GB1094853A - Improvements in or relating to compositions curing rapidly under anaerobic conditions - Google Patents
Improvements in or relating to compositions curing rapidly under anaerobic conditionsInfo
- Publication number
- GB1094853A GB1094853A GB3189264A GB3189264A GB1094853A GB 1094853 A GB1094853 A GB 1094853A GB 3189264 A GB3189264 A GB 3189264A GB 3189264 A GB3189264 A GB 3189264A GB 1094853 A GB1094853 A GB 1094853A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- monomer
- phthalic
- dimethyl
- acids
- Prior art date
- 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
Links
- 239000000203 mixture Substances 0.000 title abstract 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 239000000178 monomer Substances 0.000 abstract 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 239000000853 adhesive Substances 0.000 abstract 2
- 230000001070 adhesive effect Effects 0.000 abstract 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 2
- 239000011976 maleic acid Substances 0.000 abstract 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 2
- -1 poly-alkylene glycols Chemical class 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- ACHDPKBTRFRSQD-UHFFFAOYSA-N 2-tert-butylperoxy-2,3-dimethylbutane Chemical group CC(C)C(C)(C)OOC(C)(C)C ACHDPKBTRFRSQD-UHFFFAOYSA-N 0.000 abstract 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000005695 Ammonium acetate Substances 0.000 abstract 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229940043376 ammonium acetate Drugs 0.000 abstract 1
- 235000019257 ammonium acetate Nutrition 0.000 abstract 1
- 239000001110 calcium chloride Substances 0.000 abstract 1
- 229910001628 calcium chloride Inorganic materials 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000010494 dissociation reaction Methods 0.000 abstract 1
- 230000005593 dissociations Effects 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 239000001530 fumaric acid Substances 0.000 abstract 1
- 235000011167 hydrochloric acid Nutrition 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 abstract 1
- 150000001451 organic peroxides Chemical class 0.000 abstract 1
- 150000002978 peroxides Chemical class 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- AVTYONGGKAJVTE-OLXYHTOASA-L potassium L-tartrate Chemical compound [K+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O AVTYONGGKAJVTE-OLXYHTOASA-L 0.000 abstract 1
- 239000001472 potassium tartrate Substances 0.000 abstract 1
- 229940111695 potassium tartrate Drugs 0.000 abstract 1
- 235000011005 potassium tartrates Nutrition 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 1
- 235000011152 sodium sulphate Nutrition 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- YWYZEGXAUVWDED-UHFFFAOYSA-N triammonium citrate Chemical compound [NH4+].[NH4+].[NH4+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O YWYZEGXAUVWDED-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/02—Monocarboxylic acids having less than ten carbon atoms, Derivatives thereof
- C08F20/10—Esters
- C08F20/20—Esters of polyhydric alcohols or polyhydric phenols, e.g. 2-hydroxyethyl (meth)acrylate or glycerol mono-(meth)acrylate
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Anaerobic adhesive compositions comprise a monomer (or partial polymer thereof) of the formula <FORM:1094853/C3/1> where R is H, CH3, C2H5, CH2OH or <FORM:1094853/C3/2> R1 is H, Cl, CH3 or C2H5; R11 is H, OH or <FORM:1094853/C3/3> x and y are integers of at least 1, and n is 0 or 1, an organic peroxide (other than a hydroperoxide) having a half-life (as defined) greater than 5 hours at 100 DEG C., an acid and/or salt having a dissociation constant in water greater than 10-6, water in an amount of 0.25-5.0% of the weight of the composition, and a tertiary amine. Tetra ethylene glycol dimethacrylate, dimethyl - di - t - butylperoxy hexane and dimethyl-p-toluidine are specified as monomer, peroxide and amine respectively. The acid used may be a polymerizable compound e.g. acrylic, methacrylic or maleic acid; other suitable acids include formic, acetic, phthalic and hydrochloric acids. Specified salts are sodium chloride, calcium chloride, sodium sulphate, ammonium citrate, potassium tartrate and ammonium acetate. A plasticizer may also be included in the composition, e.g. esters of monoalkyl ethers of mono- or poly-alkylene glycols with acids such as phthalic, trimellitic malonic, maleic or fumaric acid. In one Example, the monomer includes a small amount of hydroquinone inhibitor. The adhesives are particularly suitable for bonding nuts and bolts.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3189264A GB1094853A (en) | 1963-07-05 | 1964-08-05 | Improvements in or relating to compositions curing rapidly under anaerobic conditions |
| CH1082165A CH440694A (en) | 1963-07-05 | 1965-08-02 | Sticky composition |
| FR27035A FR92901E (en) | 1963-07-05 | 1965-08-03 | Composition curing under anaerobic conditions. |
| BE667954D BE667954A (en) | 1963-07-05 | 1965-08-05 | |
| NL6510189A NL6510189A (en) | 1963-07-05 | 1965-08-05 | |
| ES0316197A ES316197A2 (en) | 1964-08-05 | 1965-08-05 | Procedure for joining especially metallic surfaces. (Machine-translation by Google Translate, not legally binding) |
| FR89465A FR93063E (en) | 1963-07-05 | 1966-12-30 | Composition curing under anaerobic conditions. |
| BE692865D BE692865A (en) | 1963-07-05 | 1967-01-19 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB26798/63A GB1090753A (en) | 1963-07-05 | 1963-07-05 | Improvements in or relating to anaerobic curing compositions |
| GB3189264A GB1094853A (en) | 1963-07-05 | 1964-08-05 | Improvements in or relating to compositions curing rapidly under anaerobic conditions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1094853A true GB1094853A (en) | 1967-12-13 |
Family
ID=26258432
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3189264A Expired GB1094853A (en) | 1963-07-05 | 1964-08-05 | Improvements in or relating to compositions curing rapidly under anaerobic conditions |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE667954A (en) |
| CH (1) | CH440694A (en) |
| FR (1) | FR92901E (en) |
| GB (1) | GB1094853A (en) |
| NL (1) | NL6510189A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11459519B2 (en) * | 2017-01-20 | 2022-10-04 | Henkel Ag & Co, Kgaa | Anaerobic lubricant sealant |
-
1964
- 1964-08-05 GB GB3189264A patent/GB1094853A/en not_active Expired
-
1965
- 1965-08-02 CH CH1082165A patent/CH440694A/en unknown
- 1965-08-03 FR FR27035A patent/FR92901E/en not_active Expired
- 1965-08-05 NL NL6510189A patent/NL6510189A/xx unknown
- 1965-08-05 BE BE667954D patent/BE667954A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11459519B2 (en) * | 2017-01-20 | 2022-10-04 | Henkel Ag & Co, Kgaa | Anaerobic lubricant sealant |
Also Published As
| Publication number | Publication date |
|---|---|
| CH440694A (en) | 1967-07-31 |
| NL6510189A (en) | 1966-02-07 |
| BE667954A (en) | 1967-07-03 |
| FR92901E (en) | 1969-01-17 |
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