GB1116725A - Surface treatment of organic polymers - Google Patents
Surface treatment of organic polymersInfo
- Publication number
- GB1116725A GB1116725A GB44642/65A GB4464265A GB1116725A GB 1116725 A GB1116725 A GB 1116725A GB 44642/65 A GB44642/65 A GB 44642/65A GB 4464265 A GB4464265 A GB 4464265A GB 1116725 A GB1116725 A GB 1116725A
- Authority
- GB
- United Kingdom
- Prior art keywords
- treated
- rubber
- polymer
- groups
- polyethylene
- 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
Classifications
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/28—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen sulfur-containing groups
-
- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/043—Improving the adhesiveness of the coatings per se, e.g. forming primers
-
- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
-
- 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
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- 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
- C08J2483/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
Abstract
The surface of a "vinylic polymer" is treated by applying a film comprising an organosilicon compound, free from aliphatic unsaturation, containing at least one HSR'Si radial, wherein R' is a divalent hydrocarbon radical free from aliphatic unsaturation, and applying energy to the surface whereby the organosilicon compound is irreversibly attached to the vinylic polymer. The term "vinylic polymer" refers to any organic polymer formed by the polymerisation of aliphatically unsaturated carbon-carbon bonds e.g. polyethylene, polypropylene, poly (acrylonitrilebutadiene-styrene), polystyrene, polymethylmethacrylate, poly (acrylonitrile-styrene), polyisobutene, polyvinyl chloride, polyvinyl acetate, poly (vinyl chloride-vinylidene chloride), and organic rubbers such as natural rubber, butyl rubber, ethylene-propylene-cyclohexadiene terpolymer, styrene-butadiene rubber, and butadiene-acrylonitrile rubber. The organo-silicon compound may be a silane of formula (HSR1-)mRn SiX4-m-n or partial hydrolysate thereof, where R is a monovalent hydrocarbon or halohydrocarbon radical free from aliphatic unsaturation, R' is a divalent hydrocarbon radical free from aliphatic unsaturation, m is 1, 2 or 3, n is 0, 1 or 2, and the sum of m and n is 1, 2 or 3, and X= is a hydroxyl radical or a hydrolysable substituent free from aliphatic unsaturation. More than one type of R and R' groups can be present. Examples of X are alkoxy radicals, halogen atoms, acyloxy groups, hydrocarbyl-substituted isocyanoxy groups, isocyanate groups. Examples of suitable silanes are listed. Energy may be applied to the surface in the form of heat in the absence of air, ultra-violet radiation. It is believed that the mercaptan groups on the organo-silicon molecules react with linkages in the organic polymeric surface. The vinylic polymer, say rubber, may be heated to the vulcanising temperature in a mould using the mercapto siloxane as a mould release fluid. There may be applied to the same surface of the treated vinylic polymer a film of a substance selected from compounds of formulae <FORM:1116725/B1-B2/1> and partial hydrolysates thereof, to impart oleophobicity to the surface, and X4-m-n <FORM:1116725/B1-B2/2> where R\yF is any alkylene radical containing not more than 4 carbon atoms, and is a positive integer, Q is a hydrogen atom or a R\yFNH2 radical, and partial hydrolysates thereof, to render the surface hydrophilic, silicic acid and partial condensates thereof to produce an essentially silica surface thus increasing the coefficient of friction, a polyglycol end blocked with a functional group that reacts with the hydrolysable groups on the surface to produce a hydrophilic or slightly hydrophilic surface. These substances may be applied simultaneously with those in the first treatment described. Water soluble dyes, inks and printing pastes, such as polyamide resins containing pigments, can be permanently affixed to the surface rendered hydrophilic as above, making possible the dyeing of thermoplastic fibres and printing on thermoplastic sheets. In another embodiment of the invention, a vinylic polymer surface is lubricated by treatment with a liquid siloxane polymer having a viscosity of at least 45cs. at 25 DEG C and consisting essentially of at least 2 units on the average of formula <FORM:1116725/B1-B2/3> per siloxane polymer molecule, at least five times as many these units of (HSR1-)mRk <FORM:1116725/B1-B2/4> units, where n is 0, 1 or 2, m is 1, 2 or 3, k is 0, 1 or 2 and the sum of m and k is not more than 3. The preferred siloxane is a linear dimethyl siloxane polymer with <FORM:1116725/B1-B2/5> groups as endblocking units. The oganosilicon compounds may be applied to the surface in pure, undiluted form or as solutions and emulsions. Methods of making the mercaptosilanes and mercaptosiloxanes are described. In Examples (1 to 4), various formulations of rubbers are vulcanised using mercapto-siloxane polymers as mould release agents, including in Example 1 a formulation comprising styrene-butadiene rubber, polybutadiene rubber, silica, zinc oxide, coumarone-indene resin, sulphur, stearic acid, and their characteristics compared with non-treated rubbers. In Example (5), steel panels primed with (CH3O)3SiCH2CH2CH2NHCH2 CH2NH2 are bonded to films of polyethylene, or acrylonitrile-butadiene-styrene terpolymer, and films of mercapto siloxanes are applied to the thermoplastic faces of the panels. In other Examples, (6) natural rubber is treated to form permanent lubricating characteristics, (7) polypropylene yarn is treated prior to dyeing with a solution of a water soluble dye, (8) a treated sheet of polyethylene was coated with (9) a thin film of 3, 3, 3-trifluoropropyltrimethoxy-silane to obtain an oleophobic surface (b) C7F15CH2CH2SiCl3 to obtain a hydrophobic surface, and a polyethylene container is treated and coated with (b), (9) a treated polyethylene sheet is further treated with (CH3O)3SiCH2CH2 CH2NHCH2CH2NH2 and coated with a polyamide resin useful as a printing paste, (10) two polyethylene sheets are treated and then coated with an aqueous dispersion of colloidal silica, the coefficients of friction then being measured, (11) a treated polyethylene sheet is treated with an ethylene-propylene polyglycol co-polymer end-blocked by reaction with <FORM:1116725/B1-B2/6> OCH2CH2CH2Si(CH3) to obtain an hydrophilic surface, (12) a ring of butadiene-acrylonitrile rubber is treated and then coated with <FORM:1116725/B1-B2/7> , a partial hydrolysate of (C4F9CH2CH2)2Si(OC2HS)2, <FORM:1116725/B1-B2/8> or <FORM:1116725/B1-B2/90> to obtain an oleophobic rubber ring resistant to swell in organic solvents.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US40557064A | 1964-10-21 | 1964-10-21 | |
US45292165A | 1965-05-03 | 1965-05-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1116725A true GB1116725A (en) | 1968-06-12 |
Family
ID=27019129
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB44642/65A Expired GB1116725A (en) | 1964-10-21 | 1965-10-21 | Surface treatment of organic polymers |
Country Status (3)
Country | Link |
---|---|
AT (1) | AT275885B (en) |
DE (1) | DE1277481B (en) |
GB (1) | GB1116725A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT513456A1 (en) * | 2012-10-09 | 2014-04-15 | Semperit Ag Holding | Process for modifying the surface of an elastomer product |
-
1965
- 1965-10-18 DE DED48449A patent/DE1277481B/en not_active Withdrawn
- 1965-10-19 AT AT946065A patent/AT275885B/en active
- 1965-10-21 GB GB44642/65A patent/GB1116725A/en not_active Expired
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AT513456A1 (en) * | 2012-10-09 | 2014-04-15 | Semperit Ag Holding | Process for modifying the surface of an elastomer product |
EP2719720A1 (en) * | 2012-10-09 | 2014-04-16 | Semperit Aktiengesellschaft Holding | Method for modifying the surface of an elastomer product |
AT513456B1 (en) * | 2012-10-09 | 2016-07-15 | Semperit Ag Holding | Process for modifying the surface of an elastomer product |
US9894946B2 (en) | 2012-10-09 | 2018-02-20 | Semperit Aktiengesellschaft Holding | Method for modifying the surface of an elastomer product |
Also Published As
Publication number | Publication date |
---|---|
AT275885B (en) | 1969-11-10 |
DE1277481B (en) | 1968-09-12 |
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