IP Library Patent Application 15313081
Patent Application
App. No. 15/313,081

COATING PROCESS

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Patent No.
US None
App. No.
15/313,081
Abstract

Methods of making components for a medicinal delivery device are described, in which a primer composition comprising a silane having two or more reactive silane groups separated by an organic linker group is applied to a surface of a component, then a coating composition comprising an at least partially fluorinated compound is applied to the primed surface. The surface may be a polymer surface. Corresponding coated components and a medicinal delivery device are disclosed. Methods of making metal components are described in which a coating composition comprising an at least partially fluorinated compound is applied to a surface cleaned with a solvent.

Claims (84)

1 . A method of making a component for a medicinal delivery device, the method comprising

a) providing a component of a medicinal delivery device,

b) providing a primer composition comprising a silane having two or more reactive silane groups separated by an organic linker group,

c) providing a coating composition comprising an at least partially fluorinated compound,

d) applying the primer composition to at least a portion of the surface of the component,

e) applying the coating composition to the portion of the surface of the component after application of the primer composition.

2 . A method as claimed in claim 1 , wherein the silane having two or more reactive silane groups is of formula

X 3-m (R 1 ) m Si-Q-Si(R 2 ) k X 3-k

wherein R 1 and R 2 are independently selected univalent groups, X is a hydrolysable or hydroxy group, m and k are independently 0, 1, or 2 and Q is a divalent organic linking group.

3 . A method as claimed in claim 2 , wherein Q is of formula —(CH 2 ) i -A-(CH 2 ) j — wherein A is NR n , O, or S; i and j are independently 0, 1, 2, 3 or 4 and wherein R n is H or C 1 to C 4 alkyl.

4 . A method as claimed in Claim 1 , wherein the partially fluorinated compound is a polyfluoropolyether silane of formula

R f Q 1 v [Q 2 w -[C(R 4 ) 2 —Si(X) 3-x (R 5 ) x ] y ] z

wherein:

R f is a polyfluoropolyether moiety;

Q 1 is a trivalent linking group;

each Q 2 is an independently selected organic divalent or trivalent linking group;

each R 4 is independently hydrogen or a C 1-4 alkyl group;

each X is independently a hydrolysable or hydroxyl group;

R 5 R is a C 1-8 alkyl or phenyl group;

v and w are independently 0 or 1, x is 0 or 1 or 2; y is 1 or 2; and z is 2, 3, or 4.

5 . A method as claimed in claim 4 , wherein the polyfluoropolyether moiety R f comprises perfluorinated repeating units selected from the group consisting of —(C n F 2n O)—, —(CF(Z)O)—, —(CF(Z)C n F 2n O)—, —(C n F 2n SF(Z)O)—, —(CF 2 CF(Z)O)—, and combinations thereof; wherein n is an integer from 1 to 6 and Z is a perfluoroalkyl group, an oxygen-containing perfluoroalkyl group, a perfluoroalkoxy group, or an oxygen-substituted perfluoroalkoxy group, each of which can be linear, branched, or cyclic, and have 1 to 5 carbon atoms and up to 4 oxygen atoms when oxygen-containing or oxygen-substituted and wherein for repeating units including Z the number of carbon atoms in sequence is at most 6.

6 . A method of making a component for a medicinal delivery device, the method comprising

a) providing a component of a medicinal delivery device,

b) providing a coating composition comprising an at least partially fluorinated compound,

d) cleaning at least a portion of the surface of the component using a solvent comprising a hydrofluoroether of formula

C g F 2g+1 OC h H 2h+1

wherein g is 2, 3, 4, 5, or 6 and h is 1, 2, 3 or 4

e) applying the coating composition to the portion of the surface of the component after cleaning with the solvent.

7 . A method as claimed in claim 6 , wherein the hydrofluoroether is selected from the group consisting of methyl heptafluoropropylether; ethyl heptafluoropropylether ; methyl nonafluorobutylether; ethyl nonafluorobutylether and mixtures thereof.

8 . A method as claimed in claim 1 , wherein said surface is a metal surface, in particular a surface of an aluminium alloy, an iron alloy, or a steel alloy.

9 . A method as claimed in claim 1 , where said medicinal delivery device is a metered dose inhaler or a dry powder inhaler.

10 . A method as claimed in claim 1 , wherein the component is a component of a metered dose inhaler and the component is selected from the group consisting of an actuator, an aerosol container, a ferrule, a valve body, a valve stem and a compression spring.

11 . A medicinal delivery device assembled from at least one component made as claimed in claim 1 .

12 . A method as referred in claim 5 , wherein the number of linked perfluorinated repeating units is in the range 20 to 40.

13 . A method as claimed in claim 1 , wherein said portion of surface is a polymer surface.

14 . A method as claimed in claim 13 wherein the component is at least partly made of said polymer.

15 . A method as claimed in claim 13 , wherein the silane having two or more reactive silane groups is of formula

X 3-m (R 1 ) m Si-Q-Si(R 2 ) k X 3-k

wherein R 1 and R 2 are independently selected univalent groups, X is a hydrolysable or hydroxy group, m and k are independently 0, 1, or 2 and Q is a divalent organic linking group, comprising a substituted C 2 to C 12 hydrocarbyl chain and one or more amine groups.

16 . A method as claimed in 13 , wherein the at least partially fluorinated compound is polyfluoropolyether silane of the Formula Ia:

R f [Q 1 -[C(R) 2 —Si(Y) 3-x (R 1a ) x ] y ] z   Ia

wherein:

R f is a monovalent or multivalent polyfluoropolyether moiety;

Q 1 is an organic divalent or trivalent linking group;

each R is independently hydrogen or a C1-4 alkyl group;

each Y is independently a hydrolysable group;

R 1a is a C1-8 alkyl or phenyl group;

x is 0 or 1 or 2;

y is 1 or 2; and

z is 1, 2, 3, or 4.

17 . A method as claimed in claim 16 , wherein the polyfluoropolyether moiety R f is C 3 F 7 O(CF(CF 3 )CF2O) p CF(CF 3 )—, wherein the average value of p is in the range 3 to 50.

18 . A method as claimed in claim 16 , wherein z=1.

19 . A method as claimed in claim 16 , wherein y=1.

20 . A method as claimed in claim 16 , wherein Q 1 contains one or more functional groups selected from the group consisting of esters, amides, sulfonamides, carbonyl, carbonates, ureylenes, and carbamates.

21 . A method as claimed in claim 20 wherein Q 1 comprises from 2 to 25 linearly arranged carbon atoms, optionally interrupted by one or more heteroatoms.

22 . A method as claimed in claim 13 , wherein the polymer is a thermoplastic.

23 . A method as claimed in claim 22 , wherein the thermoplastic material is selected from the group consisting of polyolefines, a polyesters, polyoxymethylene, nylons, and copolymers comprising acrylonitrile, butadiene and styrene.

24 . A coated component for a medicinal delivery device comprising a component and a fluorine-containing coating, wherein the fluorine-containing coating comprises two layers, a first polyfluoropolyether-containing layer comprising polyfluoropolyether silane entities of the following Formula Ib:

R f [Q 1 -[C(R) 2 —Si(O—) 3-x (R 1a ) x ] y ] z   Ib

which shares at least one covalent bond with a second non-fluorinated layer comprising entities of the following Formula

(—O) 3-m-n (X) n (R 1 ) m Si-Q-Si(R 2 ) k (X) l (O—) 3-k-l   IIb

which in turn shares at least one covalent bond with the component; and wherein:

R f is a monovalent or multivalent polyfluoropolyether segment;

Q 1 is an organic divalent or trivalent linking group;

each R is independently hydrogen or a C1-4 alkyl group;

R Ia is a C1-8 alkyl or phenyl group;

k, 1, m and n are independently 0, 1 or 2, but with the priviso that m+n and k+1 are at most 2;

x is 0 or 1 or 2;

y is 1 or 2; and

z is 1, 2, 3, or 4;

R 1 and R 2 are independently selected univalent groups, X is a hydrolysable or hydroxy group, m and k are independently 0, 1, or 2 and Q is a divalent organic linking group, comprising a substituted C 2 to C 12 hydrocarbyl chain and one or more amine groups.

25 . A coated component for a medicinal delivery device as claimed in claim 24 , wherein z=1.

26 . A coated component for a medicinal delivery device as claimed in claim 24 , wherein y=1.

27 . A coated component for a medicinal delivery device as claimed in claim 26 , wherein the entity of Formula IIb shares a covalent bond with a polymer surface of the component.

28 . A coated component for a medicinal delivery device as claimed in claim 26 , wherein Q 1 includes one or more organic linking groups selected from —C(O)N(R)—(CH 2 ) k —, —S(O) 2 N(R)—(CH 2 ) k —, —(CH 2 ) k —, —CH 2 O—(CH 2 ) k —, —C(O)S—(CH 2 ) k —, —CH 2 OC(O)N(R)—(CH 2 ) k —, wherein R is hydrogen or C1-4 alkyl, and k is 2 to about 25, preferably k is 2 to about 15, more preferably k is 2 to about 10.

29 . A coated component for a medicinal delivery device as claimed in claim 24 , wherein y=2.

30 . A coated component for a medicinal delivery device as claimed in claim 29 , wherein the entity of Formula IIb shares a covalent bond with a metal surface of the component, in particular a surface of an aluminium alloy, an iron alloy, or a steel alloy.

31 . A coated component for a medicinal delivery device as claimed in claim 29 , wherein Q 1 includes as organic linking group

—CH 2 OCH 2 CH(OC(O)NH(CH 2 ) 3 —)CH 2 OC(O)NH(CH 2 ) 3 —

or

—C(O)NHCH 2 CH[OC(O)NH—]CH 2 OC(O)NH—.

32 . A coated component for a medicinal delivery device as claimed in claim 24 , wherein the component is a component of a metered dose inhaler.

33 . A coated component as claimed in claim 32 , wherein the component is selected from the group consisting of an actuator, an aerosol container, a ferrule, a valve body, a valve stem and a compression spring.

34 . A medicinal delivery device assembled from at least one coated component as claimed in claim 24 .

Assignments (4)
TERMINATION AND RELEASE OF SECURITY INTEREST IN PATENT COLLATERAL RECORDED AT R/F 053586/0715 Recorded Dec 12, 2022
From: MIDCAP FINANCIAL TRUST, AS ADMINISTRATIVE AGENT
To: KINDEVA DRUG DELIVERY L.P.
Reel/Frame 062115/0707 →
SECURITY INTEREST Recorded Aug 24, 2020
From: KINDEVA DRUG DELIVERY L.P.
To: MIDCAP FINANCIAL TRUST, AS ADMINISTRATIVE AGENT
Reel/Frame 053586/0715 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 2, 2020
From: 3M COMPANY; 3M INNOVATIVE PROPERTIES COMPANY
To: KINDEVA DRUG DELIVERY L.P.
Reel/Frame 052818/0234 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 21, 2016
From: JINKS, PHILIP A; AUDENAERT, FRANS A
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 040395/0864 →