NZ204048A - Resins of phenol-dialdehydes or cyclic ketones having six or more carbon atoms:adhesive compositions - Google Patents

Resins of phenol-dialdehydes or cyclic ketones having six or more carbon atoms:adhesive compositions

Info

Publication number: NZ204048A
Authority: NZ; New Zealand
Prior art keywords: phenol; resin; resorcinol; parts; cyclohexanone
Prior art date: 1982-04-30

Application number

NZ204048A

Other languages

English (en)

Inventor

G Reynolds

Original Assignee

Esdan Extrusion Pty Ltd

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.)

1982-04-30

Filing date

1983-04-29

Publication date

1986-05-09

1983-04-29 Application filed by Esdan Extrusion Pty Ltd filed Critical Esdan Extrusion Pty Ltd

1986-05-09 Publication of NZ204048A publication Critical patent/NZ204048A/en

Links

239000011347 resin Substances 0.000 title claims description 47
229920005989 resin Polymers 0.000 title claims description 47
239000000853 adhesive Substances 0.000 title claims description 29
230000001070 adhesive effect Effects 0.000 title claims description 29
239000000203 mixture Substances 0.000 title claims description 21
150000003997 cyclic ketones Chemical class 0.000 title claims description 7
125000004432 carbon atom Chemical group C* 0.000 title description 3
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 45
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 34
238000000034 method Methods 0.000 claims description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
229920001778 nylon Polymers 0.000 claims description 22
239000004677 Nylon Substances 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 21
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 18
239000003054 catalyst Substances 0.000 claims description 18
238000010992 reflux Methods 0.000 claims description 16
229910052751 metal Inorganic materials 0.000 claims description 14
239000002184 metal Substances 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 10
150000002989 phenols Chemical class 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 7
150000001875 compounds Chemical class 0.000 claims description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
150000002739 metals Chemical class 0.000 claims description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
239000000945 filler Substances 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
229930040373 Paraformaldehyde Natural products 0.000 claims description 4
239000011133 lead Substances 0.000 claims description 4
235000006408 oxalic acid Nutrition 0.000 claims description 4
229920002866 paraformaldehyde Polymers 0.000 claims description 4
239000004848 polyfunctional curative Substances 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
239000004312 hexamethylene tetramine Substances 0.000 claims description 3
235000010299 hexamethylene tetramine Nutrition 0.000 claims description 3
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 3
239000002841 Lewis acid Substances 0.000 claims description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
239000004411 aluminium Substances 0.000 claims description 2
229910052782 aluminium Inorganic materials 0.000 claims description 2
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
229910017052 cobalt Inorganic materials 0.000 claims description 2
239000010941 cobalt Substances 0.000 claims description 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
150000007517 lewis acids Chemical class 0.000 claims description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 2
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 2
229910052753 mercury Inorganic materials 0.000 claims description 2
229910052759 nickel Inorganic materials 0.000 claims description 2
239000011135 tin Substances 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000007795 chemical reaction product Substances 0.000 claims 4
235000019441 ethanol Nutrition 0.000 claims 3
239000000376 reactant Substances 0.000 claims 2
239000011592 zinc chloride Substances 0.000 claims 2
235000005074 zinc chloride Nutrition 0.000 claims 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims 2
MCNQUWLLXZZZAC-UHFFFAOYSA-N 4-cyano-1-(2,4-dichlorophenyl)-5-(4-methoxyphenyl)-n-piperidin-1-ylpyrazole-3-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=C(C#N)C(C(=O)NN2CCCCC2)=NN1C1=CC=C(Cl)C=C1Cl MCNQUWLLXZZZAC-UHFFFAOYSA-N 0.000 claims 1
229910021577 Iron(II) chloride Inorganic materials 0.000 claims 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 claims 1
150000003839 salts Chemical class 0.000 claims 1
229910001868 water Inorganic materials 0.000 description 6
229920000571 Nylon 11 Polymers 0.000 description 4
KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 description 4
239000007789 gas Substances 0.000 description 4
GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 4
239000000758 substrate Substances 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
ZNZYKNKBJPZETN-WELNAUFTSA-N Dialdehyde 11678 Chemical compound N1C2=CC=CC=C2C2=C1[C@H](C[C@H](/C(=C/O)C(=O)OC)[C@@H](C=C)C=O)NCC2 ZNZYKNKBJPZETN-WELNAUFTSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
238000005304 joining Methods 0.000 description 3
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
229910052720 vanadium Inorganic materials 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000004952 Polyamide Substances 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000011049 filling Methods 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
150000002576 ketones Chemical class 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
125000002524 organometallic group Chemical group 0.000 description 2
239000004033 plastic Substances 0.000 description 2
229920003023 plastic Polymers 0.000 description 2
229920002647 polyamide Polymers 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
229910052721 tungsten Inorganic materials 0.000 description 2
HAAITRDZHUANGT-UHFFFAOYSA-N 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid Chemical compound O[N+]([O-])=O.ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 HAAITRDZHUANGT-UHFFFAOYSA-N 0.000 description 1
QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical group CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
-1 A1C13 or FeClg) Chemical class 0.000 description 1
244000183914 Dianthus superbus Species 0.000 description 1
229920000299 Nylon 12 Polymers 0.000 description 1
229920000305 Nylon 6,10 Polymers 0.000 description 1
229920000572 Nylon 6/12 Polymers 0.000 description 1
239000000654 additive Substances 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001896 cresols Chemical class 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
YMLYUTRQDMCNLD-UHFFFAOYSA-N cyclohexa-2,5-dien-1-ol Chemical compound OC1C=CCC=C1 YMLYUTRQDMCNLD-UHFFFAOYSA-N 0.000 description 1
125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
230000004992 fission Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000011572 manganese Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000011120 plywood Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000001846 repelling effect Effects 0.000 description 1
239000011342 resin composition Substances 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
239000000779 smoke Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- 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
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/02—Condensation polymers of aldehydes or ketones with phenols only of ketones
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
- 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
- C09J161/00—Adhesives based on condensation polymers of aldehydes or ketones; Adhesives based on derivatives of such polymers
- C09J161/04—Condensation polymers of aldehydes or ketones with phenols only
- 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
- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Engineering & Computer Science (AREA)
Manufacturing & Machinery (AREA)
Materials Engineering (AREA)
Adhesives Or Adhesive Processes (AREA)
Phenolic Resins Or Amino Resins (AREA)

NZ204048A 1982-04-30 1983-04-29 Resins of phenol-dialdehydes or cyclic ketones having six or more carbon atoms:adhesive compositions NZ204048A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
AUPF380382		1982-04-30

Publications (1)

Publication Number	Publication Date
NZ204048A true NZ204048A (en)	1986-05-09

Family

ID=3769505

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NZ204048A NZ204048A (en)	1982-04-30	1983-04-29	Resins of phenol-dialdehydes or cyclic ketones having six or more carbon atoms:adhesive compositions

Country Status (5)

Country	Link
EP (1)	EP0107684A1 (da)
DK (1)	DK165011C (da)
NZ (1)	NZ204048A (da)
WO (1)	WO1983003832A1 (da)
ZA (1)	ZA833048B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8708386D0 (en) *	1987-04-08	1987-05-13	Cesaroni A J	Heat sealing of polyamides
US8765853B2 (en)	2007-04-04	2014-07-01	Ppg Industries Ohio, Inc.	Coating compositions and methods for improving the adhesion of coatings to polymeric substrates

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1823127A (en) *	1925-10-21	1931-09-15	Ig Farbenindustrie Ag	Manufacture of artificial resins
US3376262A (en) *	1967-07-10	1968-04-02	Chevron Res	Phenol-formaldehyde resin modified with tetralin hydroperoxide and tetralone
US4234706A (en) *	1977-05-26	1980-11-18	General Electric Company	Quinone-coupled polyphenylene oxides
US4188476A (en) *	1979-04-06	1980-02-12	E. I. Du Pont De Nemours And Company	Aromatic polyester consisting essentially of p-oxybenzoyl units, terephthaloyl units, 2,6-dioxynaphthalene or 2,6-dioxyanthraquinone units and m-oxybenzoyl or 1,3-dioxyphenylene units
JPS56112961A (en) *	1980-02-13	1981-09-05	Mitsubishi Petrochem Co Ltd	Thermosetting resin composition

1983
- 1983-04-27 DK DK188483A patent/DK165011C/da not_active IP Right Cessation
- 1983-04-29 EP EP83901313A patent/EP0107684A1/en not_active Withdrawn
- 1983-04-29 ZA ZA833048A patent/ZA833048B/xx unknown
- 1983-04-29 WO PCT/AU1983/000052 patent/WO1983003832A1/en not_active Ceased
- 1983-04-29 NZ NZ204048A patent/NZ204048A/en unknown

Also Published As

Publication number	Publication date
EP0107684A1 (en)	1984-05-09
WO1983003832A1 (en)	1983-11-10
ZA833048B (en)	1984-01-25
DK188483D0 (da)	1983-04-27
DK188483A (da)	1983-10-31
DK165011B (da)	1992-09-28
DK165011C (da)	1993-02-08

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GB1424290A (en)	1976-02-11	Process for the production of cured resins
CA1116341A (en)	1982-01-12	Adhesion of rubber to reinforcing materials
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