CA1139495A - Anaerobic adhesive and/or sealing compositions, and methods of applying them - Google Patents

Anaerobic adhesive and/or sealing compositions, and methods of applying them

Info

Publication number: CA1139495A
Authority: CA; Canada
Prior art keywords: weight; composition according; composition; organic; layer
Prior art date: 1978-08-09
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

CA000332655A

Other languages

English (en)

French (fr)

Inventor

William D. Emmons

Vincent J. Moser

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.)

Rohm and Haas Co

Original Assignee

Rohm and Haas 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.)

1978-08-09

Filing date

1979-07-27

Publication date

1983-01-11

1979-07-27 Application filed by Rohm and Haas Co filed Critical Rohm and Haas Co

1983-01-11 Application granted granted Critical

1983-01-11 Publication of CA1139495A publication Critical patent/CA1139495A/en

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 73
230000001070 adhesive effect Effects 0.000 title claims abstract description 57
239000000853 adhesive Substances 0.000 title claims abstract description 56
238000007789 sealing Methods 0.000 title claims abstract description 11
238000000034 method Methods 0.000 title claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
239000001301 oxygen Substances 0.000 claims abstract description 12
229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
230000007717 exclusion Effects 0.000 claims abstract description 9
150000002432 hydroperoxides Chemical class 0.000 claims abstract description 9
150000001451 organic peroxides Chemical class 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
239000007788 liquid Substances 0.000 claims abstract description 6
RSVDRWTUCMTKBV-UHFFFAOYSA-N sbb057044 Chemical compound C12CC=CC2C2CC(OCCOC(=O)C=C)C1C2 RSVDRWTUCMTKBV-UHFFFAOYSA-N 0.000 claims abstract description 6
150000003949 imides Chemical class 0.000 claims abstract description 5
150000001412 amines Chemical class 0.000 claims abstract description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 12
JMIZWXDKTUGEES-UHFFFAOYSA-N 2,2-di(cyclopenten-1-yloxy)ethyl 2-methylprop-2-enoate Chemical compound C=1CCCC=1OC(COC(=O)C(=C)C)OC1=CCCC1 JMIZWXDKTUGEES-UHFFFAOYSA-N 0.000 claims description 11
239000002562 thickening agent Substances 0.000 claims description 11
238000006116 polymerization reaction Methods 0.000 claims description 9
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 claims description 7
239000000463 material Substances 0.000 claims description 6
239000004014 plasticizer Substances 0.000 claims description 6
229920005989 resin Polymers 0.000 claims description 6
239000011347 resin Substances 0.000 claims description 6
239000003623 enhancer Substances 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
230000013011 mating Effects 0.000 claims description 5
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 5
239000012530 fluid Substances 0.000 claims description 4
239000011256 inorganic filler Substances 0.000 claims description 4
229910003475 inorganic filler Inorganic materials 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
230000003014 reinforcing effect Effects 0.000 claims description 4
CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims description 3
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
229920000180 alkyd Polymers 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
239000003505 polymerization initiator Substances 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
229920001225 polyester resin Polymers 0.000 claims description 2
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 claims description 2
239000011343 solid material Substances 0.000 claims 3
SBWOBTUYQXLKSS-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propanoic acid Chemical class CC(=C)C(=O)OCCC(O)=O SBWOBTUYQXLKSS-UHFFFAOYSA-N 0.000 claims 2
150000001408 amides Chemical class 0.000 claims 1
235000019204 saccharin Nutrition 0.000 claims 1
-1 peroxy compound Chemical class 0.000 abstract description 12
CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 abstract description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
229910000975 Carbon steel Inorganic materials 0.000 description 9
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
239000010962 carbon steel Substances 0.000 description 9
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
239000004342 Benzoyl peroxide Substances 0.000 description 5
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
235000019400 benzoyl peroxide Nutrition 0.000 description 5
229910021485 fumed silica Inorganic materials 0.000 description 5
229910001220 stainless steel Inorganic materials 0.000 description 5
239000010935 stainless steel Substances 0.000 description 5
239000002023 wood Substances 0.000 description 5
239000000945 filler Substances 0.000 description 4
238000002156 mixing Methods 0.000 description 4
239000000178 monomer Substances 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
239000005977 Ethylene Substances 0.000 description 3
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000010960 cold rolled steel Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
150000002978 peroxides Chemical class 0.000 description 3
239000000565 sealant Substances 0.000 description 3
239000003381 stabilizer Substances 0.000 description 3
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
CUTWSDAQYCQTGD-UHFFFAOYSA-N 2-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)C(C)OC(=O)C=C CUTWSDAQYCQTGD-UHFFFAOYSA-N 0.000 description 2
229910001369 Brass Inorganic materials 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229920002319 Poly(methyl acrylate) Polymers 0.000 description 2
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
239000002318 adhesion promoter Substances 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
239000010951 brass Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
238000005259 measurement Methods 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
239000003921 oil Substances 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
KDGNCLDCOVTOCS-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy propan-2-yl carbonate Chemical compound CC(C)OC(=O)OOC(C)(C)C KDGNCLDCOVTOCS-UHFFFAOYSA-N 0.000 description 1
MQUUQPKBOFIRRS-UHFFFAOYSA-N 1,4,6-trimethylcyclohexa-2,4-dien-1-amine Chemical compound CC1C=C(C)C=CC1(C)N MQUUQPKBOFIRRS-UHFFFAOYSA-N 0.000 description 1
HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
VREVKZLUMZQJRI-UHFFFAOYSA-N [SH2]=N Chemical class [SH2]=N VREVKZLUMZQJRI-UHFFFAOYSA-N 0.000 description 1
YVOFKSGFOGNJHF-UHFFFAOYSA-N [SH2]=N.C(C1=CC=CC=C1)(=O)O Chemical compound [SH2]=N.C(C1=CC=CC=C1)(=O)O YVOFKSGFOGNJHF-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 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
235000012216 bentonite Nutrition 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
229910052793 cadmium Inorganic materials 0.000 description 1
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
229910017052 cobalt Inorganic materials 0.000 description 1
239000010941 cobalt Substances 0.000 description 1
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
238000005238 degreasing Methods 0.000 description 1
239000013527 degreasing agent Substances 0.000 description 1
238000005237 degreasing agent Methods 0.000 description 1
150000002009 diols Chemical class 0.000 description 1
238000007598 dipping method Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002708 enhancing effect Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000011521 glass Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000004519 grease Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
238000005555 metalworking Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000002085 persistent effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
239000004645 polyester resin Substances 0.000 description 1
229920000120 polyethyl acrylate Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
239000011148 porous material Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000008439 repair process Effects 0.000 description 1
230000035939 shock Effects 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000010959 steel Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229920003051 synthetic elastomer Polymers 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical group 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
238000005303 weighing Methods 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- 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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- 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]
- Y10T428/31678—Of metal
- Y10T428/31692—Next to addition polymer from unsaturated monomers
- Y10T428/31699—Ester, halide or nitrile of addition polymer

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Adhesives Or Adhesive Processes (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Sealing Material Composition (AREA)

CA000332655A 1978-08-09 1979-07-27 Anaerobic adhesive and/or sealing compositions, and methods of applying them Expired CA1139495A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US932,256		1978-08-09
US05/932,256 US4234711A (en)	1978-08-09	1978-08-09	Anaerobic adhesive and/or sealing compositions comprising dicyclopentenyloxyethyl (meth)acrylates

Publications (1)

Publication Number	Publication Date
CA1139495A true CA1139495A (en)	1983-01-11

Family

ID=25462035

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000332655A Expired CA1139495A (en)	1978-08-09	1979-07-27	Anaerobic adhesive and/or sealing compositions, and methods of applying them

Country Status (5)

Country	Link
US (1)	US4234711A (2)
EP (1)	EP0008202B1 (2)
JP (1)	JPS5525486A (2)
CA (1)	CA1139495A (2)
DE (1)	DE2963109D1 (2)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4346814A (en) *	1980-03-03	1982-08-31	American Can Company	Side seam stripes
US4400413A (en) *	1980-08-29	1983-08-23	Rohm And Haas Company	Acrylic polymer concrete compositions
US4460625A (en) *	1981-07-16	1984-07-17	Rohm And Haas Company	Method of coating and impregnating concrete substrates, and products obtained thereby
US4453988A (en) *	1983-01-12	1984-06-12	Grow Group, Inc.	Coatings for rusted metallic surfaces
US4620028A (en) *	1985-05-28	1986-10-28	Scm Corporation	Esters of hydroxyalkyl ethers of bornane
IT1183999B (it) *	1985-12-05	1987-10-22	Fiat Auto Spa	Procedimento per l'incollaggio delle canne cilindri al basamento di un motore a combustione interna
EP0295347B1 (en) *	1987-06-19	1991-08-28	Daiso Co., Ltd.	Thermosetting resin composition
JP2568421B2 (ja) *	1987-03-24	1997-01-08	株式会社スリーボンド	嫌気硬化性接着シール剤組成物
JPS63308903A (ja) *	1987-06-11	1988-12-16	Fuji Elelctrochem Co Ltd	樹脂結合型永久磁石の製造方法
JPH01124665U (2) *	1988-02-17	1989-08-24
JPH01301570A (ja) *	1988-02-26	1989-12-05	Hitachi Chem Co Ltd	石綿スレートの補修方法
JPH05111097A (ja) *	1991-10-15	1993-04-30	Murata Mfg Co Ltd	圧電発音体
DE637575T1 (de) *	1993-08-03	1996-03-14	Sartomer Co Inc	Harzbeton mit verbesserter Substrathaftung.
AU742504B2 (en)	1997-04-08	2002-01-03	Rohm And Haas Company	Reactive coalescents
EP4386059A4 (en) *	2021-08-11	2025-08-13	Okura Industrial Co Ltd	ANAEROBIC ADHESIVE COMPOSITION
CN115949811A (zh) *	2022-12-07	2023-04-11	毫厘机电(苏州)有限公司	能够提升粘合剂塑化强度的水接头结构及其工艺方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1719143B1 (de) *	1967-11-02	1971-03-11	Henkel & Cie Gmbh	Bei Sauerstoffausschluss erhaertende Klebstoffe und Dichtungsmittel
DE2529891A1 (de) *	1975-07-04	1977-01-27	Henkel & Cie Gmbh	Bei sauerstoffausschluss erhaertende klebstoffe oder dichtungsmittel
US4071489A (en) *	1976-03-08	1978-01-31	Rohm And Haas Company	Coating compositions from dicyclopentenyl acrylate and/or methacrylate
US4100133A (en) *	1976-06-24	1978-07-11	Rohm And Haas Company	Air-dry curable compositions comprising dicyclopentenyl (meth) acrylate copolymers and non-volatile reactive monomer, and cured coatings and impregnations obtained therefrom
ZA7803231B (en) *	1976-07-07		Rohm & Haas	Monomer compositions

1978
- 1978-08-09 US US05/932,256 patent/US4234711A/en not_active Expired - Lifetime
1979
- 1979-07-27 CA CA000332655A patent/CA1139495A/en not_active Expired
- 1979-08-03 DE DE7979301559T patent/DE2963109D1/de not_active Expired
- 1979-08-03 EP EP19790301559 patent/EP0008202B1/en not_active Expired
- 1979-08-07 JP JP9995479A patent/JPS5525486A/ja active Granted

Also Published As

Publication number	Publication date
EP0008202B1 (en)	1982-06-16
EP0008202A1 (en)	1980-02-20
JPS6349714B2 (2)	1988-10-05
US4234711A (en)	1980-11-18
JPS5525486A (en)	1980-02-23
DE2963109D1 (en)	1982-08-05

Legal Events

Date	Code	Title	Description
2000-01-11	MKEX	Expiry

Publication	Publication Date	Title
CA1139495A (en)	1983-01-11	Anaerobic adhesive and/or sealing compositions, and methods of applying them
US3922449A (en)	1975-11-25	Interfitting threaded part and process of preparing same
US3658624A (en)	1972-04-25	Bonding method employing a two part anaerobically curing adhesive composition
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