CA1123133A - Hot melt adhesives having improved thermal stability - Google Patents

Hot melt adhesives having improved thermal stability

Info

Publication number: CA1123133A
Authority: CA; Canada
Prior art keywords: acid; composition according; glycolic acid; silica; polymer
Prior art date: 1978-03-27
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

CA320,416A

Other languages

English (en)

French (fr)

Inventor

Robert Bacskai

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.)

Chevron USA Inc

Original Assignee

Chevron Research and Technology 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.)

1978-03-27

Filing date

1979-01-29

Publication date

1982-05-04

1979-01-29 Application filed by Chevron Research and Technology Co filed Critical Chevron Research and Technology Co

1982-05-04 Application granted granted Critical

1982-05-04 Publication of CA1123133A publication Critical patent/CA1123133A/en

Status Expired legal-status Critical Current

Links

239000004831 Hot glue Substances 0.000 title claims abstract description 15
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims abstract description 120
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 91
239000000203 mixture Substances 0.000 claims abstract description 69
239000000377 silicon dioxide Substances 0.000 claims abstract description 43
229920000642 polymer Polymers 0.000 claims abstract description 42
229920001577 copolymer Polymers 0.000 claims description 40
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 17
229920001519 homopolymer Polymers 0.000 claims description 16
RKDVKSZUMVYZHH-UHFFFAOYSA-N 1,4-dioxane-2,5-dione Chemical compound O=C1COC(=O)CO1 RKDVKSZUMVYZHH-UHFFFAOYSA-N 0.000 claims description 8
150000002596 lactones Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 5
238000000034 method Methods 0.000 claims description 5
239000002245 particle Substances 0.000 claims description 5
150000003077 polyols Chemical class 0.000 claims description 5
229920005862 polyol Polymers 0.000 claims description 4
QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
QEVGZEDELICMKH-UHFFFAOYSA-N Diglycolic acid Chemical compound OC(=O)COCC(O)=O QEVGZEDELICMKH-UHFFFAOYSA-N 0.000 claims description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 6
229960000250 adipic acid Drugs 0.000 claims 3
235000011037 adipic acid Nutrition 0.000 claims 3
239000001361 adipic acid Substances 0.000 claims 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 2
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 claims 2
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 claims 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 1
125000001931 aliphatic group Chemical group 0.000 claims 1
125000003118 aryl group Chemical group 0.000 claims 1
150000002009 diols Chemical group 0.000 claims 1
HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 claims 1
229960005137 succinic acid Drugs 0.000 claims 1
239000000853 adhesive Substances 0.000 abstract description 13
230000001070 adhesive effect Effects 0.000 abstract description 13
-1 clays Chemical compound 0.000 description 11
229920000728 polyester Polymers 0.000 description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
238000002156 mixing Methods 0.000 description 8
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
229920001897 terpolymer Polymers 0.000 description 6
229920000954 Polyglycolide Polymers 0.000 description 5
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
239000000945 filler Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 5
229910052753 mercury Inorganic materials 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000000178 monomer Substances 0.000 description 4
239000000123 paper Substances 0.000 description 4
229920000098 polyolefin Polymers 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
238000007334 copolymerization reaction Methods 0.000 description 3
239000004744 fabric Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000006068 polycondensation reaction Methods 0.000 description 3
229920002223 polystyrene Polymers 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
239000004698 Polyethylene Substances 0.000 description 2
229920002367 Polyisobutene Polymers 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000011575 calcium Substances 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000009826 distribution Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000010439 graphite Substances 0.000 description 2
229910002804 graphite Inorganic materials 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012943 hotmelt Substances 0.000 description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
229920000573 polyethylene Polymers 0.000 description 2
239000004633 polyglycolic acid Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
ULKFLOVGORAZDI-UHFFFAOYSA-N 3,3-dimethyloxetan-2-one Chemical compound CC1(C)COC1=O ULKFLOVGORAZDI-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
FEIQOMCWGDNMHM-UHFFFAOYSA-N 5-phenylpenta-2,4-dienoic acid Chemical compound OC(=O)C=CC=CC1=CC=CC=C1 FEIQOMCWGDNMHM-UHFFFAOYSA-N 0.000 description 1
229910001369 Brass Inorganic materials 0.000 description 1
229910000906 Bronze Inorganic materials 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
229910014570 C—OH Inorganic materials 0.000 description 1
239000004593 Epoxy Substances 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
241000257303 Hymenoptera Species 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
229920006397 acrylic thermoplastic Polymers 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000032683 aging Effects 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
229920000180 alkyd Polymers 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
238000000137 annealing Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000010951 brass Substances 0.000 description 1
239000010974 bronze Substances 0.000 description 1
DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000011111 cardboard Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
239000000919 ceramic Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000007423 decrease Effects 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
BXOUVIIITJXIKB-UHFFFAOYSA-N ethene;styrene Chemical group C=C.C=CC1=CC=CC=C1 BXOUVIIITJXIKB-UHFFFAOYSA-N 0.000 description 1
239000005038 ethylene vinyl acetate Substances 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
239000000835 fiber Substances 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
229920006158 high molecular weight polymer Polymers 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
150000001261 hydroxy acids Chemical class 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920003197 poly( p-chlorostyrene) Polymers 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
150000007519 polyprotic acids Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
229920005604 random copolymer Polymers 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
238000007151 ring opening polymerisation reaction Methods 0.000 description 1
239000000565 sealant Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
239000003356 suture material Substances 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 description 1
239000010936 titanium Substances 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000002023 wood Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- 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
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/04—Polyesters derived from hydroxycarboxylic acids, e.g. lactones
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/34—Silicon-containing compounds
- C08K3/36—Silica
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/54—Inorganic substances

Landscapes

Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Compositions Of Macromolecular Compounds (AREA)
Adhesives Or Adhesive Processes (AREA)
Polyesters Or Polycarbonates (AREA)

CA320,416A 1978-03-27 1979-01-29 Hot melt adhesives having improved thermal stability Expired CA1123133A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US05/890,169 US4156676A (en)	1978-03-27	1978-03-27	Hot melt adhesives having improved thermal stability
US890,169		1978-03-27

Publications (1)

Publication Number	Publication Date
CA1123133A true CA1123133A (en)	1982-05-04

Family

ID=25396346

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA320,416A Expired CA1123133A (en)	1978-03-27	1979-01-29	Hot melt adhesives having improved thermal stability

Country Status (9)

Country	Link
US (1)	US4156676A (2)
JP (1)	JPS54131657A (2)
BE (1)	BE874314A (2)
CA (1)	CA1123133A (2)
DE (1)	DE2911371A1 (2)
FR (1)	FR2421201A1 (2)
GB (1)	GB2017729B (2)
IT (1)	IT1114213B (2)
NL (1)	NL7901985A (2)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5798556A (en) *	1980-10-20	1982-06-18	American Cyanamid Co	Refomation of polyglycolic acid obtaining variable vital body physical properties
JPS6314020U (2) *	1986-07-14	1988-01-29
JPS6350425U (2) *	1986-09-19	1988-04-05
US5169889A (en) *	1992-01-27	1992-12-08	National Starch And Chemical Investment Holding Corporation	Poly hydroxybutyrate/hydroxyvalerate based hot melt adhesive
JPH07502069A (ja) *	1992-10-29	1995-03-02	ナショナル　スターチ　アンド　ケミカル　インベストメント　ホールディング　コーポレイション	ポリラクチド含有ホットメルト接着剤
FR2952061B1 (fr) *	2009-10-30	2012-02-10	Valagro Carbone Renouvelable Poitou Charentes	Utilisation d'oligomeres d'acide hydroxycarboxylique comme adhesifs, procede de fabrication et oligomeres d'acide hydroxycarboxylique obtenus
CN110088167B (zh) *	2016-12-22	2022-02-08	索尔维公司	乙醇酸聚合物
KR101938526B1 (ko) *	2017-09-15	2019-01-15	박희대	나노 실리카가 배합된 접착력이 우수한 열가소성 핫멜트 필름
CN113015768B (zh) *	2018-11-12	2023-11-17	索尔维公司	聚合物组合物
CN110216961B (zh) *	2019-06-03	2021-08-10	睿泊(中国)环保科技有限公司	一种可将金属、塑料分类回收的环保型复合材料及其制备方法
CN110341275B (zh) *	2019-06-03	2021-08-10	睿泊(中国)环保科技有限公司	一种可将基体材料分类回收的环保型复合材料及其制备方法
CN110253997B (zh) *	2019-06-03	2021-08-10	睿泊(中国)环保科技有限公司	一种可分类回收金属、塑料、纸的环保型复合材料及其制备方法
CN114829448B (zh) *	2019-12-18	2024-04-19	索尔维特殊聚合物美国有限责任公司	乙醇酸聚合物

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2362511A (en) *	1939-11-21	1944-11-14	Du Pont	Modified glycolide resins
US3047524A (en) *	1957-09-30	1962-07-31	Standard Oil Co	Glycolic acid polymer
US3142434A (en) *	1959-02-11	1964-07-28	Du Pont	Adhesive compositions
FR1535768A (fr) *	1966-10-28	1968-08-09	Exxon Research Engineering Co	Nouveau procédé de construction utilisant un liant organique

1978
- 1978-03-27 US US05/890,169 patent/US4156676A/en not_active Expired - Lifetime
1979
- 1979-01-29 CA CA320,416A patent/CA1123133A/en not_active Expired
- 1979-02-20 BE BE193583A patent/BE874314A/xx not_active IP Right Cessation
- 1979-03-13 NL NL7901985A patent/NL7901985A/xx not_active Application Discontinuation
- 1979-03-16 GB GB7909306A patent/GB2017729B/en not_active Expired
- 1979-03-20 FR FR7907065A patent/FR2421201A1/fr active Granted
- 1979-03-23 IT IT21253/79A patent/IT1114213B/it active
- 1979-03-23 DE DE19792911371 patent/DE2911371A1/de not_active Withdrawn
- 1979-03-26 JP JP3447279A patent/JPS54131657A/ja active Granted

Also Published As

Publication number	Publication date
GB2017729B (en)	1982-10-27
US4156676A (en)	1979-05-29
GB2017729A (en)	1979-10-10
JPS5717029B2 (2)	1982-04-08
NL7901985A (nl)	1979-10-01
IT1114213B (it)	1986-01-27
BE874314A (fr)	1979-06-18
JPS54131657A (en)	1979-10-12
FR2421201A1 (fr)	1979-10-26
FR2421201B1 (2)	1983-06-03
DE2911371A1 (de)	1979-10-11
IT7921253A0 (it)	1979-03-23

Legal Events

Date	Code	Title	Description
1999-05-04	MKEX	Expiry

Publication	Publication Date	Title
US4156676A (en)	1979-05-29	Hot melt adhesives having improved thermal stability
EP0188542B1 (en)	1990-09-05	Blends of polyamides and ethylene polymers carboxylic acid groups
US5612448A (en)	1997-03-18	Curable adhesive compositions containing polyamide resins
US4419507A (en)	1983-12-06	Copolyester adhesives
US3936426A (en)	1976-02-03	Amorphous, optically clear polyamide from a bis(4-aminocyclohexyl)methane and a phenylindan dicarboxylic acid
CA1040783A (en)	1978-10-17	Melt-stabilized segmented copolyester adhesive
US3975323A (en)	1976-08-17	Copolyesters, method of manufacturing same, and hot melt adhesive compositions incorporating same
EP0741178A2 (en)	1996-11-06	Hot melt adhesives based on hydroxy-functional polyesters
US3795644A (en)	1974-03-05	Hot melt adhesive composition
US4598142A (en)	1986-07-01	Copolyester adhesives
JPS63152684A (ja)	1988-06-25	ポリエステルを基材とするホットメルト接着剤組成物
JPS5863718A (ja)	1983-04-15	高溶融強度弾性コポリエステル
CN1254355A (zh)	2000-05-24	热熔粘合剂的防粘连涂层
US3907733A (en)	1975-09-23	Hot melt adhesive compositions
US5296557A (en)	1994-03-22	Two-component curable hot melt compositions
US4485233A (en)	1984-11-27	Poly(ester-amide) hot-melt adhesives
US4166895A (en)	1979-09-04	Copolyester from 1,4-butanediol and a dicarboxylic acid mixture
JP3212046B2 (ja)	2001-09-25	接着剤組成物
EP0182957A1 (en)	1986-06-04	Polyamides
US4254254A (en)	1981-03-03	Polyester amide fabric adhesives
JPH0241342A (ja)	1990-02-09	ポリエステル樹脂組成物
GB2173809A (en)	1986-10-22	Bonding poly(vinylidene chloride)
US4481351A (en)	1984-11-06	Branched polyester waxes
CA1141059A (en)	1983-02-08	Cavity filling with a hot melt adhesive composition and process therefor
CA1103833A (en)	1981-06-23	Poly(ester-amide) hot melt adhesive composition