Organic resin laminate

Patent metadata

Field	Value
Publication number	US-2017198110-A1
Application number	US-201515316724-A
Country	US
Kind code	A1
Filing date	Jun 8, 2015
Priority date	Jun 12, 2014
Publication date	Jul 13, 2017
Grant date	—

Abstract

An organic resin laminate comprising an organic resin substrate and a multilayer coating system on a surface of the substrate is provided. The multilayer coating system can include a plasma layer which is a dry hard coating obtained from plasma polymerization of an organosilicon compound, and an intermediate layer (II) on the substrate which is a cured coating of a wet coating composition comprising (A) a specific reactive UV absorber, (B) a multi-functional (meth)acrylate, and (C) a photopolymerization initiator. (B) a multifunctional (meth)acrylate, and (C) a photopolymerization initiator. The laminate has a high level of abrasion resistance and improved adhesion and weather resistance.

First claim

1 . A method of making an organic resin laminate, comprising:
applying a wet coating to an organic resin substrate to form to form an intermediate layer (II) on the substrate, wherein the wet coating comprises a multi-functional (meth)acrylate, a photopolymerization initiator, and a reactive UV absorber having the general formula (1):

wherein Y 1 and Y 2 are each independently a substituent group of the general formula (2):

wherein * stands for a bonding site, r is 0 or 1, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, hydroxyl, C 1 -C 20 alkyl, C 4- C 12 cycloalkyl, C 2 -C 20 alkenyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenyloxy, C 7 -C 20 aralkyl, halogen, —C≡N, C 1 -C 5 haloalkyl, —SO 2 R′, —SO 3 H, —SO 3 M (M=alkali metal), —COOR′, —CONHR′, —CONR′R″, —OCOOR′, —OCOR′, —OCONHR′, (meth)acrylamino, (meth)acryloxy, optionally substituted C 6 -C 12 aryl and optionally substituted C 3 -C 12 heteroaryl, wherein R′ and R″ are each independently hydrogen, C 1 -C 20 alkyl, C 4- C 12 cycloalkyl, optionally substituted C 6 -C 12 aryl or optionally substituted C 3 -C 12 heteroaryl,
X is a di-, tri- or tetravalent, linear or branched, saturated hydrocarbon residue which may be separated by at least one element of oxygen, nitrogen, sulfur, and phosphor,
T is a urethane group —O—(C═O)—NH—,
Q is a di- or trivalent, linear or branched, saturated hydrocarbon residue which may be separated by at least one element of oxygen, nitrogen, sulfur, and phosphor,
P is (meth)acryloxy, and
m is 1 or 2, and n is an integer of 1 to 3, with the proviso that m and n are not equal to 1 at the same time;
UV curing the wet coating to form a cured coating; and
depositing a first plasma coating on the cured coating, wherein the first plasma coating is deposited using a first oxygen flow rate of less than 250 sccm per plasma source.

2 . The method of claim 1 , wherein the first oxygen flow rate of less than or equal to 100 sccm per plasma source.

3 . The method of claim 2 , wherein the first oxygen flow rate of less than or equal to 50 sccm per plasma source.

4 . The method of claim 3 , wherein the first oxygen flow rate of less than or equal to 10 sccm per plasma source.

5 . A method of making an organic resin laminate, comprising:
applying a wet coating to an organic resin substrate to form an intermediate layer (II) on the substrate, wherein the wet coating comprises a multi-functional (meth)acrylate, a photopolymerization initiator, and a reactive UV absorber having the general formula (1):

wherein Y 1 and Y 2 are each independently a substituent group of the general formula (2):

wherein * stands for a bonding site, r is 0 or 1, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, hydroxyl, C 1 -C 20 alkyl, C 4- C 12 cycloalkyl, C 2 -C 20 alkenyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenyloxy, C 7 -C 20 aralkyl, halogen, —C≡N, C 1 -C 5 haloalkyl, —SO 2 R′, —SO 3 H, —SO 3 M (M=alkali metal), —COOR′, —CONHR′, —CONR′R″, —OCOOR′, —OCOR′, —OCONHR′, (meth)acrylamino, (meth)acryloxy, optionally substituted C 6 -C 12 aryl and optionally substituted C 3 -C 12 heteroaryl, wherein R′ and R″ are each independently hydrogen, C 1 -C 20 alkyl, C 4- C 12 cycloalkyl, optionally substituted C 6 -C 12 aryl or optionally substituted C 3 -C 12 heteroaryl,
X is a di-, tri- or tetravalent, linear or branched, saturated hydrocarbon residue which may be separated by at least one element of oxygen, nitrogen, sulfur, and phosphor,
T is a urethane group —O—(C═O)—NH—,
Q is a di- or trivalent, linear or branched, saturated hydrocarbon residue which may be separated by at least one element of oxygen, nitrogen, sulfur, and phosphor,
P is (meth)acryloxy, and
m is 1 or 2, and n is an integer of 1 to 3, with the proviso that m and n are not equal to 1 at the same time;
UV curing the wet coating to form a cured coating;
depositing a first plasma coating on the cured coating without an introduction of a molecular oxygen stream.

6 . The method of claim 1 , further comprising, depositing a second plasma coating on the first plasma coating, wherein the second plasma coating and the first plasma coating form a plasma layer, and wherein the second plasma coating is deposited using a second oxygen flow rate of greater than or equal to 250 sccm per plasma source.

7 . (canceled)

8 . (canceled)

9 . The method of claim 1 , wherein the first plasma coating is deposited using expanding thermal plasma deposition.

10 . The method of claim 1 , further comprising flashing off solvent from the wet coating before the UV curing.

11 . (canceled)

12 . (canceled)

13 . The method of claim 1 , further comprising molding the substrate prior to applying the wet coating, wherein the organic resin substrate comprises polycarbonate, a blend comprising polycarbonate, or a copolymer comprising polycarbonate.

14 . (canceled)

15 . (canceled)

16 . (canceled)

17 . (canceled)

18 . (canceled)

19 . (canceled)

20 . (canceled)

21 . (canceled)

22 . (canceled)

23 . (canceled)

24 . (canceled)

25 . (canceled)

26 . (canceled)

27 . An organic resin laminate comprising:
an organic resin substrate and a multilayer coating system on a surface of the substrate, said multilayer coating system including a plasma layer obtained from polymerization of an organosilicon compound, and an intermediate layer (II) which is a UV cured coating of a coating composition, the intermediate layer (II) disposed between the plasma layer and the organic resin substrate,
said coating composition comprising (A) a reactive UV absorber, (B) a multi-functional (meth)acrylate, and (C) a photopolymerization initiator, the reactive UV absorber having the general formula (1):

wherein Y 1 and Y 2 are each independently a substituent group of the general formula (2):

wherein * stands for a bonding site, r is 0 or 1, R 1 , R 2 and R 3 are each independently selected from the group consisting of hydrogen, hydroxyl, C 1 -C 20 alkyl, C 4- C 12 cycloalkyl, C 2 -C 20 alkenyl, C 1 -C 20 alkoxy, C 4 -C 12 cycloalkoxy, C 2 -C 20 alkenyloxy, C 7 -C 20 aralkyl, halogen, —C≡N, C 1 -C 5 haloalkyl, —SO 2 R′, —SO 3 H, —SO 3 M (M=alkali metal), —COOR′, —CONHR′, —CONR′R″, —OCOOR′, —OCOR′, —OCONHR′, (meth)acrylamino, (meth)acryloxy, optionally substituted C 6 -C 12 aryl and optionally substituted C 3 -C 12 heteroaryl, wherein R′ and R″ are each independently hydrogen, C 1 -C 20 alkyl, C 4- C 12 cycloalkyl, optionally substituted C 6 -C 12 aryl or optionally substituted

Assignees

• Exatec Llc
• Shinetsu Chemical Co

Inventors

• Higuchi Koichi
• Gasworth Steven Marc

Classifications

• C08J2433/04

  esters · CPC title

• C08J7/18 Primary

  using wave energy or particle radiation · CPC title

• C08J2433/14

  of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen · CPC title

• C08J7/123

  Treatment by wave energy or particle radiation (C08J7/18 takes precedence) · CPC title

• C09D4/00

  Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond {; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16} · CPC title