WO1994024197A1 - Primer coating process - Google Patents

Primer coating process Download PDF

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Publication number
WO1994024197A1
WO1994024197A1 PCT/US1994/002082 US9402082W WO9424197A1 WO 1994024197 A1 WO1994024197 A1 WO 1994024197A1 US 9402082 W US9402082 W US 9402082W WO 9424197 A1 WO9424197 A1 WO 9424197A1
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WO
WIPO (PCT)
Prior art keywords
range
mole percent
propylene
units
hexene
Prior art date
Application number
PCT/US1994/002082
Other languages
French (fr)
Inventor
Keith Philip Middleton
Original Assignee
Eastman Chemical Company
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.)
Filing date
Publication date
Application filed by Eastman Chemical Company filed Critical Eastman Chemical Company
Publication of WO1994024197A1 publication Critical patent/WO1994024197A1/en

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Classifications

    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/10—Homopolymers or copolymers of propene
    • 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
    • C08J7/042—Coating with two or more layers, where at least one layer of a composition contains a polymer binder
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/10—Homopolymers or copolymers of propene
    • C09D123/14—Copolymers of propene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
    • C09D123/02—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers not modified by chemical after-treatment
    • C09D123/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
    • C09D123/20—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms having four to nine carbon atoms
    • 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
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment

Definitions

  • This invention relates to a process for applying a primer to a polyolefin substrate and the resulting bicomponent structure.
  • the bicomponent structure can then be painted and the primer enhances the adhesion of the paint to the polyolefin substrate.
  • the application of paints and other coatings to substrates of polyolefin, such as polypropylene, thermoplastic olefin and polyethylene, is typically difficult because polyolefins are substantially chemically inert.
  • This problem has previously been overcome by use of two different approaches which employ adhesion promoting compositions.
  • One approach is to use an adhesion promoting composition as a separate primer coating between the polyolefin substrate and the paint.
  • the primer coating adheres adequately to both the polyolefin and the paint and thereby creates a unitary three component structure with the paint as the outer portion of the structure.
  • Another approach to coating polyolefins has been to use an adhesion promoting composition as an additive along with the paint. This technique is sometimes known in the art as use of a "stir in" adhesion promoter.
  • Numerous polymeric materials have been investigated as possible primer coating materials. Chlorinated polyolefins have been found to be very satisfactory as the polymeric component for primer compositions due to their cost and performance. For example, U.S. 3,579,485, U.S. 4,070,421, U.S. 4,966,947, U.S. 4,962,149 and U.S. 4,954,573 disclose chlorinated polyolefins which are entirely satisfactory for the polymeric component of adhesion promoting compositions useful for coating polyolefin substrates.
  • the maleated amorphous polypropylene useful in this invention has an acid number in the range of 10 to 60, preferably 18 to 30, and a molecular weight of at least 15,000. This polymer and methods for its preparation are well known in the art.
  • the amorphous propylene-hexene copolymer useful in this invention has propylene units in the range of 10 to 90 mole percent, preferably 13 to 62 mole percent, and hexene units in the range of 90 to 10 mole percent, preferably 87 to 34 mole percent, and a molecular weight of at least 20,000, preferably at least 28,000. This polymer and methods for its preparation are well known in the art.
  • the maleated amorphous propylene-hexene copolymer useful in this invention has propylene units in the range of 10 to 90 mole percent, preferably 13 to 62 mole percent, and hexene units in the range of 90 to 10 mole percent, preferably 87 to 38 mole percent, and a molecular weight of at least 20,000, preferably at least 28,000.
  • the polymer has an acid number in the range of 10 to 60, preferably 18 to 55. This polymer and methods for its preparation are well known in the art.
  • the process can be practiced using a primer coating composition comprised of one of the polymers and a solvent.
  • the amount of solvent is in the range of 90 to 99 weight parts, based on the weight of the polymer.
  • the solvent can comprise any suitable aromatic hydrocarbon and is preferably xylene.
  • the substrate can comprise any polyolefin useful in practicing the invention.
  • the polyolefin is polypropylene or propylene-ethylene copolymer, most preferably polypropylene.
  • the primer coating can be applied to the substrate using methods well known in the art.
  • the primer coating can be applied by dipping, spraying or rolling.
  • the primer coating is applied by spraying.
  • the practice of the process of this invention is illustrated by the following examples.
  • Primer coating compositions were prepared from each of these polymers by preparing an admixture of 90 weight parts xylene and 10 weight parts of the polymer using a laboratory mixer. Each of these primer coating compositions was applied to two test pieces of a polypropylene homopolymer and to two test pieces of a rubber modified polypropylene. The primer coating was applied to all of the test pieces by dipping the test pieces into the primer coating compositions.
  • test pieces were dried so that a layer of approximately 2 microns of polymer were on the surface.
  • test pieces was then immersed in a conventional thermoplastic cellulose acetate butyrate/acrylic lacquer and left to dry at ambient temperature overnight. The adhesion was evaluated by cutting five horizontal and five vertical lines intersecting each other into the coated substrate.
  • Polymer 1 75%-90% 75%-90% 75%-90% 75%-90% 75%-90% Polymer 2 100% 100% 100% 100% Polymer 3 50%-75% 50%-75% 100% 100% Polymer 4 100% 100% 100% 100% 100% Polymer 5 > 90% > 90% 100% 100%
  • the peel adhesion of each of the test pieces was studied using the following procedure.
  • the viscosity of each of the primer coating compositions was reduced to 10.5 seconds, Din 4 cup, with xylene.
  • the primer coating compositions were then sprayed onto test pieces of a polypropylene homopolymer to give a dry film thickness of less than 5 microns. After one hour a conventional urethane top coat was then spray applied to give a dry film thickness of 90—100 microns.
  • the coated test pieces were left at ambient temperature for 45 minutes prior to curing at 80°C.
  • the test pieces were then aged at room temperature for 1 week. Peel tests were then conducted using an Instron table top tensiometer.

Abstract

Disclosed is a process comprising applying to a polyolefin substrate a polymer selected from the group consisting of (A) a maleated amorphous polypropylene having an acid number in the range of 10 to 60 and a molecular weight of at least 15,000; (B) an amorphous propylene-hexene copolymer having propylene units in the range of 10 to 90 mole percent and hexene units in the range of 90 to 10 mole percent and a molecular weight of at least 20,000, and (C) a maleated amorphous propylene-hexene copolymer having propylene units in the range of 10 to 90 mole percent and hexene units inthe range of 90 to 10 mole percent, a molecular weight of at least 20,000 and an acid number in the range of 10 to 60.

Description

PRIMER COATING PROCESS This invention relates to a process for applying a primer to a polyolefin substrate and the resulting bicomponent structure. The bicomponent structure can then be painted and the primer enhances the adhesion of the paint to the polyolefin substrate. The application of paints and other coatings to substrates of polyolefin, such as polypropylene, thermoplastic olefin and polyethylene, is typically difficult because polyolefins are substantially chemically inert. This problem has previously been overcome by use of two different approaches which employ adhesion promoting compositions. One approach is to use an adhesion promoting composition as a separate primer coating between the polyolefin substrate and the paint. The primer coating adheres adequately to both the polyolefin and the paint and thereby creates a unitary three component structure with the paint as the outer portion of the structure. Another approach to coating polyolefins has been to use an adhesion promoting composition as an additive along with the paint. This technique is sometimes known in the art as use of a "stir in" adhesion promoter. Numerous polymeric materials have been investigated as possible primer coating materials. Chlorinated polyolefins have been found to be very satisfactory as the polymeric component for primer compositions due to their cost and performance. For example, U.S. 3,579,485, U.S. 4,070,421, U.S. 4,966,947, U.S. 4,962,149 and U.S. 4,954,573 disclose chlorinated polyolefins which are entirely satisfactory for the polymeric component of adhesion promoting compositions useful for coating polyolefin substrates.
We have now discovered that a several types of polymers well known in the art are effective as primer coating materials to enhance the adhesion of paints to polyolefins. These polymers are selected from the group consisting of
(A) a maleated amorphous polypropylene,
(B) an amorphous propylene-hexene copolymer, and
(C) a maleated amorphous propylene-hexene copolymer.
The maleated amorphous polypropylene useful in this invention has an acid number in the range of 10 to 60, preferably 18 to 30, and a molecular weight of at least 15,000. This polymer and methods for its preparation are well known in the art. The amorphous propylene-hexene copolymer useful in this invention has propylene units in the range of 10 to 90 mole percent, preferably 13 to 62 mole percent, and hexene units in the range of 90 to 10 mole percent, preferably 87 to 34 mole percent, and a molecular weight of at least 20,000, preferably at least 28,000. This polymer and methods for its preparation are well known in the art. The maleated amorphous propylene-hexene copolymer useful in this invention has propylene units in the range of 10 to 90 mole percent, preferably 13 to 62 mole percent, and hexene units in the range of 90 to 10 mole percent, preferably 87 to 38 mole percent, and a molecular weight of at least 20,000, preferably at least 28,000. The polymer has an acid number in the range of 10 to 60, preferably 18 to 55. This polymer and methods for its preparation are well known in the art.
Optionally, the process can be practiced using a primer coating composition comprised of one of the polymers and a solvent. In this embodiment, the amount of solvent is in the range of 90 to 99 weight parts, based on the weight of the polymer. The solvent can comprise any suitable aromatic hydrocarbon and is preferably xylene. Broadly, the substrate can comprise any polyolefin useful in practicing the invention. Preferably, the polyolefin is polypropylene or propylene-ethylene copolymer, most preferably polypropylene. The primer coating can be applied to the substrate using methods well known in the art. For example, the primer coating can be applied by dipping, spraying or rolling. Preferably, the primer coating is applied by spraying. The practice of the process of this invention is illustrated by the following examples.
The polymers described in the below table were selected for adhesion studies.
Polymer Acid Molecular
Number Type Number Wei ht
1 maleated amorphous 23 19,000 polypropylene
2 amorphous 62 mole % hexene and 0 39,000
38 mole % propylene copolymer 3 amorphous 13 mole % hexene and 0 28,000 87 mole % propylene copolymer
4 maleated amorphous 13 mole % 44 28,000 hexene and 87 mole % propylene copolymer
5 maleated amorphous 13 mole % 22 28,000 hexene and 87 mole % propylene copolymer maleated amorphous 62 mole % 40 39,000 hexene and 38 mole % propylene copolymer Initial adhesion of these polymers was studied using the following procedure. Primer coating compositions were prepared from each of these polymers by preparing an admixture of 90 weight parts xylene and 10 weight parts of the polymer using a laboratory mixer. Each of these primer coating compositions was applied to two test pieces of a polypropylene homopolymer and to two test pieces of a rubber modified polypropylene. The primer coating was applied to all of the test pieces by dipping the test pieces into the primer coating compositions. Each of the test pieces was dried so that a layer of approximately 2 microns of polymer were on the surface. Each of the test pieces was then immersed in a conventional thermoplastic cellulose acetate butyrate/acrylic lacquer and left to dry at ambient temperature overnight. The adhesion was evaluated by cutting five horizontal and five vertical lines intersecting each other into the coated substrate.
Adhesive tape was applied and firmly pressed over the cut area. The tape was then removed and amount of lacquer coating removed by the tape was observed. The results of the initial adhesion tests are shown in the below table. Primer Propylene Homopolvmer Modified Polypropylene Containing 1 2 1 2
Polymer 1 75%-90% 75%-90% 75%-90% 75%-90% Polymer 2 100% 100% 100% 100% Polymer 3 50%-75% 50%-75% 100% 100% Polymer 4 100% 100% 100% 100% Polymer 5 > 90% > 90% 100% 100%
The peel adhesion of each of the test pieces was studied using the following procedure. The viscosity of each of the primer coating compositions was reduced to 10.5 seconds, Din 4 cup, with xylene. The primer coating compositions were then sprayed onto test pieces of a polypropylene homopolymer to give a dry film thickness of less than 5 microns. After one hour a conventional urethane top coat was then spray applied to give a dry film thickness of 90—100 microns. The coated test pieces were left at ambient temperature for 45 minutes prior to curing at 80°C. The test pieces were then aged at room temperature for 1 week. Peel tests were then conducted using an Instron table top tensiometer. In this test 1 cm strips were cut down the test pieces and the test pieces were clamped into the stationary jaws of the tensiometer. Adhesive tape was then attached to the movable jaws of the tensiometer. The test was started with the movable jaws travelling at 5 cm/minute. The peel strength of the primer coating is then obtained from the tensiometer trace and is measured in grams. Results of these tests are reported in the below table.
Primer
Containing Peel Strength
Polymer 1 350-400
Polymer 2 290-380
Polymer 3 130-180
Polymer 4 130-140
Polymer 5 200-300+
Polymer 6 170-180

Claims

CLAIMS 1. A process comprising applying to a polyolefin substrate a polymer selected from the group consisting of (A) a maleated amorphous polypropylene having an acid number in the range of 10 to 60 and a molecular weight of at least 15,000,
(B) an amorphous propylene-hexene copolymer having propylene units in the range of 10 to 90 mole percent and hexene units in the range of 90 to
10 mole percent and a molecular weight of at least 20,000, and
(C) a maleated amorphous propylene-hexene copolymer having propylene units in the range of 10 to 90 mole percent and hexene units in the range of 90 to 10 mole percent, a molecular weight of at least 20,000 and an acid number in the range of 10 to 60.
2. A process comprising
(A) preparing a primer coating comprising (1) a polymer selected from the group consisting of
(a) a maleated amorphous polypropylene having an acid number in the range of 10 to 60 and a molecular weight of at least 15,000, (b) an amorphous propylene-hexene copolymer having propylene units in the range of 10 to 90 mole percent and hexene in units in the range of 90 to 10 mole percent and a molecular weight of at least 20,000, and (c) a maleated amorphous propylene- hexene copolymer having propylene units in the range of 10 to 90 mole percent and hexene units in the range of 90 to 10 mole percent, a molecular weight of at least 20,000 and an acid number in the range of 10 to 60, and (2) from 90 to 99 weight parts, based on the weight of the polymer, of a solvent, and (B) applying the primer coating composition to a substrate selected from the group consisting of polypropylene and propylene—ethylene copolymer.
3. A process comprising
(A) preparing a primer coating comprising
(1) a polymer selected from the group consisting of (a) a maleated amorphous polypropylene having an acid number in the range of 18 to 30 and a molecular weight of at least 15000,
(b) an amorphous propylene-hexene copolymer having propylene units in the range of 13 to 62 mole percent and hexene in units in the range of 87 to 38 mole percent and a molecular weight of at least 28,000, and
(c) a maleated amorphous propylene- hexene copolymer having propylene units in the range of 13 to 62 mole percent and hexene units in the range of 87 to 38 mole percent, a molecular weight of at least 28,000 and an acid number in the range of 18 to 55, and
(2) from 90 to 95 weight parts, based on the weight of the polymer, of a solvent, and (B) applying the primer coating composition to a polypropylene substrate.
4. A bicomponent structure comprising a polyolefin substrate and a primer coating which is bonded to the substrate and is selected from the group consisting of
(A) a maleated amorphous polypropylene having an acid number in the range of 10 to 60 and a molecular weight of at least 15,000,
(B) an amorphous propylene-hexene copolymer having propylene units in the range of 13 to 62 mole percent and hexene units in the range of 90 to 30 mole percent and a molecular weight of at least 28,000, and
(C) a maleated amorphous propylene-hexene copolymer having propylene units in the range of 13 to 62 mole percent and hexene units in the range of 87 to 38 mole percent, a molecular weight of at least 28,000 and an acid number in the range of 18 to 55.
5. A bicomponent structure comprising a substrate selected from the group consisting of polypropylene and propylene—ethylene copolymer and a polymer - 12 -
which is bonded to the substrate and is selected from the group consisting of
(A) a maleated amorphous polypropylene having an acid number in the range of 18 to 30 and a molecular weight of at least 15000,
(B) an amorphous propylene-hexene copolymer having propylene units in the range of 13 to 62 mole percent and hexene in units in the range of 87 to 38 mole percent and a molecular weight of at least 28,000, and
(C) a maleated amorphous propylene-hexene copolymer having propylene units in the range of 13 to 62 mole percent and hexene units in the range of 87 to 38 mole percent, a molecular weight of at least 28,000 and an acid number in the range of 18 to 55.
6. The bicomponent structure of claim 5 wherein the substrate is polypropylene.
PCT/US1994/002082 1993-04-12 1994-04-04 Primer coating process WO1994024197A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US4487493A 1993-04-12 1993-04-12
US08/044,874 1993-04-12

Publications (1)

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WO1994024197A1 true WO1994024197A1 (en) 1994-10-27

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6310134B1 (en) 1998-06-30 2001-10-30 Eastman Chemical Company Adhesion-promoting primer compositions for polyolefin substrates

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1040539A (en) * 1964-03-17 1966-08-24 Hercules Powder Co Ltd Improvements in or relating to method of coating polyolefin objects
EP0407666A1 (en) * 1987-12-28 1991-01-16 Mitsui Petrochemical Industries, Ltd. Surface-treating agent for the treatment of a moulded rubber article
JPH0349952A (en) * 1989-07-18 1991-03-04 Toray Ind Inc Polypropylene composite film and metal vapor deposition polypropylene composite film
JPH04136042A (en) * 1990-09-28 1992-05-11 Ube Ind Ltd Surface treatment of polyolefin molding to be coated
US5192620A (en) * 1991-11-08 1993-03-09 Mobil Oil Corporation Metallized composite film structure and method
EP0541273A1 (en) * 1991-11-05 1993-05-12 Mobil Oil Corporation Metallized film structure and method

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1040539A (en) * 1964-03-17 1966-08-24 Hercules Powder Co Ltd Improvements in or relating to method of coating polyolefin objects
EP0407666A1 (en) * 1987-12-28 1991-01-16 Mitsui Petrochemical Industries, Ltd. Surface-treating agent for the treatment of a moulded rubber article
JPH0349952A (en) * 1989-07-18 1991-03-04 Toray Ind Inc Polypropylene composite film and metal vapor deposition polypropylene composite film
JPH04136042A (en) * 1990-09-28 1992-05-11 Ube Ind Ltd Surface treatment of polyolefin molding to be coated
EP0541273A1 (en) * 1991-11-05 1993-05-12 Mobil Oil Corporation Metallized film structure and method
US5192620A (en) * 1991-11-08 1993-03-09 Mobil Oil Corporation Metallized composite film structure and method

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Derwent World Patents Index; AN 92-205251[25] *
PATENT ABSTRACTS OF JAPAN vol. 15, no. 194 (M - 1114) 20 May 1991 (1991-05-20) *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6310134B1 (en) 1998-06-30 2001-10-30 Eastman Chemical Company Adhesion-promoting primer compositions for polyolefin substrates

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