CA1315440C - Adhesifs au silicone et methodes de fabrication et d'utilisation connexes - Google Patents

Adhesifs au silicone et methodes de fabrication et d'utilisation connexes

Info

Publication number: CA1315440C
Authority: CA; Canada
Prior art keywords: acrylic; amount; parts; weight; present
Prior art date: 1985-03-14
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 - Fee Related

Application number

CA000504138A

Other languages

English (en)

Inventor

Wan-Li Liu

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.)

General Electric Co

Original Assignee

General Electric 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.)

1985-03-14

Filing date

1986-03-14

Publication date

1993-03-30

1986-03-14 Application filed by General Electric Co filed Critical General Electric Co

1993-03-30 Application granted granted Critical

1993-03-30 Publication of CA1315440C publication Critical patent/CA1315440C/fr

2010-03-30 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
239000013464 silicone adhesive Substances 0.000 title abstract description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 102
239000000853 adhesive Substances 0.000 claims abstract description 86
230000001070 adhesive effect Effects 0.000 claims abstract description 86
239000000203 mixture Substances 0.000 claims abstract description 63
239000000178 monomer Substances 0.000 claims abstract description 62
239000003054 catalyst Substances 0.000 claims abstract description 33
238000006116 polymerization reaction Methods 0.000 claims abstract description 26
150000003254 radicals Chemical class 0.000 claims abstract description 24
239000002243 precursor Substances 0.000 claims abstract description 15
239000007787 solid Substances 0.000 claims abstract description 11
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 24
229910000077 silane Inorganic materials 0.000 claims description 24
239000012190 activator Substances 0.000 claims description 21
125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 14
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 13
239000000758 substrate Substances 0.000 claims description 12
229910052723 transition metal Inorganic materials 0.000 claims description 12
150000003624 transition metals Chemical class 0.000 claims description 12
150000001412 amines Chemical group 0.000 claims description 9
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 9
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 claims description 7
HBOYQHJSMXAOKY-UHFFFAOYSA-N 3-[methyl-bis(trimethylsilyloxy)silyl]propyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCCC[Si](C)(O[Si](C)(C)C)O[Si](C)(C)C HBOYQHJSMXAOKY-UHFFFAOYSA-N 0.000 claims description 4
NRLCNVYHWRDHTJ-UHFFFAOYSA-L cobalt(2+);naphthalene-1-carboxylate Chemical group [Co+2].C1=CC=C2C(C(=O)[O-])=CC=CC2=C1.C1=CC=C2C(C(=O)[O-])=CC=CC2=C1 NRLCNVYHWRDHTJ-UHFFFAOYSA-L 0.000 claims description 4
RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 claims description 3
229910000360 iron(III) sulfate Inorganic materials 0.000 claims description 3
PAVJEQIFHXNOSM-UHFFFAOYSA-H manganese(3+);trisulfate Chemical compound [Mn+3].[Mn+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PAVJEQIFHXNOSM-UHFFFAOYSA-H 0.000 claims description 3
125000005474 octanoate group Chemical group 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 2
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 6
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
-1 acrylic ester Chemical class 0.000 description 11
229920000642 polymer Polymers 0.000 description 11
239000003085 diluting agent Substances 0.000 description 10
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 8
230000000694 effects Effects 0.000 description 5
238000009472 formulation Methods 0.000 description 5
150000001875 compounds Chemical class 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
239000000463 material Substances 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
125000005395 methacrylic acid group Chemical class 0.000 description 4
239000004823 Reactive adhesive Substances 0.000 description 3
CRQQGFGUEAVUIL-UHFFFAOYSA-N chlorothalonil Chemical compound ClC1=C(Cl)C(C#N)=C(Cl)C(C#N)=C1Cl CRQQGFGUEAVUIL-UHFFFAOYSA-N 0.000 description 3
229920001577 copolymer Polymers 0.000 description 3
238000001879 gelation Methods 0.000 description 3
229920013730 reactive polymer Polymers 0.000 description 3
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000004026 adhesive bonding Methods 0.000 description 2
239000004205 dimethyl polysiloxane Substances 0.000 description 2
239000003999 initiator Substances 0.000 description 2
150000002976 peresters Chemical class 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
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
229920000058 polyacrylate Polymers 0.000 description 2
229920002635 polyurethane Polymers 0.000 description 2
239000004814 polyurethane Substances 0.000 description 2
230000005855 radiation Effects 0.000 description 2
239000000126 substance Substances 0.000 description 2
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
LRDIEHDJWYRVPT-UHFFFAOYSA-N 4-amino-5-hydroxynaphthalene-1-sulfonic acid Chemical compound C1=CC(O)=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 LRDIEHDJWYRVPT-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
VJLYCOZACXQZQO-UHFFFAOYSA-N CC(=C)C(=O)OCCC[SiH2]C(O[Si](C)(C)C)O[Si](C)(C)C Chemical compound CC(=C)C(=O)OCCC[SiH2]C(O[Si](C)(C)C)O[Si](C)(C)C VJLYCOZACXQZQO-UHFFFAOYSA-N 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
239000004821 Contact adhesive Substances 0.000 description 1
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
101150089916 Miox gene Proteins 0.000 description 1
229910020489 SiO3 Inorganic materials 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
229910052787 antimony Inorganic materials 0.000 description 1
WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
230000008901 benefit Effects 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
238000006664 bond formation reaction Methods 0.000 description 1
239000007767 bonding agent Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
239000011248 coating agent 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
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000003063 flame retardant Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
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 description 1
230000007246 mechanism Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
UIUXUFNYAYAMOE-UHFFFAOYSA-N methylsilane Chemical compound [SiH3]C UIUXUFNYAYAMOE-UHFFFAOYSA-N 0.000 description 1
230000005012 migration Effects 0.000 description 1
238000013508 migration Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
229920000620 organic polymer Polymers 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
239000003505 polymerization initiator Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000010526 radical polymerization reaction Methods 0.000 description 1
238000013040 rubber vulcanization Methods 0.000 description 1
150000004756 silanes Chemical class 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000003419 tautomerization reaction Methods 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
229910052718 tin Inorganic materials 0.000 description 1
239000011135 tin Substances 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Landscapes

Adhesives Or Adhesive Processes (AREA)
Macromonomer-Based Addition Polymer (AREA)

CA000504138A 1985-03-14 1986-03-14 Adhesifs au silicone et methodes de fabrication et d'utilisation connexes Expired - Fee Related CA1315440C (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US71186585A	1985-03-14	1985-03-14
US711,865		1985-03-14

Publications (1)

Publication Number	Publication Date
CA1315440C true CA1315440C (fr)	1993-03-30

Family

ID=24859858

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000504138A Expired - Fee Related CA1315440C (fr)	1985-03-14	1986-03-14	Adhesifs au silicone et methodes de fabrication et d'utilisation connexes

Country Status (2)

Country	Link
JP (1)	JPS61246277A (fr)
CA (1)	CA1315440C (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US12503556B2 (en)	2020-01-22	2025-12-23	Dow Silicones Corporation	Silicone-acrylate polymers, copolymers, and related methods and compositions

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3419314B2 (ja) *	1998-07-08	2003-06-23	信越化学工業株式会社	液状放射線硬化型樹脂組成物及び光ファイバ
DE102010013196B4 (de) *	2010-03-29	2015-10-29	Hilti Aktiengesellschaft	Chemische Zweikomponenten-Mörtelmasse mit verbesserter Haftung an der Oberfläche von halbgereinigten und/oder feuchten Bohrlöchern in mineralischem Untergrund und ihre Verwendung
JP5765303B2 (ja) *	2012-08-20	2015-08-19	信越化学工業株式会社	光学用感圧接着剤組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5716083A (en) *	1981-05-15	1982-01-27	Hitachi Ltd	Adhesive polymerizable by action of both light and heat
JPS58173174A (ja) *	1982-04-06	1983-10-12	Japan Synthetic Rubber Co Ltd	ラジカル系接着剤組成物

1986
- 1986-03-11 JP JP5158886A patent/JPS61246277A/ja active Pending
- 1986-03-14 CA CA000504138A patent/CA1315440C/fr not_active Expired - Fee Related

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US12503556B2 (en)	2020-01-22	2025-12-23	Dow Silicones Corporation	Silicone-acrylate polymers, copolymers, and related methods and compositions

Also Published As

Publication number	Publication date
JPS61246277A (ja)	1986-11-01

Legal Events

Date	Code	Title	Description
1997-04-01	MKLA	Lapsed

Publication	Publication Date	Title
CA2010112C (fr)	2002-02-05	Adhesifs autocollants a emulsion siliconee
US2873263A (en)	1959-02-10	Polymerization of unsaturated compounds in the presence of bactericidal phenates of phenols and thiophenols
US5932638A (en)	1999-08-03	Free radical polymerizable compositions including para-halogenated aniline derivatives
GB1602401A (en)	1981-11-11	Primers for adhering silicone materials to substrates
US5610251A (en)	1997-03-11	Polymerisable compositions using air-activated latent initiator system of hydrogenated pyridine compound and acid
US5459206A (en)	1995-10-17	Two-part room temperature curable composition
US5492969A (en)	1996-02-20	Curable organopolysiloxane composition
CA1165933A (fr)	1984-04-17	Compose de scellement anaerobie fluable
CA1143087A (fr)	1983-03-15	Organopolysiloxanes vulcanisables a la temperature ambiante
CA1315440C (fr)	1993-03-30	Adhesifs au silicone et methodes de fabrication et d'utilisation connexes
CA2279354A1 (fr)	1998-08-13	Systeme en deux parties changeant de couleur et procede permettant de constater le durcissement d'un adhesif
US5268436A (en)	1993-12-07	Radically polymerizable multi-component mixtures and their use (I)
JPS5978220A (ja)	1984-05-07	室温硬化性弾性組成物
JPS5978221A (ja)	1984-05-07	室温硬化性弾性組成物
AU5471900A (en)	2001-01-02	Reactive adhesives and coatings with trifunctional olefinic monomers
CA1043498A (fr)	1978-11-28	Compose de polyester insature, de sel de cobalt et d'un accelerateur amine
US3794694A (en)	1974-02-26	Room temperature vulcanizable graft copolymers on silicone containing backbone
WO1989006666A1 (fr)	1989-07-27	Activateurs d'adherence pour preparations adhesives a base de thiolene
US5319011A (en)	1994-06-07	Compositions and method for catalytic curing of cyanoacrylate polymers
JPH04500226A (ja)	1992-01-16	新規ラジカル重合性多成分混合物およびその用途（２）
EP0563894B1 (fr)	1998-01-07	Composition à deux composants durcissable à temperature ambiante
US3290410A (en)	1966-12-06	Cold curing reaction lacquers containing at least one component containing ethylenicunsaturation curable by polymerization
CA1039879A (fr)	1978-10-03	Adhesifs pour montages metalliques colles resistants aux ambiances nefastes
CA1250082A (fr)	1989-02-14	Compositions acryliques polymerisables renfermant des additifs a base d'oxyde de vinyle
JPS585954B2 (ja)	1983-02-02	接着剤主剤組成物

CA1315440C - Adhesifs au silicone et methodes de fabrication et d'utilisation connexes - Google Patents

Info

Links

Landscapes

Applications Claiming Priority (2)

Publications (1)

Family

ID=24859858

Family Applications (1)

Country Status (2)

Cited By (1)

Families Citing this family (3)

Family Cites Families (2)

Cited By (1)

Also Published As

Similar Documents

Legal Events