、2,2′-二硫代双苯胺、4,4′-二硫代双苯胺、3,3′-二氨基二苯砜、4,4′-二氨基二苯砜、3,3′-二氨基二苯酮、4,4′-二氨基二苯酮、4,4′-二氨基N-苯甲酰苯胺、2,7-二氨基芴、3,7-二氨基-2-甲氧基芴、双对氨基苯基苯胺、1,3-双(4-氨基苯氧基)苯、1,4-双(4-氨基苯氧基)苯、4,4′-双(4-氨基苯氧基)联苯、双[4-(4-氨基苯氧基苯基]醚、双[4-(4-氨基苯氧基)苯基)砜、9,9-双(4-氨基苯基)芴等。
脂环族一元羧酸的实例由R9-COOH或R10-COOH表示,可提到的是C4-13环烷羧酸、C4-13环烯羧酸、
(其中R12如上定义)、
(其中R14如上定义)等,其实例包括:环丙烷羧酸、环丁烷羧酸、环戊烷羧酸、1-甲基环戊烷羧酸、2-甲基环戊烷羧酸、3-甲基环戊烷羧酸、1-苯基环戊烷羧酸、环戊烯羧酸、环己烷羧酸、1-甲基环己烷酸、2-甲基环己烷羧酸、3-甲基环己烷羧酸、4-甲基环己烷羧酸、4-丙基环己烷羧酸、4-丁基环己烷羧酸、4-戊基环己烷羧酸、4-己基环己烷羧酸、4-苯基环己烷羧酸、1-苯基环己烷羧酸、环己烯羧酸、4-丁基环己烯羧酸、环庚烷羧酸、1-环庚烯羧酸、1-甲基环庚烷羧酸、4-甲基环庚烷羧酸、环己基乙酸等。
芳族一元羧酸的实例由R9-COOH或R10-COOH表示,可以提到的是(其中R11定义如上)、
其中R13定义如上等),其实例是:苯甲酸、邻甲基苯甲酸、间甲基苯甲酸、对甲基苯甲酸、对乙基苯甲酸、对丙基苯甲酸、对丁基苯甲酸、对叔丁基苯甲酸、对戊基苯甲酸、对己基苯甲酸、邻苯基苯甲酸、对苯基苯甲酸、对环己基苯甲酸、苯基乙酸、苯基丙酸、苯基丁酸等。
在可由二胺与一元羧酸得到的式(2)的二酰胺化合物中,更理想的是N,N′-二环己烷羰基对苯二胺、N,N′-二苯甲酰基-1,5-二氨基萘、N,N′-二苯甲酰基-1,4-二氨基环己烷、N,N′-二环己烷羰基-1,4-二氨基环己烷等。式(3)的酰胺化合物
式(3)的酰胺化合物可通过使式(3a)的脂族,脂环族或芳族氨基酸、式R16-ROCl(其中R16定义如上)的一元酰氯和式R17-NH2(其中R17定义如上)的一元胺进行酰胺化反应而容易地制得,式(3a)为:
NH2-R15-COOH (3a)其中R15定义如上。
酰胺化反应例如可按如下方法进行:在惰性溶剂中,在约0-100℃,使式(3a)的所述氨基酸与1-2当量所述一元酰氯反应1-5小时,然后加入基于反应产物计算1-5当量的所述一元胺,在约60-200℃的温度下,优选在方法(ⅰ)所述活化剂存在下进行反应约2-8小时。惰性溶剂可以是方法(ⅰ)中为制备所述式(2)化合物所提及的任何溶剂。
由上述方法得到的化合物可通过常规方法例如色谱法、再沉淀、重结晶、分级结晶等进行分离和纯化。
在上述方法中使用的氨基酸(3a)是脂族、脂环族或芳族相应于R15的氨基酸。因此,R15是下述脂族、脂环族或芳族氨基酸脱去一个氨基和一个羧基而形成的残基。
所述脂族氨基酸的优选实例为C2-29、优选C2-13饱和或不饱和脂族氨基酸例如氨基乙酸、α-氨基丙酸、β-氨基丙酸、α-氨基丙烯酸、α-氨基丁酸、β-氨基丁酸、γ-氨基丁酸、α-氨基-α-甲基丁酸、γ-氨基-α-亚甲基丁酸、α-氨基异丁酸、γ-氨基异丁酸、α-氨基正戊酸、8-氨基正戊酸、β-氨基巴豆酸、α-氨基-β-甲基戊酸、α-氨基异戊酸、2-氨基-4-戊烯酸、α-氨基正己酸、6-氨基己酸、α-氨基异己酸、7-氨基庚酸、α-氨基正辛酸、8-氨基辛酸、9-氨基壬酸、11-氨基-十一烷酸、12-氨基-十二烷酸等。
脂环族氨基酸包括C7-13饱和或不饱和脂环族氨基酸,例如1-氨基环己烷羧酸、2-氨基环己烷羧酸、3-氨基环己烷羧酸、4-氨基环己烷羧酸、对氨基环己烷羧酸、2-氨基-2-壬烷羧酸等。
芳族氨基酸具体包括C7-15芳族氨基酸,例如α-氨基苯基乙酸、α-氨基-β-苯基丙酸、2-氨基-2-苯基丙酸、3-氨基-3-苯基丙酸、α-氨基肉桂酸、2-氨基-4-苯基丁酸、4-氨基-3-苯基丁酸、氨茴酸、间氨基苯甲酸、对氨基苯甲酸、2-氨基-4-甲基苯甲酸、2-氨基-6-甲基苯甲酸、3-氨基-4-甲基苯甲酸、2-氨基-3-甲基苯甲酸、2-氨基-5-甲基苯甲酸、4-氨基-2-甲基苯甲酸、4-氨基-3-甲基苯甲酸、2-氨基-3-甲氧基苯甲酸、3-氨基-4-甲氧基苯甲酸、4-氨基-2-甲氧基苯甲酸、4-氨基-3-甲氧基苯甲酸、2-氨基-4,5-二甲氧基苯甲酸、邻氨基苯基乙酸、间氨基苯基乙酸、对氨基苯基乙酸、4-(4-氨基苯基)丁酸、4-氨基甲基苯甲酸、4-氨基甲基苯乙酸、邻氨基肉桂酸、间氨基肉桂酸、对氨基肉桂酸、对氨基马尿酸、2-氨基-1-萘甲酸、3-氨基-1-萘甲酸、4-氨基-1-萘甲酸、5-氨基-1-萘甲酸、6-氨基-1-萘甲酸、7-氨基-1-萘甲酸、8-氨基-1-萘甲酸、1-氨基-2-萘甲酸、3-氨基-2-萘甲酸、4-氨基-2-萘甲酸、5-氨基-2-萘甲酸、6-氨基-2-萘甲酸、7-氨基-2-萘甲酸、8-氨基-2-萘甲酸等。
作为式(3)酰胺化合物的起始化合物的一元胺(R17-NH2)与用作式(1)的酰胺化合物的起始化合物的一元胺(R2-NH2或R3-NH2)相同,类似地,一元酰氯(R16COCl)源自于与作为式(2)的酰胺化合物的起始化合物的一元羧酸(R9COOH或R10COOH)相同的一元羧酸。
在各种式(3)的酰胺化合物中,特别有效的例如为N-环己基-4-(N-环己基羰基氨基)-苯甲酰胺和N-苯基-5-(N-苯甲酰氨基)-戊酰胺。
在式(1)、(2)和(3)的酰胺化合物中,优选式(1)的酰胺化合物。
所述式(1)、(2)和(3)的酰胺化合物可在制备基于聚丙烯的树脂的过程中加入或与单独制得的树脂混合。
酰胺化合物的加入量为每100重量份基于聚丙烯的树脂0.0001-5重量份,优选0.001-1重量份。如果酰胺化合物的比例小于0.0001重量份,β型结晶形成不充分,而使用超过5重量份的酰胺化合物,不会得到相应的效果,而且是不经济的,并有减小拉伸制品的断裂伸长和拉伸断裂强度的倾向。
基于聚丙烯的树脂组合物熔融温度在约190-300℃范围内,优选约200-280℃范围内。
本发明方法中树脂组合物熔体的结晶温度(冷却温度)在约15-140℃范围内,优选约20-120℃,更优选约70-120℃。在这样得到的未拉伸产品中β-型结晶含量(K值)在约0.5-1.0范围内,该范围适于实际应用。结晶步骤是这样完成的,例如将含至少一种式(1)、(2)和(3)的β-成核剂的基于聚丙烯的树脂挤压片材,然后用维持在上述特定温度范围内的冷却辊将片材冷却并固化,从而形成β型结晶,这将举例说明。
然后用常规方式,但在特定温度条件下,将含β型的基于聚丙烯树脂的未拉伸产品拉伸。在本发明中在高于20℃但低于所述未拉伸产品中β型结晶的熔点的温度使含β型结晶的基于聚丙烯的树脂的未拉伸产品拉伸是重要的。所述未拉伸产品中β型结晶的熔点可通过示差扫描量热法容易地测得,其熔点不超过150℃,具体数值取决于基于聚丙烯的树脂的种类。为了获得高的多孔率,未拉伸制品拉伸的温度上限优选为低于所述未拉伸制品中β型结晶熔点至少10度。换句话说,优选在下面等式定义的Ts(℃)以下的温度进行拉伸,Ts=Tm-10,其中Tm为未拉伸产品中β型结晶的熔点(℃)。从拉伸操作的角度考虑,拉伸温度优选不低于70℃,更优选不低于90℃。
只要在上述温度范围内进行结晶,然后在上述特定温度范围内进行拉伸就可制得本发明的具有足够多孔率(例如至少10%,优选约20-80%)的拉伸产品。
要使用的拉伸模式是单轴拉伸或同时或顺次双轴拉伸。
单轴拉伸和同时或顺次双轴拉伸可按常规方法进行。对于双轴拉伸的情况,不限制拉伸程度,在纵向优选的拉伸比,例如为1.2-5.0,更优选1.7-2.8;在横向,优选的拉伸比为1.2-5.0,更优选1.8-2.6。对于单轴拉伸的情况,也不限制拉伸程度,优选的拉伸比例如为1.5-6.0,更优选2.5-3。
在本发明中使用的压力条件可在很宽范围内变化,可以是常压、加压或减压。
必要的活,用在本发明的基于聚丙烯的树脂组合物可包含多种常规添加剂,例如稳定剂(例如环氧化合物)、抗氧化剂(例如酚类化合物和亚磷酸酯化合物)、紫外线吸收剂(例如二苯酮和苯并***化合物)、中和剂、成核剂、抗静电剂、防粘剂、润滑剂(例如脂族烃、高级脂肪酸及其碱金属盐或碱土金属盐、脂肪酸酯、高级脂肪酰胺、松香衍生物等)、着色剂、弹性体和矿物质(例如滑石和水滑石),每个添加剂都在不影响本发明效果的范围内。
这样得到的基于聚丙烯的树脂的拉伸或取向制品被用于生产不透明,该膜具有极佳的白度、遮盖力、适印性和适写性,所述拉伸或取向制品或者被用于生产具有许多互相穿插孔的多孔膜。所述不透明膜作为材料广泛用于印刷板、描图纸、食品包装膜等。多孔膜用途广泛例如以膜或中空丝的形式作各种用途,例如作为为透湿和防水目的的膜、为净化空气或处理废水的过滤器或分离膜,作为用于分离等离子体的膜或人造肺的医疗材料,作为用于电池或电解的蓄电池隔板等。
实施例
下列实施例和对比实施例旨在更具体地描述本发明。在这些实施例和对比实施例中,β型结晶含量和多孔率是按如下方法测得的:
(1)测定β型结晶含量
(ⅰ)X射线法
H(β1)为β型结晶平面(300)上的反射强度(高度);
H(α1)为α型结晶平面(110)上的反射强度(高度);
H(α2)为α型结晶平面(040)上的反射强度(高度);
H(α3)为α型结晶平面(130)上的反射强度(高度);
(ⅱ)DSC方法
从每个实施例和对比实施例得到的基于聚丙烯树脂的浇铸膜(未拉伸膜)上切下样品(约5mg),将其放于示差扫描量热仪(DSC)的样品支架中,在氮气氛下,以20℃/分钟速度加热。从如此获得的DSC热分析图上的α-和β-型结晶峰面积测出β型结晶含量(面积%,以后表示为“DSC%”)。
(2)多孔率的测定
通过在室温下将拉伸膜样品在沙拉油(ρ=0.925g/cm)中浸渍5分钟而使沙拉油渗入到样品中、将粘着于样品表面的沙拉油用浸渍甲醇的纸擦去。然后测定样品膜重量并计算渗入膜中的沙拉油的体积。多孔率按下面等式计算:
α=(Vo/Vf)×100其中α为多孔率(%),Vc为渗入膜中的沙拉油的体积;Vρ为样品膜的表观体积。
实施例1-7
向MFR为14g/10分钟的100重量份聚丙烯均聚物粉末(以后称作“PP(1)”)中加入0.1重量份N,N′-二环己基-2,6-萘二甲酰胺(以后称为“成核剂1”)作为β成核剂。将混合物在240℃在Henschel混合器中研磨并造粒。在240℃的树脂温度下,将所得丸粒由T型口模挤出机挤压成片材,并用维持在表1所示温度(冷却温度)的冷却辊对片材进行冷却和固化,从而得到厚200μm的未拉伸聚丙烯浇铸膜。下表1给出了如此得到的各未拉伸膜的β型结晶含量(K值和DSC%)。
然后在表1所示条件下将各未拉伸膜进行单轴或双轴拉伸而成为白色不透明膜。在实施例1-7的各个实施例(也包括实施例8-17和随后的对比实施例1)中,拉伸温度低于包含在未拉伸产品中的β型结晶的熔点(由示差扫描量热法(DSC)测定)。β型结晶PP(1)的熔点为152℃。
然后将沙拉油渗入到这些拉伸膜中,从而使膜全部成为半透明。这说明它们是具有极佳互相贯穿孔结构的多孔膜。
表1示出了拉伸膜的厚度以及由渗入的沙拉油的量计算出的拉伸膜的多孔率(%)。
实施例8
按类似于实施例3的方法,使用MFR为4.3g/10分钟的丙烯均聚物粉末(以后称为“PP(2)”)制备拉伸膜。PP(2)的β型结晶的熔点为147℃。所得的膜为具有极佳互相贯穿孔结构的多孔膜。
表1示出了未拉伸膜中β型结晶的含量(K值和DSC%)以及拉伸膜的厚度和多孔率(%)。
实施例9
按类似于实施例3的方法,使用MFR为1.4g/10分钟的丙烯均聚物粉末(以后称为“PP(3)”)制备拉伸膜。PP(3)的β型结晶的熔点为148℃。所得的膜为具有极佳互相贯穿孔结构的多孔膜。
表1示出了未拉伸膜中β型结晶的含量(K值和DSC%)以及拉伸膜的厚度和多孔率。
实施例10
除了使用PP(3)以外,基本上按实施例6的方法制备拉伸膜。将未拉伸膜在90℃单轴拉伸得到拉伸膜。拉伸膜为具有极佳互相贯穿孔结构的多孔膜。
表1示出了未拉伸膜中β型结晶的含量(K值和DSC%)以及拉伸膜的厚度和多孔率。
实施例11-12
按类似于实施例1的方法,使用不同量的成核剂1制得拉伸膜。拉伸膜为具有极佳互相贯穿孔结构的多孔膜。
表1示出了各未拉伸膜中β型结晶的含量(K值和DSC%)以及各拉伸膜的厚度和多孔率。
实施例13
按照类似于实施例1的方法,使用N,N′-二环己基对苯二甲酰胺(以后称为“成核剂2”)作β-成核剂制得拉伸膜。
表1示出了未拉伸膜中β型结晶的含量(K值和DSC%)以及拉伸膜的厚度和多孔率。
实施例14
按照类似于实施例1的方法,使用N,N′-二苯基己二酰二胺(以后称为“成核剂3”)作β-成核剂制得拉伸膜。
表1示出了未拉伸膜中β型结晶的含量(K值和DSC%)以及拉伸膜的厚度和多孔率。实施例15
按照类似于实施例1的方法,使用N,N′-二环己烷羰基对苯二胺(以后称为“成核剂4”)作β-成核剂制得拉伸膜。
表1示出了未拉伸膜中β型结晶的含量(K值和DSC%)以及拉伸膜的厚度和多孔率。
实施例16
按照类似于实施例1的方法,使用N,N′-二苯甲酰基-1,4-二氨基环己烷(以后称为“成核剂5”)作β-成核剂制得拉伸膜。
表1示出了未拉伸膜中β型结晶的含量(K值和DSC%)以及拉伸膜的厚度和多孔率。
实施例17
按照类似于实施例1的方法,使用N-环己基-4-(N-环己基羰基氨基)-苯甲酰胺(以后称为“成核剂6”)作β-成核剂制得拉伸膜。
表1示出了未拉伸膜中β型结晶的含量(K值和DSC%)以及拉伸膜的厚度和多孔率。对比实施例1
除了用维持在10℃的冷却辊进行冷却和固化外,按实施例1方法进行,得到未拉伸膜。表1给出了未拉伸膜中β型结晶(K值和DSC%)含量。
在130℃对未拉伸膜进行单轴拉伸得到拉伸膜。所得到的膜为半透明的且多孔率低,如表1所示。对比实施例2
除了用维持在20℃的冷却辊进行冷却和固化外,按实施例1方法进行,得到未拉伸膜。表1给出了未拉伸膜中β型结晶(K值和DSC%)含量。
在155℃对未拉伸膜进行单轴拉伸得到拉伸膜。所得到的膜为基本上透明的,沙拉油无法渗入膜中。对比实施例3
除了不使用成核剂外,重复实施例1的方法,制得未拉伸膜。表1给出了未拉伸膜的β型结晶含量(K值和DSC%)。
在125℃对未拉伸膜进行双轴拉伸得到拉伸膜。所得膜基本上是透明的,沙拉油无法渗入膜中。
表1
注:MD=纵向TD=横向
实施例 | |||||||||
1 | 2 | 3 | 4 | 5 | 6 | 7 | |||
配方(重量份) | PP(1) | 100 | 100 | 100 | 100 | 100 | 100 | 100 | |
PP(2) | - | - | - | - | - | - | - | ||
PP(3) | - | - | - | - | - | - | - | ||
成核剂1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | 0.1 | ||
成核剂2 | - | - | - | - | - | - | - | ||
成核剂3 | - | - | - | - | - | - | - | ||
成核剂4 | - | - | - | - | - | - | - | ||
成核剂5 | - | - | - | - | - | - | - | ||
成核剂6 | - | - | - | - | - | - | - | ||
成膜条件 | 冷却温度(℃) | 110 | 110 | 110 | 110 | 70 | 50 | 20 | |
拉伸温度(℃) | 125 | 125 | 110 | 150 | 110 | 100 | 90 | ||
拉伸速率 | MD | 1.7 | 2.8 | 2.8 | 2.8 | 2.8 | 2.8 | 2.5 | |
TD | 1.9 | 2.6 | - | - | - | - | - | ||
β型结晶含量 | κ值 | 0.89 | 0.89 | 0.89 | 0.89 | 0.90 | 0.90 | 0.87 | |
DSC% | 79.6 | 79.6 | 79.6 | 79.6 | 66.2 | 60.3 | 34.8 | ||
膜厚度(μm) | 70 | 35 | 135 | 130 | 125 | 120 | 130 | ||
多孔率(%) | 393 | 39.0 | 30.3 | 22.4 | 28.2 | 25.4 | 22.3 |
表1(续)
注:MD=纵向TD=横向
实施例 | |||||||||
8 | 9 | 10 | 11 | 12 | 13 | 14 | |||
配方(重量份) | PP(1) | - | - | - | 100 | 100 | 100 | 100 | |
PP(2) | 100 | - | - | - | - | - | - | ||
PP(3) | - | 100 | 100 | - | - | - | - | ||
成核剂1 | 0.1 | 0.1 | 0.1 | 0.05 | 0.2 | - | - | ||
成核剂2 | - | - | - | - | - | 0.1 | - | ||
成核剂3 | - | - | - | - | - | - | 0.1 | ||
成核剂4 | - | - | - | - | - | - | - | ||
成核剂5 | - | - | - | - | - | - | - | ||
成核剂6 | - | - | - | - | - | - | - | ||
成膜条件 | 冷却温度(℃) | 110 | 110 | 50 | 110 | 110 | 110 | 110 | |
拉伸温度(℃) | 110 | 110 | 90 | 125 | 125 | 125 | 125 | ||
拉伸速率 | MD | 3.0 | 3.0 | 2.5 | 1.8 | 2.0 | 1.9 | 2.0 | |
TD | - | - | - | 1.9 | 2.2 | 2.1 | 1.9 | ||
β型结晶含量 | K值 | 0.90 | 0.91 | 0.90 | 0.90 | 0.92 | 0.84 | 0.84 | |
DSC% | 79.4 | 78.9 | 56.6 | 77.5 | 79.4 | 77.9 | 79.1 | ||
膜厚度(μm) | 125 | 125 | 130 | 70 | 60 | 65 | 65 | ||
多孔率(%) | 23.4 | 24.2 | 21.5 | 27.2 | 40.2 | 30.5 | 33.0 |
表1(续)
注:MD=纵向TD=横向
实施例 | 对比实施例 | |||||||
15 | 16 | 17 | 1 | 2 | 3 | |||
配方(重量份) | PP(1) | 100 | 100 | 100 | 100 | 100 | 100 | |
PP(2) | - | - | - | - | - | - | ||
PP(3) | - | - | - | - | - | - | ||
成核剂1 | - | - | - | 0.1 | 0.1 | - | ||
成核剂2 | - | - | - | - | - | - | ||
成核剂3 | - | - | - | - | - | - | ||
成核剂4 | 0.1 | - | - | - | - | - | ||
成核剂5 | - | 0.1 | - | - | - | - | ||
成核剂6 | - | - | 0.1 | - | - | - | ||
成膜条件 | 冷却温度(℃) | 110 | 100 | 110 | 10 | 20 | 110 | |
拉伸温度(℃) | 125 | 125 | 125 | 130 | 155 | 125 | ||
拉伸速率 | MD | 1.9 | 2.1 | 2.1 | 2.5 | 2.5 | 2.8 | |
TD | 2.0 | 2.1 | 1.8 | - | - | 2.6 | ||
β型结晶含量 | K值 | 0.89 | 0.87 | 0.85 | 0.70 | 0.87 | 0.00 | |
DSC% | 71.4 | 70.3 | 68.7 | 14.1 | 34.8 | 0.00 | ||
膜厚度(μm) | 65 | 60 | 65 | 100 | 100 | 35 | ||
多孔率(%) | 25.0 | 26.5 | 23.8 | 2.16 | 0.00 | 0.00 |
本发明效果
当使用本发明酰胺化合物作β成核剂时,可在实用条件下,容易地制得可商用的基于聚丙烯的树脂的拉伸的多孔制品。所述拉伸制品可用于印刷板、过滤膜和分离膜的材料。
Claims (19)
1.一种制备基于聚丙烯的树脂的多孔拉伸制品的方法,该方法包括在15-140℃,使基于聚丙烯的树脂组合物的熔体结晶,以形成含β-型结晶的固化产物,并将所得固化产物在高于20℃,但低于所述固化产物中β型结晶的熔点的温度拉伸,基于聚丙烯的树脂组合物包括基于聚丙烯的树脂和0.0001-5重量份(每100重量份基于聚丙烯的树脂)至少一种选自下列一组的酰胺化合物:
(1)下式的酰胺化合物
R2-NHCO-R1-CONH-R3 (1)其中R1是C1-24饱和或不饱和脂族二羧酸残基、C4-28饱和或不饱和脂环族二羧酸残基或C6-28芳族二羧酸残基;R2和R3彼此相同或不同,各代C3-18环烷基、C3-12环烯基或式
,其中R4是氢原子、C1-12直链或支链烷基、C2-12直链或支链烯基、C6-10环烷基或苯基;R5是C1-12直链或支链烷基或C2-12直链或支链链烯基;R6和R7各自代表C1-4直链或支链烯基;
(2)下式的酰胺化合物:
R9-CONH-R8-NHCO-R10 (2)其中R8是C1-24饱和或不饱和脂族二胺残基、C4-28脂环族二胺残基、C4-14杂环族二胺残基或C6-28芳族二胺残基;R9和R10彼此相同或不同,各自代表C3-12环烷基、C3-12环烯基或
,其中R11是氢原子、C1-12直链或支链烷基、C2-12直链或支链烯基C6-10环烷基或苯基;R12是C1-12直链或支链烷基、C2-12链烯基、C6-10环烷基或苯基;R13和R14各自代表C1-4直链或支链烯基;和
(3)下式的酰胺化合物:
R16-CONH-R15-CONH-R17(3)其中R15是C1-28饱和或不饱和脂族氨基酸残基、C6-12饱和或不饱和脂环族氨基酸残基或C6-14芳族氨基酸残基;R16和R17彼此相同或不同,R16的意义与式(2)中R9或R10的相同,R17的意义与式(1)中R2或R3的相同。
2.权利要求1的方法,其中基于聚丙烯的树脂组合物包含式(1)的酰胺化合物。
3.权利要求2的方法,其中式(1)的酰胺化合物为N,N′-二苯基己二酰二胺、N,N′-二环己基对苯二甲酰胺或N,N′-二环己基-2,6-萘二甲酰胺。
4.权利要求1的方法,其中基于聚丙烯的树脂组合物包含式(2)的酰胺化合物。
5.权利要求4的方法,其中式(2)的酰胺化合物是N,N′-二环己烷羰基对苯二胺、N,N′-二苯甲酰基-1,5-二氨基萘、N,N′-二苯甲酰基-1,4-二氨基环己烷或N,N′-二环己烷羰基-1,4-二氨基环己烷。
6.权利要求1的方法,其中基于聚丙烯的树脂组合物包含式(3)的酰胺化合物。
7.权利要求6的方法,其中式(3)的酰胺化合物为N-环己基-4-(N-环己基羰基氨基)苯甲酰胺或N-苯基-5-(N-苯甲酰基氨基)戊酰胺。
8.权利要求1的方法,其中每100重量份基于聚丙烯的树脂使用0.001-1重量份的至少一种酰胺化合物。
9.权利要求1的方法,其中所述熔体在20-120℃结晶。
10.权利要求1的方法,其中所述熔体在70-120℃结晶。
11.权利要求1的方法,其中将固化产物在不低于70℃,但低于所述产物中β型结晶的熔点的温度拉伸。
12.权利要求1的方法,其中将固化产物在不低于90℃,但低于所述产物中β型结晶的熔点的温度拉伸。
13.权利要求1的方法,其中将固化产物在不低于70℃但低于Ts(℃)的温度拉伸,Ts(℃)定义为Ts=Tm-10,其中Tm为所述产物中β型结晶的熔点(℃)。
14.权利要求1的方法,其中将固化产物在不低于90℃但低于Ts(℃)的温度拉伸,Ts(℃)定义为Ts=Tm-10,其中Tm为所述产物中β型结晶的熔点(℃)。
15.权利要求1的方法,其中所述固化产物通过单轴拉伸而被拉伸。
16.权利要求1的方法,其中所述固化产物通过双轴拉伸而被拉伸。
17.一种制备基于聚丙烯的树脂的多孔拉伸制品的方法,该方法包括在15-140℃,使基于聚丙烯的树脂组合物的熔体结晶,以形成含β型结晶的固化产物,并将所得固化产物在高于70℃,但低于所述固化产物中β型结晶的熔点的温度拉伸,基于聚丙烯的树脂组合物包括基于聚丙烯树脂和0.0001-5重量份(每100重量份基于聚丙烯的树脂)下式(1)表示的酰胺化合物:
R2-NHCO-R1-CONH-R3 (1)其中R1是C1-24饱和或不饱和脂族二羧酸残基、C4-28饱和或不饱和脂环族二羧酸残基或C6-28芳族二羧酸残基;R2和R3彼此相同或不同,各代C3-18环烷基、C3-12环烯基或式
,其中R4是氢原子、C1-12直链或支链烷基、C2-12直链或支链烯基、C6-10环烷基或苯基;R4是C1-12直链或支链烷基或C2-12直链或支链烯基;R6和R7相同或不同,各自代表C1-4直链或支链烯基;
18.一种基于聚丙烯的树脂的多孔拉伸制品,其特征在于它是通过权利要求1的方法制备的。
19.一种基于聚丙烯的树脂的多孔拉伸制品,其特征在于它是通过权利要求17的方法制备的。
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JP143037/93 | 1993-05-20 | ||
JP143037/1993 | 1993-05-20 | ||
JP14303793 | 1993-05-20 |
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CN1098725A CN1098725A (zh) | 1995-02-15 |
CN1061060C true CN1061060C (zh) | 2001-01-24 |
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CN94105139A Expired - Lifetime CN1061060C (zh) | 1993-05-20 | 1994-05-20 | 基于聚丙烯树脂的多孔拉伸制品及其制备方法 |
Country Status (6)
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US (1) | US5491188A (zh) |
EP (1) | EP0632095B1 (zh) |
KR (1) | KR100297617B1 (zh) |
CN (1) | CN1061060C (zh) |
DE (1) | DE69428166T2 (zh) |
TW (1) | TW288028B (zh) |
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Also Published As
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EP0632095B1 (en) | 2001-09-05 |
EP0632095A3 (en) | 1996-02-28 |
EP0632095A2 (en) | 1995-01-04 |
KR100297617B1 (ko) | 2001-10-24 |
US5491188A (en) | 1996-02-13 |
TW288028B (zh) | 1996-10-11 |
DE69428166D1 (de) | 2001-10-11 |
CN1098725A (zh) | 1995-02-15 |
DE69428166T2 (de) | 2002-05-16 |
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