Primer compositions for injection molding

Patent metadata

Field	Value
Publication number	US-10815388-B2
Application number	US-201514951661-A
Country	US
Kind code	B2
Filing date	Nov 25, 2015
Priority date	May 30, 2013
Publication date	Oct 27, 2020
Grant date	Oct 27, 2020

Abstract

Curable compositions, such as by way of exposure to radiation in the electromagnetic spectrum, for use as a primer composition for injection molding applications, are provided.

First claim

What is claimed is:

1. A process for forming an injection molded article, comprising:
providing a photocurable primer composition comprising:
10 to 90 wt. % of one or more (meth)acrylate monomers;
optionally, 1 to 10 wt. % of a cyanate ester component;
1 to 5 wt. % of a photoinitiator component selected from selected from the group consisting of 2,4,6 trimethylbenzoyldiphosphine oxide, 1-hydrocyclohexyl-phenyl ketone, 2-hydroxy-2-methyl-1-phenyl-propan-1-one, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methyl-1-propanone, acetophenone and substituted acetophenones, benzoin and its alkyl esters, xanthone and substituted xanthones, diethoxy-acetophenone, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, diethoxyxanthone, chloro-thio-xanthone, N-methyl diethanol-amine-benzophenone, 1-benzoyl cyclohexanol, 2-benzyl-2-(dimethylamino)-1-[4-(4-morpholinyl)phenyl]-1-butanone; amino ketones, benzildimethyl-ketals, bis acyl phosphine oxide and benzophenones;
about 15 to 35 wt. % of a rubber component comprising the combination of a core shell rubber having a mean diameter in the range of about 100 to about 300 nm, a polyvinyl butyral component having a molecular weight of less than about 120,000 Mw and optionally a (meth)acrylate carrier, wherein the core shell rubber and polyvinyl butyral component are present at a weight ratio of 1 to 1 to 2 to 1; and
optionally 0.25 to about 5 wt. % of an amine component which is an aromatic amine component or a cycloaliphatic diamine component;

providing an article;
coating at least a portion of a surface of the article with the photocurable primer composition;
partially but not fully curing the coating to a tack free surface by exposure to UV radiation, visible radiation or both UV radiation and visible radiation;
providing an injection molding equipment having an open injection molding cavity;
transferring the coated article into the open injection molding cavity;
closing the injection molding cavity;
injecting a molten thermoplastic resin selected from polycarbonate, glass filled polycarbonate, polyacrylamide and polycarbonate/acrylonitrile butadiene styrene alloy into the closed molding cavity and around the coated article;
allowing the thermoplastic resin to solidify on the coated article to form the injection molded article;
opening the injection molding cavity; and
removing the injection molded article.

2. The process of claim 1 , wherein the one or more (meth)acrylate monomers of the photocurable primer composition are selected from one or more of N, N-dimethyl acrylamide, phenoxy ethyl(meth)acrylate, tetrahydrofuryral (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, butyl (meth)acrylate, hydroxyethyl (meth)acrylate, and hydroxypropyl (meth)acrylate.

3. The process of claim 1 , wherein the one or more (meth)acrylate monomers of the photocurable primer composition are present in an amount of about 40 to about 80 weight percent.

4. The process of claim 1 , wherein the core shell rubber of the photocurable primer composition has a core constructed of styrene butadiene rubber and a shell constructed of polyacrylate.

5. The process of claim 1 , wherein the rubber component of the photocurable primer composition is present in an amount of about 20 to about 30 weight percent.

6. The process of claim 1 , wherein the cyanate ester component of the photocurable primer composition is selected from one or more of bisphenol E dicyanate ester, bisphenol F dicyanate ester, dicyclopentanediol dicyanate ester, 1,1′-bis(4-cyanatophenyl)ethane), bisphenol-A cyanate ester resin, hexafluorobisphenol-A cyanate ester resin, tetramethylbisphenol-F cyanate ester resin, bisphenol-C cyanate ester resin, bisphenol-M cyanate ester resin, phenol novolac cyanate ester resin and dicyclopentadienyl-bisphenol cyanate ester resin.

7. The process of claim 1 , wherein the amine component of the photocurable primer composition is present as an aromatic amine component or a cycloaliphatic diamine component.

8. The process of claim 1 , wherein the amine component of the photocurable primer composition is present in an amount of about 1 to about 5 weight percent.

9. The process of claim 1 , wherein in the photocurable primer composition the one or more (meth)acrylate monomers are is present in an amount of about 20 to about 80 weight percent;
the cyanate ester component is present in an amount of about 1 to about 10 weight percent; and the amine component is an aminated diphenyl sulfone component that is present in an amount of about 0.25 to about 5 weight percent.

10. The process of claim 1 , wherein the amine photocurable primer component is present in the composition as aminated diphenyl sulfone.

11. An injection molded article formed from the process of claim 1 .

12. The process of claim 1 further comprising the step of storing the article and partially cured coating separately from the injection molding process prior to the step of transferring the coated article into the open injection molding cavity.

13. The process of claim 1 wherein the photocurable primer composition consists of:
the one or more (meth)acrylate monomers;
the cyanate ester component;
the photoinitiator component;
the rubber component; and
the aromatic amine component or the cycloaliphatic diamine component.

14. The process of claim 1 wherein in the photocurable primer composition the aromatic amine component is 3,3′ diaminodiphenyl sulfone and the cycloaliphatic diamine component is diaminodicyclohexylmethane.

15. The process of claim 1 , wherein the one or more (meth)acrylate monomers of the photocurable primer composition comprise N, N-dimethyl acrylamide.

Assignees

• Henkel IP & Holding GmbH

Inventors

• Konarski Mark M
• Penrose Nicholas
• Nolan Darren
• Deegan Brian

Classifications

• C09D4/06 Primary

  {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 · CPC title

• C09D109/06 Primary

  Copolymers with styrene · CPC title

• B29K2709/08

  Glass · CPC title

• B32B2250/02

  2 layers · CPC title

• B32B37/12

  characterised by using adhesives · CPC title