CA1082387A - Produits adhesifs ameliores, a base de copolyesters sequences - Google Patents

Produits adhesifs ameliores, a base de copolyesters sequences

Info

Publication number: CA1082387A
Authority: CA; Canada
Prior art keywords: weight; percent; copolyester; elastomer; composition
Prior art date: 1974-11-04
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

Application number

CA213,112A

Other languages

English (en)

Other versions

CA213112S (en

Inventor

John M. Edinger

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and Co

Priority date (The priority date 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 date listed.)

1974-11-04

Filing date

1974-11-04

Publication date

1980-07-22

1974-11-04 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1974-11-04 Priority to CA213,112A priority Critical patent/CA1082387A/fr

1980-07-22 Application granted granted Critical

1980-07-22 Publication of CA1082387A publication Critical patent/CA1082387A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 171
229920001634 Copolyester Polymers 0.000 title claims abstract description 78
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 111
150000002148 esters Chemical group 0.000 claims abstract description 88
-1 e.g. Chemical compound 0.000 claims abstract description 71
229920001971 elastomer Polymers 0.000 claims abstract description 55
239000000806 elastomer Substances 0.000 claims abstract description 55
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 54
150000001875 compounds Chemical class 0.000 claims abstract description 53
125000003118 aryl group Chemical group 0.000 claims abstract description 50
230000001070 adhesive effect Effects 0.000 claims abstract description 40
229920001169 thermoplastic Polymers 0.000 claims abstract description 40
239000004416 thermosoftening plastic Substances 0.000 claims abstract description 40
239000000853 adhesive Substances 0.000 claims abstract description 39
239000000155 melt Substances 0.000 claims abstract description 32
229920005992 thermoplastic resin Polymers 0.000 claims abstract description 31
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 30
230000008018 melting Effects 0.000 claims abstract description 30
238000002844 melting Methods 0.000 claims abstract description 30
239000003381 stabilizer Substances 0.000 claims abstract description 26
150000002009 diols Chemical class 0.000 claims abstract description 23
229920006236 copolyester elastomer Polymers 0.000 claims abstract description 22
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 21
229920001577 copolymer Chemical class 0.000 claims abstract description 18
229920000909 polytetrahydrofuran Polymers 0.000 claims abstract description 13
150000008064 anhydrides Chemical group 0.000 claims abstract description 9
CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims abstract description 7
QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract 10
150000002531 isophthalic acids Chemical class 0.000 claims abstract 2
150000003504 terephthalic acids Chemical class 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 55
239000002253 acid Substances 0.000 claims description 44
229920005989 resin Polymers 0.000 claims description 41
239000011347 resin Substances 0.000 claims description 41
150000003254 radicals Chemical class 0.000 claims description 30
229920000642 polymer Polymers 0.000 claims description 29
239000003960 organic solvent Substances 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
238000002156 mixing Methods 0.000 claims description 18
YTLYLLTVENPWFT-UPHRSURJSA-N (Z)-3-aminoacrylic acid Chemical compound N\C=C/C(O)=O YTLYLLTVENPWFT-UPHRSURJSA-N 0.000 claims description 17
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
239000011248 coating agent Substances 0.000 claims description 17
238000000576 coating method Methods 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 16
239000005977 Ethylene Substances 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
229910052739 hydrogen Inorganic materials 0.000 claims description 16
125000001931 aliphatic group Chemical group 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
239000003607 modifier Substances 0.000 claims description 13
150000002989 phenols Chemical class 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 12
229920001519 homopolymer Polymers 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 10
VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims description 10
125000004122 cyclic group Chemical group 0.000 claims description 10
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 10
JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 9
239000011280 coal tar Substances 0.000 claims description 9
RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 8
239000004215 Carbon black (E152) Substances 0.000 claims description 8
KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 claims description 8
229930195733 hydrocarbon Natural products 0.000 claims description 8
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 8
239000011295 pitch Substances 0.000 claims description 8
KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 claims description 8
239000013032 Hydrocarbon resin Substances 0.000 claims description 7
ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical group C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims description 7
229920006270 hydrocarbon resin Polymers 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
229920005604 random copolymer Polymers 0.000 claims description 7
KPAPHODVWOVUJL-UHFFFAOYSA-N 1-benzofuran;1h-indene Chemical compound C1=CC=C2CC=CC2=C1.C1=CC=C2OC=CC2=C1 KPAPHODVWOVUJL-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229920000180 alkyd Polymers 0.000 claims description 6
150000003336 secondary aromatic amines Chemical class 0.000 claims description 6
239000000758 substrate Substances 0.000 claims description 6
239000001993 wax Substances 0.000 claims description 6
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
239000012965 benzophenone Substances 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
229920001568 phenolic resin Polymers 0.000 claims description 5
239000005011 phenolic resin Substances 0.000 claims description 5
238000007789 sealing Methods 0.000 claims description 5
150000003505 terpenes Chemical class 0.000 claims description 5
235000007586 terpenes Nutrition 0.000 claims description 5
125000002947 alkylene group Chemical group 0.000 claims description 4
150000001718 carbodiimides Chemical class 0.000 claims description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
239000006185 dispersion Substances 0.000 claims 14
230000006872 improvement Effects 0.000 claims 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
238000009740 moulding (composite fabrication) Methods 0.000 claims 7
230000001804 emulsifying effect Effects 0.000 claims 6
229920005547 polycyclic aromatic hydrocarbon Polymers 0.000 claims 4
239000000839 emulsion Substances 0.000 claims 3
VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical group C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 claims 2
159000000032 aromatic acids Chemical class 0.000 claims 2
239000008199 coating composition Substances 0.000 claims 2
239000002131 composite material Substances 0.000 claims 2
230000000087 stabilizing effect Effects 0.000 claims 2
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims 1
239000010426 asphalt Substances 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
238000010030 laminating Methods 0.000 claims 1
239000010410 layer Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 1
239000002344 surface layer Substances 0.000 claims 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 3
239000004615 ingredient Substances 0.000 abstract description 2
238000012360 testing method Methods 0.000 description 20
238000003776 cleavage reaction Methods 0.000 description 19
230000007017 scission Effects 0.000 description 19
150000002500 ions Chemical class 0.000 description 18
VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 14
WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 10
239000000047 product Substances 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
WCVOGSZTONGSQY-UHFFFAOYSA-N 2,4,6-trichloroanisole Chemical compound COC1=C(Cl)C=C(Cl)C=C1Cl WCVOGSZTONGSQY-UHFFFAOYSA-N 0.000 description 7
239000000463 material Substances 0.000 description 7
239000000178 monomer Substances 0.000 description 7
238000002360 preparation method Methods 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
229920000728 polyester Polymers 0.000 description 6
229920002554 vinyl polymer Polymers 0.000 description 6
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
229920000877 Melamine resin Polymers 0.000 description 5
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 5
238000004821 distillation Methods 0.000 description 5
150000002430 hydrocarbons Chemical class 0.000 description 5
238000006116 polymerization reaction Methods 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
229920008712 Copo Polymers 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 4
DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000002245 particle Substances 0.000 description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
239000000126 substance Substances 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
239000000945 filler Substances 0.000 description 3
JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
210000004940 nucleus Anatomy 0.000 description 3
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 3
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
UGIJCMNGQCUTPI-UHFFFAOYSA-N 2-aminoethyl prop-2-enoate Chemical compound NCCOC(=O)C=C UGIJCMNGQCUTPI-UHFFFAOYSA-N 0.000 description 2
XOUQAVYLRNOXDO-UHFFFAOYSA-N 2-tert-butyl-5-methylphenol Chemical compound CC1=CC=C(C(C)(C)C)C(O)=C1 XOUQAVYLRNOXDO-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
241000736839 Chara Species 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
OPFTUNCRGUEPRZ-QLFBSQMISA-N Cyclohexane Natural products CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 2
241001251094 Formica Species 0.000 description 2
239000004831 Hot glue Substances 0.000 description 2
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 2
241001163743 Perlodes Species 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
241000022563 Rema Species 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
239000001361 adipic acid Substances 0.000 description 2
235000011037 adipic acid Nutrition 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
CRPUJAZIXJMDBK-UHFFFAOYSA-N camphene Chemical compound C1CC2C(=C)C(C)(C)C1C2 CRPUJAZIXJMDBK-UHFFFAOYSA-N 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
239000011294 coal tar pitch Substances 0.000 description 2
229910017052 cobalt Inorganic materials 0.000 description 2
239000010941 cobalt Substances 0.000 description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
125000005442 diisocyanate group Chemical group 0.000 description 2
230000000694 effects Effects 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 2
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 2
239000007789 gas Substances 0.000 description 2
150000002334 glycols Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012943 hotmelt Substances 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
CVVFFUKULYKOJR-UHFFFAOYSA-N n-phenyl-4-propan-2-yloxyaniline Chemical compound C1=CC(OC(C)C)=CC=C1NC1=CC=CC=C1 CVVFFUKULYKOJR-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
239000004033 plastic Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 2
239000000243 solution Substances 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 2
238000010998 test method Methods 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
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239000012260 resinous material Substances 0.000 description 1
239000000565 sealant Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000011269 tar Substances 0.000 description 1
239000011271 tar pitch Substances 0.000 description 1
150000001911 terphenyls Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
150000000000 tetracarboxylic acids Chemical class 0.000 description 1
230000000930 thermomechanical effect Effects 0.000 description 1
KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
125000005628 tolylene group Chemical group 0.000 description 1
NJJINPLVGVUXTF-UHFFFAOYSA-N tributan-2-yl phosphite Chemical compound CCC(C)OP(OC(C)CC)OC(C)CC NJJINPLVGVUXTF-UHFFFAOYSA-N 0.000 description 1
XTTGYFREQJCEML-UHFFFAOYSA-N tributyl phosphite Chemical compound CCCCOP(OCCCC)OCCCC XTTGYFREQJCEML-UHFFFAOYSA-N 0.000 description 1
IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
108091007668 trihex Proteins 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
DECPGQLXYYCNEZ-UHFFFAOYSA-N tris(6-methylheptyl) phosphite Chemical compound CC(C)CCCCCOP(OCCCCCC(C)C)OCCCCCC(C)C DECPGQLXYYCNEZ-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
238000009834 vaporization Methods 0.000 description 1
230000008016 vaporization Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
150000003739 xylenols Chemical class 0.000 description 1
239000004246 zinc acetate Substances 0.000 description 1

Landscapes

Adhesives Or Adhesive Processes (AREA)
Compositions Of Macromolecular Compounds (AREA)

CA213,112A 1974-11-04 1974-11-04 Produits adhesifs ameliores, a base de copolyesters sequences Expired CA1082387A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA213,112A CA1082387A (fr)	1974-11-04	1974-11-04	Produits adhesifs ameliores, a base de copolyesters sequences

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA213,112A CA1082387A (fr)	1974-11-04	1974-11-04	Produits adhesifs ameliores, a base de copolyesters sequences

Publications (1)

Publication Number	Publication Date
CA1082387A true CA1082387A (fr)	1980-07-22

Family

ID=4101551

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA213,112A Expired CA1082387A (fr)	1974-11-04	1974-11-04	Produits adhesifs ameliores, a base de copolyesters sequences

Country Status (1)

Country	Link
CA (1)	CA1082387A (fr)

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CN111902448A (zh) *	2018-03-26	2020-11-06	美敦力公司	聚(醚-碳酸酯)基聚合物以及医疗装置
US11548974B2 (en)	2018-03-26	2023-01-10	Medtronic, Inc.	Modified polyisobutylene-based polymers, methods of making, and medical devices
CN116120721A (zh) *	2018-03-12	2023-05-16	耐克创新有限合伙公司	热塑性泡沫物品
CN117844556A (zh) *	2023-12-29	2024-04-09	辽宁海华科技股份有限公司	一种支撑辊润滑方式用碳钢热轧工艺润滑剂组合物

1974
- 1974-11-04 CA CA213,112A patent/CA1082387A/fr not_active Expired

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CN116120721A (zh) *	2018-03-12	2023-05-16	耐克创新有限合伙公司	热塑性泡沫物品
CN111902448A (zh) *	2018-03-26	2020-11-06	美敦力公司	聚(醚-碳酸酯)基聚合物以及医疗装置
CN111902448B (zh) *	2018-03-26	2022-09-30	美敦力公司	聚(醚-碳酸酯)基聚合物以及医疗装置
US11548974B2 (en)	2018-03-26	2023-01-10	Medtronic, Inc.	Modified polyisobutylene-based polymers, methods of making, and medical devices
CN117844556A (zh) *	2023-12-29	2024-04-09	辽宁海华科技股份有限公司	一种支撑辊润滑方式用碳钢热轧工艺润滑剂组合物

Legal Events

Date	Code	Title	Description
1997-07-22	MKEX	Expiry

Publication	Publication Date	Title
CA1040783A (fr)	1978-10-17	Adhesif fait d'un copolyester segmente et stabilise par fusion
TWI277625B (en)	2007-04-01	Biodegradable saturated/unsaturated thermoplastic polyesters
EP0035769B1 (fr)	1986-01-08	Copolyesters et leur utilisation comme couche d'arrêt pour chlorure de polyvinyle plastifié
US5877255A (en)	1999-03-02	Kind of polyhydroxyl compounds suitable for the polyurethane synthesis
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CA2400576A1 (fr)	2002-06-27	Composition thermodurcissable en poudre pour revetements
CA1047690A (fr)	1979-01-30	Methode pour la fabrication des copolyesters et melanges adhesifs appliques a chaud, a base de copolyesters
US4247427A (en)	1981-01-27	Adhesion promoted block copolyester composition with multi-functional carboxylic compound
JPWO2011129278A1 (ja)	2013-07-18	接着剤用樹脂組成物、これを含有する接着剤、接着性シートおよびこれを接着剤層として含むプリント配線板
CN112898550B (zh)	2022-10-18	一种生物降解聚酯及其制备方法
EP0180970A2 (fr)	1986-05-14	Composition de copolymère bloc de polyester
US20070141373A1 (en)	2007-06-21	Segmented copolyesterether adhesive compositions
WO2013096373A1 (fr)	2013-06-27	Copolyétheresters aliphatiques-aromatiques
CA1082387A (fr)	1980-07-22	Produits adhesifs ameliores, a base de copolyesters sequences
US4156702A (en)	1979-05-29	Adhesion promoted block copolyester composition with multi-functional carboxylic compound
JP3950411B2 (ja)	2007-08-01	制振板用樹脂組成物およびこれを用いた制振板
KR20190087873A (ko)	2019-07-25	다이머산 또는 이의 알킬 에스테르와 에폭시화 식물유를 포함하는 열가소성 폴리에스테르, 이의 제조방법 및 이를 포함하는 핫멜트 접착제
JP2001354842A (ja)	2001-12-25	カレンダー成形用ポリエステル組成物
JPWO2006048927A1 (ja)	2008-05-22	共重合ポリエステル、その製造方法、及びポリエステルフィルム
JP2020079353A (ja)	2020-05-28	接着剤組成物、および積層体
JP2012087183A (ja)	2012-05-10	耐傷性に優れるコーティング樹脂組成物
CA1054291A (fr)	1979-05-08	Adhesif stabilise thermiquement, a base de copolyester segmente
US4481351A (en)	1984-11-06	Branched polyester waxes
JPS63264661A (ja)	1988-11-01	ポリエステル樹脂組成物