WO2001046300A1 - Polyolefin polymer and catalyst blend for bonding fluoropolymers - Google Patents
Polyolefin polymer and catalyst blend for bonding fluoropolymers Download PDFInfo
- Publication number
- WO2001046300A1 WO2001046300A1 PCT/US2000/010975 US0010975W WO0146300A1 WO 2001046300 A1 WO2001046300 A1 WO 2001046300A1 US 0010975 W US0010975 W US 0010975W WO 0146300 A1 WO0146300 A1 WO 0146300A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- article
- layer
- composition
- sodium
- potassium
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 82
- 229920002313 fluoropolymer Polymers 0.000 title claims abstract description 64
- 239000004811 fluoropolymer Substances 0.000 title claims abstract description 61
- 229920000642 polymer Polymers 0.000 title claims abstract description 21
- 239000003054 catalyst Substances 0.000 title claims abstract description 8
- 229920000098 polyolefin Polymers 0.000 title claims description 22
- 229920006120 non-fluorinated polymer Polymers 0.000 claims abstract description 23
- 150000003983 crown ethers Chemical class 0.000 claims abstract description 17
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims description 35
- 239000000178 monomer Substances 0.000 claims description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 17
- 239000004814 polyurethane Substances 0.000 claims description 15
- 229920002635 polyurethane Polymers 0.000 claims description 14
- 239000004952 Polyamide Substances 0.000 claims description 13
- 229920001577 copolymer Polymers 0.000 claims description 13
- 229920002647 polyamide Polymers 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 8
- 239000002184 metal Substances 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 7
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 229920000728 polyester Polymers 0.000 claims description 6
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 6
- MGAXYKDBRBNWKT-UHFFFAOYSA-N (5-oxooxolan-2-yl)methyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1OC(=O)CC1 MGAXYKDBRBNWKT-UHFFFAOYSA-N 0.000 claims description 5
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical group C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 238000010030 laminating Methods 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- 239000004642 Polyimide Substances 0.000 claims description 4
- 150000004703 alkoxides Chemical class 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 229920001721 polyimide Polymers 0.000 claims description 4
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- XUCNUKMRBVNAPB-UHFFFAOYSA-N fluoroethene Chemical compound FC=C XUCNUKMRBVNAPB-UHFFFAOYSA-N 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
- 150000004692 metal hydroxides Chemical class 0.000 claims description 3
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 3
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 3
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- VFTFKUDGYRBSAL-UHFFFAOYSA-N 15-crown-5 Chemical compound C1COCCOCCOCCOCCO1 VFTFKUDGYRBSAL-UHFFFAOYSA-N 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 150000003949 imides Chemical group 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical group O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 239000010410 layer Substances 0.000 description 59
- -1 polyethylene Polymers 0.000 description 19
- 229920001778 nylon Polymers 0.000 description 11
- 239000004677 Nylon Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- 238000010276 construction Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 230000004888 barrier function Effects 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 229920001897 terpolymer Polymers 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000002131 composite material Substances 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- 150000007529 inorganic bases Chemical class 0.000 description 4
- 239000011229 interlayer Substances 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920000299 Nylon 12 Polymers 0.000 description 3
- 229920002292 Nylon 6 Polymers 0.000 description 3
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 3
- 238000013329 compounding Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229920003345 Elvax® Polymers 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- 239000002033 PVDF binder Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000000536 complexating effect Effects 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000002828 fuel tank Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 229920000092 linear low density polyethylene Polymers 0.000 description 2
- 239000004707 linear low-density polyethylene Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000004005 microsphere Substances 0.000 description 2
- 229910052760 oxygen Chemical group 0.000 description 2
- SNGREZUHAYWORS-UHFFFAOYSA-N perfluorooctanoic acid Chemical class OC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F SNGREZUHAYWORS-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229920006345 thermoplastic polyamide Polymers 0.000 description 2
- BLTXWCKMNMYXEA-UHFFFAOYSA-N 1,1,2-trifluoro-2-(trifluoromethoxy)ethene Chemical compound FC(F)=C(F)OC(F)(F)F BLTXWCKMNMYXEA-UHFFFAOYSA-N 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical class FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- YTCHAEAIYHLXBK-UHFFFAOYSA-N 2-chloro-1,1,3,3,3-pentafluoroprop-1-ene Chemical compound FC(F)=C(Cl)C(F)(F)F YTCHAEAIYHLXBK-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- GVCWGFZDSIWLMO-UHFFFAOYSA-N 4-bromo-3,3,4,4-tetrafluorobut-1-ene Chemical compound FC(F)(Br)C(F)(F)C=C GVCWGFZDSIWLMO-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- KOOXYQMQLVQJHD-UHFFFAOYSA-L CCN(CC)PCC1=CC=CC=C1.CCN(CC)[P+](CC1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CN(C)[P+](CC1=CC=CC=C1)(N(C)C)N(C)C.[Cl-].[Cl-].Cl.Cl Chemical compound CCN(CC)PCC1=CC=CC=C1.CCN(CC)[P+](CC1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1.CN(C)[P+](CC1=CC=CC=C1)(N(C)C)N(C)C.[Cl-].[Cl-].Cl.Cl KOOXYQMQLVQJHD-UHFFFAOYSA-L 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004970 Chain extender Substances 0.000 description 1
- 229920001780 ECTFE Polymers 0.000 description 1
- 229920000219 Ethylene vinyl alcohol Polymers 0.000 description 1
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 description 1
- 239000005058 Isophorone diisocyanate Substances 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920001007 Nylon 4 Polymers 0.000 description 1
- 229920003189 Nylon 4,6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 102220602575 Ubiquitin conjugation factor E4 A_C88A_mutation Human genes 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- RFUGMORVSDZBLC-UHFFFAOYSA-N [Na].CC(N)=O Chemical compound [Na].CC(N)=O RFUGMORVSDZBLC-UHFFFAOYSA-N 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 229910052785 arsenic Inorganic materials 0.000 description 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- PRQROPMIIGLWRP-BZSNNMDCSA-N chemotactic peptide Chemical compound CSCC[C@H](NC=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-BZSNNMDCSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001246 colloidal dispersion Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000003028 elevating effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920000840 ethylene tetrafluoroethylene copolymer Polymers 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229920001973 fluoroelastomer Polymers 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 229920001684 low density polyethylene Polymers 0.000 description 1
- 239000004702 low-density polyethylene Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229960003574 milrinone Drugs 0.000 description 1
- VWUPWEAFIOQCGF-UHFFFAOYSA-N milrinone lactate Chemical compound [H+].CC(O)C([O-])=O.N1C(=O)C(C#N)=CC(C=2C=CN=CC=2)=C1C VWUPWEAFIOQCGF-UHFFFAOYSA-N 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical group 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 125000005496 phosphonium group Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 239000004632 polycaprolactone Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000909 polytetrahydrofuran Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 102220053011 rs727502896 Human genes 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- HSNUIYJWTSJUMS-UHFFFAOYSA-N sodium;trimethyl(oxido)silane Chemical compound [Na+].C[Si](C)(C)[O-] HSNUIYJWTSJUMS-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical group [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
- KSMYREBPTSSZDR-UHFFFAOYSA-M tributyl(prop-2-enyl)phosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CC=C KSMYREBPTSSZDR-UHFFFAOYSA-M 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B1/00—Layered products having a non-planar shape
- B32B1/08—Tubular products
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
- C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
- C08J5/128—Adhesives without diluent
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2439/00—Containers; Receptacles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2597/00—Tubular articles, e.g. hoses, pipes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2878—Adhesive compositions including addition polymer from unsaturated monomer
- Y10T428/2891—Adhesive compositions including addition polymer from unsaturated monomer including addition polymer from alpha-beta unsaturated carboxylic acid [e.g., acrylic acid, methacrylic acid, etc.] Or derivative thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
- Y10T428/2852—Adhesive compositions
- Y10T428/2896—Adhesive compositions including nitrogen containing condensation polymer [e.g., polyurethane, polyisocyanate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/3154—Of fluorinated addition polymer from unsaturated monomers
- Y10T428/31544—Addition polymer is perhalogenated
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]
- Y10T428/31573—Next to addition polymer of ethylenically unsaturated monomer
- Y10T428/3158—Halide monomer type [polyvinyl chloride, etc.]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31721—Of polyimide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/3175—Next to addition polymer from unsaturated monomer[s]
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31786—Of polyester [e.g., alkyd, etc.]
- Y10T428/31797—Next to addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31913—Monoolefin polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31913—Monoolefin polymer
- Y10T428/3192—Next to vinyl or vinylidene chloride polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31909—Next to second addition polymer from unsaturated monomers
- Y10T428/31928—Ester, halide or nitrile of addition polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31935—Ester, halide or nitrile of addition polymer
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31855—Of addition polymer from unsaturated monomers
- Y10T428/31938—Polymer of monoethylenically unsaturated hydrocarbon
Definitions
- the invention relates to bonding fluoropolymers to substantially non-fluorinated polymers and particularly to a polyolefin-catalyst mixture useful for bonding fluoropolymers to substantially non-fluorinated polymers.
- Fluorine-containing polymers that is. fluoropolymers or fluorinated polymers
- Many fluoropolymers are known to exhibit high thermal stability and usefulness at high temperatures as well as extreme toughness and flexibility at very low temperatures. Many fluoropolymers are also almost totally insoluble in a wide variety of organic solvents and resistant to many chemical compounds that might degrade other classes of less resistant materials. Additionally, many fluoropolymers are recognized for their barrier properties; that is, their ability to prevent the passage of liquids or vapors.
- Multi-layer articles such as multi-layer tubing have been used within these applications. These multi-layer products can comprise a fluoropolymer, which provides an inert vapor barrier, and one or more other layers that can add strength, rigidity, or other mechanical properties to the multi-layer article. As an example, some multi-layer articles include a fluoropolymer and a layer comprising a substantially non-fluorinated polymer.
- these multi-layer articles should not delaminate during use. That is, the adhesive bond strength between the different layers of the multi-layer article should be sufficiently strong and stable so as to prevent the different layers from separating on exposure to, for example, fuel, emission fluids, caustic or acidic solutions, or other aggressive chemicals.
- the adhesive bond strength between the different layers of the multi-layer article should be sufficiently strong and stable so as to prevent the different layers from separating on exposure to, for example, fuel, emission fluids, caustic or acidic solutions, or other aggressive chemicals.
- poor adhesion between two very dissimilar materials, fluoropolymer and hydrocarbon polymer makes the formation of these desired constructions difficult
- the layers can be adhesively bonded together by a layer of adhesive material between the two layers
- surface treatment of one or both of the layers, used independently or in conjunction with adhesive materials has been used to bond the two types of materials together
- layers comprising a fluoropolymer have been treated with a charged gaseous atmosphere followed by lamination with a layer of thermoplastic polyamide
- tie layer was a layer comprising a blend of dissimilar materials disposed between the fluoropolymer and substantially non-fluoropolymer layers
- the invention provides a composition comprising a mixture of a melt-processable, substantially non-fluorinated polymer and a catalyst system comprising a base and a crown ether
- the invention provides an article comprising a) a first layer comprising fluoropolymer, and b) a second layer bonded to the first layer, the second layer comprising a mixture of a melt processable, substantially non-fluorinated polymer, a base, and a crown ether
- the invention provides a method of bonding fluoropolymer to a substantially non-fluorinated polymer comprising the steps of a) providing a bonding composition comprising a mixture of a melt processable, substantially non-fluo ⁇ nated polymer, a base, and a crown ether, b) providing fluoropolymer, c) applying the bonding composition to a surface of the fluoropolymer, and
- compositions of the invention are useful for promoting the adhesion of fluoropolymers to hydrocarbon polymers such as functional polyolefins, polyamides.
- a "functionahzed polyolefin” is a polyolefin which has one or more functional groups, for example, lmide, amide, oxycarbonyl, anhydride, acetate, carbonyl, hydroxide, and like groups, pendant from or integral with the polyolefin polymer backbone
- compositions of the invention are useful for promoting the adhesion of fluoropolymers to hydrocarbon polymers such as polyethylene, copolymers comprising ethylene monomer, polyamides, polyurethanes, and other functionahzed polyolefins
- compositions of the invention contain one or more substantially non- fluorinated polyolefin
- Useful substantially non-fluorinated polymeric materials can comprise any of a number of well known hydrocarbon-based polymers and copolymers or mixtures thereof These polymeric materials also include substantially non-fluorinated polymeric materials considered to be pressure sensitive adhesives
- substantially non-fluorinated refers to polymers and polymeric materials having fewer than 10 percent of their carbon-bonded hydrogen atoms replaced with fluorine atoms
- the substantially non-fluorinated polymer has fewer than 2 percent of its carbon-bonded hydrogen atoms replaced with fluorine atoms, and more preferably fewer than 1 percent of
- Any melt-processable, carboxyl, carboxylate, carbonyl, anhydride, amide, imide, hydroxyl. or oxycarbonyl functional polyolefin may be used to make the substantially non- fluorinated polymeric material of the invention.
- These functional polymers can be prepared by copolymerization of functional monomers with ⁇ -olefin monomers (for example, ethylene, propylene, butylene, acrylate, vinyl ether, etc.), or, alternatively polyolefin polymers may be modified, or functionahzed, after polymerization by, for example, grafting, or oxidation.
- anhydride modified polyethylenes commercially available from the E.I. Du Pont de Nemours and Company. Wilmington, DE, under the trade designation "BYNEL”
- ELVAX oxycarboxy functional polyethylenes
- ethylene/acrylic acid copolymers commercially available from Dow Chemical Company, Midland, MI, under the trade
- Preferred functionahzed polyolefins include ethylene/vinyl acetate copolymers, ethylene/acrylic acid copolymers, ethylene/methyl acrylate copolymers, and ethylene/vinyl acetate copolymers
- Blends of the carboxyl, carboxylate, anhydride, amide, imide, hydroxyl, or oxycarbonyl functional polyolefins may also be used in the compositions of the present invention.
- Polyamides useful as the substantially non-fluorinated polymer include nylons that are generally commercially available from a number of sources. Particularly preferred polyamides include, but are not limited to, nylon 6, nylon 6.6. nylon 11, and nylon 12. It should be noted that the selection of a particular polyamide material should be based upon the physical requirements of the particular application for the resulting article. For example, nylon 6 and nylon 6,6 offer higher heat resistant properties than nylon 1 1 or nylon 12; whereas nylon 1 1 and nylon 12 offer better chemical resistant properties.
- nylons useful in the present invention include nylon 6.12, nylon 6,9, nylon 4, nylon 4,2, nylon 4,6, nylon 7, and nylon 8 Ring containing polyamides, for example, nylon 6,T and nylon 6,1 may also be used
- Polyether containing polyamides, such as PEBAXTM, may also be used
- Polyurethane polymers useful as the substantially non-fluorinated polymer include aliphatic, cycloahphatic, aromatic, and polycyclic polyurethanes These polyurethanes are typically produced by reaction of a polyfunctional isocyanate with a polyol according to well known procedures
- Useful d ⁇ socyanates employed in the production of suitable polyurethanes include dicyclohexylmethane-4,4'-dnsocyanate, isophorone diisocyanate, 1 ,6-hexamethylene diisocyanate, cyclohexyl diisocyanate, and diphenylmethane diisocyanate
- Combinations of one or more polyfunctional isocyanates may also be used
- Useful polyols include polypentyleneadipate glycol, polytetramethylene ether glycol. polyethylene glycol, polycaprolactone diol, poly- 1 ,2-butylene oxide glycol, and combinations thereof Chain extenders, such as butanediol or hexanediol, may also optionally be used in the reaction
- Commercially available polyurethanes useful in the present invention include PN-04 or 3429, available from Morton International, Inc ,
- compositions of the invention include one or more inorganic or organic bases
- Useful inorganic bases include metal hydroxides such as, but not limited to, lithium hydroxide, potassium hydroxide, and sodium hydroxide, metal alkoxides such as, but not limited to, potassium methoxide, potassium ethoxide, sodium methoxide, sodium ethoxide, potassium phenoxide, sodium phenoxide, metal amines such as, but not limited to, sodium ethyl amine and the like, and metal acetamides such as, but not limited to.
- metal hydroxides such as, but not limited to, lithium hydroxide, potassium hydroxide, and sodium hydroxide
- metal alkoxides such as, but not limited to, potassium methoxide, potassium ethoxide, sodium methoxide, sodium ethoxide, potassium phenoxide, sodium phenoxide
- metal amines such as, but not limited to, sodium ethyl amine and the like
- compositions of the invention contain one or more crown ethers that function as a phase transfer catalyst Crown ethers are macrocyc c polyethers comprising dimethylene oxide units which can coordinate to a centrally located metal atom via the oxygen atoms of the ethers, thereby functioning as electron donors to the metal atom
- Crown ethers are macrocyc c polyethers comprising dimethylene oxide units which can coordinate to a centrally located metal atom via the oxygen atoms of the ethers, thereby functioning as electron donors to the metal atom
- This class of compounds is known to have strong complexing or chelating capabilities and, depending on the number of dimethylene oxide groups, can be very metal ion specific relative to its complexing or chelating capabilities
- Crown ethers useful in the present invention that exhibit good chelating capabilities for sodium, calcium and potassium cations, include, but are not limited to, 18-crown-6 ether and 15-crown-5 ether.
- Fluoropolymer materials useful in the present invention include those fluoropolymers broadly categorized structurally into three basic classes.
- the first class includes those fluorinated polymers, copolymers, terpolymers, etc., comprising interpolymerized units derived from vinylidene fluoride or vinyl fluoride (sometimes referred to as "VF2" or “VDF” and “VF", respectively).
- fluoropolymer materials of this first class comprise at least 3 percent by weight of interpolymerized units derived from VF2 or VF.
- Such polymers may be homopolymers of VF2 or VF or copolymers of VF2 or VF and other ethylenically unsaturated monomers.
- VF2 or VF and other ethylenically unsaturated monomers are examples of fluoropolymers.
- VF2 and VF -containing polymers and copolymers can be made by well-known conventional means, for example, by free-radical polymerization of VF2 with or without other ethylenically-unsaturated monomers.
- the preparation of colloidal aqueous dispersions of such polymers and copolymers is described, for example, in U.S. Patent No. 4,335,238 (Moore et al.).
- This reference describes a process for copolymerizing fluorinated olefins in colloidal aqueous dispersions which is carried out in the presence of water-soluble initiators that produce free radicals, such as, for example, ammonium or alkali metal persulfates or alkali metal permanganates, and in the presence of emulsifiers, such as, in particular, the ammonium or alkali metal salts of perfluorooctanoic acid.
- Useful fluorine-containing monomers for copolymerization with VF2 or VF include hexafluoropropylene ("HFP"), tetrafluoroethylene (“TFE”), chlorotrifluoroethylene
- CFE CTLFE
- 2-chloropentafluoro-propene 2-chloropentafluoro-propene, perfluoroalkyl vinyl ethers
- 1-hydropentafluoropropene 2-hydro- pentafluoropropene
- dichlorodifluoroethylene trifluoroethylene
- 1,1- dichlorofluoroethylene vinyl fluoride
- perfluoro- 1 ,3-dioxoles such as those described in U.S. Patent No. 4,558,142 (Squire).
- Certain fluorine-containing di-olefins also are useful, such as perfluorodiallylether and perfluoro-l,3-butadiene.
- Said fluorine-containing monomer or monomers also may be copolymerized with fluorine-free terminally unsaturated olefinic co-monomers, for example, ethylene or propylene.
- fluorine-free terminally unsaturated olefinic co-monomers for example, ethylene or propylene.
- at least 50 percent by weight of all monomers in a polymerizable mixture are fluorine-containing monomers.
- the fluorine-containing monomer(s) may also be copolymerized with iodine- or bromine-containing cure-site monomers in order to prepare peroxide curable polymers.
- Suitable cure-site monomers include terminally unsaturated monoolefins of 2 to 4 carbon atoms such as bromodifluoroethylene, bromotrifluoroethylene, iodotrifluoroethylene, and 4-bromo-3 ,3 ,4,4-tetrafluoro-butene- 1.
- fluoropolymer materials of this first class include, for example, THV 200 fluoropolymer (available from Dyneon LLC, Saint Paul, MN), THV 500 fluoropolymer (available from Dyneon LLC), KYNARTM 740 fluoropolymer (available from Elf Atochem North America, Inc., Glen Rock, NJ), and fluoroelastomers such as FLU ORELTM FC-2178 fluoropolymer (available from Dyneon LLC) that have been crosslinked with, for example, BFg or protected polyhydroxy-aromatic compounds are also suitable for use in the preparation of the laminate constructions of the present invention.
- THV 200 fluoropolymer available from Dyneon LLC, Saint Paul, MN
- THV 500 fluoropolymer available from Dyneon LLC
- KYNARTM 740 fluoropolymer available from Elf Atochem North America, Inc., Glen Rock, NJ
- fluoroelastomers such as FLU OREL
- the second class of fluorinated materials useful in the practice of the invention broadly comprises those fluorinated polymers, copolymers, terpolymers, etc., comprising interpolymerized units derived from one or more of hexafluoropropylene (“HFP") monomers, tetrafluoroethylene (“TFE”) monomers, chlorotrifluoroethylene monomers, and or other perhalogenated monomers, and further derived from one or more hydrogen- containing and or non-fluorinated olefinically unsaturated monomers.
- HFP hexafluoropropylene
- TFE tetrafluoroethylene
- chlorotrifluoroethylene monomers and or other perhalogenated monomers
- Useful olefinically unsaturated monomers include alkylene monomers such as ethylene, propylene, 1- hydropentafluoropropene. 2-hydropentafluoropropene, etc.
- Fluoropolymers of this second class can be prepared by methods known in the fluoropolymer art. Such methods include, for example, free-radical polymerization of hexafluoropropylene and/or tetrafluoroethylene monomers with non-fluorinated ethylenically-unsaturated monomers.
- the desired olefinic monomers can be copolymerized in an aqueous colloidal dispersion in the presence of water-soluble initiators which produce free radicals such as ammonium or alkali metal persulfates or alkali metal permanganates, and in the presence of emulsifiers such as the ammonium or alkali metal salts of perfluorooctanoic acid. See, for example, U.S. Patent No. 4,335,238 (Moore et al.).
- fluoropolymer materials of the second class are poly(ethylene-co-tetrafluoroethylene) (ETFE), poly(tetrafluoroethylene-co-propylene), poly(chlorotrifluoroethylene-co-ethylene) (ECTFE), and the terpolymer poly(ethylene-co- tetrafluoroethylene-co-hexafluoropropylene), among others; all of which may be prepared by the above-described known polymerization methods.
- Many useful fluoropolymer materials also are available commercially, for example, from Dyneon LLC, under the trade designations HOSTAFLONTM X6810 and X6820; from Daikin America. Inc.. Decatur,
- the third class of fluorinated materials useful in the practice of the invention broadly comprises blends of fluoropolymers and polyolefins. Specific examples include blends of PVDF and poly(methyl methacrylate) (PMMA) and blends of PVDF and high vinyl acetate functionahzed polyolefins.
- compositions of the invention may additionally include one or more organo- onium salt catalysts.
- An organo-onium is the conjugate acid of a Lewis base (for example, phosphine, amine and ether) that can be formed by reacting the Lewis base with a suitable alkylating agent (for example, an alkyl halide or acyl halide). As a result of the reaction, there is an expansion of the valence of the electron donating atom of the Lewis base and a positive charge on the organo-onium compound.
- a suitable alkylating agent for example, an alkyl halide or acyl halide
- Many of the organo-onium compounds useful in the present invention contain at least one hetero atom (that is, a non-carbon atom such as N, P, and O bonded to the organic or inorganic moieties).
- One class of quaternary organo-onium compounds particularly useful in the present invention broadly comprises relatively positive and relatively negative ions wherein a phosphorous, arsenic, antimony, or nitrogen generally comprises the central atom of the positive ion, and the negative ion may be an organic or inorganic anion (for example, halide. sulfate, acetate, phosphate, phosphonate, hydroxide, alkoxide, phenoxide, bisphenoxide. etc.). Because of their relative stability in the presence of most inorganic bases, phosphoniums are the most preferred organo-oniums for use in the present invention.
- Sulfoniums are not chemically stable in the presence of most organic and inorganic bases and therefor are not considered useful in the invention. Many of the useful organo-onium compounds are known and described in the literature. See, for example, U.S. Patent Nos. 4,233,421 (Worm), 4,912,171 (Grootaert et al.), 5,086,123 (Guenther et al.), and 5,262, 490 (Kolb et al.). Fluorinated oniums, such as those described in U.S. Patent No.
- oniums such as those comprising two or more onium groups in the same molecule, (for example, bw-phosphoniums) may also be employed.
- Representative examples include, but are not limited to the following individually listed compounds and mixtures thereof: triphenylbenzyl phosphonium chloride tributylallyl phosphonium chloride tributylbenzyl ammonium chloride tetrabutyl ammonium bromide tetrabutyl phosphonium bromide 8-benzyl-l ,8-diazabicyclo[5,4,0]-7-unecenium chloride benzyl tris(dimethylamino) phosphonium chloride benzyl(diethylamino) phosphonium chloride benzyl(diethylamino)diphenylphosphonium chloride
- an onium catalyst may in some instances aid or increase the adhesion of the tie layer composition to a fluoropolymer and/or to another substrate.
- the bonding compositions of the present invention may be made by compounding the components of the composition in a mixing vessel using sufficient heat to melt the substantially non-fluorinated polymer and accompanying mixing to produce a uniform mixture.
- the compounding operation may be carried out in an extruder.
- the laminated structures of the present invention may be made by a coextrusion process wherein the various layers of the laminate construction are brought together with heat and pressure that may result in adequate adhesion between the various components of the laminate
- it may be desirable to further treat the resulting multi-layer composition for example, with additional heat and/or pressure to increase interlayer adhesion Extended heat exposure can be realized simply by delaying the cooling of the composition as it exits the coextrusion process
- additional heating it may also be accomplished by coextruding the laminate at a temperature higher than necessary for normal processing the components
- the finished article may be held at an elevated temperature for an extended period of time, or the finished article may be placed in a separate means for elevating the temperature of the article, such as an oven or heated liquid bath
- Yet another method of applying additional heat and pressure to the laminate is to pass it through one or more heated calendar rolls that is/are maintained at sufficient temperature and pressure to achieve the desired interlayer bond strength A combination of these methods may also be used
- the laminated structures of the present invention may also be prepared by laminating a film of the bonding composition to a fluoropolymer material by the application of heat and pressure and subsequently laminating a substantially non- fluoropolymer material to the bonding composition in a second step by the application of heat and pressure
- the laminated structures can be prepared in a single operation by assembling a stack of films comprising, in order, a fluoropolymer film, a bonding composition film, and a substantially non-fluoropolymer film and forming a consolidated laminate from the film stack be application of heat and pressure
- a third way of forming the laminated structures of the present invention is to apply the bonding composition to the fluoropolymer material as a solution coating allowing the solvent to evaporate, and subsequently forming a laminate construction by applying the substantially non-fluorinated polymeric material to the bonding composition coated portion of the fluoropolymer surface by applying sufficient heat and pressure to the laminate to produce a consolidated laminate
- the methods of this invention provide multi-layer compositions w ith improved inter-layer adhesion
- the methods and compositions of this invention are particularly useful for making articles, such as tubing and hoses, suitable for use in motor vehicles, for example, as fuel-line hoses, and for films and blow-molded articles such as bottles and anti-graffiti films where chemical resistance or barrier properties are important
- the two- layer compositions of this invention are also useful in preparing compositions having three or more layers
- a three layer composition of fluoropolymer to anhydride modified polyolefin to unmodified polyolefin could be prepared and might be useful in a fuel-tank construction
- Transparent embodiments of multi-layer compositions of the present invention may find particular utility in the construction of retroreflective sheeting articles generally, and particularly when resistance to chemical agents, solvents, soils, reduced moisture vapor transmission, or good interlayer adhesion in flexible sheetings subject to severe bending and flexing is required
- compositions of this invention may be rendered retroreflective by forming retroreflective elements on one side of the composition, or alternatively, by attaching a retroreflective base sheet by means of a transparent adhesive or by direct lamination
- the retroreflective base sheet may comprise a member with cube corner retroreflective elements or may comprise a microsphere-based retroreflective structure, for example, comprising a monolayer of transparent microspheres and reflective means disposed on the opposite side of the monolayer from the multi-layer composition It is preferred that the base layer is disposed on the non-fluoropolymer layer of the multi-layer composition
- An embodiment of this invention includes the encapsulated retroreflective sheeting article as is disclosed in U S Patent No 3,190,178 (McKenzie), in which the cover layer is provided by a multi-layer composition according to the present invention
- Retroreflective articles of the invention may be made in rigid or flexible form Multi-layer compositions of the present invention may be used as barrier layers
- An embodiment of the present invention includes articles in accordance with U S Patent No 5,069.964 (Tolliver), in which the plasticizer resistant barrier layer comprises a multi-layer composition in accordance with the present invention
- the multi-layer compositions of the present invention may find particular utility in the construction of flexible retroreflective sheeting articles
- a preferred embodiment of the present invention includes a retroreflective article in accordance with PCT Publication Nos WO 95/1 1464 or WO 95/1 1943, wherein the flexible overlay film described in PCT Publication No WO 95/1 1464 or the flexible body layer of PCT Publication No. WO 95/11943 is constituted by a multi-layer composition in accordance with this invention.
- Glossary EVAL 105 is a trade name for an ethylene vinyl alcohol copolymer, available from
- ELVAX 250, ELVAX 450, are trade names for ethylene/vinyl acetate copolymers, commercially available from E.I. DuPont de Nemours and Co., Wilmington DE.
- PRIMACOR 3150 is a trade name for an ethylene/acrylic acid copolymer. commercially available from Dow Chemical Company. Midland, MI.
- EMAC 2220 is a trade name for a ethylene/methyl acrylate copolymer, commercially available from Chevron Chemical Co.. Houston, TX.
- BYNELL 3101 is a trade name for a ethylene/vinyl acetate copolymer and having an organic acid group grafted thereon, commercially available from E.I. DuPont de Nemours.
- AT 1841 is an ethylene/vinyl acetate copolymer. commercially available from AT Polymer, Edmonton, Canada.
- THV200 is a terpolymer of tetrafluoroethylene. hexafluoropropylene, and vinylidene fluoride, commercially available from Dyneon LLC, St. Paul, MN.
- THV500 is a terpolymer of tetrafluoroethylene, hexafluoropropylene, and vinylidene fluoride, commercially available from Dyneon LLC.
- 18-crown-6 is a crown ether available from Aldrich Chemical, Milwaukee, WI.
- LLDPE is a linear, low density polyethylene film, available from Dow Chemical
- Bu4PBr is tetrabutyl phosphonium bromide.
- NaOSi(CH3)3 is sodium trimethylsilanoate.
- KP is potassium phthalimide.
- KOH is potassium hydroxide.
- LiOH is lithium hydroxide.
- NaOH is sodium hydroxide.
- KOCH3 is potassium methoxide.
- NaOPh sodium phenoxide
- Tyramine hydrochloride 4-(2-aminoethyl)-phenol, available from Aldrich Chemical.
- the bonding composition as described in Table 1 below, was prepared by compounding the substantially non-fluorinated polymer, a base, and a crown ether in an internal bowl mixer equipped with roller blades that was operated at 200 °C and a mixing speed of 60 - 70 rpm for a period of ten minutes.
- the compounded bonding composition was subsequently formed into a flat film 0.2 cm thick in a heated press operating at 200 °C and 24 KPa (3.5 psi) pressure for a period of approximately 30 seconds.
- Composites were prepared by assembling a laminate structure consisting of a fluoropolymer film, 2.54 cm by 7.62 cm (1 inch by 3 inches) in size and 0.2 cm thick, of THV200 and THV500, the bonding composition film 1.25 cm by 5.08 cm in size (0.5 inch by 2 inches), and an
- LLDPE film (2.54 cm by 7.62 cm (1 inch by 3 inches) in size and 0.32 cm thick).
- a strip of silicone liner (#7520, available from Minnesota Mining and Manufacturing Company, St. Paul, MN) 2.54 cm by 7.62 cm (1 inch by 3 inches) was inserted between the THV layer and the substantially non-fluoropolymer layer to a depth of 1.25 cm (0.5 inch) along the short edge of laminate construction prior to placing the laminate in a press to produce a composite.
- Three identical composites were simultaneously prepared in a "hot press” using a Wabash Hydraulic Press Co. heated platen press operating at 200 °C at a pressure of 24 KPa (3.5 psi) for two minutes. The composites were removed from the press, cooled to room temperature in a "cold press," and the silicone liner removed to provide samples of the consolidated laminates having THV and the substantially non-fluoropolymer layer
- the BF5 dipotassium salt was prepared by mixing one equivalent of Bisphenol-AF with two equivalents of methanolic potassium methoxide and removing the methanol by evaporation to obtain a solid salt.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Mechanical Engineering (AREA)
- Laminated Bodies (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Wrappers (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002392129A CA2392129A1 (en) | 1999-12-22 | 2000-04-21 | Polyolefin polymer and catalyst blend for bonding fluoropolymers |
DE60035524T DE60035524T2 (en) | 1999-12-22 | 2000-04-21 | POLYOLEFIN POLYMER AND CATALYST MIXTURE FOR BINDING FLUOROPOLYMERS |
JP2001547205A JP4718085B2 (en) | 1999-12-22 | 2000-04-21 | Binding composition and product using the same |
EP00928335A EP1246864B1 (en) | 1999-12-22 | 2000-04-21 | Polyolefin polymer and catalyst blend for bonding fluoropolymers |
AU46588/00A AU4658800A (en) | 1999-12-22 | 2000-04-21 | Polyolefin polymer and catalyst blend for bonding fluoropolymers |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/470,155 | 1999-12-22 | ||
US09/470,155 US6767948B1 (en) | 1999-12-22 | 1999-12-22 | Polyolefin polymer and catalyst blend for bonding fluoropolymers |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001046300A1 true WO2001046300A1 (en) | 2001-06-28 |
Family
ID=23866496
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2000/010975 WO2001046300A1 (en) | 1999-12-22 | 2000-04-21 | Polyolefin polymer and catalyst blend for bonding fluoropolymers |
Country Status (7)
Country | Link |
---|---|
US (2) | US6767948B1 (en) |
EP (1) | EP1246864B1 (en) |
JP (2) | JP4718085B2 (en) |
AU (1) | AU4658800A (en) |
CA (1) | CA2392129A1 (en) |
DE (1) | DE60035524T2 (en) |
WO (1) | WO2001046300A1 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006131563A3 (en) * | 2005-06-09 | 2007-02-22 | Uponor Innovation Ab | An improved multilayer pipe |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2003002660A1 (en) * | 2001-06-28 | 2003-01-09 | Daikin Industries, Ltd. | Aqueous emulsion resin compositions |
US7297391B2 (en) * | 2004-02-20 | 2007-11-20 | Saint-Gobain Performance Plastics Corporation | Draw resonance resistant multilayer films |
US7267865B2 (en) * | 2004-02-20 | 2007-09-11 | Saint-Gobain Performance Plastics Corporation | Draw resonant resistant multilayer films |
WO2006046533A1 (en) * | 2004-10-25 | 2006-05-04 | Sumitomo Electric Fine Polymer, Inc. | Process for producing porous composite material and porous composite material |
US7638186B2 (en) * | 2005-06-13 | 2009-12-29 | 3M Innovative Properties Company | Fluoropolymer containing laminates |
US7589140B2 (en) * | 2005-09-29 | 2009-09-15 | 3M Innovative Properties Company | Fluoropolymer bonding compositions |
US7901778B2 (en) * | 2006-01-13 | 2011-03-08 | Saint-Gobain Performance Plastics Corporation | Weatherable multilayer film |
US7993523B2 (en) * | 2007-03-06 | 2011-08-09 | E. I. Du Pont De Nemours And Company | Liquid filtration media |
US8038013B2 (en) * | 2007-03-06 | 2011-10-18 | E.I. Du Pont De Nemours And Company | Liquid filtration media |
US8765255B2 (en) | 2007-03-06 | 2014-07-01 | E I Du Pont De Nemours And Company | Breathable waterproof garment |
US7866348B2 (en) * | 2008-05-01 | 2011-01-11 | Saint-Gobain Performance Plastics Corporation | Multi-layered fuel tubing |
KR20170015552A (en) * | 2008-12-05 | 2017-02-08 | 이 아이 듀폰 디 네모아 앤드 캄파니 | Filter media with nanoweb layer |
DE102010003909A1 (en) * | 2010-04-13 | 2011-10-13 | Evonik Degussa Gmbh | Flexible tube with multilayer construction |
CN107033808B (en) * | 2010-05-10 | 2020-01-17 | 陶氏环球技术有限责任公司 | Adhesion promoter and preparation method thereof |
GB201108963D0 (en) * | 2011-05-27 | 2011-07-13 | 3M Innovative Properties Co | Composite materials comprising polyamides and fluoroelastomers |
CN102327761B (en) * | 2011-07-26 | 2013-08-07 | 东华大学 | Polymer composite micro-bead and preparation method thereof |
EP2888297B1 (en) | 2012-08-21 | 2019-12-11 | 3M Innovative Properties Company | Semi-fluorinated thermoplastic resins with low gel content |
EP3472241A1 (en) | 2016-06-20 | 2019-04-24 | 3M Innovative Properties Company | Self-priming adhesive |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4740562A (en) * | 1985-06-07 | 1988-04-26 | Agru Alois Gruber & Sohn Ohg | Method for the surface modification of objects made of polyvinylidene fluoride |
US4980086A (en) * | 1985-10-16 | 1990-12-25 | Toagosei Chemical Industry, Co., Ltd. | Curable composition |
WO1999052975A1 (en) * | 1998-04-09 | 1999-10-21 | Minnesota Mining And Manufacturing Company | Multi-layer compositions comprising a fluoropolymer |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3190178A (en) | 1961-06-29 | 1965-06-22 | Minnesota Mining & Mfg | Reflex-reflecting sheeting |
CH635610A5 (en) * | 1977-02-18 | 1983-04-15 | Hoechst Ag | Thermosetting coating MIX. |
AU525570B2 (en) * | 1977-12-07 | 1982-11-11 | Hoechst A.G. | Acid curable epoxy resin composition |
US4197380A (en) | 1978-03-01 | 1980-04-08 | Raychem Corporation | Hot melt adhesive comprising fluorocarbon elastomer, ethylene copolymer and tackifier |
US4233421A (en) | 1979-02-26 | 1980-11-11 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition containing sulfonium curing agents |
US4335238A (en) | 1980-10-06 | 1982-06-15 | E. I. Du Pont De Nemours And Company | Fluoropolymer hexafluoropropene, tetrafluorethene and 1,1-difluoroethene |
US4558142A (en) | 1981-03-11 | 1985-12-10 | Hoffmann-La Roche Inc. | 7-Fluoro-prostacyclin analogs |
US4677017A (en) | 1983-08-01 | 1987-06-30 | Ausimont, U.S.A., Inc. | Coextrusion of thermoplastic fluoropolymers with thermoplastic polymers |
US4549921A (en) | 1983-10-28 | 1985-10-29 | E. I. Du Pont De Nemours And Company | Lamination of fluorocarbon films |
US5086123A (en) | 1984-02-27 | 1992-02-04 | Minnesota Mining And Manufacturing Company | Fluoroelastomer compositions containing fluoroaliphatic sulfonamides as curing agents |
JPS617337A (en) * | 1984-06-22 | 1986-01-14 | Mitsubishi Petrochem Co Ltd | Bonding of formed article of fluorine-containing polymer |
US4600651A (en) | 1984-08-06 | 1986-07-15 | E. I. Du Pont De Nemours And Company | Fluoroelastomer laminates |
US4886689A (en) | 1986-08-29 | 1989-12-12 | Ausimont, U.S.A., Inc. | Matrix-matrix polyblend adhesives and method of bonding incompatible polymers |
US5169979A (en) * | 1987-10-01 | 1992-12-08 | Hoechst Ag | Curing component, and the use thereof |
US4912171A (en) | 1988-04-01 | 1990-03-27 | Minnesota Mining And Manufacturing Company | Fluoroelastomer curing process with phosphonium compound |
EP0489004B1 (en) | 1988-12-21 | 1995-10-25 | Raychem Corporation | Thermoplastic fluoropolymer adhesive composition |
FR2646634B1 (en) | 1989-05-05 | 1991-08-30 | Solvay | MULTIPLE POLYMERIC LAYER STRUCTURES COMPRISING A VINYLIDENE FLUORIDE POLYMER LAYER LINKED TO A POLAR POLYMER LAYER |
US5069964A (en) | 1989-05-23 | 1991-12-03 | Minnesota Mining And Manufacturing Company | Flexible, substrate-insular retroreflective sheeting |
US5227426A (en) * | 1990-12-27 | 1993-07-13 | Exxon Chemical Patents Inc. | Adhesives based on elastomeric copolymers having theromplastic polymer grafts |
US5441782A (en) | 1991-07-16 | 1995-08-15 | Central Glass Company, Limited | Plastic laminate having polyamide resin surface layer and fluororesin surface layer |
FR2687619B1 (en) | 1992-02-25 | 1994-04-08 | Elf Atochem Sa | TUBE FOR TRANSPORT OF FUEL. |
US5262490A (en) | 1992-08-24 | 1993-11-16 | Minnesota Mining And Manufacturing Company | Fluoroelastomer composition with organo-onium compounds |
DE4310884A1 (en) | 1993-04-02 | 1994-10-06 | Huels Chemische Werke Ag | Multi-layer plastic tube |
FR2705683B1 (en) | 1993-04-30 | 1995-08-04 | Atochem Elf Sa | Glutarimide patterned bonding agent and its application as a barrier material. |
EP0642921B1 (en) | 1993-09-09 | 2001-12-19 | AUSIMONT S.p.A. | Multilayer structures of fluorinated and non-flurinated thermoplastic polymers |
AU681461B2 (en) | 1993-10-20 | 1997-08-28 | Minnesota Mining And Manufacturing Company | Ultra-flexible retroreflective cube corner composite sheetings and methods of manufacture |
US5486233A (en) | 1993-10-28 | 1996-01-23 | Western Mining Corporation Limited | Pigment extenders |
DE69435291D1 (en) | 1993-10-28 | 2010-06-10 | Asahi Glass Co Ltd | Fluoride-containing polymer adhesive and this used laminate |
WO1995011940A1 (en) | 1993-10-29 | 1995-05-04 | Daikin Industries, Ltd. | Thermoplastic resin composition and laminate made therefrom |
US5427831B1 (en) | 1993-11-12 | 1998-01-06 | Du Pont | Fluoropolymer laminates |
US5320888A (en) | 1993-11-12 | 1994-06-14 | E. I. Du Pont De Nemours And Company | Fluoroelastomer laminates |
ATE180713T1 (en) | 1993-12-13 | 1999-06-15 | Atochem Elf Sa | MULTI-LAYER ITEM MADE OF A VULCANIZED ELASTOMER DIRECTLY BONDED TO A THERMOPLASTIC MATERIAL |
DE69523930T2 (en) | 1994-08-19 | 2002-06-27 | Minnesota Mining & Mfg | COMPOSITIONS OF A MULTILAYER OBJECT WITH A FLUOROPOLYMER LAYER |
US5658670A (en) | 1994-08-19 | 1997-08-19 | Minnesota Mining And Manufactury Company | Multi-layer compositions having a fluoropolymer layer |
US5656121A (en) | 1994-08-19 | 1997-08-12 | Minnesota Mining And Manufacturing Company | Method of making multi-layer composites having a fluoropolymer layer |
US5589028A (en) | 1994-11-03 | 1996-12-31 | Elf Atochem North America, Inc. | Bonding method employing tie layers for adhering polyethylene to fluoropolymers |
WO1996016801A1 (en) | 1994-11-29 | 1996-06-06 | Elf Atochem S.A. | Process for producing a multi-layered article |
US5591804A (en) | 1995-12-21 | 1997-01-07 | Minnesota Mining And Manufacturing Company | Fluorinated onium salts, curable compositions containing same, and method of curing using same |
US6197393B1 (en) | 1997-06-27 | 2001-03-06 | 3M Innovative Properties Company | Multi-layer compositions comprising a fluoropolymer |
AU8153598A (en) | 1997-06-27 | 1999-01-19 | Minnesota Mining And Manufacturing Company | Method of adhering a fluoropolymer layer to a second layer of an adhesive article and articles produced by same |
US6156400A (en) | 1998-04-09 | 2000-12-05 | 3M Innovative Properties Company | Multi-layer compositions comprising a fluoropolymer |
US6423778B1 (en) * | 1999-06-30 | 2002-07-23 | Basf Corporation | Process for coating olefinic substrates |
-
1999
- 1999-12-22 US US09/470,155 patent/US6767948B1/en not_active Expired - Lifetime
-
2000
- 2000-04-21 EP EP00928335A patent/EP1246864B1/en not_active Expired - Lifetime
- 2000-04-21 AU AU46588/00A patent/AU4658800A/en not_active Abandoned
- 2000-04-21 DE DE60035524T patent/DE60035524T2/en not_active Expired - Lifetime
- 2000-04-21 WO PCT/US2000/010975 patent/WO2001046300A1/en active IP Right Grant
- 2000-04-21 JP JP2001547205A patent/JP4718085B2/en not_active Expired - Fee Related
- 2000-04-21 CA CA002392129A patent/CA2392129A1/en not_active Abandoned
-
2004
- 2004-04-22 US US10/829,697 patent/US6869682B2/en not_active Expired - Lifetime
-
2011
- 2011-01-14 JP JP2011005784A patent/JP2011102397A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4740562A (en) * | 1985-06-07 | 1988-04-26 | Agru Alois Gruber & Sohn Ohg | Method for the surface modification of objects made of polyvinylidene fluoride |
US4980086A (en) * | 1985-10-16 | 1990-12-25 | Toagosei Chemical Industry, Co., Ltd. | Curable composition |
WO1999052975A1 (en) * | 1998-04-09 | 1999-10-21 | Minnesota Mining And Manufacturing Company | Multi-layer compositions comprising a fluoropolymer |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006131563A3 (en) * | 2005-06-09 | 2007-02-22 | Uponor Innovation Ab | An improved multilayer pipe |
Also Published As
Publication number | Publication date |
---|---|
AU4658800A (en) | 2001-07-03 |
JP2003518181A (en) | 2003-06-03 |
CA2392129A1 (en) | 2001-06-28 |
JP4718085B2 (en) | 2011-07-06 |
DE60035524D1 (en) | 2007-08-23 |
JP2011102397A (en) | 2011-05-26 |
US20040197569A1 (en) | 2004-10-07 |
US6767948B1 (en) | 2004-07-27 |
EP1246864B1 (en) | 2007-07-11 |
US6869682B2 (en) | 2005-03-22 |
DE60035524T2 (en) | 2008-03-13 |
EP1246864A1 (en) | 2002-10-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1246864B1 (en) | Polyolefin polymer and catalyst blend for bonding fluoropolymers | |
EP1165669B1 (en) | Compositions for fluoropolymer bonding to non-fluorinated polymers | |
EP1080140B1 (en) | Multi-layer compositions comprising a fluoropolymer | |
US6074719A (en) | Multi-layer compositions having a fluoropolymer layer | |
JP4701436B2 (en) | Multilayer composition comprising a fluoropolymer | |
US6077609A (en) | Composite articles including fluoropolymers and non-fluorinated polymers and method for making the same | |
EP0991519B1 (en) | Composite articles including a fluoropolymer blend | |
JP5005876B2 (en) | Multilayer product comprising a fluoroelastomer layer and a barrier layer, and a method for producing the product | |
US6096428A (en) | Multi-layer compositions comprising a fluoropolymer | |
EP0777578B1 (en) | Multi-layer compositions having a fluoropolymer layer | |
CA2195790C (en) | Multi-layer compositions having a fluoropolymer layer |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AT AU AZ BA BB BG BR BY CA CH CN CR CU CZ CZ DE DE DK DK DM DZ EE EE ES FI FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2392129 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2000928335 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref country code: JP Ref document number: 2001 547205 Kind code of ref document: A Format of ref document f/p: F |
|
WWP | Wipo information: published in national office |
Ref document number: 2000928335 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WD | Withdrawal of designations after international publication |
Free format text: ALL DESIGNATED STATES EXCEPT EP (EUROPEAN PATENT), CA AND JP |
|
WWG | Wipo information: grant in national office |
Ref document number: 2000928335 Country of ref document: EP |