CA1278131C - Colle de contact et systeme adhesif pour elastomeres epdm - Google Patents

Colle de contact et systeme adhesif pour elastomeres epdm

Info

Publication number: CA1278131C
Authority: CA; Canada
Prior art keywords: composition; weight; epdm; parts; adhesive
Prior art date: 1985-03-05
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 - Lifetime

Application number

CA000502009A

Other languages

English (en)

Inventor

John W. Fieldhouse

Mark L. Stayer

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.)

Bridgestone Firestone Inc

Original Assignee

Firestone Tire and Rubber 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.)

1985-03-05

Filing date

1986-02-17

Publication date

1990-12-18

1986-02-17 Application filed by Firestone Tire and Rubber Co filed Critical Firestone Tire and Rubber Co

1990-12-18 Application granted granted Critical

1990-12-18 Publication of CA1278131C publication Critical patent/CA1278131C/fr

2007-12-18 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000001070 adhesive effect Effects 0.000 title claims abstract description 136
239000000853 adhesive Substances 0.000 title claims abstract description 133
229920002943 EPDM rubber Polymers 0.000 title abstract description 96
239000004821 Contact adhesive Substances 0.000 title description 2
239000000203 mixture Substances 0.000 claims abstract description 164
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 36
239000000049 pigment Substances 0.000 claims abstract description 27
239000000463 material Substances 0.000 claims abstract description 26
239000004014 plasticizer Substances 0.000 claims abstract description 19
239000004215 Carbon black (E152) Substances 0.000 claims abstract description 17
229930195733 hydrocarbon Natural products 0.000 claims abstract description 17
239000000377 silicon dioxide Substances 0.000 claims abstract description 17
229920001083 polybutene Polymers 0.000 claims abstract description 16
229920005608 sulfonated EPDM Polymers 0.000 claims abstract description 16
229920002367 Polyisobutene Polymers 0.000 claims abstract description 15
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 15
239000002480 mineral oil Substances 0.000 claims abstract description 14
239000003921 oil Substances 0.000 claims abstract description 14
230000002209 hydrophobic effect Effects 0.000 claims abstract description 13
239000003208 petroleum Substances 0.000 claims abstract description 13
239000002904 solvent Substances 0.000 claims abstract description 13
239000013032 Hydrocarbon resin Substances 0.000 claims abstract description 12
229920006270 hydrocarbon resin Polymers 0.000 claims abstract description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 12
229920013728 elastomeric terpolymer Polymers 0.000 claims abstract description 10
229920001577 copolymer Polymers 0.000 claims abstract description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 31
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 24
229920000642 polymer Polymers 0.000 claims description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 22
229920005989 resin Polymers 0.000 claims description 19
239000011347 resin Substances 0.000 claims description 19
229920001897 terpolymer Polymers 0.000 claims description 19
-1 aliphatic alcohols Chemical class 0.000 claims description 16
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 15
MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 14
239000010692 aromatic oil Substances 0.000 claims description 13
239000006229 carbon black Substances 0.000 claims description 13
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 12
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239000007788 liquid Substances 0.000 claims description 9
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125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 9
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical group C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 6
XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 6
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VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 5
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
239000005977 Ethylene Substances 0.000 claims description 4
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QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 4
239000012763 reinforcing filler Substances 0.000 claims description 4
239000004408 titanium dioxide Substances 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 claims description 3
239000000292 calcium oxide Substances 0.000 claims description 3
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
239000012463 white pigment Substances 0.000 claims description 3
239000011787 zinc oxide Substances 0.000 claims description 3
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125000005270 trialkylamine group Chemical group 0.000 claims 2
239000001056 green pigment Substances 0.000 claims 1
239000010690 paraffinic oil Substances 0.000 claims 1
239000002245 particle Substances 0.000 claims 1
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239000012528 membrane Substances 0.000 abstract description 37
229920001971 elastomer Polymers 0.000 abstract description 16
239000000806 elastomer Substances 0.000 abstract description 15
239000000758 substrate Substances 0.000 abstract description 9
239000000975 dye Substances 0.000 description 20
238000000034 method Methods 0.000 description 20
238000012360 testing method Methods 0.000 description 18
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150000001993 dienes Chemical class 0.000 description 6
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239000002253 acid Substances 0.000 description 4
OIPMQULDKWSNGX-UHFFFAOYSA-N bis[[ethoxy(oxo)phosphaniumyl]oxy]alumanyloxy-ethoxy-oxophosphanium Chemical compound [Al+3].CCO[P+]([O-])=O.CCO[P+]([O-])=O.CCO[P+]([O-])=O OIPMQULDKWSNGX-UHFFFAOYSA-N 0.000 description 4
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JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 4
IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 4
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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 description 4
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239000011701 zinc Substances 0.000 description 4
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230000032683 aging Effects 0.000 description 3
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239000010426 asphalt Substances 0.000 description 3
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 3
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239000011888 foil Substances 0.000 description 3
125000003010 ionic group Chemical group 0.000 description 3
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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238000006386 neutralization reaction Methods 0.000 description 3
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HZWXJJCSDBQVLF-UHFFFAOYSA-N acetoxysulfonic acid Chemical compound CC(=O)OS(O)(=O)=O HZWXJJCSDBQVLF-UHFFFAOYSA-N 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000012790 adhesive layer Substances 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
208000002399 aphthous stomatitis Diseases 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000002585 base Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229920005549 butyl rubber Polymers 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000004568 cement Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
239000002131 composite material Substances 0.000 description 1
230000008602 contraction Effects 0.000 description 1
230000001351 cycling effect Effects 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
238000000151 deposition Methods 0.000 description 1
239000012972 dimethylethanolamine Substances 0.000 description 1
238000010494 dissociation reaction Methods 0.000 description 1
230000005593 dissociations Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
FPVGTPBMTFTMRT-NSKUCRDLSA-L fast yellow Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(N)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 FPVGTPBMTFTMRT-NSKUCRDLSA-L 0.000 description 1
235000019233 fast yellow AB Nutrition 0.000 description 1
229940083124 ganglion-blocking antiadrenergic secondary and tertiary amines Drugs 0.000 description 1
PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical compound C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000012774 insulation material Substances 0.000 description 1
229920000831 ionic polymer Polymers 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
230000003902 lesion Effects 0.000 description 1
150000007527 lewis bases Chemical class 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
SEBNPZMOBUCYCA-UHFFFAOYSA-N morpholin-4-ylmethanol Chemical compound OCN1CCOCC1 SEBNPZMOBUCYCA-UHFFFAOYSA-N 0.000 description 1
XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
TVZIWRMELPWPPR-UHFFFAOYSA-N n-(2-methylphenyl)-3-oxobutanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C TVZIWRMELPWPPR-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
239000012860 organic pigment Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 description 1
WOTPFVNWMLFMFW-ISLYRVAYSA-N para red Chemical compound OC1=CC=C2C=CC=CC2=C1\N=N\C1=CC=C(N(=O)=O)C=C1 WOTPFVNWMLFMFW-ISLYRVAYSA-N 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
150000003097 polyterpenes Chemical class 0.000 description 1
238000003825 pressing Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000011164 primary particle Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
239000012744 reinforcing agent Substances 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
AZLXCBPKSXFMET-UHFFFAOYSA-M sodium 4-[(4-sulfophenyl)diazenyl]naphthalen-1-olate Chemical compound [Na+].C12=CC=CC=C2C(O)=CC=C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 AZLXCBPKSXFMET-UHFFFAOYSA-M 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
SXNQAQBMEWMYAU-UHFFFAOYSA-N sulfo butanoate Chemical compound CCCC(=O)OS(O)(=O)=O SXNQAQBMEWMYAU-UHFFFAOYSA-N 0.000 description 1
230000008961 swelling Effects 0.000 description 1
239000011270 tar paper Substances 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
238000005382 thermal cycling Methods 0.000 description 1
JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
229940124543 ultraviolet light absorber Drugs 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Landscapes

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

CA000502009A 1985-03-05 1986-02-17 Colle de contact et systeme adhesif pour elastomeres epdm Expired - Lifetime CA1278131C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US70861685A	1985-03-05	1985-03-05
US708,616		1985-03-05

Publications (1)

Publication Number	Publication Date
CA1278131C true CA1278131C (fr)	1990-12-18

Family

ID=24846513

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000502009A Expired - Lifetime CA1278131C (fr)	1985-03-05	1986-02-17	Colle de contact et systeme adhesif pour elastomeres epdm

Country Status (2)

Country	Link
JP (1)	JPS61252282A (fr)
CA (1)	CA1278131C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2013184368A1 (fr) *	2012-06-05	2013-12-12	3M Innovative Properties Company	Adhésifs comportant des polymères de poly(isobutylène) et une alkyl amine n'ayant pas réagi

1986
- 1986-02-17 CA CA000502009A patent/CA1278131C/fr not_active Expired - Lifetime
- 1986-03-04 JP JP4550286A patent/JPS61252282A/ja active Pending

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2013184368A1 (fr) *	2012-06-05	2013-12-12	3M Innovative Properties Company	Adhésifs comportant des polymères de poly(isobutylène) et une alkyl amine n'ayant pas réagi
US8697789B2 (en)	2012-06-05	2014-04-15	3M Innovative Properties Company	Adhesives comprising poly(isobutylene) polymers and unreacted alkyl amine

Also Published As

Publication number	Publication date
JPS61252282A (ja)	1986-11-10

Legal Events

Date	Code	Title	Description
1993-06-20	MKLA	Lapsed

Publication	Publication Date	Title
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AU678261B2 (en)	1997-05-22	Primer composition for improving the bonding of a urethane adhesive to non-porous substrates
US3810707A (en)	1974-05-14	Joint structure and method
US4801346A (en)	1989-01-31	Protective coatings
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US5035934A (en)	1991-07-30	Adhesive sheet for preventing icing
US9580630B2 (en)	2017-02-28	Adhesive compound
US20100326598A1 (en)	2010-12-30	Low volatile organic compound adhesive for attaching thermoplastic polyolefin roofing membranes
JPH07138551A (ja)	1995-05-30	湿分硬化性ポリウレタン接着剤
CN102395641A (zh)	2012-03-28	粘合剂化合物
US4480012A (en)	1984-10-30	Contact adhesive and adhesive system for EPDM and related elastomers
CN101006126A (zh)	2007-07-25	水性沥青涂料组合物
CA1278131C (fr)	1990-12-18	Colle de contact et systeme adhesif pour elastomeres epdm
CA1205592A (fr)	1986-06-03	Adhesif par contact et systeme adhesif epdm et elastomeres apparentes
JP3296865B2 (ja)	2002-07-02	反応性ホットメルト型接着剤組成物
AU650244B2 (en)	1994-06-16	Contact adhering method and adhesive therefor
EP1080157B1 (fr)	2004-06-02	Ruban adhesif autocollant et produit adhesif utilisant ce ruban
DE69222990T2 (de)	1998-06-25	Harzzusammensetzung
US20240076529A1 (en)	2024-03-07	Acrylic pressure-sensitive adhesive and also adhesive tape furnished with acrylic pressure-sensitive adhesive
WO2025061882A1 (fr)	2025-03-27	Ruban adhésif ignifuge
JPS63291970A (ja)	1988-11-29	接着剤組成物
JP2000256648A (ja)	2000-09-19	防水シート用シール材組成物
NZ202379A (en)	1985-12-13	Strippable coating compositions containing atactic polypropylene
NZ209521A (en)	1987-02-20	Acrylic resin with pendant silane groups