# US 10,767,082 B2 · Polymer compositions for UV curable primers

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- Number: US 10,767,082 B2
- Document ID: US10767082B2
- Status: Granted
- Kind: B2
- Application number: 16/337,983
- Filed: 2016-09-29
- Published: 2020-01-23
- Granted: 2020-09-08
- Earliest claimed: 2016-09-29
- Assignees: Dow Global Technologies LLC
- Applicants: Dow Global Technologies LLC
- Inventors: Haiyang Yu; Qichun Wan; Yongchun Chen; Shaoguang Feng
- Web page: https://patentgrep.com/patent/US10767082B2

## CPC

- C09J 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
- C09J 153/025: {modified}
- B32B 27/00: Layered products comprising {a layer of} synthetic resin {(fibrous or filamentary layer made of a synthetic resin B32B5/02; particulate layer made of a synthetic resin B32B5/16; foamed layer made of a synthetic resin B32B5/18)}
- C08F 265/06: Polymerisation of acrylate or methacrylate esters on to polymers thereof
- C08F 285/00: Macromolecular compounds obtained by polymerising monomers on to preformed graft polymers
- C08F 287/00: Macromolecular compounds obtained by polymerising monomers on to block polymers
- C09D 4/06: {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
- C09J 127/06: Homopolymers or copolymers of vinyl chloride
- C09J 131/04: Homopolymers or copolymers of vinyl acetate
- C09J 133/16: Homopolymers or copolymers of esters containing halogen atoms
- C09J 151/003: {grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds (C09J151/04, C09J151/06 take precedence)}
- C09J 151/06: grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
- B32B 5/02: characterised by structural features of a {fibrous or filamentary} layer {(layer formed of metallic wires B32B15/02; layer formed of natural mineral fibres B32B19/02; layer formed of wood fibres B32B21/02)}
- B32B 5/18: characterised by features of a layer {of} foamed material
- B32B 5/245: {another layer next to it being a foam layer}
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 2262/062: Cellulose fibres, e.g. cotton
- B32B 2266/025: Polyolefin
- B32B 2437/02: Gloves, shoes
- C09J 133/14: of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
- C09J 2301/416: use of irradiation
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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 (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)

## Abstract

Polymer compositions for UV curable primer formulations, as described herein. The primer formulations contain a modifier selected from the following: at least one modifier selected from a) through d) below: a) R1R2C═CR3-(CO)—Z (Formula A), as described herein, b) an acrylate-containing oligomer that has a Mn≤1500 g/mol, and an acid value from 50 to 500 mg KOH/g; c) a random terpolymer comprising, in polymerized form, vinyl chloride, vinyl acetate, and at least one of the following: a hydroxyl-containing alkyl acrylate, a hydroxyl-containing alkyl meth-acrylate, or a combination thereof or d) any combination of a) through c). Such primer formulations are useful for the binding of olefin-based polymer foams.

## Claims

### Claim 1

A composition comprising at least the following:
A) at least one modifier selected from a) through d) below:
a) R1R2C═CR3—(CO)—Z (Formula A),
wherein R1, R2 and R3 are each, independently, selected from the following: H; alkyl; heteroalkyl; aryl; heteroaryl; —C(O)—OH; or —R—C(O)—OH, where R is alkylene;
Z is selected from the following: —OH; —O—R—OH, where R is alkylene; —NR′R″, where R′ and R″ are each independently H or alkyl; —N(H)—R′″OH, where R′″ is alkylene; silane;
and wherein two or more atoms of Formula A may optionally form a ring structure;
b) an acrylate-containing oligomer that has an Mn≤1500 g/mol, and an acid value from 50 to 500 mg KOH/g;
c) a random terpolymer comprising, in polymerized form, vinyl chloride, vinyl acetate, and at least one of the following: a hydroxyl-containing alkyl acrylate, a hydroxyl-containing alkyl methacrylate, or a combination thereof;
d) or any combination of a) through c);
B) at least one chlorinated olefin-based polymer and/or at least one functionalized chlorinated olefin-based polymer;
C) at least one styrene-based block interpolymer or derivative thereof; and
D) at least one compound selected from the group consisting of the following:
wherein, for Formula D1, R is independently selected from the group consisting of the following; substituted or unsubstituted hydrocarbylenes, and substituted or unsubstituted hetero-hydrocarbylenes, and x is an integer ≥1;
wherein, for Formula D2, R is independently selected from the group consisting of the following; substituted or unsubstituted hydrocarbylenes, and substituted or unsubstituted hetero-hydrocarbylenes, and x≥1.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the composition further comprises at least one photoinitiator.

### Claim 3 (depends on 1)

The composition of claim 1, wherein the weight ratio of component A to the sum weight of components B, C and D, A/(B+C+D), is from 0.10 to 0.75.

### Claim 4 (depends on 1)

The composition of claim 1, wherein the component A is present in an amount from 5 to 35 wt %, based on the weight of the composition.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the component A is a random terpolymer (subcomponent c) that comprises the following properties: i) Mw from 10,000 to 100,000 g/mole; ii) from 70 to 95 wt % vinyl chloride, based on the weight of the terpolymer, iii) from 5 to 15 wt % vinyl acetate, based on the weight of the terpolymer; and iv) from greater than zero to 15 wt %, based on the weight of the terpolymer, of a hydroxyl-containing alkyl acrylate, where alkyl group comprises 1 to 6 carbons, or a hydroxyl-containing alkyl methacrylate where the alkyl group comprises 1 to 6 carbons.

### Claim 6 (depends on 1)

The composition of claim 1, wherein component D is selected from the following: (a) through (l):

### Claim 7 (depends on 1)

The composition according to claim 1, wherein component D) is selected from the group consisting of the following: 1,6 Hexanediol diacrylate (HDDA), tri propylene glycol di-acrylate (TPGDA); dipropylene glycol diacrylate (DPGDA); 1,4-butandiol diacrylate (BDDA); Diethylene glycol diacrylate; Triethylene glycol diacrylate; Neopentyl glycol diacrylate (NPGDA); and Nonanediol Diacrylate (NDDA).

### Claim 8 (depends on 1)

The composition according to claim 1, wherein component B is a chlorinated olefin-based polymer having a chlorine content from 10 to 40 wt %, based on the weight of the chlorinated olefin-based polymer.

### Claim 9 (depends on 1)

The composition according to claim 1, wherein component C) is selected from the group consisting of the following: styrene-ethylene/butylene-styrene block copolymer (SEBS); styrene/butadiene/styrene block copolymer (SBS); and maleic anhydride grafted styrene-ethylene/butylene-styrene block copolymer (SEBS-g-MAH).

### Claim 10 (depends on 1)

An article comprising at least one component formed from the composition of claim 1.